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#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/72/7227255.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_7227255
loop_
_publ_author_name
'Leblanc, Nicolas'
'Genovese, Damiano'
'De Cola, Luisa'
'Powell, Annie K.'
_publ_section_title
;
 A platform with connections in many directions - further remarkable
 facets to the multifaceted methylbiquinoxen dication.
;
_journal_issue                   10
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              6981
_journal_page_last               6988
_journal_paper_doi               10.1039/c6cp07538j
_journal_volume                  19
_journal_year                    2017
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C22 H26 N4 O2'
_chemical_formula_sum            'C22 H26 N4 O2'
_chemical_formula_weight         378.47
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2015-07-13T13:48:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2016-05-12 deposited with the CCDC.
2016-12-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.834(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.8290(11)
_cell_length_b                   11.3130(16)
_cell_length_c                   10.4030(13)
_cell_measurement_reflns_used    3628
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.97
_cell_measurement_theta_min      2.73
_cell_measurement_wavelength     0.71073
_cell_volume                     989.1(2)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 2008)'
_diffrn_ambient_temperature      180(2)
_diffrn_detector                 'image plate ( 34 cm diameter )'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measurement_details      ' 190 frames, detector distance = 115 mm'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.5 mm, multiple pinhole'
_diffrn_radiation_monochromator  'planar graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.98
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4943
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.98
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.402
_diffrn_reflns_theta_min         2.734
_diffrn_source                   'sealed X-ray tube, 12 x 0.4 mm fine focus'
_diffrn_source_current           40
_diffrn_source_power             2.000
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.378
_exptl_crystal_size_mid          0.353
_exptl_crystal_size_min          0.156
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.094(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.927
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2205
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.927
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0687P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1075
_reflns_number_gt                1399
_reflns_number_total             2205
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6cp07538j3.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7227252--7227255.cif.'
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               7227255
_shelx_estimated_absorpt_t_min   0.969
_shelx_estimated_absorpt_t_max   0.987
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, 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_calc_flag
C1 C 0.0793(2) 0.13445(12) 0.4605(2) 0.0633(4) Uani 1 d
C9 C 0.14510(14) 0.29242(12) 0.32287(15) 0.0521(3) Uani 1 d
C8 C 0.20661(16) 0.21441(15) 0.24648(17) 0.0617(4) Uani 1 d
C7 C 0.24686(18) 0.25563(17) 0.13669(18) 0.0715(5) Uani 1 d
C6 C 0.2249(2) 0.37243(18) 0.09755(19) 0.0731(5) Uani 1 d
C5 C 0.16094(18) 0.45052(15) 0.16907(17) 0.0628(4) Uani 1 d
C4 C 0.12286(14) 0.41216(12) 0.28261(14) 0.0520(3) Uani 1 d
C3 C 0.03811(13) 0.45955(11) 0.46427(14) 0.0465(3) Uani 1 d
C2 C 0.10123(15) 0.34495(11) 0.53218(15) 0.0489(3) Uani 1 d
C10 C 0.3075(2) 0.30802(16) 0.74179(17) 0.0653(4) Uani 1 d
C11 C 0.4522(2) 0.36535(19) 0.83390(19) 0.0709(5) Uani 1 d
N1 N 0.10014(13) 0.25810(10) 0.43250(12) 0.0525(3) Uani 1 d
N2 N 0.05322(12) 0.49212(9) 0.34977(12) 0.0491(3) Uani 1 d
O1 O 0.25732(10) 0.37296(8) 0.61961(9) 0.0529(3) Uani 1 d
H1A H 0.020(2) 0.0891(16) 0.368(2) 0.079(5) Uiso 1 d
H1B H 0.179(2) 0.0926(16) 0.504(2) 0.083(5) Uiso 1 d
H1C H 0.006(3) 0.1310(18) 0.526(2) 0.100(6) Uiso 1 d
H8 H 0.221(2) 0.1265(16) 0.2741(18) 0.074(5) Uiso 1 d
H7 H 0.294(2) 0.1975(16) 0.082(2) 0.088(6) Uiso 1 d
H6 H 0.248(2) 0.4011(16) 0.022(2) 0.086(6) Uiso 1 d
H5 H 0.1383(19) 0.5353(16) 0.1444(18) 0.067(4) Uiso 1 d
H2 H 0.0338(16) 0.3139(11) 0.5899(15) 0.050(4) Uiso 1 d
H10A H 0.329(2) 0.223(2) 0.719(2) 0.094(6) Uiso 1 d
H10B H 0.214(2) 0.3061(15) 0.7854(19) 0.082(5) Uiso 1 d
H11A H 0.534(2) 0.3706(16) 0.791(2) 0.089(6) Uiso 1 d
H11B H 0.488(2) 0.3234(18) 0.919(2) 0.094(6) Uiso 1 d
H11C H 0.428(2) 0.4521(19) 0.859(2) 0.092(6) Uiso 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 0 '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 0.006 '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
N1 C9 C8 123.56(14) . .
N1 C9 C4 117.88(11) . .
C8 C9 C4 118.52(14) . .
C7 C8 C9 119.97(16) . .
C8 C7 C6 121.38(15) . .
C7 C6 C5 119.82(18) . .
C6 C5 C4 120.13(17) . .
C5 C4 N2 118.71(14) . .
C5 C4 C9 120.14(13) . .
N2 C4 C9 121.02(12) . .
N2 C3 C3 118.84(14) . 3_566
N2 C3 C2 123.52(11) . .
C3 C3 C2 117.58(15) 3_566 .
N1 C2 O1 113.85(10) . .
N1 C2 C3 109.53(12) . .
O1 C2 C3 104.71(10) . .
O1 C10 C11 108.78(14) . .
C9 N1 C2 118.01(11) . .
C9 N1 C1 121.72(12) . .
C2 N1 C1 119.38(13) . .
C3 N2 C4 117.54(11) . .
C10 O1 C2 115.45(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.4522(18) .
C9 N1 1.3735(19) .
C9 C8 1.403(2) .
C9 C4 1.414(2) .
C8 C7 1.377(3) .
C7 C6 1.379(3) .
C6 C5 1.382(2) .
C5 C4 1.393(2) .
C4 N2 1.3955(17) .
C3 N2 1.2922(18) .
C3 C3 1.466(3) 3_566
C3 C2 1.4997(18) .
C2 N1 1.4264(18) .
C2 O1 1.4350(16) .
C10 O1 1.4166(18) .
C10 C11 1.491(2) .
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
N1 C9 C8 C7 179.09(13) .
C4 C9 C8 C7 1.3(2) .
C9 C8 C7 C6 -1.4(2) .
C8 C7 C6 C5 -0.1(2) .
C7 C6 C5 C4 1.8(2) .
C6 C5 C4 N2 -177.74(13) .
C6 C5 C4 C9 -1.9(2) .
N1 C9 C4 C5 -177.59(12) .
C8 C9 C4 C5 0.31(19) .
N1 C9 C4 N2 -1.81(18) .
C8 C9 C4 N2 176.09(12) .
N2 C3 C2 N1 -30.26(16) .
C3 C3 C2 N1 152.63(13) 3_566
N2 C3 C2 O1 92.19(14) .
C3 C3 C2 O1 -84.92(15) 3_566
C8 C9 N1 C2 155.14(12) .
C4 C9 N1 C2 -27.07(17) .
C8 C9 N1 C1 -14.0(2) .
C4 C9 N1 C1 163.80(13) .
O1 C2 N1 C9 -76.27(15) .
C3 C2 N1 C9 40.56(14) .
O1 C2 N1 C1 93.12(14) .
C3 C2 N1 C1 -150.06(12) .
C3 C3 N2 C4 -178.53(13) 3_566
C2 C3 N2 C4 4.39(18) .
C5 C4 N2 C3 -171.14(12) .
C9 C4 N2 C3 13.02(18) .
C11 C10 O1 C2 -167.02(13) .
N1 C2 O1 C10 -93.61(15) .
C3 C2 O1 C10 146.80(13) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139203074
