Concise total syntheses of two flavans and structure revision assisted by quantum NMR calculations.
Zhou, Tingting; Zheng, Anquan; Zhang, Wenge; Lu, Xiuxiang; Chen, Huiyu; Tan, Haibo; Organic & biomolecular chemistry 20 (2022) 4096–4100; doi:10.1039/d2ob00634k

data_7158662
_publ_section_title
;
 Concise total syntheses of two flavans and structure revision assisted by
 quantum NMR calculations.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4096
_journal_page_last               4100
_journal_paper_doi               10.1039/d2ob00634k
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         '2(C17 H16 O5)'
_chemical_formula_sum            'C34 H32 O10'
_chemical_formula_weight         600.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-08-23 deposited with the CCDC.	2022-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.841(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.5676(5)
_cell_length_b                   13.8531(3)
_cell_length_c                   26.8877(10)
_cell_measurement_reflns_used    4895
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      73.5430
_cell_measurement_theta_min      3.0310
_cell_volume                     5713.3(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Pilatus3R 200K-A'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.970
_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     55.00  86.50   0.30    1.00    --    0.00  19.00  60.00  105
  2  \w    -23.00  19.00   0.30    1.00    --    0.00 -82.00-120.00  140
  3  \w    -24.00  23.10   0.30    1.00    --    0.00 -82.00  30.00  157
  4  \w     -6.00  19.20   0.30    1.00    --    0.00  19.00  60.00   84
  5  \w    -32.00   7.00   0.30    1.00    --    0.00 -82.00 -90.00  130
  6  \w     16.00 104.20   0.30    6.50    --   95.80 -15.00 150.00  294
  7  \w     93.00 120.00   0.30    6.50    --   95.80  82.00  60.00   90
  8  \w     95.00 158.30   0.30    6.50    --   95.80  82.00  90.00  211
  9  \w    144.00 175.20   0.30    6.50    --   95.80  82.00 -60.00  104
 10  \w     65.00  99.20   0.30    6.50    --   95.80 -30.00 -30.00  114
 11  \w      7.00  90.10   0.30    6.50    --   95.80 -61.00 -30.00  277
 12  \w      9.00 114.00   0.30    6.50    --   95.80 -45.00 -30.00  350
 13  \w    148.00 174.10   0.30    6.50    --   95.80  82.00  60.00   87
 14  \w     12.00 105.00   0.30    6.50    --   95.80 -30.00 120.00  310
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0388614000
_diffrn_orient_matrix_UB_12      0.0877260000
_diffrn_orient_matrix_UB_13      -0.0234851000
_diffrn_orient_matrix_UB_21      0.0418495000
_diffrn_orient_matrix_UB_22      0.0346680000
_diffrn_orient_matrix_UB_23      0.0530820000
_diffrn_orient_matrix_UB_31      0.0826344000
_diffrn_orient_matrix_UB_32      -0.0588749000
_diffrn_orient_matrix_UB_33      -0.0036851000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            15091
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.304
_diffrn_reflns_theta_min         3.337
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'MicroMax 007 (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.857
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_description       needle
_exptl_crystal_F_000             2528
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         5654
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0610
_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^)+(0.0547P)^2^+8.0895P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1490
_refine_ls_wR_factor_ref         0.1618
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4045
_reflns_number_total             5654
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00634k2.cif
_cod_data_source_block           zhoutingting_zt200924-1_collect
_cod_depositor_comments          'Adding full bibliography for 7158662.cif.'
_cod_database_code               7158662
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.783
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Others
 Sof(C4'A)=Sof(H4'A)=Sof(C3'A)=Sof(C2'A)=Sof(H2'A)=1-FVAR(1)
 Sof(C4')=Sof(H4')=Sof(C2')=Sof(H2')=Sof(C3')=FVAR(1)
 Fixed Sof: O009(0.5) O013(0.5) C018(0.5) H01A(0.5) H01B(0.5) H01C(0.5)
 O0(0.5) O1(0.5) C0(0.5) H0A(0.5) H0B(0.5) H0C(0.5) C0AA(0.5) H0AA(0.5)
 H0AB(0.5) H0AC(0.5) C1A(0.5) H1AA(0.5) H1AB(0.5) H1AC(0.5)
3.a Ternary CH refined with riding coordinates:
 C11'(H11'), C6'(H6'), C12(H12), C6(H6)
3.b Secondary CH2 refined with riding coordinates:
 C12'(H12A,H12B), C13(H13A,H13B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C7'(H7'), C00M(H00M), C9(H9), C8'(H8'), C4(H4), C8(H8), C7(H7),
 C4'(H4'), C2'(H2'), C4'A(H4'A), C2'A(H2'A)
3.d Idealised Me refined as rotating group:
 C00Q(H00A,H00B,H00C), C00Z(H00D,H00E,H00F), C018(H01A,H01B,H01C), C0(H0A,H0B,
 H0C), C0AA(H0AA,H0AB,H0AC), C1A(H1AA,H1AB,H1AC)
3.e Idealised tetrahedral OH refined as rotating group:
 O003(H003), O007(H007)
;
_shelx_res_checksum              72566
_shelx_hkl_checksum              64932
_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 1.075
_oxdiff_exptl_absorpt_empirical_full_min 0.914