Stereoselective total synthesis of (±)-vindeburnol and (±)-16-<i>epi</i>-vindeburnol.
Chen, Xiangtao; Yu, Lei; Wang, Huijing; Zhang, Wen; Tang, Pei; Chen, Fener; Chemical communications (Cambridge, England) 57 (2021) 11669–11672; doi:10.1039/d1cc04980a

data_7129096
_publ_section_title
;
 Stereoselective total synthesis of (+-)-vindeburnol and
 (+-)-16-<i>epi</i>-vindeburnol.
;
_journal_issue                   88
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11669
_journal_page_last               11672
_journal_paper_doi               10.1039/d1cc04980a
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C17 H20 N2 O2'
_chemical_formula_sum            'C17 H20 N2 O2'
_chemical_formula_weight         284.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc28ldcn
_audit_creation_date             2021-07-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-08-13 deposited with the CCDC.	2021-10-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.950(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.1352(3)
_cell_length_b                   18.7726(5)
_cell_length_c                   15.8738(5)
_cell_measurement_reflns_used    4752
_cell_measurement_temperature    297.1(5)
_cell_measurement_theta_max      71.2440
_cell_measurement_theta_min      5.0660
_cell_volume                     2931.14(15)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.1(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.977
_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    -73.00  37.00   1.00    1.00    --  -34.98  19.00 -30.00  110
  2  \w     16.00 103.00   1.00    1.00    --   34.98  57.00  90.00   87
  3  \w     23.00  90.00   1.00    1.00    --   34.98-125.00 -30.00   67
  4  \w     23.00  90.00   1.00    1.00    --   34.98-125.00-180.00   67
  5  \w    -34.00  64.00   1.00    1.00    --   34.98 -77.00 -60.00   98
  6  \w    -33.00  53.00   1.00    1.00    --   34.98 -57.00-150.00   86
  7  \w    -33.00  53.00   1.00    1.00    --   34.98 -57.00 150.00   86
  8  \w     39.00 127.00   1.00    3.85    --  106.90 -61.00-150.00   88
  9  \w     35.00 133.00   1.00    3.85    --  106.90 -30.00-180.00   98
 10  \w     37.00 110.00   1.00    3.85    --  106.90 -94.00-180.00   73
 11  \w     35.00 133.00   1.00    3.85    --  106.90 -30.00  30.00   98
 12  \w     87.00 177.00   1.00    3.85    --  106.90  45.00-150.00   90
 13  \w     37.00 127.00   1.00    3.85    --  106.90 -45.00 120.00   90
 14  \w     57.00  69.00   1.00    3.85    --  106.90 178.00  30.00   12
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1301468000
_diffrn_orient_matrix_UB_12      -0.0142713000
_diffrn_orient_matrix_UB_13      0.0313303000
_diffrn_orient_matrix_UB_21      -0.0871841000
_diffrn_orient_matrix_UB_22      0.0188358000
_diffrn_orient_matrix_UB_23      -0.0909176000
_diffrn_orient_matrix_UB_31      0.0027321000
_diffrn_orient_matrix_UB_32      -0.0785576000
_diffrn_orient_matrix_UB_33      -0.0274189000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13940
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.354
_diffrn_reflns_theta_min         3.712
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.681
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.289
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         5563
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0565
_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^)+(0.0900P)^2^+0.4473P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1488
_refine_ls_wR_factor_ref         0.1611
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4624
_reflns_number_total             5563
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc04980a2.cif
_cod_data_source_block           cfe-cxt-200424a
_cod_depositor_comments
'Adding full bibliography for 7129096--7129098.cif.'
_cod_database_code               7129096
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C00F(H00F), C00G(H00L), C00L(H00M), C00O(H00O)
1.b Secondary CH2 refined with riding coordinates:
 C00K(H00A,H00B), C00M(H00C,H00D), C00R(H00E,H00G), C00T(H00H,H00I), C00V(H00Q,
 H00R), C00X(H00T,H00V), C00Y(H00J,H00K), C00Z(H00X,H00Y), C012(H01C,H01D),
 C014(H01E,H01F), C015(H01A,H01B), C016(H01G,H01H)
1.c Aromatic/amide H refined with riding coordinates:
 N004(H004), N005(H005), C00N(H00N), C00S(H00S), C010(H010), C011(H011),
 C013(H013)
1.d Idealised tetrahedral OH refined as rotating group:
 O001(H001), O003(H003)
;
_shelx_res_checksum              6640
_shelx_hkl_checksum              32865
_olex2_date_sample_data_collection 2020-06-16
_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 1.281
_oxdiff_exptl_absorpt_empirical_full_min 0.804