A Diverse Library of Chiral Cyclopropane Scaffolds via Chemoenzymatic Assembly and Diversification of Cyclopropyl Ketones.
Nam, Donggeon; Steck, Viktoria; Potenzino, Robert J.; Fasan, Rudi; Journal of the American Chemical Society  (2021) –; doi:10.1021/jacs.0c09504

data_4135551
_publ_section_title
;
 A Diverse Library of Chiral Cyclopropane Scaffolds via Chemoenzymatic
 Assembly and Diversification of Cyclopropyl Ketones.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c09504
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H15 Br O'
_chemical_formula_sum            'C17 H15 Br O'
_chemical_formula_weight         315.20
_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             2018-06-13
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8732(2)
_cell_length_b                   7.3387(3)
_cell_length_c                   32.1290(14)
_cell_measurement_reflns_used    14400
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.3000
_cell_measurement_theta_min      2.7730
_cell_volume                     1384.81(10)
_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 0.995
_diffrn_measured_fraction_theta_max 0.953
_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   -121.00 -74.00   0.50    0.05    --  -49.87-119.00   4.00   94
  2  \w   -113.00 -26.00   0.50    0.05    --  -49.87 157.00-115.00  174
  3  \w   -121.00 -48.00   0.50    0.05    --  -49.87-157.00-150.00  146
  4  \w     70.00 121.00   0.50    0.05    --   49.87 157.00-115.00  102
  5  \w     27.00  92.00   0.50    0.05    --   49.87-119.00   4.00  130
  6  \w   -112.00 -26.00   0.50    0.05    --  -84.25 157.00-115.00  172
  7  \w   -156.00 -74.00   0.50    0.05    --  -84.25-119.00   4.00  164
  8  \w     48.00 138.00   0.50    0.05    --  105.75-157.00-150.00  180
  9  \w     96.00 178.00   0.50    0.05    --  105.75 119.00  89.00  164
 10  \w     70.00 166.00   0.50    0.05    --  105.75 157.00-115.00  192
 11  \w     34.00 113.00   0.50    0.05    --  105.75-119.00   4.00  158
 12  \w   -121.00 -29.00   0.50    0.05    --  -49.87 -77.00 -90.00  184
 13  \w   -121.00 -70.00   0.50    0.05    --  -49.87-125.00  30.00  102
 14  \w     34.00  72.00   0.50    0.05    --  105.75 -30.00   0.00   76
 15  \w     34.00  72.00   0.50    0.05    --  105.75 -30.00-150.00   76
 16  \w     34.00 116.00   0.50    0.05    --  105.75-125.00 -90.00  164
 17  \w     34.00 111.00   0.50    0.05    --  105.75-125.00 -30.00  154
 18  \w     37.00  72.00   0.50    0.05    --  105.75 -30.00 150.00   70
 19  \w     34.00  67.00   0.50    0.05    --  105.75 -30.00 -60.00   66
 20  \w     34.00  90.00   0.50    0.05    --  105.75 -45.00 120.00  112
 21  \w     61.00 118.00   0.50    0.05    --  105.75 -61.00 -90.00  114
 22  \w     39.00  71.00   0.50    0.05    --  105.75 -30.00 -30.00   64
 23  \w     84.00 125.00   0.50    0.05    --  105.75 -77.00-120.00   82
 24  \w     51.00  77.00   0.50    0.05    --  105.75 -15.00 150.00   52
 25  \w     35.00  90.00   0.50    0.05    --  105.75 -45.00  60.00  110
 26  \w     42.00  79.00   0.50    0.05    --  105.75 -61.00-180.00   74
 27  \w     93.00 119.00   0.50    0.05    --  105.75 -61.00-180.00   52
 28  \w     34.00  69.00   0.50    0.05    --  105.75 -30.00 120.00   70
;
_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      -0.1799037000
_diffrn_orient_matrix_UB_12      0.0571251000
_diffrn_orient_matrix_UB_13      0.0323557000
_diffrn_orient_matrix_UB_21      0.1792940000
_diffrn_orient_matrix_UB_22      -0.0154921000
_diffrn_orient_matrix_UB_23      0.0348108000
_diffrn_orient_matrix_UB_31      0.0650465000
_diffrn_orient_matrix_UB_32      0.2014754000
_diffrn_orient_matrix_UB_33      -0.0064109000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            16745
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        74.504
_diffrn_reflns_theta_max         82.168
_diffrn_reflns_theta_min         2.751
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.940
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70207
_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    1.512
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.067
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.734
_refine_diff_density_rms         0.096
_refine_ls_abs_structure_details
;
 Flack x determined using 1082 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.026(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2907
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0307
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0380P)^2^+2.0506P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0836
_reflns_Friedel_coverage         0.669
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.933
_reflns_number_gt                2830
_reflns_number_total             2907
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            compound_5d.cif
_cod_data_source_block           fasdn01
_cod_database_code               4135551
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C17H15BrO
_shelx_estimated_absorpt_t_max   0.778
_shelx_estimated_absorpt_t_min   0.432
_reflns_odcompleteness_completeness 99.48
_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)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C16(H16),
 C17(H17)
;
_shelx_res_checksum              3462
_shelx_hkl_checksum              68467
_olex2_submission_original_sample_id fasdn01
_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 3.278
_oxdiff_exptl_absorpt_empirical_full_min 0.677