Acta Crystallographica Section E
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CRYSTALLOGRAPHIC COMMUNICATIONS
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CRYSTALLOGRAPHIC
COMMUNICATIONS
Volume 69
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Part 4
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April 2013
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Page 584
https://doi.org/10.1107/S1600536813007460
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ISSN: 2056-9890
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CRYSTALLOGRAPHIC
COMMUNICATIONS
Volume 69
|
Part 4
|
April 2013
|
Page 584
https://doi.org/10.1107/S1600536813007460
Open
access
ISSN: 2056-9890
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############################################################################## # # # 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-97 _chemical_name_systematic ;\ <i>N</i>-(2,6-Dimethoxypyridin-3-yl)-9-methyl-9<i>H</i>-\ carbazole-3-sulfonamide ; _chemical_name_common ? _chemical_formula_moiety 'C20 H19 N3 O4 S' _chemical_formula_sum 'C20 H19 N3 O4 S' _chemical_formula_iupac 'C20 H19 N3 O4 S' _chemical_formula_weight 397.45 _chemical_melting_point_gt 443 _chemical_melting_point_lt 445 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.5078(2) _cell_length_b 7.92720(10) _cell_length_c 20.9276(3) _cell_angle_alpha 90.00 _cell_angle_beta 124.0270(10) _cell_angle_gamma 90.00 _cell_volume 1857.20(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 7976 _cell_measurement_theta_min 3.29 _cell_measurement_theta_max 66.73 _cell_measurement_temperature 120(2) _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.32 _exptl_crystal_density_diffrn 1.421 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 1.834 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(<i>CrysAlis PRO</i>; Agilent, 2011)' _exptl_absorpt_correction_T_min 0.475 _exptl_absorpt_correction_T_max 0.556 _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1 K. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator 'mirror' _diffrn_measurement_device_type 'Agilent Xcalibur (Atlas, Gemini ultra)' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.4713 _diffrn_reflns_number 11460 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0189 _diffrn_reflns_theta_min 3.95 _diffrn_reflns_theta_max 66.84 _diffrn_reflns_theta_full 66.84 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measured_fraction_theta_full 0.993 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_standards_number ? _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _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^ > 2sigma(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 3280 _reflns_number_gt 3161 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0350 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_gt 0.0876 _refine_ls_wR_factor_ref 0.0884 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _refine_ls_number_reflns 3280 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0468P)^2^+1.1436P] 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 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.449 _refine_diff_density_min -0.524 _refine_ls_extinction_method '<i>SHELXL97</i> (Sheldrick, 2008)' _refine_ls_extinction_coef 0.0078(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' 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 '<i>CrysAlis PRO</i> (Agilent, 2011)' _computing_cell_refinement '<i>CrysAlis PRO</i> (Agilent, 2011)' _computing_data_reduction '<i>CrysAlis PRO</i> (Agilent, 2011)' _computing_structure_solution '<i>SHELXS97</i> (Sheldrick, 2008)' _computing_structure_refinement '<i>SHELXL97</i> (Sheldrick, 2008)' _computing_molecular_graphics '<i>SHELXTL</i> (Sheldrick, 2008)' _computing_publication_material ; <i>SHELXTL</i> (Sheldrick, 2008), <i>PLATON</i> (Spek, 2009) and <i>publCIF</i> (Westrip, 2010) ; 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 0.69096(3) 0.28850(4) 0.403260(19) 0.01331(14) Uani d . 1 1 . . O O1 0.62355(9) 0.15207(14) 0.35261(6) 0.0178(3) Uani d . 1 1 . . O O2 0.68743(10) 0.45199(14) 0.37286(6) 0.0195(3) Uani d . 1 1 . . O O3 0.95214(10) -0.42247(14) 0.55767(6) 0.0209(3) Uani d . 1 1 . . O O4 0.93551(10) 0.14336(14) 0.60496(6) 0.0208(3) Uani d . 1 1 . . N N1 0.83268(12) 0.22943(17) 0.45142(8) 0.0152(3) Uani d . 1 1 . . H H1 0.8755(17) 0.301(3) 0.4817(11) 0.019(5) Uiso d . 1 1 . . N N2 0.94314(11) -0.14034(16) 0.58206(7) 0.0166(3) Uani d . 1 1 . . N N3 0.59643(11) 0.36785(16) 0.64261(7) 0.0167(3) Uani d . 1 1 . . C C1 0.65608(13) 0.30951(19) 0.47199(8) 0.0137(3) Uani d . 1 1 . . C C2 0.61415(13) 0.16778(19) 0.48958(9) 0.0161(3) Uani d . 1 1 . . H H2 0.6013 0.0675 0.4629 0.019 Uiso calc R 1 1 . . C C3 0.59167(13) 0.1756(2) 0.54624(9) 0.0169(3) Uani d . 1 1 . . H H3 0.5632 0.0822 0.5581 0.020 Uiso calc R 1 1 . . C C4 0.61299(13) 0.32797(19) 0.58516(8) 0.0148(3) Uani d . 1 1 . . C C5 0.65942(13) 0.46985(18) 0.56913(8) 0.0141(3) Uani d . 1 1 . . C C6 0.67969(13) 0.46111(19) 0.51119(8) 0.0143(3) Uani d . 1 1 . . H H6 0.7082 0.5539 0.4990 0.017 Uiso calc R 1 1 . . C C7 0.67359(13) 0.6016(2) 0.62161(8) 0.0158(3) Uani d . 1 1 . . C C8 0.63249(13) 0.5339(2) 0.66488(8) 0.0163(3) Uani d . 1 1 . . C C9 0.63143(14) 0.6286(2) 0.72079(9) 0.0203(3) Uani d . 1 1 . . H H9 0.6032 0.5837 0.7488 0.024 Uiso calc R 1 1 . . C C10 0.67411(15) 0.7918(2) 0.73269(9) 0.0224(4) Uani d . 1 1 . . H H10 0.6743 0.8583 0.7694 0.027 Uiso calc R 1 1 . . C C11 0.71695(15) 0.8595(2) 0.69094(9) 0.0219(4) Uani d . 1 1 . . H H11 0.7462 0.9693 0.7009 0.026 Uiso calc R 1 1 . . C C12 0.71658(14) 0.7660(2) 0.63491(9) 0.0188(3) Uani d . 1 1 . . H H12 0.7444 0.8121 0.6069 0.023 Uiso calc R 1 1 . . C C13 0.91249(13) 0.01614(19) 0.55524(9) 0.0150(3) Uani d . 1 1 . . C C14 0.86006(13) 0.05938(19) 0.47790(8) 0.0141(3) Uani d . 1 1 . . C C15 0.83742(13) -0.0704(2) 0.42735(9) 0.0160(3) Uani d . 1 1 . . H H15 0.8028 -0.0469 0.3754 0.019 Uiso calc R 1 1 . . C C16 0.86582(13) -0.2349(2) 0.45332(9) 0.0173(3) Uani d . 1 1 . . H H16 0.8493 -0.3239 0.4198 0.021 Uiso calc R 1 1 . . C C17 0.92017(13) -0.26123(19) 0.53180(9) 0.0163(3) Uani d . 1 1 . . C C18 0.54002(16) 0.2605(2) 0.66988(10) 0.0239(4) Uani d . 1 1 . . H H18A 0.5740 0.2834 0.7234 0.036 Uiso calc PR 0.61(2) 1 . . H H18B 0.5530 0.1443 0.6637 0.036 Uiso calc PR 0.61(2) 1 . . H H18C 0.4558 0.2831 0.6405 0.036 Uiso calc PR 0.61(2) 1 . . H H18D 0.4812 0.1905 0.6284 0.036 Uiso calc PR 0.39(2) 1 . . H H18E 0.5022 0.3296 0.6880 0.036 Uiso calc PR 0.39(2) 1 . . H H18F 0.5994 0.1908 0.7112 0.036 Uiso calc PR 0.39(2) 1 . . C C19 0.99079(19) 0.0978(2) 0.68440(10) 0.0319(4) Uani d . 1 1 . . H H19A 0.9996 0.1965 0.7137 0.048 Uiso calc R 1 1 . . H H19B 1.0680 0.0497 0.7041 0.048 Uiso calc R 1 1 . . H H19C 0.9418 0.0167 0.6885 0.048 Uiso calc R 1 1 . . C C20 1.01784(18) -0.4455(2) 0.63937(10) 0.0326(4) Uani d . 1 1 . . H H20A 1.0864 -0.3728 0.6641 0.049 Uiso calc R 1 1 . . H H20B 1.0434 -0.5608 0.6518 0.049 Uiso calc R 1 1 . . H H20C 0.9678 -0.4185 0.6571 0.049 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 0.0165(2) 0.0117(2) 0.0116(2) 0.00097(13) 0.00782(16) 0.00084(13) O1 0.0184(5) 0.0184(6) 0.0143(5) 0.0000(4) 0.0077(4) -0.0026(4) O2 0.0266(6) 0.0147(6) 0.0192(6) 0.0027(4) 0.0141(5) 0.0049(4) O3 0.0268(6) 0.0119(5) 0.0196(6) 0.0000(4) 0.0103(5) 0.0013(4) O4 0.0320(6) 0.0150(6) 0.0142(5) -0.0026(5) 0.0123(5) -0.0031(4) N1 0.0163(7) 0.0117(7) 0.0168(7) -0.0023(5) 0.0088(6) -0.0022(5) N2 0.0185(6) 0.0149(7) 0.0160(6) -0.0023(5) 0.0094(5) -0.0001(5) N3 0.0223(7) 0.0151(7) 0.0159(6) -0.0003(5) 0.0128(6) 0.0003(5) C1 0.0148(7) 0.0133(7) 0.0118(7) 0.0011(6) 0.0067(6) 0.0000(6) C2 0.0188(7) 0.0107(7) 0.0180(7) -0.0013(6) 0.0098(6) -0.0025(6) C3 0.0207(8) 0.0121(7) 0.0193(8) -0.0025(6) 0.0121(7) 0.0009(6) C4 0.0160(7) 0.0144(7) 0.0134(7) 0.0018(6) 0.0078(6) 0.0018(6) C5 0.0152(7) 0.0108(7) 0.0134(7) 0.0010(6) 0.0062(6) -0.0003(6) C6 0.0152(7) 0.0115(7) 0.0155(7) -0.0001(6) 0.0081(6) 0.0014(6) C7 0.0161(7) 0.0145(7) 0.0134(7) 0.0028(6) 0.0062(6) -0.0006(6) C8 0.0172(7) 0.0156(8) 0.0123(7) 0.0039(6) 0.0060(6) 0.0012(6) C9 0.0221(8) 0.0232(9) 0.0137(7) 0.0056(6) 0.0089(7) 0.0001(6) C10 0.0248(8) 0.0222(9) 0.0141(7) 0.0068(7) 0.0071(7) -0.0038(6) C11 0.0232(8) 0.0153(8) 0.0187(8) 0.0014(6) 0.0064(7) -0.0045(6) C12 0.0209(8) 0.0150(8) 0.0172(8) 0.0014(6) 0.0086(7) 0.0000(6) C13 0.0160(7) 0.0138(7) 0.0158(7) -0.0031(6) 0.0093(6) -0.0033(6) C14 0.0137(7) 0.0126(7) 0.0158(7) -0.0004(6) 0.0081(6) -0.0001(6) C15 0.0148(7) 0.0181(8) 0.0141(7) -0.0004(6) 0.0075(6) -0.0011(6) C16 0.0186(8) 0.0147(8) 0.0179(8) -0.0025(6) 0.0097(6) -0.0042(6) C17 0.0163(7) 0.0121(7) 0.0202(8) -0.0024(6) 0.0101(6) -0.0002(6) C18 0.0367(10) 0.0200(8) 0.0252(9) 0.0000(7) 0.0235(8) 0.0021(7) C19 0.0539(12) 0.0235(9) 0.0157(8) -0.0099(8) 0.0179(8) -0.0045(7) C20 0.0452(11) 0.0200(9) 0.0190(8) 0.0022(8) 0.0096(8) 0.0048(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 O1 . 1.4291(11) ? S1 O2 . 1.4327(11) ? S1 N1 . 1.6554(13) ? S1 C1 . 1.7542(15) ? O3 C17 . 1.3608(19) ? O3 C20 . 1.430(2) ? O4 C13 . 1.3543(18) ? O4 C19 . 1.436(2) ? N1 C14 . 1.425(2) ? N1 H1 . 0.80(2) ? N2 C17 . 1.325(2) ? N2 C13 . 1.329(2) ? N3 C4 . 1.3770(19) ? N3 C8 . 1.390(2) ? N3 C18 . 1.455(2) ? C1 C6 . 1.388(2) ? C1 C2 . 1.397(2) ? C2 C3 . 1.380(2) ? C2 H2 . 0.9300 ? C3 C4 . 1.394(2) ? C3 H3 . 0.9300 ? C4 C5 . 1.416(2) ? C5 C6 . 1.386(2) ? C5 C7 . 1.449(2) ? C6 H6 . 0.9300 ? C7 C12 . 1.390(2) ? C7 C8 . 1.407(2) ? C8 C9 . 1.397(2) ? C9 C10 . 1.381(2) ? C9 H9 . 0.9300 ? C10 C11 . 1.397(3) ? C10 H10 . 0.9300 ? C11 C12 . 1.385(2) ? C11 H11 . 0.9300 ? C12 H12 . 0.9300 ? C13 C14 . 1.399(2) ? C14 C15 . 1.382(2) ? C15 C16 . 1.382(2) ? C15 H15 . 0.9300 ? C16 C17 . 1.390(2) ? C16 H16 . 0.9300 ? C18 H18A . 0.9600 ? C18 H18B . 0.9600 ? C18 H18C . 0.9600 ? C18 H18D . 0.9600 ? C18 H18E . 0.9600 ? C18 H18F . 0.9600 ? C19 H19A . 0.9600 ? C19 H19B . 0.9600 ? C19 H19C . 0.9600 ? C20 H20A . 0.9600 ? C20 H20B . 0.9600 ? C20 H20C . 0.9600 ? 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 O1 S1 O2 . . 120.41(6) ? O1 S1 N1 . . 106.10(7) ? O2 S1 N1 . . 105.43(7) ? O1 S1 C1 . . 109.15(7) ? O2 S1 C1 . . 108.71(7) ? N1 S1 C1 . . 106.10(7) ? C17 O3 C20 . . 116.23(13) ? C13 O4 C19 . . 116.68(12) ? C14 N1 S1 . . 117.67(10) ? C14 N1 H1 . . 116.4(14) ? S1 N1 H1 . . 110.9(13) ? C17 N2 C13 . . 117.44(13) ? C4 N3 C8 . . 108.21(13) ? C4 N3 C18 . . 125.79(13) ? C8 N3 C18 . . 125.74(13) ? C6 C1 C2 . . 122.25(14) ? C6 C1 S1 . . 119.24(11) ? C2 C1 S1 . . 118.31(11) ? C3 C2 C1 . . 120.44(14) ? C3 C2 H2 . . 119.8 ? C1 C2 H2 . . 119.8 ? C2 C3 C4 . . 117.92(14) ? C2 C3 H3 . . 121.0 ? C4 C3 H3 . . 121.0 ? N3 C4 C3 . . 128.88(14) ? N3 C4 C5 . . 109.52(13) ? C3 C4 C5 . . 121.59(14) ? C6 C5 C4 . . 119.85(13) ? C6 C5 C7 . . 133.80(14) ? C4 C5 C7 . . 106.34(13) ? C5 C6 C1 . . 117.89(14) ? C5 C6 H6 . . 121.1 ? C1 C6 H6 . . 121.1 ? C12 C7 C8 . . 120.01(14) ? C12 C7 C5 . . 133.71(15) ? C8 C7 C5 . . 106.28(13) ? N3 C8 C9 . . 128.59(15) ? N3 C8 C7 . . 109.63(13) ? C9 C8 C7 . . 121.78(15) ? C10 C9 C8 . . 117.10(15) ? C10 C9 H9 . . 121.5 ? C8 C9 H9 . . 121.5 ? C9 C10 C11 . . 121.62(15) ? C9 C10 H10 . . 119.2 ? C11 C10 H10 . . 119.2 ? C12 C11 C10 . . 121.16(16) ? C12 C11 H11 . . 119.4 ? C10 C11 H11 . . 119.4 ? C11 C12 C7 . . 118.33(15) ? C11 C12 H12 . . 120.8 ? C7 C12 H12 . . 120.8 ? N2 C13 O4 . . 119.17(13) ? N2 C13 C14 . . 123.64(14) ? O4 C13 C14 . . 117.16(13) ? C15 C14 C13 . . 117.10(14) ? C15 C14 N1 . . 120.55(13) ? C13 C14 N1 . . 122.34(13) ? C14 C15 C16 . . 120.50(14) ? C14 C15 H15 . . 119.7 ? C16 C15 H15 . . 119.7 ? C15 C16 C17 . . 116.98(14) ? C15 C16 H16 . . 121.5 ? C17 C16 H16 . . 121.5 ? N2 C17 O3 . . 118.84(14) ? N2 C17 C16 . . 124.31(14) ? O3 C17 C16 . . 116.85(14) ? N3 C18 H18A . . 109.5 ? N3 C18 H18B . . 109.5 ? H18A C18 H18B . . 109.5 ? N3 C18 H18C . . 109.5 ? H18A C18 H18C . . 109.5 ? H18B C18 H18C . . 109.5 ? N3 C18 H18D . . 109.5 ? H18A C18 H18D . . 141.1 ? H18B C18 H18D . . 56.3 ? H18C C18 H18D . . 56.3 ? N3 C18 H18E . . 109.5 ? H18A C18 H18E . . 56.3 ? H18B C18 H18E . . 141.1 ? H18C C18 H18E . . 56.3 ? H18D C18 H18E . . 109.5 ? N3 C18 H18F . . 109.5 ? H18A C18 H18F . . 56.3 ? H18B C18 H18F . . 56.3 ? H18C C18 H18F . . 141.1 ? H18D C18 H18F . . 109.5 ? H18E C18 H18F . . 109.5 ? O4 C19 H19A . . 109.5 ? O4 C19 H19B . . 109.5 ? H19A C19 H19B . . 109.5 ? O4 C19 H19C . . 109.5 ? H19A C19 H19C . . 109.5 ? H19B C19 H19C . . 109.5 ? O3 C20 H20A . . 109.5 ? O3 C20 H20B . . 109.5 ? H20A C20 H20B . . 109.5 ? O3 C20 H20C . . 109.5 ? H20A C20 H20C . . 109.5 ? H20B C20 H20C . . 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 O1 S1 N1 C14 . . . . -41.52(12) ? O2 S1 N1 C14 . . . . -170.29(11) ? C1 S1 N1 C14 . . . . 74.49(12) ? O1 S1 C1 C6 . . . . -159.85(11) ? O2 S1 C1 C6 . . . . -26.75(14) ? N1 S1 C1 C6 . . . . 86.21(13) ? O1 S1 C1 C2 . . . . 25.18(14) ? O2 S1 C1 C2 . . . . 158.28(11) ? N1 S1 C1 C2 . . . . -88.76(13) ? C6 C1 C2 C3 . . . . 1.7(2) ? S1 C1 C2 C3 . . . . 176.48(11) ? C1 C2 C3 C4 . . . . -0.5(2) ? C8 N3 C4 C3 . . . . 178.69(15) ? C18 N3 C4 C3 . . . . -6.9(3) ? C8 N3 C4 C5 . . . . -0.51(16) ? C18 N3 C4 C5 . . . . 173.93(14) ? C2 C3 C4 N3 . . . . 179.15(14) ? C2 C3 C4 C5 . . . . -1.7(2) ? N3 C4 C5 C6 . . . . -177.87(13) ? C3 C4 C5 C6 . . . . 2.9(2) ? N3 C4 C5 C7 . . . . 1.19(16) ? C3 C4 C5 C7 . . . . -178.08(13) ? C4 C5 C6 C1 . . . . -1.7(2) ? C7 C5 C6 C1 . . . . 179.60(15) ? C2 C1 C6 C5 . . . . -0.5(2) ? S1 C1 C6 C5 . . . . -175.32(11) ? C6 C5 C7 C12 . . . . -2.6(3) ? C4 C5 C7 C12 . . . . 178.51(16) ? C6 C5 C7 C8 . . . . 177.48(16) ? C4 C5 C7 C8 . . . . -1.39(16) ? C4 N3 C8 C9 . . . . 179.67(15) ? C18 N3 C8 C9 . . . . 5.2(2) ? C4 N3 C8 C7 . . . . -0.40(16) ? C18 N3 C8 C7 . . . . -174.84(14) ? C12 C7 C8 N3 . . . . -178.80(13) ? C5 C7 C8 N3 . . . . 1.12(16) ? C12 C7 C8 C9 . . . . 1.1(2) ? C5 C7 C8 C9 . . . . -178.95(13) ? N3 C8 C9 C10 . . . . 179.09(15) ? C7 C8 C9 C10 . . . . -0.8(2) ? C8 C9 C10 C11 . . . . -0.2(2) ? C9 C10 C11 C12 . . . . 1.0(2) ? C10 C11 C12 C7 . . . . -0.7(2) ? C8 C7 C12 C11 . . . . -0.3(2) ? C5 C7 C12 C11 . . . . 179.77(16) ? C17 N2 C13 O4 . . . . -179.41(13) ? C17 N2 C13 C14 . . . . -1.3(2) ? C19 O4 C13 N2 . . . . -1.0(2) ? C19 O4 C13 C14 . . . . -179.21(15) ? N2 C13 C14 C15 . . . . 1.4(2) ? O4 C13 C14 C15 . . . . 179.54(13) ? N2 C13 C14 N1 . . . . -177.34(13) ? O4 C13 C14 N1 . . . . 0.8(2) ? S1 N1 C14 C15 . . . . 76.61(16) ? S1 N1 C14 C13 . . . . -104.69(15) ? C13 C14 C15 C16 . . . . 0.2(2) ? N1 C14 C15 C16 . . . . 178.92(13) ? C14 C15 C16 C17 . . . . -1.6(2) ? C13 N2 C17 O3 . . . . 179.01(13) ? C13 N2 C17 C16 . . . . -0.4(2) ? C20 O3 C17 N2 . . . . -5.0(2) ? C20 O3 C17 C16 . . . . 174.38(15) ? C15 C16 C17 N2 . . . . 1.8(2) ? C15 C16 C17 O3 . . . . -177.58(13) ? 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 N1 H1 O3 1_565 0.81(2) 2.56(2) 3.3387(18) 163(2) C18 H18A O1 4_566 0.96 2.45 3.398(2) 169.7 C10 H10 O2 4_576 0.93 2.56 3.4887(19) 176.5 data_global _journal_date_recd_electronic 2013-02-21 _journal_date_accepted 2013-03-18 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2013 _journal_volume 69 _journal_issue 4 _journal_page_first o584 _journal_page_last o584 _journal_paper_category QO _journal_paper_doi 10.1107/S1600536813007460 _journal_coeditor_code PK2469 _publ_contact_author_name 'Zongying Liu' _publ_contact_author_address ; Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Tiantan Xili 1#, Beijing, People's Republic of China ; _publ_contact_author_email 'zongyingliu@263.net' _publ_contact_author_fax '(+86)-010-63165287' _publ_contact_author_phone '(+86)-010-63150581' loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Shan, Guangzhi' . ; Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Tiantan Xili 1#, Beijing, People's Republic of China ; 'Li, Zhuorong' . ; Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Tiantan Xili 1#, Beijing, People's Republic of China ; 'Hu, Laixing' . ; Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Tiantan Xili 1#, Beijing, People's Republic of China ; 'Jiang, Jiandong' . ; Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Tiantan Xili 1#, Beijing, People's Republic of China ; 'Liu, Zongying' . ; Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Tiantan Xili 1#, Beijing, People's Republic of China ;