Reactivity of α-diazo sulfonium salts: rhodium-catalysed ring expansion of indenes to naphthalenes.
Timmann, Sven; Wu, Tun-Hui; Golz, Christopher; Alcarazo, Manuel; Chemical science 15 (2024) 5938–5943; doi:10.1039/d4sc01138d

data_1571289
_publ_section_title
;
 Reactivity of &#x3b1;-diazo sulfonium salts: rhodium-catalysed ring
 expansion of indenes to naphthalenes.
;
_journal_issue                   16
_journal_name_full               'Chemical science'
_journal_page_first              5938
_journal_page_last               5943
_journal_paper_doi               10.1039/d4sc01138d
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C23 H16 F3 S, B F4'
_chemical_formula_sum            'C23 H16 B F7 S'
_chemical_formula_weight         468.23
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-03
_audit_creation_method
;FinalCif V123 by Daniel Kratzert, Freiburg 2023, 
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2024-02-14 deposited with the CCDC.	2024-03-12 downloaded from the CCDC.
;
_cell_angle_alpha                63.826(2)
_cell_angle_beta                 68.524(4)
_cell_angle_gamma                80.590(2)
_cell_formula_units_Z            2
_cell_length_a                   9.3811(6)
_cell_length_b                   10.8726(11)
_cell_length_c                   12.1464(10)
_cell_measurement_reflns_used    9771
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      32.557
_cell_measurement_theta_min      2.333
_cell_volume                     1034.66(15)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection
'Bruker BIS V6.2.15/2021-03-15 && APEX4 2022.1-1'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Ag'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0096
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            98974
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.580
_diffrn_reflns_theta_min         1.981
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  0.9916
_exptl_absorpt_correction_T_min  0.9557
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0681 before and 0.0337 after correction.
The Ratio of minimum to maximum transmission is 0.9638.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_recrystallization_method
'from a mixture of methanol, dichloromethane and diethylether. Evaporated to dryness.'
_exptl_crystal_size_max          0.277
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         7529
_refine_ls_number_restraints     76
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0403
_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^)+(0.0500P)^2^+0.3819P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1133
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6958
_reflns_number_total             7529
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01138d2.cif
_cod_data_source_block           mo_2036_cg_0m
_cod_depositor_comments
'Adding full bibliography for 1571276--1571290.cif.'
_cod_database_code               1571289
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 F1A-C13A \\sim F2A-C13A \\sim F3A-C13A
 with sigma of 0.02
 F2B-C13B \\sim F1B-C13B \\sim F3B-C13B
 with sigma of 0.02
 F5A-B1A \\sim F5B-B1B
 with sigma of 0.02
 F7A-B1A \\sim F7B-B1B
 with sigma of 0.02
 F4A-B1A \\sim F4B-B1B
 with sigma of 0.02
 F6A-B1A \\sim F6B-B1B
 with sigma of 0.02
 F5A-F7A \\sim F5B-F7B
 with sigma of 0.04
 F5A-F4A \\sim F5B-F4B
 with sigma of 0.04
 F5A-F6A \\sim F5B-F6B
 with sigma of 0.04
 F7A-F4A \\sim F7B-F4B
 with sigma of 0.04
 F7A-F6A \\sim F7B-F6B
 with sigma of 0.04
 F4A-F6A \\sim F4B-F6B
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 F4A, F5A, F6A, F7A, B1A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 F4B, F5B, F6B, F7B, B1B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4. Others
 Sof(F1B)=Sof(F2B)=Sof(F3B)=Sof(C13B)=Sof(C15B)=Sof(H15B)=Sof(C16B)=Sof(H16B)=
 Sof(C17B)=Sof(C18B)=Sof(H18B)=Sof(C19B)=Sof(H19B)=Sof(C20B)=Sof(H20B)=
 Sof(C21B)=Sof(H21B)=Sof(C22B)=Sof(C23B)=Sof(H23C)=Sof(H23D)=1-FVAR(1)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(C13A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(H16A)=
 Sof(C17A)=Sof(C18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=Sof(C21A)=
 Sof(H21A)=Sof(C22A)=Sof(H22A)=Sof(C23A)=Sof(H23A)=Sof(H23B)=FVAR(1)
 Sof(F4B)=Sof(F5B)=Sof(F6B)=Sof(F7B)=Sof(B1B)=1-FVAR(2)
 Sof(F4A)=Sof(F5A)=Sof(F6A)=Sof(F7A)=Sof(B1A)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C15A(H15A), C15B(H15B), C16A(H16A), C16B(H16B)
5.b Secondary CH2 refined with riding coordinates:
 C23A(H23A,H23B), C23B(H23C,H23D)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
 C18B(H18B), C19A(H19A), C19B(H19B), C20A(H20A), C20B(H20B), C21A(H21A),
 C21B(H21B), C22A(H22A)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.940
_shelx_estimated_absorpt_t_max   0.975
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 800'
_shelx_res_checksum              7207