##############################################################################
# #
# This CIF contains the data in a paper accepted for publication in #
# Acta Crystallographica Section E. It conforms to the requirements of #
# Notes for Authors for Acta Crystallographica Section E, and has been #
# peer reviewed under the auspices of the IUCr Commission on Journals. #
# #
# Full details of the Crystallographic Information File format #
# are given in the paper "The Crystallographic Information File (CIF): #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H. #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. #
# #
# The current version of the core CIF dictionary is obtainable from #
# ftp://ftp.iucr.org/pub/cif_core.dic. #
# #
# Software is freely available for graphical display of the structure(s) #
# in this CIF. For information consult the CIF software page #
# http://www.iucr.org/resources/cif/software. #
# #
# This file may be used for bona fide research purposes within the #
# scientific community so long as proper attribution is given to the journal #
# article from which it was obtained. #
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##############################################################################
data_global
_audit_creation_method 'form.cif (version 2.0)'
_journal_data_validation_number ?
_journal_date_recd_electronic 2011-04-14
_journal_date_accepted 2011-04-19
_journal_name_full 'Acta Crystallographica, Section E'
_journal_year 2011
_journal_volume 67
_journal_issue 5
_journal_page_first o1218
_journal_page_last o1218
_journal_paper_category QO
_journal_coeditor_code DN2677
_publ_contact_author_name 'Hassan, Ibrahim N.'
_publ_contact_author_address
;
School of Chemical Sciences and Food Technology
Universiti Kebangsaan Malaysia
43600 Bangi Selangor
Malaysia
;
_publ_contact_author_email ibnhum@gmail.com
_publ_contact_author_fax '+603 89215410'
_publ_contact_author_phone '+603 89213980'
_publ_section_title
;
2-Bromo-N-(dibenzylcarbamothioyl)benzamide
;
loop_
_publ_author_name
_publ_author_address
'Nasir, Mohd Faizal Md'
;
Fuel Cell Institute
Universiti Kebangsaan Malaysia
UKM 43600 Bangi Selangor
Malaysia
;
'Hassan, Ibrahim N.'
;
Fuel Cell Institute
Universiti Kebangsaan Malaysia
UKM 43600 Bangi Selangor
Malaysia
;
'Wan Daud, Wan Ramli'
;
Department of Chemical and Process Engineering
Faculty of Engineering
Universiti Kebangsaan Malaysia
UKM 43600 Bangi Selangor
Malaysia
and Fuel Cell Institute
Universiti Kebangsaan Malaysia
UKM 43600 Bangi Selangor
Malaysia
;
'Yamin, Bohari M.'
;
School of Chemical Sciences and Food Technology
Faculty of Science and Technology
Universiti Kebangsaan Malaysia
UKM 43600 Bangi Selangor
Malaysia
;
'Kassim, Mohammad B.'
;
School of Chemical Sciences and Food Technology
Faculty of Science and Technology
Universiti Kebangsaan Malaysia
UKM 43600 Bangi Selangor
Malaysia
and Fuel Cell Institute
Universiti Kebangsaan Malaysia
UKM 43600 Bangi Selangor
Malaysia
;
data_I
_audit_creation_method SHELXL97
_chemical_name_systematic
;
2-Bromo-N-(dibenzylcarbamothioyl)benzamide
;
_chemical_name_common ?
_chemical_formula_moiety 'C22 H19 Br N2 O S'
_chemical_formula_sum 'C22 H19 Br N2 O S'
_chemical_formula_iupac 'C22 H19 Br N2 O S'
_chemical_formula_weight 439.36
_chemical_melting_point ?
_symmetry_cell_setting tetragonal
_symmetry_space_group_name_H-M 'P 43'
_symmetry_space_group_name_Hall 'P 4cw'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x, z+3/4'
'-x, -y, z+1/2'
'y, -x, z+1/4'
_cell_length_a 12.2833(16)
_cell_length_b 12.2833(16)
_cell_length_c 14.002(4)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 2112.6(7)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 2531
_cell_measurement_theta_min 1.66
_cell_measurement_theta_max 28.35
_cell_measurement_temperature 273(2)
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.35
_exptl_crystal_size_mid 0.31
_exptl_crystal_size_min 0.23
_exptl_crystal_density_diffrn 1.381
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 896
_exptl_absorpt_coefficient_mu 2.058
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Sheldrick, 2000)'
_exptl_absorpt_correction_T_min 0.5328
_exptl_absorpt_correction_T_max 0.6490
_exptl_special_details
;
;
_diffrn_ambient_temperature 273(2)
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method \w
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 15683
_diffrn_reflns_av_R_equivalents 0.0638
_diffrn_reflns_av_sigmaI/netI 0.0941
_diffrn_reflns_theta_min 1.66
_diffrn_reflns_theta_max 28.35
_diffrn_reflns_theta_full 28.35
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 16
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_limit_l_max 18
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_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.
;
_reflns_number_total 5217
_reflns_number_gt 2506
_reflns_threshold_expression I>2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.1280
_refine_ls_R_factor_gt 0.0498
_refine_ls_wR_factor_gt 0.0992
_refine_ls_wR_factor_ref 0.1184
_refine_ls_goodness_of_fit_ref 0.933
_refine_ls_restrained_S_all 0.933
_refine_ls_number_reflns 5217
_refine_ls_number_parameters 244
_refine_ls_number_restraints 1
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0418P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.570
_refine_diff_density_min -0.198
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details 'Flack (1983), with 2474 Friedel pairs'
_refine_ls_abs_structure_Flack -0.001(11)
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'
_computing_data_collection 'SMART (Bruker, 2000)'
_computing_cell_refinement 'SAINT (Bruker, 2000)'
_computing_data_reduction 'SAINT (Bruker, 2000)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia,
1997) and
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON
(Spek, 2009)
;
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.20156(4) 0.59332(4) 0.23207(5) 0.0975(2) Uani d . 1 1 . .
S S1 0.48743(15) 0.81061(10) -0.01270(10) 0.1136(5) Uani d . 1 1 . .
O O1 0.5373(2) 0.6765(2) 0.2480(2) 0.0656(7) Uani d . 1 1 . .
N N1 0.4138(2) 0.6950(2) 0.1306(2) 0.0552(8) Uani d . 1 1 . .
H H1A 0.3584 0.6663 0.1027 0.066 Uiso d R 1 1 . .
N N2 0.4512(3) 0.8761(3) 0.1662(2) 0.0642(9) Uani d . 1 1 . .
C C1 0.3189(3) 0.4915(3) 0.2306(3) 0.0685(11) Uani d . 1 1 . .
C C2 0.2938(5) 0.3838(5) 0.2467(4) 0.0973(16) Uani d . 1 1 . .
H H2A 0.2218 0.3628 0.2562 0.117 Uiso calc R 1 1 . .
C C3 0.3751(6) 0.3079(4) 0.2485(4) 0.1067(18) Uani d . 1 1 . .
H H3A 0.3579 0.2349 0.2578 0.128 Uiso calc R 1 1 . .
C C4 0.4787(5) 0.3375(4) 0.2371(5) 0.0959(15) Uani d . 1 1 . .
H H4A 0.5333 0.2851 0.2400 0.115 Uiso calc R 1 1 . .
C C5 0.5061(4) 0.4451(3) 0.2210(3) 0.0684(11) Uani d . 1 1 . .
H H5A 0.5786 0.4647 0.2126 0.082 Uiso calc R 1 1 . .
C C6 0.4249(3) 0.5240(3) 0.2174(3) 0.0567(10) Uani d . 1 1 . .
C C7 0.4632(3) 0.6395(3) 0.2022(3) 0.0517(10) Uani d . 1 1 . .
C C8 0.4501(4) 0.7972(3) 0.1011(3) 0.0638(11) Uani d . 1 1 . .
C C9 0.3979(4) 0.8690(3) 0.2597(3) 0.0694(12) Uani d . 1 1 . .
H H9A 0.4523 0.8763 0.3095 0.083 Uiso calc R 1 1 . .
H H9B 0.3645 0.7979 0.2663 0.083 Uiso calc R 1 1 . .
C C10 0.3114(4) 0.9563(4) 0.2731(4) 0.0733(13) Uani d . 1 1 . .
C C11 0.2355(5) 0.9757(5) 0.2031(5) 0.120(2) Uani d . 1 1 . .
H H11A 0.2383 0.9383 0.1454 0.144 Uiso calc R 1 1 . .
C C12 0.1542(6) 1.0525(7) 0.2202(8) 0.156(3) Uani d . 1 1 . .
H H12A 0.1035 1.0672 0.1726 0.187 Uiso calc R 1 1 . .
C C13 0.1477(6) 1.1055(6) 0.3037(9) 0.137(3) Uani d . 1 1 . .
H H13A 0.0923 1.1556 0.3145 0.164 Uiso calc R 1 1 . .
C C14 0.2215(7) 1.0855(5) 0.3709(6) 0.116(2) Uani d . 1 1 . .
H H14A 0.2171 1.1222 0.4289 0.139 Uiso calc R 1 1 . .
C C15 0.3049(5) 1.0111(4) 0.3565(4) 0.0841(14) Uani d . 1 1 . .
H H15A 0.3562 0.9991 0.4041 0.101 Uiso calc R 1 1 . .
C C16 0.5113(4) 0.9773(3) 0.1497(4) 0.0799(13) Uani d . 1 1 . .
H H16A 0.4655 1.0387 0.1664 0.096 Uiso calc R 1 1 . .
H H16B 0.5292 0.9831 0.0824 0.096 Uiso calc R 1 1 . .
C C17 0.6145(4) 0.9818(3) 0.2075(4) 0.0722(13) Uani d . 1 1 . .
C C18 0.6297(6) 1.0599(5) 0.2746(5) 0.117(2) Uani d . 1 1 . .
H H18A 0.5758 1.1119 0.2839 0.140 Uiso calc R 1 1 . .
C C19 0.7213(7) 1.0642(6) 0.3286(7) 0.161(4) Uani d . 1 1 . .
H H19A 0.7279 1.1164 0.3763 0.193 Uiso calc R 1 1 . .
C C20 0.8018(6) 0.9934(7) 0.3131(6) 0.134(3) Uani d . 1 1 . .
H H20A 0.8672 1.0007 0.3459 0.160 Uiso calc R 1 1 . .
C C21 0.7890(5) 0.9132(6) 0.2515(7) 0.132(3) Uani d . 1 1 . .
H H21A 0.8432 0.8609 0.2443 0.158 Uiso calc R 1 1 . .
C C22 0.6946(5) 0.9072(5) 0.1976(4) 0.1103(19) Uani d . 1 1 . .
H H22A 0.6861 0.8508 0.1539 0.132 Uiso calc R 1 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br1 0.0739(3) 0.1215(4) 0.0970(4) -0.0048(3) 0.0148(3) 0.0028(4)
S1 0.1990(16) 0.0888(8) 0.0531(7) -0.0186(9) 0.0167(10) 0.0149(8)
O1 0.0769(17) 0.0579(16) 0.0620(19) -0.0059(14) -0.0219(16) 0.0042(14)
N1 0.064(2) 0.056(2) 0.0457(18) -0.0031(16) -0.0102(15) 0.0076(14)
N2 0.082(2) 0.050(2) 0.061(2) 0.0049(18) -0.0021(18) 0.0128(18)
C1 0.083(3) 0.072(3) 0.051(2) -0.016(2) 0.003(3) 0.007(2)
C2 0.108(4) 0.097(4) 0.087(4) -0.042(4) 0.011(3) 0.011(3)
C3 0.156(6) 0.066(3) 0.098(4) -0.026(4) -0.007(4) 0.014(3)
C4 0.134(5) 0.063(3) 0.090(4) 0.012(3) -0.004(4) 0.019(3)
C5 0.092(3) 0.057(2) 0.056(3) 0.000(2) -0.005(2) 0.013(2)
C6 0.075(3) 0.055(2) 0.041(2) -0.009(2) -0.0036(19) 0.0091(18)
C7 0.060(2) 0.056(2) 0.039(2) 0.007(2) -0.0019(18) 0.0025(17)
C8 0.079(3) 0.054(3) 0.058(3) 0.001(2) -0.009(2) 0.013(2)
C9 0.076(3) 0.065(3) 0.067(3) 0.006(2) -0.003(2) 0.004(2)
C10 0.070(3) 0.056(3) 0.094(4) 0.001(2) -0.003(3) -0.004(2)
C11 0.110(4) 0.113(4) 0.135(6) 0.034(4) -0.056(4) -0.034(4)
C12 0.117(5) 0.139(6) 0.212(10) 0.046(5) -0.072(6) -0.031(7)
C13 0.082(5) 0.090(5) 0.237(10) 0.007(4) 0.039(6) -0.006(6)
C14 0.143(6) 0.065(4) 0.140(6) -0.003(4) 0.042(5) -0.017(4)
C15 0.099(4) 0.058(3) 0.095(4) -0.002(3) 0.009(3) -0.009(3)
C16 0.109(4) 0.049(3) 0.082(3) -0.004(3) 0.005(3) 0.013(2)
C17 0.080(3) 0.048(2) 0.089(4) 0.000(2) 0.011(3) -0.002(2)
C18 0.129(5) 0.079(4) 0.143(5) 0.021(4) -0.033(4) -0.041(4)
C19 0.125(6) 0.128(5) 0.229(10) 0.021(5) -0.057(6) -0.094(6)
C20 0.095(5) 0.148(6) 0.159(7) -0.013(5) -0.022(4) -0.042(5)
C21 0.087(4) 0.143(6) 0.166(7) 0.027(4) 0.004(5) -0.039(6)
C22 0.105(4) 0.110(4) 0.116(5) 0.013(4) 0.007(4) -0.041(3)
_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C1 . 1.909(4) ?
S1 C8 . 1.666(4) ?
O1 C7 . 1.203(4) ?
N1 C7 . 1.356(5) ?
N1 C8 . 1.396(5) ?
N1 H1A . 0.8602 ?
N2 C8 . 1.330(5) ?
N2 C16 . 1.464(6) ?
N2 C9 . 1.467(5) ?
C1 C6 . 1.375(5) ?
C1 C2 . 1.376(6) ?
C2 C3 . 1.367(8) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.334(8) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.382(6) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.392(5) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.509(5) ?
C9 C10 . 1.521(6) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C15 . 1.350(7) ?
C10 C11 . 1.372(7) ?
C11 C12 . 1.394(10) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.341(11) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.329(11) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.388(8) ?
C14 H14A . 0.9300 ?
C15 H15A . 0.9300 ?
C16 C17 . 1.505(7) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 C22 . 1.352(7) ?
C17 C18 . 1.355(7) ?
C18 C19 . 1.356(9) ?
C18 H18A . 0.9300 ?
C19 C20 . 1.334(9) ?
C19 H19A . 0.9300 ?
C20 C21 . 1.319(10) ?
C20 H20A . 0.9300 ?
C21 C22 . 1.386(9) ?
C21 H21A . 0.9300 ?
C22 H22A . 0.9300 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 N1 C8 . . 121.9(3) ?
C7 N1 H1A . . 119.0 ?
C8 N1 H1A . . 119.2 ?
C8 N2 C16 . . 121.0(4) ?
C8 N2 C9 . . 124.3(3) ?
C16 N2 C9 . . 114.6(4) ?
C6 C1 C2 . . 120.9(4) ?
C6 C1 Br1 . . 121.7(3) ?
C2 C1 Br1 . . 117.3(4) ?
C3 C2 C1 . . 119.7(5) ?
C3 C2 H2A . . 120.2 ?
C1 C2 H2A . . 120.2 ?
C4 C3 C2 . . 120.6(5) ?
C4 C3 H3A . . 119.7 ?
C2 C3 H3A . . 119.7 ?
C3 C4 C5 . . 120.8(5) ?
C3 C4 H4A . . 119.6 ?
C5 C4 H4A . . 119.6 ?
C4 C5 C6 . . 119.9(5) ?
C4 C5 H5A . . 120.1 ?
C6 C5 H5A . . 120.1 ?
C1 C6 C5 . . 118.1(4) ?
C1 C6 C7 . . 126.0(4) ?
C5 C6 C7 . . 115.9(4) ?
O1 C7 N1 . . 122.9(3) ?
O1 C7 C6 . . 121.1(3) ?
N1 C7 C6 . . 115.9(3) ?
N2 C8 N1 . . 117.1(3) ?
N2 C8 S1 . . 125.5(3) ?
N1 C8 S1 . . 117.4(3) ?
N2 C9 C10 . . 112.3(4) ?
N2 C9 H9A . . 109.1 ?
C10 C9 H9A . . 109.1 ?
N2 C9 H9B . . 109.1 ?
C10 C9 H9B . . 109.1 ?
H9A C9 H9B . . 107.9 ?
C15 C10 C11 . . 119.4(5) ?
C15 C10 C9 . . 119.9(5) ?
C11 C10 C9 . . 120.6(5) ?
C10 C11 C12 . . 118.7(6) ?
C10 C11 H11A . . 120.6 ?
C12 C11 H11A . . 120.6 ?
C13 C12 C11 . . 121.4(7) ?
C13 C12 H12A . . 119.3 ?
C11 C12 H12A . . 119.3 ?
C14 C13 C12 . . 119.1(7) ?
C14 C13 H13A . . 120.4 ?
C12 C13 H13A . . 120.4 ?
C13 C14 C15 . . 121.4(7) ?
C13 C14 H14A . . 119.3 ?
C15 C14 H14A . . 119.3 ?
C10 C15 C14 . . 119.9(6) ?
C10 C15 H15A . . 120.1 ?
C14 C15 H15A . . 120.1 ?
N2 C16 C17 . . 111.8(4) ?
N2 C16 H16A . . 109.3 ?
C17 C16 H16A . . 109.3 ?
N2 C16 H16B . . 109.3 ?
C17 C16 H16B . . 109.3 ?
H16A C16 H16B . . 107.9 ?
C22 C17 C18 . . 116.8(5) ?
C22 C17 C16 . . 122.2(5) ?
C18 C17 C16 . . 121.0(5) ?
C17 C18 C19 . . 121.9(6) ?
C17 C18 H18A . . 119.1 ?
C19 C18 H18A . . 119.1 ?
C20 C19 C18 . . 119.9(7) ?
C20 C19 H19A . . 120.0 ?
C18 C19 H19A . . 120.0 ?
C21 C20 C19 . . 120.3(7) ?
C21 C20 H20A . . 119.8 ?
C19 C20 H20A . . 119.8 ?
C20 C21 C22 . . 119.7(6) ?
C20 C21 H21A . . 120.2 ?
C22 C21 H21A . . 120.2 ?
C17 C22 C21 . . 121.1(5) ?
C17 C22 H22A . . 119.4 ?
C21 C22 H22A . . 119.4 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1A Br1 . 0.86 2.79 3.220(3) 112.5
N1 H1A O1 2_654 0.86 2.20 2.903(4) 138.7
_iucr_refine_instructions_details
;
TITL I P4(3) R = 0.05
CELL 0.71073 12.2833 12.2833 14.0020 90.000 90.000 90.000
ZERR 1.00 0.0016 0.0016 0.0040 0.000 0.000 0.000
LATT -1
SYMM - Y, X, 3/4 + Z
SYMM - X, - Y, 1/2 + Z
SYMM Y, - X, 1/4 + Z
SFAC C H BR N O S
UNIT 88 76 4 8 4 4
MERG 2
EQIV $1 -y+1, x, z-1/4
HTAB N1 Br1
HTAB N1 O1_$1
MPLA C1 C2 C3 C4 C5 C6
MPLA S1 N1 N2 C8
MPLA C10 C11 C12 C13 C14 C15
MPLA C17 C18 C19 C20 C21 C22
FMAP 2
PLAN 20
ACTA
BOND $H
L.S. 5
TEMP 0.00
WGHT 0.041500
FVAR 1.02569
BR1 3 0.201556 0.593323 0.232069 11.00000 0.07396 0.12156 =
0.09703 0.00282 0.01479 -0.00478
S1 6 0.487435 0.810610 -0.012701 11.00000 0.19900 0.08878 =
0.05315 0.01491 0.01669 -0.01857
O1 5 0.537337 0.676509 0.247965 11.00000 0.07686 0.05789 =
0.06197 0.00419 -0.02187 -0.00586
N1 4 0.413753 0.694961 0.130620 11.00000 0.06360 0.05645 =
0.04569 0.00761 -0.01025 -0.00314
AFIX 3
H1A 2 0.358353 0.666261 0.102720 11.00000 -1.20000
AFIX 0
N2 4 0.451247 0.876099 0.166164 11.00000 0.08211 0.04990 =
0.06066 0.01276 -0.00206 0.00494
C1 1 0.318865 0.491458 0.230603 11.00000 0.08262 0.07230 =
0.05050 0.00736 0.00340 -0.01618
C2 1 0.293759 0.383803 0.246659 11.00000 0.10786 0.09696 =
0.08699 0.01097 0.01088 -0.04190
AFIX 43
H2A 2 0.221827 0.362836 0.256209 11.00000 -1.20000
AFIX 0
C3 1 0.375050 0.307868 0.248501 11.00000 0.15577 0.06610 =
0.09823 0.01384 -0.00700 -0.02616
AFIX 43
H3A 2 0.357936 0.234879 0.257792 11.00000 -1.20000
AFIX 0
C4 1 0.478746 0.337493 0.237091 11.00000 0.13442 0.06311 =
0.09019 0.01940 -0.00439 0.01237
AFIX 43
H4A 2 0.533299 0.285097 0.239994 11.00000 -1.20000
AFIX 0
C5 1 0.506074 0.445058 0.221015 11.00000 0.09211 0.05734 =
0.05569 0.01319 -0.00548 -0.00038
AFIX 43
H5A 2 0.578571 0.464667 0.212595 11.00000 -1.20000
AFIX 0
C6 1 0.424864 0.524048 0.217445 11.00000 0.07459 0.05490 =
0.04065 0.00905 -0.00360 -0.00913
C7 1 0.463199 0.639465 0.202223 11.00000 0.06029 0.05617 =
0.03861 0.00248 -0.00189 0.00704
C8 1 0.450113 0.797227 0.101094 11.00000 0.07926 0.05383 =
0.05835 0.01305 -0.00856 0.00078
C9 1 0.397879 0.869016 0.259712 11.00000 0.07563 0.06520 =
0.06744 0.00398 -0.00297 0.00566
AFIX 23
H9A 2 0.452321 0.876344 0.309480 11.00000 -1.20000
H9B 2 0.364457 0.797868 0.266333 11.00000 -1.20000
AFIX 0
C10 1 0.311369 0.956335 0.273066 11.00000 0.07019 0.05609 =
0.09364 -0.00400 -0.00311 0.00127
C11 1 0.235538 0.975692 0.203108 11.00000 0.11038 0.11342 =
0.13506 -0.03412 -0.05571 0.03365
AFIX 43
H11A 2 0.238330 0.938294 0.145408 11.00000 -1.20000
AFIX 0
C12 1 0.154247 1.052470 0.220169 11.00000 0.11662 0.13936 =
0.21214 -0.03140 -0.07162 0.04625
AFIX 43
H12A 2 0.103479 1.067218 0.172623 11.00000 -1.20000
AFIX 0
C13 1 0.147700 1.105527 0.303707 11.00000 0.08206 0.09048 =
0.23711 -0.00556 0.03870 0.00703
AFIX 43
H13A 2 0.092281 1.155637 0.314457 11.00000 -1.20000
AFIX 0
C14 1 0.221470 1.085539 0.370932 11.00000 0.14302 0.06515 =
0.14040 -0.01663 0.04227 -0.00314
AFIX 43
H14A 2 0.217077 1.122210 0.428912 11.00000 -1.20000
AFIX 0
C15 1 0.304897 1.011144 0.356476 11.00000 0.09895 0.05837 =
0.09490 -0.00877 0.00908 -0.00195
AFIX 43
H15A 2 0.356233 0.999064 0.404131 11.00000 -1.20000
AFIX 0
C16 1 0.511343 0.977281 0.149653 11.00000 0.10934 0.04888 =
0.08159 0.01265 0.00526 -0.00432
AFIX 23
H16A 2 0.465531 1.038718 0.166362 11.00000 -1.20000
H16B 2 0.529176 0.983105 0.082360 11.00000 -1.20000
AFIX 0
C17 1 0.614525 0.981815 0.207506 11.00000 0.07956 0.04841 =
0.08853 -0.00247 0.01101 -0.00033
C18 1 0.629678 1.059853 0.274577 11.00000 0.12867 0.07863 =
0.14327 -0.04151 -0.03310 0.02131
AFIX 43
H18A 2 0.575761 1.111941 0.283867 11.00000 -1.20000
AFIX 0
C19 1 0.721265 1.064156 0.328558 11.00000 0.12460 0.12824 =
0.22934 -0.09365 -0.05750 0.02090
AFIX 43
H19A 2 0.727937 1.116365 0.376303 11.00000 -1.20000
AFIX 0
C20 1 0.801789 0.993393 0.313084 11.00000 0.09454 0.14758 =
0.15859 -0.04245 -0.02167 -0.01298
AFIX 43
H20A 2 0.867219 1.000680 0.345887 11.00000 -1.20000
AFIX 0
C21 1 0.789019 0.913183 0.251497 11.00000 0.08685 0.14291 =
0.16642 -0.03937 0.00421 0.02655
AFIX 43
H21A 2 0.843155 0.860901 0.244246 11.00000 -1.20000
AFIX 0
C22 1 0.694568 0.907151 0.197630 11.00000 0.10484 0.11005 =
0.11607 -0.04112 0.00660 0.01307
AFIX 43
H22A 2 0.686110 0.850762 0.153934 11.00000 -1.20000
HKLF 4
REM I P4(3) R = 0.05
REM R1 = 0.0498 for 2506 Fo > 4sig(Fo) and 0.1280 for all 5217 data
REM 244 parameters refined using 1 restraints
END
WGHT 0.0417 0.0000
REM Highest difference peak 0.570, deepest hole -0.199, 1-sigma level 0.045
Q1 1 0.2200 0.6204 0.2939 11.00000 0.05 0.41
Q2 1 0.2019 0.6648 0.2672 11.00000 0.05 0.37
Q3 1 0.2379 0.6454 0.1831 11.00000 0.05 0.30
Q4 1 0.2816 0.5880 0.2207 11.00000 0.05 0.24
Q5 1 0.3252 1.2027 0.4797 11.00000 0.05 0.16
Q6 1 0.4582 0.8523 -0.0574 11.00000 0.05 0.15
Q7 1 0.3943 0.6688 0.0692 11.00000 0.05 0.15
Q8 1 0.4733 0.6391 0.1319 11.00000 0.05 0.14
Q9 1 0.2579 0.3485 0.2283 11.00000 0.05 0.14
Q10 1 0.7390 0.9140 0.2339 11.00000 0.05 0.14
Q11 1 0.4434 0.5247 0.2341 11.00000 0.05 0.13
Q12 1 0.4196 0.8539 0.0083 11.00000 0.05 0.13
Q13 1 0.5502 0.8238 -0.0018 11.00000 0.05 0.13
Q14 1 0.5454 0.6603 0.1842 11.00000 0.05 0.13
Q15 1 0.6918 1.0904 0.2207 11.00000 0.05 0.13
Q16 1 0.5183 1.0232 0.3241 11.00000 0.05 0.13
Q17 1 0.3313 0.3506 0.2484 11.00000 0.05 0.13
Q18 1 0.4579 0.4415 0.2343 11.00000 0.05 0.13
Q19 1 0.6040 1.0687 0.2120 11.00000 0.05 0.12
Q20 1 0.8450 0.9955 0.3326 11.00000 0.05 0.12
;