Przewalcyrones A-F, epoxychromene-containing polycyclic polyprenylated acylphloroglucinols with immunosuppressive activity from Hypericum przewalskii Maxim.
Duan, Yulin; Xie, Shuangshuang; Guo, Yi; Qiao, Yuben; Shi, Zhengyi; Tao, Li; Deng, Mengyi; Cao, Yunfang; Xue, Yongbo; Qi, Changxing; Zhang, Yonghui; Organic & biomolecular chemistry 17 (2019) 8234–8242; doi:10.1039/c9ob01500k

data_7157037
_publ_section_title
;
 Przewalcyrones A-F, epoxychromene-containing polycyclic polyprenylated
 acylphloroglucinols with immunosuppressive activity from Hypericum
 przewalskii Maxim.
;
_journal_issue                   35
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8234
_journal_page_last               8242
_journal_paper_doi               10.1039/c9ob01500k
_journal_volume                  17
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H45 O6'
_chemical_formula_sum            'C31 H45 O6'
_chemical_formula_weight         513.67
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-10-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-05-11 deposited with the CCDC.    2019-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.97968(4)
_cell_length_b                   10.81315(5)
_cell_length_c                   27.72380(12)
_cell_measurement_reflns_used    46485
_cell_measurement_temperature    283(9)
_cell_measurement_theta_max      73.4870
_cell_measurement_theta_min      4.3780
_cell_volume                     2991.72(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (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      air
_diffrn_ambient_temperature      283(9)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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     51.00  76.00   0.50    0.50    --    0.00  38.00-150.00   50
  2  \w     -9.00  81.00   0.50    0.50    --    0.00  38.00 -30.00  180
  3  \w    -22.00   4.00   0.50    0.50    --    0.00  57.00  30.00   52
  4  \w    -22.00   8.00   0.50    0.50    --    0.00  57.00  90.00   60
  5  \w    -16.00  18.00   0.50    0.50    --    0.00  38.00-150.00   68
  6  \w     11.00  83.00   0.50    0.50    --    0.00  57.00  90.00  144
  7  \w      9.00  71.00   0.50    0.50    --    0.00  57.00  30.00  124
  8  \w    -31.00  14.00   0.50    0.50    --    0.00 -82.00 -90.00   90
  9  \w    -21.00  89.00   0.50    0.50    --    0.00  57.00 150.00  220
 10  \w    -14.00  26.00   0.50    0.50    --    0.00 -82.00 -30.00   80
 11  \w    -16.00  31.00   0.50    0.50    --    0.00 -82.00   0.00   94
 12  \w    131.00 157.00   0.50    0.50    --   94.60  72.00 -39.81   52
 13  \w    139.00 172.00   0.50    0.50    --   94.60  58.00  78.88   66
 14  \w     68.00 103.00   0.50    0.50    --   94.60  69.00   1.83   70
 15  \w     67.00  92.00   0.50    0.50    --   94.60  72.00 -39.81   50
 16  \w     68.00  93.00   0.50    0.50    --   94.60  70.00  72.17   50
 17  \w     72.00 125.00   0.50    0.50    --   94.60  58.00  78.88  106
 18  \w     72.00  97.00   0.50    0.50    --   94.60  55.00 150.56   50
 19  \w     67.00  93.00   0.50    0.50    --   94.60  73.00  90.53   52
 20  \w    134.00 176.00   0.50    0.50    --   94.60  56.00 -75.62   84
 21  \w     69.00 100.00   0.50    0.50    --   94.60  68.00-170.02   62
 22  \w     69.00  94.00   0.50    0.50    --   94.60  68.00 -66.32   50
 23  \w     68.00  93.00   0.50    0.50    --   94.60  69.00  55.37   50
 24  \w     70.00 174.00   0.50    0.50    --   94.60  65.00 -23.32  208
 25  \w     69.00 184.00   0.50    0.50    --   94.60  68.00  14.39  230
 26  \w     69.00 100.00   0.50    0.50    --   94.60  67.00  -7.88   62
 27  \w     67.00 184.00   0.50    0.50    --   94.60  72.00 161.67  234
 28  \w     69.00  94.00   0.50    0.50    --   94.60  67.00 -52.51   50
 29  \w     68.00  94.00   0.50    0.50    --   94.60  69.00  24.67   52
 30  \w     68.00 100.00   0.50    0.50    --   94.60  70.00-141.84   64
 31  \w     66.00  91.00   0.50    0.50    --   94.60  74.00-126.41   50
 32  \w     72.00 115.00   0.50    0.50    --   94.60  56.00 -75.62   86
 33  \w    132.00 158.00   0.50    0.50    --   94.60  67.00-179.95   52
 34  \w     70.00  96.00   0.50    0.50    --   94.60  65.00-123.83   52
 35  \w     71.00 128.00   0.50    0.50    --   94.60  61.00 150.00  114
 36  \w      5.00 118.00   0.50    0.50    --   94.60 -61.00  90.00  226
 37  \w     72.00  97.00   0.50    0.50    --   94.60  56.00 -67.11   50
 38  \w     31.00 118.00   0.50    0.50    --   94.60 -61.00 -30.00  174
 39  \w     75.00 143.00   0.50    0.50    --   94.60  45.00-120.00  136
 40  \w    159.00 184.00   0.50    0.50    --   94.60  45.00-120.00   50
 41  \w     71.00 184.00   0.50    0.50    --   94.60  59.00 104.57  226
 42  \w     67.00  93.00   0.50    0.50    --   94.60  71.00 109.11   52
 43  \w     75.00 169.00   0.50    0.50    --   94.60  45.00 150.00  188
 44  \w     71.00 183.00   0.50    0.50    --   94.60  61.00 -30.00  224
 45  \w      6.00 123.00   0.50    0.50    --   94.60 -82.00 -30.00  234
 46  \w     71.00  96.00   0.50    0.50    --   94.60  61.00-150.00   50
 47  \w     71.00 114.00   0.50    0.50    --   94.60  61.00  60.00   86
 48  \w     33.00 106.00   0.50    0.50    --   94.60 -82.00 -90.00  146
 49  \w      5.00 126.00   0.50    0.50    --   94.60 -82.00  90.00  242
 50  \w     68.00  93.00   0.50    0.50    --   94.60  69.00 151.89   50
 51  \w     71.00  96.00   0.50    0.50    --   94.60  61.00 -90.00   50
 52  \w     71.00  97.00   0.50    0.50    --   94.60  61.00  90.00   52
 53  \w     57.00 102.00   0.50    0.50    --   94.60 -82.00-120.00   90
 54  \w    140.00 173.00   0.50    0.50    --   94.60  69.00   1.83   66
 55  \w     71.00 172.00   0.50    0.50    --   94.60  63.00  41.62  202
 56  \w     69.00  94.00   0.50    0.50    --   94.60  67.00-179.95   50
 57  \w     74.00 105.00   0.50    0.50    --   94.60  52.00 -86.92   62
 58  \w     43.00 101.00   0.50    0.50    --   94.60 -82.00-180.00  116
 59  \w     72.00 159.00   0.50    0.50    --   94.60  56.00 -58.04  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0302277000
_diffrn_orient_matrix_UB_12      -0.0311015000
_diffrn_orient_matrix_UB_13      -0.0531284000
_diffrn_orient_matrix_UB_21      -0.1394734000
_diffrn_orient_matrix_UB_22      -0.0597097000
_diffrn_orient_matrix_UB_23      -0.0049499000
_diffrn_orient_matrix_UB_31      -0.0588673000
_diffrn_orient_matrix_UB_32      0.1255551000
_diffrn_orient_matrix_UB_33      -0.0155133000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0097
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            72742
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.982
_diffrn_reflns_theta_min         3.188
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_description       block
_exptl_crystal_F_000             1116
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 2521 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_coef       0.0027(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         6058
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0811P)^2^+0.3818P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1254
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                5923
_reflns_number_total             6058
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01500k2.cif
_cod_data_source_block           20181015-dyl1-4-1
_cod_depositor_comments          'Adding full bibliography for 7157037.cif.'
_cod_database_code               7157037
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.97
_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:
 C7(H7), C21(H21), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C6(H6A,H6B), C15(H15A,H15B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C26(H26), C16(H16), C13(H13)
2.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C24(H24A,H24B,H24C), C28(H28A,H28B,
 H28C), C23(H23A,H23B,H23C), C29(H29A,H29B,H29C), C19(H19A,H19B,H19C), C18(H18A,
 H18B,H18C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C)
2.e Idealised tetrahedral OH refined as rotating group:
 O6(H6)
;
_shelx_res_checksum              32949
_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 1.524
_oxdiff_exptl_absorpt_empirical_full_min 0.764