#------------------------------------------------------------------------------
#$Date: 2021-07-05 21:15:00 +0300 (Mon, 05 Jul 2021) $
#$Revision: 267251 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/80/7158082.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_7158082
loop_
_publ_author_name
'Meng, Beibei'
'Shi, Qian'
'Meng, Yuan'
'Chen, Jie'
'Cao, Weiguo'
'Wu, Xiaoyu'
_publ_section_title
;
 Asymmetric catalytic alkynylation of thiazolones and azlactones for
 synthesis of quaternary α-amino acid precursors.
;
_journal_issue                   23
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5087
_journal_page_last               5092
_journal_paper_doi               10.1039/d1ob00582k
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H16 Cl N O S'
_chemical_formula_weight         401.89
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2021-03-23 deposited with the CCDC.	2021-05-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.539(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.7761(5)
_cell_length_b                   8.5009(4)
_cell_length_c                   11.6925(5)
_cell_measurement_reflns_used    7894
_cell_measurement_temperature    150.(2)
_cell_measurement_theta_max      66.69
_cell_measurement_theta_min      4.09
_cell_volume                     989.30(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150.(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8458
_diffrn_reflns_theta_full        66.69
_diffrn_reflns_theta_max         66.69
_diffrn_reflns_theta_min         4.09
_exptl_absorpt_coefficient_mu    2.801
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5592
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.194
_refine_ls_abs_structure_details
;

Flack x determined using 1308 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.064(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3205
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0227
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0321P)²+0.0491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0607
_refine_ls_wR_factor_ref         0.0609
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_full    0.831
_reflns_Friedel_fraction_max     0.831
_reflns_number_gt                3168
_reflns_number_total             3205
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00582k2.cif
_cod_data_source_block           20201225d
_cod_depositor_comments          'Adding full bibliography for 7158082.cif.'
_cod_database_code               7158082
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 -0.01827(6) 0.90422(8) -0.00360(5) 0.04757(18) Uani d . . . 1 . .
S S1 0.54053(4) 0.68663(6) 0.73185(4) 0.02805(14) Uani d . . . 1 . .
O O1 0.28897(13) 0.66325(19) 0.71666(12) 0.0317(3) Uani d . . . 1 . .
N N1 0.47903(15) 0.45739(19) 0.56724(14) 0.0227(3) Uani d . . . 1 . .
C C1 0.35580(18) 0.4767(2) 0.59015(16) 0.0221(4) Uani d . . . 1 . .
C C2 0.37368(17) 0.6141(2) 0.68304(16) 0.0240(4) Uani d . . . 1 . .
C C3 0.57306(18) 0.5486(2) 0.63129(16) 0.0218(4) Uani d . . . 1 . .
C C4 0.70799(19) 0.5464(2) 0.62620(17) 0.0244(4) Uani d . . . 1 . .
C C5 0.8115(2) 0.6412(3) 0.7037(2) 0.0322(5) Uani d . . . 1 . .
H H5 0.796417 0.709393 0.76145 0.039 Uiso calc U . R 1 . .
C C6 0.9379(2) 0.6355(3) 0.6961(2) 0.0393(5) Uani d . . . 1 . .
H H6 1.008864 0.699758 0.748987 0.047 Uiso calc U . R 1 . .
C C7 0.9596(2) 0.5370(3) 0.6122(2) 0.0398(5) Uani d . . . 1 . .
H H7 1.045068 0.534943 0.606196 0.048 Uiso calc U . R 1 . .
C C8 0.8571(2) 0.4405(3) 0.5362(2) 0.0336(5) Uani d . . . 1 . .
H H8 0.873069 0.371147 0.479555 0.04 Uiso calc U . R 1 . .
C C9 0.7319(2) 0.4456(2) 0.54302(18) 0.0274(4) Uani d . . . 1 . .
H H9 0.661807 0.379943 0.490661 0.033 Uiso calc U . R 1 . .
C C10 0.24275(19) 0.5175(2) 0.47482(17) 0.0246(4) Uani d . . . 1 . .
C C11 0.14959(19) 0.5549(2) 0.38383(16) 0.0250(4) Uani d . . . 1 . .
C C12 0.03895(19) 0.6061(2) 0.27469(17) 0.0238(4) Uani d . . . 1 . .
C C13 0.06080(19) 0.7183(2) 0.19780(17) 0.0254(4) Uani d . . . 1 . .
H H13 0.148053 0.760393 0.216399 0.03 Uiso calc U . R 1 . .
C C14 -0.0462(2) 0.7676(2) 0.09418(18) 0.0285(4) Uani d . . . 1 . .
C C15 -0.1746(2) 0.7098(3) 0.06587(18) 0.0322(5) Uani d . . . 1 . .
H H15 -0.247296 0.746449 -0.005195 0.039 Uiso calc U . R 1 . .
C C16 -0.1956(2) 0.5985(3) 0.14197(19) 0.0323(5) Uani d . . . 1 . .
H H16 -0.283309 0.557654 0.122763 0.039 Uiso calc U . R 1 . .
C C17 -0.0902(2) 0.5454(3) 0.24637(18) 0.0287(4) Uani d . . . 1 . .
H H17 -0.105485 0.468285 0.29833 0.034 Uiso calc U . R 1 . .
C C18 0.32522(18) 0.3228(2) 0.64657(17) 0.0250(4) Uani d . . . 1 . .
H H18A 0.24801 0.34151 0.67091 0.03 Uiso calc U . R 1 . .
H H18B 0.298994 0.239615 0.582431 0.03 Uiso calc U . R 1 . .
C C19 0.44299(19) 0.2655(2) 0.75799(17) 0.0250(4) Uani d . . . 1 . .
C C20 0.5314(2) 0.1553(3) 0.74448(19) 0.0327(5) Uani d . . . 1 . .
H H20 0.51768 0.116168 0.664442 0.039 Uiso calc U . R 1 . .
C C21 0.6397(2) 0.1016(3) 0.8467(2) 0.0418(5) Uani d . . . 1 . .
H H21 0.699623 0.02624 0.836192 0.05 Uiso calc U . R 1 . .
C C22 0.6606(2) 0.1572(3) 0.9634(2) 0.0449(6) Uani d . . . 1 . .
H H22 0.734867 0.120729 1.033259 0.054 Uiso calc U . R 1 . .
C C23 0.5726(3) 0.2667(3) 0.9783(2) 0.0424(6) Uani d . . . 1 . .
H H23 0.586278 0.304468 1.058704 0.051 Uiso calc U . R 1 . .
C C24 0.4650(2) 0.3214(3) 0.87661(19) 0.0324(5) Uani d . . . 1 . .
H H24 0.405785 0.397343 0.887551 0.039 Uiso calc U . 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 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C2 S1 C3 . . 89.45(9) ?
C3 N1 C1 . . 113.57(16) ?
N1 C1 C10 . . 110.49(15) ?
N1 C1 C18 . . 109.77(15) ?
C10 C1 C18 . . 110.58(15) ?
N1 C1 C2 . . 109.52(15) ?
C10 C1 C2 . . 107.47(15) ?
C18 C1 C2 . . 108.96(15) ?
O1 C2 C1 . . 125.75(17) ?
O1 C2 S1 . . 125.34(15) ?
C1 C2 S1 . . 108.92(13) ?
N1 C3 C4 . . 122.97(18) ?
N1 C3 S1 . . 118.43(14) ?
C4 C3 S1 . . 118.60(14) ?
C9 C4 C5 . . 119.59(19) ?
C9 C4 C3 . . 118.98(18) ?
C5 C4 C3 . . 121.42(19) ?
C4 C5 C6 . . 119.7(2) ?
C4 C5 H5 . . 120.2 ?
C6 C5 H5 . . 120.2 ?
C7 C6 C5 . . 120.1(2) ?
C7 C6 H6 . . 119.9 ?
C5 C6 H6 . . 119.9 ?
C6 C7 C8 . . 120.3(2) ?
C6 C7 H7 . . 119.8 ?
C8 C7 H7 . . 119.8 ?
C9 C8 C7 . . 119.9(2) ?
C9 C8 H8 . . 120.0 ?
C7 C8 H8 . . 120.0 ?
C8 C9 C4 . . 120.39(19) ?
C8 C9 H9 . . 119.8 ?
C4 C9 H9 . . 119.8 ?
C11 C10 C1 . . 177.5(2) ?
C10 C11 C12 . . 177.8(2) ?
C13 C12 C17 . . 119.94(17) ?
C13 C12 C11 . . 119.49(17) ?
C17 C12 C11 . . 120.56(18) ?
C14 C13 C12 . . 118.96(18) ?
C14 C13 H13 . . 120.5 ?
C12 C13 H13 . . 120.5 ?
C13 C14 C15 . . 121.67(19) ?
C13 C14 Cl1 . . 118.97(16) ?
C15 C14 Cl1 . . 119.36(16) ?
C16 C15 C14 . . 119.13(18) ?
C16 C15 H15 . . 120.4 ?
C14 C15 H15 . . 120.4 ?
C15 C16 C17 . . 120.77(18) ?
C15 C16 H16 . . 119.6 ?
C17 C16 H16 . . 119.6 ?
C16 C17 C12 . . 119.52(19) ?
C16 C17 H17 . . 120.2 ?
C12 C17 H17 . . 120.2 ?
C19 C18 C1 . . 113.11(15) ?
C19 C18 H18A . . 109.0 ?
C1 C18 H18A . . 109.0 ?
C19 C18 H18B . . 109.0 ?
C1 C18 H18B . . 109.0 ?
H18A C18 H18B . . 107.8 ?
C20 C19 C24 . . 118.67(18) ?
C20 C19 C18 . . 120.42(18) ?
C24 C19 C18 . . 120.91(19) ?
C19 C20 C21 . . 120.7(2) ?
C19 C20 H20 . . 119.6 ?
C21 C20 H20 . . 119.6 ?
C22 C21 C20 . . 120.2(2) ?
C22 C21 H21 . . 119.9 ?
C20 C21 H21 . . 119.9 ?
C21 C22 C23 . . 119.6(2) ?
C21 C22 H22 . . 120.2 ?
C23 C22 H22 . . 120.2 ?
C24 C23 C22 . . 120.4(2) ?
C24 C23 H23 . . 119.8 ?
C22 C23 H23 . . 119.8 ?
C23 C24 C19 . . 120.4(2) ?
C23 C24 H24 . . 119.8 ?
C19 C24 H24 . . 119.8 ?
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 C14 . 1.735(2) ?
S1 C2 . 1.7753(18) ?
S1 C3 . 1.788(2) ?
O1 C2 . 1.199(2) ?
N1 C3 . 1.268(3) ?
N1 C1 . 1.461(2) ?
C1 C10 . 1.471(2) ?
C1 C18 . 1.556(3) ?
C1 C2 . 1.556(3) ?
C3 C4 . 1.478(3) ?
C4 C9 . 1.392(3) ?
C4 C5 . 1.393(3) ?
C5 C6 . 1.399(3) ?
C5 H5 . 0.95 ?
C6 C7 . 1.377(4) ?
C6 H6 . 0.95 ?
C7 C8 . 1.389(3) ?
C7 H7 . 0.95 ?
C8 C9 . 1.383(3) ?
C8 H8 . 0.95 ?
C9 H9 . 0.95 ?
C10 C11 . 1.192(3) ?
C11 C12 . 1.440(3) ?
C12 C13 . 1.392(3) ?
C12 C17 . 1.400(3) ?
C13 C14 . 1.379(3) ?
C13 H13 . 0.95 ?
C14 C15 . 1.383(3) ?
C15 C16 . 1.375(3) ?
C15 H15 . 0.95 ?
C16 C17 . 1.386(3) ?
C16 H16 . 0.95 ?
C17 H17 . 0.95 ?
C18 C19 . 1.509(3) ?
C18 H18A . 0.99 ?
C18 H18B . 0.99 ?
C19 C20 . 1.388(3) ?
C19 C24 . 1.398(3) ?
C20 C21 . 1.390(3) ?
C20 H20 . 0.95 ?
C21 C22 . 1.379(4) ?
C21 H21 . 0.95 ?
C22 C23 . 1.386(4) ?
C22 H22 . 0.95 ?
C23 C24 . 1.385(3) ?
C23 H23 . 0.95 ?
C24 H24 . 0.95 ?
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
C3 N1 C1 C10 . . . . 121.68(17) ?
C3 N1 C1 C18 . . . . -116.11(17) ?
C3 N1 C1 C2 . . . . 3.5(2) ?
N1 C1 C2 O1 . . . . 176.84(18) ?
C10 C1 C2 O1 . . . . 56.8(2) ?
C18 C1 C2 O1 . . . . -63.1(2) ?
N1 C1 C2 S1 . . . . -3.31(18) ?
C10 C1 C2 S1 . . . . -123.37(14) ?
C18 C1 C2 S1 . . . . 116.78(14) ?
C3 S1 C2 O1 . . . . -178.26(18) ?
C3 S1 C2 C1 . . . . 1.89(13) ?
C1 N1 C3 C4 . . . . 178.09(16) ?
C1 N1 C3 S1 . . . . -2.2(2) ?
C2 S1 C3 N1 . . . . 0.05(16) ?
C2 S1 C3 C4 . . . . 179.81(15) ?
N1 C3 C4 C9 . . . . 3.4(3) ?
S1 C3 C4 C9 . . . . -176.36(14) ?
N1 C3 C4 C5 . . . . -175.80(18) ?
S1 C3 C4 C5 . . . . 4.4(3) ?
C9 C4 C5 C6 . . . . 0.7(3) ?
C3 C4 C5 C6 . . . . 179.93(19) ?
C4 C5 C6 C7 . . . . 0.2(3) ?
C5 C6 C7 C8 . . . . -1.2(3) ?
C6 C7 C8 C9 . . . . 1.3(3) ?
C7 C8 C9 C4 . . . . -0.3(3) ?
C5 C4 C9 C8 . . . . -0.7(3) ?
C3 C4 C9 C8 . . . . -179.88(17) ?
C17 C12 C13 C14 . . . . -0.2(3) ?
C11 C12 C13 C14 . . . . -179.40(17) ?
C12 C13 C14 C15 . . . . 0.9(3) ?
C12 C13 C14 Cl1 . . . . -178.56(15) ?
C13 C14 C15 C16 . . . . -1.1(3) ?
Cl1 C14 C15 C16 . . . . 178.37(16) ?
C14 C15 C16 C17 . . . . 0.5(3) ?
C15 C16 C17 C12 . . . . 0.2(3) ?
C13 C12 C17 C16 . . . . -0.4(3) ?
C11 C12 C17 C16 . . . . 178.87(19) ?
N1 C1 C18 C19 . . . . 52.0(2) ?
C10 C1 C18 C19 . . . . 174.11(16) ?
C2 C1 C18 C19 . . . . -68.0(2) ?
C1 C18 C19 C20 . . . . -93.9(2) ?
C1 C18 C19 C24 . . . . 86.4(2) ?
C24 C19 C20 C21 . . . . -0.1(3) ?
C18 C19 C20 C21 . . . . -179.74(19) ?
C19 C20 C21 C22 . . . . 0.1(3) ?
C20 C21 C22 C23 . . . . 0.2(4) ?
C21 C22 C23 C24 . . . . -0.6(4) ?
C22 C23 C24 C19 . . . . 0.7(3) ?
C20 C19 C24 C23 . . . . -0.3(3) ?
C18 C19 C24 C23 . . . . 179.33(19) ?
