#------------------------------------------------------------------------------
#$Date: 2018-02-06 02:46:13 +0200 (Tue, 06 Feb 2018) $
#$Revision: 206201 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/71/4127152.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_4127152
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(C6.44 H5 Cl0.56 O2), C8 H12 N2'
_chemical_formula_sum            'C42.89 H42 Cl1.11 N6 O4'
_chemical_formula_weight         744.92
_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                97.232(16)
_cell_angle_beta                 95.305(15)
_cell_angle_gamma                92.094(10)
_cell_formula_units_Z            1
_cell_length_a                   7.572(7)
_cell_length_b                   8.832(8)
_cell_length_c                   14.537(13)
_cell_measurement_reflns_used    2659
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33.6
_cell_measurement_theta_min      1.4
_cell_volume                     959.2(15)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0970
_diffrn_reflns_av_unetI/netI     0.0787
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_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            10205
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.879
_exptl_absorpt_coefficient_mu    0.159
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_description       block
_exptl_crystal_F_000             392.2
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4392
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0559
_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)+(0.0879P)²+0.0803P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1574
_refine_ls_wR_factor_ref         0.1730
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3329
_reflns_number_total             4392
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b12501_si_003.cif
_cod_data_source_block           QN2
_cod_original_cell_volume        959.1(15)
_cod_database_code               4127152
_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
C7 C 0.5429(2) 0.56778(18) 0.30596(11) 0.0376(4) Uani 1 1 d . . .
C8 C 0.5571(2) 0.67489(19) 0.24355(12) 0.0408(4) Uani 1 1 d . . .
C9 C 0.7194(2) 0.7022(2) 0.20834(13) 0.0478(4) Uani 1 1 d . . .
H9 H 0.7296 0.7738 0.1672 0.057 Uiso 1 1 calc R U .
C10 C 0.8638(2) 0.6222(2) 0.23512(14) 0.0507(5) Uani 1 1 d . . .
H10 H 0.9720 0.6413 0.2123 0.061 Uiso 1 1 calc R U .
C11 C 0.8509(2) 0.5134(2) 0.29564(14) 0.0487(4) Uani 1 1 d . . .
H11 H 0.9493 0.4591 0.3122 0.058 Uiso 1 1 calc R U .
C12 C 0.6900(2) 0.48578(19) 0.33155(12) 0.0401(4) Uani 1 1 d . . .
O1 O 0.40809(17) 0.74834(17) 0.21882(10) 0.0573(4) Uani 1 1 d . . .
H1 H 0.4273 0.7994 0.1771 0.086 Uiso 1 1 calc R U .
O2 O 0.66782(17) 0.38151(16) 0.39167(10) 0.0523(4) Uani 1 1 d . . .
H2 H 0.7546 0.3288 0.3942 0.078 Uiso 1 1 calc R U .
C14 C 0.8577(3) 0.6798(2) -0.02341(17) 0.0637(6) Uani 1 1 d . . .
H14 H 0.8313 0.6010 0.0107 0.076 Uiso 1 1 calc R U .
C15 C 0.8264(3) 0.6527(3) -0.11886(17) 0.0631(6) Uani 1 1 d . . .
H15 H 0.7803 0.5581 -0.1484 0.076 Uiso 1 1 calc R U .
C16 C 0.8648(3) 0.7685(3) -0.16947(16) 0.0634(6) Uani 1 1 d . . .
H16 H 0.8453 0.7533 -0.2341 0.076 Uiso 1 1 calc R U .
C17 C 0.9326(3) 0.9079(2) -0.12357(15) 0.0550(5) Uani 1 1 d . . .
H17 H 0.9583 0.9880 -0.1568 0.066 Uiso 1 1 calc R U .
C18 C 0.9621(2) 0.9268(2) -0.02664(13) 0.0452(4) Uani 1 1 d . . .
C19 C 0.5827(3) 1.1258(3) 0.19061(15) 0.0621(6) Uani 1 1 d . . .
H19A H 0.6307 1.2288 0.1946 0.093 Uiso 0.5 1 calc R U P
H19B H 0.4768 1.1251 0.2222 0.093 Uiso 0.5 1 calc R U P
H19C H 0.6686 1.0645 0.2193 0.093 Uiso 0.5 1 calc R U P
H19D H 0.5534 1.0501 0.2294 0.093 Uiso 0.5 1 calc R U P
H19E H 0.7072 1.1538 0.2019 0.093 Uiso 0.5 1 calc R U P
H19F H 0.5155 1.2144 0.2047 0.093 Uiso 0.5 1 calc R U P
C20 C 0.5390(2) 1.06161(19) 0.09020(13) 0.0411(4) Uani 1 1 d . . .
C21 C 0.4317(2) 0.85440(18) -0.01686(13) 0.0416(4) Uani 1 1 d . . .
C22 C 0.3574(3) 0.6918(2) -0.03337(18) 0.0604(6) Uani 1 1 d . . .
H22A H 0.3354 0.6596 -0.0992 0.091 Uiso 0.5 1 calc R U P
H22B H 0.4412 0.6269 -0.0064 0.091 Uiso 0.5 1 calc R U P
H22C H 0.2482 0.6851 -0.0051 0.091 Uiso 0.5 1 calc R U P
H22D H 0.3478 0.6548 0.0254 0.091 Uiso 0.5 1 calc R U P
H22E H 0.2420 0.6875 -0.0673 0.091 Uiso 0.5 1 calc R U P
H22F H 0.4350 0.6293 -0.0687 0.091 Uiso 0.5 1 calc R U P
N2 N 0.47014(19) 0.91763(16) 0.07175(11) 0.0428(3) Uani 1 1 d . . .
N3 N 0.9247(2) 0.81472(19) 0.02375(13) 0.0570(4) Uani 1 1 d . . .
C1 C 1.4728(3) 0.0096(3) 0.44990(15) 0.0603(5) Uani 1 1 d . . .
H1A H 1.4734 -0.0886 0.4117 0.072 Uiso 1 1 calc R U .
H1B H 1.5591 0.0780 0.4288 0.072 Uiso 1 1 calc R U .
C2 C 1.2905(2) 0.0729(2) 0.43658(13) 0.0470(4) Uani 1 1 d . . .
C3 C 1.1444(3) -0.0120(2) 0.38758(14) 0.0538(5) Uani 1 1 d . . .
H3 H 1.1563 -0.1125 0.3618 0.065 Uiso 1 1 calc R U .
C4 C 0.9831(3) 0.0535(2) 0.37765(15) 0.0549(5) Uani 1 1 d . . .
H4 H 0.8879 -0.0054 0.3448 0.066 Uiso 1 1 calc R U .
C5 C 1.0948(3) 0.2765(2) 0.46017(16) 0.0581(5) Uani 1 1 d . . .
H5 H 1.0787 0.3762 0.4862 0.070 Uiso 1 1 calc R U .
C6 C 1.2619(3) 0.2200(2) 0.47315(16) 0.0582(5) Uani 1 1 d . . .
H6 H 1.3546 0.2814 0.5065 0.070 Uiso 1 1 calc R U .
N1 N 0.9552(2) 0.19685(19) 0.41252(12) 0.0517(4) Uani 1 1 d . . .
Cl1 Cl 0.3511(4) 0.5446(3) 0.3516(3) 0.0476(6) Uani 0.5563 1 d . . P
C100 C 0.3497(18) 0.5345(18) 0.3572(13) 0.064(5) Uani 0.4437 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
C12 C7 C8 119.96(16) . .
C12 C7 Cl1 120.99(18) . .
C8 C7 Cl1 119.02(17) . .
C12 C7 C100 117.3(6) . .
C8 C7 C100 122.7(5) . .
Cl1 C7 C100 3.7(6) . .
O1 C8 C9 122.51(16) . .
O1 C8 C7 117.49(15) . .
C9 C8 C7 119.99(15) . .
C10 C9 C8 119.45(17) . .
C10 C9 H9 120.3 . .
C8 C9 H9 120.3 . .
C9 C10 C11 121.23(17) . .
C9 C10 H10 119.4 . .
C11 C10 H10 119.4 . .
C10 C11 C12 119.82(16) . .
C10 C11 H11 120.1 . .
C12 C11 H11 120.1 . .
O2 C12 C11 123.06(15) . .
O2 C12 C7 117.40(15) . .
C11 C12 C7 119.54(16) . .
C8 O1 H1 109.5 . .
C12 O2 H2 109.5 . .
N3 C14 C15 123.7(2) . .
N3 C14 H14 118.2 . .
C15 C14 H14 118.2 . .
C16 C15 C14 118.4(2) . .
C16 C15 H15 120.8 . .
C14 C15 H15 120.8 . .
C15 C16 C17 119.4(2) . .
C15 C16 H16 120.3 . .
C17 C16 H16 120.3 . .
C16 C17 C18 119.0(2) . .
C16 C17 H17 120.5 . .
C18 C17 H17 120.5 . .
N3 C18 C17 122.19(18) . .
N3 C18 C18 116.3(2) . 2_775
C17 C18 C18 121.6(2) . 2_775
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 . .
N2 C20 C21 119.97(17) . 2_675
N2 C20 C19 117.43(16) . .
C21 C20 C19 122.61(17) 2_675 .
N2 C21 C20 120.38(16) . 2_675
N2 C21 C22 117.31(17) . .
C20 C21 C22 122.31(18) 2_675 .
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 N2 C20 119.65(15) . .
C18 N3 C14 117.3(2) . .
C1 C1 C2 112.6(2) 2_856 .
C1 C1 H1A 109.1 2_856 .
C2 C1 H1A 109.1 . .
C1 C1 H1B 109.1 2_856 .
C2 C1 H1B 109.1 . .
H1A C1 H1B 107.8 . .
C6 C2 C3 116.59(17) . .
C6 C2 C1 120.37(18) . .
C3 C2 C1 123.03(19) . .
C4 C3 C2 119.78(19) . .
C4 C3 H3 120.1 . .
C2 C3 H3 120.1 . .
N1 C4 C3 123.73(18) . .
N1 C4 H4 118.1 . .
C3 C4 H4 118.1 . .
N1 C5 C6 124.0(2) . .
N1 C5 H5 118.0 . .
C6 C5 H5 118.0 . .
C2 C6 C5 119.78(19) . .
C2 C6 H6 120.1 . .
C5 C6 H6 120.1 . .
C5 N1 C4 116.13(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C7 C12 1.398(2) .
C7 C8 1.399(2) .
C7 Cl1 1.669(4) .
C7 C100 1.734(16) .
C8 O1 1.364(2) .
C8 C9 1.399(3) .
C9 C10 1.376(3) .
C9 H9 0.9300 .
C10 C11 1.389(3) .
C10 H10 0.9300 .
C11 C12 1.394(3) .
C11 H11 0.9300 .
C12 O2 1.363(2) .
O1 H1 0.8200 .
O2 H2 0.8200 .
C14 N3 1.354(3) .
C14 C15 1.375(4) .
C14 H14 0.9300 .
C15 C16 1.371(3) .
C15 H15 0.9300 .
C16 C17 1.382(3) .
C16 H16 0.9300 .
C17 C18 1.394(3) .
C17 H17 0.9300 .
C18 N3 1.341(3) .
C18 C18 1.487(4) 2_775
C19 C20 1.500(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 N2 1.342(2) .
C20 C21 1.402(3) 2_675
C21 N2 1.339(3) .
C21 C20 1.402(3) 2_675
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 .
C1 C1 1.509(4) 2_856
C1 C2 1.512(3) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C2 C6 1.374(3) .
C2 C3 1.397(3) .
C3 C4 1.374(3) .
C3 H3 0.9300 .
C4 N1 1.335(3) .
C4 H4 0.9300 .
C5 N1 1.334(3) .
C5 C6 1.382(3) .
C5 H5 0.9300 .
C6 H6 0.9300 .
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
O1 H1 N2 0.82 2.00 2.823(3) 177.8
O2 H2 N1 0.82 1.97 2.784(3) 174.1
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
C12 C7 C8 O1 178.08(15) . .
Cl1 C7 C8 O1 -4.0(3) . .
C100 C7 C8 O1 -3.9(7) . .
C12 C7 C8 C9 -1.3(3) . .
Cl1 C7 C8 C9 176.53(18) . .
C100 C7 C8 C9 176.6(7) . .
O1 C8 C9 C10 -178.96(18) . .
C7 C8 C9 C10 0.4(3) . .
C8 C9 C10 C11 0.8(3) . .
C9 C10 C11 C12 -1.1(3) . .
C10 C11 C12 O2 -179.59(17) . .
C10 C11 C12 C7 0.2(3) . .
C8 C7 C12 O2 -179.18(15) . .
Cl1 C7 C12 O2 3.0(3) . .
C100 C7 C12 O2 2.7(7) . .
C8 C7 C12 C11 1.0(3) . .
Cl1 C7 C12 C11 -176.81(18) . .
C100 C7 C12 C11 -177.1(6) . .
N3 C14 C15 C16 -0.1(4) . .
C14 C15 C16 C17 -0.2(3) . .
C15 C16 C17 C18 0.6(3) . .
C16 C17 C18 N3 -0.9(3) . .
C16 C17 C18 C18 178.9(2) . 2_775
C20 C21 N2 C20 -0.8(3) 2_675 .
C22 C21 N2 C20 179.06(15) . .
C21 C20 N2 C21 0.8(3) 2_675 .
C19 C20 N2 C21 -178.90(16) . .
C17 C18 N3 C14 0.6(3) . .
C18 C18 N3 C14 -179.2(2) 2_775 .
C15 C14 N3 C18 -0.1(3) . .
C1 C1 C2 C6 67.7(3) 2_856 .
C1 C1 C2 C3 -112.4(3) 2_856 .
C6 C2 C3 C4 0.5(3) . .
C1 C2 C3 C4 -179.45(19) . .
C2 C3 C4 N1 0.0(3) . .
C3 C2 C6 C5 -0.2(3) . .
C1 C2 C6 C5 179.76(19) . .
N1 C5 C6 C2 -0.7(4) . .
C6 C5 N1 C4 1.1(3) . .
C3 C4 N1 C5 -0.8(3) . .
