#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/11/2011192.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_2011192 loop_ _publ_author_name 'Vladimir N. Nesterov' 'Tatiana V. Timofeeva' 'Oleg Ya. Borbulevych' 'Mikhail Yu. Antipin' 'Ronald D. Clark' _publ_section_title ; A combinatorial chemistry approach to new materials for non-linear optics. I. Five Schiff bases ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 971 _journal_page_last 975 _journal_paper_doi 10.1107/S0108270100002845 _journal_volume 56 _journal_year 2000 _chemical_formula_sum 'C17 H17 N3 O2' _chemical_formula_weight 295.34 _chemical_melting_point 195.0(10) _chemical_name_systematic ; N-{(E,2E)-3-[4-(dimethylamino)phenyl]-2-propenylidene}-4-nitroaniline ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _audit_creation_method SHELXL _cell_angle_alpha 90.70(3) _cell_angle_beta 100.10(3) _cell_angle_gamma 91.37(3) _cell_formula_units_Z 2 _cell_length_a 6.1650(12) _cell_length_b 7.2730(15) _cell_length_c 17.158(3) _cell_measurement_reflns_used 24 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 11 _cell_measurement_theta_min 10 _cell_volume 757.1(3) _computing_cell_refinement 'CAD4 Software' _computing_data_collection 'CAD4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'PROFIT (Streltsov & Zavodnik, 1989)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL-Plus (Sheldrick, 1994)' _diffrn_ambient_temperature 298(2) _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0309 _diffrn_reflns_av_sigmaI/netI .1093 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 4620 _diffrn_reflns_theta_max 28.96 _diffrn_reflns_theta_min 1.21 _diffrn_standards_decay_% 5 _diffrn_standards_interval_count 98 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu .087 _exptl_absorpt_correction_type none _exptl_crystal_colour 'dark yellow' _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'square prism' _exptl_crystal_F_000 312 _exptl_crystal_size_max .40 _exptl_crystal_size_mid .20 _exptl_crystal_size_min .20 _refine_diff_density_max .16 _refine_diff_density_min -.17 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all .988 _refine_ls_goodness_of_fit_ref 1.224 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 267 _refine_ls_number_reflns 3955 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.495 _refine_ls_restrained_S_obs 1.224 _refine_ls_R_factor_all .2117 _refine_ls_R_factor_gt .0621 _refine_ls_shift/esd_mean .000 _refine_ls_shift/su_max .001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0454P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all .2208 _refine_ls_wR_factor_ref .1069 _reflns_number_gt 1534 _reflns_number_total 4007 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bm1393.cif _cod_data_source_block 2b _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0454P)^2^] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0454P)^2^] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M P-1 _cod_database_code 2011192 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 N1 .0461(14) .0521(14) .0426(13) -.0002(11) .0149(11) .0024(10) N2 .079(2) .066(2) .0423(15) .0064(15) .0242(14) .0021(13) N3 .061(2) .060(2) .0397(13) .0056(12) .0199(12) .0030(11) O1 .107(2) .130(2) .0473(13) -.012(2) .0175(13) -.0180(13) O2 .128(2) .141(2) .073(2) -.046(2) .063(2) -.0086(14) C1 .039(2) .041(2) .0409(15) .0038(12) .0117(12) .0024(12) C2 .046(2) .043(2) .050(2) -.0074(13) .0124(14) -.0010(12) C3 .051(2) .050(2) .042(2) -.0041(14) .0075(14) -.0047(13) C4 .055(2) .042(2) .0351(15) .0067(13) .0157(13) .0042(12) C5 .047(2) .048(2) .047(2) -.0030(14) .0164(14) .0039(13) C6 .041(2) .047(2) .042(2) -.0023(13) .0062(13) -.0050(12) C7 .042(2) .050(2) .041(2) -.0002(13) .0094(13) .0010(12) C8 .048(2) .056(2) .037(2) -.0062(14) .0094(14) .0009(12) C9 .050(2) .049(2) .039(2) -.0003(14) .0100(14) .0022(12) C10 .036(2) .0402(15) .0365(14) -.0058(12) .0091(12) .0002(11) C11 .036(2) .048(2) .042(2) -.0027(13) .0044(13) .0053(12) C12 .038(2) .047(2) .044(2) .0065(13) .0115(13) .0040(12) C13 .044(2) .0368(15) .043(2) -.0057(12) .0125(13) .0003(11) C14 .045(2) .045(2) .039(2) .0027(13) .0070(13) .0065(12) C15 .036(2) .050(2) .047(2) .0062(13) .0132(13) .0039(12) C16 .094(3) .096(3) .039(2) .026(3) .015(2) .010(2) C17 .082(3) .114(4) .049(2) .027(2) .033(2) -.002(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_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol N1 .4643(4) .7254(3) -.06229(12) .0461(6) Uani d . 1 . N N2 .6366(5) .7422(3) -.37293(14) .0606(7) Uani d . 1 . N N3 -.1100(4) .7689(3) .37508(12) .0522(6) Uani d . 1 . N O1 .5158(4) .6588(4) -.42520(13) .0946(8) Uani d . 1 . O O2 .8034(5) .8222(4) -.38343(13) .1092(10) Uani d . 1 . O C1 .4906(4) .7336(3) -.14213(14) .0396(6) Uani d . 1 . C C2 .3502(5) .6457(4) -.2042(2) .0459(7) Uani d . 1 . C H2 .230(4) .577(3) -.1945(13) .053(8) Uiso d . 1 . H C3 .3962(5) .6488(4) -.2798(2) .0479(7) Uani d . 1 . C H3 .296(4) .584(3) -.3235(14) .054(7) Uiso d . 1 . H C4 .5828(4) .7427(3) -.29287(14) .0429(6) Uani d . 1 . C C5 .7240(5) .8345(4) -.2330(2) .0463(7) Uani d . 1 . C H5 .850(4) .898(3) -.2441(14) .066(9) Uiso d . 1 . H C6 .6765(4) .8284(3) -.1582(2) .0435(7) Uani d . 1 . C H6 .769(3) .894(3) -.1145(13) .034(6) Uiso d . 1 . H C7 .2721(5) .7256(4) -.0446(2) .0444(6) Uani d . 1 . C H7 .132(4) .734(3) -.0862(14) .056(8) Uiso d . 1 . H C8 .2390(5) .7133(4) .0362(2) .0467(7) Uani d . 1 . C H8 .368(4) .691(3) .0730(15) .062(9) Uiso d . 1 . H C9 .0466(5) .7398(4) .0594(2) .0457(7) Uani d . 1 . C H9 -.072(5) .773(4) .0230(15) .066(9) Uiso d . 1 . H C10 .0072(4) .7428(3) .14075(13) .0373(6) Uani d . 1 . C C11 -.1818(4) .8220(3) .1591(2) .0423(7) Uani d . 1 . C H11 -.282(4) .866(3) .1153(13) .043(7) Uiso d . 1 . H C12 -.2200(5) .8351(4) .23552(15) .0423(6) Uani d . 1 . C H12 -.349(4) .893(3) .2450(12) .038(6) Uiso d . 1 . H C13 -.0720(4) .7641(3) .29870(15) .0407(6) Uani d . 1 . C C14 .1183(5) .6836(4) .2800(2) .0428(6) Uani d . 1 . C H14 .229(4) .633(3) .3219(14) .049(7) Uiso d . 1 . H C15 .1558(4) .6747(4) .2037(2) .0438(7) Uani d . 1 . C H15 .288(4) .622(3) .1942(13) .045(7) Uiso d . 1 . H C16 .0616(7) .7185(7) .4404(2) .0754(11) Uani d . 1 . C H16A .012(5) .731(4) .490(2) .105(12) Uiso d . 1 . H H16B .198(7) .791(6) .440(2) .16(2) Uiso d . 1 . H H16C .102(5) .590(5) .4342(18) .098(12) Uiso d . 1 . H C17 -.2927(7) .8689(7) .3950(2) .0786(11) Uani d . 1 . C H17A -.316(6) .848(5) .446(2) .122(14) Uiso d . 1 . H H17B -.433(7) .837(5) .359(2) .144(18) Uiso d . 1 . H H17C -.259(7) 1.005(6) .392(3) .17(2) Uiso 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 .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .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 _geom_angle_publ_flag C7 N1 C1 120.1(2) no O1 N2 O2 122.6(3) no O1 N2 C4 118.8(3) no O2 N2 C4 118.6(3) no C13 N3 C17 120.5(3) no C13 N3 C16 120.4(3) no C17 N3 C16 117.0(3) no C2 C1 C6 118.7(2) no C2 C1 N1 124.1(2) no C6 C1 N1 117.1(2) no C3 C2 C1 120.6(3) no C4 C3 C2 118.7(3) no C3 C4 C5 122.3(2) no C3 C4 N2 119.1(3) no C5 C4 N2 118.6(3) no C6 C5 C4 118.1(3) no C5 C6 C1 121.6(3) no N1 C7 C8 121.6(3) no C9 C8 C7 124.1(3) no C8 C9 C10 126.4(3) no C15 C10 C11 116.8(2) no C15 C10 C9 122.8(3) no C11 C10 C9 120.3(3) no C12 C11 C10 122.1(3) no C11 C12 C13 121.1(3) no N3 C13 C12 122.3(2) no N3 C13 C14 121.0(2) no C12 C13 C14 116.7(2) no C15 C14 C13 121.5(3) no C14 C15 C10 121.8(3) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 C7 . . 1.274(3) no N1 C1 . . 1.409(3) no N2 O1 . . 1.208(3) no N2 O2 . . 1.211(3) no N2 C4 . . 1.469(3) no N3 C13 . . 1.372(3) no N3 C17 . . 1.443(4) no N3 C16 . . 1.457(4) no C1 C2 . . 1.387(3) no C1 C6 . . 1.394(3) no C2 C3 . . 1.377(4) no C2 H2 . . .93(2) no C3 C4 . . 1.377(3) no C3 H3 . . .99(2) no C4 C5 . . 1.378(3) no C5 C6 . . 1.366(3) no C5 H5 . . .95(2) no C6 H6 . . .97(2) no C7 C8 . . 1.439(4) no C7 H7 . . 1.02(2) no C8 C9 . . 1.333(4) no C8 H8 . . .95(3) no C9 C10 . . 1.459(3) no C9 H9 . . .91(3) no C10 C15 . . 1.392(3) no C10 C11 . . 1.394(3) no C11 C12 . . 1.375(3) no C11 H11 . . .95(2) no C12 C13 . . 1.401(3) no C12 H12 . . .95(2) no C13 C14 . . 1.408(3) no C14 C15 . . 1.370(4) no C14 H14 . . .98(2) no C15 H15 . . .95(2) no C16 H16A . . .96(3) no C16 H16B . . .98(4) no C16 H16C . . .98(4) no C17 H17A . . .92(4) no C17 H17B . . .99(4) no C17 H17C . . 1.01(4) no 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 _geom_torsion_publ_flag C7 N1 C1 C2 -37.3(4) no C7 N1 C1 C6 146.2(2) no C6 C1 C2 C3 1.4(4) no N1 C1 C2 C3 -175.1(3) no C1 C2 C3 C4 -.8(4) no C2 C3 C4 C5 -.4(4) no C2 C3 C4 N2 178.2(2) no O1 N2 C4 C3 -.2(4) no O2 N2 C4 C3 -178.6(3) no O1 N2 C4 C5 178.5(3) no O2 N2 C4 C5 .2(4) no C3 C4 C5 C6 1.0(4) no N2 C4 C5 C6 -177.6(2) no C4 C5 C6 C1 -.4(4) no C2 C1 C6 C5 -.8(4) no N1 C1 C6 C5 175.9(2) no C1 N1 C7 C8 178.6(2) no N1 C7 C8 C9 169.7(3) no C7 C8 C9 C10 -175.0(2) no C8 C9 C10 C15 -16.0(4) no C8 C9 C10 C11 161.7(3) no C15 C10 C11 C12 .8(4) no C9 C10 C11 C12 -177.0(2) no C10 C11 C12 C13 -1.8(4) no C17 N3 C13 C12 -7.8(4) no C16 N3 C13 C12 -171.0(3) no C17 N3 C13 C14 173.3(3) no C16 N3 C13 C14 10.2(4) no C11 C12 C13 N3 -177.4(2) no C11 C12 C13 C14 1.5(3) no N3 C13 C14 C15 178.7(2) no C12 C13 C14 C15 -.3(4) no C13 C14 C15 C10 -.7(4) no C11 C10 C15 C14 .4(4) no C9 C10 C15 C14 178.2(3) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 12195289