Substituent-Induced Switch of the Role of Charge-Transfer Complexes in the Diels-Alder Reactions of o-Chloranil and Styrenes
Sergiy V. Rosokha; Vasiliy Korotchenko; Charlotte L. Stern; Vladimir Zaitsev; Jeremy T. Ritzert; Journal of Organic Chemistry 77 (2012) 5971–5981; doi:10.1021/jo300614k

data_4027293
_publ_section_title
;
 Substituent-Induced Switch of the Role of Charge-Transfer Complexes in
 the Diels-Alder Reactions of o-Chloranil and Styrenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5971
_journal_page_last               5981
_journal_paper_doi               10.1021/jo300614k
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C15 H12 Cl4 O4'
_chemical_formula_sum            'C15 H12 Cl4 O4'
_chemical_formula_weight         398.05
_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
_cell_angle_alpha                85.824(6)
_cell_angle_beta                 79.449(5)
_cell_angle_gamma                89.246(5)
_cell_formula_units_Z            2
_cell_length_a                   7.1671(18)
_cell_length_b                   10.654(3)
_cell_length_c                   12.606(3)
_cell_measurement_reflns_used    7905
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.84
_cell_measurement_theta_min      2.44
_cell_volume                     943.8(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  '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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4667
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_description       pyramid
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_platon_squeeze_details
;
 Diffuse, disordered solvent molecules could not be adequately modeled.  The
 bypass procedure in Platon (Spek, 1990) was used to remove the electronic
 contribution from these solvents. The total potential solvent accessible void
 volume was 194.2 Ang^3^ and the electron count / cell = 48. As the exact
 solvent content is not known, the reported formula reflects only the atoms
 used in the refinement.

;
_refine_diff_density_max         0.935
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         4667
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0639P)^2^+0.2154P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1155
_reflns_number_gt                4151
_reflns_number_total             4667
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300614k_si_007.cif
_cod_data_source_block           vas5
_cod_database_code               4027293