data_2014562
_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'
_chemical_formula_moiety  'C23 H26 N2 O4'
_chemical_formula_sum  'C23 H26 N2 O4'
_chemical_formula_iupac  'C23 H26 N2 O4'
_chemical_formula_weight  394.46
_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  7.992(2)
_cell_length_b  12.704(3)
_cell_length_c  9.471(2)
_cell_angle_alpha  90.00
_cell_angle_beta  99.68(3)
_cell_angle_gamma  90.00
_cell_volume  947.9(4)
_cell_formula_units_Z  2
_cell_measurement_temperature  100(2)
_exptl_crystal_density_diffrn  1.382
_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 0.7195(2) -0.09506(15) 0.8236(2) 0.0240(4) Uani d . 1 . . O
  O2 0.8858(2) 0.49240(14) 1.28786(17) 0.0191(4) Uani d . 1 . . O
  O3 0.7917(2) 0.59245(15) 1.05067(18) 0.0208(4) Uani d . 1 . . O
  O4 0.8767(3) 0.09616(16) 1.24284(19) 0.0265(4) Uani d . 1 . . O
  N1 0.8383(3) 0.15842(18) 1.0145(2) 0.0185(5) Uani d . 1 . . N
  N2 0.6901(3) 0.22198(19) 0.5303(2) 0.0207(5) Uani d . 1 . . N
  C1 0.8688(3) 0.3218(2) 1.1709(3) 0.0186(5) Uani d . 1 . . C
  H1 0.9021 0.2805 1.2636 0.019 Uiso d . 1 . . H
  C2 0.8541(3) 0.4302(2) 1.1673(3) 0.0168(5) Uani d . 1 . . C
  C3 0.8060(3) 0.4855(2) 1.0380(3) 0.0164(5) Uani d . 1 . . C
  C4 0.7749(3) 0.4305(2) 0.9092(3) 0.0189(5) Uani d . 1 . . C
  H4 0.7434 0.4711 0.8118 0.024 Uiso d . 1 . . H
  C5 0.7912(3) 0.3219(2) 0.9105(3) 0.0185(5) Uani d . 1 . . C
  C6 0.8362(3) 0.2687(2) 1.0396(3) 0.0167(5) Uani d . 1 . . C
  C7 0.7786(3) 0.24670(19) 0.7862(3) 0.0168(5) Uani d . 1 . . C
  C8 0.7768(3) 0.1374(2) 0.8604(3) 0.0185(5) Uani d . 1 . . C
  H8 0.8521 0.0866 0.8207 0.019 Uiso d . 1 . . H
  C9 0.8306(3) 0.0820(2) 1.1137(3) 0.0203(5) Uani d . 1 . . C
  C10 0.7635(4) -0.0242(2) 1.0566(3) 0.0241(6) Uani d . 1 . . C
  H10A 0.8593 -0.0713 1.0488 0.039 Uiso d . 1 . . H
  H10B 0.7140 -0.0591 1.1340 0.029 Uiso d . 1 . . H
  C11 0.6394(3) -0.0275(2) 0.9124(3) 0.0222(6) Uani d . 1 . . C
  H11 0.5328 -0.0617 0.9251 0.022 Uiso d . 1 . . H
  C12 0.6137(4) -0.1262(2) 0.6922(3) 0.0285(6) Uani d . 1 . . C
  H12A 0.4928 -0.1398 0.7131 0.044 Uiso d . 1 . . H
  H12B 0.6610 -0.1946 0.6694 0.034 Uiso d . 1 . . H
  C13 0.6174(4) -0.0484(2) 0.5742(3) 0.0245(6) Uani d . 1 . . C
  H13 0.6704 -0.0741 0.4906 0.031 Uiso d . 1 . . H
  C14 0.5669(3) 0.0509(2) 0.5798(3) 0.0226(6) Uani d . 1 . . C
  C15 0.5901(4) 0.1302(2) 0.4662(3) 0.0240(6) Uani d . 1 . . C
  H15A 0.4689 0.1582 0.4163 0.032 Uiso d . 1 . . H
  H15B 0.6559 0.1006 0.3949 0.017 Uiso d . 1 . . H
  C16 0.8719(3) 0.1943(2) 0.5708(3) 0.0209(5) Uani d . 1 . . C
  H16A 0.8893 0.1159 0.5914 0.019 Uiso d . 1 . . H
  H16B 0.9326 0.2080 0.4884 0.015 Uiso d . 1 . . H
  C17 0.9328(3) 0.2548(2) 0.7076(3) 0.0193(5) Uani d . 1 . . C
  H17A 0.9462 0.3322 0.6896 0.021 Uiso d . 1 . . H
  H17B 1.0386 0.2198 0.7629 0.019 Uiso d . 1 . . H
  C18 0.6052(3) 0.0832(2) 0.8523(3) 0.0200(5) Uani d . 1 . . C
  H18 0.5424 0.1229 0.9216 0.019 Uiso d . 1 . . H
  C19 0.4924(3) 0.0951(2) 0.7045(3) 0.0217(5) Uani d . 1 . . C
  H19 0.3798 0.0606 0.7125 0.023 Uiso d . 1 . . H
  C20 0.4640(3) 0.2143(2) 0.6826(3) 0.0218(5) Uani d . 1 . . C
  H20A 0.4235 0.2443 0.7700 0.025 Uiso d . 1 . . H
  H20B 0.3695 0.2265 0.5933 0.021 Uiso d . 1 . . H
  C21 0.6304(3) 0.2647(2) 0.6607(3) 0.0195(5) Uani d . 1 . . C
  H21A 0.6114 0.3445 0.6533 0.017 Uiso d . 1 . . H
  C22 0.9123(3) 0.4396(2) 1.4230(3) 0.0229(6) Uani d . 1 . . C
  H22A 0.8143 0.3922 1.4322 0.024 Uiso d . 1 . . H
  H22B 1.0188 0.4020 1.4335 0.019 Uiso d . 1 . . H
  H22C 0.9212 0.4956 1.5009 0.031 Uiso d . 1 . . H
  C23 0.7396(4) 0.6499(2) 0.9210(3) 0.0238(6) Uani d . 1 . . C
  H23A 0.8210 0.6387 0.8485 0.027 Uiso d . 1 . . H
  H23B 0.6216 0.6279 0.8722 0.020 Uiso d . 1 . . H
  H23C 0.7404 0.7291 0.9469 0.023 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 0.0279(10) 0.0186(10) 0.0244(10) 0.0013(8) 0.0015(8) -0.0005(8)
  O2 0.0269(9) 0.0153(9) 0.0150(8) 0.0000(8) 0.0026(7) 0.0001(7)
  O3 0.0292(10) 0.0138(9) 0.0190(9) 0.0010(8) 0.0026(7) 0.0032(7)
  O4 0.0400(11) 0.0223(10) 0.0176(9) 0.0014(9) 0.0059(8) 0.0009(8)
  N1 0.0222(11) 0.0162(11) 0.0171(10) -0.0006(9) 0.0030(8) -0.0001(9)
  N2 0.0251(11) 0.0187(11) 0.0172(10) -0.0003(9) 0.0005(8) -0.0023(9)
  C1 0.0200(12) 0.0191(13) 0.0170(12) -0.0009(10) 0.0033(9) 0.0026(10)
  C2 0.0153(12) 0.0195(13) 0.0155(12) -0.0025(10) 0.0021(9) -0.0014(10)
  C3 0.0194(12) 0.0120(12) 0.0185(12) -0.0003(10) 0.0051(9) 0.0032(10)
  C4 0.0203(13) 0.0173(13) 0.0187(12) -0.0011(10) 0.0020(10) 0.0029(10)
  C5 0.0202(13) 0.0178(13) 0.0177(12) 0.0000(10) 0.0035(10) -0.0007(10)
  C6 0.0174(11) 0.0133(13) 0.0192(13) 0.0002(9) 0.0027(9) 0.0013(10)
  C7 0.0203(12) 0.0125(12) 0.0171(12) -0.0003(10) 0.0017(9) 0.0009(10)
  C8 0.0208(13) 0.0183(13) 0.0156(12) -0.0009(10) 0.0010(9) 0.0027(10)
  C9 0.0223(13) 0.0194(14) 0.0207(12) 0.0038(11) 0.0078(10) 0.0038(11)
  C10 0.0328(14) 0.0153(14) 0.0234(13) -0.0015(12) 0.0028(11) 0.0047(11)
  C11 0.0209(13) 0.0197(14) 0.0269(13) -0.0028(11) 0.0065(10) 0.0036(11)
  C12 0.0384(16) 0.0183(14) 0.0258(14) -0.0064(13) -0.0030(12) -0.0019(12)
  C13 0.0292(14) 0.0204(14) 0.0222(13) -0.0028(11) 0.0000(10) -0.0009(11)
  C14 0.0222(13) 0.0201(14) 0.0230(13) -0.0024(11) -0.0031(10) 0.0004(11)
  C15 0.0301(14) 0.0190(14) 0.0212(13) -0.0020(11) -0.0007(10) -0.0021(11)
  C16 0.0261(13) 0.0207(14) 0.0158(12) 0.0001(11) 0.0035(10) 0.0000(10)
  C17 0.0236(12) 0.0174(12) 0.0171(12) 0.0005(11) 0.0042(9) 0.0022(10)
  C18 0.0202(12) 0.0181(13) 0.0213(12) 0.0003(11) 0.0026(9) -0.0007(11)
  C19 0.0208(12) 0.0187(14) 0.0247(13) 0.0009(11) 0.0007(10) -0.0001(11)
  C20 0.0222(13) 0.0187(13) 0.0236(13) 0.0032(11) 0.0015(10) 0.0011(11)
  C21 0.0219(12) 0.0176(13) 0.0185(12) 0.0008(10) 0.0019(10) -0.0009(10)
  C22 0.0276(14) 0.0236(14) 0.0170(12) -0.0024(11) 0.0018(10) 0.0024(11)
  C23 0.0319(14) 0.0184(13) 0.0203(13) 0.0038(12) 0.0019(10) 0.0047(11)
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 . 1.426(3) ?
  O1 C12 . 1.437(3) ?
  O2 C2 . 1.376(3) ?
  O2 C22 . 1.429(3) ?
  O3 C3 . 1.370(3) ?
  O3 C23 . 1.429(3) ?
  O4 C9 . 1.230(3) ?
  N1 C9 . 1.360(3) ?
  N1 C6 . 1.421(3) ?
  N1 C8 . 1.484(3) ?
  N2 C16 . 1.481(4) ?
  N2 C15 . 1.484(3) ?
  N2 C21 . 1.498(3) ?
  C1 C2 . 1.383(4) ?
  C1 C6 . 1.400(4) ?
  C1 H1 . 1.0190 ?
  C2 C3 . 1.408(3) ?
  C3 C4 . 1.392(4) ?
  C4 C5 . 1.386(4) ?
  C4 H4 . 1.0498 ?
  C5 C6 . 1.390(4) ?
  C5 C7 . 1.506(3) ?
  C7 C17 . 1.546(3) ?
  C7 C21 . 1.548(3) ?
  C7 C8 . 1.557(4) ?
  C8 C18 . 1.525(4) ?
  C8 H8 . 0.9975 ?
  C9 C10 . 1.517(4) ?
  C10 C11 . 1.548(4) ?
  C10 H10A . 0.9836 ?
  C10 H10B . 0.9942 ?
  C11 C18 . 1.525(4) ?
  C11 H11 . 0.9812 ?
  C12 C13 . 1.496(4) ?
  C12 H12A . 1.0334 ?
  C12 H12B . 0.9858 ?
  C13 C14 . 1.329(4) ?
  C13 H13 . 1.0132 ?
  C14 C15 . 1.508(4) ?
  C14 C19 . 1.517(4) ?
  C15 H15A . 1.0650 ?
  C15 H15B . 0.9978 ?
  C16 C17 . 1.515(4) ?
  C16 H16A . 1.0203 ?
  C16 H16B . 1.0006 ?
  C17 H17A . 1.0064 ?
  C17 H17B . 1.0191 ?
  C18 C19 . 1.540(3) ?
  C18 H18 . 1.0232 ?
  C19 C20 . 1.539(4) ?
  C19 H19 . 1.0151 ?
  C20 C21 . 1.521(4) ?
  C20 H20A . 1.0125 ?
  C20 H20B . 1.0464 ?
  C21 H21A . 1.0256 ?
  C22 H22A . 1.0037 ?
  C22 H22B . 0.9665 ?
  C22 H22C . 1.0188 ?
  C23 H23A . 1.0323 ?
  C23 H23B . 1.0172 ?
  C23 H23C . 1.0344 ?