#------------------------------------------------------------------------------
#$Date: 2024-07-05 17:04:20 +0200 (Fri 05 de Jul de 2024) $
#$Revision: 292912 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/14/1571402.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1571402
loop_
_publ_author_name
'Wang, Zhuoer'
'Cao, Zhaozhen'
'Hao, Aiyou'
'Xing, Pengyao'
_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_formula_moiety         'C15 H11 Br0.975 N O3'
_chemical_formula_sum            'C15 H11 Br0.97 N O3'
_chemical_formula_weight         330.76
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-11-22
_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                96.710(4)
_cell_angle_beta                 92.275(4)
_cell_angle_gamma                111.131(6)
_cell_formula_units_Z            2
_cell_length_a                   7.4015(4)
_cell_length_b                   8.5478(6)
_cell_length_c                   11.0934(5)
_cell_measurement_reflns_used    3665
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      29.9660
_cell_measurement_theta_min      2.9530
_cell_volume                     647.62(7)
_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    'SHELXT  (Sheldrick, 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 1.000
_diffrn_measured_fraction_theta_max 0.808
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00  -4.00   1.00    3.82    --    5.67 -19.00 -30.00   65
  2  ω    -60.00 -15.00   1.00    3.82    --    5.67 -38.00  30.00   45
  3  ω    -65.00  15.00   1.00    3.82    --    5.67 -43.00  84.00   80
  4  ω     -8.00  18.00   1.00    3.82    --    5.67 -99.00  90.00   26
  5  ω     -7.00  78.00   1.00    3.82    --    5.67  43.00-123.00   85
  6  ω    -23.00  29.00   1.00    3.82    --   -4.50 -99.00  60.00   52
  7  ω    -15.00  11.00   1.00    3.82    --   -4.50 -99.00 -30.00   26
  8  ω    -23.00  14.00   1.00    3.82    --   -4.50 -99.00-150.00   37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0517099000
_diffrn_orient_matrix_UB_12      -0.0817380000
_diffrn_orient_matrix_UB_13      -0.0326895000
_diffrn_orient_matrix_UB_21      -0.0892391000
_diffrn_orient_matrix_UB_22      0.0095587000
_diffrn_orient_matrix_UB_23      0.0117240000
_diffrn_orient_matrix_UB_31      0.0010149000
_diffrn_orient_matrix_UB_32      0.0360811000
_diffrn_orient_matrix_UB_33      -0.0545100000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_unetI/netI     0.0669
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.808
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9238
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.808
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.855
_diffrn_reflns_theta_min         2.580
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86084
_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    1.696
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.785
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.142
_refine_ls_extinction_coef       0.020(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.199
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3286
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.199
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0504P)²+0.9002P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1404
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2576
_reflns_number_total             3286
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc00554f2.cif
_cod_data_source_block           20220719co2_auto
_cod_depositor_comments
'Adding full bibliography for 1571402--1571406.cif.'
_cod_database_code               1571402
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CONBr
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.913
_shelx_estimated_absorpt_t_min   0.836
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C14(H14), C15(H15), C10(H10)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_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 1.242
_oxdiff_exptl_absorpt_empirical_full_min 0.762
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br13 Br -0.03629(7) 0.23583(6) 0.70518(4) 0.02848(19) Uani 0.885(4) 1 d . . . A
1
O20 O 0.6304(4) 0.8938(4) 0.3425(2) 0.0282(7) Uani 1 1 d . . . . .
O18 O 0.3401(5) 0.8754(4) 0.0970(3) 0.0378(8) Uani 1 1 d . . . . .
O21 O 0.2631(5) 0.3791(4) 0.1346(3) 0.0367(8) Uani 1 1 d . . . . .
N6 N 0.4408(5) 0.6386(4) 0.2369(3) 0.0228(7) Uani 1 1 d . . . . .
C8 C 0.4300(5) 0.6962(5) 0.4587(3) 0.0202(8) Uani 1 1 d . . . . .
C3 C 0.2896(5) 0.5310(5) 0.4565(3) 0.0204(8) Uani 1 1 d . . . . .
C2 C 0.2150(6) 0.4783(5) 0.5678(4) 0.0251(9) Uani 1 1 d . . . . .
C7 C 0.5090(5) 0.7542(5) 0.3441(3) 0.0198(8) Uani 1 1 d . . . . .
C4 C 0.2272(5) 0.4191(5) 0.3457(4) 0.0225(8) Uani 1 1 d . . . . .
C9 C 0.4923(6) 0.8053(5) 0.5658(3) 0.0240(8) Uani 1 1 d . . . . .
H9 H 0.585795 0.916030 0.565867 0.029 Uiso 1 1 calc R U . . .
C1 C 0.0743(6) 0.3115(6) 0.5604(4) 0.0275(9) Uani 1 1 d . . . . .
C5 C 0.3073(6) 0.4731(5) 0.2312(4) 0.0251(9) Uani 1 1 d . . . . .
C14 C 0.0131(6) 0.2053(6) 0.4537(4) 0.0306(10) Uani 1 1 d . . . . .
H14 H -0.081582 0.094826 0.452494 0.037 Uiso 1 1 calc R U . . .
C15 C 0.0892(6) 0.2582(5) 0.3449(4) 0.0280(9) Uani 1 1 d . . . . .
H15 H 0.045685 0.183233 0.270476 0.034 Uiso 1 1 calc R U . . .
C11 C 0.2846(6) 0.5958(6) 0.6774(4) 0.0289(9) Uani 1 1 d . . . . .
C10 C 0.4183(6) 0.7540(6) 0.6756(4) 0.0296(9) Uani 1 1 d . . . . .
H10 H 0.462278 0.830596 0.749266 0.036 Uiso 1 1 calc R U . . .
C16 C 0.5185(7) 0.6954(6) 0.1232(4) 0.0313(10) Uani 1 1 d . . . . .
H16A H 0.556979 0.606818 0.078386 0.038 Uiso 1 1 calc R U . . .
H16B H 0.636686 0.799117 0.143234 0.038 Uiso 1 1 calc R U . . .
C17 C 0.3747(7) 0.7322(6) 0.0415(4) 0.0359(11) Uani 1 1 d . . . . .
H17A H 0.427097 0.754186 -0.038212 0.043 Uiso 1 1 calc R U . . .
H17B H 0.251146 0.632831 0.027057 0.043 Uiso 1 1 calc R U . . .
C19 C 0.2037(8) 0.9132(8) 0.0238(5) 0.0533(15) Uani 1 1 d . . . . .
H19A H 0.251231 0.932196 -0.056430 0.080 Uiso 1 1 calc R U . . .
H19B H 0.187359 1.015495 0.063118 0.080 Uiso 1 1 calc R U . . .
H19C H 0.078483 0.818100 0.014302 0.080 Uiso 1 1 calc R U . . .
Br1 Br 0.1332(8) 0.4601(8) 0.7944(4) 0.039(2) Uani 0.090(2) 1 d . . . B 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 O18 C19 111.6(4) . . ?
C7 N6 C16 117.4(3) . . ?
C5 N6 C7 124.6(3) . . ?
C5 N6 C16 118.0(3) . . ?
C3 C8 C7 120.1(3) . . ?
C9 C8 C3 120.7(3) . . ?
C9 C8 C7 119.2(4) . . ?
C8 C3 C2 119.1(3) . . ?
C4 C3 C8 120.3(3) . . ?
C4 C3 C2 120.6(4) . . ?
C3 C2 C11 118.3(4) . . ?
C1 C2 C3 116.7(4) . . ?
C1 C2 C11 124.9(4) . . ?
O20 C7 N6 120.8(3) . . ?
O20 C7 C8 122.0(3) . . ?
N6 C7 C8 117.2(3) . . ?
C3 C4 C5 120.4(3) . . ?
C15 C4 C3 119.6(4) . . ?
C15 C4 C5 120.0(4) . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.3(4) . . ?
C10 C9 H9 119.8 . . ?
C2 C1 Br13 118.8(3) . . ?
C14 C1 Br13 118.8(3) . . ?
C14 C1 C2 122.4(4) . . ?
O21 C5 N6 120.0(4) . . ?
O21 C5 C4 122.6(4) . . ?
N6 C5 C4 117.4(3) . . ?
C1 C14 H14 119.9 . . ?
C1 C14 C15 120.3(4) . . ?
C15 C14 H14 119.9 . . ?
C4 C15 C14 120.3(4) . . ?
C4 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C2 C11 Br1 100.3(3) . . ?
C10 C11 C2 120.8(4) . . ?
C10 C11 Br1 138.9(4) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.7(4) . . ?
C11 C10 H10 119.6 . . ?
N6 C16 H16A 109.0 . . ?
N6 C16 H16B 109.0 . . ?
N6 C16 C17 113.1(4) . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
O18 C17 C16 109.7(4) . . ?
O18 C17 H17A 109.7 . . ?
O18 C17 H17B 109.7 . . ?
C16 C17 H17A 109.7 . . ?
C16 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
O18 C19 H19A 109.5 . . ?
O18 C19 H19B 109.5 . . ?
O18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br13 C1 1.906(4) . ?
O20 C7 1.210(5) . ?
O18 C17 1.417(6) . ?
O18 C19 1.419(6) . ?
O21 C5 1.217(5) . ?
N6 C7 1.401(5) . ?
N6 C5 1.396(5) . ?
N6 C16 1.469(5) . ?
C8 C3 1.417(5) . ?
C8 C7 1.484(5) . ?
C8 C9 1.372(5) . ?
C3 C2 1.427(5) . ?
C3 C4 1.414(5) . ?
C2 C1 1.421(6) . ?
C2 C11 1.430(6) . ?
C4 C5 1.476(6) . ?
C4 C15 1.385(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.407(6) . ?
C1 C14 1.356(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.406(6) . ?
C15 H15 0.9500 . ?
C11 C10 1.360(7) . ?
C11 Br1 1.953(7) . ?
C10 H10 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.511(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br13 C1 C14 C15 178.9(3) . . . . ?
N6 C16 C17 O18 67.3(5) . . . . ?
C8 C3 C2 C1 179.9(3) . . . . ?
C8 C3 C2 C11 0.5(5) . . . . ?
C8 C3 C4 C5 -0.2(5) . . . . ?
C8 C3 C4 C15 -179.7(4) . . . . ?
C8 C9 C10 C11 0.1(6) . . . . ?
C3 C8 C7 O20 -179.3(4) . . . . ?
C3 C8 C7 N6 -0.9(5) . . . . ?
C3 C8 C9 C10 0.5(6) . . . . ?
C3 C2 C1 Br13 -178.2(3) . . . . ?
C3 C2 C1 C14 0.5(6) . . . . ?
C3 C2 C11 C10 0.0(6) . . . . ?
C3 C2 C11 Br1 178.9(3) . . . . ?
C3 C4 C5 O21 177.3(4) . . . . ?
C3 C4 C5 N6 -1.7(5) . . . . ?
C3 C4 C15 C14 -0.8(6) . . . . ?
C2 C3 C4 C5 -178.9(3) . . . . ?
C2 C3 C4 C15 1.5(6) . . . . ?
C2 C1 C14 C15 0.2(6) . . . . ?
C2 C11 C10 C9 -0.4(6) . . . . ?
C7 N6 C5 O21 -176.6(4) . . . . ?
C7 N6 C5 C4 2.4(6) . . . . ?
C7 N6 C16 C17 -105.8(4) . . . . ?
C7 C8 C3 C2 -179.7(3) . . . . ?
C7 C8 C3 C4 1.5(5) . . . . ?
C7 C8 C9 C10 179.4(3) . . . . ?
C4 C3 C2 C1 -1.3(5) . . . . ?
C4 C3 C2 C11 179.3(3) . . . . ?
C9 C8 C3 C2 -0.8(5) . . . . ?
C9 C8 C3 C4 -179.6(3) . . . . ?
C9 C8 C7 O20 1.8(6) . . . . ?
C9 C8 C7 N6 -179.8(3) . . . . ?
C1 C2 C11 C10 -179.3(4) . . . . ?
C1 C2 C11 Br1 -0.4(5) . . . . ?
C1 C14 C15 C4 0.0(6) . . . . ?
C5 N6 C7 O20 177.3(4) . . . . ?
C5 N6 C7 C8 -1.1(5) . . . . ?
C5 N6 C16 C17 75.2(5) . . . . ?
C5 C4 C15 C14 179.6(4) . . . . ?
C15 C4 C5 O21 -3.2(6) . . . . ?
C15 C4 C5 N6 177.8(4) . . . . ?
C11 C2 C1 Br13 1.1(5) . . . . ?
C11 C2 C1 C14 179.8(4) . . . . ?
C16 N6 C7 O20 -1.6(5) . . . . ?
C16 N6 C7 C8 180.0(3) . . . . ?
C16 N6 C5 O21 2.3(6) . . . . ?
C16 N6 C5 C4 -178.7(3) . . . . ?
C19 O18 C17 C16 -179.3(4) . . . . ?
Br1 C11 C10 C9 -178.7(4) . . . . ?
