#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/07/2200780.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_2200780
loop_
_publ_author_name
'Errington, William'
'Kumar, Rajesh'
'Kumar, Naresh'
'Parmar, Virinder S.'
'Roy, Sucharita'
_publ_section_title
;
 2-[3-(4-Chlorophenyl)pyrazol-5-yl]-1-(2-hydroxy-4-methoxyphenyl)ethanone
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1084
_journal_page_last               o1086
_journal_paper_doi               10.1107/S1600536801017421
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C18 H15 Cl N2 O3'
_chemical_formula_moiety         'C18 H15 Cl N2 O3'
_chemical_formula_sum            'C18 H15 Cl N2 O3'
_chemical_formula_weight         342.77
_chemical_name_systematic
;
2-[3-(4-Chlorophenyl)pyrazol-5-yl]-1-(2-hydroxy-4-methoxyphenyl)ethanone
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.338(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   30.1055(18)
_cell_length_b                   7.5383(11)
_cell_length_c                   13.8612(14)
_cell_measurement_reflns_used    3596
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      2.71
_cell_volume                     3145.7(6)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1994)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL/PC (Siemens, 1994)'
_computing_publication_material  SHELXTL/PC
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full .996
_diffrn_measured_fraction_theta_max .996
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0368
_diffrn_reflns_av_sigmaI/netI    .0505
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8778
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.71
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    .262
_exptl_absorpt_correction_T_max  .9793
_exptl_absorpt_correction_T_min  .9024
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          .40
_exptl_crystal_size_mid          .40
_exptl_crystal_size_min          .08
_refine_diff_density_max         .228
_refine_diff_density_min         -.266
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   .913
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3425
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .913
_refine_ls_R_factor_all          .0730
_refine_ls_R_factor_gt           .0420
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0562P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1052
_reflns_number_gt                2145
_reflns_number_total             3425
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn6060.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2 /c'
_cod_database_code               2200780
_cod_database_fobs_code          2200780
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cl1 .038277(18) .04558(8) .33182(4) .0644(2) Uani d . 1 . . Cl
O1 .26052(4) .12928(17) .90110(9) .0462(3) Uani d . 1 . . O
O2 .30704(4) .06150(17) 1.04683(9) .0443(3) Uani d . 1 . . O
H2 .2848(7) .077(3) 1.0047(18) .079(8) Uiso d . 1 . . H
O3 .46303(4) .1403(2) 1.02449(10) .0599(4) Uani d . 1 . . O
N1 .20464(5) .2725(2) .76611(11) .0420(4) Uani d . 1 . . N
H1 .2061(6) .311(3) .8304(15) .064(6) Uiso d . 1 . . H
N2 .16585(4) .2512(2) .71830(10) .0418(4) Uani d . 1 . . N
C1 .29386(5) .1709(2) .85314(12) .0358(4) Uani d . 1 . . C
C2 .28723(5) .2386(2) .75169(12) .0369(4) Uani d . 1 . . C
H2A .2964 .3647 .7495 .044 Uiso calc R 1 . . H
H2B .3071 .1716 .7082 .044 Uiso calc R 1 . . H
C1' .33797(5) .1605(2) .89635(12) .0337(4) Uani d . 1 . . C
C2' .34283(5) .1065(2) .99283(12) .0349(4) Uani d . 1 . . C
C3' .38389(6) .0970(2) 1.03825(13) .0387(4) Uani d . 1 . . C
H3'A .3863 .0593 1.1035 .046 Uiso calc R 1 . . H
C4' .42118(6) .1434(2) .98684(14) .0440(5) Uani d . 1 . . C
C5' .41779(6) .1987(3) .89104(14) .0502(5) Uani d . 1 . . C
H5'A .4437 .2313 .8566 .060 Uiso calc R 1 . . H
C6' .37724(5) .2061(2) .84693(14) .0427(5) Uani d . 1 . . C
H6'A .3754 .2426 .7814 .051 Uiso calc R 1 . . H
C7' .46876(7) .0764(3) 1.12064(16) .0625(6) Uani d . 1 . . C
H7'A .5003 .0810 1.1383 .094 Uiso calc R 1 . . H
H7'B .4582 -.0463 1.1246 .094 Uiso calc R 1 . . H
H7'C .4517 .1508 1.1651 .094 Uiso calc R 1 . . H
C3" .17761(5) .1909(2) .63156(12) .0345(4) Uani d . 1 . . C
C4" .22404(5) .1724(2) .62598(12) .0362(4) Uani d . 1 . . C
H4"A .2406 .1320 .5722 .043 Uiso calc R 1 . . H
C5" .24036(5) .2245(2) .71353(12) .0350(4) Uani d . 1 . . C
C1"' .14354(5) .1523(2) .55815(12) .0354(4) Uani d . 1 . . C
C2"' .15438(6) .0798(2) .46912(13) .0400(4) Uani d . 1 . . C
H2"A .1846 .0538 .4556 .048 Uiso calc R 1 . . H
C3"' .12251(6) .0444(2) .39991(14) .0431(5) Uani d . 1 . . C
H3"A .1305 -.0059 .3396 .052 Uiso calc R 1 . . H
C4"' .07886(6) .0835(2) .41979(14) .0442(5) Uani d . 1 . . C
C5"' .06649(6) .1524(3) .50759(14) .0492(5) Uani d . 1 . . C
H5"A .0361 .1760 .5207 .059 Uiso calc R 1 . . H
C6"' .09861(6) .1869(2) .57632(13) .0451(5) Uani d . 1 . . C
H6"A .0902 .2348 .6369 .054 Uiso calc R 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 .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl .1484 .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
C2' O2 H2 101.6(15)
C4' O3 C7' 118.07(14)
N2 N1 C5" 113.10(14)
N2 N1 H1 122.6(12)
C5" N1 H1 124.2(12)
C3" N2 N1 104.45(13)
O1 C1 C1' 120.15(15)
O1 C1 C2 118.66(15)
C1' C1 C2 121.15(14)
C5" C2 C1 114.94(13)
C5" C2 H2A 108.5
C1 C2 H2A 108.5
C5" C2 H2B 108.5
C1 C2 H2B 108.5
H2A C2 H2B 107.5
C2' C1' C6' 116.70(15)
C2' C1' C1 119.81(14)
C6' C1' C1 123.48(15)
O2 C2' C3' 116.43(15)
O2 C2' C1' 121.22(15)
C3' C2' C1' 122.36(15)
C4' C3' C2' 118.62(17)
C4' C3' H3'A 120.7
C2' C3' H3'A 120.7
O3 C4' C3' 123.52(17)
O3 C4' C5' 115.62(15)
C3' C4' C5' 120.86(17)
C6' C5' C4' 119.94(16)
C6' C5' H5'A 120.0
C4' C5' H5'A 120.0
C5' C6' C1' 121.51(17)
C5' C6' H6'A 119.2
C1' C6' H6'A 119.2
O3 C7' H7'A 109.5
O3 C7' H7'B 109.5
H7'A C7' H7'B 109.5
O3 C7' H7'C 109.5
H7'A C7' H7'C 109.5
H7'B C7' H7'C 109.5
N2 C3" C4" 110.61(15)
N2 C3" C1"' 120.21(15)
C4" C3" C1"' 129.18(15)
C5" C4" C3" 105.97(15)
C5" C4" H4"A 127.0
C3" C4" H4"A 127.0
N1 C5" C4" 105.85(15)
N1 C5" C2 122.53(15)
C4" C5" C2 131.59(15)
C2"' C1"' C6"' 117.67(17)
C2"' C1"' C3" 121.72(15)
C6"' C1"' C3" 120.60(16)
C3"' C2"' C1"' 121.84(16)
C3"' C2"' H2"A 119.1
C1"' C2"' H2"A 119.1
C4"' C3"' C2"' 118.74(18)
C4"' C3"' H3"A 120.6
C2"' C3"' H3"A 120.6
C3"' C4"' C5"' 121.41(18)
C3"' C4"' Cl1 119.38(16)
C5"' C4"' Cl1 119.20(14)
C4"' C5"' C6"' 119.35(17)
C4"' C5"' H5"A 120.3
C6"' C5"' H5"A 120.3
C5"' C6"' C1"' 120.96(18)
C5"' C6"' H6"A 119.5
C1"' C6"' H6"A 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C4"' . 1.7445(19) ?
O1 C1 . 1.2475(19) ?
O2 C2' . 1.3587(19) ?
O2 H2 . .89(2) ?
O3 C4' . 1.361(2) ?
O3 C7' . 1.426(2) ?
N1 N2 . 1.3488(19) ?
N1 C5" . 1.352(2) ?
N1 H1 . .94(2) ?
N2 C3" . 1.335(2) ?
C1 C1' . 1.455(2) ?
C1 C2 . 1.508(2) ?
C2 C5" . 1.508(2) ?
C2 H2A . .9900 ?
C2 H2B . .9900 ?
C1' C2' . 1.405(2) ?
C1' C6' . 1.412(2) ?
C2' C3' . 1.386(2) ?
C3' C4' . 1.378(2) ?
C3' H3'A . .9500 ?
C4' C5' . 1.395(3) ?
C5' C6' . 1.363(2) ?
C5' H5'A . .9500 ?
C6' H6'A . .9500 ?
C7' H7'A . .9800 ?
C7' H7'B . .9800 ?
C7' H7'C . .9800 ?
C3" C4" . 1.407(2) ?
C3" C1"' . 1.470(2) ?
C4" C5" . 1.364(2) ?
C4" H4"A . .9500 ?
C1"' C2"' . 1.391(2) ?
C1"' C6"' . 1.402(2) ?
C2"' C3"' . 1.379(2) ?
C2"' H2"A . .9500 ?
C3"' C4"' . 1.376(2) ?
C3"' H3"A . .9500 ?
C4"' C5"' . 1.377(3) ?
C5"' C6"' . 1.378(3) ?
C5"' H5"A . .9500 ?
C6"' H6"A . .9500 ?
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
O2 H2 O1 . .89(2) 1.66(2) 2.5040(18) 157(2)
N1 H1 O1 . .94(2) 2.347(19) 2.7311(19) 104.0(14)
N1 H1 O2 7_557 .94(2) 1.99(2) 2.902(2) 162.0(17)
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
_geom_torsion_publ_flag
C5" N1 N2 C3" -1.3(2) ?
O1 C1 C2 C5" -8.3(2) y
C1' C1 C2 C5" 174.18(14) y
O1 C1 C1' C2' -1.1(2) y
C2 C1 C1' C2' 176.39(15) ?
O1 C1 C1' C6' -179.72(16) ?
C2 C1 C1' C6' -2.2(3) ?
C6' C1' C2' O2 179.40(15) ?
C1 C1' C2' O2 .7(2) y
C6' C1' C2' C3' -.2(2) ?
C1 C1' C2' C3' -178.88(15) ?
O2 C2' C3' C4' -179.24(15) ?
C1' C2' C3' C4' .4(3) ?
C7' O3 C4' C3' 3.5(3) ?
C7' O3 C4' C5' -176.97(18) ?
C2' C3' C4' O3 179.49(16) ?
C2' C3' C4' C5' .0(3) ?
O3 C4' C5' C6' 179.92(17) ?
C3' C4' C5' C6' -.5(3) ?
C4' C5' C6' C1' .7(3) ?
C2' C1' C6' C5' -.4(3) ?
C1 C1' C6' C5' 178.26(17) ?
N1 N2 C3" C4" .77(19) ?
N1 N2 C3" C1"' -179.76(14) ?
N2 C3" C4" C5" -.1(2) ?
C1"' C3" C4" C5" -179.47(16) ?
N2 N1 C5" C4" 1.2(2) ?
N2 N1 C5" C2 179.31(15) ?
C3" C4" C5" N1 -.68(19) ?
C3" C4" C5" C2 -178.50(16) ?
C1 C2 C5" N1 45.3(2) ?
C1 C2 C5" C4" -137.16(19) ?
N2 C3" C1"' C2"' -176.21(16) ?
C4" C3" C1"' C2"' 3.1(3) ?
N2 C3" C1"' C6"' 3.4(3) ?
C4" C3" C1"' C6"' -177.29(16) ?
C6"' C1"' C2"' C3"' .8(3) ?
C3" C1"' C2"' C3"' -179.60(15) ?
C1"' C2"' C3"' C4"' .4(3) ?
C2"' C3"' C4"' C5"' -1.6(3) ?
C2"' C3"' C4"' Cl1 178.19(13) ?
C3"' C4"' C5"' C6"' 1.5(3) ?
Cl1 C4"' C5"' C6"' -178.30(14) ?
C4"' C5"' C6"' C1"' -.2(3) ?
C2"' C1"' C6"' C5"' -.9(3) ?
C3" C1"' C6"' C5"' 179.48(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21132633
