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_4027288
_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_sum            'C15 H10 Cl4 O3'
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_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
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_cell_angle_beta                 88.7050(10)
_cell_angle_gamma                79.6570(10)
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_cell_length_a                   8.18970(10)
_cell_length_b                   10.68760(10)
_cell_length_c                   11.0632(2)
_cell_measurement_reflns_used    5513
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.97
_cell_measurement_theta_min      2.35
_cell_volume                     909.21(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \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  0.0658
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_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
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_diffrn_reflns_limit_k_min       -15
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_diffrn_reflns_theta_max         30.02
_diffrn_reflns_theta_min         1.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_T_max  0.9620
_exptl_absorpt_correction_T_min  0.8558
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   face-indexed
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.17
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_platon_squeeze_details
;
;
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         5259
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.886
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0324P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
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_reflns_number_gt                3527
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_reflns_threshold_expression     >2sigma(I)
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