#------------------------------------------------------------------------------
#$Date: 2019-11-23 16:48:47 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234055 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/46/7124644.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_7124644
loop_
_publ_author_name
'Wang, Zhaoyang'
'Bai, Wei'
'Tong, Jiaqi'
'Wang, Yi Jia'
'Qin, Anjun'
'Sun, Jing Zhi'
'Tang, Ben Zhong'
_publ_section_title
;
 A macrocyclic 1,4-bis(4-pyridylethynyl)benzene showing unique
 aggregation-induced emission properties.
;
_journal_issue                   68
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              10365
_journal_page_last               10368
_journal_paper_doi               10.1039/c6cc02851a
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         '2(F6 P), C34 H26 N2, 2(C2 H3 N)'
_chemical_formula_sum            'C38 H32 F12 N4 P2'
_chemical_formula_weight         834.62
_chemical_name_systematic
N,N'-bisbenzyl-1,4-bis(4-pyridin-1-iumylethynyl)benzenebishexafluorophosphate
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-07-15
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2015-09-11 deposited with the CCDC.
2016-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                104.695(8)
_cell_angle_beta                 100.791(11)
_cell_angle_gamma                108.868(11)
_cell_formula_units_Z            1
_cell_length_a                   8.8259(14)
_cell_length_b                   9.7216(8)
_cell_length_c                   12.7688(13)
_cell_measurement_reflns_used    1383
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3846
_cell_measurement_theta_min      3.1852
_cell_volume                     958.4(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0305018000
_diffrn_orient_matrix_UB_12      -0.0014689000
_diffrn_orient_matrix_UB_13      0.0550270000
_diffrn_orient_matrix_UB_21      0.0745068000
_diffrn_orient_matrix_UB_22      -0.0025910000
_diffrn_orient_matrix_UB_23      -0.0120127000
_diffrn_orient_matrix_UB_31      0.0376123000
_diffrn_orient_matrix_UB_32      0.0818728000
_diffrn_orient_matrix_UB_33      0.0209322000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6002
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.19
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             426
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.753
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       0.013(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.394
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3498
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.394
_refine_ls_R_factor_all          0.1472
_refine_ls_R_factor_gt           0.1090
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3342
_refine_ls_wR_factor_ref         0.3863
_reflns_number_gt                2254
_reflns_number_total             3498
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc02851a2.cif
_cod_data_source_block           150715_bispy_2bz
_cod_database_code               7124644
_chemical_oxdiff_formula         'c10 h10 B2 Si8'
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C2(H2), C1(H1), C17(H17), C9(H9), C12(H12), C16(H16), C5(H5),
 C11(H11), C8(H8)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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_calc_flag
_atom_site_refinement_flags_posn
P1 P 0.3520(2) -0.04374(16) 0.69464(13) 0.0701(7) Uani 1 d .
F1 F 0.4843(10) 0.1117(7) 0.7133(9) 0.216(4) Uani 1 d .
F3 F 0.2198(8) -0.1906(5) 0.6936(10) 0.247(5) Uani 1 d .
F4 F 0.4892(7) -0.1090(8) 0.7165(7) 0.179(3) Uani 1 d .
F2 F 0.2212(9) 0.0187(9) 0.6604(9) 0.227(4) Uani 1 d .
F5 F 0.3508(19) 0.0280(11) 0.8091(6) 0.311(7) Uani 1 d .
N1 N 0.4070(5) 0.4889(4) 0.6788(3) 0.0468(10) Uani 1 d .
C4 C 0.2172(7) 0.3514(6) 0.9391(5) 0.0660(15) Uani 1 d .
H4 H 0.1726 0.2487 0.9348 0.079 Uiso 1 calc R
C3 C 0.1878(7) 0.4601(8) 1.0156(4) 0.0721(16) Uani 1 d .
H3 H 0.1246 0.4324 1.0631 0.086 Uiso 1 calc R
C2 C 0.2539(8) 0.6100(7) 1.0198(5) 0.0729(16) Uani 1 d .
H2 H 0.2367 0.6857 1.0717 0.087 Uiso 1 calc R
C15 C 0.0702(6) 0.0806(5) 0.1159(3) 0.0435(11) Uani 1 d .
C6 C 0.3759(6) 0.5403(5) 0.8718(3) 0.0465(11) Uani 1 d .
C10 C 0.2668(6) 0.3132(5) 0.4526(4) 0.0484(12) Uani 1 d .
C1 C 0.3463(7) 0.6508(6) 0.9478(4) 0.0624(14) Uani 1 d .
H1 H 0.3886 0.7530 0.9506 0.075 Uiso 1 calc R
C17 C 0.1468(6) -0.0046(5) 0.0572(4) 0.0490(12) Uani 1 d .
H17 H 0.2454 -0.0075 0.0959 0.059 Uiso 1 calc R
C9 C 0.1969(6) 0.4068(6) 0.5084(4) 0.0546(13) Uani 1 d .
H9 H 0.0995 0.4106 0.4686 0.065 Uiso 1 calc R
C12 C 0.4756(6) 0.3966(6) 0.6279(4) 0.0549(12) Uani 1 d .
H12 H 0.5717 0.3934 0.6700 0.066 Uiso 1 calc R
C16 C -0.0781(6) 0.0847(5) 0.0577(4) 0.0511(12) Uani 1 d .
H16 H -0.1303 0.1411 0.0961 0.061 Uiso 1 calc R
C5 C 0.3102(7) 0.3905(5) 0.8695(4) 0.0559(13) Uani 1 d .
H5 H 0.3296 0.3145 0.8196 0.067 Uiso 1 calc R
C11 C 0.4089(7) 0.3075(6) 0.5165(4) 0.0552(13) Uani 1 d .
H11 H 0.4581 0.2434 0.4835 0.066 Uiso 1 calc R
C7 C 0.4831(7) 0.5883(6) 0.7983(4) 0.0584(13) Uani 1 d .
H7A H 0.5014 0.6941 0.8039 0.070 Uiso 1 calc R
H7B H 0.5914 0.5847 0.8260 0.070 Uiso 1 calc R
C8 C 0.2661(6) 0.4919(5) 0.6181(4) 0.0546(13) Uani 1 d .
H8 H 0.2164 0.5541 0.6531 0.066 Uiso 1 calc R
C14 C 0.1413(6) 0.1626(5) 0.2339(4) 0.0513(12) Uani 1 d .
C13 C 0.2008(6) 0.2316(5) 0.3348(3) 0.0491(12) Uani 1 d .
C18 C -0.1163(8) 0.3064(8) 0.6853(5) 0.0760(17) Uani 1 d .
N2 N -0.1124(9) 0.4269(8) 0.6995(6) 0.113(2) Uani 1 d .
C19 C -0.1192(12) 0.1556(8) 0.6657(7) 0.114(3) Uani 1 d .
H19A H -0.1984 0.1005 0.6979 0.171 Uiso 1 calc GR
H19B H -0.0098 0.1616 0.7003 0.171 Uiso 1 calc GR
H19C H -0.1515 0.1022 0.5857 0.171 Uiso 1 calc GR
F6 F 0.3426(18) -0.1177(17) 0.5792(5) 0.326(8) Uani 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'
F F 0.0171 0.0103 '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'
P P 0.1023 0.0942 '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
F1 P1 F3 171.7(5) .
F1 P1 F4 90.4(4) .
F1 P1 F2 88.0(4) .
F3 P1 F4 90.7(4) .
F2 P1 F3 91.8(5) .
F2 P1 F4 173.5(5) .
F5 P1 F1 84.5(5) .
F5 P1 F3 87.2(6) .
F5 P1 F4 102.0(8) .
F5 P1 F2 84.1(8) .
F6 P1 F1 97.6(8) .
F6 P1 F3 90.7(8) .
F6 P1 F4 80.7(5) .
F6 P1 F2 93.3(5) .
F6 P1 F5 176.6(8) .
C12 N1 C7 121.5(4) .
C12 N1 C8 119.0(4) .
C8 N1 C7 119.5(4) .
C3 C4 H4 119.2 .
C5 C4 H4 119.2 .
C5 C4 C3 121.6(5) .
C4 C3 H3 120.9 .
C2 C3 C4 118.1(5) .
C2 C3 H3 120.9 .
C3 C2 H2 119.6 .
C3 C2 C1 120.8(5) .
C1 C2 H2 119.6 .
C17 C15 C16 119.5(4) .
C17 C15 C14 120.6(4) .
C16 C15 C14 119.9(4) .
C1 C6 C7 119.5(4) .
C5 C6 C1 118.1(5) .
C5 C6 C7 122.4(4) .
C9 C10 C11 117.1(4) .
C9 C10 C13 121.7(4) .
C11 C10 C13 121.2(4) .
C2 C1 H1 119.8 .
C6 C1 C2 120.4(5) .
C6 C1 H1 119.8 .
C15 C17 H17 119.6 .
C16 C17 C15 120.8(4) 2
C16 C17 H17 119.6 2
C10 C9 H9 119.2 .
C8 C9 C10 121.5(5) .
C8 C9 H9 119.2 .
N1 C12 H12 119.0 .
N1 C12 C11 122.0(4) .
C11 C12 H12 119.0 .
C15 C16 H16 120.2 .
C17 C16 C15 119.7(4) 2
C17 C16 H16 120.2 2
C4 C5 C6 121.0(5) .
C4 C5 H5 119.5 .
C6 C5 H5 119.5 .
C10 C11 H11 120.3 .
C12 C11 C10 119.4(4) .
C12 C11 H11 120.3 .
N1 C7 C6 112.5(4) .
N1 C7 H7A 109.1 .
N1 C7 H7B 109.1 .
C6 C7 H7A 109.1 .
C6 C7 H7B 109.1 .
H7A C7 H7B 107.8 .
N1 C8 H8 119.5 .
C9 C8 N1 120.9(4) .
C9 C8 H8 119.5 .
C13 C14 C15 179.3(5) .
C14 C13 C10 178.6(5) .
N2 C18 C19 178.7(9) .
C18 C19 H19A 109.5 .
C18 C19 H19B 109.5 .
C18 C19 H19C 109.5 .
H19A C19 H19B 109.5 .
H19A C19 H19C 109.5 .
H19B C19 H19C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 F1 1.509(6) .
P1 F3 1.519(6) .
P1 F4 1.551(5) .
P1 F2 1.514(6) .
P1 F5 1.455(6) .
P1 F6 1.440(6) .
N1 C12 1.340(6) .
N1 C7 1.470(5) .
N1 C8 1.350(6) .
C4 H4 0.9300 .
C4 C3 1.373(8) .
C4 C5 1.360(8) .
C3 H3 0.9300 .
C3 C2 1.365(9) .
C2 H2 0.9300 .
C2 C1 1.388(8) .
C15 C17 1.393(6) .
C15 C16 1.397(7) .
C15 C14 1.418(6) .
C6 C1 1.382(7) .
C6 C5 1.373(6) .
C6 C7 1.504(7) .
C10 C9 1.384(6) .
C10 C11 1.388(7) .
C10 C13 1.414(6) .
C1 H1 0.9300 .
C17 H17 0.9300 .
C17 C16 1.382(6) 2
C9 H9 0.9300 .
C9 C8 1.336(6) .
C12 H12 0.9300 .
C12 C11 1.361(7) .
C16 C17 1.382(6) 2
C16 H16 0.9300 .
C5 H5 0.9300 .
C11 H11 0.9300 .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 H8 0.9300 .
C14 C13 1.211(6) .
C18 N2 1.128(8) .
C18 C19 1.414(10) .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
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_4
N1 C12 C11 C10 0.9(8) .
C4 C3 C2 C1 0.9(9) .
C3 C4 C5 C6 -1.1(8) .
C3 C2 C1 C6 -1.3(8) .
C15 C14 C13 C10 -69(56) .
C10 C9 C8 N1 -0.3(8) .
C1 C6 C5 C4 0.7(7) .
C1 C6 C7 N1 -132.6(5) .
C17 C15 C16 C17 -0.1(7) 2
C17 C15 C14 C13 -109(49) .
C9 C10 C11 C12 -2.4(7) .
C9 C10 C13 C14 -7(21) .
C12 N1 C7 C6 -113.4(5) .
C12 N1 C8 C9 -1.3(7) .
C16 C15 C17 C16 0.1(7) 2
C16 C15 C14 C13 70(49) .
C5 C4 C3 C2 0.4(8) .
C5 C6 C1 C2 0.5(7) .
C5 C6 C7 N1 49.8(6) .
C11 C10 C9 C8 2.1(8) .
C11 C10 C13 C14 175(100) .
C7 N1 C12 C11 -178.1(4) .
C7 N1 C8 C9 177.8(4) .
C7 C6 C1 C2 -177.1(5) .
C7 C6 C5 C4 178.3(5) .
C8 N1 C12 C11 1.0(7) .
C8 N1 C7 C6 67.6(6) .
C14 C15 C17 C16 180.0(4) 2
C14 C15 C16 C17 -180.0(4) 2
C13 C10 C9 C8 -175.4(4) .
C13 C10 C11 C12 175.2(4) .
