#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/60/2226003.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_2226003
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Hemamalini, Madhukar'
'Siddaraju, B. P.'
'Yathirajan, H. S.'
'Narayana, B.'
_publ_section_title
;
 Bis[4-(4-chlorophenyl)-4-hydroxypiperidinium] dipicrate dimethyl
 sulfoxide solvate
;
_journal_coeditor_code           TK2662
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1212
_journal_page_last               o1213
_journal_paper_doi               10.1107/S1600536810015187
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac
'2C11 H15 Cl N O +, 2C6 H2 N3 O7 -, C2 H6 O S'
_chemical_formula_moiety
'2(C11 H15 Cl N O +), 2(C6 H2 N3 O7 -), C2 H6 O S'
_chemical_formula_sum            'C36 H40 Cl2 N8 O17 S'
_chemical_formula_weight         959.72
_chemical_name_systematic
;
Bis[4-(4-chlorophenyl)-4-hydroxypiperidinium] dipicrate dimethyl sulfoxide
solvate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.4300(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.9207(4)
_cell_length_b                   18.1230(9)
_cell_length_c                   12.9886(6)
_cell_measurement_reflns_used    9240
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      34.74
_cell_measurement_theta_min      2.57
_cell_volume                     2077.18(17)
_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 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type
;
Bruker APEX DUO CCD area-detector diffractometer
;
_diffrn_measurement_method       'φ and ω 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  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0482
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25314
_diffrn_reflns_theta_full        34.00
_diffrn_reflns_theta_max         34.00
_diffrn_reflns_theta_min         2.31
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.292
_exptl_absorpt_correction_T_max  0.9542
_exptl_absorpt_correction_T_min  0.8930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             996
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.829
_refine_diff_density_min         -0.881
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     582
_refine_ls_number_reflns         15185
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0893P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1402
_reflns_number_gt                13604
_reflns_number_total             15185
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2662.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2226003
_cod_database_fobs_code          2226003
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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 Cl1A 0.54080(6) 0.78062(3) 0.70106(3) 0.01956(9) Uani d . 1 . .
O O1A 0.61893(15) 1.07386(8) 0.41761(10) 0.0143(2) Uani d . 1 . .
H H1A 0.6671 1.0721 0.4764 0.021 Uiso calc R 1 . .
N N1A 0.66742(19) 1.05337(9) 0.15938(12) 0.0154(3) Uani d . 1 . .
H H1AB 0.6807 1.0893 0.1137 0.019 Uiso calc R 1 . .
H H1AC 0.6638 1.0100 0.1254 0.019 Uiso calc R 1 . .
C C1A 0.4866(2) 0.89223(11) 0.43262(14) 0.0162(3) Uani d . 1 . .
H H1AA 0.4188 0.8926 0.3710 0.019 Uiso calc R 1 . .
C C2A 0.4670(2) 0.84096(12) 0.51056(15) 0.0175(3) Uani d . 1 . .
H H2AA 0.3869 0.8076 0.5012 0.021 Uiso calc R 1 . .
C C3A 0.5690(2) 0.84107(11) 0.60158(14) 0.0141(3) Uani d . 1 . .
C C4A 0.6917(2) 0.88914(12) 0.61605(14) 0.0176(3) Uani d . 1 . .
H H4AA 0.7609 0.8877 0.6770 0.021 Uiso calc R 1 . .
C C5A 0.7090(2) 0.93908(11) 0.53828(14) 0.0167(3) Uani d . 1 . .
H H5AA 0.7911 0.9712 0.5475 0.020 Uiso calc R 1 . .
C C6A 0.60617(19) 0.94264(11) 0.44600(13) 0.0124(3) Uani d . 1 . .
C C7A 0.62592(19) 1.00352(10) 0.36771(13) 0.0112(3) Uani d . 1 . .
C C8A 0.77725(19) 0.99468(11) 0.32607(14) 0.0139(3) Uani d . 1 . .
H H8AA 0.8595 0.9978 0.3837 0.017 Uiso calc R 1 . .
H H8AB 0.7810 0.9462 0.2949 0.017 Uiso calc R 1 . .
C C9A 0.8002(2) 1.05298(11) 0.24570(14) 0.0154(3) Uani d . 1 . .
H H9AA 0.8103 1.1011 0.2786 0.019 Uiso calc R 1 . .
H H9AB 0.8926 1.0427 0.2172 0.019 Uiso calc R 1 . .
C C10A 0.5206(2) 1.06552(12) 0.19942(14) 0.0154(3) Uani d . 1 . .
H H10A 0.4379 1.0655 0.1419 0.018 Uiso calc R 1 . .
H H10B 0.5221 1.1130 0.2339 0.018 Uiso calc R 1 . .
C C11A 0.4964(2) 1.00446(11) 0.27584(13) 0.0138(3) Uani d . 1 . .
H H11A 0.4916 0.9572 0.2405 0.017 Uiso calc R 1 . .
H H11B 0.4008 1.0122 0.3015 0.017 Uiso calc R 1 . .
Cl Cl1B 0.08958(5) 0.91889(3) 0.68165(4) 0.02007(9) Uani d . 1 . .
O O1B 0.13549(15) 0.60441(8) 0.41992(10) 0.0136(2) Uani d . 1 . .
H H1B 0.0543 0.5928 0.4378 0.020 Uiso calc R 1 . .
N N1B 0.14188(19) 0.62391(10) 0.15802(12) 0.0149(3) Uani d . 1 . .
H H1BB 0.1508 0.5882 0.1111 0.018 Uiso calc R 1 . .
H H1BC 0.1357 0.6675 0.1245 0.018 Uiso calc R 1 . .
C C1B 0.1208(2) 0.72111(11) 0.55239(14) 0.0171(3) Uani d . 1 . .
H H1BA 0.1357 0.6727 0.5755 0.020 Uiso calc R 1 . .
C C2B 0.1142(2) 0.77734(12) 0.62472(14) 0.0179(3) Uani d . 1 . .
H H2BA 0.1244 0.7667 0.6954 0.022 Uiso calc R 1 . .
C C3B 0.0925(2) 0.84893(11) 0.59017(14) 0.0149(3) Uani d . 1 . .
C C4B 0.0750(2) 0.86606(11) 0.48428(14) 0.0161(3) Uani d . 1 . .
H H4BA 0.0601 0.9146 0.4617 0.019 Uiso calc R 1 . .
C C5B 0.0803(2) 0.80906(11) 0.41349(14) 0.0148(3) Uani d . 1 . .
H H5BA 0.0669 0.8197 0.3427 0.018 Uiso calc R 1 . .
C C6B 0.10545(19) 0.73598(10) 0.44641(13) 0.0118(3) Uani d . 1 . .
C C7B 0.12034(19) 0.67426(10) 0.36860(13) 0.0117(3) Uani d . 1 . .
C C8B 0.2656(2) 0.68375(11) 0.31946(14) 0.0141(3) Uani d . 1 . .
H H8BA 0.2647 0.7318 0.2864 0.017 Uiso calc R 1 . .
H H8BB 0.3529 0.6817 0.3735 0.017 Uiso calc R 1 . .
C C9B 0.2793(2) 0.62363(11) 0.23875(15) 0.0160(3) Uani d . 1 . .
H H9BA 0.3688 0.6323 0.2062 0.019 Uiso calc R 1 . .
H H9BB 0.2898 0.5758 0.2727 0.019 Uiso calc R 1 . .
C C10B 0.0000(2) 0.61169(11) 0.20400(14) 0.0147(3) Uani d . 1 . .
H H10C 0.0040 0.5639 0.2380 0.018 Uiso calc R 1 . .
H H10D -0.0866 0.6120 0.1493 0.018 Uiso calc R 1 . .
C C11B -0.0179(2) 0.67201(11) 0.28259(14) 0.0133(3) Uani d . 1 . .
H H11C -0.1088 0.6630 0.3135 0.016 Uiso calc R 1 . .
H H11D -0.0290 0.7194 0.2474 0.016 Uiso calc R 1 . .
O O2A 0.61771(16) 0.91428(8) 0.08706(11) 0.0167(2) Uani d . 1 . .
O O3A 0.7941(2) 0.99873(9) -0.01439(12) 0.0238(3) Uani d . 1 . .
O O4A 0.8540(2) 0.95285(9) -0.15570(12) 0.0232(3) Uani d . 1 . .
O O5A 0.9570(2) 0.69858(10) -0.17516(15) 0.0323(4) Uani d . 1 . .
O O6A 0.8761(2) 0.62139(10) -0.06713(16) 0.0306(4) Uani d . 1 . .
O O7A 0.6214(2) 0.71007(10) 0.20625(14) 0.0265(3) Uani d . 1 . .
O O8A 0.47444(18) 0.80551(10) 0.17469(13) 0.0243(3) Uani d . 1 . .
N N2A 0.80695(19) 0.94537(9) -0.07213(12) 0.0148(3) Uani d . 1 . .
N N3A 0.8834(2) 0.68406(10) -0.10369(15) 0.0206(3) Uani d . 1 . .
N N4A 0.57910(18) 0.76640(10) 0.15561(13) 0.0162(3) Uani d . 1 . .
C C12A 0.67605(19) 0.86314(10) 0.04248(13) 0.0125(3) Uani d . 1 . .
C C13A 0.76790(19) 0.87243(10) -0.04033(13) 0.0123(3) Uani d . 1 . .
C C14A 0.8299(2) 0.81494(10) -0.09002(13) 0.0131(3) Uani d . 1 . .
H H14A 0.8853 0.8242 -0.1440 0.016 Uiso calc R 1 . .
C C15A 0.8079(2) 0.74346(11) -0.05797(14) 0.0145(3) Uani d . 1 . .
C C16A 0.7243(2) 0.72826(11) 0.02189(14) 0.0147(3) Uani d . 1 . .
H H16A 0.7119 0.6799 0.0430 0.018 Uiso calc R 1 . .
C C17A 0.66026(19) 0.78560(11) 0.06925(13) 0.0132(3) Uani d . 1 . .
O O2B 0.11214(17) 0.76690(8) 0.09635(11) 0.0175(3) Uani d . 1 . .
O O3B -0.03236(16) 0.88222(9) 0.17146(11) 0.0191(3) Uani d . 1 . .
O O4B 0.1375(2) 0.96634(11) 0.21473(14) 0.0286(4) Uani d . 1 . .
O O5B 0.3832(2) 1.05229(9) -0.07138(16) 0.0295(4) Uani d . 1 . .
O O6B 0.47519(19) 0.97024(9) -0.16764(13) 0.0230(3) Uani d . 1 . .
O O7B 0.3277(2) 0.72048(9) -0.15469(13) 0.0277(4) Uani d . 1 . .
O O8B 0.2714(3) 0.67703(10) -0.01198(14) 0.0320(4) Uani d . 1 . .
N N2B 0.08429(17) 0.91522(10) 0.15888(12) 0.0145(3) Uani d . 1 . .
N N3B 0.39467(19) 0.98818(10) -0.10184(13) 0.0170(3) Uani d . 1 . .
N N4B 0.2868(2) 0.72954(10) -0.06939(12) 0.0157(3) Uani d . 1 . .
C C12B 0.17235(19) 0.81592(10) 0.04862(13) 0.0127(3) Uani d . 1 . .
C C13B 0.16278(19) 0.89373(11) 0.07279(13) 0.0123(3) Uani d . 1 . .
C C14B 0.23231(19) 0.94922(11) 0.02524(14) 0.0141(3) Uani d . 1 . .
H H14B 0.2259 0.9979 0.0466 0.017 Uiso calc R 1 . .
C C15B 0.3126(2) 0.93112(10) -0.05568(14) 0.0135(3) Uani d . 1 . .
C C16B 0.32577(19) 0.85917(11) -0.08763(13) 0.0135(3) Uani d . 1 . .
H H16B 0.3788 0.8480 -0.1422 0.016 Uiso calc R 1 . .
C C17B 0.2583(2) 0.80354(10) -0.03668(14) 0.0129(3) Uani d . 1 . .
S S1 0.74330(6) 0.56505(3) 0.52501(4) 0.02135(10) Uani d . 1 . .
O O9 0.90638(17) 0.55756(10) 0.50845(13) 0.0231(3) Uani d . 1 . .
C C18 0.7073(3) 0.66185(18) 0.5327(3) 0.0446(8) Uani d . 1 . .
H H18A 0.7794 0.6834 0.5865 0.067 Uiso calc R 1 . .
H H18B 0.6067 0.6694 0.5486 0.067 Uiso calc R 1 . .
H H18C 0.7166 0.6847 0.4672 0.067 Uiso calc R 1 . .
C C19 0.6293(2) 0.54900(15) 0.40268(18) 0.0258(4) Uani d . 1 . .
H H19A 0.6479 0.5001 0.3791 0.039 Uiso calc R 1 . .
H H19B 0.6544 0.5844 0.3529 0.039 Uiso calc R 1 . .
H H19C 0.5243 0.5539 0.4101 0.039 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'
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'
Cl Cl 0.1484 0.1585 '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
C7A O1A H1A . . 109.5 ?
C10A N1A C9A . . 112.02(14) ?
C10A N1A H1AB . . 109.2 ?
C9A N1A H1AB . . 109.2 ?
C10A N1A H1AC . . 109.2 ?
C9A N1A H1AC . . 109.2 ?
H1AB N1A H1AC . . 107.9 ?
C6A C1A C2A . . 121.15(17) ?
C6A C1A H1AA . . 119.4 ?
C2A C1A H1AA . . 119.4 ?
C3A C2A C1A . . 118.65(17) ?
C3A C2A H2AA . . 120.7 ?
C1A C2A H2AA . . 120.7 ?
C2A C3A C4A . . 121.56(17) ?
C2A C3A Cl1A . . 119.02(14) ?
C4A C3A Cl1A . . 119.41(14) ?
C5A C4A C3A . . 118.80(17) ?
C5A C4A H4AA . . 120.6 ?
C3A C4A H4AA . . 120.6 ?
C4A C5A C6A . . 121.80(17) ?
C4A C5A H5AA . . 119.1 ?
C6A C5A H5AA . . 119.1 ?
C1A C6A C5A . . 117.99(16) ?
C1A C6A C7A . . 123.39(16) ?
C5A C6A C7A . . 118.56(16) ?
O1A C7A C6A . . 108.89(13) ?
O1A C7A C8A . . 110.52(14) ?
C6A C7A C8A . . 110.63(14) ?
O1A C7A C11A . . 105.28(14) ?
C6A C7A C11A . . 112.23(14) ?
C8A C7A C11A . . 109.16(14) ?
C9A C8A C7A . . 112.54(15) ?
C9A C8A H8AA . . 109.1 ?
C7A C8A H8AA . . 109.1 ?
C9A C8A H8AB . . 109.1 ?
C7A C8A H8AB . . 109.1 ?
H8AA C8A H8AB . . 107.8 ?
N1A C9A C8A . . 110.14(15) ?
N1A C9A H9AA . . 109.6 ?
C8A C9A H9AA . . 109.6 ?
N1A C9A H9AB . . 109.6 ?
C8A C9A H9AB . . 109.6 ?
H9AA C9A H9AB . . 108.1 ?
N1A C10A C11A . . 109.57(16) ?
N1A C10A H10A . . 109.8 ?
C11A C10A H10A . . 109.8 ?
N1A C10A H10B . . 109.8 ?
C11A C10A H10B . . 109.8 ?
H10A C10A H10B . . 108.2 ?
C10A C11A C7A . . 110.63(15) ?
C10A C11A H11A . . 109.5 ?
C7A C11A H11A . . 109.5 ?
C10A C11A H11B . . 109.5 ?
C7A C11A H11B . . 109.5 ?
H11A C11A H11B . . 108.1 ?
C7B O1B H1B . . 109.5 ?
C9B N1B C10B . . 112.08(14) ?
C9B N1B H1BB . . 109.2 ?
C10B N1B H1BB . . 109.2 ?
C9B N1B H1BC . . 109.2 ?
C10B N1B H1BC . . 109.2 ?
H1BB N1B H1BC . . 107.9 ?
C6B C1B C2B . . 121.22(18) ?
C6B C1B H1BA . . 119.4 ?
C2B C1B H1BA . . 119.4 ?
C3B C2B C1B . . 119.16(17) ?
C3B C2B H2BA . . 120.4 ?
C1B C2B H2BA . . 120.4 ?
C2B C3B C4B . . 121.36(17) ?
C2B C3B Cl1B . . 118.64(14) ?
C4B C3B Cl1B . . 119.99(15) ?
C5B C4B C3B . . 118.51(18) ?
C5B C4B H4BA . . 120.7 ?
C3B C4B H4BA . . 120.7 ?
C4B C5B C6B . . 121.41(16) ?
C4B C5B H5BA . . 119.3 ?
C6B C5B H5BA . . 119.3 ?
C1B C6B C5B . . 118.31(17) ?
C1B C6B C7B . . 120.55(16) ?
C5B C6B C7B . . 121.12(15) ?
O1B C7B C6B . . 110.62(14) ?
O1B C7B C8B . . 105.39(14) ?
C6B C7B C8B . . 110.72(14) ?
O1B C7B C11B . . 109.05(14) ?
C6B C7B C11B . . 111.22(14) ?
C8B C7B C11B . . 109.66(14) ?
C9B C8B C7B . . 111.24(15) ?
C9B C8B H8BA . . 109.4 ?
C7B C8B H8BA . . 109.4 ?
C9B C8B H8BB . . 109.4 ?
C7B C8B H8BB . . 109.4 ?
H8BA C8B H8BB . . 108.0 ?
N1B C9B C8B . . 109.85(15) ?
N1B C9B H9BA . . 109.7 ?
C8B C9B H9BA . . 109.7 ?
N1B C9B H9BB . . 109.7 ?
C8B C9B H9BB . . 109.7 ?
H9BA C9B H9BB . . 108.2 ?
N1B C10B C11B . . 109.90(15) ?
N1B C10B H10C . . 109.7 ?
C11B C10B H10C . . 109.7 ?
N1B C10B H10D . . 109.7 ?
C11B C10B H10D . . 109.7 ?
H10C C10B H10D . . 108.2 ?
C10B C11B C7B . . 110.79(15) ?
C10B C11B H11C . . 109.5 ?
C7B C11B H11C . . 109.5 ?
C10B C11B H11D . . 109.5 ?
C7B C11B H11D . . 109.5 ?
H11C C11B H11D . . 108.1 ?
O4A N2A O3A . . 121.54(17) ?
O4A N2A C13A . . 118.85(16) ?
O3A N2A C13A . . 119.60(15) ?
O6A N3A O5A . . 123.05(19) ?
O6A N3A C15A . . 118.24(17) ?
O5A N3A C15A . . 118.66(18) ?
O8A N4A O7A . . 123.30(17) ?
O8A N4A C17A . . 119.63(17) ?
O7A N4A C17A . . 117.07(17) ?
O2A C12A C13A . . 125.20(17) ?
O2A C12A C17A . . 122.95(16) ?
C13A C12A C17A . . 111.85(15) ?
C14A C13A N2A . . 115.26(15) ?
C14A C13A C12A . . 124.41(17) ?
N2A C13A C12A . . 120.24(16) ?
C13A C14A C15A . . 118.76(16) ?
C13A C14A H14A . . 120.6 ?
C15A C14A H14A . . 120.6 ?
C14A C15A C16A . . 121.66(17) ?
C14A C15A N3A . . 118.66(16) ?
C16A C15A N3A . . 119.52(17) ?
C17A C16A C15A . . 119.20(17) ?
C17A C16A H16A . . 120.4 ?
C15A C16A H16A . . 120.4 ?
C16A C17A C12A . . 124.09(16) ?
C16A C17A N4A . . 116.64(17) ?
C12A C17A N4A . . 119.17(16) ?
O4B N2B O3B . . 123.28(17) ?
O4B N2B C13B . . 117.86(16) ?
O3B N2B C13B . . 118.85(16) ?
O5B N3B O6B . . 123.47(18) ?
O5B N3B C15B . . 117.93(17) ?
O6B N3B C15B . . 118.58(17) ?
O7B N4B O8B . . 121.23(18) ?
O7B N4B C17B . . 118.65(16) ?
O8B N4B C17B . . 120.11(15) ?
O2B C12B C13B . . 122.76(16) ?
O2B C12B C17B . . 125.56(17) ?
C13B C12B C17B . . 111.68(15) ?
C14B C13B C12B . . 124.71(16) ?
C14B C13B N2B . . 116.66(17) ?
C12B C13B N2B . . 118.45(16) ?
C13B C14B C15B . . 118.81(17) ?
C13B C14B H14B . . 120.6 ?
C15B C14B H14B . . 120.6 ?
C16B C15B C14B . . 121.65(17) ?
C16B C15B N3B . . 118.75(16) ?
C14B C15B N3B . . 119.41(17) ?
C15B C16B C17B . . 118.73(16) ?
C15B C16B H16B . . 120.6 ?
C17B C16B H16B . . 120.6 ?
C16B C17B N4B . . 115.28(15) ?
C16B C17B C12B . . 124.34(17) ?
N4B C17B C12B . . 120.27(16) ?
O9 S1 C19 . . 107.14(10) ?
O9 S1 C18 . . 106.33(12) ?
C19 S1 C18 . . 97.27(15) ?
S1 C18 H18A . . 109.5 ?
S1 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
S1 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
S1 C19 H19A . . 109.5 ?
S1 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
S1 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 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
Cl1A C3A . 1.7402(18) ?
O1A C7A . 1.436(2) ?
O1A H1A . 0.8200 ?
N1A C10A . 1.495(2) ?
N1A C9A . 1.507(2) ?
N1A H1AB . 0.9000 ?
N1A H1AC . 0.9000 ?
C1A C6A . 1.396(2) ?
C1A C2A . 1.404(3) ?
C1A H1AA . 0.9300 ?
C2A C3A . 1.383(3) ?
C2A H2AA . 0.9300 ?
C3A C4A . 1.390(3) ?
C4A C5A . 1.382(3) ?
C4A H4AA . 0.9300 ?
C5A C6A . 1.400(2) ?
C5A H5AA . 0.9300 ?
C6A C7A . 1.528(2) ?
C7A C8A . 1.534(2) ?
C7A C11A . 1.535(2) ?
C8A C9A . 1.520(3) ?
C8A H8AA . 0.9700 ?
C8A H8AB . 0.9700 ?
C9A H9AA . 0.9700 ?
C9A H9AB . 0.9700 ?
C10A C11A . 1.523(3) ?
C10A H10A . 0.9700 ?
C10A H10B . 0.9700 ?
C11A H11A . 0.9700 ?
C11A H11B . 0.9700 ?
Cl1B C3B . 1.7405(19) ?
O1B C7B . 1.428(2) ?
O1B H1B . 0.8200 ?
N1B C9B . 1.492(3) ?
N1B C10B . 1.493(2) ?
N1B H1BB . 0.9000 ?
N1B H1BC . 0.9000 ?
C1B C6B . 1.390(2) ?
C1B C2B . 1.393(3) ?
C1B H1BA . 0.9300 ?
C2B C3B . 1.377(3) ?
C2B H2BA . 0.9300 ?
C3B C4B . 1.396(3) ?
C4B C5B . 1.388(3) ?
C4B H4BA . 0.9300 ?
C5B C6B . 1.400(3) ?
C5B H5BA . 0.9300 ?
C6B C7B . 1.526(2) ?
C7B C8B . 1.536(2) ?
C7B C11B . 1.538(2) ?
C8B C9B . 1.529(3) ?
C8B H8BA . 0.9700 ?
C8B H8BB . 0.9700 ?
C9B H9BA . 0.9700 ?
C9B H9BB . 0.9700 ?
C10B C11B . 1.520(3) ?
C10B H10C . 0.9700 ?
C10B H10D . 0.9700 ?
C11B H11C . 0.9700 ?
C11B H11D . 0.9700 ?
O2A C12A . 1.246(2) ?
O3A N2A . 1.239(2) ?
O4A N2A . 1.227(2) ?
O5A N3A . 1.241(2) ?
O6A N3A . 1.236(2) ?
O7A N4A . 1.243(2) ?
O8A N4A . 1.226(2) ?
N2A C13A . 1.443(3) ?
N3A C15A . 1.443(3) ?
N4A C17A . 1.463(2) ?
C12A C13A . 1.454(2) ?
C12A C17A . 1.459(3) ?
C13A C14A . 1.383(3) ?
C14A C15A . 1.383(3) ?
C14A H14A . 0.9300 ?
C15A C16A . 1.391(3) ?
C16A C17A . 1.374(3) ?
C16A H16A . 0.9300 ?
O2B C12B . 1.249(2) ?
O3B N2B . 1.232(2) ?
O4B N2B . 1.228(2) ?
O5B N3B . 1.236(2) ?
O6B N3B . 1.238(2) ?
O7B N4B . 1.227(2) ?
O8B N4B . 1.229(2) ?
N2B C13B . 1.457(2) ?
N3B C15B . 1.447(2) ?
N4B C17B . 1.441(3) ?
C12B C13B . 1.450(3) ?
C12B C17B . 1.454(2) ?
C13B C14B . 1.375(3) ?
C14B C15B . 1.395(3) ?
C14B H14B . 0.9300 ?
C15B C16B . 1.379(3) ?
C16B C17B . 1.391(3) ?
C16B H16B . 0.9300 ?
S1 O9 . 1.5076(16) ?
S1 C19 . 1.780(2) ?
S1 C18 . 1.789(3) ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 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 H1AB O7B 2_655 0.90 2.44 3.030(2) 123 yes
N1A H1AB O8B 2_655 0.90 2.15 3.048(2) 176 yes
O1A H1A O1B 2_656 0.82 2.14 2.8642(19) 148 yes
O1B H1B O9 1_455 0.82 1.83 2.629(2) 165 yes
N1A H1AC O2A . 0.90 1.83 2.704(2) 162 yes
N1A H1AC O3A . 0.90 2.30 2.846(2) 119 yes
N1B H1BB O3A 2_645 0.90 2.15 3.044(2) 171 yes
N1B H1BB O4A 2_645 0.90 2.52 3.101(2) 123 yes
N1B H1BC O2B . 0.90 1.84 2.714(2) 162 yes
C4A H4AA O4A 1_556 0.93 2.51 3.311(2) 145 yes
C5A H5AA O1B 2_656 0.93 2.52 3.313(2) 143 yes
C8A H8AA O9 2_756 0.97 2.58 3.479(2) 155 yes
C9A H9AB O4B 1_655 0.97 2.59 3.469(3) 151 yes
C11A H11A O2A . 0.97 2.55 3.261(2) 130 yes
C11A H11B O4B . 0.97 2.59 3.258(3) 126 yes
C2B H2BA O7B 1_556 0.93 2.60 3.361(3) 140 yes
C14B H14B O6A 2_655 0.93 2.45 3.335(3) 160 yes
C5B H5BA O3B . 0.93 2.54 3.424(2) 160 yes
C16A H16A O5B 2_645 0.93 2.51 3.418(3) 166 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
C6A C1A C2A C3A . . . . -0.1(3) ?
C1A C2A C3A C4A . . . . -1.7(3) ?
C1A C2A C3A Cl1A . . . . 177.09(15) ?
C2A C3A C4A C5A . . . . 1.7(3) ?
Cl1A C3A C4A C5A . . . . -177.14(16) ?
C3A C4A C5A C6A . . . . 0.3(3) ?
C2A C1A C6A C5A . . . . 2.0(3) ?
C2A C1A C6A C7A . . . . -175.00(18) ?
C4A C5A C6A C1A . . . . -2.1(3) ?
C4A C5A C6A C7A . . . . 175.07(18) ?
C1A C6A C7A O1A . . . . 118.45(19) ?
C5A C6A C7A O1A . . . . -58.5(2) ?
C1A C6A C7A C8A . . . . -119.90(19) ?
C5A C6A C7A C8A . . . . 63.1(2) ?
C1A C6A C7A C11A . . . . 2.3(2) ?
C5A C6A C7A C11A . . . . -174.66(16) ?
O1A C7A C8A C9A . . . . -60.77(19) ?
C6A C7A C8A C9A . . . . 178.54(15) ?
C11A C7A C8A C9A . . . . 54.6(2) ?
C10A N1A C9A C8A . . . . 56.6(2) ?
C7A C8A C9A N1A . . . . -54.3(2) ?
C9A N1A C10A C11A . . . . -59.5(2) ?
N1A C10A C11A C7A . . . . 59.51(19) ?
O1A C7A C11A C10A . . . . 61.98(18) ?
C6A C7A C11A C10A . . . . -179.71(15) ?
C8A C7A C11A C10A . . . . -56.7(2) ?
C6B C1B C2B C3B . . . . -0.2(3) ?
C1B C2B C3B C4B . . . . 0.8(3) ?
C1B C2B C3B Cl1B . . . . -178.29(15) ?
C2B C3B C4B C5B . . . . -0.2(3) ?
Cl1B C3B C4B C5B . . . . 178.96(14) ?
C3B C4B C5B C6B . . . . -1.2(3) ?
C2B C1B C6B C5B . . . . -1.1(3) ?
C2B C1B C6B C7B . . . . 177.12(17) ?
C4B C5B C6B C1B . . . . 1.8(3) ?
C4B C5B C6B C7B . . . . -176.40(16) ?
C1B C6B C7B O1B . . . . 5.6(2) ?
C5B C6B C7B O1B . . . . -176.22(15) ?
C1B C6B C7B C8B . . . . -110.87(19) ?
C5B C6B C7B C8B . . . . 67.3(2) ?
C1B C6B C7B C11B . . . . 126.93(18) ?
C5B C6B C7B C11B . . . . -54.9(2) ?
O1B C7B C8B C9B . . . . 62.18(18) ?
C6B C7B C8B C9B . . . . -178.17(15) ?
C11B C7B C8B C9B . . . . -55.1(2) ?
C10B N1B C9B C8B . . . . -58.6(2) ?
C7B C8B C9B N1B . . . . 56.3(2) ?
C9B N1B C10B C11B . . . . 59.6(2) ?
N1B C10B C11B C7B . . . . -57.6(2) ?
O1B C7B C11B C10B . . . . -59.23(19) ?
C6B C7B C11B C10B . . . . 178.51(14) ?
C8B C7B C11B C10B . . . . 55.7(2) ?
O4A N2A C13A C14A . . . . 19.3(2) ?
O3A N2A C13A C14A . . . . -159.87(18) ?
O4A N2A C13A C12A . . . . -163.82(17) ?
O3A N2A C13A C12A . . . . 17.0(3) ?
O2A C12A C13A C14A . . . . -178.98(18) ?
C17A C12A C13A C14A . . . . 1.6(2) ?
O2A C12A C13A N2A . . . . 4.4(3) ?
C17A C12A C13A N2A . . . . -175.00(15) ?
N2A C13A C14A C15A . . . . 174.83(16) ?
C12A C13A C14A C15A . . . . -1.9(3) ?
C13A C14A C15A C16A . . . . 0.6(3) ?
C13A C14A C15A N3A . . . . -174.74(17) ?
O6A N3A C15A C14A . . . . 172.6(2) ?
O5A N3A C15A C14A . . . . -4.8(3) ?
O6A N3A C15A C16A . . . . -2.9(3) ?
O5A N3A C15A C16A . . . . 179.7(2) ?
C14A C15A C16A C17A . . . . 0.9(3) ?
N3A C15A C16A C17A . . . . 176.16(17) ?
C15A C16A C17A C12A . . . . -1.1(3) ?
C15A C16A C17A N4A . . . . -177.49(16) ?
O2A C12A C17A C16A . . . . -179.49(18) ?
C13A C12A C17A C16A . . . . 0.0(2) ?
O2A C12A C17A N4A . . . . -3.2(3) ?
C13A C12A C17A N4A . . . . 176.24(15) ?
O8A N4A C17A C16A . . . . -151.85(18) ?
O7A N4A C17A C16A . . . . 28.1(2) ?
O8A N4A C17A C12A . . . . 31.6(2) ?
O7A N4A C17A C12A . . . . -148.48(18) ?
O2B C12B C13B C14B . . . . 177.23(18) ?
C17B C12B C13B C14B . . . . -3.2(2) ?
O2B C12B C13B N2B . . . . 2.3(3) ?
C17B C12B C13B N2B . . . . -178.07(14) ?
O4B N2B C13B C14B . . . . -33.8(2) ?
O3B N2B C13B C14B . . . . 145.35(18) ?
O4B N2B C13B C12B . . . . 141.56(19) ?
O3B N2B C13B C12B . . . . -39.3(2) ?
C12B C13B C14B C15B . . . . 3.2(3) ?
N2B C13B C14B C15B . . . . 178.19(15) ?
C13B C14B C15B C16B . . . . -1.1(3) ?
C13B C14B C15B N3B . . . . -175.95(16) ?
O5B N3B C15B C16B . . . . -179.11(19) ?
O6B N3B C15B C16B . . . . -0.8(3) ?
O5B N3B C15B C14B . . . . -4.1(3) ?
O6B N3B C15B C14B . . . . 174.24(18) ?
C14B C15B C16B C17B . . . . -0.7(3) ?
N3B C15B C16B C17B . . . . 174.20(16) ?
C15B C16B C17B N4B . . . . -175.51(16) ?
C15B C16B C17B C12B . . . . 0.5(3) ?
O7B N4B C17B C16B . . . . -20.3(3) ?
O8B N4B C17B C16B . . . . 159.0(2) ?
O7B N4B C17B C12B . . . . 163.47(18) ?
O8B N4B C17B C12B . . . . -17.2(3) ?
O2B C12B C17B C16B . . . . -179.16(18) ?
C13B C12B C17B C16B . . . . 1.2(2) ?
O2B C12B C17B N4B . . . . -3.3(3) ?
C13B C12B C17B N4B . . . . 177.10(16) ?
