#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/90/2209048.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_2209048
loop_
_publ_author_name
'Duan, Xue-Min'
'Fan, Mei-Lian'
'Zheng, Peng-Wu'
'Li, Jiang-Sheng'
'Huang, Peng-Mian'
_publ_section_title
;
 2-(4-Chlorophenyl)-5-methyl-1H-pyrazol-3(2H)-one
;
_journal_coeditor_code           XU2016
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2019
_journal_page_last               o2020
_journal_paper_doi               10.1107/S1600536806013699
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C10 H9 Cl N2 O'
_chemical_formula_moiety         'C10 H9 Cl N2 O'
_chemical_formula_sum            'C10 H9 Cl N2 O'
_chemical_formula_weight         208.64
_chemical_melting_point          441
_chemical_name_systematic
;
2-(4-Chlorophenyl)-5-methyl-1H-pyrazol-3(2H)-one
;
_space_group_IT_number           2
_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                105.980(13)
_cell_angle_beta                 94.719(14)
_cell_angle_gamma                101.250(13)
_cell_formula_units_Z            2
_cell_length_a                   5.885(5)
_cell_length_b                   7.704(7)
_cell_length_c                   11.380(10)
_cell_measurement_reflns_used    1622
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.5
_cell_measurement_theta_min      2.8
_cell_volume                     481.4(7)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_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 0.99
_diffrn_measured_fraction_theta_max 0.99
_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  0.025
_diffrn_reflns_av_sigmaI/netI    0.035
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2397
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         1.9
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.361
_exptl_absorpt_correction_T_max  0.925
_exptl_absorpt_correction_T_min  0.899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.26
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         1669
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.045
_refine_ls_R_factor_gt           0.038
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.054P)²+0.1893P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.103
_refine_ls_wR_factor_ref         0.111
_reflns_number_gt                1421
_reflns_number_total             1669
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2016.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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_database_code               2209048
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Cl Cl1 0.46931(12) -0.04642(9) 0.14776(5) 0.0653(3) Uani d . 1
O O1 0.1306(2) 0.3563(2) 0.70412(13) 0.0514(4) Uani d . 1
N N1 0.5211(2) 0.3831(2) 0.67330(13) 0.0340(4) Uani d . 1
N N2 0.7367(3) 0.4918(2) 0.73944(15) 0.0397(4) Uani d . 1
C C1 0.5052(3) 0.2847(2) 0.54670(16) 0.0324(4) Uani d . 1
C C2 0.6975(3) 0.3122(3) 0.48463(18) 0.0414(5) Uani d . 1
H H2 0.8339 0.3990 0.5253 0.050 Uiso calc R 1
C C3 0.6851(4) 0.2103(3) 0.36256(18) 0.0457(5) Uani d . 1
H H3 0.8139 0.2273 0.3214 0.055 Uiso calc R 1
C C4 0.4813(4) 0.0834(3) 0.30197(17) 0.0416(5) Uani d . 1
C C5 0.2884(4) 0.0560(3) 0.36099(19) 0.0470(5) Uani d . 1
H H5 0.1514 -0.0288 0.3188 0.056 Uiso calc R 1
C C6 0.2997(3) 0.1562(3) 0.48417(19) 0.0423(5) Uani d . 1
H H6 0.1705 0.1377 0.5249 0.051 Uiso calc R 1
C C7 0.3443(3) 0.4248(3) 0.74289(17) 0.0362(4) Uani d . 1
C C8 0.4626(3) 0.5550(3) 0.85669(17) 0.0418(5) Uani d . 1
H H8 0.3916 0.6082 0.9233 0.050 Uiso calc R 1
C C9 0.6962(3) 0.5883(3) 0.85163(17) 0.0400(5) Uani d . 1
C C10 0.8974(4) 0.7108(3) 0.9465(2) 0.0594(6) Uani d . 1
H H10A 0.9931 0.6359 0.9716 0.089 Uiso calc R 1
H H10B 0.8384 0.7786 1.0169 0.089 Uiso calc R 1
H H10C 0.9895 0.7961 0.9117 0.089 Uiso calc R 1
H H2A 0.857(4) 0.450(3) 0.730(2) 0.058(7) Uiso d . 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.0860(5) 0.0646(4) 0.0351(3) 0.0180(3) 0.0105(3) -0.0028(3)
O1 0.0266(8) 0.0645(10) 0.0507(9) 0.0087(6) 0.0096(6) -0.0027(7)
N1 0.0236(8) 0.0403(8) 0.0329(8) 0.0058(6) 0.0050(6) 0.0034(7)
N2 0.0267(9) 0.0469(9) 0.0382(9) 0.0085(7) 0.0051(7) 0.0005(7)
C1 0.0320(10) 0.0351(9) 0.0309(9) 0.0114(7) 0.0062(7) 0.0080(7)
C2 0.0341(10) 0.0503(11) 0.0354(10) 0.0018(8) 0.0079(8) 0.0102(9)
C3 0.0446(12) 0.0589(13) 0.0343(10) 0.0094(10) 0.0143(9) 0.0140(9)
C4 0.0518(12) 0.0409(10) 0.0311(10) 0.0150(9) 0.0052(8) 0.0063(8)
C5 0.0426(12) 0.0437(11) 0.0431(11) 0.0037(9) 0.0004(9) 0.0002(9)
C6 0.0326(10) 0.0441(11) 0.0431(11) 0.0053(8) 0.0090(8) 0.0030(9)
C7 0.0287(10) 0.0431(10) 0.0367(10) 0.0115(8) 0.0095(7) 0.0081(8)
C8 0.0361(10) 0.0502(11) 0.0350(10) 0.0143(9) 0.0098(8) 0.0014(8)
C9 0.0376(11) 0.0431(11) 0.0351(10) 0.0124(8) 0.0049(8) 0.0025(8)
C10 0.0396(12) 0.0672(15) 0.0509(13) 0.0088(10) -0.0002(9) -0.0110(11)
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
C7 N1 N2 108.91(15)
C7 N1 C1 129.69(15)
N2 N1 C1 119.94(15)
C9 N2 N1 107.48(16)
C9 N2 H2A 122.4(17)
N1 N2 H2A 119.3(17)
C2 C1 C6 119.58(18)
C2 C1 N1 120.00(16)
C6 C1 N1 120.40(16)
C3 C2 C1 119.96(18)
C3 C2 H2 120.0
C1 C2 H2 120.0
C4 C3 C2 119.89(18)
C4 C3 H3 120.1
C2 C3 H3 120.1
C5 C4 C3 121.09(18)
C5 C4 Cl1 119.55(16)
C3 C4 Cl1 119.36(16)
C4 C5 C6 119.51(19)
C4 C5 H5 120.2
C6 C5 H5 120.2
C5 C6 C1 119.97(18)
C5 C6 H6 120.0
C1 C6 H6 120.0
O1 C7 N1 123.28(17)
O1 C7 C8 131.64(17)
N1 C7 C8 105.07(16)
C9 C8 C7 108.60(17)
C9 C8 H8 125.7
C7 C8 H8 125.7
N2 C9 C8 109.75(17)
N2 C9 C10 119.95(19)
C8 C9 C10 130.30(19)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C4 1.753(2) yes
O1 C7 1.256(2) yes
N1 N2 1.400(2) yes
N1 C1 1.417(2) yes
N1 C7 1.392(2) yes
N2 C9 1.355(3) yes
N2 H2A 0.84(3) ?
C1 C2 1.394(3) ?
C1 C6 1.397(3) ?
C2 C3 1.383(3) ?
C2 H2 0.9300 ?
C3 C4 1.380(3) ?
C3 H3 0.9300 ?
C4 C5 1.377(3) ?
C5 C6 1.391(3) ?
C5 H5 0.9300 ?
C6 H6 0.9300 ?
C7 C8 1.426(3) ?
C8 C9 1.357(3) ?
C8 H8 0.9300 ?
C9 C10 1.500(3) ?
C10 H10A 0.9600 ?
C10 H10B 0.9600 ?
C10 H10C 0.9600 ?
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
N2 H2A O1 1_655 0.84(3) 1.90(3) 2.737(3) 179(2)
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
C7 N1 N2 C9 4.5(2)
C1 N1 N2 C9 172.07(16)
C7 N1 C1 C2 157.37(19)
N2 N1 C1 C2 -7.2(3)
C7 N1 C1 C6 -24.3(3)
N2 N1 C1 C6 171.14(17)
C6 C1 C2 C3 -1.1(3)
N1 C1 C2 C3 177.26(17)
C1 C2 C3 C4 0.9(3)
C2 C3 C4 C5 0.1(3)
C2 C3 C4 Cl1 -179.35(16)
C3 C4 C5 C6 -0.8(3)
Cl1 C4 C5 C6 178.61(15)
C4 C5 C6 C1 0.6(3)
C2 C1 C6 C5 0.4(3)
N1 C1 C6 C5 -177.99(17)
N2 N1 C7 O1 175.83(18)
C1 N1 C7 O1 9.9(3)
N2 N1 C7 C8 -3.3(2)
C1 N1 C7 C8 -169.20(17)
O1 C7 C8 C9 -178.1(2)
N1 C7 C8 C9 0.9(2)
N1 N2 C9 C8 -4.0(2)
N1 N2 C9 C10 176.84(19)
C7 C8 C9 N2 2.0(2)
C7 C8 C9 C10 -179.0(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2685561
