data_06182

 

_audit_creation_method            SHELXL-97

_chemical_name_systematic

;

 ?

;

_chemical_name_common             ?

_chemical_melting_point           ?

_chemical_formula_moiety          ?

_chemical_formula_sum

 'C9 H11 N3 O4 S'

_chemical_formula_weight          257.27

 

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                    8.1746(3)

_cell_length_b                    15.1930(5)

_cell_length_c                    9.8516(3)

_cell_angle_alpha                 90.00

_cell_angle_beta                  107.4690(10)

_cell_angle_gamma                 90.00

_cell_volume                      1167.11(7)

_cell_formula_units_Z             4

_cell_measurement_temperature     100(2)

_cell_measurement_reflns_used     7813

_cell_measurement_theta_min       2.55

_cell_measurement_theta_max       30.52

 

_exptl_crystal_description        Block

_exptl_crystal_colour             colorless

_exptl_crystal_size_max           0.50

_exptl_crystal_size_mid           0.50

_exptl_crystal_size_min           0.40

_exptl_crystal_density_meas       ?

_exptl_crystal_density_diffrn     1.464

_exptl_crystal_density_method     'not measured'

_exptl_crystal_F_000              536

_exptl_absorpt_coefficient_mu     0.285

_exptl_absorpt_correction_type    multi-scan

_exptl_absorpt_correction_T_min   0.8707

_exptl_absorpt_correction_T_max   0.8946

_exptl_absorpt_process_details    'SADABS (Sheldrick, 2005)'

 

_exptl_special_details

;

 ?

;

 

_diffrn_ambient_temperature       100(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   'Bruker Smart APEX CCD'

_diffrn_measurement_method        'omega and phi scans'

_diffrn_detector_area_resol_mean  8.3

_diffrn_standards_number          0

_diffrn_standards_interval_count  0

_diffrn_standards_interval_time   0

_diffrn_standards_decay_%         0

_diffrn_reflns_number             22799

_diffrn_reflns_av_R_equivalents   0.0201

_diffrn_reflns_av_sigmaI/netI     0.0114

_diffrn_reflns_limit_h_min        -10

_diffrn_reflns_limit_h_max        11

_diffrn_reflns_limit_k_min        -21

_diffrn_reflns_limit_k_max        21

_diffrn_reflns_limit_l_min        -13

_diffrn_reflns_limit_l_max        13

_diffrn_reflns_theta_min          2.55

_diffrn_reflns_theta_max          29.57

_reflns_number_total              3274

_reflns_number_gt                 3119

_reflns_threshold_expression      >2sigma(I)

 

_computing_data_collection        'SMART 5 (Bruker-AXS, 2003)'

_computing_cell_refinement        'SAINT 7 (Bruker-AXS, 2005)'

_computing_data_reduction         'SAINT 7 (Bruker-AXS, 2005)'

_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics     'Bruker SHELXTL'

_computing_publication_material   'Bruker SHELXTL'

 

_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^ > 2sigma(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^+0.4357P] 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          3274

_refine_ls_number_parameters      159

_refine_ls_number_restraints      1

_refine_ls_R_factor_all           0.0310

_refine_ls_R_factor_gt            0.0299

_refine_ls_wR_factor_ref          0.0858

_refine_ls_wR_factor_gt           0.0848

_refine_ls_goodness_of_fit_ref    1.060

_refine_ls_restrained_S_all       1.061

_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

O4 O 1.43279(10) 0.06380(5) 1.08964(8) 0.01863(16) Uani 1 1 d . . .

O1 O 1.03527(9) 0.11772(5) 1.03340(7) 0.01578(15) Uani 1 1 d . . .

O2 O 0.85017(9) 0.22037(5) 0.85636(8) 0.01883(16) Uani 1 1 d . . .

S1 S 0.96665(3) 0.147772(15) 0.88890(2) 0.01258(8) Uani 1 1 d . . .

N2 N 0.87131(11) 0.06225(5) 0.79826(9) 0.01424(16) Uani 1 1 d D . .

H2 H 0.9188(18) 0.0134(8) 0.8292(15) 0.017 Uiso 1 1 d D . .

N1 N 0.81256(12) 0.07871(6) 0.65091(9) 0.02035(19) Uani 1 1 d . . .

C2 C 0.77426(15) 0.01100(7) 0.57041(11) 0.0213(2) Uani 1 1 d . . .

C1 C 0.7901(2) -0.08237(8) 0.61988(13) 0.0371(3) Uani 1 1 d . . .

H1A H 0.9116 -0.0978 0.6588 0.056 Uiso 1 1 calc R . .

H1B H 0.7356 -0.1211 0.5395 0.056 Uiso 1 1 calc R . .

H1C H 0.7333 -0.0895 0.6938 0.056 Uiso 1 1 calc R . .

C3 C 0.7091(2) 0.02774(9) 0.41359(13) 0.0417(4) Uani 1 1 d . . .

H3A H 0.7065 0.0913 0.3958 0.063 Uiso 1 1 calc R . .

H3B H 0.5930 0.0036 0.3757 0.063 Uiso 1 1 calc R . .

H3C H 0.7850 -0.0008 0.3665 0.063 Uiso 1 1 calc R . .

O3 O 1.23815(9) -0.00784(5) 0.92756(8) 0.01699(15) Uani 1 1 d . . .

N3 N 1.32455(10) 0.05797(5) 0.97257(9) 0.01333(16) Uani 1 1 d . . .

C4 C 1.14205(12) 0.17592(6) 0.82653(10) 0.01273(17) Uani 1 1 d . . .

C5 C 1.30122(12) 0.13420(6) 0.87630(10) 0.01287(17) Uani 1 1 d . . .

C6 C 1.44154(13) 0.15924(7) 0.83447(11) 0.01570(19) Uani 1 1 d . . .

H6 H 1.5489 0.1304 0.8713 0.019 Uiso 1 1 calc R . .

C8 C 1.26409(14) 0.27041(7) 0.68523(11) 0.0186(2) Uani 1 1 d . . .

H8 H 1.2514 0.3171 0.6186 0.022 Uiso 1 1 calc R . .

C9 C 1.12471(13) 0.24517(6) 0.73044(11) 0.01611(19) Uani 1 1 d . . .

H9 H 1.0183 0.2751 0.6958 0.019 Uiso 1 1 calc R . .

C7 C 1.42142(13) 0.22791(7) 0.73677(11) 0.01794(19) Uani 1 1 d . . .

H7 H 1.5154 0.2457 0.7053 0.022 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

O4 0.0169(3) 0.0225(4) 0.0142(3) 0.0019(3) 0.0013(3) 0.0022(3)

O1 0.0172(3) 0.0191(3) 0.0121(3) -0.0011(3) 0.0059(3) -0.0011(3)

O2 0.0157(3) 0.0171(3) 0.0244(4) -0.0005(3) 0.0071(3) 0.0046(3)

S1 0.01192(12) 0.01317(12) 0.01334(12) -0.00088(7) 0.00486(9) 0.00041(7)

N2 0.0152(4) 0.0139(4) 0.0123(4) 0.0005(3) 0.0022(3) -0.0016(3)

N1 0.0260(5) 0.0190(4) 0.0126(4) 0.0022(3) 0.0005(3) -0.0027(3)

C2 0.0271(5) 0.0193(5) 0.0150(4) 0.0011(4) 0.0026(4) -0.0033(4)

C1 0.0673(10) 0.0177(5) 0.0199(5) -0.0011(4) 0.0034(6) -0.0028(6)

C3 0.0722(11) 0.0286(6) 0.0143(5) 0.0016(4) -0.0022(6) -0.0100(7)

O3 0.0162(3) 0.0137(3) 0.0216(4) 0.0010(3) 0.0065(3) -0.0015(2)

N3 0.0121(3) 0.0146(4) 0.0142(4) 0.0018(3) 0.0054(3) 0.0018(3)

C4 0.0128(4) 0.0126(4) 0.0132(4) -0.0005(3) 0.0047(3) -0.0005(3)

C5 0.0142(4) 0.0120(4) 0.0122(4) 0.0010(3) 0.0038(3) -0.0005(3)

C6 0.0132(4) 0.0168(4) 0.0174(4) 0.0002(3) 0.0051(3) -0.0016(3)

C8 0.0225(5) 0.0161(4) 0.0175(4) 0.0034(3) 0.0067(4) -0.0022(4)

C9 0.0172(4) 0.0144(4) 0.0162(4) 0.0020(3) 0.0043(3) 0.0006(3)

C7 0.0181(4) 0.0190(4) 0.0181(4) 0.0007(4) 0.0075(4) -0.0048(4)

 

_geom_special_details

;

 All esds (except the esd in the dihedral angle between two l.s. planes)

 are estimated using the full covariance matrix.  The cell esds are taken

 into account individually in the estimation of esds in distances, angles

 and torsion angles; correlations between esds in cell parameters are only

 used when they are defined by crystal symmetry.  An approximate (isotropic)

 treatment of cell esds is used for estimating esds 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

O4 N3 1.2281(11) . ?

O1 S1 1.4388(7) . ?

O2 S1 1.4292(7) . ?

S1 N2 1.6356(9) . ?

S1 C4 1.7735(10) . ?

N2 N1 1.4077(11) . ?

N1 C2 1.2791(14) . ?

C2 C1 1.4929(16) . ?

C2 C3 1.4971(15) . ?

O3 N3 1.2277(11) . ?

N3 C5 1.4725(12) . ?

C4 C9 1.3937(13) . ?

C4 C5 1.3972(13) . ?

C5 C6 1.3836(13) . ?

C6 C7 1.3954(14) . ?

C8 C7 1.3916(15) . ?

C8 C9 1.3958(14) . ?

 

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 120.16(5) . . ?

O2 S1 N2 108.32(5) . . ?

O1 S1 N2 105.58(4) . . ?

O2 S1 C4 106.84(5) . . ?

O1 S1 C4 107.68(4) . . ?

N2 S1 C4 107.74(4) . . ?

N1 N2 S1 112.40(7) . . ?

C2 N1 N2 116.15(9) . . ?

N1 C2 C1 125.50(10) . . ?

N1 C2 C3 116.64(10) . . ?

C1 C2 C3 117.86(10) . . ?

O3 N3 O4 124.90(8) . . ?

O3 N3 C5 117.30(8) . . ?

O4 N3 C5 117.75(8) . . ?

C9 C4 C5 118.36(9) . . ?

C9 C4 S1 119.30(7) . . ?

C5 C4 S1 122.25(7) . . ?

C6 C5 C4 122.59(9) . . ?

C6 C5 N3 116.71(8) . . ?

C4 C5 N3 120.65(8) . . ?

C5 C6 C7 118.33(9) . . ?

C7 C8 C9 120.64(9) . . ?

C4 C9 C8 119.85(9) . . ?

C8 C7 C6 120.21(9) . . ?

 

loop_

 _geom_hbond_atom_site_label_D

 _geom_hbond_atom_site_label_H

 _geom_hbond_atom_site_label_A

 _geom_hbond_distance_DH

 _geom_hbond_distance_HA

 _geom_hbond_distance_DA

 _geom_hbond_angle_DHA

 _geom_hbond_site_symmetry_A

N2 H2 O3  0.851(12) 2.518(13) 3.0751(11) 123.9(12) .

N2 H2 O1  0.851(12) 2.374(13) 3.1702(11) 156.0(13) 3_757

 

_diffrn_measured_fraction_theta_max    1.000

_diffrn_reflns_theta_full              29.57

_diffrn_measured_fraction_theta_full   1.000

_refine_diff_density_max    0.485

_refine_diff_density_min   -0.387

_refine_diff_density_rms    0.056