#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/69/2016960.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_2016960
loop_
_publ_author_name
'Kiefer, Lionel'
'Dauban, Philippe'
'Dodd, Robert H.'
'Retailleau, Pascal'
_publ_section_title
;
 Two enantiomerically pure cyclic arenesulfonamide hydrochloride salts
;
_journal_coeditor_code           GD3257
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o46
_journal_page_last               o50
_journal_paper_doi               10.1107/S010827010804287X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C20 H21 N2 O2 S +, Cl -'
_chemical_formula_moiety         'C20 H21 N2 O2 S +, Cl -'
_chemical_formula_sum            'C20 H21 Cl N2 O2 S'
_chemical_formula_weight         388.90
_chemical_name_systematic
;N-[(1R)-1-(1-naphthyl)ethyl]-3,4-dihydro-2H-1,2-benzothiazin-4-aminium
 1,1-dioxide chloride
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.90(2)
_cell_angle_beta                 106.62(3)
_cell_angle_gamma                96.94(2)
_cell_formula_units_Z            2
_cell_length_a                   8.230(2)
_cell_length_b                   10.927(2)
_cell_length_c                   11.633(3)
_cell_measurement_reflns_used    2751
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.1
_cell_measurement_theta_min      1.00
_cell_volume                     952.7(4)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1999)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1999)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2009)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008) and CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_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  0.025
_diffrn_reflns_av_sigmaI/netI    0.048
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7330
_diffrn_reflns_theta_full        25.31
_diffrn_reflns_theta_max         25.31
_diffrn_reflns_theta_min         1.91
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.327
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Scalepack; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.169
_refine_ls_abs_structure_details 'Flack (1983), 2356 Friedel pairs'
_refine_ls_abs_structure_Flack   0.05(5)
_refine_ls_extinction_coef       0.018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     472
_refine_ls_number_reflns         5771
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0393
_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)+(0.0361P)²+0.1452P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0954
_reflns_number_gt                4862
_reflns_number_total             5771
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            gd3257.cif
_cod_data_source_block           I
_cod_database_code               2016960
_cod_database_fobs_code          2016960
loop_
_symmetry_equiv_pos_as_xyz
'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
Cl Cl1 0.64137(13) 0.50685(9) 0.35811(9) 0.0619(3) Uani d . 1 . .
O O2 0.5323(4) -0.0135(3) 0.2199(3) 0.0710(8) Uani d . 1 . .
S S1 0.49663(12) 0.11285(9) 0.24750(8) 0.0534(2) Uani d . 1 . .
N N2 0.6775(4) 0.2155(3) 0.3233(3) 0.0498(7) Uani d . 1 . .
H H2 0.6643 0.3023 0.3265 0.060 Uiso d R 1 . .
N N11 0.6859(3) 0.3874(2) 0.5879(2) 0.0381(6) Uani d . 1 . .
H H11A 0.5966 0.4040 0.6149 0.046 Uiso calc R 1 . .
H H11B 0.6768 0.4190 0.5221 0.046 Uiso calc R 1 . .
C C3 0.7617(4) 0.2041(4) 0.4497(3) 0.0486(8) Uani d . 1 . .
H H3A 0.8770 0.2579 0.4840 0.058 Uiso calc R 1 . .
H H3B 0.7741 0.1157 0.4425 0.058 Uiso calc R 1 . .
C C4 0.6628(4) 0.2427(3) 0.5403(3) 0.0387(7) Uani d . 1 . .
H H4 0.7120 0.2123 0.6129 0.046 Uiso calc R 1 . .
C C4A 0.4708(4) 0.1805(3) 0.4854(3) 0.0410(7) Uani d . 1 . .
C C5 0.3759(5) 0.1747(3) 0.5659(3) 0.0501(8) Uani d . 1 . .
H H5 0.4295 0.2127 0.6515 0.060 Uiso calc R 1 . .
C C6 0.2045(5) 0.1139(4) 0.5219(4) 0.0604(10) Uani d . 1 . .
H H6 0.1432 0.1125 0.5776 0.072 Uiso calc R 1 . .
C C7 0.1233(5) 0.0550(4) 0.3960(4) 0.0685(12) Uani d . 1 . .
H H7 0.0081 0.0123 0.3670 0.082 Uiso calc R 1 . .
C C8 0.2127(5) 0.0594(4) 0.3121(4) 0.0573(9) Uani d . 1 . .
H H8 0.1578 0.0216 0.2266 0.069 Uiso calc R 1 . .
C C12 0.8553(4) 0.4646(3) 0.6938(3) 0.0453(8) Uani d . 1 . .
H H12 0.8231 0.5341 0.7482 0.054 Uiso calc R 1 . .
C C14 0.9326(4) 0.3827(3) 0.7737(3) 0.0458(8) Uani d . 1 . .
C C15 1.0795(4) 0.3383(4) 0.7653(4) 0.0565(10) Uani d . 1 . .
H H15 1.1315 0.3597 0.7096 0.068 Uiso calc R 1 . .
C C16 1.1520(6) 0.2622(4) 0.8378(4) 0.0750(13) Uani d . 1 . .
H H16 1.2526 0.2349 0.8314 0.090 Uiso calc R 1 . .
C C17 1.0778(8) 0.2278(4) 0.9170(4) 0.0852(16) Uani d . 1 . .
H H17 1.1259 0.1749 0.9634 0.102 Uiso calc R 1 . .
C C18 0.8488(10) 0.2371(6) 1.0154(5) 0.114(2) Uani d . 1 . .
H H18 0.8940 0.1829 1.0612 0.137 Uiso calc R 1 . .
C C19 0.7090(11) 0.2828(8) 1.0301(5) 0.132(3) Uani d . 1 . .
H H19 0.6583 0.2581 1.0851 0.158 Uiso calc R 1 . .
C C20 0.6370(7) 0.3672(7) 0.9643(5) 0.110(2) Uani d . 1 . .
H H20 0.5425 0.3997 0.9777 0.132 Uiso calc R 1 . .
C C21 0.7089(5) 0.4007(5) 0.8799(4) 0.0736(13) Uani d . 1 . .
H H21 0.6617 0.4551 0.8352 0.088 Uiso calc R 1 . .
C C13 0.9765(5) 0.5283(4) 0.6390(4) 0.0646(11) Uani d . 1 . .
H H13A 0.9228 0.5879 0.6000 0.097 Uiso calc R 1 . .
H H13B 1.0009 0.4637 0.5777 0.097 Uiso calc R 1 . .
H H13C 1.0825 0.5735 0.7046 0.097 Uiso calc R 1 . .
O O1 0.4047(4) 0.1572(3) 0.1467(2) 0.0797(9) Uani d . 1 . .
C C8A 0.3870(4) 0.1215(3) 0.3584(3) 0.0439(8) Uani d . 1 . .
C C17A 0.9273(7) 0.2708(4) 0.9312(3) 0.0727(13) Uani d . 1 . .
C C21A 0.8546(4) 0.3524(4) 0.8608(3) 0.0550(10) Uani d . 1 . .
Cl Cl1' 0.41359(11) 0.52808(10) 0.65666(9) 0.0609(3) Uani d . 1 . .
S S1' 0.73816(11) 0.88927(9) 0.63088(9) 0.0539(2) Uani d . 1 . .
O O1' 0.8551(3) 0.8273(3) 0.7015(3) 0.0785(9) Uani d . 1 . .
O O2' 0.7986(3) 1.0188(2) 0.6349(3) 0.0679(7) Uani d . 1 . .
N N2' 0.6702(4) 0.8014(3) 0.4864(3) 0.0616(8) Uani d . 1 . .
H H2' 0.6922 0.7198 0.4930 0.074 Uiso d R 1 . .
N N11' 0.3243(3) 0.6224(2) 0.4226(3) 0.0466(7) Uani d . 1 . .
H H11C 0.4099 0.5947 0.3965 0.056 Uiso calc R 1 . .
H H11D 0.3306 0.6015 0.4938 0.056 Uiso calc R 1 . .
C C3' 0.5037(6) 0.8160(4) 0.4100(4) 0.0659(11) Uani d . 1 . .
H H3C 0.4816 0.7680 0.3234 0.079 Uiso calc R 1 . .
H H3D 0.5082 0.9061 0.4139 0.079 Uiso calc R 1 . .
C C4' 0.3565(5) 0.7691(3) 0.4524(3) 0.0488(8) Uani d . 1 . .
H H4' 0.2518 0.7915 0.4037 0.059 Uiso calc R 1 . .
C C4B 0.3857(4) 0.8316(3) 0.5889(3) 0.0460(8) Uani d . 1 . .
C C8B 0.5505(4) 0.8880(3) 0.6741(3) 0.0453(8) Uani d . 1 . .
C C5' 0.2455(5) 0.8378(4) 0.6330(4) 0.0596(10) Uani d . 1 . .
H H5' 0.1342 0.8004 0.5779 0.072 Uiso calc R 1 . .
C C6' 0.2684(6) 0.8984(4) 0.7567(4) 0.0738(12) Uani d . 1 . .
H H6' 0.1732 0.9013 0.7844 0.089 Uiso calc R 1 . .
C C7' 0.4329(6) 0.9546(5) 0.8394(4) 0.0733(12) Uani d . 1 . .
H H7' 0.4483 0.9960 0.9227 0.088 Uiso calc R 1 . .
C C8' 0.5744(5) 0.9494(4) 0.7986(4) 0.0626(10) Uani d . 1 . .
H H8' 0.6853 0.9869 0.8543 0.075 Uiso calc R 1 . .
C C17B 0.0223(6) 0.7098(4) 0.0566(4) 0.0630(10) Uani d . 1 . .
C C21B 0.0173(5) 0.6631(4) 0.1612(3) 0.0560(9) Uani d . 1 . .
C C12' 0.1529(5) 0.5512(4) 0.3246(3) 0.0564(9) Uani d . 1 . .
H H12' 0.0595 0.5779 0.3550 0.068 Uiso calc R 1 . .
C C14' 0.1400(5) 0.5905(4) 0.2051(3) 0.0556(9) Uani d . 1 . .
C C15' 0.2552(5) 0.5611(4) 0.1423(4) 0.0703(11) Uani d . 1 . .
H H15' 0.3311 0.5090 0.1681 0.084 Uiso calc R 1 . .
C C16' 0.2623(6) 0.6067(5) 0.0414(4) 0.0790(14) Uani d . 1 . .
H H16' 0.3431 0.5865 0.0019 0.095 Uiso calc R 1 . .
C C17' 0.1489(6) 0.6815(5) 0.0009(4) 0.0779(13) Uani d . 1 . .
H H17' 0.1560 0.7141 -0.0648 0.093 Uiso calc R 1 . .
C C18' -0.0995(7) 0.7809(5) 0.0122(5) 0.0898(15) Uani d . 1 . .
H H18' -0.0974 0.8096 -0.0566 0.108 Uiso calc R 1 . .
C C19' -0.2189(8) 0.8085(6) 0.0665(6) 0.1062(19) Uani d . 1 . .
H H19' -0.2962 0.8583 0.0371 0.127 Uiso calc R 1 . .
C C20' -0.2278(7) 0.7631(6) 0.1668(5) 0.0904(15) Uani d . 1 . .
H H20' -0.3132 0.7810 0.2024 0.108 Uiso calc R 1 . .
C C21' -0.1148(5) 0.6934(4) 0.2135(4) 0.0681(11) Uani d . 1 . .
H H21' -0.1232 0.6647 0.2810 0.082 Uiso calc R 1 . .
C C13' 0.1421(7) 0.4085(4) 0.3101(4) 0.0839(14) Uani d . 1 . .
H H13D 0.1664 0.3941 0.3910 0.126 Uiso calc R 1 . .
H H13E 0.2252 0.3791 0.2724 0.126 Uiso calc R 1 . .
H H13F 0.0278 0.3621 0.2578 0.126 Uiso calc R 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'
Cl Cl 0.1484 0.1585 '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 . . 118.82(19) ?
O2 S1 N2 . . 108.80(18) ?
O1 S1 N2 . . 107.58(18) ?
O2 S1 C8A . . 106.63(15) ?
O1 S1 C8A . . 110.18(17) ?
N2 S1 C8A . . 103.84(15) ?
C3 N2 S1 . . 113.3(2) ?
C3 N2 H2 . . 111.3 ?
S1 N2 H2 . . 111.9 ?
C4 N11 C12 . . 118.7(2) ?
C4 N11 H11A . . 107.6 ?
C12 N11 H11A . . 107.6 ?
C4 N11 H11B . . 107.6 ?
C12 N11 H11B . . 107.6 ?
H11A N11 H11B . . 107.1 ?
N2 C3 C4 . . 113.7(3) ?
N2 C3 H3A . . 108.8 ?
C4 C3 H3A . . 108.8 ?
N2 C3 H3B . . 108.8 ?
C4 C3 H3B . . 108.8 ?
H3A C3 H3B . . 107.7 ?
N11 C4 C3 . . 111.8(3) ?
N11 C4 C4A . . 110.2(2) ?
C3 C4 C4A . . 113.0(3) ?
N11 C4 H4 . . 107.2 ?
C3 C4 H4 . . 107.2 ?
C4A C4 H4 . . 107.2 ?
C8A C4A C5 . . 117.6(3) ?
C8A C4A C4 . . 123.2(3) ?
C5 C4A C4 . . 119.0(3) ?
C6 C5 C4A . . 121.5(3) ?
C6 C5 H5 . . 119.3 ?
C4A C5 H5 . . 119.3 ?
C5 C6 C7 . . 120.4(3) ?
C5 C6 H6 . . 119.8 ?
C7 C6 H6 . . 119.8 ?
C6 C7 C8 . . 120.1(3) ?
C6 C7 H7 . . 119.9 ?
C8 C7 H7 . . 119.9 ?
C7 C8 C8A . . 118.8(3) ?
C7 C8 H8 . . 120.6 ?
C8A C8 H8 . . 120.6 ?
C14 C12 C13 . . 115.1(3) ?
C14 C12 N11 . . 111.2(3) ?
C13 C12 N11 . . 109.9(3) ?
C14 C12 H12 . . 106.7 ?
C13 C12 H12 . . 106.7 ?
N11 C12 H12 . . 106.7 ?
C15 C14 C21A . . 119.4(4) ?
C15 C14 C12 . . 120.9(3) ?
C21A C14 C12 . . 119.7(3) ?
C14 C15 C16 . . 121.6(4) ?
C14 C15 H15 . . 119.2 ?
C16 C15 H15 . . 119.2 ?
C17 C16 C15 . . 120.4(4) ?
C17 C16 H16 . . 119.8 ?
C15 C16 H16 . . 119.8 ?
C16 C17 C17A . . 121.0(4) ?
C16 C17 H17 . . 119.5 ?
C17A C17 H17 . . 119.5 ?
C19 C18 C17A . . 120.6(7) ?
C19 C18 H18 . . 119.7 ?
C17A C18 H18 . . 119.7 ?
C18 C19 C20 . . 121.9(6) ?
C18 C19 H19 . . 119.0 ?
C20 C19 H19 . . 119.0 ?
C21 C20 C19 . . 119.0(6) ?
C21 C20 H20 . . 120.5 ?
C19 C20 H20 . . 120.5 ?
C20 C21 C21A . . 120.4(5) ?
C20 C21 H21 . . 119.8 ?
C21A C21 H21 . . 119.8 ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C4A C8A C8 . . 121.6(3) ?
C4A C8A S1 . . 122.1(2) ?
C8 C8A S1 . . 116.2(3) ?
C18 C17A C17 . . 121.8(6) ?
C18 C17A C21A . . 118.8(6) ?
C17 C17A C21A . . 119.4(4) ?
C21 C21A C17A . . 119.3(4) ?
C21 C21A C14 . . 122.6(4) ?
C17A C21A C14 . . 118.1(4) ?
O1' S1' O2' . . 118.33(17) ?
O1' S1' N2' . . 107.53(19) ?
O2' S1' N2' . . 108.52(18) ?
O1' S1' C8B . . 110.57(17) ?
O2' S1' C8B . . 106.75(17) ?
N2' S1' C8B . . 104.25(16) ?
C3' N2' S1' . . 115.6(3) ?
C3' N2' H2' . . 121.8 ?
S1' N2' H2' . . 102.9 ?
C12' N11' C4' . . 115.3(3) ?
C12' N11' H11C . . 108.4 ?
C4' N11' H11C . . 108.4 ?
C12' N11' H11D . . 108.4 ?
C4' N11' H11D . . 108.4 ?
H11C N11' H11D . . 107.5 ?
N2' C3' C4' . . 112.3(3) ?
N2' C3' H3C . . 109.1 ?
C4' C3' H3C . . 109.1 ?
N2' C3' H3D . . 109.1 ?
C4' C3' H3D . . 109.1 ?
H3C C3' H3D . . 107.9 ?
C4B C4' C3' . . 112.9(3) ?
C4B C4' N11' . . 111.1(3) ?
C3' C4' N11' . . 109.8(3) ?
C4B C4' H4' . . 107.6 ?
C3' C4' H4' . . 107.6 ?
N11' C4' H4' . . 107.6 ?
C8B C4B C5' . . 117.8(3) ?
C8B C4B C4' . . 122.0(3) ?
C5' C4B C4' . . 120.2(3) ?
C8' C8B C4B . . 121.1(3) ?
C8' C8B S1' . . 116.2(3) ?
C4B C8B S1' . . 122.6(3) ?
C6' C5' C4B . . 121.3(3) ?
C6' C5' H5' . . 119.3 ?
C4B C5' H5' . . 119.3 ?
C5' C6' C7' . . 119.9(4) ?
C5' C6' H6' . . 120.0 ?
C7' C6' H6' . . 120.0 ?
C8' C7' C6' . . 120.0(4) ?
C8' C7' H7' . . 120.0 ?
C6' C7' H7' . . 120.0 ?
C7' C8' C8B . . 119.8(4) ?
C7' C8' H8' . . 120.1 ?
C8B C8' H8' . . 120.1 ?
C18' C17B C17' . . 121.8(4) ?
C18' C17B C21B . . 119.5(4) ?
C17' C17B C21B . . 118.8(4) ?
C14' C21B C21' . . 124.3(4) ?
C14' C21B C17B . . 119.2(4) ?
C21' C21B C17B . . 116.5(4) ?
N11' C12' C13' . . 107.8(3) ?
N11' C12' C14' . . 108.3(3) ?
C13' C12' C14' . . 115.1(3) ?
N11' C12' H12' . . 108.5 ?
C13' C12' H12' . . 108.5 ?
C14' C12' H12' . . 108.5 ?
C15' C14' C21B . . 119.0(4) ?
C15' C14' C12' . . 119.8(4) ?
C21B C14' C12' . . 121.1(3) ?
C14' C15' C16' . . 122.3(4) ?
C14' C15' H15' . . 118.8 ?
C16' C15' H15' . . 118.8 ?
C17' C16' C15' . . 119.4(4) ?
C17' C16' H16' . . 120.3 ?
C15' C16' H16' . . 120.3 ?
C16' C17' C17B . . 121.2(4) ?
C16' C17' H17' . . 119.4 ?
C17B C17' H17' . . 119.4 ?
C19' C18' C17B . . 121.4(5) ?
C19' C18' H18' . . 119.3 ?
C17B C18' H18' . . 119.3 ?
C18' C19' C20' . . 120.2(5) ?
C18' C19' H19' . . 119.9 ?
C20' C19' H19' . . 119.9 ?
C21' C20' C19' . . 121.2(5) ?
C21' C20' H20' . . 119.4 ?
C19' C20' H20' . . 119.4 ?
C20' C21' C21B . . 121.2(4) ?
C20' C21' H21' . . 119.4 ?
C21B C21' H21' . . 119.4 ?
C12' C13' H13D . . 109.5 ?
C12' C13' H13E . . 109.5 ?
H13D C13' H13E . . 109.5 ?
C12' C13' H13F . . 109.5 ?
H13D C13' H13F . . 109.5 ?
H13E C13' 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
O2 S1 . 1.426(3) ?
S1 O1 . 1.427(3) ?
S1 N2 . 1.620(3) ?
S1 C8A . 1.765(3) ?
N2 C3 . 1.478(5) ?
N2 H2 . 0.9600 ?
N11 C4 . 1.513(4) ?
N11 C12 . 1.551(4) ?
N11 H11A . 0.9000 ?
N11 H11B . 0.9000 ?
C3 C4 . 1.521(4) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C4A . 1.523(4) ?
C4 H4 . 0.9800 ?
C4A C8A . 1.387(4) ?
C4A C5 . 1.388(4) ?
C5 C6 . 1.375(5) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.375(6) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.385(6) ?
C7 H7 . 0.9300 ?
C8 C8A . 1.399(5) ?
C8 H8 . 0.9300 ?
C12 C14 . 1.507(5) ?
C12 C13 . 1.514(5) ?
C12 H12 . 0.9800 ?
C14 C15 . 1.376(5) ?
C14 C21A . 1.425(5) ?
C15 C16 . 1.389(6) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.340(7) ?
C16 H16 . 0.9300 ?
C17 C17A . 1.414(7) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.346(10) ?
C18 C17A . 1.411(7) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.415(10) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.379(6) ?
C20 H20 . 0.9300 ?
C21 C21A . 1.419(6) ?
C21 H21 . 0.9300 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C17A C21A . 1.422(6) ?
S1' O1' . 1.426(3) ?
S1' O2' . 1.428(3) ?
S1' N2' . 1.618(3) ?
S1' C8B . 1.755(3) ?
N2' C3' . 1.455(6) ?
N2' H2' . 0.9477 ?
N11' C12' . 1.511(4) ?
N11' C4' . 1.529(4) ?
N11' H11C . 0.9000 ?
N11' H11D . 0.9000 ?
C3' C4' . 1.513(5) ?
C3' H3C . 0.9700 ?
C3' H3D . 0.9700 ?
C4' C4B . 1.505(5) ?
C4' H4' . 0.9800 ?
C4B C8B . 1.392(5) ?
C4B C5' . 1.393(5) ?
C8B C8' . 1.388(5) ?
C5' C6' . 1.379(6) ?
C5' H5' . 0.9300 ?
C6' C7' . 1.380(6) ?
C6' H6' . 0.9300 ?
C7' C8' . 1.380(5) ?
C7' H7' . 0.9300 ?
C8' H8' . 0.9300 ?
C17B C18' . 1.400(7) ?
C17B C17' . 1.403(6) ?
C17B C21B . 1.437(5) ?
C21B C14' . 1.415(5) ?
C21B C21' . 1.425(5) ?
C12' C13' . 1.516(6) ?
C12' C14' . 1.531(5) ?
C12' H12' . 0.9800 ?
C14' C15' . 1.375(5) ?
C15' C16' . 1.393(7) ?
C15' H15' . 0.9300 ?
C16' C17' . 1.371(7) ?
C16' H16' . 0.9300 ?
C17' H17' . 0.9300 ?
C18' C19' . 1.339(7) ?
C18' H18' . 0.9300 ?
C19' C20' . 1.390(7) ?
C19' H19' . 0.9300 ?
C20' C21' . 1.349(6) ?
C20' H20' . 0.9300 ?
C21' H21' . 0.9300 ?
C13' H13D . 0.9600 ?
C13' H13E . 0.9600 ?
C13' 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
N2 H2 Cl1 . 0.96 2.22 3.172(3) 173.2
N11 H11B Cl1 . 0.90 2.30 3.195(3) 176.4
N11 H11A Cl1' . 0.90 2.22 3.049(2) 152.5
N2' H2' Cl1 . 0.95 2.39 3.154(3) 138.1
N11' H11D Cl1' . 0.90 2.20 3.067(3) 162.6
N11' H11C Cl1 . 0.90 2.34 3.229(3) 169.9
C4 H4 O2' 1_545 0.98 2.36 3.114(4) 133.4
C19 H19 O1 1_556 0.93 2.60 3.465(7) 154.7
C6' H6' O1' 1_455 0.93 2.47 3.234(5) 139.4
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 N2 C3 . . . . -67.2(3) ?
O1 S1 N2 C3 . . . . 162.9(2) ?
C8A S1 N2 C3 . . . . 46.1(3) ?
S1 N2 C3 C4 . . . . -67.8(3) ?
C12 N11 C4 C3 . . . . -79.2(3) ?
C12 N11 C4 C4A . . . . 154.3(2) ?
N2 C3 C4 N11 . . . . -76.4(4) ?
N2 C3 C4 C4A . . . . 48.5(4) ?
N11 C4 C4A C8A . . . . 110.9(3) ?
C3 C4 C4A C8A . . . . -14.9(4) ?
N11 C4 C4A C5 . . . . -73.3(4) ?
C3 C4 C4A C5 . . . . 160.8(3) ?
C8A C4A C5 C6 . . . . -0.7(5) ?
C4 C4A C5 C6 . . . . -176.6(3) ?
C4A C5 C6 C7 . . . . 1.1(6) ?
C5 C6 C7 C8 . . . . -1.5(6) ?
C6 C7 C8 C8A . . . . 1.6(6) ?
C4 N11 C12 C14 . . . . -26.9(4) ?
C4 N11 C12 C13 . . . . 101.7(4) ?
C13 C12 C14 C15 . . . . -19.0(5) ?
N11 C12 C14 C15 . . . . 106.8(3) ?
C13 C12 C14 C21A . . . . 160.0(3) ?
N11 C12 C14 C21A . . . . -74.2(4) ?
C21A C14 C15 C16 . . . . 1.3(5) ?
C12 C14 C15 C16 . . . . -179.7(3) ?
C14 C15 C16 C17 . . . . 1.3(6) ?
C15 C16 C17 C17A . . . . -1.7(6) ?
C17A C18 C19 C20 . . . . -1.1(9) ?
C18 C19 C20 C21 . . . . 2.0(9) ?
C19 C20 C21 C21A . . . . -0.9(7) ?
C5 C4A C8A C8 . . . . 0.7(5) ?
C4 C4A C8A C8 . . . . 176.5(3) ?
C5 C4A C8A S1 . . . . -175.7(3) ?
C4 C4A C8A S1 . . . . 0.1(5) ?
C7 C8 C8A C4A . . . . -1.1(5) ?
C7 C8 C8A S1 . . . . 175.5(3) ?
O2 S1 C8A C4A . . . . 100.4(3) ?
O1 S1 C8A C4A . . . . -129.4(3) ?
N2 S1 C8A C4A . . . . -14.4(3) ?
O2 S1 C8A C8 . . . . -76.2(3) ?
O1 S1 C8A C8 . . . . 54.0(3) ?
N2 S1 C8A C8 . . . . 169.0(3) ?
C19 C18 C17A C17 . . . . 177.8(5) ?
C19 C18 C17A C21A . . . . -0.9(7) ?
C16 C17 C17A C18 . . . . -179.1(4) ?
C16 C17 C17A C21A . . . . -0.4(6) ?
C20 C21 C21A C17A . . . . -1.0(5) ?
C20 C21 C21A C14 . . . . 179.3(4) ?
C18 C17A C21A C21 . . . . 1.9(5) ?
C17 C17A C21A C21 . . . . -176.8(4) ?
C18 C17A C21A C14 . . . . -178.4(4) ?
C17 C17A C21A C14 . . . . 2.9(5) ?
C15 C14 C21A C21 . . . . 176.4(3) ?
C12 C14 C21A C21 . . . . -2.6(5) ?
C15 C14 C21A C17A . . . . -3.3(5) ?
C12 C14 C21A C17A . . . . 177.6(3) ?
O1' S1' N2' C3' . . . . 155.8(3) ?
O2' S1' N2' C3' . . . . -75.1(3) ?
C8B S1' N2' C3' . . . . 38.4(3) ?
S1' N2' C3' C4' . . . . -65.9(4) ?
N2' C3' C4' C4B . . . . 54.7(4) ?
N2' C3' C4' N11' . . . . -70.0(4) ?
C12' N11' C4' C4B . . . . 121.0(3) ?
C12' N11' C4' C3' . . . . -113.3(3) ?
C3' C4' C4B C8B . . . . -21.6(5) ?
N11' C4' C4B C8B . . . . 102.3(4) ?
C3' C4' C4B C5' . . . . 156.5(3) ?
N11' C4' C4B C5' . . . . -79.6(4) ?
C5' C4B C8B C8' . . . . -0.6(5) ?
C4' C4B C8B C8' . . . . 177.5(3) ?
C5' C4B C8B S1' . . . . -179.0(3) ?
C4' C4B C8B S1' . . . . -1.0(5) ?
O1' S1' C8B C8' . . . . 60.1(3) ?
O2' S1' C8B C8' . . . . -69.9(3) ?
N2' S1' C8B C8' . . . . 175.4(3) ?
O1' S1' C8B C4B . . . . -121.4(3) ?
O2' S1' C8B C4B . . . . 108.7(3) ?
N2' S1' C8B C4B . . . . -6.1(3) ?
C8B C4B C5' C6' . . . . 0.4(6) ?
C4' C4B C5' C6' . . . . -177.8(4) ?
C4B C5' C6' C7' . . . . 0.2(7) ?
C5' C6' C7' C8' . . . . -0.5(7) ?
C6' C7' C8' C8B . . . . 0.3(7) ?
C4B C8B C8' C7' . . . . 0.2(6) ?
S1' C8B C8' C7' . . . . 178.8(3) ?
C18' C17B C21B C14' . . . . 179.6(4) ?
C17' C17B C21B C14' . . . . 0.2(5) ?
C18' C17B C21B C21' . . . . 0.0(6) ?
C17' C17B C21B C21' . . . . -179.4(4) ?
C4' N11' C12' C13' . . . . -178.5(3) ?
C4' N11' C12' C14' . . . . 56.3(4) ?
C21' C21B C14' C15' . . . . 176.3(4) ?
C17B C21B C14' C15' . . . . -3.3(5) ?
C21' C21B C14' C12' . . . . -7.2(5) ?
C17B C21B C14' C12' . . . . 173.3(3) ?
N11' C12' C14' C15' . . . . 63.8(4) ?
C13' C12' C14' C15' . . . . -56.9(5) ?
N11' C12' C14' C21B . . . . -112.7(4) ?
C13' C12' C14' C21B . . . . 126.6(4) ?
C21B C14' C15' C16' . . . . 3.9(6) ?
C12' C14' C15' C16' . . . . -172.7(4) ?
C14' C15' C16' C17' . . . . -1.3(6) ?
C15' C16' C17' C17B . . . . -2.0(7) ?
C18' C17B C17' C16' . . . . -176.9(5) ?
C21B C17B C17' C16' . . . . 2.5(6) ?
C17' C17B C18' C19' . . . . -179.4(5) ?
C21B C17B C18' C19' . . . . 1.2(8) ?
C17B C18' C19' C20' . . . . -2.1(9) ?
C18' C19' C20' C21' . . . . 1.6(9) ?
C19' C20' C21' C21B . . . . -0.4(8) ?
C14' C21B C21' C20' . . . . -179.9(4) ?
C17B C21B C21' C20' . . . . -0.4(6) ?
