#------------------------------------------------------------------------------
#$Date: 2011-09-17 23:27:16 +0300 (Sat, 17 Sep 2011) $
#$Revision: 26029 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2014356.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_2014356
loop_
_publ_author_name
'Bourne, Susan A.'
'De Villiers, Katherine'
'Egan, Timothy J.'
_publ_section_title
;
Three 4-aminoquinolines of antimalarial interest
;
_journal_name_full               'Acta Crystallographica, Section C'
_journal_page_first              o53
_journal_page_last               o57
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C15 H20 Br N3 , 2H2 O'
_chemical_formula_moiety         'C15 H20 Br N3 , 2H2 O'
_chemical_formula_sum            'C15 H24 Br N3 O2'
_chemical_formula_weight         358.28
_chemical_melting_point          340.5(5)
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 113.61(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   28.0177(4)
_cell_length_b                   6.8221(9)
_cell_length_c                   18.9339(4)
_cell_measurement_temperature    113(2)
_cell_volume                     3316.1(9)
_diffrn_ambient_temperature      113(2)
_exptl_crystal_density_diffrn    1.435
_[local]_cod_cif_authors_sg_H-M  'C 2/c'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '340-341' was changed to '340.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               2014356
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
Br1 0.059437(10) 0.97961(4) 0.340318(17) 0.03556(11) Uani d . 1 . . Br
O1 0.29418(8) 1.2080(3) 0.29291(12) 0.0275(4) Uani d D 1 . . O
N1 0.23553(8) 0.9821(3) 0.57984(11) 0.0219(5) Uani d . 1 . . N
O2 0.19338(7) 1.1306(3) 0.18035(11) 0.0258(4) Uani d D 1 . . O
C2 0.28697(10) 0.9862(3) 0.61193(14) 0.0221(5) Uani d . 1 . . C
H2 0.3032 0.9789 0.6666 0.027 Uiso calc R 1 . . H
C3 0.31936(10) 1.0004(3) 0.57244(14) 0.0211(5) Uani d . 1 . . C
H3 0.3561 1.0040 0.6001 0.025 Uiso calc R 1 . . H
C4 0.29786(9) 1.0094(3) 0.49231(14) 0.0188(5) Uani d . 1 . . C
C5 0.24186(9) 1.0027(3) 0.45438(13) 0.0180(5) Uani d . 1 . . C
C6 0.21440(9) 1.0026(3) 0.37340(14) 0.0203(5) Uani d . 1 . . C
H6 0.2334 1.0087 0.3416 0.024 Uiso calc R 1 . . H
C7 0.16129(10) 0.9940(3) 0.33976(14) 0.0221(5) Uani d . 1 . . C
H7 0.1434 0.9918 0.2852 0.027 Uiso calc R 1 . . H
C8 0.13353(9) 0.9883(3) 0.38726(14) 0.0223(5) Uani d . 1 . . C
C9 0.15807(9) 0.9859(3) 0.46556(14) 0.0211(5) Uani d . 1 . . C
H9 0.1383 0.9809 0.4962 0.025 Uiso calc R 1 . . H
C10 0.21297(9) 0.9908(3) 0.50103(14) 0.0183(5) Uani d . 1 . . C
N11 0.32747(8) 1.0191(3) 0.45075(12) 0.0207(5) Uani d D 1 . . N
H11 0.3144(10) 1.055(4) 0.4047(15) 0.025(8) Uiso d D 1 . . H
C12 0.38398(9) 1.0288(4) 0.48757(15) 0.0221(5) Uani d . 1 . . C
H12A 0.3976 0.9087 0.5184 0.026 Uiso calc R 1 . . H
H12B 0.3945 1.1426 0.5229 0.026 Uiso calc R 1 . . H
C13 0.40721(10) 1.0483(3) 0.42820(15) 0.0221(6) Uani d . 1 . . C
H13A 0.3895 1.1571 0.3928 0.027 Uiso calc R 1 . . H
H13B 0.4444 1.0841 0.4550 0.027 Uiso calc R 1 . . H
N14 0.40334(8) 0.8709(3) 0.38220(11) 0.0199(5) Uani d . 1 . . N
C15 0.40570(11) 0.9224(4) 0.30768(15) 0.0277(6) Uani d . 1 . . C
H15A 0.3785 1.0216 0.2820 0.033 Uiso calc R 1 . . H
H15B 0.3968 0.8039 0.2747 0.033 Uiso calc R 1 . . H
C16 0.45759(12) 1.0017(4) 0.31104(19) 0.0387(7) Uani d . 1 . . C
H16C 0.4684 1.1135 0.3464 0.058 Uiso calc R 1 . . H
H16A 0.4535 1.0439 0.2595 0.058 Uiso calc R 1 . . H
H16B 0.4841 0.8985 0.3294 0.058 Uiso calc R 1 . . H
C17 0.44336(10) 0.7282(4) 0.42671(15) 0.0256(6) Uani d . 1 . . C
H17A 0.4400 0.7018 0.4760 0.031 Uiso calc R 1 . . H
H17B 0.4782 0.7865 0.4391 0.031 Uiso calc R 1 . . H
C18 0.44002(11) 0.5357(4) 0.38517(18) 0.0322(6) Uani d . 1 . . C
H18A 0.4046 0.4829 0.3682 0.048 Uiso calc R 1 . . H
H17C 0.4648 0.4422 0.4202 0.048 Uiso calc R 1 . . H
H18B 0.4484 0.5574 0.3403 0.048 Uiso calc R 1 . . H
H11W 0.3026(11) 1.338(4) 0.3064(17) 0.047(9) Uiso d D 1 . . H
H12W 0.2655(11) 1.192(4) 0.2616(17) 0.040(10) Uiso d D 1 . . H
H21W 0.1678(11) 1.207(4) 0.1614(17) 0.045(10) Uiso d D 1 . . H
H22W 0.2038(12) 1.109(5) 0.1430(17) 0.049(10) Uiso d 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
Br1 0.01681(15) 0.0525(2) 0.03318(17) 0.00043(13) 0.00561(12) -0.00042(15)
O1 0.0272(12) 0.0288(12) 0.0230(11) 0.0006(9) 0.0063(10) -0.0012(9)
N1 0.0254(12) 0.0208(11) 0.0190(11) -0.0015(9) 0.0083(10) -0.0007(9)
O2 0.0218(11) 0.0341(11) 0.0215(11) 0.0064(9) 0.0087(9) 0.0024(8)
C2 0.0236(14) 0.0236(13) 0.0159(12) -0.0007(11) 0.0044(11) 0.0002(11)
C3 0.0191(13) 0.0209(13) 0.0196(13) -0.0012(10) 0.0040(11) 0.0000(11)
C4 0.0230(13) 0.0133(12) 0.0213(12) 0.0015(10) 0.0101(11) -0.0007(10)
C5 0.0185(12) 0.0149(12) 0.0185(12) -0.0008(10) 0.0051(10) -0.0008(10)
C6 0.0218(13) 0.0189(13) 0.0199(13) 0.0008(11) 0.0082(11) 0.0001(10)
C7 0.0237(14) 0.0227(14) 0.0185(13) 0.0011(11) 0.0068(11) 0.0001(11)
C8 0.0175(13) 0.0192(13) 0.0259(14) 0.0018(10) 0.0043(11) 0.0000(11)
C9 0.0217(13) 0.0192(13) 0.0250(14) -0.0012(10) 0.0121(12) 0.0004(11)
C10 0.0226(13) 0.0130(12) 0.0210(13) -0.0010(10) 0.0105(11) -0.0017(10)
N11 0.0175(11) 0.0273(12) 0.0157(11) 0.0001(9) 0.0049(9) 0.0008(10)
C12 0.0168(13) 0.0235(13) 0.0240(13) 0.0000(10) 0.0062(11) -0.0025(11)
C13 0.0161(13) 0.0211(13) 0.0272(14) -0.0015(10) 0.0065(12) -0.0012(11)
N14 0.0171(11) 0.0210(11) 0.0206(12) -0.0002(9) 0.0064(10) 0.0010(9)
C15 0.0293(16) 0.0304(15) 0.0241(15) 0.0018(12) 0.0116(13) 0.0013(12)
C16 0.0435(18) 0.0345(17) 0.0511(19) -0.0024(14) 0.0326(16) 0.0005(14)
C17 0.0213(15) 0.0254(14) 0.0270(15) 0.0004(11) 0.0063(13) 0.0013(11)
C18 0.0254(15) 0.0264(15) 0.0419(17) 0.0015(12) 0.0103(14) -0.0012(13)
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
Br1 C8 . 1.904(3) ?
O1 H11W . 0.93(3) ?
O1 H12W . 0.79(3) ?
N1 C2 . 1.321(3) ?
N1 C10 . 1.369(3) ?
O2 H21W . 0.84(3) ?
O2 H22W . 0.88(3) ?
C2 C3 . 1.391(3) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.392(3) ?
C3 H3 . 0.9500 ?
C4 N11 . 1.354(3) ?
C4 C5 . 1.441(3) ?
C5 C6 . 1.413(3) ?
C5 C10 . 1.419(3) ?
C6 C7 . 1.366(3) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.405(3) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.362(4) ?
C9 C10 . 1.411(3) ?
C9 H9 . 0.9500 ?
N11 C12 . 1.454(3) ?
N11 H11 . 0.84(2) ?
C12 C13 . 1.514(3) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 N14 . 1.470(3) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
N14 C17 . 1.469(3) ?
N14 C15 . 1.481(3) ?
C15 C16 . 1.529(4) ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 H16C . 0.9800 ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C17 C18 . 1.514(4) ?
C17 H17A . 0.9900 ?
C17 H17B . 0.9900 ?
C18 H18A . 0.9800 ?
C18 H17C . 0.9800 ?
C18 H18B . 0.9800 ?