#------------------------------------------------------------------------------
#$Date: 2016-02-20 21:30:07 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/63/2226353.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_2226353
loop_
_publ_author_name
'Venter, Gertruida J. S.'
'Steyl, Gideon'
'Roodt, Andreas'
_publ_section_title
;
 4-(2-Methylanilino)pent-3-en-2-one
;
_journal_coeditor_code           BG2348
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1593
_journal_page_last               o1594
_journal_paper_doi               10.1107/S1600536810021045
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H15 N O'
_chemical_formula_moiety         'C12 H15 N O'
_chemical_formula_sum            'C12 H15 N O'
_chemical_formula_weight         189.25
_chemical_name_systematic
;
4-(2-Methylanilino)pent-3-en-2-one
;
_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_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 92.154(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5674(7)
_cell_length_b                   11.5075(9)
_cell_length_c                   12.0996(11)
_cell_measurement_reflns_used    2889
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.69
_cell_volume                     1052.91(16)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2004)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type
;
Bruker X8 APEXII 4K Kappa CCD
;
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10022
_diffrn_reflns_theta_full        27
_diffrn_reflns_theta_max         27
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.9595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2004)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.354
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2308
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_gt           0.0531
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0654P)²+0.9506P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1502
_reflns_number_gt                1854
_reflns_number_total             2308
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bg2348.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226353
_cod_database_fobs_code          2226353
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.4288(3) 0.30725(17) 0.73241(16) 0.0212(4) Uani d . 1 . .
H H1A 0.4068 0.3907 0.723 0.032 Uiso calc PR 0.5 . .
H H1B 0.3886 0.2659 0.6653 0.032 Uiso calc PR 0.5 . .
H H1C 0.5557 0.2939 0.7458 0.032 Uiso calc PR 0.5 . .
H H1D 0.4939 0.243 0.6998 0.032 Uiso calc PR 0.5 . .
H H1E 0.5121 0.3678 0.7575 0.032 Uiso calc PR 0.5 . .
H H1F 0.345 0.3397 0.6769 0.032 Uiso calc PR 0.5 . .
C C2 0.3300(2) 0.26340(16) 0.82877(15) 0.0172(4) Uani d . 1 . .
C C3 0.3410(2) 0.14730(15) 0.85770(15) 0.0174(4) Uani d . 1 . .
H H3 0.4142 0.0982 0.8159 0.021 Uiso calc R 1 . .
C C4 0.2494(2) 0.09702(15) 0.94616(14) 0.0162(4) Uani d . 1 . .
C C5 0.2647(3) -0.03183(16) 0.96633(16) 0.0217(4) Uani d . 1 . .
H H5A 0.1945 -0.0532 1.0296 0.033 Uiso calc PR 0.5 . .
H H5B 0.3889 -0.0521 0.982 0.033 Uiso calc PR 0.5 . .
H H5C 0.2208 -0.0739 0.9005 0.033 Uiso calc PR 0.5 . .
H H5D 0.3417 -0.0663 0.9118 0.033 Uiso calc PR 0.5 . .
H H5E 0.1472 -0.0674 0.9594 0.033 Uiso calc PR 0.5 . .
H H5F 0.3153 -0.0456 1.0409 0.033 Uiso calc PR 0.5 . .
C C12 0.2730(3) 0.49042(17) 1.07167(15) 0.0218(4) Uani d . 1 . .
H H12A 0.2961 0.4067 1.0685 0.033 Uiso calc PR 0.5 . .
H H12B 0.1797 0.5055 1.1238 0.033 Uiso calc PR 0.5 . .
H H12C 0.3812 0.5311 1.0964 0.033 Uiso calc PR 0.5 . .
H H12D 0.2752 0.5555 1.1239 0.033 Uiso calc PR 0.5 . .
H H12E 0.3917 0.4567 1.0687 0.033 Uiso calc PR 0.5 . .
H H12F 0.1901 0.4311 1.0961 0.033 Uiso calc PR 0.5 . .
O O12 0.15430(17) 0.15514(11) 1.00878(10) 0.0195(3) Uani d . 1 . .
C C111 0.1994(2) 0.45704(15) 0.86788(15) 0.0160(4) Uani d . 1 . .
C C112 0.2147(2) 0.53330(16) 0.95849(15) 0.0172(4) Uani d . 1 . .
C C113 0.1737(2) 0.64979(16) 0.94050(16) 0.0203(4) Uani d . 1 . .
H H113 0.1821 0.7026 1.0008 0.024 Uiso calc R 1 . .
C C114 0.1207(2) 0.69078(16) 0.83647(16) 0.0208(4) Uani d . 1 . .
H H114 0.0932 0.7707 0.8262 0.025 Uiso calc R 1 . .
C C115 0.1081(2) 0.61469(16) 0.74784(15) 0.0192(4) Uani d . 1 . .
H H115 0.0738 0.6426 0.6763 0.023 Uiso calc R 1 . .
C C116 0.1456(2) 0.49751(16) 0.76367(15) 0.0180(4) Uani d . 1 . .
H H116 0.1344 0.445 0.7032 0.022 Uiso calc R 1 . .
N N11 0.2320(2) 0.33691(13) 0.88747(13) 0.0176(3) Uani d . 1 . .
H H11 0.1801 0.3060 0.9471 0.021 Uiso calc R 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 0 '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 0.006 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C2 C1 H1D . . 109.5 ?
H1A C1 H1D . . 141.1 ?
H1B C1 H1D . . 56.3 ?
H1C C1 H1D . . 56.3 ?
C2 C1 H1E . . 109.5 ?
H1A C1 H1E . . 56.3 ?
H1B C1 H1E . . 141.1 ?
H1C C1 H1E . . 56.3 ?
H1D C1 H1E . . 109.5 ?
C2 C1 H1F . . 109.5 ?
H1A C1 H1F . . 56.3 ?
H1B C1 H1F . . 56.3 ?
H1C C1 H1F . . 141.1 ?
H1D C1 H1F . . 109.5 ?
H1E C1 H1F . . 109.5 ?
N11 C2 C3 . . 120.21(16) ?
N11 C2 C1 . . 120.06(16) ?
C3 C2 C1 . . 119.73(16) ?
C2 C3 C4 . . 123.91(16) ?
C2 C3 H3 . . 118 ?
C4 C3 H3 . . 118 ?
O12 C4 C3 . . 122.97(16) ?
O12 C4 C5 . . 117.93(16) ?
C3 C4 C5 . . 119.10(15) ?
C4 C5 H5A . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C4 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C4 C5 H5D . . 109.5 ?
H5A C5 H5D . . 141.1 ?
H5B C5 H5D . . 56.3 ?
H5C C5 H5D . . 56.3 ?
C4 C5 H5E . . 109.5 ?
H5A C5 H5E . . 56.3 ?
H5B C5 H5E . . 141.1 ?
H5C C5 H5E . . 56.3 ?
H5D C5 H5E . . 109.5 ?
C4 C5 H5F . . 109.5 ?
H5A C5 H5F . . 56.3 ?
H5B C5 H5F . . 56.3 ?
H5C C5 H5F . . 141.1 ?
H5D C5 H5F . . 109.5 ?
H5E C5 H5F . . 109.5 ?
C112 C12 H12A . . 109.5 ?
C112 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C112 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C112 C12 H12D . . 109.5 ?
H12A C12 H12D . . 141.1 ?
H12B C12 H12D . . 56.3 ?
H12C C12 H12D . . 56.3 ?
C112 C12 H12E . . 109.5 ?
H12A C12 H12E . . 56.3 ?
H12B C12 H12E . . 141.1 ?
H12C C12 H12E . . 56.3 ?
H12D C12 H12E . . 109.5 ?
C112 C12 H12F . . 109.5 ?
H12A C12 H12F . . 56.3 ?
H12B C12 H12F . . 56.3 ?
H12C C12 H12F . . 141.1 ?
H12D C12 H12F . . 109.5 ?
H12E C12 H12F . . 109.5 ?
C116 C111 C112 . . 120.72(16) ?
C116 C111 N11 . . 121.30(16) ?
C112 C111 N11 . . 117.91(16) ?
C113 C112 C111 . . 117.91(17) ?
C113 C112 C12 . . 120.93(16) ?
C111 C112 C12 . . 121.16(16) ?
C114 C113 C112 . . 121.61(17) ?
C114 C113 H113 . . 119.2 ?
C112 C113 H113 . . 119.2 ?
C115 C114 C113 . . 119.74(17) ?
C115 C114 H114 . . 120.1 ?
C113 C114 H114 . . 120.1 ?
C114 C115 C116 . . 119.93(17) ?
C114 C115 H115 . . 120 ?
C116 C115 H115 . . 120 ?
C115 C116 C111 . . 120.08(17) ?
C115 C116 H116 . . 120 ?
C111 C116 H116 . . 120 ?
C2 N11 C111 . . 128.22(16) ?
C2 N11 H11 . . 115.9 ?
C111 N11 H11 . . 115.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.496(2) ?
C1 H1A . 0.98 ?
C1 H1B . 0.98 ?
C1 H1C . 0.98 ?
C1 H1D . 0.98 ?
C1 H1E . 0.98 ?
C1 H1F . 0.98 ?
C2 N11 . 1.345(2) ?
C2 C3 . 1.383(3) ?
C3 C4 . 1.420(2) ?
C3 H3 . 0.95 ?
C4 O12 . 1.257(2) ?
C4 C5 . 1.506(2) ?
C5 H5A . 0.98 ?
C5 H5B . 0.98 ?
C5 H5C . 0.98 ?
C5 H5D . 0.98 ?
C5 H5E . 0.98 ?
C5 H5F . 0.98 ?
C12 C112 . 1.506(3) ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C12 H12D . 0.98 ?
C12 H12E . 0.98 ?
C12 H12F . 0.98 ?
C111 C116 . 1.391(3) ?
C111 C112 . 1.406(3) ?
C111 N11 . 1.422(2) ?
C112 C113 . 1.391(3) ?
C113 C114 . 1.389(3) ?
C113 H113 . 0.95 ?
C114 C115 . 1.385(3) ?
C114 H114 . 0.95 ?
C115 C116 . 1.390(3) ?
C115 H115 . 0.95 ?
C116 H116 . 0.95 ?
N11 H11 . 0.9071 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N11 H11 O12 . 0.91 1.90 2.6345(19) 136.4
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N11 C2 C3 C4 . . . . 1.9(3) ?
C1 C2 C3 C4 . . . . -178.62(17) ?
C2 C3 C4 O12 . . . . -2.6(3) ?
C2 C3 C4 C5 . . . . 177.01(17) ?
C116 C111 C112 C113 . . . . 0.3(3) ?
N11 C111 C112 C113 . . . . -176.63(16) ?
C116 C111 C112 C12 . . . . -179.96(16) ?
N11 C111 C112 C12 . . . . 3.1(3) ?
C111 C112 C113 C114 . . . . -0.6(3) ?
C12 C112 C113 C114 . . . . 179.64(17) ?
C112 C113 C114 C115 . . . . -0.1(3) ?
C113 C114 C115 C116 . . . . 1.1(3) ?
C114 C115 C116 C111 . . . . -1.4(3) ?
C112 C111 C116 C115 . . . . 0.7(3) ?
N11 C111 C116 C115 . . . . 177.51(16) ?
C3 C2 N11 C111 . . . . -177.32(17) ?
C1 C2 N11 C111 . . . . 3.2(3) ?
C116 C111 N11 C2 . . . . 48.9(3) ?
C112 C111 N11 C2 . . . . -134.19(19) ?
