Catalytic, Asymmetric Dearomative Synthesis of Complex Cyclohexanes via a Highly Regio- and Stereoselective Arene Cyclopropanation Using α-Cyanodiazoacetates
Smith, Kendrick L.; Padgett, Cody L.; Mackay, William D.; Johnson, Jeffrey S.; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.9b13080

data_4134588
_publ_section_title
;
 Catalytic, Asymmetric Dearomative Synthesis of Complex Cyclohexanes via a
 Highly Regio- and Stereoselective Arene Cyclopropanation Using
 \a-Cyanodiazoacetates
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b13080
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H35 N3 O7 Os1'
_chemical_formula_sum            'C20 H35 N3 O7 Os'
_chemical_formula_weight         619.71
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2020-03-13
_audit_creation_method           CRYSTALS_ver_14.61_build_6236
_cell_angle_alpha                90
_cell_angle_beta                 103.2123(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3859(2)
_cell_length_b                   15.1577(3)
_cell_length_c                   13.1632(2)
_cell_measurement_reflns_used    9890
_cell_measurement_temperature    150
_cell_measurement_theta_max      70
_cell_measurement_theta_min      3
_cell_volume                     2405.87(7)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.062
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            50943
_diffrn_reflns_theta_full        70.165
_diffrn_reflns_theta_max         70.165
_diffrn_reflns_theta_min         3.449
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    10.386
_exptl_absorpt_correction_T_max  0.35
_exptl_absorpt_correction_T_min  0.35
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'block fragment'
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.85
_refine_diff_density_min         -1.02
_refine_ls_abs_structure_details 'Flack (1983), 4246 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.018(9)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0260
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     568
_refine_ls_number_reflns         8958
_refine_ls_number_restraints     45
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0313
_refine_ls_shift/su_max          0.0197017
_refine_ls_shift/su_mean         0.0005127
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.00P)^2^ +10.65P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0686
_refine_ls_wR_factor_gt          0.0678
_refine_ls_wR_factor_ref         0.0686
_reflns_limit_h_max              14
_reflns_limit_h_min              -15
_reflns_limit_k_max              16
_reflns_limit_k_min              -18
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                8620
_reflns_number_total             8993
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0329
_oxford_refine_ls_scale          0.092251(13)
_oxford_reflns_number_all        8958
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title '20020_0m in P2(1)'
_cod_data_source_file            ja9b13080_si_002.cif
_cod_data_source_block           20020
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'Other' was changed to
'other' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/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_original_formula_sum        'C20 H35 N3 O7 Os1'
_cod_database_code               4134588