#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/31/8103151.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8103151
loop_
_publ_author_name
'Richard Betz'
'Thomas Gerber'
_publ_section_title
;
 Crystal structure of (Z)-4-(phenylamino)pent-3-en-2-one, C11H13NO, at 200
 K
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              373
_journal_volume                  226
_journal_year                    2011
_chemical_formula_moiety         'C11 H13 N O '
_chemical_formula_sum            'C11 H13 N O'
_chemical_formula_weight         175.22
_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                 107.1710(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0532(3)
_cell_length_b                   10.9311(3)
_cell_length_c                   10.1107(3)
_cell_measurement_reflns_used    9952
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      2.35
_cell_volume                     955.97(5)
_computing_cell_refinement       'Bruker SAINT (Bruker, 2010)'
_computing_data_collection       'Bruker APEX-II (Bruker, 2010)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2010)'
_computing_molecular_graphics
'ORTEPIII (Farrugia, 1997), MERCURY (Macrae, 2006)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0670
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17019
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.81
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.504
_exptl_crystal_size_mid          0.493
_exptl_crystal_size_min          0.296
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         2369
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0433
_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)+(0.0664P)²+0.2385P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1236
_reflns_number_gt                2131
_reflns_number_total             2369
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-3414.cff
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_Hall     '-P 2ybc '
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               8103151
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_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 1.12314(10) 0.62656(7) 0.04880(9) 0.0410(2) Uani 1 1 d .
N1 N 0.91300(10) 0.70551(8) 0.16374(9) 0.0288(2) Uani 1 1 d .
H71 H 0.9581(19) 0.6483(15) 0.1268(16) 0.050(4) Uiso 1 1 d .
C1 C 1.29700(14) 0.76683(12) -0.00574(14) 0.0417(3) Uani 1 1 d .
H1A H 1.3865 0.7156 0.0395 0.063 Uiso 1 1 calc R
H1B H 1.3245 0.8532 0.0126 0.063 Uiso 1 1 calc R
H1C H 1.2660 0.7521 -0.1058 0.063 Uiso 1 1 calc R
C2 C 1.16433(12) 0.73536(10) 0.05040(11) 0.0318(2) Uani 1 1 d .
C3 C 1.09153(12) 0.83324(9) 0.10073(10) 0.0310(2) Uani 1 1 d .
H3 H 1.1299 0.9137 0.0971 0.037 Uiso 1 1 calc R
C4 C 0.96920(12) 0.81876(9) 0.15431(10) 0.0283(2) Uani 1 1 d .
C5 C 0.89744(14) 0.92891(10) 0.19772(13) 0.0385(3) Uani 1 1 d .
H5A H 0.7846 0.9206 0.1666 0.058 Uiso 1 1 calc R
H5B H 0.9275 1.0022 0.1562 0.058 Uiso 1 1 calc R
H5C H 0.9331 0.9361 0.2988 0.058 Uiso 1 1 calc R
C6 C 0.78747(11) 0.66754(9) 0.20948(9) 0.0269(2) Uani 1 1 d .
C7 C 0.70674(12) 0.56444(10) 0.14636(11) 0.0328(2) Uani 1 1 d .
H7 H 0.7348 0.5249 0.0736 0.039 Uiso 1 1 calc R
C8 C 0.58544(13) 0.51933(11) 0.18939(13) 0.0392(3) Uani 1 1 d .
H8 H 0.5310 0.4488 0.1461 0.047 Uiso 1 1 calc R
C9 C 0.54294(13) 0.57632(12) 0.29509(13) 0.0406(3) Uani 1 1 d .
H9 H 0.4584 0.5461 0.3231 0.049 Uiso 1 1 calc R
C10 C 0.62473(13) 0.67748(12) 0.35925(12) 0.0393(3) Uani 1 1 d .
H10 H 0.5965 0.7165 0.4322 0.047 Uiso 1 1 calc R
C11 C 0.74756(13) 0.72283(11) 0.31848(11) 0.0340(2) Uani 1 1 d .
H11 H 0.8044 0.7914 0.3647 0.041 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0481(5) 0.0299(4) 0.0561(5) -0.0017(3) 0.0324(4) -0.0009(3)
N1 0.0327(4) 0.0262(4) 0.0326(4) 0.0000(3) 0.0174(3) 0.0021(3)
C1 0.0395(6) 0.0419(6) 0.0525(7) 0.0021(5) 0.0273(5) -0.0012(5)
C2 0.0321(5) 0.0341(5) 0.0328(5) 0.0017(4) 0.0153(4) 0.0001(4)
C3 0.0345(5) 0.0281(5) 0.0331(5) -0.0005(4) 0.0139(4) -0.0027(4)
C4 0.0317(5) 0.0280(5) 0.0258(4) -0.0007(3) 0.0093(4) 0.0017(4)
C5 0.0461(6) 0.0284(5) 0.0467(6) -0.0034(4) 0.0226(5) 0.0030(4)
C6 0.0267(4) 0.0295(5) 0.0261(4) 0.0032(3) 0.0105(3) 0.0039(3)
C7 0.0351(5) 0.0322(5) 0.0338(5) -0.0017(4) 0.0145(4) 0.0011(4)
C8 0.0356(6) 0.0381(6) 0.0457(6) -0.0031(5) 0.0148(5) -0.0057(4)
C9 0.0311(5) 0.0488(7) 0.0470(6) 0.0030(5) 0.0196(5) -0.0016(4)
C10 0.0385(6) 0.0489(7) 0.0370(5) -0.0032(5) 0.0213(5) 0.0012(5)
C11 0.0355(5) 0.0404(6) 0.0290(5) -0.0047(4) 0.0141(4) -0.0033(4)
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 130.46(9)
C4 N1 H71 112.7(10)
C6 N1 H71 116.5(10)
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
O1 C2 C3 123.56(9)
O1 C2 C1 118.72(10)
C3 C2 C1 117.71(10)
C4 C3 C2 124.30(9)
C4 C3 H3 117.9
C2 C3 H3 117.9
N1 C4 C3 119.70(9)
N1 C4 C5 120.77(9)
C3 C4 C5 119.50(9)
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
C7 C6 C11 119.33(9)
C7 C6 N1 116.94(9)
C11 C6 N1 123.61(9)
C8 C7 C6 120.12(10)
C8 C7 H7 119.9
C6 C7 H7 119.9
C7 C8 C9 120.55(11)
C7 C8 H8 119.7
C9 C8 H8 119.7
C10 C9 C8 119.31(10)
C10 C9 H9 120.3
C8 C9 H9 120.3
C9 C10 C11 120.82(10)
C9 C10 H10 119.6
C11 C10 H10 119.6
C10 C11 C6 119.84(10)
C10 C11 H11 120.1
C6 C11 H11 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.2450(13)
N1 C4 1.3525(13)
N1 C6 1.4100(12)
N1 H71 0.887(17)
C1 C2 1.5119(14)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 C3 1.4269(14)
C3 C4 1.3781(14)
C3 H3 0.9500
C4 C5 1.4943(14)
C5 H5A 0.9800
C5 H5B 0.9800
C5 H5C 0.9800
C6 C7 1.3915(14)
C6 C11 1.3947(13)
C7 C8 1.3858(15)
C7 H7 0.9500
C8 C9 1.3860(17)
C8 H8 0.9500
C9 C10 1.3814(18)
C9 H9 0.9500
C10 C11 1.3867(15)
C10 H10 0.9500
C11 H11 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H71 O1 0.887(17) 1.899(17) 2.6495(11) 141.2(15)
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 C2 C3 C4 0.70(18)
C1 C2 C3 C4 179.75(10)
C6 N1 C4 C3 -177.55(9)
C6 N1 C4 C5 0.75(16)
C2 C3 C4 N1 1.23(16)
C2 C3 C4 C5 -177.11(10)
C4 N1 C6 C7 147.59(11)
C4 N1 C6 C11 -36.47(16)
C11 C6 C7 C8 1.63(16)
N1 C6 C7 C8 177.75(9)
C6 C7 C8 C9 0.18(18)
C7 C8 C9 C10 -1.23(19)
C8 C9 C10 C11 0.45(19)
C9 C10 C11 C6 1.36(18)
C7 C6 C11 C10 -2.39(16)
N1 C6 C11 C10 -178.24(10)
