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_4026069
_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         'C12 H11 N O7'
_chemical_formula_sum            'C12 H11 N O7'
_chemical_formula_weight         281.22
_chemical_name_common            'acceptor-substituted oxirane'
_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
_cell_angle_alpha                86.198(1)
_cell_angle_beta                 74.105(1)
_cell_angle_gamma                60.673(1)
_cell_formula_units_Z            2
_cell_length_a                   7.7460(3)
_cell_length_b                   8.0800(2)
_cell_length_c                   11.8350(5)
_cell_measurement_reflns_used    2938
_cell_measurement_temperature    100
_cell_measurement_theta_max      41.81
_cell_measurement_theta_min      14.48
_cell_volume                     619.07(4)
_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 0.953
_diffrn_measured_fraction_theta_max 0.842
_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  0.0762
_diffrn_reflns_av_sigmaI/netI    0.0721
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            126224
_diffrn_reflns_theta_full        20.49
_diffrn_reflns_theta_max         41.81
_diffrn_reflns_theta_min         1.41
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.9537
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     515
_refine_ls_number_reflns         8523
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0309
_refine_ls_R_Fsqd_factor         0.0460
_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         0.0422
_reflns_number_gt                8523
_reflns_number_total             14724
_reflns_threshold_expression     >3sigma(I)
_cod_data_source_file            jo102125n_si_003.cif
_cod_data_source_block           NipheEpoxide
_cod_database_code               4026069