Asymmetric Hydroformylation-Initiated Tandem Sequences for Syntheses of (+)-Patulolide C, (-)-Pyrenophorol, (+)-Decarestrictine L, and (+)-Prelog Djerassi Lactone.
Risi, Roberto M.; Maza, Andrew M.; Burke, Steven D.; The Journal of organic chemistry 80 (2014) 204–; doi:10.1021/jo502301k

data_4030297
_publ_section_title
;
 Asymmetric Hydroformylation-Initiated Tandem Sequences for Syntheses of
 (+)-Patulolide C, (-)-Pyrenophorol, (+)-Decarestrictine L, and (+)-Prelog
 Djerassi Lactone.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              204
_journal_paper_doi               10.1021/jo502301k
_journal_volume                  80
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H19 Br O4'
_chemical_formula_sum            'C16 H19 Br O4'
_chemical_formula_weight         355.22
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2013-03-18
_audit_creation_method
;
  Olex2 1.2-dev
  (compiled Mar 13 2013 19:25:50, GUI svn.r4414)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.901(13)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.650(11)
_cell_length_b                   4.9547(18)
_cell_length_c                   22.409(8)
_cell_measurement_reflns_used    9917
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.861
_cell_measurement_theta_min      2.169
_cell_volume                     3151(2)
_computing_cell_refinement       'SAINT+ Ver. 7.68A (Bruker-AXS, 2009)'
_computing_data_collection       'APEX2 Ver. 2012.14-3 (Bruker-AXS, 2012)'
_computing_data_reduction        'SAINT+ Ver. 7.68A'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2008-2012)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '0.5\% \w and 0.5\% \f scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            35047
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.286
_diffrn_reflns_theta_min         1.435
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.622
_exptl_absorpt_correction_T_max  0.9628
_exptl_absorpt_correction_T_min  0.6501
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1470 before and 0.0682 after correction.
The Ratio of minimum to maximum transmission is 0.6752.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.395
_exptl_crystal_size_mid          0.041
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.004(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     384
_refine_ls_number_reflns         8541
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0305
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0278P)^2^+1.0859P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0595
_refine_ls_wR_factor_ref         0.0616
_reflns_Friedel_coverage         0.802
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                7670
_reflns_number_total             8541
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo502301k_si_002.cif
_cod_data_source_block           burke25
_cod_depositor_comments          'Adding full bibliography for 4030297.cif.'
_cod_database_code               4030297
_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
2.a Ternary CH refined with riding coordinates:
 C8(H8), C11(H11), C13(H13), C8A(H8A), C11A(H11A), C13A(H13A)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C14(H14A,H14B), C9A(H9AA,H9AB), C10A(H10C,H10D),
 C14A(H14C,H14D)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C1A(H1A), C2A(H2A), C4A(H4A), C5A(H5A)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C16(H16A,H16B,H16C), C12A(H12D,H12E,H12F), C16A(H16D,
 H16E,H16F)
;
_shelx_estimated_absorpt_t_max   0.902
_shelx_estimated_absorpt_t_min   0.424
_shelx_hkl_checksum              42126
_shelx_res_checksum              32835
_shelxl_version_number           2012-9