#------------------------------------------------------------------------------
#$Date: 2020-03-04 08:02:57 +0200 (Wed, 04 Mar 2020) $
#$Revision: 248731 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/33/2243305.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_2243305
loop_
_publ_author_name
'Metwally, Nadia H.'
'Elgemeie, Galal H.'
'Jones, Peter G.'
_publ_section_title
;
 Crystal structure of ethyl
 2-(5-amino-1-benzenesulfonyl-3-oxo-2,3-dihydro-1H-pyrazol-2-yl)acetate
;
_journal_coeditor_code           NR2077
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              481
_journal_page_last               483
_journal_paper_doi               10.1107/S2056989020002674
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C13 H15 N3 O5 S'
_chemical_formula_moiety         'C13 H15 N3 O5 S'
_chemical_formula_sum            'C13 H15 N3 O5 S'
_chemical_formula_weight         325.34
_chemical_name_systematic
;
Ethyl
2-(5-amino-1-benzenesulfonyl-3-oxo-2,3-dihydro-1H-pyrazol-2-yl)acetate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 104.521(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2139(4)
_cell_length_b                   8.8122(4)
_cell_length_c                   18.3486(7)
_cell_measurement_reflns_used    16307
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.2980
_cell_measurement_theta_min      2.5690
_cell_volume                     1442.22(11)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
XP (Siemens, 1994)
;
_computing_publication_material
;
SHELXL2017 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2017 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.1419
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            74051
_diffrn_reflns_theta_full        30.000
_diffrn_reflns_theta_max         30.030
_diffrn_reflns_theta_min         2.283
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.253
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.313
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         4193
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0351
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0304P)²+0.8673P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0853
_reflns_number_gt                3708
_reflns_number_total             4193
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            nr2077sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2243305
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.917
_shelx_estimated_absorpt_t_max   0.963
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_disorder_assembly
_atom_site_disorder_group
S S1 0.21827(3) 0.35269(3) 0.02872(2) 0.01371(8) Uani d 1 . .
N N1 0.33782(11) 0.22191(12) 0.08270(6) 0.01304(19) Uani d 1 . .
N N2 0.25215(11) 0.11750(12) 0.11476(6) 0.0142(2) Uani d 1 . .
N N3 0.54212(13) 0.38935(14) 0.13239(7) 0.0187(2) Uani d 1 . .
H H01 0.547(2) 0.411(2) 0.0871(11) 0.029(5) Uiso d 1 . .
H H02 0.602(2) 0.431(2) 0.1716(11) 0.027(4) Uiso d 1 . .
O O1 0.31374(10) 0.45322(11) 0.00110(5) 0.01845(19) Uani d 1 . .
O O2 0.10901(10) 0.26285(11) -0.02197(5) 0.01864(19) Uani d 1 . .
O O3 0.27967(10) 0.00832(11) 0.23139(5) 0.0201(2) Uani d 1 . .
O O4 0.32627(13) -0.17922(12) -0.00343(6) 0.0282(2) Uani d 1 . .
O O5 0.46016(11) -0.09414(11) 0.10922(5) 0.0206(2) Uani d 1 . .
C C3 0.32177(13) 0.10511(15) 0.19250(7) 0.0151(2) Uani d 1 . .
C C4 0.43781(13) 0.21500(15) 0.20999(7) 0.0159(2) Uani d 1 . .
H H4 0.497420 0.238013 0.258957 0.019 Uiso calc 1 . .
C C5 0.44943(13) 0.28208(14) 0.14470(7) 0.0139(2) Uani d 1 . .
C C6 0.13579(13) 0.44475(14) 0.09267(7) 0.0148(2) Uani d 1 . .
C C7 0.00733(14) 0.38207(15) 0.10759(7) 0.0187(2) Uani d 1 . .
H H7 -0.038852 0.294967 0.081123 0.022 Uiso calc 1 . .
C C8 -0.05126(15) 0.45024(17) 0.16212(8) 0.0219(3) Uani d 1 . .
H H8 -0.137945 0.408731 0.173735 0.026 Uiso calc 1 . .
C C9 0.01580(15) 0.57863(17) 0.19982(8) 0.0223(3) Uani d 1 . .
H H9 -0.025685 0.624603 0.236866 0.027 Uiso calc 1 . .
C C10 0.14298(15) 0.64049(16) 0.18388(7) 0.0206(3) Uani d 1 . .
H H10 0.187588 0.728962 0.209625 0.025 Uiso calc 1 . .
C C11 0.20494(14) 0.57298(15) 0.13031(7) 0.0173(2) Uani d 1 . .
H H11 0.292829 0.613492 0.119539 0.021 Uiso calc 1 . .
C C12 0.20730(14) -0.01978(15) 0.07046(7) 0.0189(2) Uani d 1 . .
H H12A 0.136124 0.008368 0.022367 0.023 Uiso calc 1 . .
H H12B 0.153689 -0.087254 0.098087 0.023 Uiso calc 1 . .
C C13 0.33651(15) -0.10706(15) 0.05324(7) 0.0185(2) Uani d 1 . .
C C14 0.59637(16) -0.16389(17) 0.09781(8) 0.0225(3) Uani d 1 . .
H H14A 0.602432 -0.149340 0.045151 0.027 Uiso calc 1 . .
H H14B 0.596692 -0.274125 0.108255 0.027 Uiso calc 1 . .
C C15 0.72666(16) -0.08824(19) 0.15109(8) 0.0263(3) Uani d 1 . .
H H15A 0.724485 0.020857 0.140513 0.039 Uiso calc 1 . .
H H15B 0.820526 -0.131624 0.144566 0.039 Uiso calc 1 . .
H H15C 0.720047 -0.104563 0.202995 0.039 Uiso calc 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'
S S 0.1246 0.1234 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 S1 O1 . . 120.63(6) y
O2 S1 N1 . . 104.37(5) ?
O1 S1 N1 . . 104.88(5) ?
O2 S1 C6 . . 109.90(6) ?
O1 S1 C6 . . 111.12(6) ?
N1 S1 C6 . . 104.30(5) y
C5 N1 N2 . . 105.78(9) ?
C5 N1 S1 . . 115.93(8) ?
N2 N1 S1 . . 109.08(7) ?
C3 N2 N1 . . 107.87(9) ?
C3 N2 C12 . . 119.46(10) ?
N1 N2 C12 . . 114.36(10) ?
C5 N3 H01 . . 120.9(12) ?
C5 N3 H02 . . 117.4(12) ?
H01 N3 H02 . . 121.5(17) ?
C13 O5 C14 . . 116.94(10) ?
O3 C3 N2 . . 120.48(12) ?
O3 C3 C4 . . 131.97(12) ?
N2 C3 C4 . . 107.53(10) ?
C5 C4 C3 . . 108.53(11) ?
C5 C4 H4 . . 125.7 ?
C3 C4 H4 . . 125.7 ?
N3 C5 C4 . . 130.69(12) ?
N3 C5 N1 . . 119.50(11) ?
C4 C5 N1 . . 109.80(11) ?
C11 C6 C7 . . 121.97(12) ?
C11 C6 S1 . . 119.17(9) ?
C7 C6 S1 . . 118.76(10) ?
C8 C7 C6 . . 118.25(12) ?
C8 C7 H7 . . 120.9 ?
C6 C7 H7 . . 120.9 ?
C7 C8 C9 . . 120.49(12) ?
C7 C8 H8 . . 119.8 ?
C9 C8 H8 . . 119.8 ?
C8 C9 C10 . . 120.59(12) ?
C8 C9 H9 . . 119.7 ?
C10 C9 H9 . . 119.7 ?
C11 C10 C9 . . 119.97(13) ?
C11 C10 H10 . . 120.0 ?
C9 C10 H10 . . 120.0 ?
C10 C11 C6 . . 118.73(12) ?
C10 C11 H11 . . 120.6 ?
C6 C11 H11 . . 120.6 ?
N2 C12 C13 . . 114.18(10) ?
N2 C12 H12A . . 108.7 ?
C13 C12 H12A . . 108.7 ?
N2 C12 H12B . . 108.7 ?
C13 C12 H12B . . 108.7 ?
H12A C12 H12B . . 107.6 ?
O4 C13 O5 . . 125.29(13) ?
O4 C13 C12 . . 123.59(12) ?
O5 C13 C12 . . 111.11(11) ?
O5 C14 C15 . . 107.20(11) ?
O5 C14 H14A . . 110.3 ?
C15 C14 H14A . . 110.3 ?
O5 C14 H14B . . 110.3 ?
C15 C14 H14B . . 110.3 ?
H14A C14 H14B . . 108.5 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
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
S1 O2 . 1.4268(9) ?
S1 O1 . 1.4280(10) ?
S1 N1 . 1.7249(10) ?
S1 C6 . 1.7491(12) ?
N1 C5 . 1.4305(15) y
N1 N2 . 1.4313(14) y
N2 C3 . 1.4139(15) y
N2 C12 . 1.4583(16) ?
N3 C5 . 1.3306(16) y
N3 H01 . 0.866(19) ?
N3 H02 . 0.871(19) ?
O3 C3 . 1.2353(16) ?
O4 C13 . 1.2023(16) ?
O5 C13 . 1.3338(16) ?
O5 C14 . 1.4589(16) ?
C3 C4 . 1.4184(18) y
C4 C5 . 1.3640(17) y
C4 H4 . 0.9500 ?
C6 C11 . 1.3926(18) ?
C6 C7 . 1.3941(17) ?
C7 C8 . 1.3871(19) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.388(2) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.388(2) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.3883(18) ?
C10 H10 . 0.9500 ?
C11 H11 . 0.9500 ?
C12 C13 . 1.5156(19) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C14 C15 . 1.501(2) ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
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
N3 H01 O1 . 0.866(19) 2.355(19) 2.8296(15) 114.8(15) yes
N3 H01 O1 3_665 0.866(19) 2.593(19) 3.3644(15) 148.8(16) yes
N3 H02 O3 2_655 0.871(19) 1.961(19) 2.8257(15) 171.5(17) yes
C12 H12A O2 . 0.99 2.38 3.0214(16) 122.1 yes
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
O2 S1 N1 C5 . . . . -172.95(9) ?
O1 S1 N1 C5 . . . . 59.29(9) ?
C6 S1 N1 C5 . . . . -57.61(10) ?
O2 S1 N1 N2 . . . . -53.74(9) ?
O1 S1 N1 N2 . . . . 178.50(8) ?
C6 S1 N1 N2 . . . . 61.60(9) ?
C5 N1 N2 C3 . . . . -5.93(12) ?
S1 N1 N2 C3 . . . . -131.28(8) ?
C5 N1 N2 C12 . . . . -141.43(10) ?
S1 N1 N2 C12 . . . . 93.23(10) ?
N1 N2 C3 O3 . . . . -171.44(11) ?
C12 N2 C3 O3 . . . . -38.61(17) ?
N1 N2 C3 C4 . . . . 7.23(13) ?
C12 N2 C3 C4 . . . . 140.06(11) ?
O3 C3 C4 C5 . . . . 172.70(13) ?
N2 C3 C4 C5 . . . . -5.75(14) ?
C3 C4 C5 N3 . . . . -179.13(13) ?
C3 C4 C5 N1 . . . . 2.02(14) ?
N2 N1 C5 N3 . . . . -176.57(11) ?
S1 N1 C5 N3 . . . . -55.56(13) ?
N2 N1 C5 C4 . . . . 2.43(13) ?
S1 N1 C5 C4 . . . . 123.44(10) ?
O2 S1 C6 C11 . . . . -159.28(10) ?
O1 S1 C6 C11 . . . . -23.16(12) ?
N1 S1 C6 C11 . . . . 89.33(10) ?
O2 S1 C6 C7 . . . . 24.42(12) ?
O1 S1 C6 C7 . . . . 160.54(10) ?
N1 S1 C6 C7 . . . . -86.97(10) ?
C11 C6 C7 C8 . . . . -0.47(19) ?
S1 C6 C7 C8 . . . . 175.72(10) ?
C6 C7 C8 C9 . . . . 0.85(19) ?
C7 C8 C9 C10 . . . . -0.3(2) ?
C8 C9 C10 C11 . . . . -0.6(2) ?
C9 C10 C11 C6 . . . . 0.97(19) ?
C7 C6 C11 C10 . . . . -0.44(19) ?
S1 C6 C11 C10 . . . . -176.61(10) ?
C3 N2 C12 C13 . . . . -74.54(14) ?
N1 N2 C12 C13 . . . . 55.45(14) ?
C14 O5 C13 O4 . . . . 5.0(2) ?
C14 O5 C13 C12 . . . . -175.81(11) y
N2 C12 C13 O4 . . . . -147.96(13) ?
N2 C12 C13 O5 . . . . 32.79(15) ?
C13 O5 C14 C15 . . . . 158.95(12) y

_cod_database_fobs_code 2243305
