#------------------------------------------------------------------------------
#$Date: 2011-09-17 23:27:16 +0300 (Sat, 17 Sep 2011) $
#$Revision: 26029 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2014564.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_2014564
_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 2-propanol solvate dihydrate'
_chemical_formula_moiety  'C23 H26 N2 O4, C3 H8 O1, 2H2 O'
_chemical_formula_sum  'C26 H38 N2 O7'
_chemical_formula_iupac  'C23 H26 N2 O4, C3 H8 O1, 2H2 O'
_chemical_formula_weight  490.58
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P 21 21 21'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, -y, z+1/2'
  '-x, y+1/2, -z+1/2'
  'x+1/2, -y+1/2, -z'
_cell_length_a  7.9297(3)
_cell_length_b  12.3289(7)
_cell_length_c  25.1631(10)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  2460.06(19)
_cell_formula_units_Z  4
_cell_measurement_temperature  100(2)
_exptl_crystal_density_diffrn  1.325
_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 0.23144(15) 0.51181(9) 0.33192(4) 0.0189(2) Uani d . 1 . . O
  O2 0.17650(15) 1.09858(8) 0.14223(4) 0.0170(2) Uani d . 1 . . O
  O3 0.23853(15) 1.21113(8) 0.22681(4) 0.0173(2) Uani d . 1 . . O
  O4 0.16424(16) 0.69525(9) 0.17113(4) 0.0216(2) Uani d . 1 . . O
  N1 0.15614(17) 0.76820(10) 0.25401(5) 0.0144(3) Uani d . 1 . . N
  N2 0.22204(18) 0.85524(11) 0.43108(5) 0.0186(3) Uani d . 1 . . N
  C1 0.16244(19) 0.92874(12) 0.19113(6) 0.0152(3) Uani d . 1 . . C
  H1 0.1454 0.8887 0.1593 0.014 Uiso d . 1 . . H
  C2 0.1843(2) 1.04026(12) 0.18844(6) 0.0146(3) Uani d . 1 . . C
  C3 0.21532(19) 1.10228(12) 0.23486(6) 0.0150(3) Uani d . 1 . . C
  C4 0.21924(19) 1.05148(12) 0.28420(6) 0.0154(3) Uani d . 1 . . C
  H4 0.2359 1.0953 0.3165 0.018 Uiso d . 1 . . H
  C5 0.19594(19) 0.93975(12) 0.28701(5) 0.0143(3) Uani d . 1 . . C
  C6 0.16979(19) 0.87991(12) 0.24107(6) 0.0142(3) Uani d . 1 . . C
  C7 0.1799(2) 0.86890(11) 0.33556(5) 0.0140(3) Uani d . 1 . . C
  C8 0.18818(19) 0.75230(12) 0.31176(5) 0.0136(3) Uani d . 1 . . C
  H8 0.0987 0.7050 0.3260 0.018 Uiso d . 1 . . H
  C9 0.1806(2) 0.68471(12) 0.21950(6) 0.0161(3) Uani d . 1 . . C
  C10 0.2305(2) 0.57641(12) 0.24344(6) 0.0180(3) Uani d . 1 . . C
  H10A 0.1303 0.5364 0.2500 0.020 Uiso d . 1 . . H
  H10B 0.2944 0.5391 0.2162 0.022 Uiso d . 1 . . H
  C11 0.3293(2) 0.57650(12) 0.29639(6) 0.0161(3) Uani d . 1 . . C
  H11 0.4378 0.5419 0.2912 0.018 Uiso d . 1 . . H
  C12 0.3153(2) 0.48521(13) 0.38102(6) 0.0227(3) Uani d . 1 . . C
  H12A 0.4390 0.4740 0.3733 0.022 Uiso d . 1 . . H
  H12B 0.2683 0.4150 0.3916 0.021 Uiso d . 1 . . H
  C13 0.2884(2) 0.57142(14) 0.42283(6) 0.0222(3) Uani d . 1 . . C
  H13 0.2257 0.5488 0.4533 0.028 Uiso d . 1 . . H
  C14 0.3435(2) 0.67244(13) 0.41731(6) 0.0193(3) Uani d . 1 . . C
  C15 0.3051(2) 0.76117(13) 0.45685(6) 0.0217(3) Uani d . 1 . . C
  H15A 0.2221 0.7346 0.4841 0.034 Uiso d . 1 . . H
  H15B 0.4158 0.7850 0.4740 0.029 Uiso d . 1 . . H
  C16 0.0419(2) 0.83283(13) 0.41857(6) 0.0198(3) Uani d . 1 . . C
  H16A -0.0316 0.8632 0.4455 0.020 Uiso d . 1 . . H
  H16B 0.0268 0.7523 0.4167 0.019 Uiso d . 1 . . H
  C17 0.0112(2) 0.88701(13) 0.36501(6) 0.0170(3) Uani d . 1 . . C
  H17A -0.0870 0.8562 0.3465 0.023 Uiso d . 1 . . H
  H17B -0.0061 0.9641 0.3704 0.014 Uiso d . 1 . . H
  C18 0.35731(19) 0.69349(12) 0.31556(6) 0.0150(3) Uani d . 1 . . C
  H18 0.4329 0.7259 0.2869 0.017 Uiso d . 1 . . H
  C19 0.4451(2) 0.71034(13) 0.36937(6) 0.0175(3) Uani d . 1 . . C
  H19 0.5561 0.6719 0.3679 0.023 Uiso d . 1 . . H
  C20 0.4772(2) 0.83300(13) 0.37365(6) 0.0186(3) Uani d . 1 . . C
  H20A 0.5570 0.8515 0.4022 0.023 Uiso d . 1 . . H
  H20B 0.5352 0.8613 0.3410 0.023 Uiso d . 1 . . H
  C21 0.3082(2) 0.88992(12) 0.38084(6) 0.0166(3) Uani d . 1 . . C
  H21 0.3266 0.9673 0.3834 0.020 Uiso d . 1 . . H
  C22 0.1644(2) 1.03768(13) 0.09384(6) 0.0211(3) Uani d . 1 . . C
  H22A 0.1672 1.0922 0.0655 0.021 Uiso d . 1 . . H
  H22B 0.2546 0.9869 0.0900 0.020 Uiso d . 1 . . H
  H22C 0.0548 0.9975 0.0933 0.032 Uiso d . 1 . . H
  C23 0.2677(2) 1.27568(13) 0.27301(6) 0.0217(3) Uani d . 1 . . C
  H23A 0.2775 1.3510 0.2609 0.023 Uiso d . 1 . . H
  H23B 0.1778 1.2737 0.2980 0.027 Uiso d . 1 . . H
  H23C 0.3713 1.2525 0.2928 0.023 Uiso d . 1 . . H
  O5 0.96333(16) 0.85804(10) 0.01511(4) 0.0244(3) Uani d . 1 . . O
  H5 1.0606 0.8842 0.0043 0.039 Uiso d . 1 . . H
  C24 0.8220(3) 0.93197(14) -0.06200(7) 0.0288(4) Uani d . 1 . . C
  H24A 0.7571 0.9857 -0.0403 0.033 Uiso d . 1 . . H
  H24B 0.9371 0.9661 -0.0734 0.040 Uiso d . 1 . . H
  H24C 0.7606 0.9147 -0.0949 0.028 Uiso d . 1 . . H
  C25 0.8648(2) 0.83044(14) -0.03123(6) 0.0214(3) Uani d . 1 . . C
  H25 0.7612 0.8000 -0.0180 0.023 Uiso d . 1 . . H
  C26 0.9559(2) 0.74772(14) -0.06552(7) 0.0264(4) Uani d . 1 . . C
  H26A 0.9767 0.6810 -0.0441 0.036 Uiso d . 1 . . H
  H26B 0.8844 0.7267 -0.0965 0.021 Uiso d . 1 . . H
  H26C 1.0601 0.7831 -0.0803 0.024 Uiso d . 1 . . H
  O1W 0.76915(16) 0.55833(9) 0.01781(4) 0.0248(3) Uani d . 1 . . O
  H11W 0.8178 0.6009 0.0436 0.039 Uiso d . 1 . . H
  H12W 0.7727 0.4908 0.0316 0.036 Uiso d . 1 . . H
  O2W 0.90769(17) 0.70439(11) 0.09222(5) 0.0298(3) Uani d . 1 . . O
  H21W 0.9854 0.6979 0.1158 0.039 Uiso d . 1 . . H
  H22W 0.9372 0.7564 0.0690 0.035 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 0.0209(5) 0.0156(5) 0.0201(5) -0.0012(4) -0.0027(5) 0.0034(4)
  O2 0.0230(6) 0.0152(5) 0.0127(5) -0.0021(5) 0.0003(4) 0.0015(4)
  O3 0.0238(6) 0.0118(5) 0.0164(5) -0.0012(4) 0.0015(4) -0.0005(4)
  O4 0.0313(6) 0.0186(5) 0.0149(5) -0.0001(5) -0.0005(5) -0.0019(4)
  N1 0.0168(6) 0.0127(6) 0.0136(5) 0.0005(5) -0.0003(5) 0.0002(5)
  N2 0.0239(7) 0.0169(6) 0.0151(6) 0.0014(6) -0.0006(5) 0.0018(5)
  C1 0.0149(7) 0.0165(7) 0.0141(6) -0.0003(6) 0.0005(6) -0.0015(5)
  C2 0.0142(7) 0.0160(7) 0.0137(6) 0.0003(6) 0.0015(6) 0.0009(5)
  C3 0.0140(7) 0.0130(7) 0.0180(7) 0.0005(6) 0.0019(6) 0.0001(5)
  C4 0.0162(7) 0.0151(7) 0.0150(6) 0.0015(6) 0.0008(6) -0.0020(6)
  C5 0.0135(7) 0.0158(7) 0.0137(6) 0.0019(6) 0.0008(5) 0.0001(5)
  C6 0.0134(7) 0.0132(7) 0.0160(6) 0.0006(6) 0.0005(6) -0.0001(5)
  C7 0.0169(7) 0.0115(6) 0.0137(6) 0.0011(6) 0.0000(6) -0.0005(5)
  C8 0.0141(7) 0.0134(6) 0.0133(6) 0.0005(6) -0.0012(5) -0.0005(5)
  C9 0.0156(7) 0.0155(7) 0.0173(6) -0.0014(6) 0.0004(6) -0.0013(6)
  C10 0.0226(8) 0.0126(7) 0.0187(7) 0.0009(6) 0.0003(6) -0.0026(6)
  C11 0.0151(7) 0.0121(6) 0.0211(7) 0.0011(6) 0.0004(6) -0.0005(5)
  C12 0.0283(8) 0.0162(7) 0.0236(7) 0.0021(7) -0.0056(7) 0.0053(6)
  C13 0.0257(8) 0.0219(8) 0.0191(7) 0.0021(7) -0.0034(6) 0.0038(6)
  C14 0.0205(7) 0.0200(7) 0.0174(7) 0.0040(7) -0.0056(6) 0.0019(6)
  C15 0.0299(9) 0.0194(7) 0.0157(7) 0.0022(7) -0.0030(6) 0.0021(6)
  C16 0.0231(8) 0.0191(7) 0.0171(7) 0.0014(7) 0.0021(6) 0.0017(6)
  C17 0.0193(7) 0.0162(7) 0.0156(7) 0.0031(6) 0.0026(6) 0.0002(6)
  C18 0.0143(7) 0.0125(7) 0.0181(7) 0.0006(6) 0.0000(6) -0.0005(5)
  C19 0.0156(7) 0.0160(7) 0.0209(7) 0.0019(6) -0.0038(6) 0.0000(6)
  C20 0.0180(7) 0.0172(7) 0.0206(7) -0.0005(6) -0.0047(6) -0.0012(6)
  C21 0.0208(8) 0.0141(7) 0.0148(7) 0.0002(6) -0.0019(6) -0.0014(5)
  C22 0.0302(9) 0.0190(7) 0.0140(6) 0.0012(7) -0.0022(7) -0.0003(6)
  C23 0.0295(9) 0.0147(7) 0.0209(7) -0.0016(7) 0.0010(7) -0.0026(6)
  O5 0.0283(6) 0.0279(6) 0.0169(5) -0.0009(5) -0.0012(5) -0.0011(5)
  C24 0.0367(10) 0.0240(8) 0.0258(8) 0.0047(8) -0.0062(8) -0.0014(7)
  C25 0.0221(8) 0.0229(8) 0.0191(7) -0.0023(7) -0.0008(6) 0.0000(6)
  C26 0.0312(9) 0.0229(8) 0.0253(8) 0.0019(8) -0.0023(7) -0.0032(7)
  O1W 0.0331(7) 0.0204(6) 0.0208(5) -0.0005(5) -0.0020(5) 0.0037(5)
  O2W 0.0302(7) 0.0336(7) 0.0255(6) -0.0047(6) -0.0055(5) 0.0053(5)
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 . 1.4274(18) ?
  O1 C12 . 1.4411(19) ?
  O2 C2 . 1.3687(17) ?
  O2 C22 . 1.4337(18) ?
  O3 C3 . 1.3697(18) ?
  O3 C23 . 1.4279(18) ?
  O4 C9 . 1.2311(18) ?
  N1 C9 . 1.3605(19) ?
  N1 C6 . 1.4192(19) ?
  N1 C8 . 1.4884(17) ?
  N2 C15 . 1.483(2) ?
  N2 C16 . 1.488(2) ?
  N2 C21 . 1.4995(19) ?
  C1 C2 . 1.387(2) ?
  C1 C6 . 1.3947(19) ?
  C1 H1 . 0.9514 ?
  C2 C3 . 1.418(2) ?
  C3 C4 . 1.391(2) ?
  C4 C5 . 1.392(2) ?
  C4 H4 . 0.9842 ?
  C5 C6 . 1.387(2) ?
  C5 C7 . 1.5071(19) ?
  C7 C17 . 1.546(2) ?
  C7 C21 . 1.549(2) ?
  C7 C8 . 1.5587(19) ?
  C8 C18 . 1.528(2) ?
  C8 H8 . 0.9854 ?
  C9 C10 . 1.517(2) ?
  C10 C11 . 1.546(2) ?
  C10 H10A . 0.9497 ?
  C10 H10B . 0.9688 ?
  C11 C18 . 1.537(2) ?
  C11 H11 . 0.9687 ?
  C12 C13 . 1.511(2) ?
  C12 H12A . 1.0091 ?
  C12 H12B . 0.9794 ?
  C13 C14 . 1.327(2) ?
  C13 H13 . 0.9549 ?
  C14 C15 . 1.509(2) ?
  C14 C19 . 1.524(2) ?
  C15 H15A . 1.0060 ?
  C15 H15B . 1.0207 ?
  C16 C17 . 1.524(2) ?
  C16 H16A . 0.9693 ?
  C16 H16B . 1.0013 ?
  C17 H17A . 0.9839 ?
  C17 H17B . 0.9698 ?
  C18 C19 . 1.537(2) ?
  C18 H18 . 1.0189 ?
  C19 C20 . 1.537(2) ?
  C19 H19 . 1.0004 ?
  C20 C21 . 1.523(2) ?
  C20 H20A . 0.9845 ?
  C20 H20B . 1.0040 ?
  C21 H21 . 0.9676 ?
  C22 H22A . 0.9810 ?
  C22 H22B . 0.9554 ?
  C22 H22C . 1.0005 ?
  C23 H23A . 0.9804 ?
  C23 H23B . 0.9505 ?
  C23 H23C . 1.0027 ?
  O5 C25 . 1.4441(19) ?
  O5 H5 . 0.8790 ?
  C24 C25 . 1.511(2) ?
  C24 H24A . 1.0016 ?
  C24 H24B . 1.0452 ?
  C24 H24C . 0.9832 ?
  C25 C26 . 1.519(2) ?
  C25 H25 . 0.9627 ?
  C26 H26A . 0.9969 ?
  C26 H26B . 0.9987 ?
  C26 H26C . 1.0051 ?
  O1W H11W . 0.9207 ?
  O1W H12W . 0.9024 ?
  O2W H21W . 0.8583 ?
  O2W H22W . 0.8977 ?
_cod_database_code 2014564