Pnictogen bonding in imide derivatives for chiral folding and self-assembly.
Wang, Zhuoer; Cao, Zhaozhen; Hao, Aiyou; Xing, Pengyao; Chemical science 15 (2024) 6924–6933; doi:10.1039/d4sc00554f

data_1571403
_publ_section_title
;
 Pnictogen bonding in imide derivatives for chiral folding and
 self-assembly.
;
_journal_issue                   18
_journal_name_full               'Chemical science'
_journal_page_first              6924
_journal_page_last               6933
_journal_paper_doi               10.1039/d4sc00554f
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C21 H16 Br N O3'
_chemical_formula_sum            'C21 H16 Br N O3'
_chemical_formula_weight         410.26
_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     iterative
_audit_creation_date             2022-05-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2023-11-22 deposited with the CCDC.	2024-04-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.310(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.5671(2)
_cell_length_b                   6.22015(11)
_cell_length_c                   14.7354(3)
_cell_measurement_reflns_used    5653
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      75.4750
_cell_measurement_theta_min      4.7470
_cell_volume                     849.68(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.943
_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     92.00 169.00   1.00    0.10    --  105.98  15.00  90.00   77
  2  \w     89.00 169.00   1.00    0.10    --  105.98  65.00 151.00   80
  3  \w     81.00 113.00   1.00    0.10    --   48.21  65.00 151.00   32
  4  \w     41.00  66.00   1.00    0.10    --   48.21 -65.00  15.00   25
  5  \w    -19.00  37.00   1.00    0.10    --   48.21 -65.00  15.00   56
  6  \w     38.00  69.00   1.00    0.10    --  105.98 -61.00 120.00   31
  7  \w     34.00  70.00   1.00    0.10    --  105.98 -61.00  60.00   36
  8  \w     33.00  78.00   1.00    0.10    --  105.98 -65.00  15.00   45
  9  \w     39.00 108.00   1.00    0.10    --  105.98-125.00 -30.00   69
 10  \w    -40.00  24.00   1.00    0.10    --  -48.21  65.00 151.00   64
 11  \w    -27.00  26.00   1.00    0.10    --  -48.21  19.00 150.00   53
 12  \w    -51.00 -26.00   1.00    0.10    --  -91.75  45.00 150.00   25
 13  \w    -47.00 -19.00   1.00    0.10    --  -91.75  65.00 151.00   28
 14  \w    -78.00 -52.00   1.00    0.10    --  -91.75  65.00 151.00   26
 15  \w    -46.00 -20.00   1.00    0.10    --  -91.75  45.00   0.00   26
 16  \w    -71.00 -19.00   1.00    0.10    --  -91.75  61.00 -30.00   52
 17  \w    -48.00 -20.00   1.00    0.10    --  -91.75  45.00-150.00   28
 18  \w    -65.00 -34.00   1.00    0.10    --  -48.21 -65.00  15.00   31
 19  \w   -112.00 -80.00   1.00    0.10    --  -48.21 -65.00  15.00   32
 20  \w   -124.00 -99.00   1.00    0.10    --  -91.75 -65.00  15.00   25
 21  \w   -163.00 -80.00   1.00    0.10    --  -91.75 -45.00  60.00   83
 22  \w   -166.00 -81.00   1.00    0.10    --  -91.75 -30.00 -60.00   85
 23  \w   -131.00 -82.00   1.00    0.10    --  -91.75 -30.00 -90.00   49
 24  \w   -165.00-138.00   1.00    0.10    --  -91.75 -30.00 -90.00   27
 25  \w   -157.00 -88.00   1.00    0.10    --  -91.75 -45.00-120.00   69
 26  \w   -116.00 -80.00   1.00    0.10    --  -91.75 -61.00 -90.00   36
 27  \w   -160.00-123.00   1.00    0.10    --  -91.75 -61.00 -90.00   37
 28  \w   -161.00-135.00   1.00    0.10    --  -91.75 -94.00 150.00   26
 29  \w   -124.00 -91.00   1.00    0.10    --  -91.75 -94.00 150.00   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1458682000
_diffrn_orient_matrix_UB_12      -0.0223871000
_diffrn_orient_matrix_UB_13      0.0258340000
_diffrn_orient_matrix_UB_21      0.0622327000
_diffrn_orient_matrix_UB_22      -0.1839197000
_diffrn_orient_matrix_UB_23      0.0680934000
_diffrn_orient_matrix_UB_31      0.0497659000
_diffrn_orient_matrix_UB_32      0.1641826000
_diffrn_orient_matrix_UB_33      0.0796483000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7846
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.087
_diffrn_reflns_theta_min         3.095
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.480
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.119a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_description       needle
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 1245 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.037(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3212
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0370
_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^)+(0.0650P)^2^+0.0088P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.0999
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.861
_reflns_number_gt                3066
_reflns_number_total             3212
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc00554f2.cif
_cod_data_source_block           20220525wzeb_auto
_cod_depositor_comments
'Adding full bibliography for 1571402--1571406.cif.'
_cod_database_code               1571403
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CONBr
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.903
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C20(H20), C19(H19), C21(H21), C5(H5), C4(H4), C3(H3A),
 C18(H18), C17(H17)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              25733
_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 1.386
_oxdiff_exptl_absorpt_empirical_full_min 0.520