##############################################################################
###                                                                        ###
###        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/  #
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#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
4-[1-(4-Chlorophenyl)-3-oxobutylamino]benzoic acid
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H16 Cl N O3'
_chemical_formula_sum     'C17 H16 Cl N O3'
_chemical_formula_iupac     'C17 H16 Cl N O3'
_chemical_formula_weight     317.76
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     6.0059(5)
_cell_length_b     34.018(3)
_cell_length_c     8.0271(6)
_cell_angle_alpha     90.00
_cell_angle_beta     107.727(6)
_cell_angle_gamma     90.00
_cell_volume     1562.1(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9512
_cell_measurement_theta_min     4.4
_cell_measurement_theta_max     26.5
_cell_measurement_temperature     173(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.22
_exptl_crystal_size_mid     0.18
_exptl_crystal_size_min     0.17
_exptl_crystal_density_diffrn     1.351
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     664
_exptl_absorpt_coefficient_mu     0.256
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(MULABS; Spek, 2003; Blessing, 1995)'
_exptl_absorpt_correction_T_min     0.9358
_exptl_absorpt_correction_T_max     0.9477
_exptl_special_details
;
;
_diffrn_ambient_temperature     173(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     'Stoe IPDSII two-circle'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10524
_diffrn_reflns_av_R_equivalents     0.0579
_diffrn_reflns_av_sigmaI/netI     0.0406
_diffrn_reflns_theta_min     2.39
_diffrn_reflns_theta_max     26.32
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -41
_diffrn_reflns_limit_k_max     42
_diffrn_reflns_limit_l_min     -8
_diffrn_reflns_limit_l_max     10
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3176
_reflns_number_gt     2693
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0462
_refine_ls_R_factor_gt     0.0382
_refine_ls_wR_factor_gt     0.1018
_refine_ls_wR_factor_ref     0.1055
_refine_ls_goodness_of_fit_ref     1.045
_refine_ls_restrained_S_all     1.045
_refine_ls_number_reflns     3176
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0636P)²+0.1867P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.254
_refine_diff_density_min     -0.342
_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'
    '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'
_computing_data_collection     'X-AREA (Stoe & Cie, 2001)'
_computing_cell_refinement     'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction     'X-AREA (Stoe & Cie, 2001)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1990)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'XP in SHELXTL-Plus (Sheldrick, 1991)'
_computing_publication_material     'SHELXL97 (Sheldrick, 1997)'
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_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 0.78406(8) 0.233987(12) 0.49552(6) 0.04873(16) Uani d . 1 . .
    O O1 1.40294(18) 0.37231(3) 1.05669(14) 0.0351(3) Uani d . 1 . .
    O O2 -0.00560(18) 0.49116(3) 0.19948(14) 0.0360(3) Uani d . 1 . .
    O O3 0.28629(19) 0.47831(3) 0.08845(14) 0.0356(3) Uani d . 1 . .
    H H3 0.186(5) 0.4902(8) -0.014(4) 0.076(8) Uiso d . 1 . .
    N N1 0.7119(2) 0.41099(3) 0.86357(16) 0.0266(3) Uani d . 1 . .
    H H1 0.623(3) 0.4061(5) 0.925(3) 0.037(5) Uiso d . 1 . .
    C C1 0.9242(2) 0.38766(4) 0.89325(18) 0.0238(3) Uani d . 1 . .
    H H1A 1.0412 0.4038 0.8574 0.029 Uiso calc R 1 . .
    C C2 1.0228(2) 0.37941(4) 1.08945(18) 0.0258(3) Uani d . 1 . .
    H H2A 1.0076 0.4035 1.1545 0.031 Uiso calc R 1 . .
    H H2B 0.9278 0.3586 1.1211 0.031 Uiso calc R 1 . .
    C C3 1.2763(2) 0.36668(4) 1.14671(18) 0.0268(3) Uani d . 1 . .
    C C4 1.3646(3) 0.34730(5) 1.3232(2) 0.0381(4) Uani d . 1 . .
    H H4A 1.3032 0.3204 1.3159 0.057 Uiso calc R 1 . .
    H H4B 1.3122 0.3623 1.4085 0.057 Uiso calc R 1 . .
    H H4C 1.5358 0.3465 1.3602 0.057 Uiso calc R 1 . .
    C C11 0.8857(2) 0.34943(4) 0.78887(17) 0.0235(3) Uani d . 1 . .
    C C12 0.7091(2) 0.32344(4) 0.79678(19) 0.0287(3) Uani d . 1 . .
    H H12 0.6102 0.3301 0.8650 0.034 Uiso calc R 1 . .
    C C13 0.6762(3) 0.28804(4) 0.7062(2) 0.0320(3) Uani d . 1 . .
    H H13 0.5563 0.2704 0.7127 0.038 Uiso calc R 1 . .
    C C14 0.8206(3) 0.27882(4) 0.60664(19) 0.0306(3) Uani d . 1 . .
    C C15 0.9960(3) 0.30408(4) 0.59526(19) 0.0315(3) Uani d . 1 . .
    H H15 1.0936 0.2974 0.5260 0.038 Uiso calc R 1 . .
    C C16 1.0272(2) 0.33933(4) 0.68662(19) 0.0271(3) Uani d . 1 . .
    H H16 1.1470 0.3569 0.6792 0.032 Uiso calc R 1 . .
    C C21 0.5924(2) 0.42668(4) 0.70343(17) 0.0227(3) Uani d . 1 . .
    C C22 0.3689(2) 0.44280(4) 0.68004(18) 0.0255(3) Uani d . 1 . .
    H H22 0.3042 0.4425 0.7743 0.031 Uiso calc R 1 . .
    C C23 0.2432(2) 0.45899(4) 0.52246(18) 0.0255(3) Uani d . 1 . .
    H H23 0.0917 0.4693 0.5089 0.031 Uiso calc R 1 . .
    C C24 0.3347(2) 0.46046(4) 0.38183(18) 0.0235(3) Uani d . 1 . .
    C C25 0.5592(2) 0.44553(4) 0.40492(18) 0.0248(3) Uani d . 1 . .
    H H25 0.6255 0.4470 0.3117 0.030 Uiso calc R 1 . .
    C C26 0.6860(2) 0.42854(4) 0.56237(18) 0.0252(3) Uani d . 1 . .
    H H26 0.8370 0.4181 0.5753 0.030 Uiso calc R 1 . .
    C C27 0.1934(2) 0.47808(4) 0.21563(18) 0.0254(3) Uani d . 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    Cl1 C14 . 1.7465(15) ?
    O1 C3 . 1.2132(18) ?
    O2 C27 . 1.2443(17) ?
    O3 C27 . 1.3041(17) ?
    O3 H3 . 0.95(3) ?
    N1 C21 . 1.3750(18) ?
    N1 C1 . 1.4586(17) ?
    N1 H1 . 0.85(2) ?
    C1 C11 . 1.5261(18) ?
    C1 C2 . 1.5304(19) ?
    C1 H1A . 1.0000 ?
    C2 C3 . 1.5133(19) ?
    C2 H2A . 0.9900 ?
    C2 H2B . 0.9900 ?
    C3 C4 . 1.505(2) ?
    C4 H4A . 0.9800 ?
    C4 H4B . 0.9800 ?
    C4 H4C . 0.9800 ?
    C11 C16 . 1.3922(19) ?
    C11 C12 . 1.3971(19) ?
    C12 C13 . 1.389(2) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.383(2) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.384(2) ?
    C15 C16 . 1.388(2) ?
    C15 H15 . 0.9500 ?
    C16 H16 . 0.9500 ?
    C21 C22 . 1.4083(18) ?
    C21 C26 . 1.4108(18) ?
    C22 C23 . 1.376(2) ?
    C22 H22 . 0.9500 ?
    C23 C24 . 1.3991(19) ?
    C23 H23 . 0.9500 ?
    C24 C25 . 1.3990(18) ?
    C24 C27 . 1.4731(19) ?
    C25 C26 . 1.3876(19) ?
    C25 H25 . 0.9500 ?
    C26 H26 . 0.9500 ?
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
    C27 O3 H3 . . 111.9(15) ?
    C21 N1 C1 . . 123.05(12) ?
    C21 N1 H1 . . 112.3(13) ?
    C1 N1 H1 . . 118.1(12) ?
    N1 C1 C11 . . 113.28(11) ?
    N1 C1 C2 . . 108.25(11) ?
    C11 C1 C2 . . 110.80(10) ?
    N1 C1 H1A . . 108.1 ?
    C11 C1 H1A . . 108.1 ?
    C2 C1 H1A . . 108.1 ?
    C3 C2 C1 . . 113.80(11) ?
    C3 C2 H2A . . 108.8 ?
    C1 C2 H2A . . 108.8 ?
    C3 C2 H2B . . 108.8 ?
    C1 C2 H2B . . 108.8 ?
    H2A C2 H2B . . 107.7 ?
    O1 C3 C4 . . 121.66(13) ?
    O1 C3 C2 . . 121.94(13) ?
    C4 C3 C2 . . 116.40(12) ?
    C3 C4 H4A . . 109.5 ?
    C3 C4 H4B . . 109.5 ?
    H4A C4 H4B . . 109.5 ?
    C3 C4 H4C . . 109.5 ?
    H4A C4 H4C . . 109.5 ?
    H4B C4 H4C . . 109.5 ?
    C16 C11 C12 . . 118.59(13) ?
    C16 C11 C1 . . 121.09(12) ?
    C12 C11 C1 . . 120.31(12) ?
    C13 C12 C11 . . 120.93(13) ?
    C13 C12 H12 . . 119.5 ?
    C11 C12 H12 . . 119.5 ?
    C14 C13 C12 . . 119.00(13) ?
    C14 C13 H13 . . 120.5 ?
    C12 C13 H13 . . 120.5 ?
    C13 C14 C15 . . 121.42(13) ?
    C13 C14 Cl1 . . 119.34(11) ?
    C15 C14 Cl1 . . 119.23(11) ?
    C14 C15 C16 . . 118.97(13) ?
    C14 C15 H15 . . 120.5 ?
    C16 C15 H15 . . 120.5 ?
    C15 C16 C11 . . 121.09(13) ?
    C15 C16 H16 . . 119.5 ?
    C11 C16 H16 . . 119.5 ?
    N1 C21 C22 . . 118.73(12) ?
    N1 C21 C26 . . 123.07(12) ?
    C22 C21 C26 . . 118.17(12) ?
    C23 C22 C21 . . 120.84(12) ?
    C23 C22 H22 . . 119.6 ?
    C21 C22 H22 . . 119.6 ?
    C22 C23 C24 . . 121.04(12) ?
    C22 C23 H23 . . 119.5 ?
    C24 C23 H23 . . 119.5 ?
    C23 C24 C25 . . 118.66(12) ?
    C23 C24 C27 . . 119.05(12) ?
    C25 C24 C27 . . 122.28(12) ?
    C26 C25 C24 . . 120.77(12) ?
    C26 C25 H25 . . 119.6 ?
    C24 C25 H25 . . 119.6 ?
    C25 C26 C21 . . 120.48(12) ?
    C25 C26 H26 . . 119.8 ?
    C21 C26 H26 . . 119.8 ?
    O2 C27 O3 . . 122.86(13) ?
    O2 C27 C24 . . 120.68(13) ?
    O3 C27 C24 . . 116.45(12) ?
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
    C21 N1 C1 C11 . . . . -63.24(16) ?
    C21 N1 C1 C2 . . . . 173.47(12) ?
    N1 C1 C2 C3 . . . . -162.23(11) ?
    C11 C1 C2 C3 . . . . 72.99(14) ?
    C1 C2 C3 O1 . . . . 17.90(19) ?
    C1 C2 C3 C4 . . . . -163.22(12) ?
    N1 C1 C11 C16 . . . . 128.90(13) ?
    C2 C1 C11 C16 . . . . -109.22(14) ?
    N1 C1 C11 C12 . . . . -52.24(16) ?
    C2 C1 C11 C12 . . . . 69.65(15) ?
    C16 C11 C12 C13 . . . . 0.7(2) ?
    C1 C11 C12 C13 . . . . -178.23(13) ?
    C11 C12 C13 C14 . . . . -0.3(2) ?
    C12 C13 C14 C15 . . . . -0.1(2) ?
    C12 C13 C14 Cl1 . . . . 178.84(11) ?
    C13 C14 C15 C16 . . . . 0.2(2) ?
    Cl1 C14 C15 C16 . . . . -178.76(11) ?
    C14 C15 C16 C11 . . . . 0.1(2) ?
    C12 C11 C16 C15 . . . . -0.6(2) ?
    C1 C11 C16 C15 . . . . 178.31(12) ?
    C1 N1 C21 C22 . . . . 169.04(12) ?
    C1 N1 C21 C26 . . . . -13.0(2) ?
    N1 C21 C22 C23 . . . . 179.71(12) ?
    C26 C21 C22 C23 . . . . 1.64(19) ?
    C21 C22 C23 C24 . . . . -1.0(2) ?
    C22 C23 C24 C25 . . . . -0.78(19) ?
    C22 C23 C24 C27 . . . . 179.97(12) ?
    C23 C24 C25 C26 . . . . 1.86(19) ?
    C27 C24 C25 C26 . . . . -178.92(12) ?
    C24 C25 C26 C21 . . . . -1.2(2) ?
    N1 C21 C26 C25 . . . . -178.54(12) ?
    C22 C21 C26 C25 . . . . -0.56(19) ?
    C23 C24 C27 O2 . . . . -0.66(19) ?
    C25 C24 C27 O2 . . . . -179.87(13) ?
    C23 C24 C27 O3 . . . . -179.32(12) ?
    C25 C24 C27 O3 . . . . 1.47(18) ?
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
    O3 H3 O2 3_565 0.95(3) 1.68(3) 2.6248(15) 177(2)
    N1 H1 O1 1_455 0.85(2) 2.24(2) 3.0543(16) 160.5(17)
data_global
_journal_date_recd_electronic     2007-10-17
_journal_date_accepted     2007-10-18
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue     11
_journal_page_first     o4420
_journal_page_last     o4421
_journal_paper_category     QO
_journal_coeditor_code     AT2438
_publ_contact_author
;
      Dr. Michael Bolte
      Institut für Anorganische Chemie
      J. W. Goethe-Universität
      Max-von-Laue-Str. 7
      60438 Frankfurt/Main
      Germany
;
_publ_contact_author_email     bolte@chemie.uni-frankfurt.de
_publ_contact_author_fax     '49 69 798 29239'
_publ_contact_author_phone     '49 69 798 29136'
_publ_section_title
;
4-[1-(4-Chlorophenyl)-3-oxobutylamino]benzoic acid
;
loop_
    _publ_author_name
    _publ_author_address
    'Narayana, B.'
;     Department of  Studies in  Chemistry,
        Mangalore University,
 Mangalagangotri 574 199,
      India
;
    'Sunil, K.'
;     Department of  Studies in  Chemistry,
        Mangalore University,
 Mangalagangotri 574 199,
      India
;
    'Sarojini, B. K.'
;     Department of  Studies in  Chemistry,
        Mangalore University,
 Mangalagangotri 574 199,
      India
;
    'Yathirajan, H. S.'
;     Department of Studies in Chemistry
      University of Mysore
      Manasagangotri,
      Mysore 570 006,
      India
;
    'Bolte, Michael'
;     Institut für Anorganische Chemie
      J. W. Goethe-Universität Frankfurt
      Max-von-Laue-Strasse 7
      60438 Frankfurt/Main
      Germany
;
