#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/84/2228416.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228416
loop_
_publ_author_name
'Loh, Wan-Sin'
'Fun, Hoong-Kun'
'Ragavan, R. Venkat'
'Vijayakumar, V.'
'Venkatesh, M.'
_publ_section_title
;
 5-Isobutyl-4-phenylsulfonyl-1H-pyrazol-3(2H)-one
;
_journal_coeditor_code           IS2619
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3050
_journal_page_last               o3051
_journal_paper_doi               10.1107/S1600536810044181
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H16 N2 O3 S'
_chemical_formula_moiety         'C13 H16 N2 O3 S'
_chemical_formula_sum            'C13 H16 N2 O3 S'
_chemical_formula_weight         280.34
_chemical_name_systematic
;
5-Isobutyl-4-phenylsulfonyl-1H-pyrazol-3(2H)-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.579(3)
_cell_angle_beta                 113.038(3)
_cell_angle_gamma                112.882(3)
_cell_formula_units_Z            4
_cell_length_a                   11.3423(8)
_cell_length_b                   11.9987(9)
_cell_length_c                   12.4657(9)
_cell_measurement_reflns_used    9939
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      35.03
_cell_measurement_theta_min      2.58
_cell_volume                     1344.42(18)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18458
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.90
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_T_max  0.9575
_exptl_absorpt_correction_T_min  0.8745
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.669
_refine_diff_density_min         -0.381
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5202
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0553P)²+1.2051P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1088
_reflns_number_gt                4816
_reflns_number_total             5202
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2619.cif
_cod_data_source_block           I
_cod_original_cell_volume        1344.42(17)
_cod_database_code               2228416
_cod_database_fobs_code          2228416
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1A 0.61779(4) 0.56939(4) 0.30323(4) 0.01287(12) Uani d . 1 . .
O O1A 0.52206(14) 0.62292(12) 0.29583(12) 0.0177(3) Uani d . 1 . .
O O2A 0.56191(14) 0.44944(12) 0.20809(11) 0.0176(3) Uani d . 1 . .
O O3A 0.81177(13) 0.88563(12) 0.44040(11) 0.0155(3) Uani d . 1 . .
N N1A 0.96797(17) 0.87383(15) 0.36853(14) 0.0144(3) Uani d . 1 . .
N N2A 0.97863(17) 0.77840(15) 0.30426(13) 0.0146(3) Uani d . 1 . .
C C1A 0.7407(2) 0.46688(18) 0.46562(17) 0.0190(4) Uani d . 1 . .
H H1AA 0.7415 0.4199 0.3996 0.023 Uiso calc R 1 . .
C C2A 0.7970(2) 0.45448(19) 0.58116(18) 0.0223(4) Uani d . 1 . .
H H2AA 0.8369 0.3998 0.5934 0.027 Uiso calc R 1 . .
C C3A 0.7936(2) 0.52380(19) 0.67853(17) 0.0221(4) Uani d . 1 . .
H H3AA 0.8317 0.5157 0.7561 0.027 Uiso calc R 1 . .
C C4A 0.7335(2) 0.60524(19) 0.66063(17) 0.0227(4) Uani d . 1 . .
H H4AA 0.7299 0.6499 0.7259 0.027 Uiso calc R 1 . .
C C5A 0.6789(2) 0.62047(18) 0.54597(17) 0.0192(4) Uani d . 1 . .
H H5AA 0.6405 0.6762 0.5341 0.023 Uiso calc R 1 . .
C C6A 0.68325(19) 0.55035(16) 0.44963(16) 0.0144(3) Uani d . 1 . .
C C7A 0.77240(19) 0.68499(17) 0.31001(15) 0.0137(3) Uani d . 1 . .
C C8A 0.84468(18) 0.82068(16) 0.37900(15) 0.0128(3) Uani d . 1 . .
C C9A 0.86263(19) 0.66367(17) 0.26817(15) 0.0132(3) Uani d . 1 . .
C C10A 0.84569(19) 0.54146(17) 0.19624(15) 0.0155(3) Uani d . 1 . .
H H10A 0.8084 0.4743 0.2277 0.019 Uiso calc R 1 . .
H H10B 0.9418 0.5559 0.2107 0.019 Uiso calc R 1 . .
C C11A 0.7416(2) 0.49321(18) 0.05437(16) 0.0190(4) Uani d . 1 . .
H H11A 0.6510 0.4944 0.0407 0.023 Uiso calc R 1 . .
C C12A 0.7026(3) 0.3539(2) -0.0044(2) 0.0394(6) Uani d . 1 . .
H H12A 0.6353 0.3223 -0.0922 0.059 Uiso calc R 1 . .
H H12B 0.6576 0.3006 0.0337 0.059 Uiso calc R 1 . .
H H12C 0.7905 0.3511 0.0084 0.059 Uiso calc R 1 . .
C C13A 0.8111(2) 0.5804(2) -0.00512(18) 0.0249(4) Uani d . 1 . .
H H13A 0.7427 0.5505 -0.0924 0.037 Uiso calc R 1 . .
H H13B 0.8986 0.5784 0.0054 0.037 Uiso calc R 1 . .
H H13C 0.8358 0.6675 0.0341 0.037 Uiso calc R 1 . .
S S1B 0.32612(5) 0.06328(4) 0.30231(4) 0.01364(12) Uani d . 1 . .
O O1B 0.44172(14) 0.19562(12) 0.37062(12) 0.0203(3) Uani d . 1 . .
O O2B 0.20554(14) 0.01636(13) 0.32778(12) 0.0184(3) Uani d . 1 . .
O O3B 0.18314(13) -0.24470(12) 0.26728(12) 0.0177(3) Uani d . 1 . .
N N1B 0.41780(16) -0.21360(15) 0.33582(14) 0.0156(3) Uani d . 1 . .
N N2B 0.55364(17) -0.11548(15) 0.36901(14) 0.0158(3) Uani d . 1 . .
C C1B 0.1298(2) -0.07887(19) 0.05619(17) 0.0221(4) Uani d . 1 . .
H H1BA 0.0925 -0.1462 0.0827 0.026 Uiso calc R 1 . .
C C2B 0.0666(2) -0.0952(2) -0.06954(19) 0.0300(5) Uani d . 1 . .
H H2BA -0.0139 -0.1743 -0.1280 0.036 Uiso calc R 1 . .
C C3B 0.1230(3) 0.0058(2) -0.10850(19) 0.0320(5) Uani d . 1 . .
H H3BA 0.0792 -0.0057 -0.1928 0.038 Uiso calc R 1 . .
C C4B 0.2432(3) 0.1227(2) -0.0231(2) 0.0304(5) Uani d . 1 . .
H H4BA 0.2810 0.1893 -0.0502 0.036 Uiso calc R 1 . .
C C5B 0.3091(2) 0.14218(19) 0.10415(19) 0.0224(4) Uani d . 1 . .
H H5BA 0.3904 0.2211 0.1623 0.027 Uiso calc R 1 . .
C C6B 0.2500(2) 0.04043(18) 0.14147(16) 0.0163(4) Uani d . 1 . .
C C7B 0.40072(19) -0.03787(17) 0.32486(15) 0.0135(3) Uani d . 1 . .
C C8B 0.31688(19) -0.17245(17) 0.30481(15) 0.0141(3) Uani d . 1 . .
C C9B 0.54630(19) -0.00867(17) 0.36371(15) 0.0139(3) Uani d . 1 . .
C C10B 0.68105(19) 0.11342(17) 0.39661(16) 0.0166(4) Uani d . 1 . .
H H10C 0.7581 0.1324 0.4788 0.020 Uiso calc R 1 . .
H H10D 0.6592 0.1840 0.4009 0.020 Uiso calc R 1 . .
C C11B 0.7392(2) 0.10832(19) 0.30404(17) 0.0207(4) Uani d . 1 . .
H H11B 0.7586 0.0355 0.2987 0.025 Uiso calc R 1 . .
C C12B 0.6260(2) 0.0862(3) 0.1743(2) 0.0346(5) Uani d . 1 . .
H H12D 0.6646 0.0825 0.1185 0.052 Uiso calc R 1 . .
H H12E 0.6043 0.1560 0.1777 0.052 Uiso calc R 1 . .
H H12F 0.5376 0.0060 0.1449 0.052 Uiso calc R 1 . .
C C13B 0.8834(2) 0.2320(2) 0.3531(2) 0.0273(4) Uani d . 1 . .
H H13D 0.9217 0.2272 0.2973 0.041 Uiso calc R 1 . .
H H13E 0.9528 0.2424 0.4342 0.041 Uiso calc R 1 . .
H H13F 0.8666 0.3047 0.3588 0.041 Uiso calc R 1 . .
H H1NA 1.035(3) 0.944(3) 0.412(2) 0.028(6) Uiso d . 1 . .
H H2NA 1.054(3) 0.795(2) 0.296(2) 0.032(7) Uiso d . 1 . .
H H1NB 0.407(3) -0.289(3) 0.332(2) 0.026(6) Uiso d . 1 . .
H H2NB 0.632(3) -0.125(2) 0.390(2) 0.026(6) Uiso d . 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
O2A S1A O1A . . 119.07(8) ?
O2A S1A C7A . . 108.50(8) ?
O1A S1A C7A . . 107.89(8) ?
O2A S1A C6A . . 108.27(8) ?
O1A S1A C6A . . 107.77(8) ?
C7A S1A C6A . . 104.39(8) ?
C8A N1A N2A . . 109.89(14) ?
C8A N1A H1NA . . 123.5(19) ?
N2A N1A H1NA . . 123.7(19) ?
C9A N2A N1A . . 110.01(15) ?
C9A N2A H2NA . . 128.6(17) ?
N1A N2A H2NA . . 121.2(17) ?
C2A C1A C6A . . 119.19(16) ?
C2A C1A H1AA . . 120.4 ?
C6A C1A H1AA . . 120.4 ?
C1A C2A C3A . . 119.87(18) ?
C1A C2A H2AA . . 120.1 ?
C3A C2A H2AA . . 120.1 ?
C2A C3A C4A . . 120.31(17) ?
C2A C3A H3AA . . 119.8 ?
C4A C3A H3AA . . 119.8 ?
C3A C4A C5A . . 120.56(17) ?
C3A C4A H4AA . . 119.7 ?
C5A C4A H4AA . . 119.7 ?
C6A C5A C4A . . 118.31(17) ?
C6A C5A H5AA . . 120.8 ?
C4A C5A H5AA . . 120.8 ?
C5A C6A C1A . . 121.74(16) ?
C5A C6A S1A . . 119.60(14) ?
C1A C6A S1A . . 118.65(13) ?
C9A C7A C8A . . 107.66(15) ?
C9A C7A S1A . . 127.02(14) ?
C8A C7A S1A . . 124.58(13) ?
O3A C8A N1A . . 123.49(16) ?
O3A C8A C7A . . 131.50(16) ?
N1A C8A C7A . . 105.00(14) ?
N2A C9A C7A . . 107.31(15) ?
N2A C9A C10A . . 121.56(15) ?
C7A C9A C10A . . 131.14(16) ?
C9A C10A C11A . . 113.81(14) ?
C9A C10A H10A . . 108.8 ?
C11A C10A H10A . . 108.8 ?
C9A C10A H10B . . 108.8 ?
C11A C10A H10B . . 108.8 ?
H10A C10A H10B . . 107.7 ?
C13A C11A C12A . . 111.09(17) ?
C13A C11A C10A . . 111.16(15) ?
C12A C11A C10A . . 109.05(16) ?
C13A C11A H11A . . 108.5 ?
C12A C11A H11A . . 108.5 ?
C10A C11A H11A . . 108.5 ?
C11A C12A H12A . . 109.5 ?
C11A C12A H12B . . 109.5 ?
H12A C12A H12B . . 109.5 ?
C11A C12A H12C . . 109.5 ?
H12A C12A H12C . . 109.5 ?
H12B C12A H12C . . 109.5 ?
C11A C13A H13A . . 109.5 ?
C11A C13A H13B . . 109.5 ?
H13A C13A H13B . . 109.5 ?
C11A C13A H13C . . 109.5 ?
H13A C13A H13C . . 109.5 ?
H13B C13A H13C . . 109.5 ?
O1B S1B O2B . . 118.68(8) ?
O1B S1B C7B . . 109.29(8) ?
O2B S1B C7B . . 106.75(8) ?
O1B S1B C6B . . 107.72(8) ?
O2B S1B C6B . . 107.22(8) ?
C7B S1B C6B . . 106.56(8) ?
C8B N1B N2B . . 110.67(15) ?
C8B N1B H1NB . . 130.6(16) ?
N2B N1B H1NB . . 118.5(16) ?
C9B N2B N1B . . 109.61(15) ?
C9B N2B H2NB . . 126.7(16) ?
N1B N2B H2NB . . 123.7(16) ?
C2B C1B C6B . . 118.48(19) ?
C2B C1B H1BA . . 120.8 ?
C6B C1B H1BA . . 120.8 ?
C3B C2B C1B . . 120.4(2) ?
C3B C2B H2BA . . 119.8 ?
C1B C2B H2BA . . 119.8 ?
C4B C3B C2B . . 120.35(19) ?
C4B C3B H3BA . . 119.8 ?
C2B C3B H3BA . . 119.8 ?
C3B C4B C5B . . 120.6(2) ?
C3B C4B H4BA . . 119.7 ?
C5B C4B H4BA . . 119.7 ?
C6B C5B C4B . . 118.23(19) ?
C6B C5B H5BA . . 120.9 ?
C4B C5B H5BA . . 120.9 ?
C1B C6B C5B . . 121.91(17) ?
C1B C6B S1B . . 118.50(14) ?
C5B C6B S1B . . 119.57(14) ?
C9B C7B C8B . . 107.90(15) ?
C9B C7B S1B . . 128.47(14) ?
C8B C7B S1B . . 123.63(13) ?
O3B C8B N1B . . 123.41(16) ?
O3B C8B C7B . . 132.46(16) ?
N1B C8B C7B . . 104.14(15) ?
N2B C9B C7B . . 107.66(16) ?
N2B C9B C10B . . 120.20(16) ?
C7B C9B C10B . . 132.14(16) ?
C9B C10B C11B . . 114.21(15) ?
C9B C10B H10C . . 108.7 ?
C11B C10B H10C . . 108.7 ?
C9B C10B H10D . . 108.7 ?
C11B C10B H10D . . 108.7 ?
H10C C10B H10D . . 107.6 ?
C13B C11B C12B . . 111.52(17) ?
C13B C11B C10B . . 109.50(16) ?
C12B C11B C10B . . 111.26(16) ?
C13B C11B H11B . . 108.1 ?
C12B C11B H11B . . 108.1 ?
C10B C11B H11B . . 108.1 ?
C11B C12B H12D . . 109.5 ?
C11B C12B H12E . . 109.5 ?
H12D C12B H12E . . 109.5 ?
C11B C12B H12F . . 109.5 ?
H12D C12B H12F . . 109.5 ?
H12E C12B H12F . . 109.5 ?
C11B C13B H13D . . 109.5 ?
C11B C13B H13E . . 109.5 ?
H13D C13B H13E . . 109.5 ?
C11B C13B H13F . . 109.5 ?
H13D C13B H13F . . 109.5 ?
H13E C13B H13F . . 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
S1A O2A . 1.4397(13) ?
S1A O1A . 1.4428(13) ?
S1A C7A . 1.7215(18) ?
S1A C6A . 1.7691(17) ?
O3A C8A . 1.267(2) ?
N1A C8A . 1.361(2) ?
N1A N2A . 1.370(2) ?
N1A H1NA . 0.79(3) ?
N2A C9A . 1.331(2) ?
N2A H2NA . 0.84(3) ?
C1A C2A . 1.386(3) ?
C1A C6A . 1.390(3) ?
C1A H1AA . 0.9300 ?
C2A C3A . 1.388(3) ?
C2A H2AA . 0.9300 ?
C3A C4A . 1.390(3) ?
C3A H3AA . 0.9300 ?
C4A C5A . 1.390(3) ?
C4A H4AA . 0.9300 ?
C5A C6A . 1.389(2) ?
C5A H5AA . 0.9300 ?
C7A C9A . 1.402(2) ?
C7A C8A . 1.433(2) ?
C9A C10A . 1.498(2) ?
C10A C11A . 1.544(2) ?
C10A H10A . 0.9700 ?
C10A H10B . 0.9700 ?
C11A C13A . 1.521(3) ?
C11A C12A . 1.528(3) ?
C11A H11A . 0.9800 ?
C12A H12A . 0.9600 ?
C12A H12B . 0.9600 ?
C12A H12C . 0.9600 ?
C13A H13A . 0.9600 ?
C13A H13B . 0.9600 ?
C13A H13C . 0.9600 ?
S1B O1B . 1.4385(13) ?
S1B O2B . 1.4431(13) ?
S1B C7B . 1.7269(17) ?
S1B C6B . 1.7713(18) ?
O3B C8B . 1.254(2) ?
N1B C8B . 1.362(2) ?
N1B N2B . 1.370(2) ?
N1B H1NB . 0.86(3) ?
N2B C9B . 1.326(2) ?
N2B H2NB . 0.88(3) ?
C1B C2B . 1.389(3) ?
C1B C6B . 1.390(3) ?
C1B H1BA . 0.9300 ?
C2B C3B . 1.389(3) ?
C2B H2BA . 0.9300 ?
C3B C4B . 1.375(3) ?
C3B H3BA . 0.9300 ?
C4B C5B . 1.398(3) ?
C4B H4BA . 0.9300 ?
C5B C6B . 1.391(3) ?
C5B H5BA . 0.9300 ?
C7B C9B . 1.399(2) ?
C7B C8B . 1.440(2) ?
C9B C10B . 1.496(2) ?
C10B C11B . 1.541(2) ?
C10B H10C . 0.9700 ?
C10B H10D . 0.9700 ?
C11B C13B . 1.520(3) ?
C11B C12B . 1.522(3) ?
C11B H11B . 0.9800 ?
C12B H12D . 0.9600 ?
C12B H12E . 0.9600 ?
C12B H12F . 0.9600 ?
C13B H13D . 0.9600 ?
C13B H13E . 0.9600 ?
C13B H13F . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1A H1NA O3A 2_776 0.79(3) 2.05(3) 2.816(2) 164(3) yes
N2A H2NA O3B 1_665 0.85(4) 1.85(4) 2.640(3) 155(2) yes
N1B H1NB O1A 1_545 0.86(3) 2.10(4) 2.733(3) 130(3) yes
N2B H2NB O3A 1_545 0.88(4) 1.83(4) 2.700(3) 170(2) yes
C5A H5AA O1B 2_666 0.9300 2.4700 3.256(3) 143.00 yes
C5B H5BA O2A . 0.9300 2.4800 3.307(3) 149.00 yes
C10A H10B O3B 1_665 0.9700 2.5700 3.324(3) 135.00 yes
C10B H10D O1B . 0.9700 2.4100 3.152(3) 133.00 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
C8A N1A N2A C9A . . . . 2.14(19) ?
C6A C1A C2A C3A . . . . 0.8(3) ?
C1A C2A C3A C4A . . . . 0.3(3) ?
C2A C3A C4A C5A . . . . -1.3(3) ?
C3A C4A C5A C6A . . . . 1.3(3) ?
C4A C5A C6A C1A . . . . -0.2(3) ?
C4A C5A C6A S1A . . . . -178.87(14) ?
C2A C1A C6A C5A . . . . -0.8(3) ?
C2A C1A C6A S1A . . . . 177.83(15) ?
O2A S1A C6A C5A . . . . -150.20(15) ?
O1A S1A C6A C5A . . . . -20.19(17) ?
C7A S1A C6A C5A . . . . 94.35(16) ?
O2A S1A C6A C1A . . . . 31.11(16) ?
O1A S1A C6A C1A . . . . 161.12(14) ?
C7A S1A C6A C1A . . . . -84.34(15) ?
O2A S1A C7A C9A . . . . -21.55(18) ?
O1A S1A C7A C9A . . . . -151.82(15) ?
C6A S1A C7A C9A . . . . 93.73(16) ?
O2A S1A C7A C8A . . . . 169.54(14) ?
O1A S1A C7A C8A . . . . 39.28(16) ?
C6A S1A C7A C8A . . . . -75.18(16) ?
N2A N1A C8A O3A . . . . 175.65(15) ?
N2A N1A C8A C7A . . . . -3.48(18) ?
C9A C7A C8A O3A . . . . -175.45(17) ?
S1A C7A C8A O3A . . . . -4.7(3) ?
C9A C7A C8A N1A . . . . 3.59(18) ?
S1A C7A C8A N1A . . . . 174.31(12) ?
N1A N2A C9A C7A . . . . 0.25(19) ?
N1A N2A C9A C10A . . . . -179.75(15) ?
C8A C7A C9A N2A . . . . -2.40(19) ?
S1A C7A C9A N2A . . . . -172.83(13) ?
C8A C7A C9A C10A . . . . 177.60(16) ?
S1A C7A C9A C10A . . . . 7.2(3) ?
N2A C9A C10A C11A . . . . -99.45(19) ?
C7A C9A C10A C11A . . . . 80.6(2) ?
C9A C10A C11A C13A . . . . 71.2(2) ?
C9A C10A C11A C12A . . . . -166.01(17) ?
C8B N1B N2B C9B . . . . 1.50(19) ?
C6B C1B C2B C3B . . . . 0.1(3) ?
C1B C2B C3B C4B . . . . 0.8(3) ?
C2B C3B C4B C5B . . . . -0.9(3) ?
C3B C4B C5B C6B . . . . 0.1(3) ?
C2B C1B C6B C5B . . . . -0.9(3) ?
C2B C1B C6B S1B . . . . 177.62(15) ?
C4B C5B C6B C1B . . . . 0.8(3) ?
C4B C5B C6B S1B . . . . -177.67(14) ?
O1B S1B C6B C1B . . . . -176.39(14) ?
O2B S1B C6B C1B . . . . -47.59(16) ?
C7B S1B C6B C1B . . . . 66.43(16) ?
O1B S1B C6B C5B . . . . 2.15(17) ?
O2B S1B C6B C5B . . . . 130.95(15) ?
C7B S1B C6B C5B . . . . -115.03(15) ?
O1B S1B C7B C9B . . . . -20.70(18) ?
O2B S1B C7B C9B . . . . -150.22(15) ?
C6B S1B C7B C9B . . . . 95.44(16) ?
O1B S1B C7B C8B . . . . 159.51(14) ?
O2B S1B C7B C8B . . . . 29.99(16) ?
C6B S1B C7B C8B . . . . -84.35(15) ?
N2B N1B C8B O3B . . . . 177.71(15) ?
N2B N1B C8B C7B . . . . -1.81(18) ?
C9B C7B C8B O3B . . . . -177.96(17) ?
S1B C7B C8B O3B . . . . 1.9(3) ?
C9B C7B C8B N1B . . . . 1.50(18) ?
S1B C7B C8B N1B . . . . -178.68(12) ?
N1B N2B C9B C7B . . . . -0.46(19) ?
N1B N2B C9B C10B . . . . 179.60(14) ?
C8B C7B C9B N2B . . . . -0.66(19) ?
S1B C7B C9B N2B . . . . 179.53(13) ?
C8B C7B C9B C10B . . . . 179.26(17) ?
S1B C7B C9B C10B . . . . -0.5(3) ?
N2B C9B C10B C11B . . . . 67.8(2) ?
C7B C9B C10B C11B . . . . -112.2(2) ?
C9B C10B C11B C13B . . . . -174.69(16) ?
C9B C10B C11B C12B . . . . 61.6(2) ?
