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_7156589
_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 rm
_chemical_formula_moiety         'C37 H50 O6, C2 H3 N'
_chemical_formula_sum            'C39 H53 N O6'
_chemical_formula_weight         631.82
_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             2018-01-26
_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            8
_cell_length_a                   13.9171(3)
_cell_length_b                   18.5603(4)
_cell_length_c                   27.1890(5)
_cell_measurement_reflns_used    9215
_cell_measurement_temperature    150
_cell_measurement_theta_max      74.40
_cell_measurement_theta_min      3.57
_cell_volume                     7023.1(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 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_temperature      150.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            38119
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.097
_diffrn_reflns_theta_min         3.568
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.631
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0838 before and 0.0590 after correction.
The Ratio of minimum to maximum transmission is 0.9089.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_description       block
_exptl_crystal_F_000             2736
_exptl_crystal_preparation       'solvent MeCN'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 4938 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     845
_refine_ls_number_reflns         13595
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0378
_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^)+(0.0408P)^2^+1.1069P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0904
_reflns_Friedel_coverage         0.801
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                12154
_reflns_number_total             13595
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02687d2.cif
_cod_data_source_block           cu_0125_2_0m
_cod_database_code               7156589
_shelx_estimated_absorpt_t_max   0.911
_shelx_estimated_absorpt_t_min   0.858
_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:
 C00M(H00M), C00Q(H00Q), C00W(H00W), C00X(H00X), C014(H014), C015(H015),
 C01L(H5AA), C01N(H6AA), C01O(H01O), C01U(H8AA), C021(H021), C02A(H02F)
2.b Secondary CH2 refined with riding coordinates:
 C00O(H00C,H00D), C00P(H00A,H00B), C00R(H00E,H00F), C00Y(H00G,H00H), C012(H01Z,
 H), C013(H01,HA), C019(H01A,H01B), C01B(H0AA,HB), C01D(H2AA,HE), C01E(H01C,
 H01D), C01F(H01E,H01F), C01H(H3AA,HF), C01I(H01G,H01H), C01K(H01I,H01J),
 C01P(H01K,H01L), C01Q(H7AA,HI), C01S(H01M,H01N), C01W(H01V,H01W), C01X(H9AA,
 HJ), C01Z(H01X,H01Y), C020(H02R,H02S), C025(H02W,H02X), C026(H02A,H02B),
 C02G(H02M,H02N)
2.c Aromatic/amide H refined with riding coordinates:
 C00S(H00S), C018(H018)
2.d Idealised Me refined as rotating group:
 C01C(H1AA,HC,HD), C01J(H4AA,HG,HH), C01T(H01P,H01Q,H01R), C01V(H01S,H01T,
 H01U), C01Y(H0BA,HK,HL), C024(H02T,H02U,H02V), C027(H02C,H02D,H02E), C02B(H1BA,
 HM,HN), C02C(H02G,H02H,H02I), C02D(H02J,H02K,H02L), C02E(H02Y,HO,HP),
 C02F(H02Z,HQ,HR), C02H(H02O,H02P,H02Q), C02J(H02,HS,HT)
2.e Idealised tetrahedral OH refined as rotating group:
 O004(H004), O007(H007)
;
_shelx_shelxl_version_number     2016/6
_olex2_submission_original_sample_id 92-51
_olex2_submission_special_instructions 'No special instructions were received'