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_1571276
_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         'C16 H13 F3 N2 O6 S3'
_chemical_formula_sum            'C16 H13 F3 N2 O6 S3'
_chemical_formula_weight         482.46
_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             2023-07-26
_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                109.349(2)
_cell_angle_beta                 98.738(2)
_cell_angle_gamma                98.497(2)
_cell_formula_units_Z            2
_cell_length_a                   8.8939(5)
_cell_length_b                   10.6953(7)
_cell_length_c                   11.3020(8)
_cell_measurement_reflns_used    9815
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      31.512
_cell_measurement_theta_min      2.273
_cell_volume                     979.70(11)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection
'Bruker BIS V6.2.15/2021-03-16 && 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 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_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  0.0362
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            50889
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.578
_diffrn_reflns_theta_min         1.956
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.444
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8313
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1057 before and 0.0482 after correction.
The Ratio of minimum to maximum transmission is 0.8313.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_description       plate
_exptl_crystal_F_000             492
_exptl_crystal_recrystallization_method
'from a mixture of acetonitrile and diethylether.'
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.179
_exptl_crystal_size_min          0.088
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         6496
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0279
_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^)+(0.0453P)^2^+0.3921P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0806
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6115
_reflns_number_total             6496
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01138d2.cif
_cod_data_source_block           mo_2056_cg_0m
_cod_depositor_comments
'Adding full bibliography for 1571276--1571290.cif.'
_cod_database_code               1571276
_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
 S3-F2A \\sim S3-F2B
 with sigma of 0.04
 S3-F3A \\sim S3-F3B
 with sigma of 0.04
 F2A-F3A \\sim F2B-F3B
 with sigma of 0.04
3. Others
 Sof(F2B)=Sof(F3B)=1-FVAR(1)
 Sof(F2A)=Sof(F3A)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12)
4.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.853
_shelx_estimated_absorpt_t_max   0.962
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 800'
_shelx_res_checksum              736