Highly stereoselective spirocyclopropanation of various diazooxindoles with olefins catalyzed using Ru(ii)-complex
Tone, Masaya; Nakagawa, Yoko; Chanthamath, Soda; Fujisawa, Ikuhide; Nakayama, Naofumi; Goto, Hitoshi; Shibatomi, Kazutaka; Iwasa, Seiji; RSC Advances 8 (2018) 39865–; doi:10.1039/C8RA09212E

data_7231900
_publ_section_title
;
 Highly stereoselective spirocyclopropanation of various diazooxindoles
 with olefins catalyzed using Ru(ii)-complex
;
_journal_issue                   70
_journal_name_full               'RSC Advances'
_journal_page_first              39865
_journal_paper_doi               10.1039/C8RA09212E
_journal_volume                  8
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H14 Br N O'
_chemical_formula_weight         328.20
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2018-10-23 deposited with the CCDC.
2018-11-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0888(8)
_cell_length_b                   12.5645(17)
_cell_length_c                   17.867(2)
_cell_measurement_reflns_used    10301
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      2.0
_cell_volume                     1366.9(3)
_computing_cell_refinement
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_data_collection
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_data_reduction
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  'Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SIR2004 (Burla, Caliandro et al., 2005)'
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 14.7059
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type
;
AFC7R, 4-circle diffractometer with Mercury CCD camera (Rigaku Corp.)
;
_diffrn_measurement_method
;
Oscillation method with Fine-Slice process
;
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            29902
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.033
_diffrn_reflns_theta_min         1.982
_diffrn_source                   'Rotating Anode X-ray tube'
_exptl_absorpt_coefficient_mu    3.001
_exptl_absorpt_correction_T_max  0.677
_exptl_absorpt_correction_T_min  0.267
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku Corp.)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_description       Block
_exptl_crystal_F_000             664
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane/hexane'
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.964
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1483 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.018(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3974
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.0228
_refine_ls_R_factor_gt           0.0207
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0204P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0481
_refine_ls_wR_factor_ref         0.0488
_reflns_Friedel_coverage         0.737
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3693
_reflns_number_total             3974
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ra09212e2.cif
_cod_data_source_block           iw0604c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Numerical' changed to
'numerical' according to
/home/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 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               7231900
_shelx_estimated_absorpt_t_min   0.380
_shelx_estimated_absorpt_t_max   0.817
_shelx_res_checksum              18431