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_7156588
_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 ad
_chemical_formula_moiety         'C25 H36 O4'
_chemical_formula_sum            'C25 H36 O4'
_chemical_formula_weight         400.54
_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   geom
_audit_creation_date             2017-11-09
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-04-20 deposited with the CCDC.
2018-11-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.827(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.2880(5)
_cell_length_b                   6.3903(2)
_cell_length_c                   14.4021(5)
_cell_measurement_reflns_used    3489
_cell_measurement_temperature    297.99(11)
_cell_measurement_theta_max      76.4720
_cell_measurement_theta_min      3.5440
_cell_volume                     1135.27(8)
_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  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.99(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.968
_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    -61.00  24.00   1.00    0.15    --  -48.45  44.00 113.00   85
  2  \w   -120.00 -36.00   1.00    0.15    --  -48.45 -44.00 -37.00   84
  3  \w     54.00  96.00   1.00    0.15    --   48.45  44.00 113.00   42
  4  \w     -6.00  20.00   1.00    0.15    --   48.45 -44.00 -37.00   26
  5  \w    -65.00 -38.00   1.00    1.50    --  -86.25  44.00 113.00   27
  6  \w   -108.00 -73.00   1.00    1.50    --  -86.25 -44.00 -37.00   35
  7  \w     55.00 119.00   1.00    1.50    --  107.75 -44.00 -37.00   64
  8  \w     95.00 177.00   1.00    1.50    --  107.75  44.00 113.00   82
  9  \w    -70.00 -16.00   1.00    1.50    --  -86.25 125.00 150.00   54
 10  \w     82.00 108.00   1.00    1.50    --  107.75 -99.00 150.00   26
 11  \w     37.00 120.00   1.00    1.50    --  107.75 -37.00 120.00   83
 12  \w     37.00 115.00   1.00    1.50    --  107.75 -57.00  60.00   78
 13  \w     36.00 115.00   1.00    1.50    --  107.75 -19.00 -60.00   79
 14  \w     42.00  68.00   1.00    1.50    --  107.75 -99.00 150.00   26
;
_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      0.0810978000
_diffrn_orient_matrix_UB_12      0.0982259000
_diffrn_orient_matrix_UB_13      0.0965159000
_diffrn_orient_matrix_UB_21      -0.0947890000
_diffrn_orient_matrix_UB_22      0.0725459000
_diffrn_orient_matrix_UB_23      0.0292385000
_diffrn_orient_matrix_UB_31      0.0051764000
_diffrn_orient_matrix_UB_32      -0.2078790000
_diffrn_orient_matrix_UB_33      0.0557647000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6212
_diffrn_reflns_point_group_measured_fraction_full 0.769
_diffrn_reflns_point_group_measured_fraction_max 0.780
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         3.583
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.614
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.01979
_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 light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 850 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       0.0077(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         3159
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0521
_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^)+(0.0810P)^2^+0.1915P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1355
_refine_ls_wR_factor_ref         0.1488
_reflns_Friedel_coverage         0.468
_reflns_Friedel_fraction_full    0.544
_reflns_Friedel_fraction_max     0.552
_reflns_number_gt                2805
_reflns_number_total             3159
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02687d2.cif
_cod_data_source_block           171109a
_cod_original_cell_volume        1135.26(8)
_cod_database_code               7156588
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         CO
_diffrn_oxdiff_ac3_digest_frames
;
015e709bf492fc39d8caff2a3eb84a1cb3007918bdd
;
_diffrn_oxdiff_ac3_digest_hkl
;
01ec23c5882e1a05a3d26502cb01c48472551a
;
_reflns_odcompleteness_completeness 97.31
_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
2.a Ternary CH refined with riding coordinates:
 C12(H12), C20(H20), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,
 H18B), C23(H23A,H23B)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C14(H14A,
 H14B,H14C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              63787
_shelx_hkl_checksum              26768
_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 20.553
_oxdiff_exptl_absorpt_empirical_full_min 0.460