#------------------------------------------------------------------------------
#$Date: 2018-02-06 02:46:13 +0200 (Tue, 06 Feb 2018) $
#$Revision: 206201 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/71/4127157.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_4127157
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(C6.45 H6.35 Br0.55 O2), C8 H12 N2'
_chemical_formula_sum            'C42.9 H44.71 Br1.1 N6 O4'
_chemical_formula_weight         796.08
_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                96.905(12)
_cell_angle_beta                 95.339(12)
_cell_angle_gamma                91.548(9)
_cell_formula_units_Z            1
_cell_length_a                   7.634(6)
_cell_length_b                   8.818(7)
_cell_length_c                   14.583(11)
_cell_measurement_reflns_used    2942
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33.4
_cell_measurement_theta_min      2.6
_cell_volume                     969.6(13)
_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 0.997
_diffrn_measurement_device_type  CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_av_unetI/netI     0.0645
_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            10383
_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         1.413
_exptl_absorpt_coefficient_mu    1.211
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       block'
_exptl_crystal_F_000             414.5
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         4441
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0668
_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)+(0.1183P)²+0.9046P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2140
_refine_ls_wR_factor_ref         0.2250
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3691
_reflns_number_total             4441
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b12501_si_003.cif
_cod_data_source_block           QN7
_cod_original_formula_sum        'C42.90 H44.71 Br1.10 N6 O4'
_cod_database_code               4127157
_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
Br1 Br 0.3374(2) 0.54498(18) 0.35863(9) 0.0481(3) Uani 0.5488 1 d . . P
C100 C 0.355(3) 0.532(3) 0.3430(15) 0.0481(3) Uani 0.4512 1 d . . P
H10A H 0.3683 0.4560 0.3852 0.072 Uiso 0.4512 1 calc R U P
H10B H 0.3151 0.6240 0.3747 0.072 Uiso 0.4512 1 calc R U P
H10C H 0.2714 0.4943 0.2916 0.072 Uiso 0.4512 1 calc R U P
O1 O 0.6667(4) 0.3763(3) 0.3898(2) 0.0544(7) Uani 1 1 d . . .
H1 H 0.7454 0.3149 0.3871 0.082 Uiso 1 1 calc R U .
C7 C 0.5437(5) 0.5661(4) 0.3053(2) 0.0393(7) Uani 1 1 d . . .
O2 O 0.4111(4) 0.7495(4) 0.2193(2) 0.0590(8) Uani 1 1 d . . .
H2 H 0.4215 0.7849 0.1705 0.088 Uiso 1 1 calc R U .
N2 N 0.9532(5) 1.1940(4) 0.4143(3) 0.0552(8) Uani 1 1 d . . .
C8 C 0.5574(5) 0.6731(4) 0.2426(2) 0.0443(8) Uani 1 1 d . . .
C12 C 0.6898(5) 0.4808(4) 0.3297(2) 0.0407(7) Uani 1 1 d . . .
C2 C 1.2881(6) 1.0719(5) 0.4376(3) 0.0512(9) Uani 1 1 d . . .
C9 C 0.7182(5) 0.6991(5) 0.2074(3) 0.0508(9) Uani 1 1 d . . .
H9 H 0.7283 0.7716 0.1667 0.061 Uiso 1 1 calc R U .
C11 C 0.8470(5) 0.5060(5) 0.2938(3) 0.0517(9) Uani 1 1 d . . .
H11 H 0.9436 0.4491 0.3097 0.062 Uiso 1 1 calc R U .
C10 C 0.8626(5) 0.6165(5) 0.2335(3) 0.0535(9) Uani 1 1 d . . .
H10 H 0.9701 0.6347 0.2108 0.064 Uiso 1 1 calc R U .
C3 C 1.1497(6) 0.9898(5) 0.3861(3) 0.0572(10) Uani 1 1 d . . .
H3 H 1.1658 0.8915 0.3579 0.069 Uiso 1 1 calc R U .
C1 C 1.4718(6) 1.0110(6) 0.4511(3) 0.0645(12) Uani 1 1 d . . .
H1A H 1.4752 0.9139 0.4124 0.077 Uiso 1 1 calc R U .
H1B H 1.5549 1.0815 0.4305 0.077 Uiso 1 1 calc R U .
C4 C 0.9860(6) 1.0532(5) 0.3759(3) 0.0586(10) Uani 1 1 d . . .
H4 H 0.8945 0.9952 0.3407 0.070 Uiso 1 1 calc R U .
C6 C 1.2529(6) 1.2166(5) 0.4793(3) 0.0623(11) Uani 1 1 d . . .
H6 H 1.3411 1.2757 0.5164 0.075 Uiso 1 1 calc R U .
C5 C 1.0883(6) 1.2717(5) 0.4654(3) 0.0619(11) Uani 1 1 d . . .
H5 H 1.0690 1.3695 0.4933 0.074 Uiso 1 1 calc R U .
N1 N 0.4720(4) 0.9176(3) 0.0717(2) 0.0449(7) Uani 1 1 d . . .
C21 C 0.5405(5) 1.0613(4) 0.0894(3) 0.0441(8) Uani 1 1 d . . .
C20 C 0.4322(5) 0.8551(4) -0.0165(3) 0.0415(7) Uani 1 1 d . . .
C18 C -0.0380(5) 0.9259(4) -0.0271(3) 0.0480(8) Uani 1 1 d . . .
N3 N -0.0750(5) 0.8141(4) 0.0235(3) 0.0605(9) Uani 1 1 d . . .
C19 C 0.3582(7) 0.6932(4) -0.0318(4) 0.0621(11) Uani 1 1 d . . .
H19A H 0.3349 0.6610 -0.0972 0.093 Uiso 0.5 1 calc R U P
H19B H 0.4417 0.6274 -0.0052 0.093 Uiso 0.5 1 calc R U P
H19C H 0.2507 0.6877 -0.0028 0.093 Uiso 0.5 1 calc R U P
H19D H 0.3500 0.6564 0.0271 0.093 Uiso 0.5 1 calc R U P
H19E H 0.2432 0.6900 -0.0649 0.093 Uiso 0.5 1 calc R U P
H19F H 0.4342 0.6297 -0.0673 0.093 Uiso 0.5 1 calc R U P
C14 C -0.1419(7) 0.6827(5) -0.0224(3) 0.0638(11) Uani 1 1 d . . .
H14 H -0.1689 0.6045 0.0120 0.077 Uiso 1 1 calc R U .
C17 C -0.0685(6) 0.9105(5) -0.1224(3) 0.0582(10) Uani 1 1 d . . .
H17 H -0.0437 0.9915 -0.1551 0.070 Uiso 1 1 calc R U .
C22 C 0.5834(7) 1.1249(6) 0.1894(3) 0.0654(12) Uani 1 1 d . . .
H22A H 0.6311 1.2276 0.1932 0.098 Uiso 0.5 1 calc R U P
H22B H 0.4783 1.1251 0.2208 0.098 Uiso 0.5 1 calc R U P
H22C H 0.6684 1.0628 0.2183 0.098 Uiso 0.5 1 calc R U P
H22D H 0.5541 1.0494 0.2283 0.098 Uiso 0.5 1 calc R U P
H22E H 0.7069 1.1519 0.2007 0.098 Uiso 0.5 1 calc R U P
H22F H 0.5168 1.2142 0.2032 0.098 Uiso 0.5 1 calc R U P
C15 C -0.1737(6) 0.6548(5) -0.1172(4) 0.0645(11) Uani 1 1 d . . .
H15 H -0.2188 0.5602 -0.1461 0.077 Uiso 1 1 calc R U .
C16 C -0.1366(7) 0.7724(5) -0.1684(3) 0.0634(11) Uani 1 1 d . . .
H16 H -0.1572 0.7585 -0.2328 0.076 Uiso 1 1 calc R U .
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'
Br Br -0.2901 2.4595 '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
C7 C100 H10A 109.5 . .
C7 C100 H10B 109.5 . .
H10A C100 H10B 109.5 . .
C7 C100 H10C 109.5 . .
H10A C100 H10C 109.5 . .
H10B C100 H10C 109.5 . .
C12 O1 H1 109.5 . .
C8 C7 C12 119.8(3) . .
C8 C7 C100 119.8(9) . .
C12 C7 C100 120.2(9) . .
C8 C7 Br1 119.4(3) . .
C12 C7 Br1 120.7(3) . .
C100 C7 Br1 6.6(9) . .
C8 O2 H2 109.5 . .
C5 N2 C4 116.1(4) . .
O2 C8 C9 122.6(3) . .
O2 C8 C7 117.5(3) . .
C9 C8 C7 119.9(3) . .
O1 C12 C11 123.3(3) . .
O1 C12 C7 116.9(3) . .
C11 C12 C7 119.8(3) . .
C3 C2 C6 116.6(4) . .
C3 C2 C1 123.2(4) . .
C6 C2 C1 120.2(4) . .
C10 C9 C8 119.8(4) . .
C10 C9 H9 120.1 . .
C8 C9 H9 120.1 . .
C12 C11 C10 120.5(3) . .
C12 C11 H11 119.8 . .
C10 C11 H11 119.8 . .
C9 C10 C11 120.2(4) . .
C9 C10 H10 119.9 . .
C11 C10 H10 119.9 . .
C2 C3 C4 120.1(4) . .
C2 C3 H3 119.9 . .
C4 C3 H3 119.9 . .
C1 C1 C2 113.6(5) 2_876 .
C1 C1 H1A 108.8 2_876 .
C2 C1 H1A 108.8 . .
C1 C1 H1B 108.8 2_876 .
C2 C1 H1B 108.8 . .
H1A C1 H1B 107.7 . .
N2 C4 C3 123.2(4) . .
N2 C4 H4 118.4 . .
C3 C4 H4 118.4 . .
C5 C6 C2 119.8(4) . .
C5 C6 H6 120.1 . .
C2 C6 H6 120.1 . .
N2 C5 C6 124.1(4) . .
N2 C5 H5 117.9 . .
C6 C5 H5 117.9 . .
C20 N1 C21 119.5(3) . .
N1 C21 C20 120.0(3) . 2_675
N1 C21 C22 117.2(4) . .
C20 C21 C22 122.8(4) 2_675 .
N1 C20 C21 120.4(3) . 2_675
N1 C20 C19 117.0(3) . .
C21 C20 C19 122.6(4) 2_675 .
N3 C18 C17 123.1(4) . .
N3 C18 C18 115.9(4) . 2_575
C17 C18 C18 121.0(4) . 2_575
C14 N3 C18 117.1(4) . .
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 C14 C15 124.4(4) . .
N3 C14 H14 117.8 . .
C15 C14 H14 117.8 . .
C18 C17 C16 118.6(4) . .
C18 C17 H17 120.7 . .
C16 C17 H17 120.7 . .
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 . .
C14 C15 C16 117.8(4) . .
C14 C15 H15 121.1 . .
C16 C15 H15 121.1 . .
C17 C16 C15 119.0(4) . .
C17 C16 H16 120.5 . .
C15 C16 H16 120.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C7 1.834(4) .
C100 C7 1.62(2) .
C100 H10A 0.9600 .
C100 H10B 0.9600 .
C100 H10C 0.9600 .
O1 C12 1.365(4) .
O1 H1 0.8200 .
C7 C8 1.399(5) .
C7 C12 1.404(5) .
O2 C8 1.357(4) .
O2 H2 0.8200 .
N2 C5 1.336(6) .
N2 C4 1.339(6) .
C8 C9 1.397(6) .
C12 C11 1.377(5) .
C2 C3 1.374(6) .
C2 C6 1.390(6) .
C2 C1 1.519(6) .
C9 C10 1.386(6) .
C9 H9 0.9300 .
C11 C10 1.399(6) .
C11 H11 0.9300 .
C10 H10 0.9300 .
C3 C4 1.385(6) .
C3 H3 0.9300 .
C1 C1 1.487(9) 2_876
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C4 H4 0.9300 .
C6 C5 1.366(6) .
C6 H6 0.9300 .
C5 H5 0.9300 .
N1 C20 1.341(5) .
N1 C21 1.344(5) .
C21 C20 1.393(5) 2_675
C21 C22 1.502(6) .
C20 C21 1.393(5) 2_675
C20 C19 1.505(5) .
C18 N3 1.339(5) .
C18 C17 1.378(6) .
C18 C18 1.515(8) 2_575
N3 C14 1.330(6) .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C19 H19D 0.9600 .
C19 H19E 0.9600 .
C19 H19F 0.9600 .
C14 C15 1.371(7) .
C14 H14 0.9300 .
C17 C16 1.381(6) .
C17 H17 0.9300 .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 0.9600 .
C22 H22D 0.9600 .
C22 H22E 0.9600 .
C22 H22F 0.9600 .
C15 C16 1.387(7) .
C15 H15 0.9300 .
C16 H16 0.9300 .
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 O2 178.2(3) . .
C100 C7 C8 O2 3.1(11) . .
Br1 C7 C8 O2 -4.5(5) . .
C12 C7 C8 C9 -2.6(5) . .
C100 C7 C8 C9 -177.7(10) . .
Br1 C7 C8 C9 174.8(3) . .
C8 C7 C12 O1 -178.8(3) . .
C100 C7 C12 O1 -3.7(11) . .
Br1 C7 C12 O1 3.9(4) . .
C8 C7 C12 C11 1.8(5) . .
C100 C7 C12 C11 176.9(10) . .
Br1 C7 C12 C11 -175.5(3) . .
O2 C8 C9 C10 -179.6(4) . .
C7 C8 C9 C10 1.2(6) . .
O1 C12 C11 C10 -179.1(4) . .
C7 C12 C11 C10 0.3(6) . .
C8 C9 C10 C11 0.9(6) . .
C12 C11 C10 C9 -1.7(6) . .
C6 C2 C3 C4 1.4(7) . .
C1 C2 C3 C4 -179.3(4) . .
C3 C2 C1 C1 -114.9(7) . 2_876
C6 C2 C1 C1 64.3(8) . 2_876
C5 N2 C4 C3 -1.0(7) . .
C2 C3 C4 N2 0.0(7) . .
C3 C2 C6 C5 -1.9(7) . .
C1 C2 C6 C5 178.8(5) . .
C4 N2 C5 C6 0.5(7) . .
C2 C6 C5 N2 1.0(8) . .
C20 N1 C21 C20 0.6(6) . 2_675
C20 N1 C21 C22 -179.7(4) . .
C21 N1 C20 C21 -0.7(6) . 2_675
C21 N1 C20 C19 179.2(3) . .
C17 C18 N3 C14 1.0(7) . .
C18 C18 N3 C14 -180.0(4) 2_575 .
C18 N3 C14 C15 0.4(7) . .
N3 C18 C17 C16 -1.6(7) . .
C18 C18 C17 C16 179.5(5) 2_575 .
N3 C14 C15 C16 -1.2(8) . .
C18 C17 C16 C15 0.7(7) . .
C14 C15 C16 C17 0.5(7) . .
