#------------------------------------------------------------------------------
#$Date: 2018-02-06 02:46:13 +0200 (Tue, 06 Feb 2018) $
#$Revision: 206201 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/71/4127154.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_4127154
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, 2(C6.24 H5.73 Cl0.76 O2), C8 H12 N2'
_chemical_formula_sum            'C42.48 H43.45 Cl1.52 N6 O4'
_chemical_formula_weight         755.84
_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                97.551(14)
_cell_angle_beta                 95.650(9)
_cell_angle_gamma                92.369(8)
_cell_formula_units_Z            1
_cell_length_a                   7.553(5)
_cell_length_b                   8.823(6)
_cell_length_c                   14.522(10)
_cell_measurement_reflns_used    3253
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33.7
_cell_measurement_theta_min      2.3
_cell_volume                     953.2(11)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_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            10120
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         1.422
_exptl_absorpt_coefficient_mu    0.188
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       block
_exptl_crystal_F_000             398.1
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.813
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         4376
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.813
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0513
_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)+(0.1601P)²+0.2538P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1712
_refine_ls_wR_factor_ref         0.1832
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3829
_reflns_number_total             4376
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b12501_si_003.cif
_cod_data_source_block           QN4
_cod_database_code               4127154
_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
C1 C 1.0476(2) 0.07127(17) 0.30536(10) 0.0337(3) Uani 1 1 d . . .
C2 C 1.1942(2) -0.01185(17) 0.33083(11) 0.0361(3) Uani 1 1 d . . .
C3 C 1.3547(2) 0.0153(2) 0.29528(13) 0.0447(4) Uani 1 1 d . . .
H3 H 1.4531 -0.0389 0.3120 0.054 Uiso 1 1 calc R U .
C4 C 1.3681(2) 0.1233(2) 0.23486(13) 0.0478(4) Uani 1 1 d . . .
H4 H 1.4767 0.1422 0.2122 0.057 Uiso 1 1 calc R U .
C5 C 1.2229(2) 0.2038(2) 0.20758(12) 0.0437(4) Uani 1 1 d . . .
H5 H 1.2336 0.2751 0.1664 0.052 Uiso 1 1 calc R U .
C6 C 1.0605(2) 0.17721(18) 0.24230(11) 0.0370(3) Uani 1 1 d . . .
C7 C 0.9743(3) -0.4889(3) 0.44944(13) 0.0524(5) Uani 1 1 d . . .
H7A H 1.0623 -0.4196 0.4303 0.063 Uiso 1 1 calc R U .
H7B H 0.9748 -0.5865 0.4100 0.063 Uiso 1 1 calc R U .
C8 C 0.7927(2) -0.4252(2) 0.43570(11) 0.0423(4) Uani 1 1 d . . .
C9 C 0.7677(3) -0.2748(2) 0.46990(14) 0.0503(4) Uani 1 1 d . . .
H9 H 0.8627 -0.2121 0.5014 0.060 Uiso 1 1 calc R U .
C10 C 0.6010(3) -0.2186(2) 0.45696(14) 0.0518(5) Uani 1 1 d . . .
H10 H 0.5870 -0.1174 0.4812 0.062 Uiso 1 1 calc R U .
C11 C 0.4820(3) -0.4455(2) 0.37878(14) 0.0510(4) Uani 1 1 d . . .
H11 H 0.3846 -0.5052 0.3475 0.061 Uiso 1 1 calc R U .
C12 C 0.6446(3) -0.5121(2) 0.38871(14) 0.0500(4) Uani 1 1 d . . .
H12 H 0.6549 -0.6138 0.3643 0.060 Uiso 1 1 calc R U .
N2 N 0.4579(2) -0.30015(18) 0.41176(11) 0.0474(4) Uani 1 1 d . . .
O1 O 1.17189(18) -0.11472(15) 0.39120(9) 0.0478(3) Uani 1 1 d . . .
H1 H 1.2579 -0.1683 0.3934 0.072 Uiso 1 1 calc R U .
O2 O 0.91177(18) 0.25043(16) 0.21798(9) 0.0520(3) Uani 1 1 d . . .
H2 H 0.9270 0.2941 0.1727 0.078 Uiso 1 1 calc R U .
C19 C 1.0876(3) 0.6270(2) 0.19093(14) 0.0560(5) Uani 1 1 d . . .
H19A H 1.1357 0.7303 0.1950 0.084 Uiso 0.5 1 calc R U P
H19B H 0.9823 0.6260 0.2230 0.084 Uiso 0.5 1 calc R U P
H19C H 1.1744 0.5661 0.2192 0.084 Uiso 0.5 1 calc R U P
H19D H 1.0592 0.5513 0.2298 0.084 Uiso 0.5 1 calc R U P
H19E H 1.2126 0.6556 0.2018 0.084 Uiso 0.5 1 calc R U P
H19F H 1.0206 0.7155 0.2056 0.084 Uiso 0.5 1 calc R U P
C20 C 1.0409(2) 0.56196(18) 0.08996(11) 0.0385(3) Uani 1 1 d . . .
C21 C 0.9308(2) 0.35387(17) -0.01711(12) 0.0380(3) Uani 1 1 d . . .
C22 C 0.8567(3) 0.1904(2) -0.03431(17) 0.0562(5) Uani 1 1 d . . .
H22A H 0.8332 0.1584 -0.1003 0.084 Uiso 0.5 1 calc R U P
H22B H 0.9416 0.1259 -0.0079 0.084 Uiso 0.5 1 calc R U P
H22C H 0.7480 0.1828 -0.0057 0.084 Uiso 0.5 1 calc R U P
H22D H 0.8487 0.1530 0.0244 0.084 Uiso 0.5 1 calc R U P
H22E H 0.7402 0.1855 -0.0680 0.084 Uiso 0.5 1 calc R U P
H22F H 0.9339 0.1286 -0.0703 0.084 Uiso 0.5 1 calc R U P
N1 N 0.97158(18) 0.41788(15) 0.07162(9) 0.0390(3) Uani 1 1 d . . .
C13 C 0.5698(3) 0.5921(2) 0.12395(13) 0.0513(4) Uani 1 1 d . . .
H13 H 0.5450 0.5115 0.1569 0.062 Uiso 1 1 calc R U .
C14 C 0.5379(2) 0.57391(19) 0.02665(12) 0.0422(4) Uani 1 1 d . . .
C16 C 0.6427(3) 0.8205(2) 0.02426(17) 0.0592(5) Uani 1 1 d . . .
H16 H 0.6691 0.8989 -0.0100 0.071 Uiso 1 1 calc R U .
C17 C 0.6759(3) 0.8495(2) 0.11967(16) 0.0579(5) Uani 1 1 d . . .
H17 H 0.7217 0.9449 0.1492 0.070 Uiso 1 1 calc R U .
C18 C 0.6389(3) 0.7324(3) 0.17058(15) 0.0592(5) Uani 1 1 d . . .
H18 H 0.6602 0.7475 0.2354 0.071 Uiso 1 1 calc R U .
N3 N 0.5748(2) 0.68651(18) -0.02278(12) 0.0525(4) Uani 1 1 d . . .
Cl1 Cl 0.85182(18) 0.04850(10) 0.35283(10) 0.0430(2) Uani 0.7582 1 d . . P
C100 C 0.859(3) 0.019(2) 0.3447(16) 0.0430(2) Uani 0.2418 1 d . . P
H10A H 0.8822 -0.0545 0.3870 0.064 Uiso 0.2418 1 calc R U P
H10B H 0.8101 0.1072 0.3768 0.064 Uiso 0.2418 1 calc R U P
H10C H 0.7759 -0.0259 0.2932 0.064 Uiso 0.2418 1 calc R U 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
C6 C1 C2 120.50(15) . .
C6 C1 C100 124.0(8) . .
C2 C1 C100 115.1(8) . .
C6 C1 Cl1 118.90(13) . .
C2 C1 Cl1 120.58(13) . .
C100 C1 Cl1 9.4(6) . .
O1 C2 C3 123.09(15) . .
O1 C2 C1 117.54(14) . .
C3 C2 C1 119.35(15) . .
C4 C3 C2 119.90(16) . .
C4 C3 H3 120.1 . .
C2 C3 H3 120.1 . .
C3 C4 C5 121.21(16) . .
C3 C4 H4 119.4 . .
C5 C4 H4 119.4 . .
C4 C5 C6 119.57(16) . .
C4 C5 H5 120.2 . .
C6 C5 H5 120.2 . .
O2 C6 C5 122.93(15) . .
O2 C6 C1 117.65(14) . .
C5 C6 C1 119.42(15) . .
C8 C7 C7 112.07(19) . 2_746
C8 C7 H7A 109.2 . .
C7 C7 H7A 109.2 2_746 .
C8 C7 H7B 109.2 . .
C7 C7 H7B 109.2 2_746 .
H7A C7 H7B 107.9 . .
C9 C8 C12 117.16(16) . .
C9 C8 C7 120.11(17) . .
C12 C8 C7 122.74(17) . .
C10 C9 C8 119.37(18) . .
C10 C9 H9 120.3 . .
C8 C9 H9 120.3 . .
N2 C10 C9 124.22(18) . .
N2 C10 H10 117.9 . .
C9 C10 H10 117.9 . .
N2 C11 C12 123.47(17) . .
N2 C11 H11 118.3 . .
C12 C11 H11 118.3 . .
C11 C12 C8 119.39(17) . .
C11 C12 H12 120.3 . .
C8 C12 H12 120.3 . .
C10 N2 C11 116.40(16) . .
C2 O1 H1 109.5 . .
C6 O2 H2 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 . .
C20 C19 H19D 109.5 . .
H19A C19 H19D 141.1 . .
H19B C19 H19D 56.3 . .
H19C C19 H19D 56.3 . .
C20 C19 H19E 109.5 . .
H19A C19 H19E 56.3 . .
H19B C19 H19E 141.1 . .
H19C C19 H19E 56.3 . .
H19D C19 H19E 109.5 . .
C20 C19 H19F 109.5 . .
H19A C19 H19F 56.3 . .
H19B C19 H19F 56.3 . .
H19C C19 H19F 141.1 . .
H19D C19 H19F 109.5 . .
H19E C19 H19F 109.5 . .
N1 C20 C21 120.41(15) . 2_765
N1 C20 C19 117.31(15) . .
C21 C20 C19 122.28(16) 2_765 .
N1 C21 C20 119.98(15) . 2_765
N1 C21 C22 117.68(16) . .
C20 C21 C22 122.34(16) 2_765 .
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 . .
C21 C22 H22D 109.5 . .
H22A C22 H22D 141.1 . .
H22B C22 H22D 56.3 . .
H22C C22 H22D 56.3 . .
C21 C22 H22E 109.5 . .
H22A C22 H22E 56.3 . .
H22B C22 H22E 141.1 . .
H22C C22 H22E 56.3 . .
H22D C22 H22E 109.5 . .
C21 C22 H22F 109.5 . .
H22A C22 H22F 56.3 . .
H22B C22 H22F 56.3 . .
H22C C22 H22F 141.1 . .
H22D C22 H22F 109.5 . .
H22E C22 H22F 109.5 . .
C21 N1 C20 119.61(14) . .
C18 C13 C14 118.83(19) . .
C18 C13 H13 120.6 . .
C14 C13 H13 120.6 . .
N3 C14 C13 122.06(17) . .
N3 C14 C14 117.0(2) . 2_665
C13 C14 C14 120.9(2) . 2_665
N3 C16 C17 124.2(2) . .
N3 C16 H16 117.9 . .
C17 C16 H16 117.9 . .
C16 C17 C18 117.93(18) . .
C16 C17 H17 121.0 . .
C18 C17 H17 121.0 . .
C17 C18 C13 119.2(2) . .
C17 C18 H18 120.4 . .
C13 C18 H18 120.4 . .
C14 N3 C16 117.71(18) . .
C1 C100 H10A 109.5 . .
C1 C100 H10B 109.5 . .
H10A C100 H10B 109.5 . .
C1 C100 H10C 109.5 . .
H10A C100 H10C 109.5 . .
H10B C100 H10C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.399(2) .
C1 C2 1.399(2) .
C1 C100 1.66(2) .
C1 Cl1 1.707(2) .
C2 O1 1.359(2) .
C2 C3 1.388(2) .
C3 C4 1.385(3) .
C3 H3 0.9300 .
C4 C5 1.385(3) .
C4 H4 0.9300 .
C5 C6 1.394(2) .
C5 H5 0.9300 .
C6 O2 1.359(2) .
C7 C8 1.509(2) .
C7 C7 1.521(4) 2_746
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 C9 1.382(3) .
C8 C12 1.394(3) .
C9 C10 1.377(3) .
C9 H9 0.9300 .
C10 N2 1.337(3) .
C10 H10 0.9300 .
C11 N2 1.335(3) .
C11 C12 1.387(3) .
C11 H11 0.9300 .
C12 H12 0.9300 .
O1 H1 0.8200 .
O2 H2 0.8200 .
C19 C20 1.505(3) .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C19 H19D 0.9600 .
C19 H19E 0.9600 .
C19 H19F 0.9600 .
C20 N1 1.338(2) .
C20 C21 1.398(2) 2_765
C21 N1 1.338(2) .
C21 C20 1.398(2) 2_765
C21 C22 1.505(2) .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 0.9600 .
C22 H22D 0.9600 .
C22 H22E 0.9600 .
C22 H22F 0.9600 .
C13 C18 1.385(3) .
C13 C14 1.397(3) .
C13 H13 0.9300 .
C14 N3 1.336(2) .
C14 C14 1.488(3) 2_665
C16 N3 1.340(3) .
C16 C17 1.371(3) .
C16 H16 0.9300 .
C17 C18 1.382(3) .
C17 H17 0.9300 .
C18 H18 0.9300 .
C100 H10A 0.9600 .
C100 H10B 0.9600 .
C100 H10C 0.9600 .
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 -178.95(14) . .
C100 C1 C2 O1 -6.0(8) . .
Cl1 C1 C2 O1 2.6(2) . .
C6 C1 C2 C3 2.1(2) . .
C100 C1 C2 C3 175.0(8) . .
Cl1 C1 C2 C3 -176.31(13) . .
O1 C2 C3 C4 -179.22(16) . .
C1 C2 C3 C4 -0.3(3) . .
C2 C3 C4 C5 -1.1(3) . .
C3 C4 C5 C6 0.8(3) . .
C4 C5 C6 O2 -179.27(16) . .
C4 C5 C6 C1 1.0(3) . .
C2 C1 C6 O2 177.82(14) . .
C100 C1 C6 O2 5.5(9) . .
Cl1 C1 C6 O2 -3.8(2) . .
C2 C1 C6 C5 -2.4(2) . .
C100 C1 C6 C5 -174.7(8) . .
Cl1 C1 C6 C5 176.01(13) . .
C7 C7 C8 C9 71.5(3) 2_746 .
C7 C7 C8 C12 -108.8(3) 2_746 .
C12 C8 C9 C10 0.4(3) . .
C7 C8 C9 C10 -179.84(18) . .
C8 C9 C10 N2 -0.8(3) . .
N2 C11 C12 C8 0.3(3) . .
C9 C8 C12 C11 -0.2(3) . .
C7 C8 C12 C11 -179.93(17) . .
C9 C10 N2 C11 0.8(3) . .
C12 C11 N2 C10 -0.5(3) . .
C20 C21 N1 C20 -0.6(3) 2_765 .
C22 C21 N1 C20 178.78(16) . .
C21 C20 N1 C21 0.6(3) 2_765 .
C19 C20 N1 C21 -178.80(16) . .
C18 C13 C14 N3 1.2(3) . .
C18 C13 C14 C14 -179.4(2) . 2_665
N3 C16 C17 C18 0.8(4) . .
C16 C17 C18 C13 -0.4(3) . .
C14 C13 C18 C17 -0.6(3) . .
C13 C14 N3 C16 -0.7(3) . .
C14 C14 N3 C16 179.9(2) 2_665 .
C17 C16 N3 C14 -0.3(3) . .
