#------------------------------------------------------------------------------
#$Date: 2016-08-11 15:44:16 +0300 (Thu, 11 Aug 2016) $
#$Revision: 185754 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/91/7119123.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_7119123
loop_
_publ_author_name
'Cory M. Widdifield'
'Harry Robson'
'Paul Hodgkinson'
_publ_section_title
;
 Furosemide's one little hydrogen atom: NMR crystallography structure
 verification of powdered molecular organics
;
_journal_name_full               Chem.Commun.
_journal_page_first              6685
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C12 H11 Cl N2 O5 S'
_chemical_formula_sum            'C12 H11 Cl N2 O5 S'
_chemical_formula_weight         330.74
_chemical_name_common            Furosemide
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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_date             2016-02-03
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.11.20 svn.r3248 for OlexSys, GUI svn.r5133)
;
_audit_update_record
;
2016-03-07 deposited with the CCDC.
2016-04-18 downloaded from the CCDC.
;
_cell_angle_alpha                92.938(5)
_cell_angle_beta                 107.085(5)
_cell_angle_gamma                116.622(6)
_cell_formula_units_Z            4
_cell_length_a                   9.5347(5)
_cell_length_b                   10.4694(6)
_cell_length_c                   15.6057(9)
_cell_measurement_reflns_used    2809
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      29.8050
_cell_measurement_theta_min      2.2170
_cell_volume                     1300.34(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -34.00   44.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587  -57.0000 -180.0000 78

  2 omega   44.00   81.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -178.0000 -150.0000 37

  3 omega   14.00   68.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -100.0000  -60.0000 54

  4 omega   44.00   71.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -100.0000   60.0000 27

  5 omega   23.00   71.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -100.0000 -180.0000 48

  6 omega    9.00   98.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   57.0000   60.0000 89

  7 omega  -44.00   67.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587  -19.0000 -120.0000 111

  8 omega    9.00   98.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   57.0000  -30.0000 89

  9 omega   35.00   94.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587  178.0000  120.0000 59

 10 omega   -1.00   99.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   77.0000 -120.0000 100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0482803000
_diffrn_orient_matrix_UB_12      -0.0335980000
_diffrn_orient_matrix_UB_13      0.0196828000
_diffrn_orient_matrix_UB_21      -0.0228266000
_diffrn_orient_matrix_UB_22      -0.0408962000
_diffrn_orient_matrix_UB_23      -0.0441273000
_diffrn_orient_matrix_UB_31      0.0712004000
_diffrn_orient_matrix_UB_32      0.0567245000
_diffrn_orient_matrix_UB_33      -0.0059058000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_av_unetI/netI     0.1153
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19564
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.23
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.479
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.662
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     467
_refine_ls_number_reflns         6913
_refine_ls_number_restraints     43
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.1193
_refine_ls_R_factor_gt           0.0561
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0240P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.1209
_reflns_number_gt                3893
_reflns_number_total             6913
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc02171a2.cif
_cod_data_source_block           fur_new_16srv043
_cod_original_cell_volume        1300.35(13)
_cod_database_code               7119123
_chemical_oxdiff_formula         'C12 H11 Cl1 N2 O5 S1'
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.44
_olex2_refinement_description
;
1. Restrained distances
 C10-H10 \\sim C11-H11 \\sim C12-H12 \\sim C12A-H12A \\sim C11A-H11A \\sim
C10A-H10A
 with sigma of 0.005
 C8-H8A \\sim C8-H8B \\sim C8A-H8AA \\sim C8A-H8AB
 with sigma of 0.005
 C3-H3 \\sim C6-H6 \\sim C3A-H3A \\sim C6A-H6A
 with sigma of 0.005
 N1-H1 \\sim N1A-H1A \\sim N2-H2B \\sim N2-H2A \\sim N2A-H2AC \\sim N2A-H2AB
 with sigma of 0.005
 O2A-H2AA \\sim O2-H2
 with sigma of 0.005
;
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 0.00523(10) 0.60204(9) 0.19321(6) 0.02161(19) Uani 1 d . . .
S1 S -0.12313(9) 0.42882(9) 0.34624(6) 0.01822(19) Uani 1 d . . .
O1 O 0.2535(3) 0.3688(3) 0.06799(17) 0.0267(6) Uani 1 d . . .
O2 O 0.3406(3) 0.3081(3) 0.49644(16) 0.0224(5) Uani 1 d . . D
O3 O 0.5000(3) 0.3242(2) 0.41250(15) 0.0228(5) Uani 1 d . . .
O4 O -0.2598(3) 0.3685(2) 0.26013(15) 0.0235(5) Uani 1 d . . .
O5 O -0.0846(3) 0.5653(2) 0.39940(16) 0.0223(5) Uani 1 d . . .
N1 N 0.4732(3) 0.4703(3) 0.2730(2) 0.0201(6) Uani 1 d . . D
N2 N -0.1639(4) 0.3123(3) 0.4093(2) 0.0219(7) Uani 1 d . . D
C1 C 0.2985(4) 0.4080(3) 0.3667(2) 0.0162(7) Uani 1 d . . .
C2 C 0.3444(4) 0.4693(3) 0.2934(2) 0.0174(7) Uani 1 d . . .
C3 C 0.2492(4) 0.5306(3) 0.2427(2) 0.0171(7) Uani 1 d . . D
C4 C 0.1117(4) 0.5224(3) 0.2590(2) 0.0174(7) Uani 1 d . . .
C5 C 0.0592(4) 0.4529(3) 0.3277(2) 0.0163(7) Uani 1 d . . .
C6 C 0.1572(4) 0.4011(3) 0.3810(2) 0.0173(7) Uani 1 d . . D
C7 C 0.3877(4) 0.3434(3) 0.4263(2) 0.0175(7) Uani 1 d . . .
C8 C 0.5189(4) 0.5213(4) 0.1944(2) 0.0213(7) Uani 1 d . . D
C9 C 0.4211(4) 0.4102(4) 0.1066(2) 0.0203(7) Uani 1 d . . .
C10 C 0.4639(5) 0.3418(4) 0.0525(3) 0.0282(8) Uani 1 d . . D
C11 C 0.3167(5) 0.2528(4) -0.0258(3) 0.0303(9) Uani 1 d . . D
C12 C 0.1944(5) 0.2710(4) -0.0136(3) 0.0301(9) Uani 1 d . . D
H1 H 0.516(4) 0.424(3) 0.303(2) 0.030(11) Uiso 1 d . . D
H2 H 0.383(4) 0.258(4) 0.531(2) 0.042(12) Uiso 1 d . . D
H2A H -0.103(4) 0.345(4) 0.4652(12) 0.056(15) Uiso 1 d . . D
H2B H -0.198(4) 0.225(2) 0.385(2) 0.045(13) Uiso 1 d . . D
H3 H 0.281(3) 0.574(3) 0.1938(16) 0.010(8) Uiso 1 d . . D
H6 H 0.130(4) 0.352(3) 0.4292(17) 0.025(9) Uiso 1 d . . D
H8A H 0.637(2) 0.548(3) 0.209(2) 0.017(8) Uiso 1 d . . D
H8B H 0.512(3) 0.611(2) 0.189(2) 0.011(8) Uiso 1 d . . D
H10 H 0.567(3) 0.351(4) 0.067(2) 0.038(11) Uiso 1 d . . D
H11 H 0.306(4) 0.199(3) -0.0767(15) 0.021(9) Uiso 1 d . . D
H12 H 0.083(2) 0.237(3) -0.040(2) 0.022(9) Uiso 1 d . . D
Cl1A Cl 0.02964(9) 1.10622(9) 0.18112(6) 0.0224(2) Uani 1 d . . .
S1A S -0.09157(9) 0.94039(9) 0.33989(6) 0.01773(19) Uani 1 d . . .
O1A O 0.3549(3) 0.7539(2) 0.09592(16) 0.0244(5) Uani 1 d . . .
O2A O 0.3614(3) 0.8055(3) 0.48035(17) 0.0242(6) Uani 1 d . . D
O3A O 0.5379(3) 0.8436(2) 0.40454(15) 0.0229(5) Uani 1 d . . .
O4A O -0.2282(3) 0.8782(2) 0.25373(15) 0.0231(5) Uani 1 d . . .
O5A O -0.0569(3) 1.0754(2) 0.39279(15) 0.0216(5) Uani 1 d . . .
N1A N 0.5043(3) 0.9849(3) 0.26234(19) 0.0185(6) Uani 1 d . . D
N2A N -0.1280(4) 0.8252(3) 0.4035(2) 0.0202(6) Uani 1 d . . D
C1A C 0.3301(4) 0.9200(3) 0.3564(2) 0.0172(7) Uani 1 d . . .
C2A C 0.3733(4) 0.9799(3) 0.2830(2) 0.0169(7) Uani 1 d . . .
C3A C 0.2753(4) 1.0378(4) 0.2307(2) 0.0192(7) Uani 1 d . . D
C4A C 0.1391(4) 1.0303(3) 0.2486(2) 0.0180(7) Uani 1 d . . .
C5A C 0.0908(4) 0.9648(3) 0.3191(2) 0.0169(7) Uani 1 d . . .
C6A C 0.1909(4) 0.9149(3) 0.3721(2) 0.0179(7) Uani 1 d . . D
C7A C 0.4182(4) 0.8534(3) 0.4148(2) 0.0167(7) Uani 1 d . . .
C8A C 0.5252(4) 1.0111(4) 0.1737(2) 0.0205(7) Uani 1 d . . D
C9A C 0.3850(4) 0.8954(3) 0.0941(2) 0.0198(7) Uani 1 d . . .
C10A C 0.2731(5) 0.8940(4) 0.0180(3) 0.0302(9) Uani 1 d . . D
C11A C 0.1683(5) 0.7466(4) -0.0313(3) 0.0310(9) Uani 1 d . . D
C12A C 0.2203(4) 0.6664(4) 0.0180(3) 0.0256(8) Uani 1 d . . D
H1A H 0.553(3) 0.941(3) 0.289(2) 0.017(9) Uiso 1 d . . D
H8AA H 0.632(3) 1.016(4) 0.178(2) 0.027(9) Uiso 1 d . . D
H2AA H 0.411(5) 0.759(5) 0.515(3) 0.072(16) Uiso 1 d . . D
H2AB H -0.076(3) 0.854(4) 0.4606(10) 0.023(10) Uiso 1 d . . D
H2AC H -0.147(4) 0.740(2) 0.386(2) 0.032(11) Uiso 1 d . . D
H3A H 0.287(4) 1.073(3) 0.1760(16) 0.027(10) Uiso 1 d . . D
H6A H 0.165(4) 0.873(3) 0.4228(17) 0.025(9) Uiso 1 d . . D
H8AB H 0.535(4) 1.106(2) 0.165(2) 0.022(9) Uiso 1 d . . D
H10A H 0.262(5) 0.972(3) 0.004(3) 0.050(13) Uiso 1 d . . D
H11A H 0.083(3) 0.713(4) -0.0854(15) 0.046(12) Uiso 1 d . . D
H12A H 0.185(5) 0.5700(19) 0.014(3) 0.059(14) Uiso 1 d . . D
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 -1 1 0.0836 0.0000 -1.0000 1.0000 0.0533 -0.0032 -0.0626
0 1 -1 0.0836 -0.0000 1.0000 -1.0000 -0.0533 0.0032 0.0626
0 0 -1 0.0213 -0.0000 0.0000 -1.0000 -0.0197 0.0441 0.0059
0 0 1 0.0213 0.0000 -0.0000 1.0000 0.0197 -0.0441 -0.0059
1 0 -1 0.0610 1.0000 0.0000 -1.0000 0.0286 0.0213 0.0771
-1 0 1 0.0610 -1.0000 -0.0000 1.0000 -0.0286 -0.0213 -0.0771
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O4 S1 O5 117.90(14) . .
O4 S1 N2 107.80(16) . .
O4 S1 C5 108.89(14) . .
O5 S1 N2 106.45(15) . .
O5 S1 C5 107.83(13) . .
N2 S1 C5 107.54(15) . .
C9 O1 C12 105.7(3) . .
C7 O2 H2 117(2) . .
C2 N1 C8 124.7(3) . .
C2 N1 H1 114(2) . .
C8 N1 H1 120(2) . .
S1 N2 H2A 115(3) . .
S1 N2 H2B 117(3) . .
H2A N2 H2B 120(4) . .
C2 C1 C7 123.1(3) . .
C6 C1 C2 119.5(3) . .
C6 C1 C7 117.4(3) . .
N1 C2 C1 121.9(3) . .
N1 C2 C3 121.2(3) . .
C3 C2 C1 116.9(3) . .
C2 C3 H3 117.3(17) . .
C4 C3 C2 121.8(3) . .
C4 C3 H3 120.9(17) . .
C3 C4 Cl1 117.8(2) . .
C3 C4 C5 121.3(3) . .
C5 C4 Cl1 120.9(2) . .
C4 C5 S1 123.1(2) . .
C6 C5 S1 119.7(2) . .
C6 C5 C4 117.2(3) . .
C1 C6 H6 114.1(19) . .
C5 C6 C1 123.1(3) . .
C5 C6 H6 122.8(19) . .
O2 C7 C1 114.4(3) . .
O3 C7 O2 122.2(3) . .
O3 C7 C1 123.4(3) . .
N1 C8 C9 114.5(3) . .
N1 C8 H8A 107.5(18) . .
N1 C8 H8B 109.1(17) . .
C9 C8 H8A 107.4(18) . .
C9 C8 H8B 111.8(18) . .
H8A C8 H8B 106(2) . .
O1 C9 C8 117.1(3) . .
C10 C9 O1 110.0(3) . .
C10 C9 C8 132.8(3) . .
C9 C10 C11 107.0(3) . .
C9 C10 H10 124(2) . .
C11 C10 H10 129(2) . .
C10 C11 H11 129(2) . .
C12 C11 C10 106.6(3) . .
C12 C11 H11 125(2) . .
O1 C12 H12 109(2) . .
C11 C12 O1 110.7(3) . .
C11 C12 H12 140(2) . .
O4A S1A O5A 117.90(14) . .
O4A S1A N2A 108.23(15) . .
O4A S1A C5A 107.66(14) . .
O5A S1A N2A 106.09(15) . .
O5A S1A C5A 109.34(13) . .
N2A S1A C5A 107.15(15) . .
C12A O1A C9A 106.5(3) . .
C7A O2A H2AA 115(3) . .
C2A N1A C8A 122.8(3) . .
C2A N1A H1A 119(2) . .
C8A N1A H1A 114(2) . .
S1A N2A H2AB 119(2) . .
S1A N2A H2AC 121(2) . .
H2AB N2A H2AC 111(3) . .
C2A C1A C7A 123.3(3) . .
C6A C1A C2A 119.3(3) . .
C6A C1A C7A 117.3(3) . .
N1A C2A C1A 122.4(3) . .
N1A C2A C3A 120.1(3) . .
C1A C2A C3A 117.5(3) . .
C2A C3A H3A 124(2) . .
C4A C3A C2A 121.2(3) . .
C4A C3A H3A 113.9(19) . .
C3A C4A Cl1A 117.2(2) . .
C3A C4A C5A 121.6(3) . .
C5A C4A Cl1A 121.2(2) . .
C4A C5A S1A 123.5(2) . .
C6A C5A S1A 119.6(2) . .
C6A C5A C4A 116.9(3) . .
C1A C6A H6A 117.2(19) . .
C5A C6A C1A 123.4(3) . .
C5A C6A H6A 119.3(19) . .
O2A C7A C1A 114.4(3) . .
O3A C7A O2A 122.0(3) . .
O3A C7A C1A 123.6(3) . .
N1A C8A C9A 112.8(3) . .
N1A C8A H8AA 106.8(19) . .
N1A C8A H8AB 110.1(19) . .
C9A C8A H8AA 110.7(19) . .
C9A C8A H8AB 109(2) . .
H8AA C8A H8AB 107(2) . .
O1A C9A C8A 116.4(3) . .
C10A C9A O1A 108.9(3) . .
C10A C9A C8A 134.7(3) . .
C9A C10A C11A 107.6(3) . .
C9A C10A H10A 125(3) . .
C11A C10A H10A 127(3) . .
C10A C11A H11A 127(3) . .
C12A C11A C10A 106.7(3) . .
C12A C11A H11A 126(3) . .
O1A C12A H12A 114(3) . .
C11A C12A O1A 110.3(3) . .
C11A C12A H12A 135(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C4 1.736(3) .
S1 O4 1.432(2) .
S1 O5 1.447(2) .
S1 N2 1.591(3) .
S1 C5 1.755(3) .
O1 C9 1.375(4) .
O1 C12 1.384(4) .
O2 C7 1.311(4) .
O2 H2 0.91(3) .
O3 C7 1.247(3) .
N1 C2 1.351(4) .
N1 C8 1.467(4) .
N1 H1 0.841(14) .
N2 H2A 0.842(14) .
N2 H2B 0.841(14) .
C1 C2 1.425(4) .
C1 C6 1.401(4) .
C1 C7 1.469(4) .
C2 C3 1.419(4) .
C3 C4 1.374(4) .
C3 H3 0.965(16) .
C4 C5 1.413(4) .
C5 C6 1.380(4) .
C6 H6 0.965(16) .
C8 C9 1.488(5) .
C8 H8A 0.975(14) .
C8 H8B 0.974(14) .
C9 C10 1.341(5) .
C10 C11 1.427(5) .
C10 H10 0.900(14) .
C11 C12 1.326(5) .
C11 H11 0.901(14) .
C12 H12 0.901(14) .
Cl1A C4A 1.735(3) .
S1A O4A 1.431(2) .
S1A O5A 1.446(2) .
S1A N2A 1.585(3) .
S1A C5A 1.771(3) .
O1A C9A 1.381(4) .
O1A C12A 1.371(4) .
O2A C7A 1.314(4) .
O2A H2AA 0.91(3) .
O3A C7A 1.244(3) .
N1A C2A 1.359(4) .
N1A C8A 1.477(4) .
N1A H1A 0.842(14) .
N2A H2AB 0.842(14) .
N2A H2AC 0.842(14) .
C1A C2A 1.413(4) .
C1A C6A 1.398(4) .
C1A C7A 1.471(4) .
C2A C3A 1.420(4) .
C3A C4A 1.377(4) .
C3A H3A 0.965(16) .
C4A C5A 1.409(4) .
C5A C6A 1.377(4) .
C6A H6A 0.965(16) .
C8A C9A 1.489(5) .
C8A H8AA 0.974(14) .
C8A H8AB 0.974(14) .
C9A C10A 1.337(5) .
C10A C11A 1.421(5) .
C10A H10A 0.900(14) .
C11A C12A 1.325(5) .
C11A H11A 0.901(14) .
C12A H12A 0.901(15) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O3 0.841(14) 2.05(2) 2.740(4) 138(3) .
O2 H2 O3A 0.91(3) 1.75(3) 2.665(3) 178(4) 2_666
N2 H2A O5 0.842(14) 2.149(16) 2.983(4) 171(4) 2_566
N2 H2B O5A 0.841(14) 2.47(3) 3.101(4) 133(3) 1_545
N1A H1A O3A 0.842(14) 2.12(2) 2.749(3) 131(3) .
O2A H2AA O3 0.91(3) 1.72(3) 2.633(3) 176(4) 2_666
N2A H2AB O5A 0.842(14) 2.162(15) 3.003(4) 179(3) 2_576
N2A H2AC O5 0.842(14) 2.16(2) 2.929(4) 151(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N1 C8 C9 O1 67.9(4) . . . .
C1 C2 N1 C8 175.1(3) . . . .
C2 C1 C7 O2 172.4(3) . . . .
C2 C1 C7 O3 -7.0(5) . . . .
C3 C2 N1 C8 -5.4(5) . . . .
C4 C5 S1 O4 48.8(3) . . . .
C4 C5 S1 O5 -80.2(3) . . . .
C4 C5 S1 N2 165.4(3) . . . .
C6 C1 C7 O2 -10.9(4) . . . .
C6 C1 C7 O3 169.7(3) . . . .
C6 C5 S1 O4 -130.4(3) . . . .
C6 C5 S1 O5 100.6(3) . . . .
C6 C5 S1 N2 -13.9(3) . . . .
C9 C8 N1 C2 -83.7(4) . . . .
C10 C9 C8 N1 -114.9(4) . . . .
N1A C8A C9A O1A -57.3(4) . . . .
C1A C2A N1A C8A 163.8(3) . . . .
C2A C1A C7A O2A 179.1(3) . . . .
C2A C1A C7A O3A -0.3(5) . . . .
C3A C2A N1A C8A -16.9(5) . . . .
C4A C5A S1A O4A 47.8(3) . . . .
C4A C5A S1A O5A -81.4(3) . . . .
C4A C5A S1A N2A 164.0(3) . . . .
C6A C1A C7A O2A -4.7(4) . . . .
C6A C1A C7A O3A 175.9(3) . . . .
C6A C5A S1A O4A -130.5(3) . . . .
C6A C5A S1A O5A 100.3(3) . . . .
C6A C5A S1A N2A -14.3(3) . . . .
C9A C8A N1A C2A -62.0(4) . . . .
C10A C9A C8A N1A 121.2(4) . . . .
