#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/22/2202264.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_2202264
loop_
_publ_author_name
'Elhadi Elbay Saad'
'Yang Farina'
'Bohari M. Yamin'
_publ_section_title
;
 o-Methoxy-N-phenylbenzohydroxamic acid
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1004
_journal_page_last               o1005
_journal_paper_doi               10.1107/S1600536803013564
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C14 H13 N O3'
_chemical_formula_moiety         'C14 H13 N O3'
_chemical_formula_sum            'C14 H13 N O3'
_chemical_formula_weight         243.25
_chemical_name_systematic
;
N-phenyl-o-methoxybenzohydroxamic acid
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 118.531(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.451(3)
_cell_length_b                   8.3709(13)
_cell_length_c                   14.921(2)
_cell_measurement_reflns_used    2709
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.1
_cell_volume                     2463.6(6)
_computing_cell_refinement       'SAINT (Seimens, 1996)'
_computing_data_collection       'SMART (Seimens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 83.66
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type
;
Bruker SMART APEX CCD area-detector
;
_diffrn_measurement_method       ω
_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  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0473
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8106
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.1
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.13
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2839
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.059
_refine_ls_R_factor_gt           0.047
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0593P)²+0.5626P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.121
_refine_ls_wR_factor_ref         0.130
_reflns_number_gt                2229
_reflns_number_total             2839
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ac6044.cif
_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_enum 1527 2010-12-29 10:47:43Z saulius 

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_H-M      'C 2/c'
_cod_database_code               2202264
_cod_database_fobs_code          2202264
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.26350(6) 0.88494(14) 0.12891(7) 0.0727(4) Uani d . 1 . . O
H1A 0.2451 0.8431 0.0724 0.109 Uiso calc R 1 . . H
O2 0.31734(5) 0.65663(14) 0.07502(7) 0.0606(3) Uani d . 1 . . O
O3 0.45786(5) 0.77742(14) 0.31765(8) 0.0679(3) Uani d . 1 . . O
N1 0.30728(6) 0.77572(14) 0.20054(8) 0.0486(3) Uani d . 1 . . N
C1 0.31973(7) 0.68471(17) 0.36362(10) 0.0490(3) Uani d . 1 . . C
H1B 0.3165 0.5792 0.3422 0.059 Uiso calc R 1 . . H
C2 0.32723(8) 0.7194(2) 0.45915(11) 0.0597(4) Uani d . 1 . . C
H2A 0.3298 0.6369 0.5026 0.072 Uiso calc R 1 . . H
C3 0.33084(8) 0.8751(2) 0.49009(11) 0.0653(4) Uani d . 1 . . C
H3A 0.3358 0.8977 0.5543 0.078 Uiso calc R 1 . . H
C4 0.32725(7) 0.9970(2) 0.42680(11) 0.0616(4) Uani d . 1 . . C
H4A 0.3294 1.1023 0.4480 0.074 Uiso calc R 1 . . H
C5 0.32045(7) 0.96475(17) 0.33104(11) 0.0529(3) Uani d . 1 . . C
H5A 0.3181 1.0478 0.2881 0.064 Uiso calc R 1 . . H
C6 0.31715(6) 0.80803(16) 0.30051(9) 0.0437(3) Uani d . 1 . . C
C7 0.33543(6) 0.66695(16) 0.16711(9) 0.0453(3) Uani d . 1 . . C
C8 0.38821(6) 0.55763(17) 0.24190(9) 0.0453(3) Uani d . 1 . . C
C9 0.37689(7) 0.39490(19) 0.23187(11) 0.0552(4) Uani d . 1 . . C
H9A 0.3352 0.3559 0.1826 0.066 Uiso calc R 1 . . H
C10 0.42684(9) 0.2898(2) 0.29427(14) 0.0684(4) Uani d . 1 . . C
H10A 0.4191 0.1802 0.2877 0.082 Uiso calc R 1 . . H
C11 0.48836(9) 0.3493(2) 0.36647(13) 0.0722(5) Uani d . 1 . . C
H11A 0.5221 0.2786 0.4086 0.087 Uiso calc R 1 . . H
C12 0.50103(7) 0.5099(2) 0.37769(11) 0.0638(4) Uani d . 1 . . C
H12A 0.5430 0.5475 0.4268 0.077 Uiso calc R 1 . . H
C13 0.45093(7) 0.61640(19) 0.31543(9) 0.0506(3) Uani d . 1 . . C
C14 0.52019(9) 0.8451(2) 0.39225(15) 0.0855(6) Uani d . 1 . . C
H14A 0.5183 0.9592 0.3850 0.128 Uiso calc R 1 . . H
H14B 0.5568 0.8043 0.3828 0.128 Uiso calc R 1 . . H
H14C 0.5275 0.8174 0.4592 0.128 Uiso calc R 1 . . H
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
_geom_angle_publ_flag
N1 O1 H1A 109.5 ?
C13 O3 C14 118.22(13) yes
C7 N1 O1 116.61(10) yes
C7 N1 C6 131.03(10) yes
O1 N1 C6 112.23(10) yes
C6 C1 C2 119.38(14) ?
C6 C1 H1B 120.3 ?
C2 C1 H1B 120.3 ?
C3 C2 C1 120.31(15) ?
C3 C2 H2A 119.8 ?
C1 C2 H2A 119.8 ?
C4 C3 C2 120.16(14) ?
C4 C3 H3A 119.9 ?
C2 C3 H3A 119.9 ?
C3 C4 C5 120.45(15) ?
C3 C4 H4A 119.8 ?
C5 C4 H4A 119.8 ?
C6 C5 C4 119.14(14) ?
C6 C5 H5A 120.4 ?
C4 C5 H5A 120.4 ?
C5 C6 C1 120.54(12) ?
C5 C6 N1 118.89(12) ?
C1 C6 N1 120.48(12) ?
O2 C7 N1 120.05(12) ?
O2 C7 C8 120.71(12) ?
N1 C7 C8 119.23(11) ?
C9 C8 C13 119.78(12) ?
C9 C8 C7 119.01(11) ?
C13 C8 C7 120.94(13) ?
C10 C9 C8 120.55(14) ?
C10 C9 H9A 119.7 ?
C8 C9 H9A 119.7 ?
C11 C10 C9 119.05(17) ?
C11 C10 H10A 120.5 ?
C9 C10 H10A 120.5 ?
C12 C11 C10 121.59(15) ?
C12 C11 H11A 119.2 ?
C10 C11 H11A 119.2 ?
C11 C12 C13 119.67(15) ?
C11 C12 H12A 120.2 ?
C13 C12 H12A 120.2 ?
O3 C13 C12 125.16(13) ?
O3 C13 C8 115.47(12) ?
C12 C13 C8 119.35(15) ?
O3 C14 H14A 109.5 ?
O3 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
O3 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
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
O1 N1 . 1.3931(14) yes
O1 H1A . 0.8200 ?
O2 C7 . 1.2359(15) yes
O3 C13 . 1.3554(19) yes
O3 C14 . 1.4251(19) yes
N1 C7 . 1.3335(17) yes
N1 C6 . 1.4252(16) yes
C1 C6 . 1.3797(19) ?
C1 C2 . 1.384(2) ?
C1 H1B . 0.9300 ?
C2 C3 . 1.372(2) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.367(2) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.389(2) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.3791(19) ?
C5 H5A . 0.9300 ?
C7 C8 . 1.4912(17) ?
C8 C9 . 1.381(2) ?
C8 C13 . 1.3975(18) ?
C9 C10 . 1.379(2) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.377(3) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.368(2) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.387(2) ?
C12 H12A . 0.9300 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
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 H1A O2 7_565 0.82 1.96 2.7200(14) 153 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
C6 C1 C2 C3 1.2(2)
C1 C2 C3 C4 -0.2(2)
C2 C3 C4 C5 -0.5(2)
C3 C4 C5 C6 0.2(2)
C4 C5 C6 C1 0.8(2)
C4 C5 C6 N1 177.36(12)
C2 C1 C6 C5 -1.5(2)
C2 C1 C6 N1 -177.99(12)
C7 N1 C6 C5 138.63(15)
O1 N1 C6 C5 -37.05(16)
C7 N1 C6 C1 -44.8(2)
O1 N1 C6 C1 139.54(13)
O1 N1 C7 O2 -7.0(2)
C6 N1 C7 O2 177.52(13)
O1 N1 C7 C8 173.63(12)
C6 N1 C7 C8 -1.9(2)
O2 C7 C8 C9 -59.39(18)
N1 C7 C8 C9 120.02(14)
O2 C7 C8 C13 114.66(15)
N1 C7 C8 C13 -65.93(17)
C13 C8 C9 C10 0.4(2)
C7 C8 C9 C10 174.53(14)
C8 C9 C10 C11 -0.3(2)
C9 C10 C11 C12 0.0(3)
C10 C11 C12 C13 0.2(3)
C14 O3 C13 C12 -2.8(2)
C14 O3 C13 C8 178.80(14)
C11 C12 C13 O3 -178.44(14)
C11 C12 C13 C8 -0.1(2)
C9 C8 C13 O3 178.29(12)
C7 C8 C13 O3 4.28(18)
C9 C8 C13 C12 -0.2(2)
C7 C8 C13 C12 -174.18(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21131696
