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_7060870
_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 S Se'
_chemical_formula_sum            'C12 H10 Br N S Se'
_chemical_formula_weight         359.14
_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             2017-03-23
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2019-09-24 deposited with the CCDC.	2021-07-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.49830(10)
_cell_length_b                   7.8011(2)
_cell_length_c                   21.5964(3)
_cell_measurement_reflns_used    7632
_cell_measurement_temperature    293
_cell_measurement_theta_max      68.7660
_cell_measurement_theta_min      4.0650
_cell_volume                     1263.28(4)
_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 0.997
_diffrn_measured_fraction_theta_max 0.994
_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    -42.00  92.00   1.00    1.00    --    0.00  57.00-150.00  134
  2  \w   -147.00 -79.00   1.00   10.00    --  -52.94 -99.00-150.00   68
  3  \w   -147.00 -79.00   1.00   10.00    --  -52.94 -99.00 150.00   68
  4  \w     94.00 145.00   1.00   10.00    --   52.94 125.00 -60.00   51
  5  \w    -47.00  96.00   1.00   10.00    --   52.94 -77.00  60.00  143
  6  \w     15.00 152.00   1.00   20.00    --  105.88 -38.00 -60.00  137
  7  \w     64.00 178.00   1.00   20.00    --  105.88  50.00-150.00  114
  8  \w     12.00 150.00   1.00   20.00    --  105.88 -63.00  90.00  138
  9  \w     59.00 178.00   1.00   20.00    --  105.88  38.00-180.00  119
 10  \w     18.00 118.00   1.00   20.00    --  105.88-118.00 111.00  100
 11  \w   -101.00 -35.00   1.00    1.00    --    0.00-178.00 -60.00   66
 12  \w   -145.00 -11.00   1.00   10.00    --  -52.94 -57.00  90.00  134
 13  \w   -144.00  -6.00   1.00   10.00    --  -52.94 -38.00-150.00  138
 14  \w   -144.00  -6.00   1.00   10.00    --  -52.94 -38.00 -30.00  138
 15  \w     59.00 178.00   1.00   20.00    --  105.88  38.00 -30.00  119
 16  \w     62.00 178.00   1.00   20.00    --  105.88  63.00  30.00  116
 17  \w    100.00 178.00   1.00   20.00    --  105.88 111.00  60.00   78
 18  \w     64.00 178.00   1.00   20.00    --  105.88  50.00 -90.00  114
 19  \w     62.00 178.00   1.00   20.00    --  105.88  63.00  90.00  116
 20  \w    -92.00  42.00   1.00    1.00    --    0.00 -57.00-150.00  134
 21  \w   -153.00-116.00   1.00   10.00    --  -52.94 -77.00-180.00   37
;
_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      0.1842338000
_diffrn_orient_matrix_UB_12      0.0234486000
_diffrn_orient_matrix_UB_13      0.0304082000
_diffrn_orient_matrix_UB_21      -0.0863863000
_diffrn_orient_matrix_UB_22      -0.0138642000
_diffrn_orient_matrix_UB_23      0.0645172000
_diffrn_orient_matrix_UB_31      0.0282937000
_diffrn_orient_matrix_UB_32      -0.1956185000
_diffrn_orient_matrix_UB_33      -0.0009570000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11206
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.845
_diffrn_reflns_theta_min         4.094
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    9.033
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55647
_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    1.888
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 890 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.033(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2313
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0243
_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^)+(0.0271P)^2^+0.7769P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0611
_refine_ls_wR_factor_ref         0.0621
_reflns_Friedel_coverage         0.687
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                2243
_reflns_number_total             2313
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj03178c2.cif
_cod_data_source_block           se5br1
_cod_depositor_comments
'Adding full bibliography for 7060869--7060872.cif.'
_cod_database_code               7060870
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'c12 h10 Br1 n1 S1 Se1 '
_diffrn_oxdiff_ac3_digest_frames
;
01566d660f1d9561259bcb6f16fbc634e400031dc5e
;
_diffrn_oxdiff_ac3_digest_hkl
;
01537d13261c39bdd5ce080d65c47b74569f0e
;
_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:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
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 1.731
_oxdiff_exptl_absorpt_empirical_full_min 0.586