#------------------------------------------------------------------------------ #$Date: 2015-04-02 12:22:18 +0100 (Thu, 02 Apr 2015) $ #$Revision: 134621 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/11/2011189.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_2011189 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 'C16 H14 N2 O3' _chemical_formula_weight 282.29 _chemical_melting_point 141.0(10) _chemical_name_systematic ; N-[(E,2E)-3-(4-methoxyphenyl)-2-propenylidene]-3-nitroaniline ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 105.7670(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 15.7883(8) _cell_length_b 3.9239(2) _cell_length_c 22.6063(11) _cell_measurement_reflns_used 5200 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 24 _cell_measurement_theta_min 2 _cell_volume 1347.80(12) _computing_cell_refinement SMART _computing_data_collection 'SMART (Siemens, 1994)' _computing_data_reduction 'SHELXTL-Plus (Sheldrick, 1994)' _computing_molecular_graphics SHELXTL-Plus _computing_publication_material SHELXTL-Plus _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 100(2) _diffrn_measurement_device 'Siemens SMART CCD area detector' _diffrn_measurement_method '\f and \w' _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 .0633 _diffrn_reflns_av_sigmaI/netI .0544 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 14296 _diffrn_reflns_theta_max 30.03 _diffrn_reflns_theta_min 1.41 _diffrn_standards_decay_% none _exptl_absorpt_coefficient_mu .098 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'square prism' _exptl_crystal_F_000 592 _exptl_crystal_size_max .3 _exptl_crystal_size_mid .1 _exptl_crystal_size_min .1 _refine_diff_density_max .50 _refine_diff_density_min -.22 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all .890 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 246 _refine_ls_number_reflns 3925 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all .921 _refine_ls_restrained_S_obs 1.024 _refine_ls_R_factor_all .0777 _refine_ls_R_factor_gt .0543 _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^)+(0.0889P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all .1412 _refine_ls_wR_factor_ref .1263 _reflns_number_gt 2603 _reflns_number_total 3938 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bm1393.cif _[local]_cod_data_source_block 1a _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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 'Monoclinic' changed to 'monoclinic' 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^)+(0.0889P)^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^)+(0.0889P)^2^] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_database_code 2011189 _cod_database_fobs_code 2011189 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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 .0232(5) .0245(5) .0222(5) .0005(4) .0075(4) -.0016(4) N2 .0297(6) .0289(6) .0371(7) .0004(5) .0183(5) -.0004(5) O1 .0295(6) .0480(7) .0441(6) .0102(5) .0158(5) .0049(5) O2 .0468(7) .0547(7) .0364(6) .0049(6) .0229(5) -.0075(5) O3 .0250(5) .0301(5) .0214(4) .0018(4) .0055(4) -.0009(4) C1 .0209(6) .0192(6) .0239(6) -.0020(5) .0080(5) .0000(5) C2 .0197(6) .0230(6) .0252(6) -.0010(5) .0062(5) .0019(5) C3 .0230(6) .0210(6) .0301(7) -.0018(5) .0129(5) -.0007(5) C4 .0305(7) .0230(6) .0251(6) -.0041(5) .0089(5) -.0014(5) C5 .0237(6) .0254(7) .0250(6) -.0020(5) .0022(5) .0016(5) C6 .0206(6) .0223(6) .0282(7) .0011(5) .0079(5) .0010(5) C7 .0214(6) .0215(6) .0261(6) -.0009(5) .0067(5) -.0008(5) C8 .0227(6) .0213(6) .0249(6) -.0018(5) .0069(5) -.0014(5) C9 .0199(6) .0213(6) .0250(6) -.0005(5) .0068(5) -.0012(5) C10 .0197(6) .0182(6) .0232(6) -.0022(5) .0060(5) -.0004(5) C11 .0189(6) .0211(6) .0262(6) -.0001(5) .0086(5) -.0009(5) C12 .0174(6) .0237(6) .0256(6) .0003(5) .0035(5) .0021(5) C13 .0220(6) .0200(6) .0215(6) -.0030(5) .0062(5) .0000(5) C14 .0190(6) .0210(6) .0266(6) .0000(5) .0082(5) .0000(5) C15 .0179(6) .0209(6) .0242(6) -.0012(5) .0041(5) .0011(5) C16 .0294(7) .0262(7) .0265(7) .0020(6) .0103(6) -.0010(5) 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 .71571(7) .8307(3) .47857(5) .0230(2) Uani d . 1 . N N2 .58671(8) 1.3183(3) .63606(6) .0301(3) Uani d . 1 . N O1 .52247(7) 1.4097(3) .59496(5) .0394(3) Uani d . 1 . O O2 .59540(8) 1.3733(3) .69088(5) .0437(3) Uani d . 1 . O O3 .54119(6) .8769(2) .06917(4) .0257(2) Uani d . 1 . O C1 .71743(8) .9150(3) .53949(6) .0210(3) Uani d . 1 . C C2 .64822(9) 1.0745(3) .55690(6) .0226(3) Uani d . 1 . C H2 .5942(11) 1.138(4) .5271(7) .028(4) Uiso d . 1 . H C3 .65833(9) 1.1368(3) .61860(6) .0236(3) Uani d . 1 . C C4 .73237(9) 1.0458(3) .66461(6) .0260(3) Uani d . 1 . C H4 .7366(11) 1.097(4) .7085(7) .038(4) Uiso d . 1 . H C5 .80030(9) .8853(3) .64703(6) .0255(3) Uani d . 1 . C H5 .8529(12) .815(4) .6774(7) .038(4) Uiso d . 1 . H C6 .79286(9) .8229(3) .58547(6) .0234(3) Uani d . 1 . C H6 .8377(11) .714(4) .5731(7) .032(4) Uiso d . 1 . H C7 .66406(8) .9937(3) .43370(6) .0230(3) Uani d . 1 . C H7 .6275(10) 1.180(4) .4396(6) .020(3) Uiso d . 1 . H C8 .65983(9) .9134(3) .37074(6) .0229(3) Uani d . 1 . C H8 .6997(11) .733(4) .3628(7) .034(4) Uiso d . 1 . H C9 .60137(8) 1.0693(3) .32388(6) .0219(3) Uani d . 1 . C H9 .5599(10) 1.227(4) .3332(6) .024(4) Uiso d . 1 . H C10 .58973(8) 1.0143(3) .25832(5) .0203(3) Uani d . 1 . C C11 .51440(8) 1.1443(3) .21595(6) .0216(3) Uani d . 1 . C H11 .4748(11) 1.273(4) .2310(7) .032(4) Uiso d . 1 . H C12 .50053(8) 1.0972(3) .15374(6) .0227(3) Uani d . 1 . C H12 .4502(11) 1.190(4) .1240(7) .032(4) Uiso d . 1 . H C13 .56219(8) .9180(3) .13143(6) .0211(3) Uani d . 1 . C C14 .63867(8) .7953(3) .17250(6) .0218(3) Uani d . 1 . C H14 .6816(10) .670(4) .1561(6) .024(4) Uiso d . 1 . H C15 .65141(8) .8408(3) .23524(6) .0213(3) Uani d . 1 . C H15 .7062(10) .747(4) .2635(6) .023(4) Uiso d . 1 . H C16 .60435(10) .7113(4) .04374(7) .0268(3) Uani d . 1 . C H16C .6175(10) .487(4) .0605(6) .027(4) Uiso d . 1 . H H16B .6583(11) .851(4) .0515(7) .032(4) Uiso d . 1 . H H16A .5766(10) .699(4) -.0017(7) .031(4) 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 119.59(11) no O2 N2 O1 123.70(12) no O2 N2 C3 118.05(12) no O1 N2 C3 118.24(11) no C13 O3 C16 117.78(10) no C6 C1 C2 118.49(12) no C6 C1 N1 116.86(11) no C2 C1 N1 124.62(11) no C3 C2 C1 118.43(12) no C2 C3 C4 123.72(12) no C2 C3 N2 117.90(12) no C4 C3 N2 118.36(12) no C3 C4 C5 117.48(12) no C6 C5 C4 120.33(12) no C5 C6 C1 121.54(12) no N1 C7 C8 121.30(12) no C9 C8 C7 121.00(12) no C8 C9 C10 126.98(12) no C15 C10 C11 117.92(11) no C15 C10 C9 122.83(11) no C11 C10 C9 119.24(11) no C12 C11 C10 121.23(12) no C11 C12 C13 120.14(12) no O3 C13 C14 124.74(11) no O3 C13 C12 115.63(11) no C14 C13 C12 119.63(11) no C15 C14 C13 119.66(12) no C14 C15 C10 121.38(11) 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 . . 1.286(2) no N1 C1 . . 1.409(2) no N2 O2 . . 1.2284(15) no N2 O1 . . 1.228(2) no N2 C3 . . 1.478(2) no O3 C13 . . 1.3651(14) no O3 C16 . . 1.435(2) no C1 C6 . . 1.399(2) no C1 C2 . . 1.405(2) no C2 C3 . . 1.382(2) no C2 H2 . . .96(2) no C3 C4 . . 1.384(2) no C4 C5 . . 1.392(2) no C4 H4 . . 1.00(2) no C5 C6 . . 1.386(2) no C5 H5 . . .96(2) no C6 H6 . . .93(2) no C7 C8 . . 1.441(2) no C7 H7 . . .964(15) no C8 C9 . . 1.348(2) no C8 H8 . . 1.00(2) no C9 C10 . . 1.459(2) no C9 H9 . . .97(2) no C10 C15 . . 1.400(2) no C10 C11 . . 1.405(2) no C11 C12 . . 1.376(2) no C11 H11 . . .94(2) no C12 C13 . . 1.401(2) no C12 H12 . . .96(2) no C13 C14 . . 1.394(2) no C14 C15 . . 1.389(2) no C14 H14 . . .99(2) no C15 H15 . . 1.00(2) no C16 H16C . . .96(2) no C16 H16B . . .99(2) no C16 H16A . . 1.002(15) 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 C6 -158.33(12) no C7 N1 C1 C2 23.5(2) no C6 C1 C2 C3 .8(2) no N1 C1 C2 C3 178.88(12) no C1 C2 C3 C4 -1.1(2) no C1 C2 C3 N2 177.37(11) no O2 N2 C3 C2 179.83(12) no O1 N2 C3 C2 -1.2(2) no O2 N2 C3 C4 -1.6(2) no O1 N2 C3 C4 177.43(12) no C2 C3 C4 C5 .6(2) no N2 C3 C4 C5 -177.89(11) no C3 C4 C5 C6 .3(2) no C4 C5 C6 C1 -.6(2) no C2 C1 C6 C5 .1(2) no N1 C1 C6 C5 -178.19(11) no C1 N1 C7 C8 -179.49(11) no N1 C7 C8 C9 175.50(12) no C7 C8 C9 C10 179.95(11) no C8 C9 C10 C15 -14.2(2) no C8 C9 C10 C11 166.91(13) no C15 C10 C11 C12 1.3(2) no C9 C10 C11 C12 -179.71(11) no C10 C11 C12 C13 -.3(2) no C16 O3 C13 C14 -3.4(2) no C16 O3 C13 C12 176.68(11) no C11 C12 C13 O3 178.24(11) no C11 C12 C13 C14 -1.6(2) no O3 C13 C14 C15 -177.44(11) no C12 C13 C14 C15 2.4(2) no C13 C14 C15 C10 -1.4(2) no C11 C10 C15 C14 -.5(2) no C9 C10 C15 C14 -179.44(11) no