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#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/41/4034114.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_4034114
loop_
_publ_author_name
'Kaleta, Jiří'
'Bastien, Guillaume'
'Wen, Jin'
'Dračínský, Martin'
'Tortorici, Edward'
'Císařová, Ivana'
'Beale, Paul D.'
'Rogers, Charles T.'
'Michl, Josef'
_publ_section_title
;
 Bulk Inclusions of Double Pyridazine Molecular Rotors in Hexagonal Tris(
 o-phenylene)cyclotriphosphazene.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8449
_journal_page_last               8467
_journal_paper_doi               10.1021/acs.joc.9b00553
_journal_volume                  84
_journal_year                    2019
_chemical_compound_source        'Synthesized by Dr. Jiri Kaleta'
_chemical_formula_moiety         'C18 H22 N4'
_chemical_formula_sum            'C18 H22 N4'
_chemical_formula_weight         294.39
_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
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 93.3070(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.8515(2)
_cell_length_b                   8.3931(3)
_cell_length_c                   16.8969(6)
_cell_measurement_reflns_used    8040
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      69.8910
_cell_measurement_theta_min      5.2451
_cell_volume                     828.46(5)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v4.2.9'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XS, VERSION 2013/1'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Helios Cu  multilayer optic'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10305
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.235
_diffrn_reflns_theta_min         5.244
_diffrn_source                   'I\mS  micro-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.561
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless-yellow
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_description       bar
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         1577
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.166
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0445
_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)+(0.0373P)²+0.6300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1201
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1427
_reflns_number_total             1577
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b00553_si_004.cif
_cod_data_source_block           01_JK665
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4034114
_shelx_shelxl_version_number     2014/7
_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   0.881
_shelx_estimated_absorpt_t_max   0.975
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
N1 N 0.5781(2) 0.69629(17) 0.57838(8) 0.0266(4) Uani 1 1 d . .
N2 N 0.5287(2) 0.55960(17) 0.61544(8) 0.0255(3) Uani 1 1 d . .
C1 C 0.4762(3) 0.9407(2) 0.51710(10) 0.0269(4) Uani 1 1 d . .
C2 C 0.4099(3) 0.7973(2) 0.55664(9) 0.0236(4) Uani 1 1 d . .
C3 C 0.1798(3) 0.7666(2) 0.57003(10) 0.0270(4) Uani 1 1 d . .
H3 H 0.0626 0.8405 0.5546 0.032 Uiso 1 1 calc R U
C4 C 0.1312(3) 0.6266(2) 0.60605(10) 0.0255(4) Uani 1 1 d . .
H4 H -0.0224 0.5988 0.6153 0.031 Uiso 1 1 calc R U
C5 C 0.3116(3) 0.5244(2) 0.62913(9) 0.0218(4) Uani 1 1 d . .
C6 C 0.2653(3) 0.3682(2) 0.67123(10) 0.0252(4) Uani 1 1 d . .
C7 C 0.4845(3) 0.2772(2) 0.69359(12) 0.0368(5) Uani 1 1 d . .
H7A H 0.5649 0.2538 0.6456 0.055 Uiso 1 1 calc R U
H7B H 0.4467 0.1772 0.7198 0.055 Uiso 1 1 calc R U
H7C H 0.5830 0.3419 0.7298 0.055 Uiso 1 1 calc R U
C8 C 0.1106(3) 0.2655(2) 0.61532(11) 0.0333(4) Uani 1 1 d . .
H8A H -0.0346 0.3211 0.6033 0.050 Uiso 1 1 calc R U
H8B H 0.0808 0.1634 0.6409 0.050 Uiso 1 1 calc R U
H8C H 0.1867 0.2465 0.5660 0.050 Uiso 1 1 calc R U
C9 C 0.1401(3) 0.4044(2) 0.74696(11) 0.0326(4) Uani 1 1 d . .
H9A H -0.0025 0.4616 0.7328 0.049 Uiso 1 1 calc R U
H9B H 0.2382 0.4703 0.7827 0.049 Uiso 1 1 calc R U
H9C H 0.1050 0.3042 0.7735 0.049 Uiso 1 1 calc R U
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'
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
C2 N1 N2 119.65(14) .
C5 N2 N1 120.00(14) .
C1 C1 C2 177.7(3) 3_676
N1 C2 C3 122.58(16) .
N1 C2 C1 116.37(15) .
C3 C2 C1 121.04(15) .
C4 C3 C2 117.30(15) .
C4 C3 H3 121.3 .
C2 C3 H3 121.3 .
C3 C4 C5 118.71(15) .
C3 C4 H4 120.6 .
C5 C4 H4 120.6 .
N2 C5 C4 121.74(15) .
N2 C5 C6 117.82(14) .
C4 C5 C6 120.43(14) .
C7 C6 C5 112.23(14) .
C7 C6 C8 109.23(15) .
C5 C6 C8 108.08(14) .
C7 C6 C9 109.09(15) .
C5 C6 C9 108.92(14) .
C8 C6 C9 109.25(14) .
C6 C7 H7A 109.5 .
C6 C7 H7B 109.5 .
H7A C7 H7B 109.5 .
C6 C7 H7C 109.5 .
H7A C7 H7C 109.5 .
H7B C7 H7C 109.5 .
C6 C8 H8A 109.5 .
C6 C8 H8B 109.5 .
H8A C8 H8B 109.5 .
C6 C8 H8C 109.5 .
H8A C8 H8C 109.5 .
H8B C8 H8C 109.5 .
C6 C9 H9A 109.5 .
C6 C9 H9B 109.5 .
H9A C9 H9B 109.5 .
C6 C9 H9C 109.5 .
H9A C9 H9C 109.5 .
H9B C9 H9C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C2 1.335(2) .
N1 N2 1.346(2) .
N2 C5 1.338(2) .
C1 C1 1.192(4) 3_676
C1 C2 1.441(2) .
C2 C3 1.402(2) .
C3 C4 1.361(3) .
C3 H3 0.9500 .
C4 C5 1.398(2) .
C4 H4 0.9500 .
C5 C6 1.523(2) .
C6 C7 1.522(2) .
C6 C8 1.535(2) .
C6 C9 1.541(2) .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168328068
