#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:09:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201973 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/84/2208453.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_2208453
loop_
_publ_author_name
'Shaheen, Farkhanda'
'Marchio, L'
'Badshah, Amin'
'Khosa, Muhammad Kaleem'
_publ_section_title
;
 (Z)-4-Anilinopent-3-en-2-one
;
_journal_coeditor_code           WN6410
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o873
_journal_page_last               o874
_journal_paper_doi               10.1107/S1600536806003205
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C11 H13 N O'
_chemical_formula_moiety         'C11 H13 N O'
_chemical_formula_sum            'C11 H13 N O'
_chemical_formula_weight         175.22
_chemical_melting_point          240
_chemical_name_systematic
;
(Z)-4-Anilinopent-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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.10(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.157(3)
_cell_length_b                   11.040(7)
_cell_length_c                   10.130(5)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17.84
_cell_measurement_theta_min      6.00
_cell_volume                     983.9(9)
_computing_cell_refinement       'local program'
_computing_data_collection       'local program'
_computing_data_reduction        'local program'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Philips PW 1100'
_diffrn_measurement_method       θ--2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1812
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.23
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.893
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details
'[local program based on Walker & Stuart (1983)]'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         1717
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0481
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.059P)²+0.3446P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1389
_reflns_number_gt                1120
_reflns_number_total             1717
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn6410.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2208453
_cod_database_fobs_code          2208453
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_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_type_symbol
N1 0.0879(2) 0.20512(18) 0.3349(2) 0.0473(5) Uani d . 1 N
C5 0.1041(3) 0.4261(2) 0.3023(3) 0.0668(8) Uani d . 1 C
H5A 0.2126 0.4187 0.3349 0.100 Uiso calc R 1 H
H5B 0.0721 0.4974 0.3408 0.100 Uiso calc R 1 H
H5C 0.0742 0.4322 0.2039 0.100 Uiso calc R 1 H
O1 -0.1231(2) 0.12712(17) 0.4494(2) 0.0677(6) Uani d . 1 O
C6 0.2128(2) 0.1669(2) 0.2893(2) 0.0421(6) Uani d . 1 C
C3 -0.0889(3) 0.3310(2) 0.3985(3) 0.0502(6) Uani d . 1 C
C4 0.0312(3) 0.3168(2) 0.3448(2) 0.0457(6) Uani d . 1 C
C2 -0.1630(3) 0.2349(2) 0.4481(2) 0.0517(6) Uani d . 1 C
C11 0.2923(3) 0.0664(2) 0.3519(3) 0.0541(7) Uani d . 1 C
C8 0.3746(3) 0.1763(3) 0.1404(3) 0.0654(8) Uani d . 1 C
C9 0.4554(3) 0.0776(3) 0.2044(3) 0.0666(8) Uani d . 1 C
C7 0.2532(3) 0.2207(3) 0.1806(3) 0.0559(7) Uani d . 1 C
C10 0.4129(3) 0.0223(3) 0.3096(3) 0.0648(8) Uani d . 1 C
C1 -0.2942(3) 0.2663(3) 0.5042(3) 0.0700(8) Uani d . 1 C
H1A -0.3787 0.2141 0.4637 0.105 Uiso calc R 1 H
H1B -0.3234 0.3490 0.4826 0.105 Uiso calc R 1 H
H1C -0.2643 0.2557 0.6021 0.105 Uiso calc R 1 H
H7 0.194(3) 0.287(2) 0.131(3) 0.059(7) Uiso d . 1 H
H3 -0.121(3) 0.413(2) 0.401(2) 0.053(7) Uiso d . 1 H
H11 0.262(3) 0.034(2) 0.422(3) 0.059(8) Uiso d . 1 H
H10 0.464(3) -0.049(3) 0.353(3) 0.073(8) Uiso d . 1 H
H9 0.542(4) 0.051(3) 0.175(3) 0.085(9) Uiso d . 1 H
H8 0.400(3) 0.211(2) 0.065(3) 0.068(8) Uiso d . 1 H
H1 0.039(3) 0.147(2) 0.365(2) 0.058(8) Uiso d . 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.0538(12) 0.0450(12) 0.0510(12) -0.0055(10) 0.0276(10) 0.0013(10)
C5 0.083(2) 0.0500(16) 0.077(2) -0.0042(14) 0.0384(17) 0.0070(14)
O1 0.0797(13) 0.0501(11) 0.0902(14) 0.0014(9) 0.0516(11) 0.0031(10)
C6 0.0441(12) 0.0466(13) 0.0385(12) -0.0061(11) 0.0162(10) -0.0056(10)
C3 0.0552(15) 0.0464(15) 0.0539(15) 0.0035(12) 0.0231(12) 0.0031(12)
C4 0.0536(14) 0.0442(14) 0.0401(13) -0.0019(11) 0.0144(11) 0.0009(10)
C2 0.0534(15) 0.0534(16) 0.0536(15) 0.0034(12) 0.0236(12) -0.0052(12)
C11 0.0629(17) 0.0532(16) 0.0523(16) -0.0013(13) 0.0261(14) 0.0048(13)
C8 0.0654(18) 0.083(2) 0.0576(17) -0.0023(16) 0.0341(15) 0.0072(16)
C9 0.0532(17) 0.082(2) 0.074(2) 0.0002(16) 0.0341(15) -0.0026(17)
C7 0.0578(16) 0.0677(18) 0.0471(15) 0.0059(13) 0.0227(13) 0.0091(13)
C10 0.0629(18) 0.0594(18) 0.077(2) 0.0109(14) 0.0271(16) 0.0076(15)
C1 0.0678(18) 0.0686(18) 0.087(2) 0.0011(15) 0.0439(16) -0.0039(16)
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
C4 N1 C6 131.2(2)
C4 N1 H1 113.5(16)
C6 N1 H1 115.2(16)
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
C11 C6 C7 119.0(2)
C11 C6 N1 117.5(2)
C7 C6 N1 123.3(2)
C4 C3 C2 124.8(2)
C4 C3 H3 113.9(14)
C2 C3 H3 121.3(14)
N1 C4 C3 120.2(2)
N1 C4 C5 120.1(2)
C3 C4 C5 119.7(2)
O1 C2 C3 123.3(2)
O1 C2 C1 118.7(2)
C3 C2 C1 118.1(2)
C10 C11 C6 120.5(2)
C10 C11 H11 123.1(16)
C6 C11 H11 116.4(16)
C9 C8 C7 121.1(3)
C9 C8 H8 119.1(16)
C7 C8 H8 119.7(17)
C8 C9 C10 119.1(3)
C8 C9 H9 118.3(18)
C10 C9 H9 122.6(18)
C8 C7 C6 119.8(3)
C8 C7 H7 120.0(15)
C6 C7 H7 120.1(15)
C9 C10 C11 120.5(3)
C9 C10 H10 120.8(16)
C11 C10 H10 118.7(17)
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
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C4 1.352(3)
N1 C6 1.412(3)
N1 H1 0.89(3)
C5 C4 1.499(3)
C5 H5A 0.9600
C5 H5B 0.9600
C5 H5C 0.9600
O1 C2 1.244(3)
C6 C11 1.381(3)
C6 C7 1.389(3)
C3 C4 1.365(3)
C3 C2 1.424(4)
C3 H3 0.95(2)
C2 C1 1.505(3)
C11 C10 1.379(4)
C11 H11 0.90(3)
C8 C9 1.374(4)
C8 C7 1.376(4)
C8 H8 0.94(3)
C9 C10 1.375(4)
C9 H9 0.96(3)
C7 H7 0.96(3)
C10 H10 0.96(3)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4648243
