#------------------------------------------------------------------------------
#$Date: 2008-01-26 15:05:32 +0200 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2014563.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_2014563
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2004
_journal_volume  60
_journal_page_first  o853
_journal_page_last  o855
_publ_section_title
;
Brucine and its solvates
;
loop_
_publ_author_name
  'Agata Bia\/lo\'nska'
  'Zbigniew Ciunik'
_chemical_name_common  'brucine acetone solvate'
_chemical_formula_moiety  'C23 H26 N2 O4, C3 H6 O1'
_chemical_formula_sum  'C26 H32 N2 O5'
_chemical_formula_iupac  'C23 H26 N2 O4, C3 H6 O1'
_chemical_formula_weight  452.54
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'P 21'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z'
_cell_length_a  12.765(3)
_cell_length_b  7.1360(14)
_cell_length_c  13.686(3)
_cell_angle_alpha  90.00
_cell_angle_beta  114.35(3)
_cell_angle_gamma  90.00
_cell_volume  1135.8(4)
_cell_formula_units_Z  2
_cell_measurement_temperature  100(2)
_exptl_crystal_density_diffrn  1.323
_diffrn_ambient_temperature  100(2)
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
  O1 -0.20202(7) 0.84329(16) 0.62098(7) 0.01909(19) Uani d . 1 . . O
  O2 0.46740(7) 0.74598(16) 0.59011(7) 0.0192(2) Uani d . 1 . . O
  O3 0.56432(7) 0.78149(17) 0.79570(7) 0.0200(2) Uani d . 1 . . O
  O4 0.03127(7) 0.80242(14) 0.42777(7) 0.01571(18) Uani d . 1 . . O
  N1 0.09290(8) 0.89447(15) 0.60258(7) 0.01126(18) Uani d . 1 . . N
  N2 0.13778(9) 0.99105(15) 0.94933(8) 0.01240(19) Uani d . 1 . . N
  C1 0.27666(9) 0.82368(19) 0.57999(8) 0.0127(2) Uani d . 1 . . C
  H1 0.2381 0.8076 0.5001 0.013 Uiso d . 1 . . H
  C2 0.39497(10) 0.79816(18) 0.63658(9) 0.0136(2) Uani d . 1 . . C
  C3 0.44846(9) 0.81867(19) 0.74958(9) 0.0138(2) Uani d . 1 . . C
  C4 0.38393(9) 0.86991(18) 0.80611(9) 0.0129(2) Uani d . 1 . . C
  H4 0.4220 0.8873 0.8831 0.021 Uiso d . 1 . . H
  C5 0.26548(9) 0.89605(17) 0.74979(9) 0.0108(2) Uani d . 1 . . C
  C6 0.21350(9) 0.87135(17) 0.63953(9) 0.0111(2) Uani d . 1 . . C
  C7 0.17850(9) 0.95351(16) 0.79250(9) 0.0100(2) Uani d . 1 . . C
  C8 0.06224(9) 0.90999(17) 0.69608(8) 0.0107(2) Uani d . 1 . . C
  H8 0.0098 1.0130 0.6844 0.015 Uiso d . 1 . . H
  C9 0.01080(10) 0.83540(18) 0.50657(9) 0.0125(2) Uani d . 1 . . C
  C10 -0.10891(9) 0.8210(2) 0.50473(9) 0.0152(2) Uani d . 1 . . C
  H10A -0.1539 0.7590 0.4394 0.015 Uiso d . 1 . . H
  H10B -0.1305 0.9534 0.5019 0.034 Uiso d . 1 . . H
  C11 -0.11740(10) 0.73107(19) 0.60445(10) 0.0147(2) Uani d . 1 . . C
  H11 -0.1464 0.6074 0.5901 0.018 Uiso d . 1 . . H
  C12 -0.23319(11) 0.7764(2) 0.70501(11) 0.0221(3) Uani d . 1 . . C
  H12A -0.2225 0.6370 0.7123 0.032 Uiso d . 1 . . H
  H12B -0.3153 0.8116 0.6826 0.025 Uiso d . 1 . . H
  C13 -0.15592(11) 0.8582(2) 0.81192(10) 0.0187(2) Uani d . 1 . . C
  H13 -0.1844 0.9507 0.8439 0.025 Uiso d . 1 . . H
  C14 -0.04417(10) 0.81492(19) 0.86031(9) 0.0144(2) Uani d . 1 . . C
  C15 0.03805(10) 0.90876(19) 0.96228(9) 0.0145(2) Uani d . 1 . . C
  H15A 0.0684 0.8164 1.0245 0.018 Uiso d . 1 . . H
  H15B -0.0004 1.0080 0.9830 0.020 Uiso d . 1 . . H
  C16 0.10836(10) 1.16577(18) 0.88598(9) 0.0130(2) Uani d . 1 . . C
  H16A 0.0280 1.1676 0.8352 0.020 Uiso d . 1 . . H
  H16B 0.1252 1.2730 0.9320 0.017 Uiso d . 1 . . H
  C17 0.18295(10) 1.16256(18) 0.82253(9) 0.0121(2) Uani d . 1 . . C
  H17A 0.1472 1.2508 0.7567 0.014 Uiso d . 1 . . H
  H17B 0.2595 1.2016 0.8636 0.019 Uiso d . 1 . . H
  C18 0.00202(10) 0.72591(17) 0.69891(9) 0.0121(2) Uani d . 1 . . C
  H18 0.0437 0.6279 0.6790 0.022 Uiso d . 1 . . H
  C19 0.01140(10) 0.67502(18) 0.81178(9) 0.0132(2) Uani d . 1 . . C
  H19 -0.0244 0.5592 0.8094 0.019 Uiso d . 1 . . H
  C20 0.14115(10) 0.66348(18) 0.88440(9) 0.0134(2) Uani d . 1 . . C
  H20A 0.1776 0.5849 0.8516 0.013 Uiso d . 1 . . H
  H20B 0.1541 0.6102 0.9552 0.022 Uiso d . 1 . . H
  C21 0.19243(9) 0.85962(17) 0.89880(9) 0.0116(2) Uani d . 1 . . C
  H21 0.2769 0.8472 0.9461 0.020 Uiso d . 1 . . H
  C22 0.41717(12) 0.7196(3) 0.47647(11) 0.0272(3) Uani d . 1 . . C
  H22A 0.3574 0.6217 0.4550 0.023 Uiso d . 1 . . H
  H22B 0.4811 0.6857 0.4606 0.025 Uiso d . 1 . . H
  H22C 0.3810 0.8303 0.4382 0.039 Uiso d . 1 . . H
  C23 0.61798(10) 0.7820(2) 0.91084(10) 0.0224(3) Uani d . 1 . . C
  H23A 0.6955 0.7311 0.9282 0.029 Uiso d . 1 . . H
  H23B 0.5796 0.7092 0.9439 0.017 Uiso d . 1 . . H
  H23C 0.6195 0.9055 0.9377 0.019 Uiso d . 1 . . H
  O5 0.50525(10) 0.3384(2) 0.90311(9) 0.0365(3) Uani d . 1 . . O
  C24 0.50798(12) 0.3265(2) 0.81547(11) 0.0246(3) Uani d . 1 . . C
  C25 0.39991(13) 0.3376(2) 0.71355(11) 0.0261(3) Uani d . 1 . . C
  H25A 0.3350 0.3910 0.7300 0.036 Uiso d . 1 . . H
  H25B 0.4080 0.4161 0.6586 0.042 Uiso d . 1 . . H
  H25C 0.3789 0.2146 0.6848 0.040 Uiso d . 1 . . H
  C26 0.61886(13) 0.2968(3) 0.80320(12) 0.0370(4) Uani d . 1 . . C
  H26A 0.6835 0.2970 0.8719 0.030 Uiso d . 1 . . H
  H26B 0.6114 0.1786 0.7602 0.034 Uiso d . 1 . . H
  H26C 0.6274 0.3938 0.7575 0.042 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
  O1 0.0121(3) 0.0264(5) 0.0199(4) 0.0027(4) 0.0078(3) 0.0003(4)
  O2 0.0143(4) 0.0318(5) 0.0135(4) 0.0038(4) 0.0079(3) 0.0004(4)
  O3 0.0096(4) 0.0369(6) 0.0128(4) 0.0043(4) 0.0037(3) 0.0027(4)
  O4 0.0158(4) 0.0183(4) 0.0120(3) -0.0012(3) 0.0046(3) -0.0022(3)
  N1 0.0095(4) 0.0133(4) 0.0102(4) 0.0002(4) 0.0033(3) -0.0015(3)
  N2 0.0143(4) 0.0113(4) 0.0138(4) -0.0003(4) 0.0080(3) -0.0002(4)
  C1 0.0127(4) 0.0144(5) 0.0107(4) 0.0004(4) 0.0047(4) 0.0007(4)
  C2 0.0130(5) 0.0170(6) 0.0126(4) 0.0012(4) 0.0071(4) 0.0016(4)
  C3 0.0098(4) 0.0180(6) 0.0130(5) 0.0014(4) 0.0040(4) 0.0018(4)
  C4 0.0109(4) 0.0161(5) 0.0106(4) -0.0003(4) 0.0031(4) 0.0003(4)
  C5 0.0106(4) 0.0110(5) 0.0105(4) -0.0007(4) 0.0043(4) -0.0003(4)
  C6 0.0103(4) 0.0115(5) 0.0106(4) 0.0000(4) 0.0033(4) -0.0001(4)
  C7 0.0097(4) 0.0101(5) 0.0098(4) -0.0008(4) 0.0037(4) -0.0011(4)
  C8 0.0104(4) 0.0116(5) 0.0101(4) -0.0002(4) 0.0042(4) -0.0010(4)
  C9 0.0117(4) 0.0115(5) 0.0117(4) 0.0001(4) 0.0023(4) -0.0007(4)
  C10 0.0106(4) 0.0189(6) 0.0138(5) 0.0007(4) 0.0028(4) -0.0019(5)
  C11 0.0110(5) 0.0157(6) 0.0164(5) -0.0022(4) 0.0046(4) -0.0028(4)
  C12 0.0124(5) 0.0335(8) 0.0223(6) -0.0047(5) 0.0089(5) -0.0030(6)
  C13 0.0157(5) 0.0233(6) 0.0201(5) -0.0007(5) 0.0104(4) -0.0012(5)
  C14 0.0158(5) 0.0137(5) 0.0168(5) -0.0019(4) 0.0097(4) 0.0001(4)
  C15 0.0153(5) 0.0151(5) 0.0160(5) -0.0011(4) 0.0092(4) -0.0017(4)
  C16 0.0156(5) 0.0101(5) 0.0143(5) -0.0003(4) 0.0072(4) -0.0013(4)
  C17 0.0131(4) 0.0107(5) 0.0128(4) -0.0014(4) 0.0058(4) -0.0016(4)
  C18 0.0115(4) 0.0110(5) 0.0137(5) -0.0013(4) 0.0050(4) -0.0018(4)
  C19 0.0143(5) 0.0111(5) 0.0155(5) -0.0010(4) 0.0072(4) 0.0004(4)
  C20 0.0150(5) 0.0107(5) 0.0145(5) 0.0005(4) 0.0060(4) 0.0015(4)
  C21 0.0128(4) 0.0116(5) 0.0110(4) 0.0005(4) 0.0054(4) -0.0001(4)
  C22 0.0217(6) 0.0472(10) 0.0147(5) 0.0059(6) 0.0097(5) -0.0017(6)
  C23 0.0130(5) 0.0379(8) 0.0130(5) 0.0032(5) 0.0022(4) 0.0031(5)
  O5 0.0351(6) 0.0546(9) 0.0206(5) -0.0084(6) 0.0123(4) -0.0019(6)
  C24 0.0255(6) 0.0265(7) 0.0189(5) -0.0057(6) 0.0060(5) -0.0008(6)
  C25 0.0264(6) 0.0233(7) 0.0221(6) -0.0037(6) 0.0035(5) 0.0038(6)
  C26 0.0271(7) 0.0614(13) 0.0209(6) 0.0029(8) 0.0082(6) -0.0044(8)
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
  O1 C11 . 1.4356(15) ?
  O1 C12 . 1.4443(16) ?
  O2 C2 . 1.3721(14) ?
  O2 C22 . 1.4294(16) ?
  O3 C3 . 1.3735(14) ?
  O3 C23 . 1.4360(15) ?
  O4 C9 . 1.2326(15) ?
  N1 C9 . 1.3663(15) ?
  N1 C6 . 1.4182(14) ?
  N1 C8 . 1.4886(14) ?
  N2 C16 . 1.4761(16) ?
  N2 C15 . 1.4776(15) ?
  N2 C21 . 1.4974(15) ?
  C1 C2 . 1.3961(16) ?
  C1 C6 . 1.4040(15) ?
  C1 H1 . 1.0037 ?
  C2 C3 . 1.4173(15) ?
  C3 C4 . 1.3915(16) ?
  C4 C5 . 1.3978(15) ?
  C4 H4 . 0.9695 ?
  C5 C6 . 1.3867(15) ?
  C5 C7 . 1.5092(15) ?
  C7 C17 . 1.5422(17) ?
  C7 C21 . 1.5439(16) ?
  C7 C8 . 1.5574(16) ?
  C8 C18 . 1.5305(17) ?
  C8 H8 . 0.9623 ?
  C9 C10 . 1.5213(16) ?
  C10 C11 . 1.5517(17) ?
  C10 H10A . 0.9495 ?
  C10 H10B . 0.9803 ?
  C11 C18 . 1.5399(17) ?
  C11 H11 . 0.9457 ?
  C12 C13 . 1.5048(19) ?
  C12 H12A . 1.0035 ?
  C12 H12B . 0.9951 ?
  C13 C14 . 1.3378(17) ?
  C13 H13 . 0.9439 ?
  C14 C15 . 1.5132(17) ?
  C14 C19 . 1.5262(17) ?
  C15 H15A . 1.0190 ?
  C15 H15B . 0.9683 ?
  C16 C17 . 1.5307(16) ?
  C16 H16A . 0.9735 ?
  C16 H16B . 0.9578 ?
  C17 H17A . 1.0380 ?
  C17 H17B . 0.9466 ?
  C18 C19 . 1.5427(16) ?
  C18 H18 . 0.9833 ?
  C19 C20 . 1.5428(17) ?
  C19 H19 . 0.9380 ?
  C20 C21 . 1.5231(17) ?
  C20 H20A . 0.9514 ?
  C20 H20B . 0.9893 ?
  C21 H21 . 1.0069 ?
  C22 H22A . 0.9857 ?
  C22 H22B . 0.9580 ?
  C22 H22C . 0.9551 ?
  C23 H23A . 0.9874 ?
  C23 H23B . 0.9484 ?
  C23 H23C . 0.9517 ?
  O5 C24 . 1.2172(18) ?
  C24 C25 . 1.506(2) ?
  C24 C26 . 1.507(2) ?
  C25 H25A . 1.0185 ?
  C25 H25B . 0.9762 ?
  C25 H25C . 0.9536 ?
  C26 H26A . 0.9616 ?
  C26 H26B . 1.0103 ?
  C26 H26C . 0.9689 ?