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#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
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#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/71/4127149.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.
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data_4127149
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, C12 H10, C8 H12 N2, 2(C6 H5 Cl O2)'
_chemical_formula_sum            'C44 H44 Cl2 N4 O4'
_chemical_formula_weight         763.73
_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                97.653(14)
_cell_angle_beta                 98.49(2)
_cell_angle_gamma                91.167(7)
_cell_formula_units_Z            1
_cell_length_a                   7.574(7)
_cell_length_b                   8.936(9)
_cell_length_c                   14.572(15)
_cell_measurement_reflns_used    2892
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      33.5
_cell_measurement_theta_min      2.5
_cell_volume                     965.9(17)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1549
_diffrn_reflns_av_unetI/netI     0.1280
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_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            10259
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         1.426
_exptl_absorpt_coefficient_mu    0.217
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       Block
_exptl_crystal_F_000             402
_exptl_crystal_size_max          0.570
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.230
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4420
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0685
_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/[σ²(Fo²)+(0.0632P)²+0.1033P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1935
_refine_ls_wR_factor_ref         0.2078
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3439
_reflns_number_total             4420
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b12501_si_003.cif
_cod_data_source_block           QT4
_cod_original_cell_volume        966.0(16)
_cod_database_code               4127149
_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   0.886
_shelx_estimated_absorpt_t_max   0.952
_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
Cl1 Cl 0.65765(8) 0.44117(7) 0.14814(5) 0.0482(2) Uani 1 1 d . .
O1 O 0.5958(3) 0.2410(2) 0.28279(15) 0.0527(5) Uani 1 1 d . .
H1 H 0.5796 0.1972 0.3270 0.079 Uiso 1 1 calc R U
C1 C 0.4616(3) 0.4233(2) 0.19474(15) 0.0348(5) Uani 1 1 d . .
O2 O 0.3394(3) 0.6122(2) 0.10872(13) 0.0485(5) Uani 1 1 d . .
H2 H 0.2517 0.6644 0.1034 0.073 Uiso 1 1 calc R U
C2 C 0.4496(3) 0.3197(3) 0.25691(16) 0.0378(5) Uani 1 1 d . .
C6 C 0.3177(3) 0.5110(3) 0.16809(16) 0.0368(5) Uani 1 1 d . .
C8 C 0.7087(3) 0.9197(3) 0.06524(17) 0.0428(6) Uani 1 1 d . .
N1 N 1.0470(3) 0.7957(3) 0.08678(17) 0.0512(6) Uani 1 1 d . .
C5 C 0.1587(3) 0.4896(3) 0.20301(19) 0.0460(6) Uani 1 1 d . .
H5 H 0.0613 0.5472 0.1862 0.055 Uiso 1 1 calc R U
C3 C 0.2885(4) 0.2991(3) 0.2897(2) 0.0481(6) Uani 1 1 d . .
H3 H 0.2776 0.2282 0.3300 0.058 Uiso 1 1 calc R U
C4 C 0.1453(3) 0.3836(3) 0.2623(2) 0.0499(6) Uani 1 1 d . .
H4 H 0.0379 0.3689 0.2842 0.060 Uiso 1 1 calc R U
C7 C 0.5265(4) 0.9860(3) 0.05073(19) 0.0510(6) Uani 1 1 d . .
H7A H 0.5274 1.0806 0.0921 0.061 Uiso 1 1 calc R U
H7B H 0.4387 0.9172 0.0666 0.061 Uiso 1 1 calc R U
C12 C 0.8612(4) 1.0070(3) 0.1085(2) 0.0506(7) Uani 1 1 d . .
H12 H 0.8526 1.1085 0.1312 0.061 Uiso 1 1 calc R U
C10 C 0.8989(4) 0.7138(3) 0.0447(2) 0.0531(7) Uani 1 1 d . .
H10 H 0.9113 0.6130 0.0218 0.064 Uiso 1 1 calc R U
C9 C 0.7314(4) 0.7699(3) 0.0334(2) 0.0509(7) Uani 1 1 d . .
H9 H 0.6336 0.7075 0.0045 0.061 Uiso 1 1 calc R U
C11 C 1.0244(4) 0.9402(3) 0.1171(2) 0.0554(7) Uani 1 1 d . .
H11 H 1.1247 0.9997 0.1458 0.066 Uiso 1 1 calc R U
N2 N 0.5255(3) 0.0809(2) 0.42885(14) 0.0396(5) Uani 1 1 d . .
C20 C 0.5648(3) 0.1450(2) 0.51861(17) 0.0376(5) Uani 1 1 d . .
C21 C 0.4605(3) -0.0619(3) 0.40982(17) 0.0402(5) Uani 1 1 d . .
C22 C 0.4145(5) -0.1286(3) 0.3085(2) 0.0593(8) Uani 1 1 d . .
H22A H 0.4416 -0.0552 0.2696 0.089 Uiso 1 1 calc R U
H22B H 0.2894 -0.1568 0.2947 0.089 Uiso 1 1 calc R U
H22C H 0.4830 -0.2163 0.2965 0.089 Uiso 1 1 calc R U
C19 C 0.6339(4) 0.3065(3) 0.5367(2) 0.0543(7) Uani 1 1 d . .
H19A H 0.6419 0.3423 0.4781 0.082 Uiso 1 1 calc R U
H19B H 0.7501 0.3131 0.5740 0.082 Uiso 1 1 calc R U
H19C H 0.5538 0.3673 0.5695 0.082 Uiso 1 1 calc R U
C18 C 0.9648(3) 0.9242(3) 0.47528(19) 0.0444(6) Uani 1 1 d . .
C15 C 0.8301(4) 0.6384(4) 0.3850(3) 0.0659(9) Uani 1 1 d . .
H15 H 0.7861 0.5437 0.3551 0.079 Uiso 1 1 calc R U
C17 C 0.9367(5) 0.8056(4) 0.5249(2) 0.0618(8) Uani 1 1 d . .
H17 H 0.9641 0.8212 0.5899 0.074 Uiso 1 1 calc R U
C13 C 0.9227(5) 0.8947(3) 0.3790(2) 0.0610(8) Uani 1 1 d . .
H13 H 0.9391 0.9713 0.3433 0.073 Uiso 1 1 calc R U
C14 C 0.8565(5) 0.7535(4) 0.3342(2) 0.0697(9) Uani 1 1 d . .
H14 H 0.8298 0.7368 0.2692 0.084 Uiso 1 1 calc R U
C16 C 0.8698(5) 0.6659(4) 0.4809(3) 0.0705(9) Uani 1 1 d . .
H16 H 0.8512 0.5895 0.5163 0.085 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'
Cl Cl 0.1484 0.1585 '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
C2 O1 H1 109.5 . .
C2 C1 C6 121.0(2) . .
C2 C1 Cl1 119.33(17) . .
C6 C1 Cl1 119.61(18) . .
C6 O2 H2 109.5 . .
O1 C2 C1 118.5(2) . .
O1 C2 C3 122.4(2) . .
C1 C2 C3 119.1(2) . .
O2 C6 C1 118.1(2) . .
O2 C6 C5 123.3(2) . .
C1 C6 C5 118.6(2) . .
C9 C8 C12 117.3(2) . .
C9 C8 C7 120.6(2) . .
C12 C8 C7 122.0(2) . .
C11 N1 C10 116.2(2) . .
C4 C5 C6 120.2(2) . .
C4 C5 H5 119.9 . .
C6 C5 H5 119.9 . .
C4 C3 C2 119.9(2) . .
C4 C3 H3 120.0 . .
C2 C3 H3 120.0 . .
C3 C4 C5 121.0(2) . .
C3 C4 H4 119.5 . .
C5 C4 H4 119.5 . .
C8 C7 C7 111.2(3) . 2_675
C8 C7 H7A 109.4 . .
C7 C7 H7A 109.4 2_675 .
C8 C7 H7B 109.4 . .
C7 C7 H7B 109.4 2_675 .
H7A C7 H7B 108.0 . .
C11 C12 C8 119.0(3) . .
C11 C12 H12 120.5 . .
C8 C12 H12 120.5 . .
N1 C10 C9 124.1(3) . .
N1 C10 H10 118.0 . .
C9 C10 H10 118.0 . .
C10 C9 C8 119.5(3) . .
C10 C9 H9 120.3 . .
C8 C9 H9 120.3 . .
N1 C11 C12 123.9(3) . .
N1 C11 H11 118.0 . .
C12 C11 H11 118.0 . .
C21 N2 C20 119.2(2) . .
N2 C20 C21 119.8(2) . 2_656
N2 C20 C19 117.4(2) . .
C21 C20 C19 122.8(2) 2_656 .
N2 C21 C20 121.0(2) . 2_656
N2 C21 C22 117.6(2) . .
C20 C21 C22 121.4(2) 2_656 .
C21 C22 H22A 109.5 . .
C21 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C21 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C20 C19 H19A 109.5 . .
C20 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C20 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C13 C18 C17 116.6(3) . .
C13 C18 C18 122.3(3) . 2_776
C17 C18 C18 121.1(3) . 2_776
C16 C15 C14 118.7(3) . .
C16 C15 H15 120.7 . .
C14 C15 H15 120.7 . .
C16 C17 C18 122.0(3) . .
C16 C17 H17 119.0 . .
C18 C17 H17 119.0 . .
C18 C13 C14 121.6(3) . .
C18 C13 H13 119.2 . .
C14 C13 H13 119.2 . .
C15 C14 C13 120.6(3) . .
C15 C14 H14 119.7 . .
C13 C14 H14 119.7 . .
C15 C16 C17 120.6(3) . .
C15 C16 H16 119.7 . .
C17 C16 H16 119.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C1 1.735(3) .
O1 C2 1.357(3) .
O1 H1 0.8200 .
C1 C2 1.390(3) .
C1 C6 1.394(3) .
O2 C6 1.356(3) .
O2 H2 0.8200 .
C2 C3 1.392(4) .
C6 C5 1.394(4) .
C8 C9 1.380(4) .
C8 C12 1.399(4) .
C8 C7 1.511(4) .
N1 C11 1.331(4) .
N1 C10 1.346(4) .
C5 C4 1.376(4) .
C5 H5 0.9300 .
C3 C4 1.375(4) .
C3 H3 0.9300 .
C4 H4 0.9300 .
C7 C7 1.529(6) 2_675
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C12 C11 1.380(4) .
C12 H12 0.9300 .
C10 C9 1.369(4) .
C10 H10 0.9300 .
C9 H9 0.9300 .
C11 H11 0.9300 .
N2 C21 1.337(3) .
N2 C20 1.344(3) .
C20 C21 1.391(4) 2_656
C20 C19 1.500(4) .
C21 C20 1.391(4) 2_656
C21 C22 1.504(4) .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 0.9600 .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C18 C13 1.380(4) .
C18 C17 1.390(4) .
C18 C18 1.495(5) 2_776
C15 C16 1.373(6) .
C15 C14 1.373(5) .
C15 H15 0.9300 .
C17 C16 1.376(5) .
C17 H17 0.9300 .
C13 C14 1.389(5) .
C13 H13 0.9300 .
C14 H14 0.9300 .
C16 H16 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 O1 -177.9(2) . .
Cl1 C1 C2 O1 3.3(3) . .
C6 C1 C2 C3 2.8(4) . .
Cl1 C1 C2 C3 -176.09(19) . .
C2 C1 C6 O2 178.7(2) . .
Cl1 C1 C6 O2 -2.5(3) . .
C2 C1 C6 C5 -1.8(3) . .
Cl1 C1 C6 C5 177.01(19) . .
O2 C6 C5 C4 179.3(2) . .
C1 C6 C5 C4 -0.2(4) . .
O1 C2 C3 C4 179.0(3) . .
C1 C2 C3 C4 -1.7(4) . .
C2 C3 C4 C5 -0.3(5) . .
C6 C5 C4 C3 1.3(4) . .
C9 C8 C7 C7 -75.6(4) . 2_675
C12 C8 C7 C7 102.5(4) . 2_675
C9 C8 C12 C11 0.1(4) . .
C7 C8 C12 C11 -178.1(3) . .
C11 N1 C10 C9 -1.1(5) . .
N1 C10 C9 C8 1.0(5) . .
C12 C8 C9 C10 -0.4(4) . .
C7 C8 C9 C10 177.8(3) . .
C10 N1 C11 C12 0.7(4) . .
C8 C12 C11 N1 -0.3(5) . .
C21 N2 C20 C21 0.7(4) . 2_656
C21 N2 C20 C19 -178.8(2) . .
C20 N2 C21 C20 -0.7(4) . 2_656
C20 N2 C21 C22 178.7(2) . .
C13 C18 C17 C16 -0.3(5) . .
C18 C18 C17 C16 179.1(3) 2_776 .
C17 C18 C13 C14 -0.3(5) . .
C18 C18 C13 C14 -179.6(3) 2_776 .
C16 C15 C14 C13 0.2(5) . .
C18 C13 C14 C15 0.3(5) . .
C14 C15 C16 C17 -0.8(6) . .
C18 C17 C16 C15 0.8(6) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139125979
