#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/67/2226750.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2226750
loop_
_publ_author_name
'Wang, Hai-Wen'
_publ_section_title
;
 (E,E)-3,3'-Dimethyl-1,1'-diphenyl-4,4'-{(ethane-1,2-diyldiimino)bis[(2-furyl)methylidyne]}di-1H-pyrazol-5(4H)-one
;
_journal_coeditor_code           ZQ2042
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1534
_journal_paper_doi               10.1107/S160053681001980X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C32 H28 N6 O4'
_chemical_formula_moiety         'C32 H28 N6 O4'
_chemical_formula_sum            'C32 H28 N6 O4'
_chemical_formula_weight         560.60
_chemical_name_systematic
;
(E,E)-3,3'-Dimethyl-1,1'-diphenyl-4,4'-{(ethane-1,2-
diyldiimino)bis[(2-furyl)methylidyne]}di-1H-pyrazol-5(4H)-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 93.9370(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.7438(6)
_cell_length_b                   7.6999(4)
_cell_length_c                   16.8273(9)
_cell_measurement_reflns_used    1740
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      22.86
_cell_measurement_theta_min      2.43
_cell_volume                     1388.77(13)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_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  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8081
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.214
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3145
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0460
_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)+(0.0585P)²+0.2282P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1331
_reflns_number_gt                1934
_reflns_number_total             3145
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            zq2042.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226750
_cod_database_fobs_code          2226750
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C C1 0.79340(17) 1.2879(2) 0.11911(11) 0.0503(4) Uani d . 1 . .
C C2 0.86997(19) 1.2531(3) 0.18661(11) 0.0628(5) Uani d . 1 . .
H H2 0.9052 1.1435 0.1942 0.075 Uiso calc R 1 . .
C C3 0.8939(2) 1.3819(4) 0.24275(14) 0.0784(7) Uani d . 1 . .
H H3 0.9448 1.3584 0.2884 0.094 Uiso calc R 1 . .
C C4 0.8430(2) 1.5442(4) 0.23149(16) 0.0832(8) Uani d . 1 . .
H H4 0.8600 1.6308 0.2692 0.100 Uiso calc R 1 . .
C C5 0.7671(2) 1.5788(3) 0.16450(15) 0.0755(7) Uani d . 1 . .
H H5 0.7329 1.6890 0.1570 0.091 Uiso calc R 1 . .
C C6 0.74101(18) 1.4516(3) 0.10811(13) 0.0598(5) Uani d . 1 . .
H H6 0.6887 1.4753 0.0631 0.072 Uiso calc R 1 . .
C C7 0.83098(17) 1.0057(2) 0.04804(11) 0.0494(4) Uani d . 1 . .
C C8 0.76317(16) 0.9266(2) -0.01917(10) 0.0477(4) Uani d . 1 . .
C C9 0.66731(17) 1.0489(3) -0.04361(11) 0.0529(5) Uani d . 1 . .
C C10 0.5737(2) 1.0478(3) -0.11395(13) 0.0757(7) Uani d . 1 . .
H H10A 0.5098 0.9640 -0.1054 0.114 Uiso calc R 1 . .
H H10B 0.6145 1.0178 -0.1610 0.114 Uiso calc R 1 . .
H H10C 0.5369 1.1610 -0.1204 0.114 Uiso calc R 1 . .
C C11 0.79841(15) 0.7652(2) -0.04839(10) 0.0453(4) Uani d . 1 . .
C C12 0.71716(18) 0.6668(2) -0.10479(10) 0.0510(5) Uani d . 1 . .
C C13 0.59548(17) 0.6410(3) -0.10780(11) 0.0566(5) Uani d . 1 . .
H H13 0.5408 0.6837 -0.0720 0.068 Uiso calc R 1 . .
C C14 0.5636(2) 0.5375(3) -0.17468(13) 0.0728(6) Uani d . 1 . .
H H14 0.4841 0.4988 -0.1915 0.087 Uiso calc R 1 . .
C C15 0.6675(2) 0.5054(3) -0.20900(13) 0.0743(6) Uani d . 1 . .
H H15 0.6733 0.4402 -0.2551 0.089 Uiso calc R 1 . .
C C16 0.95252(16) 0.5224(2) -0.03384(11) 0.0498(5) Uani d . 1 . .
H H16A 0.9908 0.5153 -0.0843 0.060 Uiso calc R 1 . .
H H16B 0.8836 0.4408 -0.0350 0.060 Uiso calc R 1 . .
H H3A 0.9502(18) 0.768(3) 0.0148(12) 0.072(6) Uiso d . 1 . .
N N1 0.76746(14) 1.1578(2) 0.06110(8) 0.0525(4) Uani d . 1 . .
N N2 0.67014(15) 1.1852(2) 0.00285(9) 0.0586(4) Uani d . 1 . .
N N3 0.90719(14) 0.6974(2) -0.02175(10) 0.0523(4) Uani d . 1 . .
O O1 0.92691(12) 0.95452(17) 0.08686(8) 0.0615(4) Uani d . 1 . .
O O2 0.76644(13) 0.5832(2) -0.16638(8) 0.0703(4) Uani d . 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
C2 C1 C6 . . 119.95(18) ?
C2 C1 N1 . . 120.52(18) ?
C6 C1 N1 . . 119.54(17) ?
C3 C2 C1 . . 119.7(2) ?
C3 C2 H2 . . 120.2 ?
C1 C2 H2 . . 120.2 ?
C4 C3 C2 . . 120.4(2) ?
C4 C3 H3 . . 119.8 ?
C2 C3 H3 . . 119.8 ?
C5 C4 C3 . . 119.9(2) ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
C4 C5 C6 . . 120.6(2) ?
C4 C5 H5 . . 119.7 ?
C6 C5 H5 . . 119.7 ?
C5 C6 C1 . . 119.5(2) ?
C5 C6 H6 . . 120.3 ?
C1 C6 H6 . . 120.3 ?
O1 C7 N1 . . 125.83(17) ?
O1 C7 C8 . . 129.37(17) ?
N1 C7 C8 . . 104.79(15) ?
C11 C8 C9 . . 133.55(16) ?
C11 C8 C7 . . 121.23(16) ?
C9 C8 C7 . . 105.20(16) ?
N2 C9 C8 . . 111.62(16) ?
N2 C9 C10 . . 117.60(17) ?
C8 C9 C10 . . 130.68(18) ?
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 ?
N3 C11 C8 . . 118.92(16) ?
N3 C11 C12 . . 119.25(17) ?
C8 C11 C12 . . 121.79(16) ?
C13 C12 O2 . . 109.65(16) ?
C13 C12 C11 . . 130.61(17) ?
O2 C12 C11 . . 119.74(16) ?
C12 C13 C14 . . 107.65(18) ?
C12 C13 H13 . . 126.2 ?
C14 C13 H13 . . 126.2 ?
C15 C14 C13 . . 106.94(18) ?
C15 C14 H14 . . 126.5 ?
C13 C14 H14 . . 126.5 ?
C14 C15 O2 . . 109.74(18) ?
C14 C15 H15 . . 125.1 ?
O2 C15 H15 . . 125.1 ?
N3 C16 C16 . 3_765 108.70(18) ?
N3 C16 H16A . . 109.9 ?
C16 C16 H16A 3_765 . 109.9 ?
N3 C16 H16B . . 109.9 ?
C16 C16 H16B 3_765 . 109.9 ?
H16A C16 H16B . . 108.3 ?
C7 N1 N2 . . 111.73(14) ?
C7 N1 C1 . . 129.44(15) ?
N2 N1 C1 . . 118.64(15) ?
C9 N2 N1 . . 106.47(15) ?
C11 N3 C16 . . 127.80(16) ?
C11 N3 H3A . . 112.4(12) ?
C16 N3 H3A . . 119.0(13) ?
C12 O2 C15 . . 106.01(15) ?
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
C1 C2 . 1.382(3) ?
C1 C6 . 1.387(3) ?
C1 N1 . 1.413(2) ?
C2 C3 . 1.382(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.372(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.371(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.379(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 O1 . 1.246(2) ?
C7 N1 . 1.380(2) ?
C7 C8 . 1.438(2) ?
C8 C11 . 1.398(3) ?
C8 C9 . 1.435(2) ?
C9 N2 . 1.307(2) ?
C9 C10 . 1.500(2) ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 N3 . 1.330(2) ?
C11 C12 . 1.457(2) ?
C12 C13 . 1.320(2) ?
C12 O2 . 1.358(2) ?
C13 C14 . 1.402(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.315(3) ?
C14 H14 . 0.9300 ?
C15 O2 . 1.378(2) ?
C15 H15 . 0.9300 ?
C16 N3 . 1.452(2) ?
C16 C16 3_765 1.516(3) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
N1 N2 . 1.399(2) ?
N3 H3A . 0.92(2) ?
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 1 0.92(2) 1.91(2) 2.693(2) 142.0(17)
C16 H16A Cg3 3_556 0.97 2.70 3.575(2) 151
C3 H3 O1 2_755 0.93 2.54 3.389(2) 152
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
C6 C1 C2 C3 . . . . -0.1(3) ?
N1 C1 C2 C3 . . . . -179.80(18) ?
C1 C2 C3 C4 . . . . -0.6(3) ?
C2 C3 C4 C5 . . . . 0.6(4) ?
C3 C4 C5 C6 . . . . 0.1(3) ?
C4 C5 C6 C1 . . . . -0.7(3) ?
C2 C1 C6 C5 . . . . 0.7(3) ?
N1 C1 C6 C5 . . . . -179.56(17) ?
O1 C7 C8 C11 . . . . 3.0(3) ?
N1 C7 C8 C11 . . . . -177.92(16) ?
O1 C7 C8 C9 . . . . -175.32(19) ?
N1 C7 C8 C9 . . . . 3.75(19) ?
C11 C8 C9 N2 . . . . -179.9(2) ?
C7 C8 C9 N2 . . . . -1.9(2) ?
C11 C8 C9 C10 . . . . -3.7(4) ?
C7 C8 C9 C10 . . . . 174.3(2) ?
C9 C8 C11 N3 . . . . 167.09(19) ?
C7 C8 C11 N3 . . . . -10.7(3) ?
C9 C8 C11 C12 . . . . -15.3(3) ?
C7 C8 C11 C12 . . . . 166.92(16) ?
N3 C11 C12 C13 . . . . 136.6(2) ?
C8 C11 C12 C13 . . . . -41.0(3) ?
N3 C11 C12 O2 . . . . -43.3(2) ?
C8 C11 C12 O2 . . . . 139.07(18) ?
O2 C12 C13 C14 . . . . -0.6(2) ?
C11 C12 C13 C14 . . . . 179.5(2) ?
C12 C13 C14 C15 . . . . 0.0(3) ?
C13 C14 C15 O2 . . . . 0.6(3) ?
O1 C7 N1 N2 . . . . 174.61(17) ?
C8 C7 N1 N2 . . . . -4.5(2) ?
O1 C7 N1 C1 . . . . -0.1(3) ?
C8 C7 N1 C1 . . . . -179.26(17) ?
C2 C1 N1 C7 . . . . -19.0(3) ?
C6 C1 N1 C7 . . . . 161.30(18) ?
C2 C1 N1 N2 . . . . 166.60(16) ?
C6 C1 N1 N2 . . . . -13.1(2) ?
C8 C9 N2 N1 . . . . -0.8(2) ?
C10 C9 N2 N1 . . . . -177.56(17) ?
C7 N1 N2 C9 . . . . 3.4(2) ?
C1 N1 N2 C9 . . . . 178.82(16) ?
C8 C11 N3 C16 . . . . 169.17(17) ?
C12 C11 N3 C16 . . . . -8.5(3) ?
C16 C16 N3 C11 3_765 . . . -154.74(19) ?
C13 C12 O2 C15 . . . . 0.9(2) ?
C11 C12 O2 C15 . . . . -179.14(18) ?
C14 C15 O2 C12 . . . . -0.9(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139079232
