Tandem Nazarov cyclization-halovinylation of divinyl ketones under Vilsmeier conditions: synthesis of highly substituted cyclopentadienes.
Wang, Mang; Han, Feng; Yuan, Hongjuan; Liu, Qun; Chemical communications (Cambridge, England) 46 (2010) 2247–2249; doi:10.1039/b917703e

data_7105347
_publ_section_title
;
 Tandem Nazarov cyclization-halovinylation of divinyl ketones under
 Vilsmeier conditions: synthesis of highly substituted
 cyclopentadienes.
;
_journal_issue                   13
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2247
_journal_page_last               2249
_journal_paper_doi               10.1039/b917703e
_journal_volume                  46
_journal_year                    2010
_chemical_formula_sum            'C20 H16 Cl N O3 S2'
_chemical_formula_weight         417.91
_chemical_name_common
;
7-chloro-6-(4-methoxyphenyl)-9-(4-nitrophenyl)-1,4-
dithiaspiro(4.4)nona-6,8-diene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.286(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.808(2)
_cell_length_b                   16.045(5)
_cell_length_c                   18.120(6)
_cell_measurement_reflns_used    376
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.07
_cell_measurement_theta_min      1.70
_cell_volume                     1967.4(11)
_computing_cell_refinement       'SMART (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL-PLUS (Sheldrick, 1990)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97(Sheldrick, 1997)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10854
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.07
_diffrn_reflns_theta_min         1.70
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.427
_exptl_absorpt_correction_T_max  0.667
_exptl_absorpt_correction_T_min  0.559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS(Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       acicular
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3885
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0603
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0718P)^2^+0.9244P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1618
_reflns_number_gt                2599
_reflns_number_total             3885
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b917703e.txt
_cod_data_source_block           12
_cod_original_sg_symbol_Hall     -P2ybc
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7105347