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#$Date: 2020-04-24 22:57:59 +0300 (Fri, 24 Apr 2020) $
#$Revision: 251150 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/47/4134799.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_4134799
loop_
_publ_author_name
'Walker, Morgan M.'
'Koronkiewicz, Brian'
'Chen, Shuming'
'Houk, K. N.'
'Mayer, James M.'
'Ellman, Jonathan A.'
_publ_section_title
;
 Highly Diastereoselective Functionalization of Piperidines by Photoredox
 Catalyzed α-Amino C-H Arylation and Epimerization.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b13165
_journal_year                    2020
_chemical_formula_moiety         'C23 H29 N2, C6 H2 N3 O9 S'
_chemical_formula_sum            'C29 H31 N5 O9 S'
_chemical_formula_weight         625.65
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     SHELXT
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 92.656(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1117(3)
_cell_length_b                   19.7564(8)
_cell_length_c                   18.3015(9)
_cell_measurement_reflns_used    9876
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      58.5180
_cell_measurement_theta_min      3.2430
_cell_volume                     2929.8(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB-2014/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 22.2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.2324
_diffrn_reflns_av_unetI/netI     0.0743
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5182
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.601
_diffrn_reflns_theta_max         66.601
_diffrn_reflns_theta_min         3.294
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    1.529
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     413
_refine_ls_number_reflns         5182
_refine_ls_number_restraints     66
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1490
_refine_ls_R_factor_gt           0.0910
_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)+(0.0939P)²+4.9072P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2056
_refine_ls_wR_factor_ref         0.2395
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3141
_reflns_number_total             5182
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja9b13165_si_005.cif
_cod_data_source_block           007b-20020
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4134799
_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   0.941
_shelx_estimated_absorpt_t_max   0.970
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
S1 S 0.74339(16) 0.36517(6) 0.51796(8) 0.0458(4) Uani 1 1 d . . . . .
O1 O 0.7866(5) 0.34529(18) 0.5928(2) 0.0567(11) Uani 1 1 d . . . . .
O2 O 0.5875(4) 0.33896(17) 0.4896(2) 0.0462(10) Uani 1 1 d . . . . .
O3 O 0.8781(4) 0.35844(19) 0.4690(2) 0.0550(11) Uani 1 1 d . . . . .
O4 O 0.4952(5) 0.4105(2) 0.6366(2) 0.0582(11) Uani 1 1 d . . . . .
O5 O 0.6636(6) 0.4633(2) 0.7127(2) 0.0602(11) Uani 1 1 d . . . . .
O6 O 0.7469(5) 0.69234(18) 0.6192(2) 0.0545(11) Uani 1 1 d . . . . .
O7 O 0.7770(5) 0.70571(19) 0.5027(2) 0.0536(11) Uani 1 1 d . . . . .
O8 O 0.6988(5) 0.4451(2) 0.3641(2) 0.0534(10) Uani 1 1 d . . . . .
O9 O 0.9471(5) 0.4883(2) 0.3766(2) 0.0549(10) Uani 1 1 d . . . . .
N3 N 0.6079(6) 0.4507(2) 0.6512(3) 0.0475(12) Uani 1 1 d . . . . .
N4 N 0.7567(5) 0.6712(2) 0.5564(3) 0.0451(12) Uani 1 1 d . . . . .
N5 N 0.8105(6) 0.4752(2) 0.3993(3) 0.0462(11) Uani 1 1 d . . . . .
C24 C 0.7191(6) 0.4565(2) 0.5264(3) 0.0384(13) Uani 1 1 d . . . . .
C25 C 0.6741(6) 0.4893(3) 0.5898(3) 0.0386(12) Uani 1 1 d . . . . .
C26 C 0.6843(6) 0.5581(3) 0.6016(3) 0.0428(13) Uani 1 1 d . . . . .
H26 H 0.6529 0.5779 0.6462 0.051 Uiso 1 1 calc R U . . .
C27 C 0.7420(6) 0.5970(2) 0.5458(3) 0.0399(13) Uani 1 1 d . . . . .
C28 C 0.7854(6) 0.5704(2) 0.4803(3) 0.0377(12) Uani 1 1 d . . . . .
H28 H 0.8237 0.5982 0.4423 0.045 Uiso 1 1 calc R U . . .
C29 C 0.7704(6) 0.5005(3) 0.4724(3) 0.0392(12) Uani 1 1 d . . . . .
N1 N 0.8360(6) 0.2522(2) 0.7152(3) 0.0541(13) Uani 1 1 d . . . . .
H1 H 0.8362 0.2829 0.6718 0.065 Uiso 1 1 calc R U . . .
N2 N 0.2811(9) 0.0102(4) 0.4985(5) 0.110(3) Uani 1 1 d . . . . .
C1 C 0.9365(8) 0.2887(4) 0.7757(4) 0.0674(19) Uani 1 1 d . . . . .
H1A H 0.9928 0.2546 0.8086 0.081 Uiso 1 1 calc R U . . .
C2 C 0.8277(10) 0.3337(3) 0.8201(4) 0.074(2) Uani 1 1 d . . . . .
H2B H 0.7719 0.3650 0.7839 0.088 Uiso 0.817(12) 1 calc R U P A 2
H2A H 0.7801 0.3706 0.7883 0.088 Uiso 0.183(12) 1 calc R U P A 1
C3 C 0.6893(10) 0.2959(4) 0.8554(4) 0.079(2) Uani 1 1 d . . . . .
H3 H 0.7330 0.2810 0.9048 0.095 Uiso 1 1 calc R U . . .
C4 C 0.6396(9) 0.2325(4) 0.8134(4) 0.073(2) Uani 1 1 d . . . . .
H4A H 0.7132 0.1947 0.8289 0.088 Uiso 1 1 calc R U . . .
H4B H 0.5252 0.2199 0.8242 0.088 Uiso 1 1 calc R U . . .
C5 C 0.6509(7) 0.2443(3) 0.7335(3) 0.0524(15) Uani 1 1 d . . . . .
H5 H 0.5965 0.2888 0.7225 0.063 Uiso 1 1 calc R U . . .
C6 C 0.5674(7) 0.1929(3) 0.6836(4) 0.0577(16) Uani 1 1 d . . . . .
C7 C 0.4983(8) 0.2134(3) 0.6159(4) 0.0630(17) Uani 1 1 d . . . . .
H7 H 0.5011 0.2598 0.6025 0.076 Uiso 1 1 calc R U . . .
C8 C 0.4262(9) 0.1670(3) 0.5681(4) 0.071(2) Uani 1 1 d . . . . .
H8 H 0.3790 0.1815 0.5223 0.086 Uiso 1 1 calc R U . . .
C9 C 0.4224(9) 0.0986(4) 0.5870(4) 0.076(2) Uani 1 1 d . . . . .
C10 C 0.4897(9) 0.0768(4) 0.6539(4) 0.080(2) Uani 1 1 d . . . . .
H10 H 0.4879 0.0302 0.6668 0.096 Uiso 1 1 calc R U . . .
C11 C 0.5595(8) 0.1241(3) 0.7016(4) 0.0679(19) Uani 1 1 d . . . . .
H11 H 0.6035 0.1096 0.7480 0.082 Uiso 1 1 calc R U . . .
C12 C 0.3424(10) 0.0493(4) 0.5365(5) 0.085(2) Uani 1 1 d . . . . .
C13 C 1.0765(11) 0.3349(8) 0.7360(8) 0.190(8) Uani 1 1 d . . . . .
H13A H 1.0202 0.3708 0.7067 0.229 Uiso 1 1 calc R U . . .
H13B H 1.1478 0.3571 0.7743 0.229 Uiso 1 1 calc R U . . .
C14 C 1.1742(15) 0.2974(7) 0.6913(9) 0.193(7) Uani 1 1 d . . . . .
H14A H 1.2126 0.2565 0.7171 0.290 Uiso 1 1 calc R U . . .
H14B H 1.2695 0.3245 0.6781 0.290 Uiso 1 1 calc R U . . .
H14C H 1.1098 0.2845 0.6468 0.290 Uiso 1 1 calc R U . . .
C15A C 0.910(7) 0.372(3) 0.913(3) 0.079(3) Uani 0.183(12) 1 d . . P A 1
H15A H 0.9322 0.3349 0.9486 0.094 Uiso 0.183(12) 1 calc R U P A 1
H15B H 1.0148 0.3959 0.9059 0.094 Uiso 0.183(12) 1 calc R U P A 1
C15B C 0.9304(14) 0.3790(5) 0.8715(7) 0.079(3) Uani 0.817(12) 1 d . . P A 2
H15C H 0.9896 0.4125 0.8422 0.094 Uiso 0.817(12) 1 calc R U P A 2
H15D H 0.8556 0.4042 0.9030 0.094 Uiso 0.817(12) 1 calc R U P A 2
C16A C 0.813(7) 0.411(3) 0.938(3) 0.120(5) Uani 0.183(12) 1 d . . P A 1
H16A H 0.7981 0.4501 0.9056 0.180 Uiso 0.183(12) 1 calc R U P A 1
H16B H 0.8549 0.4263 0.9865 0.180 Uiso 0.183(12) 1 calc R U P A 1
H16C H 0.7064 0.3883 0.9431 0.180 Uiso 0.183(12) 1 calc R U P A 1
C16B C 1.0517(15) 0.3416(6) 0.9185(7) 0.120(5) Uani 0.817(12) 1 d . . P A 2
H16D H 0.9938 0.3096 0.9492 0.180 Uiso 0.817(12) 1 calc R U P A 2
H16E H 1.1150 0.3735 0.9496 0.180 Uiso 0.817(12) 1 calc R U P A 2
H16F H 1.1269 0.3167 0.8878 0.180 Uiso 0.817(12) 1 calc R U P A 2
C17 C 0.5376(12) 0.3410(5) 0.8677(5) 0.113(3) Uani 1 1 d . . . . .
H17A H 0.4821 0.3518 0.8204 0.170 Uiso 1 1 calc R U . . .
H17B H 0.5735 0.3830 0.8921 0.170 Uiso 1 1 calc R U . . .
H17C H 0.4610 0.3169 0.8983 0.170 Uiso 1 1 calc R U . . .
C19B C 0.9671(10) 0.1404(4) 0.7420(5) 0.059(2) Uani 0.876(10) 1 d D . P B 2
H19B H 0.9707 0.1497 0.7929 0.071 Uiso 0.876(10) 1 calc R U P B 2
C20A C 1.0197(16) 0.0789(5) 0.7157(7) 0.092(3) Uani 0.876(10) 1 d D . P B 2
H20A H 1.0608 0.0456 0.7493 0.111 Uiso 0.876(10) 1 calc R U P B 2
C21A C 1.0139(17) 0.0647(5) 0.6408(6) 0.119(5) Uani 0.876(10) 1 d D . P B 2
H21A H 1.0520 0.0222 0.6241 0.142 Uiso 0.876(10) 1 calc R U P B 2
C22A C 0.9526(17) 0.1123(5) 0.5906(6) 0.115(4) Uani 0.876(10) 1 d D . P B 2
H22A H 0.9464 0.1021 0.5399 0.137 Uiso 0.876(10) 1 calc R U P B 2
C23A C 0.9005(12) 0.1749(4) 0.6152(4) 0.070(3) Uani 0.876(10) 1 d D . P B 2
H23A H 0.8604 0.2083 0.5815 0.084 Uiso 0.876(10) 1 calc R U P B 2
C23B C 0.991(5) 0.1997(17) 0.6274(14) 0.070(3) Uani 0.124(10) 1 d DG . P B 1
H23B H 0.9710 0.2401 0.6002 0.084 Uiso 0.124(10) 1 calc R U P B 1
C18 C 0.9083(8) 0.1882(3) 0.6911(3) 0.0580(16) Uani 1 1 d DG . . . .
C19A C 0.938(6) 0.1291(14) 0.731(2) 0.059(2) Uani 0.124(10) 1 d DG . P B 1
H19A H 0.8810 0.1212 0.7744 0.071 Uiso 0.124(10) 1 calc R U P B 1
C20B C 1.050(8) 0.082(2) 0.707(3) 0.092(3) Uani 0.124(10) 1 d DG . P B 1
H20B H 1.0697 0.0413 0.7343 0.111 Uiso 0.124(10) 1 calc R U P B 1
C21B C 1.132(7) 0.093(3) 0.643(3) 0.119(5) Uani 0.124(10) 1 d DG . P B 1
H21B H 1.2091 0.0608 0.6272 0.142 Uiso 0.124(10) 1 calc R U P B 1
C22B C 1.103(6) 0.152(3) 0.604(2) 0.115(4) Uani 0.124(10) 1 d DG . P B 1
H22B H 1.1597 0.1602 0.5601 0.137 Uiso 0.124(10) 1 calc R U P B 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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
O2 S1 O3 114.7(2) . . ?
O2 S1 O1 114.3(2) . . ?
O3 S1 O1 113.7(3) . . ?
O2 S1 C24 106.8(2) . . ?
O3 S1 C24 103.3(2) . . ?
O1 S1 C24 102.2(2) . . ?
O5 N3 O4 124.9(5) . . ?
O5 N3 C25 117.6(5) . . ?
O4 N3 C25 117.4(5) . . ?
O7 N4 O6 125.7(5) . . ?
O7 N4 C27 117.6(5) . . ?
O6 N4 C27 116.7(5) . . ?
O9 N5 O8 125.0(5) . . ?
O9 N5 C29 118.4(4) . . ?
O8 N5 C29 116.5(5) . . ?
C25 C24 C29 113.6(5) . . ?
C25 C24 S1 124.3(4) . . ?
C29 C24 S1 121.4(4) . . ?
C26 C25 C24 124.9(5) . . ?
C26 C25 N3 114.3(5) . . ?
C24 C25 N3 120.8(4) . . ?
C27 C26 C25 117.0(5) . . ?
C27 C26 H26 121.5 . . ?
C25 C26 H26 121.5 . . ?
C28 C27 C26 123.1(5) . . ?
C28 C27 N4 118.1(5) . . ?
C26 C27 N4 118.9(5) . . ?
C27 C28 C29 116.5(5) . . ?
C27 C28 H28 121.7 . . ?
C29 C28 H28 121.7 . . ?
C24 C29 C28 124.9(5) . . ?
C24 C29 N5 121.0(5) . . ?
C28 C29 N5 114.1(5) . . ?
C18 N1 C1 114.7(5) . . ?
C18 N1 C5 112.3(5) . . ?
C1 N1 C5 112.3(5) . . ?
C18 N1 H1 105.6 . . ?
C1 N1 H1 105.6 . . ?
C5 N1 H1 105.6 . . ?
C2 C1 N1 111.2(5) . . ?
C2 C1 C13 110.0(7) . . ?
N1 C1 C13 107.3(6) . . ?
C2 C1 H1A 109.4 . . ?
N1 C1 H1A 109.4 . . ?
C13 C1 H1A 109.4 . . ?
C1 C2 C3 113.6(6) . . ?
C1 C2 C15B 111.2(7) . . ?
C3 C2 C15B 115.0(8) . . ?
C1 C2 C15A 120.9(19) . . ?
C3 C2 C15A 92.8(18) . . ?
C1 C2 H2B 105.3 . . ?
C3 C2 H2B 105.3 . . ?
C15B C2 H2B 105.3 . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C15A C2 H2A 109.4 . . ?
C4 C3 C2 112.1(6) . . ?
C4 C3 C17 110.9(7) . . ?
C2 C3 C17 112.8(7) . . ?
C4 C3 H3 106.9 . . ?
C2 C3 H3 106.9 . . ?
C17 C3 H3 106.9 . . ?
C5 C4 C3 110.0(6) . . ?
C5 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C4 C5 C6 116.4(5) . . ?
C4 C5 N1 109.3(5) . . ?
C6 C5 N1 110.4(5) . . ?
C4 C5 H5 106.8 . . ?
C6 C5 H5 106.8 . . ?
N1 C5 H5 106.8 . . ?
C7 C6 C11 117.9(6) . . ?
C7 C6 C5 119.6(5) . . ?
C11 C6 C5 122.4(6) . . ?
C8 C7 C6 120.8(6) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 120.0(7) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 120.5(7) . . ?
C10 C9 C12 119.5(7) . . ?
C8 C9 C12 120.0(7) . . ?
C11 C10 C9 118.7(7) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C10 C11 C6 122.0(6) . . ?
C10 C11 H11 119.0 . . ?
C6 C11 H11 119.0 . . ?
N2 C12 C9 178.7(10) . . ?
C14 C13 C1 113.0(12) . . ?
C14 C13 H13A 109.0 . . ?
C1 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C1 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16A C15A C2 112(4) . . ?
C16A C15A H15A 109.2 . . ?
C2 C15A H15A 109.2 . . ?
C16A C15A H15B 109.2 . . ?
C2 C15A H15B 109.2 . . ?
H15A C15A H15B 107.9 . . ?
C16B C15B C2 113.4(8) . . ?
C16B C15B H15C 108.9 . . ?
C2 C15B H15C 108.9 . . ?
C16B C15B H15D 108.9 . . ?
C2 C15B H15D 108.9 . . ?
H15C C15B H15D 107.7 . . ?
C15A C16A H16A 109.5 . . ?
C15A C16A H16B 109.5 . . ?
H16A C16A H16B 109.5 . . ?
C15A C16A H16C 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C15B C16B H16D 109.5 . . ?
C15B C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
C15B C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
C3 C17 H17A 109.5 . . ?
C3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C20A C19B C18 117.7(8) . . ?
C20A C19B H19B 121.2 . . ?
C18 C19B H19B 121.2 . . ?
C19B C20A C21A 121.4(8) . . ?
C19B C20A H20A 119.3 . . ?
C21A C20A H20A 119.3 . . ?
C22A C21A C20A 120.4(9) . . ?
C22A C21A H21A 119.8 . . ?
C20A C21A H21A 119.8 . . ?
C23A C22A C21A 119.6(9) . . ?
C23A C22A H22A 120.2 . . ?
C21A C22A H22A 120.2 . . ?
C22A C23A C18 118.9(8) . . ?
C22A C23A H23A 120.6 . . ?
C18 C23A H23A 120.6 . . ?
C18 C23B C22B 120.0 . . ?
C18 C23B H23B 120.0 . . ?
C22B C23B H23B 120.0 . . ?
C23B C18 C19A 120.0 . . ?
C19B C18 C23A 122.0(7) . . ?
C23B C18 N1 109.0(13) . . ?
C19A C18 N1 128.7(14) . . ?
C19B C18 N1 120.7(6) . . ?
C23A C18 N1 117.0(5) . . ?
C20B C19A C18 120.0 . . ?
C20B C19A H19A 120.0 . . ?
C18 C19A H19A 120.0 . . ?
C19A C20B C21B 120.0 . . ?
C19A C20B H20B 120.0 . . ?
C21B C20B H20B 120.0 . . ?
C20B C21B C22B 120.0 . . ?
C20B C21B H21B 120.0 . . ?
C22B C21B H21B 120.0 . . ?
C21B C22B C23B 120.0 . . ?
C21B C22B H22B 120.0 . . ?
C23B C22B H22B 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 O2 1.441(4) . ?
S1 O3 1.451(4) . ?
S1 O1 1.452(4) . ?
S1 C24 1.823(5) . ?
O4 N3 1.231(6) . ?
O5 N3 1.220(6) . ?
O6 N4 1.230(6) . ?
O7 N4 1.213(6) . ?
O8 N5 1.240(5) . ?
O9 N5 1.230(6) . ?
N3 C25 1.478(7) . ?
N4 C27 1.483(6) . ?
N5 C29 1.478(7) . ?
C24 C25 1.393(7) . ?
C24 C29 1.393(7) . ?
C25 C26 1.379(7) . ?
C26 C27 1.377(8) . ?
C26 H26 0.9500 . ?
C27 C28 1.369(7) . ?
C28 C29 1.394(7) . ?
C28 H28 0.9500 . ?
N1 C18 1.471(7) . ?
N1 C1 1.526(8) . ?
N1 C5 1.561(7) . ?
N1 H1 1.0000 . ?
N2 C12 1.138(9) . ?
C1 C2 1.515(10) . ?
C1 C13 1.650(15) . ?
C1 H1A 1.0000 . ?
C2 C3 1.517(10) . ?
C2 C15B 1.518(12) . ?
C2 C15A 1.95(5) . ?
C2 H2B 1.0000 . ?
C2 H2A 1.0000 . ?
C3 C4 1.514(10) . ?
C3 C17 1.544(12) . ?
C3 H3 1.0000 . ?
C4 C5 1.488(9) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.505(9) . ?
C5 H5 1.0000 . ?
C6 C7 1.396(8) . ?
C6 C11 1.400(9) . ?
C7 C8 1.378(9) . ?
C7 H7 0.9500 . ?
C8 C9 1.394(9) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(10) . ?
C9 C12 1.473(11) . ?
C10 C11 1.382(9) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C13 C14 1.381(15) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15A C16A 1.21(7) . ?
C15A H15A 0.9900 . ?
C15A H15B 0.9900 . ?
C15B C16B 1.475(16) . ?
C15B H15C 0.9900 . ?
C15B H15D 0.9900 . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C16A H16C 0.9800 . ?
C16B H16D 0.9800 . ?
C16B H16E 0.9800 . ?
C16B H16F 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C19B C20A 1.381(9) . ?
C19B C18 1.395(8) . ?
C19B H19B 0.9500 . ?
C20A C21A 1.398(11) . ?
C20A H20A 0.9500 . ?
C21A C22A 1.391(10) . ?
C21A H21A 0.9500 . ?
C22A C23A 1.388(9) . ?
C22A H22A 0.9500 . ?
C23A C18 1.412(8) . ?
C23A H23A 0.9500 . ?
C23B C18 1.3900 . ?
C23B C22B 1.3900 . ?
C23B H23B 0.9500 . ?
C18 C19A 1.3900 . ?
C19A C20B 1.3900 . ?
C19A H19A 0.9500 . ?
C20B C21B 1.3900 . ?
C20B H20B 0.9500 . ?
C21B C22B 1.3900 . ?
C21B H21B 0.9500 . ?
C22B H22B 0.9500 . ?
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 1.00 1.93 2.911(6) 167.4 .
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
O2 S1 C24 C25 93.2(4) . . . . ?
O3 S1 C24 C25 -145.4(4) . . . . ?
O1 S1 C24 C25 -27.1(5) . . . . ?
O2 S1 C24 C29 -97.3(4) . . . . ?
O3 S1 C24 C29 24.1(5) . . . . ?
O1 S1 C24 C29 142.3(4) . . . . ?
C29 C24 C25 C26 -2.7(7) . . . . ?
S1 C24 C25 C26 167.5(4) . . . . ?
C29 C24 C25 N3 176.6(4) . . . . ?
S1 C24 C25 N3 -13.2(7) . . . . ?
O5 N3 C25 C26 -46.8(6) . . . . ?
O4 N3 C25 C26 130.0(5) . . . . ?
O5 N3 C25 C24 133.8(5) . . . . ?
O4 N3 C25 C24 -49.4(7) . . . . ?
C24 C25 C26 C27 0.6(8) . . . . ?
N3 C25 C26 C27 -178.7(4) . . . . ?
C25 C26 C27 C28 1.3(7) . . . . ?
C25 C26 C27 N4 -179.4(4) . . . . ?
O7 N4 C27 C28 13.2(7) . . . . ?
O6 N4 C27 C28 -167.0(4) . . . . ?
O7 N4 C27 C26 -166.2(5) . . . . ?
O6 N4 C27 C26 13.7(7) . . . . ?
C26 C27 C28 C29 -0.8(7) . . . . ?
N4 C27 C28 C29 179.8(4) . . . . ?
C25 C24 C29 C28 3.3(7) . . . . ?
S1 C24 C29 C28 -167.3(4) . . . . ?
C25 C24 C29 N5 -175.3(4) . . . . ?
S1 C24 C29 N5 14.2(6) . . . . ?
C27 C28 C29 C24 -1.7(7) . . . . ?
C27 C28 C29 N5 177.0(4) . . . . ?
O9 N5 C29 C24 -124.8(5) . . . . ?
O8 N5 C29 C24 59.0(6) . . . . ?
O9 N5 C29 C28 56.5(6) . . . . ?
O8 N5 C29 C28 -119.7(5) . . . . ?
C18 N1 C1 C2 -154.5(6) . . . . ?
C5 N1 C1 C2 -24.8(7) . . . . ?
C18 N1 C1 C13 85.1(8) . . . . ?
C5 N1 C1 C13 -145.1(7) . . . . ?
N1 C1 C2 C3 58.1(8) . . . . ?
C13 C1 C2 C3 176.9(7) . . . . ?
N1 C1 C2 C15B -170.3(7) . . . . ?
C13 C1 C2 C15B -51.5(10) . . . . ?
N1 C1 C2 C15A 167(2) . . . . ?
C13 C1 C2 C15A -74(2) . . . . ?
C1 C2 C3 C4 -26.4(9) . . . . ?
C15B C2 C3 C4 -156.1(7) . . . . ?
C15A C2 C3 C4 -152.0(18) . . . . ?
C1 C2 C3 C17 -152.5(7) . . . . ?
C15B C2 C3 C17 77.8(9) . . . . ?
C15A C2 C3 C17 81.9(19) . . . . ?
C2 C3 C4 C5 -36.0(9) . . . . ?
C17 C3 C4 C5 91.1(8) . . . . ?
C3 C4 C5 C6 -165.6(6) . . . . ?
C3 C4 C5 N1 68.7(7) . . . . ?
C18 N1 C5 C4 95.2(6) . . . . ?
C1 N1 C5 C4 -35.7(7) . . . . ?
C18 N1 C5 C6 -34.0(6) . . . . ?
C1 N1 C5 C6 -164.9(5) . . . . ?
C4 C5 C6 C7 147.7(6) . . . . ?
N1 C5 C6 C7 -87.1(7) . . . . ?
C4 C5 C6 C11 -34.1(9) . . . . ?
N1 C5 C6 C11 91.1(7) . . . . ?
C11 C6 C7 C8 -0.6(10) . . . . ?
C5 C6 C7 C8 177.7(6) . . . . ?
C6 C7 C8 C9 -0.4(11) . . . . ?
C7 C8 C9 C10 0.5(12) . . . . ?
C7 C8 C9 C12 178.8(7) . . . . ?
C8 C9 C10 C11 0.4(12) . . . . ?
C12 C9 C10 C11 -177.9(7) . . . . ?
C9 C10 C11 C6 -1.4(12) . . . . ?
C7 C6 C11 C10 1.5(11) . . . . ?
C5 C6 C11 C10 -176.7(7) . . . . ?
C2 C1 C13 C14 -176.6(11) . . . . ?
N1 C1 C13 C14 -55.4(13) . . . . ?
C1 C2 C15B C16B -53.1(13) . . . . ?
C3 C2 C15B C16B 77.8(12) . . . . ?
C18 C19B C20A C21A -0.3(16) . . . . ?
C19B C20A C21A C22A -1(2) . . . . ?
C20A C21A C22A C23A 1(2) . . . . ?
C21A C22A C23A C18 -1.2(17) . . . . ?
C22B C23B C18 C19A 0.0 . . . . ?
C22B C23B C18 N1 164.0(19) . . . . ?
C20A C19B C18 C23A 0.6(12) . . . . ?
C20A C19B C18 N1 174.3(8) . . . . ?
C22A C23A C18 C19B 0.2(13) . . . . ?
C22A C23A C18 N1 -173.8(9) . . . . ?
C1 N1 C18 C23B -99(2) . . . . ?
C5 N1 C18 C23B 131(2) . . . . ?
C1 N1 C18 C19A 63(3) . . . . ?
C5 N1 C18 C19A -66(3) . . . . ?
C1 N1 C18 C19B 47.1(8) . . . . ?
C5 N1 C18 C19B -82.6(7) . . . . ?
C1 N1 C18 C23A -138.9(7) . . . . ?
C5 N1 C18 C23A 91.4(7) . . . . ?
C23B C18 C19A C20B 0.0 . . . . ?
N1 C18 C19A C20B -161(2) . . . . ?
C18 C19A C20B C21B 0.0 . . . . ?
C19A C20B C21B C22B 0.0 . . . . ?
C20B C21B C22B C23B 0.0 . . . . ?
C18 C23B C22B C21B 0.0 . . . . ?
