#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006253.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2006253
_journal_name_full 'Acta Crystallographica'
_journal_year 1997
_journal_volume C53
_journal_page_first 794
_journal_page_last 797
_publ_section_title
;
Two Monoclinic Forms of Diclofenac Acid
;
loop_
_publ_author_name
 'Carlo Castellari'
 'Stefano Ottani'
_chemical_name_common 'Diclofenac acid'
_chemical_formula_moiety 'C14 H11 Cl2 N O2'
_chemical_formula_sum 'C14 H11 Cl2 N O2'
_chemical_formula_weight 296.14
_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 20.226(4)
_cell_length_b 6.971(3)
_cell_length_c 20.061(4)
_cell_angle_alpha 90.00
_cell_angle_beta 109.64(2)
_cell_angle_gamma 90.00
_cell_volume 2664.0(10)
_cell_formula_units_Z 8
_cell_measurement_temperature 293(2)
_exptl_crystal_density_diffrn 1.477
_exptl_crystal_density_meas 1.48
_diffrn_ambient_temperature 293(2)
_refine_ls_R_factor_obs  .0374
_refine_ls_wR_factor_obs  .0992
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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
 Cl1  .45078(3)  .14414(8)  .04206(4)  .0654(3) Uani d D 1 . Cl
 Cl2  .35492(3)  .66699(8)  .18564(4)  .0668(3) Uani d D 1 . Cl
 N1  .35321(10)  .2864(3)  .11453(12)  .0485(6) Uani d . 1 . N
 C1  .34015(11)  .2120(2)  .17455(13)  .0409(6) Uani d D 1 . C
 C2  .27409(11)  .1309(2)  .16456(13)  .0423(6) Uani d D 1 . C
 C3  .26116(13)  .0519(3)  .2225(2)  .0489(7) Uani d D 1 . C
 C4  .3106(2)  .0545(3)  .2885(2)  .0566(7) Uani d D 1 . C
 C5  .37533(14)  .1368(3)  .2980(2)  .0549(7) Uani d D 1 . C
 C6  .38967(12)  .2156(3)  .24144(15)  .0476(6) Uani d D 1 . C
 C7  .40997(10)  .4067(3)  .11921(12)  .0420(5) Uani d D 1 . C
 C8  .45890(11)  .3607(3)  .08690(12)  .0448(6) Uani d D 1 . C
 C9  .51385(12)  .4815(3)  .08883(14)  .0559(7) Uani d D 1 . C
 C10  .52105(13)  .6529(3)  .1239(2)  .0636(7) Uani d D 1 . C
 C11  .47315(13)  .7065(3)  .15461(15)  .0593(7) Uani d D 1 . C
 C12  .41750(11)  .5864(3)  .15144(13)  .0479(6) Uani d D 1 . C
 C13  .21783(12)  .1283(3)  .0927(2)  .0545(7) Uani d D 1 . C
 C14  .22965(11)  -.0347(3)  .04889(13)  .0508(6) Uani d . 1 . C
 O1  .27900(9)  -.0383(2)  .02719(9)  .0647(5) Uani d . 1 . O
 O2  .18401(9)  -.1733(3)  .03849(11)  .0686(6) Uani d . 1 . O
 H1  .3446(12)  .224(3) .0822(13)  .045(7) Uiso d . 1 . H
 H2  .2168(10)  -.008(3) .2153(12)  .061(6) Uiso d D 1 . H
 H3  .3042(12)  .001(3) .3289(11)  .058(7) Uiso d D 1 . H
 H4  .4092(10)  .140(3) .3442(11)  .054(8) Uiso d D 1 . H
 H5  .4370(10)  .267(3) .2470(12)  .054(6) Uiso d D 1 . H
 H6  .5467(11)  .439(3) .0665(11)  .060(6) Uiso d D 1 . H
 H7  .5605(12)  .730(4) .1273(14)  .088(9) Uiso d D 1 . H
 H8  .4732(14)  .824(3) .1787(13)  .080(8) Uiso d D 1 . H
 H9  .2202(12)  .253(3) .0667(12)  .065(7) Uiso d D 1 . H
 H10  .1711(11)  .116(3) .0965(13)  .067(7) Uiso d D 1 . H
 H11  .1969(16)  -.267(5) .0166(16)  .101(11) Uiso d . 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  .0758(4)  .0528(3)  .0771(6)  .0038(3)  .0383(4)  -.0108(3)
 Cl2  .0766(4)  .0459(3)  .0941(7)  .0089(3)  .0500(4)  -.0031(3)
 N1  .0506(11)  .0453(9)  .054(2)  -.0135(8)  .0228(12)  -.0077(10)
 C1  .0421(11)  .0300(8)  .055(2)  -.0028(7)  .0217(13)  -.0049(9)
 C2  .0409(10)  .0297(8)  .060(2)  -.0006(7)  .0221(12)  -.0088(8)
 C3  .0516(12)  .0332(9)  .073(2)  -.0051(9)  .035(2)  -.0078(10)
 C4  .079(2)  .0381(11)  .063(2)  -.0075(10)  .038(2)  -.0003(11)
 C5  .065(2)  .0408(11)  .057(2)  -.0040(10)  .018(2)  .0024(11)
 C6  .0462(12)  .0396(10)  .058(2)  -.0049(8)  .0183(14)  .0005(10)
 C7  .0438(10)  .0350(9)  .049(2)  -.0003(8)  .0185(11)  .0047(9)
 C8  .0487(11)  .0400(9)  .047(2)  .0049(8)  .0175(12)  .0064(9)
 C9  .0507(12)  .0603(13)  .065(2)  -.0008(10)  .0301(13)  .0107(12)
 C10  .0632(15)  .0547(13)  .079(2)  -.0165(11)  .032(2)  .0082(12)
 C11  .074(2)  .0373(10)  .072(2)  -.0109(10)  .0307(15)  .0007(11)
 C12  .0541(12)  .0367(9)  .060(2)  .0027(8)  .0287(13)  .0046(9)
 C13  .0415(12)  .0466(11)  .074(2)  -.0014(9)  .0176(15)  -.0068(11)
 C14  .0460(12)  .0479(11)  .053(2)  -.0091(9)  .0101(12)  -.0045(10)
 O1  .0704(10)  .0563(9)  .0776(14)  -.0221(8)  .0386(10)  -.0219(8)
 O2  .0606(10)  .0600(10)  .091(2)  -.0241(8)  .0327(11)  -.0247(9)
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 C8 . 1.736(2) y
 Cl2 C12 . 1.724(2) y
 N1 C7 . 1.399(2) y
 N1 C1 . 1.415(3) y
 N1 H1 .  .75(2) ?
 C1 C6 . 1.379(3) ?
 C1 C2 . 1.402(3) ?
 C2 C3 . 1.389(3) ?
 C2 C13 . 1.507(4) y
 C3 C4 . 1.364(4) ?
 C3 H2 .  .96(2) ?
 C4 C5 . 1.382(3) ?
 C4 H3 .  .94(2) ?
 C5 C6 . 1.376(3) ?
 C5 H4 .  .95(2) ?
 C6 H5 .  .99(2) ?
 C7 C8 . 1.390(3) ?
 C7 C12 . 1.395(3) ?
 C8 C9 . 1.385(3) ?
 C9 C10 . 1.370(3) ?
 C9 H6 .  .97(2) ?
 C10 C11 . 1.363(3) ?
 C10 H7 .  .94(2) ?
 C11 C12 . 1.387(3) ?
 C11 H8 .  .95(2) ?
 C13 C14 . 1.503(3) ?
 C13 H9 . 1.02(2) ?
 C13 H10 .  .98(2) ?
 C14 O1 . 1.216(2) y
 C14 O2 . 1.304(2) y
 O2 H11 .  .87(3) y