Catalytic (3+2) Annulation of Donor-Acceptor Aminocyclopropane Monoesters and Indoles
Pirenne, Vincent; Robert, Emma G. L.; Waser, Jerome; Chemical Science  (2021) –; doi:10.1039/D1SC01127H

data_1562389
_publ_section_title
;
 Catalytic (3+2) Annulation of Donor-Acceptor Aminocyclopropane Monoesters
 and Indoles
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC01127H
_journal_year                    2021
_chemical_formula_moiety         'C26 H32 N2 O4 S'
_chemical_formula_sum            'C26 H32 N2 O4 S'
_chemical_formula_weight         468.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-10-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-01-09 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.6343(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.36120(9)
_cell_length_b                   23.6708(4)
_cell_length_c                   15.8181(2)
_cell_measurement_reflns_used    7872
_cell_measurement_temperature    140.01(10)
_cell_measurement_theta_max      72.5650
_cell_measurement_theta_min      3.2960
_cell_volume                     2380.84(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2665
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_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   -111.00 -86.00   1.00    5.00    --  -43.13-159.00 -83.00   25
  2  \w    -92.00 -67.00   1.00    5.00    --  -43.13 159.00 -51.00   25
  3  \w    -39.00  -1.00   1.00    5.00    --  -43.13 118.00 155.00   38
  4  \w     83.00 108.00   1.00    5.00    --   43.13-159.00 -83.00   25
  5  \w     58.00  83.00   1.00    5.00    --   43.13-118.00  69.00   25
  6  \w     46.00 135.00   1.00   20.00    --  103.80-159.00 -83.00   89
  7  \w     83.00 109.00   1.00   20.00    --  103.80-118.00  69.00   26
  8  \w    115.00 140.00   1.00   20.00    --  103.80 118.00 155.00   25
  9  \w     93.00 118.00   1.00   20.00    --  103.80 159.00 -51.00   25
 10  \w   -117.00 -19.00   1.00    5.00    --  -43.13 -37.00  60.00   98
 11  \w    -73.00 -15.00   1.00    5.00    --  -43.13 125.00-150.00   58
 12  \w   -117.00 -32.00   1.00    5.00    --  -43.13 -37.00 -30.00   85
 13  \w     28.00  88.00   1.00    5.00    --   43.13-125.00 150.00   60
 14  \w     79.00 144.00   1.00   20.00    --  103.80 178.00-120.00   65
 15  \w     32.00 108.00   1.00   20.00    --  103.80-111.00 -90.00   76
 16  \w     78.00 166.00   1.00   20.00    --  103.80  45.00 150.00   88
 17  \w     33.00  59.00   1.00   20.00    --  103.80 -45.00  60.00   26
 18  \w     29.00 132.00   1.00   20.00    --  103.80 -30.00 -90.00  103
 19  \w    101.00 129.00   1.00   20.00    --  103.80 -45.00  60.00   28
 20  \w    152.00 177.00   1.00   20.00    --  103.80  45.00-150.00   25
 21  \w     27.00  99.00   1.00   20.00    --  103.80-111.00 -30.00   72
 22  \w    108.00 177.00   1.00   20.00    --  103.80 111.00-150.00   69
 23  \w     94.00 119.00   1.00   20.00    --  103.80  45.00-150.00   25
 24  \w     67.00 134.00   1.00   20.00    --  103.80 -77.00 -60.00   67
 25  \w    103.00 178.00   1.00   20.00    --  103.80  77.00  30.00   75
 26  \w    101.00 150.00   1.00   20.00    --  103.80  61.00  90.00   49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0410184000
_diffrn_orient_matrix_UB_12      0.0249465000
_diffrn_orient_matrix_UB_13      -0.0889004000
_diffrn_orient_matrix_UB_21      -0.0530046000
_diffrn_orient_matrix_UB_22      -0.0594033000
_diffrn_orient_matrix_UB_23      -0.0341600000
_diffrn_orient_matrix_UB_31      -0.2328502000
_diffrn_orient_matrix_UB_32      0.0091353000
_diffrn_orient_matrix_UB_33      0.0205780000
_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  0.0278
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20793
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.575
_diffrn_reflns_theta_min         3.361
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.494
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.582
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_description       needle
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.835
_exptl_crystal_size_mid          0.049
_exptl_crystal_size_min          0.029
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4656
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0347
_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^)+(0.0455P)^2^+1.0227P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0928
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4063
_reflns_number_total             4656
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc01127h2.cif
_cod_data_source_block           pv02-354
_cod_original_cell_volume        2380.84(7)
_cod_database_code               1562389
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C26 H32 N2 O4 S1'
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.369
_reflns_odcompleteness_completeness 99.98
_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, All C(H,H,H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H19D)=Sof(H19E)=Sof(H19F)=1-FVAR(1)
 Sof(H19A)=Sof(H19B)=Sof(H19C)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C2(H2), C9(H9), C10(H10)
3.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C16(H16A,H16B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C13(H13), C21(H21), C22(H22), C24(H24),
 C25(H25)
3.d X=CH2 refined with riding coordinates:
 C14(H14A,H14B)
3.e Disordered Me refined as rotating group:
 C19(H19A,H19B,H19C,H19D,H19E,H19F)
3.f Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              76715
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.193
_oxdiff_exptl_absorpt_empirical_full_min 0.867