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#$Date: 2023-10-12 11:19:46 +0300 (Thu, 12 Oct 2023) $
#$Revision: 286918 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/76/8107615.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_8107615
loop_
_publ_author_name
'Fujisawa, Kiyoshi'
'Ageishi, Keigo'
'Tiekink, Edward R. T.'
_publ_section_title
;
 Crystal structure of
 [N(E),N′(E)]-N,N′-(1,4-phenylenedimethylidyne)bis-3,5-bis(propan-2-yl)-1H-pyrazol-4-amine,
 C26H36N6
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              973
_journal_page_last               976
_journal_paper_doi               10.1515/ncrs-2023-0305
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C26 H36 N6'
_chemical_formula_sum            'C26 H36 N6'
_chemical_formula_weight         432.61
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                104.980(3)
_cell_angle_beta                 94.279(3)
_cell_angle_gamma                93.876(3)
_cell_formula_units_Z            1
_cell_length_a                   5.7137(2)
_cell_length_b                   10.4374(3)
_cell_length_c                   11.1141(3)
_cell_measurement_reflns_used    6430
_cell_measurement_temperature    178(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.00
_cell_volume                     635.89(4)
_computing_cell_refinement       'CrysAlisPRO [1]'
_computing_data_collection       'CrysAlisPRO [1]'
_computing_data_reduction        'CrysAlisPRO [1]'
_computing_molecular_graphics    'ORTEP-3 for Windows [4]'
_computing_publication_material  'SHELXL-2018/3 [3]'
_computing_structure_refinement  'SHELXL-2018/3 [3]'
_computing_structure_solution    'SIR2008 [2]'
_diffrn_ambient_temperature      178(2)
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21711
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.451
_diffrn_reflns_theta_min         3.130
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro [1]
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.130
_exptl_crystal_description       plate
_exptl_crystal_F_000             234
_exptl_crystal_size_max          0.074
_exptl_crystal_size_mid          0.064
_exptl_crystal_size_min          0.013
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         3240
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0503
_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)+(0.0528P)²+0.1191P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1220
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2113
_reflns_number_total             3240
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0305_suppl_001.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        635.89(3)
_cod_database_code               8107615
_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_min   0.995
_shelx_estimated_absorpt_t_max   0.999
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
N1 N 0.1000(2) 0.12351(11) 0.46106(11) 0.0293(3) Uani 1 1 d D . . . .
H1N H 0.133(3) 0.1034(15) 0.5329(10) 0.035 Uiso 1 1 d D U . . .
N2 N -0.0513(2) 0.03672(11) 0.37231(11) 0.0292(3) Uani 1 1 d . . . . .
N3 N 0.0993(2) 0.30851(11) 0.23643(10) 0.0260(3) Uani 1 1 d . . . . .
C1 C 0.5676(3) 0.28535(19) 0.54768(19) 0.0532(5) Uani 1 1 d . . . . .
H1A H 0.527942 0.225032 0.599105 0.080 Uiso 1 1 calc R U . . .
H1B H 0.678888 0.359121 0.596878 0.080 Uiso 1 1 calc R U . . .
H1C H 0.639602 0.236620 0.474085 0.080 Uiso 1 1 calc R U . . .
C2 C 0.2369(3) 0.42227(16) 0.61729(16) 0.0453(4) Uani 1 1 d . . . . .
H2A H 0.098711 0.460681 0.588170 0.068 Uiso 1 1 calc R U . . .
H2B H 0.352990 0.494022 0.665484 0.068 Uiso 1 1 calc R U . . .
H2C H 0.188932 0.365351 0.670439 0.068 Uiso 1 1 calc R U . . .
C3 C 0.3449(3) 0.34005(14) 0.50578(14) 0.0303(4) Uani 1 1 d . . . . .
H3 H 0.391519 0.400907 0.453679 0.036 Uiso 1 1 calc R U . . .
C4 C 0.1730(2) 0.23160(13) 0.42531(13) 0.0243(3) Uani 1 1 d . . . . .
C5 C 0.0581(2) 0.21652(13) 0.30708(12) 0.0232(3) Uani 1 1 d . . . . .
C6 C -0.0787(2) 0.09167(13) 0.27724(12) 0.0237(3) Uani 1 1 d . . . . .
C7 C -0.2304(3) 0.01690(13) 0.16101(13) 0.0279(3) Uani 1 1 d . . . . .
H7 H -0.185876 0.054919 0.091160 0.033 Uiso 1 1 calc R U . . .
C8 C -0.4896(3) 0.03591(18) 0.17697(15) 0.0435(4) Uani 1 1 d . . . . .
H8A H -0.536192 0.002564 0.247220 0.065 Uiso 1 1 calc R U . . .
H8B H -0.585968 -0.013431 0.100224 0.065 Uiso 1 1 calc R U . . .
H8C H -0.513273 0.130798 0.193737 0.065 Uiso 1 1 calc R U . . .
C9 C -0.1904(3) -0.13078(15) 0.12481(16) 0.0457(4) Uani 1 1 d . . . . .
H9A H -0.021933 -0.140534 0.118713 0.069 Uiso 1 1 calc R U . . .
H9B H -0.278414 -0.174477 0.043833 0.069 Uiso 1 1 calc R U . . .
H9C H -0.244996 -0.172129 0.188661 0.069 Uiso 1 1 calc R U . . .
C10 C -0.0620(3) 0.32335(13) 0.15701(13) 0.0263(3) Uani 1 1 d . . . . .
H10 H -0.210474 0.273495 0.148718 0.032 Uiso 1 1 calc R U . . .
C11 C -0.0273(2) 0.41457(13) 0.07777(12) 0.0247(3) Uani 1 1 d . . . . .
C12 C 0.1824(3) 0.49322(14) 0.08688(14) 0.0307(3) Uani 1 1 d . . . . .
H12 H 0.308503 0.489268 0.146214 0.037 Uiso 1 1 calc R U . . .
C13 C -0.2088(3) 0.42275(14) -0.01003(14) 0.0312(3) Uani 1 1 d . . . . .
H13 H -0.353387 0.369568 -0.017252 0.037 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 0.0033 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'
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
C4 N1 N2 112.59(11) . .
C4 N1 H1N 129.6(10) . .
N2 N1 H1N 117.8(10) . .
C6 N2 N1 106.10(11) . .
C10 N3 C5 119.91(12) . .
C3 C1 H1A 109.5 . .
C3 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C3 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C3 C2 H2A 109.5 . .
C3 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
C3 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
C4 C3 C2 112.12(12) . .
C4 C3 C1 111.60(12) . .
C2 C3 C1 110.70(14) . .
C4 C3 H3 107.4 . .
C2 C3 H3 107.4 . .
C1 C3 H3 107.4 . .
N1 C4 C5 105.99(12) . .
N1 C4 C3 122.60(12) . .
C5 C4 C3 131.41(12) . .
C4 C5 N3 122.44(12) . .
C4 C5 C6 105.83(11) . .
N3 C5 C6 131.52(12) . .
N2 C6 C5 109.47(12) . .
N2 C6 C7 119.20(12) . .
C5 C6 C7 131.29(12) . .
C6 C7 C9 111.69(12) . .
C6 C7 C8 110.58(12) . .
C9 C7 C8 110.88(13) . .
C6 C7 H7 107.8 . .
C9 C7 H7 107.8 . .
C8 C7 H7 107.8 . .
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 . .
C7 C9 H9A 109.5 . .
C7 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C7 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
N3 C10 C11 122.49(13) . .
N3 C10 H10 118.8 . .
C11 C10 H10 118.8 . .
C12 C11 C13 118.45(12) . .
C12 C11 C10 122.04(13) . .
C13 C11 C10 119.51(13) . .
C13 C12 C11 120.30(13) 2_565 .
C13 C12 H12 119.9 2_565 .
C11 C12 H12 119.9 . .
C12 C13 C11 121.25(13) 2_565 .
C12 C13 H13 119.4 2_565 .
C11 C13 H13 119.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C4 1.3406(17) .
N1 N2 1.3585(16) .
N1 H1N 0.887(9) .
N2 C6 1.3307(17) .
N3 C10 1.2736(17) .
N3 C5 1.4074(16) .
C1 C3 1.519(2) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 C3 1.513(2) .
C2 H2A 0.9800 .
C2 H2B 0.9800 .
C2 H2C 0.9800 .
C3 C4 1.4971(19) .
C3 H3 1.0000 .
C4 C5 1.3903(19) .
C5 C6 1.4210(18) .
C6 C7 1.4998(19) .
C7 C9 1.527(2) .
C7 C8 1.525(2) .
C7 H7 1.0000 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 C11 1.4681(17) .
C10 H10 0.9500 .
C11 C12 1.388(2) .
C11 C13 1.392(2) .
C12 C13 1.3820(19) 2_565
C12 H12 0.9500 .
C13 H13 0.9500 .
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
C4 N1 N2 C6 -0.84(16) . . . .
N2 N1 C4 C5 1.55(16) . . . .
N2 N1 C4 C3 -178.49(12) . . . .
C2 C3 C4 N1 -71.57(18) . . . .
C1 C3 C4 N1 53.26(19) . . . .
C2 C3 C4 C5 108.37(18) . . . .
C1 C3 C4 C5 -126.80(17) . . . .
N1 C4 C5 N3 -176.96(12) . . . .
C3 C4 C5 N3 3.1(2) . . . .
N1 C4 C5 C6 -1.58(15) . . . .
C3 C4 C5 C6 178.47(14) . . . .
C10 N3 C5 C4 -152.37(14) . . . .
C10 N3 C5 C6 33.6(2) . . . .
N1 N2 C6 C5 -0.23(15) . . . .
N1 N2 C6 C7 177.68(12) . . . .
C4 C5 C6 N2 1.14(15) . . . .
N3 C5 C6 N2 175.93(13) . . . .
C4 C5 C6 C7 -176.43(14) . . . .
N3 C5 C6 C7 -1.6(3) . . . .
N2 C6 C7 C9 -41.50(18) . . . .
C5 C6 C7 C9 135.88(16) . . . .
N2 C6 C7 C8 82.49(16) . . . .
C5 C6 C7 C8 -100.13(17) . . . .
C5 N3 C10 C11 -178.05(12) . . . .
N3 C10 C11 C12 -1.7(2) . . . .
N3 C10 C11 C13 177.92(13) . . . .
C13 C11 C12 C13 -0.1(2) . . . 2_565
C10 C11 C12 C13 179.58(13) . . . 2_565
C12 C11 C13 C12 0.1(2) . . . 2_565
C10 C11 C13 C12 -179.59(14) . . . 2_565
