data_global
_publcif_datablock.id '{e6c00078-b2a2-48fe-bade-f4053a1f4afd}'
_audit_update_record
;
2015-04-30 # Formatted by IUCr publCIF system
;
_journal_date_recd_electronic 2014-12-16
_journal_date_to_coeditor ?
_journal_date_from_coeditor ?
_journal_date_accepted 2015-03-11
_journal_date_printers_first ?
_journal_date_printers_final ?
_journal_date_proofs_out ?
_journal_date_proofs_in ?
_journal_coeditor_name ?
_journal_coeditor_code ZX5004
_journal_coeditor_notes
; ?
;
_journal_paper_category FA
_journal_techeditor_code M150496
_iucr_compatibility_tag ACTA95
_journal_techeditor_notes
; ?
;
_journal_coden_ASTM ?
_journal_name_full ?
_journal_year ?
_journal_volume ?
_journal_issue ?
_journal_page_first ?
_journal_page_last ?
_journal_suppl_publ_number ?
_journal_suppl_publ_pages ?
data_2ABSACPR
_publcif_datablock.id '{ff55f32d-463c-46a0-a5da-c6956429db7c}'
_database_code_depnum_ccdc_archive 'CCDC 1039189'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point 341
_chemical_formula_moiety C6H8N2O2S,C6H11NO
_chemical_formula_sum
'C12 H19 N3 O3 S'
_chemical_formula_weight 285.36
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'S' 'S' 0.1246 0.1234
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P121/n1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a 7.2731(4)
_cell_length_b 15.9052(10)
_cell_length_c 12.7766(6)
_cell_angle_alpha 90.00
_cell_angle_beta 99.291(5)
_cell_angle_gamma 90.00
_cell_volume 1458.60(15)
_cell_formula_units_Z 4
_cell_measurement_temperature 298(2)
_cell_measurement_reflns_used 2272
_cell_measurement_theta_min 3.1280
_cell_measurement_theta_max 28.7260
_exptl_crystal_description PLATE
_exptl_crystal_colour COLORLES
_exptl_crystal_size_max 0.22
_exptl_crystal_size_mid 0.21
_exptl_crystal_size_min 0.20
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.299
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 608
_exptl_absorpt_coefficient_mu 0.230
_exptl_absorpt_correction_type 'multi-scan'
_exptl_absorpt_correction_T_min 0.87418
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_process_details SADABS
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 298(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Xcalibur, Eos, Gemini'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 5525
_diffrn_reflns_av_R_equivalents 0.0204
_diffrn_reflns_av_sigmaI/netI 0.0293
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_k_max 18
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_theta_min 3.03
_diffrn_reflns_theta_max 24.71
_reflns_number_total 2488
_reflns_number_gt 1993
_reflns_threshold_expression >2sigma(I)
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^2^, conventional
R-factors R are based on F, with F set to zero for
negative F^2^. The threshold expression of F^2^ >
\s(F^2^) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^2^ are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0513P)^2^+0.2431P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 2488
_refine_ls_number_parameters 179
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0508
_refine_ls_R_factor_gt 0.0383
_refine_ls_wR_factor_ref 0.0995
_refine_ls_wR_factor_gt 0.0932
_refine_ls_goodness_of_fit_ref 1.017
_refine_ls_restrained_S_all 1.017
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.03105(7) 0.83445(3) 0.15700(4) 0.04286(18) Uani 1 1 d . . .
O3 O -0.19797(19) 0.47718(9) 0.56486(11) 0.0533(4) Uani 1 1 d . . .
O2 O 0.1587(2) 0.84605(10) 0.25335(11) 0.0589(4) Uani 1 1 d . . .
N3 N 0.0943(2) 0.43705(11) 0.62356(13) 0.0507(4) Uani 1 1 d . . .
H3A H 0.1222 0.4525 0.5636 0.061 Uiso 1 1 calc R . .
O1 O -0.1464(2) 0.79747(10) 0.16181(12) 0.0603(4) Uani 1 1 d . . .
C6 C 0.0484(3) 0.74236(12) -0.02378(16) 0.0451(5) Uani 1 1 d . . .
N1 N -0.0085(3) 0.92530(12) 0.10533(15) 0.0484(5) Uani 1 1 d . . .
H1A H -0.094(3) 0.9264(14) 0.0607(19) 0.058 Uiso 1 1 d . . .
H1B H 0.094(3) 0.9551(14) 0.0993(17) 0.058 Uiso 1 1 d . . .
C1 C 0.1442(3) 0.77321(12) 0.07254(15) 0.0397(5) Uani 1 1 d . . .
C7 C -0.0815(3) 0.44355(12) 0.63577(16) 0.0444(5) Uani 1 1 d . . .
N2 N -0.1366(3) 0.75970(12) -0.05867(15) 0.0623(5) Uani 1 1 d . . .
H2A H -0.1843 0.7206 -0.1015 0.075 Uiso 1 1 d R . .
H2B H -0.1948 0.7615 -0.0050 0.075 Uiso 1 1 d R . .
C4 C 0.3371(4) 0.68114(16) -0.0565(2) 0.0709(7) Uani 1 1 d . . .
H4 H 0.4020 0.6502 -0.1004 0.085 Uiso 1 1 calc R . .
C2 C 0.3335(3) 0.75770(14) 0.10226(18) 0.0548(6) Uani 1 1 d . . .
H2 H 0.3958 0.7791 0.1660 0.066 Uiso 1 1 calc R . .
C12 C 0.2458(3) 0.40596(15) 0.70280(18) 0.0571(6) Uani 1 1 d . . .
H12A H 0.3589 0.4036 0.6717 0.069 Uiso 1 1 calc R . .
H12B H 0.2168 0.3492 0.7226 0.069 Uiso 1 1 calc R . .
C5 C 0.1519(4) 0.69616(14) -0.08703(19) 0.0616(6) Uani 1 1 d . . .
H5 H 0.0927 0.6751 -0.1517 0.074 Uiso 1 1 calc R . .
C8 C -0.1377(3) 0.41193(16) 0.73576(17) 0.0586(6) Uani 1 1 d . . .
H8A H -0.0966 0.3541 0.7468 0.070 Uiso 1 1 calc R . .
H8B H -0.2726 0.4124 0.7280 0.070 Uiso 1 1 calc R . .
C11 C 0.2803(3) 0.45962(16) 0.80099(19) 0.0643(6) Uani 1 1 d . . .
H11A H 0.2742 0.5183 0.7800 0.077 Uiso 1 1 calc R . .
H11B H 0.4053 0.4488 0.8379 0.077 Uiso 1 1 calc R . .
C9 C -0.0588(3) 0.46304(17) 0.83262(19) 0.0688(7) Uani 1 1 d . . .
H9A H -0.1332 0.4525 0.8878 0.083 Uiso 1 1 calc R . .
H9B H -0.0708 0.5222 0.8145 0.083 Uiso 1 1 calc R . .
C10 C 0.1438(3) 0.44484(17) 0.87691(18) 0.0690(7) Uani 1 1 d . . .
H10A H 0.1802 0.4797 0.9391 0.083 Uiso 1 1 calc R . .
H10B H 0.1539 0.3866 0.8998 0.083 Uiso 1 1 calc R . .
C3 C 0.4291(3) 0.71126(16) 0.0386(2) 0.0696(7) Uani 1 1 d . . .
H3 H 0.5552 0.7002 0.0595 0.083 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0492(3) 0.0467(3) 0.0322(3) 0.0030(2) 0.0050(2) -0.0020(2)
O3 0.0480(8) 0.0652(9) 0.0446(8) 0.0064(7) 0.0011(7) 0.0006(7)
O2 0.0724(10) 0.0662(10) 0.0335(8) -0.0019(7) -0.0049(7) 0.0041(8)
N3 0.0524(10) 0.0610(11) 0.0399(10) 0.0068(8) 0.0112(8) 0.0056(9)
O1 0.0579(9) 0.0670(10) 0.0602(10) 0.0016(8) 0.0223(7) -0.0130(8)
C6 0.0564(12) 0.0396(10) 0.0376(11) 0.0039(9) 0.0029(9) -0.0034(9)
N1 0.0477(10) 0.0479(10) 0.0468(11) 0.0035(9) -0.0005(8) 0.0001(9)
C1 0.0449(10) 0.0387(10) 0.0351(11) 0.0057(8) 0.0050(8) -0.0035(9)
C7 0.0483(11) 0.0428(11) 0.0419(11) -0.0004(10) 0.0061(9) -0.0044(10)
N2 0.0644(12) 0.0665(12) 0.0494(11) -0.0080(10) -0.0104(9) -0.0059(10)
C4 0.0858(19) 0.0631(15) 0.0726(18) 0.0013(14) 0.0393(15) 0.0115(14)
C2 0.0480(12) 0.0614(14) 0.0538(14) 0.0040(11) 0.0048(10) -0.0017(11)
C12 0.0512(12) 0.0625(14) 0.0590(14) 0.0121(12) 0.0131(10) 0.0117(11)
C5 0.0923(19) 0.0513(13) 0.0419(13) -0.0046(11) 0.0130(12) -0.0024(13)
C8 0.0512(12) 0.0729(15) 0.0530(14) 0.0141(12) 0.0124(10) -0.0060(11)
C11 0.0612(14) 0.0700(15) 0.0572(15) 0.0110(13) -0.0037(11) -0.0081(12)
C9 0.0814(17) 0.0810(17) 0.0478(14) 0.0040(13) 0.0221(12) 0.0121(14)
C10 0.0879(18) 0.0730(16) 0.0430(13) 0.0024(12) 0.0013(12) -0.0026(14)
C3 0.0549(14) 0.0759(17) 0.0813(19) 0.0082(15) 0.0213(13) 0.0084(13)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4283(15) . ?
S1 O2 1.4290(14) . ?
S1 N1 1.5954(18) . ?
S1 C1 1.754(2) . ?
O3 C7 1.256(2) . ?
N3 C7 1.317(2) . ?
N3 C12 1.457(3) . ?
N3 H3A 0.8600 . ?
C6 N2 1.375(2) . ?
C6 C5 1.399(3) . ?
C6 C1 1.401(3) . ?
N1 H1A 0.77(2) . ?
N1 H1B 0.90(2) . ?
C1 C2 1.390(3) . ?
C7 C8 1.490(3) . ?
N2 H2A 0.8631 . ?
N2 H2B 0.8626 . ?
C4 C5 1.361(3) . ?
C4 C3 1.375(4) . ?
C4 H4 0.9300 . ?
C2 C3 1.369(3) . ?
C2 H2 0.9300 . ?
C12 C11 1.505(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C5 H5 0.9300 . ?
C8 C9 1.514(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C11 C10 1.514(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C9 C10 1.519(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C3 H3 0.9300 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 118.80(10) . . ?
O1 S1 N1 106.67(10) . . ?
O2 S1 N1 106.76(10) . . ?
O1 S1 C1 108.34(9) . . ?
O2 S1 C1 107.32(9) . . ?
N1 S1 C1 108.63(9) . . ?
C7 N3 C12 125.74(18) . . ?
C7 N3 H3A 117.1 . . ?
C12 N3 H3A 117.1 . . ?
N2 C6 C5 120.5(2) . . ?
N2 C6 C1 122.43(19) . . ?
C5 C6 C1 116.96(19) . . ?
S1 N1 H1A 113.3(17) . . ?
S1 N1 H1B 114.7(14) . . ?
H1A N1 H1B 120(2) . . ?
C2 C1 C6 120.54(19) . . ?
C2 C1 S1 118.23(15) . . ?
C6 C1 S1 121.22(15) . . ?
O3 C7 N3 120.19(19) . . ?
O3 C7 C8 121.05(18) . . ?
N3 C7 C8 118.75(18) . . ?
C6 N2 H2A 109.4 . . ?
C6 N2 H2B 109.2 . . ?
H2A N2 H2B 109.2 . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C3 C2 C1 120.6(2) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
N3 C12 C11 113.09(18) . . ?
N3 C12 H12A 109.0 . . ?
C11 C12 H12A 109.0 . . ?
N3 C12 H12B 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C4 C5 C6 121.8(2) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C7 C8 C9 113.53(19) . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
C9 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C12 C11 C10 114.09(19) . . ?
C12 C11 H11A 108.7 . . ?
C10 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
C10 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C8 C9 C10 114.8(2) . . ?
C8 C9 H9A 108.6 . . ?
C10 C9 H9A 108.6 . . ?
C8 C9 H9B 108.6 . . ?
C10 C9 H9B 108.6 . . ?
H9A C9 H9B 107.5 . . ?
C11 C10 C9 115.38(19) . . ?
C11 C10 H10A 108.4 . . ?
C9 C10 H10A 108.4 . . ?
C11 C10 H10B 108.4 . . ?
C9 C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
C2 C3 C4 119.4(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 24.71
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max 0.150
_refine_diff_density_min -0.320
_refine_diff_density_rms 0.040
data_BSAAZL
_publcif_datablock.id '{6ae9f214-f6c1-4470-8cfd-e02939af13f3}'
_database_code_depnum_ccdc_archive 'CCDC 1039196'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety C6H7NO2S,C7H13NO
_chemical_formula_sum
'C13 H20 N2 O3 S'
_chemical_formula_weight 284.37
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'S' 'S' 0.1246 0.1234
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting 'Monoclinic'
_symmetry_space_group_name_H-M 'P2(1)/n '
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a 7.3020(9)
_cell_length_b 17.189(2)
_cell_length_c 12.2835(16)
_cell_angle_alpha 90.00
_cell_angle_beta 106.760(2)
_cell_angle_gamma 90.00
_cell_volume 1476.2(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 298(2)
_cell_measurement_reflns_used 3397
_cell_measurement_theta_min 2.93
_cell_measurement_theta_max 23.26
_exptl_crystal_description PLATE
_exptl_crystal_colour COLORLES
_exptl_crystal_size_max 0.22
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.20
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.279
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 608
_exptl_absorpt_coefficient_mu 0.225
_exptl_absorpt_correction_type 'none'
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 298(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 13710
_diffrn_reflns_av_R_equivalents 0.0373
_diffrn_reflns_av_sigmaI/netI 0.0252
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_k_min -20
_diffrn_reflns_limit_k_max 20
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_theta_min 2.10
_diffrn_reflns_theta_max 24.71
_reflns_number_total 2520
_reflns_number_gt 2154
_reflns_threshold_expression >2sigma(I)
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^2^, conventional
R-factors R are based on F, with F set to zero for
negative F^2^. The threshold expression of F^2^ >
\s(F^2^) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^2^ are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0573P)^2^+0.8349P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 2520
_refine_ls_number_parameters 184
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0699
_refine_ls_R_factor_gt 0.0597
_refine_ls_wR_factor_ref 0.1419
_refine_ls_wR_factor_gt 0.1353
_refine_ls_goodness_of_fit_ref 1.092
_refine_ls_restrained_S_all 1.092
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.38938(11) 0.14789(5) 0.32694(6) 0.0614(3) Uani 1 1 d . . .
O3 O 0.6840(3) 0.53498(12) 0.94445(16) 0.0631(5) Uani 1 1 d . . .
N2 N 0.3761(3) 0.56077(15) 0.8646(2) 0.0566(6) Uani 1 1 d . . .
C7 C 0.5577(4) 0.57061(15) 0.8708(2) 0.0519(7) Uani 1 1 d . . .
N1 N 0.4595(4) 0.06644(16) 0.3858(2) 0.0624(7) Uani 1 1 d . . .
C1 C 0.2838(4) 0.20092(15) 0.4165(2) 0.0509(7) Uani 1 1 d . . .
C6 C 0.3969(5) 0.24554(18) 0.5024(2) 0.0649(8) Uani 1 1 d . . .
H6 H 0.5285 0.2473 0.5140 0.078 Uiso 1 1 calc R . .
O1 O 0.5566(4) 0.18886(15) 0.3219(2) 0.0918(8) Uani 1 1 d . . .
C2 C 0.0897(4) 0.19751(18) 0.4000(3) 0.0649(8) Uani 1 1 d . . .
H2 H 0.0131 0.1669 0.3422 0.078 Uiso 1 1 calc R . .
O2 O 0.2438(4) 0.13196(16) 0.22504(17) 0.0936(8) Uani 1 1 d . . .
C13 C 0.2123(4) 0.5940(2) 0.7798(3) 0.0677(8) Uani 1 1 d . . .
H13A H 0.2483 0.6442 0.7562 0.081 Uiso 1 1 calc R . .
H13B H 0.1099 0.6026 0.8142 0.081 Uiso 1 1 calc R . .
C12 C 0.1394(4) 0.5429(2) 0.6764(3) 0.0764(10) Uani 1 1 d . . .
H12A H 0.0416 0.5712 0.6200 0.092 Uiso 1 1 calc R . .
H12B H 0.0791 0.4974 0.6979 0.092 Uiso 1 1 calc R . .
C8 C 0.6142(4) 0.62429(18) 0.7904(3) 0.0678(8) Uani 1 1 d . . .
H8A H 0.7423 0.6434 0.8265 0.081 Uiso 1 1 calc R . .
H8B H 0.5286 0.6687 0.7760 0.081 Uiso 1 1 calc R . .
C10 C 0.4123(5) 0.5781(2) 0.5924(3) 0.0832(10) Uani 1 1 d . . .
H10A H 0.3448 0.6273 0.5867 0.100 Uiso 1 1 calc R . .
H10B H 0.4280 0.5668 0.5182 0.100 Uiso 1 1 calc R . .
C9 C 0.6104(5) 0.5875(2) 0.6774(3) 0.0773(10) Uani 1 1 d . . .
H9A H 0.6696 0.5366 0.6922 0.093 Uiso 1 1 calc R . .
H9B H 0.6881 0.6190 0.6424 0.093 Uiso 1 1 calc R . .
C11 C 0.2909(6) 0.5156(2) 0.6214(3) 0.0867(11) Uani 1 1 d . . .
H11A H 0.3745 0.4791 0.6726 0.104 Uiso 1 1 calc R . .
H11B H 0.2272 0.4876 0.5523 0.104 Uiso 1 1 calc R . .
C3 C 0.0098(5) 0.2398(2) 0.4696(3) 0.0812(10) Uani 1 1 d . . .
H3 H -0.1215 0.2380 0.4589 0.097 Uiso 1 1 calc R . .
C4 C 0.1229(7) 0.2846(2) 0.5545(3) 0.0874(11) Uani 1 1 d . . .
H4 H 0.0684 0.3133 0.6013 0.105 Uiso 1 1 calc R . .
C5 C 0.3157(7) 0.2872(2) 0.5707(3) 0.0856(11) Uani 1 1 d . . .
H5 H 0.3921 0.3177 0.6288 0.103 Uiso 1 1 calc R . .
H1A H 0.556(4) 0.0704(17) 0.437(3) 0.055(9) Uiso 1 1 d . . .
H1B H 0.367(4) 0.0358(18) 0.394(2) 0.063(9) Uiso 1 1 d . . .
H2A H 0.350(4) 0.5300(17) 0.910(3) 0.056(9) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0675(5) 0.0681(5) 0.0491(4) 0.0095(3) 0.0176(3) 0.0087(4)
O3 0.0502(11) 0.0787(14) 0.0541(11) 0.0086(10) 0.0050(9) 0.0043(10)
N2 0.0512(14) 0.0715(16) 0.0477(13) 0.0093(12) 0.0155(11) 0.0044(12)
C7 0.0542(16) 0.0519(15) 0.0465(15) -0.0062(12) 0.0093(13) -0.0030(13)
N1 0.0509(15) 0.0663(17) 0.0639(17) 0.0031(13) 0.0072(14) 0.0013(13)
C1 0.0572(16) 0.0496(15) 0.0417(14) 0.0096(12) 0.0077(12) 0.0015(12)
C6 0.0689(19) 0.0658(19) 0.0542(17) 0.0034(15) 0.0086(15) -0.0071(15)
O1 0.0985(18) 0.0885(17) 0.1086(19) 0.0215(14) 0.0617(15) -0.0026(14)
C2 0.0614(19) 0.071(2) 0.0570(17) 0.0009(15) 0.0087(14) -0.0012(15)
O2 0.1033(18) 0.118(2) 0.0458(12) -0.0055(12) -0.0006(12) 0.0350(15)
C13 0.0514(17) 0.086(2) 0.0670(19) 0.0105(17) 0.0195(14) 0.0184(15)
C12 0.0546(18) 0.103(3) 0.0623(19) 0.0138(18) 0.0027(15) -0.0069(17)
C8 0.0568(18) 0.0632(19) 0.080(2) 0.0119(16) 0.0139(16) -0.0092(14)
C10 0.102(3) 0.093(3) 0.0595(19) 0.0084(18) 0.0313(19) 0.012(2)
C9 0.070(2) 0.095(2) 0.076(2) 0.0293(19) 0.0355(18) 0.0144(18)
C11 0.103(3) 0.089(3) 0.062(2) -0.0165(18) 0.014(2) -0.014(2)
C3 0.074(2) 0.091(3) 0.087(3) 0.014(2) 0.037(2) 0.0150(19)
C4 0.134(4) 0.073(2) 0.069(2) 0.0041(19) 0.051(2) 0.017(2)
C5 0.122(3) 0.074(2) 0.0550(19) -0.0068(17) 0.015(2) -0.013(2)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.416(2) . ?
S1 O1 1.426(2) . ?
S1 N1 1.591(3) . ?
S1 C1 1.768(3) . ?
O3 C7 1.250(3) . ?
N2 C7 1.317(3) . ?
N2 C13 1.457(3) . ?
N2 H2A 0.83(3) . ?
C7 C8 1.495(4) . ?
N1 H1A 0.80(3) . ?
N1 H1B 0.88(3) . ?
C1 C6 1.372(4) . ?
C1 C2 1.374(4) . ?
C6 C5 1.363(5) . ?
C6 H6 0.9300 . ?
C2 C3 1.375(4) . ?
C2 H2 0.9300 . ?
C13 C12 1.511(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C12 C11 1.526(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C8 C9 1.517(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C10 C11 1.500(5) . ?
C10 C9 1.529(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C3 C4 1.365(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.364(5) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 119.42(17) . . ?
O2 S1 N1 107.04(17) . . ?
O1 S1 N1 106.66(16) . . ?
O2 S1 C1 107.39(14) . . ?
O1 S1 C1 107.74(14) . . ?
N1 S1 C1 108.17(13) . . ?
C7 N2 C13 126.6(3) . . ?
C7 N2 H2A 118(2) . . ?
C13 N2 H2A 116(2) . . ?
O3 C7 N2 120.0(3) . . ?
O3 C7 C8 119.6(2) . . ?
N2 C7 C8 120.4(3) . . ?
S1 N1 H1A 112(2) . . ?
S1 N1 H1B 114.8(19) . . ?
H1A N1 H1B 119(3) . . ?
C6 C1 C2 120.3(3) . . ?
C6 C1 S1 119.5(2) . . ?
C2 C1 S1 120.2(2) . . ?
C5 C6 C1 119.7(3) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C1 C2 C3 119.3(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
N2 C13 C12 113.0(3) . . ?
N2 C13 H13A 109.0 . . ?
C12 C13 H13A 109.0 . . ?
N2 C13 H13B 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C13 C12 C11 115.2(3) . . ?
C13 C12 H12A 108.5 . . ?
C11 C12 H12A 108.5 . . ?
C13 C12 H12B 108.5 . . ?
C11 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C7 C8 C9 114.3(3) . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C11 C10 C9 114.9(3) . . ?
C11 C10 H10A 108.5 . . ?
C9 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C9 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C8 C9 C10 115.6(3) . . ?
C8 C9 H9A 108.4 . . ?
C10 C9 H9A 108.4 . . ?
C8 C9 H9B 108.4 . . ?
C10 C9 H9B 108.4 . . ?
H9A C9 H9B 107.4 . . ?
C10 C11 C12 116.0(3) . . ?
C10 C11 H11A 108.3 . . ?
C12 C11 H11A 108.3 . . ?
C10 C11 H11B 108.3 . . ?
C12 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full 24.71
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max 0.258
_refine_diff_density_min -0.270
_refine_diff_density_rms 0.049
data_4ClBSACPR
_publcif_datablock.id '{44fb6c3f-7f62-4ff1-8b5d-03e1a9d7af91}'
_database_code_depnum_ccdc_archive 'CCDC 1039194'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point 355
_chemical_formula_moiety C6H6ClNO2S,C6H11NO
_chemical_formula_sum
'C12 H17 Cl N2 O3 S'
_chemical_formula_weight 304.79
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'S' 'S' 0.1246 0.1234
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'Cl' 'Cl' 0.1484 0.1585
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_H-M 'P 21 21 21'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
_cell_length_a 7.1564(13)
_cell_length_b 13.369(2)
_cell_length_c 15.276(3)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 1461.5(5)
_cell_formula_units_Z 4
_cell_measurement_temperature 297(2)
_cell_measurement_reflns_used 543
_cell_measurement_theta_min 2.8406
_cell_measurement_theta_max 26.3142
_exptl_crystal_description PLATE
_exptl_crystal_colour COLORLES
_exptl_crystal_size_max 0.23
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.20
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.385
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 640
_exptl_absorpt_coefficient_mu 0.409
_exptl_absorpt_correction_type 'multi-scan'
_exptl_absorpt_correction_T_min 0.33312
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_process_details SADABS
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 297(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Xcalibur, Eos, Gemini'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 4403
_diffrn_reflns_av_R_equivalents 0.0823
_diffrn_reflns_av_sigmaI/netI 0.2202
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_limit_l_max 19
_diffrn_reflns_theta_min 3.05
_diffrn_reflns_theta_max 26.37
_reflns_number_total 2851
_reflns_number_gt 1152
_reflns_threshold_expression >2sigma(I)
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^2^, conventional
R-factors R are based on F, with F set to zero for
negative F^2^. The threshold expression of F^2^ >
\s(F^2^) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^2^ are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0114P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.11(15)
_refine_ls_number_reflns 2851
_refine_ls_number_parameters 178
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.2263
_refine_ls_R_factor_gt 0.0896
_refine_ls_wR_factor_ref 0.1141
_refine_ls_wR_factor_gt 0.0874
_refine_ls_goodness_of_fit_ref 0.968
_refine_ls_restrained_S_all 0.968
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S3 S 0.0196(3) 0.35614(15) 0.88356(14) 0.0535(6) Uani 1 1 d . . .
Cl1 Cl 0.5566(3) 0.07660(16) 0.67777(13) 0.0877(8) Uani 1 1 d . . .
O2 O 0.0844(6) 0.4564(3) 0.8748(3) 0.0713(16) Uani 1 1 d . . .
O3 O -0.0805(7) 1.1190(3) 0.9736(3) 0.0632(17) Uani 1 1 d . . .
C7 C 0.0056(12) 1.0508(6) 0.9436(5) 0.054(2) Uani 1 1 d . . .
C6 C 0.0971(10) 0.1977(5) 0.7767(4) 0.0458(19) Uani 1 1 d . . .
H6 H -0.0304 0.1844 0.7780 0.055 Uiso 1 1 calc R . .
C3 C 0.4741(11) 0.2386(5) 0.7731(5) 0.055(2) Uani 1 1 d . . .
H3 H 0.6014 0.2523 0.7714 0.066 Uiso 1 1 calc R . .
C4 C 0.4035(11) 0.1560(5) 0.7312(4) 0.048(2) Uani 1 1 d . . .
O1 O -0.1687(6) 0.3320(4) 0.8608(3) 0.0827(19) Uani 1 1 d . . .
C2 C 0.3530(10) 0.3013(5) 0.8181(4) 0.052(2) Uani 1 1 d . . .
H2 H 0.3983 0.3579 0.8464 0.063 Uiso 1 1 calc R . .
C5 C 0.2143(11) 0.1350(5) 0.7310(4) 0.055(2) Uani 1 1 d . . .
H5 H 0.1675 0.0801 0.7009 0.066 Uiso 1 1 calc R . .
C1 C 0.1653(9) 0.2791(5) 0.8203(4) 0.0382(18) Uani 1 1 d . . .
N1 N 0.0459(9) 0.3254(4) 0.9837(4) 0.0539(19) Uani 1 1 d . . .
H1A H 0.005(11) 0.273(4) 1.002(5) 0.065 Uiso 1 1 d . . .
H1B H 0.167(8) 0.349(5) 1.003(4) 0.065 Uiso 1 1 d . . .
N2 N 0.1869(9) 1.0380(4) 0.9556(4) 0.065(2) Uani 1 1 d . . .
H2A H 0.2385 1.0812 0.9896 0.078 Uiso 1 1 calc R . .
C8 C -0.0874(10) 0.9702(6) 0.8853(5) 0.072(2) Uani 1 1 d . . .
H8A H -0.2174 0.9883 0.8768 0.086 Uiso 1 1 calc R . .
H8B H -0.0275 0.9711 0.8284 0.086 Uiso 1 1 calc R . .
C10 C 0.1078(11) 0.8120(6) 0.9053(6) 0.078(3) Uani 1 1 d . . .
H10A H 0.0981 0.7442 0.9275 0.093 Uiso 1 1 calc R . .
H10B H 0.1291 0.8076 0.8427 0.093 Uiso 1 1 calc R . .
C12 C 0.3120(11) 0.9637(7) 0.9210(6) 0.092(3) Uani 1 1 d . . .
H12A H 0.4381 0.9809 0.9387 0.110 Uiso 1 1 calc R . .
H12B H 0.3075 0.9672 0.8576 0.110 Uiso 1 1 calc R . .
C9 C -0.0795(11) 0.8652(6) 0.9207(5) 0.083(3) Uani 1 1 d . . .
H9A H -0.1781 0.8262 0.8936 0.099 Uiso 1 1 calc R . .
H9B H -0.1039 0.8672 0.9831 0.099 Uiso 1 1 calc R . .
C11 C 0.2757(12) 0.8613(7) 0.9469(6) 0.094(3) Uani 1 1 d . . .
H11A H 0.2595 0.8598 1.0100 0.112 Uiso 1 1 calc R . .
H11B H 0.3854 0.8216 0.9333 0.112 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S3 0.0373(13) 0.0552(14) 0.0680(14) 0.0000(13) 0.0053(11) 0.0072(12)
Cl1 0.095(2) 0.0763(14) 0.0922(16) -0.0156(15) 0.0284(15) 0.0242(15)
O2 0.067(4) 0.044(3) 0.103(4) 0.021(3) 0.016(3) 0.018(3)
O3 0.060(4) 0.050(4) 0.080(4) -0.019(3) 0.014(3) 0.002(3)
C7 0.036(6) 0.056(6) 0.071(6) 0.007(5) -0.006(5) -0.028(5)
C6 0.035(5) 0.053(5) 0.050(5) 0.009(4) -0.001(4) -0.013(4)
C3 0.040(5) 0.059(5) 0.066(5) -0.012(5) 0.006(5) -0.006(5)
C4 0.056(6) 0.043(5) 0.045(5) 0.005(4) 0.007(4) 0.014(5)
O1 0.026(3) 0.108(5) 0.114(5) -0.023(4) -0.007(3) 0.014(3)
C2 0.050(6) 0.057(5) 0.049(5) -0.014(5) 0.001(4) 0.001(5)
C5 0.068(6) 0.042(5) 0.054(5) -0.016(5) -0.005(5) -0.010(5)
C1 0.032(5) 0.038(5) 0.044(4) -0.004(4) 0.000(4) -0.005(4)
N1 0.049(5) 0.045(4) 0.068(5) 0.007(4) 0.018(4) -0.011(4)
N2 0.055(5) 0.039(4) 0.100(5) -0.024(4) -0.019(4) 0.009(4)
C8 0.046(5) 0.072(6) 0.097(7) -0.002(6) 0.002(5) -0.011(5)
C10 0.079(7) 0.050(5) 0.104(7) 0.004(5) 0.007(6) -0.003(6)
C12 0.044(6) 0.079(7) 0.152(10) -0.012(8) -0.015(6) 0.003(6)
C9 0.065(7) 0.072(7) 0.112(8) -0.011(6) -0.007(5) -0.027(6)
C11 0.075(8) 0.068(7) 0.138(8) 0.003(7) -0.037(6) 0.018(7)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S3 O2 1.424(5) . ?
S3 O1 1.429(5) . ?
S3 N1 1.595(6) . ?
S3 C1 1.756(7) . ?
Cl1 C4 1.730(7) . ?
O3 C7 1.192(8) . ?
C7 N2 1.321(8) . ?
C7 C8 1.549(9) . ?
C6 C1 1.366(8) . ?
C6 C5 1.375(8) . ?
C6 H6 0.9300 . ?
C3 C4 1.373(8) . ?
C3 C2 1.388(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(9) . ?
C2 C1 1.376(8) . ?
C2 H2 0.9300 . ?
C5 H5 0.9300 . ?
N1 H1A 0.82(6) . ?
N1 H1B 0.97(6) . ?
N2 C12 1.438(8) . ?
N2 H2A 0.8600 . ?
C8 C9 1.505(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C10 C11 1.512(10) . ?
C10 C9 1.535(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 C11 1.449(9) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S3 O1 119.8(3) . . ?
O2 S3 N1 107.1(3) . . ?
O1 S3 N1 106.6(3) . . ?
O2 S3 C1 107.9(3) . . ?
O1 S3 C1 107.1(3) . . ?
N1 S3 C1 107.8(3) . . ?
O3 C7 N2 123.6(8) . . ?
O3 C7 C8 122.1(7) . . ?
N2 C7 C8 114.3(8) . . ?
C1 C6 C5 121.0(7) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C4 C3 C2 119.2(7) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 121.6(7) . . ?
C3 C4 Cl1 118.7(7) . . ?
C5 C4 Cl1 119.7(7) . . ?
C1 C2 C3 119.4(7) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C6 C5 C4 118.2(7) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C6 C1 C2 120.6(7) . . ?
C6 C1 S3 121.6(6) . . ?
C2 C1 S3 117.8(6) . . ?
S3 N1 H1A 121(5) . . ?
S3 N1 H1B 108(4) . . ?
H1A N1 H1B 120(7) . . ?
C7 N2 C12 130.5(7) . . ?
C7 N2 H2A 114.7 . . ?
C12 N2 H2A 114.7 . . ?
C9 C8 C7 115.2(7) . . ?
C9 C8 H8A 108.5 . . ?
C7 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
C7 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C11 C10 C9 115.3(6) . . ?
C11 C10 H10A 108.4 . . ?
C9 C10 H10A 108.4 . . ?
C11 C10 H10B 108.4 . . ?
C9 C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
N2 C12 C11 116.1(8) . . ?
N2 C12 H12A 108.2 . . ?
C11 C12 H12A 108.2 . . ?
N2 C12 H12B 108.2 . . ?
C11 C12 H12B 108.2 . . ?
H12A C12 H12B 107.4 . . ?
C8 C9 C10 114.2(7) . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
C10 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C12 C11 C10 116.1(8) . . ?
C12 C11 H11A 108.3 . . ?
C10 C11 H11A 108.3 . . ?
C12 C11 H11B 108.3 . . ?
C10 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 26.37
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max 0.247
_refine_diff_density_min -0.247
_refine_diff_density_rms 0.055
data_SNACPR
_publcif_datablock.id '{e9413eff-41ec-4c5a-b79f-512e0244b8cb}'
_database_code_depnum_ccdc_archive 'CCDC 1039188'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point 368
_chemical_formula_moiety C6H8N2O2S,C6H11NO
_chemical_formula_sum
'C12 H19 N3 O3 S'
_chemical_formula_weight 285.36
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'S' 'S' 0.1246 0.1234
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_H-M 'P 21 21 21'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
_cell_length_a 7.0957(6)
_cell_length_b 13.1280(13)
_cell_length_c 15.3425(18)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 1429.2(2)
_cell_formula_units_Z 4
_cell_measurement_temperature 298(2)
_cell_measurement_reflns_used 831
_cell_measurement_theta_min 2.6498
_cell_measurement_theta_max 24.6592
_exptl_crystal_description PLATE
_exptl_crystal_colour COLORLES
_exptl_crystal_size_max 0.22
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.20
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.326
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 608
_exptl_absorpt_coefficient_mu 0.235
_exptl_absorpt_correction_type 'multi-scan'
_exptl_absorpt_correction_T_min 0.66726
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_process_details SADABS
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 298(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Xcalibur, Eos, Gemini'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 3692
_diffrn_reflns_av_R_equivalents 0.0417
_diffrn_reflns_av_sigmaI/netI 0.1027
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_theta_min 2.66
_diffrn_reflns_theta_max 24.71
_reflns_number_total 2354
_reflns_number_gt 1318
_reflns_threshold_expression >2sigma(I)
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^2^, conventional
R-factors R are based on F, with F set to zero for
negative F^2^. The threshold expression of F^2^ >
\s(F^2^) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^2^ are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0117P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.03(14)
_refine_ls_number_reflns 2354
_refine_ls_number_parameters 179
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1062
_refine_ls_R_factor_gt 0.0529
_refine_ls_wR_factor_ref 0.0796
_refine_ls_wR_factor_gt 0.0638
_refine_ls_goodness_of_fit_ref 0.901
_refine_ls_restrained_S_all 0.901
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C11 C 0.1350(6) 0.8611(4) 0.0600(3) 0.0805(15) Uani 1 1 d . . .
H11A H 0.1392 0.8645 -0.0031 0.097 Uiso 1 1 calc R . .
H11B H 0.0275 0.8195 0.0761 0.097 Uiso 1 1 calc R . .
S1 S 0.90765(16) 0.13847(9) 0.87588(9) 0.0599(3) Uani 1 1 d . . .
O1 O 1.1072(3) 0.1426(2) 0.8626(2) 0.0811(10) Uani 1 1 d . . .
O3 O 0.4913(4) 1.1203(2) 0.0183(2) 0.0694(9) Uani 1 1 d . . .
N3 N 0.2251(5) 1.0426(3) 0.0533(2) 0.0660(11) Uani 1 1 d . . .
H3A H 0.1666 1.0888 0.0242 0.079 Uiso 1 1 calc R . .
O2 O 0.8131(4) 0.0430(2) 0.8621(2) 0.0735(9) Uani 1 1 d . . .
C4 C 0.6531(7) 0.3859(3) 0.7083(3) 0.0562(13) Uani 1 1 d . . .
C3 C 0.8468(6) 0.3754(4) 0.7166(3) 0.0591(13) Uani 1 1 d . . .
H3 H 0.9266 0.4201 0.6875 0.071 Uiso 1 1 calc R . .
C5 C 0.5389(6) 0.3167(3) 0.7511(3) 0.0640(14) Uani 1 1 d . . .
H5 H 0.4088 0.3224 0.7459 0.077 Uiso 1 1 calc R . .
C6 C 0.6134(6) 0.2399(3) 0.8012(3) 0.0583(13) Uani 1 1 d . . .
H6 H 0.5342 0.1944 0.8297 0.070 Uiso 1 1 calc R . .
N1 N 0.8708(5) 0.1686(3) 0.9750(3) 0.0589(12) Uani 1 1 d . . .
H1A H 0.899(6) 0.224(3) 0.997(3) 0.071 Uiso 1 1 d . . .
H1B H 0.759(5) 0.148(3) 0.999(2) 0.071 Uiso 1 1 d . . .
N2 N 0.5796(6) 0.4620(3) 0.6575(2) 0.0828(13) Uani 1 1 d . . .
H2A H 0.6504 0.5161 0.6592 0.099 Uiso 1 1 d R . .
H2B H 0.4693 0.4781 0.6780 0.099 Uiso 1 1 d R . .
C1 C 0.8058(6) 0.2308(3) 0.8090(3) 0.0462(11) Uani 1 1 d . . .
C7 C 0.4103(7) 1.0499(4) 0.0552(3) 0.0565(12) Uani 1 1 d . . .
C2 C 0.9211(6) 0.3000(3) 0.7672(3) 0.0542(12) Uani 1 1 d . . .
H2 H 1.0511 0.2951 0.7736 0.065 Uiso 1 1 calc R . .
C9 C 0.4958(7) 0.8638(4) 0.0672(3) 0.0813(15) Uani 1 1 d . . .
H9A H 0.6011 0.8224 0.0865 0.098 Uiso 1 1 calc R . .
H9B H 0.5021 0.8679 0.0041 0.098 Uiso 1 1 calc R . .
C8 C 0.5188(6) 0.9689(4) 0.1037(3) 0.0744(15) Uani 1 1 d . . .
H8A H 0.6516 0.9866 0.1029 0.089 Uiso 1 1 calc R . .
H8B H 0.4780 0.9686 0.1641 0.089 Uiso 1 1 calc R . .
C12 C 0.1071(6) 0.9650(3) 0.0948(3) 0.0763(15) Uani 1 1 d . . .
H12A H -0.0242 0.9837 0.0875 0.092 Uiso 1 1 calc R . .
H12B H 0.1336 0.9644 0.1568 0.092 Uiso 1 1 calc R . .
C10 C 0.3129(7) 0.8098(3) 0.0924(3) 0.0804(15) Uani 1 1 d . . .
H10A H 0.3166 0.7409 0.0696 0.096 Uiso 1 1 calc R . .
H10B H 0.3070 0.8051 0.1554 0.096 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C11 0.081(3) 0.064(3) 0.096(4) -0.006(4) -0.008(3) -0.013(3)
S1 0.0530(6) 0.0473(6) 0.0794(9) 0.0010(9) -0.0003(7) 0.0085(7)
O1 0.0404(15) 0.084(2) 0.119(3) 0.014(3) 0.0020(17) 0.0153(18)
O3 0.0709(19) 0.0444(18) 0.093(2) 0.007(2) 0.0158(18) -0.0027(18)
N3 0.058(2) 0.046(2) 0.094(3) 0.016(3) -0.011(2) 0.006(2)
O2 0.079(2) 0.0400(16) 0.102(2) -0.005(2) -0.006(2) 0.0026(17)
C4 0.069(3) 0.051(3) 0.048(3) -0.006(3) -0.011(2) -0.001(3)
C3 0.056(3) 0.063(3) 0.058(3) 0.003(3) 0.008(2) -0.007(3)
C5 0.046(3) 0.062(3) 0.085(4) 0.003(3) -0.016(3) -0.003(3)
C6 0.043(3) 0.052(3) 0.080(4) 0.005(3) -0.007(2) -0.008(2)
N1 0.065(2) 0.047(2) 0.064(3) 0.004(2) 0.001(2) -0.001(2)
N2 0.093(3) 0.069(3) 0.086(3) 0.007(3) -0.006(3) 0.011(3)
C1 0.047(2) 0.045(3) 0.046(3) -0.002(3) -0.004(2) 0.006(2)
C7 0.052(3) 0.051(3) 0.067(3) -0.002(3) -0.005(3) 0.012(3)
C2 0.044(2) 0.060(3) 0.059(3) 0.000(3) -0.001(2) 0.008(3)
C9 0.086(3) 0.061(3) 0.097(4) 0.002(4) -0.003(3) 0.032(4)
C8 0.049(3) 0.075(3) 0.100(4) 0.007(4) -0.003(3) 0.011(3)
C12 0.057(3) 0.064(3) 0.107(4) 0.002(4) -0.006(3) -0.003(3)
C10 0.101(4) 0.046(3) 0.094(4) 0.005(3) 0.007(4) 0.004(3)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C11 C12 1.478(6) . ?
C11 C10 1.514(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
S1 O1 1.431(2) . ?
S1 O2 1.437(3) . ?
S1 N1 1.593(4) . ?
S1 C1 1.745(4) . ?
O3 C7 1.227(5) . ?
N3 C7 1.318(5) . ?
N3 C12 1.465(5) . ?
N3 H3A 0.8600 . ?
C4 N2 1.370(5) . ?
C4 C5 1.383(5) . ?
C4 C3 1.387(5) . ?
C3 C2 1.364(5) . ?
C3 H3 0.9300 . ?
C5 C6 1.373(5) . ?
C5 H5 0.9300 . ?
C6 C1 1.376(5) . ?
C6 H6 0.9300 . ?
N1 H1A 0.83(4) . ?
N1 H1B 0.91(3) . ?
N2 H2A 0.8706 . ?
N2 H2B 0.8693 . ?
C1 C2 1.380(5) . ?
C7 C8 1.510(5) . ?
C2 H2 0.9300 . ?
C9 C8 1.499(6) . ?
C9 C10 1.528(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 C11 C10 113.8(4) . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
O1 S1 O2 118.3(2) . . ?
O1 S1 N1 106.8(2) . . ?
O2 S1 N1 106.3(2) . . ?
O1 S1 C1 107.5(2) . . ?
O2 S1 C1 109.03(19) . . ?
N1 S1 C1 108.7(2) . . ?
C7 N3 C12 127.7(4) . . ?
C7 N3 H3A 116.2 . . ?
C12 N3 H3A 116.2 . . ?
N2 C4 C5 121.7(4) . . ?
N2 C4 C3 120.1(5) . . ?
C5 C4 C3 118.1(4) . . ?
C2 C3 C4 120.5(4) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C6 C5 C4 121.5(4) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C1 119.6(4) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
S1 N1 H1A 124(4) . . ?
S1 N1 H1B 117(2) . . ?
H1A N1 H1B 108(4) . . ?
C4 N2 H2A 111.0 . . ?
C4 N2 H2B 108.3 . . ?
H2A N2 H2B 108.0 . . ?
C6 C1 C2 119.4(4) . . ?
C6 C1 S1 121.5(3) . . ?
C2 C1 S1 119.0(3) . . ?
O3 C7 N3 120.8(4) . . ?
O3 C7 C8 121.3(4) . . ?
N3 C7 C8 117.9(4) . . ?
C3 C2 C1 120.8(4) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C8 C9 C10 115.1(4) . . ?
C8 C9 H9A 108.5 . . ?
C10 C9 H9A 108.5 . . ?
C8 C9 H9B 108.5 . . ?
C10 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C9 C8 C7 114.1(4) . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
N3 C12 C11 114.1(4) . . ?
N3 C12 H12A 108.7 . . ?
C11 C12 H12A 108.7 . . ?
N3 C12 H12B 108.7 . . ?
C11 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C11 C10 C9 114.8(4) . . ?
C11 C10 H10A 108.6 . . ?
C9 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 24.71
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max 0.181
_refine_diff_density_min -0.207
_refine_diff_density_rms 0.036
data_4BrBSACPR
_publcif_datablock.id '{665b0f37-4d51-4f60-aad4-cd323a567d2e}'
_database_code_depnum_ccdc_archive 'CCDC 1039192'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point 363
_chemical_formula_moiety C6H6BrNO2S,C6H11NO
_chemical_formula_sum
'C12 H17 Br N2 O3 S'
_chemical_formula_weight 349.25
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'S' 'S' 0.1246 0.1234
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'Br' 'Br' -0.2901 2.4595
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting 'Orthorhombic'
_symmetry_space_group_name_H-M 'P2(1)2(1)2(1) '
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
_cell_length_a 7.156(3)
_cell_length_b 13.538(5)
_cell_length_c 15.406(6)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 1492.3(9)
_cell_formula_units_Z 4
_cell_measurement_temperature 298(2)
_cell_measurement_reflns_used 3565
_cell_measurement_theta_min 2.64
_cell_measurement_theta_max 20.14
_exptl_crystal_description PLATE
_exptl_crystal_colour COLORLES
_exptl_crystal_size_max 0.22
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.20
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.554
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 712
_exptl_absorpt_coefficient_mu 2.899
_exptl_absorpt_correction_type 'none'
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 298(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 15786
_diffrn_reflns_av_R_equivalents 0.0569
_diffrn_reflns_av_sigmaI/netI 0.0525
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_limit_l_max 19
_diffrn_reflns_theta_min 2.00
_diffrn_reflns_theta_max 26.38
_reflns_number_total 3029
_reflns_number_gt 2405
_reflns_threshold_expression >2sigma(I)
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^2^, conventional
R-factors R are based on F, with F set to zero for
negative F^2^. The threshold expression of F^2^ >
\s(F^2^) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^2^ are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0368P)^2^+0.1698P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.018(11)
_refine_ls_number_reflns 3029
_refine_ls_number_parameters 184
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0557
_refine_ls_R_factor_gt 0.0398
_refine_ls_wR_factor_ref 0.0931
_refine_ls_wR_factor_gt 0.0858
_refine_ls_goodness_of_fit_ref 1.025
_refine_ls_restrained_S_all 1.025
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br 1.06812(7) 0.57142(4) 0.17536(3) 0.0783(2) Uani 1 1 d . . .
S1 S 0.51258(13) 0.85223(8) 0.38623(7) 0.0535(3) Uani 1 1 d . . .
O2 O 0.3242(4) 0.8284(3) 0.3656(2) 0.0826(11) Uani 1 1 d . . .
C2 C 0.5904(5) 0.6967(3) 0.2777(2) 0.0499(9) Uani 1 1 d . . .
H2 H 0.4628 0.6838 0.2782 0.060 Uiso 1 1 calc R . .
O1 O 0.5740(4) 0.9520(2) 0.3772(2) 0.0722(8) Uani 1 1 d . . .
O3 O 1.0804(4) 0.3851(2) 0.97299(19) 0.0658(8) Uani 1 1 d . . .
C7 C 0.9938(6) 0.4547(3) 0.9408(3) 0.0538(10) Uani 1 1 d . . .
C4 C 0.8969(5) 0.6561(3) 0.2329(2) 0.0494(9) Uani 1 1 d . . .
C6 C 0.8509(5) 0.7955(3) 0.3230(3) 0.0534(9) Uani 1 1 d . . .
H6 H 0.8987 0.8488 0.3540 0.064 Uiso 1 1 calc R . .
N1 N 0.5439(6) 0.8229(3) 0.4860(2) 0.0564(9) Uani 1 1 d . . .
C12 C 0.6865(7) 0.5376(4) 0.9179(4) 0.0802(15) Uani 1 1 d . . .
H12A H 0.5591 0.5213 0.9340 0.096 Uiso 1 1 calc R . .
H12B H 0.6944 0.5350 0.8551 0.096 Uiso 1 1 calc R . .
C10 C 0.8940(8) 0.6866(3) 0.9025(4) 0.0803(15) Uani 1 1 d . . .
H10A H 0.8698 0.6895 0.8406 0.096 Uiso 1 1 calc R . .
H10B H 0.9062 0.7540 0.9231 0.096 Uiso 1 1 calc R . .
C1 C 0.6596(5) 0.7767(3) 0.3234(3) 0.0456(8) Uani 1 1 d . . .
C5 C 0.9678(6) 0.7358(3) 0.2773(3) 0.0566(10) Uani 1 1 d . . .
H5 H 1.0953 0.7488 0.2760 0.068 Uiso 1 1 calc R . .
C3 C 0.7081(6) 0.6364(3) 0.2317(2) 0.0536(10) Uani 1 1 d . . .
H3 H 0.6613 0.5831 0.2003 0.064 Uiso 1 1 calc R . .
C8 C 1.0852(6) 0.5294(3) 0.8836(3) 0.0651(11) Uani 1 1 d . . .
H8A H 1.0259 0.5271 0.8270 0.078 Uiso 1 1 calc R . .
H8B H 1.2151 0.5109 0.8759 0.078 Uiso 1 1 calc R . .
C9 C 1.0780(8) 0.6342(3) 0.9166(3) 0.0745(13) Uani 1 1 d . . .
H9A H 1.1758 0.6718 0.8882 0.089 Uiso 1 1 calc R . .
H9B H 1.1050 0.6338 0.9783 0.089 Uiso 1 1 calc R . .
N2 N 0.8108(5) 0.4630(3) 0.9539(3) 0.0706(12) Uani 1 1 d . . .
C11 C 0.7264(8) 0.6401(4) 0.9465(4) 0.0852(16) Uani 1 1 d . . .
H11A H 0.7472 0.6400 1.0087 0.102 Uiso 1 1 calc R . .
H11B H 0.6173 0.6806 0.9351 0.102 Uiso 1 1 calc R . .
H1B H 0.525(6) 0.773(3) 0.495(3) 0.045(14) Uiso 1 1 d . . .
H1A H 0.662(6) 0.841(3) 0.507(3) 0.060(13) Uiso 1 1 d . . .
H2A H 0.764(6) 0.413(3) 0.979(3) 0.064(14) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br 0.0896(4) 0.0694(3) 0.0759(3) -0.0139(3) 0.0210(3) 0.0173(3)
S1 0.0395(5) 0.0528(5) 0.0681(6) -0.0021(5) 0.0024(5) 0.0072(4)
O2 0.0397(16) 0.100(3) 0.108(3) -0.021(2) -0.0044(16) 0.0112(16)
C2 0.042(2) 0.056(2) 0.052(2) 0.0051(17) -0.0039(18) -0.0043(19)
O1 0.0761(19) 0.0488(17) 0.092(2) 0.0098(14) 0.0176(17) 0.0170(15)
O3 0.0651(17) 0.0500(16) 0.082(2) 0.0108(14) -0.0087(17) 0.0012(15)
C7 0.055(2) 0.044(2) 0.063(2) -0.0002(18) 0.000(2) -0.0067(18)
C4 0.054(3) 0.048(2) 0.046(2) -0.0008(16) 0.0045(18) 0.0043(19)
C6 0.049(2) 0.052(2) 0.059(2) -0.013(2) -0.003(2) -0.0033(17)
N1 0.056(3) 0.046(2) 0.067(2) -0.0053(18) 0.0105(19) -0.0012(19)
C12 0.051(3) 0.070(3) 0.119(4) 0.014(3) 0.005(3) 0.004(2)
C10 0.098(4) 0.050(2) 0.094(4) 0.013(2) 0.010(3) -0.005(3)
C1 0.0398(19) 0.049(2) 0.048(2) 0.0058(19) -0.0010(18) 0.0001(15)
C5 0.040(2) 0.069(3) 0.062(2) -0.009(2) 0.0007(18) 0.0010(19)
C3 0.067(3) 0.047(2) 0.047(2) -0.0039(18) -0.0047(19) -0.012(2)
C8 0.052(2) 0.074(3) 0.069(3) 0.004(2) 0.006(2) -0.005(2)
C9 0.079(3) 0.065(3) 0.080(3) 0.012(2) -0.007(3) -0.023(3)
N2 0.056(2) 0.056(2) 0.099(3) 0.022(2) 0.014(2) -0.0046(19)
C11 0.088(4) 0.071(3) 0.097(4) -0.002(3) 0.017(3) 0.026(3)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br C4 1.898(4) . ?
S1 O2 1.422(3) . ?
S1 O1 1.427(3) . ?
S1 N1 1.602(4) . ?
S1 C1 1.757(4) . ?
C2 C3 1.371(6) . ?
C2 C1 1.383(5) . ?
O3 C7 1.232(5) . ?
C7 N2 1.329(6) . ?
C7 C8 1.492(6) . ?
C4 C5 1.374(5) . ?
C4 C3 1.377(6) . ?
C6 C5 1.360(5) . ?
C6 C1 1.392(5) . ?
C12 N2 1.456(6) . ?
C12 C11 1.483(7) . ?
C10 C9 1.511(7) . ?
C10 C11 1.515(7) . ?
C8 C9 1.508(6) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 119.0(2) . . ?
O2 S1 N1 106.9(2) . . ?
O1 S1 N1 106.5(2) . . ?
O2 S1 C1 108.2(2) . . ?
O1 S1 C1 108.21(18) . . ?
N1 S1 C1 107.49(19) . . ?
C3 C2 C1 120.7(4) . . ?
O3 C7 N2 120.0(4) . . ?
O3 C7 C8 122.3(4) . . ?
N2 C7 C8 117.7(4) . . ?
C5 C4 C3 121.4(4) . . ?
C5 C4 Br 117.9(3) . . ?
C3 C4 Br 120.7(3) . . ?
C5 C6 C1 119.9(4) . . ?
N2 C12 C11 114.7(5) . . ?
C9 C10 C11 115.5(4) . . ?
C2 C1 C6 119.5(4) . . ?
C2 C1 S1 121.4(3) . . ?
C6 C1 S1 119.0(3) . . ?
C6 C5 C4 119.8(4) . . ?
C2 C3 C4 118.7(4) . . ?
C7 C8 C9 115.0(4) . . ?
C8 C9 C10 115.0(4) . . ?
C7 N2 C12 127.1(4) . . ?
C12 C11 C10 114.1(5) . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 26.38
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max 0.455
_refine_diff_density_min -0.229
_refine_diff_density_rms 0.050
data_OTSAVLM
_publcif_datablock.id '{200e1bba-1993-492f-a49a-bfd9dfb1fd04}'
_database_code_depnum_ccdc_archive 'CCDC 1039199'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point 343
_chemical_formula_moiety C7H9NO2S,C5H9NO
_chemical_formula_sum
'C12 H18 N2 O3 S'
_chemical_formula_weight 270.34
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'S' 'S' 0.1246 0.1234
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 1 21/n 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a 5.3367(6)
_cell_length_b 15.9206(17)
_cell_length_c 16.070(3)
_cell_angle_alpha 90.00
_cell_angle_beta 98.308(12)
_cell_angle_gamma 90.00
_cell_volume 1351.0(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 298(2)
_cell_measurement_reflns_used 735
_cell_measurement_theta_min 2.5535
_cell_measurement_theta_max 26.3132
_exptl_crystal_description PLATE
_exptl_crystal_colour COLORLES
_exptl_crystal_size_max 0.22
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.20
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.329
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 576
_exptl_absorpt_coefficient_mu 0.242
_exptl_absorpt_correction_type 'multi-scan'
_exptl_absorpt_correction_T_min 0.75527
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_process_details SADABS
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 298(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Xcalibur, Eos, Gemini'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 5072
_diffrn_reflns_av_R_equivalents 0.0671
_diffrn_reflns_av_sigmaI/netI 0.0969
_diffrn_reflns_limit_h_min -6
_diffrn_reflns_limit_h_max 6
_diffrn_reflns_limit_k_min -19
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_limit_l_max 20
_diffrn_reflns_theta_min 2.56
_diffrn_reflns_theta_max 26.37
_reflns_number_total 2759
_reflns_number_gt 1420
_reflns_threshold_expression >2sigma(I)
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^2^, conventional
R-factors R are based on F, with F set to zero for
negative F^2^. The threshold expression of F^2^ >
\s(F^2^) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^2^ are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0264P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 2759
_refine_ls_number_parameters 170
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1379
_refine_ls_R_factor_gt 0.0645
_refine_ls_wR_factor_ref 0.1183
_refine_ls_wR_factor_gt 0.0930
_refine_ls_goodness_of_fit_ref 1.019
_refine_ls_restrained_S_all 1.019
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.21166(16) 0.62191(5) 0.22403(6) 0.0519(3) Uani 1 1 d . . .
O1 O 0.4643(4) 0.63090(14) 0.26693(16) 0.0674(7) Uani 1 1 d . . .
N1 N 0.0300(5) 0.63558(19) 0.29386(19) 0.0519(8) Uani 1 1 d . . .
H1B H -0.142(6) 0.6375(19) 0.270(2) 0.062 Uiso 1 1 d . . .
H1A H 0.071(6) 0.608(2) 0.340(2) 0.062 Uiso 1 1 d . . .
O2 O 0.1267(5) 0.67551(15) 0.15492(16) 0.0756(8) Uani 1 1 d . . .
C6 C 0.3592(7) 0.4596(2) 0.2264(2) 0.0591(10) Uani 1 1 d . . .
H6 H 0.4935 0.4790 0.2650 0.071 Uiso 1 1 calc R . .
C1 C 0.1792(6) 0.5159(2) 0.1901(2) 0.0450(8) Uani 1 1 d . . .
C2 C -0.0255(6) 0.4890(2) 0.1329(2) 0.0561(9) Uani 1 1 d . . .
C5 C 0.3448(8) 0.3759(3) 0.2070(3) 0.0780(12) Uani 1 1 d . . .
H5 H 0.4691 0.3389 0.2311 0.094 Uiso 1 1 calc R . .
C4 C 0.1447(10) 0.3478(3) 0.1515(3) 0.0837(13) Uani 1 1 d . . .
H4 H 0.1301 0.2910 0.1384 0.100 Uiso 1 1 calc R . .
C3 C -0.0337(8) 0.4028(3) 0.1153(3) 0.0807(13) Uani 1 1 d . . .
H3 H -0.1670 0.3822 0.0770 0.097 Uiso 1 1 calc R . .
C7 C -0.2302(7) 0.5456(3) 0.0899(2) 0.0835(13) Uani 1 1 d . . .
H7A H -0.2841 0.5834 0.1304 0.125 Uiso 1 1 calc R . .
H7B H -0.3714 0.5122 0.0652 0.125 Uiso 1 1 calc R . .
H7C H -0.1657 0.5772 0.0468 0.125 Uiso 1 1 calc R . .
O3 O 0.2324(4) 0.52137(14) 0.42358(14) 0.0557(7) Uani 1 1 d . . .
N2 N 0.3028(5) 0.39875(16) 0.49027(17) 0.0488(7) Uani 1 1 d . . .
H2A H 0.4360 0.4209 0.5183 0.059 Uiso 1 1 calc R . .
C8 C 0.1675(6) 0.4473(2) 0.4342(2) 0.0432(8) Uani 1 1 d . . .
C9 C -0.0668(6) 0.4125(2) 0.3845(2) 0.0495(9) Uani 1 1 d . . .
H9A H -0.0685 0.4275 0.3259 0.059 Uiso 1 1 calc R . .
H9B H -0.2122 0.4389 0.4034 0.059 Uiso 1 1 calc R . .
C11 C -0.0199(6) 0.2893(2) 0.4793(2) 0.0649(11) Uani 1 1 d . . .
H11A H -0.0413 0.2290 0.4825 0.078 Uiso 1 1 calc R . .
H11B H -0.1287 0.3156 0.5151 0.078 Uiso 1 1 calc R . .
C12 C 0.2510(6) 0.3118(2) 0.5098(2) 0.0582(10) Uani 1 1 d . . .
H12A H 0.2862 0.3033 0.5702 0.070 Uiso 1 1 calc R . .
H12B H 0.3617 0.2751 0.4836 0.070 Uiso 1 1 calc R . .
C10 C -0.0955(7) 0.3178(2) 0.3903(2) 0.0667(11) Uani 1 1 d . . .
H10A H -0.2701 0.3022 0.3714 0.080 Uiso 1 1 calc R . .
H10B H 0.0101 0.2904 0.3541 0.080 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0399(5) 0.0461(5) 0.0694(7) 0.0066(5) 0.0071(5) -0.0035(4)
O1 0.0331(13) 0.0648(16) 0.103(2) -0.0125(15) 0.0054(13) -0.0082(12)
N1 0.0356(16) 0.059(2) 0.060(2) -0.0034(15) 0.0014(16) 0.0025(15)
O2 0.0841(19) 0.0597(16) 0.083(2) 0.0323(15) 0.0125(15) 0.0004(14)
C6 0.055(2) 0.051(2) 0.067(3) 0.005(2) -0.002(2) 0.0044(19)
C1 0.042(2) 0.049(2) 0.044(2) 0.0022(17) 0.0068(17) -0.0017(17)
C2 0.056(2) 0.067(3) 0.045(2) -0.006(2) 0.0045(19) 0.001(2)
C5 0.089(3) 0.059(3) 0.084(3) 0.008(2) 0.007(3) 0.020(2)
C4 0.103(4) 0.064(3) 0.084(4) -0.018(3) 0.015(3) 0.001(3)
C3 0.082(3) 0.085(3) 0.070(3) -0.026(3) -0.006(2) -0.013(3)
C7 0.064(3) 0.115(4) 0.062(3) -0.003(3) -0.024(2) 0.011(3)
O3 0.0553(15) 0.0478(15) 0.0601(17) 0.0014(12) -0.0047(12) -0.0090(12)
N2 0.0392(16) 0.0479(18) 0.055(2) -0.0025(15) -0.0066(14) -0.0017(14)
C8 0.0371(19) 0.051(2) 0.041(2) -0.0084(19) 0.0046(17) 0.0009(18)
C9 0.043(2) 0.059(2) 0.044(2) -0.0055(18) -0.0035(17) -0.0045(17)
C11 0.062(3) 0.050(2) 0.080(3) 0.002(2) 0.003(2) -0.0144(19)
C12 0.063(3) 0.049(2) 0.061(3) 0.0023(19) 0.0023(19) 0.0006(19)
C10 0.056(2) 0.068(3) 0.071(3) -0.009(2) -0.006(2) -0.011(2)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.422(2) . ?
S1 O1 1.430(2) . ?
S1 N1 1.600(3) . ?
S1 C1 1.775(3) . ?
N1 H1B 0.95(3) . ?
N1 H1A 0.86(3) . ?
C6 C5 1.368(5) . ?
C6 C1 1.380(4) . ?
C6 H6 0.9300 . ?
C1 C2 1.389(4) . ?
C2 C3 1.401(5) . ?
C2 C7 1.504(5) . ?
C5 C4 1.364(5) . ?
C5 H5 0.9300 . ?
C4 C3 1.361(5) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
O3 C8 1.248(4) . ?
N2 C8 1.320(4) . ?
N2 C12 1.456(4) . ?
N2 H2A 0.8600 . ?
C8 C9 1.489(4) . ?
C9 C10 1.519(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 C10 1.498(5) . ?
C11 C12 1.501(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 119.24(15) . . ?
O2 S1 N1 108.01(16) . . ?
O1 S1 N1 105.83(16) . . ?
O2 S1 C1 108.95(16) . . ?
O1 S1 C1 106.66(15) . . ?
N1 S1 C1 107.62(15) . . ?
S1 N1 H1B 111.7(19) . . ?
S1 N1 H1A 115(2) . . ?
H1B N1 H1A 118(3) . . ?
C5 C6 C1 121.5(4) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
C6 C1 C2 120.9(3) . . ?
C6 C1 S1 117.1(3) . . ?
C2 C1 S1 121.9(3) . . ?
C1 C2 C3 115.7(3) . . ?
C1 C2 C7 124.7(3) . . ?
C3 C2 C7 119.6(4) . . ?
C4 C5 C6 118.8(4) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C3 C4 C5 120.1(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C3 C2 123.0(4) . . ?
C4 C3 H3 118.5 . . ?
C2 C3 H3 118.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C8 N2 C12 127.0(3) . . ?
C8 N2 H2A 116.5 . . ?
C12 N2 H2A 116.5 . . ?
O3 C8 N2 120.7(3) . . ?
O3 C8 C9 120.4(3) . . ?
N2 C8 C9 118.9(3) . . ?
C8 C9 C10 114.8(3) . . ?
C8 C9 H9A 108.6 . . ?
C10 C9 H9A 108.6 . . ?
C8 C9 H9B 108.6 . . ?
C10 C9 H9B 108.6 . . ?
H9A C9 H9B 107.5 . . ?
C10 C11 C12 110.7(3) . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
N2 C12 C11 111.1(3) . . ?
N2 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
N2 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C11 C10 C9 110.1(3) . . ?
C11 C10 H10A 109.6 . . ?
C9 C10 H10A 109.6 . . ?
C11 C10 H10B 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.2 . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 26.37
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max 0.205
_refine_diff_density_min -0.237
_refine_diff_density_rms 0.047
data_2ClBSACPR
_publcif_datablock.id '{a30a02d8-6f92-42e6-ac6b-60c701facf4a}'
_database_code_depnum_ccdc_archive 'CCDC 1039190'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point 355
_chemical_formula_moiety C6H6ClNO2S,C6H11NO
_chemical_formula_sum
'C12 H17 Cl N2 O3 S'
_chemical_formula_weight 304.79
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'S' 'S' 0.1246 0.1234
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'Cl' 'Cl' 0.1484 0.1585
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P121/c1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 9.8782(6)
_cell_length_b 14.1720(6)
_cell_length_c 10.8753(6)
_cell_angle_alpha 90.00
_cell_angle_beta 112.850(7)
_cell_angle_gamma 90.00
_cell_volume 1402.98(12)
_cell_formula_units_Z 4
_cell_measurement_temperature 298(2)
_cell_measurement_reflns_used 2558
_cell_measurement_theta_min 3.6470
_cell_measurement_theta_max 28.9370
_exptl_crystal_description BLOCK
_exptl_crystal_colour COLORLES
_exptl_crystal_size_max 0.22
_exptl_crystal_size_mid 0.22
_exptl_crystal_size_min 0.20
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.443
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 640
_exptl_absorpt_coefficient_mu 0.426
_exptl_absorpt_correction_type 'multi-scan'
_exptl_absorpt_correction_T_min 0.87589
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_process_details SADABS
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 298(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Xcalibur, Eos, Gemini'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 5810
_diffrn_reflns_av_R_equivalents 0.0209
_diffrn_reflns_av_sigmaI/netI 0.0253
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -17
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_limit_l_max 10
_diffrn_reflns_theta_min 2.87
_diffrn_reflns_theta_max 26.37
_reflns_number_total 2870
_reflns_number_gt 2483
_reflns_threshold_expression >2sigma(I)
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^2^, conventional
R-factors R are based on F, with F set to zero for
negative F^2^. The threshold expression of F^2^ >
\s(F^2^) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^2^ are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0514P)^2^+0.3887P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 2870
_refine_ls_number_parameters 178
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0454
_refine_ls_R_factor_gt 0.0385
_refine_ls_wR_factor_ref 0.1031
_refine_ls_wR_factor_gt 0.0975
_refine_ls_goodness_of_fit_ref 1.093
_refine_ls_restrained_S_all 1.093
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.88136(5) 0.24056(3) 0.00962(4) 0.03143(14) Uani 1 1 d . . .
Cl1 Cl 1.11885(6) 0.31602(4) -0.10232(6) 0.05419(18) Uani 1 1 d . . .
O3 O 0.53802(18) 0.37511(10) 0.98172(13) 0.0492(4) Uani 1 1 d . . .
O2 O 0.80116(16) 0.25905(10) -0.12931(13) 0.0427(3) Uani 1 1 d . . .
N1 N 0.7628(2) 0.23340(13) 0.07521(18) 0.0398(4) Uani 1 1 d . . .
H1A H 0.689(3) 0.2760(17) 0.045(2) 0.048 Uiso 1 1 d . . .
H1B H 0.797(3) 0.2214(17) 0.155(2) 0.048 Uiso 1 1 d . . .
N2 N 0.39497(19) 0.47318(11) 0.82491(15) 0.0422(4) Uani 1 1 d . . .
H2A H 0.4202 0.5170 0.8843 0.051 Uiso 1 1 calc R . .
C1 C 0.99475(18) 0.34009(12) 0.08009(16) 0.0301(4) Uani 1 1 d . . .
C7 C 0.4489(2) 0.38834(13) 0.86453(18) 0.0370(4) Uani 1 1 d . . .
O1 O 0.97322(16) 0.15904(9) 0.04756(16) 0.0488(4) Uani 1 1 d . . .
C6 C 0.9817(2) 0.38791(13) 0.18640(17) 0.0388(4) Uani 1 1 d . . .
H6 H 0.9127 0.3683 0.2197 0.047 Uiso 1 1 calc R . .
C2 C 1.0992(2) 0.37035(13) 0.03259(18) 0.0361(4) Uani 1 1 d . . .
C12 C 0.2965(2) 0.50019(16) 0.6900(2) 0.0490(5) Uani 1 1 d . . .
H12A H 0.2686 0.5657 0.6907 0.059 Uiso 1 1 calc R . .
H12B H 0.2079 0.4624 0.6637 0.059 Uiso 1 1 calc R . .
C5 C 1.0706(3) 0.46446(15) 0.2428(2) 0.0507(5) Uani 1 1 d . . .
H5 H 1.0612 0.4964 0.3138 0.061 Uiso 1 1 calc R . .
C9 C 0.4531(2) 0.31855(15) 0.6516(2) 0.0447(5) Uani 1 1 d . . .
H9A H 0.5545 0.3396 0.6875 0.054 Uiso 1 1 calc R . .
H9B H 0.4504 0.2569 0.6119 0.054 Uiso 1 1 calc R . .
C10 C 0.3633(3) 0.38646(16) 0.5430(2) 0.0531(6) Uani 1 1 d . . .
H10A H 0.2626 0.3643 0.5054 0.064 Uiso 1 1 calc R . .
H10B H 0.4005 0.3852 0.4726 0.064 Uiso 1 1 calc R . .
C8 C 0.4020(2) 0.30847(14) 0.76585(19) 0.0441(5) Uani 1 1 d . . .
H8A H 0.2956 0.3044 0.7293 0.053 Uiso 1 1 calc R . .
H8B H 0.4403 0.2499 0.8125 0.053 Uiso 1 1 calc R . .
C3 C 1.1882(2) 0.44687(15) 0.0899(2) 0.0498(5) Uani 1 1 d . . .
H3 H 1.2582 0.4668 0.0580 0.060 Uiso 1 1 calc R . .
C11 C 0.3639(3) 0.48789(16) 0.5881(2) 0.0521(5) Uani 1 1 d . . .
H11A H 0.4644 0.5105 0.6258 0.063 Uiso 1 1 calc R . .
H11B H 0.3103 0.5266 0.5109 0.063 Uiso 1 1 calc R . .
C4 C 1.1723(3) 0.49336(15) 0.1947(2) 0.0542(6) Uani 1 1 d . . .
H4 H 1.2316 0.5451 0.2331 0.065 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0345(2) 0.0300(2) 0.0307(2) -0.00086(16) 0.01362(18) -0.00041(17)
Cl1 0.0570(3) 0.0622(4) 0.0593(3) -0.0022(3) 0.0400(3) 0.0006(3)
O3 0.0688(10) 0.0419(8) 0.0327(7) -0.0008(6) 0.0151(7) 0.0099(7)
O2 0.0435(7) 0.0539(8) 0.0287(7) -0.0045(6) 0.0117(6) -0.0061(6)
N1 0.0392(9) 0.0446(9) 0.0378(9) 0.0043(7) 0.0175(7) -0.0019(7)
N2 0.0559(10) 0.0352(8) 0.0331(8) -0.0044(7) 0.0143(7) 0.0062(7)
C1 0.0310(8) 0.0289(8) 0.0281(8) 0.0039(7) 0.0088(7) 0.0030(7)
C7 0.0460(10) 0.0360(10) 0.0344(9) -0.0013(8) 0.0215(8) -0.0002(8)
O1 0.0524(8) 0.0315(7) 0.0640(9) 0.0019(6) 0.0242(7) 0.0074(6)
C6 0.0451(10) 0.0395(10) 0.0304(9) -0.0006(8) 0.0129(8) 0.0010(8)
C2 0.0335(9) 0.0368(9) 0.0375(9) 0.0051(8) 0.0133(8) 0.0034(7)
C12 0.0503(12) 0.0453(12) 0.0444(11) -0.0003(9) 0.0107(9) 0.0120(9)
C5 0.0599(13) 0.0414(11) 0.0405(11) -0.0094(9) 0.0083(10) 0.0000(10)
C9 0.0466(11) 0.0471(11) 0.0435(11) -0.0121(9) 0.0208(9) 0.0016(9)
C10 0.0668(14) 0.0595(14) 0.0351(10) -0.0057(10) 0.0219(10) -0.0040(11)
C8 0.0582(12) 0.0341(10) 0.0415(11) -0.0052(8) 0.0211(9) -0.0034(9)
C3 0.0379(11) 0.0472(12) 0.0591(13) 0.0095(10) 0.0132(10) -0.0066(9)
C11 0.0651(14) 0.0502(12) 0.0368(11) 0.0048(9) 0.0151(10) -0.0015(11)
C4 0.0515(13) 0.0397(11) 0.0553(13) -0.0033(10) 0.0031(10) -0.0097(10)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4274(14) . ?
S1 O2 1.4315(14) . ?
S1 N1 1.5934(17) . ?
S1 C1 1.7791(18) . ?
Cl1 C2 1.7334(19) . ?
O3 C7 1.250(2) . ?
N1 H1A 0.91(2) . ?
N1 H1B 0.81(2) . ?
N2 C7 1.318(2) . ?
N2 C12 1.462(2) . ?
N2 H2A 0.8600 . ?
C1 C2 1.389(2) . ?
C1 C6 1.389(2) . ?
C7 C8 1.504(3) . ?
C6 C5 1.381(3) . ?
C6 H6 0.9300 . ?
C2 C3 1.383(3) . ?
C12 C11 1.508(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C5 C4 1.363(3) . ?
C5 H5 0.9300 . ?
C9 C10 1.514(3) . ?
C9 C8 1.519(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.518(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C3 C4 1.376(3) . ?
C3 H3 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C4 H4 0.9300 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 118.84(9) . . ?
O1 S1 N1 108.32(9) . . ?
O2 S1 N1 106.41(9) . . ?
O1 S1 C1 107.09(8) . . ?
O2 S1 C1 107.90(8) . . ?
N1 S1 C1 107.86(9) . . ?
S1 N1 H1A 114.9(15) . . ?
S1 N1 H1B 114.5(17) . . ?
H1A N1 H1B 118(2) . . ?
C7 N2 C12 126.44(16) . . ?
C7 N2 H2A 116.8 . . ?
C12 N2 H2A 116.8 . . ?
C2 C1 C6 118.80(17) . . ?
C2 C1 S1 121.26(14) . . ?
C6 C1 S1 119.93(14) . . ?
O3 C7 N2 120.35(17) . . ?
O3 C7 C8 120.97(17) . . ?
N2 C7 C8 118.68(17) . . ?
C5 C6 C1 120.27(19) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C3 C2 C1 120.54(18) . . ?
C3 C2 Cl1 118.01(15) . . ?
C1 C2 Cl1 121.42(14) . . ?
N2 C12 C11 113.33(18) . . ?
N2 C12 H12A 108.9 . . ?
C11 C12 H12A 108.9 . . ?
N2 C12 H12B 108.9 . . ?
C11 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C10 C9 C8 114.67(18) . . ?
C10 C9 H9A 108.6 . . ?
C8 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
C8 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C9 C10 C11 114.99(17) . . ?
C9 C10 H10A 108.5 . . ?
C11 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
C11 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C7 C8 C9 113.88(17) . . ?
C7 C8 H8A 108.8 . . ?
C9 C8 H8A 108.8 . . ?
C7 C8 H8B 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C12 C11 C10 113.55(19) . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 26.37
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max 0.249
_refine_diff_density_min -0.479
_refine_diff_density_rms 0.075
data_BSACPR
_publcif_datablock.id '{649310c0-c732-4b83-9218-60674abe29ca}'
_database_code_depnum_ccdc_archive 'CCDC 1039197'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point 353
_chemical_formula_moiety C6H7NO2S,C6H11NO
_chemical_formula_sum
'C12 H18 N2 O3 S'
_chemical_formula_weight 270.34
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'S' 'S' 0.1246 0.1234
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_H-M 'P 21 21 21'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
_cell_length_a 7.0700(9)
_cell_length_b 12.7624(13)
_cell_length_c 14.977(2)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 1351.4(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 298(2)
_cell_measurement_reflns_used 1165
_cell_measurement_theta_min 3.9620
_cell_measurement_theta_max 26.7220
_exptl_crystal_description PLATE
_exptl_crystal_colour COLORLES
_exptl_crystal_size_max 0.22
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.20
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.329
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 576
_exptl_absorpt_coefficient_mu 0.242
_exptl_absorpt_correction_type 'multi-scan'
_exptl_absorpt_correction_T_min 0.78752
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_process_details SADABS
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 298(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Xcalibur, Eos, Gemini'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 3348
_diffrn_reflns_av_R_equivalents 0.0386
_diffrn_reflns_av_sigmaI/netI 0.0631
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_theta_min 2.72
_diffrn_reflns_theta_max 24.99
_reflns_number_total 2197
_reflns_number_gt 1595
_reflns_threshold_expression >2sigma(I)
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^2^, conventional
R-factors R are based on F, with F set to zero for
negative F^2^. The threshold expression of F^2^ >
\s(F^2^) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^2^ are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0352P)^2^+2.5208P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.0(2)
_refine_ls_number_reflns 2197
_refine_ls_number_parameters 169
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1088
_refine_ls_R_factor_gt 0.0777
_refine_ls_wR_factor_ref 0.1806
_refine_ls_wR_factor_gt 0.1703
_refine_ls_goodness_of_fit_ref 1.231
_refine_ls_restrained_S_all 1.231
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.9052(3) 0.65992(13) 0.85943(13) 0.0524(5) Uani 1 1 d . . .
O3 O -0.0036(7) 0.3842(3) 0.5082(4) 0.0641(15) Uani 1 1 d . . .
O1 O 1.0954(7) 0.6811(4) 0.8374(4) 0.0775(17) Uani 1 1 d . . .
N1 N 0.8857(10) 0.6723(4) 0.9646(5) 0.0551(16) Uani 1 1 d . . .
N2 N 0.2566(10) 0.4789(5) 0.5098(5) 0.078(2) Uani 1 1 d . . .
H2A H 0.3203 0.4215 0.5094 0.094 Uiso 1 1 calc R . .
O2 O 0.8294(8) 0.5611(3) 0.8371(4) 0.0693(16) Uani 1 1 d . . .
C1 C 0.7647(10) 0.7583(5) 0.8109(4) 0.0435(17) Uani 1 1 d . . .
C6 C 0.8499(10) 0.8423(6) 0.7703(4) 0.0527(17) Uani 1 1 d . . .
H6 H 0.9810 0.8473 0.7675 0.063 Uiso 1 1 calc R . .
C5 C 0.7369(13) 0.9193(6) 0.7339(5) 0.066(2) Uani 1 1 d . . .
H5 H 0.7921 0.9769 0.7062 0.079 Uiso 1 1 calc R . .
C4 C 0.5473(12) 0.9116(7) 0.7381(6) 0.071(3) Uani 1 1 d . . .
H4 H 0.4724 0.9639 0.7132 0.085 Uiso 1 1 calc R . .
C7 C 0.0729(12) 0.4691(5) 0.5108(6) 0.064(2) Uani 1 1 d . . .
C3 C 0.4644(11) 0.8276(7) 0.7785(5) 0.068(2) Uani 1 1 d . . .
H3 H 0.3333 0.8233 0.7819 0.082 Uiso 1 1 calc R . .
C2 C 0.5738(11) 0.7495(6) 0.8142(5) 0.060(2) Uani 1 1 d . . .
H2 H 0.5177 0.6912 0.8404 0.072 Uiso 1 1 calc R . .
C11 C 0.3443(14) 0.6399(7) 0.5866(7) 0.094(3) Uani 1 1 d . . .
H11A H 0.4467 0.6905 0.5869 0.113 Uiso 1 1 calc R . .
H11B H 0.3599 0.5961 0.6390 0.113 Uiso 1 1 calc R . .
C12 C 0.3665(13) 0.5750(7) 0.5093(9) 0.109(4) Uani 1 1 d . . .
H12A H 0.4992 0.5569 0.5035 0.131 Uiso 1 1 calc R . .
H12B H 0.3315 0.6154 0.4570 0.131 Uiso 1 1 calc R . .
C10 C 0.1627(13) 0.6987(6) 0.5965(6) 0.076(3) Uani 1 1 d . . .
H10A H 0.1544 0.7498 0.5487 0.092 Uiso 1 1 calc R . .
H10B H 0.1661 0.7369 0.6524 0.092 Uiso 1 1 calc R . .
C8 C -0.0411(12) 0.5691(6) 0.5152(8) 0.090(3) Uani 1 1 d . . .
H8A H -0.0103 0.6114 0.4634 0.108 Uiso 1 1 calc R . .
H8B H -0.1742 0.5511 0.5112 0.108 Uiso 1 1 calc R . .
C9 C -0.0129(13) 0.6327(7) 0.5950(7) 0.085(3) Uani 1 1 d . . .
H9A H -0.0103 0.5864 0.6463 0.102 Uiso 1 1 calc R . .
H9B H -0.1214 0.6786 0.6018 0.102 Uiso 1 1 calc R . .
H1A H 0.785(13) 0.646(7) 0.988(7) 0.102 Uiso 1 1 d . . .
H1B H 0.906(14) 0.730(7) 0.975(7) 0.102 Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0468(10) 0.0466(8) 0.0640(12) -0.0008(10) 0.0053(10) 0.0048(9)
O3 0.064(3) 0.044(3) 0.085(4) -0.006(3) -0.014(3) -0.001(3)
O1 0.046(3) 0.082(4) 0.105(5) 0.013(3) 0.016(3) 0.010(3)
N1 0.058(4) 0.038(3) 0.070(4) 0.005(3) -0.011(3) 0.000(3)
N2 0.055(4) 0.044(4) 0.135(7) -0.016(4) 0.008(5) 0.004(3)
O2 0.084(4) 0.046(3) 0.078(4) -0.014(3) 0.008(3) 0.003(3)
C1 0.043(5) 0.056(4) 0.032(4) -0.002(3) -0.008(3) -0.001(3)
C6 0.045(4) 0.066(4) 0.046(4) 0.007(4) 0.007(3) -0.004(4)
C5 0.076(6) 0.066(5) 0.055(6) 0.016(4) -0.002(5) -0.008(5)
C4 0.071(8) 0.072(6) 0.068(6) 0.012(5) -0.031(5) 0.008(5)
C7 0.063(6) 0.044(4) 0.085(6) -0.018(4) -0.011(5) 0.006(4)
C3 0.044(5) 0.091(6) 0.070(6) 0.005(5) -0.016(4) 0.001(5)
C2 0.048(5) 0.063(4) 0.068(5) 0.011(4) -0.010(4) -0.009(4)
C11 0.079(6) 0.068(5) 0.136(9) -0.010(6) -0.002(6) -0.019(5)
C12 0.067(7) 0.069(6) 0.191(12) -0.036(7) 0.019(8) -0.010(5)
C10 0.092(7) 0.061(4) 0.077(6) -0.023(4) 0.005(6) -0.004(5)
C8 0.063(6) 0.065(5) 0.141(10) -0.025(6) -0.015(6) 0.015(4)
C9 0.075(6) 0.075(6) 0.105(8) -0.037(5) 0.012(5) 0.009(5)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.410(5) . ?
S1 O1 1.410(5) . ?
S1 N1 1.589(7) . ?
S1 C1 1.758(7) . ?
O3 C7 1.212(8) . ?
N1 H1A 0.86(9) . ?
N1 H1B 0.76(8) . ?
N2 C7 1.305(9) . ?
N2 C12 1.451(10) . ?
N2 H2A 0.8600 . ?
C1 C2 1.356(10) . ?
C1 C6 1.372(9) . ?
C6 C5 1.379(10) . ?
C6 H6 0.9300 . ?
C5 C4 1.345(11) . ?
C5 H5 0.9300 . ?
C4 C3 1.364(11) . ?
C4 H4 0.9300 . ?
C7 C8 1.511(10) . ?
C3 C2 1.370(10) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C11 C12 1.433(13) . ?
C11 C10 1.494(12) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C10 C9 1.500(11) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C8 C9 1.458(12) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 118.6(3) . . ?
O2 S1 N1 106.9(3) . . ?
O1 S1 N1 107.2(4) . . ?
O2 S1 C1 109.0(3) . . ?
O1 S1 C1 107.7(3) . . ?
N1 S1 C1 106.9(3) . . ?
S1 N1 H1A 116(7) . . ?
S1 N1 H1B 106(8) . . ?
H1A N1 H1B 116(10) . . ?
C7 N2 C12 127.9(7) . . ?
C7 N2 H2A 116.0 . . ?
C12 N2 H2A 116.0 . . ?
C2 C1 C6 121.2(7) . . ?
C2 C1 S1 119.2(6) . . ?
C6 C1 S1 119.6(6) . . ?
C1 C6 C5 118.5(7) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C4 C5 C6 120.5(8) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C4 C3 120.4(8) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
O3 C7 N2 122.0(7) . . ?
O3 C7 C8 121.2(8) . . ?
N2 C7 C8 116.7(7) . . ?
C4 C3 C2 120.2(7) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C1 C2 C3 119.2(7) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C12 C11 C10 117.6(9) . . ?
C12 C11 H11A 107.9 . . ?
C10 C11 H11A 107.9 . . ?
C12 C11 H11B 107.9 . . ?
C10 C11 H11B 107.9 . . ?
H11A C11 H11B 107.2 . . ?
C11 C12 N2 115.2(9) . . ?
C11 C12 H12A 108.5 . . ?
N2 C12 H12A 108.5 . . ?
C11 C12 H12B 108.5 . . ?
N2 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C11 C10 C9 115.4(6) . . ?
C11 C10 H10A 108.4 . . ?
C9 C10 H10A 108.4 . . ?
C11 C10 H10B 108.4 . . ?
C9 C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
C9 C8 C7 115.7(8) . . ?
C9 C8 H8A 108.4 . . ?
C7 C8 H8A 108.4 . . ?
C9 C8 H8B 108.4 . . ?
C7 C8 H8B 108.4 . . ?
H8A C8 H8B 107.4 . . ?
C8 C9 C10 116.0(8) . . ?
C8 C9 H9A 108.3 . . ?
C10 C9 H9A 108.3 . . ?
C8 C9 H9B 108.3 . . ?
C10 C9 H9B 108.3 . . ?
H9A C9 H9B 107.4 . . ?
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full 24.99
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max 0.371
_refine_diff_density_min -0.237
_refine_diff_density_rms 0.061
data_4ClBSAVLM
_publcif_datablock.id '{2198d17f-4001-4fe3-b6eb-2ea6e9e3e8e1}'
_database_code_depnum_ccdc_archive 'CCDC 1039195'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point 363
_chemical_formula_moiety C6H6ClNO2S,C5H9NO
_chemical_formula_sum
'C11 H15 Cl N2 O3 S'
_chemical_formula_weight 290.76
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'S' 'S' 0.1246 0.1234
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'Cl' 'Cl' 0.1484 0.1585
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'C2/c'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a 25.701(4)
_cell_length_b 6.8096(4)
_cell_length_c 19.177(3)
_cell_angle_alpha 90.00
_cell_angle_beta 127.40(2)
_cell_angle_gamma 90.00
_cell_volume 2666.3(6)
_cell_formula_units_Z 8
_cell_measurement_temperature 297(2)
_cell_measurement_reflns_used 1025
_cell_measurement_theta_min 2.6686
_cell_measurement_theta_max 26.3134
_exptl_crystal_description PLATE
_exptl_crystal_colour ?
_exptl_crystal_size_max 0.22
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.20
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.449
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1216
_exptl_absorpt_coefficient_mu 0.445
_exptl_absorpt_correction_type 'multi-scan'
_exptl_absorpt_correction_T_min 0.84418
_exptl_absorpt_correction_T_max 1.0000
_exptl_absorpt_process_details SADABS
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 297(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Xcalibur, Eos, Gemini'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 5127
_diffrn_reflns_av_R_equivalents 0.0434
_diffrn_reflns_av_sigmaI/netI 0.0651
_diffrn_reflns_limit_h_min -32
_diffrn_reflns_limit_h_max 30
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_l_min -23
_diffrn_reflns_limit_l_max 22
_diffrn_reflns_theta_min 2.67
_diffrn_reflns_theta_max 26.37
_reflns_number_total 2732
_reflns_number_gt 1677
_reflns_threshold_expression >2sigma(I)
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^2^, conventional
R-factors R are based on F, with F set to zero for
negative F^2^. The threshold expression of F^2^ >
\s(F^2^) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^2^ are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0486P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 2732
_refine_ls_number_parameters 169
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1080
_refine_ls_R_factor_gt 0.0595
_refine_ls_wR_factor_ref 0.1344
_refine_ls_wR_factor_gt 0.1105
_refine_ls_goodness_of_fit_ref 1.067
_refine_ls_restrained_S_all 1.067
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.16418(4) 0.16415(12) 0.08089(6) 0.0460(3) Uani 1 1 d . . .
Cl1 Cl -0.00099(5) 0.68185(17) 0.14868(7) 0.0780(4) Uani 1 1 d . . .
O3 O 0.20659(12) 0.9636(3) 0.79188(15) 0.0587(7) Uani 1 1 d . . .
O1 O 0.13721(13) -0.0290(3) 0.06081(17) 0.0665(7) Uani 1 1 d . . .
N2 N 0.19285(13) 0.6912(4) 0.84382(18) 0.0490(7) Uani 1 1 d . . .
H2A H 0.2174 0.6308 0.8343 0.059 Uiso 1 1 calc R . .
C1 C 0.11457(15) 0.3131(4) 0.09443(19) 0.0388(7) Uani 1 1 d . . .
N1 N 0.23469(14) 0.1540(4) 0.17504(19) 0.0473(8) Uani 1 1 d . . .
H1A H 0.2575(17) 0.251(5) 0.186(2) 0.057 Uiso 1 1 d . . .
H1B H 0.2308(16) 0.120(5) 0.213(2) 0.057 Uiso 1 1 d . . .
C7 C 0.18276(15) 0.8793(5) 0.8239(2) 0.0414(8) Uani 1 1 d . . .
C2 C 0.12843(16) 0.5096(4) 0.1121(2) 0.0454(8) Uani 1 1 d . . .
H2 H 0.1615 0.5658 0.1124 0.054 Uiso 1 1 calc R . .
C5 C 0.02822(17) 0.3436(5) 0.1073(2) 0.0558(9) Uani 1 1 d . . .
H5 H -0.0061 0.2893 0.1046 0.067 Uiso 1 1 calc R . .
C4 C 0.04376(16) 0.5395(5) 0.1269(2) 0.0481(8) Uani 1 1 d . . .
O2 O 0.17318(12) 0.2594(3) 0.02267(15) 0.0593(7) Uani 1 1 d . . .
C6 C 0.06435(16) 0.2295(5) 0.0916(2) 0.0508(9) Uani 1 1 d . . .
H6 H 0.0550 0.0966 0.0791 0.061 Uiso 1 1 calc R . .
C8 C 0.14281(18) 0.9907(5) 0.8431(2) 0.0559(9) Uani 1 1 d . . .
H8A H 0.1134 1.0774 0.7940 0.067 Uiso 1 1 calc R . .
H8B H 0.1719 1.0722 0.8944 0.067 Uiso 1 1 calc R . .
C3 C 0.09319(16) 0.6229(5) 0.1294(2) 0.0497(8) Uani 1 1 d . . .
H3 H 0.1030 0.7554 0.1428 0.060 Uiso 1 1 calc R . .
C10 C 0.14434(18) 0.7008(5) 0.9207(2) 0.0555(9) Uani 1 1 d . . .
H10A H 0.1192 0.6229 0.9331 0.067 Uiso 1 1 calc R . .
H10B H 0.1819 0.7547 0.9756 0.067 Uiso 1 1 calc R . .
C11 C 0.16699(18) 0.5738(5) 0.8803(2) 0.0578(10) Uani 1 1 d . . .
H11A H 0.2008 0.4852 0.9244 0.069 Uiso 1 1 calc R . .
H11B H 0.1306 0.4950 0.8341 0.069 Uiso 1 1 calc R . .
C9 C 0.10283(18) 0.8639(5) 0.8592(2) 0.0596(10) Uani 1 1 d . . .
H9A H 0.0865 0.9429 0.8843 0.071 Uiso 1 1 calc R . .
H9B H 0.0656 0.8099 0.8041 0.071 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0600(6) 0.0403(5) 0.0533(5) -0.0008(4) 0.0425(5) 0.0038(4)
Cl1 0.0590(6) 0.1005(8) 0.0823(7) -0.0150(6) 0.0469(6) 0.0162(6)
O3 0.0755(17) 0.0565(14) 0.0664(16) -0.0072(12) 0.0548(15) -0.0120(13)
O1 0.0878(19) 0.0430(14) 0.0893(19) -0.0178(13) 0.0646(17) -0.0110(13)
N2 0.0567(18) 0.0414(16) 0.0651(19) 0.0011(13) 0.0455(17) 0.0096(13)
C1 0.0409(19) 0.0375(18) 0.0385(18) 0.0011(13) 0.0243(16) 0.0013(14)
N1 0.055(2) 0.0468(17) 0.0545(19) 0.0086(15) 0.0408(17) 0.0087(14)
C7 0.0422(19) 0.044(2) 0.0386(18) -0.0044(15) 0.0251(16) -0.0015(15)
C2 0.047(2) 0.0433(19) 0.056(2) 0.0034(16) 0.0359(18) 0.0021(16)
C5 0.043(2) 0.068(2) 0.065(2) 0.0023(19) 0.0373(19) -0.0016(19)
C4 0.042(2) 0.059(2) 0.0411(19) -0.0003(16) 0.0246(17) 0.0105(18)
O2 0.0809(18) 0.0635(15) 0.0573(15) 0.0087(12) 0.0543(15) 0.0092(13)
C6 0.052(2) 0.0448(19) 0.059(2) -0.0002(16) 0.0359(19) -0.0034(17)
C8 0.073(2) 0.046(2) 0.064(2) 0.0114(17) 0.050(2) 0.0189(18)
C3 0.049(2) 0.0406(18) 0.060(2) -0.0016(16) 0.0335(19) 0.0012(16)
C10 0.062(2) 0.061(2) 0.061(2) 0.0058(18) 0.046(2) 0.0044(19)
C11 0.070(3) 0.045(2) 0.066(2) 0.0063(17) 0.045(2) 0.0030(18)
C9 0.058(2) 0.072(2) 0.065(2) 0.001(2) 0.046(2) 0.010(2)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.426(2) . ?
S1 O1 1.427(2) . ?
S1 N1 1.604(3) . ?
S1 C1 1.768(3) . ?
Cl1 C4 1.738(3) . ?
O3 C7 1.241(4) . ?
N2 C7 1.316(4) . ?
N2 C11 1.461(4) . ?
N2 H2A 0.8600 . ?
C1 C2 1.373(4) . ?
C1 C6 1.381(4) . ?
N1 H1A 0.82(3) . ?
N1 H1B 0.83(3) . ?
C7 C8 1.491(4) . ?
C2 C3 1.375(4) . ?
C2 H2 0.9300 . ?
C5 C6 1.377(5) . ?
C5 C4 1.378(5) . ?
C5 H5 0.9300 . ?
C4 C3 1.365(4) . ?
C6 H6 0.9300 . ?
C8 C9 1.511(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C3 H3 0.9300 . ?
C10 C9 1.495(5) . ?
C10 C11 1.495(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 119.42(15) . . ?
O2 S1 N1 106.94(15) . . ?
O1 S1 N1 107.19(16) . . ?
O2 S1 C1 109.17(14) . . ?
O1 S1 C1 107.05(15) . . ?
N1 S1 C1 106.37(14) . . ?
C7 N2 C11 127.2(3) . . ?
C7 N2 H2A 116.4 . . ?
C11 N2 H2A 116.4 . . ?
C2 C1 C6 120.5(3) . . ?
C2 C1 S1 119.6(2) . . ?
C6 C1 S1 119.9(2) . . ?
S1 N1 H1A 113(2) . . ?
S1 N1 H1B 110(2) . . ?
H1A N1 H1B 117(4) . . ?
O3 C7 N2 121.6(3) . . ?
O3 C7 C8 120.5(3) . . ?
N2 C7 C8 117.9(3) . . ?
C1 C2 C3 119.8(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C6 C5 C4 118.9(3) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C3 C4 C5 121.4(3) . . ?
C3 C4 Cl1 119.8(3) . . ?
C5 C4 Cl1 118.8(3) . . ?
C5 C6 C1 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C7 C8 C9 114.5(3) . . ?
C7 C8 H8A 108.6 . . ?
C9 C8 H8A 108.6 . . ?
C7 C8 H8B 108.6 . . ?
C9 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C4 C3 C2 119.5(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C9 C10 C11 109.7(3) . . ?
C9 C10 H10A 109.7 . . ?
C11 C10 H10A 109.7 . . ?
C9 C10 H10B 109.7 . . ?
C11 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
N2 C11 C10 111.4(3) . . ?
N2 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
N2 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C10 C9 C8 109.8(3) . . ?
C10 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 26.37
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max 0.267
_refine_diff_density_min -0.381
_refine_diff_density_rms 0.079
data_4BrBSAVLM
_publcif_datablock.id '{e69b45eb-4585-4770-9ddd-4016e8a94097}'
_database_code_depnum_ccdc_archive 'CCDC 1039193'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point 367
_chemical_formula_moiety C6H6BrNO2S,C5H9NO
_chemical_formula_sum
'C11 H15 Br N2 O3 S'
_chemical_formula_weight 335.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'S' 'S' 0.1246 0.1234
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'Br' 'Br' -0.2901 2.4595
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting 'Monoclinic'
_symmetry_space_group_name_H-M 'C2/c '
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a 25.914(3)
_cell_length_b 6.8687(9)
_cell_length_c 19.202(2)
_cell_angle_alpha 90.00
_cell_angle_beta 126.873(2)
_cell_angle_gamma 90.00
_cell_volume 2734.1(6)
_cell_formula_units_Z 8
_cell_measurement_temperature 298(2)
_cell_measurement_reflns_used 4015
_cell_measurement_theta_min 2.65
_cell_measurement_theta_max 25.39
_exptl_crystal_description PLATE
_exptl_crystal_colour COLORLES
_exptl_crystal_size_max 0.22
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.20
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.629
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1360
_exptl_absorpt_coefficient_mu 3.161
_exptl_absorpt_correction_type 'none'
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 298(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 14029
_diffrn_reflns_av_R_equivalents 0.0304
_diffrn_reflns_av_sigmaI/netI 0.0241
_diffrn_reflns_limit_h_min -32
_diffrn_reflns_limit_h_max 32
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_l_min -23
_diffrn_reflns_limit_l_max 23
_diffrn_reflns_theta_min 1.96
_diffrn_reflns_theta_max 26.35
_reflns_number_total 2790
_reflns_number_gt 2216
_reflns_threshold_expression >2sigma(I)
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^2^, conventional
R-factors R are based on F, with F set to zero for
negative F^2^. The threshold expression of F^2^ >
\s(F^2^) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^2^ are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0541P)^2^+0.8825P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 2790
_refine_ls_number_parameters 175
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0468
_refine_ls_R_factor_gt 0.0348
_refine_ls_wR_factor_ref 0.0939
_refine_ls_wR_factor_gt 0.0877
_refine_ls_goodness_of_fit_ref 1.029
_refine_ls_restrained_S_all 1.029
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.003156(14) 0.69679(5) 0.14703(2) 0.07718(16) Uani 1 1 d . . .
S1 S 0.16814(3) 0.16446(9) 0.08449(4) 0.04800(18) Uani 1 1 d . . .
O1 O 0.14262(10) -0.0289(3) 0.06658(13) 0.0690(5) Uani 1 1 d . . .
N2 N 0.19222(12) 0.3131(3) 0.34335(16) 0.0533(6) Uani 1 1 d . . .
O3 O 0.20743(10) 0.0431(3) 0.29329(12) 0.0617(5) Uani 1 1 d . . .
C7 C 0.18364(12) 0.1262(4) 0.32543(15) 0.0440(5) Uani 1 1 d . . .
N1 N 0.23788(12) 0.1604(4) 0.17853(15) 0.0510(5) Uani 1 1 d . . .
C1 C 0.11787(12) 0.3130(3) 0.09613(15) 0.0431(5) Uani 1 1 d . . .
C4 C 0.04600(11) 0.5392(4) 0.12539(15) 0.0492(6) Uani 1 1 d . . .
O2 O 0.17723(10) 0.2564(3) 0.02588(12) 0.0622(5) Uani 1 1 d . . .
C5 C 0.03196(13) 0.3442(4) 0.10870(19) 0.0588(7) Uani 1 1 d . . .
H5 H -0.0017 0.2903 0.1069 0.071 Uiso 1 1 calc R . .
C6 C 0.06871(13) 0.2296(4) 0.09456(19) 0.0551(6) Uani 1 1 d . . .
H6 H 0.0604 0.0970 0.0840 0.066 Uiso 1 1 calc R . .
C10 C 0.14516(15) 0.3028(4) 0.42200(19) 0.0596(7) Uani 1 1 d . . .
H10A H 0.1825 0.2517 0.4766 0.072 Uiso 1 1 calc R . .
H10B H 0.1200 0.3793 0.4343 0.072 Uiso 1 1 calc R . .
C2 C 0.13035(12) 0.5088(3) 0.11092(16) 0.0491(6) Uani 1 1 d . . .
H2 H 0.1629 0.5643 0.1105 0.059 Uiso 1 1 calc R . .
C3 C 0.09429(13) 0.6235(4) 0.12650(17) 0.0532(6) Uani 1 1 d . . .
H3 H 0.1028 0.7559 0.1375 0.064 Uiso 1 1 calc R . .
C8 C 0.14546(14) 0.0129(4) 0.34662(19) 0.0586(7) Uani 1 1 d . . .
H8A H 0.1749 -0.0650 0.3981 0.070 Uiso 1 1 calc R . .
H8B H 0.1170 -0.0756 0.2990 0.070 Uiso 1 1 calc R . .
C11 C 0.16695(14) 0.4302(4) 0.38022(18) 0.0607(7) Uani 1 1 d . . .
H11A H 0.1309 0.5075 0.3346 0.073 Uiso 1 1 calc R . .
H11B H 0.2002 0.5186 0.4234 0.073 Uiso 1 1 calc R . .
C9 C 0.10520(15) 0.1386(5) 0.3626(2) 0.0667(8) Uani 1 1 d . . .
H9A H 0.0682 0.1897 0.3077 0.080 Uiso 1 1 calc R . .
H9B H 0.0896 0.0605 0.3885 0.080 Uiso 1 1 calc R . .
H1A H 0.2336(13) 0.127(4) 0.2156(18) 0.059(8) Uiso 1 1 d . . .
H1B H 0.2591(15) 0.271(4) 0.190(2) 0.066(9) Uiso 1 1 d . . .
H2A H 0.2102(13) 0.365(4) 0.3314(18) 0.053(8) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0590(2) 0.1037(3) 0.0761(2) -0.01461(16) 0.04444(19) 0.01633(16)
S1 0.0623(4) 0.0435(3) 0.0554(4) -0.0004(3) 0.0445(3) 0.0047(3)
O1 0.0909(14) 0.0480(10) 0.0923(14) -0.0169(10) 0.0678(13) -0.0075(10)
N2 0.0642(14) 0.0494(14) 0.0668(15) -0.0004(10) 0.0502(13) -0.0107(10)
O3 0.0793(13) 0.0598(11) 0.0699(12) 0.0079(9) 0.0576(11) 0.0112(9)
C7 0.0466(13) 0.0466(14) 0.0430(12) 0.0034(10) 0.0290(11) 0.0008(11)
N1 0.0607(14) 0.0504(13) 0.0586(14) 0.0088(10) 0.0447(12) 0.0128(11)
C1 0.0467(13) 0.0456(14) 0.0446(12) 0.0044(10) 0.0315(11) 0.0062(10)
C4 0.0433(13) 0.0624(16) 0.0445(13) 0.0028(11) 0.0277(11) 0.0126(11)
O2 0.0821(13) 0.0688(11) 0.0610(11) 0.0079(9) 0.0565(11) 0.0116(10)
C5 0.0530(15) 0.0697(18) 0.0695(18) 0.0058(14) 0.0452(15) 0.0036(13)
C6 0.0597(16) 0.0467(13) 0.0700(17) -0.0006(12) 0.0449(15) -0.0023(12)
C10 0.0682(18) 0.0629(17) 0.0658(17) -0.0024(13) 0.0498(16) 0.0011(13)
C2 0.0520(14) 0.0454(13) 0.0612(15) 0.0010(11) 0.0400(13) -0.0007(11)
C3 0.0564(15) 0.0450(13) 0.0634(16) -0.0016(12) 0.0387(14) 0.0061(11)
C8 0.0753(18) 0.0506(15) 0.0666(16) -0.0091(12) 0.0515(15) -0.0187(13)
C11 0.0800(19) 0.0451(15) 0.0711(18) -0.0027(12) 0.0528(17) -0.0009(13)
C9 0.0657(18) 0.0780(19) 0.0761(19) -0.0058(15) 0.0530(16) -0.0168(15)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C4 1.898(2) . ?
S1 O2 1.4280(18) . ?
S1 O1 1.431(2) . ?
S1 N1 1.616(2) . ?
S1 C1 1.771(2) . ?
N2 C7 1.313(3) . ?
N2 C11 1.461(3) . ?
O3 C7 1.242(3) . ?
C7 C8 1.494(3) . ?
C1 C2 1.373(3) . ?
C1 C6 1.380(3) . ?
C4 C3 1.367(4) . ?
C4 C5 1.374(4) . ?
C5 C6 1.382(4) . ?
C10 C9 1.493(4) . ?
C10 C11 1.507(4) . ?
C2 C3 1.385(3) . ?
C8 C9 1.520(4) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 119.48(12) . . ?
O2 S1 N1 106.60(13) . . ?
O1 S1 N1 107.35(13) . . ?
O2 S1 C1 109.04(11) . . ?
O1 S1 C1 107.23(11) . . ?
N1 S1 C1 106.45(11) . . ?
C7 N2 C11 127.6(2) . . ?
O3 C7 N2 121.5(2) . . ?
O3 C7 C8 120.2(2) . . ?
N2 C7 C8 118.3(2) . . ?
C2 C1 C6 120.7(2) . . ?
C2 C1 S1 119.39(18) . . ?
C6 C1 S1 119.82(18) . . ?
C3 C4 C5 121.9(2) . . ?
C3 C4 Br1 118.89(19) . . ?
C5 C4 Br1 119.23(19) . . ?
C4 C5 C6 118.9(2) . . ?
C1 C6 C5 119.7(2) . . ?
C9 C10 C11 110.0(2) . . ?
C1 C2 C3 119.8(2) . . ?
C4 C3 C2 119.0(2) . . ?
C7 C8 C9 113.9(2) . . ?
N2 C11 C10 111.0(2) . . ?
C10 C9 C8 109.8(2) . . ?
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full 26.35
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max 0.564
_refine_diff_density_min -0.389
_refine_diff_density_rms 0.060
data_PTSAVLM
_publcif_datablock.id '{7e11362c-8d94-464e-b874-a95e4fa90ee4}'
_database_code_depnum_ccdc_archive 'CCDC 1039200'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point 347
_chemical_formula_moiety C7H9NO2S,C5H9NO
_chemical_formula_sum
'C12 H18 N2 O3 S'
_chemical_formula_weight 270.34
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'S' 'S' 0.1246 0.1234
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting 'Triclinic'
_symmetry_space_group_name_H-M 'P-1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 5.210(3)
_cell_length_b 8.449(4)
_cell_length_c 16.104(8)
_cell_angle_alpha 82.894(8)
_cell_angle_beta 82.798(8)
_cell_angle_gamma 81.772(8)
_cell_volume 692.0(6)
_cell_formula_units_Z 2
_cell_measurement_temperature 298(2)
_cell_measurement_reflns_used 1964
_cell_measurement_theta_min 2.45
_cell_measurement_theta_max 23.82
_exptl_crystal_description PLATE
_exptl_crystal_colour COLORLES
_exptl_crystal_size_max 0.22
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.20
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.298
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 288
_exptl_absorpt_coefficient_mu 0.236
_exptl_absorpt_correction_type 'none'
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 298(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 7341
_diffrn_reflns_av_R_equivalents 0.0234
_diffrn_reflns_av_sigmaI/netI 0.0300
_diffrn_reflns_limit_h_min -6
_diffrn_reflns_limit_h_max 6
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -20
_diffrn_reflns_limit_l_max 19
_diffrn_reflns_theta_min 1.28
_diffrn_reflns_theta_max 26.37
_reflns_number_total 2819
_reflns_number_gt 1969
_reflns_threshold_expression >2sigma(I)
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^2^, conventional
R-factors R are based on F, with F set to zero for
negative F^2^. The threshold expression of F^2^ >
\s(F^2^) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^2^ are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0881P)^2^+0.0472P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 2819
_refine_ls_number_parameters 176
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0734
_refine_ls_R_factor_gt 0.0504
_refine_ls_wR_factor_ref 0.1526
_refine_ls_wR_factor_gt 0.1391
_refine_ls_goodness_of_fit_ref 1.042
_refine_ls_restrained_S_all 1.042
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.10112(11) 0.19293(7) 0.72741(4) 0.0619(3) Uani 1 1 d . . .
O3 O 0.8702(3) 0.41356(19) 0.91796(10) 0.0688(5) Uani 1 1 d . . .
N2 N 0.7568(4) 0.6588(2) 0.95856(14) 0.0597(5) Uani 1 1 d . . .
C8 C 0.7356(4) 0.5482(3) 0.91038(14) 0.0537(5) Uani 1 1 d . . .
N1 N 0.8887(4) 0.1678(3) 0.80706(15) 0.0599(5) Uani 1 1 d . . .
C1 C 1.0056(4) 0.3814(3) 0.67244(14) 0.0535(5) Uani 1 1 d . . .
O2 O 1.0896(4) 0.0718(2) 0.67443(13) 0.0934(7) Uani 1 1 d . . .
O1 O 1.3393(3) 0.2030(2) 0.76034(15) 0.0947(7) Uani 1 1 d . . .
C12 C 0.6188(5) 0.8210(3) 0.95606(18) 0.0737(7) Uani 1 1 d . . .
H12A H 0.7382 0.8964 0.9311 0.088 Uiso 1 1 calc R . .
H12B H 0.5601 0.8456 1.0132 0.088 Uiso 1 1 calc R . .
C4 C 0.8259(5) 0.6833(3) 0.59678(16) 0.0682(7) Uani 1 1 d . . .
C11 C 0.3906(6) 0.8430(4) 0.9073(2) 0.0909(9) Uani 1 1 d . . .
H11A H 0.2450 0.8012 0.9425 0.109 Uiso 1 1 calc R . .
H11B H 0.3405 0.9571 0.8924 0.109 Uiso 1 1 calc R . .
C6 C 1.1026(5) 0.5156(3) 0.68710(19) 0.0790(8) Uani 1 1 d . . .
H6 H 1.2325 0.5064 0.7227 0.095 Uiso 1 1 calc R . .
C2 C 0.8195(6) 0.3973(3) 0.61818(17) 0.0821(8) Uani 1 1 d . . .
H2 H 0.7526 0.3073 0.6062 0.099 Uiso 1 1 calc R . .
C10 C 0.4426(7) 0.7627(4) 0.8306(2) 0.1003(11) Uani 1 1 d . . .
H10A H 0.5719 0.8144 0.7922 0.120 Uiso 1 1 calc R . .
H10B H 0.2837 0.7751 0.8036 0.120 Uiso 1 1 calc R . .
C9 C 0.5402(5) 0.5845(3) 0.84744(16) 0.0707(7) Uani 1 1 d . . .
H9A H 0.3924 0.5270 0.8677 0.085 Uiso 1 1 calc R . .
H9B H 0.6190 0.5450 0.7949 0.085 Uiso 1 1 calc R . .
C5 C 1.0095(6) 0.6651(3) 0.64949(19) 0.0792(8) Uani 1 1 d . . .
H5 H 1.0762 0.7554 0.6611 0.095 Uiso 1 1 calc R . .
C7 C 0.7207(7) 0.8483(4) 0.5574(2) 0.1055(11) Uani 1 1 d . . .
H7A H 0.8460 0.9213 0.5573 0.158 Uiso 1 1 calc R . .
H7B H 0.5606 0.8866 0.5893 0.158 Uiso 1 1 calc R . .
H7C H 0.6889 0.8415 0.5006 0.158 Uiso 1 1 calc R . .
C3 C 0.7320(7) 0.5486(4) 0.5813(2) 0.0975(10) Uani 1 1 d . . .
H3 H 0.6047 0.5589 0.5447 0.117 Uiso 1 1 calc R . .
H1A H 0.756(5) 0.158(3) 0.7922(15) 0.054(7) Uiso 1 1 d . . .
H1B H 0.885(5) 0.240(3) 0.8399(16) 0.071(9) Uiso 1 1 d . . .
H2A H 0.850(5) 0.637(3) 0.9921(16) 0.058(7) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0507(4) 0.0481(4) 0.0836(5) 0.0001(3) -0.0138(3) 0.0045(2)
O3 0.0761(11) 0.0595(10) 0.0727(11) -0.0121(8) -0.0338(9) 0.0114(8)
N2 0.0561(12) 0.0552(12) 0.0694(13) -0.0061(10) -0.0288(11) 0.0057(9)
C8 0.0486(12) 0.0555(13) 0.0563(13) 0.0003(11) -0.0154(10) -0.0016(10)
N1 0.0556(13) 0.0507(12) 0.0747(15) 0.0014(10) -0.0215(11) -0.0055(9)
C1 0.0452(11) 0.0502(12) 0.0630(14) -0.0021(10) -0.0085(10) 0.0000(9)
O2 0.1218(17) 0.0521(10) 0.1003(14) -0.0214(10) -0.0043(12) 0.0137(10)
O1 0.0483(10) 0.0814(13) 0.1487(18) 0.0282(12) -0.0358(11) -0.0023(8)
C12 0.0704(16) 0.0559(14) 0.0935(19) -0.0057(13) -0.0284(14) 0.0117(12)
C4 0.0780(17) 0.0606(15) 0.0592(14) 0.0070(11) -0.0071(13) 0.0017(12)
C11 0.087(2) 0.0695(18) 0.114(2) -0.0013(17) -0.0433(18) 0.0168(14)
C6 0.0770(18) 0.0620(16) 0.105(2) 0.0058(14) -0.0459(16) -0.0155(13)
C2 0.111(2) 0.0632(17) 0.0815(18) -0.0033(14) -0.0445(17) -0.0175(15)
C10 0.116(3) 0.093(2) 0.089(2) -0.0051(17) -0.0550(19) 0.0324(18)
C9 0.0697(16) 0.0709(16) 0.0732(16) -0.0021(13) -0.0332(13) 0.0026(12)
C5 0.091(2) 0.0518(15) 0.098(2) 0.0037(14) -0.0275(17) -0.0144(13)
C7 0.127(3) 0.077(2) 0.100(2) 0.0254(17) -0.025(2) 0.0079(18)
C3 0.123(3) 0.082(2) 0.094(2) 0.0120(17) -0.067(2) -0.0061(18)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.423(2) . ?
S1 O1 1.426(2) . ?
S1 N1 1.600(2) . ?
S1 C1 1.762(2) . ?
O3 C8 1.249(3) . ?
N2 C8 1.311(3) . ?
N2 C12 1.452(3) . ?
N2 H2A 0.76(3) . ?
C8 C9 1.500(3) . ?
N1 H1A 0.78(3) . ?
N1 H1B 0.85(3) . ?
C1 C6 1.362(3) . ?
C1 C2 1.366(3) . ?
C12 C11 1.483(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C4 C5 1.337(4) . ?
C4 C3 1.362(4) . ?
C4 C7 1.516(3) . ?
C11 C10 1.459(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C6 C5 1.381(4) . ?
C6 H6 0.9300 . ?
C2 C3 1.381(4) . ?
C2 H2 0.9300 . ?
C10 C9 1.521(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C5 H5 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C3 H3 0.9300 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 119.81(13) . . ?
O2 S1 N1 107.32(14) . . ?
O1 S1 N1 106.20(14) . . ?
O2 S1 C1 108.18(12) . . ?
O1 S1 C1 107.38(11) . . ?
N1 S1 C1 107.36(10) . . ?
C8 N2 C12 127.3(2) . . ?
C8 N2 H2A 117.7(19) . . ?
C12 N2 H2A 115.0(19) . . ?
O3 C8 N2 120.9(2) . . ?
O3 C8 C9 120.4(2) . . ?
N2 C8 C9 118.7(2) . . ?
S1 N1 H1A 110.0(17) . . ?
S1 N1 H1B 110.7(17) . . ?
H1A N1 H1B 116(3) . . ?
C6 C1 C2 118.7(2) . . ?
C6 C1 S1 120.85(19) . . ?
C2 C1 S1 120.30(19) . . ?
N2 C12 C11 112.7(2) . . ?
N2 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
N2 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C5 C4 C3 117.7(2) . . ?
C5 C4 C7 121.2(3) . . ?
C3 C4 C7 121.1(3) . . ?
C10 C11 C12 112.8(3) . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C1 C6 C5 120.5(2) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C1 C2 C3 119.2(3) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C11 C10 C9 112.7(2) . . ?
C11 C10 H10A 109.1 . . ?
C9 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C8 C9 C10 113.6(2) . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C4 C5 C6 121.6(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C3 C2 122.3(3) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full 26.37
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max 0.429
_refine_diff_density_min -0.146
_refine_diff_density_rms 0.044
data_2ClBSAVLM
_publcif_datablock.id '{de896d98-b227-42e6-891d-35361ee6a1de}'
_database_code_depnum_ccdc_archive 'CCDC 1039191'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point 353
_chemical_formula_moiety C6H6ClNO2S,C5H9NO
_chemical_formula_sum
'C11 H15 Cl N2 O3 S'
_chemical_formula_weight 290.76
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'S' 'S' 0.1246 0.1234
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'Cl' 'Cl' 0.1484 0.1585
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P121/c1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 10.521(2)
_cell_length_b 13.7661(12)
_cell_length_c 10.3407(16)
_cell_angle_alpha 90.00
_cell_angle_beta 116.31(2)
_cell_angle_gamma 90.00
_cell_volume 1342.5(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 298(2)
_cell_measurement_reflns_used 1920
_cell_measurement_theta_min 3.7420
_cell_measurement_theta_max 28.7950
_exptl_crystal_description BLOCK
_exptl_crystal_colour COLORLES
_exptl_crystal_size_max 0.22
_exptl_crystal_size_mid 0.22
_exptl_crystal_size_min 0.20
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.439
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 608
_exptl_absorpt_coefficient_mu 0.442
_exptl_absorpt_correction_type 'multi-scan'
_exptl_absorpt_correction_T_min 0.70693
_exptl_absorpt_correction_T_max 1.0000
_exptl_absorpt_process_details SADABS
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 298(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Xcalibur, Eos, Gemini'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 5058
_diffrn_reflns_av_R_equivalents 0.0383
_diffrn_reflns_av_sigmaI/netI 0.0517
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_k_max 17
_diffrn_reflns_limit_l_min -11
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 2.73
_diffrn_reflns_theta_max 26.37
_reflns_number_total 2731
_reflns_number_gt 2039
_reflns_threshold_expression >2sigma(I)
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^2^, conventional
R-factors R are based on F, with F set to zero for
negative F^2^. The threshold expression of F^2^ >
\s(F^2^) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^2^ are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0596P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 2731
_refine_ls_number_parameters 169
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0618
_refine_ls_R_factor_gt 0.0435
_refine_ls_wR_factor_ref 0.1144
_refine_ls_wR_factor_gt 0.1052
_refine_ls_goodness_of_fit_ref 0.983
_refine_ls_restrained_S_all 0.983
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.19111(6) 0.19966(4) 0.48704(5) 0.03615(18) Uani 1 1 d . . .
Cl1 Cl 0.05379(7) 0.11264(4) 0.16036(6) 0.0540(2) Uani 1 1 d . . .
O1 O 0.26755(18) 0.20526(11) 0.64070(15) 0.0487(4) Uani 1 1 d . . .
O2 O 0.05885(17) 0.24899(11) 0.41564(16) 0.0495(4) Uani 1 1 d . . .
C1 C 0.1601(2) 0.07383(14) 0.4485(2) 0.0328(5) Uani 1 1 d . . .
N1 N 0.2947(2) 0.24040(14) 0.4250(2) 0.0437(5) Uani 1 1 d . . .
H1B H 0.257(3) 0.2485(18) 0.335(3) 0.052 Uiso 1 1 d . . .
H1A H 0.372(3) 0.2141(19) 0.462(3) 0.052 Uiso 1 1 d . . .
O3 O 0.54379(19) 0.12661(13) 0.55417(18) 0.0610(5) Uani 1 1 d . . .
C2 C 0.1944(2) 0.01049(17) 0.5627(2) 0.0437(6) Uani 1 1 d . . .
H2 H 0.2366 0.0337 0.6569 0.052 Uiso 1 1 calc R . .
N2 N 0.5607(2) 0.00213(15) 0.6987(2) 0.0525(5) Uani 1 1 d . . .
H2A H 0.5325 -0.0349 0.6242 0.063 Uiso 1 1 calc R . .
C5 C 0.0690(3) -0.06037(17) 0.2835(3) 0.0506(6) Uani 1 1 d . . .
H5 H 0.0269 -0.0842 0.1896 0.061 Uiso 1 1 calc R . .
C6 C 0.0966(2) 0.03718(16) 0.3083(2) 0.0387(5) Uani 1 1 d . . .
C3 C 0.1659(3) -0.08749(19) 0.5367(3) 0.0584(7) Uani 1 1 d . . .
H3 H 0.1888 -0.1300 0.6137 0.070 Uiso 1 1 calc R . .
C4 C 0.1040(3) -0.12237(18) 0.3982(3) 0.0590(7) Uani 1 1 d . . .
H4 H 0.0857 -0.1885 0.3819 0.071 Uiso 1 1 calc R . .
C8 C 0.5756(3) 0.09436(19) 0.6778(3) 0.0504(6) Uani 1 1 d . . .
C10 C 0.6294(4) 0.1197(2) 0.9393(3) 0.0769(9) Uani 1 1 d . . .
H10A H 0.6889 0.1581 1.0231 0.092 Uiso 1 1 calc R . .
H10B H 0.5329 0.1226 0.9282 0.092 Uiso 1 1 calc R . .
C12 C 0.5869(3) -0.0445(2) 0.8350(3) 0.0620(7) Uani 1 1 d . . .
H12A H 0.6321 -0.1069 0.8412 0.074 Uiso 1 1 calc R . .
H12B H 0.4972 -0.0561 0.8377 0.074 Uiso 1 1 calc R . .
C11 C 0.6794(3) 0.0165(3) 0.9618(3) 0.0742(9) Uani 1 1 d . . .
H11A H 0.7765 0.0137 0.9747 0.089 Uiso 1 1 calc R . .
H11B H 0.6774 -0.0089 1.0484 0.089 Uiso 1 1 calc R . .
C9 C 0.6348(3) 0.1615(2) 0.8064(3) 0.0674(8) Uani 1 1 d . . .
H9A H 0.5818 0.2219 0.7810 0.081 Uiso 1 1 calc R . .
H9B H 0.7325 0.1765 0.8291 0.081 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0502(4) 0.0291(3) 0.0311(3) -0.0019(2) 0.0198(3) 0.0002(3)
Cl1 0.0700(5) 0.0501(4) 0.0350(3) -0.0051(2) 0.0170(3) -0.0103(3)
O1 0.0696(12) 0.0471(9) 0.0308(8) -0.0062(7) 0.0235(8) -0.0030(9)
O2 0.0581(11) 0.0373(9) 0.0523(10) 0.0027(7) 0.0236(9) 0.0128(8)
C1 0.0346(11) 0.0276(10) 0.0395(11) 0.0012(9) 0.0194(9) 0.0007(9)
N1 0.0544(13) 0.0405(11) 0.0349(10) 0.0001(8) 0.0185(10) -0.0103(10)
O3 0.0692(13) 0.0589(11) 0.0577(11) 0.0064(9) 0.0307(9) 0.0052(10)
C2 0.0449(13) 0.0395(12) 0.0484(13) 0.0068(10) 0.0223(11) 0.0034(11)
N2 0.0594(14) 0.0497(12) 0.0456(11) -0.0017(9) 0.0207(10) 0.0039(11)
C5 0.0541(16) 0.0360(12) 0.0662(15) -0.0136(12) 0.0308(13) -0.0100(12)
C6 0.0379(12) 0.0357(11) 0.0459(13) -0.0026(9) 0.0216(10) -0.0037(10)
C3 0.0583(17) 0.0398(13) 0.0824(19) 0.0222(13) 0.0360(14) 0.0068(13)
C4 0.0581(17) 0.0299(12) 0.093(2) -0.0035(13) 0.0375(15) -0.0039(12)
C8 0.0419(14) 0.0527(15) 0.0562(16) -0.0011(12) 0.0214(12) 0.0052(12)
C10 0.087(2) 0.082(2) 0.0587(18) -0.0146(16) 0.0297(16) 0.002(2)
C12 0.0659(18) 0.0641(17) 0.0532(15) 0.0097(13) 0.0239(14) 0.0105(15)
C11 0.073(2) 0.090(2) 0.0475(15) 0.0012(15) 0.0159(14) 0.0098(18)
C9 0.0657(19) 0.0590(17) 0.075(2) -0.0106(15) 0.0296(16) -0.0006(16)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4254(16) . ?
S1 O1 1.4299(16) . ?
S1 N1 1.592(2) . ?
S1 C1 1.775(2) . ?
Cl1 C6 1.735(2) . ?
C1 C2 1.380(3) . ?
C1 C6 1.395(3) . ?
N1 H1B 0.84(3) . ?
N1 H1A 0.81(3) . ?
O3 C8 1.251(3) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9300 . ?
N2 C8 1.309(3) . ?
N2 C12 1.460(3) . ?
N2 H2A 0.8600 . ?
C5 C4 1.373(4) . ?
C5 C6 1.374(3) . ?
C5 H5 0.9300 . ?
C3 C4 1.370(4) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C8 C9 1.508(3) . ?
C10 C11 1.497(4) . ?
C10 C9 1.514(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 C11 1.497(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 119.27(10) . . ?
O2 S1 N1 108.00(11) . . ?
O1 S1 N1 106.29(11) . . ?
O2 S1 C1 107.98(10) . . ?
O1 S1 C1 105.00(10) . . ?
N1 S1 C1 110.12(10) . . ?
C2 C1 C6 118.9(2) . . ?
C2 C1 S1 118.18(16) . . ?
C6 C1 S1 122.81(15) . . ?
S1 N1 H1B 115.1(17) . . ?
S1 N1 H1A 112.1(19) . . ?
H1B N1 H1A 117(3) . . ?
C1 C2 C3 119.9(2) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C8 N2 C12 126.9(2) . . ?
C8 N2 H2A 116.5 . . ?
C12 N2 H2A 116.5 . . ?
C4 C5 C6 119.5(2) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 120.8(2) . . ?
C5 C6 Cl1 118.02(18) . . ?
C1 C6 Cl1 121.17(17) . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
O3 C8 N2 121.0(2) . . ?
O3 C8 C9 120.2(2) . . ?
N2 C8 C9 118.8(2) . . ?
C11 C10 C9 110.5(3) . . ?
C11 C10 H10A 109.6 . . ?
C9 C10 H10A 109.6 . . ?
C11 C10 H10B 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
N2 C12 C11 111.7(2) . . ?
N2 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
N2 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C12 C11 C10 110.4(2) . . ?
C12 C11 H11A 109.6 . . ?
C10 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C8 C9 C10 113.6(2) . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 26.37
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max 0.381
_refine_diff_density_min -0.359
_refine_diff_density_rms 0.080
data_BSAVLM
_publcif_datablock.id '{74658a82-f34d-477f-b943-ad79ef3bb075}'
_database_code_depnum_ccdc_archive 'CCDC 1039198'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point 352
_chemical_formula_moiety C6H7NO2S,C5H9NO
_chemical_formula_sum
'C11 H16 N2 O3 S'
_chemical_formula_weight 256.32
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'S' 'S' 0.1246 0.1234
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_H-M 'P 21 21 21'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
_cell_length_a 7.1043(5)
_cell_length_b 12.7937(10)
_cell_length_c 14.0302(16)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 1275.2(2)
_cell_formula_units_Z 4
_cell_measurement_temperature 298(2)
_cell_measurement_reflns_used 1374
_cell_measurement_theta_min 3.5910
_cell_measurement_theta_max 27.8320
_exptl_crystal_description PLATE
_exptl_crystal_colour COLORLES
_exptl_crystal_size_max 0.22
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.20
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.335
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 544
_exptl_absorpt_coefficient_mu 0.253
_exptl_absorpt_correction_type 'multi-scan'
_exptl_absorpt_correction_T_min 0.67919
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_process_details SADABS
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 298(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Xcalibur, Eos, Gemini'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 3791
_diffrn_reflns_av_R_equivalents 0.0252
_diffrn_reflns_av_sigmaI/netI 0.0379
_diffrn_reflns_limit_h_min -4
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 2.90
_diffrn_reflns_theta_max 26.35
_reflns_number_total 2493
_reflns_number_gt 2175
_reflns_threshold_expression >2sigma(I)
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^2^, conventional
R-factors R are based on F, with F set to zero for
negative F^2^. The threshold expression of F^2^ >
\s(F^2^) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^2^ are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0594P)^2^+0.2685P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack -0.01(12)
_refine_ls_number_reflns 2493
_refine_ls_number_parameters 160
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0543
_refine_ls_R_factor_gt 0.0466
_refine_ls_wR_factor_ref 0.1201
_refine_ls_wR_factor_gt 0.1138
_refine_ls_goodness_of_fit_ref 1.059
_refine_ls_restrained_S_all 1.059
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.09979(9) 0.66876(5) 0.35518(6) 0.0479(2) Uani 1 1 d . . .
O2 O -0.0932(3) 0.69509(18) 0.34129(19) 0.0701(7) Uani 1 1 d . . .
C1 C 0.2366(4) 0.7664(2) 0.29907(19) 0.0400(6) Uani 1 1 d . . .
N1 N 0.1392(4) 0.6744(2) 0.4676(2) 0.0536(6) Uani 1 1 d . . .
H1A H 0.243(5) 0.647(3) 0.484(3) 0.064 Uiso 1 1 d . . .
H1B H 0.114(5) 0.732(3) 0.489(3) 0.064 Uiso 1 1 d . . .
O1 O 0.1650(4) 0.56864(17) 0.32366(19) 0.0672(7) Uani 1 1 d . . .
C6 C 0.4304(4) 0.7576(2) 0.3012(2) 0.0493(7) Uani 1 1 d . . .
H6 H 0.4877 0.6997 0.3287 0.059 Uiso 1 1 calc R . .
C4 C 0.4533(5) 0.9224(3) 0.2214(2) 0.0611(9) Uani 1 1 d . . .
H4 H 0.5273 0.9753 0.1957 0.073 Uiso 1 1 calc R . .
C2 C 0.1514(4) 0.8530(2) 0.2593(2) 0.0488(7) Uani 1 1 d . . .
H2 H 0.0209 0.8591 0.2596 0.059 Uiso 1 1 calc R . .
C3 C 0.2607(5) 0.9305(3) 0.2191(2) 0.0571(8) Uani 1 1 d . . .
H3 H 0.2040 0.9880 0.1905 0.069 Uiso 1 1 calc R . .
C5 C 0.5370(4) 0.8361(3) 0.2618(3) 0.0648(9) Uani 1 1 d . . .
H5 H 0.6675 0.8308 0.2625 0.078 Uiso 1 1 calc R . .
O3 O 0.0223(3) -0.11055(17) 0.49917(18) 0.0627(6) Uani 1 1 d . . .
N2 N 0.2865(4) -0.0211(2) 0.4788(2) 0.0569(7) Uani 1 1 d . . .
H2A H 0.3463 -0.0769 0.4947 0.068 Uiso 1 1 calc R . .
C7 C 0.1024(5) -0.0281(2) 0.47661(19) 0.0468(6) Uani 1 1 d . . .
C8 C -0.0072(6) 0.0650(3) 0.4470(3) 0.0718(10) Uani 1 1 d . . .
H8A H -0.0990 0.0805 0.4962 0.086 Uiso 1 1 calc R . .
H8B H -0.0759 0.0480 0.3893 0.086 Uiso 1 1 calc R . .
C11 C 0.4012(6) 0.0702(3) 0.4577(3) 0.0807(11) Uani 1 1 d . . .
H11A H 0.4743 0.0889 0.5135 0.097 Uiso 1 1 calc R . .
H11B H 0.4883 0.0536 0.4066 0.097 Uiso 1 1 calc R . .
C10 C 0.2857(13) 0.1574(5) 0.4298(8) 0.220(6) Uani 1 1 d . . .
H10A H 0.3255 0.2153 0.4697 0.264 Uiso 1 1 calc R . .
H10B H 0.3246 0.1749 0.3655 0.264 Uiso 1 1 calc R . .
C9 C 0.1069(11) 0.1609(4) 0.4291(6) 0.152(3) Uani 1 1 d . . .
H9A H 0.0694 0.1879 0.3673 0.182 Uiso 1 1 calc R . .
H9B H 0.0692 0.2124 0.4761 0.182 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0358(3) 0.0397(3) 0.0682(5) -0.0019(3) 0.0010(3) -0.0044(3)
O2 0.0330(10) 0.0707(14) 0.1068(19) 0.0053(13) -0.0080(12) -0.0073(10)
C1 0.0353(13) 0.0443(15) 0.0403(14) -0.0022(12) 0.0009(11) -0.0009(12)
N1 0.0528(15) 0.0441(13) 0.0639(16) 0.0057(13) 0.0097(13) -0.0006(13)
O1 0.0668(14) 0.0453(11) 0.0894(17) -0.0154(11) 0.0060(13) -0.0056(11)
C6 0.0383(15) 0.0501(15) 0.0595(18) 0.0067(14) 0.0017(13) 0.0040(13)
C4 0.064(2) 0.062(2) 0.057(2) 0.0095(16) 0.0116(16) -0.0070(17)
C2 0.0399(15) 0.0538(17) 0.0526(16) 0.0031(14) -0.0051(13) 0.0088(12)
C3 0.069(2) 0.0525(18) 0.0498(18) 0.0114(15) 0.0030(17) 0.0071(17)
C5 0.0399(16) 0.079(2) 0.075(2) 0.011(2) 0.0091(15) -0.0058(17)
O3 0.0593(14) 0.0482(12) 0.0807(16) 0.0037(11) 0.0135(12) -0.0039(11)
N2 0.0517(16) 0.0493(15) 0.0697(18) 0.0039(13) -0.0102(13) 0.0006(12)
C7 0.0556(17) 0.0424(14) 0.0424(14) -0.0017(12) 0.0016(14) 0.0061(15)
C8 0.075(2) 0.060(2) 0.081(3) 0.0070(18) -0.006(2) 0.0233(19)
C11 0.078(3) 0.077(2) 0.087(3) 0.004(2) -0.004(2) -0.031(2)
C10 0.148(7) 0.095(4) 0.417(15) 0.137(7) -0.117(9) -0.060(5)
C9 0.154(6) 0.056(3) 0.245(8) 0.060(4) 0.057(6) 0.035(4)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.425(2) . ?
S1 O1 1.432(2) . ?
S1 N1 1.604(3) . ?
S1 C1 1.768(3) . ?
C1 C2 1.380(4) . ?
C1 C6 1.382(4) . ?
N1 H1A 0.85(4) . ?
N1 H1B 0.82(4) . ?
C6 C5 1.373(5) . ?
C6 H6 0.9300 . ?
C4 C3 1.373(5) . ?
C4 C5 1.376(5) . ?
C4 H4 0.9300 . ?
C2 C3 1.380(5) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C5 H5 0.9300 . ?
O3 C7 1.239(3) . ?
N2 C7 1.312(4) . ?
N2 C11 1.454(4) . ?
N2 H2A 0.8600 . ?
C7 C8 1.483(4) . ?
C8 C9 1.492(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C11 C10 1.439(8) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C10 C9 1.271(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 118.70(15) . . ?
O2 S1 N1 106.96(16) . . ?
O1 S1 N1 106.72(16) . . ?
O2 S1 C1 107.52(14) . . ?
O1 S1 C1 108.47(14) . . ?
N1 S1 C1 108.07(13) . . ?
C2 C1 C6 120.7(3) . . ?
C2 C1 S1 120.4(2) . . ?
C6 C1 S1 118.7(2) . . ?
S1 N1 H1A 113(3) . . ?
S1 N1 H1B 111(3) . . ?
H1A N1 H1B 118(4) . . ?
C5 C6 C1 118.8(3) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C2 C1 119.6(3) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C7 N2 C11 127.5(3) . . ?
C7 N2 H2A 116.2 . . ?
C11 N2 H2A 116.2 . . ?
O3 C7 N2 120.7(3) . . ?
O3 C7 C8 120.9(3) . . ?
N2 C7 C8 118.4(3) . . ?
C7 C8 C9 115.0(4) . . ?
C7 C8 H8A 108.5 . . ?
C9 C8 H8A 108.5 . . ?
C7 C8 H8B 108.5 . . ?
C9 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C10 C11 N2 111.0(4) . . ?
C10 C11 H11A 109.4 . . ?
N2 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
N2 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C9 C10 C11 126.8(5) . . ?
C9 C10 H10A 105.6 . . ?
C11 C10 H10A 105.6 . . ?
C9 C10 H10B 105.6 . . ?
C11 C10 H10B 105.6 . . ?
H10A C10 H10B 106.1 . . ?
C10 C9 C8 120.9(5) . . ?
C10 C9 H9A 107.1 . . ?
C8 C9 H9A 107.1 . . ?
C10 C9 H9B 107.1 . . ?
C8 C9 H9B 107.1 . . ?
H9A C9 H9B 106.8 . . ?
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full 26.35
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max 0.246
_refine_diff_density_min -0.238
_refine_diff_density_rms 0.044
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
'{e6c00078-b2a2-48fe-bade-f4053a1f4afd}' ? ? ?
'{ff55f32d-463c-46a0-a5da-c6956429db7c}' y y y
'{6ae9f214-f6c1-4470-8cfd-e02939af13f3}' y y y
'{44fb6c3f-7f62-4ff1-8b5d-03e1a9d7af91}' y y y
'{e9413eff-41ec-4c5a-b79f-512e0244b8cb}' y y y
'{665b0f37-4d51-4f60-aad4-cd323a567d2e}' y y y
'{200e1bba-1993-492f-a49a-bfd9dfb1fd04}' y y y
'{a30a02d8-6f92-42e6-ac6b-60c701facf4a}' y y y
'{649310c0-c732-4b83-9218-60674abe29ca}' y y y
'{2198d17f-4001-4fe3-b6eb-2ea6e9e3e8e1}' y y y
'{e69b45eb-4585-4770-9ddd-4016e8a94097}' y y y
'{7e11362c-8d94-464e-b874-a95e4fa90ee4}' y y y
'{de896d98-b227-42e6-891d-35361ee6a1de}' y y y
'{74658a82-f34d-477f-b943-ad79ef3bb075}' y y y
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
loop_
_publcif_info_exptl_table_header_item
?