#------------------------------------------------------------------------------
#$Date: 2018-02-06 02:46:13 +0200 (Tue, 06 Feb 2018) $
#$Revision: 206201 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/71/4127148.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_4127148
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
'C8 H4 S2, C12 H12 N2, C8 H12 N2, 2(C6 H5 Cl O2)'
_chemical_formula_sum            'C40 H38 Cl2 N4 O4 S2'
_chemical_formula_weight         773.76
_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                97.722(13)
_cell_angle_beta                 97.118(16)
_cell_angle_gamma                94.181(14)
_cell_formula_units_Z            1
_cell_length_a                   7.542(7)
_cell_length_b                   8.625(8)
_cell_length_c                   14.890(13)
_cell_measurement_reflns_used    2896
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      33.9
_cell_measurement_theta_min      2.4
_cell_volume                     948.5(15)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1101
_diffrn_reflns_av_unetI/netI     0.0891
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_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       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10021
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.733
_exptl_absorpt_coefficient_mu    0.328
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       Block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.670
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4322
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0569
_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)+(0.0591P)²+0.1957P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1540
_refine_ls_wR_factor_ref         0.1635
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3596
_reflns_number_total             4322
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b12501_si_003.cif
_cod_data_source_block           QT3
_cod_original_cell_volume        948.4(15)
_cod_database_code               4127148
_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   0.810
_shelx_estimated_absorpt_t_max   0.934
_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 0.4408(2) 0.4288(2) 0.19862(12) 0.0352(4) Uani 1 1 d . . .
C2 C 0.4282(3) 0.3248(2) 0.26189(13) 0.0406(4) Uani 1 1 d . . .
C3 C 0.2650(3) 0.2998(2) 0.29477(14) 0.0474(5) Uani 1 1 d . . .
H3 H 0.2529 0.2297 0.3364 0.057 Uiso 1 1 calc R U .
C4 C 0.1223(3) 0.3787(3) 0.26574(15) 0.0478(5) Uani 1 1 d . . .
H4 H 0.0137 0.3606 0.2878 0.057 Uiso 1 1 calc R U .
C5 C 0.1363(3) 0.4847(2) 0.20439(14) 0.0448(4) Uani 1 1 d . . .
H5 H 0.0383 0.5379 0.1860 0.054 Uiso 1 1 calc R U .
C6 C 0.2975(2) 0.5111(2) 0.17049(12) 0.0359(4) Uani 1 1 d . . .
C11 C 0.5281(3) 0.9897(3) 0.04948(14) 0.0511(5) Uani 1 1 d . . .
H11A H 0.5332 1.0904 0.0880 0.061 Uiso 1 1 calc R U .
H11B H 0.4385 0.9190 0.0684 0.061 Uiso 1 1 calc R U .
C12 C 0.7080(3) 0.9249(2) 0.06312(12) 0.0410(4) Uani 1 1 d . . .
C13 C 0.7253(3) 0.7685(2) 0.03160(14) 0.0453(4) Uani 1 1 d . . .
H13 H 0.6261 0.7027 0.0020 0.054 Uiso 1 1 calc R U .
C14 C 0.8904(3) 0.7121(2) 0.04456(14) 0.0468(5) Uani 1 1 d . . .
H14 H 0.8992 0.6071 0.0227 0.056 Uiso 1 1 calc R U .
C15 C 1.0227(3) 0.9482(3) 0.11652(15) 0.0497(5) Uani 1 1 d . . .
H15 H 1.1243 1.0107 0.1462 0.060 Uiso 1 1 calc R U .
C16 C 0.8624(3) 1.0158(2) 0.10578(14) 0.0493(5) Uani 1 1 d . . .
H16 H 0.8580 1.1217 0.1270 0.059 Uiso 1 1 calc R U .
C17 C 0.9619(3) 0.9388(3) 0.46294(16) 0.0598(6) Uani 1 1 d . . .
C19 C 0.8349(4) 0.6961(5) 0.3740(2) 0.0828(9) Uani 1 1 d . . .
H19 H 0.7848 0.5925 0.3627 0.099 Uiso 1 1 calc R U .
C20 C 0.8469(4) 0.7973(4) 0.3147(2) 0.0789(8) Uani 1 1 d . . .
H20 H 0.8086 0.7810 0.2521 0.095 Uiso 1 1 calc R U .
N2 N 1.0396(2) 0.7978(2) 0.08645(12) 0.0463(4) Uani 1 1 d . . .
O1 O 0.5755(2) 0.2539(2) 0.28834(11) 0.0591(4) Uani 1 1 d . . .
H1 H 0.5580 0.2077 0.3316 0.089 Uiso 1 1 calc R U .
O2 O 0.3210(2) 0.61308(17) 0.11042(10) 0.0479(4) Uani 1 1 d . . .
H2 H 0.2357 0.6668 0.1067 0.072 Uiso 1 1 calc R U .
Cl1 Cl 0.64053(6) 0.45432(6) 0.15393(4) 0.04917(18) Uani 1 1 d . . .
S1A S 0.9235(4) 0.9869(3) 0.35277(18) 0.0639(5) Uani 0.5189 1 d . . P
C18A C 0.931(2) 0.9352(14) 0.3693(8) 0.073(3) Uani 0.4811 1 d . . P
S1B S 0.8999(6) 0.7502(6) 0.4845(3) 0.0831(8) Uani 0.482 1 d . . P
C18B C 0.922(2) 0.7896(19) 0.4650(10) 0.078(3) Uani 0.518 1 d . . P
C7 C 0.3956(4) -0.1287(3) 0.31289(15) 0.0640(6) Uani 1 1 d . . .
H7A H 0.4174 -0.0487 0.2755 0.096 Uiso 1 1 calc R U .
H7B H 0.2701 -0.1640 0.3034 0.096 Uiso 1 1 calc R U .
H7C H 0.4636 -0.2155 0.2965 0.096 Uiso 1 1 calc R U .
C8 C 0.4514(3) -0.0629(2) 0.41161(13) 0.0436(4) Uani 1 1 d . . .
C9 C 0.5644(3) 0.1523(2) 0.51804(14) 0.0428(4) Uani 1 1 d . . .
C10 C 0.6325(4) 0.3230(3) 0.5368(2) 0.0685(7) Uani 1 1 d . . .
H10A H 0.6335 0.3639 0.4800 0.103 Uiso 1 1 calc R U .
H10B H 0.7520 0.3343 0.5692 0.103 Uiso 1 1 calc R U .
H10C H 0.5555 0.3799 0.5733 0.103 Uiso 1 1 calc R U .
N1 N 0.5159(2) 0.08754(19) 0.43099(11) 0.0449(4) Uani 1 1 d . . .
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'
S S 0.1246 0.1234 '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
C6 C1 C2 121.64(18) . .
C6 C1 Cl1 119.62(15) . .
C2 C1 Cl1 118.74(14) . .
O1 C2 C1 118.02(18) . .
O1 C2 C3 123.49(18) . .
C1 C2 C3 118.49(17) . .
C4 C3 C2 119.94(18) . .
C4 C3 H3 120.0 . .
C2 C3 H3 120.0 . .
C3 C4 C5 121.48(19) . .
C3 C4 H4 119.3 . .
C5 C4 H4 119.3 . .
C4 C5 C6 119.59(18) . .
C4 C5 H5 120.2 . .
C6 C5 H5 120.2 . .
O2 C6 C1 118.35(17) . .
O2 C6 C5 122.82(17) . .
C1 C6 C5 118.83(17) . .
C12 C11 C11 112.2(2) . 2_675
C12 C11 H11A 109.2 . .
C11 C11 H11A 109.2 2_675 .
C12 C11 H11B 109.2 . .
C11 C11 H11B 109.2 2_675 .
H11A C11 H11B 107.9 . .
C13 C12 C16 117.01(18) . .
C13 C12 C11 120.20(19) . .
C16 C12 C11 122.8(2) . .
C14 C13 C12 119.21(19) . .
C14 C13 H13 120.4 . .
C12 C13 H13 120.4 . .
N2 C14 C13 124.39(19) . .
N2 C14 H14 117.8 . .
C13 C14 H14 117.8 . .
N2 C15 C16 123.4(2) . .
N2 C15 H15 118.3 . .
C16 C15 H15 118.3 . .
C15 C16 C12 119.6(2) . .
C15 C16 H16 120.2 . .
C12 C16 H16 120.2 . .
C18B C17 C18A 97.9(9) . .
C18B C17 C17 129.1(7) . 2_776
C18A C17 C17 132.5(6) . 2_776
C18B C17 S1A 112.2(7) . .
C18A C17 S1A 15.0(5) . .
C17 C17 S1A 118.6(3) 2_776 .
C18B C17 S1B 9.9(7) . .
C18A C17 S1B 106.7(6) . .
C17 C17 S1B 120.7(3) 2_776 .
S1A C17 S1B 120.7(2) . .
C20 C19 C18B 103.9(5) . .
C20 C19 S1B 121.3(3) . .
C18B C19 S1B 17.9(4) . .
C20 C19 H19 128.1 . .
C18B C19 H19 128.1 . .
S1B C19 H19 110.6 . .
C19 C20 C18A 103.5(5) . .
C19 C20 S1A 119.8(3) . .
C18A C20 S1A 17.2(4) . .
C19 C20 H20 128.3 . .
C18A C20 H20 128.3 . .
S1A C20 H20 111.7 . .
C14 N2 C15 116.32(17) . .
C2 O1 H1 109.5 . .
C6 O2 H2 109.5 . .
C18A S1A C20 50.2(18) . .
C18A S1A C17 41.2(16) . .
C20 S1A C17 88.73(18) . .
S1A C18A C17 124(2) . .
S1A C18A C20 113(2) . .
C17 C18A C20 118.8(8) . .
S1A C18A C18B 160(2) . .
C17 C18A C18B 39.7(6) . .
C20 C18A C18B 79.7(7) . .
C18B S1B C19 67(2) . .
C18B S1B C17 26(2) . .
C19 S1B C17 89.4(2) . .
S1B C18B C17 144(3) . .
S1B C18B C19 95(3) . .
C17 C18B C19 114.8(9) . .
S1B C18B C18A 162(3) . .
C17 C18B C18A 42.5(5) . .
C19 C18B C18A 73.0(7) . .
C8 C7 H7A 109.5 . .
C8 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C8 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
N1 C8 C9 120.05(18) . 2_656
N1 C8 C7 117.52(19) . .
C9 C8 C7 122.4(2) 2_656 .
N1 C9 C8 120.18(19) . 2_656
N1 C9 C10 118.0(2) . .
C8 C9 C10 121.8(2) 2_656 .
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 . .
C8 N1 C9 119.78(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.388(3) .
C1 C2 1.392(3) .
C1 Cl1 1.732(2) .
C2 O1 1.348(2) .
C2 C3 1.393(3) .
C3 C4 1.371(3) .
C3 H3 0.9300 .
C4 C5 1.384(3) .
C4 H4 0.9300 .
C5 C6 1.389(3) .
C5 H5 0.9300 .
C6 O2 1.354(2) .
C11 C12 1.506(3) .
C11 C11 1.520(4) 2_675
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 C13 1.388(3) .
C12 C16 1.387(3) .
C13 C14 1.370(3) .
C13 H13 0.9300 .
C14 N2 1.334(3) .
C14 H14 0.9300 .
C15 N2 1.335(3) .
C15 C16 1.381(3) .
C15 H15 0.9300 .
C16 H16 0.9300 .
C17 C18B 1.305(15) .
C17 C18A 1.380(12) .
C17 C17 1.450(5) 2_776
C17 S1A 1.741(4) .
C17 S1B 1.742(5) .
C19 C20 1.329(5) .
C19 C18B 1.525(18) .
C19 S1B 1.651(6) .
C19 H19 0.9300 .
C20 C18A 1.408(15) .
C20 S1A 1.691(5) .
C20 H20 0.9300 .
O1 H1 0.8200 .
O2 H2 0.8200 .
S1A C18A 0.542(9) .
C18A C18B 2.025(14) .
S1B C18B 0.509(10) .
C7 C8 1.499(3) .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C8 N1 1.333(3) .
C8 C9 1.393(3) 2_656
C9 N1 1.336(3) .
C9 C8 1.393(3) 2_656
C9 C10 1.501(3) .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 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
O2 H2 N2 0.82 1.94 2.762(3) 174.4 1_455
C3 H3 S1B 0.93 3.02 3.721(5) 133.2 2_666
C3 H3 N1 0.93 2.75 3.406(3) 128.5 .
O1 H1 N1 0.82 1.96 2.781(3) 177.2 .
C10 H10B S1B 0.96 2.95 3.673(7) 133.0 2_766
C5 H5 Cl1 0.93 3.00 3.704(4) 134.0 1_455
O2 H2 N2 0.82 1.94 2.762(3) 174.4 1_455
C3 H3 S1B 0.93 3.02 3.721(5) 133.2 2_666
C3 H3 N1 0.93 2.75 3.406(3) 128.5 .
O1 H1 N1 0.82 1.96 2.781(3) 177.2 .
C10 H10B S1B 0.96 2.95 3.673(7) 133.0 2_766
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
C6 C1 C2 O1 -177.49(18) .
Cl1 C1 C2 O1 2.9(3) .
C6 C1 C2 C3 2.2(3) .
Cl1 C1 C2 C3 -177.40(15) .
O1 C2 C3 C4 178.8(2) .
C1 C2 C3 C4 -1.0(3) .
C2 C3 C4 C5 -0.5(3) .
C3 C4 C5 C6 0.7(3) .
C2 C1 C6 O2 178.43(17) .
Cl1 C1 C6 O2 -1.9(2) .
C2 C1 C6 C5 -2.1(3) .
Cl1 C1 C6 C5 177.57(14) .
C4 C5 C6 O2 -179.93(19) .
C4 C5 C6 C1 0.6(3) .
C11 C11 C12 C13 -72.9(3) 2_675
C11 C11 C12 C16 106.4(3) 2_675
C16 C12 C13 C14 0.6(3) .
C11 C12 C13 C14 179.84(18) .
C12 C13 C14 N2 0.3(3) .
N2 C15 C16 C12 1.1(3) .
C13 C12 C16 C15 -1.2(3) .
C11 C12 C16 C15 179.55(19) .
C18B C19 C20 C18A -0.8(9) .
S1B C19 C20 C18A 3.8(7) .
C18B C19 C20 S1A -6.7(7) .
S1B C19 C20 S1A -2.1(5) .
C13 C14 N2 C15 -0.4(3) .
C16 C15 N2 C14 -0.3(3) .
C19 C20 S1A C18A 20(2) .
C19 C20 S1A C17 3.5(3) .
C18A C20 S1A C17 -16(2) .
C18B C17 S1A C18A -17(3) .
C17 C17 S1A C18A 160(3) 2_776
S1B C17 S1A C18A -23(3) .
C18B C17 S1A C20 1.8(8) .
C18A C17 S1A C20 19(3) .
C17 C17 S1A C20 179.1(3) 2_776
S1B C17 S1A C20 -4.1(3) .
C20 S1A C18A C17 -155(3) .
C17 S1A C18A C20 155(3) .
C20 S1A C18A C18B -124(8) .
C17 S1A C18A C18B 31(5) .
C18B C17 C18A S1A 164(3) .
C17 C17 C18A S1A -24(3) 2_776
S1B C17 C18A S1A 159(2) .
C18B C17 C18A C20 10.5(13) .
C17 C17 C18A C20 -177.4(5) 2_776
S1A C17 C18A C20 -153(4) .
S1B C17 C18A C20 5.9(12) .
C17 C17 C18A C18B 172.1(11) 2_776
S1A C17 C18A C18B -164(3) .
S1B C17 C18A C18B -4.6(9) .
C19 C20 C18A S1A -162(2) .
C19 C20 C18A C17 -6.2(11) .
S1A C20 C18A C17 156(3) .
C19 C20 C18A C18B 0.6(7) .
S1A C20 C18A C18B 163(2) .
C20 C19 S1B C18B -15(3) .
C20 C19 S1B C17 -0.7(4) .
C18B C19 S1B C17 14(3) .
C18A C17 S1B C18B 27(6) .
C17 C17 S1B C18B -150(5) 2_776
S1A C17 S1B C18B 33(6) .
C18B C17 S1B C19 -30(5) .
C18A C17 S1B C19 -2.8(7) .
C17 C17 S1B C19 -179.9(3) 2_776
S1A C17 S1B C19 3.3(3) .
C19 S1B C18B C17 147(6) .
C17 S1B C18B C19 -147(6) .
C19 S1B C18B C18A 47(9) .
C17 S1B C18B C18A -100(12) .
C18A C17 C18B S1B -154(5) .
C17 C17 C18B S1B 34(6) 2_776
S1A C17 C18B S1B -149(5) .
C18A C17 C18B C19 -10.4(13) .
C17 C17 C18B C19 177.1(5) 2_776
S1A C17 C18B C19 -5.9(13) .
S1B C17 C18B C19 143(6) .
C17 C17 C18B C18A -172.5(10) 2_776
S1A C17 C18B C18A 4.4(7) .
S1B C17 C18B C18A 154(5) .
C20 C19 C18B S1B 167(3) .
C20 C19 C18B C17 7.9(13) .
S1B C19 C18B C17 -159(4) .
C20 C19 C18B C18A 0.6(7) .
S1B C19 C18B C18A -167(3) .
C9 C8 N1 C9 -0.3(3) 2_656
C7 C8 N1 C9 178.80(18) .
C8 C9 N1 C8 0.3(3) 2_656
C10 C9 N1 C8 -178.7(2) .
