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#$Date: 2022-11-28 11:21:50 +0200 (Mon, 28 Nov 2022) $
#$Revision: 279590 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/62/8106269.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_8106269
loop_
_publ_author_name
'Zhao, Li-Xia'
'Wang, Qing-Rui'
'Zou, Yue-Li'
'Wu, Hao'
'Ye, Fei'
_publ_section_title
;
 Crystal structure of methyl
 (R)-4-(o-chlorobenzoyl)-1-thia-4-azaspiro[4.5]decane-3-carboxylate,
 C17H20ClNO3S
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              709
_journal_page_last               710
_journal_paper_doi               10.1515/ncrs-2018-0032
_journal_volume                  233
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C17 H20 Cl N O3 S'
_chemical_formula_sum            'C17 H20 Cl N O3 S'
_chemical_formula_weight         353.85
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1984(2)
_cell_length_b                   14.3940(5)
_cell_length_c                   18.9651(6)
_cell_measurement_reflns_used    7570
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.20
_cell_measurement_theta_min      3.86
_cell_volume                     1692.06(10)
_computing_cell_refinement       'Bruker D8 Venture'
_computing_data_collection       'Bruker D8 Venture'
_computing_data_reduction        'Bruker D8 Venture'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'D8 VENTURE PHOTON II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8944
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.191
_diffrn_reflns_theta_min         3.855
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.271
_exptl_absorpt_correction_T_max  0.736
_exptl_absorpt_correction_T_min  0.676
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;

 Flack x determined using 1191 quotients [(I+)-(I-)]/[(I+)+(I-)]

 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).

;
_refine_ls_abs_structure_Flack   0.050(6)
_refine_ls_extinction_coef       0.0096(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3042
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0263
_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)+(0.0360P)²+0.1440P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0683
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                2976
_reflns_number_total             3042
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0032_suppl.cif
_cod_data_source_block           cu_dbnd_wh_2_0m
_cod_database_code               8106269
_shelx_shelxl_version_number     2014/7
_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.

;
_shelx_estimated_absorpt_t_min   0.676
_shelx_estimated_absorpt_t_max   0.736
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -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
C1 C 0.6229(4) 0.37442(17) 0.41523(11) 0.0454(6) Uani 1 1 d . . . . .
N1 N 0.6930(3) 0.57346(11) 0.33722(8) 0.0301(3) Uani 1 1 d . . . . .
O1 O 0.9396(3) 0.55611(11) 0.42518(8) 0.0457(4) Uani 1 1 d . . . . .
S1 S 0.48528(9) 0.70955(4) 0.27335(3) 0.04108(17) Uani 1 1 d . . . . .
C2 C 0.6169(6) 0.27880(19) 0.42294(14) 0.0635(8) Uani 1 1 d . . . . .
H2 H 0.5021 0.2505 0.4461 0.076 Uiso 1 1 calc R U . . .
Cl1 Cl 0.41335(12) 0.44100(5) 0.44965(4) 0.0627(2) Uani 1 1 d . . . . .
O2 O 0.5836(3) 0.52343(12) 0.15470(8) 0.0460(4) Uani 1 1 d . . . . .
C3 C 0.7821(8) 0.22632(19) 0.39603(16) 0.0723(10) Uani 1 1 d . . . . .
H3 H 0.7798 0.1621 0.4015 0.087 Uiso 1 1 calc R U . . .
O3 O 0.8978(3) 0.54158(13) 0.21032(9) 0.0509(4) Uani 1 1 d . . . . .
C4 C 0.9509(7) 0.2675(2) 0.36108(15) 0.0689(9) Uani 1 1 d . . . . .
H4 H 1.0610 0.2312 0.3425 0.083 Uiso 1 1 calc R U . . .
C5 C 0.9573(5) 0.36366(17) 0.35344(12) 0.0510(6) Uani 1 1 d . . . . .
H5 H 1.0723 0.3914 0.3300 0.061 Uiso 1 1 calc R U . . .
C6 C 0.7927(4) 0.41821(14) 0.38075(10) 0.0371(5) Uani 1 1 d . . . . .
C7 C 0.8155(3) 0.52242(14) 0.38206(10) 0.0323(4) Uani 1 1 d . . . . .
C8 C 0.5693(3) 0.53352(13) 0.27917(10) 0.0318(4) Uani 1 1 d . . . . .
H8 H 0.5267 0.4698 0.2908 0.038 Uiso 1 1 calc R U . . .
C9 C 0.3708(3) 0.59423(16) 0.27211(13) 0.0409(5) Uani 1 1 d . . . . .
H9A H 0.2723 0.5850 0.3112 0.049 Uiso 1 1 calc R U . . .
H9B H 0.2955 0.5822 0.2282 0.049 Uiso 1 1 calc R U . . .
C10 C 0.7059(3) 0.53394(13) 0.21172(10) 0.0324(4) Uani 1 1 d . . . . .
C11 C 0.6937(5) 0.5281(2) 0.08768(12) 0.0553(6) Uani 1 1 d . . . . .
H11A H 0.7656 0.5869 0.0835 0.083 Uiso 1 1 calc R U . . .
H11B H 0.5907 0.5217 0.0502 0.083 Uiso 1 1 calc R U . . .
H11C H 0.7978 0.4789 0.0848 0.083 Uiso 1 1 calc R U . . .
C12 C 0.6773(3) 0.67701(13) 0.34371(10) 0.0310(4) Uani 1 1 d . . . . .
C13 C 0.8920(3) 0.72515(14) 0.33014(11) 0.0355(4) Uani 1 1 d . . . . .
H13A H 0.9421 0.7098 0.2831 0.043 Uiso 1 1 calc R U . . .
H13B H 0.9982 0.7028 0.3636 0.043 Uiso 1 1 calc R U . . .
C14 C 0.8705(5) 0.83019(16) 0.33698(13) 0.0479(6) Uani 1 1 d . . . . .
H14A H 1.0101 0.8590 0.3296 0.057 Uiso 1 1 calc R U . . .
H14B H 0.7727 0.8532 0.3011 0.057 Uiso 1 1 calc R U . . .
C15 C 0.7856(5) 0.85626(17) 0.40944(14) 0.0551(7) Uani 1 1 d . . . . .
H15A H 0.7670 0.9231 0.4120 0.066 Uiso 1 1 calc R U . . .
H15B H 0.8901 0.8383 0.4450 0.066 Uiso 1 1 calc R U . . .
C16 C 0.5715(5) 0.80891(17) 0.42468(14) 0.0541(6) Uani 1 1 d . . . . .
H16A H 0.4625 0.8332 0.3929 0.065 Uiso 1 1 calc R U . . .
H16B H 0.5273 0.8233 0.4725 0.065 Uiso 1 1 calc R U . . .
C17 C 0.5851(4) 0.70318(16) 0.41594(11) 0.0416(5) Uani 1 1 d . . . . .
H17A H 0.6761 0.6775 0.4527 0.050 Uiso 1 1 calc R U . . .
H17B H 0.4422 0.6765 0.4210 0.050 Uiso 1 1 calc R U . . .
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'
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'
Cl Cl 0.3639 0.7018 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C6 121.4(3) . .
C2 C1 Cl1 119.2(2) . .
C6 C1 Cl1 119.44(18) . .
C7 N1 C8 123.62(16) . .
C7 N1 C12 121.56(16) . .
C8 N1 C12 114.82(15) . .
C9 S1 C12 91.70(9) . .
C3 C2 C1 119.2(3) . .
C3 C2 H2 120.4 . .
C1 C2 H2 120.4 . .
C10 O2 C11 116.2(2) . .
C2 C3 C4 120.7(3) . .
C2 C3 H3 119.7 . .
C4 C3 H3 119.7 . .
C3 C4 C5 120.1(3) . .
C3 C4 H4 119.9 . .
C5 C4 H4 119.9 . .
C6 C5 C4 120.1(3) . .
C6 C5 H5 119.9 . .
C4 C5 H5 119.9 . .
C5 C6 C1 118.4(2) . .
C5 C6 C7 120.0(2) . .
C1 C6 C7 121.0(2) . .
O1 C7 N1 123.83(18) . .
O1 C7 C6 117.70(18) . .
N1 C7 C6 118.44(17) . .
N1 C8 C9 105.43(16) . .
N1 C8 C10 109.73(16) . .
C9 C8 C10 111.85(17) . .
N1 C8 H8 109.9 . .
C9 C8 H8 109.9 . .
C10 C8 H8 109.9 . .
C8 C9 S1 102.11(13) . .
C8 C9 H9A 111.3 . .
S1 C9 H9A 111.3 . .
C8 C9 H9B 111.3 . .
S1 C9 H9B 111.3 . .
H9A C9 H9B 109.2 . .
O3 C10 O2 124.08(19) . .
O3 C10 C8 124.64(18) . .
O2 C10 C8 111.28(17) . .
O2 C11 H11A 109.5 . .
O2 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
O2 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
N1 C12 C13 112.48(16) . .
N1 C12 C17 110.01(16) . .
C13 C12 C17 111.45(17) . .
N1 C12 S1 103.55(12) . .
C13 C12 S1 109.00(13) . .
C17 C12 S1 110.05(15) . .
C12 C13 C14 111.17(19) . .
C12 C13 H13A 109.4 . .
C14 C13 H13A 109.4 . .
C12 C13 H13B 109.4 . .
C14 C13 H13B 109.4 . .
H13A C13 H13B 108.0 . .
C15 C14 C13 110.65(19) . .
C15 C14 H14A 109.5 . .
C13 C14 H14A 109.5 . .
C15 C14 H14B 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 108.1 . .
C14 C15 C16 111.3(2) . .
C14 C15 H15A 109.4 . .
C16 C15 H15A 109.4 . .
C14 C15 H15B 109.4 . .
C16 C15 H15B 109.4 . .
H15A C15 H15B 108.0 . .
C15 C16 C17 112.1(2) . .
C15 C16 H16A 109.2 . .
C17 C16 H16A 109.2 . .
C15 C16 H16B 109.2 . .
C17 C16 H16B 109.2 . .
H16A C16 H16B 107.9 . .
C12 C17 C16 111.18(19) . .
C12 C17 H17A 109.4 . .
C16 C17 H17A 109.4 . .
C12 C17 H17B 109.4 . .
C16 C17 H17B 109.4 . .
H17A C17 H17B 108.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.385(4) .
C1 C6 1.390(4) .
C1 Cl1 1.741(3) .
N1 C7 1.356(3) .
N1 C8 1.459(2) .
N1 C12 1.499(2) .
O1 C7 1.223(3) .
S1 C9 1.805(2) .
S1 C12 1.849(2) .
C2 C3 1.371(5) .
C2 H2 0.9300 .
O2 C10 1.329(3) .
O2 C11 1.444(3) .
C3 C4 1.373(6) .
C3 H3 0.9300 .
O3 C10 1.195(3) .
C4 C5 1.392(4) .
C4 H4 0.9300 .
C5 C6 1.388(4) .
C5 H5 0.9300 .
C6 C7 1.507(3) .
C8 C9 1.515(3) .
C8 C10 1.534(3) .
C8 H8 0.9800 .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 C13 1.522(3) .
C12 C17 1.532(3) .
C13 C14 1.523(3) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 C15 1.519(4) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 C16 1.520(4) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 C17 1.533(3) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 0.1(4) . . . .
Cl1 C1 C2 C3 -179.8(2) . . . .
C1 C2 C3 C4 -0.7(4) . . . .
C2 C3 C4 C5 0.9(4) . . . .
C3 C4 C5 C6 -0.4(4) . . . .
C4 C5 C6 C1 -0.3(3) . . . .
C4 C5 C6 C7 170.9(2) . . . .
C2 C1 C6 C5 0.4(3) . . . .
Cl1 C1 C6 C5 -179.68(17) . . . .
C2 C1 C6 C7 -170.7(2) . . . .
Cl1 C1 C6 C7 9.2(3) . . . .
C8 N1 C7 O1 170.70(19) . . . .
C12 N1 C7 O1 -8.6(3) . . . .
C8 N1 C7 C6 -11.5(3) . . . .
C12 N1 C7 C6 169.21(18) . . . .
C5 C6 C7 O1 -73.2(3) . . . .
C1 C6 C7 O1 97.7(3) . . . .
C5 C6 C7 N1 108.9(2) . . . .
C1 C6 C7 N1 -80.2(2) . . . .
C7 N1 C8 C9 147.27(19) . . . .
C12 N1 C8 C9 -33.4(2) . . . .
C7 N1 C8 C10 -92.1(2) . . . .
C12 N1 C8 C10 87.22(19) . . . .
N1 C8 C9 S1 47.71(17) . . . .
C10 C8 C9 S1 -71.51(18) . . . .
C12 S1 C9 C8 -40.86(15) . . . .
C11 O2 C10 O3 -4.3(3) . . . .
C11 O2 C10 C8 176.55(19) . . . .
N1 C8 C10 O3 18.6(3) . . . .
C9 C8 C10 O3 135.2(2) . . . .
N1 C8 C10 O2 -162.27(16) . . . .
C9 C8 C10 O2 -45.6(2) . . . .
C7 N1 C12 C13 64.7(2) . . . .
C8 N1 C12 C13 -114.69(18) . . . .
C7 N1 C12 C17 -60.2(3) . . . .
C8 N1 C12 C17 120.42(18) . . . .
C7 N1 C12 S1 -177.82(16) . . . .
C8 N1 C12 S1 2.83(19) . . . .
C9 S1 C12 N1 22.62(14) . . . .
C9 S1 C12 C13 142.56(15) . . . .
C9 S1 C12 C17 -94.94(16) . . . .
N1 C12 C13 C14 179.88(17) . . . .
C17 C12 C13 C14 -56.0(2) . . . .
S1 C12 C13 C14 65.63(19) . . . .
C12 C13 C14 C15 57.4(3) . . . .
C13 C14 C15 C16 -56.5(3) . . . .
C14 C15 C16 C17 54.6(3) . . . .
N1 C12 C17 C16 178.8(2) . . . .
C13 C12 C17 C16 53.4(3) . . . .
S1 C12 C17 C16 -67.7(2) . . . .
C15 C16 C17 C12 -52.8(3) . . . .
