Total Syntheses of Highly Oxidized ent-Kaurenoids Pharicin A, Pharicinin B, 7-O-Acetylpseurata C, and Pseurata C: A [5+2] Cascade Approach.
He, Chi; Hu, Jialei; Wu, Yubing; Ding, Hanfeng; Journal of the American Chemical Society 139 (2017) 6098–6101; doi:10.1021/jacs.7b02746

data_4125961
_publ_section_title
;
 Total Syntheses of Highly Oxidized ent-Kaurenoids Pharicin A, Pharicinin
 B, 7-O-Acetylpseurata C, and Pseurata C: A [5+2] Cascade Approach.
;
_journal_issue                   17
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6098
_journal_page_last               6101
_journal_paper_doi               10.1021/jacs.7b02746
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C11 H11 Br O2'
_chemical_formula_sum            'C11 H11 Br O2'
_chemical_formula_weight         255.11
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-01-09
_audit_creation_method
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Olex2 1.2
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_cell_length_b                   8.2879(9)
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_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -14.00   77.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8433   38.0000  150.0000 91

  2 omega  -60.00   34.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8433  -38.0000  -30.0000 94

  3 omega  -78.00   21.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.5621  -77.0000 -150.0000 99
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
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_diffrn_orient_matrix_UB_11      0.0347764000
_diffrn_orient_matrix_UB_12      0.0038298000
_diffrn_orient_matrix_UB_13      0.0747323000
_diffrn_orient_matrix_UB_21      -0.0444334000
_diffrn_orient_matrix_UB_22      0.0054644000
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_diffrn_orient_matrix_UB_31      -0.0012194000
_diffrn_orient_matrix_UB_32      -0.0852669000
_diffrn_orient_matrix_UB_33      0.0049169000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6135
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.344
_diffrn_reflns_theta_min         2.944
_diffrn_source                   'Enhance (Mo) X-ray Source'
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_exptl_absorpt_correction_T_max  1.00000
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_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
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_exptl_crystal_description       needle
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.610
_refine_diff_density_min         -0.782
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_parameters     146
_refine_ls_number_reflns         1834
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0513
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
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'w=1/[\s^2^(Fo^2^)+(0.0666P)^2^+0.7096P] where P=(Fo^2^+2Fc^2^)/3'
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_cod_depositor_comments          'Adding full bibliography for 4125961.cif.'
_cod_original_cell_volume        1008.84(16)
_cod_database_code               4125961
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c10 h10 o10 br1'
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_cell_oxdiff_angle_beta          110.765(10)
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_reflns_odcompleteness_completeness 99.73
_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, All C(H,H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C6 \\sim C7 \\sim C7A \\sim C8 \\sim C8A: within 3.8A with sigma of 0.01 and
sigma for terminal atoms of 0.02
3. Others
 Sof(H6BC)=Sof(H6BD)=Sof(H9B)=Sof(C7A)=Sof(H7AA)=Sof(H7AB)=Sof(C8A)=Sof(H8AA)=
 Sof(H8AB)=1-FVAR(1)
 Sof(H6AB)=Sof(H6AA)=Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(C8)=Sof(H8A)=Sof(H8B)=
 Sof(H9A)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C3(H3), C9(H9A), C9(H9B)
4.b Secondary CH2 refined with riding coordinates:
 C6(H6AB,H6AA), C6(H6BC,H6BD), C7(H7A,H7B), C8(H8A,H8B), C10(H10A,H10B),
 C7A(H7AA,H7AB), C8A(H8AA,H8AB)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2)
;
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_olex2_submission_special_instructions 'No special instructions were received'