Stereodivergent Intramolecular Cyclopropanation Enabled by Engineered Carbene Transferases.
Chandgude, Ajay L.; Ren, Xinkun; Fasan, Rudi; Journal of the American Chemical Society 141 (2019) 9145–9150; doi:10.1021/jacs.9b02700

data_4128746
_publ_section_title
;
 Stereodivergent Intramolecular Cyclopropanation Enabled by Engineered
 Carbene Transferases.
;
_journal_issue                   23
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9145
_journal_page_last               9150
_journal_paper_doi               10.1021/jacs.9b02700
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C11 H10 O2'
_chemical_formula_sum            'C11 H10 O2'
_chemical_formula_weight         174.19
_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   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-12-09
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.8530(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.56590(10)
_cell_length_b                   9.7305(2)
_cell_length_c                   7.66930(10)
_cell_measurement_reflns_used    13700
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.7360
_cell_measurement_theta_min      5.7560
_cell_volume                     414.847(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_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   -122.00 -42.00   0.50    0.05    --  -49.75 -28.00 110.00  160
  2  \w     42.00 122.00   0.50    0.05    --   49.75  28.00 -87.00  160
  3  \w    -23.00  57.00   0.50    0.05    --   49.75 -28.00 110.00  160
  4  \w   -158.00 -77.00   0.50    0.05    --  -84.25 -28.00 110.00  162
  5  \w    -51.00 -11.00   0.50    0.05    --  -84.25  28.00 -87.00   80
  6  \w     98.00 178.00   0.50    0.05    --  105.75  28.00 -87.00  160
  7  \w     32.00  71.00   0.50    0.05    --  105.75 -28.00 110.00   78
  8  \w   -121.00 -70.00   0.50    0.05    --  -49.75-125.00-120.00  102
  9  \w    -51.00  24.00   0.50    0.05    --  -49.75  28.00 -87.00  150
 10  \w   -121.00 -29.00   0.50    0.05    --  -49.75 -77.00-120.00  184
 11  \w     29.00 121.00   0.50    0.05    --   49.75  77.00   0.00  184
 12  \w     29.00 121.00   0.50    0.05    --   49.75  77.00  30.00  184
 13  \w     29.00 121.00   0.50    0.05    --   49.75  77.00-120.00  184
 14  \w     29.00 121.00   0.50    0.05    --   49.75  77.00  90.00  184
 15  \w     29.00 121.00   0.50    0.05    --   49.75  77.00 120.00  184
 16  \w     29.00 121.00   0.50    0.05    --   49.75  77.00-180.00  184
 17  \w     42.00 121.00   0.50    0.05    --   49.75  38.00 -30.00  158
 18  \w     31.00  95.00   0.50    0.05    --   49.75-125.00 -90.00  128
 19  \w     29.00 121.00   0.50    0.05    --   49.75  77.00 -60.00  184
 20  \w     42.00 121.00   0.50    0.05    --   49.75  38.00-180.00  158
 21  \w     29.00 121.00   0.50    0.05    --   49.75  77.00 150.00  184
 22  \w     31.00  95.00   0.50    0.05    --   49.75-125.00-180.00  128
 23  \w   -156.00 -63.00   0.50    0.05    --  -84.25 -77.00 -60.00  186
 24  \w   -156.00 -65.00   0.50    0.05    --  -84.25 -74.00 -13.01  182
 25  \w   -156.00 -62.00   0.50    0.05    --  -84.25 -81.00  81.97  188
 26  \w   -156.00 -65.00   0.50    0.05    --  -84.25 -74.00  11.76  182
 27  \w   -156.00 -63.00   0.50    0.05    --  -84.25 -77.00  60.00  186
 28  \w   -156.00 -63.00   0.50    0.05    --  -84.25 -77.00-150.00  186
 29  \w   -156.00 -63.00   0.50    0.05    --  -84.25 -77.00 120.00  186
 30  \w   -156.00 -69.00   0.50    0.05    --  -84.25 -63.00 139.80  174
 31  \w   -156.00 -65.00   0.50    0.05    --  -84.25 -73.00 -47.43  182
 32  \w   -156.00 -70.00   0.50    0.05    --  -84.25 -61.00 120.00  172
 33  \w   -156.00 -63.00   0.50    0.05    --  -84.25 -79.00 128.09  186
 34  \w   -156.00 -63.00   0.50    0.05    --  -84.25 -77.00 -68.50  186
 35  \w   -156.00 -63.00   0.50    0.05    --  -84.25 -77.00-180.00  186
 36  \w   -156.00 -63.00   0.50    0.05    --  -84.25 -77.00  30.00  186
 37  \w   -156.00 -63.00   0.50    0.05    --  -84.25 -77.00-120.00  186
 38  \w   -156.00 -65.00   0.50    0.05    --  -84.25 -73.00 -88.60  182
 39  \w   -156.00 -63.00   0.50    0.05    --  -84.25 -77.00  90.00  186
 40  \w   -156.00 -70.00   0.50    0.05    --  -84.25 -60.00-123.93  172
 41  \w     98.00 124.00   0.50    0.05    --  105.75  61.00 -90.00   52
 42  \w     95.00 142.00   0.50    0.05    --  105.75  61.00 120.00   94
 43  \w     93.00 154.00   0.50    0.05    --  105.75  61.00  60.00  122
 44  \w    103.00 139.00   0.50    0.05    --  105.75  61.00-120.00   72
 45  \w     34.00 115.00   0.50    0.05    --  105.75-125.00-120.00  162
 46  \w     34.00  71.00   0.50    0.05    --  105.75 -30.00  30.00   74
 47  \w     85.00 136.00   0.50    0.05    --  105.75  77.00 -60.00  102
 48  \w    116.00 177.00   0.50    0.05    --  105.75  77.00 150.00  122
 49  \w     86.00 113.00   0.50    0.05    --  105.75  77.00 150.00   54
 50  \w     92.00 151.00   0.50    0.05    --  105.75  77.00 120.00  118
 51  \w     61.00 109.00   0.50    0.05    --  105.75 -94.00-120.00   96
 52  \w     92.00 120.00   0.50    0.05    --  105.75  61.00-150.00   56
 53  \w     88.00 154.00   0.50    0.05    --  105.75  77.00  30.00  132
 54  \w     52.00 109.00   0.50    0.05    --  105.75 -94.00  30.00  114
 55  \w     90.00 140.00   0.50    0.05    --  105.75  77.00-150.00  100
 56  \w     76.00 107.00   0.50    0.05    --  105.75 -94.00 150.00   62
 57  \w     98.00 139.00   0.50    0.05    --  105.75  61.00 -30.00   82
 58  \w     73.00 106.00   0.50    0.05    --  105.75 -94.00  90.00   66
 59  \w     36.00  81.00   0.50    0.05    --  105.75 -45.00-120.00   90
 60  \w    129.00 155.00   0.50    0.05    --  105.75  77.00-180.00   52
 61  \w     90.00 116.00   0.50    0.05    --  105.75  77.00-180.00   52
 62  \w     34.00  73.00   0.50    0.05    --  105.75 -94.00 150.00   78
 63  \w     61.00 128.00   0.50    0.05    --  105.75-140.00  31.07  134
 64  \w     94.00 129.00   0.50    0.05    --  105.75  61.00  30.00   70
 65  \w     92.00 127.00   0.50    0.05    --  105.75  61.00  90.00   70
 66  \w     59.00  85.00   0.50    0.05    --  105.75 -94.00 -90.00   52
 67  \w     45.00  71.00   0.50    0.05    --  105.75 -45.00   0.00   52
 68  \w     55.00  86.00   0.50    0.05    --  105.75 -94.00 120.00   62
 69  \w    135.00 175.00   0.50    0.05    --  105.75  77.00  90.00   80
 70  \w     87.00 131.00   0.50    0.05    --  105.75  77.00 -30.00   88
 71  \w     41.00  90.00   0.50    0.05    --  105.75 -45.00  30.00   98
 72  \w     90.00 116.00   0.50    0.05    --  105.75  77.00  90.00   52
 73  \w    146.00 174.00   0.50    0.05    --  105.75  77.00   0.00   56
 74  \w     34.00 111.00   0.50    0.05    --  105.75-125.00  30.00  154
 75  \w     86.00 129.00   0.50    0.05    --  105.75  77.00   0.00   86
 76  \w     86.00 112.00   0.50    0.05    --  105.75  77.00 -90.00   52
 77  \w    130.00 158.00   0.50    0.05    --  105.75  61.00 -90.00   56
 78  \w     34.00  82.00   0.50    0.05    --  105.75 -45.00-150.00   96
 79  \w     99.00 161.00   0.50    0.05    --  105.75 125.00 150.00  124
;
_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      -0.0489266000
_diffrn_orient_matrix_UB_12      0.0556436000
_diffrn_orient_matrix_UB_13      0.1829276000
_diffrn_orient_matrix_UB_21      0.2727183000
_diffrn_orient_matrix_UB_22      0.0114005000
_diffrn_orient_matrix_UB_23      0.0422012000
_diffrn_orient_matrix_UB_31      -0.0026268000
_diffrn_orient_matrix_UB_32      0.1478123000
_diffrn_orient_matrix_UB_33      -0.0721453000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15070
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        74.504
_diffrn_reflns_theta_max         77.899
_diffrn_reflns_theta_min         5.776
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.773
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.01562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.394
_exptl_crystal_description       needle
_exptl_crystal_F_000             184
_exptl_crystal_size_max          0.305
_exptl_crystal_size_mid          0.236
_exptl_crystal_size_min          0.144
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 763 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).

 Hooft y = 0.04(5).
;
_refine_ls_abs_structure_Flack   0.03(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1701
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0280
_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^)+(0.0383P)^2^+0.0884P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0690
_refine_ls_wR_factor_ref         0.0691
_reflns_Friedel_coverage         0.837
_reflns_Friedel_fraction_full    0.965
_reflns_Friedel_fraction_max     0.927
_reflns_number_gt                1691
_reflns_number_total             1701
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b02700_si_002.cif
_cod_data_source_block           fasac08
_cod_database_code               4128746
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.897
_shelx_estimated_absorpt_t_min   0.798
_reflns_odcompleteness_completeness 99.89
_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
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), C9(H9), C10(H10), C11(H11)
;
_shelx_res_checksum              5915
_shelx_hkl_checksum              15848
_olex2_submission_original_sample_id fasac08
_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 6.615
_oxdiff_exptl_absorpt_empirical_full_min 0.682