Rhodium-catalysed alkoxylation/acetalization of diazo compounds: one-step synthesis of highly functionalised quaternary carbon centres
Jola Pospech; Alastair J. J. Lennox; Matthias Beller; Chem.Commun. 51 (2015) 14505–; doi:10.1039/C5cc03903G

data_7117795
_publ_section_title
;
 Rhodium-catalysed alkoxylation/acetalization of diazo compounds: one-step
 synthesis of highly functionalised quaternary carbon centres
;
_journal_name_full               Chem.Commun.
_journal_page_first              14505
_journal_paper_doi               10.1039/C5cc03903G
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C13 H17 Br O5'
_chemical_formula_weight         333.17
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2015-01-13 deposited with the CCDC.
2015-08-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3578(16)
_cell_length_b                   11.7005(14)
_cell_length_c                   8.2619(9)
_cell_measurement_reflns_used    8498
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.66
_cell_measurement_theta_min      2.25
_cell_volume                     1387.9(3)
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        SAINT
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            21187
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.701
_diffrn_reflns_theta_min         2.245
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.975
_exptl_absorpt_correction_T_max  0.67
_exptl_absorpt_correction_T_min  0.48
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.298
_exptl_crystal_size_min          0.145
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1248 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.021(5)
_refine_ls_extinction_coef       .
_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     176
_refine_ls_number_reflns         3366
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0219
_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^)+(0.0200P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0472
_refine_ls_wR_factor_ref         0.0483
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_full    0.884
_reflns_Friedel_fraction_max     0.865
_reflns_number_gt                3054
_reflns_number_total             3366
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc03903g2.cif
_cod_data_source_block           AX0625
_cod_database_code               7117795
_shelxl_version_number           2014-3
_shelx_res_checksum              57164