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_1571279
_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         '2(C20 H13 N2 O S), 2(C1 F3 O3 S1), C4 H10 O'
_chemical_formula_sum            'C48 H39 F6 N5 O9 S4'
_chemical_formula_weight         1072.08
_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             2022-12-12
_audit_creation_method
;FinalCif V113 by Daniel Kratzert, Freiburg 2022,
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                103.841(5)
_cell_angle_beta                 96.946(4)
_cell_angle_gamma                107.996(5)
_cell_formula_units_Z            2
_cell_length_a                   10.5731(18)
_cell_length_b                   13.509(2)
_cell_length_c                   18.976(3)
_cell_measurement_reflns_used    9780
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      27.884
_cell_measurement_theta_min      2.263
_cell_volume                     2446.6(7)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       'Bruker BIS V6.2.14/2020-04-30'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_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 0.996
_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  0.0479
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            92894
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.954
_diffrn_reflns_theta_min         2.072
_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    0.278
_exptl_absorpt_correction_T_max  0.6654
_exptl_absorpt_correction_T_min  0.5943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1168 before and 0.0622 after correction.
The Ratio of minimum to maximum transmission is 0.8931.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_description       needle
_exptl_crystal_F_000             1104
_exptl_crystal_recrystallization_method
'Crystallized from a mixture of acetonitrile and diethylether.'
_exptl_crystal_size_max          0.233
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     697
_refine_ls_number_reflns         11682
_refine_ls_number_restraints     125
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0449
_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^)+(0.0578P)^2^+0.9916P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1230
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9120
_reflns_number_total             11682
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01138d2.cif
_cod_data_source_block           mo_1847_cg_0m
_cod_depositor_comments
'Adding full bibliography for 1571276--1571290.cif.'
_cod_database_code               1571279
_shelx_shelxl_version_number     2018/3
_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
 S3A-O3A \\sim S3B-O3B
 with sigma of 0.02
 S3A-O4A \\sim S3B-O4B
 with sigma of 0.02
 S3A-O5A \\sim S3B-O5B
 with sigma of 0.02
 S3A-C41A \\sim S3B-C41B
 with sigma of 0.02
 O3A-O4A \\sim O3B-O4B
 with sigma of 0.04
 O4A-O5A \\sim O4B-O5B
 with sigma of 0.04
 F2A-C41A \\sim F2B-C41B
 with sigma of 0.02
 O3A-C41A \\sim O3B-C41B
 with sigma of 0.04
 F3A-C41A \\sim F3B-C41B
 with sigma of 0.02
 F1A-C41A \\sim F1B-C41B
 with sigma of 0.02
 F2A-F3A \\sim F2B-F3B
 with sigma of 0.04
 O3A-O5A \\sim O3B-O5B
 with sigma of 0.04
 S3A-F1A \\sim S3B-F1B
 with sigma of 0.04
 S3A-F2A \\sim S3B-F2B
 with sigma of 0.04
 O4A-C41A \\sim O4B-C41B
 with sigma of 0.04
 S3A-F3A \\sim S3B-F3B
 with sigma of 0.04
 O5A-C41A \\sim O5B-C41B
 with sigma of 0.04
 F1A-F2A \\sim F1B-F2B
 with sigma of 0.04
 F1A-F3A \\sim F1B-F3B
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 S3B, F1B, F2B, F3B, O3B, O4B, O5B, C41B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 S3A, F1A, F2A, F3A, O3A, O4A, O5A, C41A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(S3B)=Sof(F1B)=Sof(F2B)=Sof(F3B)=Sof(O3B)=Sof(O4B)=Sof(O5B)=Sof(C41B)=1-
 FVAR(1)
 Sof(S3A)=Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(O3A)=Sof(O4A)=Sof(O5A)=Sof(C41A)=
 FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C45(H45A,H45B), C47(H47A,H47B)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C23(H23), C24(H24), C25(H25),
  C26(H26), C29(H29), C30(H30), C31(H31), C32(H32), C36(H36), C37(H37),
 C38(H38), C39(H39), C40(H40)
5.c Idealised Me refined as rotating group:
 C46(H46A,H46B,H46C), C48(H48A,H48B,H48C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_estimated_absorpt_t_min   0.938
_shelx_estimated_absorpt_t_max   0.990
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_shelx_res_checksum              43908
_shelx_fab_checksum              3461