#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/35/2013555.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_2013555
loop_
_publ_author_name
'Kennedy, Alan R. '
'Okoth, Maurice O. '
'Sheen, David B. '
'Sherwood, John N. '
'Teat, Simon J. '
'Vrcelj, Ranko M. '
_publ_section_title
;
 Cephalexin: a channel hydrate
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o650
_journal_page_last               o652
_journal_paper_doi               10.1107/S0108270103022649
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C16 H17 N3 O4 S, 1.9H2 O'
_chemical_formula_moiety         'C16 H17 N3 O4 S, 1.9H2 O'
_chemical_formula_sum            'C16 H20.8 N3 O5.9 S'
_chemical_formula_weight         381.88
_chemical_name_systematic        ?
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 112.364(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   31.548(2)
_cell_length_b                   11.8574(9)
_cell_length_c                   15.6654(11)
_cell_measurement_reflns_used    14822
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.10
_cell_volume                     5419.3(7)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 1995)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEPII (Johnson, 1974)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker AXS SMART CCD'
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_radiation_monochromator  'Si 111'
_diffrn_radiation_source         'Daresbury SRS Station 9.8'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.6891
_diffrn_reflns_av_R_equivalents  0.047
_diffrn_reflns_av_sigmaI/netI    0.102
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14822
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.09
_diffrn_standards_decay_%        28.2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2414
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.58
_refine_diff_density_min         -0.47
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.21(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     717
_refine_ls_number_reflns         10703
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0740
_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)+(0.1215P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1825
_refine_ls_wR_factor_ref         0.1929
_reflns_number_gt                8136
_reflns_number_total             10703
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm1543.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 

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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               2013555
_cod_database_fobs_code          2013555
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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 0.30860(4) 0.01130(11) 0.40610(8) 0.0236(3) Uani d . 1 . . S
O1 0.19989(14) -0.3407(4) 0.2921(3) 0.0390(10) Uani d . 1 . . O
O2 0.23321(12) -0.3796(3) 0.4426(2) 0.0301(8) Uani d . 1 . . O
O3 0.16511(11) -0.1020(3) 0.3409(2) 0.0261(8) Uani d . 1 . . O
O4 0.19007(12) 0.2541(3) 0.2256(2) 0.0298(8) Uani d . 1 . . O
N1 0.23724(13) -0.1280(4) 0.3328(3) 0.0212(8) Uani d . 1 . . N
N2 0.21788(14) 0.1343(4) 0.3462(3) 0.0228(9) Uani d . 1 . . N
H2 0.2267 0.1275 0.4064 0.027 Uiso calc R 1 . . H
N3 0.19169(14) 0.4254(4) 0.3497(3) 0.0266(9) Uani d . 1 . . N
H3A 0.2025 0.4867 0.3865 0.040 Uiso calc R 1 . . H
H3B 0.1658 0.4000 0.3559 0.040 Uiso calc R 1 . . H
H3C 0.1852 0.4449 0.2899 0.040 Uiso calc R 1 . . H
C1 0.33549(16) -0.1257(4) 0.4209(3) 0.0223(10) Uani d . 1 . . C
H1A 0.3468 -0.1369 0.3706 0.027 Uiso calc R 1 . . H
H1B 0.3625 -0.1254 0.4798 0.027 Uiso calc R 1 . . H
C2 0.30577(16) -0.2263(4) 0.4216(3) 0.0182(9) Uani d . 1 . . C
C3 0.26017(15) -0.2251(4) 0.3810(3) 0.0177(9) Uani d . 1 . . C
C4 0.25885(16) -0.0312(4) 0.3079(3) 0.0223(10) Uani d . 1 . . C
H4 0.2651 -0.0429 0.2505 0.027 Uiso calc R 1 . . H
C5 0.21423(16) 0.0355(4) 0.2917(3) 0.0199(10) Uani d . 1 . . C
H5 0.1964 0.0501 0.2247 0.024 Uiso calc R 1 . . H
C6 0.19767(16) -0.0737(4) 0.3254(3) 0.0211(10) Uani d . 1 . . C
C7 0.33213(18) -0.3275(5) 0.4670(4) 0.0308(12) Uani d . 1 . . C
H7A 0.3111 -0.3907 0.4600 0.046 Uiso calc R 1 . . H
H7B 0.3489 -0.3119 0.5327 0.046 Uiso calc R 1 . . H
H7C 0.3539 -0.3468 0.4383 0.046 Uiso calc R 1 . . H
C8 0.22826(16) -0.3217(4) 0.3714(3) 0.0224(10) Uani d . 1 . . C
C9 0.20835(16) 0.2367(4) 0.3085(3) 0.0231(10) Uani d . 1 . . C
C10 0.22680(16) 0.3353(4) 0.3772(3) 0.0227(10) Uani d . 1 . . C
H10 0.2320 0.3090 0.4410 0.027 Uiso calc R 1 . . H
C11 0.27147(16) 0.3723(4) 0.3730(3) 0.0245(10) Uani d . 1 . . C
C12 0.31180(19) 0.3494(5) 0.4463(4) 0.0365(13) Uani d . 1 . . C
H12 0.3109 0.3124 0.4994 0.044 Uiso calc R 1 . . H
C13 0.35360(19) 0.3796(6) 0.4434(5) 0.0454(16) Uani d . 1 . . C
H13 0.3813 0.3633 0.4940 0.054 Uiso calc R 1 . . H
C14 0.3548(2) 0.4344(6) 0.3654(5) 0.0437(16) Uani d . 1 . . C
H14 0.3832 0.4573 0.3633 0.052 Uiso calc R 1 . . H
C15 0.3152(2) 0.4547(6) 0.2927(4) 0.0403(14) Uani d . 1 . . C
H15 0.3161 0.4894 0.2388 0.048 Uiso calc R 1 . . H
C16 0.27354(19) 0.4255(5) 0.2961(4) 0.0293(11) Uani d . 1 . . C
H16 0.2460 0.4421 0.2451 0.035 Uiso calc R 1 . . H
S2 0.03365(4) 0.94752(12) 0.34163(9) 0.0296(3) Uani d . 1 . . S
O5 0.11181(12) 1.3454(3) 0.3529(2) 0.0256(8) Uani d . 1 . . O
O6 0.06821(16) 1.3330(3) 0.2033(3) 0.0381(10) Uani d . 1 . . O
O7 0.11226(11) 1.0941(3) 0.1899(2) 0.0234(7) Uani d . 1 . . O
O8 0.02084(12) 0.7409(3) 0.1037(2) 0.0285(8) Uani d . 1 . . O
N4 0.05036(13) 1.1100(3) 0.2383(3) 0.0192(8) Uani d . 1 . . N
N5 0.07413(13) 0.8519(3) 0.2084(3) 0.0208(8) Uani d . 1 . . N
H5A 0.1009 0.8546 0.2547 0.025 Uiso calc R 1 . . H
N6 0.07344(15) 0.5556(4) 0.1525(3) 0.0263(9) Uani d . 1 . . N
H6A 0.0753 0.4887 0.1821 0.039 Uiso calc R 1 . . H
H6B 0.0937 0.5559 0.1239 0.039 Uiso calc R 1 . . H
H6C 0.0445 0.5649 0.1097 0.039 Uiso calc R 1 . . H
C17 0.02042(19) 1.0766(5) 0.3875(4) 0.0305(12) Uani d . 1 . . C
H17A -0.0132 1.0879 0.3600 0.037 Uiso calc R 1 . . H
H17B 0.0292 1.0669 0.4548 0.037 Uiso calc R 1 . . H
C18 0.04298(16) 1.1819(5) 0.3720(3) 0.0279(11) Uani d . 1 . . C
C19 0.05790(15) 1.1967(4) 0.3033(3) 0.0193(9) Uani d . 1 . . C
C20 0.04900(15) 0.9538(4) 0.1746(3) 0.0183(9) Uani d . 1 . . C
H20 0.0298 0.9492 0.1071 0.022 Uiso calc R 1 . . H
C21 0.02259(15) 1.0082(4) 0.2292(3) 0.0201(9) Uani d . 1 . . C
H21 -0.0107 1.0198 0.1916 0.024 Uiso calc R 1 . . H
C22 0.07791(16) 1.0618(4) 0.1990(3) 0.0192(10) Uani d . 1 . . C
C23 0.04504(18) 1.2751(5) 0.4392(4) 0.0332(13) Uani d . 1 . . C
H23A 0.0579 1.3432 0.4230 0.050 Uiso calc R 1 . . H
H23B 0.0645 1.2514 0.5019 0.050 Uiso calc R 1 . . H
H23C 0.0141 1.2912 0.4364 0.050 Uiso calc R 1 . . H
C24 0.08137(16) 1.3010(4) 0.2851(3) 0.0209(10) Uani d . 1 . . C
C25 0.05692(16) 0.7514(4) 0.1697(3) 0.0194(9) Uani d . 1 . . C
C26 0.08443(16) 0.6491(4) 0.2203(3) 0.0215(10) Uani d . 1 . . C
H26 0.1180 0.6662 0.2441 0.026 Uiso calc R 1 . . H
C27 0.06980(17) 0.6227(4) 0.3003(3) 0.0235(10) Uani d . 1 . . C
C28 0.10077(18) 0.6407(5) 0.3891(4) 0.0308(12) Uani d . 1 . . C
H28 0.1313 0.6626 0.3997 0.037 Uiso calc R 1 . . H
C29 0.0872(2) 0.6267(6) 0.4630(4) 0.0366(13) Uani d . 1 . . C
H29 0.1080 0.6419 0.5242 0.044 Uiso calc R 1 . . H
C30 0.0434(2) 0.5905(7) 0.4470(4) 0.0467(17) Uani d . 1 . . C
H30 0.0344 0.5780 0.4977 0.056 Uiso calc R 1 . . H
C31 0.0120(2) 0.5721(7) 0.3578(5) 0.0504(17) Uani d . 1 . . C
H31 -0.0184 0.5491 0.3474 0.060 Uiso calc R 1 . . H
C32 0.02550(19) 0.5876(5) 0.2843(4) 0.0326(12) Uani d . 1 . . C
H32 0.0045 0.5743 0.2230 0.039 Uiso calc R 1 . . H
S3 0.38897(8) 0.35790(15) 0.18246(13) 0.0574(5) Uani d . 1 . . S
O9 0.3285(3) -0.0229(5) 0.0085(5) 0.085(2) Uani d . 1 . . O
O10 0.3989(3) -0.0226(5) 0.0104(6) 0.094(2) Uani d . 1 . . O
O11 0.37462(15) 0.2227(4) -0.0865(3) 0.0417(10) Uani d . 1 . . O
O12 0.45530(12) 0.5732(3) 0.0199(2) 0.0241(7) Uani d . 1 . . O
N7 0.40532(19) 0.2020(4) 0.0744(4) 0.0387(12) Uani d . 1 . . N
N8 0.39530(14) 0.4642(4) 0.0118(3) 0.0246(9) Uani d . 1 . . N
H8 0.3656 0.4629 -0.0014 0.030 Uiso calc R 1 . . H
N9 0.39751(17) 0.7552(4) -0.0509(3) 0.0310(10) Uani d . 1 . . N
H9A 0.4280 0.7511 -0.0391 0.047 Uiso calc R 1 . . H
H9B 0.3909 0.8240 -0.0334 0.047 Uiso calc R 1 . . H
H9C 0.3813 0.7453 -0.1124 0.047 Uiso calc R 1 . . H
C33 0.3774(4) 0.2175(9) 0.2268(8) 0.035(3) Uiso d P 0.58(2) . . C
H33A 0.4053 0.1959 0.2803 0.042 Uiso calc PR 0.58(2) . . H
H33B 0.3526 0.2288 0.2501 0.042 Uiso calc PR 0.58(2) . . H
C34 0.3641(5) 0.1190(10) 0.1606(10) 0.040(3) Uiso d P 0.58(2) . . C
C35 0.3831(3) 0.1136(5) 0.1007(6) 0.057(2) Uani d . 1 . . C
C36 0.4257(2) 0.3037(5) 0.1282(4) 0.0367(13) Uani d . 1 . . C
H36 0.4583 0.2933 0.1717 0.044 Uiso calc R 1 . . H
C37 0.42095(18) 0.3599(5) 0.0363(4) 0.0275(11) Uani d . 1 . . C
H37 0.4512 0.3660 0.0297 0.033 Uiso calc R 1 . . H
C38 0.39532(19) 0.2533(5) -0.0092(4) 0.0292(12) Uani d . 1 . . C
C39 0.3428(5) 0.0277(11) 0.1970(9) 0.044(3) Uiso d P 0.58(2) . . C
H39A 0.3507 -0.0459 0.1787 0.066 Uiso calc PR 0.58(2) . . H
H39B 0.3094 0.0370 0.1715 0.066 Uiso calc PR 0.58(2) . . H
H39C 0.3544 0.0324 0.2644 0.066 Uiso calc PR 0.58(2) . . H
C40 0.3694(4) 0.0133(7) 0.0344(7) 0.073(3) Uani d . 1 . . C
C41 0.41541(17) 0.5627(4) 0.0085(3) 0.0221(10) Uani d . 1 . . C
C42 0.38497(18) 0.6656(4) 0.0017(3) 0.0239(10) Uani d . 1 . . C
H42 0.3520 0.6445 -0.0312 0.029 Uiso calc R 1 . . H
C43 0.39311(17) 0.7045(4) 0.0996(3) 0.0252(11) Uani d . 1 . . C
C44 0.3612(2) 0.6805(5) 0.1375(4) 0.0355(13) Uani d . 1 . . C
H44 0.3338 0.6411 0.1028 0.043 Uiso calc R 1 . . H
C45 0.3697(3) 0.7153(6) 0.2279(5) 0.0464(16) Uani d . 1 . . C
H45 0.3479 0.7004 0.2549 0.056 Uiso calc R 1 . . H
C46 0.4090(2) 0.7702(6) 0.2768(4) 0.0450(17) Uani d . 1 . . C
H46 0.4150 0.7906 0.3390 0.054 Uiso calc R 1 . . H
C47 0.4405(2) 0.7975(7) 0.2390(4) 0.0504(18) Uani d . 1 . . C
H47 0.4670 0.8404 0.2730 0.060 Uiso calc R 1 . . H
C48 0.43266(18) 0.7610(6) 0.1501(4) 0.0372(14) Uani d . 1 . . C
H48 0.4549 0.7752 0.1241 0.045 Uiso calc R 1 . . H
C100 0.3646(8) 0.0353(16) 0.2328(15) 0.053(5) Uiso d P 0.42(2) . . C
C101 0.3825(5) 0.1304(10) 0.1922(9) 0.018(3) Uiso d P 0.42(2) . . C
C102 0.3993(6) 0.2337(14) 0.2559(11) 0.035(4) Uiso d P 0.42(2) . . C
O13 0.29840(15) 0.4602(5) -0.0604(3) 0.0522(12) Uani d . 1 . . O
O14 0.23811(19) 0.7581(5) 0.1559(4) 0.050(2) Uani d P 0.860(15) . . O
O15 0.1647(2) 0.5017(5) 0.1667(4) 0.043(2) Uani d P 0.716(18) . . O
O16 0.2499(2) 0.6052(7) 0.0212(4) 0.063(3) Uani d P 0.793(15) . . O
O21 0.2440(8) 0.475(2) 0.0549(17) 0.058(9) Uiso d P 0.207(15) . . O
O22 0.2516(8) 0.667(2) 0.1584(17) 0.027(9) Uiso d P 0.140(15) . . O
O17 0.0119(2) 0.2744(6) 0.0345(4) 0.0251(15) Uiso d P 0.50 . . O
O18 0.2201(3) 0.2776(8) 0.0743(6) 0.063(3) Uiso d P 0.67(2) . . O
O19 0.4856(3) -0.0100(8) 0.0342(6) 0.047(2) Uiso d P 0.50 . . O
O20 0.2498(8) 0.236(2) 0.1159(16) 0.089(9) Uiso d P 0.33(2) . . O
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
C4 S1 C1 94.1(2) y
C6 N1 C3 133.8(4) y
C6 N1 C4 96.3(4) y
C3 N1 C4 125.8(4) y
C9 N2 C5 121.9(4) y
C9 N2 H2 119.0 ?
C5 N2 H2 119.0 ?
C10 N3 H3A 109.5 ?
C10 N3 H3B 109.5 ?
H3A N3 H3B 109.5 ?
C10 N3 H3C 109.5 ?
H3A N3 H3C 109.5 ?
H3B N3 H3C 109.5 ?
C2 C1 S1 116.5(3) y
C2 C1 H1A 108.2 ?
S1 C1 H1A 108.2 ?
C2 C1 H1B 108.2 ?
S1 C1 H1B 108.2 ?
H1A C1 H1B 107.3 ?
C3 C2 C7 123.0(4) y
C3 C2 C1 123.0(4) y
C7 C2 C1 113.9(4) y
C2 C3 N1 120.2(4) y
C2 C3 C8 127.1(4) y
N1 C3 C8 112.5(4) y
N1 C4 C5 87.6(3) y
N1 C4 S1 109.6(3) y
C5 C4 S1 116.0(3) y
N1 C4 H4 113.6 .
C5 C4 H4 113.6 ?
S1 C4 H4 113.6 ?
N2 C5 C4 117.4(4) y
N2 C5 C6 116.1(4) y
C4 C5 C6 85.5(4) y
N2 C5 H5 111.8 ?
C4 C5 H5 111.8 ?
C6 C5 H5 111.8 ?
O3 C6 N1 132.8(5) y
O3 C6 C5 136.8(5) y
N1 C6 C5 90.4(4) y
C2 C7 H7A 109.5 ?
C2 C7 H7B 109.5 ?
H7A C7 H7B 109.5 ?
C2 C7 H7C 109.5 ?
H7A C7 H7C 109.5 ?
H7B C7 H7C 109.5 ?
O1 C8 O2 125.6(5) y
O1 C8 C3 116.1(4) y
O2 C8 C3 118.3(4) y
O4 C9 N2 124.1(5) y
O4 C9 C10 120.8(5) y
N2 C9 C10 114.8(4) y
N3 C10 C11 112.8(4) y
N3 C10 C9 107.6(4) y
C11 C10 C9 107.6(4) y
N3 C10 H10 109.6 ?
C11 C10 H10 109.6 ?
C9 C10 H10 109.6 ?
C12 C11 C16 118.7(5) y
C12 C11 C10 119.4(5) y
C16 C11 C10 121.8(5) y
C11 C12 C13 120.7(6) y
C11 C12 H12 119.6 ?
C13 C12 H12 119.7 ?
C12 C13 C14 119.5(6) y
C12 C13 H13 120.2 ?
C14 C13 H13 120.2 ?
C15 C14 C13 119.6(5) y
C15 C14 H14 120.2 ?
C13 C14 H14 120.2 ?
C14 C15 C16 120.8(6) y
C14 C15 H15 119.6 ?
C16 C15 H15 119.6 ?
C15 C16 C11 120.6(5) y
C15 C16 H16 119.7 ?
C11 C16 H16 119.7 ?
C17 S2 C21 93.6(2) y
C22 N4 C19 132.3(4) y
C22 N4 C21 94.1(4) y
C19 N4 C21 127.1(4) y
C25 N5 C20 120.4(4) y
C25 N5 H5A 119.8 ?
C20 N5 H5A 119.8 ?
C26 N6 H6A 109.5 ?
C26 N6 H6B 109.5 ?
H6A N6 H6B 109.5 ?
C26 N6 H6C 109.5 ?
H6A N6 H6C 109.5 ?
H6B N6 H6C 109.5 ?
C18 C17 S2 116.4(3) y
C18 C17 H17A 108.2 ?
S2 C17 H17A 108.2 ?
C18 C17 H17B 108.2 ?
S2 C17 H17B 108.2 ?
H17A C17 H17B 107.3 ?
C19 C18 C17 124.9(5) y
C19 C18 C23 121.9(5) y
C17 C18 C23 113.1(4) y
C18 C19 N4 118.2(4) y
C18 C19 C24 127.0(4) y
N4 C19 C24 114.8(4) y
N5 C20 C22 114.8(4) y
N5 C20 C21 119.1(4) y
C22 C20 C21 84.7(3) y
N5 C20 H20 111.9 ?
C22 C20 H20 111.9 ?
C21 C20 H20 111.9 ?
N4 C21 C20 88.2(3) y
N4 C21 S2 110.3(3) y
C20 C21 S2 115.4(3) y
N4 C21 H21 113.5 ?
C20 C21 H21 113.5 ?
S2 C21 H21 113.5 ?
O7 C22 N4 132.3(5) y
O7 C22 C20 135.3(4) y
N4 C22 C20 92.4(4) y
C18 C23 H23A 109.5 ?
C18 C23 H23B 109.5 ?
H23A C23 H23B 109.5 ?
C18 C23 H23C 109.5 ?
H23A C23 H23C 109.5 ?
H23B C23 H23C 109.5 ?
O6 C24 O5 126.5(5) y
O6 C24 C19 116.4(4) y
O5 C24 C19 117.1(4) y
O8 C25 N5 123.8(5) y
O8 C25 C26 121.5(4) y
N5 C25 C26 114.5(4) y
N6 C26 C27 112.0(4) y
N6 C26 C25 106.9(4) y
C27 C26 C25 107.5(4) y
N6 C26 H26 110.1 ?
C27 C26 H26 110.1 ?
C25 C26 H26 110.1 ?
C28 C27 C32 120.5(5) y
C28 C27 C26 118.6(4) y
C32 C27 C26 120.8(5) y
C27 C28 C29 119.9(5) y
C27 C28 H28 120.1 ?
C29 C28 H28 120.1 ?
C30 C29 C28 119.5(5) y
C30 C29 H29 120.3 ?
C28 C29 H29 120.3 ?
C29 C30 C31 121.0(5) y
C29 C30 H30 119.5 ?
C31 C30 H30 119.5 ?
C32 C31 C30 119.3(6) y
C32 C31 H31 120.3 ?
C30 C31 H31 120.4 ?
C31 C32 C27 119.9(5) y
C31 C32 H32 120.1 ?
C27 C32 H32 120.1 ?
C36 S3 C102 91.0(5) y
C36 S3 C33 96.2(4) y
C38 N7 C35 130.8(6) y
C38 N7 C36 94.3(4) y
C35 N7 C36 127.0(5) y
C41 N8 C37 122.0(4) y
C41 N8 H8 119.0 ?
C37 N8 H8 119.0 ?
C42 N9 H9A 109.5 ?
C42 N9 H9B 109.5 ?
H9A N9 H9B 109.5 ?
C42 N9 H9C 109.5 ?
H9A N9 H9C 109.5 ?
H9B N9 H9C 109.5 ?
C34 C33 S3 118.0(7) y
C34 C33 H33A 107.8 ?
S3 C33 H33A 107.8 ?
C34 C33 H33B 107.8 ?
S3 C33 H33B 107.8 ?
H33A C33 H33B 107.1 ?
C35 C34 C39 129.8(11) y
C35 C34 C33 116.9(11) y
C39 C34 C33 110.2(9) y
C34 C35 N7 126.5(8) y
C34 C35 C40 116.2(9) y
N7 C35 C40 115.1(5) y
N7 C36 C37 87.3(4) y
N7 C36 S3 110.1(4) y
C37 C36 S3 115.8(4) y
N7 C36 H36 113.6 ?
C37 C36 H36 113.6 ?
S3 C36 H36 113.6 ?
N8 C37 C38 116.2(4) y
N8 C37 C36 117.6(4) y
C38 C37 C36 85.7(4) y
N8 C37 H37 111.7 ?
C38 C37 H37 111.7 ?
C36 C37 H37 111.7 ?
O11 C38 N7 132.4(5) y
O11 C38 C37 135.7(5) y
N7 C38 C37 91.9(4) y
C34 C39 H39A 109.5 ?
C34 C39 H39B 109.5 ?
H39A C39 H39B 109.5 ?
C34 C39 H39C 109.5 ?
H39A C39 H39C 109.5 ?
H39B C39 H39C 109.5 ?
O10 C40 O9 126.3(9) y
O10 C40 C35 115.6(9) y
O9 C40 C35 118.0(7) y
O12 C41 N8 124.5(5) y
O12 C41 C42 121.2(5) y
N8 C41 C42 113.8(4) y
N9 C42 C43 111.2(4) y
N9 C42 C41 108.4(4) y
C43 C42 C41 108.0(4) y
N9 C42 H42 109.7 ?
C43 C42 H42 109.7 ?
C41 C42 H42 109.7 ?
C48 C43 C44 120.3(5) y
C48 C43 C42 119.7(5) y
C44 C43 C42 119.9(5) y
C43 C44 C45 118.9(6) y
C43 C44 H44 120.5 ?
C45 C44 H44 120.5 ?
C46 C45 C44 119.8(6) y
C46 C45 H45 120.1 ?
C44 C45 H45 120.1 ?
C45 C46 C47 121.8(5) y
C45 C46 H46 119.1 ?
C47 C46 H46 119.1 ?
C46 C47 C48 118.5(6) y
C46 C47 H47 120.8 ?
C48 C47 H47 120.8 ?
C43 C48 C47 120.5(6) y
C43 C48 H48 119.8 ?
C47 C48 H48 119.8 ?
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
S1 C4 . 1.802(5) y
S1 C1 . 1.807(5) y
O1 C8 . 1.244(6) y
O2 C8 . 1.268(6) y
O3 C6 . 1.190(6) y
O4 C9 . 1.221(6) y
N1 C6 . 1.370(7) y
N1 C3 . 1.415(6) y
N1 C4 . 1.462(6) y
N2 C9 . 1.333(7) y
N2 C5 . 1.428(6) y
N2 H2 . 0.8800 ?
N3 C10 . 1.480(7) y
N3 H3A . 0.9100 ?
N3 H3B . 0.9100 ?
N3 H3C . 0.9100 ?
C1 C2 . 1.519(7) y
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C2 C3 . 1.333(6) y
C2 C7 . 1.478(7) y
C3 C8 . 1.495(7) y
C4 C5 . 1.549(7) y
C4 H4 . 1.0000 ?
C5 C6 . 1.561(7) y
C5 H5 . 1.0000 ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
C9 C10 . 1.545(7) y
C10 C11 . 1.501(7) y
C10 H10 . 1.0000 .
C11 C12 . 1.378(8) y
C11 C16 . 1.384(7) y
C12 C13 . 1.384(9) y
C12 H12 . 0.9500 ?
C13 C14 . 1.397(10) y
C13 H13 . 0.9500 ?
C14 C15 . 1.354(10) y
C14 H14 . 0.9500 ?
C15 C16 . 1.378(8) y
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
S2 C17 . 1.806(6) y
S2 C21 . 1.809(5) y
O5 C24 . 1.246(6) y
O6 C24 . 1.246(6) y
O7 C22 . 1.208(6) y
O8 C25 . 1.219(6) y
N4 C22 . 1.367(6) y
N4 C19 . 1.403(6) y
N4 C21 . 1.466(6) y
N5 C25 . 1.354(6) y
N5 C20 . 1.432(6) y
N5 H5A . 0.8800 ?
N6 C26 . 1.482(7) y
N6 H6A . 0.9100 ?
N6 H6B . 0.9100 ?
N6 H6C . 0.9100 ?
C17 C18 . 1.502(8) y
C17 H17A . 0.9900 ?
C17 H17B . 0.9900 ?
C18 C19 . 1.340(7) y
C18 C23 . 1.511(8) y
C19 C24 . 1.523(7) y
C20 C22 . 1.533(7) y
C20 C21 . 1.544(6) y
C20 H20 . 1.0000 ?
C21 H21 . 1.0000 ?
C23 H23A . 0.9800 ?
C23 H23B . 0.9800 ?
C23 H23C . 0.9800 ?
C25 C26 . 1.526(7) y
C26 C27 . 1.524(7) y
C26 H26 . 1.0000 ?
C27 C28 . 1.379(8) y
C27 C32 . 1.387(8) y
C28 C29 . 1.389(8) y
C28 H28 . 0.9500 ?
C29 C30 . 1.377(9) y
C29 H29 . 0.9500 ?
C30 C31 . 1.388(10) y
C30 H30 . 0.9500 ?
C31 C32 . 1.384(8) y
C31 H31 . 0.9500 ?
C32 H32 . 0.9500 ?
S3 C36 . 1.798(6) y
S3 C102 . 1.820(15) y
S3 C33 . 1.892(11) y
O9 C40 . 1.271(12) y
O10 C40 . 1.207(9) y
O11 C38 . 1.192(7) y
O12 C41 . 1.208(6) y
N7 C38 . 1.368(8) y
N7 C35 . 1.407(8) y
N7 C36 . 1.472(8) y
N8 C41 . 1.339(7) y
N8 C37 . 1.448(7) y
N8 H8 . 0.8800 ?
N9 C42 . 1.487(7) y
N9 H9A . 0.9100 .
N9 H9B . 0.9100 ?
N9 H9C . 0.9100 ?
C33 C34 . 1.512(17) y
C33 H33A . 0.9900 ?
C33 H33B . 0.9900 ?
C34 C35 . 1.294(13) y
C34 C39 . 1.496(17) y
C35 C101 . 1.455(14) y
C35 C40 . 1.530(13) y
C36 C37 . 1.541(8) y
C36 H36 . 1.0000 ?
C37 C38 . 1.523(8) y
C37 H37 . 1.0000 ?
C39 H39A . 0.9800 ?
C39 H39B . 0.9800 ?
C39 H39C . 0.9800 ?
C41 C42 . 1.531(7) y
C42 C43 . 1.527(7) y
C42 H42 . 1.0000 ?
C43 C48 . 1.371(8) y
C43 C44 . 1.381(8) y
C44 C45 . 1.399(9) y
C44 H44 . 0.9500 ?
C45 C46 . 1.350(10) y
C45 H45 . 0.9500 ?
C46 C47 . 1.374(10) y
C46 H46 . 0.9500 ?
C47 C48 . 1.388(8) y
C47 H47 . 0.9500 ?
C48 H48 . 0.9500 ?
C100 C101 . 1.51(2) y
C101 C102 . 1.54(2) y
O14 O22 . 1.15(3) y
O16 O21 . 1.67(3) y
O17 O17 2 1.056(12) .
O18 O20 . 1.04(2) y
O19 O19 2_655 1.646(18) ?
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 O2 4_556 0.88 2.22 3.077(5) 164.9
N3 H3A O2 1_565 0.91 1.89 2.780(6) 165.2
N3 H3B O5 1_545 0.91 1.81 2.711(5) 172.8
N3 H3C O15 . 0.91 1.91 2.811(7) 171.0
N5 H5A O3 1_565 0.88 2.03 2.883(5) 164.0
N6 H6A O6 1_545 0.91 1.90 2.781(6) 161.0
N6 H6B O15 . 0.91 2.18 2.874(8) 133.0
N6 H6B O11 4 0.91 2.39 2.995(6) 124.2
N6 H6B O10 4 0.91 2.39 3.134(8) 138.8
N6 H6C O19 3_455 0.91 1.99 2.794(10) 146.2
N6 H6C O8 . 0.91 2.21 2.683(6) 111.9
N6 H6C O19 4 0.91 2.27 2.912(10) 127.5
N8 H8 O13 . 0.88 1.96 2.827(6) 166.7
N9 H9A O17 4 0.91 1.89 2.779(8) 165.6
N9 H9A O17 3 0.91 2.47 3.346(8) 162.3
N9 H9B O10 1_565 0.91 1.93 2.799(7) 160.0
N9 H9C O7 4_545 0.91 2.22 2.824(5) 123.5
N9 H9C O4 4 0.91 2.28 3.061(6) 144.1
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
C4 S1 C1 C2 -49.0(4)
S1 C1 C2 C3 24.6(6)
S1 C1 C2 C7 -158.5(4)
C7 C2 C3 N1 -175.3(4)
C1 C2 C3 N1 1.3(7)
C7 C2 C3 C8 -1.8(7)
C1 C2 C3 C8 174.8(4)
C6 N1 C3 C2 -140.3(5)
C4 N1 C3 C2 11.4(7)
C6 N1 C3 C8 45.3(7)
C4 N1 C3 C8 -162.9(4)
C6 N1 C4 C5 -3.3(4)
C3 N1 C4 C5 -163.2(4)
C6 N1 C4 S1 113.5(3)
C3 N1 C4 S1 -46.4(5)
C1 S1 C4 N1 56.3(4)
C1 S1 C4 C5 153.5(4)
C9 N2 C5 C4 116.1(5)
C9 N2 C5 C6 -145.0(4)
N1 C4 C5 N2 120.0(4)
S1 C4 C5 N2 9.4(5)
N1 C4 C5 C6 2.9(3)
S1 C4 C5 C6 -107.8(4)
C3 N1 C6 O3 -18.3(9)
C4 N1 C6 O3 -175.6(5)
C3 N1 C6 C5 160.6(5)
C4 N1 C6 C5 3.3(4)
N2 C5 C6 O3 57.4(8)
C4 C5 C6 O3 175.7(6)
N2 C5 C6 N1 -121.5(4)
C4 C5 C6 N1 -3.1(3)
C2 C3 C8 O1 -128.3(5)
N1 C3 C8 O1 45.6(6)
C2 C3 C8 O2 49.1(7)
N1 C3 C8 O2 -137.0(4)
C5 N2 C9 O4 10.4(7)
C5 N2 C9 C10 -163.5(4)
O4 C9 C10 N3 44.5(6)
N2 C9 C10 N3 -141.5(4)
O4 C9 C10 C11 -77.3(6)
N2 C9 C10 C11 96.7(5)
N3 C10 C11 C12 132.8(5)
C9 C10 C11 C12 -108.7(5)
N3 C10 C11 C16 -49.6(6)
C9 C10 C11 C16 68.9(6)
C16 C11 C12 C13 0.4(8)
C10 C11 C12 C13 178.1(5)
C11 C12 C13 C14 0.3(9)
C12 C13 C14 C15 -1.7(9)
C13 C14 C15 C16 2.3(9)
C14 C15 C16 C11 -1.6(9)
C12 C11 C16 C15 0.2(8)
C10 C11 C16 C15 -177.4(5)
C21 S2 C17 C18 -48.9(4)
S2 C17 C18 C19 24.7(7)
S2 C17 C18 C23 -158.7(4)
C17 C18 C19 N4 2.9(7)
C23 C18 C19 N4 -173.4(4)
C17 C18 C19 C24 -179.3(5)
C23 C18 C19 C24 4.4(8)
C22 N4 C19 C18 -135.7(5)
C21 N4 C19 C18 8.3(7)
C22 N4 C19 C24 46.3(7)
C21 N4 C19 C24 -169.8(4)
C25 N5 C20 C22 -159.5(4)
C25 N5 C20 C21 102.3(5)
C22 N4 C21 C20 -6.0(3)
C19 N4 C21 C20 -160.1(4)
C22 N4 C21 S2 110.5(3)
C19 N4 C21 S2 -43.7(5)
N5 C20 C21 N4 120.9(4)
C22 C20 C21 N4 5.4(3)
N5 C20 C21 S2 9.2(5)
C22 C20 C21 S2 -106.3(3)
C17 S2 C21 N4 54.9(4)
C17 S2 C21 C20 152.9(4)
C19 N4 C22 O7 -20.9(9)
C21 N4 C22 O7 -172.8(5)
C19 N4 C22 C20 158.0(5)
C21 N4 C22 C20 6.0(3)
N5 C20 C22 O7 53.4(7)
C21 C20 C22 O7 173.1(6)
N5 C20 C22 N4 -125.5(4)
C21 C20 C22 N4 -5.8(3)
C18 C19 C24 O6 -136.2(5)
N4 C19 C24 O6 41.7(6)
C18 C19 C24 O5 44.1(7)
N4 C19 C24 O5 -138.1(4)
C20 N5 C25 O8 2.5(7)
C20 N5 C25 C26 -172.7(4)
O8 C25 C26 N6 27.3(6)
N5 C25 C26 N6 -157.4(4)
O8 C25 C26 C27 -93.1(5)
N5 C25 C26 C27 82.2(5)
N6 C26 C27 C28 131.8(5)
C25 C26 C27 C28 -111.1(5)
N6 C26 C27 C32 -51.9(6)
C25 C26 C27 C32 65.2(6)
C32 C27 C28 C29 -1.8(9)
C26 C27 C28 C29 174.5(5)
C27 C28 C29 C30 2.6(10)
C28 C29 C30 C31 -2.5(11)
C29 C30 C31 C32 1.7(11)
C30 C31 C32 C27 -0.9(10)
C28 C27 C32 C31 1.0(9)
C26 C27 C32 C31 -175.3(6)
C36 S3 C33 C34 -47.6(9)
S3 C33 C34 C35 35.3(14)
S3 C33 C34 C39 -162.8(9)
C39 C34 C35 N7 -175.3(11)
C33 C34 C35 N7 -17.6(17)
C102 C34 C35 N7 -31.1(14)
C39 C34 C35 C101 -113(2)
C33 C34 C35 C101 44.8(16)
C39 C34 C35 C40 22.1(19)
C33 C34 C35 C40 179.9(9)
C38 N7 C35 C34 -117.7(12)
C36 N7 C35 C34 23.0(14)
C38 N7 C35 C101 -141.6(8)
C36 N7 C35 C101 -1.0(11)
C38 N7 C35 C40 45.0(9)
C36 N7 C35 C40 -174.4(7)
C38 N7 C36 C37 -7.0(4)
C35 N7 C36 C37 -158.2(6)
C38 N7 C36 S3 109.5(4)
C35 N7 C36 S3 -41.7(8)
C102 S3 C36 N7 66.6(7)
C33 S3 C36 N7 45.8(6)
C102 S3 C36 C37 163.6(7)
C33 S3 C36 C37 142.8(6)
C41 N8 C37 C38 -148.2(4)
C41 N8 C37 C36 112.5(6)
N7 C36 C37 N8 123.7(5)
S3 C36 C37 N8 12.7(7)
N7 C36 C37 C38 6.3(4)
S3 C36 C37 C38 -104.7(5)
C35 N7 C38 O11 -23.9(10)
C36 N7 C38 O11 -173.3(6)
C35 N7 C38 C37 156.6(6)
C36 N7 C38 C37 7.1(4)
N8 C37 C38 O11 55.0(8)
C36 C37 C38 O11 173.7(6)
N8 C37 C38 N7 -125.5(4)
C36 C37 C38 N7 -6.8(4)
C34 C35 C40 O10 -147.0(10)
N7 C35 C40 O10 48.5(11)
C101 C35 C40 O10 -123.2(11)
C34 C35 C40 O9 34.3(13)
N7 C35 C40 O9 -130.2(8)
C101 C35 C40 O9 58.0(14)
C37 N8 C41 O12 4.6(7)
C37 N8 C41 C42 -167.7(4)
O12 C41 C42 N9 38.2(6)
N8 C41 C42 N9 -149.3(4)
O12 C41 C42 C43 -82.4(6)
N8 C41 C42 C43 90.1(5)
N9 C42 C43 C48 -43.8(7)
C41 C42 C43 C48 75.1(6)
N9 C42 C43 C44 137.6(5)
C41 C42 C43 C44 -103.6(6)
C48 C43 C44 C45 0.3(9)
C42 C43 C44 C45 178.9(5)
C43 C44 C45 C46 -0.8(10)
C44 C45 C46 C47 2.7(11)
C45 C46 C47 C48 -4.1(11)
C44 C43 C48 C47 -1.8(10)
C42 C43 C48 C47 179.6(6)
C46 C47 C48 C43 3.6(11)
