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#$Date: 2025-04-28 14:31:21 +0300 (Mon, 28 Apr 2025) $
#$Revision: 299433 $
#$URL: file:///home/coder/svn-repositories/cod/cif/3/00/04/3000470.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_3000470
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_moiety         '2(O), C20 H10 N4'
_chemical_formula_sum            'C20 H10 N4 O2'
_chemical_formula_weight         338.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-11-03
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_cell_angle_alpha                97.17
_cell_angle_beta                 96.81
_cell_angle_gamma                99.79
_cell_formula_units_Z            2
_cell_length_a                   3.795
_cell_length_b                   14.526
_cell_length_c                   17.715
_cell_measurement_reflns_used    5084
_cell_measurement_temperature    79
_cell_measurement_theta_max      0.870595921720824
_cell_measurement_theta_min      0.10288693714916029
_cell_volume                     945.003
_computing_cell_refinement
'dials.two_theta_refine (Waterman et al., 2016)'
_computing_data_collection
'Verlox (Thermo Fisher Scientific) and SerialEM (Mastronarde, 2005)'
_computing_data_reduction        'dials.scale (Beilsten-Edmands et al., 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      79
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
;
Talos Arctica G2
;
_diffrn_radiation_type           electrons
_diffrn_radiation_wavelength     0.02508
_diffrn_reflns_av_R_equivalents  0.2838
_diffrn_reflns_av_unetI/netI     0.2347
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            31259
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        0.845
_diffrn_reflns_theta_max         0.845
_diffrn_reflns_theta_min         0.104
_exptl_absorpt_coefficient_mu    0.000
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_description       plate
_exptl_crystal_F_000             135
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       38194(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.281
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         3221
_refine_ls_number_restraints     228
_refine_ls_restrained_S_all      1.241
_refine_ls_R_factor_all          0.2225
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4048
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1615
_reflns_number_total             3221
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            BP1_ADD.cif
_cod_data_source_block           bp1
_cod_depositor_comments
'Releasing structure 3000470 into public domain as published material.'
_cod_original_cell_volume        945.0
_cod_database_code               3000470
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Restrained distances
 C17-H17 \\sim C18-H18 \\sim C15-H15 \\sim C14-H14 \\sim C8-H8 \\sim C7-H7
\\sim C5-H5 \\sim C4-H4 \\sim C2-H2
 \\sim C12-H12
 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
Uanis(O2B) \\sim Ueq, Uanis(O2A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(O2B)=1-FVAR(1)
 Sof(O2A)=FVAR(1)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2A O 0.767(6) 0.911(2) 0.0090(12) 0.078(11) Uani 0.45(5) 1 d . U P A 1
O2B O 0.614(14) 0.956(4) -0.008(3) 0.202(19) Uani 0.55(5) 1 d . U P A 2
C13 C 0.3917(19) 0.8367(6) 0.2640(4) 0.0348(17) Uani 1 1 d . . . . .
C4 C 0.5837(18) 0.6887(6) 0.3063(4) 0.0373(18) Uani 1 1 d D . . . .
C18 C 0.3337(18) 0.8779(6) 0.3357(4) 0.0371(18) Uani 1 1 d D . . . .
C16 C 0.3053(18) 1.0297(6) 0.2903(4) 0.0373(18) Uani 1 1 d . . . . .
C15 C 0.378(2) 0.9904(6) 0.2186(4) 0.041(2) Uani 1 1 d D . . . .
C11 C 0.1853(18) 1.1858(6) 0.3592(4) 0.0382(18) Uani 1 1 d . . . . .
C7 C 0.383(2) 0.5883(6) 0.1566(4) 0.0394(19) Uani 1 1 d D . . . .
C5 C 0.6357(19) 0.5944(6) 0.2907(4) 0.0394(19) Uani 1 1 d D . . . .
C3 C 0.4417(19) 0.7375(6) 0.2481(4) 0.0410(19) Uani 1 1 d . . . . .
C6 C 0.5364(18) 0.5439(6) 0.2158(4) 0.0378(18) Uani 1 1 d . . . . .
C17 C 0.2854(19) 0.9721(6) 0.3497(4) 0.0365(18) Uani 1 1 d D . . . .
C14 C 0.413(2) 0.8941(6) 0.2032(5) 0.045(2) Uani 1 1 d D . . . .
C12 C 0.264(2) 1.1276(7) 0.2985(5) 0.045(2) Uani 1 1 d D . . . .
C8 C 0.3358(19) 0.6838(6) 0.1711(4) 0.0401(19) Uani 1 1 d D . . . .
C2 C 0.6143(18) 0.4492(6) 0.2064(4) 0.0371(18) Uani 1 1 d D . . . .
C1 C 0.5320(19) 0.3775(6) 0.1415(4) 0.0406(19) Uani 1 1 d . . . . .
C9 C 0.647(2) 0.2897(6) 0.1494(4) 0.040(2) Uani 1 1 d . . . . .
N1 N 0.741(2) 0.2165(6) 0.1551(4) 0.048(2) Uani 1 1 d . . . . .
N4 N 0.131(2) 1.3605(6) 0.3382(4) 0.048(2) Uani 1 1 d . . . . .
C20 C 0.1623(19) 1.2836(6) 0.3482(5) 0.044(2) Uani 1 1 d . . . . .
N2 N 0.170(2) 0.3833(7) 0.0078(4) 0.055(2) Uani 1 1 d . . . . .
C10 C 0.334(2) 0.3839(7) 0.0693(5) 0.050(2) Uani 1 1 d . . . . .
N3 N 0.037(2) 1.1419(7) 0.4918(4) 0.058(2) Uani 1 1 d . . . . .
C19 C 0.112(2) 1.1606(7) 0.4323(4) 0.048(2) Uani 1 1 d . . . . .
O1 O -0.254(3) 1.4040(18) 0.5184(7) 0.192(10) Uani 1 1 d . . . . .
H5 H 0.780(10) 0.560(3) 0.337(2) 0.061(11) Uiso 1 1 d D . . . .
H17 H 0.189(12) 1.001(3) 0.4061(17) 0.070(13) Uiso 1 1 d D . . . .
H15 H 0.357(13) 1.025(4) 0.163(2) 0.076(14) Uiso 1 1 d D . . . .
H2 H 0.769(11) 0.418(4) 0.254(2) 0.067(12) Uiso 1 1 d D . . . .
H12 H 0.326(12) 1.165(4) 0.247(2) 0.073(13) Uiso 1 1 d D . . . .
H18 H 0.313(12) 0.835(3) 0.386(2) 0.074(13) Uiso 1 1 d D . . . .
H14 H 0.525(13) 0.874(4) 0.1463(18) 0.083(15) Uiso 1 1 d D . . . .
H7 H 0.330(12) 0.547(3) 0.0950(16) 0.077(14) Uiso 1 1 d D . . . .
H4 H 0.679(10) 0.733(3) 0.3668(16) 0.061(11) Uiso 1 1 d D . . . .
H8 H 0.209(12) 0.724(4) 0.125(2) 0.076(13) Uiso 1 1 d D . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0000 0.0000 '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
C18 C13 C3 122.9(7) . .
C18 C13 C14 118.4(8) . .
C14 C13 C3 118.7(7) . .
C5 C4 C3 122.6(8) . .
C5 C4 H4 121(2) . .
C3 C4 H4 116(2) . .
C13 C18 C17 122.2(7) . .
C13 C18 H18 121(3) . .
C17 C18 H18 117(3) . .
C15 C16 C17 118.4(7) . .
C15 C16 C12 116.7(7) . .
C17 C16 C12 124.9(7) . .
C16 C15 C14 121.7(7) . .
C16 C15 H15 126(3) . .
C14 C15 H15 111(3) . .
C12 C11 C20 117.5(7) . .
C12 C11 C19 126.8(8) . .
C19 C11 C20 115.7(7) . .
C6 C7 C8 121.1(8) . .
C6 C7 H7 117(3) . .
C8 C7 H7 121(3) . .
C4 C5 H5 121(2) . .
C6 C5 C4 120.1(7) . .
C6 C5 H5 119(2) . .
C4 C3 C13 122.7(7) . .
C4 C3 C8 116.6(8) . .
C8 C3 C13 120.7(6) . .
C7 C6 C2 125.6(8) . .
C5 C6 C7 119.4(8) . .
C5 C6 C2 115.0(7) . .
C18 C17 C16 120.2(7) . .
C18 C17 H17 121(3) . .
C16 C17 H17 119(3) . .
C13 C14 H14 124(3) . .
C15 C14 C13 119.1(7) . .
C15 C14 H14 115(3) . .
C16 C12 H12 115(3) . .
C11 C12 C16 131.4(7) . .
C11 C12 H12 114(3) . .
C7 C8 C3 120.2(7) . .
C7 C8 H8 124(3) . .
C3 C8 H8 116(3) . .
C6 C2 H2 124(3) . .
C1 C2 C6 130.2(7) . .
C1 C2 H2 106(3) . .
C2 C1 C9 117.6(7) . .
C2 C1 C10 125.6(7) . .
C10 C1 C9 116.8(8) . .
N1 C9 C1 179.3(9) . .
N4 C20 C11 177.6(9) . .
N2 C10 C1 175.8(10) . .
N3 C19 C11 176.7(8) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O2B O2B 1.68(11) 2_675
C13 C18 1.394(10) .
C13 C3 1.482(11) .
C13 C14 1.444(10) .
C4 C5 1.415(12) .
C4 C3 1.426(10) .
C4 H4 1.16(2) .
C18 C17 1.406(11) .
C18 H18 1.16(2) .
C16 C15 1.404(11) .
C16 C17 1.425(10) .
C16 C12 1.447(11) .
C15 C14 1.424(11) .
C15 H15 1.16(2) .
C11 C12 1.378(11) .
C11 C20 1.474(11) .
C11 C19 1.435(10) .
C7 C6 1.416(10) .
C7 C8 1.424(11) .
C7 H7 1.15(2) .
C5 C6 1.409(11) .
C5 H5 1.15(2) .
C3 C8 1.459(11) .
C6 C2 1.450(11) .
C17 H17 1.16(2) .
C14 H14 1.16(2) .
C12 H12 1.15(2) .
C8 H8 1.17(2) .
C2 C1 1.417(11) .
C2 H2 1.16(2) .
C1 C9 1.432(12) .
C1 C10 1.426(10) .
C9 N1 1.189(10) .
N4 C20 1.176(11) .
N2 C10 1.187(9) .
N3 C19 1.175(10) .
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
C13 C18 C17 C16 -1.8(11) . . . .
C13 C3 C8 C7 -179.6(6) . . . .
C4 C5 C6 C7 -0.3(10) . . . .
C4 C5 C6 C2 178.0(6) . . . .
C4 C3 C8 C7 -1.3(10) . . . .
C18 C13 C3 C4 -27.0(11) . . . .
C18 C13 C3 C8 151.1(7) . . . .
C18 C13 C14 C15 0.7(11) . . . .
C16 C15 C14 C13 -3.4(12) . . . .
C15 C16 C17 C18 -0.8(10) . . . .
C15 C16 C12 C11 178.4(8) . . . .
C7 C6 C2 C1 -6.3(11) . . . .
C5 C4 C3 C13 -179.1(7) . . . .
C5 C4 C3 C8 2.6(10) . . . .
C5 C6 C2 C1 175.5(7) . . . .
C3 C13 C18 C17 -179.8(7) . . . .
C3 C13 C14 C15 -177.7(7) . . . .
C3 C4 C5 C6 -1.9(10) . . . .
C6 C7 C8 C3 -0.8(10) . . . .
C6 C2 C1 C9 179.7(6) . . . .
C6 C2 C1 C10 -2.4(12) . . . .
C17 C16 C15 C14 3.4(11) . . . .
C17 C16 C12 C11 -3.2(13) . . . .
C14 C13 C18 C17 1.9(11) . . . .
C14 C13 C3 C4 151.3(7) . . . .
C14 C13 C3 C8 -30.5(10) . . . .
C12 C16 C15 C14 -178.0(7) . . . .
C12 C16 C17 C18 -179.2(7) . . . .
C8 C7 C6 C5 1.6(10) . . . .
C8 C7 C6 C2 -176.4(7) . . . .
C20 C11 C12 C16 -179.9(7) . . . .
C19 C11 C12 C16 -1.7(14) . . . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
_cod_related_entry_description
1 XRDa 00261 DOI:10.51093/xrd-00261
