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#$Date: 2024-09-17 04:16:28 +0300 (Tue, 17 Sep 2024) $
#$Revision: 294772 $
#$URL: file:///home/coder/svn-repositories/cod/cif/3/00/04/3000475.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_3000475
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         'C9 H8 N O2'
_chemical_formula_sum            'C9 H8 N O2'
_chemical_formula_weight         162.16
_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   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                74.649(7)
_cell_angle_beta                 84.853(9)
_cell_angle_gamma                78.442(7)
_cell_formula_units_Z            2
_cell_length_a                   4.6343(8)
_cell_length_b                   7.5342(12)
_cell_length_c                   12.9284(19)
_cell_measurement_reflns_used    2832
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.11
_cell_measurement_theta_min      2.85
_cell_volume                     426.15(12)
_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 0.995
_diffrn_measured_fraction_theta_max 0.982
_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  0.0448
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7282
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.700
_diffrn_reflns_theta_min         3.758
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       block
_exptl_crystal_F_000             170
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       0.37(9)
_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   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1774
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1205
_refine_ls_R_factor_gt           0.0959
_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)+(0.1960P)²+0.0589P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2574
_refine_ls_wR_factor_ref         0.2851
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1176
_reflns_number_total             1774
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            TP-2_SCXRD.cif
_cod_data_source_block           TP-2
_cod_depositor_comments
'Releasing structure 3000475 into public domain as published material.'
_cod_database_code               3000475
_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   0.981
_shelx_estimated_absorpt_t_max   0.992
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
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
O1 O 0.6393(6) 0.5865(3) 0.35583(18) 0.0845(9) Uani 1 1 d . . . . .
N1 N 0.5318(9) 0.1566(5) 0.1667(2) 0.0958(12) Uani 1 1 d . . . . .
C1 C 0.3431(6) 0.2840(3) 0.4085(2) 0.0475(7) Uani 1 1 d . . . . .
H1 H 0.348967 0.360339 0.453974 0.057 Uiso 1 1 calc R U . . .
O2 O 0.7682(5) 0.5295(3) 0.19717(16) 0.0681(8) Uani 1 1 d . . . . .
C2 C 0.1728(5) 0.1362(3) 0.4518(2) 0.0436(7) Uani 1 1 d . . . . .
C3 C 0.0157(6) 0.1383(4) 0.5490(2) 0.0508(8) Uani 1 1 d . . . . .
H3 H 0.026055 0.231769 0.582497 0.061 Uiso 1 1 calc R U . . .
C4 C -0.1529(6) 0.0067(4) 0.5962(2) 0.0518(8) Uani 1 1 d . . . . .
H4 H -0.255246 0.012186 0.660895 0.062 Uiso 1 1 calc R U . . .
C5 C 0.4924(6) 0.3292(3) 0.3150(2) 0.0475(7) Uani 1 1 d . . . . .
C6 C 0.6401(6) 0.4956(4) 0.2930(2) 0.0533(8) Uani 1 1 d . . . . .
C7 C 0.9054(9) 0.6966(5) 0.1648(3) 0.0822(11) Uani 1 1 d . . . . .
H7A H 0.756624 0.807918 0.163219 0.099 Uiso 1 1 calc R U . . .
H7B H 1.050133 0.689554 0.216200 0.099 Uiso 1 1 calc R U . . .
C8 C 1.0461(13) 0.7071(7) 0.0597(4) 0.1163(17) Uani 1 1 d . . . . .
H8A H 1.191522 0.595953 0.061628 0.174 Uiso 1 1 calc R U . . .
H8B H 1.139430 0.814724 0.038697 0.174 Uiso 1 1 calc R U . . .
H8C H 0.900905 0.717502 0.008871 0.174 Uiso 1 1 calc R U . . .
C9 C 0.5147(7) 0.2321(4) 0.2324(2) 0.0606(8) 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'
O O 0.0106 0.0060 '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
C5 C1 C2 131.3(2) . .
C5 C1 H1 114.4 . .
C2 C1 H1 114.4 . .
C6 O2 C7 116.7(2) . .
C3 C2 C4 117.6(2) . 2_556
C3 C2 C1 117.1(2) . .
C4 C2 C1 125.3(2) 2_556 .
C4 C3 C2 121.8(2) . .
C4 C3 H3 119.1 . .
C2 C3 H3 119.1 . .
C3 C4 C2 120.6(2) . 2_556
C3 C4 H4 119.7 . .
C2 C4 H4 119.7 2_556 .
C1 C5 C9 124.4(2) . .
C1 C5 C6 118.2(2) . .
C9 C5 C6 117.4(2) . .
O1 C6 O2 124.3(2) . .
O1 C6 C5 123.6(3) . .
O2 C6 C5 112.2(2) . .
C8 C7 O2 109.1(3) . .
C8 C7 H7A 109.9 . .
O2 C7 H7A 109.9 . .
C8 C7 H7B 109.9 . .
O2 C7 H7B 109.9 . .
H7A C7 H7B 108.3 . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
N1 C9 C5 179.5(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C6 1.192(3) .
N1 C9 1.130(4) .
C1 C5 1.335(4) .
C1 C2 1.456(3) .
C1 H1 0.9300 .
O2 C6 1.310(4) .
O2 C7 1.469(4) .
C2 C3 1.396(4) .
C2 C4 1.399(3) 2_556
C3 C4 1.368(4) .
C3 H3 0.9300 .
C4 H4 0.9300 .
C5 C9 1.432(4) .
C5 C6 1.497(4) .
C7 C8 1.443(6) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
