#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006253.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_2006253
loop_
_publ_author_name
'Castellari, C.'
'Ottani, S.'
_publ_section_title
;
 Two Monoclinic Forms of Diclofenac Acid
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              794
_journal_page_last               797
_journal_volume                  53
_journal_year                    1997
_chemical_formula_moiety         'C14 H11 Cl2 N O2'
_chemical_formula_sum            'C14 H11 Cl2 N O2'
_chemical_formula_weight         296.14
_chemical_name_common            'Diclofenac acid'
_chemical_name_systematic
;
 (2-((2,6-Dichlorophenyl)amino-phenyl)acetic acid (HD)
;
_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'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 109.64(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.226(4)
_cell_length_b                   6.971(3)
_cell_length_c                   20.061(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17
_cell_measurement_theta_min      7
_cell_volume                     2664.0(14)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'MolEN (Fair, 1990)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'ENRAF NONIUS CAD-4 diffractometer'
_diffrn_measurement_method       'profile data from \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4383
_diffrn_reflns_theta_max         31.54
_diffrn_reflns_theta_min         3.11
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  160
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.483
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_meas      1.48
_exptl_crystal_density_method
;
flotation in a mixture of 1-bromo-3-chloropropane and p-xylene
;
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.249
_refine_ls_extinction_coef       0.0063(6)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   1.057
_refine_ls_goodness_of_fit_obs   1.178
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2582
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.075
_refine_ls_restrained_S_obs      1.169
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_obs          0.0374
_refine_ls_shift/esd_max         0.018
_refine_ls_shift/esd_mean        0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0635P)^2^+0.3396P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1126
_refine_ls_wR_factor_obs         0.0992
_reflns_number_observed          1743
_reflns_number_total             2589
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    sk1077.cif
_[local]_cod_data_source_block   HD2
_[local]_cod_cif_authors_sg_H-M  'C 2/c '
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2664.0(10)
_cod_database_code               2006253
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_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 0.0758(4) 0.0528(3) 0.0771(6) 0.0038(3) 0.0383(4) -0.0108(3)
Cl2 0.0766(4) 0.0459(3) 0.0941(7) 0.0089(3) 0.0500(4) -0.0031(3)
N1 0.0506(11) 0.0453(9) 0.054(2) -0.0135(8) 0.0228(12) -0.0077(10)
C1 0.0421(11) 0.0300(8) 0.055(2) -0.0028(7) 0.0217(13) -0.0049(9)
C2 0.0409(10) 0.0297(8) 0.060(2) -0.0006(7) 0.0221(12) -0.0088(8)
C3 0.0516(12) 0.0332(9) 0.073(2) -0.0051(9) 0.035(2) -0.0078(10)
C4 0.079(2) 0.0381(11) 0.063(2) -0.0075(10) 0.038(2) -0.0003(11)
C5 0.065(2) 0.0408(11) 0.057(2) -0.0040(10) 0.018(2) 0.0024(11)
C6 0.0462(12) 0.0396(10) 0.058(2) -0.0049(8) 0.0183(14) 0.0005(10)
C7 0.0438(10) 0.0350(9) 0.049(2) -0.0003(8) 0.0185(11) 0.0047(9)
C8 0.0487(11) 0.0400(9) 0.047(2) 0.0049(8) 0.0175(12) 0.0064(9)
C9 0.0507(12) 0.0603(13) 0.065(2) -0.0008(10) 0.0301(13) 0.0107(12)
C10 0.0632(15) 0.0547(13) 0.079(2) -0.0165(11) 0.032(2) 0.0082(12)
C11 0.074(2) 0.0373(10) 0.072(2) -0.0109(10) 0.0307(15) 0.0007(11)
C12 0.0541(12) 0.0367(9) 0.060(2) 0.0027(8) 0.0287(13) 0.0046(9)
C13 0.0415(12) 0.0466(11) 0.074(2) -0.0014(9) 0.0176(15) -0.0068(11)
C14 0.0460(12) 0.0479(11) 0.053(2) -0.0091(9) 0.0101(12) -0.0045(10)
O1 0.0704(10) 0.0563(9) 0.0776(14) -0.0221(8) 0.0386(10) -0.0219(8)
O2 0.0606(10) 0.0600(10) 0.091(2) -0.0241(8) 0.0327(11) -0.0247(9)
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_type_symbol
Cl1 0.45078(3) 0.14414(8) 0.04206(4) 0.0654(3) Uani d D 1 Cl
Cl2 0.35492(3) 0.66699(8) 0.18564(4) 0.0668(3) Uani d D 1 Cl
N1 0.35321(10) 0.2864(3) 0.11453(12) 0.0485(6) Uani d . 1 N
C1 0.34015(11) 0.2120(2) 0.17455(13) 0.0409(6) Uani d D 1 C
C2 0.27409(11) 0.1309(2) 0.16456(13) 0.0423(6) Uani d D 1 C
C3 0.26116(13) 0.0519(3) 0.2225(2) 0.0489(7) Uani d D 1 C
C4 0.3106(2) 0.0545(3) 0.2885(2) 0.0566(7) Uani d D 1 C
C5 0.37533(14) 0.1368(3) 0.2980(2) 0.0549(7) Uani d D 1 C
C6 0.38967(12) 0.2156(3) 0.24144(15) 0.0476(6) Uani d D 1 C
C7 0.40997(10) 0.4067(3) 0.11921(12) 0.0420(5) Uani d D 1 C
C8 0.45890(11) 0.3607(3) 0.08690(12) 0.0448(6) Uani d D 1 C
C9 0.51385(12) 0.4815(3) 0.08883(14) 0.0559(7) Uani d D 1 C
C10 0.52105(13) 0.6529(3) 0.1239(2) 0.0636(7) Uani d D 1 C
C11 0.47315(13) 0.7065(3) 0.15461(15) 0.0593(7) Uani d D 1 C
C12 0.41750(11) 0.5864(3) 0.15144(13) 0.0479(6) Uani d D 1 C
C13 0.21783(12) 0.1283(3) 0.0927(2) 0.0545(7) Uani d D 1 C
C14 0.22965(11) -0.0347(3) 0.04889(13) 0.0508(6) Uani d . 1 C
O1 0.27900(9) -0.0383(2) 0.02719(9) 0.0647(5) Uani d . 1 O
O2 0.18401(9) -0.1733(3) 0.03849(11) 0.0686(6) Uani d . 1 O
H1 0.3446(12) 0.224(3) 0.0822(13) 0.045(7) Uiso d . 1 H
H2 0.2168(10) -0.008(3) 0.2153(12) 0.061(6) Uiso d D 1 H
H3 0.3042(12) 0.001(3) 0.3289(11) 0.058(7) Uiso d D 1 H
H4 0.4092(10) 0.140(3) 0.3442(11) 0.054(8) Uiso d D 1 H
H5 0.4370(10) 0.267(3) 0.2470(12) 0.054(6) Uiso d D 1 H
H6 0.5467(11) 0.439(3) 0.0665(11) 0.060(6) Uiso d D 1 H
H7 0.5605(12) 0.730(4) 0.1273(14) 0.088(9) Uiso d D 1 H
H8 0.4732(14) 0.824(3) 0.1787(13) 0.080(8) Uiso d D 1 H
H9 0.2202(12) 0.253(3) 0.0667(12) 0.065(7) Uiso d D 1 H
H10 0.1711(11) 0.116(3) 0.0965(13) 0.067(7) Uiso d D 1 H
H11 0.1969(16) -0.267(5) 0.0166(16) 0.101(11) Uiso d . 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'
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 '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
C7 N1 C1 123.1(2) y
C7 N1 H1 110.6(17) y
C1 N1 H1 117.8(18) y
C6 C1 C2 119.5(2) ?
C6 C1 N1 122.6(2) ?
C2 C1 N1 117.9(2) ?
C3 C2 C1 118.6(2) ?
C3 C2 C13 120.2(2) ?
C1 C2 C13 121.2(2) ?
C4 C3 C2 121.6(2) ?
C4 C3 H2 119.9(14) ?
C2 C3 H2 118.5(14) ?
C3 C4 C5 119.4(2) ?
C3 C4 H3 124.2(15) ?
C5 C4 H3 116.4(15) ?
C6 C5 C4 120.3(3) ?
C6 C5 H4 120.8(13) ?
C4 C5 H4 118.9(13) ?
C5 C6 C1 120.6(2) ?
C5 C6 H5 120.8(13) ?
C1 C6 H5 118.3(13) ?
C8 C7 C12 116.1(2) ?
C8 C7 N1 121.8(2) ?
C12 C7 N1 121.9(2) ?
C9 C8 C7 122.5(2) ?
C9 C8 Cl1 118.6(2) ?
C7 C8 Cl1 118.93(15) ?
C10 C9 C8 119.4(2) ?
C10 C9 H6 122.5(14) ?
C8 C9 H6 118.1(14) ?
C11 C10 C9 120.1(2) ?
C11 C10 H7 121.6(17) ?
C9 C10 H7 118.2(17) ?
C10 C11 C12 120.2(2) ?
C10 C11 H8 125.9(16) ?
C12 C11 H8 113.9(16) ?
C11 C12 C7 121.6(2) ?
C11 C12 Cl2 118.6(2) ?
C7 C12 Cl2 119.80(14) ?
C14 C13 C2 110.5(2) ?
C14 C13 H9 107.4(13) ?
C2 C13 H9 109.2(14) ?
C14 C13 H10 109.2(14) ?
C2 C13 H10 111.4(15) ?
H9 C13 H10 109.1(19) ?
O1 C14 O2 123.3(2) y
O1 C14 C13 122.4(2) y
O2 C14 C13 114.2(2) y
C14 O2 H11 109(2) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_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 0.75(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 0.96(2) ?
C4 C5 1.382(3) ?
C4 H3 0.94(2) ?
C5 C6 1.376(3) ?
C5 H4 0.95(2) ?
C6 H5 0.99(2) ?
C7 C8 1.390(3) ?
C7 C12 1.395(3) ?
C8 C9 1.385(3) ?
C9 C10 1.370(3) ?
C9 H6 0.97(2) ?
C10 C11 1.363(3) ?
C10 H7 0.94(2) ?
C11 C12 1.387(3) ?
C11 H8 0.95(2) ?
C13 C14 1.503(3) ?
C13 H9 1.02(2) ?
C13 H10 0.98(2) ?
C14 O1 1.216(2) y
C14 O2 1.304(2) y
O2 H11 0.87(3) 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
C7 N1 C1 C6 -14.8(3) ?
C7 N1 C1 C2 165.6(2) ?
C6 C1 C2 C3 -1.6(2) ?
N1 C1 C2 C3 178.0(2) ?
C6 C1 C2 C13 178.5(2) ?
N1 C1 C2 C13 -1.9(2) ?
C1 C2 C3 C4 1.0(3) ?
C13 C2 C3 C4 -179.1(2) ?
C2 C3 C4 C5 -0.3(3) ?
C3 C4 C5 C6 0.0(3) ?
C4 C5 C6 C1 -0.6(3) ?
C2 C1 C6 C5 1.4(3) ?
N1 C1 C6 C5 -178.2(2) ?
C1 N1 C7 C8 123.2(2) ?
C1 N1 C7 C12 -62.2(3) ?
C12 C7 C8 C9 2.7(3) ?
N1 C7 C8 C9 177.5(2) ?
C12 C7 C8 Cl1 -177.1(2) ?
N1 C7 C8 Cl1 -2.2(3) ?
C7 C8 C9 C10 0.2(4) ?
Cl1 C8 C9 C10 179.9(2) ?
C8 C9 C10 C11 -2.1(4) ?
C9 C10 C11 C12 1.0(4) ?
C10 C11 C12 C7 2.1(4) ?
C10 C11 C12 Cl2 -175.6(2) ?
C8 C7 C12 C11 -3.8(3) ?
N1 C7 C12 C11 -178.6(2) ?
C8 C7 C12 Cl2 173.8(2) ?
N1 C7 C12 Cl2 -1.0(3) ?
C3 C2 C13 C14 -98.9(2) ?
C1 C2 C13 C14 81.0(2) ?
C2 C13 C14 O1 -68.3(3) y
C2 C13 C14 O2 109.4(2) y