Transformation of azulenes to bicyclic [4]dendralene and heptafulvene derivatives via photochemical cycloaddition of dialkylsilylene
Tomoyuki Kosai; Shintaro Ishida; Takeaki Iwamoto; Chem.Commun. 51 (2015) 10707–; doi:10.1039/C5cc03424H

data_7117363
_publ_section_title
;
 Transformation of azulenes to bicyclic [4]dendralene and heptafulvene
 derivatives via photochemical cycloaddition of dialkylsilylene
;
_journal_name_full               Chem.Commun.
_journal_page_first              10707
_journal_paper_doi               10.1039/C5cc03424H
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C31 H58 Si5'
_chemical_formula_sum            'C31 H58 Si5'
_chemical_formula_weight         571.22
_chemical_melting_point          402.5(5)
_chemical_name_systematic        'bicyclic heptafulvene'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-04-21 deposited with the CCDC.
2015-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                105.877(2)
_cell_angle_beta                 92.815(2)
_cell_angle_gamma                110.499(2)
_cell_formula_units_Z            2
_cell_length_a                   9.5864(15)
_cell_length_b                   10.9534(17)
_cell_length_c                   18.638(3)
_cell_measurement_reflns_used    9953
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.78
_cell_measurement_theta_min      2.30
_cell_volume                     1740.2(5)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16560
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.15
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  0.9780
_exptl_absorpt_correction_T_min  0.9360
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.090
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             628
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         6099
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0348
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0551P)^2^+0.7140P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.0980
_reflns_number_gt                5531
_reflns_number_total             6099
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc03424h2.cif
_cod_data_source_block           si337a_a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '402-403' was changed to '402.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 3392 2015-05-12 13:50:21Z andrius 
;
_cod_original_cell_volume        1740.3(5)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7117363