Withapubesides A‒D, natural inducible nitric oxide synthase (iNOS) inhibitors from Physalis pubescens
Xia, Guiyang; Yao, Tie; Zhang, Bing-Yang; Li, Yang; Kang, Ning; Cao, Shijie; Ding, Liqin; Chen, Lixia; Qiu, Feng; Organic & Biomolecular Chemistry  (2017) –; doi:10.1039/C7OB02551C

data_7155978
_publ_section_title
;
 Withapubesides A--D, natural inducible nitric oxide synthase (iNOS)
 inhibitors from Physalis pubescens
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/C7OB02551C
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_compound_source        'Physalis pubescens'
_chemical_formula_moiety         'C41 H65 O15, H2 O'
_chemical_formula_sum            'C41 H67 O16'
_chemical_formula_weight         815.94
_chemical_name_systematic        'Withapubeside A'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2016-11-18
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2017-08-22 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9929(4)
_cell_length_b                   9.2895(5)
_cell_length_c                   54.987(4)
_cell_measurement_reflns_used    5171
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.9050
_cell_measurement_theta_min      4.7950
_cell_volume                     4082.8(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5368
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -114.00 -11.00   1.00    3.50    --  -40.46 -56.00  96.00  103
  2  \w    -96.00  -2.00   1.00    3.50    --  -40.46 125.00-150.00   94
  3  \w      1.00  82.00   1.00    3.50    --   40.46 -99.00  60.00   81
  4  \w    100.00 178.00   1.00   20.00    --  107.48 111.00 -60.00   78
  5  \w     29.00 115.00   1.00   20.00    --  107.48-111.00 -90.00   86
  6  \w    100.00 178.00   1.00   20.00    --  107.48 111.00 -30.00   78
  7  \w     80.00 178.00   1.00   20.00    --  107.48  45.00  30.00   98
  8  \w     23.00 109.00   1.00   20.00    --  107.48 -94.00 -60.00   86
  9  \w     57.00 151.00   1.00   20.00    --  107.48 178.00 150.00   94
 10  \w   -114.00 -11.00   1.00    3.50    --  -40.46 -57.00 -60.00  103
 11  \w   -117.00 -14.00   1.00    3.50    --  -40.46 -37.00-180.00  103
 12  \w     77.00 178.00   1.00   20.00    --  107.48  30.00 150.00  101
 13  \w     77.00 178.00   1.00   20.00    --  107.48  61.00-150.00  101
 14  \w     80.00 178.00   1.00   20.00    --  107.48  45.00  90.00   98
 15  \w     80.00 178.00   1.00   20.00    --  107.48  45.00 -90.00   98
 16  \w   -115.00 -69.00   1.00    3.50    --  -40.46-132.00  41.00   46
 17  \w   -119.00  -7.00   1.00    3.50    --  -40.46 -77.00  30.00  112
 18  \w     80.00 166.00   1.00   20.00    --  107.48  45.00 -30.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1256568000
_diffrn_orient_matrix_UB_12      0.1197041000
_diffrn_orient_matrix_UB_13      -0.0065041000
_diffrn_orient_matrix_UB_21      0.0276807000
_diffrn_orient_matrix_UB_22      -0.0306914000
_diffrn_orient_matrix_UB_23      -0.0272313000
_diffrn_orient_matrix_UB_31      -0.1436333000
_diffrn_orient_matrix_UB_32      -0.1106106000
_diffrn_orient_matrix_UB_33      0.0005271000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1016
_diffrn_reflns_av_unetI/netI     0.0728
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       67
_diffrn_reflns_limit_l_min       -67
_diffrn_reflns_number            38558
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.685
_diffrn_reflns_theta_min         4.825
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.842
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       block
_exptl_crystal_F_000             1764
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.005
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Flack x determined using 2275 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     542
_refine_ls_number_reflns         8112
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0756
_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/[\s^2^(Fo^2^)+(0.0601P)^2^+5.4341P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1749
_refine_ls_wR_factor_ref         0.1829
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                6881
_reflns_number_total             8112
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02551c2.cif
_cod_data_source_block           exp_61
_cod_database_code               7155978
_shelx_estimated_absorpt_t_max   0.850
_shelx_estimated_absorpt_t_min   0.786
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Others
 Sof(H6"A)=Sof(O4A")=Sof(H4A")=1-FVAR(1)
 Sof(H6")=Sof(O4B")=Sof(H4B")=FVAR(1)
3.a Free rotating group:
 O1W(H1WA,H1WB)
3.b Ternary CH refined with riding coordinates:
 C8(H8), C2"(H2"A), C2'(H2'A), C3(H3), C9(H9), C4'(H4'A), C5"(H5"), C3'(H3'A),
 C0AA(H0AA), C3"(H3"A), C5'(H5'), C1"(H1"A), C1'(H1'), C4"(H4"), C20(H20),
 C17(H17), C14(H14), C25(H25), C22(H22)
3.c Secondary CH2 refined with riding coordinates:
 C6'(H6'A,H6'B), C2(H2A,H2B), C23(H23A,H23B), C4(H4A,H4B), C12(H12A,H12B),
 C16(H16A,H16B), C15(H15A,H15B), C7(H7A,H7B), C11(H11A,H11B)
3.d Aromatic/amide H refined with riding coordinates:
 C6(H6), C6"(H6"), C6"(H6"A)
3.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C18(H18A,H18B,H18C), C29(H29A,H29B,H29C), C28(H28A,H28B,
 H28C), C27(H27A,H27B,H27C), C21(H21A,H21B,H21C)
3.f Idealised tetrahedral OH refined as rotating group:
 O1"(H1"), O2"(H2"), O2'(H2'), O4'(H4'), O3"(H3"), O3'(H3'), O1(H1),
 O4B"(H4B"), O4A"(H4A")
;
_shelx_res_checksum              60674
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.245
_oxdiff_exptl_absorpt_empirical_full_min 0.831