Meroterpene-like compounds derived from β-caryophyllene as potent α-glucosidase inhibitors
Ma, Shuang-Jiang; Yu, Jie; Yan, Da-Wei; Wang, Da-Cheng; Gao, Jin-Ming; Zhang, Qiang; Organic & Biomolecular Chemistry  (2018) –; doi:10.1039/C8OB02687D

data_7156587
_publ_section_title
;
 Meroterpene-like compounds derived from \b-caryophyllene as potent
 \a-glucosidase inhibitors
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/C8OB02687D
_journal_year                    2018
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C25 H30 O4, C H4 O'
_chemical_formula_sum            'C26 H34 O5'
_chemical_formula_weight         426.56
_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_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_date             2018-02-25
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2018-04-20 deposited with the CCDC.
2018-11-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7671(1)
_cell_length_b                   16.3554(3)
_cell_length_c                   17.5789(3)
_cell_measurement_reflns_used    7740
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      76.5690
_cell_measurement_theta_min      4.9990
_cell_volume                     2233.12(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.30d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.30d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.30d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9939
_diffrn_measured_fraction_theta_max 0.9123
_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    -72.00 -14.00   1.00    0.50    --  -86.25 125.00 150.00   58
  2  \w    -60.00  24.00   1.00    0.10    --  -48.45  57.00  90.00   84
  3  \w    -61.00 -22.00   1.00    0.10    --  -48.45  19.00  28.00   39
  4  \w     40.00 104.00   1.00    0.10    --   48.45  19.00  28.00   64
  5  \w    106.00 135.00   1.00    0.50    --  107.75  19.00  28.00   29
  6  \w    -79.00 -54.00   1.00    0.50    --  -86.25  19.00  28.00   25
  7  \w   -159.00-127.00   1.00    0.50    --  -86.25 -19.00-139.00   32
  8  \w   -104.00 -79.00   1.00    0.10    --  -48.45 -19.00-139.00   25
  9  \w    -26.00  39.00   1.00    0.10    --   48.45 -19.00-139.00   65
 10  \w     33.00 113.00   1.00    0.50    --  107.75 -19.00-139.00   80
 11  \w     37.00 119.00   1.00    0.50    --  107.75 -37.00-120.00   82
 12  \w     38.00 110.00   1.00    0.50    --  107.75 -99.00-120.00   72
 13  \w     45.00 116.00   1.00    0.50    --  107.75-125.00-120.00   71
 14  \w     36.00 104.00   1.00    0.50    --  107.75 -99.00  60.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0402806000
_diffrn_orient_matrix_UB_12      -0.0149198000
_diffrn_orient_matrix_UB_13      -0.0846651000
_diffrn_orient_matrix_UB_21      -0.1879066000
_diffrn_orient_matrix_UB_22      0.0205758000
_diffrn_orient_matrix_UB_23      -0.0206306000
_diffrn_orient_matrix_UB_31      0.0492548000
_diffrn_orient_matrix_UB_32      0.0906859000
_diffrn_orient_matrix_UB_33      -0.0092664000
_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  0.0487
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12629
_diffrn_reflns_theta_full        67.0752
_diffrn_reflns_theta_max         67.08
_diffrn_reflns_theta_min         5.03
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.695
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.30d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.2686
_exptl_crystal_description       block
_exptl_crystal_F_000             922.9450
_exptl_crystal_preparation       'in MeOH'
_exptl_crystal_recrystallization_method MeOH
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.3978
_refine_diff_density_min         -0.4977
_refine_diff_density_rms         0.0602
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -9.43(3)
_refine_ls_d_res_high            0.8370
_refine_ls_d_res_low             8.7895
_refine_ls_goodness_of_fit_ref   1.0301
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    54
_refine_ls_number_parameters     285
_refine_ls_number_reflns         3861
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0301
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0482
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0728P)^2^+1.2933P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1404
_reflns_Friedel_coverage         0.939
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              19
_reflns_limit_k_min              -19
_reflns_limit_l_max              20
_reflns_limit_l_min              -20
_reflns_number_gt                3521
_reflns_number_total             3861
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c8ob02687d2.cif
_cod_data_source_block           171204B
_cod_database_code               7156587
_chemical_oxdiff_formula         CHO
_diffrn_oxdiff_ac3_digest_frames
;
01d91ef1a8feaffe57d7fb2bed105e11d90004491e1
;
_diffrn_oxdiff_ac3_digest_hkl
;
0101cda8dc46fdb7cca871b59959bf53636ae9
;
_reflns_odcompleteness_completeness 99.39
_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:
 C11(H11), C8(H8), C4(H4), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13a,H13b), C9(H9a,H9b), C12(H12a,H12b), C5(H5a,H5b), C6(H6a,H6b), C3(H3a,
 H3b)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C18(H18), C20(H20), C19(H19)
2.d Idealised Me refined as rotating group:
 C28(H28a,H28b,H28c), C29(H29a,H29b,H29c), C27(H27a,H27b,H27c), C30(H30a,H30b,
 H30c)
2.e Idealised tetrahedral OH refined as rotating group:
 O26(H26), O31(H31)
;
_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 1.839
_oxdiff_exptl_absorpt_empirical_full_min 0.631