data_2202423
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o986
_journal_page_last  o988
_publ_section_title
;
\g-Indomethacin at 120 K
;
loop_
_publ_author_name
  'Philip J. Cox'
  'Pamela L. Manson'
_chemical_formula_moiety  'C19 H16 Cl1 N1 O4'
_chemical_formula_sum  'C19 H16 Cl N O4'
_chemical_formula_iupac  'C19 H16 Cl1 N1 O4'
_chemical_formula_weight  357.78
_symmetry_cell_setting  triclinic
_symmetry_space_group_name_H-M  'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  9.236(5)
_cell_length_b  9.620(5)
_cell_length_c  10.887(5)
_cell_angle_alpha  69.897(5)
_cell_angle_beta  87.328(5)
_cell_angle_gamma  69.501(5)
_cell_volume  847.9(7)
_cell_formula_units_Z  2
_cell_measurement_temperature  120(2)
_exptl_crystal_density_diffrn  1.401
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 0.80746(6) -0.45402(6) 0.57008(5) 0.03666(18) Uani d . 1 . . Cl
  O1 0.03608(16) -0.17070(16) 0.50769(12) 0.0279(3) Uani d . 1 . . O
  O2 0.22313(17) 0.42194(16) -0.09306(13) 0.0322(4) Uani d . 1 . . O
  O3 -0.41729(18) 0.39171(18) -0.11120(13) 0.0349(4) Uani d . 1 . . O
  H3 -0.490(3) 0.481(3) -0.105(2) 0.042 Uiso d . 1 . . H
  O4 -0.38537(15) 0.33417(15) 0.10489(12) 0.0257(3) Uani d . 1 . . O
  N1 0.06753(17) -0.04055(17) 0.29426(14) 0.0195(4) Uani d . 1 . . N
  C2 -0.0734(2) -0.0227(2) 0.23317(18) 0.0198(4) Uani d . 1 . . C
  C3 -0.0977(2) 0.0896(2) 0.11135(17) 0.0187(4) Uani d . 1 . . C
  C4 0.0257(2) 0.1515(2) 0.09355(17) 0.0181(4) Uani d . 1 . . C
  C5 0.0524(2) 0.2719(2) -0.01188(18) 0.0200(4) Uani d . 1 . . C
  H5 -0.0166 0.3268 -0.0892 0.024 Uiso calc R 1 . . H
  C6 0.1818(2) 0.3074(2) 0.00067(18) 0.0228(4) Uani d . 1 . . C
  C7 0.2815(2) 0.2272(2) 0.11648(19) 0.0268(5) Uani d . 1 . . C
  H7 0.3695 0.2545 0.1232 0.032 Uiso calc R 1 . . H
  C8 0.2551(2) 0.1095(2) 0.22104(19) 0.0245(4) Uani d . 1 . . C
  H8 0.3224 0.0573 0.2994 0.029 Uiso calc R 1 . . H
  C9 0.1272(2) 0.0705(2) 0.20744(17) 0.0184(4) Uani d . 1 . . C
  C10 0.1238(2) -0.1381(2) 0.42508(18) 0.0206(4) Uani d . 1 . . C
  C11 0.2954(2) -0.2061(2) 0.45484(17) 0.0194(4) Uani d . 1 . . C
  C12 0.3937(2) -0.2635(2) 0.36842(18) 0.0227(4) Uani d . 1 . . C
  H12 0.352 -0.2502 0.2853 0.027 Uiso calc R 1 . . H
  C13 0.5518(2) -0.3399(2) 0.40265(18) 0.0252(5) Uani d . 1 . . C
  H13 0.6188 -0.3811 0.3447 0.03 Uiso calc R 1 . . H
  C14 0.6100(2) -0.3547(2) 0.52357(19) 0.0239(4) Uani d . 1 . . C
  C15 0.5142(2) -0.2964(2) 0.60978(18) 0.0246(4) Uani d . 1 . . C
  H15 0.5565 -0.3061 0.6914 0.03 Uiso calc R 1 . . H
  C16 0.3566(2) -0.2242(2) 0.57606(18) 0.0231(4) Uani d . 1 . . C
  H16 0.2896 -0.1866 0.6358 0.028 Uiso calc R 1 . . H
  C17 -0.1655(2) -0.1244(2) 0.29603(19) 0.0273(5) Uani d . 1 . . C
  H17A -0.2408 -0.1145 0.2301 0.035 Uiso calc R 1 . . H
  H17B -0.2205 -0.0907 0.3659 0.035 Uiso calc R 1 . . H
  H17C -0.0958 -0.2351 0.3335 0.035 Uiso calc R 1 . . H
  C18 -0.2287(2) 0.1459(2) 0.01031(18) 0.0212(4) Uani d . 1 . . C
  H18A -0.2769 0.0643 0.029 0.025 Uiso calc R 1 . . H
  H18B -0.1878 0.1595 -0.077 0.025 Uiso calc R 1 . . H
  C19 -0.3506(2) 0.3000(2) 0.00690(18) 0.0200(4) Uani d . 1 . . C
  C20 0.1179(2) 0.5202(2) -0.20739(18) 0.0282(5) Uani d . 1 . . C
  H20A 0.015 0.5686 -0.1808 0.037 Uiso calc R 1 . . H
  H20B 0.1112 0.4557 -0.2582 0.037 Uiso calc R 1 . . H
  H20C 0.1554 0.6035 -0.2614 0.037 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 0.0219(3) 0.0375(3) 0.0394(3) -0.0077(2) -0.0060(2) -0.0018(2)
  O1 0.0272(8) 0.0292(8) 0.0209(7) -0.0083(7) 0.0048(6) -0.0034(6)
  O2 0.0329(8) 0.0307(8) 0.0275(8) -0.0181(7) -0.0013(6) 0.0036(6)
  O3 0.0355(9) 0.0301(8) 0.0200(7) 0.0117(7) -0.0045(6) -0.0091(7)
  O4 0.0257(8) 0.0253(7) 0.0195(7) -0.0005(6) 0.0007(6) -0.0087(6)
  N1 0.0187(8) 0.0185(8) 0.0168(8) -0.0053(7) -0.0013(6) -0.0018(6)
  C2 0.0168(10) 0.0191(10) 0.0227(10) -0.0038(8) 0.0019(8) -0.0090(8)
  C3 0.0164(9) 0.0172(9) 0.0203(10) -0.0023(8) 0.0003(8) -0.0077(8)
  C4 0.0186(10) 0.0168(9) 0.0176(9) -0.0031(8) 0.0010(8) -0.0079(8)
  C5 0.0211(10) 0.0172(9) 0.0169(9) -0.0022(8) -0.0011(8) -0.0045(8)
  C6 0.0261(11) 0.0192(10) 0.0208(10) -0.0090(9) 0.0032(8) -0.0035(8)
  C7 0.0226(11) 0.0312(11) 0.0293(11) -0.0143(9) 0.0000(9) -0.0088(9)
  C8 0.0230(11) 0.0230(10) 0.0226(10) -0.0059(9) -0.0047(8) -0.0038(9)
  C9 0.0189(10) 0.0152(9) 0.0184(9) -0.0040(8) 0.0024(8) -0.0047(8)
  C10 0.0249(11) 0.0156(9) 0.0192(10) -0.0052(8) -0.0015(8) -0.0052(8)
  C11 0.0235(10) 0.0149(9) 0.0164(9) -0.0057(8) 0.0004(8) -0.0023(7)
  C12 0.0267(11) 0.0221(10) 0.0153(9) -0.0050(9) -0.0028(8) -0.0051(8)
  C13 0.0256(11) 0.0247(11) 0.0218(10) -0.0061(9) 0.0013(9) -0.0067(9)
  C14 0.0187(10) 0.0192(10) 0.0270(11) -0.0066(8) -0.0036(8) 0.0005(8)
  C15 0.0289(11) 0.0274(11) 0.0171(10) -0.0128(9) -0.0034(8) -0.0036(8)
  C16 0.0293(11) 0.0207(10) 0.0177(10) -0.0088(9) 0.0027(8) -0.0052(8)
  C17 0.0266(11) 0.0269(11) 0.0281(11) -0.0118(9) 0.0025(9) -0.0070(9)
  C18 0.0196(10) 0.0192(10) 0.0224(10) -0.0042(8) -0.0012(8) -0.0069(8)
  C19 0.0168(10) 0.0229(10) 0.0190(10) -0.0063(8) -0.0003(8) -0.0063(8)
  C20 0.0338(12) 0.0255(11) 0.0222(10) -0.0122(9) 0.0030(9) -0.0034(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 C14 . 1.740(2) Y
  O1 C10 . 1.216(2) Y
  O2 C6 . 1.373(2) N
  O2 C20 . 1.431(2) N
  O3 C19 . 1.313(2) Y
  O3 H3 . 0.91(2) N
  O4 C19 . 1.218(2) Y
  N1 C10 . 1.410(2) N
  N1 C9 . 1.417(2) N
  N1 C2 . 1.418(2) N
  C2 C3 . 1.360(3) N
  C2 C17 . 1.489(3) N
  C3 C4 . 1.437(3) N
  C3 C18 . 1.491(3) N
  C4 C9 . 1.399(3) N
  C4 C5 . 1.407(3) N
  C5 C6 . 1.378(3) N
  C5 H5 . 0.95 N
  C6 C7 . 1.405(3) N
  C7 C8 . 1.385(3) N
  C7 H7 . 0.95 N
  C8 C9 . 1.387(3) N
  C8 H8 . 0.95 N
  C10 C11 . 1.490(3) N
  C11 C16 . 1.391(3) N
  C11 C12 . 1.393(3) N
  C12 C13 . 1.386(3) N
  C12 H12 . 0.95 N
  C13 C14 . 1.388(3) N
  C13 H13 . 0.95 N
  C14 C15 . 1.384(3) N
  C15 C16 . 1.379(3) 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 . 1.505(3) Y
  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