Xanthchrysones A-C: Rearranged Phenylpropanoyl-Phloroglucinol Dimers with Unusual Skeletons from Xanthostemon chrysanthus.
Liu, Fen; Tian, Hai-Yan; Huang, Xiao-Lin; Wang, Wen-Jing; Li, Ni-Ping; He, Jun; Ye, Wen-Cai; Wang, Lei; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02373

data_4036079
_publ_section_title
;
 Xanthchrysones A-C: Rearranged Phenylpropanoyl-Phloroglucinol Dimers with
 Unusual Skeletons from Xanthostemon chrysanthus.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02373
_journal_year                    2019
_chemical_formula_moiety         'C18 H18 O5'
_chemical_formula_sum            'C18 H18 O5'
_chemical_formula_weight         314.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_cell_angle_alpha                90.0
_cell_angle_beta                 98.6865(10)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   17.90301(18)
_cell_length_b                   7.47461(9)
_cell_length_c                   11.71091(12)
_cell_measurement_reflns_used    22511
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.4620
_cell_measurement_theta_min      2.4680
_cell_volume                     1549.15(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9952
_diffrn_measured_fraction_theta_max 0.9952
_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   -117.00  -8.00   1.00    1.00    --  -40.98 -77.00 -90.00  109
  2  \w   -113.00 -13.00   1.00    1.00    --  -40.98 -57.00  30.00  100
  3  \w   -117.00  -8.00   1.00    1.00    --  -40.98 -77.00  30.00  109
  4  \w    -66.00  33.00   1.00    1.00    --  -40.98  38.00-180.00   99
  5  \w   -115.00 -16.00   1.00    1.00    --  -40.98 -38.00 -90.00   99
  6  \w      1.00  82.00   1.00    1.00    --   40.98 -99.00-120.00   81
  7  \w     23.00  97.00   1.00    1.00    --   40.98-125.00 150.00   74
  8  \w     25.00 109.00   1.00    1.00    --  106.95 -95.00 150.00   84
  9  \w     81.00 178.00   1.00    1.00    --  106.95  45.00  30.00   97
 10  \w     78.00 178.00   1.00    1.00    --  106.95  61.00  60.00  100
 11  \w     74.00 178.00   1.00    1.00    --  106.95  77.00  60.00  104
 12  \w     74.00 178.00   1.00    1.00    --  106.95  77.00 -30.00  104
 13  \w     31.00 135.00   1.00    1.00    --  106.95 -30.00 -30.00  104
 14  \w     74.00 178.00   1.00    1.00    --  106.95  77.00   0.00  104
 15  \w     74.00 178.00   1.00    1.00    --  106.95  77.00 -60.00  104
 16  \w     78.00 178.00   1.00    1.00    --  106.95  61.00   0.00  100
 17  \w     74.00 178.00   1.00    1.00    --  106.95  77.00  30.00  104
 18  \w     94.00 178.00   1.00    1.00    --  106.95 125.00 150.00   84
 19  \w     78.00 178.00   1.00    1.00    --  106.95  61.00  30.00  100
 20  \w     81.00 178.00   1.00    1.00    --  106.95  45.00  60.00   97
 21  \w     81.00 178.00   1.00    1.00    --  106.95  45.00   0.00   97
 22  \w     81.00 178.00   1.00    1.00    --  106.95  45.00  90.00   97
 23  \w     81.00 178.00   1.00    1.00    --  106.95  45.00 -30.00   97
 24  \w     94.00 178.00   1.00    1.00    --  106.95 125.00  90.00   84
 25  \w     78.00 178.00   1.00    1.00    --  106.95  61.00 -30.00  100
 26  \w     34.00 121.00   1.00    1.00    --  106.95-125.00  30.00   87
 27  \w   -117.00 -13.00   1.00    1.00    --  -40.98 -30.00 124.00  104
 28  \w   -113.00 -13.00   1.00    1.00    --  -40.98 -57.00 150.00  100
 29  \w   -117.00  -8.00   1.00    1.00    --  -40.98 -77.00 120.00  109
 30  \w   -117.00  -8.00   1.00    1.00    --  -40.98 -77.00   0.00  109
 31  \w    -96.00  -2.00   1.00    1.00    --  -40.98 125.00 -30.00   94
 32  \w    -69.00  32.00   1.00    1.00    --  -40.98  57.00 -30.00  101
 33  \w   -115.00 -16.00   1.00    1.00    --  -40.98 -38.00 120.00   99
 34  \w      8.00 117.00   1.00    1.00    --   40.98  77.00 -90.00  109
 35  \w     54.00 162.00   1.00    1.00    --  106.95  15.00-150.00  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0807924000
_diffrn_orient_matrix_UB_12      0.0765325000
_diffrn_orient_matrix_UB_13      0.0220380000
_diffrn_orient_matrix_UB_21      -0.0032151000
_diffrn_orient_matrix_UB_22      0.0331720000
_diffrn_orient_matrix_UB_23      -0.1304815000
_diffrn_orient_matrix_UB_31      -0.0322068000
_diffrn_orient_matrix_UB_32      0.1885196000
_diffrn_orient_matrix_UB_33      0.0140139000
_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  0.0460
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            29614
_diffrn_reflns_theta_full        73.6349
_diffrn_reflns_theta_max         73.63
_diffrn_reflns_theta_min         2.50
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.813
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.3477
_exptl_crystal_description       block
_exptl_crystal_F_000             666.3589
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.3416
_refine_diff_density_min         -0.2342
_refine_diff_density_rms         0.0520
_refine_ls_d_res_high            0.8035
_refine_ls_d_res_low             17.6976
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.7373
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3125
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.7373
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0440
_refine_ls_shift/su_max          0.0023
_refine_ls_shift/su_mean         0.0005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0772P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1530
_refine_ls_wR_factor_ref         0.1538
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              21
_reflns_limit_h_min              -22
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                3035
_reflns_number_total             3125
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo9b02373_si_003.cif
_cod_data_source_block           J_3
_cod_original_cell_volume        1549.16(3)
_cod_database_code               4036079
_cell_oxdiff_angle_alpha         89.9980(14)
_cell_oxdiff_angle_beta          98.6840(13)
_cell_oxdiff_angle_gamma         90.0160(14)
_cell_oxdiff_length_a            17.9059(3)
_cell_oxdiff_length_b            7.47307(14)
_cell_oxdiff_length_c            11.71140(19)
_cell_oxdiff_measurement_reflns_used 22511
_cell_oxdiff_volume              1549.16(4)
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C7(H7), C10(H10), C14(H14), C13(H13), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c), C17(H17a,H17b,H17c), C16(H16a,H16b,H16c)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4), O1(H1)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.108
_oxdiff_exptl_absorpt_empirical_full_min 0.508