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_1565605
_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         'C20 H16 Br N O2'
_chemical_formula_sum            'C20 H16 Br N O2'
_chemical_formula_weight         382.25
_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
_audit_creation_date             2018-12-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-12-08 deposited with the CCDC.	2021-11-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.2510(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.95590(10)
_cell_length_b                   6.80800(10)
_cell_length_c                   30.8630(2)
_cell_measurement_reflns_used    26008
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      75.2140
_cell_measurement_theta_min      2.8450
_cell_volume                     1671.26(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 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.959
_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   -120.00 -72.00   0.50    0.20    --  -47.20-124.00  22.00   96
  2  \w    -94.00  -9.00   0.50    0.20    --  -47.20 124.00 101.00  170
  3  \w   -107.00 -22.00   0.50    0.20    --  -47.20 147.00 -93.00  170
  4  \w   -120.00 -56.00   0.50    0.20    --  -47.20-147.00-142.00  128
  5  \w     16.00  94.00   0.50    0.20    --   47.20-124.00  22.00  156
  6  \w     28.00 107.00   0.50    0.20    --   47.20-147.00-142.00  158
  7  \w   -168.00 -72.00   0.50    0.30    --  -99.00-124.00  22.00  192
  8  \w   -132.00 -26.00   0.50    0.30    --  -99.00 147.00 -93.00  212
  9  \w     31.00 132.00   0.50    0.30    --  103.25-147.00-142.00  202
 10  \w     62.00 169.00   0.50    0.30    --  103.25 147.00 -93.00  214
 11  \w     78.00 169.00   0.50    0.30    --  103.25 124.00 101.00  182
 12  \w     78.00 169.00   0.50    0.30    --  103.25 124.00 101.00  182
 13  \w   -120.00 -71.00   0.50    0.20    --  -47.20-125.00  90.00   98
 14  \w     35.00 120.00   0.50    0.20    --   47.20  38.00 -90.00  170
 15  \w    -26.00  60.00   0.50    0.20    --   47.20 -38.00 150.00  172
 16  \w     25.00 120.00   0.50    0.20    --   47.20  77.00-180.00  190
 17  \w   -168.00 -76.00   0.50    0.30    --  -99.00 -77.00 120.00  184
 18  \w   -168.00 -81.00   0.50    0.30    --  -99.00 -94.00 -30.00  174
 19  \w   -112.00 -27.00   0.50    0.30    --  -99.00  45.00 -30.00  170
 20  \w   -116.00 -26.00   0.50    0.30    --  -99.00 124.00 101.00  180
 21  \w   -168.00 -82.00   0.50    0.30    --  -99.00 -61.00 -60.00  172
 22  \w   -168.00 -86.00   0.50    0.30    --  -99.00 -30.00  90.00  164
 23  \w   -168.00 -56.00   0.50    0.30    --  -99.00-147.00-142.00  224
 24  \w   -122.00 -26.00   0.50    0.30    --  -99.00  77.00 -60.00  192
 25  \w     91.00 169.00   0.50    0.30    --  103.25  45.00-150.00  156
 26  \w     31.00 120.00   0.50    0.30    --  103.25 -61.00   0.00  178
 27  \w     32.00 116.00   0.50    0.30    --  103.25 -45.00   0.00  168
 28  \w    113.00 169.00   0.50    0.30    --  103.25  45.00   0.00  112
 29  \w     39.00 106.00   0.50    0.30    --  103.25 -61.00-180.00  134
;
_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      -0.1067757000
_diffrn_orient_matrix_UB_12      -0.1051962000
_diffrn_orient_matrix_UB_13      -0.0352011000
_diffrn_orient_matrix_UB_21      0.0412711000
_diffrn_orient_matrix_UB_22      -0.1994127000
_diffrn_orient_matrix_UB_23      0.0212480000
_diffrn_orient_matrix_UB_31      -0.1561990000
_diffrn_orient_matrix_UB_32      0.0191447000
_diffrn_orient_matrix_UB_33      0.0283423000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0086
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            29345
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.356
_diffrn_reflns_theta_min         2.864
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.444
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61350
_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            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.289
_exptl_crystal_size_mid          0.255
_exptl_crystal_size_min          0.251
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3324
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0273
_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^)+(0.0227P)^2^+1.6836P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0646
_refine_ls_wR_factor_ref         0.0655
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3307
_reflns_number_total             3324
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc05429e2.cif
_cod_data_source_block           tx165a
_cod_depositor_comments
'Adding full bibliography for 1565604--1565606.cif.'
_cod_database_code               1565605
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         CHNOBr
_reflns_odcompleteness_completeness 99.33
_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
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17),
 C19(H19), C20(H20)
;
_shelx_res_checksum              88670
_shelx_hkl_checksum              20343
_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 1.532
_oxdiff_exptl_absorpt_empirical_full_min 0.750