#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/81/2208102.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_2208102
loop_
_publ_author_name
'Ding-Ben Chen'
'Ling Huang'
_publ_section_title
4-{[(1E)-(3,5-Dichloro-2-hydroxyphenyl)methylene]amino}-1,5-dimethyl-2-phenyl-3H-pyrazol-3(2H)-one
_journal_coeditor_code           JH6032
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o757
_journal_page_last               o758
_journal_paper_doi               10.1107/S1600536806001000
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C18 H15 Cl2 N3 O2'
_chemical_formula_moiety         'C18 H15 Cl2 N3 O2'
_chemical_formula_sum            'C18 H15 Cl2 N3 O2'
_chemical_formula_weight         376.23
_chemical_melting_point          498.9(3)
_chemical_name_systematic
;
4-{[(1E)-(3,5-Dichloro-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 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 90.921(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0146(6)
_cell_length_b                   8.0466(7)
_cell_length_c                   30.510(3)
_cell_measurement_reflns_used    3109
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.27
_cell_measurement_theta_min      1.34
_cell_volume                     1721.9(3)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 7.07
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_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  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            8818
_diffrn_reflns_theta_full        25.27
_diffrn_reflns_theta_max         25.27
_diffrn_reflns_theta_min         1.34
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.394
_exptl_absorpt_correction_T_max  0.939
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.259
_refine_ls_extinction_coef       0.0028(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3109
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0472
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0670P)²+0.3379P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1355
_reflns_number_gt                2510
_reflns_number_total             3109
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jh6032.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '498.6-499.1' was changed to
'498.9(3)' - the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '498.6-499.1' was changed to
'498.9(3)' - the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2208102
_cod_database_fobs_code          2208102
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_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_type_symbol
Cl1 1.04525(10) 0.97152(9) 0.59085(2) 0.0543(3) Uani d . 1 Cl
Cl2 0.40859(11) 0.64875(11) 0.63686(2) 0.0619(3) Uani d . 1 Cl
O1 0.3259(3) 0.6426(3) 0.54276(7) 0.0511(5) Uani d . 1 O
H1A 0.314(5) 0.647(4) 0.5164(11) 0.064(11) Uiso d . 1 H
O2 0.6109(2) 0.8324(3) 0.37899(6) 0.0505(5) Uani d . 1 O
N1 0.3971(3) 0.7104(3) 0.46139(7) 0.0384(5) Uani d . 1 N
N2 0.1761(3) 0.6432(3) 0.35663(7) 0.0403(5) Uani d . 1 N
N3 0.3354(3) 0.7373(3) 0.34370(7) 0.0399(5) Uani d . 1 N
C1 0.6055(3) 0.7900(3) 0.52031(8) 0.0385(6) Uani d . 1 C
C2 0.7765(4) 0.8682(3) 0.53280(9) 0.0418(6) Uani d . 1 C
H2A 0.8541 0.9141 0.5115 0.050 Uiso calc R 1 H
C3 0.8298(4) 0.8777(3) 0.57585(9) 0.0418(6) Uani d . 1 C
C4 0.7173(4) 0.8118(3) 0.60835(9) 0.0440(6) Uani d . 1 C
H4A 0.7547 0.8191 0.6377 0.053 Uiso calc R 1 H
C5 0.5487(4) 0.7349(3) 0.59637(8) 0.0421(6) Uani d . 1 C
C6 0.4894(3) 0.7205(3) 0.55304(8) 0.0379(6) Uani d . 1 C
C7 0.5514(4) 0.7840(3) 0.47445(8) 0.0409(6) Uani d . 1 C
H7A 0.6293 0.8341 0.4539 0.049 Uiso calc R 1 H
C8 0.3460(3) 0.7068(3) 0.41703(8) 0.0359(6) Uani d . 1 C
C9 0.1816(3) 0.6376(3) 0.40130(8) 0.0376(6) Uani d . 1 C
C10 0.4514(3) 0.7686(3) 0.38069(8) 0.0383(6) Uani d . 1 C
C11 0.0206(4) 0.5663(5) 0.42656(11) 0.0509(7) Uani d . 1 C
C12 -0.0033(4) 0.6759(5) 0.33272(11) 0.0488(7) Uani d . 1 C
C13 0.4074(3) 0.7176(3) 0.30086(8) 0.0383(6) Uani d . 1 C
C14 0.3562(4) 0.5848(4) 0.27448(9) 0.0481(7) Uani d . 1 C
H14A 0.2736 0.5037 0.2848 0.058 Uiso calc R 1 H
C15 0.4283(4) 0.5732(4) 0.23278(10) 0.0608(8) Uani d . 1 C
H15A 0.3905 0.4856 0.2148 0.073 Uiso calc R 1 H
C16 0.5546(4) 0.6883(5) 0.21737(10) 0.0640(9) Uani d . 1 C
H16A 0.6030 0.6783 0.1893 0.077 Uiso calc R 1 H
C17 0.6089(4) 0.8186(4) 0.24387(9) 0.0577(8) Uani d . 1 C
H17A 0.6972 0.8954 0.2339 0.069 Uiso calc R 1 H
C18 0.5341(4) 0.8371(4) 0.28513(9) 0.0472(7) Uani d . 1 C
H18A 0.5675 0.9282 0.3024 0.057 Uiso calc R 1 H
H11A -0.090(6) 0.631(5) 0.4215(12) 0.086(12) Uiso d . 1 H
H11B -0.015(5) 0.462(5) 0.4143(12) 0.095(13) Uiso d . 1 H
H11C 0.059(5) 0.541(4) 0.4545(13) 0.081(12) Uiso d . 1 H
H12A -0.053(4) 0.790(4) 0.3372(10) 0.067(10) Uiso d . 1 H
H12B -0.083(5) 0.591(4) 0.3370(11) 0.071(10) Uiso d . 1 H
H12C 0.014(4) 0.670(3) 0.3017(11) 0.053(8) Uiso d . 1 H
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'
Cl Cl 0.1484 0.1585 '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
C6 O1 H1A 107(2) ?
C7 N1 C8 120.7(2) yes
C9 N2 N3 106.69(18) ?
C9 N2 C12 120.9(2) ?
N3 N2 C12 116.2(2) ?
C10 N3 N2 108.84(19) ?
C10 N3 C13 123.4(2) ?
N2 N3 C13 119.54(19) ?
C2 C1 C6 119.0(2) ?
C2 C1 C7 119.2(2) ?
C6 C1 C7 121.7(2) ?
C3 C2 C1 120.5(2) ?
C3 C2 H2A 119.8 ?
C1 C2 H2A 119.8 ?
C2 C3 C4 121.3(2) yes
C2 C3 Cl1 120.0(2) ?
C4 C3 Cl1 118.7(2) ?
C5 C4 C3 118.6(2) ?
C5 C4 H4A 120.7 ?
C3 C4 H4A 120.7 ?
C4 C5 C6 122.3(2) ?
C4 C5 Cl2 118.9(2) ?
C6 C5 Cl2 118.8(2) ?
O1 C6 C5 120.4(2) yes
O1 C6 C1 121.3(2) yes
C5 C6 C1 118.3(2) ?
N1 C7 C1 121.3(2) ?
N1 C7 H7A 119.3 ?
C1 C7 H7A 119.3 ?
C9 C8 N1 123.6(2) ?
C9 C8 C10 108.3(2) ?
N1 C8 C10 128.0(2) ?
C8 C9 N2 110.4(2) ?
C8 C9 C11 128.3(2) ?
N2 C9 C11 121.3(2) ?
O2 C10 N3 123.8(2) ?
O2 C10 C8 131.1(2) ?
N3 C10 C8 105.1(2) ?
C9 C11 H11A 109(2) ?
C9 C11 H11B 109(2) ?
H11A C11 H11B 102(3) ?
C9 C11 H11C 111(2) ?
H11A C11 H11C 120(3) ?
H11B C11 H11C 104(3) ?
N2 C12 H12A 113.3(18) ?
N2 C12 H12B 109(2) ?
H12A C12 H12B 118(3) ?
N2 C12 H12C 111.1(17) ?
H12A C12 H12C 104(2) ?
H12B C12 H12C 101(3) ?
C14 C13 C18 119.5(2) ?
C14 C13 N3 122.0(2) ?
C18 C13 N3 118.5(2) ?
C15 C14 C13 119.6(3) ?
C15 C14 H14A 120.2 ?
C13 C14 H14A 120.2 ?
C16 C15 C14 121.3(3) ?
C16 C15 H15A 119.3 ?
C14 C15 H15A 119.3 ?
C15 C16 C17 119.2(3) ?
C15 C16 H16A 120.4 ?
C17 C16 H16A 120.4 ?
C16 C17 C18 120.9(3) ?
C16 C17 H17A 119.6 ?
C18 C17 H17A 119.6 ?
C17 C18 C13 119.5(3) ?
C17 C18 H18A 120.3 ?
C13 C18 H18A 120.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C3 1.744(3) yes
Cl2 C5 1.736(3) yes
O1 C6 1.340(3) yes
O1 H1A 0.81(3) ?
O2 C10 1.233(3) yes
N1 C7 1.291(3) ?
N1 C8 1.395(3) yes
N2 C9 1.364(3) ?
N2 N3 1.412(3) yes
N2 C12 1.468(3) ?
N3 C10 1.403(3) yes
N3 C13 1.418(3) ?
C1 C2 1.402(3) ?
C1 C6 1.414(4) ?
C1 C7 1.445(4) ?
C2 C3 1.362(4) ?
C2 H2A 0.9300 ?
C3 C4 1.383(4) ?
C4 C5 1.379(4) ?
C4 H4A 0.9300 ?
C5 C6 1.384(4) ?
C7 H7A 0.9300 ?
C8 C9 1.361(3) ?
C8 C10 1.432(3) ?
C9 C11 1.492(4) ?
C11 H11A 0.95(4) ?
C11 H11B 0.95(4) ?
C11 H11C 0.91(4) ?
C12 H12A 0.99(3) ?
C12 H12B 0.89(4) ?
C12 H12C 0.96(3) ?
C13 C14 1.382(4) ?
C13 C18 1.399(4) ?
C14 C15 1.380(4) ?
C14 H14A 0.9300 ?
C15 C16 1.369(5) ?
C15 H15A 0.9300 ?
C16 C17 1.375(4) ?
C16 H16A 0.9300 ?
C17 C18 1.380(4) ?
C17 H17A 0.9300 ?
C18 H18A 0.9300 ?
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 H1A N1 0.81(3) 1.86(3) 2.598(3) 152(3) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654919
