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#$Date: 2025-08-20 17:59:05 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301833 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/79/4117939.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_4117939
loop_
_publ_author_name
'Ming Bian'
'Zhen Wang'
'Xiaochun Xiong'
'Yu Sun'
'Carlo Matera'
'K. C. Nicolaou'
'Ang Li'
_publ_section_title
;
 Total Syntheses of Anominine and Tubingensin A
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8078
_journal_page_last               8081
_journal_paper_doi               10.1021/ja302765m
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C32 H37 N O4 S'
_chemical_formula_weight         531.69
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                91.331(2)
_cell_angle_beta                 94.771(2)
_cell_angle_gamma                90.583(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0406(10)
_cell_length_b                   9.7562(12)
_cell_length_c                   17.270(2)
_cell_measurement_reflns_used    2956
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      28.95
_cell_measurement_theta_min      2.37
_cell_volume                     1349.6(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0469
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10408
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  0.9720
_exptl_absorpt_correction_T_min  0.9568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.874
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         5859
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.874
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0406
_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)+(0.0982P)²+0.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1375
_reflns_number_gt                4441
_reflns_number_total             5859
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja302765m_si_002.cif
_cod_data_source_block           mo_dm12044_0m
_cod_database_code               4117939
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.03811(6) 0.20330(5) -0.09565(3) 0.01784(13) Uani 1 1 d .
O1 O 0.55016(16) 0.31280(14) 0.40918(8) 0.0205(3) Uani 1 1 d .
O2 O 0.57274(17) 0.07417(15) 0.39517(8) 0.0260(3) Uani 1 1 d .
O3 O -0.06130(17) 0.09493(14) -0.06877(8) 0.0227(3) Uani 1 1 d .
O4 O -0.02692(18) 0.29040(15) -0.15580(8) 0.0253(3) Uani 1 1 d .
N1 N 0.09373(19) 0.30183(16) -0.01822(9) 0.0170(3) Uani 1 1 d .
C1 C 0.1819(2) 0.42784(19) -0.02004(10) 0.0163(4) Uani 1 1 d .
C2 C 0.1905(2) 0.5202(2) -0.07965(11) 0.0203(4) Uani 1 1 d .
H2A H 0.1347 0.5029 -0.1297 0.024 Uiso 1 1 calc R
C3 C 0.2841(2) 0.6386(2) -0.06275(12) 0.0241(4) Uani 1 1 d .
H3A H 0.2932 0.7039 -0.1022 0.029 Uiso 1 1 calc R
C4 C 0.3654(2) 0.6642(2) 0.01094(12) 0.0243(4) Uani 1 1 d .
H4A H 0.4294 0.7462 0.0206 0.029 Uiso 1 1 calc R
C5 C 0.3544(2) 0.5724(2) 0.06982(11) 0.0208(4) Uani 1 1 d .
H5A H 0.4077 0.5915 0.1201 0.025 Uiso 1 1 calc R
C6 C 0.2630(2) 0.45075(19) 0.05413(10) 0.0167(4) Uani 1 1 d .
C7 C 0.2265(2) 0.33531(19) 0.10196(10) 0.0159(4) Uani 1 1 d .
C8 C 0.1280(2) 0.2470(2) 0.05649(10) 0.0176(4) Uani 1 1 d .
H8A H 0.0880 0.1611 0.0724 0.021 Uiso 1 1 calc R
C9 C 0.2942(2) 0.33148(19) 0.18351(10) 0.0166(4) Uani 1 1 d .
H9A H 0.4101 0.3516 0.1927 0.020 Uiso 1 1 calc R
C10 C 0.2155(2) 0.30355(19) 0.24673(10) 0.0163(4) Uani 1 1 d .
C11 C 0.2961(2) 0.32019(19) 0.33044(10) 0.0152(4) Uani 1 1 d .
C12 C 0.1913(2) 0.4255(2) 0.37733(10) 0.0192(4) Uani 1 1 d .
C13 C 0.0050(2) 0.3854(3) 0.36656(11) 0.0271(5) Uani 1 1 d .
H13A H -0.0112 0.2982 0.3933 0.032 Uiso 1 1 calc R
H13B H -0.0594 0.4566 0.3924 0.032 Uiso 1 1 calc R
C14 C -0.0666(2) 0.3683(3) 0.28210(12) 0.0282(5) Uani 1 1 d .
H14A H -0.1844 0.3369 0.2799 0.034 Uiso 1 1 calc R
H14B H -0.0623 0.4568 0.2555 0.034 Uiso 1 1 calc R
C15 C 0.0365(2) 0.2639(2) 0.24314(11) 0.0212(4) Uani 1 1 d .
C16 C -0.0229(3) 0.1440(2) 0.21596(12) 0.0291(5) Uani 1 1 d .
H16A H 0.0504 0.0774 0.1973 0.035 Uiso 1 1 calc R
H16B H -0.1390 0.1242 0.2151 0.035 Uiso 1 1 calc R
C17 C 0.2373(3) 0.4231(2) 0.46570(11) 0.0243(4) Uani 1 1 d .
H17A H 0.1742 0.4936 0.4916 0.036 Uiso 1 1 calc R
H17B H 0.3571 0.4415 0.4766 0.036 Uiso 1 1 calc R
H17C H 0.2098 0.3328 0.4851 0.036 Uiso 1 1 calc R
C18 C 0.1122(3) 0.6830(2) 0.37474(15) 0.0375(6) Uani 1 1 d .
H18A H 0.1264 0.6897 0.4316 0.056 Uiso 1 1 calc R
H18B H -0.0045 0.6604 0.3580 0.056 Uiso 1 1 calc R
H18C H 0.1424 0.7709 0.3531 0.056 Uiso 1 1 calc R
C19 C 0.2254(2) 0.5703(2) 0.34579(11) 0.0234(4) Uani 1 1 d .
H19 H 0.2053 0.5642 0.2879 0.028 Uiso 1 1 calc R
C20 C 0.4087(3) 0.6105(2) 0.36520(11) 0.0237(4) Uani 1 1 d .
H20A H 0.4281 0.7043 0.3470 0.028 Uiso 1 1 calc R
H20B H 0.4342 0.6112 0.4223 0.028 Uiso 1 1 calc R
C21 C 0.5256(2) 0.5117(2) 0.32746(11) 0.0215(4) Uani 1 1 d .
H21A H 0.5247 0.5325 0.2716 0.026 Uiso 1 1 calc R
H21B H 0.6406 0.5285 0.3512 0.026 Uiso 1 1 calc R
C22 C 0.4828(2) 0.36044(19) 0.33472(10) 0.0171(4) Uani 1 1 d .
H22 H 0.5358 0.3077 0.2932 0.020 Uiso 1 1 calc R
C23 C 0.3091(2) 0.1779(2) 0.36920(11) 0.0214(4) Uani 1 1 d .
H23A H 0.2142 0.1625 0.4011 0.026 Uiso 1 1 calc R
H23B H 0.3097 0.1034 0.3294 0.026 Uiso 1 1 calc R
C24 C 0.4746(2) 0.1833(2) 0.42032(11) 0.0213(4) Uani 1 1 d .
H24 H 0.4539 0.1728 0.4762 0.026 Uiso 1 1 calc R
C25 C 0.7264(3) 0.0610(2) 0.44273(13) 0.0292(5) Uani 1 1 d .
H25A H 0.7035 0.0427 0.4970 0.035 Uiso 1 1 calc R
H25B H 0.7932 0.1467 0.4424 0.035 Uiso 1 1 calc R
C26 C 0.8201(3) -0.0567(3) 0.40957(16) 0.0437(6) Uani 1 1 d .
H26A H 0.7493 -0.1393 0.4063 0.065 Uiso 1 1 calc R
H26B H 0.9217 -0.0732 0.4433 0.065 Uiso 1 1 calc R
H26C H 0.8503 -0.0341 0.3575 0.065 Uiso 1 1 calc R
C27 C 0.2280(2) 0.1350(2) -0.12260(11) 0.0192(4) Uani 1 1 d .
C28 C 0.3007(2) 0.0277(2) -0.08091(11) 0.0203(4) Uani 1 1 d .
H28 H 0.2489 -0.0093 -0.0384 0.024 Uiso 1 1 calc R
C29 C 0.4504(2) -0.0244(2) -0.10253(12) 0.0241(4) Uani 1 1 d .
H29 H 0.5017 -0.0977 -0.0747 0.029 Uiso 1 1 calc R
C30 C 0.5252(3) 0.0298(2) -0.16413(14) 0.0347(5) Uani 1 1 d .
H30 H 0.6281 -0.0061 -0.1783 0.042 Uiso 1 1 calc R
C31 C 0.4511(4) 0.1361(3) -0.20544(16) 0.0469(7) Uani 1 1 d .
H31 H 0.5028 0.1723 -0.2482 0.056 Uiso 1 1 calc R
C32 C 0.3019(3) 0.1900(2) -0.18463(13) 0.0328(5) Uani 1 1 d .
H32 H 0.2511 0.2636 -0.2125 0.039 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'
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'
N N 0.0061 0.0033 '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
O4 S1 O3 120.86(9)
O4 S1 N1 107.52(8)
O3 S1 N1 105.85(8)
O4 S1 C27 108.36(9)
O3 S1 C27 108.85(9)
N1 S1 C27 104.13(8)
C24 O1 C22 107.20(13)
C24 O2 C25 112.60(16)
C8 N1 C1 107.86(14)
C8 N1 S1 122.04(13)
C1 N1 S1 124.54(12)
C2 C1 C6 122.72(18)
C2 C1 N1 130.32(17)
C6 C1 N1 106.93(15)
C3 C2 C1 116.85(18)
C3 C2 H2A 121.6
C1 C2 H2A 121.6
C2 C3 C4 121.54(19)
C2 C3 H3A 119.2
C4 C3 H3A 119.2
C5 C4 C3 121.01(19)
C5 C4 H4A 119.5
C3 C4 H4A 119.5
C4 C5 C6 118.76(18)
C4 C5 H5A 120.6
C6 C5 H5A 120.6
C5 C6 C1 119.09(17)
C5 C6 C7 132.60(17)
C1 C6 C7 108.28(16)
C8 C7 C6 106.92(16)
C8 C7 C9 132.51(17)
C6 C7 C9 120.57(16)
C7 C8 N1 109.94(16)
C7 C8 H8A 125.0
N1 C8 H8A 125.0
C10 C9 C7 129.05(17)
C10 C9 H9A 115.5
C7 C9 H9A 115.5
C9 C10 C15 122.94(16)
C9 C10 C11 123.91(16)
C15 C10 C11 112.98(15)
C10 C11 C22 113.33(14)
C10 C11 C23 109.89(15)
C22 C11 C23 99.74(14)
C10 C11 C12 109.29(14)
C22 C11 C12 112.06(15)
C23 C11 C12 112.28(14)
C13 C12 C17 105.09(15)
C13 C12 C19 112.10(16)
C17 C12 C19 110.42(16)
C13 C12 C11 109.68(16)
C17 C12 C11 112.69(15)
C19 C12 C11 106.94(14)
C14 C13 C12 114.88(16)
C14 C13 H13A 108.5
C12 C13 H13A 108.5
C14 C13 H13B 108.5
C12 C13 H13B 108.5
H13A C13 H13B 107.5
C15 C14 C13 107.80(16)
C15 C14 H14A 110.1
C13 C14 H14A 110.1
C15 C14 H14B 110.1
C13 C14 H14B 110.1
H14A C14 H14B 108.5
C16 C15 C10 123.71(19)
C16 C15 C14 123.41(18)
C10 C15 C14 112.53(17)
C15 C16 H16A 120.0
C15 C16 H16B 120.0
H16A C16 H16B 120.0
C12 C17 H17A 109.5
C12 C17 H17B 109.5
H17A C17 H17B 109.5
C12 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C19 C18 H18A 109.5
C19 C18 H18B 109.5
H18A C18 H18B 109.5
C19 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C20 C19 C18 110.04(18)
C20 C19 C12 109.80(15)
C18 C19 C12 114.40(18)
C20 C19 H19 107.4
C18 C19 H19 107.4
C12 C19 H19 107.4
C21 C20 C19 111.82(16)
C21 C20 H20A 109.3
C19 C20 H20A 109.3
C21 C20 H20B 109.3
C19 C20 H20B 109.3
H20A C20 H20B 107.9
C22 C21 C20 114.93(16)
C22 C21 H21A 108.5
C20 C21 H21A 108.5
C22 C21 H21B 108.5
C20 C21 H21B 108.5
H21A C21 H21B 107.5
O1 C22 C21 109.79(15)
O1 C22 C11 104.46(14)
C21 C22 C11 117.26(15)
O1 C22 H22 108.3
C21 C22 H22 108.3
C11 C22 H22 108.3
C24 C23 C11 105.11(15)
C24 C23 H23A 110.7
C11 C23 H23A 110.7
C24 C23 H23B 110.7
C11 C23 H23B 110.7
H23A C23 H23B 108.8
O2 C24 O1 111.73(15)
O2 C24 C23 107.10(16)
O1 C24 C23 107.02(15)
O2 C24 H24 110.3
O1 C24 H24 110.3
C23 C24 H24 110.3
O2 C25 C26 107.52(19)
O2 C25 H25A 110.2
C26 C25 H25A 110.2
O2 C25 H25B 110.2
C26 C25 H25B 110.2
H25A C25 H25B 108.5
C25 C26 H26A 109.5
C25 C26 H26B 109.5
H26A C26 H26B 109.5
C25 C26 H26C 109.5
H26A C26 H26C 109.5
H26B C26 H26C 109.5
C32 C27 C28 121.36(18)
C32 C27 S1 119.19(16)
C28 C27 S1 119.45(14)
C29 C28 C27 118.75(18)
C29 C28 H28 120.6
C27 C28 H28 120.6
C30 C29 C28 120.4(2)
C30 C29 H29 119.8
C28 C29 H29 119.8
C29 C30 C31 120.3(2)
C29 C30 H30 119.8
C31 C30 H30 119.8
C30 C31 C32 120.2(2)
C30 C31 H31 119.9
C32 C31 H31 119.9
C27 C32 C31 118.9(2)
C27 C32 H32 120.5
C31 C32 H32 120.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O4 1.4264(14)
S1 O3 1.4281(14)
S1 N1 1.6566(16)
S1 C27 1.7652(19)
O1 C24 1.421(2)
O1 C22 1.442(2)
O2 C24 1.413(2)
O2 C25 1.434(2)
N1 C8 1.415(2)
N1 C1 1.415(2)
C1 C2 1.389(3)
C1 C6 1.400(2)
C2 C3 1.384(3)
C2 H2A 0.9500
C3 C4 1.398(3)
C3 H3A 0.9500
C4 C5 1.378(3)
C4 H4A 0.9500
C5 C6 1.399(3)
C5 H5A 0.9500
C6 C7 1.454(3)
C7 C8 1.355(3)
C7 C9 1.469(2)
C8 H8A 0.9500
C9 C10 1.339(3)
C9 H9A 0.9500
C10 C15 1.482(2)
C10 C11 1.539(2)
C11 C22 1.543(2)
C11 C23 1.556(3)
C11 C12 1.586(2)
C12 C13 1.540(3)
C12 C17 1.541(2)
C12 C19 1.556(3)
C13 C14 1.528(3)
C13 H13A 0.9900
C13 H13B 0.9900
C14 C15 1.502(3)
C14 H14A 0.9900
C14 H14B 0.9900
C15 C16 1.321(3)
C16 H16A 0.9500
C16 H16B 0.9500
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
C18 C19 1.536(3)
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
C19 C20 1.530(3)
C19 H19 1.0000
C20 C21 1.526(3)
C20 H20A 0.9900
C20 H20B 0.9900
C21 C22 1.522(3)
C21 H21A 0.9900
C21 H21B 0.9900
C22 H22 1.0000
C23 C24 1.534(3)
C23 H23A 0.9900
C23 H23B 0.9900
C24 H24 1.0000
C25 C26 1.508(3)
C25 H25A 0.9900
C25 H25B 0.9900
C26 H26A 0.9800
C26 H26B 0.9800
C26 H26C 0.9800
C27 C32 1.384(3)
C27 C28 1.391(3)
C28 C29 1.387(3)
C28 H28 0.9500
C29 C30 1.378(3)
C29 H29 0.9500
C30 C31 1.385(4)
C30 H30 0.9500
C31 C32 1.386(3)
C31 H31 0.9500
C32 H32 0.9500
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139121119
