#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/18/2231878.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_2231878
loop_
_publ_author_name
'Lokhande, Pradeep'
'Hasanzadeh, Kamal'
'Khaledi, Hamid'
'Mohd Ali, Hapipah'
_publ_section_title
;
 3-(3-Chloro-2-hydroxyphenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde
;
_journal_coeditor_code           GK2410
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2736
_journal_paper_doi               10.1107/S1600536811038025
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H11 Cl N2 O2'
_chemical_formula_moiety         'C16 H11 Cl N2 O2'
_chemical_formula_sum            'C16 H11 Cl N2 O2'
_chemical_formula_weight         298.72
_chemical_name_systematic
;
3-(3-Chloro-2-hydroxyphenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde
;
_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                   3.81420(10)
_cell_length_b                   15.9367(3)
_cell_length_c                   21.4121(5)
_cell_measurement_reflns_used    1835
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.65
_cell_measurement_theta_min      2.29
_cell_volume                     1301.55(5)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material
;
'SHELXL97 (Sheldrick, 2008) and publCIF
(Westrip, 2010)'
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω 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  0.0611
_diffrn_reflns_av_sigmaI/netI    0.0536
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            11133
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    0.299
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.231
_refine_ls_abs_structure_details 'Flack (1983), 1005 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.03(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2563
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0380
_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)+(0.0338P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0711
_refine_ls_wR_factor_ref         0.0750
_reflns_number_gt                2195
_reflns_number_total             2563
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            gk2410.cif
_cod_data_source_block           I
_cod_database_code               2231878
_cod_database_fobs_code          2231878
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_occupancy
_atom_site_symmetry_multiplicity
Cl Cl1 -0.15696(17) 0.83249(4) 0.11291(3) 0.02120(16) Uani d 1 1
O O1 0.1795(5) 0.74015(10) 0.21221(7) 0.0193(4) Uani d 1 1
H H1 0.288(8) 0.7150(17) 0.2372(12) 0.029 Uiso d 1 1
O O2 0.2257(7) 0.38231(11) 0.14904(10) 0.0523(8) Uani d 1 1
N N1 0.6317(6) 0.55861(11) 0.30360(8) 0.0146(4) Uani d 1 1
N N2 0.4904(5) 0.61122(12) 0.26021(8) 0.0152(5) Uani d 1 1
C C1 0.1243(7) 0.69086(14) 0.16139(10) 0.0146(5) Uani d 1 1
C C2 -0.0338(6) 0.72717(14) 0.10952(12) 0.0166(5) Uani d 1 1
C C3 -0.0909(6) 0.68296(14) 0.05499(11) 0.0170(6) Uani d 1 1
H H3 -0.205(7) 0.7091(14) 0.0212(11) 0.020 Uiso d 1 1
C C4 0.0085(7) 0.59966(16) 0.05228(11) 0.0189(6) Uani d 1 1
H H4 -0.027(6) 0.5695(15) 0.0148(11) 0.023 Uiso d 1 1
C C5 0.1558(7) 0.56110(14) 0.10338(10) 0.0169(5) Uani d 1 1
H H5 0.217(7) 0.5034(14) 0.1021(11) 0.020 Uiso d 1 1
C C6 0.2166(6) 0.60481(14) 0.15903(10) 0.0136(5) Uani d 1 1
C C7 0.3790(7) 0.56342(13) 0.21291(11) 0.0145(5) Uani d 1 1
C C8 0.4516(7) 0.47684(15) 0.22672(11) 0.0193(6) Uani d 1 1
C C9 0.6108(7) 0.47880(15) 0.28431(11) 0.0185(6) Uani d 1 1
H H9 0.705(7) 0.4337(15) 0.3073(11) 0.022 Uiso d 1 1
C C10 0.3808(9) 0.39580(16) 0.19719(13) 0.0340(8) Uani d 1 1
H H10 0.478(7) 0.3494(17) 0.2230(13) 0.041 Uiso d 1 1
C C11 0.7764(6) 0.59165(14) 0.36014(10) 0.0148(6) Uani d 1 1
C C12 0.8074(7) 0.54004(15) 0.41212(11) 0.0177(5) Uani d 1 1
H H12 0.726(7) 0.4860(15) 0.4085(10) 0.021 Uiso d 1 1
C C13 0.9498(7) 0.57231(16) 0.46616(12) 0.0205(6) Uani d 1 1
H H13 0.959(7) 0.5372(16) 0.5017(11) 0.025 Uiso d 1 1
C C14 1.0616(6) 0.65466(16) 0.46938(12) 0.0194(6) Uani d 1 1
H H14 1.158(7) 0.6750(14) 0.5087(11) 0.023 Uiso d 1 1
C C15 1.0272(7) 0.70584(16) 0.41707(11) 0.0192(6) Uani d 1 1
H H15 1.114(7) 0.7627(15) 0.4189(10) 0.023 Uiso d 1 1
C C16 0.8840(6) 0.67472(15) 0.36244(11) 0.0161(5) Uani d 1 1
H H16 0.865(7) 0.7101(14) 0.3265(11) 0.019 Uiso d 1 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'
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
C1 O1 H1 109(2)
C9 N1 N2 110.51(19)
C9 N1 C11 129.3(2)
N2 N1 C11 120.21(17)
C7 N2 N1 106.97(18)
O1 C1 C2 117.8(2)
O1 C1 C6 123.4(2)
C2 C1 C6 118.8(2)
C3 C2 C1 122.1(2)
C3 C2 Cl1 118.92(19)
C1 C2 Cl1 118.95(18)
C2 C3 C4 118.8(2)
C2 C3 H3 119.8(14)
C4 C3 H3 121.3(14)
C5 C4 C3 120.5(2)
C5 C4 H4 120.4(15)
C3 C4 H4 119.1(15)
C4 C5 C6 121.5(2)
C4 C5 H5 120.7(14)
C6 C5 H5 117.8(14)
C5 C6 C1 118.1(2)
C5 C6 C7 121.1(2)
C1 C6 C7 120.8(2)
N2 C7 C8 109.3(2)
N2 C7 C6 118.3(2)
C8 C7 C6 132.4(2)
C9 C8 C7 104.3(2)
C9 C8 C10 119.3(2)
C7 C8 C10 136.3(2)
N1 C9 C8 108.9(2)
N1 C9 H9 122.7(15)
C8 C9 H9 128.2(15)
O2 C10 C8 128.1(3)
O2 C10 H10 121.6(16)
C8 C10 H10 110.3(16)
C16 C11 C12 120.8(2)
C16 C11 N1 119.7(2)
C12 C11 N1 119.5(2)
C13 C12 C11 119.0(2)
C13 C12 H12 123.6(15)
C11 C12 H12 117.3(15)
C12 C13 C14 121.2(2)
C12 C13 H13 118.1(15)
C14 C13 H13 120.6(15)
C13 C14 C15 119.2(2)
C13 C14 H14 118.4(14)
C15 C14 H14 122.4(14)
C16 C15 C14 120.5(2)
C16 C15 H15 120.4(14)
C14 C15 H15 119.0(14)
C15 C16 C11 119.3(2)
C15 C16 H16 120.0(14)
C11 C16 H16 120.7(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C2 1.745(2) ?
O1 C1 1.358(3) ?
O1 H1 0.79(3) ?
O2 C10 1.208(3) n
N1 C9 1.340(3) n
N1 N2 1.363(3) n
N1 C11 1.431(3) n
N2 C7 1.337(3) n
C1 C2 1.390(3) ?
C1 C6 1.417(3) ?
C2 C3 1.381(3) ?
C3 C4 1.382(3) ?
C3 H3 0.94(2) ?
C4 C5 1.375(3) ?
C4 H4 0.94(2) ?
C5 C6 1.400(3) ?
C5 H5 0.95(2) ?
C6 C7 1.466(3) ?
C7 C8 1.438(3) ?
C8 C9 1.375(3) ?
C8 C10 1.463(3) ?
C9 H9 0.94(2) ?
C10 H10 1.00(3) ?
C11 C16 1.387(3) ?
C11 C12 1.389(3) ?
C12 C13 1.378(3) ?
C12 H12 0.92(2) ?
C13 C14 1.382(3) ?
C13 H13 0.95(2) ?
C14 C15 1.392(3) ?
C14 H14 0.98(2) ?
C15 C16 1.383(3) ?
C15 H15 0.97(2) ?
C16 H16 0.96(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
O1 H1 N2 . 0.79(3) 1.89(3) 2.585(2) 147(3)
C5 H5 O2 . 0.95(2) 2.18(2) 3.024(3) 148(2)
C10 H10 O1 3_645 1.00(3) 2.58(3) 3.568(3) 171(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657027
