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_1571285
_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         'C26 H20 F3 O2 S, B F4'
_chemical_formula_sum            'C26 H20 B F7 O2 S'
_chemical_formula_weight         540.29
_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
_audit_creation_date             2024-02-08
_audit_creation_method
;FinalCif V133 by Daniel Kratzert, Freiburg 2024, 
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                95.044(7)
_cell_angle_beta                 109.263(11)
_cell_angle_gamma                93.731(9)
_cell_formula_units_Z            2
_cell_length_a                   8.946(2)
_cell_length_b                   10.892(3)
_cell_length_c                   12.669(4)
_cell_measurement_reflns_used    9767
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      30.463
_cell_measurement_theta_min      2.424
_cell_volume                     1155.0(6)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection
'Bruker BIS 8.5.1.2 Release/2023-09-07 and APEX5 2023.9-2'
_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 0.999
_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  0.0353
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            85969
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.543
_diffrn_reflns_theta_min         1.886
_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    0.221
_exptl_absorpt_correction_T_max  0.7251
_exptl_absorpt_correction_T_min  0.7025
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0765 before and 0.0408 after correction.
The Ratio of minimum to maximum transmission is 0.9688.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_recrystallization_method
'from a mixture of acetonitrile and diethylether by vapor diffusion method.'
_exptl_crystal_size_max          0.223
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.039
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         7081
_refine_ls_number_restraints     129
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0375
_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^)+(0.0488P)^2^+0.6574P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1006
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6206
_reflns_number_total             7081
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01138d2.cif
_cod_data_source_block           mo_2227_cg_0m
_cod_depositor_comments
'Adding full bibliography for 1571276--1571290.cif.'
_cod_original_cell_volume        1155.1(5)
_cod_database_code               1571285
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C3-H3 = C4-H4
 1 with sigma of 0.02
 F1A-C12 \\sim F1B-C12
 with sigma of 0.02
 F2A-C12 \\sim F2B-C12
 with sigma of 0.02
 F3A-C12 \\sim F3B-C12
 with sigma of 0.02
 C12-F1B \\sim C12-F1C
 with sigma of 0.02
 C12-F2B \\sim C12-F2C
 with sigma of 0.02
 C12-F3B \\sim C12-F3C
 with sigma of 0.02
 F1A-F2A \\sim F2A-F3A \\sim F3A-F1A
 with sigma of 0.02
 F1B-F2B \\sim F2B-F3B \\sim F3B-F1B
 with sigma of 0.02
 F1C-F2C \\sim F2C-F3C \\sim F3C-F1C
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F2C \\sim F3A \\sim F3B: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
F2B \\sim F2A \\sim F1C: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
F1B \\sim F1A \\sim F3C: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 F1A, F2A, F3A, C12
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 F1B, F2B, F3B, C12
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 F1C, F2C, F3C, C12
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
5. Others
 1*[Sof(F1A)+Sof(F2A)+Sof(F3A)]+1*[Sof(F1B)+Sof(F2B)+Sof(F3B)]+1*[Sof(F1C)+
 Sof(F2C)+Sof(F3C)]=1 with esd of 0.0001
 Sof(F1A)=Sof(F2A)=Sof(F3A)=FVAR(1)
 Sof(F1B)=Sof(F2B)=Sof(F3B)=FVAR(2)
 Sof(F1C)=Sof(F2C)=Sof(F3C)=FVAR(3)
6.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B)
6.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23),
 C24(H24), C25(H25), C26(H26)
6.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.952
_shelx_estimated_absorpt_t_max   0.991
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 800'
_shelx_res_checksum              45972