#------------------------------------------------------------------------------
#$Date: 2018-02-06 02:46:13 +0200 (Tue, 06 Feb 2018) $
#$Revision: 206201 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/71/4127146.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_4127146
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, C8 H12 N2, 2(C6 H5 Cl O2)'
_chemical_formula_sum            'C42 H42 Cl2 N6 O4'
_chemical_formula_weight         765.71
_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                97.863(13)
_cell_angle_beta                 95.939(15)
_cell_angle_gamma                92.493(10)
_cell_formula_units_Z            1
_cell_length_a                   7.542(7)
_cell_length_b                   8.824(8)
_cell_length_c                   14.579(14)
_cell_measurement_reflns_used    2480
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33.5
_cell_measurement_theta_min      2.3
_cell_volume                     954.3(15)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_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  0.1067
_diffrn_reflns_av_unetI/netI     0.0999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_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            10236
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_min         1.419
_exptl_absorpt_coefficient_mu    0.221
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       Block
_exptl_crystal_F_000             402
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4377
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0614
_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)+(0.0573P)²+0.0490P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1515
_refine_ls_wR_factor_ref         0.1709
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3185
_reflns_number_total             4377
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b12501_si_003.cif
_cod_data_source_block           QT1
_cod_database_code               4127146
_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   0.927
_shelx_estimated_absorpt_t_max   0.965
_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
Cl1 Cl 0.85354(7) 0.54974(7) 0.35194(4) 0.0468(2) Uani 1 1 d . .
O1 O 1.1754(2) 0.38846(19) 0.39024(12) 0.0467(4) Uani 1 1 d . .
H1 H 1.2630 0.3368 0.3937 0.070 Uiso 1 1 calc R U
O2 O 0.9150(2) 0.7526(2) 0.21739(12) 0.0512(5) Uani 1 1 d . .
H2 H 0.9266 0.7899 0.1697 0.077 Uiso 1 1 calc R U
C19 C 1.0518(3) 0.5744(2) 0.30427(14) 0.0327(5) Uani 1 1 d . .
C20 C 1.0636(3) 0.6801(2) 0.24146(15) 0.0358(5) Uani 1 1 d . .
C21 C 1.1976(3) 0.4914(2) 0.33020(15) 0.0353(5) Uani 1 1 d . .
C22 C 1.3583(3) 0.5180(3) 0.29445(17) 0.0441(6) Uani 1 1 d . .
H22 H 1.4570 0.4639 0.3110 0.053 Uiso 1 1 calc R U
C24 C 1.2269(3) 0.7049(3) 0.20711(17) 0.0441(6) Uani 1 1 d . .
H24 H 1.2384 0.7755 0.1659 0.053 Uiso 1 1 calc R U
C23 C 1.3707(3) 0.6249(3) 0.23449(17) 0.0462(6) Uani 1 1 d . .
H23 H 1.4793 0.6434 0.2119 0.055 Uiso 1 1 calc R U
N1 N 0.9732(2) 0.9180(2) 0.07160(13) 0.0387(4) Uani 1 1 d . .
C17 C 1.0420(3) 1.0632(2) 0.09016(16) 0.0377(5) Uani 1 1 d . .
C15 C 0.9302(3) 0.8534(2) -0.01769(16) 0.0377(5) Uani 1 1 d . .
C14 C 0.8563(4) 0.6903(3) -0.0348(2) 0.0550(7) Uani 1 1 d . .
H14A H 0.8476 0.6538 0.0238 0.082 Uiso 1 1 calc R U
H14B H 0.9340 0.6281 -0.0700 0.082 Uiso 1 1 calc R U
H14C H 0.7398 0.6845 -0.0690 0.082 Uiso 1 1 calc R U
C18 C 1.0899(4) 1.1288(3) 0.19084(17) 0.0563(7) Uani 1 1 d . .
H18A H 1.0608 1.0536 0.2295 0.084 Uiso 1 1 calc R U
H18B H 1.0240 1.2180 0.2054 0.084 Uiso 1 1 calc R U
H18C H 1.2156 1.1567 0.2019 0.084 Uiso 1 1 calc R U
N3 N 0.4601(3) 0.2032(2) 0.41116(15) 0.0470(5) Uani 1 1 d . .
C1 C 0.7947(3) 0.0769(3) 0.43510(16) 0.0403(5) Uani 1 1 d . .
C2 C 0.6439(3) -0.0109(3) 0.39018(18) 0.0487(6) Uani 1 1 d . .
H2A H 0.6520 -0.1137 0.3674 0.058 Uiso 1 1 calc R U
C7 C 0.9749(3) 0.0112(3) 0.44973(17) 0.0504(6) Uani 1 1 d . .
H7A H 1.0647 0.0794 0.4312 0.060 Uiso 1 1 calc R U
H7B H 0.9739 -0.0867 0.4102 0.060 Uiso 1 1 calc R U
C6 C 0.7713(3) 0.2293(3) 0.46711(17) 0.0463(6) Uani 1 1 d . .
H6 H 0.8678 0.2930 0.4968 0.056 Uiso 1 1 calc R U
C3 C 0.4833(3) 0.0566(3) 0.38010(19) 0.0514(6) Uani 1 1 d . .
H3 H 0.3846 -0.0036 0.3497 0.062 Uiso 1 1 calc R U
C5 C 0.6055(3) 0.2857(3) 0.45478(18) 0.0492(6) Uani 1 1 d . .
H5 H 0.5929 0.3877 0.4781 0.059 Uiso 1 1 calc R U
C11 C 0.5382(3) 0.0737(3) 0.02705(17) 0.0413(5) Uani 1 1 d . .
N2 N 0.5741(3) 0.1865(2) -0.02258(15) 0.0530(6) Uani 1 1 d . .
C10 C 0.5718(3) 0.0934(3) 0.12377(18) 0.0499(6) Uani 1 1 d . .
H10 H 0.5470 0.0130 0.1565 0.060 Uiso 1 1 calc R U
C8 C 0.6767(4) 0.3507(3) 0.1198(2) 0.0580(7) Uani 1 1 d . .
H8 H 0.7216 0.4468 0.1494 0.070 Uiso 1 1 calc R U
C9 C 0.6423(4) 0.2334(3) 0.17088(19) 0.0573(7) Uani 1 1 d . .
H9 H 0.6661 0.2484 0.2355 0.069 Uiso 1 1 calc R U
C13 C 0.6429(4) 0.3213(3) 0.0248(2) 0.0592(7) Uani 1 1 d . .
H13 H 0.6692 0.3996 -0.0092 0.071 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'
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
C21 O1 H1 109.5 . .
C20 O2 H2 109.5 . .
C21 C19 C20 121.22(19) . .
C21 C19 Cl1 119.77(17) . .
C20 C19 Cl1 119.00(16) . .
O2 C20 C24 123.6(2) . .
O2 C20 C19 117.83(19) . .
C24 C20 C19 118.5(2) . .
O1 C21 C22 123.1(2) . .
O1 C21 C19 117.98(19) . .
C22 C21 C19 118.9(2) . .
C23 C22 C21 119.7(2) . .
C23 C22 H22 120.2 . .
C21 C22 H22 120.2 . .
C23 C24 C20 119.8(2) . .
C23 C24 H24 120.1 . .
C20 C24 H24 120.1 . .
C24 C23 C22 121.8(2) . .
C24 C23 H23 119.1 . .
C22 C23 H23 119.1 . .
C17 N1 C15 119.52(19) . .
N1 C17 C15 120.3(2) . 2_775
N1 C17 C18 117.3(2) . .
C15 C17 C18 122.3(2) 2_775 .
N1 C15 C17 120.1(2) . 2_775
N1 C15 C14 117.5(2) . .
C17 C15 C14 122.4(2) 2_775 .
C15 C14 H14A 109.5 . .
C15 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C15 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C3 N3 C5 116.0(2) . .
C6 C1 C2 116.8(2) . .
C6 C1 C7 120.7(2) . .
C2 C1 C7 122.5(2) . .
C3 C2 C1 119.3(2) . .
C3 C2 H2A 120.4 . .
C1 C2 H2A 120.4 . .
C1 C7 C7 112.3(2) . 2_756
C1 C7 H7A 109.1 . .
C7 C7 H7A 109.1 2_756 .
C1 C7 H7B 109.1 . .
C7 C7 H7B 109.1 2_756 .
H7A C7 H7B 107.9 . .
C5 C6 C1 119.7(2) . .
C5 C6 H6 120.2 . .
C1 C6 H6 120.2 . .
N3 C3 C2 124.1(2) . .
N3 C3 H3 117.9 . .
C2 C3 H3 117.9 . .
N3 C5 C6 124.1(2) . .
N3 C5 H5 117.9 . .
C6 C5 H5 117.9 . .
N2 C11 C10 121.9(2) . .
N2 C11 C11 116.3(3) . 2_655
C10 C11 C11 121.8(3) . 2_655
C11 N2 C13 117.4(2) . .
C9 C10 C11 119.5(2) . .
C9 C10 H10 120.2 . .
C11 C10 H10 120.2 . .
C13 C8 C9 118.2(3) . .
C13 C8 H8 120.9 . .
C9 C8 H8 120.9 . .
C10 C9 C8 118.6(3) . .
C10 C9 H9 120.7 . .
C8 C9 H9 120.7 . .
N2 C13 C8 124.3(3) . .
N2 C13 H13 117.9 . .
C8 C13 H13 117.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C19 1.730(2) .
O1 C21 1.362(3) .
O1 H1 0.8200 .
O2 C20 1.353(3) .
O2 H2 0.8200 .
C19 C21 1.395(3) .
C19 C20 1.400(3) .
C20 C24 1.397(3) .
C21 C22 1.391(3) .
C22 C23 1.377(4) .
C22 H22 0.9300 .
C24 C23 1.374(3) .
C24 H24 0.9300 .
C23 H23 0.9300 .
N1 C17 1.342(3) .
N1 C15 1.348(3) .
C17 C15 1.395(3) 2_775
C17 C18 1.503(3) .
C15 C17 1.395(3) 2_775
C15 C14 1.500(3) .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
N3 C3 1.336(3) .
N3 C5 1.340(3) .
C1 C6 1.387(4) .
C1 C2 1.397(4) .
C1 C7 1.508(3) .
C2 C3 1.376(4) .
C2 H2A 0.9300 .
C7 C7 1.517(5) 2_756
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C6 C5 1.370(3) .
C6 H6 0.9300 .
C3 H3 0.9300 .
C5 H5 0.9300 .
C11 N2 1.342(3) .
C11 C10 1.392(4) .
C11 C11 1.486(5) 2_655
N2 C13 1.345(3) .
C10 C9 1.384(4) .
C10 H10 0.9300 .
C8 C13 1.369(4) .
C8 C9 1.385(4) .
C8 H8 0.9300 .
C9 H9 0.9300 .
C13 H13 0.9300 .
