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#$Date: 2018-02-06 02:46:13 +0200 (Tue, 06 Feb 2018) $
#$Revision: 206201 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/71/4127147.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_4127147
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 H10 N2, C10 H8 N2, C8 H12 N2, 2(C6 H5 Cl O2)'
_chemical_formula_sum            'C42 H40 Cl2 N6 O4'
_chemical_formula_weight         763.70
_chemical_name_systematic
;
 ?
;
_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                97.218(15)
_cell_angle_beta                 94.706(12)
_cell_angle_gamma                92.604(16)
_cell_formula_units_Z            1
_cell_length_a                   7.522(7)
_cell_length_b                   8.820(8)
_cell_length_c                   14.383(14)
_cell_measurement_reflns_used    3056
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33.7
_cell_measurement_theta_min      2.3
_cell_volume                     942.0(15)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      293(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  0.1019
_diffrn_reflns_av_unetI/netI     0.0849
_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            10059
_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         27.499
_diffrn_reflns_theta_min         1.433
_exptl_absorpt_coefficient_mu    0.224
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       Block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.610
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4319
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0577
_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)+(0.0671P)²+0.1791P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1548
_refine_ls_wR_factor_ref         0.1651
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3604
_reflns_number_total             4319
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b12501_si_003.cif
_cod_data_source_block           QT2
_cod_database_code               4127147
_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   0.875
_shelx_estimated_absorpt_t_max   0.967
_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 0.65635(6) 0.96224(6) 0.14653(4) 0.04711(17) Uani 1 1 d . .
C17 C 0.4567(2) 0.9328(2) 0.19445(12) 0.0334(4) Uani 1 1 d . .
O2 O 0.3336(2) 1.11970(19) 0.10944(10) 0.0505(4) Uani 1 1 d . .
H2 H 0.2472 1.1731 0.1079 0.076 Uiso 1 1 calc R U
O1 O 0.5929(2) 0.7523(2) 0.28036(11) 0.0528(4) Uani 1 1 d . .
H1 H 0.5731 0.6994 0.3218 0.079 Uiso 1 1 calc R U
C18 C 0.4436(2) 0.8245(2) 0.25662(13) 0.0366(4) Uani 1 1 d . .
C22 C 0.3100(3) 1.0150(2) 0.16914(12) 0.0373(4) Uani 1 1 d . .
C19 C 0.2794(3) 0.7950(2) 0.29149(14) 0.0446(5) Uani 1 1 d . .
H19 H 0.2678 0.7219 0.3323 0.053 Uiso 1 1 calc R U
C21 C 0.1492(3) 0.9848(3) 0.20513(15) 0.0460(5) Uani 1 1 d . .
H21 H 0.0502 1.0387 0.1890 0.055 Uiso 1 1 calc R U
C20 C 0.1351(3) 0.8749(3) 0.26504(15) 0.0471(5) Uani 1 1 d . .
H20 H 0.0257 0.8545 0.2879 0.057 Uiso 1 1 calc R U
N1 N 0.5303(2) 0.58249(18) 0.42756(11) 0.0398(4) Uani 1 1 d . .
C8 C 0.5677(3) 0.6463(2) 0.51710(14) 0.0387(4) Uani 1 1 d . .
C9 C 0.4618(3) 0.4381(2) 0.40954(14) 0.0389(4) Uani 1 1 d . .
C7 C 0.6418(3) 0.8091(2) 0.53405(19) 0.0574(6) Uani 1 1 d . .
H7A H 0.6522 0.8467 0.4748 0.086 Uiso 1 1 calc R U
H7B H 0.7574 0.8141 0.5682 0.086 Uiso 1 1 calc R U
H7C H 0.5630 0.8707 0.5699 0.086 Uiso 1 1 calc R U
C10 C 0.4185(3) 0.3731(3) 0.30836(16) 0.0570(6) Uani 1 1 d . .
H10A H 0.4484 0.4488 0.2689 0.086 Uiso 1 1 calc R U
H10B H 0.2932 0.3442 0.2974 0.086 Uiso 1 1 calc R U
H10C H 0.4862 0.2848 0.2941 0.086 Uiso 1 1 calc R U
C5 C 0.7272(3) 0.4444(2) 0.05334(14) 0.0410(4) Uani 1 1 d . .
N2 N 1.0444(2) 0.2987(2) 0.09155(13) 0.0479(4) Uani 1 1 d . .
C4 C 0.8740(3) 0.5211(2) 0.10733(15) 0.0475(5) Uani 1 1 d . .
H4 H 0.8688 0.6232 0.1322 0.057 Uiso 1 1 calc R U
C1 C 0.7430(3) 0.2902(2) 0.02200(16) 0.0494(5) Uani 1 1 d . .
H1A H 0.6471 0.2325 -0.0119 0.059 Uiso 1 1 calc R U
C6 C 0.5676(3) 0.5264(2) 0.03080(15) 0.0470(5) Uani 1 1 d . .
H6 H 0.5609 0.6241 0.0627 0.056 Uiso 1 1 calc R U
C3 C 1.0265(3) 0.4450(3) 0.12366(15) 0.0503(5) Uani 1 1 d . .
H3 H 1.1232 0.4990 0.1593 0.060 Uiso 1 1 calc R U
C2 C 0.9006(3) 0.2242(3) 0.04142(16) 0.0516(5) Uani 1 1 d . .
H2A H 0.9089 0.1215 0.0186 0.062 Uiso 1 1 calc R U
C15 C 0.9626(3) 0.4263(2) 0.47319(14) 0.0412(4) Uani 1 1 d . .
N3 N 0.9270(3) 0.3130(2) 0.52394(13) 0.0516(5) Uani 1 1 d . .
C16 C 0.9320(3) 0.4078(3) 0.37592(15) 0.0501(5) Uani 1 1 d . .
H16 H 0.9567 0.4886 0.3423 0.060 Uiso 1 1 calc R U
C13 C 0.8607(3) 0.1790(3) 0.47714(18) 0.0585(6) Uani 1 1 d . .
H13 H 0.8353 0.0998 0.5118 0.070 Uiso 1 1 calc R U
C12 C 0.8281(3) 0.1513(3) 0.38108(18) 0.0558(6) Uani 1 1 d . .
H12 H 0.7825 0.0560 0.3516 0.067 Uiso 1 1 calc R U
C11 C 0.8646(3) 0.2684(3) 0.32972(17) 0.0570(6) Uani 1 1 d . .
H11 H 0.8440 0.2536 0.2645 0.068 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
C18 C17 C22 120.99(17) . .
C18 C17 Cl1 119.18(14) . .
C22 C17 Cl1 119.82(15) . .
C22 O2 H2 109.5 . .
C18 O1 H1 109.5 . .
O1 C18 C17 117.85(17) . .
O1 C18 C19 123.03(18) . .
C17 C18 C19 119.12(17) . .
O2 C22 C21 123.52(18) . .
O2 C22 C17 117.59(17) . .
C21 C22 C17 118.88(18) . .
C20 C19 C18 119.4(2) . .
C20 C19 H19 120.3 . .
C18 C19 H19 120.3 . .
C20 C21 C22 120.13(19) . .
C20 C21 H21 119.9 . .
C22 C21 H21 119.9 . .
C19 C20 C21 121.4(2) . .
C19 C20 H20 119.3 . .
C21 C20 H20 119.3 . .
C9 N1 C8 119.42(17) . .
N1 C8 C9 120.16(18) . 2_666
N1 C8 C7 117.62(19) . .
C9 C8 C7 122.22(19) 2_666 .
N1 C9 C8 120.42(18) . 2_666
N1 C9 C10 117.38(19) . .
C8 C9 C10 122.20(19) 2_666 .
C8 C7 H7A 109.5 . .
C8 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C8 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C1 C5 C4 116.67(18) . .
C1 C5 C6 123.14(18) . .
C4 C5 C6 120.18(19) . .
C3 N2 C2 116.09(18) . .
C3 C4 C5 119.6(2) . .
C3 C4 H4 120.2 . .
C5 C4 H4 120.2 . .
C2 C1 C5 119.6(2) . .
C2 C1 H1A 120.2 . .
C5 C1 H1A 120.2 . .
C6 C6 C5 125.7(2) 2_665 .
C6 C6 H6 117.2 2_665 .
C5 C6 H6 117.2 . .
N2 C3 C4 124.0(2) . .
N2 C3 H3 118.0 . .
C4 C3 H3 118.0 . .
N2 C2 C1 124.0(2) . .
N2 C2 H2A 118.0 . .
C1 C2 H2A 118.0 . .
N3 C15 C16 122.10(19) . .
N3 C15 C15 116.4(2) . 2_766
C16 C15 C15 121.5(2) . 2_766
C13 N3 C15 117.4(2) . .
C11 C16 C15 119.1(2) . .
C11 C16 H16 120.4 . .
C15 C16 H16 120.4 . .
N3 C13 C12 124.0(2) . .
N3 C13 H13 118.0 . .
C12 C13 H13 118.0 . .
C13 C12 C11 118.1(2) . .
C13 C12 H12 120.9 . .
C11 C12 H12 120.9 . .
C12 C11 C16 119.2(2) . .
C12 C11 H11 120.4 . .
C16 C11 H11 120.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C17 1.726(2) .
C17 C18 1.394(3) .
C17 C22 1.395(3) .
O2 C22 1.353(3) .
O2 H2 0.8200 .
O1 C18 1.356(2) .
O1 H1 0.8200 .
C18 C19 1.397(3) .
C22 C21 1.382(3) .
C19 C20 1.374(3) .
C19 H19 0.9300 .
C21 C20 1.382(3) .
C21 H21 0.9300 .
C20 H20 0.9300 .
N1 C9 1.338(3) .
N1 C8 1.341(3) .
C8 C9 1.392(3) 2_666
C8 C7 1.499(3) .
C9 C8 1.392(3) 2_666
C9 C10 1.499(3) .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C5 C1 1.391(3) .
C5 C4 1.393(3) .
C5 C6 1.464(3) .
N2 C3 1.332(3) .
N2 C2 1.345(3) .
C4 C3 1.374(3) .
C4 H4 0.9300 .
C1 C2 1.369(3) .
C1 H1A 0.9300 .
C6 C6 1.319(4) 2_665
C6 H6 0.9300 .
C3 H3 0.9300 .
C2 H2A 0.9300 .
C15 N3 1.340(3) .
C15 C16 1.387(3) .
C15 C15 1.487(4) 2_766
N3 C13 1.338(3) .
C16 C11 1.376(3) .
C16 H16 0.9300 .
C13 C12 1.372(4) .
C13 H13 0.9300 .
C12 C11 1.374(4) .
C12 H12 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
C22 C17 C18 O1 -178.02(17) . .
Cl1 C17 C18 O1 3.3(2) . .
C22 C17 C18 C19 2.0(3) . .
Cl1 C17 C18 C19 -176.65(14) . .
C18 C17 C22 O2 179.12(17) . .
Cl1 C17 C22 O2 -2.2(2) . .
C18 C17 C22 C21 -1.4(3) . .
Cl1 C17 C22 C21 177.19(15) . .
O1 C18 C19 C20 179.01(19) . .
C17 C18 C19 C20 -1.0(3) . .
O2 C22 C21 C20 179.31(19) . .
C17 C22 C21 C20 -0.1(3) . .
C18 C19 C20 C21 -0.5(3) . .
C22 C21 C20 C19 1.1(3) . .
C9 N1 C8 C9 1.0(3) . 2_666
C9 N1 C8 C7 -179.13(18) . .
C8 N1 C9 C8 -1.0(3) . 2_666
C8 N1 C9 C10 178.70(18) . .
C1 C5 C4 C3 2.5(3) . .
C6 C5 C4 C3 -176.5(2) . .
C4 C5 C1 C2 -2.9(3) . .
C6 C5 C1 C2 176.1(2) . .
C1 C5 C6 C6 -10.0(5) . 2_665
C4 C5 C6 C6 168.9(3) . 2_665
C2 N2 C3 C4 -0.9(3) . .
C5 C4 C3 N2 -0.7(4) . .
C3 N2 C2 C1 0.6(4) . .
C5 C1 C2 N2 1.4(4) . .
C16 C15 N3 C13 0.3(3) . .
C15 C15 N3 C13 -179.6(2) 2_766 .
N3 C15 C16 C11 -0.7(3) . .
C15 C15 C16 C11 179.2(2) 2_766 .
C15 N3 C13 C12 0.2(4) . .
N3 C13 C12 C11 -0.4(4) . .
C13 C12 C11 C16 0.0(4) . .
C15 C16 C11 C12 0.5(4) . .
