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_4036080
_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         'C34 H32 O10'
_chemical_formula_sum            'C34 H32 O10'
_chemical_formula_weight         600.59
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-02-16
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.754(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   35.1338(16)
_cell_length_b                   24.4548(9)
_cell_length_c                   8.3344(2)
_cell_measurement_reflns_used    4089
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      73.2220
_cell_measurement_theta_min      2.1730
_cell_volume                     7157.5(5)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0775
_diffrn_reflns_av_unetI/netI     0.1073
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            28037
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.626
_diffrn_reflns_theta_min         2.202
_exptl_absorpt_coefficient_mu    0.684
_exptl_crystal_density_diffrn    1.115
_exptl_crystal_description       needle
_exptl_crystal_F_000             2528
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_refine_diff_density_max         1.015
_refine_diff_density_min         -1.138
_refine_diff_density_rms         0.167
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     670
_refine_ls_number_reflns         13926
_refine_ls_number_restraints     192
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.2713
_refine_ls_R_factor_gt           0.2491
_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^)+(0.1489P)^2^+198.9616P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.5237
_refine_ls_wR_factor_ref         0.5354
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10327
_reflns_number_total             13926
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02373_si_002.cif
_cod_data_source_block           300h_sqd_sqd
_cod_database_code               4036080
_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. Uiso/Uaniso restraints and constraints
C7B \\sim C8B \\sim C9B \\sim C14B \\sim C13B \\sim C12B \\sim C11B \\sim C10B:
within 1.7A with sigma of 0.001 and sigma for terminal atoms of 0.01
C8A \\sim C9A \\sim C10A \\sim C15A \\sim C14A \\sim C13A \\sim C12A \\sim
C11A: within 1.7A with sigma of 0.001 and sigma for terminal atoms of 0.01
C7' \\sim C8' \\sim C9' \\sim C14' \\sim C13' \\sim C12' \\sim C11' \\sim C10':
within 1.7A with sigma of 0.001 and sigma for terminal atoms of 0.01
C8 \\sim C9 \\sim C10 \\sim C15 \\sim C14 \\sim C13 \\sim C12 \\sim C11: within
1.7A with sigma of 0.001 and sigma for terminal atoms of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C7B(H7BA,H7BB), C8A(H8AA,H8AB), C8B(H8BA,H8BB), C9A(H9AA,H9AB), C16A(H16A,
 H16B), C7'(H7'A,H7'B), C8(H8A,H8B), C8'(H8'A,H8'B), C9(H9A,H9B), C16(H16F,H16G)
3.b Aromatic/amide H refined with riding coordinates:
 C10B(H10B), C11A(H11A), C11B(H11B), C12A(H12A), C12B(H12B), C13A(H13A),
 C13B(H13B), C14A(H14A), C14B(H14B), C15A(H15A), C10'(H10'), C11(H11),
 C11'(H11'), C12(H12), C12'(H12'), C13(H13), C13'(H13'), C14(H14), C14'(H14'),
 C15(H15)
3.c Idealised Me refined as rotating group:
 C16B(H16C,H16D,H16E), C17A(H17A,H17B,H17C), C17B(H17D,H17E,H17F), C16'(H16H,
 H16I,H16J), C17(H17G,H17H,H17I), C17'(H17J,H17K,H17L)
3.d Idealised tetrahedral OH refined as rotating group:
 O3A(H3A), O6A(H6A), O10A(H10A), O3(H3), O4(H4), O6(H6)
;
_platon_squeeze_void_probe_radius 1.20
_shelx_res_checksum              11805
_shelx_hkl_checksum              27381
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'