#------------------------------------------------------------------------------
#$Date: 2018-02-06 02:46:13 +0200 (Tue, 06 Feb 2018) $
#$Revision: 206201 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/71/4127153.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_4127153
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(C6.68 H7.03 Cl0.32 O2), C8 H12 N2'
_chemical_formula_sum            'C43.36 H46.07 Cl0.64 N6 O4'
_chemical_formula_weight         738.05
_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   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                96.925(15)
_cell_angle_beta                 94.732(9)
_cell_angle_gamma                92.000(13)
_cell_formula_units_Z            1
_cell_length_a                   7.576(6)
_cell_length_b                   8.823(7)
_cell_length_c                   14.487(12)
_cell_measurement_reflns_used    2565
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      33.7
_cell_measurement_theta_min      2.3
_cell_volume                     957.0(13)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_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            10216
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.844
_exptl_absorpt_coefficient_mu    0.127
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             391.2
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         4383
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0605
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1051P)²+0.1068P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1718
_refine_ls_wR_factor_ref         0.1908
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3250
_reflns_number_total             4383
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b12501_si_003.cif
_cod_data_source_block           QN3
_cod_original_cell_volume        957.1(14)
_cod_database_code               4127153
_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
C25 C 0.3596(3) 0.6921(2) 0.46640(19) 0.0600(6) Uani 1 1 d . . .
H25A H 0.3393 0.6600 0.4006 0.090 Uiso 0.5 1 calc R U P
H25B H 0.4429 0.6273 0.4938 0.090 Uiso 0.5 1 calc R U P
H25C H 0.2497 0.6853 0.4946 0.090 Uiso 0.5 1 calc R U P
H25D H 0.3487 0.6551 0.5254 0.090 Uiso 0.5 1 calc R U P
H25E H 0.2450 0.6877 0.4322 0.090 Uiso 0.5 1 calc R U P
H25F H 0.4382 0.6297 0.4313 0.090 Uiso 0.5 1 calc R U P
C26 C 0.4221(4) 0.8757(3) 0.30927(16) 0.0615(6) Uani 1 1 d . . .
H26A H 0.3747 0.7726 0.3053 0.092 Uiso 0.5 1 calc R U P
H26B H 0.3366 0.9371 0.2805 0.092 Uiso 0.5 1 calc R U P
H26C H 0.5285 0.8768 0.2776 0.092 Uiso 0.5 1 calc R U P
H26D H 0.4518 0.9517 0.2703 0.092 Uiso 0.5 1 calc R U P
H26E H 0.4899 0.7872 0.2951 0.092 Uiso 0.5 1 calc R U P
H26F H 0.2980 0.8475 0.2980 0.092 Uiso 0.5 1 calc R U P
C1 C 0.8297(3) 0.6526(3) 0.38294(19) 0.0654(7) Uani 1 1 d . . .
H100 H 0.7849 0.5576 0.3541 0.078 Uiso 1 1 calc R U .
C2 C 0.8591(4) 0.6813(3) 0.47790(19) 0.0670(7) Uani 1 1 d . . .
H2 H 0.8316 0.6030 0.5126 0.080 Uiso 1 1 calc R U .
C4 C 0.9637(3) 0.9273(2) 0.47369(15) 0.0472(5) Uani 1 1 d . . .
C5 C 0.9360(3) 0.9083(3) 0.37688(17) 0.0584(6) Uani 1 1 d . . .
H5 H 0.9625 0.9883 0.3433 0.070 Uiso 1 1 calc R U .
C6 C 0.8687(4) 0.7695(3) 0.33114(18) 0.0673(7) Uani 1 1 d . . .
H6 H 0.8498 0.7547 0.2664 0.081 Uiso 1 1 calc R U .
C7 C -0.0894(3) 0.7283(3) 0.03583(17) 0.0596(6) Uani 1 1 d . . .
H7 H -0.0709 0.6306 0.0074 0.072 Uiso 1 1 calc R U .
C8 C -0.2559(3) 0.7834(3) 0.02268(18) 0.0599(6) Uani 1 1 d . . .
H8 H -0.3461 0.7229 -0.0126 0.072 Uiso 1 1 calc R U .
C9 C -0.2884(3) 0.9287(2) 0.06206(14) 0.0475(5) Uani 1 1 d . . .
C10 C -0.1456(3) 1.0112(2) 0.11404(15) 0.0538(5) Uani 1 1 d . . .
H10 H -0.1598 1.1101 0.1420 0.065 Uiso 1 1 calc R U .
C11 C 0.0160(3) 0.9463(3) 0.12385(16) 0.0548(5) Uani 1 1 d . . .
H11 H 0.1090 1.0040 0.1587 0.066 Uiso 1 1 calc R U .
C12 C -0.4706(3) 0.9917(3) 0.04978(16) 0.0619(6) Uani 1 1 d . . .
H12A H -0.5555 0.9244 0.0733 0.074 Uiso 1 1 calc R U .
H12B H -0.4704 1.0908 0.0869 0.074 Uiso 1 1 calc R U .
C13 C 0.4631(2) 0.4355(2) 0.19275(12) 0.0372(4) Uani 1 1 d . . .
C14 C 0.4471(2) 0.3284(2) 0.25616(13) 0.0401(4) Uani 1 1 d . . .
C15 C 0.2853(3) 0.2997(2) 0.29086(15) 0.0477(5) Uani 1 1 d . . .
H15 H 0.2746 0.2268 0.3317 0.057 Uiso 1 1 calc R U .
C16 C 0.1402(3) 0.3803(2) 0.26428(16) 0.0507(5) Uani 1 1 d . . .
H16 H 0.0319 0.3611 0.2875 0.061 Uiso 1 1 calc R U .
C17 C 0.1541(3) 0.4892(2) 0.20354(15) 0.0490(5) Uani 1 1 d . . .
H17 H 0.0559 0.5432 0.1865 0.059 Uiso 1 1 calc R U .
C18 C 0.3151(3) 0.5171(2) 0.16833(12) 0.0393(4) Uani 1 1 d . . .
C23 C 0.4637(3) 0.9391(2) 0.40987(13) 0.0413(4) Uani 1 1 d . . .
C24 C 0.4325(2) 0.8544(2) 0.48243(14) 0.0406(4) Uani 1 1 d . . .
N1 N 0.0472(2) 0.8048(2) 0.08626(13) 0.0511(4) Uani 1 1 d . . .
N3 N 0.4684(2) 0.91689(17) 0.57185(11) 0.0420(4) Uani 1 1 d . . .
N4 N 0.9247(3) 0.8145(2) 0.52447(14) 0.0601(5) Uani 1 1 d . . .
O1 O 0.5961(2) 0.25424(19) 0.28059(12) 0.0558(4) Uani 1 1 d . . .
O2 O 0.3370(2) 0.62199(17) 0.10789(10) 0.0511(4) Uani 1 1 d . . .
Cl1 Cl 0.6528(8) 0.4581(8) 0.1480(5) 0.0462(14) Uani 0.3224 1 d . . P
C100 C 0.6414(18) 0.4662(18) 0.1492(10) 0.061(4) Uani 0.6776 1 d . . P
H10A H 0.7298 0.4018 0.1726 0.091 Uiso 0.6776 1 calc R U P
H10B H 0.6235 0.4441 0.0825 0.091 Uiso 0.6776 1 calc R U P
H10C H 0.6802 0.5714 0.1658 0.091 Uiso 0.6776 1 calc R U P
H101 H 0.248(3) 0.678(3) 0.1004(17) 0.056(7) Uiso 1 1 d . . .
H20 H 0.583(6) 0.206(5) 0.327(3) 0.131(15) Uiso 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'
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
C24 C25 H25A 109.5 . .
C24 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
C24 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
C24 C25 H25D 109.5 . .
H25A C25 H25D 141.1 . .
H25B C25 H25D 56.3 . .
H25C C25 H25D 56.3 . .
C24 C25 H25E 109.5 . .
H25A C25 H25E 56.3 . .
H25B C25 H25E 141.1 . .
H25C C25 H25E 56.3 . .
H25D C25 H25E 109.5 . .
C24 C25 H25F 109.5 . .
H25A C25 H25F 56.3 . .
H25B C25 H25F 56.3 . .
H25C C25 H25F 141.1 . .
H25D C25 H25F 109.5 . .
H25E C25 H25F 109.5 . .
C23 C26 H26A 109.5 . .
C23 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
C23 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
C23 C26 H26D 109.5 . .
H26A C26 H26D 141.1 . .
H26B C26 H26D 56.3 . .
H26C C26 H26D 56.3 . .
C23 C26 H26E 109.5 . .
H26A C26 H26E 56.3 . .
H26B C26 H26E 141.1 . .
H26C C26 H26E 56.3 . .
H26D C26 H26E 109.5 . .
C23 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 . .
C2 C1 C6 117.8(2) . .
C2 C1 H1 121.1 . .
C6 C1 H1 121.1 . .
N4 C2 C1 124.6(2) . .
N4 C2 H2 117.7 . .
C1 C2 H2 117.7 . .
N4 C4 C5 121.8(2) . .
N4 C4 C4 116.4(2) . 2_776
C5 C4 C4 121.7(2) . 2_776
C6 C5 C4 119.3(2) . .
C6 C5 H5 120.3 . .
C4 C5 H5 120.3 . .
C5 C6 C1 119.1(2) . .
C5 C6 H6 120.4 . .
C1 C6 H6 120.4 . .
N1 C7 C8 124.7(2) . .
N1 C7 H7 117.7 . .
C8 C7 H7 117.7 . .
C7 C8 C9 119.7(2) . .
C7 C8 H8 120.2 . .
C9 C8 H8 120.2 . .
C8 C9 C10 116.3(2) . .
C8 C9 C12 120.9(2) . .
C10 C9 C12 122.8(2) . .
C11 C10 C9 119.9(2) . .
C11 C10 H10 120.1 . .
C9 C10 H10 120.1 . .
N1 C11 C10 123.8(2) . .
N1 C11 H11 118.1 . .
C10 C11 H11 118.1 . .
C12 C12 C9 113.4(2) 2_475 .
C12 C12 H12A 108.9 2_475 .
C9 C12 H12A 108.9 . .
C12 C12 H12B 108.9 2_475 .
C9 C12 H12B 108.9 . .
H12A C12 H12B 107.7 . .
C18 C13 C14 118.70(17) . .
C18 C13 C100 119.4(6) . .
C14 C13 C100 121.9(6) . .
C18 C13 Cl1 122.2(3) . .
C14 C13 Cl1 119.1(3) . .
C100 C13 Cl1 3.1(8) . .
O1 C14 C15 122.45(18) . .
O1 C14 C13 117.02(17) . .
C15 C14 C13 120.53(17) . .
C16 C15 C14 119.51(19) . .
C16 C15 H15 120.2 . .
C14 C15 H15 120.2 . .
C15 C16 C17 120.90(19) . .
C15 C16 H16 119.5 . .
C17 C16 H16 119.5 . .
C16 C17 C18 119.66(18) . .
C16 C17 H17 120.2 . .
C18 C17 H17 120.2 . .
O2 C18 C17 122.45(17) . .
O2 C18 C13 116.89(17) . .
C17 C18 C13 120.66(18) . .
N3 C23 C24 120.43(17) 2_676 .
N3 C23 C26 117.37(18) 2_676 .
C24 C23 C26 122.20(19) . .
N3 C24 C23 120.27(18) . .
N3 C24 C25 116.84(18) . .
C23 C24 C25 122.89(19) . .
C7 N1 C11 115.62(19) . .
C23 N3 C24 119.30(16) 2_676 .
C2 N4 C4 117.3(2) . .
C14 O1 H20 112(3) . .
C18 O2 H1 114.2(16) . .
C13 C100 H10A 109.5 . .
C13 C100 H10B 109.5 . .
H10A C100 H10B 109.5 . .
C13 C100 H10C 109.5 . .
H10A C100 H10C 109.5 . .
H10B C100 H10C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C25 C24 1.501(3) .
C25 H25A 0.9600 .
C25 H25B 0.9600 .
C25 H25C 0.9600 .
C25 H25D 0.9600 .
C25 H25E 0.9600 .
C25 H25F 0.9600 .
C26 C23 1.501(3) .
C26 H26A 0.9600 .
C26 H26B 0.9600 .
C26 H26C 0.9600 .
C26 H26D 0.9600 .
C26 H26E 0.9600 .
C26 H26F 0.9600 .
C1 C2 1.367(4) .
C1 C6 1.385(4) .
C1 H1 0.9300 .
C2 N4 1.340(3) .
C2 H2 0.9300 .
C4 N4 1.346(3) .
C4 C5 1.390(3) .
C4 C4 1.475(4) 2_776
C5 C6 1.379(4) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 N1 1.330(3) .
C7 C8 1.374(3) .
C7 H7 0.9300 .
C8 C9 1.378(3) .
C8 H8 0.9300 .
C9 C10 1.395(3) .
C9 C12 1.511(3) .
C10 C11 1.374(3) .
C10 H10 0.9300 .
C11 N1 1.337(3) .
C11 H11 0.9300 .
C12 C12 1.500(5) 2_475
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 C18 1.397(3) .
C13 C14 1.405(3) .
C13 C100 1.566(11) .
C13 Cl1 1.640(5) .
C14 O1 1.367(2) .
C14 C15 1.389(3) .
C15 C16 1.383(3) .
C15 H15 0.9300 .
C16 C17 1.386(3) .
C16 H16 0.9300 .
C17 C18 1.386(3) .
C17 H17 0.9300 .
C18 O2 1.363(2) .
C23 N3 1.342(3) 2_676
C23 C24 1.392(3) .
C24 N3 1.347(3) .
N3 C23 1.342(3) 2_676
O1 H20 0.85(5) .
O2 H1 0.86(3) .
C100 H10A 0.9600 .
C100 H10B 0.9600 .
C100 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
Cl1 H10A O1 0.86 2.41 2.833(6) 110.5 .
O2 H1 N1 0.86(3) 1.93(3) 2.788(3) 179(2) .
O1 H20 N3 0.85(5) 1.98(5) 2.826(3) 174(4) 2_666
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 N4 -0.7(4) . .
N4 C4 C5 C6 -0.8(4) . .
C4 C4 C5 C6 179.6(2) 2_776 .
C4 C5 C6 C1 0.3(4) . .
C2 C1 C6 C5 0.4(4) . .
N1 C7 C8 C9 1.2(4) . .
C7 C8 C9 C10 -0.2(4) . .
C7 C8 C9 C12 -179.3(2) . .
C8 C9 C10 C11 -0.3(3) . .
C12 C9 C10 C11 178.8(2) . .
C9 C10 C11 N1 -0.3(4) . .
C8 C9 C12 C12 -63.8(4) . 2_475
C10 C9 C12 C12 117.1(3) . 2_475
C18 C13 C14 O1 -178.02(16) . .
C100 C13 C14 O1 1.8(7) . .
Cl1 C13 C14 O1 3.4(4) . .
C18 C13 C14 C15 2.6(3) . .
C100 C13 C14 C15 -177.6(7) . .
Cl1 C13 C14 C15 -176.0(3) . .
O1 C14 C15 C16 179.11(19) . .
C13 C14 C15 C16 -1.6(3) . .
C14 C15 C16 C17 0.0(3) . .
C15 C16 C17 C18 0.5(3) . .
C16 C17 C18 O2 179.57(19) . .
C16 C17 C18 C13 0.6(3) . .
C14 C13 C18 O2 178.86(16) . .
C100 C13 C18 O2 -1.0(7) . .
Cl1 C13 C18 O2 -2.6(4) . .
C14 C13 C18 C17 -2.1(3) . .
C100 C13 C18 C17 178.0(7) . .
Cl1 C13 C18 C17 176.4(4) . .
N3 C23 C24 N3 0.8(3) 2_676 .
C26 C23 C24 N3 -178.58(18) . .
N3 C23 C24 C25 -179.02(18) 2_676 .
C26 C23 C24 C25 1.6(3) . .
C8 C7 N1 C11 -1.6(4) . .
C10 C11 N1 C7 1.2(3) . .
C23 C24 N3 C23 -0.8(3) . 2_676
C25 C24 N3 C23 179.04(17) . 2_676
C1 C2 N4 C4 0.1(4) . .
C5 C4 N4 C2 0.6(3) . .
C4 C4 N4 C2 -179.8(2) 2_776 .
