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_7155511
_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         'C12 H14 O3 S'
_chemical_formula_sum            'C12 H14 O3 S'
_chemical_formula_weight         238.29
_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   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                 110.492(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8164(18)
_cell_length_b                   9.2321(11)
_cell_length_c                   11.9043(19)
_cell_measurement_reflns_used    3948
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      22.7146
_cell_measurement_theta_min      3.0156
_cell_volume                     1216.5(3)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_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      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0367
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13855
_diffrn_reflns_theta_full        26.38
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         1.83
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              Bruker
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6041
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.208
_refine_ls_abs_structure_details
;
Flack x determined using 1478 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4845
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0414
_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^)+(0.0574P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1063
_reflns_number_gt                3941
_reflns_number_total             4845
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob00214a2.cif
_cod_data_source_block           2R_3R-14j
_cod_depositor_comments
'Adding full bibliography for 7155511--7155513.cif.'
_cod_database_code               7155511
_shelx_res_checksum              84163