#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/11/2011195.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_2011195 loop_ _publ_author_name 'Nesterov, Vladimir N.' 'Timofeeva, Tatiana V.' 'Antipin, Mikhail Yu.' 'Clark, Ronald D.' _publ_section_title ; A combinatorial chemistry approach to new materials for nonlinear optics. II. 4,4-Dimethylaminocinnamaldehyde and a molecular complex of 4-methoxycinnamaldehyde with 2,4-dinitroaniline ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 976 _journal_page_last 978 _journal_paper_doi 10.1107/S0108270100006351 _journal_volume 56 _journal_year 2000 _chemical_formula_sum 'C11 H13 N O' _chemical_formula_weight 175.22 _chemical_name_systematic 4,4-dimethylaminocinnamaldehyde _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 10.040(6) _cell_length_b 7.733(3) _cell_length_c 25.620(13) _cell_measurement_reflns_used 24 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 11 _cell_measurement_theta_min 10 _cell_volume 1989.1(17) _computing_cell_refinement 'P3/PC Diffractometer Program' _computing_data_collection 'P3/PC Diffractometer Program (Siemens, 1989)' _computing_data_reduction 'SHELXTL-Plus (Sheldrick, 1994)' _computing_molecular_graphics SHELXTL-Plus _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full .999 _diffrn_measured_fraction_theta_max .999 _diffrn_measurement_device_type 'Siemens P3/PC' _diffrn_measurement_method '\q/2\q scan' _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 .000 _diffrn_reflns_av_sigmaI/netI .047 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_number 1755 _diffrn_reflns_theta_full 25.05 _diffrn_reflns_theta_max 25.05 _diffrn_reflns_theta_min 1.59 _diffrn_standards_decay_% 5 _diffrn_standards_interval_count 98 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu .075 _exptl_absorpt_correction_type none _exptl_crystal_colour 'light green' _exptl_crystal_density_diffrn 1.170 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 752 _exptl_crystal_size_max .5 _exptl_crystal_size_mid .4 _exptl_crystal_size_min .1 _refine_diff_density_max .26 _refine_diff_density_min -.25 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.141 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 120 _refine_ls_number_reflns 1755 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.141 _refine_ls_R_factor_all .173 _refine_ls_R_factor_gt .123 _refine_ls_shift/su_max .014 _refine_ls_shift/su_mean .003 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.038P)^2^+5.11P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .257 _reflns_number_gt 1070 _reflns_number_total 1755 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bm1394.cif _cod_data_source_block b _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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 ; _cod_database_code 2011195 _cod_database_fobs_code 2011195 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' 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 O1 .8310(6) .2284(9) .07694(18) .132(2) Uani d . 1 . . O N1 .8845(5) .1833(7) .42486(17) .0711(14) Uani d . 1 . . N C1 .9056(5) .2802(6) .2636(2) .0563(14) Uani d . 1 . . C C2 .7997(5) .1853(7) .2850(2) .0586(14) Uani d . 1 . . C H2A .7336 .1433 .2630 .070 Uiso calc R 1 . . H C3 .7908(5) .1528(7) .3379(2) .0606(14) Uani d . 1 . . C H3A .7196 .0894 .3509 .073 Uiso calc R 1 . . H C4 .8901(6) .2157(7) .3722(2) .0590(14) Uani d . 1 . . C C5 .9951(5) .3109(7) .3507(2) .0634(15) Uani d . 1 . . C H5A 1.0620 .3529 .3723 .076 Uiso calc R 1 . . H C6 1.0006(6) .3431(7) .2979(2) .0613(15) Uani d . 1 . . C H6A 1.0704 .4092 .2849 .074 Uiso calc R 1 . . H C7 .9181(6) .3140(7) .2075(2) .0667(16) Uani d . 1 . . C H7A .9840 .3927 .1982 .080 Uiso calc R 1 . . H C8 .8492(6) .2487(8) .1683(2) .0660(15) Uani d . 1 . . C H8A .7778 .1756 .1752 .079 Uiso calc R 1 . . H C9 .8824(7) .2885(10) .1153(2) .091(2) Uani d . 1 . . C H9A .9503 .3685 .1101 .110 Uiso calc R 1 . . H C10 .9896(7) .2453(9) .4593(2) .091(2) Uani d . 1 . . C H10A .9977 .3685 .4559 .136 Uiso calc R 1 . . H H10B 1.0724 .1916 .4499 .136 Uiso calc R 1 . . H H10C .9680 .2167 .4948 .136 Uiso calc R 1 . . H C11 .7728(7) .0906(9) .4478(2) .088(2) Uani d . 1 . . C H11A .6911 .1470 .4384 .132 Uiso calc R 1 . . H H11B .7818 .0898 .4851 .132 Uiso calc R 1 . . H H11C .7719 -.0262 .4351 .132 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 O1 .140(5) .197(7) .059(3) -.004(5) -.005(3) .009(4) N1 .080(3) .076(3) .057(3) -.007(3) .009(3) -.004(2) C1 .061(3) .040(3) .068(3) -.003(3) .003(3) .000(2) C2 .057(3) .051(3) .068(3) .001(3) -.006(3) -.007(3) C3 .064(4) .053(3) .065(3) -.004(3) .008(3) .001(3) C4 .068(4) .047(3) .061(3) -.002(3) .002(3) -.009(3) C5 .059(3) .061(3) .071(4) -.009(3) -.006(3) -.012(3) C6 .064(3) .046(3) .074(4) -.008(3) .006(3) .000(3) C7 .078(4) .052(3) .070(4) .002(3) .001(3) .006(3) C8 .068(3) .071(4) .059(3) .002(3) -.005(3) .010(3) C9 .103(5) .108(6) .063(4) .013(5) .002(4) .021(4) C10 .101(5) .110(5) .062(4) -.005(5) -.015(4) -.012(4) C11 .120(6) .077(4) .067(4) -.012(4) .015(4) .008(3) 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_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C4 N1 C10 . . . 120.3(5) no C4 N1 C11 . . . 121.3(5) no C10 N1 C11 . . . 118.4(5) no C6 C1 C2 . . . 117.1(5) no C6 C1 C7 . . . 120.1(5) no C2 C1 C7 . . . 122.8(5) no C3 C2 C1 . . . 121.9(5) no C2 C3 C4 . . . 120.1(5) no N1 C4 C5 . . . 120.9(5) no N1 C4 C3 . . . 121.2(5) no C5 C4 C3 . . . 117.8(5) no C6 C5 C4 . . . 120.8(5) no C5 C6 C1 . . . 122.2(5) no C8 C7 C1 . . . 129.3(6) yes C7 C8 C9 . . . 121.2(6) yes O1 C9 C8 . . . 126.3(8) yes 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 O1 C9 . . 1.204(8) yes N1 C4 . . 1.374(6) yes N1 C10 . . 1.457(7) no N1 C11 . . 1.455(7) no C1 C6 . . 1.387(7) no C1 C2 . . 1.404(7) no C1 C7 . . 1.466(7) yes C2 C3 . . 1.379(7) no C3 C4 . . 1.415(7) no C4 C5 . . 1.399(7) no C5 C6 . . 1.375(7) no C7 C8 . . 1.320(7) yes C8 C9 . . 1.430(8) yes 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C6 C1 C2 C3 . . . . -1.2(8) no C7 C1 C2 C3 . . . . 179.0(5) no C1 C2 C3 C4 . . . . .1(8) no C10 N1 C4 C5 . . . . -1.0(8) no C11 N1 C4 C5 . . . . 177.4(5) no C10 N1 C4 C3 . . . . 178.3(5) no C11 N1 C4 C3 . . . . -3.2(8) no C2 C3 C4 N1 . . . . -179.2(5) no C2 C3 C4 C5 . . . . .2(8) no N1 C4 C5 C6 . . . . 179.9(5) no C3 C4 C5 C6 . . . . .5(8) no C4 C5 C6 C1 . . . . -1.6(8) no C2 C1 C6 C5 . . . . 1.9(8) no C7 C1 C6 C5 . . . . -178.3(5) no C6 C1 C7 C8 . . . . 170.6(6) no C2 C1 C7 C8 . . . . -9.6(9) yes C1 C7 C8 C9 . . . . -175.5(6) yes C7 C8 C9 O1 . . . . 175.5(7) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 23646677 2 PubChem 5284506