#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/23/2212332.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_2212332
loop_
_publ_author_name
'Zhou, Qing-Li'
'Jing, Zuo-Liang'
'Chen, Xin'
'Yu Ming'
_publ_section_title
4-(1H-Indol-3-ylmethyleneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one
_journal_coeditor_code           RN2013
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o418
_journal_page_last               o419
_journal_paper_doi               10.1107/S1600536806054213
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C20 H18 N4 O'
_chemical_formula_moiety         'C20 H18 N4 O'
_chemical_formula_sum            'C20 H18 N4 O'
_chemical_formula_weight         330.38
_chemical_name_systematic
;
4-(1H-Indol-3-ylmethyleneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.857(3)
_cell_length_b                   15.729(8)
_cell_length_c                   16.436(8)
_cell_measurement_reflns_used    3170
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      22.61
_cell_measurement_theta_min      2.48
_cell_volume                     1772.7(15)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0160
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9604
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.48
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9843
_exptl_absorpt_correction_T_min  0.9722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.098
_refine_diff_density_min         -0.079
_refine_ls_abs_structure_details 'None, Friedel Pairs merged'
_refine_ls_extinction_coef       0.0116(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         1822
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0274
_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)+(0.0458P)²+0.0654P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0714
_refine_ls_wR_factor_ref         0.0743
_reflns_number_gt                1583
_reflns_number_total             1822
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rn2013.cif
_cod_data_source_block           I
_cod_original_cell_volume        1772.5(15)
_cod_database_code               2212332
_cod_database_fobs_code          2212332
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
O O1 0.1024(2) 0.55371(8) 0.86273(9) 0.0653(4) Uani d . 1
N N1 0.0833(3) 0.94127(12) 0.74363(12) 0.0726(6) Uani d . 1
H H1A 0.005(4) 0.9733(16) 0.7128(14) 0.087 Uiso d . 1
N N2 0.3726(2) 0.71601(9) 0.87248(8) 0.0473(4) Uani d . 1
N N3 0.5515(2) 0.52172(9) 0.95224(9) 0.0517(4) Uani d . 1
N N4 0.3622(2) 0.49576(9) 0.93378(10) 0.0528(4) Uani d . 1
C C1 0.0494(3) 0.85907(14) 0.76359(13) 0.0685(6) Uani d . 1
H H1 -0.0624 0.8289 0.7498 0.082 Uiso calc R 1
C C2 0.2609(3) 0.96502(12) 0.77334(10) 0.0585(5) Uani d . 1
C C3 0.3578(4) 1.04178(13) 0.76686(13) 0.0722(7) Uani d . 1
H H3 0.3024 1.0875 0.7395 0.087 Uiso calc R 1
C C4 0.5372(4) 1.04821(15) 0.80194(16) 0.0831(7) Uani d . 1
H H4 0.6059 1.0990 0.7980 0.100 Uiso calc R 1
C C5 0.6192(4) 0.98001(14) 0.84352(14) 0.0756(6) Uani d . 1
H H5 0.7415 0.9864 0.8673 0.091 Uiso calc R 1
C C6 0.5238(3) 0.90333(13) 0.85030(12) 0.0575(5) Uani d . 1
H H6 0.5801 0.8582 0.8784 0.069 Uiso calc R 1
C C7 0.3420(3) 0.89493(11) 0.81435(10) 0.0493(4) Uani d . 1
C C8 0.2028(3) 0.82678(12) 0.80681(10) 0.0518(5) Uani d . 1
C C9 0.2191(3) 0.74111(11) 0.83565(10) 0.0520(5) Uani d . 1
H H9 0.1166 0.7033 0.8275 0.062 Uiso calc R 1
C C10 0.3929(3) 0.63343(10) 0.90088(9) 0.0441(4) Uani d . 1
C C11 0.2648(3) 0.56186(11) 0.89520(10) 0.0491(4) Uani d . 1
C C12 0.5609(3) 0.60628(11) 0.93733(10) 0.0459(4) Uani d . 1
C C13 0.6468(4) 0.48017(15) 1.01966(14) 0.0775(7) Uani d . 1
H H13A 0.7773 0.5016 1.0250 0.116 Uiso calc R 1
H H13B 0.6508 0.4200 1.0101 0.116 Uiso calc R 1
H H13C 0.5756 0.4913 1.0688 0.116 Uiso calc R 1
C C14 0.7360(3) 0.65717(12) 0.95830(12) 0.0612(5) Uani d . 1
H H14A 0.7476 0.6611 1.0164 0.092 Uiso calc R 1
H H14B 0.7236 0.7132 0.9357 0.092 Uiso calc R 1
H H14C 0.8500 0.6301 0.9364 0.092 Uiso calc R 1
C C15 0.3236(3) 0.40821(11) 0.91910(10) 0.0517(5) Uani d . 1
C C16 0.1600(3) 0.37157(14) 0.95148(13) 0.0702(6) Uani d . 1
H H16 0.0767 0.4033 0.9842 0.084 Uiso calc R 1
C C17 0.1192(4) 0.28697(14) 0.93517(15) 0.0839(7) Uani d . 1
H H17 0.0073 0.2621 0.9565 0.101 Uiso calc R 1
C C18 0.2420(4) 0.24012(13) 0.88809(12) 0.0802(7) Uani d . 1
H H18 0.2143 0.1834 0.8773 0.096 Uiso calc R 1
C C19 0.4049(4) 0.27646(13) 0.85694(14) 0.0835(8) Uani d . 1
H H19 0.4892 0.2443 0.8250 0.100 Uiso calc R 1
C C20 0.4467(4) 0.36102(12) 0.87230(12) 0.0685(6) Uani d . 1
H H20 0.5586 0.3856 0.8507 0.082 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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_publ_flag
C1 N1 C2 109.17(18) ?
C1 N1 H1A 124.9(16) ?
C2 N1 H1A 125.8(16) ?
C9 N2 C10 122.13(16) yes
C12 N3 N4 107.02(15) ?
C12 N3 C13 124.22(17) ?
N4 N3 C13 117.14(17) ?
C11 N4 N3 109.13(15) ?
C11 N4 C15 123.87(16) ?
N3 N4 C15 119.60(15) ?
N1 C1 C8 110.4(2) ?
N1 C1 H1 124.8 ?
C8 C1 H1 124.8 ?
N1 C2 C3 129.8(2) ?
N1 C2 C7 108.05(19) ?
C3 C2 C7 122.1(2) ?
C4 C3 C2 117.8(2) ?
C4 C3 H3 121.1 ?
C2 C3 H3 121.1 ?
C3 C4 C5 121.1(2) ?
C3 C4 H4 119.5 ?
C5 C4 H4 119.5 ?
C6 C5 C4 121.6(2) ?
C6 C5 H5 119.2 ?
C4 C5 H5 119.2 ?
C5 C6 C7 118.46(19) ?
C5 C6 H6 120.8 ?
C7 C6 H6 120.8 ?
C6 C7 C2 119.03(19) ?
C6 C7 C8 134.72(17) ?
C2 C7 C8 106.25(18) ?
C1 C8 C9 125.5(2) yes
C1 C8 C7 106.15(17) ?
C9 C8 C7 128.29(17) ?
N2 C9 C8 120.78(18) yes
N2 C9 H9 119.6 ?
C8 C9 H9 119.6 ?
C12 C10 N2 121.65(16) ?
C12 C10 C11 107.46(15) ?
N2 C10 C11 130.77(16) yes
O1 C11 N4 123.39(17) ?
O1 C11 C10 131.29(17) yes
N4 C11 C10 105.30(15) ?
N3 C12 C10 110.25(16) ?
N3 C12 C14 121.77(17) ?
C10 C12 C14 127.97(16) ?
N3 C13 H13A 109.5 ?
N3 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
N3 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
C12 C14 H14A 109.5 ?
C12 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
C12 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
C20 C15 C16 119.86(19) ?
C20 C15 N4 120.51(19) ?
C16 C15 N4 119.62(18) ?
C15 C16 C17 119.6(2) ?
C15 C16 H16 120.2 ?
C17 C16 H16 120.2 ?
C18 C17 C16 120.3(2) ?
C18 C17 H17 119.8 ?
C16 C17 H17 119.8 ?
C19 C18 C17 119.8(2) ?
C19 C18 H18 120.1 ?
C17 C18 H18 120.1 ?
C18 C19 C20 120.5(2) ?
C18 C19 H19 119.8 ?
C20 C19 H19 119.8 ?
C15 C20 C19 119.9(2) ?
C15 C20 H20 120.0 ?
C19 C20 H20 120.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C11 1.241(2) yes
N1 C1 1.354(3) ?
N1 C2 1.364(3) ?
N1 H1A 0.89(3) ?
N2 C9 1.277(2) yes
N2 C10 1.387(2) yes
N3 C12 1.354(2) ?
N3 N4 1.394(2) ?
N3 C13 1.443(3) ?
N4 C11 1.389(2) ?
N4 C15 1.423(2) ?
C1 C8 1.367(3) yes
C1 H1 0.9300 ?
C2 C3 1.382(3) ?
C2 C7 1.407(3) ?
C3 C4 1.362(4) ?
C3 H3 0.9300 ?
C4 C5 1.391(3) ?
C4 H4 0.9300 ?
C5 C6 1.377(3) ?
C5 H5 0.9300 ?
C6 C7 1.386(3) ?
C6 H6 0.9300 ?
C7 C8 1.441(3) ?
C8 C9 1.433(3) yes
C9 H9 0.9300 ?
C10 C12 1.366(2) ?
C10 C11 1.431(3) yes
C12 C14 1.484(3) ?
C13 H13A 0.9600 ?
C13 H13B 0.9600 ?
C13 H13C 0.9600 ?
C14 H14A 0.9600 ?
C14 H14B 0.9600 ?
C14 H14C 0.9600 ?
C15 C20 1.362(3) ?
C15 C16 1.369(3) ?
C16 C17 1.386(3) ?
C16 H16 0.9300 ?
C17 C18 1.360(4) ?
C17 H17 0.9300 ?
C18 C19 1.355(4) ?
C18 H18 0.9300 ?
C19 C20 1.384(3) ?
C19 H19 0.9300 ?
C20 H20 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
_geom_hbond_publ_flag
N1 H1A O1 3_556 0.89(3) 1.92(3) 2.794(2) 166(2) yes
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
C12 N3 N4 C11 9.48(19)
C13 N3 N4 C11 154.35(17)
C12 N3 N4 C15 160.60(15)
C13 N3 N4 C15 -54.5(2)
C2 N1 C1 C8 0.1(2)
C1 N1 C2 C3 178.8(2)
C1 N1 C2 C7 -0.4(2)
N1 C2 C3 C4 -179.22(19)
C7 C2 C3 C4 -0.1(3)
C2 C3 C4 C5 -0.6(3)
C3 C4 C5 C6 0.6(4)
C4 C5 C6 C7 0.1(3)
C5 C6 C7 C2 -0.8(3)
C5 C6 C7 C8 178.5(2)
N1 C2 C7 C6 -179.91(15)
C3 C2 C7 C6 0.8(3)
N1 C2 C7 C8 0.61(19)
C3 C2 C7 C8 -178.67(17)
N1 C1 C8 C9 -178.00(18)
N1 C1 C8 C7 0.3(2)
C6 C7 C8 C1 -179.92(19)
C2 C7 C8 C1 -0.6(2)
C6 C7 C8 C9 -1.7(3)
C2 C7 C8 C9 177.68(17)
C10 N2 C9 C8 -179.80(15)
C1 C8 C9 N2 176.85(19)
C7 C8 C9 N2 -1.1(3)
C9 N2 C10 C12 177.34(16)
C9 N2 C10 C11 1.8(3)
N3 N4 C11 O1 170.72(16)
C15 N4 C11 O1 21.1(3)
N3 N4 C11 C10 -7.85(19)
C15 N4 C11 C10 -157.46(17)
C12 C10 C11 O1 -175.03(18)
N2 C10 C11 O1 1.0(3)
C12 C10 C11 N4 3.39(19)
N2 C10 C11 N4 179.37(17)
N4 N3 C12 C10 -7.30(19)
C13 N3 C12 C10 -149.03(19)
N4 N3 C12 C14 173.66(15)
C13 N3 C12 C14 31.9(3)
N2 C10 C12 N3 -173.99(15)
C11 C10 C12 N3 2.44(19)
N2 C10 C12 C14 5.0(3)
C11 C10 C12 C14 -178.59(17)
C11 N4 C15 C20 103.3(2)
N3 N4 C15 C20 -43.3(3)
C11 N4 C15 C16 -75.8(2)
N3 N4 C15 C16 137.5(2)
C20 C15 C16 C17 -1.1(3)
N4 C15 C16 C17 178.1(2)
C15 C16 C17 C18 0.8(4)
C16 C17 C18 C19 -0.1(4)
C17 C18 C19 C20 -0.4(4)
C16 C15 C20 C19 0.7(3)
N4 C15 C20 C19 -178.5(2)
C18 C19 C20 C15 0.1(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12978417
