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_7060871
_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_absolute_configuration ad
_chemical_formula_moiety         'C12 H10 Br N S2'
_chemical_formula_sum            'C12 H10 Br N S2'
_chemical_formula_weight         312.24
_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     direct
_audit_creation_date             2017-01-06
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_audit_update_record
;
2019-09-24 deposited with the CCDC.	2021-07-30 downloaded from the CCDC.
;
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   7.39679(7)
_cell_length_b                   7.70635(7)
_cell_length_c                   21.7345(2)
_cell_measurement_reflns_used    10538
_cell_measurement_temperature    293
_cell_measurement_theta_max      67.5830
_cell_measurement_theta_min      4.0630
_cell_volume                     1238.92(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -39.00  58.00   1.00    1.00    --    0.00  77.00   0.00   97
  2  \w     63.00 103.00   1.00    1.00    --    0.00  77.00   0.00   40
  3  \w     59.00 103.00   1.00    1.00    --    0.00 178.00 -30.00   44
  4  \w    109.00 158.00   1.00    2.00    --   54.32 125.00-150.00   49
  5  \w    118.00 173.00   1.00    2.00    --   74.00  71.00-123.52   55
  6  \w    122.00 149.00   1.00    2.00    --   74.00  68.00 -21.62   27
  7  \w    147.00 172.00   1.00    5.00    --   86.00  65.00  36.67   25
  8  \w    147.00 178.00   1.00    5.00    --  108.65 104.00   0.00   31
  9  \w    123.00 176.00   1.00    5.00    --  108.65 104.00 -30.00   53
 10  \w    125.00 171.00   1.00    5.00    --  108.65 104.00-120.00   46
 11  \w     95.00 176.00   1.00    5.00    --  108.65  77.00  30.00   81
 12  \w    132.00 175.00   1.00    2.00    --   70.00  68.00 131.96   43
 13  \w    152.00 178.00   1.00    2.00    --   74.00  71.00 147.45   26
 14  \w     58.00 176.00   1.00    5.00    --  108.65  77.00  90.00  118
 15  \w     59.00  86.00   1.00    5.00    --  108.65  63.00  60.00   27
 16  \w     58.00 178.00   1.00    5.00    --  108.65  77.00  60.00  120
 17  \w     71.00  98.00   1.00    1.00    --    0.00  77.00-150.00   27
 18  \w     67.00  94.00   1.00    2.00    --   62.00  77.00-147.56   27
 19  \w     59.00 176.00   1.00    5.00    --  108.65  77.00 -60.00  117
 20  \w     58.00 149.00   1.00    5.00    --  108.65  77.00 -30.00   91
 21  \w     59.00 178.00   1.00    5.00    --  108.65  77.00-150.00  119
 22  \w     58.00 164.00   1.00    5.00    --  108.65  77.00   0.00  106
 23  \w     59.00 155.00   1.00    5.00    --  108.65  77.00-180.00   96
 24  \w     58.00 145.00   1.00    5.00    --  108.65  77.00-120.00   87
 25  \w     58.00  84.00   1.00    5.00    --  108.65  77.00  30.00   26
 26  \w     58.00 175.00   1.00    5.00    --  108.65  77.00 120.00  117
 27  \w     58.00 178.00   1.00    5.00    --  108.65  77.00 -90.00  120
 28  \w     58.00 177.00   1.00    5.00    --  108.65  77.00 150.00  119
 29  \w     49.00  74.00   1.00    5.00    --  108.65-104.00   0.00   25
 30  \w     60.00 111.00   1.00    5.00    --  108.65-104.00  30.00   51
 31  \w     50.00 103.00   1.00    5.00    --  108.65-104.00 -60.00   53
 32  \w     57.00 113.00   1.00    5.00    --  108.65-104.00-180.00   56
 33  \w     18.00  94.00   1.00    2.00    --   70.00  68.00 -56.98   76
 34  \w     34.00  68.00   1.00    5.00    --   86.00  65.00  36.67   34
 35  \w     23.00  95.00   1.00    2.00    --   74.00  68.00 -21.62   72
 36  \w     24.00  87.00   1.00    2.00    --   74.00  71.00-123.52   63
 37  \w     16.00  48.00   1.00    2.00    --   66.00  78.00-118.28   32
 38  \w      7.00  46.00   1.00    2.00    --   58.00  81.00 -54.10   39
 39  \w     11.00  36.00   1.00    2.00    --   62.00  84.00 -55.21   25
 40  \w     -2.00  23.00   1.00    2.00    --   54.32  95.00 -43.48   25
 41  \w      7.00  32.00   1.00    2.00    --   58.00  80.00  27.56   25
 42  \w     13.00  45.00   1.00    2.00    --   58.00  80.00  50.14   32
 43  \w     11.00  36.00   1.00    2.00    --   62.00  79.00 119.89   25
 44  \w     23.00  66.00   1.00    2.00    --   74.00  71.00 147.45   43
 45  \w     41.00 128.00   1.00    2.00    --   70.00  68.00 170.46   87
 46  \w     20.00  50.00   1.00    2.00    --   70.00  68.00 131.96   30
 47  \w      8.00 158.00   1.00    2.00    --   54.32  45.00 120.00  150
 48  \w     32.00 144.00   1.00    5.00    --  108.65 -91.00  60.00  112
 49  \w      9.00  68.00   1.00    1.00    --    0.00  77.00-150.00   59
 50  \w     -2.00  23.00   1.00    2.00    --   54.32  95.00  85.49   25
 51  \w      8.00  33.00   1.00    2.00    --   58.00  88.00 132.24   25
 52  \w    -89.00 -57.00   1.00    1.00    --    0.00 178.00  90.00   32
 53  \w    -95.00 -19.00   1.00    2.00    --  -54.32 125.00 -90.00   76
 54  \w    -51.00 -23.00   1.00    1.00    --    0.00  77.00-150.00   28
 55  \w    -44.00 -12.00   1.00    1.00    --   14.00 132.00-114.97   32
 56  \w     -1.00  24.00   1.00    2.00    --   54.32  94.00-153.38   25
 57  \w     12.00  45.00   1.00    2.00    --   62.00  77.00-147.56   33
 58  \w    -98.00  32.00   1.00    2.00    --  -54.32  77.00-120.00  130
 59  \w   -162.00  46.00   1.00    2.00    --  -54.32  15.00-120.00  208
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0706271000
_diffrn_orient_matrix_UB_12      -0.1244447000
_diffrn_orient_matrix_UB_13      -0.0499800000
_diffrn_orient_matrix_UB_21      -0.0141789000
_diffrn_orient_matrix_UB_22      -0.1462367000
_diffrn_orient_matrix_UB_23      0.0480986000
_diffrn_orient_matrix_UB_31      -0.1954079000
_diffrn_orient_matrix_UB_32      0.0556210000
_diffrn_orient_matrix_UB_33      0.0145924000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0105
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14017
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.648
_diffrn_reflns_theta_max         67.648
_diffrn_reflns_theta_min         4.068
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.425
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (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    1.674
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 885 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.012(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2225
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0210
_refine_ls_R_factor_gt           0.0208
_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/[\s^2^(Fo^2^)+(0.0250P)^2^+0.5649P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0546
_refine_ls_wR_factor_ref         0.0548
_reflns_Friedel_coverage         0.686
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                2202
_reflns_number_total             2225
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj03178c2.cif
_cod_data_source_block           t5br1
_cod_depositor_comments
'Adding full bibliography for 7060869--7060872.cif.'
_cod_original_cell_volume        1238.91(2)
_cod_database_code               7060871
_shelx_shelxl_version_number     2016/4
_cell_oxdiff_angle_alpha         89.9903(15)
_cell_oxdiff_angle_beta          89.9863(15)
_cell_oxdiff_angle_gamma         89.9915(14)
_cell_oxdiff_length_a            7.39720(13)
_cell_oxdiff_length_b            7.70615(14)
_cell_oxdiff_length_c            21.7339(4)
_cell_oxdiff_measurement_reflns_used 10538
_cell_oxdiff_volume              1238.91(4)
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11)
;
_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 1.375
_oxdiff_exptl_absorpt_empirical_full_min 0.711