Highly Stereoselective Synthesis of Fused Cyclopropane-γ-Lactams via Biocatalytic Iron-Catalyzed Intramolecular Cyclopropanation
Ren, Xinkun; Chandgude, Ajay L.; Fasan, Rudi; ACS Catalysis  (2020) 2308–2313; doi:10.1021/acscatal.9b05383

data_4517359
_publ_section_title
;
 Highly Stereoselective Synthesis of Fused Cyclopropane-\g-Lactams via
 Biocatalytic Iron-Catalyzed Intramolecular Cyclopropanation
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              2308
_journal_page_last               2313
_journal_paper_doi               10.1021/acscatal.9b05383
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H12 Cl N O2'
_chemical_formula_sum            'C12 H12 Cl N O2'
_chemical_formula_weight         237.68
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-08-21
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2690(2)
_cell_length_b                   9.9012(2)
_cell_length_c                   13.5986(2)
_cell_measurement_reflns_used    9052
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.2940
_cell_measurement_theta_min      5.4990
_cell_volume                     1113.36(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015b)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_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    -75.00  22.00   0.50    0.05    --  -49.75  87.00  50.00  194
  2  \w   -156.00 -64.00   0.50    0.05    --  -84.25 -75.00 178.00  184
  3  \w    101.00 178.00   0.50    0.05    --  105.75  87.00  50.00  154
  4  \w   -121.00 -73.00   0.50    0.05    --  -49.75-125.00  90.00   96
  5  \w     -5.00  24.00   0.50    0.05    --  -49.75  19.00-150.00   58
  6  \w     -5.00  24.00   0.50    0.05    --  -49.75  19.00 -30.00   58
  7  \w     -5.00  24.00   0.50    0.05    --  -49.75  19.00 120.00   58
  8  \w    -44.00 -12.00   0.50    0.05    --  -84.25  45.00-120.00   64
  9  \w     97.00 178.00   0.50    0.05    --  105.75  45.00 -90.00  162
 10  \w     34.00  80.00   0.50    0.05    --  105.75 -61.00-120.00   92
 11  \w     98.00 175.00   0.50    0.05    --  105.75  15.00 -90.00  154
 12  \w     34.00 106.00   0.50    0.05    --  105.75 -94.00 -90.00  144
 13  \w     92.00 178.00   0.50    0.05    --  105.75  61.00 150.00  172
 14  \w     98.00 175.00   0.50    0.05    --  105.75  15.00 150.00  154
 15  \w     34.00 106.00   0.50    0.05    --  105.75 -94.00  60.00  144
 16  \w     34.00 106.00   0.50    0.05    --  105.75 -94.00-180.00  144
 17  \w     34.00 106.00   0.50    0.05    --  105.75 -94.00  30.00  144
 18  \w     34.00 111.00   0.50    0.05    --  105.75-125.00 -90.00  154
 19  \w     92.00 178.00   0.50    0.05    --  105.75  61.00-179.00  172
 20  \w   -121.00 -94.00   0.50    0.05    --  -49.75 -77.00 -60.00   54
 21  \w   -121.00 -35.00   0.50    0.05    --  -49.75 -61.00  41.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0471127000
_diffrn_orient_matrix_UB_12      0.0589275000
_diffrn_orient_matrix_UB_13      -0.1008062000
_diffrn_orient_matrix_UB_21      -0.1240439000
_diffrn_orient_matrix_UB_22      0.1143743000
_diffrn_orient_matrix_UB_23      0.0141819000
_diffrn_orient_matrix_UB_31      0.1309853000
_diffrn_orient_matrix_UB_32      0.0872769000
_diffrn_orient_matrix_UB_33      0.0497141000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11869
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        74.504
_diffrn_reflns_theta_max         78.818
_diffrn_reflns_theta_min         5.527
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.913
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.58a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.248
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.113
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 925 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.008(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2356
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0296
_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^)+(0.0243P)^2^+0.4148P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0702
_refine_ls_wR_factor_ref         0.0721
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                2306
_reflns_number_total             2356
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b05383_si_003.cif
_cod_data_source_block           fasac11
_cod_depositor_comments
'Adding full bibliography for 4517359--4517360.cif.'
_cod_database_code               4517359
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.734
_shelx_estimated_absorpt_t_min   0.532
_diffrn_oxdiff_digest_frames
;
013cdbd6e347f907b09af0cd836006774e00157dfbb
;
_diffrn_oxdiff_digest_hkl
;
0122cef441b94cb6b63850d3a77bfbb8c521c0
;
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_shelx_res_checksum              74500
_shelx_hkl_checksum              87301
_olex2_submission_original_sample_id fasac11
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.374
_oxdiff_exptl_absorpt_empirical_full_min 0.735