#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:08:27 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178422 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/43/4024331.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_4024331
loop_
_publ_author_name
'Khalil I. Shaikh'
'Surender Kumar'
'Lene Lundhus'
'Andrew D. Bond'
'Pawan K. Sharma'
'Poul Nielsen'
_publ_contact_author_address
;
 University of Southern Denmark
 Department of Physics and Chemistry
 Campusvej 55
 5230 Odense
 Denmark
;
_publ_contact_author_email       adb@chem.sdu.dk
_publ_contact_author_fax         '+45 6615 8780'
_publ_contact_author_name        'Andrew D. Bond'
_publ_contact_author_phone       '+45 6650 2545'
_publ_section_title
;
Synthesis of Bicyclic 2'-Deoxynucleosides with α-l-ribo- and
β-d-xylo-Configurations and Restricted S- and N-Type Conformations
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1557
_journal_page_last               1566
_journal_paper_doi               10.1021/jo8023472
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H28 N2 O8 S'
_chemical_formula_sum            'C22 H28 N2 O8 S'
_chemical_formula_weight         480.52
_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 plus manual editing'
_cell_angle_alpha                90.00
_cell_angle_beta                 103.267(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.2038(9)
_cell_length_b                   13.1226(9)
_cell_length_c                   16.2129(13)
_cell_measurement_reflns_used    6283
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      24.44
_cell_measurement_theta_min      2.43
_cell_volume                     2320.1(3)
_computing_cell_refinement       'SAINT v.7.06a (Bruker, 2003)'
_computing_data_collection       'APEX2 v.1.0-22 (Bruker Nonius, 2004)'
_computing_data_reduction        'SAINT v.7.06a'
_computing_molecular_graphics    'SHELXTL v.6.10'
_computing_publication_material  'SHELXTL v.6.10'
_computing_structure_refinement  'SHELXTL v.6.10'
_computing_structure_solution    'SHELXTL v.6.10 (Sheldrick, 2000)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker-Nonius X8APEX-II CCD'
_diffrn_measurement_method       'thin-slice ω and φ 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  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            26301
_diffrn_reflns_theta_full        26.44
_diffrn_reflns_theta_max         26.44
_diffrn_reflns_theta_min         3.52
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS v.2.10 (Sheldrick, 2003)
 Ratio of minimum to maximum apparent transmission:  0.902393
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack, 1983; 4177 Friedel pairs'
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     607
_refine_ls_number_reflns         9075
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0352
_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)+(0.0450P)²+0.2859P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0848
_reflns_number_gt                7982
_reflns_number_total             9075
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo8023472_si_003.cif
_cod_data_source_block           21
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4024331
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.80241(5) 0.80263(4) -0.04001(3) 0.03094(12) Uani 1 1 d . . .
O1 O 0.64454(12) 0.56579(10) 0.08328(8) 0.0249(3) Uani 1 1 d . . .
O2 O 0.53615(14) 0.43597(14) 0.26882(9) 0.0428(4) Uani 1 1 d . . .
O3 O 0.83417(14) 0.40400(12) 0.09751(10) 0.0320(3) Uani 1 1 d . . .
H3 H 0.857(2) 0.424(2) 0.1469(17) 0.043(8) Uiso 1 1 d . . .
O4 O 0.14557(14) 0.54713(13) 0.18707(9) 0.0410(4) Uani 1 1 d . . .
O5 O 0.51168(12) 0.50755(10) -0.08346(8) 0.0264(3) Uani 1 1 d . . .
O6 O 0.79068(14) 0.69728(11) 0.00343(9) 0.0351(4) Uani 1 1 d . . .
O7 O 0.8393(2) 0.87222(14) 0.02771(12) 0.0703(6) Uani 1 1 d . . .
O8 O 0.69215(14) 0.82164(12) -0.10281(11) 0.0437(4) Uani 1 1 d . . .
N1 N 0.47929(14) 0.51416(12) 0.13960(10) 0.0231(3) Uani 1 1 d . . .
N3 N 0.34605(15) 0.50406(14) 0.22935(10) 0.0289(4) Uani 1 1 d . . .
H3B H 0.3346 0.4923 0.2804 0.035 Uiso 1 1 calc R . .
C1' C 0.59147(18) 0.47962(15) 0.11482(13) 0.0257(4) Uani 1 1 d . . .
H1A H 0.6506 0.4514 0.1654 0.031 Uiso 1 1 calc R . .
C2' C 0.60969(18) 0.44921(14) -0.03049(12) 0.0236(4) Uani 1 1 d . . .
C3' C 0.56670(19) 0.39983(14) 0.04361(12) 0.0258(4) Uani 1 1 d . . .
H3C H 0.4782 0.3832 0.0269 0.031 Uiso 1 1 calc R . .
H3D H 0.6132 0.3365 0.0621 0.031 Uiso 1 1 calc R . .
C4' C 0.69923(18) 0.53330(14) 0.01491(12) 0.0235(4) Uani 1 1 d . . .
C5' C 0.83032(18) 0.49584(16) 0.05087(13) 0.0285(5) Uani 1 1 d . . .
H5A H 0.8713 0.4849 0.0036 0.034 Uiso 1 1 calc R . .
H5B H 0.8765 0.5492 0.0882 0.034 Uiso 1 1 calc R . .
C6' C 0.70000(19) 0.62410(15) -0.04229(13) 0.0274(4) Uani 1 1 d . . .
H6A H 0.7221 0.6024 -0.0953 0.033 Uiso 1 1 calc R . .
H6B H 0.6177 0.6559 -0.0570 0.033 Uiso 1 1 calc R . .
C2 C 0.46003(18) 0.48130(16) 0.21605(12) 0.0283(5) Uani 1 1 d . . .
C4 C 0.24764(19) 0.54360(16) 0.17047(13) 0.0285(5) Uani 1 1 d . . .
C5 C 0.27430(19) 0.57734(14) 0.09175(13) 0.0257(4) Uani 1 1 d . . .
C6 C 0.38650(18) 0.56036(14) 0.07994(12) 0.0245(4) Uani 1 1 d . . .
H6C H 0.4038 0.5811 0.0278 0.029 Uiso 1 1 calc R . .
C7 C 0.1714(2) 0.62258(16) 0.02576(14) 0.0329(5) Uani 1 1 d . . .
H7A H 0.2041 0.6502 -0.0207 0.049 Uiso 1 1 calc R . .
H7B H 0.1324 0.6773 0.0512 0.049 Uiso 1 1 calc R . .
H7C H 0.1108 0.5696 0.0038 0.049 Uiso 1 1 calc R . .
C8 C 0.40884(19) 0.45551(16) -0.13397(15) 0.0347(5) Uani 1 1 d . . .
H8A H 0.3749 0.4069 -0.0986 0.042 Uiso 1 1 calc R . .
H8B H 0.4340 0.4169 -0.1796 0.042 Uiso 1 1 calc R . .
C9 C 0.31339(19) 0.53404(16) -0.17166(12) 0.0281(4) Uani 1 1 d . . .
C10 C 0.1908(2) 0.50811(19) -0.19228(15) 0.0398(5) Uani 1 1 d . . .
H10A H 0.1666 0.4407 -0.1823 0.048 Uiso 1 1 calc R . .
C11 C 0.1024(2) 0.5795(2) -0.22751(17) 0.0493(7) Uani 1 1 d . . .
H11A H 0.0183 0.5604 -0.2415 0.059 Uiso 1 1 calc R . .
C12 C 0.1351(2) 0.6768(2) -0.24219(16) 0.0489(7) Uani 1 1 d . . .
H12A H 0.0742 0.7255 -0.2661 0.059 Uiso 1 1 calc R . .
C13 C 0.2564(2) 0.70374(19) -0.22215(16) 0.0482(6) Uani 1 1 d . . .
H13A H 0.2797 0.7713 -0.2325 0.058 Uiso 1 1 calc R . .
C14 C 0.3457(2) 0.63292(17) -0.18671(14) 0.0392(6) Uani 1 1 d . . .
H14A H 0.4296 0.6525 -0.1727 0.047 Uiso 1 1 calc R . .
C15 C 0.9222(2) 0.7856(2) -0.09014(16) 0.0463(6) Uani 1 1 d . . .
H15A H 0.9313 0.8470 -0.1226 0.070 Uiso 1 1 calc R . .
H15B H 0.9045 0.7271 -0.1285 0.070 Uiso 1 1 calc R . .
H15C H 0.9983 0.7732 -0.0476 0.070 Uiso 1 1 calc R . .
C16 C 0.6638(2) 0.37037(16) -0.08165(13) 0.0295(5) Uani 1 1 d . . .
H16A H 0.7320 0.3348 -0.0426 0.035 Uiso 1 1 calc R . .
H16B H 0.5999 0.3190 -0.1040 0.035 Uiso 1 1 calc R . .
C17 C 0.7109(2) 0.41155(17) -0.15428(14) 0.0356(5) Uani 1 1 d . . .
H17A H 0.6566 0.4515 -0.1953 0.043 Uiso 1 1 calc R . .
C18 C 0.8214(3) 0.3963(2) -0.16505(16) 0.0482(6) Uani 1 1 d . . .
H18A H 0.8781 0.3567 -0.1252 0.058 Uiso 1 1 calc R . .
H18B H 0.8451 0.4248 -0.2127 0.058 Uiso 1 1 calc R . .
S1A S 0.72516(6) 0.69812(4) 0.69075(4) 0.04176(15) Uani 1 1 d . . .
N1A N 0.93071(14) 0.45780(13) 0.41009(10) 0.0267(4) Uani 1 1 d . . .
N3A N 1.08383(14) 0.48246(12) 0.33731(10) 0.0250(4) Uani 1 1 d . . .
H3E H 1.1053 0.4905 0.2888 0.030 Uiso 1 1 calc R . .
O1A O 0.78930(12) 0.52787(10) 0.47670(9) 0.0287(3) Uani 1 1 d . . .
O2A O 0.88611(13) 0.45559(12) 0.26603(9) 0.0345(4) Uani 1 1 d . . .
O3A O 0.49319(15) 0.51942(15) 0.52914(10) 0.0440(4) Uani 1 1 d . . .
H3A H 0.417(3) 0.511(3) 0.495(2) 0.086(11) Uiso 1 1 d . . .
O4A O 1.28218(12) 0.50610(12) 0.40312(9) 0.0338(3) Uani 1 1 d . . .
O5A O 0.83171(13) 0.34931(10) 0.58070(10) 0.0340(4) Uani 1 1 d . . .
O6A O 0.73156(16) 0.63981(12) 0.60733(10) 0.0408(4) Uani 1 1 d . . .
O7A O 0.7674(3) 0.79646(18) 0.68320(17) 0.1159(12) Uani 1 1 d . . .
O8A O 0.78116(19) 0.63810(14) 0.76142(10) 0.0574(5) Uani 1 1 d . . .
C1A' C 0.79871(18) 0.46047(17) 0.41045(13) 0.0289(4) Uani 1 1 d . . .
H1B H 0.7510 0.4882 0.3552 0.035 Uiso 1 1 calc R . .
C2A' C 0.72001(19) 0.37098(16) 0.51845(13) 0.0292(5) Uani 1 1 d . . .
C3A' C 0.7427(2) 0.35874(17) 0.42913(14) 0.0329(5) Uani 1 1 d . . .
H3F H 0.8000 0.3018 0.4274 0.039 Uiso 1 1 calc R . .
H3G H 0.6648 0.3454 0.3873 0.039 Uiso 1 1 calc R . .
C4A' C 0.70430(17) 0.48854(16) 0.52310(12) 0.0267(4) Uani 1 1 d . . .
C5A' C 0.57836(18) 0.52937(19) 0.47714(13) 0.0337(5) Uani 1 1 d . . .
H5C H 0.5857 0.6020 0.4626 0.040 Uiso 1 1 calc R . .
H5D H 0.5486 0.4910 0.4238 0.040 Uiso 1 1 calc R . .
C6A' C 0.74283(19) 0.52909(16) 0.61227(13) 0.0299(5) Uani 1 1 d . . .
H6D H 0.6895 0.5010 0.6477 0.036 Uiso 1 1 calc R . .
H6E H 0.8286 0.5094 0.6378 0.036 Uiso 1 1 calc R . .
C2A C 0.96142(18) 0.46488(15) 0.33320(12) 0.0249(4) Uani 1 1 d . . .
C4A C 1.17552(18) 0.48874(15) 0.40934(13) 0.0272(4) Uani 1 1 d . . .
C5A C 1.13862(19) 0.47702(17) 0.48844(13) 0.0315(5) Uani 1 1 d . . .
C6A C 1.01907(19) 0.46278(18) 0.48483(13) 0.0326(5) Uani 1 1 d . . .
H6F H 0.9938 0.4557 0.5366 0.039 Uiso 1 1 calc R . .
C7A C 1.2325(2) 0.4837(3) 0.57129(14) 0.0525(7) Uani 1 1 d . . .
H7D H 1.1919 0.4752 0.6183 0.079 Uiso 1 1 calc R . .
H7E H 1.2730 0.5503 0.5757 0.079 Uiso 1 1 calc R . .
H7F H 1.2938 0.4298 0.5737 0.079 Uiso 1 1 calc R . .
C8A C 0.8686(3) 0.24417(19) 0.5878(2) 0.0646(9) Uani 1 1 d . . .
H8C H 0.8641 0.2153 0.5307 0.077 Uiso 1 1 calc R . .
H8D H 0.8129 0.2046 0.6150 0.077 Uiso 1 1 calc R . .
C9A C 0.9965(2) 0.23721(16) 0.63964(14) 0.0365(5) Uani 1 1 d . . .
C10A C 1.0218(3) 0.2336(2) 0.72734(18) 0.0602(8) Uani 1 1 d . . .
H10B H 0.9569 0.2380 0.7560 0.072 Uiso 1 1 calc R . .
C11A C 1.1455(5) 0.2232(2) 0.7745(2) 0.0922(15) Uani 1 1 d . . .
H11B H 1.1644 0.2200 0.8346 0.111 Uiso 1 1 calc R . .
C12A C 1.2361(4) 0.2181(2) 0.7307(4) 0.0930(14) Uani 1 1 d . . .
H12B H 1.3190 0.2127 0.7612 0.112 Uiso 1 1 calc R . .
C13A C 1.2117(3) 0.2202(3) 0.6481(3) 0.0853(12) Uani 1 1 d . . .
H13B H 1.2765 0.2152 0.6194 0.102 Uiso 1 1 calc R . .
C14A C 1.0940(3) 0.2295(2) 0.60290(19) 0.0563(7) Uani 1 1 d . . .
H14B H 1.0790 0.2307 0.5428 0.068 Uiso 1 1 calc R . .
C15A C 0.5678(3) 0.6989(3) 0.6882(2) 0.0864(12) Uani 1 1 d . . .
H15D H 0.5544 0.7309 0.7400 0.130 Uiso 1 1 calc R . .
H15E H 0.5370 0.6288 0.6845 0.130 Uiso 1 1 calc R . .
H15F H 0.5241 0.7376 0.6388 0.130 Uiso 1 1 calc R . .
C16A C 0.6111(2) 0.3063(2) 0.53111(14) 0.0396(5) Uani 1 1 d . . .
H16C H 0.5366 0.3293 0.4898 0.048 Uiso 1 1 calc R . .
H16D H 0.6261 0.2346 0.5174 0.048 Uiso 1 1 calc R . .
C17A C 0.5849(3) 0.3090(2) 0.61821(16) 0.0554(7) Uani 1 1 d . . .
H17B H 0.5677 0.3738 0.6388 0.066 Uiso 1 1 calc R . .
C18A C 0.5836(3) 0.2345(3) 0.66634(19) 0.0763(10) Uani 1 1 d . . .
H18C H 0.6003 0.1679 0.6488 0.092 Uiso 1 1 calc R . .
H18D H 0.5660 0.2445 0.7203 0.092 Uiso 1 1 calc R . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O7 S1 O8 119.36(12) . . ?
O7 S1 O6 105.05(10) . . ?
O8 S1 O6 108.97(9) . . ?
O7 S1 C15 109.09(14) . . ?
O8 S1 C15 108.86(11) . . ?
O6 S1 C15 104.49(11) . . ?
C1' O1 C4' 108.99(14) . . ?
C5' O3 H3 102.1(18) . . ?
C8 O5 C2' 119.37(14) . . ?
C6' O6 S1 117.93(12) . . ?
C2 N1 C6 121.21(16) . . ?
C2 N1 C1' 117.94(15) . . ?
C6 N1 C1' 119.56(15) . . ?
C2 N3 C4 126.50(17) . . ?
C2 N3 H3B 116.7 . . ?
C4 N3 H3B 116.7 . . ?
O1 C1' N1 107.78(14) . . ?
O1 C1' C3' 106.82(15) . . ?
N1 C1' C3' 113.31(15) . . ?
O1 C1' H1A 109.6 . . ?
N1 C1' H1A 109.6 . . ?
C3' C1' H1A 109.6 . . ?
O5 C2' C16 112.06(15) . . ?
O5 C2' C3' 110.83(16) . . ?
C16 C2' C3' 111.83(15) . . ?
O5 C2' C4' 102.95(14) . . ?
C16 C2' C4' 116.18(17) . . ?
C3' C2' C4' 102.28(15) . . ?
C1' C3' C2' 105.38(15) . . ?
C1' C3' H3C 110.7 . . ?
C2' C3' H3C 110.7 . . ?
C1' C3' H3D 110.7 . . ?
C2' C3' H3D 110.7 . . ?
H3C C3' H3D 108.8 . . ?
O1 C4' C6' 107.49(15) . . ?
O1 C4' C5' 109.90(15) . . ?
C6' C4' C5' 110.28(16) . . ?
O1 C4' C2' 103.33(15) . . ?
C6' C4' C2' 111.24(15) . . ?
C5' C4' C2' 114.19(16) . . ?
O3 C5' C4' 112.64(16) . . ?
O3 C5' H5A 109.1 . . ?
C4' C5' H5A 109.1 . . ?
O3 C5' H5B 109.1 . . ?
C4' C5' H5B 109.1 . . ?
H5A C5' H5B 107.8 . . ?
O6 C6' C4' 107.84(15) . . ?
O6 C6' H6A 110.1 . . ?
C4' C6' H6A 110.1 . . ?
O6 C6' H6B 110.1 . . ?
C4' C6' H6B 110.1 . . ?
H6A C6' H6B 108.5 . . ?
O2 C2 N1 123.90(19) . . ?
O2 C2 N3 121.49(19) . . ?
N1 C2 N3 114.61(17) . . ?
O4 C4 N3 119.68(19) . . ?
O4 C4 C5 124.80(19) . . ?
N3 C4 C5 115.52(18) . . ?
C6 C5 C4 117.94(18) . . ?
C6 C5 C7 123.92(19) . . ?
C4 C5 C7 118.00(18) . . ?
C5 C6 N1 123.62(18) . . ?
C5 C6 H6C 118.2 . . ?
N1 C6 H6C 118.2 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O5 C8 C9 108.04(16) . . ?
O5 C8 H8A 110.1 . . ?
C9 C8 H8A 110.1 . . ?
O5 C8 H8B 110.1 . . ?
C9 C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
C10 C9 C14 118.4(2) . . ?
C10 C9 C8 120.21(19) . . ?
C14 C9 C8 121.4(2) . . ?
C9 C10 C11 120.7(2) . . ?
C9 C10 H10A 119.7 . . ?
C11 C10 H10A 119.7 . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11A 119.7 . . ?
C10 C11 H11A 119.7 . . ?
C11 C12 C13 119.5(2) . . ?
C11 C12 H12A 120.3 . . ?
C13 C12 H12A 120.3 . . ?
C12 C13 C14 120.5(2) . . ?
C12 C13 H13A 119.8 . . ?
C14 C13 H13A 119.8 . . ?
C9 C14 C13 120.5(2) . . ?
C9 C14 H14A 119.8 . . ?
C13 C14 H14A 119.8 . . ?
S1 C15 H15A 109.5 . . ?
S1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
S1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C2' 115.84(17) . . ?
C17 C16 H16A 108.3 . . ?
C2' C16 H16A 108.3 . . ?
C17 C16 H16B 108.3 . . ?
C2' C16 H16B 108.3 . . ?
H16A C16 H16B 107.4 . . ?
C18 C17 C16 124.5(2) . . ?
C18 C17 H17A 117.8 . . ?
C16 C17 H17A 117.8 . . ?
C17 C18 H18A 120.0 . . ?
C17 C18 H18B 120.0 . . ?
H18A C18 H18B 120.0 . . ?
O7A S1A O8A 119.48(17) . . ?
O7A S1A O6A 107.04(11) . . ?
O8A S1A O6A 109.11(10) . . ?
O7A S1A C15A 110.7(2) . . ?
O8A S1A C15A 106.20(17) . . ?
O6A S1A C15A 103.13(14) . . ?
C2A N1A C6A 121.10(16) . . ?
C2A N1A C1A' 117.48(16) . . ?
C6A N1A C1A' 120.78(16) . . ?
C4A N3A C2A 126.52(17) . . ?
C4A N3A H3E 116.7 . . ?
C2A N3A H3E 116.7 . . ?
C1A' O1A C4A' 110.29(15) . . ?
C5A' O3A H3A 109(2) . . ?
C8A O5A C2A' 115.60(17) . . ?
C6A' O6A S1A 117.30(13) . . ?
O1A C1A' N1A 105.45(15) . . ?
O1A C1A' C3A' 106.80(16) . . ?
N1A C1A' C3A' 115.75(17) . . ?
O1A C1A' H1B 109.5 . . ?
N1A C1A' H1B 109.5 . . ?
C3A' C1A' H1B 109.5 . . ?
O5A C2A' C3A' 109.52(17) . . ?
O5A C2A' C16A 112.64(18) . . ?
C3A' C2A' C16A 112.10(17) . . ?
O5A C2A' C4A' 104.53(15) . . ?
C3A' C2A' C4A' 101.21(17) . . ?
C16A C2A' C4A' 116.00(18) . . ?
C1A' C3A' C2A' 105.00(17) . . ?
C1A' C3A' H3F 110.7 . . ?
C2A' C3A' H3F 110.7 . . ?
C1A' C3A' H3G 110.7 . . ?
C2A' C3A' H3G 110.7 . . ?
H3F C3A' H3G 108.8 . . ?
O1A C4A' C6A' 107.26(16) . . ?
O1A C4A' C5A' 105.46(16) . . ?
C6A' C4A' C5A' 111.82(17) . . ?
O1A C4A' C2A' 103.57(16) . . ?
C6A' C4A' C2A' 112.67(17) . . ?
C5A' C4A' C2A' 115.12(17) . . ?
O3A C5A' C4A' 110.43(17) . . ?
O3A C5A' H5C 109.6 . . ?
C4A' C5A' H5C 109.6 . . ?
O3A C5A' H5D 109.6 . . ?
C4A' C5A' H5D 109.6 . . ?
H5C C5A' H5D 108.1 . . ?
O6A C6A' C4A' 107.26(16) . . ?
O6A C6A' H6D 110.3 . . ?
C4A' C6A' H6D 110.3 . . ?
O6A C6A' H6E 110.3 . . ?
C4A' C6A' H6E 110.3 . . ?
H6D C6A' H6E 108.5 . . ?
O2A C2A N1A 122.56(18) . . ?
O2A C2A N3A 122.44(18) . . ?
N1A C2A N3A 115.00(16) . . ?
O4A C4A N3A 119.26(18) . . ?
O4A C4A C5A 124.63(18) . . ?
N3A C4A C5A 116.08(17) . . ?
C6A C5A C4A 117.60(18) . . ?
C6A C5A C7A 122.24(19) . . ?
C4A C5A C7A 120.14(19) . . ?
C5A C6A N1A 123.61(19) . . ?
C5A C6A H6F 118.2 . . ?
N1A C6A H6F 118.2 . . ?
C5A C7A H7D 109.5 . . ?
C5A C7A H7E 109.5 . . ?
H7D C7A H7E 109.5 . . ?
C5A C7A H7F 109.5 . . ?
H7D C7A H7F 109.5 . . ?
H7E C7A H7F 109.5 . . ?
O5A C8A C9A 109.02(19) . . ?
O5A C8A H8C 109.9 . . ?
C9A C8A H8C 109.9 . . ?
O5A C8A H8D 109.9 . . ?
C9A C8A H8D 109.9 . . ?
H8C C8A H8D 108.3 . . ?
C14A C9A C10A 116.8(2) . . ?
C14A C9A C8A 121.5(3) . . ?
C10A C9A C8A 121.7(3) . . ?
C9A C10A C11A 119.8(3) . . ?
C9A C10A H10B 120.1 . . ?
C11A C10A H10B 120.1 . . ?
C12A C11A C10A 118.2(3) . . ?
C12A C11A H11B 120.9 . . ?
C10A C11A H11B 120.9 . . ?
C13A C12A C11A 121.7(4) . . ?
C13A C12A H12B 119.1 . . ?
C11A C12A H12B 119.1 . . ?
C12A C13A C14A 120.3(4) . . ?
C12A C13A H13B 119.8 . . ?
C14A C13A H13B 119.8 . . ?
C13A C14A C9A 123.1(3) . . ?
C13A C14A H14B 118.4 . . ?
C9A C14A H14B 118.4 . . ?
S1A C15A H15D 109.5 . . ?
S1A C15A H15E 109.5 . . ?
H15D C15A H15E 109.5 . . ?
S1A C15A H15F 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?
C17A C16A C2A' 116.28(19) . . ?
C17A C16A H16C 108.2 . . ?
C2A' C16A H16C 108.2 . . ?
C17A C16A H16D 108.2 . . ?
C2A' C16A H16D 108.2 . . ?
H16C C16A H16D 107.4 . . ?
C18A C17A C16A 126.7(3) . . ?
C18A C17A H17B 116.6 . . ?
C16A C17A H17B 116.6 . . ?
C17A C18A H18C 120.0 . . ?
C17A C18A H18D 120.0 . . ?
H18C C18A H18D 120.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O7 1.4150(19) . ?
S1 O8 1.4310(17) . ?
S1 O6 1.5708(15) . ?
S1 C15 1.735(3) . ?
O1 C1' 1.426(2) . ?
O1 C4' 1.448(2) . ?
O2 C2 1.216(2) . ?
O3 C5' 1.418(2) . ?
O3 H3 0.83(3) . ?
O4 C4 1.234(3) . ?
O5 C8 1.425(2) . ?
O5 C2' 1.448(2) . ?
O6 C6' 1.469(2) . ?
N1 C2 1.375(3) . ?
N1 C6 1.387(2) . ?
N1 C1' 1.476(3) . ?
N3 C2 1.376(3) . ?
N3 C4 1.383(3) . ?
N3 H3B 0.880 . ?
C1' C3' 1.536(3) . ?
C1' H1A 1.000 . ?
C2' C16 1.535(3) . ?
C2' C3' 1.536(3) . ?
C2' C4' 1.558(3) . ?
C3' H3C 0.990 . ?
C3' H3D 0.990 . ?
C4' C6' 1.511(3) . ?
C4' C5' 1.532(3) . ?
C5' H5A 0.990 . ?
C5' H5B 0.990 . ?
C6' H6A 0.990 . ?
C6' H6B 0.990 . ?
C4 C5 1.445(3) . ?
C5 C6 1.333(3) . ?
C5 C7 1.503(3) . ?
C6 H6C 0.950 . ?
C7 H7A 0.980 . ?
C7 H7B 0.980 . ?
C7 H7C 0.980 . ?
C8 C9 1.510(3) . ?
C8 H8A 0.990 . ?
C8 H8B 0.990 . ?
C9 C10 1.380(3) . ?
C9 C14 1.384(3) . ?
C10 C11 1.387(3) . ?
C10 H10A 0.950 . ?
C11 C12 1.365(4) . ?
C11 H11A 0.950 . ?
C12 C13 1.369(4) . ?
C12 H12A 0.950 . ?
C13 C14 1.390(3) . ?
C13 H13A 0.950 . ?
C14 H14A 0.950 . ?
C15 H15A 0.980 . ?
C15 H15B 0.980 . ?
C15 H15C 0.980 . ?
C16 C17 1.497(3) . ?
C16 H16A 0.990 . ?
C16 H16B 0.990 . ?
C17 C18 1.304(3) . ?
C17 H17A 0.950 . ?
C18 H18A 0.950 . ?
C18 H18B 0.950 . ?
S1A O7A 1.390(2) . ?
S1A O8A 1.4131(18) . ?
S1A O6A 1.5698(17) . ?
S1A C15A 1.754(4) . ?
N1A C2A 1.370(3) . ?
N1A C6A 1.379(3) . ?
N1A C1A' 1.481(3) . ?
N3A C4A 1.369(3) . ?
N3A C2A 1.377(2) . ?
N3A H3E 0.880 . ?
O1A C1A' 1.414(2) . ?
O1A C4A' 1.438(2) . ?
O2A C2A 1.221(2) . ?
O3A C5A' 1.417(3) . ?
O3A H3A 0.91(4) . ?
O4A C4A 1.243(2) . ?
O5A C8A 1.437(3) . ?
O5A C2A' 1.444(2) . ?
O6A C6A' 1.459(3) . ?
C1A' C3A' 1.535(3) . ?
C1A' H1B 1.000 . ?
C2A' C3A' 1.535(3) . ?
C2A' C16A 1.539(3) . ?
C2A' C4A' 1.556(3) . ?
C3A' H3F 0.990 . ?
C3A' H3G 0.990 . ?
C4A' C6A' 1.508(3) . ?
C4A' C5A' 1.533(3) . ?
C5A' H5C 0.990 . ?
C5A' H5D 0.990 . ?
C6A' H6D 0.990 . ?
C6A' H6E 0.990 . ?
C4A C5A 1.443(3) . ?
C5A C6A 1.340(3) . ?
C5A C7A 1.507(3) . ?
C6A H6F 0.950 . ?
C7A H7D 0.980 . ?
C7A H7E 0.980 . ?
C7A H7F 0.980 . ?
C8A C9A 1.489(3) . ?
C8A H8C 0.990 . ?
C8A H8D 0.990 . ?
C9A C14A 1.362(4) . ?
C9A C10A 1.385(4) . ?
C10A C11A 1.428(6) . ?
C10A H10B 0.950 . ?
C11A C12A 1.367(6) . ?
C11A H11B 0.950 . ?
C12A C13A 1.303(6) . ?
C12A H12B 0.950 . ?
C13A C14A 1.359(5) . ?
C13A H13B 0.950 . ?
C14A H14B 0.950 . ?
C15A H15D 0.980 . ?
C15A H15E 0.980 . ?
C15A H15F 0.980 . ?
C16A C17A 1.507(3) . ?
C16A H16C 0.990 . ?
C16A H16D 0.990 . ?
C17A C18A 1.253(4) . ?
C17A H17B 0.950 . ?
C18A H18C 0.950 . ?
C18A H18D 0.950 . ?
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
O3 H3 O2A 0.83(3) 1.93(3) 2.744(2) 169(3) .
O3A H3A O4A 0.91(4) 1.87(4) 2.753(2) 164(3) 1_455
N3 H3B O4A 0.88 2.21 3.062(2) 163.7 1_455
N3A H3E O4 0.88 1.95 2.812(2) 164.4 1_655
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
_geom_torsion_publ_flag
O7 S1 O6 C6' 149.72(17) . . . . ?
O8 S1 O6 C6' 20.72(17) . . . . ?
C15 S1 O6 C6' -95.50(17) . . . . ?
C4' O1 C1' N1 -144.79(15) . . . . ?
C4' O1 C1' C3' -22.71(19) . . . . ?
C2 N1 C1' O1 -134.85(17) . . . . ?
C6 N1 C1' O1 57.9(2) . . . . ?
C2 N1 C1' C3' 107.18(19) . . . . ?
C6 N1 C1' C3' -60.1(2) . . . . ?
C8 O5 C2' C16 56.1(2) . . . . ?
C8 O5 C2' C3' -69.6(2) . . . . ?
C8 O5 C2' C4' -178.29(17) . . . . ?
O1 C1' C3' C2' -0.4(2) . . . . ?
N1 C1' C3' C2' 118.15(17) . . . . ?
O5 C2' C3' C1' -88.27(18) . . . . ?
C16 C2' C3' C1' 145.91(17) . . . . ?
C4' C2' C3' C1' 20.90(19) . . . . ?
C1' O1 C4' C6' 153.79(15) . . . . ?
C1' O1 C4' C5' -86.17(18) . . . . ?
C1' O1 C4' C2' 36.08(18) . . . . ?
O5 C2' C4' O1 80.91(16) . . . . ?
C16 C2' C4' O1 -156.23(15) . . . . ?
C3' C2' C4' O1 -34.15(17) . . . . ?
O5 C2' C4' C6' -34.1(2) . . . . ?
C16 C2' C4' C6' 88.7(2) . . . . ?
C3' C2' C4' C6' -149.20(16) . . . . ?
O5 C2' C4' C5' -159.76(16) . . . . ?
C16 C2' C4' C5' -36.9(2) . . . . ?
C3' C2' C4' C5' 85.19(19) . . . . ?
O1 C4' C5' O3 68.2(2) . . . . ?
C6' C4' C5' O3 -173.48(16) . . . . ?
C2' C4' C5' O3 -47.4(2) . . . . ?
S1 O6 C6' C4' -175.60(13) . . . . ?
O1 C4' C6' O6 70.33(19) . . . . ?
C5' C4' C6' O6 -49.5(2) . . . . ?
C2' C4' C6' O6 -177.23(16) . . . . ?
C6 N1 C2 O2 176.27(19) . . . . ?
C1' N1 C2 O2 9.3(3) . . . . ?
C6 N1 C2 N3 -4.0(3) . . . . ?
C1' N1 C2 N3 -170.98(16) . . . . ?
C4 N3 C2 O2 -171.4(2) . . . . ?
C4 N3 C2 N1 8.8(3) . . . . ?
C2 N3 C4 O4 169.9(2) . . . . ?
C2 N3 C4 C5 -9.5(3) . . . . ?
O4 C4 C5 C6 -174.1(2) . . . . ?
N3 C4 C5 C6 5.2(3) . . . . ?
O4 C4 C5 C7 1.6(3) . . . . ?
N3 C4 C5 C7 -179.06(18) . . . . ?
C4 C5 C6 N1 -1.4(3) . . . . ?
C7 C5 C6 N1 -176.81(18) . . . . ?
C2 N1 C6 C5 0.7(3) . . . . ?
C1' N1 C6 C5 167.55(18) . . . . ?
C2' O5 C8 C9 171.46(16) . . . . ?
O5 C8 C9 C10 -152.70(19) . . . . ?
O5 C8 C9 C14 27.5(3) . . . . ?
C14 C9 C10 C11 0.2(4) . . . . ?
C8 C9 C10 C11 -179.5(2) . . . . ?
C9 C10 C11 C12 -0.2(4) . . . . ?
C10 C11 C12 C13 0.3(4) . . . . ?
C11 C12 C13 C14 -0.4(4) . . . . ?
C10 C9 C14 C13 -0.3(3) . . . . ?
C8 C9 C14 C13 179.4(2) . . . . ?
C12 C13 C14 C9 0.4(4) . . . . ?
O5 C2' C16 C17 56.1(2) . . . . ?
C3' C2' C16 C17 -178.72(18) . . . . ?
C4' C2' C16 C17 -61.8(2) . . . . ?
C2' C16 C17 C18 125.8(2) . . . . ?
O7A S1A O6A C6A' 154.7(2) . . . . ?
O8A S1A O6A C6A' 24.1(2) . . . . ?
C15A S1A O6A C6A' -88.5(2) . . . . ?
C4A' O1A C1A' N1A -139.08(15) . . . . ?
C4A' O1A C1A' C3A' -15.4(2) . . . . ?
C2A N1A C1A' O1A -134.92(17) . . . . ?
C6A N1A C1A' O1A 36.0(2) . . . . ?
C2A N1A C1A' C3A' 107.3(2) . . . . ?
C6A N1A C1A' C3A' -81.8(2) . . . . ?
C8A O5A C2A' C3A' -71.1(3) . . . . ?
C8A O5A C2A' C16A 54.4(3) . . . . ?
C8A O5A C2A' C4A' -178.8(2) . . . . ?
O1A C1A' C3A' C2A' -8.6(2) . . . . ?
N1A C1A' C3A' C2A' 108.45(19) . . . . ?
O5A C2A' C3A' C1A' -83.35(19) . . . . ?
C16A C2A' C3A' C1A' 150.87(19) . . . . ?
C4A' C2A' C3A' C1A' 26.6(2) . . . . ?
C1A' O1A C4A' C6A' 152.08(16) . . . . ?
C1A' O1A C4A' C5A' -88.59(19) . . . . ?
C1A' O1A C4A' C2A' 32.73(19) . . . . ?
O5A C2A' C4A' O1A 78.08(18) . . . . ?
C3A' C2A' C4A' O1A -35.70(18) . . . . ?
C16A C2A' C4A' O1A -157.26(17) . . . . ?
O5A C2A' C4A' C6A' -37.5(2) . . . . ?
C3A' C2A' C4A' C6A' -151.27(17) . . . . ?
C16A C2A' C4A' C6A' 87.2(2) . . . . ?
O5A C2A' C4A' C5A' -167.34(16) . . . . ?
C3A' C2A' C4A' C5A' 78.9(2) . . . . ?
C16A C2A' C4A' C5A' -42.7(3) . . . . ?
O1A C4A' C5A' O3A -164.08(17) . . . . ?
C6A' C4A' C5A' O3A -47.8(2) . . . . ?
C2A' C4A' C5A' O3A 82.4(2) . . . . ?
S1A O6A C6A' C4A' 161.01(14) . . . . ?
O1A C4A' C6A' O6A 63.0(2) . . . . ?
C5A' C4A' C6A' O6A -52.2(2) . . . . ?
C2A' C4A' C6A' O6A 176.28(16) . . . . ?
C6A N1A C2A O2A 176.2(2) . . . . ?
C1A' N1A C2A O2A -12.9(3) . . . . ?
C6A N1A C2A N3A -3.3(3) . . . . ?
C1A' N1A C2A N3A 167.61(17) . . . . ?
C4A N3A C2A O2A -176.45(19) . . . . ?
C4A N3A C2A N1A 3.1(3) . . . . ?
C2A N3A C4A O4A -179.28(18) . . . . ?
C2A N3A C4A C5A -0.9(3) . . . . ?
O4A C4A C5A C6A 177.2(2) . . . . ?
N3A C4A C5A C6A -1.0(3) . . . . ?
O4A C4A C5A C7A -1.2(3) . . . . ?
N3A C4A C5A C7A -179.4(2) . . . . ?
C4A C5A C6A N1A 0.7(3) . . . . ?
C7A C5A C6A N1A 179.1(2) . . . . ?
C2A N1A C6A C5A 1.6(3) . . . . ?
C1A' N1A C6A C5A -169.0(2) . . . . ?
C2A' O5A C8A C9A 167.8(2) . . . . ?
O5A C8A C9A C14A -97.9(3) . . . . ?
O5A C8A C9A C10A 85.1(3) . . . . ?
C14A C9A C10A C11A 0.6(4) . . . . ?
C8A C9A C10A C11A 177.7(2) . . . . ?
C9A C10A C11A C12A 0.6(4) . . . . ?
C10A C11A C12A C13A -1.4(5) . . . . ?
C11A C12A C13A C14A 1.1(6) . . . . ?
C12A C13A C14A C9A 0.1(5) . . . . ?
C10A C9A C14A C13A -0.9(4) . . . . ?
C8A C9A C14A C13A -178.1(3) . . . . ?
O5A C2A' C16A C17A 53.1(3) . . . . ?
C3A' C2A' C16A C17A 177.1(2) . . . . ?
C4A' C2A' C16A C17A -67.3(3) . . . . ?
C2A' C16A C17A C18A -121.1(3) . . . . ?
