#------------------------------------------------------------------------------
#$Date: 2023-03-07 10:43:20 +0200 (Tue, 07 Mar 2023) $
#$Revision: 281684 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/68/8106850.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_8106850
loop_
_publ_author_name
'Zhang, Bao-Qi'
'Zhang, Lin'
'Zhang, Heng-Qiang'
'Zhao, Cheng-Liang'
'Chen, Bin'
_publ_section_title
;
 Crystal structure of
 (Z)-4-(furan-2-yl(p-tolylamino)methylene)-3-methyl-1-p-tolyl-1H-pyrazol-5(4H)-one,
 C23H21N3O2
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              281
_journal_page_last               283
_journal_paper_doi               10.1515/ncrs-2015-0120
_journal_volume                  231
_journal_year                    2016
_chemical_formula_moiety         'C23 H21 N3 O2'
_chemical_formula_sum            'C23 H21 N3 O2'
_chemical_formula_weight         371.43
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                113.368(3)
_cell_angle_beta                 101.139(4)
_cell_angle_gamma                101.310(4)
_cell_formula_units_Z            2
_cell_length_a                   10.305(3)
_cell_length_b                   10.4528(16)
_cell_length_c                   10.6351(17)
_cell_measurement_temperature    295(2)
_cell_volume                     983.4(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  '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  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0649
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6446
_diffrn_reflns_theta_full        27.62
_diffrn_reflns_theta_max         27.62
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             392.0
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         4455
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.1185
_refine_ls_R_factor_gt           0.0559
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0681P)²+0.1033P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1607
_reflns_number_gt                2424
_reflns_number_total             4576
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2015-0120_suppl.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               8106850
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1161(2) 0.2541(2) -0.1854(2) 0.0466(5) Uani 1 1 d . . .
C2 C 0.0298(2) 0.3146(2) -0.1105(2) 0.0541(6) Uani 1 1 d . . .
H2 H 0.0593 0.3614 -0.0106 0.065 Uiso 1 1 calc R . .
C3 C -0.1008(2) 0.3051(2) -0.1852(3) 0.0558(6) Uani 1 1 d . . .
H3 H -0.1580 0.3462 -0.1341 0.067 Uiso 1 1 calc R . .
C4 C -0.1483(2) 0.2361(2) -0.3337(2) 0.0529(6) Uani 1 1 d . . .
C5 C -0.2924(3) 0.2244(3) -0.4135(3) 0.0764(8) Uani 1 1 d . . .
H5A H -0.3562 0.1332 -0.4345 0.115 Uiso 1 1 calc R . .
H5B H -0.2909 0.2291 -0.5016 0.115 Uiso 1 1 calc R . .
H5C H -0.3212 0.3037 -0.3549 0.115 Uiso 1 1 calc R . .
C6 C -0.0611(3) 0.1741(2) -0.4056(2) 0.0575(6) Uani 1 1 d . . .
H6 H -0.0915 0.1252 -0.5054 0.069 Uiso 1 1 calc R . .
C7 C 0.0684(2) 0.1823(2) -0.3347(2) 0.0537(6) Uani 1 1 d . . .
H7 H 0.1245 0.1398 -0.3864 0.064 Uiso 1 1 calc R . .
C8 C 0.3378(2) 0.3769(2) 0.0192(2) 0.0485(5) Uani 1 1 d . . .
C9 C 0.4617(2) 0.3343(2) 0.0423(2) 0.0477(5) Uani 1 1 d . . .
C10 C 0.4413(2) 0.2054(2) -0.0859(2) 0.0495(5) Uani 1 1 d . . .
C11 C 0.5384(3) 0.1193(3) -0.1306(3) 0.0632(7) Uani 1 1 d . . .
H11A H 0.5460 0.0617 -0.0797 0.095 Uiso 1 1 calc R . .
H11B H 0.6281 0.1849 -0.1087 0.095 Uiso 1 1 calc R . .
H11C H 0.5033 0.0560 -0.2320 0.095 Uiso 1 1 calc R . .
C12 C 0.5697(2) 0.4136(2) 0.1720(2) 0.0485(5) Uani 1 1 d . . .
C13 C 0.6875(2) 0.3637(2) 0.2077(2) 0.0506(6) Uani 1 1 d . . .
C14 C 0.8255(3) 0.4271(3) 0.2570(3) 0.0778(8) Uani 1 1 d . . .
H14 H 0.8725 0.5223 0.2785 0.093 Uiso 1 1 calc R . .
C15 C 0.8854(3) 0.3202(4) 0.2700(3) 0.0845(9) Uani 1 1 d . . .
H15 H 0.9797 0.3320 0.3008 0.101 Uiso 1 1 calc R . .
C16 C 0.7837(3) 0.2018(3) 0.2308(3) 0.0769(8) Uani 1 1 d . . .
H16 H 0.7949 0.1153 0.2296 0.092 Uiso 1 1 calc R . .
C17 C 0.6313(2) 0.6241(2) 0.4163(2) 0.0470(5) Uani 1 1 d . . .
C18 C 0.6545(2) 0.7733(2) 0.4769(2) 0.0532(6) Uani 1 1 d . . .
H18 H 0.6297 0.8172 0.4191 0.064 Uiso 1 1 calc R . .
C19 C 0.7147(3) 0.8577(3) 0.6233(3) 0.0593(6) Uani 1 1 d . . .
H19 H 0.7297 0.9582 0.6628 0.071 Uiso 1 1 calc R . .
C20 C 0.7530(2) 0.7957(3) 0.7122(2) 0.0551(6) Uani 1 1 d . . .
C21 C 0.8181(4) 0.8897(3) 0.8716(3) 0.0888(9) Uani 1 1 d . . .
H21A H 0.7466 0.8994 0.9176 0.133 Uiso 1 1 calc R . .
H21B H 0.8717 0.9846 0.8893 0.133 Uiso 1 1 calc R . .
H21C H 0.8775 0.8449 0.9094 0.133 Uiso 1 1 calc R . .
C22 C 0.7271(3) 0.6464(3) 0.6507(3) 0.0604(6) Uani 1 1 d . . .
H22 H 0.7513 0.6025 0.7088 0.072 Uiso 1 1 calc R . .
C23 C 0.6659(2) 0.5601(3) 0.5046(3) 0.0569(6) Uani 1 1 d . . .
H23 H 0.6480 0.4592 0.4657 0.068 Uiso 1 1 calc R . .
H3A H 0.480(3) 0.561(3) 0.222(3) 0.095(10) Uiso 1 1 d . . .
N1 N 0.25096(19) 0.26655(19) -0.11167(18) 0.0496(5) Uani 1 1 d . . .
N2 N 0.3180(2) 0.16476(19) -0.17702(19) 0.0510(5) Uani 1 1 d . . .
N3 N 0.5637(2) 0.5422(2) 0.2661(2) 0.0532(5) Uani 1 1 d . . .
O1 O 0.31007(17) 0.48708(16) 0.09622(16) 0.0601(4) Uani 1 1 d . . .
O2 O 0.65852(18) 0.22381(17) 0.19167(18) 0.0660(5) Uani 1 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 0.0000 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C7 119.0(2) . .
C2 C1 N1 120.63(19) . .
C7 C1 N1 120.40(19) . .
C1 C2 C3 119.7(2) . .
C1 C2 H2 120.1 . .
C3 C2 H2 120.1 . .
C4 C3 C2 121.7(2) . .
C4 C3 H3 119.1 . .
C2 C3 H3 119.1 . .
C6 C4 C3 117.3(2) . .
C6 C4 C5 121.6(2) . .
C3 C4 C5 121.0(2) . .
C4 C5 H5A 109.5 . .
C4 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C4 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
C7 C6 C4 122.2(2) . .
C7 C6 H6 118.9 . .
C4 C6 H6 118.9 . .
C6 C7 C1 120.1(2) . .
C6 C7 H7 120.0 . .
C1 C7 H7 120.0 . .
O1 C8 N1 125.5(2) . .
O1 C8 C9 129.7(2) . .
N1 C8 C9 104.78(18) . .
C12 C9 C10 133.1(2) . .
C12 C9 C8 121.31(19) . .
C10 C9 C8 105.58(18) . .
N2 C10 C9 111.45(19) . .
N2 C10 C11 118.16(19) . .
C9 C10 C11 130.3(2) . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
N3 C12 C9 117.81(19) . .
N3 C12 C13 119.0(2) . .
C9 C12 C13 123.14(19) . .
C14 C13 O2 109.4(2) . .
C14 C13 C12 133.7(2) . .
O2 C13 C12 116.87(19) . .
C13 C14 C15 106.4(2) . .
C13 C14 H14 126.8 . .
C15 C14 H14 126.8 . .
C16 C15 C14 107.5(3) . .
C16 C15 H15 126.2 . .
C14 C15 H15 126.2 . .
C15 C16 O2 110.2(2) . .
C15 C16 H16 124.9 . .
O2 C16 H16 124.9 . .
C18 C17 C23 119.0(2) . .
C18 C17 N3 117.7(2) . .
C23 C17 N3 123.1(2) . .
C17 C18 C19 120.3(2) . .
C17 C18 H18 119.9 . .
C19 C18 H18 119.9 . .
C18 C19 C20 121.3(2) . .
C18 C19 H19 119.4 . .
C20 C19 H19 119.4 . .
C22 C20 C19 117.9(2) . .
C22 C20 C21 121.7(2) . .
C19 C20 C21 120.4(2) . .
C20 C21 H21A 109.5 . .
C20 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C20 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C20 C22 C23 121.6(2) . .
C20 C22 H22 119.2 . .
C23 C22 H22 119.2 . .
C22 C23 C17 119.9(2) . .
C22 C23 H23 120.1 . .
C17 C23 H23 120.1 . .
C8 N1 N2 111.30(17) . .
C8 N1 C1 128.31(17) . .
N2 N1 C1 120.17(16) . .
C10 N2 N1 106.61(16) . .
C12 N3 C17 129.95(19) . .
C12 N3 H3A 108.2(17) . .
C17 N3 H3A 119.5(17) . .
C13 O2 C16 106.4(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.386(3) .
C1 C7 1.391(3) .
C1 N1 1.411(3) .
C2 C3 1.387(3) .
C2 H2 0.9300 .
C3 C4 1.383(3) .
C3 H3 0.9300 .
C4 C6 1.383(3) .
C4 C5 1.517(3) .
C5 H5A 0.9600 .
C5 H5B 0.9600 .
C5 H5C 0.9600 .
C6 C7 1.368(3) .
C6 H6 0.9300 .
C7 H7 0.9300 .
C8 O1 1.245(2) .
C8 N1 1.382(3) .
C8 C9 1.441(3) .
C9 C12 1.402(3) .
C9 C10 1.428(3) .
C10 N2 1.312(3) .
C10 C11 1.495(3) .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 N3 1.343(3) .
C12 C13 1.455(3) .
C13 C14 1.342(3) .
C13 O2 1.367(3) .
C14 C15 1.417(4) .
C14 H14 0.9300 .
C15 C16 1.310(4) .
C15 H15 0.9300 .
C16 O2 1.369(3) .
C16 H16 0.9300 .
C17 C18 1.378(3) .
C17 C23 1.386(3) .
C17 N3 1.421(3) .
C18 C19 1.382(3) .
C18 H18 0.9300 .
C19 C20 1.383(3) .
C19 H19 0.9300 .
C20 C22 1.377(3) .
C20 C21 1.506(3) .
C21 H21A 0.9600 .
C21 H21B 0.9600 .
C21 H21C 0.9600 .
C22 C23 1.382(3) .
C22 H22 0.9300 .
C23 H23 0.9300 .
N1 N2 1.407(2) .
N3 H3A 1.00(3) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3A O1 1.00(3) 1.79(3) 2.680(3) 148(2) .
