#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/77/2207793.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_2207793
loop_
_publ_author_name
'K. Anitha'
'S. Athimoolam'
'R. K. Rajaram'
_publ_section_title
;
 <small>DL</small>-Methionine <small>DL</small>-methioninium picrate
;
_journal_coeditor_code           HK6032
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o8
_journal_page_last               o10
_journal_paper_doi               10.1107/S1600536805038948
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac
'C5 H11 N O2 S, C5 H12 N O2 S +, C6 H2 N3 O7 -'
_chemical_formula_moiety
'C5 H11 N O2 S, C5 H12 N O2 S +, C6 H2 N3 O7 -'
_chemical_formula_sum            'C16 H25 N5 O11 S2'
_chemical_formula_weight         527.53
_chemical_name_common            'DL-methionine DL-methioninium picrate'
_chemical_name_systematic
;
DL-methionine DL-methioninium picrate
;
_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                103.900(10)
_cell_angle_beta                 97.04(2)
_cell_angle_gamma                101.73(2)
_cell_formula_units_Z            2
_cell_length_a                   7.0760(10)
_cell_length_b                   12.1020(10)
_cell_length_c                   14.895(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14.20
_cell_measurement_theta_min      6.76
_cell_volume                     1192.4(3)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  SHELXTL/PC
_computing_structure_solution    'SHELXTL/PC (Bruker, 2000)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius MACH3 four-circle'
_diffrn_measurement_method       ω-2θ
_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  0.0141
_diffrn_reflns_av_sigmaI/netI    0.0444
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4940
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.58
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_meas      1.460
_exptl_crystal_density_method
'flotation in a mixture of carbon tetrachloride and xylene'
_exptl_crystal_description       needle
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.804
_refine_diff_density_min         -0.559
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         4217
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1303
_refine_ls_R_factor_gt           0.0721
_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)+(0.1091P)²+0.8526P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1984
_refine_ls_wR_factor_ref         0.2370
_reflns_number_gt                2516
_reflns_number_total             4217
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk6032.cif
_cod_data_source_block           I
_cod_database_code               2207793
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_type_symbol
S1 0.2509(17) 0.0585(9) 0.6210(7) 0.158(4) Uani d P 0.55 B 1 S
S11 0.218(4) 0.0339(18) 0.5625(13) 0.111(6) Uani d P 0.21 B 2 S
S12 0.196(2) 0.0260(10) 0.5974(10) 0.053(2) Uani d P 0.24 B 3 S
S2 1.153(3) 0.9057(19) 0.9041(15) 0.074(4) Uani d P 0.55 D 1 S
S21 1.187(7) 1.028(4) 0.868(3) 0.219(17) Uiso d P 0.10 D 2 S
S22 1.171(6) 0.891(3) 0.901(3) 0.070(5) Uani d P 0.35 D 3 S
O1 0.5379(5) 0.4989(4) 0.7445(2) 0.0776(11) Uani d . 1 . . O
O1A -0.0396(4) 0.3706(3) 0.42963(19) 0.0537(8) Uani d . 1 . . O
O1B -0.2265(5) 0.2605(3) 0.5002(2) 0.0691(10) Uani d . 1 . . O
O2 0.2200(7) 0.5794(4) 0.7647(3) 0.0907(13) Uani d . 1 . . O
O2A 0.5877(5) 0.6334(3) 0.5883(2) 0.0548(8) Uani d . 1 . . O
O2B 0.4874(5) 0.7963(3) 0.6390(3) 0.0691(10) Uani d . 1 . . O
O3 0.1344(8) 0.5922(4) 0.8995(3) 0.1067(16) Uani d . 1 . . O
O4 0.1992(7) 0.3067(5) 1.0576(3) 0.1073(16) Uani d . 1 . . O
O5 0.4230(8) 0.2122(5) 1.0373(4) 0.1134(17) Uani d . 1 . . O
O6 0.8341(6) 0.2702(5) 0.8164(3) 0.1004(12) Uani d . 1 . . O
O7 0.8363(10) 0.4007(6) 0.7498(5) 0.156(3) Uani d . 1 . . O
N1 0.2243(7) 0.5521(4) 0.8388(3) 0.0712(12) Uani d . 1 . . N
N2 0.3302(7) 0.2801(4) 1.0177(3) 0.0701(12) Uani d . 1 . . N
N3 0.7622(8) 0.3449(6) 0.7973(4) 0.1004(12) Uani d . 1 . . N
N11 0.2558(5) 0.4510(3) 0.5766(2) 0.0473(9) Uani d . 1 B . N
N21 0.8588(5) 0.6776(3) 0.7398(2) 0.0536(9) Uani d . 1 . . N
C1 0.4937(6) 0.4498(4) 0.8070(3) 0.0514(11) Uani d . 1 . . C
C2 0.3349(7) 0.4685(4) 0.8558(3) 0.0501(10) Uani d . 1 . . C
C3 0.2829(6) 0.4131(4) 0.9224(3) 0.0510(11) Uani d . 1 . . C
C4 0.3833(7) 0.3357(4) 0.9450(3) 0.0507(11) Uani d . 1 . . C
C5 0.5410(7) 0.3135(4) 0.9038(3) 0.0526(11) Uani d . 1 . . C
C6 0.5940(6) 0.3699(4) 0.8375(3) 0.0510(11) Uani d . 1 . . C
C11 -0.0678(6) 0.3269(4) 0.4952(3) 0.0439(10) Uani d . 1 B . C
C12 0.0955(7) 0.3520(4) 0.5787(3) 0.0537(11) Uani d . 1 . . C
C14 0.1235(15) 0.1645(8) 0.6194(9) 0.157(3) Uani d . 1 . . C
C15 0.4668(16) 0.0792(8) 0.6337(9) 0.157(3) Uani d . 1 . . C
C21 0.5973(6) 0.7260(4) 0.6456(3) 0.0479(10) Uani d . 1 . . C
C22 0.7468(6) 0.7684(4) 0.7363(3) 0.0508(11) Uani d . 1 . . C
C23 0.8796(8) 0.8878(4) 0.7478(4) 0.0699(14) Uani d . 1 D . C
C24 0.9766(9) 0.9572(5) 0.8492(4) 0.0896(19) Uani d . 1 . . C
C25 1.3616(10) 0.9459(7) 0.8475(5) 0.100(2) Uani d . 1 . . C
C131 0.118(2) 0.2552(12) 0.6108(11) 0.061(3) Uiso d P 0.35 B 1 C
C132 0.2035(11) 0.2375(7) 0.5659(5) 0.0575(18) Uani d P 0.65 B 2 C
H2B 0.3954 0.7644 0.5950 0.104 Uiso calc R 1 . . H
H3 0.1792 0.4283 0.9522 0.061 Uiso calc R 1 . . H
H5 0.6100 0.2616 0.9206 0.063 Uiso calc R 1 . . H
H22A 0.0353 0.3922 0.6287 0.064 Uiso calc PR 0.35 A 1 H
H11A 0.2052 0.5015 0.5526 0.071 Uiso calc R 1 . . H
H11B 0.3377 0.4238 0.5412 0.071 Uiso calc R 1 . . H
H11C 0.3206 0.4871 0.6348 0.071 Uiso calc R 1 . . H
H12B 0.0453 0.3698 0.6377 0.064 Uiso d PR 0.65 A 2 H
H13A 0.2518 0.2915 0.6432 0.073 Uiso calc PR 0.35 B 1 H
H13B 0.0417 0.2719 0.6602 0.073 Uiso calc PR 0.35 B 1 H
H13C 0.1799 0.1938 0.5002 0.069 Uiso calc PR 0.65 B 2 H
H13D 0.3441 0.2660 0.5875 0.069 Uiso calc PR 0.65 B 2 H
H14A 0.0075 0.1178 0.5741 0.188 Uiso calc PR 0.35 B 1 H
H14B 0.0815 0.1714 0.6797 0.188 Uiso calc PR 0.35 B 1 H
H14C 0.0067 0.1095 0.5799 0.188 Uiso d PR 0.65 B 2 H
H14D 0.0879 0.2032 0.6776 0.188 Uiso d PR 0.65 B 2 H
H15A 0.5027 0.0054 0.6238 0.236 Uiso calc PR 0.55 B 1 H
H15B 0.5240 0.1268 0.6964 0.236 Uiso calc PR 0.55 B 1 H
H15C 0.5140 0.1188 0.5892 0.236 Uiso calc PR 0.55 B 1 H
H15D 0.4739 -0.0008 0.6267 0.236 Uiso d PR 0.21 B 2 H
H15E 0.5581 0.1290 0.6884 0.236 Uiso d PR 0.21 B 2 H
H15F 0.4990 0.1023 0.5791 0.236 Uiso d PR 0.21 B 2 H
H15G 0.5225 0.0122 0.6254 0.236 Uiso d PR 0.24 B 3 H
H15H 0.4631 0.1093 0.6991 0.236 Uiso d PR 0.24 B 3 H
H15I 0.5457 0.1387 0.6124 0.236 Uiso d PR 0.24 B 3 H
H21A 0.9458 0.7007 0.7932 0.080 Uiso calc R 1 . . H
H21B 0.9212 0.6676 0.6912 0.080 Uiso calc R 1 . . H
H21C 0.7764 0.6103 0.7372 0.080 Uiso calc R 1 . . H
H22 0.6747 0.7749 0.7887 0.061 Uiso calc R 1 . . H
H23A 0.8036 0.9344 0.7214 0.084 Uiso calc R 1 . . H
H23B 0.9823 0.8776 0.7112 0.084 Uiso calc R 1 . . H
H24A 0.8742 0.9606 0.8868 0.107 Uiso calc PR 0.55 C 1 H
H24B 1.0349 1.0370 0.8491 0.107 Uiso calc PR 0.55 C 1 H
H24C 0.9014 1.0148 0.8681 0.107 Uiso d PR 0.10 C 2 H
H24D 0.9497 0.9019 0.8863 0.107 Uiso d PR 0.10 C 2 H
H24E 0.8761 0.9598 0.8880 0.107 Uiso d PR 0.35 C 3 H
H24F 1.0368 1.0373 0.8506 0.107 Uiso d PR 0.35 C 3 H
H25A 1.4700 0.9192 0.8726 0.150 Uiso calc PR 0.55 D 1 H
H25B 1.3988 1.0297 0.8593 0.150 Uiso calc PR 0.55 D 1 H
H25C 1.3256 0.9101 0.7810 0.150 Uiso calc PR 0.55 D 1 H
H25D 1.4356 0.9351 0.9019 0.150 Uiso d PR 0.10 D 2 H
H25E 1.4475 0.9929 0.8185 0.150 Uiso d PR 0.10 D 2 H
H25F 1.3019 0.8709 0.8035 0.150 Uiso d PR 0.10 D 2 H
H25G 1.4767 0.9226 0.8693 0.150 Uiso d PR 0.35 D 3 H
H25H 1.3881 1.0300 0.8640 0.150 Uiso d PR 0.35 D 3 H
H25I 1.3258 0.9152 0.7804 0.150 Uiso d PR 0.35 D 3 H
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
_geom_angle_publ_flag
O1A C11 O1B 125.3(4) y
O1A C11 C12 120.1(4) y
O1B C11 C12 114.6(3) y
C131 C12 N11 126.1(7) ?
C131 C12 C11 115.5(7) ?
N11 C12 C11 109.8(3) ?
C131 C12 C132 34.9(7) ?
N11 C12 C132 103.3(4) ?
C11 C12 C132 109.1(4) ?
C131 C12 H22A 99.8 ?
N11 C12 H22A 99.8 ?
C11 C12 H22A 99.8 ?
C132 C12 H22A 133.6 ?
C131 C12 H12B 79.6 ?
N11 C12 H12B 110.5 ?
C11 C12 H12B 110.5 ?
C132 C12 H12B 113.4 ?
H22A C12 H12B 20.3 ?
C12 N11 H11A 109.5 ?
C12 N11 H11B 109.5 ?
H11A N11 H11B 109.5 ?
C12 N11 H11C 109.5 ?
H11A N11 H11C 109.5 ?
H11B N11 H11C 109.5 ?
C14 C131 C12 166.8(15) ?
C14 C131 H12B 150.6 ?
C12 C131 H12B 38.3 ?
C14 C131 H13A 94.1 ?
C12 C131 H13A 94.1 ?
H12B C131 H13A 94.7 ?
C14 C131 H13B 94.1 ?
C12 C131 H13B 94.1 ?
H12B C131 H13B 56.6 ?
H13A C131 H13B 103.1 ?
C14 C131 H14D 45.8 ?
C12 C131 H14D 144.5 ?
H12B C131 H14D 106.2 ?
H13A C131 H14D 89.7 ?
H13B C131 H14D 50.8 ?
C14 C132 C12 108.4(6) ?
C14 C132 H13C 110.0 ?
C12 C132 H13C 110.0 ?
C14 C132 H13D 110.0 ?
C12 C132 H13D 110.0 ?
H13C C132 H13D 108.4 ?
C131 C14 C132 43.3(9) ?
C131 C14 S1 149.6(13) ?
C132 C14 S1 109.9(9) ?
C131 C14 S12 156.5(14) ?
C132 C14 S12 113.2(9) ?
S1 C14 S12 16.5(5) ?
C131 C14 S11 139.0(14) ?
C132 C14 S11 96.0(10) ?
S1 C14 S11 26.2(7) ?
S12 C14 S11 18.0(5) ?
C131 C14 H14A 99.3 ?
C132 C14 H14A 99.0 ?
S1 C14 H14A 99.3 ?
S12 C14 H14A 82.8 ?
S11 C14 H14A 79.7 ?
C131 C14 H14B 99.3 ?
C132 C14 H14B 139.1 ?
S1 C14 H14B 99.3 ?
S12 C14 H14B 103.0 ?
S11 C14 H14B 120.9 ?
H14A C14 H14B 104.0 ?
C131 C14 H14C 107.0 ?
C132 C14 H14C 107.2 ?
S1 C14 H14C 93.8 ?
S12 C14 H14C 77.3 ?
S11 C14 H14C 76.6 ?
H14A C14 H14C 8.7 ?
H14B C14 H14C 98.5 ?
C131 C14 H14D 76.5 ?
C132 C14 H14D 116.4 ?
S1 C14 H14D 118.3 ?
S12 C14 H14D 125.0 ?
S11 C14 H14D 142.7 ?
H14A C14 H14D 110.8 ?
H14B C14 H14D 23.0 ?
H14C C14 H14D 108.2 ?
C15 S1 C14 124.8(9) ?
C15 S1 H15H 34.6 ?
C14 S1 H15H 112.2 ?
C15 S11 C14 98.4(11) ?
C14 S12 C15 100.6(7) ?
S1 C15 S11 26.3(9) ?
S1 C15 S12 12.1(6) ?
S11 C15 S12 18.2(6) ?
S1 C15 H15A 109.5 ?
S11 C15 H15A 101.0 ?
S12 C15 H15A 99.8 ?
S1 C15 H15B 109.5 ?
S11 C15 H15B 134.6 ?
S12 C15 H15B 120.6 ?
H15A C15 H15B 109.5 ?
S1 C15 H15C 109.5 ?
S11 C15 H15C 90.1 ?
S12 C15 H15C 107.4 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
S1 C15 H15D 97.3 ?
S11 C15 H15D 92.1 ?
S12 C15 H15D 88.4 ?
H15A C15 H15D 12.9 ?
H15B C15 H15D 111.0 ?
H15C C15 H15D 119.3 ?
S1 C15 H15E 125.7 ?
S11 C15 H15E 149.5 ?
S12 C15 H15E 137.1 ?
H15A C15 H15E 104.2 ?
H15B C15 H15E 16.8 ?
H15C C15 H15E 97.4 ?
H15D C15 H15E 109.5 ?
S1 C15 H15F 104.2 ?
S11 C15 H15F 81.8 ?
S12 C15 H15F 99.8 ?
H15A C15 H15F 101.3 ?
H15B C15 H15F 122.3 ?
H15C C15 H15F 12.9 ?
H15D C15 H15F 109.5 ?
H15E C15 H15F 109.5 ?
S1 C15 H15G 118.0 ?
S11 C15 H15G 108.6 ?
S12 C15 H15G 108.2 ?
H15A C15 H15G 8.5 ?
H15B C15 H15G 105.3 ?
H15C C15 H15G 104.8 ?
H15D C15 H15G 21.2 ?
H15E C15 H15G 98.1 ?
H15F C15 H15G 98.1 ?
S1 C15 H15H 84.6 ?
S11 C15 H15H 110.9 ?
S12 C15 H15H 94.7 ?
H15A C15 H15H 109.6 ?
H15B C15 H15H 27.2 ?
H15C C15 H15H 130.4 ?
H15D C15 H15H 104.8 ?
H15E C15 H15H 43.8 ?
H15F C15 H15H 142.9 ?
H15G C15 H15H 109.5 ?
S1 C15 H15I 122.1 ?
S11 C15 H15I 109.0 ?
S12 C15 H15I 124.1 ?
H15A C15 H15I 116.6 ?
H15B C15 H15I 86.7 ?
H15C C15 H15I 23.0 ?
H15D C15 H15I 129.0 ?
H15E C15 H15I 74.4 ?
H15F C15 H15I 35.6 ?
H15G C15 H15I 109.5 ?
H15H C15 H15I 109.5 ?
C21 O2B H2B 109.5 ?
O2A C21 O2B 126.1(4) y
O2A C21 C22 121.3(4) y
O2B C21 C22 112.6(4) y
N21 C22 C23 112.3(4) ?
N21 C22 C21 108.4(4) ?
C23 C22 C21 112.8(4) ?
N21 C22 H22 107.7 ?
C23 C22 H22 107.7 ?
C21 C22 H22 107.7 ?
C22 N21 H21A 109.5 ?
C22 N21 H21B 109.5 ?
H21A N21 H21B 109.5 ?
C22 N21 H21C 109.5 ?
H21A N21 H21C 109.5 ?
H21B N21 H21C 109.5 ?
C22 C23 C24 115.7(5) ?
C22 C23 H23A 108.4 ?
C24 C23 H23A 108.4 ?
C22 C23 H23B 108.4 ?
C24 C23 H23B 108.4 ?
H23A C23 H23B 107.4 ?
S21 C24 C23 119.2(19) ?
S21 C24 S2 62(2) ?
C23 C24 S2 117.2(8) ?
S21 C24 S22 63(2) ?
C23 C24 S22 112.8(12) ?
S2 C24 S22 4.4(19) ?
S21 C24 H24A 131.0 ?
C23 C24 H24A 108.0 ?
S2 C24 H24A 108.0 ?
S22 C24 H24A 110.7 ?
S21 C24 H24B 47.2 ?
C23 C24 H24B 108.0 ?
S2 C24 H24B 108.0 ?
S22 C24 H24B 109.9 ?
H24A C24 H24B 107.2 ?
S21 C24 H24C 104.5 ?
C23 C24 H24C 105.7 ?
S2 C24 H24C 136.2 ?
S22 C24 H24C 140.6 ?
H24A C24 H24C 46.8 ?
H24B C24 H24C 63.5 ?
S21 C24 H24D 115.3 ?
C23 C24 H24D 105.1 ?
S2 C24 H24D 56.1 ?
S22 C24 H24D 56.7 ?
H24A C24 H24D 60.1 ?
H24B C24 H24D 146.9 ?
H24C C24 H24D 106.0 ?
S21 C24 H24E 130.4 ?
C23 C24 H24E 108.9 ?
S2 C24 H24E 106.5 ?
S22 C24 H24E 109.1 ?
H24A C24 H24E 1.5 ?
H24B C24 H24E 107.9 ?
H24C C24 H24E 48.0 ?
H24D C24 H24E 58.7 ?
S21 C24 H24F 46.2 ?
C23 C24 H24F 109.3 ?
S2 C24 H24F 106.8 ?
S22 C24 H24F 108.9 ?
H24A C24 H24F 107.1 ?
H24B C24 H24F 1.4 ?
H24C C24 H24F 63.8 ?
H24D C24 H24F 145.7 ?
H24E C24 H24F 107.7 ?
C24 S2 C25 102.4(12) ?
C24 S2 H24D 34.6 ?
C25 S2 H24D 135.4 ?
C24 S21 C25 115(3) ?
C24 S21 H24F 39.7 ?
C25 S21 H24F 148.5 ?
C24 S21 H25H 148.0 ?
C25 S21 H25H 33.2 ?
H24F S21 H25H 160.5 ?
C25 S22 C24 98.1(18) ?
C25 S22 H24D 128.5 ?
C24 S22 H24D 30.7 ?
C25 S22 H25D 30.9 ?
C24 S22 H25D 125.6 ?
H24D S22 H25D 155.7 ?
C25 S22 H25F 31.2 ?
C24 S22 H25F 98.1 ?
H24D S22 H25F 121.0 ?
H25D S22 H25F 50.8 ?
S21 C25 S22 62.9(19) ?
S21 C25 S2 55.8(18) ?
S22 C25 S2 7.2(18) ?
S21 C25 H25A 148.3 ?
S22 C25 H25A 103.8 ?
S2 C25 H25A 109.5 ?
S21 C25 H25B 60.1 ?
S22 C25 H25B 116.1 ?
S2 C25 H25B 109.5 ?
H25A C25 H25B 109.5 ?
S21 C25 H25C 102.2 ?
S22 C25 H25C 108.3 ?
S2 C25 H25C 109.5 ?
H25A C25 H25C 109.5 ?
H25B C25 H25C 109.5 ?
S21 C25 H25D 116.3 ?
S22 C25 H25D 79.7 ?
S2 C25 H25D 83.5 ?
H25A C25 H25D 32.7 ?
H25B C25 H25D 101.5 ?
H25C C25 H25D 139.2 ?
S21 C25 H25E 101.3 ?
S22 C25 H25E 164.1 ?
S2 C25 H25E 157.0 ?
H25A C25 H25E 90.0 ?
H25B C25 H25E 50.4 ?
H25C C25 H25E 73.6 ?
H25D C25 H25E 109.5 ?
S21 C25 H25F 110.4 ?
S22 C25 H25F 78.1 ?
S2 C25 H25F 82.4 ?
H25A C25 H25F 93.1 ?
H25B C25 H25F 148.0 ?
H25C C25 H25F 39.6 ?
H25D C25 H25F 109.5 ?
H25E C25 H25F 109.5 ?
S21 C25 H25G 150.5 ?
S22 C25 H25G 108.8 ?
S2 C25 H25G 114.5 ?
H25A C25 H25G 5.0 ?
H25B C25 H25G 106.6 ?
H25C C25 H25G 107.2 ?
H25D C25 H25G 36.5 ?
H25E C25 H25G 85.0 ?
H25F C25 H25G 94.1 ?
S21 C25 H25H 54.7 ?
S22 C25 H25H 109.6 ?
S2 C25 H25H 103.0 ?
H25A C25 H25H 111.9 ?
H25B C25 H25H 6.5 ?
H25C C25 H25H 113.3 ?
H25D C25 H25H 100.3 ?
H25E C25 H25H 56.9 ?
H25F C25 H25H 150.2 ?
H25G C25 H25H 109.5 ?
S21 C25 H25I 99.8 ?
S22 C25 H25I 110.0 ?
S2 C25 H25I 110.7 ?
H25A C25 H25I 112.0 ?
H25B C25 H25I 105.7 ?
H25C C25 H25I 3.9 ?
H25D C25 H25I 142.4 ?
H25E C25 H25I 71.0 ?
H25F C25 H25I 43.2 ?
H25G C25 H25I 109.5 ?
H25H C25 H25I 109.5 ?
O2 N1 O3 121.9(5) ?
O2 N1 C2 119.7(4) ?
O3 N1 C2 118.4(4) ?
O5 N2 O4 123.6(5) ?
O5 N2 C4 118.3(5) ?
O4 N2 C4 118.1(5) ?
O7 N3 O6 119.2(6) ?
O7 N3 C6 121.6(6) ?
O6 N3 C6 119.1(6) ?
O1 C1 C6 124.4(4) ?
O1 C1 C2 123.0(5) ?
C6 C1 C2 112.7(4) ?
C3 C2 C1 123.3(4) ?
C3 C2 N1 116.0(4) ?
C1 C2 N1 120.7(4) ?
C4 C3 C2 120.0(4) ?
C4 C3 H3 120.0 ?
C2 C3 H3 120.0 ?
C3 C4 C5 121.4(4) ?
C3 C4 N2 119.4(4) ?
C5 C4 N2 119.1(4) ?
C6 C5 C4 118.5(4) ?
C6 C5 H5 120.7 ?
C4 C5 H5 120.7 ?
C5 C6 C1 124.1(4) ?
C5 C6 N3 116.5(5) ?
C1 C6 N3 119.5(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1A C11 1.236(5) y
O1B C11 1.263(5) y
C11 C12 1.515(6) ?
C12 C131 1.398(15) ?
C12 N11 1.482(5) ?
C12 C132 1.697(9) ?
C12 H22A 0.9800 ?
C12 H12B 0.9800 ?
N11 H11A 0.8900 ?
N11 H11B 0.8900 ?
N11 H11C 0.8900 ?
C131 C14 1.143(15) ?
C131 H13A 0.9700 ?
C131 H13B 0.9700 ?
C132 C14 1.408(11) ?
C132 H13C 0.9700 ?
C132 H13D 0.9700 ?
C14 S1 1.714(12) ?
C14 S12 1.818(15) ?
C14 S11 1.89(2) ?
C14 H14A 0.9700 ?
C14 H14B 0.9700 ?
C14 H14C 0.9700 ?
C14 H14D 0.9700 ?
S1 C15 1.478(14) ?
S1 H15H 1.6850 ?
S11 C15 1.84(3) ?
S12 C15 1.861(17) ?
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 0.9600 ?
C15 H15D 0.9600 ?
C15 H15E 0.9600 ?
C15 H15F 0.9600 ?
C15 H15G 0.9600 ?
C15 H15H 0.9600 ?
C15 H15I 0.9600 ?
O2A C21 1.218(5) y
O2B C21 1.276(5) y
O2B H2B 0.8200 ?
C21 C22 1.518(6) ?
C22 N21 1.486(6) ?
C22 C23 1.513(7) ?
C22 H22 0.9800 ?
N21 H21A 0.8900 ?
N21 H21B 0.8900 ?
N21 H21C 0.8900 ?
C23 C24 1.537(8) ?
C23 H23A 0.9700 ?
C23 H23B 0.9700 ?
C24 S21 1.51(5) ?
C24 S2 1.71(2) ?
C24 S22 1.90(3) ?
C24 H24A 0.9700 ?
C24 H24B 0.9700 ?
C24 H24C 0.9699 ?
C24 H24D 0.9700 ?
C24 H24E 0.9700 ?
C24 H24F 0.9699 ?
S2 C25 1.83(3) ?
S2 H24D 1.4200 ?
S21 C25 1.75(5) ?
S21 H24F 1.0961 ?
S21 H25H 1.4301 ?
S22 C25 1.75(4) ?
S22 H24D 1.5898 ?
S22 H25D 1.8386 ?
S22 H25F 1.8131 ?
C25 H25A 0.9600 ?
C25 H25B 0.9600 ?
C25 H25C 0.9600 ?
C25 H25D 0.9600 ?
C25 H25E 0.9600 ?
C25 H25F 0.9600 ?
C25 H25G 0.9600 ?
C25 H25H 0.9600 ?
C25 H25I 0.9600 ?
O1 C1 1.255(5) ?
O2 N1 1.225(5) ?
O3 N1 1.229(6) ?
O4 N2 1.217(6) ?
O5 N2 1.216(6) ?
O6 N3 1.197(7) ?
O7 N3 1.187(7) ?
N1 C2 1.448(6) ?
N2 C4 1.455(6) ?
N3 C6 1.449(7) ?
C1 C6 1.435(7) ?
C1 C2 1.438(6) ?
C2 C3 1.371(6) ?
C3 C4 1.363(6) ?
C3 H3 0.9300 ?
C4 C5 1.380(6) ?
C5 C6 1.376(6) ?
C5 H5 0.9300 ?
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
O2B H2B O1B 2_566 0.82 1.66 2.457(5) 163
N11 H11A O1A 2_566 0.89 2.11 2.901(5) 147
N11 H11B O2A 2_666 0.89 2.06 2.868(4) 151
N11 H11C O1 . 0.89 2.06 2.861(5) 149
N11 H11C O2 . 0.89 2.26 2.928(5) 131
N21 H21A O4 2_667 0.89 2.57 3.062(5) 115
N21 H21B O1A 2_666 0.89 2.07 2.955(4) 174
N21 H21C O1 . 0.89 1.97 2.820(5) 160
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_publ_flag
O1A C11 C12 C131 -136.7(9) ?
O1B C11 C12 C131 43.4(10) ?
O1A C11 C12 N11 13.2(6) y
O1B C11 C12 N11 -166.7(4) y
O1A C11 C12 C132 -99.4(5) ?
O1B C11 C12 C132 80.7(5) ?
N11 C12 C131 C14 -113(7) ?
C11 C12 C131 C14 31(8) ?
C132 C12 C131 C14 -56(7) ?
C131 C12 C132 C14 9.3(12) ?
N11 C12 C132 C14 145.1(6) y
C11 C12 C132 C14 -98.1(7) ?
C12 C131 C14 C132 56(7) ?
C12 C131 C14 S1 90(7) ?
C12 C131 C14 S12 56(9) ?
C12 C131 C14 S11 48(8) ?
C12 C132 C14 C131 -9.5(12) ?
C12 C132 C14 S1 -172.1(6) ?
C12 C132 C14 S12 170.5(7) ?
C12 C132 C14 S11 165.0(8) ?
C131 C14 S1 C15 19(3) ?
C132 C14 S1 C15 42.8(14) y
S12 C14 S1 C15 148(3) ?
S11 C14 S1 C15 104(3) ?
C131 C14 S11 C15 89.6(19) ?
C132 C14 S11 C15 83.8(10) ?
S1 C14 S11 C15 -40.2(17) ?
S12 C14 S11 C15 -80(3) ?
C131 C14 S12 C15 61(3) ?
C132 C14 S12 C15 60.8(11) ?
S1 C14 S12 C15 -21(2) ?
S11 C14 S12 C15 79(3) ?
C14 S1 C15 S11 -97(2) ?
C14 S1 C15 S12 -134(4) ?
C14 S11 C15 S1 48.2(15) ?
C14 S11 C15 S12 72(3) ?
C14 S12 C15 S1 34(3) ?
C14 S12 C15 S11 -86(3) ?
O2A C21 C22 N21 -2.4(5) y
O2B C21 C22 N21 176.6(3) y
O2A C21 C22 C23 122.6(5) ?
O2B C21 C22 C23 -58.4(5) ?
N21 C22 C23 C24 -80.0(6) y
C21 C22 C23 C24 157.2(4) ?
C22 C23 C24 S21 141(2) ?
C22 C23 C24 S2 69.5(11) ?
C22 C23 C24 S22 69.9(15) y
S21 C24 S2 C25 -36(2) ?
C23 C24 S2 C25 74.4(11) y
C23 C24 S21 C25 -66(3) ?
S2 C24 S21 C25 41(2) ?
S22 C24 S21 C25 37(2) ?
S21 C24 S22 C25 -33(2) ?
C23 C24 S22 C25 79.3(16) ?
C24 S21 C25 S22 -41(3) ?
C24 S21 C25 S2 -42(2) ?
C24 S22 C25 S21 28(2) ?
C24 S22 C25 S2 34(12) ?
C24 S2 C25 S21 33(2) ?
C24 S2 C25 S22 -141(14) ?
O1 C1 C2 C3 178.4(4) ?
C6 C1 C2 C3 -1.6(6) ?
O1 C1 C2 N1 -3.9(7) ?
C6 C1 C2 N1 176.1(4) ?
O2 N1 C2 C3 -159.0(5) ?
O3 N1 C2 C3 19.9(7) y
O2 N1 C2 C1 23.2(7) y
O3 N1 C2 C1 -158.0(5) ?
C1 C2 C3 C4 -0.2(7) ?
N1 C2 C3 C4 -178.0(4) ?
C2 C3 C4 C5 1.7(7) ?
C2 C3 C4 N2 178.3(4) ?
O5 N2 C4 C3 -179.3(5) ?
O4 N2 C4 C3 -1.5(7) y
O5 N2 C4 C5 -2.6(7) y
O4 N2 C4 C5 175.2(5) ?
C3 C4 C5 C6 -1.2(7) ?
N2 C4 C5 C6 -177.8(4) ?
C4 C5 C6 C1 -0.9(7) ?
C4 C5 C6 N3 179.2(4) ?
O1 C1 C6 C5 -177.9(4) ?
C2 C1 C6 C5 2.1(6) ?
O1 C1 C6 N3 2.1(7) ?
C2 C1 C6 N3 -177.9(4) ?
O7 N3 C6 C5 -169.3(7) ?
O6 N3 C6 C5 6.8(8) y
O7 N3 C6 C1 10.8(9) y
O6 N3 C6 C1 -173.1(5) ?
