A systematic investigation on the impact of the level of oxidation at sulfur and the configuration of R/S-sulfoxide on the solid structure
Zhou, Yanan; Ma, Hongzhi; Yang, Zhongxing; Wu, Chengjun; Sun, Tiemin; CrystEngComm 23 (2021) 4181–4193; doi:10.1039/D1CE00346A

data_7242856
_publ_section_title
;
 A systematic investigation on the impact of the level of oxidation at
 sulfur and the configuration of R/S-sulfoxide on the solid structure
;
_journal_issue                   23
_journal_name_full               CrystEngComm
_journal_page_first              4181
_journal_page_last               4193
_journal_paper_doi               10.1039/D1CE00346A
_journal_volume                  23
_journal_year                    2021
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C21 H20 Br N O4 S'
_chemical_formula_sum            'C21 H20 Br N O4 S'
_chemical_formula_weight         462.35
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2019-12-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-07 deposited with the CCDC.	2021-05-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.354(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.4439(3)
_cell_length_b                   7.6636(4)
_cell_length_c                   20.6198(10)
_cell_measurement_reflns_used    1859
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      70.3290
_cell_measurement_theta_min      4.3040
_cell_volume                     1013.83(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -22.00  69.00   1.00    2.00    --    0.00  57.00 -60.00   91
  2  \w    -58.00  -2.00   1.00    2.00    --    0.00 125.00 179.00   56
  3  \w    -17.00  85.00   1.00    2.00    --   53.63 -77.00-180.00  102
  4  \w     32.00 123.00   1.00    2.00    --   53.63  57.00 -60.00   91
  5  \w      4.00 128.00   1.00    2.00    --   53.63  19.00  60.00  124
  6  \w     64.00  92.00   1.00    2.00    --   53.63-125.00 -60.00   28
  7  \w    113.00 140.00   1.00    2.00    --  107.26 111.00-180.00   27
  8  \w     71.00 147.00   1.00    2.00    --  107.26 -25.00  90.00   76
  9  \w     95.00 171.00   1.00    2.00    --  107.26  38.00  90.00   76
 10  \w     50.00 131.00   1.00    2.00    --  107.26 -63.00 -90.00   81
 11  \w     36.00 131.00   1.00    2.00    --  107.26 -91.00-180.00   95
 12  \w     97.00 168.00   1.00    2.00    --  107.26  63.00 -60.00   71
 13  \w     65.00 119.00   1.00    2.00    --  107.26 -91.00   0.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0639897000
_diffrn_orient_matrix_UB_12      0.1216245000
_diffrn_orient_matrix_UB_13      -0.0579321000
_diffrn_orient_matrix_UB_21      -0.0159916000
_diffrn_orient_matrix_UB_22      0.1538599000
_diffrn_orient_matrix_UB_23      0.0474244000
_diffrn_orient_matrix_UB_31      0.2306419000
_diffrn_orient_matrix_UB_32      0.0446970000
_diffrn_orient_matrix_UB_33      -0.0054586000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            3920
_diffrn_reflns_point_group_measured_fraction_full 0.767
_diffrn_reflns_point_group_measured_fraction_max 0.741
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.793
_diffrn_reflns_theta_min         1.984
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.157
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.706
_refine_diff_density_min         -1.097
_refine_diff_density_rms         0.142
_refine_ls_abs_structure_details
;
 Flack x determined using 709 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.37(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         2897
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0683
_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/[\s^2^(Fo^2^)+(0.1291P)^2^+2.1821P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1848
_refine_ls_wR_factor_ref         0.1911
_reflns_Friedel_coverage         0.416
_reflns_Friedel_fraction_full    0.500
_reflns_Friedel_fraction_max     0.473
_reflns_number_gt                2655
_reflns_number_total             2897
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00346a2.cif
_cod_data_source_block           13
_cod_depositor_comments
'Adding full bibliography for 7242854--7242857.cif.'
_cod_original_cell_volume        1013.85(8)
_cod_database_code               7242856
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H O'
_shelx_estimated_absorpt_t_max   0.900
_shelx_estimated_absorpt_t_min   0.813
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C7(H7), C9(H9), C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C10(H10), C11(H11), C13(H13), C15(H15), C16(H16), C17(H17), C18(H18),
 C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              74709
_shelx_hkl_checksum              56120
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.087
_oxdiff_exptl_absorpt_empirical_full_min 0.503