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_1516153
_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         'C11 H11 Br O3'
_chemical_formula_sum            'C11 H11 Br O3'
_chemical_formula_weight         271.11
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-03-19
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.03.12 svn.r2899 for OlexSys, GUI svn.r4796)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.060(2)
_cell_length_b                   12.066(2)
_cell_length_c                   14.641(3)
_cell_measurement_reflns_used    8641
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      25.840
_cell_measurement_theta_min      2.388
_cell_volume                     2130.5(7)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 512
_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_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0858
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            26029
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.130
_diffrn_reflns_theta_min         1.689
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.842
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.3793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1594 before and 0.0920 after correction.
The Ratio of minimum to maximum transmission is 0.5083.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_description       prism
_exptl_crystal_F_000             1088
_exptl_crystal_recrystallization_method
'The material was recrystallised from hexane by slow evaporation'
_exptl_crystal_size_max          0.732
_exptl_crystal_size_mid          0.729
_exptl_crystal_size_min          0.154
_refine_diff_density_max         1.019
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.109
_refine_ls_abs_structure_details
;
 Flack x determined using 1975 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.029(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         5736
_refine_ls_number_restraints     64
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0424
_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^)+(0.0346P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0875
_reflns_Friedel_coverage         0.780
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                5086
_reflns_number_total             5736
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5011505_si_004.cif
_cod_data_source_block           lfu-ii-99t
_cod_depositor_comments
'Adding full bibliography for 1516152--1516154.cif.'
_cod_original_cell_volume        2130.5(6)
_cod_database_code               1516153
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.589
_shelx_estimated_absorpt_t_min   0.165
_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. Restrained distances
 C2-H2
 0.975 with sigma of 0.01
3. Rigid body (RIGU) restrains
 C6, C5, C10, C9, C8, C7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C2, C3, O1, C1, C4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Ternary CH refined with riding coordinates:
 C2'(H2'), C1'(H1'), C1(H1)
4.b Aromatic/amide H refined with riding coordinates:
 C8'(H8'), C7'(H7'), C10'(H10'), C8(H8), C10(H10), C7(H7)
4.c Idealised Me refined as rotating group:
 C4'(H4'A,H4'B,H4'C), C11'(H11A,H11B,H11C), C11(H11D,H11E,H11F), C4(H4A,H4B,H4C)
;
_shelx_res_checksum              78436
_shelx_hkl_checksum              34184
_olex2_computing_structure_refinement_long 'SHELXL-97 (Sheldrick, 2008)'
_olex2_computing_structure_solution_long 'SHELXS-97 (Sheldrick, 2008)'