Anti-inflammatory Grayanane Diterpenoids from the Leaves of Rhododendron molle
Zhou, Junfei; Liu, Tingting; Zhang, Hanqi; Zheng, Guijuan; Qiu, Yue; Deng, Mengyi; Zhang, Chun; Yao, Guangmin; Journal of Natural Products  (2017) –; doi:10.1021/acs.jnatprod.7b00799

data_1548537
_publ_section_title
;
 Anti-inflammatory Grayanane Diterpenoids from the Leaves of Rhododendron
 molle
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.7b00799
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H34 O6'
_chemical_formula_sum            'C23 H34 O6'
_chemical_formula_weight         406.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-09-07
_audit_creation_method
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.0090(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.81810(10)
_cell_length_b                   16.3996(2)
_cell_length_c                   13.9736(2)
_cell_measurement_reflns_used    15860
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4870
_cell_measurement_theta_min      4.7020
_cell_volume                     2151.52(5)
_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  'XH (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.986
_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   -113.00 -13.00   1.00    1.00    --  -40.98 -57.00  90.00  100
  2  \w   -115.00 -17.00   1.00    1.00    --  -40.98 -37.00 -60.00   98
  3  \w    -74.00  35.00   1.00    1.00    --  -40.98  77.00-150.00  109
  4  \w   -113.00 -13.00   1.00    1.00    --  -40.98 -57.00   0.00  100
  5  \w    -96.00  -2.00   1.00    1.00    --  -40.98 125.00 -90.00   94
  6  \w     13.00 113.00   1.00    1.00    --   40.98  57.00 120.00  100
  7  \w     31.00 135.00   1.00    1.74    --  106.95 -30.00  30.00  104
  8  \w     74.00 178.00   1.00    1.74    --  106.95  77.00  30.00  104
  9  \w     34.00 121.00   1.00    1.74    --  106.95-125.00 -60.00   87
 10  \w     74.00 178.00   1.00    1.74    --  106.95  77.00  60.00  104
 11  \w     94.00 178.00   1.00    1.74    --  106.95 125.00-180.00   84
 12  \w     74.00 178.00   1.00    1.74    --  106.95  77.00  90.00  104
 13  \w     78.00 178.00   1.00    1.74    --  106.95  61.00   0.00  100
 14  \w     78.00 178.00   1.00    1.74    --  106.95  61.00 120.00  100
 15  \w     81.00 178.00   1.00    1.74    --  106.95  45.00 150.00   97
 16  \w     74.00 178.00   1.00    1.74    --  106.95  77.00   0.00  104
 17  \w     78.00 134.00   1.00    1.74    --  106.95  61.00  30.00   56
;
_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      0.1436770000
_diffrn_orient_matrix_UB_12      -0.0132143000
_diffrn_orient_matrix_UB_13      0.0804959000
_diffrn_orient_matrix_UB_21      -0.0787264000
_diffrn_orient_matrix_UB_22      -0.0351105000
_diffrn_orient_matrix_UB_23      0.0714174000
_diffrn_orient_matrix_UB_31      0.0102453000
_diffrn_orient_matrix_UB_32      -0.0860848000
_diffrn_orient_matrix_UB_33      -0.0413007000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21222
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.567
_diffrn_reflns_theta_min         4.268
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.728
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57574
_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    1.255
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 3414 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     542
_refine_ls_number_reflns         8055
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0371
_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^)+(0.0675P)^2^+0.2019P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.0998
_reflns_Friedel_coverage         0.817
_reflns_Friedel_fraction_full    0.908
_reflns_Friedel_fraction_max     0.868
_reflns_number_gt                7861
_reflns_number_total             8055
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b00799_si_005.cif
_cod_data_source_block           3-6-8
_cod_database_code               1548537
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.924
_shelx_estimated_absorpt_t_min   0.880
_reflns_odcompleteness_completeness 99.70
_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
2.a Ternary CH refined with riding coordinates:
 C00G(H00G), C2(H2a), C1(H1), C00R(H00R), C00S(H00S), C14(H14), C6(H6a),
 C00X(H00X), C00Z(H00Z), C3(H3), C016(H016), C10(H10), C01A(H01g), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11a,H11b), C7(H7a,H7b), C010(H01a,H01b), C013(H01c,H01d), C12(H12a,H12b),
  C015(H01e,H01f)
2.c Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C15(H15)
2.d Idealised Me refined as rotating group:
 C19(H19a,H19b,H19c), C20(H20a,H20b,H20c), C01D(H01h,H01i,H01j), C01E(H01k,
 H01l,H01m), C01F(H01n,H01o,H01p), C18(H18a,H18b,H18c), C23(H23a,H23b,H23c),
 C01I(H01q,H01r,H01s), C01J(H01t,H01u,H01v), C22(H22a,H22b,H22c), C17(H17a,H17b,
 H17c), C01M(H01w,H01x,H01y)
2.e Idealised tetrahedral OH refined as rotating group:
 O005(H005), O2(H2), O009(H009)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.496
_oxdiff_exptl_absorpt_empirical_full_min 0.622