Anti-inflammatory Dimeric 2-(2-Phenylethyl)chromones from the Resinous Wood of Aquilaria sinensis.
Huo, Hui-Xia; Zhu, Zhi-Xiang; Song, Yue-Lin; Shi, She-Po; Sun, Jing; Sun, Hui; Zhao, Yun-Fang; Zheng, Jiao; Ferreira, Daneel; Zjawiony, Jordan K.; Tu, Peng-Fei; Li, Jun; Journal of natural products  (2017) –; doi:10.1021/acs.jnatprod.7b00919

data_1548447
_publ_section_title
;
 Anti-inflammatory Dimeric 2-(2-Phenylethyl)chromones from the Resinous
 Wood of Aquilaria sinensis.
;
_journal_name_full               'Journal of natural products'
_journal_paper_doi               10.1021/acs.jnatprod.7b00919
_journal_year                    2017
_chemical_formula_moiety         'C34 H28 O7, C H4 O'
_chemical_formula_sum            'C35 H32 O8'
_chemical_formula_weight         580.61
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-03-10
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                110.146(4)
_cell_angle_beta                 98.926(4)
_cell_angle_gamma                99.616(4)
_cell_formula_units_Z            2
_cell_length_a                   9.6731(4)
_cell_length_b                   11.8776(6)
_cell_length_c                   13.3871(6)
_cell_measurement_reflns_used    7417
_cell_measurement_temperature    107.2
_cell_measurement_theta_max      70.8408
_cell_measurement_theta_min      3.6105
_cell_volume                     1385.60(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_temperature      107.2
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
  1 omega  -53.00   34.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   45.0000 -150.0000 87

  2 omega  -47.00   -5.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000    0.0000 42

  3 omega -101.00  -76.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -54.0000  108.0000 25

  4 omega  -77.00  -12.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  111.0000   60.0000 65

  5 omega -102.00  -75.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000    0.0000 27

  6 omega  -95.00  -56.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -45.0000 -150.0000 39

  7 omega  -54.00  -16.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -45.0000 -150.0000 38

  8 omega  -55.00  -16.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -54.0000  108.0000 39

  9 omega  -53.00   33.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   45.0000   30.0000 86

 10 omega  -80.00   15.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  111.0000 -120.0000 95

 11 omega    3.00   28.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       34.7391   83.0000   19.0000 25

 12 omega    1.00   26.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.0000   97.0000  114.0000 25

 13 omega    2.00   27.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.0000   94.0000 -179.0000 25

 14 omega   13.00   38.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   88.0000  -79.0000 25

 15 omega   20.00   45.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   83.0000   96.0000 25

 16 omega   20.00   45.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   84.0000  -47.0000 25

 17 omega   20.00   45.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   84.0000   56.0000 25

 18 omega   20.00   45.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   84.0000  151.0000 25

 19 omega   20.00   45.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   84.0000 -161.0000 25

 20 omega   20.00   45.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   84.0000    9.0000 25

 21 omega   87.00  114.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   69.0000 -119.0000 27

 22 omega   35.00   65.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   69.0000 -119.0000 30

 23 omega   32.00   74.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   69.0000 -162.0000 42

 24 omega   94.00  128.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   74.0000  -97.0000 34

 25 omega   34.00   76.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   74.0000  -97.0000 42

 26 omega   44.00   93.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   67.0000  149.0000 49

 27 omega   36.00  107.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   72.0000  -39.0000 71

 28 omega   34.00  128.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   72.0000   41.0000 94

 29 omega   31.00   61.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   77.0000  122.0000 30

 30 omega   79.00  162.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 83

 31 omega   46.00  114.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -128.0000  -80.0000 68

 32 omega   79.00  170.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 91

 33 omega  139.00  177.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 38

 34 omega   64.00  116.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -113.0000  -14.0000 52

 35 omega   79.00  136.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 57

 36 omega   95.00  136.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -90.0000 41

 37 omega   40.00   73.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -90.0000 33

 38 omega   79.00  149.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 70

 39 omega   79.00  177.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 98

 40 omega   79.00  176.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 97

 41 omega   79.00  170.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 91

 42 omega   41.00  106.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  120.0000 65

 43 omega   79.00  175.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 96

 44 omega   79.00  167.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 88

 45 omega   79.00  170.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 91

 46 omega   79.00  159.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 80

 47 omega   79.00  158.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 79

 48 omega   42.00  107.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -105.0000  102.0000 65
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0923129000
_diffrn_orient_matrix_UB_12      0.0953919000
_diffrn_orient_matrix_UB_13      0.0286942000
_diffrn_orient_matrix_UB_21      0.0084464000
_diffrn_orient_matrix_UB_22      0.0206676000
_diffrn_orient_matrix_UB_23      -0.1065775000
_diffrn_orient_matrix_UB_31      -0.1376734000
_diffrn_orient_matrix_UB_32      -0.1034589000
_diffrn_orient_matrix_UB_33      -0.0606696000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17394
_diffrn_reflns_theta_full        70.98
_diffrn_reflns_theta_max         70.98
_diffrn_reflns_theta_min         3.61
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.808
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         5259
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0390
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0574P)^2^+0.4261P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1064
_reflns_number_gt                4608
_reflns_number_total             5259
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np7b00919_si_002.cif
_cod_data_source_block           exp_3891
_cod_original_cell_volume        1385.60(11)
_cod_database_code               1548447
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97