#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/56/2235634.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_2235634
loop_
_publ_author_name
'Fatiha, Benghanem'
'Saida, Keraghel'
'Safia, Chahmana'
'Ali, Ourari'
'Lydia, Brelot'
_publ_section_title
;
 (Z)-4-(2-Hydroxyanilino)pent-3-en-2-one
;
_journal_coeditor_code           SU2455
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2188
_journal_page_last               o2189
_journal_paper_doi               10.1107/S1600536812027894
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C11 H13 N O2'
_chemical_formula_moiety         'C11 H13 N O2'
_chemical_formula_sum            'C11 H13 N O2'
_chemical_formula_weight         191.22
_chemical_name_systematic
;
(Z)-4-(2-Hydroxyanilino)pent-3-en-2-one
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7826(4)
_cell_length_b                   10.3999(5)
_cell_length_c                   11.1827(3)
_cell_measurement_reflns_used    4219
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1021.41(7)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'DENZO (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi and omega 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  0.1046
_diffrn_reflns_av_sigmaI/netI    0.0523
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7005
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.67
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.291
_refine_ls_abs_structure_details 'none; Friedel pairs merged'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1359
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0472
_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)+(0.0792P)²+0.0946P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1255
_reflns_number_gt                1260
_reflns_number_total             1359
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            su2455.cif
_cod_data_source_block           I
_cod_database_code               2235634
_cod_database_fobs_code          2235634
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z
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
O1 0.0344(8) 0.0336(8) 0.0281(7) -0.0051(7) -0.0054(6) 0.0101(6)
O2 0.0357(7) 0.0395(8) 0.0241(7) -0.0059(7) 0.0004(6) 0.0062(6)
N1 0.0271(8) 0.0257(8) 0.0217(7) -0.0021(7) 0.0009(6) 0.0040(6)
C1 0.0274(9) 0.0234(9) 0.0263(9) 0.0023(8) 0.0021(8) 0.0009(7)
C2 0.0305(10) 0.0324(10) 0.0336(10) 0.0031(10) -0.0033(8) -0.0031(9)
C3 0.0308(10) 0.0342(11) 0.0511(13) -0.0023(10) -0.0051(10) -0.0075(10)
C4 0.0403(12) 0.0300(11) 0.0503(14) -0.0086(11) -0.0004(10) 0.0027(10)
C5 0.0407(12) 0.0263(10) 0.0377(11) -0.0044(10) -0.0006(9) 0.0057(8)
C6 0.0271(9) 0.0236(9) 0.0261(9) 0.0004(8) -0.0002(7) -0.0003(7)
C7 0.0319(9) 0.0236(8) 0.0205(9) 0.0043(8) 0.0006(7) 0.0043(7)
C8 0.0406(12) 0.0513(13) 0.0258(10) -0.0059(12) 0.0040(9) 0.0093(10)
C9 0.0324(10) 0.0281(10) 0.0223(8) 0.0029(9) -0.0028(8) 0.0042(7)
C10 0.0304(9) 0.0250(9) 0.0272(9) 0.0023(9) 0.0004(7) -0.0007(7)
C11 0.0374(11) 0.0434(13) 0.0393(11) -0.0088(12) -0.0011(10) -0.0005(10)
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.58388(17) 0.70724(15) 0.03852(14) 0.0320(4) Uani d . 1.000
O O2 0.95582(17) 0.68677(15) 0.15060(12) 0.0331(4) Uani d . 1.000
N N1 0.69854(19) 0.57884(17) 0.22040(14) 0.0248(4) Uani d . 1.000
C C1 0.4942(2) 0.61181(19) 0.08258(17) 0.0257(5) Uani d . 1.000
C C2 0.3527(2) 0.5805(2) 0.03503(19) 0.0322(6) Uani d . 1.000
C C3 0.2679(3) 0.4816(2) 0.0850(2) 0.0387(7) Uani d . 1.000
C C4 0.3242(3) 0.4126(2) 0.1812(2) 0.0402(7) Uani d . 1.000
C C5 0.4665(3) 0.4415(2) 0.2282(2) 0.0349(6) Uani d . 1.000
C C6 0.5510(2) 0.54332(18) 0.18138(17) 0.0256(5) Uani d . 1.000
C C7 0.7611(2) 0.57778(19) 0.33025(16) 0.0253(5) Uani d . 1.000
C C8 0.6698(3) 0.5315(3) 0.43570(18) 0.0392(7) Uani d . 1.000
C C9 0.9069(2) 0.6227(2) 0.34810(17) 0.0276(5) Uani d . 1.000
C C10 0.9993(2) 0.6778(2) 0.25800(17) 0.0275(5) Uani d . 1.000
C C11 1.1530(3) 0.7300(3) 0.2911(2) 0.0400(7) Uani d . 1.000
H H1 0.542(3) 0.738(3) -0.032(3) 0.044(7) Uiso d . 1.000
H H1N 0.762(3) 0.619(3) 0.162(2) 0.033(6) Uiso d . 1.000
H H2 0.31400 0.62690 -0.03160 0.0390 Uiso c R 1.000
H H3 0.17070 0.46110 0.05310 0.0460 Uiso c R 1.000
H H4 0.26530 0.34520 0.21510 0.0480 Uiso c R 1.000
H H5 0.50630 0.39190 0.29240 0.0420 Uiso c R 1.000
H H8A 0.56570 0.56470 0.42990 0.0590 Uiso c R 1.000
H H8B 0.71680 0.56240 0.50980 0.0590 Uiso c R 1.000
H H8C 0.66760 0.43730 0.43600 0.0590 Uiso c R 1.000
H H9 0.94840 0.61620 0.42630 0.0330 Uiso c R 1.000
H H11A 1.23200 0.68290 0.24730 0.0600 Uiso c R 1.000
H H11B 1.16920 0.71960 0.37730 0.0600 Uiso c R 1.000
H H11C 1.15810 0.82140 0.27030 0.0600 Uiso c R 1.000
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
_geom_angle_publ_flag
C1 O1 H1 109.3(18) no
C6 N1 C7 130.74(16) no
C6 N1 H1N 115.9(15) no
C7 N1 H1N 112.9(15) no
O1 C1 C2 123.38(18) no
O1 C1 C6 116.69(16) no
C2 C1 C6 119.93(18) no
C1 C2 C3 120.0(2) no
C2 C3 C4 120.4(2) no
C3 C4 C5 120.2(2) no
C4 C5 C6 120.1(2) no
N1 C6 C1 115.76(16) no
N1 C6 C5 124.68(18) no
C1 C6 C5 119.39(18) no
C8 C7 C9 119.35(17) no
N1 C7 C8 120.02(17) no
N1 C7 C9 120.60(17) no
C7 C9 C10 124.56(17) no
O2 C10 C9 122.23(17) no
O2 C10 C11 118.64(18) no
C9 C10 C11 119.12(17) no
C1 C2 H2 120.00 no
C3 C2 H2 120.00 no
C2 C3 H3 120.00 no
C4 C3 H3 120.00 no
C3 C4 H4 120.00 no
C5 C4 H4 120.00 no
C4 C5 H5 120.00 no
C6 C5 H5 120.00 no
C7 C8 H8A 109.00 no
C7 C8 H8B 109.00 no
C7 C8 H8C 109.00 no
H8A C8 H8B 109.00 no
H8A C8 H8C 110.00 no
H8B C8 H8C 109.00 no
C7 C9 H9 118.00 no
C10 C9 H9 118.00 no
C10 C11 H11A 109.00 no
C10 C11 H11B 109.00 no
C10 C11 H11C 109.00 no
H11A C11 H11B 109.00 no
H11A C11 H11C 110.00 no
H11B C11 H11C 110.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.359(2) no
O2 C10 1.264(2) no
O1 H1 0.93(3) no
N1 C6 1.416(2) no
N1 C7 1.346(2) no
N1 H1N 0.96(3) no
C1 C2 1.390(3) no
C1 C6 1.406(3) no
C2 C3 1.387(3) no
C3 C4 1.385(3) no
C4 C5 1.389(4) no
C5 C6 1.395(3) no
C7 C8 1.505(3) no
C7 C9 1.378(3) no
C9 C10 1.415(3) no
C10 C11 1.501(3) no
C2 H2 0.9500 no
C3 H3 0.9500 no
C4 H4 0.9500 no
C5 H5 0.9500 no
C8 H8A 0.9800 no
C8 H8B 0.9800 no
C8 H8C 0.9800 no
C9 H9 0.9500 no
C11 H11A 0.9800 no
C11 H11B 0.9800 no
C11 H11C 0.9800 no
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
_geom_hbond_publ_flag
N1 H1N O1 . 0.96(3) 2.28(3) 2.633(2) 100.9(18) yes
N1 H1N O2 . 0.96(3) 1.85(3) 2.641(2) 139(2) yes
O1 H1 O2 3_465 0.93(3) 1.72(3) 2.637(2) 172(3) yes
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
_geom_torsion_publ_flag
C6 N1 C7 C9 -177.06(19) no
C7 N1 C6 C1 148.6(2) no
C7 N1 C6 C5 -36.2(3) no
C6 N1 C7 C8 0.8(3) no
C6 C1 C2 C3 -0.1(3) no
O1 C1 C6 N1 -2.5(3) no
O1 C1 C6 C5 -177.92(18) no
O1 C1 C2 C3 179.93(18) no
C2 C1 C6 N1 177.60(17) no
C2 C1 C6 C5 2.1(3) no
C1 C2 C3 C4 -0.8(3) no
C2 C3 C4 C5 -0.3(3) no
C3 C4 C5 C6 2.3(3) no
C4 C5 C6 N1 -178.26(19) no
C4 C5 C6 C1 -3.2(3) no
N1 C7 C9 C10 3.0(3) no
C8 C7 C9 C10 -174.9(2) no
C7 C9 C10 O2 -2.2(3) no
C7 C9 C10 C11 176.5(2) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12999424
