Nitrogen-interrupted <i>halo</i>-Prins/<i>halo</i>-Nazarov fragment coupling cascade for the synthesis of indolines.
Milosavljevic, Aleksa; Holt, Connor; Frontier, Alison J.; Chemical science 14 (2023) 5431–5437; doi:10.1039/d3sc00986f

data_1568948
_publ_section_title
;
 Nitrogen-interrupted <i>halo</i>-Prins/<i>halo</i>-Nazarov fragment
 coupling cascade for the synthesis of indolines.
;
_journal_issue                   20
_journal_name_full               'Chemical science'
_journal_page_first              5431
_journal_page_last               5437
_journal_paper_doi               10.1039/d3sc00986f
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C27 H25 I N2 O5 S'
_chemical_formula_sum            'C27 H25 I N2 O5 S'
_chemical_formula_weight         616.45
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-12-31
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-02-07 deposited with the CCDC.	2023-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                83.790(2)
_cell_angle_beta                 76.551(2)
_cell_angle_gamma                65.058(2)
_cell_formula_units_Z            2
_cell_length_a                   10.3499(2)
_cell_length_b                   11.4812(2)
_cell_length_c                   11.8168(2)
_cell_measurement_reflns_used    30095
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.9050
_cell_measurement_theta_min      3.8400
_cell_volume                     1238.22(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2018/2 (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 0.997
_diffrn_measured_fraction_theta_max 0.979
_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   -119.00 -32.00   0.50    0.31    --  -47.28 -59.00 -40.00  174
  2  \w    -24.00  63.00   0.50    0.31    --   47.28 -59.00 -40.00  174
  3  \w     32.00 120.00   0.50    0.31    --   47.28  59.00  99.00  176
  4  \w   -163.00 -76.00   0.50    1.23    --  -91.75 -59.00 -40.00  174
  5  \w    -68.00 -19.00   0.50    1.23    --  -91.75  59.00  99.00   98
  6  \w     98.00 178.00   0.50    1.23    --  113.25  59.00  99.00  160
  7  \w     42.00  72.00   0.50    1.23    --  113.25 -59.00 -40.00   60
  8  \w    -63.00  25.00   0.50    0.31    --  -47.28  59.00  99.00  176
  9  \w    -14.00  28.00   0.50    0.31    --  -47.28  19.00-150.00   84
 10  \w    -14.00  28.00   0.50    0.31    --  -47.28  19.00-180.00   84
 11  \w     34.00  93.00   0.50    0.31    --   47.28-125.00-180.00  118
 12  \w    -27.00  18.00   0.50    0.31    --   47.28 -19.00-150.00   90
 13  \w    -24.00  70.00   0.50    0.31    --   47.28 -77.00-180.00  188
 14  \w    -27.00  18.00   0.50    0.31    --   47.28 -19.00 -30.00   90
 15  \w    -47.00 -20.00   0.50    1.23    --  -91.75  45.00  90.00   54
 16  \w    -47.00 -20.00   0.50    1.23    --  -91.75  45.00 -60.00   54
 17  \w    -72.00 -19.00   0.50    1.23    --  -91.75  61.00 -90.00  106
 18  \w     44.00 111.00   0.50    1.23    --  113.25-125.00  90.00  134
 19  \w    100.00 178.00   0.50    1.23    --  113.25  15.00-180.00  156
 20  \w     44.00 111.00   0.50    1.23    --  113.25-125.00  60.00  134
 21  \w    100.00 178.00   0.50    1.23    --  113.25  15.00 -60.00  156
 22  \w     42.00 106.00   0.50    1.23    --  113.25 -94.00 120.00  128
 23  \w     42.00  76.00   0.50    1.23    --  113.25 -61.00  90.00   68
 24  \w     42.00  76.00   0.50    1.23    --  113.25 -61.00 120.00   68
 25  \w     97.00 178.00   0.50    1.23    --  113.25  61.00  30.00  162
 26  \w    101.00 178.00   0.50    1.23    --  113.25  45.00-120.00  154
 27  \w     42.00 106.00   0.50    1.23    --  113.25 -94.00 -90.00  128
 28  \w    101.00 178.00   0.50    1.23    --  113.25  45.00 -30.00  154
 29  \w     42.00 106.00   0.50    1.23    --  113.25 -94.00 -60.00  128
 30  \w     44.00 111.00   0.50    1.23    --  113.25-125.00-150.00  134
 31  \w     44.00 111.00   0.50    1.23    --  113.25-125.00 120.00  134
 32  \w     42.00 106.00   0.50    1.23    --  113.25 -94.00-120.00  128
 33  \w     42.00  76.00   0.50    1.23    --  113.25 -61.00 -60.00   68
 34  \w     42.00  76.00   0.50    1.23    --  113.25 -61.00 -30.00   68
 35  \w     43.00 105.00   0.50    1.23    --  113.25 -96.00-151.48  124
 36  \w     42.00 106.00   0.50    1.23    --  113.25 -94.00 -30.00  128
 37  \w     42.00  76.00   0.50    1.23    --  113.25 -61.00 150.00   68
 38  \w     42.00 106.00   0.50    1.23    --  113.25 -94.00  60.00  128
 39  \w     42.00 106.00   0.50    1.23    --  113.25 -94.00   0.00  128
 40  \w     91.00 178.00   0.50    1.23    --  113.25  77.00  60.00  174
 41  \w     95.00 178.00   0.50    1.23    --  113.25 125.00   0.00  166
 42  \w     44.00 111.00   0.50    1.23    --  113.25-125.00-120.00  134
 43  \w     42.00  76.00   0.50    1.23    --  113.25 -61.00-120.00   68
 44  \w    101.00 178.00   0.50    1.23    --  113.25  45.00 150.00  154
 45  \w    101.00 178.00   0.50    1.23    --  113.25  45.00-180.00  154
 46  \w    101.00 178.00   0.50    1.23    --  113.25  45.00   0.00  154
 47  \w   -119.00 -25.00   0.50    0.31    --  -47.28 -77.00  60.00  188
 48  \w   -119.00 -25.00   0.50    0.31    --  -47.28 -77.00 120.00  188
 49  \w   -120.00 -34.00   0.50    0.31    --  -47.28 -38.00  90.00  172
 50  \w     25.00 120.00   0.50    0.31    --   47.28  77.00 -90.00  190
 51  \w     25.00 120.00   0.50    0.31    --   47.28  77.00  30.00  190
 52  \w     32.00 120.00   0.50    0.31    --   47.28  57.00 -90.00  176
 53  \w     25.00 120.00   0.50    0.31    --   47.28  77.00 120.00  190
 54  \w     25.00 120.00   0.50    0.31    --   47.28  77.00-150.00  190
 55  \w     32.00 120.00   0.50    0.31    --   47.28  57.00-150.00  176
 56  \w     25.00 120.00   0.50    0.31    --   47.28  77.00 -30.00  190
 57  \w   -163.00 -72.00   0.50    1.23    --  -91.75 -70.00 -77.20  182
 58  \w   -163.00 -69.00   0.50    1.23    --  -91.75 -76.00 144.27  188
 59  \w   -163.00 -71.00   0.50    1.23    --  -91.75 -72.00  75.85  184
 60  \w   -163.00 -70.00   0.50    1.23    --  -91.75 -74.00  15.47  186
 61  \w   -163.00 -69.00   0.50    1.23    --  -91.75 -76.00 -94.72  188
 62  \w   -163.00 -69.00   0.50    1.23    --  -91.75 -76.00 -49.90  188
 63  \w   -163.00 -73.00   0.50    1.23    --  -91.75 -67.00  36.22  180
 64  \w   -163.00 -69.00   0.50    1.23    --  -91.75 -77.00 120.00  188
 65  \w   -163.00 -69.00   0.50    1.23    --  -91.75 -77.00-120.00  188
 66  \w   -163.00 -70.00   0.50    1.23    --  -91.75 -75.00-165.78  186
 67  \w    101.00 178.00   0.50    1.23    --  113.25  45.00-150.00  154
;
_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      0.0828605000
_diffrn_orient_matrix_UB_12      -0.1158018000
_diffrn_orient_matrix_UB_13      -0.0820348000
_diffrn_orient_matrix_UB_21      0.1215844000
_diffrn_orient_matrix_UB_22      0.0475380000
_diffrn_orient_matrix_UB_23      -0.0458938000
_diffrn_orient_matrix_UB_31      0.0806873000
_diffrn_orient_matrix_UB_32      -0.0789432000
_diffrn_orient_matrix_UB_33      0.0955759000
_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  0.0455
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            41813
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        74.504
_diffrn_reflns_theta_max         80.507
_diffrn_reflns_theta_min         3.846
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    11.303
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
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    1.653
_exptl_crystal_description       block
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_min          0.036
_refine_diff_density_max         1.014
_refine_diff_density_min         -1.014
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         5316
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.140
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0281
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0459P)^2^+1.2837P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0800
_refine_ls_wR_factor_ref         0.0807
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5092
_reflns_number_total             5316
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc00986f2.cif
_cod_data_source_block           froam05
_cod_depositor_comments
'Adding full bibliography for 1568947--1568949.cif.'
_cod_original_cell_volume        1238.23(4)
_cod_database_code               1568948
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.686
_shelx_estimated_absorpt_t_min   0.550
_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) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Sof(O1')=Sof(H1')=Sof(H22C)=Sof(H22D)=1-FVAR(1)
 Sof(O1)=Sof(H1)=Sof(H22A)=Sof(H22B)=FVAR(1)
3.a Riding coordinates:
 O1'(H1'), O1(H1)
3.b Ternary CH refined with riding coordinates:
 C3(H3), C4(H4)
3.c Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C21(H21A,H21B), C22(H22C,H22D), C22(H22A,H22B)
3.d Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15), C16(H16),
 C17(H17), C25(H25), C26(H26), C27(H27), C28(H28)
3.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_shelx_res_checksum              3905
_shelx_hkl_checksum              39989
_olex2_submission_original_sample_id froam05
_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 1.190
_oxdiff_exptl_absorpt_empirical_full_min 0.812