##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, 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 2.4.    #
#                                                                            #
# 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/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
3-[1-(4-Sulfamoylphenyl)-5-p-tolyl-1H-pyrazol-3-yl]propanoic acid
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H19 N3 O4 S'
_chemical_formula_sum     'C19 H19 N3 O4 S'
_chemical_formula_iupac     'C19 H19 N3 O4 S'
_chemical_formula_weight     385.43
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     5.8382(14)
_cell_length_b     12.582(3)
_cell_length_c     13.279(3)
_cell_angle_alpha     106.928(3)
_cell_angle_beta     97.777(3)
_cell_angle_gamma     101.077(3)
_cell_volume     896.5(4)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     3944
_cell_measurement_theta_min     2.75
_cell_measurement_theta_max     26.0
_cell_measurement_temperature     115(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.52
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.428
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     404
_exptl_absorpt_coefficient_mu     0.212
_exptl_absorpt_correction_type     numerical
_exptl_absorpt_process_details     '(SADABS Version 2008/1; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.8977
_exptl_absorpt_correction_T_max     0.9889
_exptl_special_details
;
4,6-dioxo-6-p-tolylhexanoic acid
1.1 M of NaHMDS solution (56.8 ml, 62.5 mmol) and THF (100 ml) were
added to a nitrogen-filled dry round-bottomed flask containing a stirrer and
addition funnel maintained at 253 K. 4'-Methylacetophenone (8.386 g,) in THF
(50 ml) was added to this solution slowly over 5 min and the solution was
stirred at 253 K for 30 min. Succinic anhydride (2.5 g, 25 mmol) in THF
(100 ml) was added to this solution. It was stirred for 1 h at 253 K, allowed
to warm to room temperature and stirred overnight. At this time, 3 N aqueous
HCl (50 ml) and Et₂O (250 ml) were added. The layers were separated, and the
Et₂O/THF layer was extracted with 1 N NaOH (2 × 50 ml). The base
extracts were combined and acidified to the cloudpoint (approximately pH 2)
with 3 N aqueous HCl. The precipitate which formed was collected by filtration
and dried under high vacuum. The residue was recrystallized from EtOAc.
4,6-Dioxo-6-p-tolylhexanoic acid, C₁₃H₁₄O₄, white solid (yield
1.93 g, 33%). Mass calculated: 234.25; mass observed: LCQ-ESI MS 235.0.
;
_diffrn_ambient_temperature     115(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART 1000 CCD area-detector'
_diffrn_measurement_method     'thin-slice ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6690
_diffrn_reflns_av_R_equivalents     0.0254
_diffrn_reflns_av_sigmaI/netI     0.0351
_diffrn_reflns_theta_min     1.64
_diffrn_reflns_theta_max     25.53
_diffrn_reflns_theta_full     25.53
_diffrn_measured_fraction_theta_max     0.987
_diffrn_measured_fraction_theta_full     0.987
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     16
_diffrn_standards_decay_%     ?
_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 >
σ(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     3300
_reflns_number_gt     2824
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0452
_refine_ls_R_factor_gt     0.0374
_refine_ls_wR_factor_gt     0.1020
_refine_ls_wR_factor_ref     0.1090
_refine_ls_goodness_of_fit_ref     1.063
_refine_ls_restrained_S_all     1.063
_refine_ls_number_reflns     3300
_refine_ls_number_parameters     320
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0648P)²+0.3322P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.426
_refine_diff_density_min     -0.408
_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' 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'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 2007)'
_computing_cell_refinement     'SAINT (Bruker, 2007)'
_computing_data_reduction     'SAINT (Bruker, 2007)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP3 for Windows (Farrugia, 1997) and Mercury (Version 2.2; Macrae
et al.,  2008)
;
_computing_publication_material
                                  'SHELXTL (Sheldrick, 2008) and local programs'
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 -0.48826(7) 0.25029(4) 0.42341(3) 0.01551(15) Uani d . 1 . .
    O O1 -0.6249(2) 0.15155(11) 0.33376(10) 0.0221(3) Uani d . 1 . .
    O O2 -0.6121(2) 0.32605(11) 0.48363(10) 0.0209(3) Uani d . 1 . .
    O O3 0.8431(2) 1.01701(11) 0.38423(11) 0.0269(3) Uani d . 1 . .
    O O4 1.1563(2) 0.94718(12) 0.34640(12) 0.0247(3) Uani d . 1 . .
    H H4O 1.222(5) 1.021(3) 0.354(2) 0.054(8) Uiso d . 1 . .
    N N1 0.2549(3) 0.63100(12) 0.27877(12) 0.0171(3) Uani d . 1 . .
    N N2 0.1831(3) 0.51422(12) 0.23132(12) 0.0164(3) Uani d . 1 . .
    N N3 -0.3459(3) 0.20193(15) 0.50397(13) 0.0191(4) Uani d . 1 . .
    H H3A -0.286(4) 0.250(2) 0.563(2) 0.028(6) Uiso d . 1 . .
    H H3B -0.278(4) 0.150(2) 0.475(2) 0.040(7) Uiso d . 1 . .
    C C1 0.2966(3) 0.47763(16) 0.14826(14) 0.0175(4) Uani d . 1 . .
    C C2 0.4473(3) 0.57394(16) 0.14405(15) 0.0195(4) Uani d . 1 . .
    H H2 0.554(4) 0.5750(17) 0.0932(17) 0.021(5) Uiso d . 1 . .
    C C3 0.4159(3) 0.66676(15) 0.22625(14) 0.0171(4) Uani d . 1 . .
    C C4 0.0243(3) 0.45057(15) 0.27776(13) 0.0156(4) Uani d . 1 . .
    C C5 0.0334(3) 0.33912(16) 0.27229(14) 0.0175(4) Uani d . 1 . .
    H H5 0.149(3) 0.3030(16) 0.2403(16) 0.013(5) Uiso d . 1 . .
    C C6 -0.1226(3) 0.27852(16) 0.31774(14) 0.0175(4) Uani d . 1 . .
    H H6 -0.112(3) 0.2031(18) 0.3141(16) 0.018(5) Uiso d . 1 . .
    C C7 -0.2840(3) 0.33043(15) 0.36936(14) 0.0154(4) Uani d . 1 . .
    C C8 -0.2889(3) 0.44215(15) 0.37791(14) 0.0180(4) Uani d . 1 . .
    H H8 -0.402(4) 0.4767(17) 0.4124(17) 0.019(5) Uiso d . 1 . .
    C C9 -0.1349(3) 0.50225(16) 0.33127(14) 0.0180(4) Uani d . 1 . .
    H H9 -0.143(3) 0.5755(18) 0.3359(16) 0.018(5) Uiso d . 1 . .
    C C10 0.2531(3) 0.35711(15) 0.07841(14) 0.0168(4) Uani d . 1 . .
    C C11 0.4297(3) 0.29761(17) 0.08549(15) 0.0214(4) Uani d . 1 . .
    H H11 0.578(4) 0.334(2) 0.1343(19) 0.032(6) Uiso d . 1 . .
    C C12 0.3909(4) 0.18445(17) 0.02208(15) 0.0225(4) Uani d . 1 . .
    H H12 0.516(4) 0.142(2) 0.029(2) 0.041(7) Uiso d . 1 . .
    C C13 0.1770(3) 0.12691(16) -0.05111(14) 0.0203(4) Uani d . 1 . .
    C C14 0.0036(4) 0.18796(17) -0.06031(15) 0.0227(4) Uani d . 1 . .
    H H14 -0.143(4) 0.151(2) -0.114(2) 0.034(6) Uiso d . 1 . .
    C C15 0.0396(3) 0.30120(17) 0.00393(15) 0.0211(4) Uani d . 1 . .
    H H15 -0.085(4) 0.3428(19) -0.0031(18) 0.027(6) Uiso d . 1 . .
    C C16 0.5447(3) 0.79016(16) 0.25976(16) 0.0187(4) Uani d . 1 . .
    H H16A 0.452(4) 0.8383(19) 0.3009(18) 0.028(6) Uiso d . 1 . .
    H H16B 0.557(4) 0.8101(18) 0.1985(18) 0.024(6) Uiso d . 1 . .
    C C17 0.7966(3) 0.81288(16) 0.32558(16) 0.0198(4) Uani d . 1 . .
    H H17A 0.890(4) 0.7658(18) 0.2871(17) 0.020(5) Uiso d . 1 . .
    H H17B 0.792(4) 0.7959(18) 0.3901(19) 0.026(6) Uiso d . 1 . .
    C C18 0.9303(3) 0.93609(15) 0.35570(14) 0.0177(4) Uani d . 1 . .
    C C19 0.1375(4) 0.00314(17) -0.11757(17) 0.0266(5) Uani d . 1 . .
    H H19A 0.155(4) -0.042(2) -0.071(2) 0.035(6) Uiso d . 1 . .
    H H19B 0.250(4) -0.008(2) -0.165(2) 0.038(7) Uiso d . 1 . .
    H H19C -0.017(5) -0.027(2) -0.164(2) 0.054(8) Uiso d . 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    S1 O1 . 1.4485(13) ?
    S1 O2 . 1.4313(13) ?
    S1 N3 . 1.5931(17) ?
    S1 C7 . 1.7735(18) ?
    O3 C18 . 1.211(2) ?
    O4 H4O . 0.90(3) ?
    O4 C18 . 1.326(2) ?
    N1 N2 . 1.373(2) ?
    N1 C3 . 1.330(2) ?
    N2 C1 . 1.374(2) ?
    N2 C4 . 1.428(2) ?
    N3 H3A . 0.82(3) ?
    N3 H3B . 0.85(3) ?
    C1 C2 . 1.374(3) ?
    C1 C10 . 1.481(2) ?
    C2 H2 . 0.98(2) ?
    C2 C3 . 1.408(2) ?
    C3 C16 . 1.494(3) ?
    C4 C5 . 1.394(3) ?
    C4 C9 . 1.390(3) ?
    C5 H5 . 0.96(2) ?
    C5 C6 . 1.387(3) ?
    C6 H6 . 0.95(2) ?
    C6 C7 . 1.391(3) ?
    C7 C8 . 1.383(3) ?
    C8 H8 . 0.95(2) ?
    C8 C9 . 1.388(3) ?
    C9 H9 . 0.92(2) ?
    C10 C11 . 1.394(3) ?
    C10 C15 . 1.397(3) ?
    C11 H11 . 0.95(2) ?
    C11 C12 . 1.383(3) ?
    C12 H12 . 0.99(3) ?
    C12 C13 . 1.394(3) ?
    C13 C14 . 1.396(3) ?
    C13 C19 . 1.505(3) ?
    C14 H14 . 0.97(2) ?
    C14 C15 . 1.389(3) ?
    C15 H15 . 0.98(2) ?
    C16 H16A . 0.98(2) ?
    C16 H16B . 0.93(2) ?
    C16 C17 . 1.534(3) ?
    C17 H17A . 0.97(2) ?
    C17 H17B . 0.94(2) ?
    C17 C18 . 1.504(3) ?
    C19 H19A . 0.96(3) ?
    C19 H19B . 0.98(3) ?
    C19 H19C . 0.96(3) ?
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
    O1 S1 O2 . . 118.72(8) ?
    O1 S1 N3 . . 106.37(9) ?
    O1 S1 C7 . . 105.96(8) ?
    O2 S1 N3 . . 107.94(9) ?
    O2 S1 C7 . . 108.10(8) ?
    N3 S1 C7 . . 109.54(9) ?
    H4O O4 C18 . . 109.3(18) ?
    N2 N1 C3 . . 105.55(14) ?
    N1 N2 C1 . . 111.17(14) ?
    N1 N2 C4 . . 118.11(14) ?
    C1 N2 C4 . . 130.52(15) ?
    S1 N3 H3A . . 113.0(16) ?
    S1 N3 H3B . . 116.1(17) ?
    H3A N3 H3B . . 121(2) ?
    N2 C1 C2 . . 106.25(16) ?
    N2 C1 C10 . . 124.67(16) ?
    C2 C1 C10 . . 129.06(17) ?
    C1 C2 H2 . . 125.3(12) ?
    C1 C2 C3 . . 106.23(17) ?
    H2 C2 C3 . . 128.5(12) ?
    N1 C3 C2 . . 110.79(16) ?
    N1 C3 C16 . . 120.90(16) ?
    C2 C3 C16 . . 128.24(17) ?
    N2 C4 C5 . . 120.44(16) ?
    N2 C4 C9 . . 119.17(16) ?
    C5 C4 C9 . . 120.37(16) ?
    C4 C5 H5 . . 122.3(12) ?
    C4 C5 C6 . . 119.62(17) ?
    H5 C5 C6 . . 118.0(12) ?
    C5 C6 H6 . . 118.3(12) ?
    C5 C6 C7 . . 119.45(17) ?
    H6 C6 C7 . . 122.2(12) ?
    S1 C7 C6 . . 118.87(14) ?
    S1 C7 C8 . . 119.94(14) ?
    C6 C7 C8 . . 121.18(16) ?
    C7 C8 H8 . . 120.7(12) ?
    C7 C8 C9 . . 119.33(17) ?
    H8 C8 C9 . . 119.9(12) ?
    C4 C9 C8 . . 120.00(17) ?
    C4 C9 H9 . . 121.7(13) ?
    C8 C9 H9 . . 118.3(13) ?
    C1 C10 C11 . . 119.66(16) ?
    C1 C10 C15 . . 121.67(17) ?
    C11 C10 C15 . . 118.66(17) ?
    C10 C11 H11 . . 120.2(14) ?
    C10 C11 C12 . . 120.48(18) ?
    H11 C11 C12 . . 119.3(14) ?
    C11 C12 H12 . . 120.0(15) ?
    C11 C12 C13 . . 121.46(18) ?
    H12 C12 C13 . . 118.6(15) ?
    C12 C13 C14 . . 117.82(17) ?
    C12 C13 C19 . . 120.40(18) ?
    C14 C13 C19 . . 121.78(18) ?
    C13 C14 H14 . . 119.1(14) ?
    C13 C14 C15 . . 121.17(18) ?
    H14 C14 C15 . . 119.7(14) ?
    C10 C15 C14 . . 120.36(18) ?
    C10 C15 H15 . . 119.4(13) ?
    C14 C15 H15 . . 120.2(13) ?
    C3 C16 H16A . . 110.0(13) ?
    C3 C16 H16B . . 108.4(13) ?
    C3 C16 C17 . . 111.73(15) ?
    H16A C16 H16B . . 107.5(18) ?
    H16A C16 C17 . . 110.5(13) ?
    H16B C16 C17 . . 108.6(13) ?
    C16 C17 H17A . . 112.0(12) ?
    C16 C17 H17B . . 111.4(14) ?
    C16 C17 C18 . . 111.88(15) ?
    H17A C17 H17B . . 106.2(18) ?
    H17A C17 C18 . . 107.9(12) ?
    H17B C17 C18 . . 107.2(13) ?
    O3 C18 O4 . . 123.06(17) ?
    O3 C18 C17 . . 124.42(17) ?
    O4 C18 C17 . . 112.52(15) ?
    C13 C19 H19A . . 110.1(14) ?
    C13 C19 H19B . . 111.8(14) ?
    C13 C19 H19C . . 112.4(16) ?
    H19A C19 H19B . . 108(2) ?
    H19A C19 H19C . . 109(2) ?
    H19B C19 H19C . . 105(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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C3 N1 N2 C1 . . . . -0.96(19) ?
    C3 N1 N2 C4 . . . . 174.50(15) ?
    N1 N2 C1 C2 . . . . 0.9(2) ?
    N1 N2 C1 C10 . . . . -177.90(16) ?
    C4 N2 C1 C2 . . . . -173.84(17) ?
    C4 N2 C1 C10 . . . . 7.4(3) ?
    N2 C1 C2 C3 . . . . -0.5(2) ?
    C10 C1 C2 C3 . . . . 178.26(18) ?
    N2 N1 C3 C2 . . . . 0.6(2) ?
    N2 N1 C3 C16 . . . . -176.73(15) ?
    C1 C2 C3 N1 . . . . -0.1(2) ?
    C1 C2 C3 C16 . . . . 177.01(18) ?
    N1 N2 C4 C5 . . . . -148.48(16) ?
    N1 N2 C4 C9 . . . . 29.7(2) ?
    C1 N2 C4 C5 . . . . 25.9(3) ?
    C1 N2 C4 C9 . . . . -155.91(18) ?
    N2 C4 C5 C6 . . . . -179.90(15) ?
    C9 C4 C5 C6 . . . . 2.0(3) ?
    C4 C5 C6 C7 . . . . -0.8(3) ?
    C5 C6 C7 S1 . . . . 178.08(13) ?
    C5 C6 C7 C8 . . . . -1.2(3) ?
    O1 S1 C7 C6 . . . . -59.09(16) ?
    O1 S1 C7 C8 . . . . 120.17(15) ?
    O2 S1 C7 C6 . . . . 172.65(13) ?
    O2 S1 C7 C8 . . . . -8.09(17) ?
    N3 S1 C7 C6 . . . . 55.27(16) ?
    N3 S1 C7 C8 . . . . -125.47(15) ?
    S1 C7 C8 C9 . . . . -177.27(13) ?
    C6 C7 C8 C9 . . . . 2.0(3) ?
    C7 C8 C9 C4 . . . . -0.8(3) ?
    N2 C4 C9 C8 . . . . -179.32(15) ?
    C5 C4 C9 C8 . . . . -1.2(3) ?
    N2 C1 C10 C11 . . . . -110.9(2) ?
    N2 C1 C10 C15 . . . . 69.9(2) ?
    C2 C1 C10 C11 . . . . 70.6(3) ?
    C2 C1 C10 C15 . . . . -108.6(2) ?
    C1 C10 C11 C12 . . . . 179.00(17) ?
    C15 C10 C11 C12 . . . . -1.8(3) ?
    C10 C11 C12 C13 . . . . 0.6(3) ?
    C11 C12 C13 C14 . . . . 1.4(3) ?
    C11 C12 C13 C19 . . . . -178.80(18) ?
    C12 C13 C14 C15 . . . . -2.2(3) ?
    C19 C13 C14 C15 . . . . 177.99(18) ?
    C13 C14 C15 C10 . . . . 1.0(3) ?
    C1 C10 C15 C14 . . . . -179.82(17) ?
    C11 C10 C15 C14 . . . . 1.0(3) ?
    N1 C3 C16 C17 . . . . 100.8(2) ?
    C2 C3 C16 C17 . . . . -76.0(2) ?
    C3 C16 C17 C18 . . . . 177.72(16) ?
    C16 C17 C18 O3 . . . . 40.4(3) ?
    C16 C17 C18 O4 . . . . -138.85(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
    _geom_hbond_publ_flag
    O4 H4O O1 1_765 0.90(3) 1.83(3) 2.705(2) 164(3) y
    N3 H3A N1 2_566 0.82(3) 2.16(3) 2.941(2) 160(2) y
    N3 H3B O3 1_445 0.85(3) 2.07(3) 2.910(2) 170(2) y
    C8 H8 O2 2_466 0.95(2) 2.44(2) 3.167(2) 132.6(16) y
    C16 H16A O4 1_455 0.98(2) 2.44(2) 3.387(2) 162.1(18) n
data_II
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
Bis{3-[5-(4-bromophenyl)-1-(4-sulfamoylphenyl)-1H-pyrazol-3-yl]propanoic
acid} dichloromethane 0.72-solvate diethyl ether solvate monohydrate
;
_chemical_name_common     ?
_chemical_formula_moiety
                        '2 C18 H16 Br N3 O4 S , 0.72 C H2 Cl2 , C4 H10 O , H2 O'
_chemical_formula_sum     'C40.72 H45.44 Br2 Cl1.45 N6 O10 S2'
_chemical_formula_iupac
                        '2 C18 H16 Br N3 O4 S , 0.72 C H2 Cl2 , C4 H10 O , H2 O'
_chemical_formula_weight     1054.11
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
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     49.255(15)
_cell_length_b     11.702(3)
_cell_length_c     16.181(5)
_cell_angle_alpha     90.00
_cell_angle_beta     95.567(4)
_cell_angle_gamma     90.00
_cell_volume     9283(5)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     8341
_cell_measurement_theta_min     2.22
_cell_measurement_theta_max     25.50
_cell_measurement_temperature     115(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.51
_exptl_crystal_size_mid     0.31
_exptl_crystal_size_min     0.05
_exptl_crystal_density_diffrn     1.508
_exptl_crystal_density_meas     0
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     4307
_exptl_absorpt_coefficient_mu     1.981
_exptl_absorpt_correction_type     numerical
_exptl_absorpt_process_details     '(SADABS, Version 2008/1; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.4316
_exptl_absorpt_correction_T_max     0.9075
_exptl_special_details
;
6-(4-bromophenyl)-4, 6-dioxohexanoic acid
1.1 M of NaHMDS solution (56.8 ml, 62.5 mmol) and THF (100 ml) were
added to a nitrogen-filled dry round-bottomed flask containing a stirrer and
addition funnel, and maintained at 253 K. 4'-Bromoacetophenone (12.44 g, 62.5
mmol) in THF (50 ml) was added to this solution slowly over 5 min and the
solution was stirred at 253 K for 30 min. Succinic anhydride (2.5 g, 25 mmol)
in THF (100 ml) was added to this solution. It was stirred for 1 h at 253 K,
allowed to warm to room temperature and stirred overnight. At this time, 3 N
aqueous HCl 50 ml and Et₂O 250 ml was added. The layers were separated, and
the Et₂O/THF layer was extracted with 1 N NaOH (2 × 50 ml). The base
extracts were combined and acidified to the cloudpoint (approximately pH 2)
with 3 N aqueous HCl. The precipitate which formed was collected by filtration
and dried under high vacuum. The residue was recrystallized from EtOAc.
6-(4-bromophenyl)-4,6-dioxohexanoic acid, C₁₂H₁₁BrO₄, white solid (yield
3.63 g, 48.5%). Mass calculated: 299.12; mass observed: LCQ-ESI MS 298.8.
;
_diffrn_ambient_temperature     115(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART 1000 CCD area-detector'
_diffrn_measurement_method     'thin-slice ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     23405
_diffrn_reflns_av_R_equivalents     0.0325
_diffrn_reflns_av_sigmaI/netI     0.0385
_diffrn_reflns_theta_min     1.79
_diffrn_reflns_theta_max     25.53
_diffrn_reflns_theta_full     25.53
_diffrn_measured_fraction_theta_max     0.992
_diffrn_measured_fraction_theta_full     0.992
_diffrn_reflns_limit_h_min     -51
_diffrn_reflns_limit_h_max     59
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     19
_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 >
σ(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     8605
_reflns_number_gt     6781
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0526
_refine_ls_R_factor_gt     0.0371
_refine_ls_wR_factor_gt     0.0971
_refine_ls_wR_factor_ref     0.1047
_refine_ls_goodness_of_fit_ref     1.015
_refine_ls_restrained_S_all     1.015
_refine_ls_number_reflns     8605
_refine_ls_number_parameters     595
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
      'calc w = 1/[σ²(Fo²)+(0.0604P)²+10.1055P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.844
_refine_diff_density_min     -0.433
_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' 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'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Br' 'Br' -0.2901 2.4595
                         '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'
_computing_data_collection     'SMART (Bruker, 2007)'
_computing_cell_refinement     'SAINT (Bruker, 2007)'
_computing_data_reduction     'SAINT (Bruker, 2007)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP3 for Windows (Farrugia, 1997) and Mercury (Version 2.2; Macrae
et al.,  2008)
;
_computing_publication_material
                                  'SHELXTL (Sheldrick, 2008) and local programs'
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Br Br1 0.053486(6) 0.58331(3) 0.22339(2) 0.03752(11) Uani d . 1 . .
    S S1 0.171923(13) 1.14155(6) 0.29404(4) 0.01934(15) Uani d . 1 . .
    O O1 0.15423(4) 1.19084(17) 0.34983(12) 0.0281(5) Uani d . 1 . .
    O O2 0.16411(4) 1.15060(17) 0.20642(12) 0.0257(4) Uani d . 1 . .
    O O3 0.28741(4) 0.31142(16) 0.49517(11) 0.0214(4) Uani d . 1 . .
    O O4 0.29017(4) 0.26197(17) 0.36315(11) 0.0229(4) Uani d D 1 . .
    H H4O 0.3038(4) 0.228(2) 0.3827(18) 0.028 Uiso d D 1 . .
    N N1 0.21614(4) 0.61947(18) 0.40372(13) 0.0166(5) Uani d . 1 . .
    N N2 0.19044(4) 0.64946(18) 0.37132(13) 0.0161(5) Uani d . 1 . .
    N N3 0.20128(5) 1.2017(2) 0.31365(16) 0.0244(5) Uani d . 1 . .
    H H3A 0.2139(7) 1.169(3) 0.292(2) 0.029 Uiso d . 1 . .
    H H3B 0.2063(6) 1.204(3) 0.367(2) 0.029 Uiso d . 1 . .
    C C1 0.17324(5) 0.5572(2) 0.36694(15) 0.0160(5) Uani d . 1 . .
    C C2 0.18858(5) 0.4656(2) 0.39690(16) 0.0180(6) Uani d . 1 . .
    H H2 0.1825 0.3890 0.4017 0.022 Uiso calc R 1 . .
    C C3 0.21497(5) 0.5077(2) 0.41900(15) 0.0166(5) Uani d . 1 . .
    C C4 0.18517(5) 0.7672(2) 0.35227(15) 0.0152(5) Uani d . 1 . .
    C C5 0.17103(5) 0.7975(2) 0.27739(15) 0.0180(6) Uani d . 1 . .
    H H5 0.1644 0.7404 0.2389 0.022 Uiso calc R 1 . .
    C C6 0.16672(5) 0.9125(2) 0.25928(16) 0.0192(6) Uani d . 1 . .
    H H6 0.1572 0.9350 0.2080 0.023 Uiso calc R 1 . .
    C C7 0.17644(5) 0.9940(2) 0.31673(15) 0.0162(5) Uani d . 1 . .
    C C8 0.19055(5) 0.9633(2) 0.39217(16) 0.0193(6) Uani d . 1 . .
    H H8 0.1970 1.0204 0.4309 0.023 Uiso calc R 1 . .
    C C9 0.19502(5) 0.8490(2) 0.41004(16) 0.0187(6) Uani d . 1 . .
    H H9 0.2047 0.8265 0.4611 0.022 Uiso calc R 1 . .
    C C10 0.14423(5) 0.5628(2) 0.33579(15) 0.0169(5) Uani d . 1 . .
    C C11 0.13328(6) 0.4779(2) 0.28209(16) 0.0219(6) Uani d . 1 . .
    H H11 0.1445 0.4165 0.2676 0.026 Uiso calc R 1 . .
    C C12 0.10613(6) 0.4818(3) 0.24947(17) 0.0256(6) Uani d . 1 . .
    H H12 0.0988 0.4241 0.2125 0.031 Uiso calc R 1 . .
    C C13 0.09004(5) 0.5712(3) 0.27178(16) 0.0227(6) Uani d . 1 . .
    C C14 0.10003(5) 0.6541(2) 0.32799(17) 0.0217(6) Uani d . 1 . .
    H H14 0.0884 0.7132 0.3443 0.026 Uiso calc R 1 . .
    C C15 0.12708(5) 0.6495(2) 0.35991(16) 0.0191(6) Uani d . 1 . .
    H H15 0.1341 0.7057 0.3986 0.023 Uiso calc R 1 . .
    C C16 0.24003(5) 0.4457(2) 0.45524(16) 0.0187(6) Uani d . 1 . .
    H H16A 0.2346 0.3838 0.4920 0.022 Uiso calc R 1 . .
    H H16B 0.2519 0.4995 0.4895 0.022 Uiso calc R 1 . .
    C C17 0.25610(5) 0.3946(2) 0.38805(16) 0.0191(6) Uani d . 1 . .
    H H17A 0.2435 0.3494 0.3493 0.023 Uiso calc R 1 . .
    H H17B 0.2635 0.4575 0.3560 0.023 Uiso calc R 1 . .
    C C18 0.27922(5) 0.3193(2) 0.42215(16) 0.0164(5) Uani d . 1 . .
    Br Br51 0.492625(6) 1.03361(3) 0.61729(2) 0.04198(12) Uani d . 1 . .
    S S51 0.399305(14) 1.63701(6) 0.43441(4) 0.01941(15) Uani d . 1 . .
    O O51 0.38078(4) 1.70006(16) 0.47994(12) 0.0281(5) Uani d . 1 . .
    O O52 0.42773(4) 1.63621(17) 0.46228(12) 0.0285(5) Uani d . 1 . .
    O O53 0.25523(4) 0.86444(18) 0.33345(13) 0.0316(5) Uani d . 1 . .
    O O54 0.26711(4) 0.71210(17) 0.41108(12) 0.0248(4) Uani d D 1 . .
    H H54O 0.2518(3) 0.686(3) 0.4019(19) 0.030 Uiso d D 1 . .
    N N51 0.33516(4) 1.13208(19) 0.40102(13) 0.0169(5) Uani d . 1 . .
    N N52 0.36116(4) 1.15427(18) 0.43420(13) 0.0159(5) Uani d . 1 . .
    N N53 0.39626(5) 1.6870(2) 0.34092(14) 0.0217(5) Uani d . 1 . .
    H H53A 0.3798(7) 1.688(3) 0.3222(19) 0.026 Uiso d . 1 . .
    H H53B 0.4078(7) 1.662(3) 0.315(2) 0.026 Uiso d . 1 . .
    C C51 0.37494(5) 1.0551(2) 0.45528(15) 0.0169(5) Uani d . 1 . .
    C C52 0.35705(5) 0.9671(2) 0.43323(16) 0.0183(6) Uani d . 1 . .
    H H52 0.3605 0.8875 0.4393 0.022 Uiso calc R 1 . .
    C C53 0.33273(5) 1.0185(2) 0.40016(15) 0.0160(5) Uani d . 1 . .
    C C54 0.37061(5) 1.2695(2) 0.43335(15) 0.0153(5) Uani d . 1 . .
    C C55 0.39497(5) 1.2957(2) 0.40020(16) 0.0185(6) Uani d . 1 . .
    H H55 0.4054 1.2371 0.3777 0.022 Uiso calc R 1 . .
    C C56 0.40379(5) 1.4081(2) 0.40053(16) 0.0191(6) Uani d . 1 . .
    H H56 0.4206 1.4271 0.3796 0.023 Uiso calc R 1 . .
    C C57 0.38785(5) 1.4933(2) 0.43187(15) 0.0176(6) Uani d . 1 . .
    C C58 0.36334(5) 1.4673(2) 0.46264(16) 0.0189(6) Uani d . 1 . .
    H H58 0.3525 1.5263 0.4827 0.023 Uiso calc R 1 . .
    C C59 0.35481(5) 1.3545(2) 0.46392(15) 0.0173(5) Uani d . 1 . .
    H H59 0.3382 1.3355 0.4857 0.021 Uiso calc R 1 . .
    C C60 0.40282(5) 1.0513(2) 0.49616(16) 0.0184(6) Uani d . 1 . .
    C C61 0.41998(5) 0.9615(2) 0.47758(17) 0.0213(6) Uani d . 1 . .
    H H61 0.4134 0.9044 0.4391 0.026 Uiso calc R 1 . .
    C C62 0.44630(6) 0.9549(3) 0.51439(18) 0.0270(7) Uani d . 1 . .
    H H62 0.4578 0.8932 0.5019 0.032 Uiso calc R 1 . .
    C C63 0.45587(5) 1.0388(3) 0.56956(18) 0.0268(7) Uani d . 1 . .
    C C64 0.43928(6) 1.1266(3) 0.59094(18) 0.0290(7) Uani d . 1 . .
    H H64 0.4460 1.1825 0.6302 0.035 Uiso calc R 1 . .
    C C65 0.41279(6) 1.1325(2) 0.55485(17) 0.0233(6) Uani d . 1 . .
    H H65 0.4012 1.1922 0.5700 0.028 Uiso calc R 1 . .
    C C66 0.30632(5) 0.9671(2) 0.36527(17) 0.0200(6) Uani d . 1 . .
    H H66A 0.3059 0.9649 0.3040 0.024 Uiso calc R 1 . .
    H H66B 0.2912 1.0172 0.3793 0.024 Uiso calc R 1 . .
    C C67 0.30137(5) 0.8481(2) 0.39636(16) 0.0171(5) Uani d . 1 . .
    H H67A 0.3136 0.7940 0.3710 0.020 Uiso calc R 1 . .
    H H67B 0.3059 0.8459 0.4573 0.020 Uiso calc R 1 . .
    C C68 0.27235(5) 0.8103(2) 0.37624(15) 0.0174(6) Uani d . 1 . .
    O O70 0.06540(4) 1.0870(2) 0.26448(13) 0.0363(5) Uani d . 1 . .
    C C73 0.10180(7) 0.9800(3) 0.3327(2) 0.0388(8) Uani d . 1 . .
    H H73A 0.1087 0.9627 0.2794 0.058 Uiso calc R 1 . .
    H H73B 0.1064 0.9172 0.3717 0.058 Uiso calc R 1 . .
    H H73C 0.1101 1.0508 0.3553 0.058 Uiso calc R 1 . .
    C C70 0.03701(7) 1.1042(4) 0.2460(3) 0.0520(10) Uani d . 1 . .
    H H70A 0.0283 1.1140 0.2982 0.062 Uiso calc R 1 . .
    H H70B 0.0288 1.0365 0.2166 0.062 Uiso calc R 1 . .
    C C72 0.07185(7) 0.9939(3) 0.3204(2) 0.0425(9) Uani d . 1 . .
    H H72A 0.0633 0.9227 0.2972 0.051 Uiso calc R 1 . .
    H H72B 0.0646 1.0094 0.3743 0.051 Uiso calc R 1 . .
    C C71 0.03203(7) 1.2075(3) 0.1930(2) 0.0465(9) Uani d . 1 . .
    H H71A 0.0408 1.2738 0.2214 0.070 Uiso calc R 1 . .
    H H71B 0.0124 1.2211 0.1829 0.070 Uiso calc R 1 . .
    H H71C 0.0397 1.1957 0.1400 0.070 Uiso calc R 1 . .
    Cl Cl1 -0.02610(3) 0.88634(17) 0.49011(12) 0.0792(7) Uani d P 0.722(3) . .
    Cl Cl2 0.00563(4) 0.81360(17) 0.35698(10) 0.0813(7) Uani d P 0.722(3) . .
    C C74 0.00165(12) 0.8135(6) 0.4615(4) 0.0620(16) Uani d P 0.722(3) . .
    H H74A 0.0004 0.7332 0.4800 0.074 Uiso calc PR 0.722(3) . .
    H H74B 0.0183 0.8468 0.4916 0.074 Uiso calc PR 0.722(3) . .
    O O7 0.24801(5) 1.0920(2) 0.26813(14) 0.0340(5) Uani d . 1 . .
    H H7A 0.2520(7) 1.026(3) 0.289(2) 0.041 Uiso d . 1 . .
    H H7B 0.2636(8) 1.145(3) 0.277(2) 0.041 Uiso d . 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    Br1 C13 . 1.898(3) ?
    S1 O1 . 1.435(2) ?
    S1 O2 . 1.436(2) ?
    S1 N3 . 1.612(3) ?
    S1 C7 . 1.775(3) ?
    O3 C18 . 1.214(3) ?
    O4 H4O . 0.816(10) ?
    O4 C18 . 1.324(3) ?
    N1 N2 . 1.368(3) ?
    N1 C3 . 1.333(3) ?
    N2 C1 . 1.370(3) ?
    N2 C4 . 1.430(3) ?
    N3 H3A . 0.84(3) ?
    N3 H3B . 0.88(3) ?
    C1 C2 . 1.372(4) ?
    C1 C10 . 1.470(4) ?
    C2 H2 . 0.950 ?
    C2 C3 . 1.403(4) ?
    C3 C16 . 1.501(4) ?
    C4 C5 . 1.384(4) ?
    C4 C9 . 1.392(4) ?
    C5 H5 . 0.950 ?
    C5 C6 . 1.390(4) ?
    C6 H6 . 0.950 ?
    C6 C7 . 1.384(4) ?
    C7 C8 . 1.392(4) ?
    C8 H8 . 0.950 ?
    C8 C9 . 1.383(4) ?
    C9 H9 . 0.950 ?
    C10 C11 . 1.393(4) ?
    C10 C15 . 1.400(4) ?
    C11 H11 . 0.950 ?
    C11 C12 . 1.390(4) ?
    C12 H12 . 0.950 ?
    C12 C13 . 1.381(4) ?
    C13 C14 . 1.387(4) ?
    C14 H14 . 0.950 ?
    C14 C15 . 1.383(4) ?
    C15 H15 . 0.950 ?
    C16 H16A . 0.990 ?
    C16 H16B . 0.990 ?
    C16 C17 . 1.527(4) ?
    C17 H17A . 0.990 ?
    C17 H17B . 0.990 ?
    C17 C18 . 1.502(4) ?
    Br51 C63 . 1.899(3) ?
    S51 O51 . 1.432(2) ?
    S51 O52 . 1.429(2) ?
    S51 N53 . 1.615(2) ?
    S51 C57 . 1.773(3) ?
    O53 C68 . 1.216(3) ?
    O54 H54O . 0.814(10) ?
    O54 C68 . 1.317(3) ?
    N51 N52 . 1.365(3) ?
    N51 C53 . 1.334(3) ?
    N52 C51 . 1.371(3) ?
    N52 C54 . 1.427(3) ?
    N53 H53A . 0.84(3) ?
    N53 H53B . 0.79(3) ?
    C51 C52 . 1.380(4) ?
    C51 C60 . 1.466(4) ?
    C52 H52 . 0.950 ?
    C52 C53 . 1.400(4) ?
    C53 C66 . 1.494(4) ?
    C54 C55 . 1.395(4) ?
    C54 C59 . 1.384(4) ?
    C55 H55 . 0.950 ?
    C55 C56 . 1.386(4) ?
    C56 H56 . 0.950 ?
    C56 C57 . 1.394(4) ?
    C57 C58 . 1.384(4) ?
    C58 H58 . 0.950 ?
    C58 C59 . 1.387(4) ?
    C59 H59 . 0.950 ?
    C60 C61 . 1.399(4) ?
    C60 C65 . 1.398(4) ?
    C61 H61 . 0.950 ?
    C61 C62 . 1.375(4) ?
    C62 H62 . 0.950 ?
    C62 C63 . 1.379(4) ?
    C63 C64 . 1.377(4) ?
    C64 H64 . 0.950 ?
    C64 C65 . 1.378(4) ?
    C65 H65 . 0.950 ?
    C66 H66A . 0.990 ?
    C66 H66B . 0.990 ?
    C66 C67 . 1.509(4) ?
    C67 H67A . 0.990 ?
    C67 H67B . 0.990 ?
    C67 C68 . 1.501(3) ?
    O70 C70 . 1.416(4) ?
    O70 C72 . 1.432(4) ?
    C73 H73A . 0.980 ?
    C73 H73B . 0.980 ?
    C73 H73C . 0.980 ?
    C73 C72 . 1.478(5) ?
    C70 H70A . 0.990 ?
    C70 H70B . 0.990 ?
    C70 C71 . 1.489(5) ?
    C72 H72A . 0.990 ?
    C72 H72B . 0.990 ?
    C71 H71A . 0.980 ?
    C71 H71B . 0.980 ?
    C71 H71C . 0.980 ?
    Cl1 C74 . 1.712(6) ?
    Cl2 C74 . 1.722(6) ?
    C74 H74A . 0.990 ?
    C74 H74B . 0.990 ?
    O7 H7A . 0.86(4) ?
    O7 H7B . 0.98(4) ?
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
    O1 S1 O2 . . 118.06(12) ?
    O1 S1 N3 . . 106.76(14) ?
    O1 S1 C7 . . 109.42(12) ?
    O2 S1 N3 . . 108.15(13) ?
    O2 S1 C7 . . 106.98(12) ?
    N3 S1 C7 . . 106.99(13) ?
    H4O O4 C18 . . 110(2) ?
    N2 N1 C3 . . 105.5(2) ?
    N1 N2 C1 . . 111.2(2) ?
    N1 N2 C4 . . 118.1(2) ?
    C1 N2 C4 . . 130.5(2) ?
    S1 N3 H3A . . 114(2) ?
    S1 N3 H3B . . 111(2) ?
    H3A N3 H3B . . 107(3) ?
    N2 C1 C2 . . 106.3(2) ?
    N2 C1 C10 . . 123.9(2) ?
    C2 C1 C10 . . 129.8(2) ?
    C1 C2 H2 . . 126.9 ?
    C1 C2 C3 . . 106.3(2) ?
    H2 C2 C3 . . 126.9 ?
    N1 C3 C2 . . 110.7(2) ?
    N1 C3 C16 . . 119.8(2) ?
    C2 C3 C16 . . 129.5(2) ?
    N2 C4 C5 . . 120.1(2) ?
    N2 C4 C9 . . 118.3(2) ?
    C5 C4 C9 . . 121.7(2) ?
    C4 C5 H5 . . 120.4 ?
    C4 C5 C6 . . 119.1(2) ?
    H5 C5 C6 . . 120.4 ?
    C5 C6 H6 . . 120.3 ?
    C5 C6 C7 . . 119.3(2) ?
    H6 C6 C7 . . 120.3 ?
    S1 C7 C6 . . 120.2(2) ?
    S1 C7 C8 . . 118.3(2) ?
    C6 C7 C8 . . 121.5(2) ?
    C7 C8 H8 . . 120.4 ?
    C7 C8 C9 . . 119.3(2) ?
    H8 C8 C9 . . 120.4 ?
    C4 C9 C8 . . 119.1(2) ?
    C4 C9 H9 . . 120.4 ?
    C8 C9 H9 . . 120.4 ?
    C1 C10 C11 . . 119.1(2) ?
    C1 C10 C15 . . 122.0(2) ?
    C11 C10 C15 . . 118.9(2) ?
    C10 C11 H11 . . 119.6 ?
    C10 C11 C12 . . 120.9(3) ?
    H11 C11 C12 . . 119.6 ?
    C11 C12 H12 . . 120.6 ?
    C11 C12 C13 . . 118.8(3) ?
    H12 C12 C13 . . 120.6 ?
    Br1 C13 C12 . . 119.6(2) ?
    Br1 C13 C14 . . 118.7(2) ?
    C12 C13 C14 . . 121.7(2) ?
    C13 C14 H14 . . 120.5 ?
    C13 C14 C15 . . 119.1(3) ?
    H14 C14 C15 . . 120.5 ?
    C10 C15 C14 . . 120.7(2) ?
    C10 C15 H15 . . 119.7 ?
    C14 C15 H15 . . 119.7 ?
    C3 C16 H16A . . 109.2 ?
    C3 C16 H16B . . 109.2 ?
    C3 C16 C17 . . 112.0(2) ?
    H16A C16 H16B . . 107.9 ?
    H16A C16 C17 . . 109.2 ?
    H16B C16 C17 . . 109.2 ?
    C16 C17 H17A . . 108.9 ?
    C16 C17 H17B . . 108.9 ?
    C16 C17 C18 . . 113.3(2) ?
    H17A C17 H17B . . 107.7 ?
    H17A C17 C18 . . 108.9 ?
    H17B C17 C18 . . 108.9 ?
    O3 C18 O4 . . 122.9(2) ?
    O3 C18 C17 . . 124.8(2) ?
    O4 C18 C17 . . 112.3(2) ?
    O51 S51 O52 . . 119.66(13) ?
    O51 S51 N53 . . 106.84(13) ?
    O51 S51 C57 . . 106.46(12) ?
    O52 S51 N53 . . 107.28(13) ?
    O52 S51 C57 . . 107.51(12) ?
    N53 S51 C57 . . 108.74(12) ?
    H54O O54 C68 . . 117(2) ?
    N52 N51 C53 . . 105.9(2) ?
    N51 N52 C51 . . 111.1(2) ?
    N51 N52 C54 . . 118.1(2) ?
    C51 N52 C54 . . 130.4(2) ?
    S51 N53 H53A . . 110(2) ?
    S51 N53 H53B . . 110(2) ?
    H53A N53 H53B . . 122(3) ?
    N52 C51 C52 . . 106.2(2) ?
    N52 C51 C60 . . 123.9(2) ?
    C52 C51 C60 . . 129.8(2) ?
    C51 C52 H52 . . 126.9 ?
    C51 C52 C53 . . 106.2(2) ?
    H52 C52 C53 . . 126.9 ?
    N51 C53 C52 . . 110.6(2) ?
    N51 C53 C66 . . 118.6(2) ?
    C52 C53 C66 . . 130.8(2) ?
    N52 C54 C55 . . 120.3(2) ?
    N52 C54 C59 . . 118.7(2) ?
    C55 C54 C59 . . 121.0(2) ?
    C54 C55 H55 . . 120.4 ?
    C54 C55 C56 . . 119.2(2) ?
    H55 C55 C56 . . 120.4 ?
    C55 C56 H56 . . 120.2 ?
    C55 C56 C57 . . 119.5(2) ?
    H56 C56 C57 . . 120.2 ?
    S51 C57 C56 . . 119.8(2) ?
    S51 C57 C58 . . 119.1(2) ?
    C56 C57 C58 . . 121.1(2) ?
    C57 C58 H58 . . 120.3 ?
    C57 C58 C59 . . 119.4(2) ?
    H58 C58 C59 . . 120.3 ?
    C54 C59 C58 . . 119.8(2) ?
    C54 C59 H59 . . 120.1 ?
    C58 C59 H59 . . 120.1 ?
    C51 C60 C61 . . 119.0(2) ?
    C51 C60 C65 . . 122.5(2) ?
    C61 C60 C65 . . 118.4(2) ?
    C60 C61 H61 . . 119.6 ?
    C60 C61 C62 . . 120.8(3) ?
    H61 C61 C62 . . 119.6 ?
    C61 C62 H62 . . 120.4 ?
    C61 C62 C63 . . 119.3(3) ?
    H62 C62 C63 . . 120.4 ?
    Br51 C63 C62 . . 119.5(2) ?
    Br51 C63 C64 . . 119.2(2) ?
    C62 C63 C64 . . 121.3(3) ?
    C63 C64 H64 . . 120.3 ?
    C63 C64 C65 . . 119.4(3) ?
    H64 C64 C65 . . 120.3 ?
    C60 C65 C64 . . 120.6(3) ?
    C60 C65 H65 . . 119.7 ?
    C64 C65 H65 . . 119.7 ?
    C53 C66 H66A . . 108.7 ?
    C53 C66 H66B . . 108.7 ?
    C53 C66 C67 . . 114.1(2) ?
    H66A C66 H66B . . 107.6 ?
    H66A C66 C67 . . 108.7 ?
    H66B C66 C67 . . 108.7 ?
    C66 C67 H67A . . 109.1 ?
    C66 C67 H67B . . 109.1 ?
    C66 C67 C68 . . 112.4(2) ?
    H67A C67 H67B . . 107.9 ?
    H67A C67 C68 . . 109.1 ?
    H67B C67 C68 . . 109.1 ?
    O53 C68 O54 . . 123.0(2) ?
    O53 C68 C67 . . 124.3(2) ?
    O54 C68 C67 . . 112.7(2) ?
    C70 O70 C72 . . 113.3(2) ?
    H73A C73 H73B . . 109.5 ?
    H73A C73 H73C . . 109.5 ?
    H73A C73 C72 . . 109.5 ?
    H73B C73 H73C . . 109.5 ?
    H73B C73 C72 . . 109.5 ?
    H73C C73 C72 . . 109.5 ?
    O70 C70 H70A . . 109.7 ?
    O70 C70 H70B . . 109.7 ?
    O70 C70 C71 . . 110.0(3) ?
    H70A C70 H70B . . 108.2 ?
    H70A C70 C71 . . 109.7 ?
    H70B C70 C71 . . 109.7 ?
    O70 C72 C73 . . 109.0(3) ?
    O70 C72 H72A . . 109.9 ?
    O70 C72 H72B . . 109.9 ?
    C73 C72 H72A . . 109.9 ?
    C73 C72 H72B . . 109.9 ?
    H72A C72 H72B . . 108.3 ?
    C70 C71 H71A . . 109.5 ?
    C70 C71 H71B . . 109.5 ?
    C70 C71 H71C . . 109.5 ?
    H71A C71 H71B . . 109.5 ?
    H71A C71 H71C . . 109.5 ?
    H71B C71 H71C . . 109.5 ?
    Cl1 C74 Cl2 . . 115.8(3) ?
    Cl1 C74 H74A . . 108.3 ?
    Cl1 C74 H74B . . 108.3 ?
    Cl2 C74 H74A . . 108.3 ?
    Cl2 C74 H74B . . 108.3 ?
    H74A C74 H74B . . 107.4 ?
    H7A O7 H7B . . 111(3) ?
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
    C3 N1 N2 C1 . . . . 0.4(3) ?
    C3 N1 N2 C4 . . . . 177.1(2) ?
    N1 N2 C1 C2 . . . . -0.5(3) ?
    N1 N2 C1 C10 . . . . 179.2(2) ?
    C4 N2 C1 C2 . . . . -176.6(2) ?
    C4 N2 C1 C10 . . . . 3.1(4) ?
    N2 C1 C2 C3 . . . . 0.3(3) ?
    C10 C1 C2 C3 . . . . -179.4(2) ?
    N2 N1 C3 C2 . . . . -0.2(3) ?
    N2 N1 C3 C16 . . . . 179.9(2) ?
    C1 C2 C3 N1 . . . . 0.0(3) ?
    C1 C2 C3 C16 . . . . 179.8(2) ?
    N1 N2 C4 C5 . . . . 134.3(2) ?
    N1 N2 C4 C9 . . . . -44.5(3) ?
    C1 N2 C4 C5 . . . . -49.7(4) ?
    C1 N2 C4 C9 . . . . 131.4(3) ?
    N2 C4 C5 C6 . . . . -178.4(2) ?
    C9 C4 C5 C6 . . . . 0.4(4) ?
    C4 C5 C6 C7 . . . . -0.6(4) ?
    C5 C6 C7 S1 . . . . 178.47(19) ?
    C5 C6 C7 C8 . . . . 0.3(4) ?
    O1 S1 C7 C6 . . . . 114.7(2) ?
    O1 S1 C7 C8 . . . . -67.1(2) ?
    O2 S1 C7 C6 . . . . -14.3(2) ?
    O2 S1 C7 C8 . . . . 164.0(2) ?
    N3 S1 C7 C6 . . . . -130.0(2) ?
    N3 S1 C7 C8 . . . . 48.2(2) ?
    S1 C7 C8 C9 . . . . -178.05(19) ?
    C6 C7 C8 C9 . . . . 0.2(4) ?
    C7 C8 C9 C4 . . . . -0.3(4) ?
    N2 C4 C9 C8 . . . . 178.9(2) ?
    C5 C4 C9 C8 . . . . 0.0(4) ?
    N2 C1 C10 C11 . . . . 136.1(3) ?
    N2 C1 C10 C15 . . . . -45.3(4) ?
    C2 C1 C10 C11 . . . . -44.3(4) ?
    C2 C1 C10 C15 . . . . 134.3(3) ?
    C1 C10 C11 C12 . . . . -178.2(2) ?
    C15 C10 C11 C12 . . . . 3.2(4) ?
    C10 C11 C12 C13 . . . . -0.5(4) ?
    C11 C12 C13 Br1 . . . . 176.5(2) ?
    C11 C12 C13 C14 . . . . -2.4(4) ?
    Br1 C13 C14 C15 . . . . -176.4(2) ?
    C12 C13 C14 C15 . . . . 2.6(4) ?
    C13 C14 C15 C10 . . . . 0.2(4) ?
    C1 C10 C15 C14 . . . . 178.4(2) ?
    C11 C10 C15 C14 . . . . -3.1(4) ?
    N1 C3 C16 C17 . . . . -92.2(3) ?
    C2 C3 C16 C17 . . . . 87.9(3) ?
    C3 C16 C17 C18 . . . . -172.5(2) ?
    C16 C17 C18 O3 . . . . -10.5(4) ?
    C16 C17 C18 O4 . . . . 170.1(2) ?
    C53 N51 N52 C51 . . . . -0.9(3) ?
    C53 N51 N52 C54 . . . . 172.4(2) ?
    N51 N52 C51 C52 . . . . 1.0(3) ?
    N51 N52 C51 C60 . . . . -176.8(2) ?
    C54 N52 C51 C52 . . . . -171.3(2) ?
    C54 N52 C51 C60 . . . . 10.9(4) ?
    N52 C51 C52 C53 . . . . -0.7(3) ?
    C60 C51 C52 C53 . . . . 176.9(3) ?
    N52 N51 C53 C52 . . . . 0.4(3) ?
    N52 N51 C53 C66 . . . . -178.8(2) ?
    C51 C52 C53 N51 . . . . 0.2(3) ?
    C51 C52 C53 C66 . . . . 179.3(3) ?
    N51 N52 C54 C55 . . . . -127.4(2) ?
    N51 N52 C54 C59 . . . . 50.9(3) ?
    C51 N52 C54 C55 . . . . 44.5(4) ?
    C51 N52 C54 C59 . . . . -137.2(3) ?
    N52 C54 C55 C56 . . . . -179.6(2) ?
    C59 C54 C55 C56 . . . . 2.1(4) ?
    C54 C55 C56 C57 . . . . -1.7(4) ?
    C55 C56 C57 S51 . . . . 178.8(2) ?
    C55 C56 C57 C58 . . . . 0.0(4) ?
    O51 S51 C57 C56 . . . . -172.0(2) ?
    O51 S51 C57 C58 . . . . 6.8(2) ?
    O52 S51 C57 C56 . . . . -42.6(2) ?
    O52 S51 C57 C58 . . . . 136.2(2) ?
    N53 S51 C57 C56 . . . . 73.2(2) ?
    N53 S51 C57 C58 . . . . -108.0(2) ?
    S51 C57 C58 C59 . . . . -177.40(19) ?
    C56 C57 C58 C59 . . . . 1.4(4) ?
    N52 C54 C59 C58 . . . . -179.0(2) ?
    C55 C54 C59 C58 . . . . -0.7(4) ?
    C57 C58 C59 C54 . . . . -1.0(4) ?
    N52 C51 C60 C61 . . . . -146.7(3) ?
    N52 C51 C60 C65 . . . . 35.0(4) ?
    C52 C51 C60 C61 . . . . 36.0(4) ?
    C52 C51 C60 C65 . . . . -142.2(3) ?
    C51 C60 C61 C62 . . . . 179.8(2) ?
    C65 C60 C61 C62 . . . . -1.8(4) ?
    C60 C61 C62 C63 . . . . -0.7(4) ?
    C61 C62 C63 Br51 . . . . -177.5(2) ?
    C61 C62 C63 C64 . . . . 2.6(4) ?
    Br51 C63 C64 C65 . . . . 178.3(2) ?
    C62 C63 C64 C65 . . . . -1.8(4) ?
    C63 C64 C65 C60 . . . . -0.9(4) ?
    C51 C60 C65 C64 . . . . -179.1(3) ?
    C61 C60 C65 C64 . . . . 2.6(4) ?
    N51 C53 C66 C67 . . . . -157.0(2) ?
    C52 C53 C66 C67 . . . . 24.0(4) ?
    C53 C66 C67 C68 . . . . 166.6(2) ?
    C66 C67 C68 O53 . . . . 6.2(4) ?
    C66 C67 C68 O54 . . . . -172.8(2) ?
    C72 O70 C70 C71 . . . . 175.6(3) ?
    C70 O70 C72 C73 . . . . 177.5(3) ?
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
    _geom_hbond_publ_flag
    O7 H7A O53 . 0.86(4) 2.02(4) 2.874(3) 171(3) y
    O7 H7B O4 1_565 0.98(4) 2.28(4) 3.164(3) 149(3) y
    O4 H4O N51 1_545 0.816(10) 1.910(13) 2.708(3) 165(3) y
    O54 H54O N1 . 0.814(10) 1.924(12) 2.726(3) 169(3) y
    N3 H3A O7 . 0.84(3) 1.97(3) 2.796(4) 166(3) y
    N3 H3B O3 7_566 0.88(3) 2.22(3) 3.094(3) 170(3) y
    N53 H53A O2 4 0.84(3) 2.21(3) 3.028(3) 165(3) y
    N53 H53B O70 4 0.79(3) 2.12(3) 2.910(3) 172(3) y
    C8 H8 O3 7_566 0.95 2.39 3.327(3) 168.5 y
    C9 H9 O54 7_566 0.95 2.42 3.364(3) 173.2 y
    C15 H15 O51 7_576 0.95 2.43 3.187(3) 136.8 y
    C52 H52 O51 1_545 0.95 2.47 3.395(3) 164.0 y
    C59 H59 O3 1_565 0.95 2.53 3.443(3) 160.1 y
    C5 H5 N51 4_545 0.95 2.60 3.465(3) 152.0 n
    C17 H17B O7 4_545 0.99 2.57 3.415(4) 143.1 n
    C67 H67A O2 4_545 0.99 2.42 3.398(3) 169.3 n
    C71 H71C O52 4_545 0.98 2.51 3.451(4) 160.1 n
    C67 H67A O2 4_545 0.99 2.42 3.398(3) 169.3 n
    C71 H71C O52 4_545 0.98 2.51 3.451(4) 160.1 n
data_global
_journal_date_recd_electronic     2009-04-10
_journal_date_accepted     2009-05-04
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2009
_journal_volume     65
_journal_issue      6
_journal_page_first     o296
_journal_page_last     o299
_journal_paper_category     FO
_journal_coeditor_code     FN3023
_publ_contact_author_name     'Dr Gary S. Nichol'
_publ_contact_author_address
;
Department of Chemistry
University of Arizona
1306 E. University Boulevard
Tucson
AZ 85721
USA
;
_publ_contact_author_email     gsnichol@email.arizona.edu
_publ_contact_author_fax     '520 621 8407'
_publ_contact_author_phone     '520 621 4168'
_publ_section_title
;\
3-[1-(4-Sulfamoylphenyl)-5-p-tolyl-1H-pyrazol-3-yl]propanoic acid
and
bis{3-[5-(4-bromophenyl)-1-(4-sulfamoylphenyl)-1H-pyrazol-3-yl]\
propanoic acid} dichloromethane 0.72-solvate diethyl ether solvate
monohydrate
;
loop_
    _publ_author_name
    _publ_author_address
    'Kumarasinghe, Isuru R.'
;
Department of Chemistry
University of Arizona
1306 E. University Boulevard
Tucson
AZ 85721
USA
;
    'Hruby, Victor J.'
;
Department of Chemistry
University of Arizona
1306 E. University Boulevard
Tucson
AZ 85721
USA
;
    'Nichol, Gary S.'
;
Department of Chemistry
University of Arizona
1306 E. University Boulevard
Tucson
AZ 85721
USA
;
