#------------------------------------------------------------------------------
#$Date: 2023-09-26 09:40:26 +0300 (Tue, 26 Sep 2023) $
#$Revision: 286521 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/75/8107542.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_8107542
loop_
_publ_author_name
'Wang, Zhen'
'Zhao, Feng-Lan'
'Hou, Gui-Ge'
'Meng, Qing-Guo'
_publ_section_title
;
 Crystal structure of methyl ((4-aminobenzyl)sulfonyl)-L-prolinate,
 C13H18N2O4S
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              725
_journal_page_last               727
_journal_paper_doi               10.1515/ncrs-2023-0173
_journal_volume                  238
_journal_year                    2023
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C13 H18 N2 O4 S'
_chemical_formula_sum            'C13 H18 N2 O4 S'
_chemical_formula_weight         298.35
_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   mixed
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8619(2)
_cell_length_b                   12.0735(4)
_cell_length_c                   16.6591(5)
_cell_measurement_reflns_used    9876
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      78.95
_cell_measurement_theta_min      4.52
_cell_volume                     1380.16(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXL-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20828
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         78.982
_diffrn_reflns_theta_min         4.523
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    2.235
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1171 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.035(5)
_refine_ls_extinction_coef       0.0041(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2946
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0245
_refine_ls_R_factor_gt           0.0236
_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)+(0.0339P)²+0.1780P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0599
_refine_ls_wR_factor_ref         0.0604
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                2872
_reflns_number_total             2946
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0173_suppl_001.cif
_cod_data_source_block           cu_0909_4_0m
_cod_database_code               8107542
_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   0.745
_shelx_estimated_absorpt_t_max   0.807
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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 0.5972(3) 0.10403(16) 0.13039(11) 0.0262(4) Uani 1 1 d . . . . .
H1 H 0.517115 0.168137 0.128250 0.031 Uiso 1 1 calc R U . . .
C2 C 0.5164(3) 0.00354(16) 0.15321(10) 0.0250(4) Uani 1 1 d . . . . .
H2 H 0.381954 -0.000393 0.166545 0.030 Uiso 1 1 calc R U . . .
C3 C 0.6311(3) -0.09186(15) 0.15674(9) 0.0198(3) Uani 1 1 d . . . . .
C4 C 0.8288(3) -0.08351(15) 0.13699(10) 0.0201(3) Uani 1 1 d . . . . .
H4 H 0.909299 -0.147475 0.138953 0.024 Uiso 1 1 calc R U . . .
C5 C 0.9078(3) 0.01737(15) 0.11460(10) 0.0214(4) Uani 1 1 d . . . . .
H5 H 1.042463 0.021778 0.101744 0.026 Uiso 1 1 calc R U . . .
C6 C 0.7935(3) 0.11253(15) 0.11059(10) 0.0224(4) Uani 1 1 d . . . . .
C7 C 0.8846(3) 0.22168(16) 0.08884(10) 0.0261(4) Uani 1 1 d . . . . .
H7A H 0.786612 0.269128 0.062011 0.031 Uiso 1 1 calc R U . . .
H7B H 0.993146 0.209151 0.050759 0.031 Uiso 1 1 calc R U . . .
C8 C 1.2917(3) 0.40152(16) 0.12293(10) 0.0227(4) Uani 1 1 d . . . . .
H8A H 1.314161 0.356074 0.074345 0.027 Uiso 1 1 calc R U . . .
H8B H 1.375060 0.373634 0.167020 0.027 Uiso 1 1 calc R U . . .
C9 C 1.3305(3) 0.52418(16) 0.10640(11) 0.0252(4) Uani 1 1 d . . . . .
H9A H 1.465720 0.544398 0.121083 0.030 Uiso 1 1 calc R U . . .
H9B H 1.308981 0.541944 0.049063 0.030 Uiso 1 1 calc R U . . .
C10 C 1.1842(3) 0.58433(15) 0.15935(10) 0.0207(3) Uani 1 1 d . . . . .
H10A H 1.160560 0.660597 0.139818 0.025 Uiso 1 1 calc R U . . .
H10B H 1.229401 0.587452 0.215737 0.025 Uiso 1 1 calc R U . . .
C11 C 1.0013(2) 0.51285(13) 0.15131(9) 0.0177(3) Uani 1 1 d . . . . .
H11 H 0.919980 0.519648 0.200867 0.021 Uiso 1 1 calc R U . . .
C12 C 0.8778(2) 0.53899(14) 0.07726(10) 0.0185(3) Uani 1 1 d . . . . .
C13 C 0.7337(3) 0.68444(15) 0.00261(10) 0.0237(4) Uani 1 1 d . . . . .
H13A H 0.611150 0.642766 0.001641 0.036 Uiso 1 1 calc R U . . .
H13B H 0.805258 0.671372 -0.047409 0.036 Uiso 1 1 calc R U . . .
H13C H 0.705502 0.763671 0.007956 0.036 Uiso 1 1 calc R U . . .
N1 N 0.5498(2) -0.19452(12) 0.17535(9) 0.0238(3) Uani 1 1 d . . . . .
H1A H 0.437345 -0.187300 0.201944 0.025 Uiso 1 1 d . . . . .
H1B H 0.631536 -0.240553 0.194209 0.035 Uiso 1 1 d . . . . .
N2 N 1.0839(2) 0.40101(12) 0.14615(9) 0.0191(3) Uani 1 1 d . . . . .
O1 O 1.1177(2) 0.21852(11) 0.21203(7) 0.0263(3) Uani 1 1 d . . . . .
O2 O 0.8100(2) 0.32514(11) 0.22329(8) 0.0276(3) Uani 1 1 d . . . . .
O3 O 0.8086(2) 0.47123(11) 0.03267(8) 0.0301(3) Uani 1 1 d . . . . .
O4 O 0.8508(2) 0.64820(11) 0.07014(7) 0.0244(3) Uani 1 1 d . . . . .
S1 S 0.97480(6) 0.29069(3) 0.17654(2) 0.01842(13) Uani 1 1 d . . . . .
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'
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 121.13(17) . .
C2 C1 H1 119.4 . .
C6 C1 H1 119.4 . .
C1 C2 C3 120.51(17) . .
C1 C2 H2 119.7 . .
C3 C2 H2 119.7 . .
N1 C3 C2 121.15(16) . .
N1 C3 C4 120.27(17) . .
C2 C3 C4 118.49(17) . .
C5 C4 C3 120.41(17) . .
C5 C4 H4 119.8 . .
C3 C4 H4 119.8 . .
C4 C5 C6 121.21(17) . .
C4 C5 H5 119.4 . .
C6 C5 H5 119.4 . .
C1 C6 C5 118.25(17) . .
C1 C6 C7 121.67(17) . .
C5 C6 C7 120.03(17) . .
C6 C7 S1 110.79(12) . .
C6 C7 H7A 109.5 . .
S1 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
S1 C7 H7B 109.5 . .
H7A C7 H7B 108.1 . .
N2 C8 C9 102.67(15) . .
N2 C8 H8A 111.2 . .
C9 C8 H8A 111.2 . .
N2 C8 H8B 111.2 . .
C9 C8 H8B 111.2 . .
H8A C8 H8B 109.1 . .
C10 C9 C8 104.05(14) . .
C10 C9 H9A 110.9 . .
C8 C9 H9A 110.9 . .
C10 C9 H9B 110.9 . .
C8 C9 H9B 110.9 . .
H9A C9 H9B 109.0 . .
C9 C10 C11 102.80(14) . .
C9 C10 H10A 111.2 . .
C11 C10 H10A 111.2 . .
C9 C10 H10B 111.2 . .
C11 C10 H10B 111.2 . .
H10A C10 H10B 109.1 . .
N2 C11 C10 101.99(13) . .
N2 C11 C12 110.90(13) . .
C10 C11 C12 114.14(13) . .
N2 C11 H11 109.8 . .
C10 C11 H11 109.8 . .
C12 C11 H11 109.8 . .
O3 C12 O4 124.15(16) . .
O3 C12 C11 125.21(16) . .
O4 C12 C11 110.60(14) . .
O4 C13 H13A 109.5 . .
O4 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
O4 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C3 N1 H1A 111.6 . .
C3 N1 H1B 113.5 . .
H1A N1 H1B 116.8 . .
C11 N2 C8 112.60(14) . .
C11 N2 S1 124.32(11) . .
C8 N2 S1 122.32(12) . .
C12 O4 C13 116.31(14) . .
O2 S1 O1 119.31(8) . .
O2 S1 N2 107.30(8) . .
O1 S1 N2 108.27(8) . .
O2 S1 C7 107.77(9) . .
O1 S1 C7 106.79(9) . .
N2 S1 C7 106.80(8) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.387(3) .
C1 C6 1.390(3) .
C1 H1 0.9500 .
C2 C3 1.396(3) .
C2 H2 0.9500 .
C3 N1 1.394(2) .
C3 C4 1.400(3) .
C4 C5 1.384(3) .
C4 H4 0.9500 .
C5 C6 1.393(3) .
C5 H5 0.9500 .
C6 C7 1.503(2) .
C7 S1 1.7921(18) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 N2 1.477(2) .
C8 C9 1.530(3) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.521(3) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C11 1.529(2) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 N2 1.467(2) .
C11 C12 1.530(2) .
C11 H11 1.0000 .
C12 O3 1.203(2) .
C12 O4 1.337(2) .
C13 O4 1.450(2) .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
N1 H1A 0.8939 .
N1 H1B 0.8499 .
N2 S1 1.6096(15) .
O1 S1 1.4387(14) .
O2 S1 1.4346(14) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1B O1 0.85 2.38 3.135(2) 149.0 3_745 yes
N1 H1A O2 0.89 2.11 3.001(2) 173.4 3_645 yes
C7 H7A O3 0.99 2.49 3.198(2) 127.9 . yes
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(3) . . . .
C1 C2 C3 N1 -176.49(15) . . . .
C1 C2 C3 C4 0.2(3) . . . .
N1 C3 C4 C5 176.77(15) . . . .
C2 C3 C4 C5 0.1(2) . . . .
C3 C4 C5 C6 -0.4(3) . . . .
C2 C1 C6 C5 -0.3(3) . . . .
C2 C1 C6 C7 -177.60(16) . . . .
C4 C5 C6 C1 0.6(3) . . . .
C4 C5 C6 C7 177.90(15) . . . .
C1 C6 C7 S1 89.22(19) . . . .
C5 C6 C7 S1 -88.03(19) . . . .
N2 C8 C9 C10 27.42(17) . . . .
C8 C9 C10 C11 -39.74(17) . . . .
C9 C10 C11 N2 35.72(16) . . . .
C9 C10 C11 C12 -83.94(17) . . . .
N2 C11 C12 O3 20.4(2) . . . .
C10 C11 C12 O3 134.91(18) . . . .
N2 C11 C12 O4 -161.82(14) . . . .
C10 C11 C12 O4 -47.31(19) . . . .
C10 C11 N2 C8 -19.48(16) . . . .
C12 C11 N2 C8 102.44(16) . . . .
C10 C11 N2 S1 150.64(12) . . . .
C12 C11 N2 S1 -87.44(16) . . . .
C9 C8 N2 C11 -4.78(18) . . . .
C9 C8 N2 S1 -175.13(12) . . . .
O3 C12 O4 C13 -1.5(3) . . . .
C11 C12 O4 C13 -179.32(14) . . . .
C11 N2 S1 O2 -12.22(15) . . . .
C8 N2 S1 O2 156.98(13) . . . .
C11 N2 S1 O1 -142.22(13) . . . .
C8 N2 S1 O1 26.98(15) . . . .
C11 N2 S1 C7 103.12(15) . . . .
C8 N2 S1 C7 -87.69(15) . . . .
C6 C7 S1 O2 -69.42(16) . . . .
C6 C7 S1 O1 59.89(16) . . . .
C6 C7 S1 N2 175.56(13) . . . .
