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_1562388
_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         'C31 H31 N3 O6 S'
_chemical_formula_sum            'C31 H31 N3 O6 S'
_chemical_formula_weight         573.65
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-09-04
_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                 98.870(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.0965(8)
_cell_length_b                   5.88104(18)
_cell_length_c                   26.5867(10)
_cell_measurement_reflns_used    15017
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      75.7330
_cell_measurement_theta_min      4.4070
_cell_volume                     3104.7(2)
_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      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.980
_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    -80.00   5.00   1.00    2.00    --  -40.91 112.00  67.00   85
  2  \w     43.00  76.00   1.00    2.00    --   40.91-112.00 -24.00   33
  3  \w    112.00 142.00   1.00    8.00    --  112.00 112.00  67.00   30
  4  \w     59.00  94.00   1.00    8.00    --  112.00-112.00 -24.00   35
  5  \w   -113.00 -26.00   1.00    2.00    --  -40.91 -38.00   0.00   87
  6  \w    -65.00  29.00   1.00    2.00    --  -40.91  38.00   0.00   94
  7  \w     78.00 110.00   1.00    2.00    --   40.91  38.00-120.00   32
  8  \w     28.00  53.00   1.00    2.00    --   40.91 -38.00-120.00   25
  9  \w    -20.00  71.00   1.00    2.00    --   40.91 -77.00-180.00   91
 10  \w    -13.00  14.00   1.00    2.00    --   40.91 -38.00-120.00   27
 11  \w     38.00 108.00   1.00    8.00    --  112.00-104.00-105.82   70
 12  \w     62.00 102.00   1.00    8.00    --  112.00 178.00   0.00   40
 13  \w     90.00 177.00   1.00    8.00    --  112.00  45.00  30.00   87
 14  \w     44.00  71.00   1.00    8.00    --  112.00-111.00   0.00   27
 15  \w     81.00 109.00   1.00    8.00    --  112.00-111.00   0.00   28
 16  \w     37.00 103.00   1.00    8.00    --  112.00-111.00 150.00   66
 17  \w     95.00 143.00   1.00    8.00    --  112.00 -77.00 -60.00   48
 18  \w     87.00 167.00   1.00    8.00    --  112.00  45.00 120.00   80
 19  \w     62.00 113.00   1.00    8.00    --  112.00 178.00  30.00   51
 20  \w     37.00 109.00   1.00    8.00    --  112.00-111.00 120.00   72
 21  \w    106.00 150.00   1.00    8.00    --  112.00  77.00 -60.00   44
 22  \w    109.00 177.00   1.00    8.00    --  112.00 111.00 -30.00   68
 23  \w     44.00  69.00   1.00    8.00    --  112.00-111.00-150.00   25
 24  \w     79.00 137.00   1.00    8.00    --  112.00 -45.00 120.00   58
 25  \w    104.00 178.00   1.00    8.00    --  112.00  61.00  60.00   74
 26  \w     61.00 100.00   1.00    8.00    --  112.00 -77.00   0.00   39
 27  \w     30.00  56.00   1.00    8.00    --  112.00 -15.00 120.00   26
 28  \w     78.00 125.00   1.00    8.00    --  112.00 -15.00 120.00   47
 29  \w     62.00 109.00   1.00    8.00    --  112.00-111.00  60.00   47
 30  \w     41.00 134.00   1.00    8.00    --  112.00 -61.00-120.00   93
 31  \w     39.00 109.00   1.00    8.00    --  112.00-111.00-180.00   70
 32  \w     43.00 107.00   1.00    8.00    --  112.00 -94.00-180.00   64
 33  \w     42.00  95.00   1.00    8.00    --  112.00 -45.00   0.00   53
 34  \w     72.00 109.00   1.00    8.00    --  112.00-111.00 -60.00   37
 35  \w    130.00 155.00   1.00    8.00    --  112.00  77.00 150.00   25
 36  \w    103.00 138.00   1.00    8.00    --  112.00  77.00 -30.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0177864000
_diffrn_orient_matrix_UB_12      -0.0413178000
_diffrn_orient_matrix_UB_13      -0.0535805000
_diffrn_orient_matrix_UB_21      -0.0469006000
_diffrn_orient_matrix_UB_22      0.1965730000
_diffrn_orient_matrix_UB_23      -0.0210232000
_diffrn_orient_matrix_UB_31      0.0591202000
_diffrn_orient_matrix_UB_32      0.1683123000
_diffrn_orient_matrix_UB_33      0.0113810000
_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  0.0311
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            32676
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.763
_diffrn_reflns_theta_min         3.365
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.304
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.321
_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 intense yellow'
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_description       prism
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.538
_exptl_crystal_size_mid          0.228
_exptl_crystal_size_min          0.132
_refine_diff_density_max         0.627
_refine_diff_density_min         -0.615
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.00077(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     542
_refine_ls_number_reflns         6437
_refine_ls_number_restraints     731
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0753
_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^)+(0.0650P)^2^+4.4569P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1829
_refine_ls_wR_factor_ref         0.1849
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6031
_reflns_number_total             6437
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc01127h2.cif
_cod_data_source_block           pv02-245
_cod_original_cell_volume        3104.65(19)
_cod_database_code               1562388
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C31 H31 N3 O6 S1'
_shelx_estimated_absorpt_t_max   0.847
_shelx_estimated_absorpt_t_min   0.541
_reflns_odcompleteness_completeness 99.66
_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, All C(H,H,H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O5-C36 = O6-C36
 1.2 with sigma of 0.01
 C39-C40 = C38-C37
 1.54 with sigma of 0.01
 O8-C39 = O7-C37
 1.43 with sigma of 0.01
 S1-C28 \\sim S1-C22
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O5 \\sim O6 \\sim O7 \\sim O8 \\sim C36 \\sim C37 \\sim C38 \\sim C39 \\sim
C40: within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01 within
2A
C22 \\sim C23 \\sim C24 \\sim C25 \\sim C26 \\sim C27 \\sim C28 \\sim C29 \\sim
C30 \\sim C31 \\sim C32 \\sim C33 \\sim C34 \\sim C35: within 2A with sigma of
0.02 and sigma for terminal atoms of 0.04 within 2A
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(O6)=Sof(O8)=Sof(C39)=Sof(H39A)=Sof(H39B)=Sof(C40)=Sof(H40A)=Sof(H40B)=
 Sof(H40C)=1-FVAR(1)
 Sof(O5)=Sof(O7)=Sof(C37)=Sof(H37A)=Sof(H37B)=Sof(C38)=Sof(H38A)=Sof(H38B)=
 Sof(H38C)=FVAR(1)
 Sof(C28)=Sof(C29)=Sof(H29)=Sof(C30)=Sof(H30)=Sof(C31)=Sof(C32)=Sof(H32)=
 Sof(C33)=Sof(H33)=Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(H35C)=1-FVAR(2)
 Sof(C22)=Sof(C23)=Sof(H23)=Sof(C24)=Sof(H24)=Sof(C25)=Sof(C26)=Sof(H26)=
 Sof(C27)=Sof(H27)=Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(H34C)=FVAR(2)
 Sof(H21D)=Sof(H21E)=Sof(H21F)=1-FVAR(3)
 Sof(H21A)=Sof(H21B)=Sof(H21C)=FVAR(3)
6.a Secondary CH2 refined with riding coordinates:
 C37(H37A,H37B), C39(H39A,H39B)
6.b Aromatic/amide H refined with riding coordinates:
 C23(H23), C24(H24), C26(H26), C27(H27), C29(H29), C30(H30), C32(H32), C33(H33)
6.c Disordered Me refined as rotating group:
 C21(H21A,H21B,H21C,H21D,H21E,H21F)
6.d Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C38(H38A,H38B,H38C), C40(H40A,H40B,
 H40C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              96602
_shelx_fab_checksum              63259
_olex2_date_sample_data_collection 2020-09-04
_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 2.435
_oxdiff_exptl_absorpt_empirical_full_min 0.614