#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/50/7235017.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_7235017
loop_
_publ_author_name
'Lingyan Zhu'
'Fei Tong'
'Norhan Zaghloul'
'Omar Baz'
'Christopher J. Bardeen'
'Rabih O. Al-Kaysi'
_publ_section_title
;
 Characterization of a P-type photomechanical molecular crystal based on
 the E -> Z photoisomerization of 9-divinylanthracene malonitrile
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              8245
_journal_page_last               8252
_journal_paper_doi               10.1039/C6TC02517J
_journal_volume                  4
_journal_year                    2016
_chemical_formula_sum            'C20 H12 N2'
_chemical_formula_weight         280.32
_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'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 118.107(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.293(3)
_cell_length_b                   4.0674(7)
_cell_length_c                   20.370(4)
_cell_measurement_reflns_used    3621
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.54
_cell_measurement_theta_min      2.27
_cell_volume                     1410.0(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0795
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            23666
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.342
_diffrn_reflns_theta_min         1.999
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'needle frag'
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.587
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.010
_exptl_transmission_factor_max   0.745
_exptl_transmission_factor_min   0.537
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2577
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0519
_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)+(0.0621P)²+1.0822P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1413
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1839
_reflns_number_total             2577
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            J-Mater-Chem-C-2016-4-8245.cif
_cod_data_source_block           cb74_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' 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      'P 21/n'
_cod_database_code               7235017
_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   0.955
_shelx_estimated_absorpt_t_max   0.999
_shelxl_version_number           2013-4
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.88487(13) 0.3609(6) 0.14523(11) 0.0262(5) Uani 1 1 d . . . . .
H1 H 0.8452 0.4657 0.1528 0.031 Uiso 1 1 calc R U . . .
C2 C 0.96208(13) 0.3914(6) 0.19796(12) 0.0298(6) Uani 1 1 d . . . . .
H2 H 0.9752 0.5133 0.2420 0.036 Uiso 1 1 calc R U . . .
C3 C 1.02232(13) 0.2433(6) 0.18739(12) 0.0304(6) Uani 1 1 d . . . . .
H3 H 1.0756 0.2670 0.2244 0.037 Uiso 1 1 calc R U . . .
C4 C 1.00497(13) 0.0685(6) 0.12532(12) 0.0286(5) Uani 1 1 d . . . . .
H4 H 1.0462 -0.0298 0.1191 0.034 Uiso 1 1 calc R U . . .
C4A C 0.92527(12) 0.0291(6) 0.06862(11) 0.0249(5) Uani 1 1 d . . . . .
C5 C 0.81318(13) -0.3516(6) -0.12086(12) 0.0282(5) Uani 1 1 d . . . . .
H5 H 0.8548 -0.4456 -0.1270 0.034 Uiso 1 1 calc R U . . .
C6 C 0.73754(14) -0.3857(6) -0.17586(12) 0.0297(6) Uani 1 1 d . . . . .
H6 H 0.7268 -0.4996 -0.2204 0.036 Uiso 1 1 calc R U . . .
C7 C 0.67535(13) -0.2514(6) -0.16647(12) 0.0297(6) Uani 1 1 d . . . . .
H7 H 0.6228 -0.2801 -0.2045 0.036 Uiso 1 1 calc R U . . .
C8 C 0.68931(13) -0.0807(6) -0.10364(11) 0.0255(5) Uani 1 1 d . . . . .
H8 H 0.6463 0.0068 -0.0988 0.031 Uiso 1 1 calc R U . . .
C8A C 0.76779(12) -0.0316(6) -0.04488(11) 0.0236(5) Uani 1 1 d . . . . .
C9 C 0.78389(12) 0.1417(6) 0.02140(11) 0.0228(5) Uani 1 1 d . . . . .
C9A C 0.86315(12) 0.1737(6) 0.07899(11) 0.0238(5) Uani 1 1 d . . . . .
C10 C 0.90760(13) -0.1444(6) 0.00326(12) 0.0255(5) Uani 1 1 d . . . . .
H10 H 0.9491 -0.2434 -0.0024 0.031 Uiso 1 1 calc R U . . .
C10A C 0.83052(13) -0.1757(6) -0.05392(12) 0.0250(5) Uani 1 1 d . . . . .
C11 C 0.71788(12) 0.3024(6) 0.02514(12) 0.0249(5) Uani 1 1 d . . . . .
H11 H 0.6802 0.3993 -0.0201 0.030 Uiso 1 1 calc R U . . .
C12 C 0.70213(12) 0.3347(6) 0.08282(11) 0.0255(5) Uani 1 1 d . . . . .
H12 H 0.7354 0.2357 0.1295 0.031 Uiso 1 1 calc R U . . .
C13 C 0.63482(12) 0.5193(6) 0.07297(12) 0.0256(5) Uani 1 1 d . . . . .
H13 H 0.6042 0.6165 0.0255 0.031 Uiso 1 1 calc R U . . .
C14 C 0.61040(12) 0.5696(6) 0.12456(12) 0.0265(5) Uani 1 1 d . . . . .
C15 C 0.65056(13) 0.4322(6) 0.19838(13) 0.0281(5) Uani 1 1 d . . . . .
N16 N 0.68248(12) 0.3174(6) 0.25699(11) 0.0376(5) Uani 1 1 d . . . . .
C17 C 0.54086(13) 0.7611(6) 0.10678(12) 0.0300(6) Uani 1 1 d . . . . .
N18 N 0.48513(12) 0.9144(6) 0.09115(11) 0.0398(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
_geom_angle_site_symmetry_3
C2 C1 C9A 121.0(2) . .
C2 C1 H1 119.5 . .
C9A C1 H1 119.5 . .
C1 C2 C3 120.7(2) . .
C1 C2 H2 119.7 . .
C3 C2 H2 119.7 . .
C4 C3 C2 120.6(2) . .
C4 C3 H3 119.7 . .
C2 C3 H3 119.7 . .
C3 C4 C4A 120.9(2) . .
C3 C4 H4 119.6 . .
C4A C4 H4 119.6 . .
C10 C4A C4 120.8(2) . .
C10 C4A C9A 119.99(19) . .
C4 C4A C9A 119.2(2) . .
C6 C5 C10A 120.8(2) . .
C6 C5 H5 119.6 . .
C10A C5 H5 119.6 . .
C5 C6 C7 119.9(2) . .
C5 C6 H6 120.1 . .
C7 C6 H6 120.1 . .
C8 C7 C6 121.2(2) . .
C8 C7 H7 119.4 . .
C6 C7 H7 119.4 . .
C7 C8 C8A 121.1(2) . .
C7 C8 H8 119.4 . .
C8A C8 H8 119.4 . .
C9 C8A C10A 120.34(19) . .
C9 C8A C8 122.3(2) . .
C10A C8A C8 117.3(2) . .
C8A C9 C9A 119.7(2) . .
C8A C9 C11 117.67(18) . .
C9A C9 C11 122.48(19) . .
C9 C9A C1 123.2(2) . .
C9 C9A C4A 119.1(2) . .
C1 C9A C4A 117.57(19) . .
C10A C10 C4A 121.7(2) . .
C10A C10 H10 119.2 . .
C4A C10 H10 119.2 . .
C10 C10A C8A 119.2(2) . .
C10 C10A C5 121.2(2) . .
C8A C10A C5 119.60(19) . .
C12 C11 C9 130.2(2) . .
C12 C11 H11 114.9 . .
C9 C11 H11 114.9 . .
C11 C12 C13 119.3(2) . .
C11 C12 H12 120.3 . .
C13 C12 H12 120.3 . .
C14 C13 C12 126.5(2) . .
C14 C13 H13 116.7 . .
C12 C13 H13 116.7 . .
C13 C14 C15 122.6(2) . .
C13 C14 C17 120.6(2) . .
C15 C14 C17 116.8(2) . .
N16 C15 C14 178.9(3) . .
N18 C17 C14 178.6(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.371(3) .
C1 C9A 1.429(3) .
C1 H1 0.9500 .
C2 C3 1.413(3) .
C2 H2 0.9500 .
C3 C4 1.348(3) .
C3 H3 0.9500 .
C4 C4A 1.432(3) .
C4 H4 0.9500 .
C4A C10 1.400(3) .
C4A C9A 1.437(3) .
C5 C6 1.365(3) .
C5 C10A 1.433(3) .
C5 H5 0.9500 .
C6 C7 1.411(3) .
C6 H6 0.9500 .
C7 C8 1.367(3) .
C7 H7 0.9500 .
C8 C8A 1.435(3) .
C8 H8 0.9500 .
C8A C9 1.422(3) .
C8A C10A 1.433(3) .
C9 C9A 1.429(3) .
C9 C11 1.465(3) .
C10 C10A 1.397(3) .
C10 H10 0.9500 .
C11 C12 1.352(3) .
C11 H11 0.9500 .
C12 C13 1.430(3) .
C12 H12 0.9500 .
C13 C14 1.355(3) .
C13 H13 0.9500 .
C14 C15 1.441(3) .
C14 C17 1.442(3) .
C15 N16 1.153(3) .
C17 N18 1.151(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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C9A C1 C2 C3 1.2(4) . . . .
C1 C2 C3 C4 -0.2(4) . . . .
C2 C3 C4 C4A 0.1(4) . . . .
C3 C4 C4A C10 178.1(2) . . . .
C3 C4 C4A C9A -1.1(3) . . . .
C10A C5 C6 C7 -1.1(3) . . . .
C5 C6 C7 C8 1.3(4) . . . .
C6 C7 C8 C8A 0.1(3) . . . .
C7 C8 C8A C9 -179.3(2) . . . .
C7 C8 C8A C10A -1.6(3) . . . .
C10A C8A C9 C9A 0.4(3) . . . .
C8 C8A C9 C9A 178.0(2) . . . .
C10A C8A C9 C11 175.9(2) . . . .
C8 C8A C9 C11 -6.5(3) . . . .
C8A C9 C9A C1 176.0(2) . . . .
C11 C9 C9A C1 0.7(3) . . . .
C8A C9 C9A C4A 0.0(3) . . . .
C11 C9 C9A C4A -175.3(2) . . . .
C2 C1 C9A C9 -178.2(2) . . . .
C2 C1 C9A C4A -2.1(3) . . . .
C10 C4A C9A C9 -0.9(3) . . . .
C4 C4A C9A C9 178.3(2) . . . .
C10 C4A C9A C1 -177.2(2) . . . .
C4 C4A C9A C1 2.0(3) . . . .
C4 C4A C10 C10A -177.7(2) . . . .
C9A C4A C10 C10A 1.5(3) . . . .
C4A C10 C10A C8A -1.1(3) . . . .
C4A C10 C10A C5 179.5(2) . . . .
C9 C8A C10A C10 0.1(3) . . . .
C8 C8A C10A C10 -177.6(2) . . . .
C9 C8A C10A C5 179.5(2) . . . .
C8 C8A C10A C5 1.8(3) . . . .
C6 C5 C10A C10 178.9(2) . . . .
C6 C5 C10A C8A -0.5(3) . . . .
C8A C9 C11 C12 142.4(2) . . . .
C9A C9 C11 C12 -42.2(4) . . . .
C9 C11 C12 C13 176.9(2) . . . .
C11 C12 C13 C14 178.8(2) . . . .
C12 C13 C14 C15 -1.0(4) . . . .
C12 C13 C14 C17 -179.8(2) . . . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 137395515
