Rearrangement of a carboxy-substituted spiro[4.4]nonatriene to annulated fulvenes through a Pd(ii)-mediated 1,5-vinyl shift.
Goyal, Karan; Kukier, Garrett A.; Chen, Xiangyang; Turlik, Aneta; Houk, K. N.; Sarpong, Richmond; Chemical science 14 (2023) 11809–11817; doi:10.1039/d3sc03222a

data_1570040
_publ_section_title
;
 Rearrangement of a carboxy-substituted spiro[4.4]nonatriene to annulated
 fulvenes through a Pd(ii)-mediated 1,5-vinyl shift.
;
_journal_issue                   42
_journal_name_full               'Chemical science'
_journal_page_first              11809
_journal_page_last               11817
_journal_paper_doi               10.1039/d3sc03222a
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C12 H12 O4'
_chemical_formula_sum            'C12 H12 O4'
_chemical_formula_weight         220.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2023-03-02 deposited with the CCDC.	2023-09-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.1660(10)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   17.1400(2)
_cell_length_b                   8.09620(10)
_cell_length_c                   31.5007(4)
_cell_measurement_reflns_used    17270
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.4400
_cell_measurement_theta_min      5.3660
_cell_volume                     4219.07(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            26165
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        74.000
_diffrn_reflns_theta_max         74.480
_diffrn_reflns_theta_min         5.348
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.873
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       block
_exptl_crystal_F_000             1856
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: 30% ethyl acetate in hexanes'
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4271
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0423
_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^)+(0.0667P)^2^+2.6239P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1168
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3926
_reflns_number_total             4271
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc03222a1.cif
_cod_data_source_block           KGoyal001_Sarpong
_cod_depositor_comments
'Adding full bibliography for 1570039--1570041.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1570040
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.738
_shelx_estimated_absorpt_t_max   0.902
_shelx_res_checksum              82642