Nickel(ii)-catalyzed enantioselective cyclopropanation of 3-alkenyl-oxindoles with phenyliodonium ylide via free carbene
Guo, Jing; Liu, Yangbin; Li, Xiangqiang; Liu, Xiaohua; Lin, Lili; Feng, Xiaoming; Chem. Sci. 7 (2016) 2717–; doi:10.1039/C5SC03658E

data_1541883
_publ_section_title
;
 Nickel(ii)-catalyzed enantioselective cyclopropanation of
 3-alkenyl-oxindoles with phenyliodonium ylide via free carbene
;
_journal_issue                   4
_journal_name_full               'Chem. Sci.'
_journal_page_first              2717
_journal_paper_doi               10.1039/C5SC03658E
_journal_volume                  7
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H22 O4'
_chemical_formula_weight         254.32
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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_block_doi                 10.5517/cc13qf4d
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-11-15 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2942(11)
_cell_length_b                   12.3961(18)
_cell_length_c                   13.909(2)
_cell_measurement_reflns_used    4753
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      55.021
_cell_measurement_theta_min      5.585
_cell_volume                     1257.6(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_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_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8860
_diffrn_reflns_theta_full        25.98
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.134
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.9(9)
_refine_ls_extinction_coef       0.0058(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0308
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0308P)^2^+0.3738P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0751
_reflns_number_gt                2353
_reflns_number_total             2462
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5sc03658e2.cif
_cod_data_source_block           dm13746
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 1541883--1541884.cif.
;
_cod_original_cell_volume        1257.7(3)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1541883