Role of Ortho-Substituents on Rhodium-Catalyzed Asymmetric Synthesis of β-Lactones by Intramolecular C-H Insertions of Aryldiazoacetates.
Fu, Liangbing; Wang, Hengbin; Davies, Huw M. L.; Organic letters 16 (2014) 3036–3039; doi:10.1021/ol5011505

data_1516154
_publ_section_title
;
 Role of Ortho-Substituents on Rhodium-Catalyzed Asymmetric Synthesis of
 \b-Lactones by Intramolecular C-H Insertions of Aryldiazoacetates.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              3036
_journal_page_last               3039
_journal_paper_doi               10.1021/ol5011505
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C10 H9 Br O3'
_chemical_formula_sum            'C10 H9 Br O3'
_chemical_formula_weight         257.08
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-09-09
_audit_creation_method
;
  Olex2 1.1-alpha
  (compiled 2011.09.06 svn.r1969, GUI svn.r3851)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.715(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.2085(15)
_cell_length_b                   5.3383(12)
_cell_length_c                   15.239(4)
_cell_measurement_reflns_used    1541
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.58
_cell_measurement_theta_min      2.69
_cell_volume                     502.6(2)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3795
_diffrn_reflns_theta_full        29.57
_diffrn_reflns_theta_max         30.78
_diffrn_reflns_theta_min         2.69
_diffrn_source                   'sealed tube'
_diffrn_source_current           35.0
_diffrn_source_power             1.575
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.067
_exptl_absorpt_correction_T_max  0.3895
_exptl_absorpt_correction_T_min  0.3174
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
R(int) was 0.0460 before and 0.0286 after correction.
The Ratio of minimum to maximum transmission is 0.8149.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.699
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.173
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.694
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.012(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         2353
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0599P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0813
_reflns_number_gt                2423
_reflns_number_total             2647
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5011505_si_002.cif
_cod_data_source_block           hwxii114s
_cod_depositor_comments
'Adding full bibliography for 1516152--1516154.cif.'
_cod_original_cell_volume        502.5(2)
_cod_original_sg_symbol_H-M      'P21 '
_cod_database_code               1516154