##############################################################################
# #
# This CIF contains the data in a paper accepted for publication in #
# Acta Crystallographica Section E. It conforms to the requirements of #
# Notes for Authors for Acta Crystallographica Section E, and has been #
# peer reviewed under the auspices of the IUCr Commission on Journals. #
# #
# Full details of the Crystallographic Information File format #
# are given in the paper "The Crystallographic Information File (CIF): #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H. #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. #
# #
# The current version of the core CIF dictionary is obtainable from #
# ftp://ftp.iucr.org/pub/cif_core.dic. #
# #
# Software is freely available for graphical display of the structure(s) #
# in this CIF. For information consult the CIF software page #
# http://www.iucr.org/resources/cif/software. #
# #
# This file may be used for bona fide research purposes within the #
# scientific community so long as proper attribution is given to the journal #
# article from which it was obtained. #
# #
##############################################################################
data_I
_audit_creation_method 'SHELXL'
_chemical_name_systematic
;
(E)-(1S,5S,6R,9S,20R)-6-[(2S)-
butan-2-yl]-5-hydroxy-20-[2-(methylsulfanyl)ethyl]-2-oxa-11,12-dithia-
7,19,22-triazabicyclo[7.7.6]docosa-15-ene-3,8,18,21-tetraone
;
_chemical_name_common 'Thailandepsin A'
_chemical_formula_moiety 'C23 H37 N3 O6 S3'
_chemical_formula_sum 'C23 H37 N3 O6 S3'
_chemical_formula_iupac 'C23 H37 N3 O6 S3'
_chemical_formula_weight 547.74
_chemical_melting_point ?
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_H-M 'P 21 21 21'
_symmetry_space_group_name_Hall 'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
_cell_length_a 12.7747(3)
_cell_length_b 13.2926(3)
_cell_length_c 15.4218(4)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 2618.76(11)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 9793
_cell_measurement_theta_min 3.4598
_cell_measurement_theta_max 71.2185
_cell_measurement_temperature 100.0(10)
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.45
_exptl_crystal_size_mid 0.42
_exptl_crystal_size_min 0.38
_exptl_crystal_density_diffrn 1.389
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1168
_exptl_absorpt_coefficient_mu 2.955
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2007)
;
_exptl_absorpt_correction_T_min 0.3518
_exptl_absorpt_correction_T_max 0.4029
_exptl_special_details ?
_diffrn_ambient_temperature 100.0(10)
_diffrn_radiation_type 'Cu K\a'
_diffrn_radiation_wavelength 1.54178
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker SMART APEXII area-detector'
_diffrn_measurement_method '0.50\% \w and 0.5 \% \f'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 34598
_diffrn_reflns_av_R_equivalents 0.0245
_diffrn_reflns_av_sigmaI/netI 0.0127
_diffrn_reflns_theta_min 4.39
_diffrn_reflns_theta_max 71.71
_diffrn_reflns_theta_full 67.00
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min -15
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_limit_l_max 17
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^2^, conventional
R-factors R are based on F, with F set to zero for
negative F^2^. The threshold expression of F^2^ >
\s(F^2^) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^2^ are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total 4990
_reflns_number_gt 4981
_reflns_threshold_expression I>2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0269
_refine_ls_R_factor_gt 0.0269
_refine_ls_wR_factor_gt 0.0711
_refine_ls_wR_factor_ref 0.0711
_refine_ls_goodness_of_fit_ref 1.045
_refine_ls_restrained_S_all 1.044
_refine_ls_number_reflns 4990
_refine_ls_number_parameters 326
_refine_ls_number_restraints 4
_refine_ls_hydrogen_treatment mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0510P)^2^+0.7593P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.346
_refine_diff_density_min -0.363
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details 'Flack (1983), ???? Friedel pairs'
_refine_ls_abs_structure_Flack 0.000(9)
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'
_computing_data_collection 'APEX2 (Bruker, 2007)'
_computing_cell_refinement 'SAINT (Bruker, 2007)'
_computing_data_reduction 'SAINT (Bruker, 2007)'
_computing_structure_solution 'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, 2008) and OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material 'SHELXTL'
loop_
_atom_site_type_symbol
_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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 1.10290(3) -0.14637(3) 0.38774(2) 0.02184(10) Uani d . 1 1 . .
S S2 0.97356(3) -0.08216(3) 0.33328(2) 0.01709(9) Uani d . 1 1 . .
S S3 0.91337(3) 0.40012(3) 0.40152(3) 0.02362(10) Uani d . 1 1 . .
O O1 1.08885(10) -0.18335(9) 0.67591(8) 0.0223(3) Uani d . 1 1 . .
O O2 0.77376(8) -0.09984(8) 0.61157(7) 0.0141(2) Uani d . 1 1 . .
O O3 0.69383(9) -0.08629(9) 0.74184(7) 0.0190(2) Uani d . 1 1 . .
O O4 0.85790(9) -0.16775(8) 0.88174(7) 0.0140(2) Uani d D 1 1 . .
H H4 0.8699(17) -0.2254(7) 0.9016(13) 0.021 Uiso d D 1 1 . .
O O5 1.11125(9) 0.14154(8) 0.55597(7) 0.0179(2) Uani d . 1 1 . .
O O6 0.86120(9) 0.12479(8) 0.64747(7) 0.0158(2) Uani d . 1 1 . .
N N1 0.99720(10) -0.04020(10) 0.70173(8) 0.0128(3) Uani d D 1 1 . .
H H1 0.9652(14) 0.0126(9) 0.6798(12) 0.015 Uiso d D 1 1 . .
N N2 1.00458(10) 0.00984(9) 0.52676(8) 0.0121(2) Uani d D 1 1 . .
H H2 0.9444(8) -0.0082(14) 0.5038(12) 0.014 Uiso d D 1 1 . .
N N3 0.83857(10) 0.13784(10) 0.50282(8) 0.0138(3) Uani d D 1 1 . .
H H3 0.7955(12) 0.1335(15) 0.4584(8) 0.017 Uiso d D 1 1 . .
C C1 1.05386(12) -0.10227(12) 0.65205(10) 0.0143(3) Uani d . 1 1 . .
C C2 1.07489(12) -0.06840(11) 0.55727(9) 0.0131(3) Uani d . 1 1 . .
H H2A 1.1482 -0.0423 0.5537 0.016 Uiso calc R 1 1 . .
C C3 1.06714(13) -0.16258(12) 0.50086(10) 0.0174(3) Uani d . 1 1 . .
H H3A 0.9943 -0.1877 0.5034 0.021 Uiso calc R 1 1 . .
H H3B 1.1128 -0.2151 0.5262 0.021 Uiso calc R 1 1 . .
C C4 0.88346(14) -0.18723(13) 0.31638(11) 0.0202(3) Uani d . 1 1 . .
H H4A 0.8850 -0.2082 0.2548 0.024 Uiso calc R 1 1 . .
H H4B 0.9052 -0.2453 0.3524 0.024 Uiso calc R 1 1 . .
C C5 0.77251(12) -0.15466(13) 0.34132(11) 0.0190(3) Uani d . 1 1 . .
H H5A 0.7542 -0.0927 0.3091 0.023 Uiso calc R 1 1 . .
H H5B 0.7225 -0.2079 0.3240 0.023 Uiso calc R 1 1 . .
C C6 0.76184(12) -0.13526(13) 0.43705(10) 0.0173(3) Uani d . 1 1 . .
H H6 0.7980 -0.1793 0.4752 0.021 Uiso calc R 1 1 . .
C C7 0.70632(12) -0.06202(12) 0.47258(10) 0.0162(3) Uani d . 1 1 . .
H H7 0.6720 -0.0170 0.4341 0.019 Uiso calc R 1 1 . .
C C8 0.69224(12) -0.04303(12) 0.56827(10) 0.0154(3) Uani d . 1 1 . .
H H8 0.6227 -0.0704 0.5865 0.018 Uiso calc R 1 1 . .
C C9 0.76158(12) -0.12126(11) 0.69723(10) 0.0136(3) Uani d . 1 1 . .
C C10 0.84280(12) -0.19799(11) 0.72498(10) 0.0138(3) Uani d . 1 1 . .
H H10A 0.8877 -0.2133 0.6743 0.017 Uiso calc R 1 1 . .
H H10B 0.8059 -0.2608 0.7409 0.017 Uiso calc R 1 1 . .
C C11 0.91409(12) -0.16801(11) 0.80094(9) 0.0127(3) Uani d . 1 1 . .
H H11 0.9724 -0.2180 0.8051 0.015 Uiso calc R 1 1 . .
C C12 0.96190(12) -0.06200(11) 0.79096(9) 0.0125(3) Uani d . 1 1 . .
H H12 0.9029 -0.0143 0.8019 0.015 Uiso calc R 1 1 . .
C C13 1.04416(12) -0.03790(11) 0.86101(10) 0.0146(3) Uani d . 1 1 . .
H H13 1.0124 -0.0559 0.9182 0.017 Uiso calc R 1 1 . .
C C14 1.06664(13) 0.07539(12) 0.86315(10) 0.0184(3) Uani d . 1 1 . .
H H14A 1.1138 0.0927 0.8144 0.022 Uiso calc R 1 1 . .
H H14B 1.0002 0.1125 0.8548 0.022 Uiso calc R 1 1 . .
C C15 1.11702(14) 0.10927(13) 0.94810(11) 0.0222(3) Uani d . 1 1 . .
H H15A 1.0677 0.0988 0.9960 0.033 Uiso calc R 1 1 . .
H H15B 1.1350 0.1808 0.9443 0.033 Uiso calc R 1 1 . .
H H15C 1.1807 0.0700 0.9585 0.033 Uiso calc R 1 1 . .
C C16 1.14602(12) -0.09806(13) 0.85283(10) 0.0184(3) Uani d . 1 1 . .
H H16A 1.1848 -0.0752 0.8017 0.028 Uiso calc R 1 1 . .
H H16B 1.1296 -0.1697 0.8467 0.028 Uiso calc R 1 1 . .
H H16C 1.1888 -0.0878 0.9048 0.028 Uiso calc R 1 1 . .
C C17 1.02739(12) 0.10824(11) 0.52881(9) 0.0134(3) Uani d . 1 1 . .
C C18 0.94399(12) 0.17890(11) 0.49209(10) 0.0138(3) Uani d . 1 1 . .
H H18 0.9480 0.2442 0.5241 0.017 Uiso calc R 1 1 . .
C C19 0.80478(12) 0.11430(11) 0.58346(10) 0.0141(3) Uani d . 1 1 . .
C C20 0.69604(12) 0.06994(12) 0.59060(10) 0.0160(3) Uani d . 1 1 . .
H H20A 0.6486 0.1068 0.5510 0.019 Uiso calc R 1 1 . .
H H20B 0.6701 0.0797 0.6505 0.019 Uiso calc R 1 1 . .
C C21 0.96752(13) 0.19916(11) 0.39575(10) 0.0158(3) Uani d . 1 1 . .
H H21A 1.0409 0.2224 0.3904 0.019 Uiso calc R 1 1 . .
H H21B 0.9613 0.1351 0.3634 0.019 Uiso calc R 1 1 . .
C C22 0.89580(13) 0.27705(12) 0.35353(10) 0.0168(3) Uani d . 1 1 . .
H H22A 0.8220 0.2558 0.3605 0.020 Uiso calc R 1 1 . .
H H22B 0.9112 0.2807 0.2907 0.020 Uiso calc R 1 1 . .
C C23 0.82077(15) 0.46899(14) 0.33643(12) 0.0250(4) Uani d . 1 1 . .
H H23A 0.8190 0.5393 0.3554 0.037 Uiso calc R 1 1 . .
H H23B 0.7510 0.4392 0.3431 0.037 Uiso calc R 1 1 . .
H H23C 0.8419 0.4659 0.2754 0.037 Uiso calc R 1 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.01829(19) 0.0340(2) 0.01321(18) 0.00771(17) -0.00022(14) -0.00696(15)
S2 0.01714(18) 0.02111(19) 0.01302(16) 0.00009(15) -0.00063(14) -0.00078(14)
S3 0.0279(2) 0.0207(2) 0.0222(2) 0.00109(16) -0.00648(16) 0.00032(16)
O1 0.0286(6) 0.0210(6) 0.0172(6) 0.0118(5) 0.0048(5) 0.0045(5)
O2 0.0140(5) 0.0171(5) 0.0112(5) 0.0017(4) 0.0001(4) 0.0034(4)
O3 0.0199(5) 0.0216(6) 0.0156(5) 0.0040(5) 0.0037(4) 0.0017(5)
O4 0.0190(5) 0.0131(5) 0.0098(5) 0.0019(4) 0.0019(4) 0.0018(4)
O5 0.0167(5) 0.0166(5) 0.0205(5) -0.0020(4) -0.0032(5) -0.0018(5)
O6 0.0197(5) 0.0159(5) 0.0119(5) 0.0022(4) 0.0004(4) -0.0001(4)
N1 0.0161(6) 0.0129(6) 0.0093(6) 0.0026(5) -0.0002(5) 0.0029(5)
N2 0.0122(6) 0.0137(6) 0.0103(6) -0.0004(5) -0.0003(4) -0.0003(5)
N3 0.0139(6) 0.0155(6) 0.0121(6) 0.0005(5) -0.0008(5) 0.0010(5)
C1 0.0145(7) 0.0156(7) 0.0129(7) 0.0005(6) 0.0002(5) 0.0013(6)
C2 0.0146(7) 0.0142(7) 0.0104(6) 0.0017(6) 0.0001(5) -0.0004(6)
C3 0.0227(7) 0.0153(7) 0.0142(7) 0.0037(6) -0.0015(6) -0.0014(6)
C4 0.0243(8) 0.0191(7) 0.0170(8) -0.0014(7) -0.0020(7) -0.0043(6)
C5 0.0184(8) 0.0213(8) 0.0172(8) -0.0030(6) -0.0031(6) -0.0015(6)
C6 0.0167(7) 0.0196(7) 0.0156(7) -0.0045(6) -0.0035(6) 0.0037(6)
C7 0.0150(7) 0.0194(7) 0.0143(7) -0.0019(6) -0.0042(6) 0.0040(6)
C8 0.0126(7) 0.0182(7) 0.0154(7) 0.0001(6) -0.0011(6) 0.0038(6)
C9 0.0165(7) 0.0135(7) 0.0107(6) -0.0032(6) -0.0007(6) 0.0002(5)
C10 0.0183(7) 0.0118(7) 0.0111(7) 0.0006(6) -0.0002(6) -0.0001(5)
C11 0.0157(7) 0.0136(7) 0.0087(6) 0.0015(6) 0.0001(6) 0.0010(5)
C12 0.0152(7) 0.0133(6) 0.0089(6) 0.0014(6) 0.0010(6) 0.0009(5)
C13 0.0176(7) 0.0156(7) 0.0106(7) 0.0009(6) -0.0008(6) 0.0000(5)
C14 0.0249(8) 0.0155(7) 0.0148(7) -0.0014(6) -0.0034(6) 0.0017(6)
C15 0.0287(9) 0.0189(8) 0.0190(8) -0.0025(7) -0.0021(7) -0.0013(6)
C16 0.0161(7) 0.0208(8) 0.0182(8) 0.0011(6) -0.0020(6) 0.0011(6)
C17 0.0164(7) 0.0158(7) 0.0079(6) -0.0003(6) 0.0022(6) -0.0004(5)
C18 0.0153(7) 0.0133(7) 0.0127(7) -0.0014(6) 0.0000(6) 0.0000(6)
C19 0.0160(7) 0.0119(7) 0.0144(7) 0.0037(6) 0.0017(6) 0.0005(6)
C20 0.0154(7) 0.0184(7) 0.0142(7) 0.0036(6) 0.0020(6) 0.0026(6)
C21 0.0192(7) 0.0154(7) 0.0128(7) -0.0013(6) 0.0012(6) 0.0013(6)
C22 0.0210(8) 0.0171(7) 0.0122(7) -0.0029(6) -0.0026(6) 0.0015(5)
C23 0.0259(8) 0.0281(9) 0.0209(8) 0.0081(7) 0.0006(7) 0.0028(7)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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 C3 . 1.8162(17) ?
S1 S2 . 2.0406(6) ?
S2 C4 . 1.8285(17) ?
S3 C23 . 1.8014(18) ?
S3 C22 . 1.8095(16) ?
O1 C1 . 1.223(2) ?
O2 C9 . 1.3602(18) ?
O2 C8 . 1.4494(18) ?
O3 C9 . 1.199(2) ?
O4 C11 . 1.4380(17) ?
O4 H4 . 0.8399(10) ?
O5 C17 . 1.233(2) ?
O6 C19 . 1.230(2) ?
N1 C1 . 1.338(2) ?
N1 C12 . 1.4769(18) ?
N1 H1 . 0.8797(10) ?
N2 C17 . 1.340(2) ?
N2 C2 . 1.4524(19) ?
N2 H2 . 0.8798(10) ?
N3 C19 . 1.353(2) ?
N3 C18 . 1.4624(18) ?
N3 H3 . 0.8799(10) ?
C1 C2 . 1.553(2) ?
C2 C3 . 1.528(2) ?
C2 H2A . 1.0000 ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 C5 . 1.531(2) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 C6 . 1.505(2) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 C7 . 1.323(2) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.508(2) ?
C7 H7 . 0.9500 ?
C8 C20 . 1.541(2) ?
C8 H8 . 1.0000 ?
C9 C10 . 1.517(2) ?
C10 C11 . 1.536(2) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.543(2) ?
C11 H11 . 1.0000 ?
C12 C13 . 1.541(2) ?
C12 H12 . 1.0000 ?
C13 C16 . 1.533(2) ?
C13 C14 . 1.533(2) ?
C13 H13 . 1.0000 ?
C14 C15 . 1.528(2) ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
C17 C18 . 1.529(2) ?
C18 C21 . 1.540(2) ?
C18 H18 . 1.0000 ?
C19 C20 . 1.513(2) ?
C20 H20A . 0.9900 ?
C20 H20B . 0.9900 ?
C21 C22 . 1.528(2) ?
C21 H21A . 0.9900 ?
C21 H21B . 0.9900 ?
C22 H22A . 0.9900 ?
C22 H22B . 0.9900 ?
C23 H23A . 0.9800 ?
C23 H23B . 0.9800 ?
C23 H23C . 0.9800 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 S1 S2 . . 103.96(6) ?
C4 S2 S1 . . 104.41(6) ?
C23 S3 C22 . . 98.63(8) ?
C9 O2 C8 . . 118.31(12) ?
C11 O4 H4 . . 102.9(15) ?
C1 N1 C12 . . 125.27(13) ?
C1 N1 H1 . . 121.5(13) ?
C12 N1 H1 . . 111.9(13) ?
C17 N2 C2 . . 123.82(13) ?
C17 N2 H2 . . 117.7(13) ?
C2 N2 H2 . . 118.4(13) ?
C19 N3 C18 . . 118.95(13) ?
C19 N3 H3 . . 120.1(13) ?
C18 N3 H3 . . 120.8(13) ?
O1 C1 N1 . . 124.65(14) ?
O1 C1 C2 . . 118.38(14) ?
N1 C1 C2 . . 116.97(13) ?
N2 C2 C3 . . 111.24(12) ?
N2 C2 C1 . . 113.92(12) ?
C3 C2 C1 . . 106.69(12) ?
N2 C2 H2A . . 108.3 ?
C3 C2 H2A . . 108.3 ?
C1 C2 H2A . . 108.3 ?
C2 C3 S1 . . 115.69(11) ?
C2 C3 H3A . . 108.4 ?
S1 C3 H3A . . 108.4 ?
C2 C3 H3B . . 108.4 ?
S1 C3 H3B . . 108.4 ?
H3A C3 H3B . . 107.4 ?
C5 C4 S2 . . 109.33(11) ?
C5 C4 H4A . . 109.8 ?
S2 C4 H4A . . 109.8 ?
C5 C4 H4B . . 109.8 ?
S2 C4 H4B . . 109.8 ?
H4A C4 H4B . . 108.3 ?
C6 C5 C4 . . 112.26(13) ?
C6 C5 H5A . . 109.2 ?
C4 C5 H5A . . 109.2 ?
C6 C5 H5B . . 109.2 ?
C4 C5 H5B . . 109.2 ?
H5A C5 H5B . . 107.9 ?
C7 C6 C5 . . 125.51(15) ?
C7 C6 H6 . . 117.2 ?
C5 C6 H6 . . 117.2 ?
C6 C7 C8 . . 126.32(14) ?
C6 C7 H7 . . 116.8 ?
C8 C7 H7 . . 116.8 ?
O2 C8 C7 . . 106.14(12) ?
O2 C8 C20 . . 112.45(12) ?
C7 C8 C20 . . 112.21(13) ?
O2 C8 H8 . . 108.6 ?
C7 C8 H8 . . 108.6 ?
C20 C8 H8 . . 108.6 ?
O3 C9 O2 . . 123.95(14) ?
O3 C9 C10 . . 126.34(14) ?
O2 C9 C10 . . 109.66(12) ?
C9 C10 C11 . . 116.50(12) ?
C9 C10 H10A . . 108.2 ?
C11 C10 H10A . . 108.2 ?
C9 C10 H10B . . 108.2 ?
C11 C10 H10B . . 108.2 ?
H10A C10 H10B . . 107.3 ?
O4 C11 C10 . . 111.44(12) ?
O4 C11 C12 . . 106.37(11) ?
C10 C11 C12 . . 113.29(12) ?
O4 C11 H11 . . 108.5 ?
C10 C11 H11 . . 108.5 ?
C12 C11 H11 . . 108.5 ?
N1 C12 C13 . . 113.84(12) ?
N1 C12 C11 . . 113.14(12) ?
C13 C12 C11 . . 112.95(12) ?
N1 C12 H12 . . 105.3 ?
C13 C12 H12 . . 105.3 ?
C11 C12 H12 . . 105.3 ?
C16 C13 C14 . . 110.81(13) ?
C16 C13 C12 . . 114.39(13) ?
C14 C13 C12 . . 110.31(12) ?
C16 C13 H13 . . 107.0 ?
C14 C13 H13 . . 107.0 ?
C12 C13 H13 . . 107.0 ?
C15 C14 C13 . . 112.76(13) ?
C15 C14 H14A . . 109.0 ?
C13 C14 H14A . . 109.0 ?
C15 C14 H14B . . 109.0 ?
C13 C14 H14B . . 109.0 ?
H14A C14 H14B . . 107.8 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C13 C16 H16A . . 109.5 ?
C13 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C13 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
O5 C17 N2 . . 123.19(14) ?
O5 C17 C18 . . 120.72(13) ?
N2 C17 C18 . . 116.05(13) ?
N3 C18 C17 . . 111.75(12) ?
N3 C18 C21 . . 110.75(12) ?
C17 C18 C21 . . 109.20(12) ?
N3 C18 H18 . . 108.4 ?
C17 C18 H18 . . 108.4 ?
C21 C18 H18 . . 108.4 ?
O6 C19 N3 . . 121.62(14) ?
O6 C19 C20 . . 121.58(14) ?
N3 C19 C20 . . 116.73(14) ?
C19 C20 C8 . . 113.10(13) ?
C19 C20 H20A . . 109.0 ?
C8 C20 H20A . . 109.0 ?
C19 C20 H20B . . 109.0 ?
C8 C20 H20B . . 109.0 ?
H20A C20 H20B . . 107.8 ?
C22 C21 C18 . . 114.37(13) ?
C22 C21 H21A . . 108.7 ?
C18 C21 H21A . . 108.7 ?
C22 C21 H21B . . 108.7 ?
C18 C21 H21B . . 108.7 ?
H21A C21 H21B . . 107.6 ?
C21 C22 S3 . . 111.34(11) ?
C21 C22 H22A . . 109.4 ?
S3 C22 H22A . . 109.4 ?
C21 C22 H22B . . 109.4 ?
S3 C22 H22B . . 109.4 ?
H22A C22 H22B . . 108.0 ?
S3 C23 H23A . . 109.5 ?
S3 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
S3 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 S1 S2 C4 . . . . -79.45(8) ?
C12 N1 C1 O1 . . . . -4.2(2) ?
C12 N1 C1 C2 . . . . 175.04(13) ?
C17 N2 C2 C3 . . . . -143.88(14) ?
C17 N2 C2 C1 . . . . 95.49(16) ?
O1 C1 C2 N2 . . . . 161.20(14) ?
N1 C1 C2 N2 . . . . -18.11(19) ?
O1 C1 C2 C3 . . . . 38.06(19) ?
N1 C1 C2 C3 . . . . -141.25(14) ?
N2 C2 C3 S1 . . . . 61.75(15) ?
C1 C2 C3 S1 . . . . -173.45(10) ?
S2 S1 C3 C2 . . . . -79.42(12) ?
S1 S2 C4 C5 . . . . 138.27(10) ?
S2 C4 C5 C6 . . . . -67.15(16) ?
C4 C5 C6 C7 . . . . 141.33(16) ?
C5 C6 C7 C8 . . . . 178.20(15) ?
C9 O2 C8 C7 . . . . -160.50(12) ?
C9 O2 C8 C20 . . . . 76.45(16) ?
C6 C7 C8 O2 . . . . 16.4(2) ?
C6 C7 C8 C20 . . . . 139.65(16) ?
C8 O2 C9 O3 . . . . -9.1(2) ?
C8 O2 C9 C10 . . . . 168.50(12) ?
O3 C9 C10 C11 . . . . -58.7(2) ?
O2 C9 C10 C11 . . . . 123.75(13) ?
C9 C10 C11 O4 . . . . 71.69(16) ?
C9 C10 C11 C12 . . . . -48.21(17) ?
C1 N1 C12 C13 . . . . 84.41(18) ?
C1 N1 C12 C11 . . . . -46.31(19) ?
O4 C11 C12 N1 . . . . -164.12(12) ?
C10 C11 C12 N1 . . . . -41.37(17) ?
O4 C11 C12 C13 . . . . 64.71(15) ?
C10 C11 C12 C13 . . . . -172.53(12) ?
N1 C12 C13 C16 . . . . -61.27(17) ?
C11 C12 C13 C16 . . . . 69.54(16) ?
N1 C12 C13 C14 . . . . 64.44(16) ?
C11 C12 C13 C14 . . . . -164.75(12) ?
C16 C13 C14 C15 . . . . -71.70(17) ?
C12 C13 C14 C15 . . . . 160.60(13) ?
C2 N2 C17 O5 . . . . 0.9(2) ?
C2 N2 C17 C18 . . . . 178.86(12) ?
C19 N3 C18 C17 . . . . 57.26(17) ?
C19 N3 C18 C21 . . . . 179.24(13) ?
O5 C17 C18 N3 . . . . -152.25(13) ?
N2 C17 C18 N3 . . . . 29.76(18) ?
O5 C17 C18 C21 . . . . 84.87(16) ?
N2 C17 C18 C21 . . . . -93.11(15) ?
C18 N3 C19 O6 . . . . -1.4(2) ?
C18 N3 C19 C20 . . . . -178.68(12) ?
O6 C19 C20 C8 . . . . -97.53(17) ?
N3 C19 C20 C8 . . . . 79.73(16) ?
O2 C8 C20 C19 . . . . 47.62(17) ?
C7 C8 C20 C19 . . . . -71.95(17) ?
N3 C18 C21 C22 . . . . 62.21(16) ?
C17 C18 C21 C22 . . . . -174.33(13) ?
C18 C21 C22 S3 . . . . 64.71(15) ?
C23 S3 C22 C21 . . . . 179.27(12) ?
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
O4 H4 O5 3_746 0.8399(10) 1.901(2) 2.7394(15) 176(2)
N1 H1 O6 . 0.8797(10) 2.059(5) 2.9203(17) 166.1(18)
N2 H2 S2 . 0.8798(10) 2.833(19) 3.2491(13) 110.7(15)
N3 H3 O4 2_654 0.8799(10) 2.334(9) 3.1534(16) 155.0(18)
data_global
_journal_date_recd_electronic 2011-10-02
_journal_date_accepted 2011-10-07
_journal_name_full 'Acta Crystallographica, Section E'
_journal_year 2011
_journal_volume 67
_journal_issue 11
_journal_page_first o2948
_journal_page_last o2949
_journal_paper_category QO
_journal_coeditor_code ZL2411
loop_
_publ_contact_author_name
_publ_contact_author_address
_publ_contact_author_email
'Dr Cheng Wang'
;
Department of Biological Sciences
University of Wisconsin - Milwaukee
3209 North Maryland Avenue
Milwaukee, WI 53211, USA
;
wang35@uwm.edu
'Dr Yi-Qiang Cheng'
;Department of Biological Sciences
University of Wisconsin - Milwaukee
3209 North Maryland Avenue
Milwaukee, WI 53211, USA
;
ycheng@uwm.edu
_publ_contact_author_fax '414-229-3926'
_publ_contact_author_phone '414-229-4739'
_publ_section_title
;
A new depsipeptide, thailandepsin A
;
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
'Wang, Cheng' ?
;
Department of Biological Sciences
Department of Chemistry and Biochemistry
Univeristy of Wisconsin--Milwaukee
PO Box 413
Milwaukee, WI 53201
USA
;
'Cheng, Yi-Qiang' ?
;
Department of Biological Sciences
Department of Chemistry and Biochemistry
Univeristy of Wisconsin--Milwaukee
PO Box 413
Milwaukee, WI 53201
USA
;