#------------------------------------------------------------------------------
#$Date: 2018-02-06 02:46:13 +0200 (Tue, 06 Feb 2018) $
#$Revision: 206201 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/71/4127161.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_4127161
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 H5 Br0.59 Cl0.28 O2), C8 H12 N2'
_chemical_formula_sum            'C42.28 H42 Br1.17 Cl0.55 N6 O4'
_chemical_formula_weight         811.33
_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                97.199(11)
_cell_angle_beta                 95.753(8)
_cell_angle_gamma                91.696(9)
_cell_formula_units_Z            1
_cell_length_a                   7.625(5)
_cell_length_b                   8.825(6)
_cell_length_c                   14.596(10)
_cell_measurement_reflns_used    2177
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      33.6
_cell_measurement_theta_min      2.3
_cell_volume                     968.6(11)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      143(2)
_diffrn_measured_fraction_theta_full 0.997
_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  0.0964
_diffrn_reflns_av_unetI/netI     0.1020
_diffrn_reflns_Laue_measured_fraction_full 0.997
_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            10380
_diffrn_reflns_point_group_measured_fraction_full 0.997
_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         2.564
_exptl_absorpt_coefficient_mu    1.327
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       block
_exptl_crystal_F_000             420.1
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         4441
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0602
_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)+(0.0493P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1408
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2883
_reflns_number_total             4441
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b12501_si_003.cif
_cod_data_source_block           S3
_cod_database_code               4127161
_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 0.5148(5) 0.4476(4) 0.6226(3) 0.0585(10) Uani 1 1 d . . .
H1 H 0.6083 0.5069 0.6561 0.070 Uiso 1 1 calc R U .
C2 C 0.3521(5) 0.5114(4) 0.6126(3) 0.0555(10) Uani 1 1 d . . .
H2 H 0.3381 0.6111 0.6393 0.067 Uiso 1 1 calc R U .
C3 C 0.4091(5) 0.2264(4) 0.5379(3) 0.0613(11) Uani 1 1 d . . .
H3 H 0.4278 0.1282 0.5103 0.074 Uiso 1 1 calc R U .
C4 C 0.2412(5) 0.2798(4) 0.5249(3) 0.0595(10) Uani 1 1 d . . .
H4 H 0.1504 0.2177 0.4910 0.071 Uiso 1 1 calc R U .
C5 C 0.2097(4) 0.4271(4) 0.5629(2) 0.0457(8) Uani 1 1 d . . .
C6 C 0.0277(5) 0.4892(5) 0.5495(2) 0.0612(11) Uani 1 1 d . . .
H6A H -0.0568 0.4194 0.5697 0.073 Uiso 1 1 calc R U .
H6B H 0.0257 0.5866 0.5883 0.073 Uiso 1 1 calc R U .
C20 C 0.0476(4) 0.0697(4) 0.3046(2) 0.0383(7) Uani 1 1 d . . .
C21 C 0.1929(4) -0.0167(4) 0.3294(2) 0.0401(7) Uani 1 1 d . . .
C22 C 0.3522(4) 0.0077(4) 0.2932(2) 0.0493(9) Uani 1 1 d . . .
H22 H 0.4492 -0.0486 0.3093 0.059 Uiso 1 1 calc R U .
C23 C 0.3654(4) 0.1168(4) 0.2330(2) 0.0512(9) Uani 1 1 d . . .
H23 H 0.4725 0.1342 0.2098 0.061 Uiso 1 1 calc R U .
C24 C 0.2216(5) 0.2001(4) 0.2067(2) 0.0484(9) Uani 1 1 d . . .
H24 H 0.2319 0.2713 0.1655 0.058 Uiso 1 1 calc R U .
C25 C 0.0621(4) 0.1766(4) 0.2423(2) 0.0406(8) Uani 1 1 d . . .
C26 C 1.0879(5) 0.6258(5) 0.1894(3) 0.0632(11) Uani 1 1 d . . .
H26A H 1.1355 0.7286 0.1931 0.095 Uiso 0.5 1 calc R U P
H26B H 0.9841 0.6257 0.2215 0.095 Uiso 0.5 1 calc R U P
H26C H 1.1742 0.5640 0.2175 0.095 Uiso 0.5 1 calc R U P
H26D H 1.0604 0.5503 0.2283 0.095 Uiso 0.5 1 calc R U P
H26E H 1.2118 0.6531 0.1999 0.095 Uiso 0.5 1 calc R U P
H26F H 1.0217 0.7149 0.2039 0.095 Uiso 0.5 1 calc R U P
C27 C 0.8572(5) 0.1922(4) -0.0320(3) 0.0617(10) Uani 1 1 d . . .
H27A H 0.8333 0.1593 -0.0974 0.093 Uiso 0.5 1 calc R U P
H27B H 0.9412 0.1271 -0.0051 0.093 Uiso 0.5 1 calc R U P
H27C H 0.7499 0.1869 -0.0031 0.093 Uiso 0.5 1 calc R U P
H27D H 0.8496 0.1562 0.0270 0.093 Uiso 0.5 1 calc R U P
H27E H 0.7417 0.1885 -0.0653 0.093 Uiso 0.5 1 calc R U P
H27F H 0.9330 0.1286 -0.0673 0.093 Uiso 0.5 1 calc R U P
C28 C 0.9316(4) 0.3546(4) -0.0167(2) 0.0425(8) Uani 1 1 d . . .
C29 C 1.0409(4) 0.5616(4) 0.0891(2) 0.0427(8) Uani 1 1 d . . .
C34 C 0.6773(5) 0.8457(5) 0.1184(3) 0.0618(11) Uani 1 1 d . . .
H34 H 0.7235 0.9403 0.1475 0.074 Uiso 1 1 calc R U .
C35 C 0.6414(5) 0.7291(5) 0.1692(3) 0.0634(11) Uani 1 1 d . . .
H35 H 0.6642 0.7432 0.2336 0.076 Uiso 1 1 calc R U .
C36 C 0.5711(5) 0.5908(5) 0.1232(3) 0.0564(10) Uani 1 1 d . . .
H36 H 0.5454 0.5107 0.1561 0.068 Uiso 1 1 calc R U .
C37 C 0.5391(4) 0.5730(4) 0.0265(2) 0.0458(8) Uani 1 1 d . . .
C44 C 0.6433(5) 0.8185(5) 0.0241(3) 0.0644(11) Uani 1 1 d . . .
H44 H 0.6691 0.8971 -0.0100 0.077 Uiso 1 1 calc R U .
N1 N 0.5453(4) 0.3048(4) 0.5866(2) 0.0531(8) Uani 1 1 d . . .
N3 N 0.9726(3) 0.4186(3) 0.07194(19) 0.0441(7) Uani 1 1 d . . .
N4 N 0.5744(4) 0.6851(4) -0.0231(2) 0.0583(8) Uani 1 1 d . . .
O3 O -0.0858(3) 0.2522(3) 0.21803(17) 0.0586(7) Uani 1 1 d . . .
H3A H -0.0639 0.3105 0.1807 0.088 Uiso 1 1 calc R U .
O4 O 0.1696(3) -0.1206(3) 0.38917(16) 0.0540(6) Uani 1 1 d . . .
H4A H 0.2616 -0.1645 0.3989 0.081 Uiso 1 1 calc R U .
Cl1 Cl -0.157(2) 0.0240(16) 0.3599(13) 0.0425(4) Uani 0.2766 1 d . . P
C100 C -0.172(7) 0.024(6) 0.332(3) 0.0425(4) Uani 0.1379 1 d . . P
Br1 Br -0.1597(4) 0.0522(2) 0.3575(2) 0.0425(4) Uani 0.5857 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'
Br Br -0.2901 2.4595 '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'
H H 0.0000 0.0000 '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
N1 C1 C2 123.5(3) . .
N1 C1 H1 118.3 . .
C2 C1 H1 118.3 . .
C1 C2 C5 120.0(3) . .
C1 C2 H2 120.0 . .
C5 C2 H2 120.0 . .
N1 C3 C4 124.8(4) . .
N1 C3 H3 117.6 . .
C4 C3 H3 117.6 . .
C3 C4 C5 119.2(4) . .
C3 C4 H4 120.4 . .
C5 C4 H4 120.4 . .
C2 C5 C4 116.6(3) . .
C2 C5 C6 122.9(3) . .
C4 C5 C6 120.4(3) . .
C6 C6 C5 112.9(4) 2_566 .
C6 C6 H6A 109.0 2_566 .
C5 C6 H6A 109.0 . .
C6 C6 H6B 109.0 2_566 .
C5 C6 H6B 109.0 . .
H6A C6 H6B 107.8 . .
C25 C20 C21 120.1(3) . .
C25 C20 C100 116.4(17) . .
C21 C20 C100 122.4(17) . .
C25 C20 Br1 118.8(2) . .
C21 C20 Br1 121.0(3) . .
C100 C20 Br1 13.3(14) . .
C25 C20 Cl1 125.6(5) . .
C21 C20 Cl1 114.3(5) . .
C100 C20 Cl1 12.7(16) . .
Br1 C20 Cl1 7.8(4) . .
O4 C21 C22 123.2(3) . .
O4 C21 C20 117.3(3) . .
C22 C21 C20 119.5(3) . .
C23 C22 C21 119.7(3) . .
C23 C22 H22 120.2 . .
C21 C22 H22 120.2 . .
C24 C23 C22 121.1(3) . .
C24 C23 H23 119.4 . .
C22 C23 H23 119.4 . .
C25 C24 C23 119.7(3) . .
C25 C24 H24 120.1 . .
C23 C24 H24 120.1 . .
O3 C25 C24 122.9(3) . .
O3 C25 C20 117.2(3) . .
C24 C25 C20 119.9(3) . .
C29 C26 H26A 109.5 . .
C29 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
C29 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
C29 C26 H26D 109.5 . .
H26A C26 H26D 141.1 . .
H26B C26 H26D 56.3 . .
H26C C26 H26D 56.3 . .
C29 C26 H26E 109.5 . .
H26A C26 H26E 56.3 . .
H26B C26 H26E 141.1 . .
H26C C26 H26E 56.3 . .
H26D C26 H26E 109.5 . .
C29 C26 H26F 109.5 . .
H26A C26 H26F 56.3 . .
H26B C26 H26F 56.3 . .
H26C C26 H26F 141.1 . .
H26D C26 H26F 109.5 . .
H26E C26 H26F 109.5 . .
C28 C27 H27A 109.5 . .
C28 C27 H27B 109.5 . .
H27A C27 H27B 109.5 . .
C28 C27 H27C 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
C28 C27 H27D 109.5 . .
H27A C27 H27D 141.1 . .
H27B C27 H27D 56.3 . .
H27C C27 H27D 56.3 . .
C28 C27 H27E 109.5 . .
H27A C27 H27E 56.3 . .
H27B C27 H27E 141.1 . .
H27C C27 H27E 56.3 . .
H27D C27 H27E 109.5 . .
C28 C27 H27F 109.5 . .
H27A C27 H27F 56.3 . .
H27B C27 H27F 56.3 . .
H27C C27 H27F 141.1 . .
H27D C27 H27F 109.5 . .
H27E C27 H27F 109.5 . .
N3 C28 C29 119.8(3) . 2_765
N3 C28 C27 117.1(3) . .
C29 C28 C27 123.1(3) 2_765 .
N3 C29 C28 120.8(3) . 2_765
N3 C29 C26 117.0(3) . .
C28 C29 C26 122.2(3) 2_765 .
C44 C34 C35 118.1(4) . .
C44 C34 H34 120.9 . .
C35 C34 H34 120.9 . .
C34 C35 C36 119.1(4) . .
C34 C35 H35 120.5 . .
C36 C35 H35 120.5 . .
C35 C36 C37 119.1(4) . .
C35 C36 H36 120.5 . .
C37 C36 H36 120.5 . .
N4 C37 C36 122.2(3) . .
N4 C37 C37 116.5(4) . 2_665
C36 C37 C37 121.3(4) . 2_665
N4 C44 C34 124.4(4) . .
N4 C44 H44 117.8 . .
C34 C44 H44 117.8 . .
C3 N1 C1 115.9(3) . .
C29 N3 C28 119.4(3) . .
C37 N4 C44 117.2(3) . .
C25 O3 H3A 109.5 . .
C21 O4 H4A 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.340(5) .
C1 C2 1.379(5) .
C1 H1 0.9300 .
C2 C5 1.385(5) .
C2 H2 0.9300 .
C3 N1 1.322(5) .
C3 C4 1.381(5) .
C3 H3 0.9300 .
C4 C5 1.385(5) .
C4 H4 0.9300 .
C5 C6 1.511(5) .
C6 C6 1.501(7) 2_566
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C20 C25 1.400(4) .
C20 C21 1.407(4) .
C20 C100 1.80(5) .
C20 Br1 1.838(5) .
C20 Cl1 1.883(19) .
C21 O4 1.362(4) .
C21 C22 1.393(4) .
C22 C23 1.391(5) .
C22 H22 0.9300 .
C23 C24 1.387(5) .
C23 H23 0.9300 .
C24 C25 1.389(5) .
C24 H24 0.9300 .
C25 O3 1.366(4) .
C26 C29 1.506(5) .
C26 H26A 0.9600 .
C26 H26B 0.9600 .
C26 H26C 0.9600 .
C26 H26D 0.9600 .
C26 H26E 0.9600 .
C26 H26F 0.9600 .
C27 C28 1.506(5) .
C27 H27A 0.9600 .
C27 H27B 0.9600 .
C27 H27C 0.9600 .
C27 H27D 0.9600 .
C27 H27E 0.9600 .
C27 H27F 0.9600 .
C28 N3 1.347(4) .
C28 C29 1.393(5) 2_765
C29 N3 1.335(4) .
C29 C28 1.393(5) 2_765
C34 C44 1.364(5) .
C34 C35 1.379(6) .
C34 H34 0.9300 .
C35 C36 1.383(5) .
C35 H35 0.9300 .
C36 C37 1.395(5) .
C36 H36 0.9300 .
C37 N4 1.334(5) .
C37 C37 1.493(7) 2_665
C44 N4 1.351(5) .
C44 H44 0.9300 .
O3 H3A 0.8200 .
O4 H4A 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
C4 H4 Br1 0.93 3.11 4.032(5) 170.7 .
C22 H22 Br1 0.93 3.07 3.743(5) 130.3 1_655
C34 H34 Br1 0.93 3.13 3.801(6) 130.5 1_665
O3 H3A N3 0.82 1.99 2.800(4) 169.0 1_455
O4 H4A N1 0.82 1.96 2.773(4) 169.2 2_656
C4 H4 Br1 0.93 3.11 4.032(5) 170.7 .
C22 H22 Br1 0.93 3.07 3.743(5) 130.3 1_655
C34 H34 Br1 0.93 3.13 3.801(6) 130.5 1_665
O3 H3A N3 0.82 1.99 2.800(4) 169.0 1_455
O4 H4A N1 0.82 1.96 2.773(4) 169.2 2_656
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
N1 C1 C2 C5 -0.3(6) . .
N1 C3 C4 C5 1.6(7) . .
C1 C2 C5 C4 -0.3(6) . .
C1 C2 C5 C6 179.7(4) . .
C3 C4 C5 C2 -0.3(6) . .
C3 C4 C5 C6 179.7(4) . .
C2 C5 C6 C6 112.6(5) . 2_566
C4 C5 C6 C6 -67.4(6) . 2_566
C25 C20 C21 O4 -178.9(3) . .
C100 C20 C21 O4 -11.4(17) . .
Br1 C20 C21 O4 4.2(4) . .
Cl1 C20 C21 O4 -0.2(7) . .
C25 C20 C21 C22 1.6(5) . .
C100 C20 C21 C22 169.2(17) . .
Br1 C20 C21 C22 -175.2(3) . .
Cl1 C20 C21 C22 -179.6(7) . .
O4 C21 C22 C23 -179.6(3) . .
C20 C21 C22 C23 -0.2(5) . .
C21 C22 C23 C24 -1.2(5) . .
C22 C23 C24 C25 1.1(5) . .
C23 C24 C25 O3 -178.6(3) . .
C23 C24 C25 C20 0.3(5) . .
C21 C20 C25 O3 177.3(3) . .
C100 C20 C25 O3 9.0(17) . .
Br1 C20 C25 O3 -5.8(4) . .
Cl1 C20 C25 O3 -1.3(8) . .
C21 C20 C25 C24 -1.7(5) . .
C100 C20 C25 C24 -170.0(17) . .
Br1 C20 C25 C24 175.2(3) . .
Cl1 C20 C25 C24 179.7(7) . .
C44 C34 C35 C36 -0.7(6) . .
C34 C35 C36 C37 0.3(6) . .
C35 C36 C37 N4 0.1(5) . .
C35 C36 C37 C37 -179.1(4) . 2_665
C35 C34 C44 N4 0.8(6) . .
C4 C3 N1 C1 -2.2(6) . .
C2 C1 N1 C3 1.5(6) . .
C28 C29 N3 C28 0.6(5) 2_765 .
C26 C29 N3 C28 -178.7(3) . .
C29 C28 N3 C29 -0.6(5) 2_765 .
C27 C28 N3 C29 179.2(3) . .
C36 C37 N4 C44 0.0(5) . .
C37 C37 N4 C44 179.2(4) 2_665 .
C34 C44 N4 C37 -0.5(6) . .
