##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2003-05-21
_journal_date_accepted     2003-06-17
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2003
_journal_volume     59
_journal_issue      7
_journal_page_first     o1004
_journal_page_last     o1005
_journal_paper_category     EO
_publ_contact_author_name     'Prof. Bohari M. Yamin'
_publ_contact_author_address
;
      X-ray Crystallography Laboratory
      School of Chemical Sciences and Food Technology
      Universiti Kebangsaan Malaysia
      43600 Bangi, Selangor
      MALAYSIA
;
_publ_contact_author_email     'bohari@pkrisc.cc.ukm.my'
_publ_contact_author_fax     '6 03 89292410 '
_publ_contact_author_phone     '6 03 89293880'
_publ_section_title
;
o-Methoxy-N-phenylbenzohydroxamic acid
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Elhadi Elbay Saad' ?
;     School of Chemical Sciences and Food Technology
      Universiti Kebangsaan Malaysia
      43600 Bangi, Selangor
      Malaysia
;
    'Yang Farina' ?
;     School of Chemical Sciences and Food Technology
      Universiti Kebangsaan Malaysia
      43600 Bangi, Selangor
      Malaysia
;
    'Bohari M. Yamin' ?
;     School of Chemical Sciences and Food Technology
      Universiti Kebangsaan Malaysia
      43600 Bangi, Selangor
      Malaysia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N-phenyl-o-methoxybenzohydroxamic acid
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H13 N O3'
_chemical_formula_sum     'C14 H13 N O3'
_chemical_formula_iupac     'C14 H13 N O3'
_chemical_formula_weight     243.25
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
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'
_cell_length_a     22.451(3)
_cell_length_b     8.3709(13)
_cell_length_c     14.921(2)
_cell_angle_alpha     90.00
_cell_angle_beta     118.531(3)
_cell_angle_gamma     90.00
_cell_volume     2463.6(6)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     2709
_cell_measurement_theta_min     2.1
_cell_measurement_theta_max     27.5
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.32
_exptl_crystal_size_min     0.25
_exptl_crystal_density_diffrn     1.312
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1024
_exptl_absorpt_coefficient_mu     0.093
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
;
Bruker SMART APEX CCD area-detector
;
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     83.66
_diffrn_reflns_number     8106
_diffrn_reflns_av_R_equivalents     0.0331
_diffrn_reflns_av_sigmaI/netI     0.0473
_diffrn_reflns_theta_min     2.1
_diffrn_reflns_theta_max     27.5
_diffrn_reflns_theta_full     27.5
_diffrn_measured_fraction_theta_max     0.99
_diffrn_measured_fraction_theta_full     0.99
_diffrn_reflns_limit_h_min     -29
_diffrn_reflns_limit_h_max     28
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     none
_refine_special_details
;
?
;
_reflns_number_total     2839
_reflns_number_gt     2229
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.059
_refine_ls_R_factor_gt     0.047
_refine_ls_wR_factor_gt     0.121
_refine_ls_wR_factor_ref     0.130
_refine_ls_goodness_of_fit_ref     1.04
_refine_ls_restrained_S_all     1.04
_refine_ls_number_reflns     2839
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0593P)²+0.5626P] where P = (Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     <0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.23
_refine_diff_density_min     -0.13
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'SMART (Seimens, 1996)'
_computing_cell_refinement     'SAINT (Seimens, 1996)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXTL (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL'
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
;
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_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 0.0888(8) 0.0716(7) 0.0385(5) 0.0328(6) 0.0149(5) 0.0087(5)
    O2 0.0616(6) 0.0812(7) 0.0329(5) 0.0130(5) 0.0176(4) 0.0033(4)
    O3 0.0464(6) 0.0718(8) 0.0695(7) -0.0063(5) 0.0149(5) -0.0083(5)
    N1 0.0502(6) 0.0547(7) 0.0347(5) 0.0101(5) 0.0154(5) 0.0065(5)
    C1 0.0468(7) 0.0557(8) 0.0441(7) -0.0014(6) 0.0213(6) -0.0010(6)
    C2 0.0601(9) 0.0766(11) 0.0448(7) 0.0012(7) 0.0270(7) 0.0041(7)
    C3 0.0599(9) 0.0905(12) 0.0415(7) 0.0036(8) 0.0211(7) -0.0098(8)
    C4 0.0504(8) 0.0654(9) 0.0540(8) 0.0007(7) 0.0129(6) -0.0177(7)
    C5 0.0456(7) 0.0552(8) 0.0480(7) -0.0008(6) 0.0143(6) -0.0001(6)
    C6 0.0348(6) 0.0550(8) 0.0362(6) 0.0003(5) 0.0128(5) -0.0007(5)
    C7 0.0398(6) 0.0575(8) 0.0341(6) -0.0006(5) 0.0141(5) 0.0009(5)
    C8 0.0411(6) 0.0613(8) 0.0345(6) 0.0052(5) 0.0188(5) 0.0027(5)
    C9 0.0497(7) 0.0635(9) 0.0501(7) 0.0028(6) 0.0221(6) 0.0019(6)
    C10 0.0670(10) 0.0629(10) 0.0756(10) 0.0119(8) 0.0343(9) 0.0151(8)
    C11 0.0574(9) 0.0854(13) 0.0658(10) 0.0233(8) 0.0230(8) 0.0234(9)
    C12 0.0439(8) 0.0914(12) 0.0471(7) 0.0090(7) 0.0145(6) 0.0038(8)
    C13 0.0421(6) 0.0695(9) 0.0397(6) 0.0024(6) 0.0190(5) -0.0009(6)
    C14 0.0601(10) 0.0968(14) 0.0812(12) -0.0163(9) 0.0188(9) -0.0276(11)
_geom_special_details
;
?
;
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_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_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_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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    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_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _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
