Highly functionalized alkenes produced from base-free organocatalytic Wittig reactions: (E)-3-benzylidenepyrrolidine-2,5-dione, (E)-3-benzylidene-1-methylpyrrolidine-2,5-dione and (E)-3-benzylidene-1-tert-butylpyrrolidine-2,5-dione.
Schirmer, Marie Luis; Spannenberg, Anke; Werner, Thomas; Acta crystallographica. Section C, Structural chemistry 72 (2016) 504–508; doi:10.1107/S2053229616008159

data_2311855
_publ_section_title
;
 Highly functionalized alkenes produced from base-free organocatalytic
 Wittig reactions: (E)-3-benzylidenepyrrolidine-2,5-dione,
 (E)-3-benzylidene-1-methylpyrrolidine-2,5-dione and
 (E)-3-benzylidene-1-tert-butylpyrrolidine-2,5-dione.
;
_journal_issue                   'Pt 6'
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first              504
_journal_page_last               508
_journal_paper_doi               10.1107/S2053229616008159
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C12 H11 N O2'
_chemical_formula_moiety         'C12 H11 N O2'
_chemical_formula_sum            'C12 H11 N O2'
_chemical_formula_weight         201.22
_chemical_name_systematic
;
(<i>E</i>)-3-Benzylidene-1-methylpyrrolidine-2,5-dione
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 116.7270(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5977(4)
_cell_length_b                   18.2537(9)
_cell_length_c                   8.0187(4)
_cell_measurement_reflns_used    5561
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.92
_cell_measurement_theta_min      3.06
_cell_volume                     993.27(9)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction        SAINT
_computing_molecular_graphics
;
XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae <i>et al.</i>,
2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11747
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_min         2.231
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       'part of a plate'
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.555
_exptl_crystal_size_mid          0.417
_exptl_crystal_size_min          0.194
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.220
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2395
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0531P)^2^+0.3356P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1097
_reflns_number_gt                2033
_reflns_number_total             2395
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ov3077sup1.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2311855
_shelx_hkl_checksum              88515
_shelx_res_checksum              35086
_shelxl_version_number           2.014