#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/55/2225588.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2225588
loop_
_publ_author_name
'Huang, Hui-Ming'
'Chen, Gen-Lin'
'Li, Min'
'Tu, Guo-Gang'
'Liu, Cheng-Mei'
_publ_section_title
;
 (2R,3R)-N-(4-Chlorophenyl)-2,3-dihydroxy-N'-(5-phenyl-1,3,4-thiadiazol-2-yl)succinamide
;
_journal_coeditor_code           IM2182
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o765
_journal_paper_doi               10.1107/S1600536810007919
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H15 Cl N4 O4 S'
_chemical_formula_moiety         'C18 H15 Cl N4 O4 S'
_chemical_formula_sum            'C18 H15 Cl N4 O4 S'
_chemical_formula_weight         418.85
_chemical_name_systematic
;
(2R,3R)-N-(4-Chlorophenyl)-2,3-dihydroxy-N'-(5-
phenyl-1,3,4-thiadiazol-2-yl)succinamide
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.3150(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   41.381(3)
_cell_length_b                   5.1744(5)
_cell_length_c                   8.7442(9)
_cell_measurement_reflns_used    2277
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.943
_cell_measurement_theta_min      2.354
_cell_volume                     1852.6(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4632
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.353
_exptl_absorpt_correction_T_max  0.9622
_exptl_absorpt_correction_T_min  0.8545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.151
_refine_ls_abs_structure_details 'Flack (1983), 863 Friedel pairs'
_refine_ls_abs_structure_Flack   0.03(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2697
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0355
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0471P)²+0.5765P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0910
_reflns_number_gt                2319
_reflns_number_total             2697
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            im2182.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               2225588
_cod_database_fobs_code          2225588
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
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_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.51651(2) 0.5674(3) 0.31490(11) 0.0776(4) Uani d . 1 . .
N N1 0.82422(6) 0.6761(7) 0.6878(3) 0.0533(8) Uani d . 1 . .
N N2 0.85606(6) 0.7102(6) 0.7553(3) 0.0510(8) Uani d . 1 . .
N N3 0.77780(5) 0.4311(5) 0.7013(3) 0.0438(7) Uani d . 1 . .
H H3B 0.7686 0.5112 0.6203 0.053 Uiso calc R 1 . .
N N4 0.64966(5) 0.5279(6) 0.6689(3) 0.0412(6) Uani d . 1 . .
H H4A 0.6589 0.6749 0.6906 0.049 Uiso calc R 1 . .
O O1 0.76958(5) 0.1304(5) 0.8778(3) 0.0567(7) Uani d . 1 . .
O O2 0.65669(5) 0.0938(5) 0.7001(3) 0.0587(6) Uani d . 1 . .
O O3 0.72236(4) 0.3604(6) 0.5396(2) 0.0508(6) Uani d . 1 . .
H H3 0.7052 0.3206 0.4860 0.076 Uiso calc R 1 . .
O O4 0.70977(5) 0.6252(4) 0.8040(2) 0.0485(6) Uani d . 1 . .
H H4 0.7120 0.6645 0.8958 0.073 Uiso calc R 1 . .
S S1 0.833503(16) 0.34609(19) 0.90607(8) 0.0471(2) Uani d . 1 . .
C C1 0.75941(7) 0.2576(6) 0.7638(3) 0.0394(8) Uani d . 1 . .
C C2 0.72451(6) 0.2352(7) 0.6839(3) 0.0404(8) Uani d . 1 . .
H H2 0.7187 0.0524 0.6681 0.048 Uiso calc R 1 . .
C C3 0.70219(6) 0.3600(7) 0.7875(3) 0.0378(6) Uani d . 1 . .
H H3A 0.7059 0.2776 0.8894 0.045 Uiso calc R 1 . .
C C4 0.66679(6) 0.3166(7) 0.7157(3) 0.0386(7) Uani d . 1 . .
C C5 0.80992(7) 0.4943(7) 0.7539(3) 0.0412(8) Uani d . 1 . .
C C6 0.86447(6) 0.5530(7) 0.8697(3) 0.0374(7) Uani d . 1 . .
C C7 0.89748(6) 0.5497(7) 0.9587(3) 0.0363(7) Uani d . 1 . .
C C8 0.92006(7) 0.7319(7) 0.9290(4) 0.0510(9) Uani d . 1 . .
H H8 0.9142 0.8595 0.8553 0.061 Uiso calc R 1 . .
C C9 0.95150(8) 0.7257(8) 1.0084(4) 0.0590(10) Uani d . 1 . .
H H9 0.9667 0.8478 0.9869 0.071 Uiso calc R 1 . .
C C10 0.96029(7) 0.5415(8) 1.1180(4) 0.0557(9) Uani d . 1 . .
H H10 0.9814 0.5391 1.1716 0.067 Uiso calc R 1 . .
C C11 0.93800(7) 0.3592(9) 1.1492(4) 0.0558(9) Uani d . 1 . .
H H11 0.9441 0.2335 1.2238 0.067 Uiso calc R 1 . .
C C12 0.90653(7) 0.3624(8) 1.0698(3) 0.0469(8) Uani d . 1 . .
H H12 0.8915 0.2389 1.0911 0.056 Uiso calc R 1 . .
C C13 0.61733(6) 0.5301(7) 0.5857(3) 0.0373(7) Uani d . 1 . .
C C14 0.60929(7) 0.7228(7) 0.4779(3) 0.0464(8) Uani d . 1 . .
H H14 0.6250 0.8437 0.4602 0.056 Uiso calc R 1 . .
C C15 0.57817(8) 0.7379(7) 0.3959(4) 0.0505(9) Uani d . 1 . .
H H15 0.5727 0.8704 0.3251 0.061 Uiso calc R 1 . .
C C16 0.55547(7) 0.5544(7) 0.4205(3) 0.0465(8) Uani d . 1 . .
C C17 0.56310(6) 0.3612(8) 0.5266(4) 0.0505(8) Uani d . 1 . .
H H17 0.5475 0.2388 0.5428 0.061 Uiso calc R 1 . .
C C18 0.59436(6) 0.3490(8) 0.6101(3) 0.0455(7) Uani d . 1 . .
H H18 0.5997 0.2183 0.6824 0.055 Uiso calc R 1 . .
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'
O O 0.0106 0.0060 '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'
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'
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
C5 N1 N2 . . 112.0(2) ?
C6 N2 N1 . . 112.6(3) ?
C1 N3 C5 . . 126.7(2) ?
C1 N3 H3B . . 116.7 ?
C5 N3 H3B . . 116.7 ?
C4 N4 C13 . . 125.5(3) ?
C4 N4 H4A . . 117.3 ?
C13 N4 H4A . . 117.3 ?
C2 O3 H3 . . 109.5 ?
C3 O4 H4 . . 109.5 ?
C5 S1 C6 . . 86.24(14) ?
O1 C1 N3 . . 123.0(3) ?
O1 C1 C2 . . 122.0(3) ?
N3 C1 C2 . . 115.0(2) ?
O3 C2 C1 . . 108.1(2) ?
O3 C2 C3 . . 111.8(3) ?
C1 C2 C3 . . 108.2(2) ?
O3 C2 H2 . . 109.6 ?
C1 C2 H2 . . 109.6 ?
C3 C2 H2 . . 109.6 ?
O4 C3 C4 . . 111.8(3) ?
O4 C3 C2 . . 109.1(2) ?
C4 C3 C2 . . 108.7(2) ?
O4 C3 H3A . . 109.0 ?
C4 C3 H3A . . 109.0 ?
C2 C3 H3A . . 109.0 ?
O2 C4 N4 . . 125.3(3) ?
O2 C4 C3 . . 118.4(3) ?
N4 C4 C3 . . 116.2(3) ?
N1 C5 N3 . . 120.3(3) ?
N1 C5 S1 . . 115.3(2) ?
N3 C5 S1 . . 124.4(3) ?
N2 C6 C7 . . 122.7(3) ?
N2 C6 S1 . . 113.92(19) ?
C7 C6 S1 . . 123.4(2) ?
C8 C7 C12 . . 119.3(2) ?
C8 C7 C6 . . 119.7(3) ?
C12 C7 C6 . . 121.0(3) ?
C7 C8 C9 . . 120.2(3) ?
C7 C8 H8 . . 119.9 ?
C9 C8 H8 . . 119.9 ?
C10 C9 C8 . . 120.3(3) ?
C10 C9 H9 . . 119.8 ?
C8 C9 H9 . . 119.8 ?
C9 C10 C11 . . 120.1(3) ?
C9 C10 H10 . . 120.0 ?
C11 C10 H10 . . 120.0 ?
C10 C11 C12 . . 120.1(3) ?
C10 C11 H11 . . 119.9 ?
C12 C11 H11 . . 119.9 ?
C11 C12 C7 . . 120.0(3) ?
C11 C12 H12 . . 120.0 ?
C7 C12 H12 . . 120.0 ?
C18 C13 C14 . . 119.7(3) ?
C18 C13 N4 . . 122.3(3) ?
C14 C13 N4 . . 118.0(3) ?
C13 C14 C15 . . 120.6(3) ?
C13 C14 H14 . . 119.7 ?
C15 C14 H14 . . 119.7 ?
C16 C15 C14 . . 119.1(3) ?
C16 C15 H15 . . 120.4 ?
C14 C15 H15 . . 120.4 ?
C17 C16 C15 . . 121.0(3) ?
C17 C16 Cl1 . . 119.6(3) ?
C15 C16 Cl1 . . 119.5(3) ?
C16 C17 C18 . . 119.6(3) ?
C16 C17 H17 . . 120.2 ?
C18 C17 H17 . . 120.2 ?
C13 C18 C17 . . 120.0(3) ?
C13 C18 H18 . . 120.0 ?
C17 C18 H18 . . 120.0 ?
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
Cl1 C16 . 1.739(3) ?
N1 C5 . 1.292(4) ?
N1 N2 . 1.375(3) ?
N2 C6 . 1.297(4) ?
N3 C1 . 1.343(4) ?
N3 C5 . 1.381(3) ?
N3 H3B . 0.8600 ?
N4 C4 . 1.335(4) ?
N4 C13 . 1.427(3) ?
N4 H4A . 0.8600 ?
O1 C1 . 1.218(3) ?
O2 C4 . 1.227(4) ?
O3 C2 . 1.410(4) ?
O3 H3 . 0.8200 ?
O4 C3 . 1.411(4) ?
O4 H4 . 0.8200 ?
S1 C5 . 1.713(3) ?
S1 C6 . 1.734(3) ?
C1 C2 . 1.515(4) ?
C2 C3 . 1.528(4) ?
C2 H2 . 0.9800 ?
C3 C4 . 1.525(3) ?
C3 H3A . 0.9800 ?
C6 C7 . 1.471(3) ?
C7 C8 . 1.379(4) ?
C7 C12 . 1.385(5) ?
C8 C9 . 1.384(4) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.363(5) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.374(5) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.384(4) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C13 C18 . 1.373(4) ?
C13 C14 . 1.380(5) ?
C14 C15 . 1.383(4) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.374(5) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.369(5) ?
C17 C18 . 1.392(4) ?
C17 H17 . 0.9300 ?
C18 H18 . 0.9300 ?
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
O3 H3 N1 4_646 0.82 1.95 2.733(3) 159
N3 H3B O3 4_656 0.86 2.35 3.061(4) 140
O4 H4 O1 4_657 0.82 2.02 2.790(3) 155
N4 H4A O2 1_565 0.86 2.17 2.951(4) 151
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 N2 C6 . . . . -0.1(4) ?
C5 N3 C1 O1 . . . . -0.5(5) ?
C5 N3 C1 C2 . . . . 178.1(3) ?
O1 C1 C2 O3 . . . . -167.3(3) ?
N3 C1 C2 O3 . . . . 14.1(4) ?
O1 C1 C2 C3 . . . . 71.5(4) ?
N3 C1 C2 C3 . . . . -107.1(3) ?
O3 C2 C3 O4 . . . . -55.8(3) ?
C1 C2 C3 O4 . . . . 63.0(3) ?
O3 C2 C3 C4 . . . . 66.4(3) ?
C1 C2 C3 C4 . . . . -174.8(3) ?
C13 N4 C4 O2 . . . . -3.5(5) ?
C13 N4 C4 C3 . . . . 173.6(2) ?
O4 C3 C4 O2 . . . . -177.4(3) ?
C2 C3 C4 O2 . . . . 62.1(4) ?
O4 C3 C4 N4 . . . . 5.3(3) ?
C2 C3 C4 N4 . . . . -115.3(3) ?
N2 N1 C5 N3 . . . . -179.7(3) ?
N2 N1 C5 S1 . . . . 0.4(4) ?
C1 N3 C5 N1 . . . . -176.0(3) ?
C1 N3 C5 S1 . . . . 3.9(5) ?
C6 S1 C5 N1 . . . . -0.4(3) ?
C6 S1 C5 N3 . . . . 179.6(3) ?
N1 N2 C6 C7 . . . . 179.1(3) ?
N1 N2 C6 S1 . . . . -0.2(4) ?
C5 S1 C6 N2 . . . . 0.4(3) ?
C5 S1 C6 C7 . . . . -179.0(3) ?
N2 C6 C7 C8 . . . . 5.0(5) ?
S1 C6 C7 C8 . . . . -175.8(2) ?
N2 C6 C7 C12 . . . . -173.5(3) ?
S1 C6 C7 C12 . . . . 5.8(4) ?
C12 C7 C8 C9 . . . . 0.6(5) ?
C6 C7 C8 C9 . . . . -177.9(3) ?
C7 C8 C9 C10 . . . . -0.8(6) ?
C8 C9 C10 C11 . . . . 0.6(6) ?
C9 C10 C11 C12 . . . . -0.2(6) ?
C10 C11 C12 C7 . . . . 0.0(6) ?
C8 C7 C12 C11 . . . . -0.2(5) ?
C6 C7 C12 C11 . . . . 178.3(3) ?
C4 N4 C13 C18 . . . . 34.5(4) ?
C4 N4 C13 C14 . . . . -145.7(3) ?
C18 C13 C14 C15 . . . . 1.1(5) ?
N4 C13 C14 C15 . . . . -178.7(3) ?
C13 C14 C15 C16 . . . . -1.5(5) ?
C14 C15 C16 C17 . . . . 1.2(5) ?
C14 C15 C16 Cl1 . . . . -178.6(2) ?
C15 C16 C17 C18 . . . . -0.5(5) ?
Cl1 C16 C17 C18 . . . . 179.4(3) ?
C14 C13 C18 C17 . . . . -0.2(5) ?
N4 C13 C18 C17 . . . . 179.5(3) ?
C16 C17 C18 C13 . . . . -0.1(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744625
