#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:28:49 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179665 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/18/4511814.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_4511814
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      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 91.544(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.460(7)
_cell_length_b                   4.0402(15)
_cell_length_c                   19.941(7)
_cell_measurement_reflns_used    2387
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.21
_cell_volume                     1486.7(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEXII'
_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 0.993
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9502
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.331
_diffrn_reflns_theta_min         1.483
_diffrn_source                   'rotating unit'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9963
_exptl_absorpt_correction_T_min  0.9565
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       needle
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2680
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0506
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0657P)²+0.1654P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1282
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1868
_reflns_number_total             2680
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg5009363_si_002.cif
_cod_data_source_block           shelx_sonoCNortho7
_cod_depositor_comments
'Adding full bibliography for 4511813--4511815.cif.'
_cod_database_code               4511814
#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   0.957
_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1A C 0.93691(11) 0.8075(5) 0.79048(9) 0.0324(5) Uani 1 1 d . .
C2A C 0.96181(11) 0.8544(5) 0.72481(9) 0.0333(5) Uani 1 1 d . .
C3A C 0.92365(13) 0.7299(6) 0.66908(10) 0.0446(6) Uani 1 1 d . .
H3A H 0.9413 0.7661 0.6254 0.054 Uiso 1 1 calc R U
C4A C 0.86096(14) 0.5560(6) 0.67697(12) 0.0525(7) Uani 1 1 d . .
H4A H 0.8349 0.4712 0.6390 0.063 Uiso 1 1 calc R U
C5A C 0.83568(13) 0.5046(6) 0.74102(14) 0.0525(7) Uani 1 1 d . .
H5A H 0.7924 0.3815 0.7468 0.063 Uiso 1 1 calc R U
C6A C 0.87251(11) 0.6296(6) 0.79637(11) 0.0428(6) Uani 1 1 d . .
H6A H 0.8537 0.5939 0.8396 0.051 Uiso 1 1 calc R U
C7A C 0.97685(11) 0.9448(5) 0.84773(9) 0.0339(5) Uani 1 1 d . .
H7A H 1.0159 1.0891 0.8383 0.041 Uiso 1 1 calc R U
C8A C 0.96397(11) 0.8877(5) 0.91278(9) 0.0337(5) Uani 1 1 d . .
H8A H 0.9255 0.7420 0.9233 0.040 Uiso 1 1 calc R U
C9A C 1.00484(11) 1.0338(5) 0.96709(9) 0.0336(5) Uani 1 1 d . .
H9A H 1.0414 1.1892 0.9563 0.040 Uiso 1 1 calc R U
C10A C 1.02778(13) 1.0354(6) 0.71376(9) 0.0367(5) Uani 1 1 d . .
C1B C 0.28651(10) 0.3589(5) 0.92967(9) 0.0284(5) Uani 1 1 d . .
C2B C 0.22587(10) 0.5339(5) 0.95252(9) 0.0297(5) Uani 1 1 d . .
C3B C 0.16503(11) 0.5897(5) 0.91103(10) 0.0355(5) Uani 1 1 d . .
H3B H 0.1249 0.7089 0.9276 0.043 Uiso 1 1 calc R U
C4B C 0.16304(11) 0.4728(6) 0.84639(10) 0.0385(5) Uani 1 1 d . .
H4B H 0.1219 0.5126 0.8178 0.046 Uiso 1 1 calc R U
C5B C 0.22164(11) 0.2961(5) 0.82318(9) 0.0353(5) Uani 1 1 d . .
H5B H 0.2199 0.2104 0.7788 0.042 Uiso 1 1 calc R U
C6B C 0.28224(11) 0.2428(5) 0.86338(9) 0.0326(5) Uani 1 1 d . .
H6B H 0.3220 0.1248 0.8459 0.039 Uiso 1 1 calc R U
C7B C 0.35033(10) 0.3100(5) 0.97358(9) 0.0318(5) Uani 1 1 d . .
H7B H 0.3503 0.4182 1.0159 0.038 Uiso 1 1 calc R U
C8B C 0.40902(10) 0.1276(5) 0.96013(9) 0.0308(5) Uani 1 1 d . .
H8B H 0.4099 0.0147 0.9184 0.037 Uiso 1 1 calc R U
C9B C 0.47062(10) 0.0936(5) 1.00551(9) 0.0316(5) Uani 1 1 d . .
H9B H 0.4697 0.2129 1.0465 0.038 Uiso 1 1 calc R U
C10B C 0.22431(11) 0.6620(6) 1.01955(10) 0.0378(5) Uani 1 1 d . .
N1A N 1.07990(11) 1.1803(5) 0.70314(9) 0.0494(5) Uani 1 1 d . .
N1B N 0.22013(11) 0.7712(5) 1.07265(9) 0.0548(6) 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 116.49(18) .
C6A C1A C7A 123.06(18) .
C2A C1A C7A 120.45(19) .
C3A C2A C1A 121.4(2) .
C3A C2A C10A 118.16(19) .
C1A C2A C10A 120.45(17) .
C4A C3A C2A 120.3(2) .
C4A C3A H3A 119.8 .
C2A C3A H3A 119.8 .
C3A C4A C5A 119.3(2) .
C3A C4A H4A 120.3 .
C5A C4A H4A 120.3 .
C6A C5A C4A 120.8(2) .
C6A C5A H5A 119.6 .
C4A C5A H5A 119.6 .
C5A C6A C1A 121.6(2) .
C5A C6A H6A 119.2 .
C1A C6A H6A 119.2 .
C8A C7A C1A 126.4(2) .
C8A C7A H7A 116.8 .
C1A C7A H7A 116.8 .
C7A C8A C9A 123.8(2) .
C7A C8A H8A 118.1 .
C9A C8A H8A 118.1 .
C9A C9A C8A 124.6(3) 3_777
C9A C9A H9A 117.7 3_777
C8A C9A H9A 117.7 .
N1A C10A C2A 178.2(2) .
C6B C1B C2B 116.57(17) .
C6B C1B C7B 122.88(18) .
C2B C1B C7B 120.54(17) .
C3B C2B C1B 121.51(17) .
C3B C2B C10B 117.29(18) .
C1B C2B C10B 121.20(17) .
C4B C3B C2B 120.15(19) .
C4B C3B H3B 119.9 .
C2B C3B H3B 119.9 .
C3B C4B C5B 119.31(19) .
C3B C4B H4B 120.3 .
C5B C4B H4B 120.3 .
C6B C5B C4B 121.05(19) .
C6B C5B H5B 119.5 .
C4B C5B H5B 119.5 .
C5B C6B C1B 121.39(19) .
C5B C6B H6B 119.3 .
C1B C6B H6B 119.3 .
C8B C7B C1B 126.55(18) .
C8B C7B H7B 116.7 .
C1B C7B H7B 116.7 .
C7B C8B C9B 123.64(18) .
C7B C8B H8B 118.2 .
C9B C8B H8B 118.2 .
C9B C9B C8B 125.3(2) 3_657
C9B C9B H9B 117.4 3_657
C8B C9B H9B 117.4 .
N1B C10B C2B 176.9(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1A C6A 1.397(3) .
C1A C2A 1.412(3) .
C1A C7A 1.452(3) .
C2A C3A 1.393(3) .
C2A C10A 1.442(3) .
C3A C4A 1.366(3) .
C3A H3A 0.9500 .
C4A C5A 1.387(4) .
C4A H4A 0.9500 .
C5A C6A 1.377(3) .
C5A H5A 0.9500 .
C6A H6A 0.9500 .
C7A C8A 1.345(3) .
C7A H7A 0.9500 .
C8A C9A 1.431(3) .
C8A H8A 0.9500 .
C9A C9A 1.357(4) 3_777
C9A H9A 0.9500 .
C10A N1A 1.151(3) .
C1B C6B 1.403(3) .
C1B C2B 1.410(3) .
C1B C7B 1.462(3) .
C2B C3B 1.395(3) .
C2B C10B 1.434(3) .
C3B C4B 1.372(3) .
C3B H3B 0.9500 .
C4B C5B 1.386(3) .
C4B H4B 0.9500 .
C5B C6B 1.376(3) .
C5B H5B 0.9500 .
C6B H6B 0.9500 .
C7B C8B 1.343(3) .
C7B H7B 0.9500 .
C8B C9B 1.441(3) .
C8B H8B 0.9500 .
C9B C9B 1.345(4) 3_657
C9B H9B 0.9500 .
C10B N1B 1.152(3) .
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 0.2(3) .
C7A C1A C2A C3A -178.84(19) .
C6A C1A C2A C10A 179.94(19) .
C7A C1A C2A C10A 0.8(3) .
C1A C2A C3A C4A -0.5(3) .
C10A C2A C3A C4A 179.8(2) .
C2A C3A C4A C5A 0.0(3) .
C3A C4A C5A C6A 0.7(4) .
C4A C5A C6A C1A -1.0(4) .
C2A C1A C6A C5A 0.5(3) .
C7A C1A C6A C5A 179.6(2) .
C6A C1A C7A C8A 9.1(3) .
C2A C1A C7A C8A -171.9(2) .
C1A C7A C8A C9A -179.2(2) .
C7A C8A C9A C9A -176.4(2) 3_777
C6B C1B C2B C3B -0.4(3) .
C7B C1B C2B C3B 178.60(19) .
C6B C1B C2B C10B 179.65(19) .
C7B C1B C2B C10B -1.4(3) .
C1B C2B C3B C4B 0.2(3) .
C10B C2B C3B C4B -179.8(2) .
C2B C3B C4B C5B 0.7(3) .
C3B C4B C5B C6B -1.5(3) .
C4B C5B C6B C1B 1.3(3) .
C2B C1B C6B C5B -0.4(3) .
C7B C1B C6B C5B -179.31(19) .
C6B C1B C7B C8B -6.7(3) .
C2B C1B C7B C8B 174.4(2) .
C1B C7B C8B C9B 179.15(19) .
C7B C8B C9B C9B 178.2(2) 3_657
