Enantioselective Assembly of Congested Cyclopropanes using Redox-Active Aryldiazoacetates
Yu, Zhunzhun; Mendoza, Abraham; ACS Catalysis 9 (2019) 7870–; doi:10.1021/acscatal.9b02615

data_4514819
_publ_section_title
;
 Enantioselective Assembly of Congested Cyclopropanes using Redox-Active
 Aryldiazoacetates
;
_journal_issue                   9
_journal_name_full               'ACS Catalysis'
_journal_page_first              7870
_journal_paper_doi               10.1021/acscatal.9b02615
_journal_volume                  9
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H16 Br N O4'
_chemical_formula_sum            'C24 H16 Br N O4'
_chemical_formula_weight         462.29
_chemical_name_systematic
'1,3-dioxoisoindolin-2-yl (1R,2S)-2-(4-chlorophenyl)-1-phenylcyclopropane-1-carboxylate'
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-07-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-07-19 # Formatted by publCIF

;
_cell_angle_alpha                90.0
_cell_angle_beta                 102.827(2)
_cell_angle_gamma                90.0
_cell_formula_units_Z            2
_cell_length_a                   9.72130(19)
_cell_length_b                   9.12937(16)
_cell_length_c                   12.1367(3)
_cell_measurement_reflns_used    6326
_cell_measurement_temperature    293
_cell_measurement_theta_max      55.3750
_cell_measurement_theta_min      3.6260
_cell_volume                     1050.24(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    213.96 272.96   1.00   10.00    -- -112.92 -59.25 -51.92   59
  2  \w    213.96 272.96   1.00   10.00    -- -112.92 -59.25  20.08   59
  3  \w   -134.04 -22.04   1.00   10.00    -- -112.92  83.74 -29.95  112
  4  \w    213.96 272.96   1.00   10.00    -- -112.92 -59.25 148.08   59
  5  \w    213.96 272.96   1.00   10.00    -- -112.92 -59.25-115.92   59
  6  \w    213.96 272.96   1.00   10.00    -- -112.92 -59.25  84.08   59
  7  \w   -134.04 -22.04   1.00   10.00    -- -112.92  83.74 130.05  112
  8  \f   -339.92  20.08   1.00   10.00 -43.57 -69.44 -59.25    --   360
  9  \w    -26.19  77.81   1.00   10.00    --   38.56 -83.74 -50.05  104
 10  \w    -26.19  77.81   1.00   10.00    --   38.56 -83.74 109.95  104
 11  \f     -9.39 350.61   1.00   10.00 -21.98-112.92  28.85    --   360
 12  \f   -339.92  20.08   1.00   10.00 -72.04 -97.92 -59.25    --   360
 13  \w   -134.04 -22.04   1.00   10.00    -- -112.92  83.74-101.95  112
 14  \w     -2.24 104.76   1.00   10.00    --   23.56  59.25  69.92  107
 15  \w    251.21 307.21   1.00   10.00    -- -112.92 114.09  51.24   56
 16  \w    213.96 272.96   1.00   10.00    -- -112.92 -59.25-147.92   59
 17  \f     -9.39 350.61   1.00   10.00   6.50 -84.44  28.85    --   360
 18  \w    251.21 307.21   1.00   10.00    -- -112.92 114.09 179.24   56
 19  \w     -2.24 104.76   1.00   10.00    --   23.56  59.25-110.08  107
 20  \w   -134.04 -22.04   1.00   10.00    -- -112.92  83.74  34.05  112
 21  \w    213.96 272.96   1.00   10.00    -- -112.92 -59.25 -19.92   59
 22  \w    213.96 272.96   1.00   10.00    -- -112.92 -59.25  52.08   59
 23  \w    213.96 272.96   1.00   10.00    -- -112.92 -59.25 116.08   59
 24  \w    251.21 307.21   1.00   10.00    -- -112.92 114.09 -84.76   56
 25  \w    213.96 272.96   1.00   10.00    -- -112.92 -59.25 -83.92   59
 26  \w    213.96 272.96   1.00   10.00    -- -112.92 -59.25-179.92   59
 27  \w   -134.04 -22.04   1.00   10.00    -- -112.92  83.74 162.05  112
 28  \w    -26.19  77.81   1.00   10.00    --   38.56 -83.74-170.05  104
 29  \w     -2.24 104.76   1.00   10.00    --   23.56  59.25 159.92  107
 30  \f   -339.92  20.08   1.00   10.00 -87.04-112.92 -59.25    --   360
 31  \w   -134.04 -22.04   1.00   10.00    -- -112.92  83.74-133.95  112
 32  \w   -134.04 -22.04   1.00   10.00    -- -112.92  83.74   2.05  112
 33  \w   -134.04 -22.04   1.00   10.00    -- -112.92  83.74 -69.95  112
 34  \w   -134.04 -22.04   1.00   10.00    -- -112.92  83.74  66.05  112
 35  \f   -339.92  20.08   1.00   10.00 -58.57 -84.44 -59.25    --   360
 36  \w    -26.19  77.81   1.00   10.00    --   38.56 -83.74  29.95  104
 37  \w   -134.04 -22.04   1.00   10.00    -- -112.92  83.74  98.05  112
 38  \w   -134.04 -22.04   1.00   10.00    -- -112.92  83.74-165.95  112
 39  \w    251.21 307.21   1.00   10.00    -- -112.92 114.09-116.76   56
 40  \w    251.21 307.21   1.00   10.00    -- -112.92 114.09  19.24   56
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1612192000
_diffrn_orient_matrix_UB_12      0.0185266000
_diffrn_orient_matrix_UB_13      -0.0364540000
_diffrn_orient_matrix_UB_21      -0.0083547000
_diffrn_orient_matrix_UB_22      -0.1348206000
_diffrn_orient_matrix_UB_23      -0.0774889000
_diffrn_orient_matrix_UB_31      -0.0186770000
_diffrn_orient_matrix_UB_32      -0.0997612000
_diffrn_orient_matrix_UB_33      0.0980723000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            36300
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.220
_diffrn_reflns_theta_min         3.735
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.924
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_description       plate
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_min          0.024
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.719
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 1523 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.043(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4496
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0722P)^2^+0.2687P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1396
_reflns_Friedel_coverage         0.864
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                3804
_reflns_number_total             4496
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b02615_si_002.cif
_cod_data_source_block           cu_am_zzy_pbrcp_2
_cod_database_code               4514819
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C24 H16 Br N O4'
_cell_oxdiff_angle_alpha         89.966(3)
_cell_oxdiff_angle_beta          102.814(3)
_cell_oxdiff_angle_gamma         90.013(3)
_cell_oxdiff_length_a            9.7218(4)
_cell_oxdiff_length_b            9.1300(3)
_cell_oxdiff_length_c            12.1346(5)
_cell_oxdiff_measurement_reflns_used 6326
_cell_oxdiff_volume              1050.24(7)
_shelx_estimated_absorpt_t_max   0.933
_shelx_estimated_absorpt_t_min   0.564
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C16(H16), C17(H17), C20(H20), C21(H21), C23(H23), C26(H26),
 C27(H27), C31(H31), C32(H32), C34(H34), C35(H35), C36(H36)
;
_shelx_res_checksum              56913
_shelx_hkl_checksum              30734
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.657
_oxdiff_exptl_absorpt_empirical_full_min 0.628
_publcif_funding_html
;
;