#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/08/2210892.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_2210892
loop_
_publ_author_name
'Ding-Ben Chen'
'Ling Huang'
_publ_section_title
4-{[(1E)-(5-Chloro-2-hydroxyphenyl)methylene]amino}-1,5-dimethyl-2-phenyl-3H-pyrazol-3(2H)-one
_journal_coeditor_code           BT2191
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4853
_journal_page_last               o4854
_journal_paper_doi               10.1107/S1600536806039870
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C18 H16 Cl N3 O2'
_chemical_formula_moiety         'C18 H16 Cl N3 O2'
_chemical_formula_sum            'C18 H16 Cl N3 O2'
_chemical_formula_weight         341.79
_chemical_name_systematic
;
4-{[(1E)-(5-Chloro-2-hydroxyphenyl)methylene]amino}-1,5-dimethyl-
2-phenyl-3H-pyrazol-3(2H)-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                 109.34(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.967(7)
_cell_length_b                   7.041(4)
_cell_length_c                   20.947(10)
_cell_measurement_reflns_used    1946
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.18
_cell_measurement_theta_min      3.07
_cell_volume                     1665.4(16)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2002)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker APEX 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  0.0644
_diffrn_reflns_av_sigmaI/netI    0.0868
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7432
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.80
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  0.9692
_exptl_absorpt_correction_T_min  0.9391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.285
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2830
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.1171
_refine_ls_R_factor_gt           0.0706
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0862P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1579
_refine_ls_wR_factor_ref         0.1876
_reflns_number_gt                1956
_reflns_number_total             2830
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2191.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2210892
_cod_database_fobs_code          2210892
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
Cl Cl1 0.56443(10) -0.03057(16) 0.41796(7) 0.0872(5) Uani d . 1
O O1 0.8325(2) 0.6811(4) 0.48286(14) 0.0671(8) Uani d . 1
H H1 0.8804 0.6893 0.4626 0.101 Uiso calc R 1
O O2 1.04477(18) 0.3305(3) 0.30864(13) 0.0538(7) Uani d . 1
N N1 0.9423(2) 0.5782(4) 0.40023(14) 0.0425(7) Uani d . 1
N N2 1.1741(2) 0.7748(3) 0.34951(15) 0.0432(7) Uani d . 1
N N3 1.15811(19) 0.6017(3) 0.31420(14) 0.0409(7) Uani d . 1
C C5 0.6463(3) 0.1800(5) 0.43720(19) 0.0542(10) Uani d . 1
C C6 0.7301(3) 0.2165(5) 0.40757(19) 0.0508(9) Uani d . 1
H H6 0.7440 0.1281 0.3781 0.061 Uiso calc R 1
C C1 0.7951(3) 0.3860(4) 0.42126(17) 0.0423(8) Uani d . 1
C C2 0.7727(3) 0.5162(5) 0.46655(18) 0.0487(9) Uani d . 1
C C3 0.6867(3) 0.4746(6) 0.4956(2) 0.0610(11) Uani d . 1
H H3 0.6713 0.5612 0.5252 0.073 Uiso calc R 1
C C4 0.6241(3) 0.3079(6) 0.4813(2) 0.0592(10) Uani d . 1
H H4 0.5670 0.2814 0.5013 0.071 Uiso calc R 1
C C7 0.8829(3) 0.4227(4) 0.38941(18) 0.0454(9) Uani d . 1
H H7 0.8968 0.3322 0.3606 0.054 Uiso calc R 1
C C8 1.0282(2) 0.6165(4) 0.37059(16) 0.0385(8) Uani d . 1
C C10 1.0706(2) 0.4948(4) 0.32853(18) 0.0406(8) Uani d . 1
C C9 1.0903(3) 0.7843(4) 0.37986(17) 0.0421(8) Uani d . 1
C C13 1.2530(2) 0.5220(4) 0.29700(17) 0.0382(8) Uani d . 1
C C14 1.2286(3) 0.4004(5) 0.24218(19) 0.0500(9) Uani d . 1
H H14 1.1506 0.3758 0.2159 0.060 Uiso calc R 1
C C15 1.3200(3) 0.3162(5) 0.2267(2) 0.0638(11) Uani d . 1
H H15 1.3036 0.2324 0.1905 0.077 Uiso calc R 1
C C16 1.4352(3) 0.3549(5) 0.2645(2) 0.0635(11) Uani d . 1
H H16 1.4969 0.2984 0.2537 0.076 Uiso calc R 1
C C17 1.4591(3) 0.4771(5) 0.31822(19) 0.0502(9) Uani d . 1
H H17 1.5373 0.5048 0.3434 0.060 Uiso calc R 1
C C18 1.3691(3) 0.5590(4) 0.33530(17) 0.0412(8) Uani d . 1
H H18 1.3862 0.6392 0.3726 0.049 Uiso calc R 1
C C12 1.2123(3) 0.9391(4) 0.3189(2) 0.0549(10) Uani d . 1
H H12A 1.1501 0.9753 0.2783 0.082 Uiso calc R 1
H H12B 1.2818 0.9063 0.3080 0.082 Uiso calc R 1
H H12C 1.2301 1.0433 0.3502 0.082 Uiso calc R 1
C C11 1.0755(3) 0.9571(5) 0.4171(2) 0.0579(10) Uani d . 1
H H11A 1.1502 0.9906 0.4500 0.087 Uiso calc R 1
H H11B 1.0189 0.9321 0.4396 0.087 Uiso calc R 1
H H11C 1.0478 1.0600 0.3858 0.087 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'
Cl Cl 0.1484 0.1585 '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_publ_flag
C2 O1 H1 109.5 ?
C7 N1 C8 122.3(3) yes
C9 N2 N3 107.3(2) ?
C9 N2 C12 123.5(3) ?
N3 N2 C12 117.5(3) ?
C10 N3 N2 109.5(3) yes
C10 N3 C13 124.1(2) yes
N2 N3 C13 119.8(2) yes
C6 C5 C4 121.0(4) ?
C6 C5 Cl1 119.6(3) ?
C4 C5 Cl1 119.4(3) ?
C5 C6 C1 120.5(3) ?
C5 C6 H6 119.7 ?
C1 C6 H6 119.7 ?
C6 C1 C2 118.4(3) ?
C6 C1 C7 119.9(3) ?
C2 C1 C7 121.7(3) yes
O1 C2 C3 118.6(3) yes
O1 C2 C1 121.9(3) yes
C3 C2 C1 119.5(3) ?
C4 C3 C2 121.0(4) ?
C4 C3 H3 119.5 ?
C2 C3 H3 119.5 ?
C3 C4 C5 119.5(4) ?
C3 C4 H4 120.2 ?
C5 C4 H4 120.2 ?
N1 C7 C1 121.1(3) ?
N1 C7 H7 119.4 ?
C1 C7 H7 119.4 ?
C9 C8 N1 123.2(3) ?
C9 C8 C10 108.4(3) ?
N1 C8 C10 128.4(3) ?
O2 C10 N3 123.5(3) ?
O2 C10 C8 131.8(3) ?
N3 C10 C8 104.6(3) ?
N2 C9 C8 109.9(3) ?
N2 C9 C11 121.5(3) ?
C8 C9 C11 128.6(3) ?
C18 C13 C14 119.6(3) ?
C18 C13 N3 121.0(3) ?
C14 C13 N3 119.3(3) ?
C15 C14 C13 119.8(3) ?
C15 C14 H14 120.1 ?
C13 C14 H14 120.1 ?
C16 C15 C14 120.4(4) ?
C16 C15 H15 119.8 ?
C14 C15 H15 119.8 ?
C17 C16 C15 119.7(4) ?
C17 C16 H16 120.2 ?
C15 C16 H16 120.2 ?
C16 C17 C18 120.7(3) ?
C16 C17 H17 119.6 ?
C18 C17 H17 119.6 ?
C17 C18 C13 119.8(3) ?
C17 C18 H18 120.1 ?
C13 C18 H18 120.1 ?
N2 C12 H12A 109.5 ?
N2 C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
N2 C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
C9 C11 H11A 109.5 ?
C9 C11 H11B 109.5 ?
H11A C11 H11B 109.5 ?
C9 C11 H11C 109.5 ?
H11A C11 H11C 109.5 ?
H11B C11 H11C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C5 1.749(4) yes
O1 C2 1.348(4) yes
O1 H1 0.8200 ?
O2 C10 1.234(3) yes
N1 C7 1.284(4) yes
N1 C8 1.392(4) yes
N2 C9 1.355(4) ?
N2 N3 1.405(3) ?
N2 C12 1.468(4) ?
N3 C10 1.401(4) ?
N3 C13 1.416(4) ?
C5 C6 1.367(5) ?
C5 C4 1.378(5) ?
C6 C1 1.402(4) ?
C6 H6 0.9300 ?
C1 C2 1.407(5) ?
C1 C7 1.443(5) ?
C2 C3 1.389(5) ?
C3 C4 1.371(5) ?
C3 H3 0.9300 ?
C4 H4 0.9300 ?
C7 H7 0.9300 ?
C8 C9 1.375(4) ?
C8 C10 1.436(5) ?
C9 C11 1.487(5) ?
C13 C18 1.380(4) ?
C13 C14 1.384(5) ?
C14 C15 1.374(5) ?
C14 H14 0.9300 ?
C15 C16 1.371(5) ?
C15 H15 0.9300 ?
C16 C17 1.369(5) ?
C16 H16 0.9300 ?
C17 C18 1.369(5) ?
C17 H17 0.9300 ?
C18 H18 0.9300 ?
C12 H12A 0.9600 ?
C12 H12B 0.9600 ?
C12 H12C 0.9600 ?
C11 H11A 0.9600 ?
C11 H11B 0.9600 ?
C11 H11C 0.9600 ?
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_publ_flag
O1 H1 N1 0.82 1.87 2.599(4) 146.8 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
C9 N2 N3 C10 -5.9(3)
C12 N2 N3 C10 -150.3(3)
C9 N2 N3 C13 -158.6(3)
C12 N2 N3 C13 57.0(4)
C4 C5 C6 C1 -0.3(5)
Cl1 C5 C6 C1 178.8(2)
C5 C6 C1 C2 0.5(5)
C5 C6 C1 C7 -179.8(3)
C6 C1 C2 O1 179.2(3)
C7 C1 C2 O1 -0.4(5)
C6 C1 C2 C3 -0.7(5)
C7 C1 C2 C3 179.7(3)
O1 C2 C3 C4 -179.3(3)
C1 C2 C3 C4 0.6(5)
C2 C3 C4 C5 -0.3(5)
C6 C5 C4 C3 0.2(5)
Cl1 C5 C4 C3 -178.9(3)
C8 N1 C7 C1 179.5(3)
C6 C1 C7 N1 178.8(3)
C2 C1 C7 N1 -1.5(5)
C7 N1 C8 C9 178.0(3)
C7 N1 C8 C10 -4.1(5)
N2 N3 C10 O2 -174.1(3)
C13 N3 C10 O2 -22.9(5)
N2 N3 C10 C8 3.8(3)
C13 N3 C10 C8 155.1(3)
C9 C8 C10 O2 177.3(3)
N1 C8 C10 O2 -0.8(6)
C9 C8 C10 N3 -0.5(3)
N1 C8 C10 N3 -178.6(3)
N3 N2 C9 C8 5.6(3)
C12 N2 C9 C8 147.3(3)
N3 N2 C9 C11 -174.9(3)
C12 N2 C9 C11 -33.2(5)
N1 C8 C9 N2 175.0(3)
C10 C8 C9 N2 -3.2(4)
N1 C8 C9 C11 -4.4(5)
C10 C8 C9 C11 177.3(3)
C10 N3 C13 C18 -121.3(3)
N2 N3 C13 C18 27.3(4)
C10 N3 C13 C14 56.7(4)
N2 N3 C13 C14 -154.8(3)
C18 C13 C14 C15 0.6(5)
N3 C13 C14 C15 -177.3(3)
C13 C14 C15 C16 -1.3(6)
C14 C15 C16 C17 0.5(6)
C15 C16 C17 C18 1.0(6)
C16 C17 C18 C13 -1.7(5)
C14 C13 C18 C17 0.9(5)
N3 C13 C18 C17 178.8(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655049
