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#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/82/2228279.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_2228279
loop_
_publ_author_name
'Zhang, Zhao-Po'
'Wang, Yuan'
'Li, Xiao-Xia'
'Li, Yan-Wei'
_publ_section_title
;
 (E,E)-3,3'-Dimethyl-1,1'-diphenyl-4,4'-{[3-azapentane-1,5-diylbis(azanediyl)]bis(phenylmethylidyne)}di-1H-pyrazol-5(4H)-one
;
_journal_coeditor_code           CV5005
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3326
_journal_paper_doi               10.1107/S1600536810048981
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C38 H37 N7 O2'
_chemical_formula_moiety         'C38 H37 N7 O2'
_chemical_formula_sum            'C38 H37 N7 O2'
_chemical_formula_weight         623.75
_chemical_name_systematic
;
(E,E)-3,3'-Dimethyl-1,1'-diphenyl-4,4'-{[3-azapentane-
1,5-diylbis(azanediyl)]bis(phenylmethylidyne)}di-1H-pyrazol-
5(4H)-one
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.748(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.3219(8)
_cell_length_b                   8.1990(2)
_cell_length_c                   20.5468(6)
_cell_measurement_reflns_used    1721
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.00
_cell_measurement_theta_min      2.48
_cell_volume                     3278.27(18)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            8269
_diffrn_reflns_theta_full        27.73
_diffrn_reflns_theta_max         27.73
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.294
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3765
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1139
_refine_ls_R_factor_gt           0.0535
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0884P)²+0.1149P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1473
_refine_ls_wR_factor_ref         0.1789
_reflns_number_gt                1886
_reflns_number_total             3765
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cv5005.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               2228279
_cod_database_fobs_code          2228279
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.06573(8) 0.23883(18) 0.35444(8) 0.0809(5) Uani d . 1 . .
N N1 0.14838(9) 0.0606(2) 0.41990(8) 0.0707(5) Uani d . 1 . .
C C7 0.12657(11) 0.1980(3) 0.38051(10) 0.0645(6) Uani d . 1 . .
C C12 0.25215(10) 0.4844(3) 0.32781(11) 0.0661(6) Uani d . 1 . .
N N2 0.21985(10) 0.0439(3) 0.43823(10) 0.0819(6) Uani d . 1 . .
N N3 0.12874(9) 0.4629(2) 0.29494(10) 0.0833(6) Uani d . 1 . .
H H3A 0.0927 0.4145 0.2992 0.100 Uiso calc R 1 . .
C C11 0.18821(10) 0.4066(3) 0.33364(11) 0.0657(6) Uani d . 1 . .
N N4 0.0000 0.6106(3) 0.2500 0.0898(9) Uani d S 1 . .
H H4 0.0000 0.5057 0.2500 0.108 Uiso calc SR 1 . .
C C8 0.18835(10) 0.2749(3) 0.37639(10) 0.0635(6) Uani d . 1 . .
C C6 0.10856(13) -0.0732(3) 0.42954(10) 0.0719(6) Uani d . 1 . .
C C17 0.27276(12) 0.4657(3) 0.27000(11) 0.0738(6) Uani d . 1 . .
H H17 0.2456 0.4070 0.2333 0.089 Uiso calc R 1 . .
C C9 0.24330(11) 0.1713(3) 0.41344(10) 0.0715(6) Uani d . 1 . .
C C19 0.06028(11) 0.7026(3) 0.25289(12) 0.0802(7) Uani d . 1 . .
H H19A 0.0749 0.7608 0.2958 0.096 Uiso calc R 1 . .
H H19B 0.0500 0.7825 0.2165 0.096 Uiso calc R 1 . .
C C15 0.37336(13) 0.6229(3) 0.32006(17) 0.0930(8) Uani d . 1 . .
H H15 0.4144 0.6685 0.3174 0.112 Uiso calc R 1 . .
C C13 0.29269(12) 0.5747(3) 0.38196(12) 0.0822(7) Uani d . 1 . .
H H13 0.2791 0.5876 0.4212 0.099 Uiso calc R 1 . .
C C16 0.33348(14) 0.5339(3) 0.26650(14) 0.0840(7) Uani d . 1 . .
H H16 0.3476 0.5196 0.2277 0.101 Uiso calc R 1 . .
C C5 0.04144(14) -0.0517(3) 0.42877(12) 0.0830(7) Uani d . 1 . .
H H5 0.0224 0.0524 0.4239 0.100 Uiso calc R 1 . .
C C18 0.11649(12) 0.5955(3) 0.24635(13) 0.0913(8) Uani d . 1 . .
H H18A 0.1048 0.5511 0.2007 0.110 Uiso calc R 1 . .
H H18B 0.1582 0.6592 0.2535 0.110 Uiso calc R 1 . .
C C14 0.35261(13) 0.6447(3) 0.37766(15) 0.0951(8) Uani d . 1 . .
H H14 0.3792 0.7068 0.4136 0.114 Uiso calc R 1 . .
C C10 0.31871(12) 0.1867(4) 0.42487(13) 0.0961(8) Uani d . 1 . .
H H10A 0.3412 0.0905 0.4472 0.144 Uiso calc R 1 . .
H H10B 0.3354 0.2803 0.4528 0.144 Uiso calc R 1 . .
H H10C 0.3281 0.1991 0.3820 0.144 Uiso calc R 1 . .
C C1 0.13730(17) -0.2275(3) 0.43868(12) 0.0930(8) Uani d . 1 . .
H H1 0.1832 -0.2428 0.4409 0.112 Uiso calc R 1 . .
C C2 0.0968(2) -0.3578(4) 0.44439(14) 0.1196(12) Uani d . 1 . .
H H2 0.1156 -0.4621 0.4496 0.144 Uiso calc R 1 . .
C C4 0.00213(17) -0.1842(4) 0.43516(14) 0.1080(9) Uani d . 1 . .
H H4A -0.0435 -0.1692 0.4344 0.130 Uiso calc R 1 . .
C C3 0.0297(3) -0.3380(5) 0.44262(15) 0.1220(12) Uani d . 1 . .
H H3 0.0030 -0.4276 0.4464 0.146 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 N1 N2 . . 111.73(18) ?
C7 N1 C6 . . 127.98(19) ?
N2 N1 C6 . . 118.64(18) ?
O1 C7 N1 . . 125.6(2) ?
O1 C7 C8 . . 129.6(2) ?
N1 C7 C8 . . 104.77(18) ?
C17 C12 C13 . . 119.5(2) ?
C17 C12 C11 . . 120.9(2) ?
C13 C12 C11 . . 119.66(19) ?
C9 N2 N1 . . 106.44(17) ?
C11 N3 C18 . . 128.4(2) ?
C11 N3 H3A . . 115.8 ?
C18 N3 H3A . . 115.8 ?
N3 C11 C8 . . 119.03(19) ?
N3 C11 C12 . . 118.1(2) ?
C8 C11 C12 . . 122.84(18) ?
C19 N4 C19 . 2 116.1(3) ?
C19 N4 H4 . . 122.0 ?
C19 N4 H4 2 . 122.0 ?
C11 C8 C7 . . 122.52(18) ?
C11 C8 C9 . . 130.9(2) ?
C7 C8 C9 . . 105.7(2) ?
C5 C6 C1 . . 119.9(2) ?
C5 C6 N1 . . 120.5(2) ?
C1 C6 N1 . . 119.6(2) ?
C16 C17 C12 . . 120.0(2) ?
C16 C17 H17 . . 120.0 ?
C12 C17 H17 . . 120.0 ?
N2 C9 C8 . . 111.3(2) ?
N2 C9 C10 . . 118.7(2) ?
C8 C9 C10 . . 130.0(2) ?
N4 C19 C18 . . 111.1(2) ?
N4 C19 H19A . . 109.4 ?
C18 C19 H19A . . 109.4 ?
N4 C19 H19B . . 109.4 ?
C18 C19 H19B . . 109.4 ?
H19A C19 H19B . . 108.0 ?
C16 C15 C14 . . 120.1(2) ?
C16 C15 H15 . . 120.0 ?
C14 C15 H15 . . 120.0 ?
C14 C13 C12 . . 120.2(2) ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C15 C16 C17 . . 120.3(2) ?
C15 C16 H16 . . 119.8 ?
C17 C16 H16 . . 119.8 ?
C6 C5 C4 . . 120.0(3) ?
C6 C5 H5 . . 120.0 ?
C4 C5 H5 . . 120.0 ?
N3 C18 C19 . . 111.5(2) ?
N3 C18 H18A . . 109.3 ?
C19 C18 H18A . . 109.3 ?
N3 C18 H18B . . 109.3 ?
C19 C18 H18B . . 109.3 ?
H18A C18 H18B . . 108.0 ?
C13 C14 C15 . . 119.9(3) ?
C13 C14 H14 . . 120.1 ?
C15 C14 H14 . . 120.1 ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C2 C1 C6 . . 118.8(3) ?
C2 C1 H1 . . 120.6 ?
C6 C1 H1 . . 120.6 ?
C3 C2 C1 . . 121.6(3) ?
C3 C2 H2 . . 119.2 ?
C1 C2 H2 . . 119.2 ?
C3 C4 C5 . . 120.4(3) ?
C3 C4 H4A . . 119.8 ?
C5 C4 H4A . . 119.8 ?
C2 C3 C4 . . 119.1(3) ?
C2 C3 H3 . . 120.4 ?
C4 C3 H3 . . 120.4 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 . 1.243(2) ?
N1 C7 . 1.383(3) ?
N1 N2 . 1.398(2) ?
N1 C6 . 1.411(3) ?
C7 C8 . 1.429(3) ?
C12 C17 . 1.377(3) ?
C12 C13 . 1.391(3) ?
C12 C11 . 1.483(3) ?
N2 C9 . 1.310(3) ?
N3 C11 . 1.324(3) ?
N3 C18 . 1.448(3) ?
N3 H3A . 0.8600 ?
C11 C8 . 1.392(3) ?
N4 C19 . 1.425(3) ?
N4 C19 2 1.425(3) ?
N4 H4 . 0.8600 ?
C8 C9 . 1.435(3) ?
C6 C5 . 1.371(3) ?
C6 C1 . 1.384(3) ?
C17 C16 . 1.375(3) ?
C17 H17 . 0.9300 ?
C9 C10 . 1.487(3) ?
C19 C18 . 1.477(3) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C15 C16 . 1.374(4) ?
C15 C14 . 1.378(4) ?
C15 H15 . 0.9300 ?
C13 C14 . 1.372(3) ?
C13 H13 . 0.9300 ?
C16 H16 . 0.9300 ?
C5 C4 . 1.377(4) ?
C5 H5 . 0.9300 ?
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
C14 H14 . 0.9300 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C1 C2 . 1.375(4) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.362(5) ?
C2 H2 . 0.9300 ?
C4 C3 . 1.370(5) ?
C4 H4A . 0.9300 ?
C3 H3 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N3 H3A O1 . 0.86 2.00 2.722(2) 140.3
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N2 N1 C7 O1 . . . . 176.4(2) ?
C6 N1 C7 O1 . . . . 11.4(3) ?
N2 N1 C7 C8 . . . . -2.4(2) ?
C6 N1 C7 C8 . . . . -167.39(18) ?
C7 N1 N2 C9 . . . . 2.5(2) ?
C6 N1 N2 C9 . . . . 169.01(18) ?
C18 N3 C11 C8 . . . . -178.9(2) ?
C18 N3 C11 C12 . . . . -0.7(3) ?
C17 C12 C11 N3 . . . . -69.2(3) ?
C13 C12 C11 N3 . . . . 112.2(2) ?
C17 C12 C11 C8 . . . . 108.9(2) ?
C13 C12 C11 C8 . . . . -69.7(3) ?
N3 C11 C8 C7 . . . . -0.3(3) ?
C12 C11 C8 C7 . . . . -178.43(19) ?
N3 C11 C8 C9 . . . . 166.9(2) ?
C12 C11 C8 C9 . . . . -11.2(3) ?
O1 C7 C8 C11 . . . . -7.3(4) ?
N1 C7 C8 C11 . . . . 171.45(18) ?
O1 C7 C8 C9 . . . . -177.3(2) ?
N1 C7 C8 C9 . . . . 1.4(2) ?
C7 N1 C6 C5 . . . . -32.3(3) ?
N2 N1 C6 C5 . . . . 163.56(19) ?
C7 N1 C6 C1 . . . . 146.5(2) ?
N2 N1 C6 C1 . . . . -17.5(3) ?
C13 C12 C17 C16 . . . . 1.0(3) ?
C11 C12 C17 C16 . . . . -177.64(19) ?
N1 N2 C9 C8 . . . . -1.4(2) ?
N1 N2 C9 C10 . . . . -179.79(19) ?
C11 C8 C9 N2 . . . . -168.8(2) ?
C7 C8 C9 N2 . . . . 0.0(2) ?
C11 C8 C9 C10 . . . . 9.3(4) ?
C7 C8 C9 C10 . . . . 178.1(2) ?
C19 N4 C19 C18 2 . . . -172.3(2) ?
C17 C12 C13 C14 . . . . 0.1(4) ?
C11 C12 C13 C14 . . . . 178.8(2) ?
C14 C15 C16 C17 . . . . -0.1(4) ?
C12 C17 C16 C15 . . . . -1.0(3) ?
C1 C6 C5 C4 . . . . -1.8(3) ?
N1 C6 C5 C4 . . . . 177.1(2) ?
C11 N3 C18 C19 . . . . -135.6(3) ?
N4 C19 C18 N3 . . . . -52.7(3) ?
C12 C13 C14 C15 . . . . -1.3(4) ?
C16 C15 C14 C13 . . . . 1.3(4) ?
C5 C6 C1 C2 . . . . 2.3(3) ?
N1 C6 C1 C2 . . . . -176.6(2) ?
C6 C1 C2 C3 . . . . -1.3(4) ?
C6 C5 C4 C3 . . . . 0.3(4) ?
C1 C2 C3 C4 . . . . -0.2(5) ?
C5 C4 C3 C2 . . . . 0.7(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 136869857
