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_1571286
_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 H25 O2 S, B F4'
_chemical_formula_sum            'C23 H25 B F4 O2 S'
_chemical_formula_weight         452.30
_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             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                75.560(3)
_cell_angle_beta                 84.910(4)
_cell_angle_gamma                85.280(5)
_cell_formula_units_Z            2
_cell_length_a                   7.4771(6)
_cell_length_b                   9.2628(8)
_cell_length_c                   15.6995(14)
_cell_measurement_reflns_used    1824
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      25.34
_cell_measurement_theta_min      2.69
_cell_volume                     1046.79(16)
_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 0.996
_diffrn_measured_fraction_theta_max 0.992
_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  0.0557
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10696
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.607
_diffrn_reflns_theta_min         2.275
_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    0.208
_exptl_absorpt_correction_T_max  0.735311
_exptl_absorpt_correction_T_min  0.603714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1574 before and 0.0629 after correction.
 The Ratio of minimum to maximum transmission is 0.82.

Final HKLF 4 output contains 112095 reflections, Rint = 0.0557
 (49988 with I > 3sig(I), Rint = 0.0489)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_description       plate
_exptl_crystal_F_000             472
_exptl_crystal_recrystallization_method
'from dichloromethane and diethylether by vapor diffusion method.'
_exptl_crystal_size_max          0.634
_exptl_crystal_size_mid          0.367
_exptl_crystal_size_min          0.098
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         10696
_refine_ls_number_restraints     64
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0394
_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^)+(0.0483P)^2^+0.4043P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1053
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9586
_reflns_number_total             10696
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01138d2.cif
_cod_data_source_block           mo_2229_cg_0m_4
_cod_depositor_comments
'Adding full bibliography for 1571276--1571290.cif.'
_cod_database_code               1571286
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.860(2)
 0.122(2) 0.0183(14)
2. 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
3. Restrained distances
 F1A-B1 \\sim F1B-B1
 with sigma of 0.02
 F2A-B1 \\sim F2B-B1
 with sigma of 0.02
 F3A-B1 \\sim F3B-B1
 with sigma of 0.02
 F4A-B1 \\sim F4B-B1
 with sigma of 0.02
4. Rigid body (RIGU) restrains
 B1, F3B, F1B, F4B, F2B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 F1A, F2A, F3A, F4A, B1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
5. Others
 Sof(F3B)=Sof(F1B)=Sof(F4B)=Sof(F2B)=1-FVAR(1)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F4A)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3)
6.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C10(H10A,H10B)
6.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
6.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.879
_shelx_estimated_absorpt_t_max   0.980
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 800'
_shelx_res_checksum              86765