Assembly of fluorinated benzodiazepines via Rh(iii)-catalysed [5+2] annulation of N-benzo[d]imidazole indolines with 2,2-difluorovinyl tosylate
Liu, Fu-Xiaomin; Chen, Weijie; Ma, Lei; Cheng, Kui; Zhou, Zhi; Yi, Wei; New Journal of Chemistry 47 (2023) 12589–12594; doi:10.1039/D3NJ01544K

data_7062513
_publ_section_title
;
 Assembly of fluorinated benzodiazepines via Rh(iii)-catalysed [5+2]
 annulation of N-benzo[d]imidazole indolines with 2,2-difluorovinyl
 tosylate
;
_journal_issue                   27
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              12589
_journal_page_last               12594
_journal_paper_doi               10.1039/D3NJ01544K
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C17 H13 F2 N3'
_chemical_formula_sum            'C17 H13 F2 N3'
_chemical_formula_weight         297.30
_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             2021-04-10
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_audit_update_record
;
2022-10-18 deposited with the CCDC.	2023-06-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.803(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6045(10)
_cell_length_b                   8.9631(8)
_cell_length_c                   13.1233(10)
_cell_measurement_reflns_used    2859
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.1490
_cell_measurement_theta_min      2.8890
_cell_volume                     1345.1(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -34.00  -4.00   1.00    2.50    --   11.90 -38.00 -30.00   30
  2  \w    -19.00  21.00   1.00    2.50    --  -11.27 -99.00 -30.00   40
  3  \w    -58.00  28.00   1.00    2.50    --   11.90 -38.00  30.00   86
  4  \w     42.00  90.00   1.00    2.50    --   11.90 178.00 -30.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0603264000
_diffrn_orient_matrix_UB_12      0.0019197000
_diffrn_orient_matrix_UB_13      -0.0215618000
_diffrn_orient_matrix_UB_21      0.0035525000
_diffrn_orient_matrix_UB_22      -0.0743387000
_diffrn_orient_matrix_UB_23      -0.0176009000
_diffrn_orient_matrix_UB_31      -0.0140164000
_diffrn_orient_matrix_UB_32      -0.0269737000
_diffrn_orient_matrix_UB_33      0.0472697000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5944
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.765
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.468
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2370
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0387
_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^)+(0.0385P)^2^+0.4629P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0936
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2054
_reflns_number_total             2370
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj01544k2.cif
_cod_data_source_block           exp_2968
_cod_depositor_comments
'Adding full bibliography for 7062512--7062513.cif.'
_cod_database_code               7062513
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14)
;
_shelx_res_checksum              60501
_shelx_hkl_checksum              62583
_olex2_date_sample_data_collection 2021-04-10
_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 1.210
_oxdiff_exptl_absorpt_empirical_full_min 0.825