#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:28:49 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179665 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/18/4511815.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_4511815
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
_chemical_name_systematic
;
 ?
;
_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
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                71.769(3)
_cell_angle_beta                 79.633(3)
_cell_angle_gamma                78.979(3)
_cell_formula_units_Z            2
_cell_length_a                   5.4806(16)
_cell_length_b                   12.043(3)
_cell_length_c                   12.301(4)
_cell_measurement_reflns_used    4538
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      28.45
_cell_measurement_theta_min      2.86
_cell_volume                     750.6(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APRX II'
_computing_data_reduction        'Bruker SAINT'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldric, 2008)'
_diffrn_ambient_temperature      183(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.986
_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  0.0107
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5819
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         1.758
_diffrn_source                   'rotating unit'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.9963
_exptl_absorpt_correction_T_min  0.9674
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2911
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.950
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0331
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0619P)²+0.1416P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0965
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2643
_reflns_number_total             2911
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg5009363_si_003.cif
_cod_data_source_block           shelx_sonoCNmeta
_cod_depositor_comments
'Adding full bibliography for 4511813--4511815.cif.'
_cod_database_code               4511815
#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.
;
_shelx_estimated_absorpt_t_min   0.967
_shelx_estimated_absorpt_t_max   0.996
_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 0.81699(18) 0.22299(8) 0.64350(8) 0.0292(2) Uani 1 1 d . .
C2A C 0.8153(2) 0.24341(9) 0.74937(8) 0.0349(2) Uani 1 1 d . .
H2A H 0.6992 0.2102 0.8132 0.042 Uiso 1 1 calc R U
C3A C 0.9786(2) 0.31093(10) 0.76344(9) 0.0388(2) Uani 1 1 d . .
H3A H 0.9750 0.3224 0.8367 0.047 Uiso 1 1 calc R U
C4A C 1.14728(19) 0.36185(9) 0.67157(9) 0.0351(2) Uani 1 1 d . .
H4A H 1.2610 0.4076 0.6811 0.042 Uiso 1 1 calc R U
C5A C 1.14649(17) 0.34448(8) 0.56458(8) 0.0301(2) Uani 1 1 d . .
C6A C 0.98349(18) 0.27636(8) 0.55032(8) 0.0299(2) Uani 1 1 d . .
H6A H 0.9854 0.2660 0.4767 0.036 Uiso 1 1 calc R U
C7A C 0.65009(18) 0.14620(8) 0.63387(8) 0.0317(2) Uani 1 1 d . .
H7A H 0.5214 0.1258 0.6964 0.038 Uiso 1 1 calc R U
C8A C 0.66046(18) 0.10172(8) 0.54569(9) 0.0328(2) Uani 1 1 d . .
H8A H 0.7850 0.1226 0.4813 0.039 Uiso 1 1 calc R U
C9A C 0.49346(19) 0.02407(9) 0.54312(9) 0.0342(2) Uani 1 1 d . .
H9A H 0.3656 0.0056 0.6065 0.041 Uiso 1 1 calc R U
C10A C 1.32130(19) 0.39447(9) 0.46657(9) 0.0353(2) Uani 1 1 d . .
C1B C 0.90119(18) 0.18403(9) 0.15330(8) 0.0329(2) Uani 1 1 d . .
C2B C 1.0978(2) 0.16087(10) 0.21940(9) 0.0382(2) Uani 1 1 d . .
H2B H 1.1808 0.0822 0.2447 0.046 Uiso 1 1 calc R U
C3B C 1.1746(2) 0.24965(10) 0.24892(9) 0.0401(3) Uani 1 1 d . .
H3B H 1.3095 0.2313 0.2934 0.048 Uiso 1 1 calc R U
C4B C 1.05643(19) 0.36440(10) 0.21419(9) 0.0368(2) Uani 1 1 d . .
H4B H 1.1086 0.4256 0.2341 0.044 Uiso 1 1 calc R U
C5B C 0.85802(18) 0.38877(9) 0.14901(8) 0.0317(2) Uani 1 1 d . .
C6B C 0.78152(18) 0.30051(9) 0.11823(8) 0.0317(2) Uani 1 1 d . .
H6B H 0.6474 0.3193 0.0732 0.038 Uiso 1 1 calc R U
C7B C 0.8306(2) 0.08741(9) 0.12280(9) 0.0360(2) Uani 1 1 d . .
H7B H 0.9236 0.0114 0.1502 0.043 Uiso 1 1 calc R U
C8B C 0.64813(19) 0.09510(9) 0.06019(8) 0.0339(2) Uani 1 1 d . .
H8B H 0.5506 0.1700 0.0331 0.041 Uiso 1 1 calc R U
C9B C 0.59126(19) -0.00359(9) 0.03152(9) 0.0348(2) Uani 1 1 d . .
H9B H 0.6888 -0.0785 0.0588 0.042 Uiso 1 1 calc R U
C10B C 0.73156(19) 0.50833(9) 0.11187(8) 0.0347(2) Uani 1 1 d . .
N1A N 1.45992(19) 0.43095(9) 0.38739(8) 0.0482(3) Uani 1 1 d . .
N1B N 0.6346(2) 0.60359(8) 0.08208(8) 0.0458(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
C6A C1A C2A 117.90(9) .
C6A C1A C7A 122.31(9) .
C2A C1A C7A 119.78(9) .
C3A C2A C1A 121.55(9) .
C3A C2A H2A 119.2 .
C1A C2A H2A 119.2 .
C4A C3A C2A 120.50(9) .
C4A C3A H3A 119.8 .
C2A C3A H3A 119.8 .
C3A C4A C5A 118.46(9) .
C3A C4A H4A 120.8 .
C5A C4A H4A 120.8 .
C6A C5A C4A 121.17(9) .
C6A C5A C10A 118.32(9) .
C4A C5A C10A 120.48(9) .
C5A C6A C1A 120.38(9) .
C5A C6A H6A 119.8 .
C1A C6A H6A 119.8 .
C8A C7A C1A 126.54(9) .
C8A C7A H7A 116.7 .
C1A C7A H7A 116.7 .
C7A C8A C9A 123.63(10) .
C7A C8A H8A 118.2 .
C9A C8A H8A 118.2 .
C9A C9A C8A 124.27(12) 2_656
C9A C9A H9A 117.9 2_656
C8A C9A H9A 117.9 .
N1A C10A C5A 177.65(11) .
C6B C1B C2B 117.71(9) .
C6B C1B C7B 122.77(9) .
C2B C1B C7B 119.51(9) .
C3B C2B C1B 121.73(10) .
C3B C2B H2B 119.1 .
C1B C2B H2B 119.1 .
C4B C3B C2B 120.45(10) .
C4B C3B H3B 119.8 .
C2B C3B H3B 119.8 .
C3B C4B C5B 118.50(10) .
C3B C4B H4B 120.8 .
C5B C4B H4B 120.8 .
C6B C5B C4B 121.38(9) .
C6B C5B C10B 119.22(9) .
C4B C5B C10B 119.39(9) .
C5B C6B C1B 120.22(9) .
C5B C6B H6B 119.9 .
C1B C6B H6B 119.9 .
C8B C7B C1B 126.74(9) .
C8B C7B H7B 116.6 .
C1B C7B H7B 116.6 .
C7B C8B C9B 123.88(10) .
C7B C8B H8B 118.1 .
C9B C8B H8B 118.1 .
C9B C9B C8B 124.18(12) 2_655
C9B C9B H9B 117.9 2_655
C8B C9B H9B 117.9 .
N1B C10B C5B 179.03(11) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1A C6A 1.3951(14) .
C1A C2A 1.3971(14) .
C1A C7A 1.4618(13) .
C2A C3A 1.3839(14) .
C2A H2A 0.9500 .
C3A C4A 1.3837(15) .
C3A H3A 0.9500 .
C4A C5A 1.3966(14) .
C4A H4A 0.9500 .
C5A C6A 1.3888(13) .
C5A C10A 1.4438(14) .
C6A H6A 0.9500 .
C7A C8A 1.3402(15) .
C7A H7A 0.9500 .
C8A C9A 1.4386(14) .
C8A H8A 0.9500 .
C9A C9A 1.345(2) 2_656
C9A H9A 0.9500 .
C10A N1A 1.1455(14) .
C1B C6B 1.3984(14) .
C1B C2B 1.3995(15) .
C1B C7B 1.4637(15) .
C2B C3B 1.3864(16) .
C2B H2B 0.9500 .
C3B C4B 1.3783(16) .
C3B H3B 0.9500 .
C4B C5B 1.3986(14) .
C4B H4B 0.9500 .
C5B C6B 1.3886(14) .
C5B C10B 1.4433(14) .
C6B H6B 0.9500 .
C7B C8B 1.3412(15) .
C7B H7B 0.9500 .
C8B C9B 1.4414(15) .
C8B H8B 0.9500 .
C9B C9B 1.347(2) 2_655
C9B H9B 0.9500 .
C10B N1B 1.1432(14) .
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 -2.20(15) .
C7A C1A C2A C3A 176.88(9) .
C1A C2A C3A C4A 0.92(16) .
C2A C3A C4A C5A 0.68(16) .
C3A C4A C5A C6A -0.95(15) .
C3A C4A C5A C10A -179.13(9) .
C4A C5A C6A C1A -0.36(15) .
C10A C5A C6A C1A 177.86(8) .
C2A C1A C6A C5A 1.90(14) .
C7A C1A C6A C5A -177.15(9) .
C6A C1A C7A C8A 11.68(16) .
C2A C1A C7A C8A -167.35(10) .
C1A C7A C8A C9A 178.40(9) .
C7A C8A C9A C9A -177.87(13) 2_656
C6B C1B C2B C3B -0.52(15) .
C7B C1B C2B C3B 178.90(9) .
C1B C2B C3B C4B 0.49(16) .
C2B C3B C4B C5B 0.13(15) .
C3B C4B C5B C6B -0.72(15) .
C3B C4B C5B C10B 179.93(9) .
C4B C5B C6B C1B 0.69(15) .
C10B C5B C6B C1B -179.96(9) .
C2B C1B C6B C5B -0.07(14) .
C7B C1B C6B C5B -179.47(9) .
C6B C1B C7B C8B -0.43(16) .
C2B C1B C7B C8B -179.82(10) .
C1B C7B C8B C9B 178.84(9) .
C7B C8B C9B C9B -179.84(12) 2_655
