Atropisomeric 9,10-dihydrophenanthrene/bibenzyl trimers with anti-inflammatory and PTP1B inhibitory activities from Bletilla striata
Sun, Mohan; Ma, Xianjie; Shao, Siyuan; Jiang, Jianwei; Li, Jiaan; Tian, Jinying; Zhang, Jianjun; Li, Li; Ye, Fei; Li, Shuai; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00489E

data_7158709
_publ_section_title
;
 Atropisomeric 9,10-dihydrophenanthrene/bibenzyl trimers with
 anti-inflammatory and PTP1B inhibitory activities from Bletilla striata
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00489E
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H20 O4'
_chemical_formula_sum            'C22 H20 O4'
_chemical_formula_weight         348.38
_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             2021-03-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-08-02 deposited with the CCDC.	2022-05-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.34810(10)
_cell_length_b                   14.9237(2)
_cell_length_c                   19.9392(3)
_cell_measurement_reflns_used    21338
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.0810
_cell_measurement_theta_min      3.6910
_cell_volume                     3376.82(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.975
_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     31.00 106.00   0.50    0.62    --  103.25 -95.00  -7.00  150
  2  \w     91.00 178.00   0.50    0.62    --  103.25  30.00-180.00  174
  3  \w     82.00 176.00   0.50    0.62    --  103.25  74.00-142.00  188
  4  \w     33.00 120.00   0.50    0.15    --   47.70  57.00-150.00  174
  5  \w    -23.00  28.00   0.50    0.15    --  -47.70  19.00   0.00  102
  6  \w    -23.00  28.00   0.50    0.15    --  -47.70  19.00 -60.00  102
  7  \w    -69.00  25.00   0.50    0.15    --  -47.70  74.00-142.00  188
  8  \w    -68.00 -28.00   0.50    0.62    -- -101.00  61.00 -30.00   80
  9  \w    -61.00 -28.00   0.50    0.62    -- -101.00  56.00   3.00   66
 10  \w    -68.00 -28.00   0.50    0.62    -- -101.00  61.00  60.00   80
 11  \w     31.00  75.00   0.50    0.62    --  103.25 -61.00  90.00   88
 12  \w     31.00  75.00   0.50    0.62    --  103.25 -61.00 150.00   88
 13  \w     31.00  75.00   0.50    0.62    --  103.25 -61.00 120.00   88
 14  \w     31.00  75.00   0.50    0.62    --  103.25 -61.00  60.00   88
 15  \w     31.00  68.00   0.50    0.62    --  103.25 -56.00-138.00   74
 16  \w    -27.00  30.00   0.50    0.15    --   47.70 -19.00  90.00  114
 17  \w   -173.00 -84.00   0.50    0.62    -- -101.00 -61.00  30.00  178
 18  \w   -119.00 -59.00   0.50    0.15    --  -47.70 -57.00  60.00  120
 19  \w   -173.00 -88.00   0.50    0.62    -- -101.00 -45.00 -90.00  170
 20  \w   -173.00 -84.00   0.50    0.62    -- -101.00 -61.00 -60.00  178
 21  \w   -126.00 -84.00   0.50    0.62    -- -101.00 -95.00  -7.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0860040000
_diffrn_orient_matrix_UB_12      -0.0754500000
_diffrn_orient_matrix_UB_13      0.0198278000
_diffrn_orient_matrix_UB_21      -0.0927749000
_diffrn_orient_matrix_UB_22      0.0383034000
_diffrn_orient_matrix_UB_23      -0.0486038000
_diffrn_orient_matrix_UB_31      0.0494656000
_diffrn_orient_matrix_UB_32      -0.0590929000
_diffrn_orient_matrix_UB_33      -0.0566547000
_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  0.0527
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            29039
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.435
_diffrn_reflns_theta_min         3.700
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.760
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76319
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
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    1.371
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 2670 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     477
_refine_ls_number_reflns         6708
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0341
_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^)+(0.0446P)^2^+0.7523P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0879
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.937
_reflns_number_gt                6402
_reflns_number_total             6708
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00489e2.cif
_cod_data_source_block           smh_1_auto
_cod_database_code               7158709
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.888
_reflns_odcompleteness_completeness 99.77
_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 Secondary CH2 refined with riding coordinates:
 C16(H16a,H16b), C42(H42a,H42b), C5(H5a,H5b), C6(H6a,H6b), C30(H30a,H30b),
 C29(H29a,H29b)
2.b Aromatic/amide H refined with riding coordinates:
 C37(H37), C22(H22), C34(H34), C10(H10), C40(H40), C14(H14), C12(H12),
 C11(H11), C18(H18), C21(H21), C38(H38), C19(H19), C47(H47), C44(H44), C45(H45),
  C48(H48)
2.c Idealised Me refined as rotating group:
 C51(H51a,H51b,H51c), C25(H25a,H25b,H25c)
2.d Idealised tetrahedral OH refined as rotating group:
 O26(H26), O49(H49), O52(H52), O15(H15), O23(H23), O41(H41)
;
_shelx_res_checksum              57521
_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 1.832
_oxdiff_exptl_absorpt_empirical_full_min 0.584