Hypervalent iodine promoted the synthesis of cycloheptatrienes and cyclopropanes
Yuan, Da-Fu; Wang, Zi-Chen; Geng, Rui-Sen; Ren, Guang-Yi; Wright, James S.; Ni, Shao-Fei; Li, Ming; Wen, Li-Rong; Zhang, Lin-Bao; Chemical Science 13 (2022) 478–485; doi:10.1039/D1SC05429E

data_1565606
_publ_section_title
;
 Hypervalent iodine promoted the synthesis of cycloheptatrienes and
 cyclopropanes
;
_journal_issue                   2
_journal_name_full               'Chemical Science'
_journal_page_first              478
_journal_page_last               485
_journal_paper_doi               10.1039/D1SC05429E
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C19 H16 F3 N O2'
_chemical_formula_sum            'C19 H16 F3 N O2'
_chemical_formula_weight         347.33
_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   geom
_audit_creation_date             2019-04-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-04-29 deposited with the CCDC.	2021-11-29 downloaded from the CCDC.
;
_cell_angle_alpha                94.9390(10)
_cell_angle_beta                 96.7790(10)
_cell_angle_gamma                110.5760(10)
_cell_formula_units_Z            4
_cell_length_a                   9.42120(10)
_cell_length_b                   10.76290(10)
_cell_length_c                   18.7421(2)
_cell_measurement_reflns_used    45791
_cell_measurement_temperature    169.99(13)
_cell_measurement_theta_max      75.2870
_cell_measurement_theta_min      2.4290
_cell_volume                     1750.05(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_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   -116.00 -28.00   0.50    0.05    --  -47.20 159.00 -14.00  176
  2  \w   -120.00 -48.00   0.50    0.05    --  -47.20-159.00 -46.00  144
  3  \w    -91.00  -5.00   0.50    0.05    --  -47.20 118.00-167.00  172
  4  \w     12.00  91.00   0.50    0.05    --   47.20-118.00 106.00  158
  5  \w     34.00 116.00   0.50    0.05    --   47.20-159.00 -46.00  164
  6  \w     54.00 120.00   0.50    0.05    --   47.20 159.00 -14.00  132
  7  \w   -140.00 -28.00   0.50    0.05    --  -99.00 159.00 -14.00  224
  8  \w   -168.00 -75.00   0.50    0.05    --  -99.00-118.00 106.00  186
  9  \w   -112.00 -26.00   0.50    0.05    --  -99.00 118.00-167.00  172
 10  \w   -164.00 -48.00   0.50    0.05    --  -99.00-159.00 -46.00  232
 11  \w     54.00 164.00   0.50    0.05    --  103.25 159.00 -14.00  220
 12  \w     75.00 138.00   0.50    0.05    --  103.25-159.00 -46.00  126
 13  \w     54.00  80.00   0.50    0.05    --  103.25-118.00 106.00   52
 14  \w    107.00 133.00   0.50    0.05    --  103.25 118.00-167.00   52
 15  \w    -57.00 -31.00   0.50    0.05    --   14.00 163.00 -92.50   52
 16  \w     -7.00  21.00   0.50    0.05    --   26.00 100.00  14.75   56
 17  \w      2.00  27.00   0.50    0.05    --   34.00  97.00 151.07   50
 18  \w      8.00  36.00   0.50    0.05    --   38.00  93.00 -75.06   56
 19  \w     12.00  37.00   0.50    0.05    --   38.00  87.00  49.16   50
 20  \w    -82.00 -36.00   0.50    0.05    --  -47.20 -41.00 -25.46   92
 21  \w    -49.00 -24.00   0.50    0.05    --  -47.20 -77.00 -90.00   50
 22  \w   -121.00 -56.00   0.50    0.05    --  -47.20 -19.00   0.00  130
 23  \w   -105.00 -79.00   0.50    0.05    --  -47.20 -77.00 -90.00   52
 24  \w     87.00 117.00   0.50    0.05    --   47.20  19.00 120.00   60
 25  \w     77.00 116.00   0.50    0.05    --   47.20  38.00-180.00   78
 26  \w     38.00  70.00   0.50    0.05    --   47.20  38.00-180.00   64
 27  \w     41.00  80.00   0.50    0.05    --   47.20  19.00 120.00   78
 28  \w     25.00  54.00   0.50    0.05    --   50.00  82.00 152.43   58
 29  \w     26.00  55.00   0.50    0.05    --   50.00  81.00-165.49   58
 30  \w     29.00  93.00   0.50    0.05    --   50.00  77.00   4.74  128
 31  \w    -57.00 -31.00   0.50    0.05    --  -54.00 -77.00  43.27   52
 32  \w     34.00  60.00   0.50    0.05    --   54.00  74.00-133.02   52
 33  \w     33.00  59.00   0.50    0.05    --   54.00  77.00 121.08   52
 34  \w     30.00  56.00   0.50    0.05    --   54.00  81.00  76.51   52
 35  \w     34.00  65.00   0.50    0.05    --   58.00  80.00-115.73   62
 36  \w     33.00  59.00   0.50    0.05    --   58.00  83.00 -12.68   52
 37  \w     36.00  73.00   0.50    0.05    --   58.00  78.00 -76.14   74
 38  \w     38.00  64.00   0.50    0.05    --   58.00  75.00  74.85   52
 39  \w    -79.00 -41.00   0.50    0.05    --  -62.00 -73.00-137.52   76
 40  \w    -64.00 -38.00   0.50    0.05    --  -62.00 -82.00 -93.44   52
 41  \w     43.00  68.00   0.50    0.05    --   62.00  77.00  76.64   50
 42  \w     38.00  72.00   0.50    0.05    --   62.00  80.00  34.93   68
 43  \w     40.00  78.00   0.50    0.05    --   62.00  76.00 -65.67   76
 44  \w     40.00  66.00   0.50    0.05    --   62.00  75.00 176.30   52
 45  \w    -75.00 -48.00   0.50    0.05    --  -66.00 -66.00-178.22   54
 46  \w     42.00  69.00   0.50    0.05    --   66.00  79.00 -44.58   54
 47  \w     51.00  77.00   0.50    0.05    --   66.00  66.00  97.02   52
 48  \w     43.00  69.00   0.50    0.05    --   66.00  79.00   7.69   52
 49  \w    -79.00 -53.00   0.50    0.05    --  -70.00 -63.00 171.30   52
 50  \w    -76.00 -49.00   0.50    0.05    --  -70.00 -80.00  33.02   54
 51  \w    -79.00 -48.00   0.50    0.05    --  -70.00 -76.00-136.03   62
 52  \w    -96.00 -54.00   0.50    0.05    --  -70.00 -62.00  61.73   84
 53  \w     47.00  74.00   0.50    0.05    --   70.00  79.00 123.95   54
 54  \w    -78.00 -51.00   0.50    0.05    --  -74.00 -83.00 -52.97   54
 55  \w    -75.00 -49.00   0.50    0.05    --  -74.00 -82.00 128.72   52
 56  \w    -75.00 -49.00   0.50    0.05    --  -74.00 -81.00-106.53   52
 57  \w    -85.00 -59.00   0.50    0.05    --  -74.00 -62.00 167.65   52
 58  \w    -76.00 -50.00   0.50    0.05    --  -74.00 -79.00  50.32   52
 59  \w    -78.00 -52.00   0.50    0.05    --  -78.00 -83.00  20.08   52
 60  \w    -80.00 -53.00   0.50    0.05    --  -78.00 -81.00 -12.08   54
 61  \w    -77.00 -52.00   0.50    0.05    --  -78.00 -83.00 145.40   50
 62  \w    -85.00 -59.00   0.50    0.05    --  -82.00 -77.00 178.84   52
 63  \w    -82.00 -56.00   0.50    0.05    --  -82.00 -83.00 129.62   52
 64  \w    -87.00 -60.00   0.50    0.05    --  -82.00 -74.00 102.75   54
 65  \w    -81.00 -56.00   0.50    0.05    --  -82.00 -83.00 -96.27   50
 66  \w    -91.00 -65.00   0.50    0.05    --  -82.00 -63.00-163.74   52
 67  \w   -154.00 -59.00   0.50    0.05    --  -82.00 -76.00 -36.85  190
 68  \w    -90.00 -57.00   0.50    0.05    --  -82.00 -81.00 -79.40   66
 69  \w    -86.00 -60.00   0.50    0.05    --  -86.00 -83.00  53.80   52
 70  \w   -152.00-126.00   0.50    0.05    --  -86.00 -83.00  53.80   52
 71  \w    -92.00 -64.00   0.50    0.05    --  -86.00 -74.00   3.93   56
 72  \w   -157.00-131.00   0.50    0.05    --  -86.00 -74.00   3.93   52
 73  \w   -159.00 -64.00   0.50    0.05    --  -86.00 -74.00 -88.34  190
 74  \w   -161.00 -73.00   0.50    0.05    --  -90.00 -62.00  64.22  176
 75  \w   -100.00 -73.00   0.50    0.05    --  -90.00 -62.00-164.15   54
 76  \w    -92.00 -67.00   0.50    0.05    --  -90.00 -76.00  99.75   50
 77  \w   -119.00 -94.00   0.50    0.05    --  -90.00 -76.00  99.75   50
 78  \w    -98.00 -71.00   0.50    0.05    --  -90.00 -68.00 117.61   54
 79  \w   -151.00 -71.00   0.50    0.05    --  -90.00 -67.00-130.25  160
 80  \w   -114.00 -72.00   0.50    0.05    --  -90.00 -64.00  43.29   84
 81  \w   -154.00-128.00   0.50    0.05    --  -90.00 -69.00 155.39   52
 82  \w   -102.00 -70.00   0.50    0.05    --  -90.00 -69.00 155.39   64
 83  \w    -95.00 -68.00   0.50    0.05    --  -90.00 -76.00 -92.78   54
 84  \w   -165.00 -80.00   0.50    0.05    --  -94.00 -53.00-103.71  170
 85  \w   -167.00 -75.00   0.50    0.05    --  -94.00 -68.00 146.72  184
 86  \w    -98.00 -71.00   0.50    0.05    --  -94.00 -76.00 123.06   54
 87  \w   -151.00-124.00   0.50    0.05    --  -94.00 -76.00 123.06   54
 88  \w   -102.00 -74.00   0.50    0.05    --  -98.00 -80.00-161.80   56
 89  \w   -157.00-113.00   0.50    0.05    --  -98.00 -80.00-161.80   88
 90  \w   -121.00 -28.00   0.50    0.05    --  -99.00  77.00  30.00  186
 91  \w   -117.00 -54.00   0.50    0.05    --  -99.00 125.00  60.00  126
 92  \w   -167.00 -78.00   0.50    0.05    --  -99.00 -73.00-145.26  178
 93  \w   -167.00 -80.00   0.50    0.05    --  -99.00 -68.00 -53.26  174
 94  \w   -111.00 -74.00   0.50    0.05    --  -99.00 -81.00 104.35   74
 95  \w   -148.00 -76.00   0.50    0.05    --  -99.00 -77.00   0.00  144
 96  \w   -107.00 -75.00   0.50    0.05    --  -99.00 -79.00  32.72   64
 97  \w   -168.00 -77.00   0.50    0.05    --  -99.00 -78.00  47.24  182
 98  \w   -105.00 -76.00   0.50    0.05    --  -99.00 -78.00 -98.27   58
 99  \w   -123.00 -82.00   0.50    0.05    --  -99.00 -61.00 -30.00   82
100  \w   -117.00 -27.00   0.50    0.05    --  -99.00 125.00-150.00  180
101  \w   -168.00 -79.00   0.50    0.05    --  -99.00 -70.00 128.32  178
102  \w   -168.00 -76.00   0.50    0.05    --  -99.00 -77.00 -30.00  184
103  \w   -167.00-141.00   0.50    0.05    --  -99.00-125.00-120.00   52
104  \w     67.00 117.00   0.50    0.05    --  103.25 -61.00-120.00  100
105  \w     32.00  60.00   0.50    0.05    --  103.25 -61.00-120.00   56
106  \w     38.00 115.00   0.50    0.05    --  103.25 -45.00  90.00  154
107  \w     71.00  97.00   0.50    0.05    --  103.25 -94.00  30.00   52
108  \w     43.00  69.00   0.50    0.05    --  103.25 -94.00  30.00   52
109  \w     62.00 113.00   0.50    0.05    --  103.25 -45.00-120.00  102
110  \w     54.00 100.00   0.50    0.05    --  103.25 -61.00  90.00   92
111  \w     81.00 108.00   0.50    0.05    --  103.25  77.00-180.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0089942000
_diffrn_orient_matrix_UB_12      0.0614342000
_diffrn_orient_matrix_UB_13      -0.0708825000
_diffrn_orient_matrix_UB_21      0.0824459000
_diffrn_orient_matrix_UB_22      0.1414147000
_diffrn_orient_matrix_UB_23      0.0427214000
_diffrn_orient_matrix_UB_31      0.1562697000
_diffrn_orient_matrix_UB_32      -0.0072006000
_diffrn_orient_matrix_UB_33      -0.0115772000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_unetI/netI     0.0074
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            63483
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.509
_diffrn_reflns_theta_min         2.397
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.913
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.14e (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    1.318
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.322
_exptl_crystal_size_mid          0.235
_exptl_crystal_size_min          0.211
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         6919
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0428
_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^)+(0.0491P)^2^+0.6120P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1081
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6582
_reflns_number_total             6919
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc05429e2.cif
_cod_data_source_block           tx560
_cod_depositor_comments
'Adding full bibliography for 1565604--1565606.cif.'
_cod_database_code               1565606
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         CHNO
_reflns_odcompleteness_completeness 99.76
_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 N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C18A(H18C,H18D)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11),
 C12(H12), C13(H13), C15(H15), N1A(H1A), C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A),
  C6A(H6A), C9A(H9A), C10A(H10A), C11A(H11A), C12A(H12A), C13A(H13A), C15A(H15A)
2.c X=CH2 refined with riding coordinates:
 C16(H16A,H16B), C16A(H16C,H16D)
;
_shelx_res_checksum              97230
_shelx_hkl_checksum              92828
_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 1.221
_oxdiff_exptl_absorpt_empirical_full_min 0.845