Effect of Electron-Withdrawing Substituents on the Epoxide Ring: An Experimental and Theoretical Electron Density Analysis of a Series of Epoxide Derivatives
Simon Grabowsky; Tanja Schirmeister; Carsten Paulmann; Thomas Pfeuffer; Peter Luger; Journal of Organic Chemistry 76 (2011) 1305–1318; doi:10.1021/jo102125n

data_4026070
_publ_contact_author
;
  Dr. Simon Grabowsky
  Freie Universitaet Berlin
  Institut fuer Chemie und Biochemie
  Anorganische Chemie
  Fabeckstr. 36a
  14195 Berlin
  Germany

;
_publ_contact_author_email       vongrabo@chemie.fu-berlin.de
_publ_contact_author_fax         0049-30-838-53464
_publ_contact_author_phone       0049-30-838-53450
_publ_section_title
;
 Effect of Electron-Withdrawing Substituents on the Epoxide Ring: An
 Experimental and Theoretical Electron Density Analysis of a Series of
 Epoxide Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1305
_journal_page_last               1318
_journal_paper_doi               10.1021/jo102125n
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C6 N4 O'
_chemical_formula_sum            'C6 N4 O'
_chemical_formula_weight         144.09
_chemical_name_common            'tetra-cyano epoxide'
_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_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 110.79(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5860(19)
_cell_length_b                   6.0820(12)
_cell_length_c                   11.994(2)
_cell_measurement_reflns_used    186756
_cell_measurement_temperature    100
_cell_measurement_theta_max      52.67
_cell_measurement_theta_min      1.79
_cell_volume                     653.7(2)
_computing_cell_refinement       'XDS Kabsch, W. J. Appl. Cryst. 26, 795 (1993)'
_computing_data_collection       'XDS Kabsch, W. J. Appl. Cryst. 26, 795 (1993)'
_computing_data_reduction
'SORTAV Blessing, R. J. Appl. Cryst. 22, 396 (1989)'
_computing_molecular_graphics    'Volkov et al, (2006)'
_computing_publication_material  'Volkov et al, (2006)'
_computing_structure_refinement  'Volkov et al, (2006)'
_computing_structure_solution
'SHELXS-97 Sheldrick, Acta Cryst.A 64, 112 (2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'MarCCD 165 detector'
_diffrn_measurement_method       'phi scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.56000
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_sigmaI/netI    0.0822
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            186756
_diffrn_reflns_theta_full        52.67
_diffrn_reflns_theta_max         52.67
_diffrn_reflns_theta_min         1.79
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.5523
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         9689
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0187
_refine_ls_R_Fsqd_factor         0.0426
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
calc w1 = 1/[s^2^(Fo)]
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0287
_reflns_number_gt                9689
_reflns_number_total             15522
_reflns_threshold_expression     >3sigma(I)
_cod_data_source_file            jo102125n_si_004.cif
_cod_data_source_block           CyanoEpoxid
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4026070