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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/4/12/71/4127156.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_4127156
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, 2(C6.69 H5 Cl0.31 O2), C8 H12 N2'
_chemical_formula_sum            'C43.39 H40 Cl0.61 N6 O4'
_chemical_formula_weight         731.21
_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-2014/7
_cell_angle_alpha                96.481(13)
_cell_angle_beta                 93.678(14)
_cell_angle_gamma                91.954(10)
_cell_formula_units_Z            1
_cell_length_a                   7.547(5)
_cell_length_b                   8.833(6)
_cell_length_c                   14.336(10)
_cell_measurement_reflns_used    2900
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33.5
_cell_measurement_theta_min      1.4
_cell_volume                     946.8(11)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0860
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_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            10063
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         2.707
_exptl_absorpt_coefficient_mu    0.125
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       block
_exptl_crystal_F_000             384.8
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4333
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0661
_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)+(0.1068P)²+0.1568P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1927
_refine_ls_wR_factor_ref         0.2051
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3481
_reflns_number_total             4333
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b12501_si_003.cif
_cod_data_source_block           QN6
_cod_original_cell_volume        946.7(12)
_cod_database_code               4127156
_shelx_shelxl_version_number     2014/7
_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.
;
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
C25 C 0.5713(4) -0.3766(3) 0.19198(16) 0.0585(6) Uani 1 1 d . . .
H25A H 0.6188 -0.2737 0.1953 0.088 Uiso 1 1 calc R U .
H25B H 0.4633 -0.3775 0.2238 0.088 Uiso 1 1 calc R U .
H25C H 0.6561 -0.4378 0.2215 0.088 Uiso 1 1 calc R U .
C1 C 1.2722(3) -0.4443(2) 0.44794(14) 0.0426(4) Uani 1 1 d . . .
C2 C 1.1354(3) -0.5165(2) 0.38835(15) 0.0500(5) Uani 1 1 d . . .
H2 H 1.1488 -0.6142 0.3586 0.060 Uiso 1 1 calc R U .
C3 C 0.9797(3) -0.4436(3) 0.37317(16) 0.0521(5) Uani 1 1 d . . .
H3 H 0.8895 -0.4949 0.3334 0.063 Uiso 1 1 calc R U .
C5 C 1.0832(3) -0.2337(2) 0.46913(18) 0.0580(6) Uani 1 1 d . . .
H5 H 1.0660 -0.1358 0.4975 0.070 Uiso 1 1 calc R U .
C6 C 1.2439(3) -0.2977(2) 0.48843(18) 0.0556(6) Uani 1 1 d . . .
H6 H 1.3321 -0.2432 0.5281 0.067 Uiso 1 1 calc R U .
C7 C 1.4361(3) -0.5235(2) 0.46743(16) 0.0495(5) Uani 1 1 d . . .
H7 H 1.4514 -0.6150 0.4305 0.059 Uiso 1 1 calc R U .
C8 C 0.1644(3) -0.1524(3) 0.11483(19) 0.0595(6) Uani 1 1 d . . .
H8 H 0.2072 -0.0573 0.1434 0.071 Uiso 1 1 calc R U .
C9 C 0.1259(3) -0.2678(3) 0.16763(18) 0.0616(6) Uani 1 1 d . . .
H9 H 0.1431 -0.2522 0.2329 0.074 Uiso 1 1 calc R U .
C10 C 0.0613(3) -0.4073(3) 0.12309(16) 0.0534(5) Uani 1 1 d . . .
H10 H 0.0354 -0.4872 0.1577 0.064 Uiso 1 1 calc R U .
C11 C 0.0356(2) -0.4262(2) 0.02582(14) 0.0420(4) Uani 1 1 d . . .
C13 C 0.1382(3) -0.1808(3) 0.01893(18) 0.0604(6) Uani 1 1 d . . .
H13 H 0.1658 -0.1027 -0.0168 0.073 Uiso 1 1 calc R U .
C14 C 0.5267(2) 0.0594(2) 0.30924(12) 0.0358(4) Uani 1 1 d . . .
C15 C 0.6755(3) -0.0216(2) 0.33340(12) 0.0383(4) Uani 1 1 d . . .
C16 C 0.8381(3) 0.0093(2) 0.29759(15) 0.0470(5) Uani 1 1 d . . .
H16 H 0.9367 -0.0451 0.3137 0.056 Uiso 1 1 calc R U .
C17 C 0.8529(3) 0.1213(3) 0.23799(16) 0.0504(5) Uani 1 1 d . . .
H17 H 0.9624 0.1429 0.2151 0.060 Uiso 1 1 calc R U .
C18 C 0.7075(3) 0.2009(2) 0.21221(15) 0.0461(5) Uani 1 1 d . . .
H18 H 0.7185 0.2755 0.1718 0.055 Uiso 1 1 calc R U .
C19 C 0.5441(2) 0.1692(2) 0.24682(13) 0.0390(4) Uani 1 1 d . . .
C20 C 0.6392(3) -0.1932(2) 0.03216(19) 0.0578(6) Uani 1 1 d . . .
H20A H 0.6575 -0.1616 0.0985 0.087 Uiso 1 1 calc R U .
H20B H 0.7503 -0.1862 0.0035 0.087 Uiso 1 1 calc R U .
H20C H 0.5562 -0.1284 0.0045 0.087 Uiso 1 1 calc R U .
C22 C 0.5669(2) -0.3549(2) 0.01655(14) 0.0398(4) Uani 1 1 d . . .
C23 C 0.5334(2) -0.4402(2) 0.09071(14) 0.0405(4) Uani 1 1 d . . .
N1 N 0.9517(2) -0.3033(2) 0.41255(13) 0.0506(4) Uani 1 1 d . . .
N2 N 0.4662(2) -0.58328(17) 0.07266(11) 0.0404(4) Uani 1 1 d . . .
N3 N 0.0751(3) -0.3148(2) -0.02644(14) 0.0549(5) Uani 1 1 d . . .
O1 O 0.6527(2) -0.12967(17) 0.39257(10) 0.0510(4) Uani 1 1 d . . .
H1 H 0.7376 -0.1852 0.3914 0.076 Uiso 1 1 calc R U .
O2 O 0.3948(2) 0.24361(19) 0.22285(11) 0.0547(4) Uani 1 1 d . . .
H2A H 0.4140 0.2932 0.1792 0.082 Uiso 1 1 calc R U .
Cl1 Cl 0.3426(5) 0.0312(4) 0.3527(2) 0.0423(8) Uani 0.3069 1 d . . P
C100 C 0.3291(14) 0.0260(13) 0.3542(8) 0.086(3) Uani 0.6931 1 d . . P
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
C23 C25 H25A 109.5 . .
C23 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
C23 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
C6 C1 C2 116.79(19) . .
C6 C1 C7 122.83(19) . .
C2 C1 C7 120.36(19) . .
C3 C2 C1 120.0(2) . .
C3 C2 H2 120.0 . .
C1 C2 H2 120.0 . .
N1 C3 C2 123.3(2) . .
N1 C3 H3 118.3 . .
C2 C3 H3 118.3 . .
N1 C5 C6 124.0(2) . .
N1 C5 H5 118.0 . .
C6 C5 H5 118.0 . .
C5 C6 C1 119.1(2) . .
C5 C6 H6 120.4 . .
C1 C6 H6 120.4 . .
C7 C7 C1 126.0(3) 2_846 .
C7 C7 H7 117.0 2_846 .
C1 C7 H7 117.0 . .
C9 C8 C13 118.3(2) . .
C9 C8 H8 120.8 . .
C13 C8 H8 120.8 . .
C8 C9 C10 119.4(2) . .
C8 C9 H9 120.3 . .
C10 C9 H9 120.3 . .
C9 C10 C11 118.8(2) . .
C9 C10 H10 120.6 . .
C11 C10 H10 120.6 . .
N3 C11 C10 122.23(19) . .
N3 C11 C11 116.7(2) . 2_545
C10 C11 C11 121.1(2) . 2_545
N3 C13 C8 123.7(2) . .
N3 C13 H13 118.1 . .
C8 C13 H13 118.1 . .
C15 C14 C19 118.67(17) . .
C15 C14 Cl1 121.15(17) . .
C19 C14 Cl1 120.16(16) . .
C15 C14 C100 120.9(4) . .
C19 C14 C100 120.4(4) . .
Cl1 C14 C100 1.1(5) . .
O1 C15 C16 122.60(17) . .
O1 C15 C14 117.06(17) . .
C16 C15 C14 120.34(17) . .
C17 C16 C15 119.84(18) . .
C17 C16 H16 120.1 . .
C15 C16 H16 120.1 . .
C18 C17 C16 120.76(19) . .
C18 C17 H17 119.6 . .
C16 C17 H17 119.6 . .
C17 C18 C19 119.65(19) . .
C17 C18 H18 120.2 . .
C19 C18 H18 120.2 . .
O2 C19 C18 122.18(17) . .
O2 C19 C14 117.12(17) . .
C18 C19 C14 120.69(17) . .
C22 C20 H20A 109.5 . .
C22 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C22 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
N2 C22 C23 120.22(17) 2_645 .
N2 C22 C20 117.07(18) 2_645 .
C23 C22 C20 122.7(2) . .
N2 C23 C22 120.16(18) . .
N2 C23 C25 117.69(18) . .
C22 C23 C25 122.15(18) . .
C5 N1 C3 116.70(18) . .
C23 N2 C22 119.62(16) . 2_645
C11 N3 C13 117.5(2) . .
C15 O1 H1 109.5 . .
C19 O2 H2A 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C25 C23 1.502(3) .
C25 H25A 0.9600 .
C25 H25B 0.9600 .
C25 H25C 0.9600 .
C1 C6 1.387(3) .
C1 C2 1.386(3) .
C1 C7 1.468(3) .
C2 C3 1.375(3) .
C2 H2 0.9300 .
C3 N1 1.333(3) .
C3 H3 0.9300 .
C5 N1 1.328(3) .
C5 C6 1.381(3) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 C7 1.320(4) 2_846
C7 H7 0.9300 .
C8 C9 1.370(4) .
C8 C13 1.370(4) .
C8 H8 0.9300 .
C9 C10 1.380(3) .
C9 H9 0.9300 .
C10 C11 1.386(3) .
C10 H10 0.9300 .
C11 N3 1.339(3) .
C11 C11 1.490(4) 2_545
C13 N3 1.341(3) .
C13 H13 0.9300 .
C14 C15 1.398(3) .
C14 C19 1.400(3) .
C14 Cl1 1.582(5) .
C14 C100 1.692(10) .
C15 O1 1.360(2) .
C15 C16 1.391(3) .
C16 C17 1.384(3) .
C16 H16 0.9300 .
C17 C18 1.377(3) .
C17 H17 0.9300 .
C18 C19 1.389(3) .
C18 H18 0.9300 .
C19 O2 1.368(2) .
C20 C22 1.499(3) .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C22 N2 1.337(3) 2_645
C22 C23 1.401(3) .
C23 N2 1.337(3) .
N2 C22 1.337(3) 2_645
O1 H1 0.8200 .
O2 H2A 0.8200 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.82 1.98 2.789(3) 169.6 .
O2 H2A N2 0.82 2.03 2.846(3) 178.9 1_565
