Highly Stereoselective Intramolecular Buchner Reaction of Diazoacetamides Catalyzed by a Ru(II)-Pheox Complex
Phan Thi Thanh , Nga; Tone, Masaya; Inoue, Hayato; Fujisawa, Ikuhide; Iwasa, Seiji; Chemical Communications  (2019) –; doi:10.1039/C9CC06889A

data_7124299
_publ_section_title
;
 Highly Stereoselective Intramolecular Buchner Reaction of Diazoacetamides
 Catalyzed by a Ru(II)-Pheox Complex
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC06889A
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C16 H13 Cl2 N O'
_chemical_formula_weight         306.17
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2019-09-05 deposited with the CCDC.    2019-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7489(4)
_cell_length_b                   10.8111(7)
_cell_length_c                   22.1649(14)
_cell_measurement_reflns_used    6506
_cell_measurement_temperature    120
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.6
_cell_volume                     1377.59(16)
_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    'SIR2014 (Burla, Caliandro et al., 2015)'
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 14.7059
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
;
AFC7R, 4-circle diffractometer with Mercury CCD camera (Rigaku Corp.)
Rigaku CrystalClear-SM Expert 2.0 r16
;
_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  0.0353
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            17718
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.991
_diffrn_reflns_theta_min         2.632
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.465
_exptl_absorpt_correction_T_max  0.915
_exptl_absorpt_correction_T_min  0.819
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku Corp.)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_description       Block
_exptl_crystal_F_000             632
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 1546 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         4377
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0365
_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^)+(0.0451P)^2^+0.2020P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0895
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3996
_reflns_number_total             4377
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc06889a2.cif
_cod_data_source_block           iw1203
_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               7124299
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.836
_shelx_estimated_absorpt_t_max   0.955
_shelx_res_checksum              18757