Unusual reactivity of rhodium carbenes with allenes: an efficient asymmetric synthesis of methylenetetrahydropyran scaffolds
Torres, Òscar; Solà, Miquel; Roglans, Anna; Pla Quintana, Anna; Chem. Commun.  (2017) –; doi:10.1039/C7CC04803C

data_7120558
_publ_section_title
;
 Unusual reactivity of rhodium carbenes with allenes: an efficient
 asymmetric synthesis of methylenetetrahydropyran scaffolds
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC04803C
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H27 N O5 S2'
_chemical_formula_sum            'C24 H27 N O5 S2'
_chemical_formula_weight         473.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-07-14 deposited with the CCDC.
2017-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.393(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.607(4)
_cell_length_b                   7.076(3)
_cell_length_c                   15.851(8)
_cell_measurement_reflns_used    1555
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.59
_cell_measurement_theta_min      2.28
_cell_volume                     1189.3(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0680
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7368
_diffrn_reflns_point_group_measured_fraction_full 0.917
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         1.285
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.099975
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS v2.10 BRUKER 2001'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.612
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Flack x determined using 815 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4812
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.146
_refine_ls_R_factor_all          0.1229
_refine_ls_R_factor_gt           0.0762
_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^)+(0.0811P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1653
_refine_ls_wR_factor_ref         0.1912
_reflns_Friedel_coverage         0.649
_reflns_Friedel_fraction_full    0.820
_reflns_Friedel_fraction_max     0.753
_reflns_number_gt                2992
_reflns_number_total             4812
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc04803c2.cif
_cod_data_source_block           ot498
_cod_database_code               7120558
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              28300