#------------------------------------------------------------------------------ #$Date: 2018-10-05 13:19:55 +0100 (Fri, 05 Oct 2018) $ #$Revision: 211332 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/25/2012525.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_2012525 loop_ _publ_author_name 'Linden, Anthony' 'Awad, Enas M.' 'Elwan, Nehal M.' 'Hassaneen, Hamdi M.' 'Heimgartner, Heinz' _publ_section_title ;2-(4-Chlorophenyl)-1,3-dicyano-6,7-dihydro-4-imino-9,10-dimethoxybenzo[a]quinolizine--water (2/5) ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o122 _journal_page_last o124 _journal_paper_doi 10.1107/S010827010102090X _journal_volume 58 _journal_year 2002 _chemical_formula_iupac 'C23 H17 Cl N4 O2, 2.5H2 O' _chemical_formula_moiety 'C23 H17 Cl N4 O2, 2.5H2 O' _chemical_formula_sum 'C23 H22 Cl N4 O4.5' _chemical_formula_weight 461.90 _chemical_melting_point 495 _chemical_name_systematic ; 2-(4-chlorophenyl)-1,3-dicyano-6,7-dihydro-4-imino- 9,10-dimethoxybenzo[a]quinolizine-water (2/5) ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 94.566(18) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 17.4665(18) _cell_length_b 17.0031(16) _cell_length_c 7.347(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 173.0(10) _cell_measurement_theta_max 19.4 _cell_measurement_theta_min 17.8 _cell_volume 2175.0(9) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1991) ; _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1999)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2001)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 173.0(10) _diffrn_measured_fraction_theta_full .998 _diffrn_measured_fraction_theta_max .998 _diffrn_measurement_device_type 'Rigaku AFC-5R' _diffrn_measurement_method \w--2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Rigaku RU200 rotating-anode generator' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength .71069 _diffrn_reflns_av_R_equivalents .0335 _diffrn_reflns_av_sigmaI/netI .0772 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 5556 _diffrn_reflns_theta_full 27.5 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 2.6 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .217 _exptl_absorpt_correction_type none _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.410 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 964 _exptl_crystal_size_max .38 _exptl_crystal_size_mid .25 _exptl_crystal_size_min .20 _refine_diff_density_max .308 _refine_diff_density_min -.257 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref .967 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 277 _refine_ls_number_reflns 4982 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all .967 _refine_ls_R_factor_all .0990 _refine_ls_R_factor_gt .0511 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0795P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt .1383 _refine_ls_wR_factor_ref .1513 _reflns_number_gt 3141 _reflns_number_total 4982 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file sk1527.cif _cod_data_source_block IVa _cod_depositor_comments ; The following automatic conversions were performed: '_atom_sites_solution_hydrogens' value 'geom & difmap' was changed to 'mixed'. Automatic conversion script Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius ; _cod_original_cell_volume 2175.1(9) _cod_original_sg_symbol_H-M 'P 21/c' _cod_original_formula_sum 'C23 H22 Cl N4 O4.50' _cod_database_code 2012525 _cod_database_fobs_code 2012525 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 Cl 1.14227(3) -.07018(4) .77710(9) .03323(18) Uani d . 1 . . Cl O1 .54027(9) -.16805(9) .6463(3) .0282(4) Uani d . 1 . . O O2 .41839(9) -.09609(10) .7392(2) .0282(4) Uani d . 1 . . O N1 .68661(10) .15474(11) .6712(3) .0217(4) Uani d . 1 . . N N2 .73743(13) .27135(12) .5728(3) .0287(5) Uani d . 1 . . N H2 .7780(17) .2927(18) .553(4) .033(8) Uiso d . 1 . . H N3 .93636(13) .24227(13) .5427(4) .0367(6) Uani d . 1 . . N N4 .77546(13) -.08956(13) .9225(4) .0387(6) Uani d . 1 . . N C2 .75026(13) .20086(13) .6294(3) .0221(5) Uani d . 1 . . C C3 .82417(13) .16009(13) .6519(3) .0206(5) Uani d . 1 . . C C4 .83223(12) .08375(13) .7119(3) .0201(5) Uani d . 1 . . C C5 .76401(12) .04181(13) .7472(3) .0204(5) Uani d . 1 . . C C6 .69150(13) .07681(13) .7138(3) .0207(5) Uani d . 1 . . C C7 .61938(12) .03240(13) .7193(3) .0200(5) Uani d . 1 . . C C8 .61645(12) -.04838(13) .6777(3) .0214(5) Uani d . 1 . . C H8 .6611 -.0746 .6433 .026 Uiso calc R 1 . . H C9 .54894(13) -.08934(13) .6869(3) .0230(5) Uani d . 1 . . C C10 .48218(12) -.05017(14) .7347(3) .0223(5) Uani d . 1 . . C C11 .48465(13) .02980(14) .7689(3) .0230(5) Uani d . 1 . . C H11 .4394 .0564 .7978 .028 Uiso calc R 1 . . H C12 .55264(13) .07156(14) .7615(3) .0230(5) Uani d . 1 . . C C13 .55935(14) .15881(14) .7942(4) .0273(5) Uani d . 1 . . C H131 .5806 .1687 .9211 .033 Uiso calc R 1 . . H H132 .5078 .1833 .7778 .033 Uiso calc R 1 . . H C14 .61121(13) .19514(13) .6623(4) .0242(5) Uani d . 1 . . C H141 .5864 .1915 .5366 .029 Uiso calc R 1 . . H H142 .6190 .2515 .6921 .029 Uiso calc R 1 . . H C15 .88814(14) .20438(14) .5941(3) .0255(5) Uani d . 1 . . C C16 .90869(12) .04449(13) .7329(3) .0208(5) Uani d . 1 . . C C17 .97199(13) .08429(13) .8167(3) .0230(5) Uani d . 1 . . C H17 .9657 .1355 .8652 .028 Uiso calc R 1 . . H C18 1.04439(13) .04907(14) .8294(3) .0242(5) Uani d . 1 . . C H18 1.0878 .0762 .8841 .029 Uiso calc R 1 . . H C19 1.05174(13) -.02608(14) .7609(3) .0244(5) Uani d . 1 . . C C20 .98963(13) -.06739(14) .6794(3) .0262(5) Uani d . 1 . . C H20 .9959 -.1192 .6347 .031 Uiso calc R 1 . . H C21 .91809(13) -.03133(13) .6646(3) .0227(5) Uani d . 1 . . C H21 .8751 -.0585 .6075 .027 Uiso calc R 1 . . H C22 .77011(12) -.03215(14) .8407(3) .0254(5) Uani d . 1 . . C C23 .60612(15) -.20684(15) .5826(4) .0382(7) Uani d . 1 . . C H231 .6237 -.1779 .4784 .057 Uiso calc R 1 . . H H232 .5922 -.2606 .5449 .057 Uiso calc R 1 . . H H233 .6474 -.2085 .6811 .057 Uiso calc R 1 . . H C24 .34736(13) -.05812(15) .7727(4) .0304(6) Uani d . 1 . . C H241 .3528 -.0321 .8920 .046 Uiso calc R 1 . . H H242 .3063 -.0975 .7718 .046 Uiso calc R 1 . . H H243 .3346 -.0190 .6772 .046 Uiso calc R 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 Cl .0241(3) .0388(4) .0367(4) .0113(3) .0021(2) -.0003(3) O1 .0235(8) .0182(8) .0435(11) -.0026(7) .0067(7) -.0021(8) O2 .0203(8) .0260(9) .0391(10) -.0021(7) .0076(7) .0000(8) N1 .0201(9) .0194(10) .0250(10) .0011(7) -.0005(8) .0005(8) N2 .0281(11) .0200(10) .0378(13) -.0009(8) .0020(9) .0032(9) N3 .0321(12) .0277(12) .0513(15) -.0021(9) .0107(11) .0072(10) N4 .0309(12) .0318(12) .0517(16) -.0042(9) -.0066(11) .0164(11) C2 .0258(11) .0183(11) .0221(12) .0004(9) .0019(9) -.0009(9) C3 .0227(11) .0181(11) .0210(11) -.0019(9) .0020(9) -.0007(9) C4 .0205(11) .0216(11) .0184(11) .0007(9) .0026(8) -.0020(9) C5 .0200(11) .0178(10) .0232(12) .0001(8) .0004(9) .0003(9) C6 .0239(11) .0197(11) .0185(11) -.0005(9) .0013(9) -.0009(9) C7 .0192(10) .0194(11) .0211(11) -.0002(8) -.0005(8) .0012(9) C8 .0174(10) .0222(11) .0238(12) .0020(8) -.0025(9) .0016(9) C9 .0250(12) .0180(11) .0255(12) -.0006(9) -.0011(10) .0001(9) C10 .0185(11) .0267(12) .0215(11) -.0025(9) .0002(9) .0034(9) C11 .0195(11) .0261(12) .0233(12) .0028(9) .0019(9) -.0014(9) C12 .0233(11) .0238(12) .0215(11) .0010(9) -.0013(9) .0000(9) C13 .0258(12) .0235(12) .0327(14) .0038(10) .0026(10) -.0046(10) C14 .0231(11) .0146(10) .0343(13) .0035(9) -.0021(10) .0003(10) C15 .0286(12) .0193(11) .0287(13) .0034(9) .0030(10) .0019(10) C16 .0187(10) .0208(11) .0231(11) -.0001(8) .0021(9) .0015(9) C17 .0246(11) .0214(12) .0232(12) .0012(9) .0024(9) .0002(9) C18 .0203(11) .0269(12) .0255(12) -.0016(9) .0026(9) .0006(10) C19 .0208(11) .0307(13) .0219(12) .0053(10) .0038(9) .0043(10) C20 .0289(12) .0222(11) .0281(13) .0030(10) .0058(10) .0006(10) C21 .0199(11) .0215(11) .0265(12) -.0007(9) .0010(9) -.0007(9) C22 .0171(11) .0270(13) .0318(13) -.0024(9) -.0001(9) .0022(11) C23 .0338(14) .0203(12) .063(2) -.0026(11) .0173(13) -.0068(12) C24 .0204(11) .0332(14) .0382(15) .0009(10) .0068(10) .0029(11) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; H H .0000 .0000 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; Cl Cl .1484 .1585 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; N N .0061 .0033 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; O O .0106 .0060 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 0 -2 -1 1 -2 2 -1 -2 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C9 O1 C23 116.10(18) C10 O2 C24 117.73(19) C6 N1 C2 123.59(19) C6 N1 C14 119.99(18) C2 N1 C14 116.40(18) C2 N2 H2 110(2) N2 C2 N1 117.9(2) N2 C2 C3 127.5(2) N1 C2 C3 114.50(19) C4 C3 C15 121.8(2) C4 C3 C2 123.4(2) C15 C3 C2 114.68(19) C3 C4 C5 117.6(2) C3 C4 C16 121.6(2) C5 C4 C16 120.7(2) C6 C5 C4 120.7(2) C6 C5 C22 119.2(2) C4 C5 C22 119.56(19) N1 C6 C5 119.5(2) N1 C6 C7 117.84(19) C5 C6 C7 122.7(2) C12 C7 C8 119.8(2) C12 C7 C6 119.5(2) C8 C7 C6 120.8(2) C9 C8 C7 120.0(2) C9 C8 H8 120.0 C7 C8 H8 120.0 C8 C9 O1 124.1(2) C8 C9 C10 120.1(2) O1 C9 C10 115.72(19) O2 C10 C11 124.9(2) O2 C10 C9 115.4(2) C11 C10 C9 119.7(2) C10 C11 C12 120.7(2) C10 C11 H11 119.7 C12 C11 H11 119.7 C11 C12 C7 119.7(2) C11 C12 C13 123.6(2) C7 C12 C13 116.7(2) C12 C13 C14 110.1(2) C12 C13 H131 109.6 C14 C13 H131 109.6 C12 C13 H132 109.6 C14 C13 H132 109.6 H131 C13 H132 108.2 N1 C14 C13 111.01(19) N1 C14 H141 109.4 C13 C14 H141 109.4 N1 C14 H142 109.4 C13 C14 H142 109.4 H141 C14 H142 108.0 N3 C15 C3 176.3(3) C17 C16 C21 119.6(2) C17 C16 C4 120.0(2) C21 C16 C4 120.4(2) C18 C17 C16 120.2(2) C18 C17 H17 119.9 C16 C17 H17 119.9 C19 C18 C17 118.8(2) C19 C18 H18 120.6 C17 C18 H18 120.6 C18 C19 C20 122.2(2) C18 C19 Cl 118.80(18) C20 C19 Cl 119.01(19) C19 C20 C21 118.6(2) C19 C20 H20 120.7 C21 C20 H20 120.7 C20 C21 C16 120.7(2) C20 C21 H21 119.7 C16 C21 H21 119.7 N4 C22 C5 177.0(3) O1 C23 H231 109.5 O1 C23 H232 109.5 H231 C23 H232 109.5 O1 C23 H233 109.5 H231 C23 H233 109.5 H232 C23 H233 109.5 O2 C24 H241 109.5 O2 C24 H242 109.5 H241 C24 H242 109.5 O2 C24 H243 109.5 H241 C24 H243 109.5 H242 C24 H243 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 Cl C19 . 1.746(2) ? O1 C9 . 1.377(3) ? O1 C23 . 1.436(3) ? O2 C10 . 1.363(3) ? O2 C24 . 1.437(3) ? N1 C6 . 1.363(3) yes N1 C2 . 1.414(3) yes N1 C14 . 1.482(3) yes N2 C2 . 1.283(3) yes N2 H2 . .82(3) ? N3 C15 . 1.148(3) ? N4 C22 . 1.146(3) ? C2 C3 . 1.463(3) yes C3 C4 . 1.374(3) yes C3 C15 . 1.439(3) ? C4 C5 . 1.430(3) yes C4 C16 . 1.490(3) ? C5 C6 . 1.403(3) yes C5 C22 . 1.433(3) ? C6 C7 . 1.472(3) ? C7 C12 . 1.399(3) ? C7 C8 . 1.407(3) ? C8 C9 . 1.376(3) ? C8 H8 . .95 ? C9 C10 . 1.411(3) ? C10 C11 . 1.383(3) ? C11 C12 . 1.388(3) ? C11 H11 . .95 ? C12 C13 . 1.506(3) ? C13 C14 . 1.510(3) ? C13 H131 . .99 ? C13 H132 . .99 ? C14 H141 . .99 ? C14 H142 . .99 ? C16 C17 . 1.397(3) ? C16 C21 . 1.398(3) ? C17 C18 . 1.396(3) ? C17 H17 . .95 ? C18 C19 . 1.383(3) ? C18 H18 . .95 ? C19 C20 . 1.388(3) ? C20 C21 . 1.388(3) ? C20 H20 . .95 ? C21 H21 . .95 ? C23 H231 . .98 ? C23 H232 . .98 ? C23 H233 . .98 ? C24 H241 . .98 ? C24 H242 . .98 ? C24 H243 . .98 ? 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 C6 N1 C2 N2 172.8(2) C14 N1 C2 N2 -5.7(3) C6 N1 C2 C3 -5.4(3) C14 N1 C2 C3 176.06(19) N2 C2 C3 C4 -179.2(2) N1 C2 C3 C4 -1.2(3) N2 C2 C3 C15 -3.3(4) N1 C2 C3 C15 174.7(2) C15 C3 C4 C5 -173.3(2) C2 C3 C4 C5 2.4(3) C15 C3 C4 C16 4.4(3) C2 C3 C4 C16 -180.0(2) C3 C4 C5 C6 2.7(3) C16 C4 C5 C6 -175.0(2) C3 C4 C5 C22 -168.7(2) C16 C4 C5 C22 13.6(3) C2 N1 C6 C5 10.5(3) C14 N1 C6 C5 -171.0(2) C2 N1 C6 C7 -168.4(2) C14 N1 C6 C7 10.2(3) C4 C5 C6 N1 -8.9(3) C22 C5 C6 N1 162.5(2) C4 C5 C6 C7 169.8(2) C22 C5 C6 C7 -18.8(3) N1 C6 C7 C12 -28.0(3) C5 C6 C7 C12 153.2(2) N1 C6 C7 C8 150.3(2) C5 C6 C7 C8 -28.5(3) C12 C7 C8 C9 -3.0(3) C6 C7 C8 C9 178.7(2) C7 C8 C9 O1 179.0(2) C7 C8 C9 C10 1.2(3) C23 O1 C9 C8 -3.0(3) C23 O1 C9 C10 174.9(2) C24 O2 C10 C11 3.4(3) C24 O2 C10 C9 -175.1(2) C8 C9 C10 O2 179.8(2) O1 C9 C10 O2 1.7(3) C8 C9 C10 C11 1.2(3) O1 C9 C10 C11 -176.8(2) O2 C10 C11 C12 179.8(2) C9 C10 C11 C12 -1.8(3) C10 C11 C12 C7 -.1(3) C10 C11 C12 C13 179.0(2) C8 C7 C12 C11 2.5(3) C6 C7 C12 C11 -179.2(2) C8 C7 C12 C13 -176.7(2) C6 C7 C12 C13 1.6(3) C11 C12 C13 C14 -140.4(2) C7 C12 C13 C14 38.7(3) C6 N1 C14 C13 30.8(3) C2 N1 C14 C13 -150.6(2) C12 C13 C14 N1 -54.0(3) C3 C4 C16 C17 45.0(3) C5 C4 C16 C17 -137.4(2) C3 C4 C16 C21 -133.2(2) C5 C4 C16 C21 44.4(3) C21 C16 C17 C18 1.1(3) C4 C16 C17 C18 -177.2(2) C16 C17 C18 C19 -1.2(3) C17 C18 C19 C20 .3(4) C17 C18 C19 Cl -179.90(18) C18 C19 C20 C21 .8(4) Cl C19 C20 C21 -179.02(18) C19 C20 C21 C16 -1.0(4) C17 C16 C21 C20 .0(4) C4 C16 C21 C20 178.3(2) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21134956