Titanium-mediated rearrangement of cyclopropenylmethyl acetates to (E)-halodienes.
Gallego, Gary; Ariafard, Alireza; Tran, Kiet; Sandoval, David; Choi, Leera; Chen, Yi-Hsun; Yates, Brian F.; Tao, Fu-Ming; Hyland, Christopher J. T.; Organic & biomolecular chemistry 9 (2011) 3359–3363; doi:10.1039/c0ob01046d

data_7151810
_publ_section_title
;
 Titanium-mediated rearrangement of cyclopropenylmethyl acetates to
 (E)-halodienes.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3359
_journal_page_last               3363
_journal_paper_doi               10.1039/c0ob01046d
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C13 H14 Cl N O2'
_chemical_formula_sum            'C13 H14 Cl N O2'
_chemical_formula_weight         251.70
_chemical_name_common
(E)-(2-chloro-3,4-dimethylpenta-1,3-dienyl)benzene
_chemical_name_systematic
;
(E)-(2-chloro-3,4-dimethylpenta-1,3-dienyl)benzene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 111.3350(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.0021(13)
_cell_length_b                   7.2565(7)
_cell_length_c                   14.3625(15)
_cell_measurement_reflns_used    3609
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.3
_cell_measurement_theta_min      4
_cell_volume                     1262.2(2)
_computing_cell_refinement       'Bruker SMART (Bruker, 1997)'
_computing_data_collection       'APEX II (CCD2 - upgrade)'
_computing_data_reduction        'XPREP (Broker-AXS, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'SMART 1K CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0172
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9111
_diffrn_reflns_theta_full        30.62
_diffrn_reflns_theta_max         30.62
_diffrn_reflns_theta_min         4.03
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.292
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.18
_refine_diff_density_max         2.390
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.100
_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     171
_refine_ls_number_reflns         3699
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0758
_refine_ls_shift/su_max          0.033
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1312P)^2^+1.3762P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2230
_refine_ls_wR_factor_ref         0.2348
_reflns_number_gt                3013
_reflns_number_total             3699
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob01046d.txt
_cod_data_source_block           csuf5_0m
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7151810