#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/40/2014008.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_2014008
loop_
_publ_author_name
'Glidewell, Christopher'
'Low, John N.'
'Skakle, Janet M. S.'
'Wardell, James L.'
_publ_section_title
;
 (Cyclohexylideneamino)oxyacetic acid and
 [chloro(phenyl)methyleneamino]oxyacetic acid: hydrogen-bonded
 R_2^2(8) dimers and aromatic π--π stacking interactions
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o270
_journal_page_last               o272
_journal_paper_doi               10.1107/S0108270104004299
_journal_volume                  60
_journal_year                    2004
_chemical_formula_moiety         'C9 H8 Cl N O3'
_chemical_formula_sum            'C9 H8 Cl N O3'
_chemical_formula_weight         213.61
_chemical_name_systematic
;
[Chloro(phenyl)methyleneamino]oxyacetic acid
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                98.4852(9)
_cell_angle_beta                 93.4156(10)
_cell_angle_gamma                117.0191(12)
_cell_formula_units_Z            2
_cell_length_a                   6.79610(10)
_cell_length_b                   7.3857(2)
_cell_length_c                   10.8173(3)
_cell_measurement_reflns_used    2133
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      3.16
_cell_volume                     473.44(2)
_computing_cell_refinement       'DENZO--SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD Server Software (Nonius, 1997)'
_computing_data_reduction        'DENZO--SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 and PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement  'OSCAIL and SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution
'OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans, and ω scans with κ offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0758
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3988
_diffrn_reflns_theta_full        27.41
_diffrn_reflns_theta_max         27.41
_diffrn_reflns_theta_min         3.16
_diffrn_standards_decay_%        negligible
_exptl_absorpt_coefficient_mu    0.382
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.481
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.200
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2132
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.200
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0766P)²+0.1738P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1293
_refine_ls_wR_factor_ref         0.1412
_reflns_number_gt                1980
_reflns_number_total             2133
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg1209.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' 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_database_code               2014008
_cod_database_fobs_code          2014008
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cl1 0.82919(7) 0.00737(7) 0.78680(4) 0.02459(19) Uani d . 1 . . Cl
O1 0.2370(2) 0.27726(19) 0.50408(13) 0.0235(3) Uani d . 1 . . O
O2 0.5944(2) 0.36247(19) 0.56736(12) 0.0229(3) Uani d . 1 . . O
O3 0.4685(2) 0.00535(19) 0.65729(11) 0.0211(3) Uani d . 1 . . O
N4 0.5117(3) 0.1192(2) 0.78071(14) 0.0197(3) Uani d . 1 . . N
C1 0.3942(3) 0.2414(3) 0.55267(16) 0.0193(4) Uani d . 1 . . C
C2 0.3016(3) 0.0310(3) 0.58876(17) 0.0219(4) Uani d . 1 . . C
C5 0.6749(3) 0.1242(2) 0.84810(16) 0.0175(4) Uani d . 1 . . C
C11 0.7394(3) 0.2326(2) 0.98149(16) 0.0183(4) Uani d . 1 . . C
C12 0.9281(3) 0.2563(3) 1.05444(17) 0.0219(4) Uani d . 1 . . C
C13 0.9880(3) 0.3636(3) 1.17899(18) 0.0264(4) Uani d . 1 . . C
C14 0.8604(3) 0.4479(3) 1.23152(18) 0.0276(4) Uani d . 1 . . C
C15 0.6704(3) 0.4242(3) 1.15935(19) 0.0272(4) Uani d . 1 . . C
C16 0.6092(3) 0.3170(3) 1.03528(18) 0.0230(4) Uani d . 1 . . C
H1 0.2951 0.3949 0.4848 0.028 Uiso calc R 1 . . H
H2A 0.1816 0.0141 0.6408 0.026 Uiso calc R 1 . . H
H2B 0.2353 -0.0780 0.5113 0.026 Uiso calc R 1 . . H
H12 1.0167 0.1987 1.0190 0.026 Uiso calc R 1 . . H
H13 1.1172 0.3790 1.2281 0.032 Uiso calc R 1 . . H
H14 0.9020 0.5217 1.3165 0.033 Uiso calc R 1 . . H
H15 0.5823 0.4819 1.1954 0.033 Uiso calc R 1 . . H
H16 0.4790 0.3007 0.9867 0.028 Uiso calc R 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
Cl1 0.0273(3) 0.0281(3) 0.0234(3) 0.0181(2) 0.00411(19) 0.00161(19)
O1 0.0176(6) 0.0243(7) 0.0273(7) 0.0094(5) -0.0010(5) 0.0045(5)
O2 0.0174(6) 0.0228(6) 0.0254(7) 0.0076(5) -0.0016(5) 0.0039(5)
O3 0.0230(6) 0.0223(6) 0.0172(6) 0.0109(5) 0.0008(5) 0.0014(5)
N4 0.0228(7) 0.0193(7) 0.0160(7) 0.0091(6) 0.0037(6) 0.0030(5)
C1 0.0188(8) 0.0226(8) 0.0149(8) 0.0097(7) 0.0009(6) -0.0004(6)
C2 0.0176(8) 0.0241(8) 0.0216(8) 0.0079(7) 0.0005(6) 0.0044(7)
C5 0.0185(8) 0.0143(7) 0.0210(8) 0.0078(6) 0.0058(6) 0.0053(6)
C11 0.0211(8) 0.0134(7) 0.0193(8) 0.0063(6) 0.0050(6) 0.0059(6)
C12 0.0245(9) 0.0174(8) 0.0229(9) 0.0092(7) 0.0021(7) 0.0043(7)
C13 0.0287(9) 0.0225(9) 0.0241(9) 0.0097(7) -0.0019(7) 0.0036(7)
C14 0.0360(10) 0.0202(9) 0.0196(9) 0.0080(8) 0.0038(7) 0.0018(7)
C15 0.0326(10) 0.0246(9) 0.0258(10) 0.0145(8) 0.0091(8) 0.0029(7)
C16 0.0243(9) 0.0232(8) 0.0232(9) 0.0124(7) 0.0050(7) 0.0048(7)
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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
O1 C1 O2 124.64(16) y
O1 C1 C2 112.36(14) y
O2 C1 C2 123.00(16) y
C1 O1 H1 109.5 no
O3 C2 C1 111.90(14) no
O3 C2 H2A 109.2 no
C1 C2 H2A 109.2 no
O3 C2 H2B 109.2 no
C1 C2 H2B 109.2 no
H2A C2 H2B 107.9 no
C2 O3 N4 107.45(13) y
O3 N4 C5 113.12(14) y
N4 C5 C11 120.30(15) no
N4 C5 Cl1 121.60(14) no
C11 C5 Cl1 118.09(13) no
C12 C11 C16 119.17(17) no
C12 C11 C5 121.68(16) no
C16 C11 C5 119.14(16) no
C11 C12 C13 120.46(18) no
C11 C12 H12 119.8 no
C13 C12 H12 119.8 no
C14 C13 C12 120.27(18) no
C14 C13 H13 119.9 no
C12 C13 H13 119.9 no
C13 C14 C15 119.69(18) no
C13 C14 H14 120.2 no
C15 C14 H14 120.2 no
C16 C15 C14 120.40(18) no
C16 C15 H15 119.8 no
C14 C15 H15 119.8 no
C15 C16 C11 120.00(17) no
C15 C16 H16 120.0 no
C11 C16 H16 120.0 no
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
C5 Cl1 . 1.738(2) y
C1 O1 . 1.311(2) y
C1 O2 . 1.226(2) y
C1 C2 . 1.510(2) no
O1 H1 . 0.84 no
C2 O3 . 1.418(2) no
C2 H2A . 0.99 no
C2 H2B . 0.99 no
O3 N4 . 1.405(2) y
N4 C5 . 1.273(2) y
C5 C11 . 1.477(2) no
C11 C12 . 1.390(3) no
C11 C16 . 1.402(3) no
C12 C13 . 1.391(3) no
C12 H12 . 0.95 no
C13 C14 . 1.381(3) no
C13 H13 . 0.95 no
C14 C15 . 1.393(3) no
C14 H14 . 0.95 no
C15 C16 . 1.386(3) no
C15 H15 . 0.95 no
C16 H16 . 0.95 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
O1 H1 O2 2_666 0.84 1.79 2.6329(17) 176 y
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
O2 C1 C2 O3 8.7(2) no
O1 C1 C2 O3 -171.61(14) y
C1 C2 O3 N4 75.87(17) y
C2 O3 N4 C5 -173.61(14) y
O3 N4 C5 C11 -178.38(13) no
O3 N4 C5 Cl1 2.2(2) no
N4 C5 C11 C12 -174.38(15) no
Cl1 C5 C11 C12 5.0(2) no
N4 C5 C11 C16 4.5(2) no
Cl1 C5 C11 C16 -176.09(12) no
C16 C11 C12 C13 -0.5(3) no
C5 C11 C12 C13 178.41(15) no
C11 C12 C13 C14 0.0(3) no
C12 C13 C14 C15 0.3(3) no
C13 C14 C15 C16 -0.1(3) no
C14 C15 C16 C11 -0.4(3) no
C12 C11 C16 C15 0.6(3) no
C5 C11 C16 C15 -178.26(15) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21181391
