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#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/71/4127150.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_4127150
loop_
_publ_author_name
'Paul, Mithun'
'Chakraborty, Shaunak'
'Desiraju, Gautam R.'
_publ_section_title
;
 Six-component Molecular Solids, ABC[D1-(x+y)ExFy]2.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b12501
_journal_year                    2018
_chemical_formula_moiety
'C12 H12 N2, C10 H8 N2, C8 H12 N2, 2(C6 H5 Br O2)'
_chemical_formula_sum            'C42 H42 Br2 N6 O4'
_chemical_formula_weight         854.63
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                97.665(10)
_cell_angle_beta                 96.437(9)
_cell_angle_gamma                91.771(4)
_cell_formula_units_Z            1
_cell_length_a                   7.569(4)
_cell_length_b                   8.821(5)
_cell_length_c                   14.499(8)
_cell_measurement_reflns_used    3578
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33.6
_cell_measurement_theta_min      2.3
_cell_volume                     952.3(9)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0879
_diffrn_reflns_av_unetI/netI     0.0819
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10156
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         1.427
_exptl_absorpt_coefficient_mu    2.180
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.662
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_description       Block
_exptl_crystal_F_000             438
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.160
_refine_diff_density_max         1.027
_refine_diff_density_min         -1.115
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.872
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4368
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.872
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0447
_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/[σ²(Fo²)+(0.0853P)²+0.7095P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1307
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3994
_reflns_number_total             4368
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b12501_si_003.cif
_cod_data_source_block           QT5
_cod_original_cell_volume        952.4(9)
_cod_database_code               4127150
_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_min   0.571
_shelx_estimated_absorpt_t_max   0.722
_shelxl_version_number           2013-2
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
Br1 Br 0.83557(3) 0.55531(3) 0.35959(2) 0.02574(12) Uani 1 1 d . .
O1 O 1.1680(3) 0.3825(2) 0.38947(14) 0.0273(4) Uani 1 1 d . .
H1 H 1.2491 0.3230 0.3890 0.041 Uiso 1 1 calc R U
O2 O 0.9148(3) 0.7582(3) 0.21836(15) 0.0296(4) Uani 1 1 d . .
H2 H 0.9320 0.8054 0.1749 0.044 Uiso 1 1 calc R U
C1 C 1.0485(3) 0.5742(3) 0.30447(18) 0.0197(5) Uani 1 1 d . .
C2 C 1.0609(4) 0.6797(3) 0.24147(18) 0.0222(5) Uani 1 1 d . .
C6 C 1.1919(4) 0.4848(3) 0.32916(18) 0.0210(5) Uani 1 1 d . .
C3 C 1.2228(4) 0.7019(3) 0.2062(2) 0.0258(6) Uani 1 1 d . .
H3 H 1.2344 0.7741 0.1658 0.031 Uiso 1 1 calc R U
C5 C 1.3514(4) 0.5070(3) 0.2918(2) 0.0253(5) Uani 1 1 d . .
H5 H 1.4479 0.4487 0.3072 0.030 Uiso 1 1 calc R U
C4 C 1.3664(4) 0.6157(4) 0.2319(2) 0.0285(6) Uani 1 1 d . .
H4 H 1.4741 0.6311 0.2085 0.034 Uiso 1 1 calc R U
N2 N 0.9713(3) 0.9192(3) 0.07224(16) 0.0232(5) Uani 1 1 d . .
C14 C 0.9291(4) 0.8547(3) -0.0173(2) 0.0227(5) Uani 1 1 d . .
C15 C 1.0427(4) 1.0630(3) 0.09087(19) 0.0230(5) Uani 1 1 d . .
C17 C 0.4603(4) 0.9266(3) -0.0273(2) 0.0263(6) Uani 1 1 d . .
N3 N 0.4240(4) 0.8147(3) 0.02280(18) 0.0322(6) Uani 1 1 d . .
C18 C 0.4277(4) 0.9089(4) -0.1246(2) 0.0305(6) Uani 1 1 d . .
H18 H 0.4538 0.9889 -0.1574 0.037 Uiso 1 1 calc R U
C21 C 0.3555(5) 0.6806(4) -0.0242(2) 0.0364(7) Uani 1 1 d . .
H21 H 0.3305 0.6022 0.0100 0.044 Uiso 1 1 calc R U
C20 C 0.3201(4) 0.6525(4) -0.1206(2) 0.0344(7) Uani 1 1 d . .
H20 H 0.2737 0.5574 -0.1505 0.041 Uiso 1 1 calc R U
C16 C 1.0898(4) 1.1294(4) 0.1916(2) 0.0325(6) Uani 1 1 d . .
H16A H 1.0600 1.0554 0.2310 0.049 Uiso 1 1 calc R U
H16B H 1.0243 1.2196 0.2052 0.049 Uiso 1 1 calc R U
H16C H 1.2150 1.1557 0.2033 0.049 Uiso 1 1 calc R U
C19 C 0.3556(4) 0.7698(4) -0.1719(2) 0.0337(7) Uani 1 1 d . .
H19 H 0.3315 0.7554 -0.2369 0.040 Uiso 1 1 calc R U
C13 C 0.8531(4) 0.6927(3) -0.0338(2) 0.0335(7) Uani 1 1 d . .
H13A H 0.8442 0.6571 0.0253 0.050 Uiso 1 1 calc R U
H13B H 0.9295 0.6286 -0.0688 0.050 Uiso 1 1 calc R U
H13C H 0.7369 0.6891 -0.0685 0.050 Uiso 1 1 calc R U
N1 N 0.4503(3) 0.1951(3) 0.41288(18) 0.0280(5) Uani 1 1 d . .
C8 C 0.7911(4) 0.0751(3) 0.43498(18) 0.0231(5) Uani 1 1 d . .
C7 C 0.9754(4) 0.0132(3) 0.44895(19) 0.0260(6) Uani 1 1 d . .
H7A H 1.0619 0.0853 0.4323 0.031 Uiso 1 1 calc R U
H7B H 0.9792 -0.0826 0.4079 0.031 Uiso 1 1 calc R U
C12 C 0.7603(4) 0.2246(3) 0.4724(2) 0.0297(6) Uani 1 1 d . .
H12 H 0.8533 0.2879 0.5053 0.036 Uiso 1 1 calc R U
C9 C 0.6445(4) -0.0126(3) 0.3867(2) 0.0283(6) Uani 1 1 d . .
H9 H 0.6575 -0.1133 0.3607 0.034 Uiso 1 1 calc R U
C10 C 0.4790(4) 0.0514(3) 0.3776(2) 0.0296(6) Uani 1 1 d . .
H10 H 0.3830 -0.0092 0.3453 0.035 Uiso 1 1 calc R U
C11 C 0.5917(4) 0.2779(3) 0.4603(2) 0.0316(6) Uani 1 1 d . .
H11 H 0.5744 0.3776 0.4867 0.038 Uiso 1 1 calc R U
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'
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'
Br Br -0.2901 2.4595 '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
C6 O1 H1 109.5 . .
C2 O2 H2 109.5 . .
C2 C1 C6 121.4(2) . .
C2 C1 Br1 119.1(2) . .
C6 C1 Br1 119.5(2) . .
O2 C2 C1 118.1(2) . .
O2 C2 C3 122.8(2) . .
C1 C2 C3 119.0(2) . .
O1 C6 C5 123.6(2) . .
O1 C6 C1 117.8(2) . .
C5 C6 C1 118.5(2) . .
C4 C3 C2 119.8(3) . .
C4 C3 H3 120.1 . .
C2 C3 H3 120.1 . .
C6 C5 C4 120.2(3) . .
C6 C5 H5 119.9 . .
C4 C5 H5 119.9 . .
C3 C4 C5 121.0(3) . .
C3 C4 H4 119.5 . .
C5 C4 H4 119.5 . .
C15 N2 C14 119.7(2) . .
N2 C14 C15 120.4(2) . 2_775
N2 C14 C13 117.3(3) . .
C15 C14 C13 122.3(3) 2_775 .
N2 C15 C14 120.0(2) . 2_775
N2 C15 C16 117.7(3) . .
C14 C15 C16 122.3(3) 2_775 .
N3 C17 C18 122.6(3) . .
N3 C17 C17 116.3(3) . 2_675
C18 C17 C17 121.2(3) . 2_675
C17 N3 C21 117.7(3) . .
C19 C18 C17 118.9(3) . .
C19 C18 H18 120.6 . .
C17 C18 H18 120.6 . .
N3 C21 C20 123.6(3) . .
N3 C21 H21 118.2 . .
C20 C21 H21 118.2 . .
C21 C20 C19 118.3(3) . .
C21 C20 H20 120.8 . .
C19 C20 H20 120.8 . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C20 C19 C18 118.9(3) . .
C20 C19 H19 120.5 . .
C18 C19 H19 120.5 . .
C14 C13 H13A 109.5 . .
C14 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C14 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C10 N1 C11 116.4(3) . .
C9 C8 C12 116.7(3) . .
C9 C8 C7 122.8(3) . .
C12 C8 C7 120.5(3) . .
C8 C7 C7 111.0(3) . 2_756
C8 C7 H7A 109.4 . .
C7 C7 H7A 109.4 2_756 .
C8 C7 H7B 109.4 . .
C7 C7 H7B 109.4 2_756 .
H7A C7 H7B 108.0 . .
C11 C12 C8 119.6(3) . .
C11 C12 H12 120.2 . .
C8 C12 H12 120.2 . .
C8 C9 C10 119.6(3) . .
C8 C9 H9 120.2 . .
C10 C9 H9 120.2 . .
N1 C10 C9 123.5(3) . .
N1 C10 H10 118.2 . .
C9 C10 H10 118.2 . .
N1 C11 C12 124.1(3) . .
N1 C11 H11 117.9 . .
C12 C11 H11 117.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C1 1.890(3) .
O1 C6 1.359(3) .
O1 H1 0.8200 .
O2 C2 1.357(3) .
O2 H2 0.8200 .
C1 C2 1.396(4) .
C1 C6 1.404(4) .
C2 C3 1.398(4) .
C6 C5 1.396(4) .
C3 C4 1.391(4) .
C3 H3 0.9300 .
C5 C4 1.388(4) .
C5 H5 0.9300 .
C4 H4 0.9300 .
N2 C15 1.345(4) .
N2 C14 1.345(4) .
C14 C15 1.400(4) 2_775
C14 C13 1.502(4) .
C15 C14 1.400(4) 2_775
C15 C16 1.499(4) .
C17 N3 1.340(4) .
C17 C18 1.392(4) .
C17 C17 1.495(6) 2_675
N3 C21 1.342(4) .
C18 C19 1.386(4) .
C18 H18 0.9300 .
C21 C20 1.381(5) .
C21 H21 0.9300 .
C20 C19 1.389(5) .
C20 H20 0.9300 .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
C19 H19 0.9300 .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
N1 C10 1.336(4) .
N1 C11 1.343(4) .
C8 C9 1.396(4) .
C8 C12 1.394(4) .
C8 C7 1.517(4) .
C7 C7 1.536(6) 2_756
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C12 C11 1.375(4) .
C12 H12 0.9300 .
C9 C10 1.390(4) .
C9 H9 0.9300 .
C10 H10 0.9300 .
C11 H11 0.9300 .
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_4
C6 C1 C2 O2 177.7(2) . .
Br1 C1 C2 O2 -3.7(3) . .
C6 C1 C2 C3 -3.4(4) . .
Br1 C1 C2 C3 175.2(2) . .
C2 C1 C6 O1 -178.7(2) . .
Br1 C1 C6 O1 2.8(3) . .
C2 C1 C6 C5 2.3(4) . .
Br1 C1 C6 C5 -176.29(19) . .
O2 C2 C3 C4 -179.0(3) . .
C1 C2 C3 C4 2.1(4) . .
O1 C6 C5 C4 -178.8(3) . .
C1 C6 C5 C4 0.1(4) . .
C2 C3 C4 C5 0.3(4) . .
C6 C5 C4 C3 -1.4(4) . .
C15 N2 C14 C15 -0.7(4) . 2_775
C15 N2 C14 C13 178.9(3) . .
C14 N2 C15 C14 0.7(4) . 2_775
C14 N2 C15 C16 -179.2(3) . .
C18 C17 N3 C21 0.7(5) . .
C17 C17 N3 C21 -178.8(3) 2_675 .
N3 C17 C18 C19 -0.3(5) . .
C17 C17 C18 C19 179.3(3) 2_675 .
C17 N3 C21 C20 -0.3(5) . .
N3 C21 C20 C19 -0.7(5) . .
C21 C20 C19 C18 1.1(5) . .
C17 C18 C19 C20 -0.7(5) . .
C9 C8 C7 C7 -107.5(4) . 2_756
C12 C8 C7 C7 71.2(4) . 2_756
C9 C8 C12 C11 -0.1(4) . .
C7 C8 C12 C11 -178.9(3) . .
C12 C8 C9 C10 0.4(4) . .
C7 C8 C9 C10 179.2(3) . .
C11 N1 C10 C9 -1.0(5) . .
C8 C9 C10 N1 0.1(5) . .
C10 N1 C11 C12 1.4(5) . .
C8 C12 C11 N1 -0.8(5) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139125980
