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#$Date: 2019-12-26 22:04:29 +0200 (Thu, 26 Dec 2019) $
#$Revision: 246140 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/18/2311855.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2311855
loop_
_publ_author_name
'Schirmer, Marie Luis'
'Spannenberg, Anke'
'Werner, Thomas'
_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
;
(E)-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 et al.,
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       'φ and ω 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/[σ²(Fo²)+(0.0531P)²+0.3356P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2.014
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
C C1 0.50222(17) 1.10435(6) 0.09662(16) 0.0243(3) Uani d 1
C C2 0.52368(16) 1.03432(6) 0.19853(15) 0.0220(2) Uani d 1
C C3 0.73937(16) 1.01798(7) 0.30244(16) 0.0252(3) Uani d 1
H H3A 0.7717 0.9714 0.2590 0.030 Uiso calc 1
H H3B 0.7818 1.0146 0.4384 0.030 Uiso calc 1
C C4 0.83624(17) 1.08221(7) 0.25761(16) 0.0283(3) Uani d 1
C C5 0.7309(2) 1.19886(7) 0.07720(19) 0.0342(3) Uani d 1
H H5A 0.7210 1.2390 0.1538 0.051 Uiso calc 1
H H5B 0.6348 1.2065 -0.0533 0.051 Uiso calc 1
H H5C 0.8640 1.1978 0.0867 0.051 Uiso calc 1
C C6 0.36379(16) 1.00024(6) 0.18933(15) 0.0234(2) Uani d 1
H H6 0.2422 1.0235 0.1122 0.028 Uiso calc 1
C C7 0.34682(16) 0.93296(6) 0.27917(15) 0.0228(2) Uani d 1
C C8 0.50773(17) 0.89385(7) 0.41127(16) 0.0253(3) Uani d 1
H H8 0.6379 0.9105 0.4454 0.030 Uiso calc 1
C C9 0.47829(19) 0.83109(7) 0.49242(17) 0.0292(3) Uani d 1
H H9 0.5886 0.8054 0.5832 0.035 Uiso calc 1
C C10 0.2892(2) 0.80520(7) 0.44260(18) 0.0318(3) Uani d 1
H H10 0.2702 0.7617 0.4976 0.038 Uiso calc 1
C C11 0.12847(19) 0.84332(7) 0.31191(18) 0.0328(3) Uani d 1
H H11 -0.0013 0.8260 0.2772 0.039 Uiso calc 1
C C12 0.15702(17) 0.90641(7) 0.23218(17) 0.0280(3) Uani d 1
H H12 0.0458 0.9324 0.1437 0.034 Uiso calc 1
N N1 0.69048(14) 1.12976(5) 0.14293(13) 0.0256(2) Uani d 1
O O1 0.35222(13) 1.13563(5) -0.00940(13) 0.0341(2) Uani d 1
O O2 1.01060(14) 1.09208(6) 0.31004(15) 0.0447(3) Uani d 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 N1 124.08(11)
O1 C1 C2 128.71(11)
N1 C1 C2 107.20(9)
C6 C2 C1 119.85(10)
C6 C2 C3 132.69(11)
C1 C2 C3 107.42(9)
C2 C3 C4 103.97(9)
C2 C3 H3A 111.0
C4 C3 H3A 111.0
C2 C3 H3B 111.0
C4 C3 H3B 111.0
H3A C3 H3B 109.0
O2 C4 N1 124.22(12)
O2 C4 C3 127.40(12)
N1 C4 C3 108.38(10)
N1 C5 H5A 109.5
N1 C5 H5B 109.5
H5A C5 H5B 109.5
N1 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C2 C6 C7 130.13(11)
C2 C6 H6 114.9
C7 C6 H6 114.9
C8 C7 C12 117.98(11)
C8 C7 C6 124.18(10)
C12 C7 C6 117.83(10)
C9 C8 C7 120.45(11)
C9 C8 H8 119.8
C7 C8 H8 119.8
C8 C9 C10 120.73(12)
C8 C9 H9 119.6
C10 C9 H9 119.6
C11 C10 C9 119.46(12)
C11 C10 H10 120.3
C9 C10 H10 120.3
C12 C11 C10 120.01(12)
C12 C11 H11 120.0
C10 C11 H11 120.0
C11 C12 C7 121.36(11)
C11 C12 H12 119.3
C7 C12 H12 119.3
C4 N1 C1 112.94(10)
C4 N1 C5 123.38(10)
C1 N1 C5 123.68(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.2150(14)
C1 N1 1.3860(15)
C1 C2 1.4861(16)
C2 C6 1.3370(16)
C2 C3 1.4969(15)
C3 C4 1.5111(17)
C3 H3A 0.9900
C3 H3B 0.9900
C4 O2 1.2096(15)
C4 N1 1.3818(15)
C5 N1 1.4521(15)
C5 H5A 0.9800
C5 H5B 0.9800
C5 H5C 0.9800
C6 C7 1.4585(16)
C6 H6 0.9500
C7 C8 1.4006(16)
C7 C12 1.4027(16)
C8 C9 1.3844(17)
C8 H8 0.9500
C9 C10 1.3896(18)
C9 H9 0.9500
C10 C11 1.3866(19)
C10 H10 0.9500
C11 C12 1.3807(18)
C11 H11 0.9500
C12 H12 0.9500
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O1 C1 C2 C6 -5.00(19)
N1 C1 C2 C6 175.35(10)
O1 C1 C2 C3 177.04(12)
N1 C1 C2 C3 -2.61(12)
C6 C2 C3 C4 -176.43(12)
C1 C2 C3 C4 1.16(12)
C2 C3 C4 O2 -179.14(13)
C2 C3 C4 N1 0.68(12)
C1 C2 C6 C7 -178.27(11)
C3 C2 C6 C7 -0.9(2)
C2 C6 C7 C8 6.08(19)
C2 C6 C7 C12 -174.91(12)
C12 C7 C8 C9 -0.21(17)
C6 C7 C8 C9 178.80(11)
C7 C8 C9 C10 0.91(18)
C8 C9 C10 C11 -0.85(19)
C9 C10 C11 C12 0.10(19)
C10 C11 C12 C7 0.61(19)
C8 C7 C12 C11 -0.55(17)
C6 C7 C12 C11 -179.61(11)
O2 C4 N1 C1 177.36(12)
C3 C4 N1 C1 -2.47(13)
O2 C4 N1 C5 -2.30(19)
C3 C4 N1 C5 177.87(10)
O1 C1 N1 C4 -176.46(11)
C2 C1 N1 C4 3.20(13)
O1 C1 N1 C5 3.19(18)
C2 C1 N1 C5 -177.14(10)
