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_1571283
_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         'C29 H20 O S'
_chemical_formula_sum            'C29 H20 O S'
_chemical_formula_weight         416.51
_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             2023-03-22
_audit_creation_method
;FinalCif V118 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                97.773(8)
_cell_angle_beta                 102.840(8)
_cell_angle_gamma                111.165(8)
_cell_formula_units_Z            2
_cell_length_a                   8.945(2)
_cell_length_b                   9.215(3)
_cell_length_c                   14.225(4)
_cell_measurement_reflns_used    6738
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      30.514
_cell_measurement_theta_min      2.547
_cell_volume                     1035.7(5)
_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 0.992
_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  0.0493
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10570
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.551
_diffrn_reflns_theta_min         2.440
_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    0.176
_exptl_absorpt_correction_T_max  0.767772
_exptl_absorpt_correction_T_min  0.585212
_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 0.0802 before and 0.0557 after correction.
 
For component 2:
 wR2(int) was 0.1262 before and 0.0666 after correction.
 The Ratio of minimum to maximum transmission is 0.76.

Final HKLF 4 output contains 74460 reflections, Rint = 0.0502
 (47757 with I > 3sig(I), Rint = 0.0458)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_recrystallization_method
'from diethylether by cooling down in fridge.'
_exptl_crystal_size_max          0.164
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.088
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         10570
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0426
_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^)+(0.0585P)^2^+0.3395P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1197
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9123
_reflns_number_total             10570
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
'The data was integrated as a 2-component twin.'
_twin_individual_id              2
_twin_individual_twin_matrix_11  -0.0436
_twin_individual_twin_matrix_12  -0.03128
_twin_individual_twin_matrix_13  0.97117
_twin_individual_twin_matrix_21  1.008
_twin_individual_twin_matrix_22  -0.00754
_twin_individual_twin_matrix_23  0.02872
_twin_individual_twin_matrix_31  0.06285
_twin_individual_twin_matrix_32  1.01682
_twin_individual_twin_matrix_33  0.09142
_cod_data_source_file            d4sc01138d2.cif
_cod_data_source_block           mo_1939_cg_0m_4
_cod_depositor_comments
'Adding full bibliography for 1571276--1571290.cif.'
_cod_original_cell_volume        1035.8(5)
_cod_database_code               1571283
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.800(4)
 0.200(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
3. Others
 Sof(H11)=Sof(H18A)=Sof(H18B)=1-FVAR(1)
 Sof(H18)=Sof(H11A)=Sof(H11B)=FVAR(1)
 Fixed X: H11(0.55064) H18A(0.2054) H18B(0.34565) H18(0.25879) H11A(0.45038)
 H11B(0.5843)
 Fixed Y: H11(0.902069) H18A(0.474408) H18B(0.499089) H18(0.442269)
 H11A(0.861771) H11B(0.87294)
 Fixed Z: H11(0.71004) H18A(0.57356) H18B(0.51597) H18(0.535069)
 H11A(0.720361) H11B(0.658821)
4.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C14(H14), C15(H15), C16(H16), C17(H17),
 C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28),
  C29(H29)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.972
_shelx_estimated_absorpt_t_max   0.985
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 800'
_shelx_res_checksum              533