Triangeliphthalides A-D: Bioactive Phthalide Trimers with New Skeletons from Angelica sinensis and Their Production Mechanism
Zou, Jian; Chen, Guo-Dong; Zhao, Huan; Wang, Xiao-Xia; Zhang, Zaijun; Qu, Yi-Bo; He, Rong-Rong; So, Kwok-Fai; Yao, Xin-Sheng; Gao, Hao; Chemical Communications  (2019) –; doi:10.1039/C9CC02681A

data_7123383
_publ_section_title
;
 Triangeliphthalides A-D: Bioactive Phthalide Trimers with New Skeletons
 from Angelica sinensis and Their Production Mechanism
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC02681A
_journal_year                    2019
_chemical_formula_moiety         'C36 H40 O6'
_chemical_formula_sum            'C36 H40 O6'
_chemical_formula_weight         568.68
_chemical_name_systematic        'triangeliphthalide A'
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-12-05
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2018-12-05 deposited with the CCDC.    2019-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.221(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1653(12)
_cell_length_b                   27.523(2)
_cell_length_c                   8.5035(7)
_cell_measurement_reflns_used    11555
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      62.9330
_cell_measurement_theta_min      3.7890
_cell_volume                     3011.4(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0288
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega  -83.00   -8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.9934  113.0000 -175.0000 75

  2 omega  -63.00   37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.9934   77.0000  150.0000 100

  3 omega   13.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.9934   57.0000  120.0000 89

  4 omega  -36.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.9934  -57.0000  -90.0000 90

  5 omega   13.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.9934   57.0000  -90.0000 89

  6 omega  -11.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.9934   19.0000   90.0000 117

  7 omega   19.00  125.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -84.0000  172.2710 106

  8 omega   19.00  129.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000   65.7242 110

  9 omega   18.00   69.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000  -60.0000 51

 10 omega   19.00   77.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000 -120.0000 58

 11 omega   69.00  159.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000  -60.0000 90

 12 omega   19.00   77.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000   30.0000 58

 13 omega   69.00  159.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000  -30.0000 90

 14 omega   18.00   90.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000    0.0000 72

 15 omega   19.00  129.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -92.0000  -32.1005 110

 16 omega   69.00  159.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000  120.0000 90

 17 omega   19.00   83.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000  150.0000 64

 18 omega   18.00   69.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000   90.0000 51

 19 omega   79.00  163.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000 -120.0000 84

 20 omega   19.00   83.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000 -150.0000 64

 21 omega   79.00  163.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000   30.0000 84

 22 omega   17.00  144.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -15.0000  120.0000 127

 23 omega   17.00  144.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -15.0000  120.0000 127

 24 omega   60.00  161.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000   90.0000 101

 25 omega   79.00  163.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000 -150.0000 84

 26 omega   22.00  112.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -61.0000  120.0000 90

 27 omega   18.00  163.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -       90.5000    0.0000  -90.0000 145

 28 omega   19.00  129.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -92.0000 -127.3262 110

 29 omega   69.00  159.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000 -150.0000 90

 30 omega   62.00  160.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -       90.5000   75.0000 -131.1121 98

 31 omega   19.00   77.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000    0.0000 58

 32 omega   19.00   83.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000  -90.0000 64

 33 omega   19.00   83.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000  -60.0000 64

 34 omega   19.00  129.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000  177.4750 110

 35 omega -109.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.9934 -178.0000  -90.0000 52

 36 omega    3.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.9934   77.0000  -30.0000 100

 37 omega   35.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.9934  178.0000  120.0000 74

 38 omega    3.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.9934   77.0000   30.0000 100

 39 omega   13.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.9934   57.0000 -150.0000 89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0765860000
_diffrn_orient_matrix_UB_12      -0.0414132000
_diffrn_orient_matrix_UB_13      -0.0177490000
_diffrn_orient_matrix_UB_21      0.0905253000
_diffrn_orient_matrix_UB_22      0.0362696000
_diffrn_orient_matrix_UB_23      0.0325325000
_diffrn_orient_matrix_UB_31      0.0167569000
_diffrn_orient_matrix_UB_32      -0.0101847000
_diffrn_orient_matrix_UB_33      0.1814318000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0895
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            23463
_diffrn_reflns_point_group_measured_fraction_full 0.850
_diffrn_reflns_point_group_measured_fraction_max 0.850
_diffrn_reflns_theta_full        63.139
_diffrn_reflns_theta_max         63.139
_diffrn_reflns_theta_min         3.211
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1216
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1448 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.27(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         4147
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0502
_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^)+(0.0431P)^2^+3.9175P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1208
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_full    0.707
_reflns_Friedel_fraction_max     0.707
_reflns_number_gt                3980
_reflns_number_total             4147
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc02681a2.cif
_cod_data_source_block           GAOHAO41
_cod_original_cell_volume        3011.5(5)
_cod_database_code               7123383
_reflns_odcompleteness_completeness 97.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     63.60
_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:
 C9'(H9'), C3'(H3'), C9"(H9"), C4'(H4')
2.b Secondary CH2 refined with riding coordinates:
 C5'(H5'A,H5'B), C10'(H10A,H10B), C6'(H6'A,H6'B), C10"(H10C,H10D), C10(H10E,
 H10F), C5(H5A,H5B), C6(H6A,H6B), C11(H11A,H11B), C11"(H11C,H11D), C11'(H11E,
 H11F)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C5"(H5"), C3"(H3"), C3(H3), C6"(H6"), C4"(H4"), C4(H4)
2.d Idealised Me refined as rotating group:
 C12'(H12A,H12B,H12C), C12"(H12D,H12E,H12F), C12(H12G,H12H,H12I)
;
_shelx_res_checksum              77599
_shelx_hkl_checksum              49633
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'