##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-[3-(4-Chlorophenyl)pyrazol-5-yl]-1-(2-hydroxy-4-methoxyphenyl)ethanone
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H15 Cl N2 O3'
_chemical_formula_sum     'C18 H15 Cl N2 O3'
_chemical_formula_iupac     'C18 H15 Cl N2 O3'
_chemical_formula_weight     342.77
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C 2 /c'
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'
_cell_length_a     30.1055(18)
_cell_length_b     7.5383(11)
_cell_length_c     13.8612(14)
_cell_angle_alpha     90.00
_cell_angle_beta     90.338(4)
_cell_angle_gamma     90.00
_cell_volume     3145.7(6)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     3596
_cell_measurement_theta_min     2.71
_cell_measurement_theta_max     27.00
_cell_measurement_temperature     200(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     yellow
_exptl_crystal_size_max      .40
_exptl_crystal_size_mid      .40
_exptl_crystal_size_min      .08
_exptl_crystal_density_diffrn     1.448
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1424
_exptl_absorpt_coefficient_mu      .262
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min      .9024
_exptl_absorpt_correction_T_max      .9793
_exptl_special_details
;The temperature of the crystal was controlled using the Oxford Cryosystem
Cryostream Cooler (Cosier & Glazer, 1986).  Data were collected over a
hemisphere of reciprocal space, by a combination of three sets of exposures.
Each set had a different φ angle for the crystal and each exposure of 10 s
covered 0.3° in ω. The crystal to detector distance was 5.01 cm.   Crystal
decay was monitored by repeating the initial frames at the end of the data
collection and analyzing the duplicate reflections.
;
_diffrn_ambient_temperature     200(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71073
_diffrn_radiation_source     'normal-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Siemens SMART CCD area-detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     8.192
_diffrn_reflns_number     8778
_diffrn_reflns_av_R_equivalents      .0368
_diffrn_reflns_av_sigmaI/netI      .0505
_diffrn_reflns_theta_min     2.71
_diffrn_reflns_theta_max     27.00
_diffrn_reflns_theta_full     27.00
_diffrn_measured_fraction_theta_max      .996
_diffrn_measured_fraction_theta_full      .996
_diffrn_reflns_limit_h_min     -38
_diffrn_reflns_limit_h_max     34
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     10
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3425
_reflns_number_gt     2145
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .0730
_refine_ls_R_factor_gt      .0420
_refine_ls_wR_factor_ref      .1052
_refine_ls_goodness_of_fit_ref      .913
_refine_ls_restrained_S_all      .913
_refine_ls_number_reflns     3425
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
             'calc w = 1/[σ²(Fo²)+(0.0562P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_shift/su_max     <0.001
_refine_ls_shift/su_mean      .000
_refine_diff_density_max      .228
_refine_diff_density_min      -.266
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'SMART (Siemens, 1994)'
_computing_cell_refinement     'SAINT (Siemens, 1995)'
_computing_data_reduction     SAINT
_computing_structure_solution     'SHELXS97 (Sheldrick, 1990)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL/PC (Siemens, 1994)'
_computing_publication_material     SHELXTL/PC
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
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    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_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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_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_
    _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)
data_global
_journal_date_recd_electronic     2001-10-04
_journal_date_accepted     2001-10-15
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2001
_journal_volume     57
_journal_issue     11
_journal_page_first     o1084
_journal_page_last     o1086
_journal_paper_category     EO
_publ_contact_author_name     'Dr W. Errington'
_publ_contact_author_address
;
Department of Chemistry
University of Warwick
Coventry CV4 7AL
England
;
_publ_contact_author_email     w.errington@warwick.ac.uk
_publ_contact_author_fax     '02476 524112'
_publ_contact_author_phone     '02476 524803'
_publ_section_title
;
2-[3-(4-Chlorophenyl)pyrazol-5-yl]-1-(2-hydroxy-4-methoxyphenyl)ethanone
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Errington, William' .
; Department of Chemistry
University of Warwick
Coventry CV4 7AL
England
;
    'Kumar, Rajesh' .
;Department of Chemistry
University of Delhi
Delhi 110 007
India
;
    'Kumar, Naresh' .
;Department of Chemistry
University of Delhi
Delhi 110 007
India
;
    'Parmar, Virinder S.' .
;Department of Chemistry
University of Delhi
Delhi 110 007
India
;
    'Roy, Sucharita' .
;Department of Chemistry
University of Delhi
Delhi 110 007
India
;
