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#$Date: 2024-09-17 04:14:26 +0300 (Tue, 17 Sep 2024) $
#$Revision: 294770 $
#$URL: file:///home/coder/svn-repositories/cod/cif/3/00/04/3000473.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_3000473
loop_
_publ_author_name
'Deka, Poonam'
'Jaiswal, Shilpi'
'Sarma, Parishmita'
'Bora, Debajit'
'Nakane, Takanori'
'Kawamoto, Akihiro'
'Kurisu, Genji'
'Mahanta, Sanjeev Pran'
'Patra, Abhijit'
'Ichiyanagi, Kouhei'
'Sasaki, Toshiyuki'
'Thakuria, Ranjit'
_publ_section_title
;
 Analysis of Solid-State Emission of the p-Bis(2,2-dicyanovinyl)benzene
 Analogue through Combined X-ray, Synchrotron, and Microcrystal Electron
 Diffraction
;
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              7222
_journal_page_last               7234
_journal_paper_doi               10.1021/acs.cgd.4c00856
_journal_volume                  24
_journal_year                    2024
_chemical_formula_sum            'C14 H6 N4'
_chemical_formula_weight         230.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 99.465(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1560(3)
_cell_length_b                   12.5164(5)
_cell_length_c                   13.2162(6)
_cell_measurement_reflns_used    6316
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.26
_cell_volume                     1167.62(9)
_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-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_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  0.0284
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10004
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.404
_diffrn_reflns_theta_min         3.313
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       0.55(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2380
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0586
_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)+(0.0815P)²+0.2211P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1415
_refine_ls_wR_factor_ref         0.1484
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2070
_reflns_number_total             2380
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            IP-1_SCXRD.cif
_cod_data_source_block           IP-1
_cod_depositor_comments
'Releasing structure 3000473 into public domain as published material.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               3000473
_shelx_shelxl_version_number     2016/6
_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   0.983
_shelx_estimated_absorpt_t_max   0.988
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
N1 N 0.4802(3) 0.21209(13) 0.33151(11) 0.0725(5) Uani 1 1 d . . . . .
N2 N 0.5882(4) 0.04808(15) 0.62705(15) 0.1062(9) Uani 1 1 d . . . . .
N3 N 0.0629(3) 0.31943(13) 0.20352(12) 0.0734(5) Uani 1 1 d . . . . .
N4 N 0.0254(4) 0.63496(17) 0.05595(15) 0.0987(7) Uani 1 1 d . . . . .
C1 C 0.31755(19) 0.39859(11) 0.54009(10) 0.0397(4) Uani 1 1 d . . . . .
C2 C 0.27100(19) 0.43106(11) 0.43802(10) 0.0394(4) Uani 1 1 d . . . . .
H2 H 0.284323 0.383458 0.385653 0.047 Uiso 1 1 calc R U . . .
C3 C 0.20474(19) 0.53416(11) 0.41386(11) 0.0411(4) Uani 1 1 d . . . . .
C4 C 0.1873(2) 0.60525(13) 0.49368(13) 0.0483(4) Uani 1 1 d . . . . .
H4 H 0.145201 0.674601 0.478407 0.058 Uiso 1 1 calc R U . . .
C5 C 0.2318(2) 0.57345(14) 0.59445(13) 0.0534(4) Uani 1 1 d . . . . .
H5 H 0.218655 0.621123 0.646792 0.064 Uiso 1 1 calc R U . . .
C6 C 0.2958(2) 0.47139(13) 0.61797(12) 0.0483(4) Uani 1 1 d . . . . .
H6 H 0.324970 0.450429 0.686252 0.058 Uiso 1 1 calc R U . . .
C7 C 0.3907(2) 0.29413(12) 0.57404(10) 0.0443(4) Uani 1 1 d . . . . .
H7 H 0.393804 0.281199 0.643592 0.053 Uiso 1 1 calc R U . . .
C8 C 0.4546(2) 0.21285(11) 0.52287(11) 0.0462(4) Uani 1 1 d . . . . .
C9 C 0.4660(3) 0.21201(11) 0.41566(11) 0.0503(4) Uani 1 1 d . . . . .
C10 C 0.5281(3) 0.11937(14) 0.57928(13) 0.0651(6) Uani 1 1 d . . . . .
C11 C 0.1541(2) 0.57487(11) 0.30986(12) 0.0481(4) Uani 1 1 d . . . . .
H11 H 0.156963 0.648888 0.304204 0.058 Uiso 1 1 calc R U . . .
C12 C 0.1040(2) 0.52294(12) 0.22101(12) 0.0476(4) Uani 1 1 d . . . . .
C13 C 0.0829(2) 0.40941(13) 0.21114(11) 0.0508(4) Uani 1 1 d . . . . .
C14 C 0.0588(3) 0.58365(15) 0.12769(14) 0.0652(5) 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 C6 118.85(14) . .
C2 C1 C7 125.28(13) . .
C6 C1 C7 115.87(13) . .
C3 C2 C1 120.61(13) . .
C3 C2 H2 119.7 . .
C1 C2 H2 119.7 . .
C2 C3 C4 118.99(14) . .
C2 C3 C11 124.28(13) . .
C4 C3 C11 116.72(14) . .
C5 C4 C3 120.65(15) . .
C5 C4 H4 119.7 . .
C3 C4 H4 119.7 . .
C6 C5 C4 120.19(14) . .
C6 C5 H5 119.9 . .
C4 C5 H5 119.9 . .
C5 C6 C1 120.71(15) . .
C5 C6 H6 119.6 . .
C1 C6 H6 119.6 . .
C8 C7 C1 131.46(13) . .
C8 C7 H7 114.3 . .
C1 C7 H7 114.3 . .
C7 C8 C9 125.67(14) . .
C7 C8 C10 118.73(14) . .
C9 C8 C10 115.53(14) . .
N1 C9 C8 178.1(2) . .
N2 C10 C8 177.3(2) . .
C12 C11 C3 130.39(14) . .
C12 C11 H11 114.8 . .
C3 C11 H11 114.8 . .
C11 C12 C13 124.79(14) . .
C11 C12 C14 119.04(15) . .
C13 C12 C14 116.11(15) . .
N3 C13 C12 178.8(2) . .
N4 C14 C12 177.4(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C9 1.133(2) .
N2 C10 1.136(2) .
N3 C13 1.138(2) .
N4 C14 1.137(2) .
C1 C2 1.3957(19) .
C1 C6 1.402(2) .
C1 C7 1.452(2) .
C2 C3 1.3936(19) .
C2 H2 0.9300 .
C3 C4 1.401(2) .
C3 C11 1.455(2) .
C4 C5 1.376(2) .
C4 H4 0.9300 .
C5 C6 1.375(2) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 C8 1.343(2) .
C7 H7 0.9300 .
C8 C9 1.433(2) .
C8 C10 1.440(2) .
C11 C12 1.338(2) .
C11 H11 0.9300 .
C12 C13 1.433(2) .
C12 C14 1.439(2) .
