#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/43/2014356.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
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_coeditor_code           HJ1079
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o53
_journal_page_last               o57
_journal_paper_doi               10.1107/S0108270105041235
_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)
_chemical_name_systematic
;
N-(7-bromoquinolin-4-yl)-N',N'-diethylethane-1,2-diamine dihydrate
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_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_reflns_used    8774
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.40
_cell_measurement_theta_min      1.59
_cell_volume                     3316.1(9)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997)'
_computing_data_reduction        DENZO
_computing_molecular_graphics    'POV-RAY (Cason, 2003)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0735
_diffrn_reflns_av_sigmaI/netI    0.0461
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            26586
_diffrn_reflns_theta_full        26.40
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    2.488
_exptl_absorpt_correction_T_max  0.7890
_exptl_absorpt_correction_T_min  0.7381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.509
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3403
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0305P)²+3.5408P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0701
_refine_ls_wR_factor_ref         0.0799
_reflns_number_gt                2470
_reflns_number_total             3403
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hj1079.cif
_cod_data_source_block           II
_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 

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 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2014356
_cod_database_fobs_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_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
H11W O1 H12W 114(3)
C2 N1 C10 116.3(2)
H21W O2 H22W 105(3)
N1 C2 C3 125.5(2)
N1 C2 H2 117.3
C3 C2 H2 117.3
C2 C3 C4 119.9(2)
C2 C3 H3 120.1
C4 C3 H3 120.1
N11 C4 C3 122.5(2)
N11 C4 C5 120.7(2)
C3 C4 C5 116.8(2)
C6 C5 C10 118.5(2)
C6 C5 C4 123.5(2)
C10 C5 C4 118.0(2)
C7 C6 C5 121.6(2)
C7 C6 H6 119.2
C5 C6 H6 119.2
C6 C7 C8 118.8(2)
C6 C7 H7 120.6
C8 C7 H7 120.6
C9 C8 C7 122.0(2)
C9 C8 Br1 119.25(19)
C7 C8 Br1 118.78(19)
C8 C9 C10 119.8(2)
C8 C9 H9 120.1
C10 C9 H9 120.1
N1 C10 C9 117.2(2)
N1 C10 C5 123.5(2)
C9 C10 C5 119.3(2)
C4 N11 C12 121.8(2)
C4 N11 H11 120.4(19)
C12 N11 H11 115.1(19)
N11 C12 C13 110.9(2)
N11 C12 H12A 109.4
C13 C12 H12A 109.4
N11 C12 H12B 109.4
C13 C12 H12B 109.4
H12A C12 H12B 108.0
N14 C13 C12 114.6(2)
N14 C13 H13A 108.6
C12 C13 H13A 108.6
N14 C13 H13B 108.6
C12 C13 H13B 108.6
H13A C13 H13B 107.6
C17 N14 C13 110.35(19)
C17 N14 C15 112.87(19)
C13 N14 C15 110.40(19)
N14 C15 C16 116.7(2)
N14 C15 H15A 108.1
C16 C15 H15A 108.1
N14 C15 H15B 108.1
C16 C15 H15B 108.1
H15A C15 H15B 107.3
C15 C16 H16C 109.5
C15 C16 H16A 109.5
H16C C16 H16A 109.5
C15 C16 H16B 109.5
H16C C16 H16B 109.5
H16A C16 H16B 109.5
N14 C17 C18 113.7(2)
N14 C17 H17A 108.8
C18 C17 H17A 108.8
N14 C17 H17B 108.8
C18 C17 H17B 108.8
H17A C17 H17B 107.7
C17 C18 H18A 109.5
C17 C18 H17C 109.5
H18A C18 H17C 109.5
C17 C18 H18B 109.5
H18A C18 H18B 109.5
H17C C18 H18B 109.5
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
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 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N11 H11 O1 . 0.84(2) 2.22(3) 3.038(3) 166(3) y
O1 H11W O2 4 0.93(3) 2.01(3) 2.924(3) 169(3) y
O1 H12W O2 . 0.79(3) 2.03(3) 2.824(3) 176(3) y
O2 H22W N1 6_575 0.88(3) 1.86(3) 2.722(3) 166(3) y
O2 H21W N14 4 0.84(3) 2.14(3) 2.977(3) 172(3) y
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C10 N1 C2 C3 0.6(3)
N1 C2 C3 C4 -0.7(4)
C2 C3 C4 N11 -178.6(2)
C2 C3 C4 C5 -0.2(3)
N11 C4 C5 C6 1.0(3)
C3 C4 C5 C6 -177.4(2)
N11 C4 C5 C10 179.4(2)
C3 C4 C5 C10 1.0(3)
C10 C5 C6 C7 0.8(3)
C4 C5 C6 C7 179.3(2)
C5 C6 C7 C8 1.1(3)
C6 C7 C8 C9 -1.8(4)
C6 C7 C8 Br1 179.21(18)
C7 C8 C9 C10 0.5(4)
Br1 C8 C9 C10 179.55(16)
C2 N1 C10 C9 179.8(2)
C2 N1 C10 C5 0.4(3)
C8 C9 C10 N1 -178.1(2)
C8 C9 C10 C5 1.4(3)
C6 C5 C10 N1 177.4(2)
C4 C5 C10 N1 -1.2(3)
C6 C5 C10 C9 -2.1(3)
C4 C5 C10 C9 179.4(2)
C3 C4 N11 C12 -2.6(3)
C5 C4 N11 C12 179.1(2)
C4 N11 C12 C13 -177.3(2)
N11 C12 C13 N14 -70.9(3)
C12 C13 N14 C17 -78.3(3)
C12 C13 N14 C15 156.2(2)
C17 N14 C15 C16 -56.2(3)
C13 N14 C15 C16 67.9(3)
C13 N14 C17 C18 176.5(2)
C15 N14 C17 C18 -59.5(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21133647
