#------------------------------------------------------------------------------
#$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $
#$Revision: 14 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2202430.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_2202430
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o1189
_journal_page_last  o1191
_publ_section_title
;
Indomethacin tert-butanol solvate at 120 K
;
loop_
_publ_author_name
  'Philip J. Cox'
  'Pamela L. Manson'
_chemical_formula_moiety  'C19 H16 Cl N O4, C4 H10 O'
_chemical_formula_sum  'C23 H26 Cl N O5'
_chemical_formula_weight  431.9
_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  11.98060(10)
_cell_length_b  12.27490(10)
_cell_length_c  14.7679(2)
_cell_angle_alpha  90
_cell_angle_beta  91.561(4)
_cell_angle_gamma  90
_cell_volume  2170.97(4)
_cell_formula_units_Z  4
_cell_measurement_temperature  120(2)
_exptl_crystal_density_diffrn  1.321
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
  Cl1 0.53744(3) 0.11454(2) 0.05621(2) 0.02768(10) Uani d . 1 . . Cl
  O1 0.39237(9) 0.49721(8) 0.34830(6) 0.0305(2) Uani d . 1 . . O
  O2 0.80140(7) 0.81999(8) 0.06995(6) 0.0254(2) Uani d . 1 . . O
  O3 0.50660(7) 0.99582(7) 0.33048(6) 0.0236(2) Uani d . 1 . . O
  O4 0.32713(8) 0.97083(9) 0.36370(7) 0.0299(2) Uani d . 1 . . O
  H4 0.3480(14) 1.0012(15) 0.4161(12) 0.036 Uiso d . 1 . . H
  N1 0.45321(8) 0.61486(8) 0.24050(7) 0.0174(2) Uani d . 1 . . N
  C2 0.38544(10) 0.70631(10) 0.25850(8) 0.0175(2) Uani d . 1 . . C
  C3 0.43169(9) 0.79601(9) 0.22054(8) 0.0164(2) Uani d . 1 . . C
  C4 0.53547(9) 0.76410(9) 0.18074(7) 0.0158(2) Uani d . 1 . . C
  C5 0.61917(10) 0.82526(10) 0.14003(8) 0.0170(2) Uani d . 1 . . C
  H5A 0.6115 0.9017 0.1319 0.02 Uiso calc R 1 . . H
  C6 0.71351(10) 0.77079(10) 0.11206(8) 0.0188(2) Uani d . 1 . . C
  C7 0.72567(10) 0.65809(10) 0.12564(9) 0.0216(3) Uani d . 1 . . C
  H7 0.7916 0.6229 0.1064 0.026 Uiso calc R 1 . . H
  C8 0.64368(10) 0.59707(10) 0.16644(8) 0.0203(2) Uani d . 1 . . C
  H8 0.6527 0.521 0.1762 0.024 Uiso calc R 1 . . H
  C9 0.54714(10) 0.65136(10) 0.19282(8) 0.0166(2) Uani d . 1 . . C
  C10 0.43581(10) 0.51033(10) 0.27556(8) 0.0196(2) Uani d . 1 . . C
  C11 0.46740(10) 0.41597(9) 0.21822(8) 0.0175(2) Uani d . 1 . . C
  C12 0.44942(10) 0.41659(10) 0.12441(8) 0.0185(2) Uani d . 1 . . C
  H12 0.4234 0.4809 0.0949 0.022 Uiso calc R 1 . . H
  C13 0.46952(10) 0.32326(10) 0.07407(8) 0.0192(2) Uani d . 1 . . C
  H13 0.4563 0.3225 0.0104 0.023 Uiso calc R 1 . . H
  C14 0.50936(10) 0.23112(9) 0.11890(8) 0.0188(2) Uani d . 1 . . C
  C15 0.52904(10) 0.22873(10) 0.21180(8) 0.0203(2) Uani d . 1 . . C
  H15 0.5572 0.1649 0.2408 0.024 Uiso calc R 1 . . H
  C16 0.50667(10) 0.32171(10) 0.26147(8) 0.0199(2) Uani d . 1 . . C
  H16 0.5181 0.3213 0.3254 0.024 Uiso calc R 1 . . H
  C17 0.27818(10) 0.69725(11) 0.30715(9) 0.0232(3) Uani d . 1 . . C
  H17A 0.294 0.6882 0.3722 0.03 Uiso calc R 1 . . H
  H17B 0.2361 0.6341 0.2842 0.03 Uiso calc R 1 . . H
  H17C 0.234 0.7635 0.297 0.03 Uiso calc R 1 . . H
  C18 0.38432(10) 0.90966(10) 0.22037(8) 0.0191(2) Uani d . 1 . . C
  H18A 0.3022 0.9066 0.211 0.025 Uiso calc R 1 . . H
  H18B 0.4158 0.9522 0.1701 0.025 Uiso calc R 1 . . H
  C19 0.41293(10) 0.96445(9) 0.30993(8) 0.0179(2) Uani d . 1 . . C
  C20 0.79578(12) 0.93475(12) 0.05756(11) 0.0326(3) Uani d . 1 . . C
  H20A 0.7296 0.953 0.0201 0.042 Uiso calc R 1 . . H
  H20B 0.863 0.9599 0.0274 0.042 Uiso calc R 1 . . H
  H20C 0.7909 0.9705 0.1166 0.042 Uiso calc R 1 . . H
  O5 0.36383(9) 0.06827(8) 0.51688(6) 0.0293(2) Uani d . 1 . . O
  H51 0.4084(15) 0.0423(15) 0.5603(12) 0.035 Uiso d . 1 . . H
  C21 0.35108(11) 0.18542(10) 0.52502(8) 0.0216(3) Uani d . 1 . . C
  C22 0.27654(13) 0.22029(13) 0.44516(9) 0.0341(3) Uani d . 1 . . C
  H22A 0.2052 0.1815 0.4472 0.044 Uiso calc R 1 . . H
  H22B 0.3133 0.2029 0.3885 0.044 Uiso calc R 1 . . H
  H22C 0.2631 0.2989 0.4484 0.044 Uiso calc R 1 . . H
  C23 0.46498(14) 0.23816(15) 0.52097(13) 0.0466(4) Uani d . 1 . . C
  H23A 0.5015 0.2151 0.4656 0.061 Uiso calc R 1 . . H
  H23B 0.5106 0.216 0.5739 0.061 Uiso calc R 1 . . H
  H23C 0.4566 0.3176 0.5208 0.061 Uiso calc R 1 . . H
  C24 0.29574(13) 0.20767(14) 0.61433(9) 0.0367(4) Uani d . 1 . . C
  H24A 0.3426 0.1788 0.6642 0.048 Uiso calc R 1 . . H
  H24B 0.2224 0.1722 0.6144 0.048 Uiso calc R 1 . . H
  H24C 0.2864 0.2864 0.6221 0.048 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
  Cl1 0.03772(19) 0.01558(15) 0.02960(17) 0.00434(12) -0.00167(13)
  -0.00534(11)
  O1 0.0437(6) 0.0250(5) 0.0232(5) 0.0010(4) 0.0110(4) 0.0006(4)
  O2 0.0198(4) 0.0242(5) 0.0325(5) 0.0000(3) 0.0081(4) 0.0018(4)
  O3 0.0219(4) 0.0217(5) 0.0270(5) -0.0018(3) -0.0032(4) 0.0007(4)
  O4 0.0229(5) 0.0408(6) 0.0262(5) -0.0010(4) 0.0035(4) -0.0159(4)
  N1 0.0181(5) 0.0148(5) 0.0195(5) 0.0008(4) 0.0020(4) -0.0034(4)
  C2 0.0174(6) 0.0179(6) 0.0170(5) 0.0019(4) -0.0010(4) -0.0046(4)
  C3 0.0167(5) 0.0174(6) 0.0149(5) 0.0030(4) -0.0016(4) -0.0037(4)
  C4 0.0168(5) 0.0172(6) 0.0131(5) 0.0025(4) -0.0019(4) -0.0031(4)
  C5 0.0190(6) 0.0157(5) 0.0161(5) 0.0016(4) -0.0014(4) -0.0013(4)
  C6 0.0163(5) 0.0218(6) 0.0183(5) -0.0011(4) 0.0002(4) -0.0016(4)
  C7 0.0169(6) 0.0212(6) 0.0269(6) 0.0044(5) 0.0021(5) -0.0045(5)
  C8 0.0201(6) 0.0155(6) 0.0253(6) 0.0030(4) -0.0001(5) -0.0032(5)
  C9 0.0166(5) 0.0170(5) 0.0161(5) -0.0004(4) -0.0005(4) -0.0027(4)
  C10 0.0211(6) 0.0182(6) 0.0195(6) -0.0006(4) -0.0007(4) -0.0012(4)
  C11 0.0178(5) 0.0147(5) 0.0200(6) -0.0021(4) 0.0008(4) -0.0012(4)
  C12 0.0194(6) 0.0145(5) 0.0215(6) 0.0005(4) -0.0015(4) 0.0016(4)
  C13 0.0202(6) 0.0186(6) 0.0186(6) -0.0007(4) -0.0025(4) -0.0007(4)
  C14 0.0185(6) 0.0134(5) 0.0245(6) -0.0011(4) 0.0010(4) -0.0028(4)
  C15 0.0209(6) 0.0153(6) 0.0246(6) -0.0001(4) -0.0013(5) 0.0047(5)
  C16 0.0220(6) 0.0195(6) 0.0180(5) -0.0023(5) -0.0010(4) 0.0027(4)
  C17 0.0194(6) 0.0240(6) 0.0264(6) 0.0002(5) 0.0045(5) -0.0034(5)
  C18 0.0200(6) 0.0178(6) 0.0194(6) 0.0056(4) -0.0013(4) -0.0014(4)
  C19 0.0214(6) 0.0112(5) 0.0211(6) 0.0041(4) -0.0004(4) 0.0002(4)
  C20 0.0321(7) 0.0255(7) 0.0408(8) -0.0015(6) 0.0133(6) 0.0051(6)
  O5 0.0399(6) 0.0255(5) 0.0221(5) 0.0055(4) -0.0078(4) -0.0054(4)
  C21 0.0226(6) 0.0227(6) 0.0194(6) 0.0010(5) -0.0030(5) 0.0000(5)
  C22 0.0388(8) 0.0385(8) 0.0244(7) 0.0064(6) -0.0090(6) 0.0018(6)
  C23 0.0343(8) 0.0483(10) 0.0565(10) -0.0150(7) -0.0096(7) 0.0267(8)
  C24 0.0398(8) 0.0480(9) 0.0223(7) 0.0174(7) -0.0018(6) -0.0065(6)
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 . 1.7422(12) Y
  O1 C10 . 1.2169(15) N
  O2 C6 . 1.3769(14) N
  O2 C20 . 1.4219(17) N
  O3 C19 . 1.2170(15) Y
  O4 C19 . 1.3183(15) Y
  O4 H4 . 0.889(18) N
  N1 C10 . 1.4014(15) N
  N1 C2 . 1.4148(14) N
  N1 C9 . 1.4164(15) N
  C2 C3 . 1.3604(17) N
  C2 C17 . 1.4934(16) N
  C3 C4 . 1.4438(15) N
  C3 C18 . 1.5061(16) N
  C4 C5 . 1.4013(16) N
  C4 C9 . 1.4019(16) N
  C5 C6 . 1.3859(16) N
  C5 H5A . 0.95 N
  C6 C7 . 1.4049(18) N
  C7 C8 . 1.3861(18) N
  C7 H7 . 0.95 N
  C8 C9 . 1.3992(16) N
  C8 H8 . 0.95 N
  C10 C11 . 1.4898(16) N
  C11 C12 . 1.3963(17) N
  C11 C16 . 1.3970(17) N
  C12 C13 . 1.3903(17) N
  C12 H12 . 0.95 N
  C13 C14 . 1.3886(17) N
  C13 H13 . 0.95 N
  C14 C15 . 1.3860(17) N
  C15 C16 . 1.3868(17) N
  C15 H15 . 0.95 N
  C16 H16 . 0.95 N
  C17 H17A . 0.98 N
  C17 H17B . 0.98 N
  C17 H17C . 0.98 N
  C18 C19 . 1.5146(16) N
  C18 H18A . 0.99 N
  C18 H18B . 0.99 N
  C20 H20A . 0.98 N
  C20 H20B . 0.98 N
  C20 H20C . 0.98 N
  O5 C21 . 1.4514(16) Y
  O5 H51 . 0.883(18) N
  C21 C23 . 1.5130(19) N
  C21 C24 . 1.5170(18) N
  C21 C22 . 1.5213(17) N
  C22 H22A . 0.98 N
  C22 H22B . 0.98 N
  C22 H22C . 0.98 N
  C23 H23A . 0.98 N
  C23 H23B . 0.98 N
  C23 H23C . 0.98 N
  C24 H24A . 0.98 N
  C24 H24B . 0.98 N
  C24 H24C . 0.98 N