#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$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_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 '\w and \f' _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/[\s^2^(Fo^2^)+(0.0305P)^2^+3.5408P] where P=(Fo^2^+2Fc^2^)/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>2\s(I) _[local]_cod_data_source_file hj1079.cif _[local]_cod_data_source_block II _[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 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_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 ? 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_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) _cod_database_fobs_code 2014356 _journal_paper_doi 10.1107/S0108270105041235