#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:59:37 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180326 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/40/7154093.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_7154093
loop_
_publ_author_name
'Zhang, Rong-Rong'
'Tian, Hai-Yan'
'Tan, Ya-Fang'
'Chung, Tse-Yu'
'Sun, Xiao-Hui'
'Xia, Xue'
'Ye, Wen-Cai'
'Middleton, David A.'
'Fedosova, Natalya'
'Esmann, Mikael'
'Tzen, Jason T. C.'
'Jiang, Ren-Wang'
_publ_section_title
;
 Structures, chemotaxonomic significance, cytotoxic and Na(+),K(+)-ATPase
 inhibitory activities of new cardenolides from Asclepias curassavica.
;
_journal_issue                   44
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8919
_journal_page_last               8929
_journal_paper_doi               10.1039/c4ob01545b
_journal_volume                  12
_journal_year                    2014
_chemical_absolute_configuration rm
_chemical_formula_sum            'C26 H38 N O6'
_chemical_formula_weight         460.57
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4301(3)
_cell_length_b                   11.8072(3)
_cell_length_c                   18.7440(5)
_cell_measurement_reflns_used    4122
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      62.9260
_cell_measurement_theta_min      4.7200
_cell_volume                     2308.33(11)
_computing_cell_refinement       'CrysAlis PRO '
_computing_data_collection       'CrysAlis PRO '
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  'XP (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Agilent Gemini S ultra'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6737
_diffrn_reflns_theta_full        62.74
_diffrn_reflns_theta_max         62.74
_diffrn_reflns_theta_min         4.72
_exptl_absorpt_coefficient_mu    0.755
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'not measured'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       columnar
_exptl_crystal_F_000             996
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3514
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0315
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0433P)²+0.4457P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0810
_reflns_number_gt                3400
_reflns_number_total             3514
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob01545b2.cif
_cod_data_source_block           qr12
_cod_depositor_comments
'Adding full bibliography for 7154092--7154095.cif.'
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7154093
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'
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
O1 O 0.09189(14) 0.68472(12) 0.44504(8) 0.0429(4) Uani 1 1 d .
O2 O 0.19967(12) 0.53384(11) 0.40799(7) 0.0315(3) Uani 1 1 d .
O3 O 0.52266(12) 0.49987(11) 0.28381(6) 0.0323(3) Uani 1 1 d .
H3A H 0.5142 0.5177 0.2418 0.049 Uiso 1 1 calc R
O1' O 1.29038(11) 0.56473(10) 0.07568(6) 0.0278(3) Uani 1 1 d .
O2' O 1.46547(15) 0.5482(2) 0.14264(8) 0.0716(6) Uani 1 1 d .
O3' O 1.56732(13) 0.48610(13) 0.00326(8) 0.0461(4) Uani 1 1 d .
H3'A H 1.5214 0.4367 -0.0138 0.069 Uiso 1 1 calc R
C1 C 1.09470(17) 0.65696(15) 0.23676(10) 0.0282(4) Uani 1 1 d .
H1A H 1.0893 0.7299 0.2603 0.034 Uiso 1 1 calc R
H1B H 1.1204 0.6014 0.2721 0.034 Uiso 1 1 calc R
C2 C 1.19742(18) 0.66294(16) 0.17854(10) 0.0291(4) Uani 1 1 d .
H2A H 1.1762 0.7229 0.1452 0.035 Uiso 1 1 calc R
H2B H 1.2796 0.6809 0.2000 0.035 Uiso 1 1 calc R
C3 C 1.20740(17) 0.55115(15) 0.13867(9) 0.0255(4) Uani 1 1 d .
H3B H 1.2436 0.4933 0.1703 0.031 Uiso 1 1 calc R
C4 C 1.07823(17) 0.51152(15) 0.11102(9) 0.0260(4) Uani 1 1 d .
H4A H 1.0871 0.4362 0.0909 0.031 Uiso 1 1 calc R
H4B H 1.0498 0.5619 0.0733 0.031 Uiso 1 1 calc R
C5 C 0.97737(17) 0.50917(14) 0.17047(8) 0.0227(4) Uani 1 1 d .
H5A H 1.0103 0.4571 0.2068 0.027 Uiso 1 1 calc R
C6 C 0.85041(18) 0.45974(16) 0.14568(10) 0.0300(4) Uani 1 1 d .
H6A H 0.8121 0.5095 0.1105 0.036 Uiso 1 1 calc R
H6B H 0.8652 0.3868 0.1234 0.036 Uiso 1 1 calc R
C7 C 0.75910(18) 0.44546(15) 0.20820(10) 0.0295(4) Uani 1 1 d .
H7A H 0.7938 0.3899 0.2410 0.035 Uiso 1 1 calc R
H7B H 0.6775 0.4173 0.1909 0.035 Uiso 1 1 calc R
C8 C 0.73775(16) 0.55722(14) 0.24778(8) 0.0217(4) Uani 1 1 d .
H8A H 0.6980 0.6097 0.2139 0.026 Uiso 1 1 calc R
C9 C 0.86598(16) 0.61053(14) 0.27107(9) 0.0212(4) Uani 1 1 d .
H9A H 0.9057 0.5577 0.3048 0.025 Uiso 1 1 calc R
C10 C 0.96155(17) 0.62510(13) 0.20792(9) 0.0217(4) Uani 1 1 d .
C11 C 0.84068(17) 0.72093(15) 0.31220(10) 0.0278(4) Uani 1 1 d .
H11A H 0.9213 0.7504 0.3301 0.033 Uiso 1 1 calc R
H11B H 0.8049 0.7767 0.2799 0.033 Uiso 1 1 calc R
C12 C 0.74862(17) 0.70329(15) 0.37456(10) 0.0281(4) Uani 1 1 d .
H12A H 0.7340 0.7755 0.3979 0.034 Uiso 1 1 calc R
H12B H 0.7885 0.6531 0.4090 0.034 Uiso 1 1 calc R
C13 C 0.61803(16) 0.65281(14) 0.35217(9) 0.0234(4) Uani 1 1 d .
C14 C 0.64303(16) 0.54240(14) 0.31016(9) 0.0226(4) Uani 1 1 d .
C15 C 0.68312(18) 0.45748(14) 0.36765(9) 0.0284(4) Uani 1 1 d .
H15A H 0.7756 0.4571 0.3731 0.034 Uiso 1 1 calc R
H15B H 0.6553 0.3818 0.3549 0.034 Uiso 1 1 calc R
C16 C 0.61827(18) 0.49563(16) 0.43760(9) 0.0311(4) Uani 1 1 d .
H16A H 0.6818 0.5044 0.4750 0.037 Uiso 1 1 calc R
H16B H 0.5558 0.4398 0.4529 0.037 Uiso 1 1 calc R
C17 C 0.55152(16) 0.61014(15) 0.42248(9) 0.0261(4) Uani 1 1 d .
H17A H 0.5751 0.6624 0.4609 0.031 Uiso 1 1 calc R
C18 C 0.54000(19) 0.74077(16) 0.31168(11) 0.0339(4) Uani 1 1 d .
H18A H 0.5856 0.7630 0.2694 0.051 Uiso 1 1 calc R
H18B H 0.5266 0.8058 0.3415 0.051 Uiso 1 1 calc R
H18C H 0.4586 0.7090 0.2986 0.051 Uiso 1 1 calc R
C19 C 0.91431(19) 0.71775(15) 0.15624(10) 0.0309(4) Uani 1 1 d .
H19A H 0.9747 0.7261 0.1179 0.046 Uiso 1 1 calc R
H19B H 0.9066 0.7882 0.1814 0.046 Uiso 1 1 calc R
H19C H 0.8323 0.6966 0.1372 0.046 Uiso 1 1 calc R
C20 C 0.40764(17) 0.60393(14) 0.42002(9) 0.0250(4) Uani 1 1 d .
C21 C 0.33232(18) 0.50025(17) 0.40198(11) 0.0369(5) Uani 1 1 d .
H21A H 0.3514 0.4750 0.3539 0.044 Uiso 1 1 calc R
H21B H 0.3517 0.4393 0.4350 0.044 Uiso 1 1 calc R
C22 C 0.32465(17) 0.68506(16) 0.43701(10) 0.0312(4) Uani 1 1 d .
H22A H 0.3464 0.7584 0.4505 0.037 Uiso 1 1 calc R
C23 C 0.19472(18) 0.64164(15) 0.43123(10) 0.0296(4) Uani 1 1 d .
C1' C 1.41557(18) 0.56318(16) 0.08587(9) 0.0301(4) Uani 1 1 d .
C2' C 1.49249(17) 0.58375(16) 0.01797(10) 0.0290(4) Uani 1 1 d .
H2'A H 1.4348 0.5999 -0.0220 0.035 Uiso 1 1 calc R
C3' C 1.5834(2) 0.68102(19) 0.02928(13) 0.0471(5) Uani 1 1 d .
H3'B H 1.6320 0.6936 -0.0135 0.071 Uiso 1 1 calc R
H3'C H 1.6406 0.6635 0.0678 0.071 Uiso 1 1 calc R
H3'D H 1.5355 0.7481 0.0407 0.071 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 0.0181 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C23 O2 C21 108.77(14)
C1' O1' C3 117.64(13)
C2 C1 C10 113.14(14)
C3 C2 C1 110.99(15)
O1' C3 C4 106.35(13)
O1' C3 C2 109.86(14)
C4 C3 C2 112.01(15)
C3 C4 C5 111.51(13)
C6 C5 C4 112.50(13)
C6 C5 C10 112.68(14)
C4 C5 C10 112.77(13)
C7 C6 C5 110.66(14)
C6 C7 C8 111.68(14)
C7 C8 C14 111.31(13)
C7 C8 C9 111.30(14)
C14 C8 C9 112.82(13)
C11 C9 C8 109.84(14)
C11 C9 C10 113.42(13)
C8 C9 C10 112.67(13)
C1 C10 C19 109.63(14)
C1 C10 C5 106.25(14)
C19 C10 C5 112.13(14)
C1 C10 C9 109.77(13)
C19 C10 C9 110.57(14)
C5 C10 C9 108.39(13)
C12 C11 C9 112.10(14)
C11 C12 C13 113.52(15)
C18 C13 C12 110.10(15)
C18 C13 C14 114.32(15)
C12 C13 C14 108.37(14)
C18 C13 C17 113.62(14)
C12 C13 C17 106.55(14)
C14 C13 C17 103.36(13)
O3 C14 C15 104.56(14)
O3 C14 C8 109.78(13)
C15 C14 C8 115.69(14)
O3 C14 C13 108.78(13)
C15 C14 C13 103.90(13)
C8 C14 C13 113.52(13)
C14 C15 C16 106.70(14)
C15 C16 C17 107.26(14)
C20 C17 C16 114.35(15)
C20 C17 C13 115.50(14)
C16 C17 C13 103.60(13)
C22 C20 C21 107.60(16)
C22 C20 C17 127.40(17)
C21 C20 C17 124.89(16)
O2 C21 C20 105.14(15)
C20 C22 C23 109.57(17)
O1 C23 O2 119.91(17)
O1 C23 C22 131.27(17)
O2 C23 C22 108.79(15)
O2' C1' O1' 124.09(18)
O2' C1' C2' 122.47(17)
O1' C1' C2' 113.44(15)
O3' C2' C3' 107.52(16)
O3' C2' C1' 108.81(15)
C3' C2' C1' 109.61(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C23 1.215(2)
O2 C23 1.346(2)
O2 C21 1.444(2)
O3 C14 1.440(2)
O1' C1' 1.320(2)
O1' C3 1.473(2)
O2' C1' 1.198(2)
O3' C2' 1.419(2)
C1 C2 1.531(2)
C1 C10 1.537(2)
C2 C3 1.520(2)
C3 C4 1.517(2)
C4 C5 1.533(2)
C5 C6 1.520(2)
C5 C10 1.547(2)
C6 C7 1.519(2)
C7 C8 1.530(2)
C8 C14 1.541(2)
C8 C9 1.541(2)
C9 C11 1.537(2)
C9 C10 1.557(2)
C10 C19 1.542(2)
C11 C12 1.527(3)
C12 C13 1.545(2)
C13 C18 1.522(2)
C13 C14 1.545(2)
C13 C17 1.572(2)
C14 C15 1.530(2)
C15 C16 1.543(2)
C16 C17 1.547(3)
C17 C20 1.503(2)
C20 C22 1.330(3)
C20 C21 1.493(3)
C22 C23 1.453(3)
C1' C2' 1.524(3)
C2' C3' 1.504(3)
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
C10 C1 C2 C3 -57.3(2)
C1' O1' C3 C4 -158.88(15)
C1' O1' C3 C2 79.69(19)
C1 C2 C3 O1' 170.51(14)
C1 C2 C3 C4 52.5(2)
O1' C3 C4 C5 -172.46(13)
C2 C3 C4 C5 -52.42(19)
C3 C4 C5 C6 -174.84(14)
C3 C4 C5 C10 56.38(19)
C4 C5 C6 C7 172.94(15)
C10 C5 C6 C7 -58.22(19)
C5 C6 C7 C8 56.3(2)
C6 C7 C8 C14 178.89(15)
C6 C7 C8 C9 -54.32(19)
C7 C8 C9 C11 -178.61(14)
C14 C8 C9 C11 -52.65(19)
C7 C8 C9 C10 53.91(18)
C14 C8 C9 C10 179.86(13)
C2 C1 C10 C19 -63.31(19)
C2 C1 C10 C5 58.05(18)
C2 C1 C10 C9 175.04(14)
C6 C5 C10 C1 173.93(14)
C4 C5 C10 C1 -57.38(17)
C6 C5 C10 C19 -66.32(18)
C4 C5 C10 C19 62.37(19)
C6 C5 C10 C9 56.02(18)
C4 C5 C10 C9 -175.29(14)
C11 C9 C10 C1 65.13(18)
C8 C9 C10 C1 -169.30(14)
C11 C9 C10 C19 -55.95(19)
C8 C9 C10 C19 69.62(17)
C11 C9 C10 C5 -179.23(14)
C8 C9 C10 C5 -53.66(18)
C8 C9 C11 C12 54.00(19)
C10 C9 C11 C12 -178.93(15)
C9 C11 C12 C13 -57.0(2)
C11 C12 C13 C18 -71.33(19)
C11 C12 C13 C14 54.38(19)
C11 C12 C13 C17 165.04(14)
C7 C8 C14 O3 -58.10(18)
C9 C8 C14 O3 175.95(13)
C7 C8 C14 C15 59.90(19)
C9 C8 C14 C15 -66.05(19)
C7 C8 C14 C13 179.91(14)
C9 C8 C14 C13 53.96(19)
C18 C13 C14 O3 -51.93(18)
C12 C13 C14 O3 -175.12(13)
C17 C13 C14 O3 72.08(15)
C18 C13 C14 C15 -162.89(15)
C12 C13 C14 C15 73.92(17)
C17 C13 C14 C15 -38.88(16)
C18 C13 C14 C8 70.61(19)
C12 C13 C14 C8 -52.58(18)
C17 C13 C14 C8 -165.38(13)
O3 C14 C15 C16 -86.22(16)
C8 C14 C15 C16 152.92(15)
C13 C14 C15 C16 27.80(18)
C14 C15 C16 C17 -5.75(19)
C15 C16 C17 C20 108.44(17)
C15 C16 C17 C13 -18.12(18)
C18 C13 C17 C20 33.7(2)
C12 C13 C17 C20 155.08(15)
C14 C13 C17 C20 -90.80(17)
C18 C13 C17 C16 159.50(15)
C12 C13 C17 C16 -79.09(16)
C14 C13 C17 C16 35.03(16)
C16 C17 C20 C22 150.23(18)
C13 C17 C20 C22 -89.7(2)
C16 C17 C20 C21 -25.6(2)
C13 C17 C20 C21 94.6(2)
C23 O2 C21 C20 -3.6(2)
C22 C20 C21 O2 2.2(2)
C17 C20 C21 O2 178.72(16)
C21 C20 C22 C23 -0.2(2)
C17 C20 C22 C23 -176.55(17)
C21 O2 C23 O1 -174.72(18)
C21 O2 C23 C22 3.6(2)
C20 C22 C23 O1 175.9(2)
C20 C22 C23 O2 -2.1(2)
C3 O1' C1' O2' 2.3(3)
C3 O1' C1' C2' -177.13(14)
O2' C1' C2' O3' 63.2(3)
O1' C1' C2' O3' -117.34(17)
O2' C1' C2' C3' -54.1(3)
O1' C1' C2' C3' 125.33(18)
