#------------------------------------------------------------------------------
#$Date: 2019-11-23 15:27:43 +0200 (Sat, 23 Nov 2019) $
#$Revision: 233824 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/60/7236005.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_7236005
loop_
_publ_author_name
'Gabr, Moustafa T.'
'Pigge, F. Christopher'
_publ_section_title
;
 Synthesis and aggregation-induced emission properties of pyridine and
 pyridinium analogues of tetraphenylethylene
;
_journal_issue                   110
_journal_name_full               'RSC Advances'
_journal_page_first              90226
_journal_paper_doi               10.1039/C5RA18724A
_journal_volume                  5
_journal_year                    2015
_chemical_formula_sum            'C24 H18 N2'
_chemical_formula_weight         334.40
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-09-02 deposited with the CCDC.
2015-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                68.944(5)
_cell_angle_beta                 80.486(5)
_cell_angle_gamma                86.159(5)
_cell_formula_units_Z            2
_cell_length_a                   9.0727(9)
_cell_length_b                   9.4508(9)
_cell_length_c                   11.5627(12)
_cell_measurement_reflns_used    3799
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      1.00
_cell_volume                     912.48(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      190(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  Enraf-Nonius
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_sigmaI/netI    0.0901
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7909
_diffrn_reflns_theta_full        27.84
_diffrn_reflns_theta_max         27.84
_diffrn_reflns_theta_min         2.74
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.9929
_exptl_absorpt_correction_T_min  0.9837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2010)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'colorless irregular prism'
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.240(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4294
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.925
_refine_ls_R_factor_all          0.1284
_refine_ls_R_factor_gt           0.0577
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0956P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1653
_reflns_number_gt                2351
_reflns_number_total             4294
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra18724a2.cif
_cod_data_source_block           fcp1516-3
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7236005
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.4665(2) 0.40185(19) 0.77798(17) 0.0306(4) Uani 1 1 d .
C19 C 0.3121(2) 0.35399(18) 0.84411(18) 0.0308(5) Uani 1 1 d .
C8 C 0.5689(2) 0.27444(19) 0.76869(18) 0.0303(4) Uani 1 1 d .
C14 C 0.4162(2) 0.67927(19) 0.73508(18) 0.0325(5) Uani 1 1 d .
C2 C 0.5148(2) 0.54671(19) 0.73321(17) 0.0316(5) Uani 1 1 d .
C3 C 0.6741(2) 0.58685(19) 0.67879(18) 0.0332(5) Uani 1 1 d .
C13 C 0.5991(2) 0.15973(19) 0.87758(19) 0.0349(5) Uani 1 1 d .
H13A H 0.5508 0.1613 0.9566 0.042 Uiso 1 1 calc R
C24 C 0.2327(2) 0.26023(19) 0.80717(19) 0.0345(5) Uani 1 1 d .
H24A H 0.2755 0.2326 0.7375 0.041 Uiso 1 1 calc R
C17 C 0.2003(2) 0.8358(2) 0.68846(19) 0.0400(5) Uani 1 1 d .
H17A H 0.1087 0.8526 0.6557 0.048 Uiso 1 1 calc R
C20 C 0.2479(2) 0.3903(2) 0.94798(19) 0.0383(5) Uani 1 1 d .
H20A H 0.3002 0.4531 0.9755 0.046 Uiso 1 1 calc R
C4 C 0.7913(2) 0.5145(2) 0.7416(2) 0.0395(5) Uani 1 1 d .
H4A H 0.7720 0.4357 0.8210 0.047 Uiso 1 1 calc R
N2 N 0.2420(2) 0.93846(18) 0.73223(17) 0.0440(5) Uani 1 1 d .
C18 C 0.2820(2) 0.7076(2) 0.68806(18) 0.0340(5) Uani 1 1 d .
H18A H 0.2465 0.6391 0.6558 0.041 Uiso 1 1 calc R
C9 C 0.6376(2) 0.2675(2) 0.65444(19) 0.0394(5) Uani 1 1 d .
H9A H 0.6174 0.3438 0.5787 0.047 Uiso 1 1 calc R
C12 C 0.6980(2) 0.0434(2) 0.8732(2) 0.0400(5) Uani 1 1 d .
H12A H 0.7185 -0.0333 0.9486 0.048 Uiso 1 1 calc R
N1 N 0.9731(2) 0.6671(2) 0.57594(18) 0.0517(5) Uani 1 1 d .
C15 C 0.4604(2) 0.7853(2) 0.7797(2) 0.0432(5) Uani 1 1 d .
H15A H 0.5522 0.7721 0.8120 0.052 Uiso 1 1 calc R
C23 C 0.0924(2) 0.2065(2) 0.8703(2) 0.0417(5) Uani 1 1 d .
H23A H 0.0390 0.1443 0.8429 0.050 Uiso 1 1 calc R
C11 C 0.7666(2) 0.0389(2) 0.7592(2) 0.0450(6) Uani 1 1 d .
H11A H 0.8351 -0.0405 0.7558 0.054 Uiso 1 1 calc R
C22 C 0.0305(2) 0.2441(2) 0.9732(2) 0.0456(6) Uani 1 1 d .
H22A H -0.0652 0.2070 1.0173 0.055 Uiso 1 1 calc R
C7 C 0.7113(2) 0.7020(2) 0.5637(2) 0.0435(5) Uani 1 1 d .
H7A H 0.6352 0.7566 0.5177 0.052 Uiso 1 1 calc R
C21 C 0.1082(2) 0.3355(2) 1.0117(2) 0.0445(5) Uani 1 1 d .
H21A H 0.0656 0.3612 1.0824 0.053 Uiso 1 1 calc R
C5 C 0.9358(2) 0.5581(2) 0.6874(2) 0.0466(6) Uani 1 1 d .
H5A H 1.0142 0.5074 0.7323 0.056 Uiso 1 1 calc R
C16 C 0.3711(2) 0.9096(2) 0.7773(2) 0.0464(6) Uani 1 1 d .
H16A H 0.4036 0.9793 0.8098 0.056 Uiso 1 1 calc R
C10 C 0.7358(2) 0.1496(2) 0.6502(2) 0.0482(6) Uani 1 1 d .
H10A H 0.7820 0.1454 0.5715 0.058 Uiso 1 1 calc R
C6 C 0.8596(2) 0.7365(2) 0.5165(2) 0.0504(6) Uani 1 1 d .
H6A H 0.8824 0.8144 0.4369 0.061 Uiso 1 1 calc R
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C8 121.36(16)
C2 C1 C19 124.15(16)
C8 C1 C19 114.45(14)
C20 C19 C24 118.13(17)
C20 C19 C1 122.33(16)
C24 C19 C1 119.37(16)
C9 C8 C13 118.31(16)
C9 C8 C1 122.24(17)
C13 C8 C1 119.44(17)
C18 C14 C15 116.60(16)
C18 C14 C2 123.00(15)
C15 C14 C2 120.33(17)
C1 C2 C14 123.73(17)
C1 C2 C3 122.07(15)
C14 C2 C3 114.20(14)
C4 C3 C7 116.89(18)
C4 C3 C2 121.98(17)
C7 C3 C2 121.11(17)
C12 C13 C8 121.23(18)
C23 C24 C19 121.26(18)
N2 C17 C18 124.16(19)
C21 C20 C19 120.58(19)
C5 C4 C3 119.31(19)
C16 N2 C17 115.61(16)
C17 C18 C14 119.54(17)
C8 C9 C10 120.36(19)
C11 C12 C13 119.79(19)
C5 N1 C6 115.90(19)
C16 C15 C14 119.90(19)
C24 C23 C22 119.67(19)
C10 C11 C12 119.93(18)
C21 C22 C23 119.78(19)
C6 C7 C3 119.54(19)
C22 C21 C20 120.56(19)
N1 C5 C4 124.4(2)
N2 C16 C15 124.18(18)
C11 C10 C9 120.3(2)
N1 C6 C7 124.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.353(2)
C1 C8 1.495(2)
C1 C19 1.495(3)
C19 C20 1.392(3)
C19 C24 1.395(3)
C8 C9 1.386(3)
C8 C13 1.389(3)
C14 C18 1.386(3)
C14 C15 1.388(3)
C14 C2 1.494(2)
C2 C3 1.493(3)
C3 C4 1.387(3)
C3 C7 1.389(3)
C13 C12 1.382(3)
C24 C23 1.387(3)
C17 N2 1.344(2)
C17 C18 1.378(2)
C20 C21 1.386(3)
C4 C5 1.377(3)
N2 C16 1.332(3)
C9 C10 1.390(3)
C12 C11 1.375(3)
N1 C5 1.336(3)
N1 C6 1.335(3)
C15 C16 1.376(3)
C23 C22 1.383(3)
C11 C10 1.375(3)
C22 C21 1.379(3)
C7 C6 1.379(3)
