#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/00/36/2003650.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_2003650 loop_ _publ_author_name 'Mague, J. T.' 'De, D.' 'Krogstad, D. J.' _publ_section_title ; An Intermediate for Chloroquine Analogs: (E)-2-(4,7-Dichloro-2-quinolinyl)-3-(dimethylamino)-2-propenal ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1423 _journal_page_last 1425 _journal_volume 51 _journal_year 1995 _chemical_compound_source 'see text' _chemical_formula_moiety 'C14 H12 Cl2 N2 O1' _chemical_formula_sum 'C14 H12 Cl2 N2 O' _chemical_formula_weight 295.17 _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_type_scat_source IntTabIV _cell_angle_alpha 97.84(1) _cell_angle_beta 104.36(1) _cell_angle_gamma 115.03(1) _cell_formula_units_Z 2 _cell_length_a 8.2796(9) _cell_length_b 8.644(1) _cell_length_c 11.336(1) _cell_measurement_reflns_used 23 _cell_measurement_temperature 293 _cell_measurement_theta_max 16.91 _cell_measurement_theta_min 11.01 _cell_volume 684.70(16) _computing_cell_refinement 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'MolEN (Fair, 1990)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_structure_refinement MolEN _computing_structure_solution ;SIR88 (Burla, Camalli, Cascarano, Giocavazzo, Polidori, Spagna & Veterbo, 1989) ; _diffrn_measurement_device 'Enraf-Nonius CAD4' _diffrn_measurement_method \w/2\q _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.018 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 2581 _diffrn_reflns_theta_max 25.0 _diffrn_standards_decay_% -1.8 _diffrn_standards_interval_time 120 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 0.46 _exptl_absorpt_correction_T_max 0.9988 _exptl_absorpt_correction_T_min 0.8987 _exptl_absorpt_correction_type empirical _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.43 _exptl_crystal_description 'triclinic prism' _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.17 _refine_diff_density_max 0.05 _refine_diff_density_min -0.19 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_obs 1.56 _refine_ls_hydrogen_treatment 'H atoms refined isotropically' _refine_ls_number_parameters 220 _refine_ls_number_reflns 1567 _refine_ls_R_factor_obs 0.038 _refine_ls_shift/esd_max 0.05 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme 1/\s^2^(F) _refine_ls_wR_factor_obs 0.049 _reflns_number_observed 1567 _reflns_number_total 2389 _reflns_observed_criterion >2\s(I) _[local]_cod_data_source_file cr1173.cif _[local]_cod_data_source_block cr1173a _[local]_cod_chemical_formula_sum_orig 'C14 H12 Cl2 N2 O1' _cod_original_cell_volume 684.7(2) _cod_database_code 2003650 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_B_iso_or_equiv Cl(1) .8660(1) .11070(9) .90276(8) 5.47(2) Cl(2) .2690(1) -.4944(1) 1.15541(7) 6.59(2) O .2894(3) -.0432(2) .5232(2) 5.51(6) N(1) .2823(2) -.3673(2) .7351(2) 3.07(5) N(2) .1830(3) -.6411(2) .4559(2) 3.48(5) C(1) .3795(3) -.3151(3) .8621(2) 3.15(6) C(2) .2911(3) -.4167(3) .9369(2) 3.83(7) C(3) .3795(4) -.3694(3) 1.0639(2) 4.16(7) C(4) .5585(4) -.2198(4) 1.1235(3) 4.83(8) C(5) .6465(4) -.1231(3) 1.0535(3) 4.38(7) C(6) .5621(3) -.1658(3) .9213(2) 3.22(6) C(7) .6409(3) -.0712(3) .8402(3) 3.44(6) C(8) .5458(3) -.1209(3) .7147(2) 3.28(6) C(9) .3644(3) -.2733(3) .6635(2) 2.81(5) C(10) .2586(3) -.3275(3) .5265(2) 2.99(5) C(11) .2310(3) -.1989(3) .4704(3) 4.10(7) C(12) .1719(3) -.4958(3) .4451(2) 3.09(5) C(13) .3110(4) -.6496(3) .5651(3) 4.86(7) C(14) .0656(4) -.8036(4) .3523(3) 5.06(8) H(2) .172(3) -.519(3) .893(2) 4.4(6) H(4) .608(4) -.194(3) 1.209(2) 5.5(7) H(5) .766(4) -.026(3) 1.096(3) 6.4(8) H(8) .591(3) -.063(3) .657(2) 4.3(6) H(11) .148(3) -.251(3) .377(2) 5.5(7) H(12) .093(3) -.510(3) .361(2) 3.2(5) H(13a) .336(3) -.739(3) .548(2) 5.0(6) H(13b) .253(4) -.665(4) .626(3) 7.7(9) H(13c) .432(4) -.536(4) .597(3) 7.0(8) H(14a) -.000(5) -.782(5) .281(4) 11(1) H(14b) -.020(4) -.884(4) .374(3) 8.0(9) H(14c) .127(4) -.853(4) .328(3) 9(1) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C(9) C(10) C(11) 118.5(2) yes C(9) C(10) C(12) 126.7(2) yes C(11) C(10) C(12) 114.7(2) yes C(10) C(11) O 126.9(3) yes C(10) C(12) N(2) 132.6(2) yes C(12) N(2) C(13) 123.7(2) yes C(12) N(2) C(14) 119.6(3) yes C(13) N(2) C(14) 116.7(3) yes C(1) N(1) C(9) 118.0(2) no N(1) C(1) C(2) 117.4(2) no N(1) C(1) C(6) 123.5(2) no C(2) C(1) C(6) 119.1(2) no C(1) C(2) C(3) 120.0(3) no C(1) C(2) H(2) 116(2) no C(3) C(2) H(2) 124(2) no Cl(2) C(3) C(2) 119.7(3) no Cl(2) C(3) C(4) 119.1(2) no C(2) C(3) C(4) 121.2(3) no C(3) C(4) C(5) 119.7(3) no C(3) C(4) H(4) 116(2) no C(5) C(4) H(4) 124(2) no C(4) C(5) C(6) 121.7(3) no C(4) C(5) H(5) 118(2) no C(6) C(5) H(5) 121(2) no C(1) C(6) C(5) 118.2(3) no C(1) C(6) C(7) 115.8(2) no C(5) C(6) C(7) 126(3) no Cl(1) C(7) C(6) 119.4(2) no Cl(1) C(7) C(8) 119.3(2) no C(6) C(7) C(8) 121.3(2) no C(7) C(8) C(9) 119(3) no C(7) C(8) H(8) 125(2) no C(9) C(8) H(8) 116(2) no N(1) C(9) C(8) 122.4(2) no N(1) C(9) C(10) 118.2(2) no C(8) C(9) C(10) 119.4(2) no O C(11) H(11) 120(3) no C(10) C(11) H(11) 113(2) no N(2) C(12) H(12) 112(2) no C(10) C(12) H(12) 115(2) no N(2) C(13) H(13a) 113(2) no N(2) C(13) H(13b) 107(3) no N(2) C(13) H(13c) 109(2) no H(13a) C(13) H(13b) 109(3) no H(13a) C(13) H(13c) 109(3) no H(13b) C(13) H(13c) 110(3) no N(2) C(14) H(14a) 111(3) no N(2) C(14) H(14b) 111(3) no N(2) C(14) H(14c) 114(3) no H(14a) C(14) H(14b) 107(4) no H(14a) C(14) H(14c) 108(4) no H(14b) C(14) H(14c) 105(4) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C(9) C(10) 1.476(3) yes C(10) C(11) 1.425(4) yes C(11) O 1.220(4) yes C(10) C(12) 1.380(4) yes C(12) N(2) 1.318(3) yes C(13) N(2) 1.450(4) yes C(14) N(2) 1.458(4) yes Cl(1) C(7) 1.735(3) no Cl(2) C(3) 1.738(3) no N(1) C(1) 1.365(3) no N(1) C(9) 1.329(3) no C(1) C(2) 1.411(4) no C(1) C(6) 1.418(4) no C(2) C(3) 1.356(4) no C(2) H(2) .95(3) no C(3) C(4) 1.403(5) no C(4) C(5) 1.346(5) no C(4) H(4) .91(3) no C(5) C(6) 1.409(4) no C(5) H(5) .93(4) no C(6) C(7) 1.410(4) no C(7) C(8) 1.349(4) no C(8) C(9) 1.419(4) no C(8) H(8) .93(3) no C(11) H(11) 1.02(3) no C(12) H(12) .97(3) no C(13) H(13a) .89(3) no C(13) H(13b) .93(4) no C(13) H(13c) 1.00(4) no C(14) H(14a) .94(5) no C(14) H(14b) .87(4) no C(14) H(14c) .86(5) no