#------------------------------------------------------------------------------
#$Date: 2021-08-21 01:40:42 +0300 (Sat, 21 Aug 2021) $
#$Revision: 268153 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/34/7243403.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_7243403
loop_
_publ_author_name
'Sanda Bawa, Ali'
'Meunier-Prest, Rita'
'Rousselin, Yoann'
'Couvercelle, Jean-Pierre'
'Christine, Stern'
'Malézieux, Bernard'
'Bouvet, Marcel'
_publ_section_title
;
 Series of charge transfer complexes obtained as crystals in a confined
 environment
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D1CE00929J
_journal_year                    2021
_chemical_formula_moiety         'C10 H2 N4, C6 H6 O2'
_chemical_formula_sum            'C16 H8 N4 O2'
_chemical_formula_weight         288.26
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-19
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-04-01 deposited with the CCDC.	2021-08-19 downloaded from the CCDC.
;
_cell_angle_alpha                108.309(5)
_cell_angle_beta                 109.791(4)
_cell_angle_gamma                92.810(5)
_cell_formula_units_Z            1
_cell_length_a                   6.3120(4)
_cell_length_b                   7.4057(5)
_cell_length_c                   8.1661(5)
_cell_measurement_reflns_used    1700
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      66.59
_cell_measurement_theta_min      6.15
_cell_volume                     335.79(4)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 CMOS
_diffrn_detector_area_resol_mean '1024 x 1024'
_diffrn_detector_type            'Photon 100'
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans''
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'QUAZAR MX multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_av_unetI/netI     0.0734
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2906
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        66.706
_diffrn_reflns_theta_max         66.706
_diffrn_reflns_theta_min         6.153
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Cu
_diffrn_source_type              'high brilliance microfocus sealed tube, Cu'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.817
_exptl_absorpt_correction_T_max  0.9287
_exptl_absorpt_correction_T_min  0.7394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1231 before and 0.0720 after correction.
The Ratio of minimum to maximum transmission is 0.7962.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_description       plate
_exptl_crystal_F_000             148
_exptl_crystal_recrystallization_method
'The material was recrystallised by sublimation'
_exptl_crystal_size_max          0.158
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.290
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1163
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.290
_refine_ls_R_factor_all          0.1149
_refine_ls_R_factor_gt           0.0934
_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)+0.9100P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1831
_refine_ls_wR_factor_ref         0.1915
_reflns_Friedel_coverage         0.000
_reflns_number_gt                927
_reflns_number_total             1163
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce00929j2.cif
_cod_data_source_block           TCNB-H2Q
_cod_database_code               7243403
_publcif_datablock.id            {0bb0e9a7-9b7e-4a94-8f6c-62024d4e67ff}
_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.
;
_shelx_estimated_absorpt_t_max   0.952
_shelx_estimated_absorpt_t_min   0.882
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C1(H1)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder oil'
_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
O1 O 0.1688(5) 0.3875(5) 0.1172(5) 0.0301(8) Uani 1 1 d . . . . .
H1A H 0.185578 0.463717 0.223347 0.045 Uiso 1 1 calc GR . . . .
C6 C 0.5300(7) 0.5853(6) 0.1860(6) 0.0234(10) Uani 1 1 d . . . . .
H6 H 0.548905 0.645633 0.312543 0.028 Uiso 1 1 calc R . . . .
C7 C 0.3352(7) 0.4474(6) 0.0638(6) 0.0220(10) Uani 1 1 d . . . . .
C8 C 0.3041(7) 0.3653(7) -0.1239(6) 0.0250(10) Uani 1 1 d . . . . .
H8 H 0.169270 0.275597 -0.209014 0.030 Uiso 1 1 calc R . . . .
N1 N 0.2146(7) 0.6324(6) 0.4801(6) 0.0307(10) Uani 1 1 d . . . . .
N2 N 0.7980(7) 0.9585(6) 0.6344(6) 0.0340(11) Uani 1 1 d . . . . .
C1 C 0.2869(8) 0.8852(6) 0.9452(7) 0.0252(10) Uani 1 1 d . . . . .
H1 H 0.142580 0.807905 0.908293 0.030 Uiso 1 1 calc R . . . .
C2 C 0.3919(8) 0.8725(6) 0.8182(6) 0.0230(10) Uani 1 1 d . . . . .
C3 C 0.6041(7) 0.9875(7) 0.8732(7) 0.0236(10) Uani 1 1 d . . . . .
C4 C 0.2873(8) 0.7402(7) 0.6297(7) 0.0270(11) Uani 1 1 d . . . . .
C5 C 0.7129(8) 0.9741(7) 0.7403(7) 0.0264(10) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_publ_flag
C7 O1 H1A 109.5 . . ?
C7 C6 H6 119.7 . . ?
C8 C6 H6 119.7 2_665 . ?
C8 C6 C7 120.5(4) 2_665 . ?
O1 C7 C6 123.5(4) . . ?
O1 C7 C8 117.2(4) . . ?
C8 C7 C6 119.4(4) . . ?
C6 C8 C7 120.1(4) 2_665 . ?
C6 C8 H8 120.0 2_665 . ?
C7 C8 H8 120.0 . . ?
C2 C1 H1 120.5 . . ?
C3 C1 H1 120.5 2_677 . ?
C3 C1 C2 119.0(4) 2_677 . ?
C1 C2 C3 120.2(4) . . ?
C1 C2 C4 121.0(4) . . ?
C3 C2 C4 118.8(4) . . ?
C1 C3 C2 120.7(4) 2_677 . ?
C1 C3 C5 119.2(4) 2_677 . ?
C2 C3 C5 120.1(4) . . ?
N1 C4 C2 176.5(5) . . ?
N2 C5 C3 178.3(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1A 0.8400 . ?
O1 C7 1.370(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.399(6) . ?
C6 C8 1.388(6) 2_665 ?
C7 C8 1.399(6) . ?
C8 H8 0.9500 . ?
N1 C4 1.145(6) . ?
N2 C5 1.143(6) . ?
C1 H1 0.9500 . ?
C1 C2 1.391(7) . ?
C1 C3 1.388(7) 2_677 ?
C2 C3 1.400(6) . ?
C2 C4 1.438(7) . ?
C3 C5 1.450(7) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1A N1 0.84 2.02 2.854(5) 176.2 . yes
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
_geom_torsion_publ_flag
O1 C7 C8 C6 -177.8(4) . . . 2_665 ?
C6 C7 C8 C6 2.6(7) . . . 2_665 ?
C8 C6 C7 O1 177.8(4) 2_665 . . . ?
C8 C6 C7 C8 -2.7(7) 2_665 . . . ?
C1 C2 C3 C1 0.3(7) . . . 2_677 ?
C1 C2 C3 C5 -179.9(4) . . . . ?
C3 C1 C2 C3 -0.3(7) 2_677 . . . ?
C3 C1 C2 C4 178.8(4) 2_677 . . . ?
C4 C2 C3 C1 -178.9(4) . . . 2_677 ?
C4 C2 C3 C5 0.9(7) . . . . ?
