#------------------------------------------------------------------------------
#$Date: 2018-02-06 02:46:13 +0200 (Tue, 06 Feb 2018) $
#$Revision: 206201 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/71/4127155.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_4127155
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(C6.81 H7.44 Cl0.19 O2), C8 H12 N2'
_chemical_formula_sum            'C43.63 H46.88 Cl0.37 N6 O4'
_chemical_formula_weight         732.50
_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                96.635(8)
_cell_angle_beta                 94.539(13)
_cell_angle_gamma                91.885(12)
_cell_formula_units_Z            1
_cell_length_a                   7.578(5)
_cell_length_b                   8.815(6)
_cell_length_c                   14.496(10)
_cell_measurement_reflns_used    2897
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33.7
_cell_measurement_theta_min      2.3
_cell_volume                     958.0(11)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_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  0.0512
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.997
_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            10225
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.839
_exptl_absorpt_coefficient_mu    0.108
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       block
_exptl_crystal_F_000             389.0
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0601
_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)+(0.1081P)²+0.1347P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1750
_refine_ls_wR_factor_ref         0.1873
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3474
_reflns_number_total             4387
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b12501_si_003.cif
_cod_data_source_block           QN5
_cod_original_cell_volume        957.9(11)
_cod_database_code               4127155
_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 0.5329(2) 0.06320(18) 0.30810(10) 0.0356(3) Uani 1 1 d . . .
C2 C 0.6818(2) -0.01818(19) 0.33247(11) 0.0384(4) Uani 1 1 d . . .
C3 C 0.8438(2) 0.0102(2) 0.29702(13) 0.0473(4) Uani 1 1 d . . .
H3 H 0.9422 -0.0439 0.3139 0.057 Uiso 1 1 calc R U .
C4 C 0.8569(2) 0.1199(2) 0.23638(14) 0.0508(5) Uani 1 1 d . . .
H4 H 0.9651 0.1395 0.2130 0.061 Uiso 1 1 calc R U .
C5 C 0.7119(3) 0.2004(2) 0.21014(13) 0.0465(4) Uani 1 1 d . . .
H5 H 0.7221 0.2740 0.1695 0.056 Uiso 1 1 calc R U .
C6 C 0.5494(2) 0.17043(19) 0.24523(11) 0.0385(4) Uani 1 1 d . . .
C7 C 0.7126(2) -0.5710(2) 0.56129(12) 0.0472(4) Uani 1 1 d . . .
C8 C 0.8535(3) -0.4895(2) 0.61473(14) 0.0529(5) Uani 1 1 d . . .
H8 H 0.8379 -0.3915 0.6435 0.063 Uiso 1 1 calc R U .
C9 C 1.0156(3) -0.5542(2) 0.62482(14) 0.0535(5) Uani 1 1 d . . .
H9 H 1.1072 -0.4977 0.6610 0.064 Uiso 1 1 calc R U .
C10 C 0.9139(3) -0.7694(2) 0.53340(15) 0.0580(5) Uani 1 1 d . . .
H10 H 0.9335 -0.8665 0.5045 0.070 Uiso 1 1 calc R U .
C11 C 0.7479(3) -0.7133(2) 0.51949(16) 0.0598(5) Uani 1 1 d . . .
H11 H 0.6597 -0.7718 0.4818 0.072 Uiso 1 1 calc R U .
C12 C 0.5299(3) -0.5085(3) 0.54922(15) 0.0641(6) Uani 1 1 d . . .
H12A H 0.4457 -0.5762 0.5731 0.077 Uiso 1 1 calc R U .
H12B H 0.5294 -0.4095 0.5862 0.077 Uiso 1 1 calc R U .
C13 C 0.9380(3) 1.4075(2) -0.12271(14) 0.0535(5) Uani 1 1 d . . .
H13 H 0.9647 1.4877 -0.1564 0.064 Uiso 1 1 calc R U .
C14 C 0.9639(2) 1.4260(2) -0.02604(12) 0.0431(4) Uani 1 1 d . . .
C16 C 0.8585(3) 1.1814(2) -0.02092(17) 0.0618(6) Uani 1 1 d . . .
H16 H 0.8298 1.1033 0.0140 0.074 Uiso 1 1 calc R U .
C17 C 0.8313(3) 1.1529(2) -0.11616(17) 0.0615(6) Uani 1 1 d . . .
H17 H 0.7866 1.0580 -0.1448 0.074 Uiso 1 1 calc R U .
C18 C 0.8717(3) 1.2679(3) -0.16811(16) 0.0626(6) Uani 1 1 d . . .
H18 H 0.8549 1.2524 -0.2328 0.075 Uiso 1 1 calc R U .
C19 C 0.6406(3) 0.8074(2) 0.03275(17) 0.0569(5) Uani 1 1 d . . .
H19A H 0.6605 0.8389 0.0985 0.085 Uiso 0.5 1 calc R U P
H19B H 0.7505 0.8143 0.0045 0.085 Uiso 0.5 1 calc R U P
H19C H 0.5573 0.8726 0.0055 0.085 Uiso 0.5 1 calc R U P
H19D H 0.6517 0.8450 -0.0262 0.085 Uiso 0.5 1 calc R U P
H19E H 0.5617 0.8696 0.0678 0.085 Uiso 0.5 1 calc R U P
H19F H 0.7549 0.8113 0.0668 0.085 Uiso 0.5 1 calc R U P
C20 C 0.5678(2) 0.64509(17) 0.01677(12) 0.0390(4) Uani 1 1 d . . .
C21 C 0.5352(2) 0.56056(19) 0.08982(12) 0.0396(4) Uani 1 1 d . . .
C22 C 0.5760(3) 0.6243(3) 0.19038(14) 0.0588(5) Uani 1 1 d . . .
H22A H 0.6234 0.7273 0.1940 0.088 Uiso 0.5 1 calc R U P
H22B H 0.4693 0.6234 0.2220 0.088 Uiso 0.5 1 calc R U P
H22C H 0.6613 0.5627 0.2194 0.088 Uiso 0.5 1 calc R U P
H22D H 0.5459 0.5483 0.2296 0.088 Uiso 0.5 1 calc R U P
H22E H 0.7000 0.6522 0.2016 0.088 Uiso 0.5 1 calc R U P
H22F H 0.5081 0.7129 0.2041 0.088 Uiso 0.5 1 calc R U P
N1 N 1.0483(2) -0.69358(19) 0.58553(11) 0.0506(4) Uani 1 1 d . . .
N2 N 0.9239(2) 1.31498(19) 0.02502(12) 0.0556(4) Uani 1 1 d . . .
N3 N 0.46768(19) 0.41712(15) 0.07196(10) 0.0401(3) Uani 1 1 d . . .
O1 O 0.40039(17) 0.24477(17) 0.22033(10) 0.0546(4) Uani 1 1 d . . .
H1 H 0.4220 0.3000 0.1804 0.082 Uiso 1 1 calc R U .
O2 O 0.66053(18) -0.12387(15) 0.39267(9) 0.0508(3) Uani 1 1 d . . .
H2 H 0.7490 -0.1748 0.3958 0.076 Uiso 1 1 calc R U .
Cl1 Cl 0.3530(6) 0.0331(8) 0.3552(5) 0.0536(19) Uani 0.1866 1 d . . P
C100 C 0.3504(7) 0.0421(7) 0.3483(4) 0.0539(19) Uani 0.8134 1 d . . P
H10A H 0.3575 -0.0345 0.3903 0.081 Uiso 0.8134 1 calc R U P
H10B H 0.3196 0.1371 0.3812 0.081 Uiso 0.8134 1 calc R U P
H10C H 0.2615 0.0107 0.2982 0.081 Uiso 0.8134 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 118.30(15) . .
C6 C1 C100 118.1(3) . .
C2 C1 C100 123.6(3) . .
C6 C1 Cl1 122.7(3) . .
C2 C1 Cl1 119.0(3) . .
C100 C1 Cl1 4.7(4) . .
O2 C2 C3 122.23(15) . .
O2 C2 C1 116.85(15) . .
C3 C2 C1 120.92(15) . .
C4 C3 C2 119.39(16) . .
C4 C3 H3 120.3 . .
C2 C3 H3 120.3 . .
C5 C4 C3 121.01(16) . .
C5 C4 H4 119.5 . .
C3 C4 H4 119.5 . .
C4 C5 C6 119.33(16) . .
C4 C5 H5 120.3 . .
C6 C5 H5 120.3 . .
O1 C6 C1 117.09(15) . .
O1 C6 C5 121.89(15) . .
C1 C6 C5 121.01(15) . .
C11 C7 C8 116.36(18) . .
C11 C7 C12 120.92(19) . .
C8 C7 C12 122.72(19) . .
C9 C8 C7 119.90(18) . .
C9 C8 H8 120.1 . .
C7 C8 H8 120.1 . .
N1 C9 C8 123.53(18) . .
N1 C9 H9 118.2 . .
C8 C9 H9 118.2 . .
N1 C10 C11 124.16(19) . .
N1 C10 H10 117.9 . .
C11 C10 H10 117.9 . .
C7 C11 C10 119.91(19) . .
C7 C11 H11 120.0 . .
C10 C11 H11 120.0 . .
C12 C12 C7 113.7(2) 2_646 .
C12 C12 H12A 108.8 2_646 .
C7 C12 H12A 108.8 . .
C12 C12 H12B 108.8 2_646 .
C7 C12 H12B 108.8 . .
H12A C12 H12B 107.7 . .
C18 C13 C14 119.0(2) . .
C18 C13 H13 120.5 . .
C14 C13 H13 120.5 . .
N2 C14 C13 122.40(17) . .
N2 C14 C14 116.6(2) . 2_785
C13 C14 C14 121.0(2) . 2_785
N2 C16 C17 124.1(2) . .
N2 C16 H16 118.0 . .
C17 C16 H16 118.0 . .
C18 C17 C16 118.31(19) . .
C18 C17 H17 120.8 . .
C16 C17 H17 120.8 . .
C17 C18 C13 119.0(2) . .
C17 C18 H18 120.5 . .
C13 C18 H18 120.5 . .
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 . .
N3 C20 C21 120.27(15) 2_665 .
N3 C20 C19 117.16(16) 2_665 .
C21 C20 C19 122.56(17) . .
N3 C21 C20 120.29(15) . .
N3 C21 C22 117.47(16) . .
C20 C21 C22 122.23(16) . .
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 . .
C10 N1 C9 116.12(17) . .
C14 N2 C16 117.24(18) . .
C21 N3 C20 119.44(14) . 2_665
C6 O1 H1 109.5 . .
C2 O2 H2 109.5 . .
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 1.396(2) .
C1 C2 1.401(2) .
C1 C100 1.556(6) .
C1 Cl1 1.600(5) .
C2 O2 1.362(2) .
C2 C3 1.394(3) .
C3 C4 1.386(3) .
C3 H3 0.9300 .
C4 C5 1.380(3) .
C4 H4 0.9300 .
C5 C6 1.398(3) .
C5 H5 0.9300 .
C6 O1 1.368(2) .
C7 C11 1.373(3) .
C7 C8 1.395(3) .
C7 C12 1.512(3) .
C8 C9 1.375(3) .
C8 H8 0.9300 .
C9 N1 1.333(3) .
C9 H9 0.9300 .
C10 N1 1.331(3) .
C10 C11 1.375(3) .
C10 H10 0.9300 .
C11 H11 0.9300 .
C12 C12 1.488(4) 2_646
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 C18 1.386(3) .
C13 C14 1.389(3) .
C13 H13 0.9300 .
C14 N2 1.334(2) .
C14 C14 1.494(3) 2_785
C16 N2 1.343(3) .
C16 C17 1.372(3) .
C16 H16 0.9300 .
C17 C18 1.371(3) .
C17 H17 0.9300 .
C18 H18 0.9300 .
C19 C20 1.502(2) .
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 N3 1.342(2) 2_665
C20 C21 1.396(2) .
C21 N3 1.337(2) .
C21 C22 1.505(3) .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 0.9600 .
C22 H22D 0.9600 .
C22 H22E 0.9600 .
C22 H22F 0.9600 .
N3 C20 1.342(2) 2_665
O1 H1 0.8200 .
O2 H2 0.8200 .
C100 H10A 0.9600 .
C100 H10B 0.9600 .
C100 H10C 0.9600 .
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 N3 0.82 2.02 2.841(2) 174.0 .
O2 H2 N1 0.82 1.98 2.792(2) 174.0 2_746
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 -178.87(14) . .
C100 C1 C2 O2 1.9(3) . .
Cl1 C1 C2 O2 2.8(4) . .
C6 C1 C2 C3 1.8(2) . .
C100 C1 C2 C3 -177.4(3) . .
Cl1 C1 C2 C3 -176.5(3) . .
O2 C2 C3 C4 -179.66(16) . .
C1 C2 C3 C4 -0.4(3) . .
C2 C3 C4 C5 -0.5(3) . .
C3 C4 C5 C6 -0.1(3) . .
C2 C1 C6 O1 177.96(14) . .
C100 C1 C6 O1 -2.8(3) . .
Cl1 C1 C6 O1 -3.7(4) . .
C2 C1 C6 C5 -2.5(2) . .
C100 C1 C6 C5 176.8(2) . .
Cl1 C1 C6 C5 175.9(3) . .
C4 C5 C6 O1 -178.79(17) . .
C4 C5 C6 C1 1.6(3) . .
C11 C7 C8 C9 -1.5(3) . .
C12 C7 C8 C9 178.42(19) . .
C7 C8 C9 N1 0.3(3) . .
C8 C7 C11 C10 1.6(3) . .
C12 C7 C11 C10 -178.3(2) . .
N1 C10 C11 C7 -0.5(4) . .
C11 C7 C12 C12 -61.3(4) . 2_646
C8 C7 C12 C12 118.8(3) . 2_646
C18 C13 C14 N2 -1.4(3) . .
C18 C13 C14 C14 179.6(2) . 2_785
N2 C16 C17 C18 -0.6(4) . .
C16 C17 C18 C13 0.0(3) . .
C14 C13 C18 C17 0.9(3) . .
N3 C20 C21 N3 -0.2(3) 2_665 .
C19 C20 C21 N3 178.96(16) . .
N3 C20 C21 C22 178.82(16) 2_665 .
C19 C20 C21 C22 -2.0(3) . .
C11 C10 N1 C9 -0.7(3) . .
C8 C9 N1 C10 0.9(3) . .
C13 C14 N2 C16 0.8(3) . .
C14 C14 N2 C16 179.8(2) 2_785 .
C17 C16 N2 C14 0.2(3) . .
C20 C21 N3 C20 0.2(3) . 2_665
C22 C21 N3 C20 -178.87(16) . 2_665
