Slight structural modulation around a pivotal bond: high impact on enantiomeric stability
Farran, Daniel; Vanthuyne, Nicolas; Bossa, Giulia; Belot, Vincent; Albalat, Muriel; Jean, Marion; Roussel, Christian; New Journal of Chemistry 45 (2021) 16039–16047; doi:10.1039/D1NJ03178C

data_7060869
_publ_section_title
;
 Slight structural modulation around a pivotal bond: high impact on
 enantiomeric stability
;
_journal_issue                   35
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              16039
_journal_page_last               16047
_journal_paper_doi               10.1039/D1NJ03178C
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C10 H8 Br N S2'
_chemical_formula_sum            'C10 H8 Br N S2'
_chemical_formula_weight         286.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-07-04
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2019-09-24 deposited with the CCDC.	2021-07-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.882(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0030(2)
_cell_length_b                   11.3382(3)
_cell_length_c                   12.9419(3)
_cell_measurement_reflns_used    5054
_cell_measurement_temperature    293
_cell_measurement_theta_max      70.7030
_cell_measurement_theta_min      5.2640
_cell_volume                     1123.73(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_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    -93.00 -63.00   1.00    1.00    --  -17.77 -77.00 -60.00   30
  2  \w    -80.00 -23.00   1.00    1.00    --  -17.77 -38.00  60.00   57
  3  \w   -104.00 -68.00   1.00    1.00    --  -17.77 178.00  30.00   36
  4  \w    -92.00 -63.00   1.00    1.00    --  -17.77 -38.00  90.00   29
  5  \w    -74.00 -47.00   1.00    1.00    --  -17.77 -38.00 120.00   27
  6  \w   -107.00 -60.00   1.00    1.00    --  -17.77-178.00-150.00   47
  7  \w    -59.00  14.00   1.00    1.00    --  -17.77 -77.00 -60.00   73
  8  \w    -32.00  -1.00   1.00    1.00    --  -17.77 -38.00  90.00   31
  9  \w     -5.00  89.00   1.00    1.00    --   17.77  57.00  90.00   94
 10  \w      7.00  57.00   1.00    1.00    --   17.77 -98.00  81.00   50
 11  \w    121.00 148.00   1.00    5.00    --  101.41  61.00  90.00   27
 12  \w     69.00  96.00   1.00    5.00    --  101.41  77.00 150.00   27
 13  \w    116.00 178.00   1.00    5.00    --  101.41  77.00 150.00   62
 14  \w     72.00  99.00   1.00    5.00    --  101.41  61.00 120.00   27
 15  \w     70.00  95.00   1.00    5.00    --  101.41  77.00  90.00   25
 16  \w     72.00  98.00   1.00    5.00    --  101.41  61.00  90.00   26
 17  \w     77.00 120.00   1.00    5.00    --  101.41  45.00 150.00   43
 18  \w    117.00 144.00   1.00    5.00    --  101.41  61.00-180.00   27
 19  \w     73.00  98.00   1.00    5.00    --  101.41  61.00-180.00   25
 20  \w     51.00 113.00   1.00    5.00    --  101.41-125.00-180.00   62
 21  \w     73.00  99.00   1.00    5.00    --  101.41  61.00 150.00   26
 22  \w     30.00 128.00   1.00    5.00    --  101.41 -61.00-180.00   98
 23  \w    116.00 172.00   1.00    5.00    --  101.41  77.00-180.00   56
 24  \w     69.00  96.00   1.00    5.00    --  101.41  77.00 120.00   27
 25  \w    118.00 175.00   1.00    5.00    --  101.41  77.00 120.00   57
 26  \w     73.00 102.00   1.00    5.00    --  101.41  61.00-150.00   29
 27  \w     70.00 114.00   1.00    5.00    --  101.41  77.00-150.00   44
 28  \w    147.00 173.00   1.00    5.00    --  101.41  77.00-150.00   26
 29  \w     77.00 103.00   1.00    5.00    --  101.41  45.00-180.00   26
 30  \w     78.00 105.00   1.00    5.00    --  101.41  45.00 120.00   27
 31  \w     75.00 100.00   1.00    5.00    --  101.41  30.00 120.00   25
 32  \w     69.00  95.00   1.00    5.00    --  101.41  77.00-180.00   26
 33  \w     19.00 109.00   1.00    5.00    --  101.41 -94.00 -30.00   90
 34  \w     76.00 103.00   1.00    5.00    --  101.41  30.00-150.00   27
 35  \w     76.00 103.00   1.00    5.00    --  101.41  30.00 150.00   27
 36  \w    115.00 178.00   1.00    5.00    --  101.41  30.00  60.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1669379000
_diffrn_orient_matrix_UB_12      -0.0459115000
_diffrn_orient_matrix_UB_13      -0.0828295000
_diffrn_orient_matrix_UB_21      -0.1025747000
_diffrn_orient_matrix_UB_22      0.0180525000
_diffrn_orient_matrix_UB_23      0.0827934000
_diffrn_orient_matrix_UB_31      -0.0459906000
_diffrn_orient_matrix_UB_32      0.1265640000
_diffrn_orient_matrix_UB_33      -0.0418246000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9043
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.875
_diffrn_reflns_theta_min         5.289
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    8.122
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.18b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.830
_refine_diff_density_min         -0.760
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2137
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0603P)^2^+0.8094P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1155
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1915
_reflns_number_total             2137
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj03178c2.cif
_cod_data_source_block           s2nbr
_cod_depositor_comments
'Adding full bibliography for 7060869--7060872.cif.'
_cod_database_code               7060869
_shelx_shelxl_version_number     2016/4
_diffrn_oxdiff_ac3_digest_frames
;
01ce9fc470d50645b54cdb0afff71c379f00031762f
;
_diffrn_oxdiff_ac3_digest_hkl
;
011a1ba0913974d4ac2c80cfea3187a7161cd2
;
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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 Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C7(H7), C8(H8), C9(H9)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_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 2.210
_oxdiff_exptl_absorpt_empirical_full_min 0.619