#------------------------------------------------------------------------------
#$Date: 2019-10-11 12:32:05 +0300 (Fri, 11 Oct 2019) $
#$Revision: 219293 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/45/7234562.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_7234562
loop_
_publ_author_name
'Yuanxiang Xu'
'Kai Wang'
'Yujian Zhang'
'Zengqi Xie'
'Bo Zou'
'Yuguang Ma'
_publ_section_title
;
 Fluorescence mutation and structural evolution of a pi-conjugated
 molecular crystal during phase transition
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              1257
_journal_page_last               1262
_journal_paper_doi               10.1039/C5TC03745J
_journal_volume                  4
_journal_year                    2016
_chemical_formula_moiety         'C24 H16 N2'
_chemical_formula_sum            'C24 H16 N2'
_chemical_formula_weight         332.39
_chemical_melting_point          ?
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 100.45(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   26.930(6)
_cell_length_b                   6.9117(14)
_cell_length_c                   9.772(2)
_cell_measurement_reflns_used    3106
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.98
_cell_measurement_theta_min      3.05
_cell_volume                     1788.7(7)
_computing_cell_refinement       Process-auto
_computing_data_collection       Process-auto
_computing_data_reduction        Process-auto
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       omega-scan
_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  0.0551
_diffrn_reflns_av_sigmaI/netI    0.0554
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13195
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         3.05
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.9841
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   Process-auto
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.697
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3106
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.1382
_refine_ls_R_factor_gt           0.0924
_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)+(0.1958P)²+0.4187P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3063
_refine_ls_wR_factor_ref         0.3333
_reflns_number_gt                1680
_reflns_number_total             3106
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2016-4-1257.cif
_cod_data_source_block           p1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'not measured' was changed
to '?' -- the value is undefined or not given.

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2/c
_cod_database_code               7234562
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4194(15) 0.476(7) 0.711(4) 0.086(7) Uani 0.50 1 d P . .
N1' N 0.4032(15) 0.468(7) 0.662(4) 0.086(7) Uani 0.50 1 d P . .
N2 N 0.0955(19) 0.018(8) 0.254(5) 0.089(9) Uani 0.50 1 d P . .
N2' N 0.0814(19) 0.027(8) 0.289(5) 0.089(9) Uani 0.50 1 d P . .
C1 C 0.52254(17) 0.1429(7) 0.4353(5) 0.0568(13) Uani 1 1 d . . .
H1 H 0.5374 0.2417 0.3922 0.080 Uiso 1 1 calc . . .
C2 C 0.48655(18) 0.1880(6) 0.5150(6) 0.0556(12) Uani 1 1 d . . .
H2 H 0.4778 0.3168 0.5244 0.080 Uiso 1 1 calc . . .
C3 C 0.46326(15) 0.0461(7) 0.5811(5) 0.0499(12) Uani 1 1 d . . .
C4 C 0.42418(16) 0.1012(6) 0.6669(5) 0.0495(11) Uani 1 1 d . . .
C5 C 0.4164(2) 0.3010(8) 0.6788(7) 0.0721(17) Uani 1 1 d . . .
C6 C 0.39811(15) -0.0246(6) 0.7271(5) 0.0455(11) Uani 1 1 d . . .
H6 H 0.4064 -0.1523 0.7114 0.080 Uiso 1 1 calc . . .
C7 C 0.35921(15) -0.0076(6) 0.8127(4) 0.0433(11) Uani 1 1 d . . .
C8 C 0.3439(2) 0.1685(8) 0.8627(6) 0.0657(15) Uani 1 1 d . . .
H8 H 0.3589 0.2834 0.8419 0.080 Uiso 1 1 calc . . .
C9 C 0.3060(2) 0.1717(9) 0.9439(6) 0.0757(17) Uani 1 1 d . . .
H9 H 0.2958 0.2886 0.9770 0.080 Uiso 1 1 calc . . .
C10 C 0.28396(18) 0.0000(9) 0.9747(6) 0.0690(16) Uani 1 1 d . . .
H10 H 0.2585 0.0018 1.0274 0.080 Uiso 1 1 calc . . .
C11 C 0.2992(2) -0.1698(9) 0.9285(6) 0.0767(17) Uani 1 1 d . . .
H11 H 0.2846 -0.2848 0.9506 0.080 Uiso 1 1 calc . . .
C12 C 0.33627(19) -0.1732(8) 0.8489(6) 0.0622(14) Uani 1 1 d . . .
H12 H 0.3463 -0.2919 0.8182 0.080 Uiso 1 1 calc . . .
C13 C 0.02211(17) 0.6418(7) 0.0888(5) 0.0544(12) Uani 1 1 d . . .
H13 H 0.0369 0.7391 0.1482 0.080 Uiso 1 1 calc . . .
C14 C 0.01365(17) 0.3100(6) 0.0255(5) 0.0524(12) Uani 1 1 d . . .
H14 H 0.0226 0.1809 0.0415 0.080 Uiso 1 1 calc . . .
C15 C 0.03663(14) 0.4503(7) 0.1175(4) 0.0444(11) Uani 1 1 d . . .
C16 C 0.07526(15) 0.3944(6) 0.2406(5) 0.0471(11) Uani 1 1 d . . .
C17 C 0.0833(2) 0.1885(8) 0.2600(6) 0.0702(17) Uani 1 1 d . . .
C18 C 0.10190(16) 0.5185(6) 0.3289(5) 0.0453(11) Uani 1 1 d . . .
H18 H 0.0944 0.6475 0.3075 0.080 Uiso 1 1 calc . . .
C19 C 0.14060(15) 0.4915(6) 0.4529(4) 0.0417(10) Uani 1 1 d . . .
C20 C 0.1538(2) 0.3156(8) 0.5158(6) 0.0659(15) Uani 1 1 d . . .
H20 H 0.1378 0.2027 0.4795 0.080 Uiso 1 1 calc . . .
C21 C 0.1921(2) 0.3086(9) 0.6359(6) 0.0737(17) Uani 1 1 d . . .
H21 H 0.2011 0.1907 0.6791 0.080 Uiso 1 1 calc . . .
C22 C 0.21592(18) 0.4766(10) 0.6894(6) 0.0685(16) Uani 1 1 d . . .
H22 H 0.2416 0.4713 0.7671 0.080 Uiso 1 1 calc . . .
C23 C 0.2020(2) 0.6479(9) 0.6287(6) 0.0766(18) Uani 1 1 d . . .
H23 H 0.2176 0.7607 0.6662 0.080 Uiso 1 1 calc . . .
C24 C 0.16505(18) 0.6581(8) 0.5129(5) 0.0607(14) Uani 1 1 d . . .
H24 H 0.1560 0.7780 0.4730 0.080 Uiso 1 1 calc . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1' N1 C5 72(8) . .
N1 N1' C5 80(9) . .
N2' N2 C17 69(10) . .
N2 N2' C17 84(10) . .
C3 C1 C2 121.0(4) 3_656 .
C3 C1 H1 119.5 3_656 .
C2 C1 H1 119.5 . .
C1 C2 C3 121.7(4) . .
C1 C2 H2 119.2 . .
C3 C2 H2 119.2 . .
C1 C3 C2 117.3(4) 3_656 .
C1 C3 C4 122.7(4) 3_656 .
C2 C3 C4 120.1(4) . .
C6 C4 C5 120.7(4) . .
C6 C4 C3 124.2(4) . .
C5 C4 C3 115.0(4) . .
N1' C5 N1 28(2) . .
N1' C5 C4 166.1(14) . .
N1 C5 C4 165.8(16) . .
C4 C6 C7 134.2(4) . .
C4 C6 H6 112.9 . .
C7 C6 H6 112.9 . .
C12 C7 C8 117.3(4) . .
C12 C7 C6 118.9(4) . .
C8 C7 C6 123.8(4) . .
C7 C8 C9 120.1(5) . .
C7 C8 H8 120.0 . .
C9 C8 H8 120.0 . .
C10 C9 C8 119.6(5) . .
C10 C9 H9 120.2 . .
C8 C9 H9 120.2 . .
C11 C10 C9 120.3(5) . .
C11 C10 H10 119.8 . .
C9 C10 H10 119.8 . .
C10 C11 C12 120.1(5) . .
C10 C11 H11 119.9 . .
C12 C11 H11 119.9 . .
C11 C12 C7 122.5(5) . .
C11 C12 H12 118.7 . .
C7 C12 H12 118.7 . .
C14 C13 C15 121.5(4) 3_565 .
C14 C13 H13 119.2 3_565 .
C15 C13 H13 119.2 . .
C13 C14 C15 121.3(4) 3_565 .
C13 C14 H14 119.3 3_565 .
C15 C14 H14 119.3 . .
C14 C15 C13 117.2(4) . .
C14 C15 C16 120.3(4) . .
C13 C15 C16 122.5(4) . .
C18 C16 C17 119.9(4) . .
C18 C16 C15 124.8(4) . .
C17 C16 C15 115.2(4) . .
N2' C17 N2 27(3) . .
N2' C17 C16 165.9(19) . .
N2 C17 C16 166(2) . .
C16 C18 C19 132.5(4) . .
C16 C18 H18 113.7 . .
C19 C18 H18 113.7 . .
C20 C19 C24 118.3(4) . .
C20 C19 C18 124.8(4) . .
C24 C19 C18 116.9(4) . .
C19 C20 C21 119.3(5) . .
C19 C20 H20 120.3 . .
C21 C20 H20 120.3 . .
C22 C21 C20 120.2(5) . .
C22 C21 H21 119.9 . .
C20 C21 H21 119.9 . .
C23 C22 C21 119.9(4) . .
C23 C22 H22 120.1 . .
C21 C22 H22 120.1 . .
C22 C23 C24 120.9(5) . .
C22 C23 H23 119.6 . .
C24 C23 H23 119.6 . .
C23 C24 C19 121.3(5) . .
C23 C24 H24 119.3 . .
C19 C24 H24 119.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 N1' 0.59(5) .
N1 C5 1.25(4) .
N1' C5 1.21(5) .
N2 N2' 0.56(7) .
N2 C17 1.23(5) .
N2' C17 1.15(6) .
C1 C3 1.379(7) 3_656
C1 C2 1.385(7) .
C1 H1 0.9300 .
C2 C3 1.385(7) .
C2 H2 0.9300 .
C3 C1 1.379(7) 3_656
C3 C4 1.508(6) .
C4 C6 1.321(6) .
C4 C5 1.405(7) .
C6 C7 1.459(6) .
C6 H6 0.9300 .
C7 C12 1.377(7) .
C7 C8 1.401(6) .
C8 C9 1.401(7) .
C8 H8 0.9300 .
C9 C10 1.385(8) .
C9 H9 0.9300 .
C10 C11 1.348(8) .
C10 H10 0.9300 .
C11 C12 1.372(7) .
C11 H11 0.9300 .
C12 H12 0.9300 .
C13 C14 1.377(7) 3_565
C13 C15 1.394(6) .
C13 H13 0.9300 .
C14 C13 1.377(7) 3_565
C14 C15 1.389(6) .
C14 H14 0.9300 .
C15 C16 1.491(6) .
C16 C18 1.331(6) .
C16 C17 1.447(7) .
C18 C19 1.460(6) .
C18 H18 0.9300 .
C19 C20 1.379(6) .
C19 C24 1.401(6) .
C20 C21 1.415(7) .
C20 H20 0.9300 .
C21 C22 1.383(8) .
C21 H21 0.9300 .
C22 C23 1.346(8) .
C22 H22 0.9300 .
C23 C24 1.366(7) .
C23 H23 0.9300 .
C24 H24 0.9300 .
