A catalytic, enantioselective formal synthesis of (+)-dichroanone and (+)-taiwaniaquinone H.
Shockley, Samantha E.; Holder, Jeffrey C.; Stoltz, Brian M.; Organic letters 16 (2014) 6362–6365; doi:10.1021/ol5031537

data_1518417
_publ_section_title
;
 A catalytic, enantioselective formal synthesis of (+)-dichroanone and
 (+)-taiwaniaquinone H.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6362
_journal_page_last               6365
_journal_paper_doi               10.1021/ol5031537
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H21 Br O4, H2 O'
_chemical_formula_sum            'C17 H23 Br O5'
_chemical_formula_weight         387.26
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2014-03-26
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.12 svn.r2899 for OlexSys, GUI svn.r4796),
 SHELXL-2014,
 and manual edit
;
_cell_angle_alpha                90
_cell_angle_beta                 95.208(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.8295(9)
_cell_length_b                   7.8451(4)
_cell_length_c                   11.4443(5)
_cell_measurement_reflns_used    9869
_cell_measurement_temperature    100
_cell_measurement_theta_max      45.67
_cell_measurement_theta_min      2.82
_cell_volume                     1683.57(14)
_computing_cell_refinement       'SAINT V8.34A (Bruker-AXS, 2007)'
_computing_data_collection       'APEX2 2014.1-1 (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT V8.34A (Bruker-AXS, 2007)'
_computing_molecular_graphics    'DIAMOND 3 (Crystal Impact, 1999)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/2 (Sheldrick, 2014)'
_computing_structure_solution    'XT-2014/1 (Sheldrick, 2012)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            78240
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         48.826
_diffrn_reflns_theta_min         1.787
_diffrn_source_current           30
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.464
_exptl_absorpt_correction_T_max  0.5777
_exptl_absorpt_correction_T_min  0.4462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
A face-indexed correction (linear absorption coefficient refined 
to 2.58 mm-1) was followed by default multi-scan.
wR2(int) was 0.0809 before and 0.0746 after correction.
The Ratio of minimum to maximum transmission is 0.7724.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_description       chunk
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.653
_refine_diff_density_min         -0.707
_refine_diff_density_rms         0.100
_refine_ls_abs_structure_details
;
 Flack x determined using 5880 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0289(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         16574
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0256
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0157P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0521
_refine_ls_wR_factor_ref         0.0538
_reflns_Friedel_coverage         0.899
_reflns_Friedel_fraction_full    0.952
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                14231
_reflns_number_total             16574
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5031537_si_002.cif
_cod_data_source_block           a14105
_cod_depositor_comments          'Adding full bibliography for 1518417.cif.'
_cod_original_cell_volume        1683.56(14)
_cod_database_code               1518417
_shelxl_version_number           2014-2
_shelx_estimated_absorpt_t_max   0.535
_shelx_estimated_absorpt_t_min   0.417
_refine_ls_abs_structure_hooft   0.045(2)
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All H(H) groups
2. Others
 Fixed Sof: H5B(0.5)
;