The Structural Revision and Total Synthesis of Carambolaflavone A.
Wang, Yong; Liu, Miao; Liu, Lei; Xia, Jian-Hui; Du, Yu-Guo; Sun, Jian-Song; The Journal of organic chemistry 83 (2018) 4111–4118; doi:10.1021/acs.joc.8b00008

data_4035453
_publ_section_title
;
 The Structural Revision and Total Synthesis of Carambolaflavone A.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4111
_journal_page_last               4118
_journal_paper_doi               10.1021/acs.joc.8b00008
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C42 H42 O8'
_chemical_formula_sum            'C42 H42 O8'
_chemical_formula_weight         674.75
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-04-11
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.5648(12)
_cell_length_b                   20.7782(14)
_cell_length_c                   7.6518(4)
_cell_measurement_reflns_used    5494
_cell_measurement_temperature    283.15(10)
_cell_measurement_theta_max      24.5620
_cell_measurement_theta_min      3.9090
_cell_volume                     3587.6(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      283.15(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0353
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_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    -85.00   3.00   1.00   58.62    --  -15.92 -37.00   0.00   88
  2  \w    -83.00   1.00   1.00   58.62    --  -15.92 -57.00 -90.00   84
  3  \w      8.00  56.00   1.00   58.62    --   16.85 -99.00  90.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0109881000
_diffrn_orient_matrix_UB_12      0.0316393000
_diffrn_orient_matrix_UB_13      -0.0130832000
_diffrn_orient_matrix_UB_21      0.0294161000
_diffrn_orient_matrix_UB_22      0.0116102000
_diffrn_orient_matrix_UB_23      -0.0077781000
_diffrn_orient_matrix_UB_31      -0.0009546000
_diffrn_orient_matrix_UB_32      -0.0055396000
_diffrn_orient_matrix_UB_33      -0.0914531000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            16329
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         3.307
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88455
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_description       acicular
_exptl_crystal_F_000             1432
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1855 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     455
_refine_ls_number_reflns         6930
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0370P)^2^+0.4120P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0984
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_full    0.970
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                5602
_reflns_number_total             6930
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00008_si_002.cif
_cod_data_source_block           1
_cod_database_code               4035453
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C2(H2A), C3(H3), C4(H4A), C5(H5), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C22(H22A,H22B), C29(H29A,H29B), C36(H36A,H36B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C24(H24),
 C25(H25), C26(H26), C27(H27), C28(H28), C31(H31), C32(H32), C33(H33), C34(H34),
  C35(H35), C38(H38), C39(H39), C40(H40), C41(H41), C42(H42)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C11(H11A,H11B,H11C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.309
_oxdiff_exptl_absorpt_empirical_full_min 0.747