Rhodium-Catalyzed Asymmetric [2 + 2 + 2] Cyclization of 1,6-Enynes with Aliphatic and Aromatic Alkenes.
Ueda, Hiroki; Masutomi, Koji; Shibata, Yu; Tanaka, Ken; Organic letters 19 (2017) 2913–2916; doi:10.1021/acs.orglett.7b01149

data_1546087
_publ_section_title
;
 Rhodium-Catalyzed Asymmetric [2 + 2 + 2] Cyclization of 1,6-Enynes with
 Aliphatic and Aromatic Alkenes.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2913
_journal_page_last               2916
_journal_paper_doi               10.1021/acs.orglett.7b01149
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C22 H24 Br N O3 S'
_chemical_formula_sum            'C22 H24 Br N O3 S'
_chemical_formula_weight         462.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-04-14
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2016.03.30 svn.r3266 for Rigaku Oxford Diffraction, GUI svn.r5168)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.730(2)
_cell_length_b                   10.167(2)
_cell_length_c                   21.994(6)
_cell_measurement_reflns_used    2756
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      21.6090
_cell_measurement_theta_min      2.2020
_cell_volume                     2175.8(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.12b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.12b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.12b (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.960
_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    -46.00 -20.00   0.50   60.00    --   20.00  54.00 -90.00   52
  2  \w     22.00  83.00   0.50   60.00    --   20.00  54.00 -90.00  122
  3  \w     -8.00  80.00   0.50   60.00    --   20.00  54.00 150.00  176
  4  \w    -74.00 109.00   0.50   60.00    --   20.00  54.00  60.00  366
  5  \w    -34.00  -9.00   0.50   60.00    --   20.00  54.00-150.00   50
  6  \w     63.00  88.00   0.50   60.00    --   20.00  54.00-180.00   50
  7  \w    -52.00   9.00   0.50   60.00    --   20.00  54.00-120.00  122
  8  \w     38.00  63.00   0.50   60.00    --   20.00  54.00-120.00   50
  9  \w    -73.00 -46.00   0.50   60.00    --   20.00  54.00 120.00   54
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0216111000
_diffrn_orient_matrix_UB_12      -0.0582023000
_diffrn_orient_matrix_UB_13      -0.0150437000
_diffrn_orient_matrix_UB_21      0.0184100000
_diffrn_orient_matrix_UB_22      -0.0278846000
_diffrn_orient_matrix_UB_23      0.0283515000
_diffrn_orient_matrix_UB_31      -0.0672437000
_diffrn_orient_matrix_UB_32      -0.0264316000
_diffrn_orient_matrix_UB_33      0.0028990000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0871
_diffrn_reflns_av_unetI/netI     0.1024
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            19408
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.745
_diffrn_reflns_theta_min         2.207
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.007
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.12b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.757
_refine_diff_density_min         -0.768
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details
;
 Flack x determined using 914 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.004(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         6297
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1496
_refine_ls_R_factor_gt           0.0731
_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^)+(0.0958P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1767
_refine_ls_wR_factor_ref         0.2087
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.890
_reflns_number_gt                3166
_reflns_number_total             6297
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01149_si_001.cif
_cod_data_source_block           y6220f
_cod_depositor_comments          'Adding full bibliography for 1546087.cif.'
_cod_original_cell_volume        2175.7(9)
_cod_database_code               1546087
_chemical_oxdiff_formula         C30H40NO3Br
_chemical_oxdiff_usercomment     ueda-diene-chiral,-80
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C17(H17), C21(H21), C10(H10), C20(H20), C11(H11), C7(H7), C8(H8)
2.d X=CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.e Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C13(H13A,H13B,H13C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              85114
_shelx_hkl_checksum              21344
_shelx_shelxl_version_number     2016/6
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.691
_oxdiff_exptl_absorpt_empirical_full_min 0.712