Cryptoyunnanones A‒H, Complex Flavanones from Cryptocarya yunnanensis
He, Qian; Fan, Yue; Liu, Yu; Rao, Li; You, Yun-Xia; Su, Yu; Zhou, Zhen; Xu, You-Kai; Zhang, Chuan-Rui; Journal of Natural Products  (2021) –; doi:10.1021/acs.jnatprod.1c00287

data_1564218
_publ_section_title
;
 Cryptoyunnanones A--H, Complex Flavanones from Cryptocarya yunnanensis
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.1c00287
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C33 H32 O7'
_chemical_formula_sum            'C33 H32 O7'
_chemical_formula_weight         540.58
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-01-19
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6226)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.89630(10)
_cell_length_b                   16.0260(3)
_cell_length_c                   21.3509(4)
_cell_measurement_reflns_used    9426
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.6760
_cell_measurement_theta_min      3.4320
_cell_volume                     2701.87(8)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_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     23.00 118.00   0.50    0.05    --   46.37  77.00 -90.00  190
  2  \w     86.00 178.00   0.50    0.50    --  107.00 112.00  58.00  184
  3  \w     79.00 178.00   0.50    0.50    --  107.00 125.00 120.00  198
  4  \w     90.00 178.00   0.50    0.50    --  107.00  61.00 120.00  176
  5  \w     34.00 106.00   0.50    0.50    --  107.00 -94.00 -60.00  144
  6  \w     34.00 112.00   0.50    0.50    --  107.00-125.00 -90.00  156
  7  \w     34.00 112.00   0.50    0.50    --  107.00-125.00-180.00  156
  8  \w     34.00 112.00   0.50    0.50    --  107.00-125.00   0.00  156
  9  \w     34.00 113.00   0.50    0.50    --  107.00-127.00  64.00  158
 10  \w     34.00 107.00   0.50    0.50    --  107.00 -77.00  30.00  146
 11  \w     34.00  73.00   0.50    0.50    --  107.00 -61.00  30.00   78
 12  \w     34.00  73.00   0.50    0.50    --  107.00 -61.00  60.00   78
 13  \w     34.00  73.00   0.50    0.50    --  107.00 -61.00-150.00   78
 14  \w    -29.00  28.00   0.50    0.05    --   46.37 -19.00  30.00  114
 15  \w    -29.00  26.00   0.50    0.05    --   46.37 -15.00 123.00  110
 16  \w     34.00  73.00   0.50    0.50    --  107.00 -61.00 150.00   78
 17  \w    -22.00  30.00   0.50    0.05    --  -46.37  15.00 -66.00  104
 18  \w    -69.00 -27.00   0.50    0.50    -- -100.00  61.00-120.00   84
 19  \w    -41.00  27.00   0.50    0.05    --  -46.37  38.00   0.00  136
 20  \w    -41.00  27.00   0.50    0.05    --  -46.37  38.00  60.00  136
 21  \w   -113.00 -27.00   0.50    0.50    -- -100.00 127.00 140.00  172
 22  \w   -175.00 -82.00   0.50    0.50    -- -100.00 -15.00 123.00  186
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0328515000
_diffrn_orient_matrix_UB_12      -0.0208317000
_diffrn_orient_matrix_UB_13      -0.0694266000
_diffrn_orient_matrix_UB_21      0.0192128000
_diffrn_orient_matrix_UB_22      0.0936317000
_diffrn_orient_matrix_UB_23      -0.0145965000
_diffrn_orient_matrix_UB_31      0.1913074000
_diffrn_orient_matrix_UB_32      -0.0058272000
_diffrn_orient_matrix_UB_33      0.0133702000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0694
_diffrn_reflns_av_unetI/netI     0.0491
_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       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            27200
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.095
_diffrn_reflns_theta_min         3.448
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.757
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       block
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 2033 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         5610
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0508
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0699P)^2^+0.9854P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1303
_refine_ls_wR_factor_ref         0.1335
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                5133
_reflns_number_total             5610
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00287_si_003.cif
_cod_data_source_block           liw_hq-08_201231
_cod_database_code               1564218
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.863
_shelx_estimated_absorpt_t_min   0.805
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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. Others
 Sof(C7A)=Sof(H7A)=1-FVAR(1)
 Sof(C7)=Sof(H7)=FVAR(1)
 Fixed Sof: C29B(0.5) H29A(0.5) H29B(0.5) C29A(0.5) H29C(0.5) H29D(0.5)
3.a Ternary CH refined with riding coordinates:
 C11(H11), C9(H9), C7(H7), C7A(H7A)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C8(H8A,H8B), C21(H21A,H21B), C20(H20A,H20B), C22(H22A,H22B),
 C29B(H29A,H29B), C29A(H29C,H29D)
3.c Aromatic/amide H refined with riding coordinates:
 C33(H33), C13(H13), C18(H18), C12(H12), C19(H19), C15(H15), C16(H16),
 C17(H17), C37(H37), C35(H35), C36(H36), C34(H34), C39(H39)
3.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
3.e Idealised tetrahedral OH refined as rotating group:
 O31(H31)
;
_shelx_res_checksum              69720
_shelx_hkl_checksum              95179
_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 1.821
_oxdiff_exptl_absorpt_empirical_full_min 0.540