#------------------------------------------------------------------------------
#$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $
#$Revision: 91933 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/90/2009074.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_2009074
loop_
_publ_author_name
'Arici, Cengiz'
'Tahir, M. Nawaz'
'\"Ulk\"u, Din\,cer'
'Atakol, Orhan'
_publ_section_title
;
 4-Chloro-2-(4-oxopent-2-en-2-ylamino)phenol
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1691
_journal_page_last               1692
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C11 H12 Cl N O2'
_chemical_formula_sum            'C11 H12 Cl N O2'
_chemical_formula_weight         225.677
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90.00
_cell_angle_beta                 115.830(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1911(11)
_cell_length_b                   11.3039(13)
_cell_length_c                   11.0983(11)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295
_cell_measurement_theta_max      20.92
_cell_measurement_theta_min      11.47
_cell_volume                     1150.8(2)
_computing_data_collection       'CAD-4 EXPRESS (Enraf-Nonius, 1993)'
_computing_data_reduction        'MolEN (Fair, 1990)'
_computing_molecular_graphics    'PLATON99 (Spek, 1999)'
_computing_publication_material  MolEN
_computing_structure_refinement  MolEN
_computing_structure_solution    'SIR (Giacovazzo, 1980)'
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.010
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2265
_diffrn_reflns_theta_max         25.04
_diffrn_standards_decay_%        -1.16
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_T_max  0.939
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   'emprical via \y scans (Fair, 1990)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.198
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.96
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1557
_refine_ls_R_factor_gt           0.036
_refine_ls_shift/su_max          <0.001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme
'w = 1/[\sF^2^ + (0.02F)^2^ + 1.0], except w = 0 if F^2^ < 3\sF^2^'
_refine_ls_wR_factor_ref         0.045
_reflns_number_gt                1557
_reflns_number_total             2019
_reflns_observed_criterion       I>3\s(I)
_[local]_cod_data_source_file    sk1291.cif
_[local]_cod_data_source_block   ORCECL
_[local]_cod_cif_authors_sg_H-M  'P 21/a'
_cod_database_code               2009074
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,1/2+y,-z
-x,-y,-z
1/2+x,1/2-y,z
loop_
_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_calc_attached_atom
_atom_site_type_symbol
Cl .73299(7) .19707(6) .04180(6) .0806(2) Ueq . . Cl
O1 .57080(10) -.20000(10) .28720(10) .0517(4) Ueq . . O
O2 .2164(2) -.10660(10) .29040(10) .0590(4) Ueq . . O
N1 .4341(2) .00670(10) .2641(2) .0443(4) Ueq . . N
C1 .6137(2) -.1101(2) .2320(2) .0411(5) Ueq . . C
C2 .7216(2) -.1216(2) .1889(2) .0505(5) Ueq . . C
C3 .7601(2) -.0276(2) .1322(2) .0570(5) Ueq . . C
C4 .6888(2) .0785(2) .1176(2) .0518(5) Ueq . . C
C5 .5806(2) .0928(2) .1588(2) .0475(5) Ueq . . C
C6 .5444(2) -.0010(2) .2191(2) .0403(5) Ueq . . C
C7 .4163(2) .0885(2) .3430(2) .0428(5) Ueq . . C
C8 .3104(2) .0761(2) .3876(2) .0477(5) Ueq . . C
C9 .2178(2) -.0214(2) .3636(2) .0461(5) Ueq . . C
C10 .5140(2) .1944(2) .3858(2) .0580(6) Ueq . . C
C11 .1181(2) -.0248(2) .4306(2) .0627(6) Ueq . . C
H1 .619 -.260 .289 .0811 Uiso . . H
H1' .380 -.055 .253 .0671 Uiso . . H
H2 .770 -.195 .199 .0659 Uiso . . H
H3 .835 -.035 .103 .0722 Uiso . . H
H5 .531 .166 .145 .0633 Uiso . . H
H8 .312 .130 .451 .0595 Uiso . . H
H101 .512 .220 .464 .0760 Uiso . . H
H102 .609 .172 .397 .0760 Uiso . . H
H103 .483 .251 .314 .0760 Uiso . . H
H111 .144 .030 .502 .0811 Uiso . . H
H112 .022 -.009 .370 .0811 Uiso . . H
H113 .100 -.095 .450 .0811 Uiso . . 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
_atom_site_aniso_type_symbol
Cl .0915(3) .0828(4) .0724(3) -.0351(3) .0402(2) .0123(3) Cl
O1 .0708(6) .0330(7) .0693(6) .0071(6) .0472(4) .0042(6) O
O2 .0756(7) .0419(8) .0813(7) -.0165(6) .0544(4) -.0165(6) O
N1 .0499(7) .0292(8) .0627(7) -.0040(6) .0329(5) -.0045(7) N
C1 .0484(8) .0380(10) .0419(7) -.0019(8) .0243(6) -.0029(8) C
C2 .0552(9) .0510(10) .0536(9) .0030(9) .0313(6) -.0047(9) C
C3 .0528(9) .0740(10) .0537(9) -.0100(10) .0319(6) -.0060(10) C
C4 .0553(9) .0570(10) .0445(8) -.0197(9) .0231(6) -.0001(9) C
C5 .0503(9) .0390(10) .0509(9) -.0059(9) .0198(7) .0025(9) C
C6 .0426(8) .0370(10) .0443(8) -.0042(8) .0216(6) -.0031(7) C
C7 .0469(8) .0290(9) .0512(9) .0032(8) .0202(6) -.0013(8) C
C8 .0534(9) .0360(10) .0592(9) .0029(8) .0296(6) -.0091(8) C
C9 .0488(8) .0410(10) .0543(9) .0049(8) .0279(6) -.0004(9) C
C10 .0640(10) .0420(10) .0710(10) -.0100(10) .0322(8) -.0130(10) C
C11 .0589(9) .0660(10) .0790(10) -.0030(10) .0446(7) -.0080(10) C
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl C4 . . 1.743(2) yes
O1 C1 . . 1.353(3) yes
O1 H1 . . .833 no
O2 C9 . . 1.256(3) yes
N1 C6 . . 1.418(3) yes
N1 C7 . . 1.339(3) yes
N1 H1' . . .864 no
C1 C2 . . 1.383(3) no
C1 C6 . . 1.397(3) no
C2 C3 . . 1.376(3) no
C2 H2 . . .950 no
C3 C4 . . 1.374(3) no
C3 H3 . . .950 no
C4 C5 . . 1.375(4) no
C5 C6 . . 1.388(3) no
C5 H5 . . .950 no
C7 C8 . . 1.377(3) no
C7 C10 . . 1.496(3) yes
C8 C9 . . 1.399(3) no
C8 H8 . . .925 no
C9 C11 . . 1.499(4) yes
C10 H101 . . .927 no
C10 H102 . . .956 no
C10 H103 . . .964 no
C11 H111 . . .946 no
C11 H112 . . .935 no
C11 H113 . . .864 no
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 109.1 no
C6 N1 C7 128.9(2) yes
C6 N1 H1' 116.8 no
C7 N1 H1' 113.2 no
O1 C1 C2 123.2(2) yes
O1 C1 C6 117.5(2) yes
C2 C1 C6 119.3(2) no
C1 C2 C3 120.9(2) no
C1 C2 H2 119.5 no
C3 C2 H2 119.6 no
C2 C3 C4 119.1(2) no
C2 C3 H3 120.9 no
C4 C3 H3 120.0 no
Cl C4 C3 119.6(2) yes
Cl C4 C5 118.9(2) yes
C3 C4 C5 121.5(2) no
C4 C5 C6 119.4(2) no
C4 C5 H5 120.1 no
C6 C5 H5 120.6 no
N1 C6 C1 117.5(2) yes
N1 C6 C5 122.7(2) yes
C1 C6 C5 119.7(2) no
N1 C7 C8 121.0(2) yes
N1 C7 C10 119.9(2) yes
C8 C7 C10 119.0(2) no
C7 C8 C9 125.5(2) no
C7 C8 H8 117.0 no
C9 C8 H8 116.5 no
O2 C9 C8 123.0(2) yes
O2 C9 C11 118.8(2) yes
C8 C9 C11 118.2(2) no
C7 C10 H101 105.1 no
C7 C10 H102 108.8 no
C7 C10 H103 109.6 no
H101 C10 H102 113.7 no
H101 C10 H103 116.2 no
H102 C10 H103 103.4 no
C9 C11 H111 113.1 no
C9 C11 H112 111.1 no
C9 C11 H113 114.4 no
H111 C11 H112 107.6 no
H111 C11 H113 113.9 no
H112 C11 H113 95.1 no
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
H1 O1 C1 C6 179.4 no
C7 N1 C6 C1 131.6(2) no
C7 N1 C6 C5 -51.0(3) no
H1' N1 C6 C1 -35.56 no
H1' N1 C6 C5 141.77 no
C6 N1 C7 C8 -173.6(2) no
C6 N1 C7 C10 5.4(3) no
H1' N1 C7 C8 -6.05 no
H1' N1 C7 C10 173.00 no
O1 C1 C2 C3 179.3(2) no
C6 C1 C2 H2 179.24 no
O1 C1 C6 C5 -177.7(2) no
C2 C1 C6 N1 179.8(2) no
C2 C1 C6 C5 2.4(3) no
C1 C2 C3 H3 179.67 no
H2 C2 C3 C4 179.44 no
C2 C3 C4 CL -178.2(2) no
H3 C3 C4 C5 -179.98 no
Cl C4 C5 C6 179.9(2) no
C3 C4 C5 H5 -178.30 no
C4 C5 C6 N1 -179.9(2) no
C4 C5 C6 C1 -2.7(3) no
H5 C5 C6 C1 176.98 no
N1 C7 C8 C9 3.6(3) no
N1 C7 C8 H8 171.62 no
C10 C7 C8 C9 -175.5(2) no
C10 C7 C8 H8 -7.44 no
N1 C7 C10 H101 -155.93 no
N1 C7 C10 H102 -33.86 no
N1 C7 C10 H103 78.48 no
C8 C7 C10 H101 23.14 no
C8 C7 C10 H102 145.21 no
C8 C7 C10 H103 -102.45 no
C7 C8 C9 O2 -4.4(3) no
C7 C8 C9 C11 174.4(2) no
H8 C8 C9 O2 -172.53 no
H8 C8 C9 C11 6.33 no
O2 C9 C11 H111 163.57 no
O2 C9 C11 H112 -75.37 no
O2 C9 C11 H113 30.93 no
C8 C9 C11 H111 -15.35 no
C8 C9 C11 H112 105.72 no
C8 C9 C11 H113 -147.98 no
_journal_paper_doi 10.1107/S0108270199008501