Highly Enantioselective Synthesis of Norcaradiene Derivatives from Naphthyl Diazoacetamides Using a Ru(II)-Pheox Complex
Otog, Nansalmaa; Gantogos, Bilguun; Fujisawa, Ikuhide; Iwasa, Seiji; Chemical Communications  (2022) –; doi:10.1039/D2CC04355F

data_7130852
_publ_section_title
;
 Highly Enantioselective Synthesis of Norcaradiene Derivatives from
 Naphthyl Diazoacetamides Using a Ru(II)-Pheox Complex
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC04355F
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H15 N O S'
_chemical_formula_sum            'C15 H15 N O S'
_chemical_formula_weight         257.34
_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'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2022-01-21 deposited with the CCDC.	2022-10-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.163(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.4659(14)
_cell_length_b                   7.0218(15)
_cell_length_c                   14.113(3)
_cell_measurement_reflns_used    6365
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      2.9
_cell_volume                     639.1(2)
_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 (G.M. Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2014/5 (G.M. Sheldrick, 2014)'
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 14.7059
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
AFC7R, 4-circle diffractometer with Mercury CCD camera (Rigaku Corp.)
;
_diffrn_measurement_method
;
Oscillation method with Fine-Slice process
profile data from \f-scans
;
_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  0.0329
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12012
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.033
_diffrn_reflns_theta_min         2.894
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.876
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku Corp.)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             272
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane/Hexane'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 1733 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         4426
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0399
_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^)+(0.0460P)^2^+0.0863P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.0977
_reflns_Friedel_coverage         0.858
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                4097
_reflns_number_total             4426
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc04355f2.cif
_cod_data_source_block           iw2201
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Numerical' was
changed to 'numerical' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7130852
_shelx_estimated_absorpt_t_min   0.921
_shelx_estimated_absorpt_t_max   0.993
_shelx_res_checksum              35853
_shelx_hkl_checksum              76126