#------------------------------------------------------------------------------
#$Date: 2020-02-22 02:18:01 +0200 (Sat, 22 Feb 2020) $
#$Revision: 248385 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/79/4037951.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_4037951
loop_
_publ_author_name
'Kramer, Philipp'
'Ha Aczkiewicz, Miro'
'Sun, Yu'
'Kelm, Harald'
'Manolikakes, Georg'
_publ_section_title
;
 Iron(III)-Mediated Oxy-Sulfonylation of Enamides with Sodium and Lithium
 Sulfinates.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03299
_journal_year                    2020
_chemical_formula_moiety         'C18 H21 N O4 S'
_chemical_formula_sum            'C18 H21 N O4 S'
_chemical_formula_weight         347.42
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-10-23 deposited with the CCDC.	2019-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.7230(4)
_cell_length_b                   9.9980(2)
_cell_length_c                   15.8190(5)
_cell_measurement_reflns_used    6519
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      62.7540
_cell_measurement_theta_min      4.7680
_cell_volume                     3593.83(15)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 16.1399
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16661
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        62.579
_diffrn_reflns_theta_max         62.579
_diffrn_reflns_theta_min         3.891
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.779
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69599
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       rod
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.661
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.08(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     440
_refine_ls_number_reflns         5350
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0518
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0872P)²+1.5390P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1388
_refine_ls_wR_factor_ref         0.1425
_reflns_Friedel_coverage         0.920
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4980
_reflns_number_total             5350
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b03299_si_003.cif
_cod_data_source_block           shelx
_cod_database_code               4037951
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.464
_shelx_estimated_absorpt_t_max   0.932
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.88920(15) 0.3298(3) 0.8384(3) 0.0382(9) Uani 1 1 d . . . . .
C1 C 0.9002(2) 0.4500(5) 0.8298(4) 0.0271(11) Uani 1 1 d . . . . .
C11 C 0.9579(3) 0.4967(5) 0.7984(4) 0.0234(13) Uani 1 1 d . . . . .
C12 C 0.9906(2) 0.4085(5) 0.7481(4) 0.0346(12) Uani 1 1 d . . . . .
H12 H 0.9746 0.3238 0.7335 0.042 Uiso 1 1 calc R U . . .
C13 C 1.0464(3) 0.4445(6) 0.7194(5) 0.0441(17) Uani 1 1 d . . . . .
H13 H 1.0686 0.3841 0.6858 0.053 Uiso 1 1 calc R U . . .
C14 C 1.0691(2) 0.5670(6) 0.7399(6) 0.0469(17) Uani 1 1 d . . . . .
H14 H 1.1069 0.5916 0.7195 0.056 Uiso 1 1 calc R U . . .
C15 C 1.0378(2) 0.6557(6) 0.7899(5) 0.0453(15) Uani 1 1 d . . . . .
H15 H 1.0541 0.7402 0.8043 0.054 Uiso 1 1 calc R U . . .
C16 C 0.9819(2) 0.6200(5) 0.8191(4) 0.0349(12) Uani 1 1 d . . . . .
H16 H 0.9602 0.6805 0.8534 0.042 Uiso 1 1 calc R U . . .
N1 N 0.86006(18) 0.5442(4) 0.8478(3) 0.0246(9) Uani 1 1 d . . . . .
H1 H 0.8689 0.6283 0.8374 0.030 Uiso 1 1 calc R U . . .
C2 C 0.8022(3) 0.5138(5) 0.8838(4) 0.0265(13) Uani 1 1 d . . . . .
H2 H 0.7937 0.4162 0.8773 0.032 Uiso 1 1 calc R U . . .
O4 O 0.80063(18) 0.5484(5) 0.9699(3) 0.0447(10) Uani 1 1 d . . . . .
C21 C 0.8362(5) 0.4610(11) 1.0195(6) 0.080(3) Uani 1 1 d . . . . .
H21A H 0.8245 0.3681 1.0091 0.120 Uiso 1 1 calc R U . . .
H21B H 0.8310 0.4820 1.0796 0.120 Uiso 1 1 calc R U . . .
H21C H 0.8777 0.4728 1.0040 0.120 Uiso 1 1 calc R U . . .
C3 C 0.7547(2) 0.5952(5) 0.8393(4) 0.0296(11) Uani 1 1 d . . . . .
H3 H 0.7686 0.6896 0.8336 0.035 Uiso 1 1 calc R U . . .
C4 C 0.6962(2) 0.5946(6) 0.8880(4) 0.0398(14) Uani 1 1 d . . . . .
H4A H 0.6832 0.5021 0.8965 0.060 Uiso 1 1 calc R U . . .
H4B H 0.6664 0.6434 0.8556 0.060 Uiso 1 1 calc R U . . .
H4C H 0.7017 0.6379 0.9430 0.060 Uiso 1 1 calc R U . . .
O2 O 0.71829(17) 0.3959(4) 0.7446(3) 0.0405(9) Uani 1 1 d . . . . .
O3 O 0.69836(18) 0.6279(4) 0.6986(3) 0.0450(10) Uani 1 1 d . . . . .
S1 S 0.73769(6) 0.53077(13) 0.73555(9) 0.0314(3) Uani 1 1 d . . . . .
C31 C 0.8021(3) 0.5262(6) 0.6735(4) 0.0312(14) Uani 1 1 d . . . . .
C32 C 0.8248(3) 0.4035(6) 0.6482(4) 0.0403(15) Uani 1 1 d . . . . .
H32 H 0.8069 0.3227 0.6666 0.048 Uiso 1 1 calc R U . . .
C33 C 0.8742(3) 0.4001(6) 0.5956(5) 0.0430(15) Uani 1 1 d . . . . .
H33 H 0.8891 0.3165 0.5766 0.052 Uiso 1 1 calc R U . . .
C34 C 0.9018(3) 0.5176(6) 0.5706(5) 0.0360(15) Uani 1 1 d . . . . .
C35 C 0.8777(3) 0.6401(6) 0.5966(4) 0.0366(13) Uani 1 1 d . . . . .
H35 H 0.8954 0.7211 0.5783 0.044 Uiso 1 1 calc R U . . .
C36 C 0.8288(3) 0.6453(6) 0.6479(4) 0.0346(13) Uani 1 1 d . . . . .
H36 H 0.8134 0.7290 0.6656 0.041 Uiso 1 1 calc R U . . .
C37 C 0.9541(4) 0.5140(8) 0.5135(6) 0.057(2) Uani 1 1 d . . . . .
H37A H 0.9532 0.5918 0.4758 0.085 Uiso 1 1 calc R U . . .
H37B H 0.9532 0.4319 0.4797 0.085 Uiso 1 1 calc R U . . .
H37C H 0.9902 0.5160 0.5474 0.085 Uiso 1 1 calc R U . . .
O1' O 0.85788(15) 0.8330(4) 0.8531(3) 0.0387(9) Uani 1 1 d . . . . .
C1' C 0.8488(2) 0.9527(5) 0.8651(4) 0.0269(11) Uani 1 1 d . . . . .
C11' C 0.7898(2) 1.0013(4) 0.8963(4) 0.0213(13) Uani 1 1 d . . . . .
C12' C 0.7566(2) 0.9160(5) 0.9462(4) 0.0336(12) Uani 1 1 d . . . . .
H12' H 0.7717 0.8306 0.9613 0.040 Uiso 1 1 calc R U . . .
C13' C 0.7016(3) 0.9551(6) 0.9740(5) 0.0416(15) Uani 1 1 d . . . . .
H13' H 0.6786 0.8965 1.0078 0.050 Uiso 1 1 calc R U . . .
C14' C 0.6803(2) 1.0790(6) 0.9525(5) 0.0411(14) Uani 1 1 d . . . . .
H14' H 0.6428 1.1066 0.9727 0.049 Uiso 1 1 calc R U . . .
C15' C 0.7127(2) 1.1642(6) 0.9019(4) 0.0396(13) Uani 1 1 d . . . . .
H15' H 0.6972 1.2490 0.8863 0.048 Uiso 1 1 calc R U . . .
C16' C 0.7678(2) 1.1256(5) 0.8738(4) 0.0335(12) Uani 1 1 d . . . . .
H16' H 0.7905 1.1840 0.8394 0.040 Uiso 1 1 calc R U . . .
N1' N 0.88986(19) 1.0468(4) 0.8510(3) 0.0277(10) Uani 1 1 d . . . . .
H1' H 0.8822 1.1296 0.8663 0.033 Uiso 1 1 calc R U . . .
C2' C 0.9452(3) 1.0190(5) 0.8126(5) 0.0292(14) Uani 1 1 d . . . . .
H2' H 0.9526 0.9204 0.8115 0.035 Uiso 1 1 calc R U . . .
O4' O 0.94718(18) 1.0724(4) 0.7288(3) 0.0422(9) Uani 1 1 d . . . . .
C21' C 0.9050(4) 1.0142(9) 0.6752(6) 0.070(3) Uani 1 1 d . . . . .
H21D H 0.9083 0.9166 0.6779 0.105 Uiso 1 1 calc R U . . .
H21E H 0.9117 1.0442 0.6170 0.105 Uiso 1 1 calc R U . . .
H21F H 0.8655 1.0414 0.6932 0.105 Uiso 1 1 calc R U . . .
C3' C 0.9952(2) 1.0910(5) 0.8592(4) 0.0317(12) Uani 1 1 d . . . . .
H3' H 0.9835 1.1862 0.8688 0.038 Uiso 1 1 calc R U . . .
C4' C 1.0536(2) 1.0881(6) 0.8096(5) 0.0470(16) Uani 1 1 d . . . . .
H4'1 H 1.0645 0.9951 0.7977 0.071 Uiso 1 1 calc R U . . .
H4'2 H 1.0846 1.1304 0.8433 0.071 Uiso 1 1 calc R U . . .
H4'3 H 1.0489 1.1368 0.7562 0.071 Uiso 1 1 calc R U . . .
O2' O 1.02997(18) 0.8790(4) 0.9458(3) 0.0453(11) Uani 1 1 d . . . . .
O3' O 1.05286(19) 1.1074(5) 0.9985(3) 0.0499(12) Uani 1 1 d . . . . .
S1' S 1.01180(6) 1.01435(12) 0.96017(11) 0.0324(4) Uani 1 1 d . . . . .
C31' C 0.9477(3) 1.0111(5) 1.0234(4) 0.0301(14) Uani 1 1 d . . . . .
C32' C 0.9210(3) 0.8906(5) 1.0397(4) 0.0354(13) Uani 1 1 d . . . . .
H32' H 0.9364 0.8108 1.0157 0.042 Uiso 1 1 calc R U . . .
C33' C 0.8718(3) 0.8849(6) 1.0909(4) 0.0390(14) Uani 1 1 d . . . . .
H33' H 0.8529 0.8018 1.1012 0.047 Uiso 1 1 calc R U . . .
C34' C 0.8500(3) 1.0024(6) 1.1276(5) 0.0419(17) Uani 1 1 d . . . . .
C35' C 0.8773(3) 1.1231(6) 1.1100(5) 0.0461(17) Uani 1 1 d . . . . .
H35' H 0.8619 1.2037 1.1329 0.055 Uiso 1 1 calc R U . . .
C36' C 0.9267(3) 1.1268(6) 1.0597(5) 0.0421(15) Uani 1 1 d . . . . .
H36' H 0.9463 1.2093 1.0499 0.051 Uiso 1 1 calc R U . . .
C37' C 0.7955(4) 0.9976(8) 1.1822(7) 0.063(2) Uani 1 1 d . . . . .
H37D H 0.7726 0.9173 1.1685 0.095 Uiso 1 1 calc R U . . .
H37E H 0.7714 1.0772 1.1717 0.095 Uiso 1 1 calc R U . . .
H37F H 0.8070 0.9950 1.2419 0.095 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
O1 C1 N1 121.5(5) . . ?
O1 C1 C11 121.6(5) . . ?
N1 C1 C11 116.9(4) . . ?
C16 C11 C12 119.0(5) . . ?
C16 C11 C1 123.4(5) . . ?
C12 C11 C1 117.5(5) . . ?
C13 C12 C11 120.3(5) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 119.8(5) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 120.9(5) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C14 C15 C16 119.5(6) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C11 C16 C15 120.4(6) . . ?
C11 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C1 N1 C2 123.2(4) . . ?
C1 N1 H1 118.4 . . ?
C2 N1 H1 118.4 . . ?
O4 C2 N1 110.4(5) . . ?
O4 C2 C3 107.3(5) . . ?
N1 C2 C3 110.2(5) . . ?
O4 C2 H2 109.6 . . ?
N1 C2 H2 109.6 . . ?
C3 C2 H2 109.6 . . ?
C2 O4 C21 111.6(6) . . ?
O4 C21 H21A 109.5 . . ?
O4 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O4 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C2 C3 C4 112.3(5) . . ?
C2 C3 S1 112.4(4) . . ?
C4 C3 S1 105.6(4) . . ?
C2 C3 H3 108.8 . . ?
C4 C3 H3 108.8 . . ?
S1 C3 H3 108.8 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O2 S1 O3 119.0(2) . . ?
O2 S1 C31 106.7(3) . . ?
O3 S1 C31 107.8(3) . . ?
O2 S1 C3 108.2(3) . . ?
O3 S1 C3 105.2(3) . . ?
C31 S1 C3 109.7(3) . . ?
C32 C31 C36 120.6(6) . . ?
C32 C31 S1 119.4(5) . . ?
C36 C31 S1 120.0(4) . . ?
C31 C32 C33 119.4(6) . . ?
C31 C32 H32 120.3 . . ?
C33 C32 H32 120.3 . . ?
C34 C33 C32 120.8(6) . . ?
C34 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?
C33 C34 C35 118.6(6) . . ?
C33 C34 C37 120.7(6) . . ?
C35 C34 C37 120.6(6) . . ?
C36 C35 C34 121.4(5) . . ?
C36 C35 H35 119.3 . . ?
C34 C35 H35 119.3 . . ?
C35 C36 C31 119.3(5) . . ?
C35 C36 H36 120.4 . . ?
C31 C36 H36 120.4 . . ?
C34 C37 H37A 109.5 . . ?
C34 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C34 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
O1' C1' N1' 122.7(5) . . ?
O1' C1' C11' 120.8(5) . . ?
N1' C1' C11' 116.4(4) . . ?
C12' C11' C16' 120.2(5) . . ?
C12' C11' C1' 118.1(4) . . ?
C16' C11' C1' 121.7(5) . . ?
C13' C12' C11' 119.9(5) . . ?
C13' C12' H12' 120.0 . . ?
C11' C12' H12' 120.0 . . ?
C14' C13' C12' 119.7(6) . . ?
C14' C13' H13' 120.1 . . ?
C12' C13' H13' 120.1 . . ?
C13' C14' C15' 120.8(5) . . ?
C13' C14' H14' 119.6 . . ?
C15' C14' H14' 119.6 . . ?
C14' C15' C16' 119.8(5) . . ?
C14' C15' H15' 120.1 . . ?
C16' C15' H15' 120.1 . . ?
C15' C16' C11' 119.6(5) . . ?
C15' C16' H16' 120.2 . . ?
C11' C16' H16' 120.2 . . ?
C1' N1' C2' 123.2(4) . . ?
C1' N1' H1' 118.4 . . ?
C2' N1' H1' 118.4 . . ?
N1' C2' O4' 110.5(5) . . ?
N1' C2' C3' 110.9(5) . . ?
O4' C2' C3' 104.4(5) . . ?
N1' C2' H2' 110.3 . . ?
O4' C2' H2' 110.3 . . ?
C3' C2' H2' 110.3 . . ?
C21' O4' C2' 112.6(5) . . ?
O4' C21' H21D 109.5 . . ?
O4' C21' H21E 109.5 . . ?
H21D C21' H21E 109.5 . . ?
O4' C21' H21F 109.5 . . ?
H21D C21' H21F 109.5 . . ?
H21E C21' H21F 109.5 . . ?
C2' C3' C4' 112.5(5) . . ?
C2' C3' S1' 112.4(4) . . ?
C4' C3' S1' 105.1(4) . . ?
C2' C3' H3' 108.9 . . ?
C4' C3' H3' 108.9 . . ?
S1' C3' H3' 108.9 . . ?
C3' C4' H4'1 109.5 . . ?
C3' C4' H4'2 109.5 . . ?
H4'1 C4' H4'2 109.5 . . ?
C3' C4' H4'3 109.5 . . ?
H4'1 C4' H4'3 109.5 . . ?
H4'2 C4' H4'3 109.5 . . ?
O2' S1' O3' 119.1(3) . . ?
O2' S1' C31' 108.0(3) . . ?
O3' S1' C31' 107.8(3) . . ?
O2' S1' C3' 108.7(3) . . ?
O3' S1' C3' 103.4(3) . . ?
C31' S1' C3' 109.6(3) . . ?
C32' C31' C36' 120.4(6) . . ?
C32' C31' S1' 119.1(5) . . ?
C36' C31' S1' 120.4(5) . . ?
C31' C32' C33' 120.2(6) . . ?
C31' C32' H32' 119.9 . . ?
C33' C32' H32' 119.9 . . ?
C32' C33' C34' 119.7(6) . . ?
C32' C33' H33' 120.2 . . ?
C34' C33' H33' 120.2 . . ?
C35' C34' C33' 119.3(7) . . ?
C35' C34' C37' 120.7(7) . . ?
C33' C34' C37' 120.0(6) . . ?
C36' C35' C34' 120.3(6) . . ?
C36' C35' H35' 119.9 . . ?
C34' C35' H35' 119.9 . . ?
C31' C36' C35' 120.1(6) . . ?
C31' C36' H36' 120.0 . . ?
C35' C36' H36' 120.0 . . ?
C34' C37' H37D 109.5 . . ?
C34' C37' H37E 109.5 . . ?
H37D C37' H37E 109.5 . . ?
C34' C37' H37F 109.5 . . ?
H37D C37' H37F 109.5 . . ?
H37E C37' H37F 109.5 . . ?
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
O1 C1 1.235(6) . ?
C1 N1 1.341(7) . ?
C1 C11 1.479(8) . ?
C11 C16 1.387(8) . ?
C11 C12 1.401(8) . ?
C12 C13 1.394(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.368(10) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(10) . ?
C14 H14 0.9500 . ?
C15 C16 1.398(8) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
N1 C2 1.465(8) . ?
N1 H1 0.8800 . ?
C2 O4 1.405(8) . ?
C2 C3 1.524(8) . ?
C2 H2 1.0000 . ?
O4 C21 1.426(9) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C3 C4 1.536(7) . ?
C3 S1 1.805(6) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
O2 S1 1.426(4) . ?
O3 S1 1.444(4) . ?
S1 C31 1.764(7) . ?
C31 C32 1.389(9) . ?
C31 C36 1.396(8) . ?
C32 C33 1.399(10) . ?
C32 H32 0.9500 . ?
C33 C34 1.389(9) . ?
C33 H33 0.9500 . ?
C34 C35 1.403(9) . ?
C34 C37 1.493(10) . ?
C35 C36 1.376(9) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
O1' C1' 1.229(6) . ?
C1' N1' 1.343(7) . ?
C1' C11' 1.510(8) . ?
C11' C12' 1.385(8) . ?
C11' C16' 1.385(7) . ?
C12' C13' 1.383(8) . ?
C12' H12' 0.9500 . ?
C13' C14' 1.373(9) . ?
C13' H13' 0.9500 . ?
C14' C15' 1.381(9) . ?
C14' H14' 0.9500 . ?
C15' C16' 1.384(8) . ?
C15' H15' 0.9500 . ?
C16' H16' 0.9500 . ?
N1' C2' 1.425(8) . ?
N1' H1' 0.8800 . ?
C2' O4' 1.429(8) . ?
C2' C3' 1.532(8) . ?
C2' H2' 1.0000 . ?
O4' C21' 1.407(9) . ?
C21' H21D 0.9800 . ?
C21' H21E 0.9800 . ?
C21' H21F 0.9800 . ?
C3' C4' 1.544(8) . ?
C3' S1' 1.812(6) . ?
C3' H3' 1.0000 . ?
C4' H4'1 0.9800 . ?
C4' H4'2 0.9800 . ?
C4' H4'3 0.9800 . ?
O2' S1' 1.433(4) . ?
O3' S1' 1.450(5) . ?
S1' C31' 1.767(7) . ?
C31' C32' 1.374(8) . ?
C31' C36' 1.377(9) . ?
C32' C33' 1.381(10) . ?
C32' H32' 0.9500 . ?
C33' C34' 1.401(10) . ?
C33' H33' 0.9500 . ?
C34' C35' 1.385(10) . ?
C34' C37' 1.511(12) . ?
C35' C36' 1.377(10) . ?
C35' H35' 0.9500 . ?
C36' H36' 0.9500 . ?
C37' H37D 0.9800 . ?
C37' H37E 0.9800 . ?
C37' H37F 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1' 0.88 2.08 2.890(5) 153.1 .
C21 H21B O3 0.98 2.47 3.380(11) 153.8 3_655
C21 H21B S1 0.98 2.96 3.871(10) 155.1 3_655
C3 H3 O1' 1.00 2.50 3.346(6) 141.8 .
N1' H1' O1 0.88 2.06 2.836(5) 147.3 1_565
C21' H21E O3' 0.98 2.54 3.195(10) 124.1 2_774
C3' H3' O1 1.00 2.62 3.406(6) 135.2 1_565
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
O1 C1 C11 C16 -152.3(6) . . . . ?
N1 C1 C11 C16 28.3(8) . . . . ?
O1 C1 C11 C12 24.9(9) . . . . ?
N1 C1 C11 C12 -154.5(5) . . . . ?
C16 C11 C12 C13 0.0(9) . . . . ?
C1 C11 C12 C13 -177.3(6) . . . . ?
C11 C12 C13 C14 -0.6(11) . . . . ?
C12 C13 C14 C15 1.0(12) . . . . ?
C13 C14 C15 C16 -0.7(11) . . . . ?
C12 C11 C16 C15 0.3(9) . . . . ?
C1 C11 C16 C15 177.4(6) . . . . ?
C14 C15 C16 C11 0.1(10) . . . . ?
O1 C1 N1 C2 4.1(9) . . . . ?
C11 C1 N1 C2 -176.5(5) . . . . ?
C1 N1 C2 O4 105.1(6) . . . . ?
C1 N1 C2 C3 -136.4(5) . . . . ?
N1 C2 O4 C21 -70.1(7) . . . . ?
C3 C2 O4 C21 169.8(6) . . . . ?
O4 C2 C3 C4 -45.4(6) . . . . ?
N1 C2 C3 C4 -165.7(4) . . . . ?
O4 C2 C3 S1 -164.4(4) . . . . ?
N1 C2 C3 S1 75.4(5) . . . . ?
C2 C3 S1 O2 59.0(4) . . . . ?
C4 C3 S1 O2 -63.7(4) . . . . ?
C2 C3 S1 O3 -172.8(4) . . . . ?
C4 C3 S1 O3 64.5(4) . . . . ?
C2 C3 S1 C31 -57.1(5) . . . . ?
C4 C3 S1 C31 -179.8(4) . . . . ?
O2 S1 C31 C32 -3.2(6) . . . . ?
O3 S1 C31 C32 -132.2(5) . . . . ?
C3 S1 C31 C32 113.8(5) . . . . ?
O2 S1 C31 C36 174.7(5) . . . . ?
O3 S1 C31 C36 45.7(6) . . . . ?
C3 S1 C31 C36 -68.3(6) . . . . ?
C36 C31 C32 C33 -1.0(10) . . . . ?
S1 C31 C32 C33 176.9(5) . . . . ?
C31 C32 C33 C34 2.1(10) . . . . ?
C32 C33 C34 C35 -2.5(11) . . . . ?
C32 C33 C34 C37 -179.2(7) . . . . ?
C33 C34 C35 C36 2.1(11) . . . . ?
C37 C34 C35 C36 178.7(7) . . . . ?
C34 C35 C36 C31 -1.1(10) . . . . ?
C32 C31 C36 C35 0.5(10) . . . . ?
S1 C31 C36 C35 -177.4(5) . . . . ?
O1' C1' C11' C12' 29.1(9) . . . . ?
N1' C1' C11' C12' -151.4(6) . . . . ?
O1' C1' C11' C16' -148.8(6) . . . . ?
N1' C1' C11' C16' 30.8(8) . . . . ?
C16' C11' C12' C13' -0.2(10) . . . . ?
C1' C11' C12' C13' -178.1(6) . . . . ?
C11' C12' C13' C14' -0.6(10) . . . . ?
C12' C13' C14' C15' 1.4(11) . . . . ?
C13' C14' C15' C16' -1.4(10) . . . . ?
C14' C15' C16' C11' 0.5(10) . . . . ?
C12' C11' C16' C15' 0.3(9) . . . . ?
C1' C11' C16' C15' 178.1(5) . . . . ?
O1' C1' N1' C2' 6.9(9) . . . . ?
C11' C1' N1' C2' -172.6(6) . . . . ?
C1' N1' C2' O4' 108.2(6) . . . . ?
C1' N1' C2' C3' -136.6(5) . . . . ?
N1' C2' O4' C21' -62.6(7) . . . . ?
C3' C2' O4' C21' 178.2(6) . . . . ?
N1' C2' C3' C4' -168.1(5) . . . . ?
O4' C2' C3' C4' -49.1(6) . . . . ?
N1' C2' C3' S1' 73.5(5) . . . . ?
O4' C2' C3' S1' -167.5(3) . . . . ?
C2' C3' S1' O2' 60.8(4) . . . . ?
C4' C3' S1' O2' -62.0(4) . . . . ?
C2' C3' S1' O3' -171.8(4) . . . . ?
C4' C3' S1' O3' 65.5(4) . . . . ?
C2' C3' S1' C31' -57.1(4) . . . . ?
C4' C3' S1' C31' -179.8(4) . . . . ?
O2' S1' C31' C32' -8.2(6) . . . . ?
O3' S1' C31' C32' -138.2(5) . . . . ?
C3' S1' C31' C32' 110.0(6) . . . . ?
O2' S1' C31' C36' 168.2(6) . . . . ?
O3' S1' C31' C36' 38.2(6) . . . . ?
C3' S1' C31' C36' -73.6(6) . . . . ?
C36' C31' C32' C33' 1.8(10) . . . . ?
S1' C31' C32' C33' 178.2(5) . . . . ?
C31' C32' C33' C34' -1.3(10) . . . . ?
C32' C33' C34' C35' 1.7(11) . . . . ?
C32' C33' C34' C37' 178.7(7) . . . . ?
C33' C34' C35' C36' -2.4(12) . . . . ?
C37' C34' C35' C36' -179.5(8) . . . . ?
C32' C31' C36' C35' -2.5(11) . . . . ?
S1' C31' C36' C35' -178.9(5) . . . . ?
C34' C35' C36' C31' 2.9(11) . . . . ?
