#------------------------------------------------------------------------------
#$Date: 2018-02-06 02:46:13 +0200 (Tue, 06 Feb 2018) $
#$Revision: 206201 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/71/4127151.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_4127151
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(C6.51 H6.53 Cl0.49 O2), C8 H12 N2'
_chemical_formula_sum            'C43.02 H45.06 Cl0.98 N6 O4'
_chemical_formula_weight         744.89
_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                96.914(9)
_cell_angle_beta                 94.745(13)
_cell_angle_gamma                91.997(13)
_cell_formula_units_Z            1
_cell_length_a                   7.555(6)
_cell_length_b                   8.801(7)
_cell_length_c                   14.445(12)
_cell_measurement_reflns_used    2525
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33.5
_cell_measurement_theta_min      2.3
_cell_volume                     949.2(13)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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  0.0788
_diffrn_reflns_av_unetI/netI     0.0737
_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            10138
_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         27.498
_diffrn_reflns_theta_min         2.708
_exptl_absorpt_coefficient_mu    0.151
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       Block
_exptl_crystal_F_000             394
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.224
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         4337
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.224
_refine_ls_R_factor_all          0.0981
_refine_ls_R_factor_gt           0.0747
_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)+(0.0860P)²+0.1353P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2021
_refine_ls_wR_factor_ref         0.2165
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3191
_reflns_number_total             4337
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b12501_si_003.cif
_cod_data_source_block           QN1
_cod_original_cell_volume        949.3(14)
_cod_database_code               4127151
_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   0.941
_shelx_estimated_absorpt_t_max   0.972
_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
_atom_site_refinement_flags_occupancy
C1 C 0.0372(3) 0.0649(2) 0.30739(15) 0.0349(5) Uani 1 1 d . . .
C2 C 0.1853(3) -0.0167(2) 0.33193(15) 0.0363(5) Uani 1 1 d . . .
C3 C 0.3465(3) 0.0113(3) 0.29602(18) 0.0454(6) Uani 1 1 d . . .
H3 H 0.4451 -0.0432 0.3125 0.054 Uiso 1 1 calc R U .
C4 C 0.3592(3) 0.1200(3) 0.23595(19) 0.0483(6) Uani 1 1 d . . .
H4 H 0.4677 0.1394 0.2126 0.058 Uiso 1 1 calc R U .
C5 C 0.2149(3) 0.2010(3) 0.20962(17) 0.0445(6) Uani 1 1 d . . .
H5 H 0.2259 0.2742 0.1688 0.053 Uiso 1 1 calc R U .
C6 C 0.0521(3) 0.1725(3) 0.24452(15) 0.0371(5) Uani 1 1 d . . .
C7 C 0.0297(4) 0.4914(4) 0.5493(2) 0.0601(8) Uani 1 1 d . . .
H7A H -0.0550 0.4232 0.5727 0.072 Uiso 1 1 calc R U .
H7B H 0.0290 0.5905 0.5867 0.072 Uiso 1 1 calc R U .
C8 C 0.0368(3) 0.5611(3) 0.09005(16) 0.0373(5) Uani 1 1 d . . .
C9 C -0.0683(3) 0.3543(2) -0.01701(17) 0.0379(5) Uani 1 1 d . . .
C10 C -0.1422(4) 0.1925(3) -0.0331(2) 0.0557(7) Uani 1 1 d . . .
H10A H -0.1631 0.1605 -0.0991 0.084 Uiso 0.5 1 calc R U P
H10B H -0.2522 0.1860 -0.0046 0.084 Uiso 0.5 1 calc R U P
H10C H -0.0589 0.1270 -0.0059 0.084 Uiso 0.5 1 calc R U P
H10D H -0.1530 0.1552 0.0261 0.084 Uiso 0.5 1 calc R U P
H10E H -0.0640 0.1297 -0.0685 0.084 Uiso 0.5 1 calc R U P
H10F H -0.2572 0.1887 -0.0672 0.084 Uiso 0.5 1 calc R U P
C11 C 0.2124(3) 0.4295(3) 0.56198(17) 0.0448(6) Uani 1 1 d . . .
C12 C 0.2448(4) 0.2835(3) 0.5225(2) 0.0568(7) Uani 1 1 d . . .
H12 H 0.1543 0.2229 0.4870 0.068 Uiso 1 1 calc R U .
C13 C 0.4102(4) 0.2287(3) 0.5357(2) 0.0568(7) Uani 1 1 d . . .
H13 H 0.4284 0.1305 0.5075 0.068 Uiso 1 1 calc R U .
C14 C 0.5164(4) 0.4464(3) 0.62381(19) 0.0514(6) Uani 1 1 d . . .
H14 H 0.6096 0.5044 0.6588 0.062 Uiso 1 1 calc R U .
C15 C 0.3547(4) 0.5105(3) 0.61378(18) 0.0503(6) Uani 1 1 d . . .
H15 H 0.3404 0.6094 0.6421 0.060 Uiso 1 1 calc R U .
C50 C 0.4356(4) 0.4078(3) -0.12332(19) 0.0514(6) Uani 1 1 d . . .
H50 H 0.4617 0.4881 -0.1571 0.062 Uiso 1 1 calc R U .
C60 C 0.3292(4) 0.1533(3) -0.1173(2) 0.0608(8) Uani 1 1 d . . .
H60 H 0.2833 0.0585 -0.1463 0.073 Uiso 1 1 calc R U .
C70 C 0.0791(4) 0.6247(3) 0.19002(19) 0.0566(7) Uani 1 1 d . . .
H70A H 0.1268 0.7280 0.1936 0.085 Uiso 0.5 1 calc R U P
H70B H 0.1650 0.5632 0.2188 0.085 Uiso 0.5 1 calc R U P
H70C H -0.0273 0.6240 0.2220 0.085 Uiso 0.5 1 calc R U P
H70D H 0.0495 0.5488 0.2294 0.085 Uiso 0.5 1 calc R U P
H70E H 0.0114 0.7136 0.2041 0.085 Uiso 0.5 1 calc R U P
H70F H 0.2036 0.6528 0.2010 0.085 Uiso 0.5 1 calc R U P
C80 C 0.3693(4) 0.2687(3) -0.1687(2) 0.0605(8) Uani 1 1 d . . .
H80 H 0.3518 0.2531 -0.2337 0.073 Uiso 1 1 calc R U .
C90 C 0.3587(4) 0.1816(3) -0.0218(2) 0.0593(8) Uani 1 1 d . . .
H90 H 0.3318 0.1029 0.0130 0.071 Uiso 1 1 calc R U .
C101 C 0.4630(3) 0.4265(3) -0.02643(17) 0.0415(5) Uani 1 1 d . . .
N1 N -0.0314(3) 0.4175(2) 0.07189(14) 0.0390(5) Uani 1 1 d . . .
N2 N 0.5474(3) 0.3051(2) 0.58594(15) 0.0474(5) Uani 1 1 d . . .
N3 N 0.4233(3) 0.3146(2) 0.02436(16) 0.0525(6) Uani 1 1 d . . .
O1 O -0.0959(2) 0.2462(2) 0.21998(13) 0.0521(5) Uani 1 1 d . . .
H1 H -0.0797 0.2900 0.1742 0.078 Uiso 1 1 calc R U .
O2 O 0.1636(2) -0.1221(2) 0.39216(12) 0.0485(5) Uani 1 1 d . . .
H2 H 0.2486 -0.1774 0.3924 0.073 Uiso 1 1 calc R U .
Cl1 Cl -0.1476(5) 0.0455(3) 0.3519(3) 0.0599(6) Uani 0.4902 1 d . . P
C150 C -0.159(2) 0.0082(16) 0.3527(13) 0.0599(6) Uani 0.5098 1 d . . P
H15A H -0.2542 0.0682 0.3314 0.090 Uiso 0.5098 1 calc R U P
H15B H -0.1430 0.0236 0.4199 0.090 Uiso 0.5098 1 calc R U P
H15C H -0.1867 -0.0982 0.3317 0.090 Uiso 0.5098 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
C2 C1 C6 119.1(2) . .
C2 C1 Cl1 122.5(2) . .
C6 C1 Cl1 118.3(2) . .
C2 C1 C150 114.8(5) . .
C6 C1 C150 125.8(6) . .
Cl1 C1 C150 10.3(6) . .
O2 C2 C3 122.6(2) . .
O2 C2 C1 117.0(2) . .
C3 C2 C1 120.4(2) . .
C4 C3 C2 119.5(2) . .
C4 C3 H3 120.3 . .
C2 C3 H3 120.3 . .
C5 C4 C3 121.4(2) . .
C5 C4 H4 119.3 . .
C3 C4 H4 119.3 . .
C4 C5 C6 119.5(2) . .
C4 C5 H5 120.2 . .
C6 C5 H5 120.2 . .
O1 C6 C5 122.4(2) . .
O1 C6 C1 117.5(2) . .
C5 C6 C1 120.0(2) . .
C7 C7 C11 113.9(3) 2_566 .
C7 C7 H7A 108.8 2_566 .
C11 C7 H7A 108.8 . .
C7 C7 H7B 108.8 2_566 .
C11 C7 H7B 108.8 . .
H7A C7 H7B 107.7 . .
N1 C8 C9 120.3(2) . 2_565
N1 C8 C70 117.6(2) . .
C9 C8 C70 122.1(2) 2_565 .
N1 C9 C8 119.9(2) . 2_565
N1 C9 C10 117.4(2) . .
C8 C9 C10 122.7(2) 2_565 .
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 . .
C9 C10 H10D 109.5 . .
H10A C10 H10D 141.1 . .
H10B C10 H10D 56.3 . .
H10C C10 H10D 56.3 . .
C9 C10 H10E 109.5 . .
H10A C10 H10E 56.3 . .
H10B C10 H10E 141.1 . .
H10C C10 H10E 56.3 . .
H10D C10 H10E 109.5 . .
C9 C10 H10F 109.5 . .
H10A C10 H10F 56.3 . .
H10B C10 H10F 56.3 . .
H10C C10 H10F 141.1 . .
H10D C10 H10F 109.5 . .
H10E C10 H10F 109.5 . .
C12 C11 C15 116.0(2) . .
C12 C11 C7 120.4(3) . .
C15 C11 C7 123.6(2) . .
C13 C12 C11 119.6(3) . .
C13 C12 H12 120.2 . .
C11 C12 H12 120.2 . .
N2 C13 C12 124.9(3) . .
N2 C13 H13 117.6 . .
C12 C13 H13 117.6 . .
N2 C14 C15 123.3(3) . .
N2 C14 H14 118.3 . .
C15 C14 H14 118.3 . .
C14 C15 C11 120.6(2) . .
C14 C15 H15 119.7 . .
C11 C15 H15 119.7 . .
C80 C50 C101 118.9(3) . .
C80 C50 H50 120.5 . .
C101 C50 H50 120.5 . .
C90 C60 C80 118.1(3) . .
C90 C60 H60 121.0 . .
C80 C60 H60 121.0 . .
C8 C70 H70A 109.5 . .
C8 C70 H70B 109.5 . .
H70A C70 H70B 109.5 . .
C8 C70 H70C 109.5 . .
H70A C70 H70C 109.5 . .
H70B C70 H70C 109.5 . .
C8 C70 H70D 109.5 . .
H70A C70 H70D 141.1 . .
H70B C70 H70D 56.3 . .
H70C C70 H70D 56.3 . .
C8 C70 H70E 109.5 . .
H70A C70 H70E 56.3 . .
H70B C70 H70E 141.1 . .
H70C C70 H70E 56.3 . .
H70D C70 H70E 109.5 . .
C8 C70 H70F 109.5 . .
H70A C70 H70F 56.3 . .
H70B C70 H70F 56.3 . .
H70C C70 H70F 141.1 . .
H70D C70 H70F 109.5 . .
H70E C70 H70F 109.5 . .
C60 C80 C50 119.3(3) . .
C60 C80 H80 120.3 . .
C50 C80 H80 120.3 . .
N3 C90 C60 124.1(3) . .
N3 C90 H90 117.9 . .
C60 C90 H90 117.9 . .
N3 C101 C50 122.1(2) . .
N3 C101 C101 116.5(3) . 2_665
C50 C101 C101 121.4(3) . 2_665
C8 N1 C9 119.76(19) . .
C13 N2 C14 115.6(2) . .
C90 N3 C101 117.4(2) . .
C6 O1 H1 109.5 . .
C2 O2 H2 109.5 . .
C1 C150 H15A 109.5 . .
C1 C150 H15B 109.5 . .
H15A C150 H15B 109.5 . .
C1 C150 H15C 109.5 . .
H15A C150 H15C 109.5 . .
H15B C150 H15C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.395(3) .
C1 C6 1.396(3) .
C1 Cl1 1.597(4) .
C1 C150 1.749(15) .
C2 O2 1.361(3) .
C2 C3 1.388(3) .
C3 C4 1.373(4) .
C3 H3 0.9300 .
C4 C5 1.375(4) .
C4 H4 0.9300 .
C5 C6 1.393(3) .
C5 H5 0.9300 .
C6 O1 1.355(3) .
C7 C7 1.483(6) 2_566
C7 C11 1.507(4) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 N1 1.335(3) .
C8 C9 1.394(3) 2_565
C8 C70 1.489(4) .
C9 N1 1.340(3) .
C9 C8 1.394(3) 2_565
C9 C10 1.496(3) .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C10 H10D 0.9600 .
C10 H10E 0.9600 .
C10 H10F 0.9600 .
C11 C12 1.381(4) .
C11 C15 1.382(4) .
C12 C13 1.362(4) .
C12 H12 0.9300 .
C13 N2 1.327(4) .
C13 H13 0.9300 .
C14 N2 1.334(4) .
C14 C15 1.367(4) .
C14 H14 0.9300 .
C15 H15 0.9300 .
C50 C80 1.375(4) .
C50 C101 1.387(4) .
C50 H50 0.9300 .
C60 C90 1.370(5) .
C60 C80 1.367(5) .
C60 H60 0.9300 .
C70 H70A 0.9600 .
C70 H70B 0.9600 .
C70 H70C 0.9600 .
C70 H70D 0.9600 .
C70 H70E 0.9600 .
C70 H70F 0.9600 .
C80 H80 0.9300 .
C90 N3 1.331(4) .
C90 H90 0.9300 .
C101 N3 1.337(3) .
C101 C101 1.487(5) 2_665
O1 H1 0.8200 .
O2 H2 0.8200 .
C150 H15A 0.9600 .
C150 H15B 0.9600 .
C150 H15C 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 N1 0.82 2.01 2.826(3) 173.7 .
O2 H2 N2 0.82 1.97 2.778(3) 171.1 2_656
O1 H1 N1 0.82 2.01 2.826(3) 173.7 .
O2 H2 N2 0.82 1.97 2.778(3) 171.1 2_656
Cl1 H15B O2 1.02 2.77 3.691(5) 150.4 2_556
C150 H15B O2 0.96 2.77 3.704(19) 165.3 2_556
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 -178.9(2) . .
Cl1 C1 C2 O2 3.8(3) . .
C150 C1 C2 O2 -4.2(7) . .
C6 C1 C2 C3 1.5(3) . .
Cl1 C1 C2 C3 -175.8(2) . .
C150 C1 C2 C3 176.3(7) . .
O2 C2 C3 C4 -179.6(2) . .
C1 C2 C3 C4 -0.1(4) . .
C2 C3 C4 C5 -0.7(4) . .
C3 C4 C5 C6 0.0(4) . .
C4 C5 C6 O1 -178.7(2) . .
C4 C5 C6 C1 1.4(4) . .
C2 C1 C6 O1 178.0(2) . .
Cl1 C1 C6 O1 -4.6(3) . .
C150 C1 C6 O1 3.8(8) . .
C2 C1 C6 C5 -2.2(3) . .
Cl1 C1 C6 C5 175.2(2) . .
C150 C1 C6 C5 -176.3(8) . .
C7 C7 C11 C12 -64.1(5) 2_566 .
C7 C7 C11 C15 117.1(4) 2_566 .
C15 C11 C12 C13 -0.3(4) . .
C7 C11 C12 C13 -179.1(3) . .
C11 C12 C13 N2 0.8(5) . .
N2 C14 C15 C11 -0.4(4) . .
C12 C11 C15 C14 0.1(4) . .
C7 C11 C15 C14 178.9(3) . .
C90 C60 C80 C50 -0.5(5) . .
C101 C50 C80 C60 1.1(4) . .
C80 C60 C90 N3 0.2(5) . .
C80 C50 C101 N3 -1.5(4) . .
C80 C50 C101 C101 179.0(3) . 2_665
C9 C8 N1 C9 0.5(4) 2_565 .
C70 C8 N1 C9 -178.7(2) . .
C8 C9 N1 C8 -0.5(4) 2_565 .
C10 C9 N1 C8 179.2(2) . .
C12 C13 N2 C14 -1.1(4) . .
C15 C14 N2 C13 0.9(4) . .
C60 C90 N3 C101 -0.6(4) . .
C50 C101 N3 C90 1.2(4) . .
C101 C101 N3 C90 -179.3(3) 2_665 .
