Enantioselective copper catalysed intramolecular C-H insertion reactions of α-diazo-β-keto sulfones, α-diazo-β-keto phosphine oxides and 2-diazo-1,3-diketones; the influence of the carbene substituent.
Shiely, Amy E.; Slattery, Catherine N.; Ford, Alan; Eccles, Kevin S.; Lawrence, Simon E.; Maguire, Anita R.; Organic & biomolecular chemistry 15 (2017) 2609–2628; doi:10.1039/c7ob00214a

data_7155512
_publ_section_title
;
 Enantioselective copper catalysed intramolecular C-H insertion reactions
 of \a-diazo-\b-keto sulfones, \a-diazo-\b-keto phosphine oxides and
 2-diazo-1,3-diketones; the influence of the carbene substituent.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2609
_journal_page_last               2628
_journal_paper_doi               10.1039/c7ob00214a
_journal_volume                  15
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H15 Br O3 S'
_chemical_formula_sum            'C17 H15 Br O3 S'
_chemical_formula_weight         379.26
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2017-01-24 deposited with the CCDC.
2017-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8117(10)
_cell_length_b                   12.6388(16)
_cell_length_c                   16.816(2)
_cell_measurement_reflns_used    5607
_cell_measurement_temperature    292.(2)
_cell_measurement_theta_max      24.4402
_cell_measurement_theta_min      2.8752
_cell_volume                     1660.3(4)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection       'Bruker Instrument Service v2010, 1, 0, 0'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      292.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX II DUO'
_diffrn_measurement_method       '\f & \w  scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20445
_diffrn_reflns_theta_full        27.11
_diffrn_reflns_theta_max         27.11
_diffrn_reflns_theta_min         2.02
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              Bruker
_exptl_absorpt_coefficient_mu    2.610
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.575
_refine_diff_density_min         -0.510
_refine_ls_abs_structure_details
;
Flack x determined using 1123 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.018(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3628
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0211P)^2^+0.6542P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0819
_reflns_number_gt                3045
_reflns_number_total             3628
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob00214a2.cif
_cod_data_source_block           2R_3R-14i
_cod_depositor_comments
'Adding full bibliography for 7155511--7155513.cif.'
_cod_database_code               7155512
_shelx_res_checksum              65011