#------------------------------------------------------------------------------
#$Date: 2023-12-21 10:55:17 +0200 (Thu, 21 Dec 2023) $
#$Revision: 288466 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/18/4511813.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_4511813
loop_
_publ_author_name
'Sonoda, Yoriko'
'Goto, Midori'
'Norikane, Yasuo'
'Azumi, Reiko'
_publ_section_title
;
 Crystal Structures and Fluorescence Spectroscopic Properties of
 Cyano-Substituted Diphenylhexatrienes
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4781
_journal_paper_doi               10.1021/cg5009363
_journal_volume                  14
_journal_year                    2014
_chemical_formula_sum            'C20 H14 N2'
_chemical_formula_weight         282.33
_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-2014
_cell_angle_alpha                100.9800(10)
_cell_angle_beta                 91.2140(10)
_cell_angle_gamma                94.8330(10)
_cell_formula_units_Z            2
_cell_length_a                   3.9187(3)
_cell_length_b                   11.9054(10)
_cell_length_c                   16.2554(14)
_cell_measurement_reflns_used    3011
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.55
_cell_volume                     741.31(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      183(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans '
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0136
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5720
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_min         1.957
_diffrn_source                   'rotating unit'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9978
_exptl_absorpt_correction_T_min  0.9706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       plate
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.107
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2861
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.962
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0619P)²+0.1305P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1056
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2361
_reflns_number_total             2861
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg5009363_si_004.cif
_cod_data_source_block           shelx_sonoCNpara
_cod_depositor_comments
'Adding full bibliography for 4511813--4511815.cif.'
_cod_database_code               4511813
#BEGIN Tags that were not found in dictionaries:
_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.
;
_shelxl_version_number           2014-3
#END Tags that were not found in dictionaries
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
C1A C 0.3417(3) 0.22940(10) 0.23658(7) 0.0303(3) Uani 1 1 d . .
C2A C 0.3862(3) 0.34679(10) 0.27051(7) 0.0393(3) Uani 1 1 d . .
H2A H 0.3081 0.3996 0.2389 0.047 Uiso 1 1 calc R U
C3A C 0.5406(3) 0.38810(10) 0.34874(7) 0.0401(3) Uani 1 1 d . .
H3A H 0.5690 0.4684 0.3704 0.048 Uiso 1 1 calc R U
C4A C 0.6543(3) 0.31131(10) 0.39557(7) 0.0327(3) Uani 1 1 d . .
C5A C 0.6135(3) 0.19375(10) 0.36271(7) 0.0335(3) Uani 1 1 d . .
H5A H 0.6925 0.1411 0.3944 0.040 Uiso 1 1 calc R U
C6A C 0.4596(3) 0.15378(10) 0.28481(7) 0.0327(3) Uani 1 1 d . .
H6A H 0.4326 0.0735 0.2632 0.039 Uiso 1 1 calc R U
C7A C 0.1711(3) 0.19003(10) 0.15421(7) 0.0330(3) Uani 1 1 d . .
H7A H 0.0489 0.2442 0.1324 0.040 Uiso 1 1 calc R U
C8A C 0.1698(3) 0.08499(10) 0.10632(7) 0.0316(3) Uani 1 1 d . .
H8A H 0.2927 0.0298 0.1267 0.038 Uiso 1 1 calc R U
C9A C -0.0065(3) 0.05106(10) 0.02595(7) 0.0318(3) Uani 1 1 d . .
H9A H -0.1430 0.1048 0.0080 0.038 Uiso 1 1 calc R U
C10A C 0.8103(3) 0.35028(10) 0.47812(7) 0.0376(3) Uani 1 1 d . .
C1B C 0.5672(3) 0.77575(9) 0.26933(7) 0.0295(2) Uani 1 1 d . .
C2B C 0.3683(3) 0.67087(10) 0.24461(7) 0.0338(3) Uani 1 1 d . .
H2B H 0.2844 0.6308 0.2863 0.041 Uiso 1 1 calc R U
C3B C 0.2907(3) 0.62410(10) 0.16118(7) 0.0352(3) Uani 1 1 d . .
H3B H 0.1572 0.5524 0.1458 0.042 Uiso 1 1 calc R U
C4B C 0.4107(3) 0.68329(10) 0.09978(7) 0.0323(3) Uani 1 1 d . .
C5B C 0.6063(3) 0.78851(10) 0.12307(7) 0.0336(3) Uani 1 1 d . .
H5B H 0.6861 0.8291 0.0812 0.040 Uiso 1 1 calc R U
C6B C 0.6841(3) 0.83379(9) 0.20627(7) 0.0321(3) Uani 1 1 d . .
H6B H 0.8188 0.9053 0.2213 0.038 Uiso 1 1 calc R U
C7B C 0.6414(3) 0.81998(10) 0.35824(7) 0.0322(3) Uani 1 1 d . .
H7B H 0.5311 0.7781 0.3960 0.039 Uiso 1 1 calc R U
C8B C 0.8482(3) 0.91332(9) 0.39273(7) 0.0310(3) Uani 1 1 d . .
H8B H 0.9663 0.9557 0.3565 0.037 Uiso 1 1 calc R U
C9B C 0.9007(3) 0.95259(10) 0.48163(7) 0.0320(3) Uani 1 1 d . .
H9B H 0.7864 0.9082 0.5172 0.038 Uiso 1 1 calc R U
C10B C 0.3287(3) 0.63829(10) 0.01235(8) 0.0381(3) Uani 1 1 d . .
N1A N 0.9323(3) 0.37762(10) 0.54451(6) 0.0484(3) Uani 1 1 d . .
N1B N 0.2641(3) 0.60633(10) -0.05769(6) 0.0501(3) 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'
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
C2A C1A C6A 117.69(10) .
C2A C1A C7A 119.60(10) .
C6A C1A C7A 122.70(10) .
C3A C2A C1A 121.75(10) .
C3A C2A H2A 119.1 .
C1A C2A H2A 119.1 .
C2A C3A C4A 119.49(11) .
C2A C3A H3A 120.3 .
C4A C3A H3A 120.3 .
C3A C4A C5A 119.66(11) .
C3A C4A C10A 121.43(11) .
C5A C4A C10A 118.90(10) .
C6A C5A C4A 120.27(10) .
C6A C5A H5A 119.9 .
C4A C5A H5A 119.9 .
C5A C6A C1A 121.13(11) .
C5A C6A H6A 119.4 .
C1A C6A H6A 119.4 .
C8A C7A C1A 126.42(10) .
C8A C7A H7A 116.8 .
C1A C7A H7A 116.8 .
C7A C8A C9A 123.77(11) .
C7A C8A H8A 118.1 .
C9A C8A H8A 118.1 .
C9A C9A C8A 125.05(13) 2
C9A C9A H9A 117.5 2
C8A C9A H9A 117.5 .
N1A C10A C4A 177.63(12) .
C2B C1B C6B 117.83(10) .
C2B C1B C7B 119.06(10) .
C6B C1B C7B 123.11(10) .
C3B C2B C1B 121.79(10) .
C3B C2B H2B 119.1 .
C1B C2B H2B 119.1 .
C2B C3B C4B 119.26(11) .
C2B C3B H3B 120.4 .
C4B C3B H3B 120.4 .
C5B C4B C3B 119.89(10) .
C5B C4B C10B 119.35(10) .
C3B C4B C10B 120.75(11) .
C6B C5B C4B 120.34(10) .
C6B C5B H5B 119.8 .
C4B C5B H5B 119.8 .
C5B C6B C1B 120.89(10) .
C5B C6B H6B 119.6 .
C1B C6B H6B 119.6 .
C8B C7B C1B 127.12(10) .
C8B C7B H7B 116.4 .
C1B C7B H7B 116.4 .
C7B C8B C9B 123.47(10) .
C7B C8B H8B 118.3 .
C9B C8B H8B 118.3 .
C9B C9B C8B 125.05(13) 2_776
C9B C9B H9B 117.5 2_776
C8B C9B H9B 117.5 .
N1B C10B C4B 177.62(12) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1A C2A 1.3960(16) .
C1A C6A 1.4008(15) .
C1A C7A 1.4593(15) .
C2A C3A 1.3800(16) .
C2A H2A 0.9500 .
C3A C4A 1.3904(16) .
C3A H3A 0.9500 .
C4A C5A 1.3942(16) .
C4A C10A 1.4387(16) .
C5A C6A 1.3723(15) .
C5A H5A 0.9500 .
C6A H6A 0.9500 .
C7A C8A 1.3409(16) .
C7A H7A 0.9500 .
C8A C9A 1.4356(15) .
C8A H8A 0.9500 .
C9A C9A 1.347(2) 2
C9A H9A 0.9500 .
C10A N1A 1.1477(15) .
C1B C2B 1.3998(16) .
C1B C6B 1.4053(15) .
C1B C7B 1.4550(15) .
C2B C3B 1.3812(16) .
C2B H2B 0.9500 .
C3B C4B 1.3950(16) .
C3B H3B 0.9500 .
C4B C5B 1.3947(16) .
C4B C10B 1.4394(16) .
C5B C6B 1.3746(15) .
C5B H5B 0.9500 .
C6B H6B 0.9500 .
C7B C8B 1.3410(16) .
C7B H7B 0.9500 .
C8B C9B 1.4362(15) .
C8B H8B 0.9500 .
C9B C9B 1.346(2) 2_776
C9B H9B 0.9500 .
C10B N1B 1.1452(15) .
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
C6A C1A C2A C3A 0.02(18) .
C7A C1A C2A C3A 178.87(10) .
C1A C2A C3A C4A -0.28(19) .
C2A C3A C4A C5A 0.50(17) .
C2A C3A C4A C10A -178.70(11) .
C3A C4A C5A C6A -0.49(17) .
C10A C4A C5A C6A 178.74(10) .
C4A C5A C6A C1A 0.23(17) .
C2A C1A C6A C5A 0.00(16) .
C7A C1A C6A C5A -178.81(10) .
C2A C1A C7A C8A 165.59(11) .
C6A C1A C7A C8A -15.62(18) .
C1A C7A C8A C9A 179.30(10) .
C7A C8A C9A C9A 175.27(13) 2
C6B C1B C2B C3B 0.78(16) .
C7B C1B C2B C3B -179.64(10) .
C1B C2B C3B C4B -0.61(17) .
C2B C3B C4B C5B -0.07(16) .
C2B C3B C4B C10B -178.66(10) .
C3B C4B C5B C6B 0.57(16) .
C10B C4B C5B C6B 179.18(10) .
C4B C5B C6B C1B -0.40(16) .
C2B C1B C6B C5B -0.26(16) .
C7B C1B C6B C5B -179.83(10) .
C2B C1B C7B C8B 174.22(10) .
C6B C1B C7B C8B -6.22(17) .
C1B C7B C8B C9B 178.44(10) .
C7B C8B C9B C9B -178.22(13) 2_776
loop_
_cod_changelog_entry_id
_cod_changelog_entry_author
_cod_changelog_entry_date
_cod_changelog_entry_text
1 'Vaitkus, Antanas' 2023-12-21T10:51:51+02:00
;
 Changed data name '_shelx1_res_file' to '_shelx_res_file'.
;
