Asymmetric Total Synthesis of (-)-Clovan-2,9-dione Using Rh(I)-Catalyzed [3 + 2 + 1] Cycloaddition of 1-Yne-vinylcyclopropane and CO.
Yang, Jun; Xu, Wenbo; Cui, Qi; Fan, Xing; Wang, Lu-Ning; Yu, Zhi-Xiang; Organic letters 19 (2017) 6040–6043; doi:10.1021/acs.orglett.7b02656

data_1547905
_publ_section_title
;
 Asymmetric Total Synthesis of (-)-Clovan-2,9-dione Using Rh(I)-Catalyzed
 [3 + 2 + 1] Cycloaddition of 1-Yne-vinylcyclopropane and CO.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              6040
_journal_page_last               6043
_journal_paper_doi               10.1021/acs.orglett.7b02656
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C29 H33 Br O4'
_chemical_formula_sum            'C29 H33 Br O4'
_chemical_formula_weight         525.46
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-09-12
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                70.001(9)
_cell_angle_beta                 80.759(8)
_cell_angle_gamma                83.195(9)
_cell_formula_units_Z            2
_cell_length_a                   9.8378(11)
_cell_length_b                   10.0606(10)
_cell_length_c                   14.0335(12)
_cell_measurement_reflns_used    1346
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      23.6320
_cell_measurement_theta_min      3.2700
_cell_volume                     1285.2(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
  1 omega   34.00   99.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017 -178.0000  -60.0000 65

  2 omega  -38.00   62.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7954   57.0000   90.0000 100

  3 omega  -77.00   15.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7954  -57.0000  -60.0000 92
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0593706000
_diffrn_orient_matrix_UB_12      -0.0202045000
_diffrn_orient_matrix_UB_13      -0.0129624000
_diffrn_orient_matrix_UB_21      0.0317999000
_diffrn_orient_matrix_UB_22      -0.0691329000
_diffrn_orient_matrix_UB_23      0.0068917000
_diffrn_orient_matrix_UB_31      -0.0287233000
_diffrn_orient_matrix_UB_32      -0.0216349000
_diffrn_orient_matrix_UB_33      0.0522129000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.1214
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7667
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.013
_diffrn_reflns_theta_min         3.115
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.631
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       block
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.908
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4975
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1742
_refine_ls_R_factor_gt           0.0841
_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^)+(0.1065P)^2^+0.4325P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1968
_refine_ls_wR_factor_ref         0.2466
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2453
_reflns_number_total             4975
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02656_si_002.cif
_cod_data_source_block           exp_8114
_cod_depositor_comments          'Adding full bibliography for 1547905.cif.'
_cod_database_code               1547905
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         C29H33Br1O4
_shelx_estimated_absorpt_t_max   0.854
_shelx_estimated_absorpt_t_min   0.792
_reflns_odcompleteness_completeness 98.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_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
2.a Ternary CH refined with riding coordinates:
 C3(H3), C7(H7), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C8(H8A,H8B), C11(H11A,H11B), C12(H12A,H12B),
 C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19), C21(H21), C22(H22), C25(H25), C26(H26), C27(H27),
 C28(H28), C29(H29)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_olex2_submission_special_instructions 'No special instructions were received'