#------------------------------------------------------------------------------
#$Date: 2022-10-07 03:48:55 +0300 (Fri, 07 Oct 2022) $
#$Revision: 278410 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/74/1567487.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_1567487
loop_
_publ_author_name
'Lai, Junshan'
'Reid, Jolene P.'
_publ_section_title
;
 Interrogating the thionium hydrogen bond as a noncovalent
 stereocontrolling interaction in chiral phosphate catalysis
;
_journal_issue                   37
_journal_name_full               'Chemical Science'
_journal_page_first              11065
_journal_page_last               11073
_journal_paper_doi               10.1039/D2SC02171D
_journal_volume                  13
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H17 N O2 S2'
_chemical_formula_sum            'C16 H17 N O2 S2'
_chemical_formula_weight         319.42
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2022-02-01
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-02-03 deposited with the CCDC.	2022-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2635(5)
_cell_length_b                   11.4411(10)
_cell_length_c                   20.8675(18)
_cell_measurement_reflns_used    9906
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      67.78
_cell_measurement_theta_min      4.24
_cell_volume                     1495.4(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Bruker D8 Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'cross coupled multi-layer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            40112
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.189
_diffrn_reflns_theta_min         4.237
_diffrn_source                   'microsource sealed X-ray tube'
_diffrn_source_current           0.59
_diffrn_source_power             0.0263612
_diffrn_source_voltage           44.68
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.255
_exptl_absorpt_correction_T_max  0.907
_exptl_absorpt_correction_T_min  0.800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0913 before and 0.0712 after correction.
The ratio of minimum to maximum transmission is 0.8821.
The λ/2 correction factor is not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of DCM and pentane  by slow evaporation'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1043 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.010(7)
_refine_ls_extinction_coef       0.0008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2735
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0262
_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)+(0.0255P)²+0.7576P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0591
_refine_ls_wR_factor_ref         0.0620
_reflns_Friedel_coverage         0.699
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                2604
_reflns_number_total             2735
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc02171d4.cif
_cod_data_source_block           reid001
_cod_depositor_comments          'Adding full bibliography for 1567487.cif.'
_cod_database_code               1567487
_shelx_shelxl_version_number     2018/3
_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_max   0.909
_shelx_estimated_absorpt_t_min   0.737
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a mylar loop in oil'
_olex2_submission_original_sample_id jlai50-trip
_olex2_submission_special_instructions 'No special instructions were received'
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
S1 S 0.06473(9) 0.24574(5) 0.67311(3) 0.01287(16) Uani 1 1 d . . . . .
S2 S 0.50595(10) 0.45536(6) 0.71370(3) 0.01870(17) Uani 1 1 d . . . . .
O1 O -0.1622(3) 0.24961(17) 0.68163(9) 0.0174(4) Uani 1 1 d . . . . .
O2 O 0.1734(3) 0.13576(15) 0.67265(9) 0.0182(4) Uani 1 1 d . . . . .
N1 N 0.1670(3) 0.32017(19) 0.73278(10) 0.0128(5) Uani 1 1 d . . . . .
C1 C 0.1239(4) 0.3186(2) 0.60120(12) 0.0136(6) Uani 1 1 d . . . . .
C2 C -0.0301(5) 0.3892(2) 0.57250(12) 0.0168(6) Uani 1 1 d . . . . .
H2 H -0.166417 0.398896 0.591763 0.020 Uiso 1 1 calc R U . . .
C3 C 0.0186(5) 0.4450(2) 0.51546(12) 0.0177(6) Uani 1 1 d . . . . .
H3 H -0.086051 0.492735 0.495450 0.021 Uiso 1 1 calc R U . . .
C4 C 0.2190(5) 0.4324(2) 0.48677(13) 0.0180(6) Uani 1 1 d . . . . .
C5 C 0.3702(5) 0.3634(2) 0.51707(13) 0.0187(6) Uani 1 1 d . . . . .
H5 H 0.507988 0.355316 0.498555 0.022 Uiso 1 1 calc R U . . .
C6 C 0.3241(5) 0.3058(2) 0.57396(13) 0.0168(6) Uani 1 1 d . . . . .
H6 H 0.428871 0.258098 0.593990 0.020 Uiso 1 1 calc R U . . .
C7 C 0.2669(5) 0.4910(3) 0.42378(14) 0.0245(7) Uani 1 1 d . . . . .
H7A H 0.189525 0.450932 0.389359 0.037 Uiso 1 1 calc R U . . .
H7B H 0.420614 0.487208 0.415332 0.037 Uiso 1 1 calc R U . . .
H7C H 0.221610 0.572891 0.425655 0.037 Uiso 1 1 calc R U . . .
C8 C 0.0924(4) 0.4415(2) 0.74315(13) 0.0160(6) Uani 1 1 d . . . . .
H8A H 0.088416 0.459108 0.789588 0.019 Uiso 1 1 calc R U . . .
H8B H -0.053476 0.451156 0.725664 0.019 Uiso 1 1 calc R U . . .
C9 C 0.2455(4) 0.5244(2) 0.70944(14) 0.0169(6) Uani 1 1 d . . . . .
H9A H 0.247779 0.601337 0.731177 0.020 Uiso 1 1 calc R U . . .
H9B H 0.202171 0.536060 0.664258 0.020 Uiso 1 1 calc R U . . .
C10 C 0.3979(4) 0.3150(2) 0.74300(12) 0.0136(6) Uani 1 1 d . . . . .
H10 H 0.457315 0.250786 0.715809 0.016 Uiso 1 1 calc R U . . .
C11 C 0.4507(4) 0.2883(2) 0.81296(12) 0.0137(6) Uani 1 1 d . . . . .
C12 C 0.6381(4) 0.3286(3) 0.84103(13) 0.0199(6) Uani 1 1 d . . . . .
H12 H 0.727661 0.380951 0.818068 0.024 Uiso 1 1 calc R U . . .
C13 C 0.6955(5) 0.2933(3) 0.90222(14) 0.0240(7) Uani 1 1 d . . . . .
H13 H 0.824750 0.320621 0.920724 0.029 Uiso 1 1 calc R U . . .
C14 C 0.5651(5) 0.2184(2) 0.93629(14) 0.0240(7) Uani 1 1 d . . . . .
H14 H 0.604653 0.194007 0.978158 0.029 Uiso 1 1 calc R U . . .
C15 C 0.3765(5) 0.1790(2) 0.90920(14) 0.0219(7) Uani 1 1 d . . . . .
H15 H 0.285034 0.128651 0.932793 0.026 Uiso 1 1 calc R U . . .
C16 C 0.3210(5) 0.2132(2) 0.84737(13) 0.0171(6) Uani 1 1 d . . . . .
H16 H 0.192958 0.184736 0.828653 0.020 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'
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
_geom_angle_publ_flag
O1 S1 N1 106.09(11) . . ?
O1 S1 C1 107.50(12) . . ?
O2 S1 O1 119.99(12) . . ?
O2 S1 N1 106.04(11) . . ?
O2 S1 C1 108.13(12) . . ?
N1 S1 C1 108.68(12) . . ?
C9 S2 C10 93.76(12) . . ?
C8 N1 S1 118.37(18) . . ?
C10 N1 S1 118.42(18) . . ?
C10 N1 C8 109.2(2) . . ?
C2 C1 S1 119.7(2) . . ?
C6 C1 S1 119.5(2) . . ?
C6 C1 C2 120.8(2) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 118.9(3) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.2(3) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C7 120.4(2) . . ?
C5 C4 C3 118.5(2) . . ?
C5 C4 C7 121.0(3) . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.2(3) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 119.3(3) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 H8A 110.0 . . ?
N1 C8 H8B 110.0 . . ?
N1 C8 C9 108.6(2) . . ?
H8A C8 H8B 108.4 . . ?
C9 C8 H8A 110.0 . . ?
C9 C8 H8B 110.0 . . ?
S2 C9 H9A 110.6 . . ?
S2 C9 H9B 110.6 . . ?
C8 C9 S2 105.80(17) . . ?
C8 C9 H9A 110.6 . . ?
C8 C9 H9B 110.6 . . ?
H9A C9 H9B 108.7 . . ?
S2 C10 H10 108.3 . . ?
N1 C10 S2 106.19(18) . . ?
N1 C10 H10 108.3 . . ?
N1 C10 C11 111.2(2) . . ?
C11 C10 S2 114.27(18) . . ?
C11 C10 H10 108.3 . . ?
C12 C11 C10 121.2(2) . . ?
C16 C11 C10 119.6(2) . . ?
C16 C11 C12 118.9(2) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.1(3) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.7(3) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
C11 C16 C15 120.6(3) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
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
S1 O1 1.4334(18) . ?
S1 O2 1.4305(18) . ?
S1 N1 1.639(2) . ?
S1 C1 1.756(3) . ?
S2 C9 1.815(3) . ?
S2 C10 1.847(3) . ?
N1 C8 1.481(3) . ?
N1 C10 1.464(3) . ?
C1 C2 1.394(4) . ?
C1 C6 1.385(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.398(4) . ?
C4 C5 1.386(4) . ?
C4 C7 1.506(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(4) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.521(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10 1.0000 . ?
C10 C11 1.528(3) . ?
C11 C12 1.391(4) . ?
C11 C16 1.383(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.380(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.392(4) . ?
C16 H16 0.9500 . ?
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
_geom_torsion_publ_flag
S1 N1 C8 C9 -94.7(2) . . . . ?
S1 N1 C10 S2 104.45(18) . . . . ?
S1 N1 C10 C11 -130.7(2) . . . . ?
S1 C1 C2 C3 -179.3(2) . . . . ?
S1 C1 C6 C5 179.9(2) . . . . ?
S2 C10 C11 C12 -30.5(3) . . . . ?
S2 C10 C11 C16 156.0(2) . . . . ?
O1 S1 N1 C8 -54.4(2) . . . . ?
O1 S1 N1 C10 169.79(19) . . . . ?
O1 S1 C1 C2 14.8(2) . . . . ?
O1 S1 C1 C6 -165.7(2) . . . . ?
O2 S1 N1 C8 176.93(18) . . . . ?
O2 S1 N1 C10 41.2(2) . . . . ?
O2 S1 C1 C2 145.7(2) . . . . ?
O2 S1 C1 C6 -34.8(3) . . . . ?
N1 S1 C1 C2 -99.6(2) . . . . ?
N1 S1 C1 C6 79.9(2) . . . . ?
N1 C8 C9 S2 -32.3(2) . . . . ?
N1 C10 C11 C12 -150.7(2) . . . . ?
N1 C10 C11 C16 35.8(3) . . . . ?
C1 S1 N1 C8 60.9(2) . . . . ?
C1 S1 N1 C10 -74.9(2) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C2 C1 C6 C5 -0.6(4) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C2 C3 C4 C7 178.2(3) . . . . ?
C3 C4 C5 C6 1.3(4) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
C6 C1 C2 C3 1.2(4) . . . . ?
C7 C4 C5 C6 -177.6(3) . . . . ?
C8 N1 C10 S2 -35.0(2) . . . . ?
C8 N1 C10 C11 89.8(3) . . . . ?
C9 S2 C10 N1 13.56(19) . . . . ?
C9 S2 C10 C11 -109.3(2) . . . . ?
C10 S2 C9 C8 10.47(19) . . . . ?
C10 N1 C8 C9 44.8(3) . . . . ?
C10 C11 C12 C13 -172.9(3) . . . . ?
C10 C11 C16 C15 174.0(2) . . . . ?
C11 C12 C13 C14 -0.8(4) . . . . ?
C12 C11 C16 C15 0.3(4) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
C13 C14 C15 C16 1.2(4) . . . . ?
C14 C15 C16 C11 -1.3(4) . . . . ?
C16 C11 C12 C13 0.7(4) . . . . ?
