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_4026067
_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         'C2 H4 O'
_chemical_formula_sum            'C2 H4 O'
_chemical_formula_weight         44.05
_chemical_name_common            'epoxide or oxirane'
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_atom_sites_solution_hydrogens   geom
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_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 100.37(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.633(5)
_cell_length_b                   8.400(1)
_cell_length_c                   6.577(3)
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_cell_measurement_temperature    100
_cell_measurement_theta_max      45.0
_cell_measurement_theta_min      3.98
_cell_volume                     251.8(3)
_computing_cell_refinement       REDUC
_computing_data_collection       REDUC
_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 1.0
_diffrn_measured_fraction_theta_max 1.0
_diffrn_measurement_device_type  'point detector'
_diffrn_measurement_method       'phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_theta_full        45.0
_diffrn_reflns_theta_max         45.00
_diffrn_reflns_theta_min         3.98
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_description       block
_exptl_crystal_F_000             96
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.107
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.028
_refine_ls_extinction_method     none
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_refine_ls_number_reflns         1314
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_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0261
_refine_ls_R_Fsqd_factor         0.0315
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
calc w1 = 1/[s^2^(Fo)]
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0221
_reflns_number_gt                1314
_reflns_number_total             2081
_reflns_threshold_expression     >4sigma(F)
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_cod_data_source_block           etox
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