#------------------------------------------------------------------------------
#$Date: 2022-10-14 03:35:35 +0300 (Fri, 14 Oct 2022) $
#$Revision: 278576 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/89/7158927.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7158927
loop_
_publ_author_name
'Dong, Zhi-Bing'
'Xu, Xiao-Hu'
_publ_section_title
;
 Iodine promoted cyclization of N,N'-diphenylthiocarbamides with
 enaminones：a protocol for the synthesis of poly-substituted
 2-iminothiazolines
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01477G
_journal_year                    2022
_chemical_formula_moiety         'C22 H16 N2 O S'
_chemical_formula_sum            'C22 H16 N2 O S'
_chemical_formula_weight         356.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2bks90
_audit_creation_date             2022-03-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-03-25 deposited with the CCDC.	2022-10-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.110(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.8239(14)
_cell_length_b                   15.770(4)
_cell_length_c                   9.954(3)
_cell_measurement_reflns_used    2833
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.89
_cell_measurement_theta_min      2.44
_cell_volume                     905.1(4)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_av_unetI/netI     0.0674
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10105
_diffrn_reflns_point_group_measured_fraction_full 0.863
_diffrn_reflns_point_group_measured_fraction_max 0.864
_diffrn_reflns_theta_full        25.046
_diffrn_reflns_theta_max         25.046
_diffrn_reflns_theta_min         2.437
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6691
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 747 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2760
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0330P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0886
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    0.735
_reflns_Friedel_fraction_max     0.735
_reflns_number_gt                2037
_reflns_number_total             2760
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01477g2.cif
_cod_data_source_block           0324dzb_0m
_cod_original_cell_volume        905.0(4)
_cod_database_code               7158927
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F),
 C00G(H00G), C00H(H00H), C00I(H00I), C00K(H00K), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.5735(2) 0.30766(8) 0.27648(13) 0.0478(4) Uani 1 1 d . . . . .
O002 O 0.4477(6) 0.4887(2) 0.2095(3) 0.0556(10) Uani 1 1 d . . . . .
N003 N 0.6918(7) 0.1625(3) 0.4257(4) 0.0479(11) Uani 1 1 d . . . . .
N004 N 0.5000(7) 0.2726(2) 0.5199(4) 0.0454(10) Uani 1 1 d . . . . .
C005 C 0.7967(8) 0.1285(3) 0.3175(5) 0.0410(12) Uani 1 1 d . . . . .
C006 C 0.3648(8) 0.4642(3) 0.3091(5) 0.0429(12) Uani 1 1 d . . . . .
C007 C 0.6033(8) 0.2364(3) 0.4152(4) 0.0403(12) Uani 1 1 d . . . . .
C008 C 0.2150(8) 0.5199(3) 0.3816(5) 0.0402(12) Uani 1 1 d . . . . .
C009 C 0.7120(9) 0.0533(3) 0.2580(5) 0.0508(13) Uani 1 1 d . . . . .
H009 H 0.582906 0.027733 0.286143 0.061 Uiso 1 1 calc R . . . .
C00A C 0.4899(9) 0.2279(3) 0.6448(4) 0.0412(12) Uani 1 1 d . . . . .
C00B C 0.0233(9) 0.4901(3) 0.4343(5) 0.0504(14) Uani 1 1 d . . . . .
H00B H -0.021375 0.433686 0.421481 0.060 Uiso 1 1 calc R . . . .
C00C C 1.0986(9) 0.1263(4) 0.1762(5) 0.0569(14) Uani 1 1 d . . . . .
H00C H 1.230041 0.150708 0.149234 0.068 Uiso 1 1 calc R . . . .
C00D C 0.2736(8) 0.6049(3) 0.3961(5) 0.0469(13) Uani 1 1 d . . . . .
H00D H 0.398030 0.626093 0.357247 0.056 Uiso 1 1 calc R . . . .
C00E C 0.6625(10) 0.1877(4) 0.8654(6) 0.0636(16) Uani 1 1 d . . . . .
H00E H 0.787639 0.189253 0.934624 0.076 Uiso 1 1 calc R . . . .
C00F C 0.8177(11) 0.0159(4) 0.1574(6) 0.0629(16) Uani 1 1 d . . . . .
H00F H 0.757905 -0.033952 0.116685 0.076 Uiso 1 1 calc R . . . .
C00G C 0.4704(10) 0.1419(3) 0.8821(5) 0.0571(15) Uani 1 1 d . . . . .
H00G H 0.464459 0.112668 0.962734 0.069 Uiso 1 1 calc R . . . .
C00H C 0.6733(9) 0.2320(3) 0.7462(5) 0.0558(14) Uani 1 1 d . . . . .
H00H H 0.803651 0.263983 0.735591 0.067 Uiso 1 1 calc R . . . .
C00I C 0.9915(8) 0.1646(3) 0.2757(5) 0.0492(14) Uani 1 1 d . . . . .
H00I H 1.050788 0.214936 0.314997 0.059 Uiso 1 1 calc R . . . .
C00J C 0.4217(7) 0.3801(3) 0.3655(5) 0.0409(12) Uani 1 1 d . . . . .
C00K C 0.2969(9) 0.1824(4) 0.6613(5) 0.0579(15) Uani 1 1 d . . . . .
H00K H 0.171552 0.180736 0.592234 0.069 Uiso 1 1 calc R . . . .
C00L C 1.0115(11) 0.0524(4) 0.1171(5) 0.0634(16) Uani 1 1 d . . . . .
H00L H 1.083365 0.026916 0.049831 0.076 Uiso 1 1 calc R . . . .
C00M C 0.4043(8) 0.3507(3) 0.4907(5) 0.0438(13) Uani 1 1 d . . . . .
H00M H 0.332260 0.381385 0.552842 0.053 Uiso 1 1 calc R . . . .
C00N C 0.1496(10) 0.6575(4) 0.4669(6) 0.0611(15) Uani 1 1 d . . . . .
H00N H 0.190680 0.714364 0.477280 0.073 Uiso 1 1 calc R . . . .
C00O C 0.2876(10) 0.1387(4) 0.7812(6) 0.0634(15) Uani 1 1 d . . . . .
H00O H 0.156456 0.107341 0.792523 0.076 Uiso 1 1 calc R . . . .
C00P C -0.0358(10) 0.6270(4) 0.5232(6) 0.0663(17) Uani 1 1 d . . . . .
H00P H -0.117439 0.662892 0.573556 0.080 Uiso 1 1 calc R . . . .
C00Q C -0.1017(9) 0.5434(4) 0.5055(5) 0.0623(16) Uani 1 1 d . . . . .
H00Q H -0.229993 0.523248 0.541631 0.075 Uiso 1 1 calc R . . . .
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'
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
C00J S001 C007 91.2(2) . . ?
C007 N003 C005 119.8(4) . . ?
C007 N004 C00A 121.3(4) . . ?
C00M N004 C007 114.5(4) . . ?
C00M N004 C00A 124.1(4) . . ?
C009 C005 N003 118.9(5) . . ?
C00I C005 N003 122.2(4) . . ?
C00I C005 C009 118.8(5) . . ?
O002 C006 C008 122.0(4) . . ?
O002 C006 C00J 120.3(4) . . ?
C00J C006 C008 117.7(4) . . ?
N003 C007 S001 129.8(4) . . ?
N003 C007 N004 121.6(4) . . ?
N004 C007 S001 108.5(3) . . ?
C00B C008 C006 122.8(4) . . ?
C00B C008 C00D 119.4(4) . . ?
C00D C008 C006 117.8(4) . . ?
C00F C009 C005 120.5(5) . . ?
C00H C00A N004 119.6(5) . . ?
C00K C00A N004 119.8(4) . . ?
C00K C00A C00H 120.6(5) . . ?
C00Q C00B C008 120.2(5) . . ?
C00L C00C C00I 120.2(5) . . ?
C00N C00D C008 120.2(5) . . ?
C00G C00E C00H 120.6(5) . . ?
C00L C00F C009 120.1(5) . . ?
C00O C00G C00E 120.1(5) . . ?
C00A C00H C00E 119.0(5) . . ?
C00C C00I C005 120.5(5) . . ?
C006 C00J S001 120.0(4) . . ?
C00M C00J S001 110.6(3) . . ?
C00M C00J C006 128.7(4) . . ?
C00A C00K C00O 119.9(5) . . ?
C00C C00L C00F 120.0(5) . . ?
C00J C00M N004 115.2(4) . . ?
C00D C00N C00P 120.3(5) . . ?
C00G C00O C00K 119.8(5) . . ?
C00N C00P C00Q 120.3(5) . . ?
C00B C00Q C00P 119.6(5) . . ?
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
S001 C007 1.769(5) . ?
S001 C00J 1.759(4) . ?
O002 C006 1.225(6) . ?
N003 C005 1.416(6) . ?
N003 C007 1.273(6) . ?
N004 C007 1.397(5) . ?
N004 C00A 1.437(5) . ?
N004 C00M 1.367(6) . ?
C005 C009 1.385(6) . ?
C005 C00I 1.384(6) . ?
C006 C008 1.494(7) . ?
C006 C00J 1.459(6) . ?
C008 C00B 1.381(7) . ?
C008 C00D 1.387(6) . ?
C009 C00F 1.379(7) . ?
C00A C00H 1.364(6) . ?
C00A C00K 1.363(7) . ?
C00B C00Q 1.373(7) . ?
C00C C00I 1.382(7) . ?
C00C C00L 1.369(8) . ?
C00D C00N 1.360(7) . ?
C00E C00G 1.361(8) . ?
C00E C00H 1.386(7) . ?
C00F C00L 1.376(8) . ?
C00G C00O 1.358(7) . ?
C00J C00M 1.348(6) . ?
C00K C00O 1.386(7) . ?
C00N C00P 1.372(8) . ?
C00P C00Q 1.376(7) . ?
