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_1516152
_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         'C16 H13 Br O3'
_chemical_formula_sum            'C16 H13 Br O3'
_chemical_formula_weight         333.17
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-03-21
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4813)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.596(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.952(2)
_cell_length_b                   12.184(4)
_cell_length_c                   14.721(4)
_cell_measurement_reflns_used    2781
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      26.179
_cell_measurement_theta_min      2.771
_cell_volume                     1424.8(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 with a narrow frame width'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0777
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10404
_diffrn_reflns_point_group_measured_fraction_full 0.819
_diffrn_reflns_point_group_measured_fraction_max 0.792
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         1.385
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.889
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0905 before and 0.0629 after correction.
The Ratio of minimum to maximum transmission is 0.6417.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_recrystallization_method
'The material was recrystallised from hexane.'
_exptl_crystal_size_max          0.674
_exptl_crystal_size_mid          0.219
_exptl_crystal_size_min          0.132
_refine_diff_density_max         1.157
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.107
_refine_ls_abs_structure_details
;
 Flack x determined using 1223 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.045(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         5160
_refine_ls_number_restraints     148
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0471
_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^)+(0.0409P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1092
_reflns_Friedel_coverage         0.511
_reflns_Friedel_fraction_full    0.617
_reflns_Friedel_fraction_max     0.563
_reflns_number_gt                3987
_reflns_number_total             5160
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5011505_si_003.cif
_cod_data_source_block           lfu-ii-85
_cod_depositor_comments
'Adding full bibliography for 1516152--1516154.cif.'
_cod_database_code               1516152
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.702
_shelx_estimated_absorpt_t_min   0.246
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C1-H1
 0.995 with sigma of 0.005
 C1'-H1'
 0.995 with sigma of 0.002
 C2'-H2'
 0.995 with sigma of 0.002
3. Uiso/Uaniso restraints and constraints
Uiso(H1') = Uiso(H2')
4. Rigid body (RIGU) restrains
 C3', O2', O1', C1', C2'
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C4, C5, C6, C7, C8, C9
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
 C10, C15, C14, C13, C12, C11
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
 C4', C5', C6', C7', C8', C9', C1'
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
5.a Ternary CH refined with riding coordinates:
 C2(H2)
5.b Aromatic/amide H refined with riding coordinates:
 C15'(H15'), C7'(H7'), C13'(H13'), C8'(H8'), C12'(H12'), C9'(H9'), C6'(H6'),
 C5'(H5'), C6(H6), C13(H13), C15(H15), C12(H12), C9(H9), C5(H5), C8(H8), C7(H7)
5.c Idealised Me refined as rotating group:
 C16'(H16A,H16B,H16C), C16(H16D,H16E,H16F)
;
_shelx_res_checksum              24059
_shelx_hkl_checksum              14164