#------------------------------------------------------------------------------ #$Date: 2011-06-03 12:59:57 +0300 (Fri, 03 Jun 2011) $ #$Revision: 20162 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2230092.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_2230092 loop_ _publ_author_name 'Qiu, Jing-Bo' 'Yin, Bing-Zhu' _publ_section_title ; 4-(Diethylamino)salicylaldehyde azine ; _journal_coeditor_code NG5147 _journal_issue 5 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1092 _journal_volume 67 _journal_year 2011 _chemical_formula_iupac 'C22 H30 N4 O2' _chemical_formula_moiety 'C22 H30 N4 O2' _chemical_formula_sum 'C22 H30 N4 O2' _chemical_formula_weight 382.50 _chemical_name_common ; 4-(Diethylamino)salicylaldehyde azine ; _chemical_name_systematic ; 4-(Diethylamino)-2-hydroxybenzaldehyde azine ; _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 geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 103.57(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 8.736(5) _cell_length_b 7.809(5) _cell_length_c 16.122(10) _cell_measurement_reflns_used 5162 _cell_measurement_temperature 290(2) _cell_measurement_theta_max 27.66 _cell_measurement_theta_min 3.10 _cell_volume 1069.1(11) _computing_cell_refinement 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_data_collection 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_data_reduction 'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 290(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0456 _diffrn_reflns_av_sigmaI/netI 0.0420 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 9903 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 3.10 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_T_max 0.9907 _exptl_absorpt_correction_T_min 0.9884 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(ABSCOR; Higashi, 1995)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.188 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 412 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.450 _refine_diff_density_min -0.250 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 129 _refine_ls_number_reflns 2431 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.095 _refine_ls_R_factor_all 0.1379 _refine_ls_R_factor_gt 0.0739 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0919P)^2^+0.3133P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1956 _refine_ls_wR_factor_ref 0.2284 _reflns_number_gt 1227 _reflns_number_total 2431 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file ng5147.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2230092 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_type_symbol _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 O O1 0.2021(2) 0.6394(3) 0.57469(13) 0.0809(8) Uani d D 1 . . H H1 0.2663 0.6244 0.5433 0.121 Uiso d RD 1 . . C C1 0.4983(3) 0.4599(4) 0.60317(18) 0.0556(7) Uani d . 1 . . H H1A 0.5914 0.3972 0.6165 0.067 Uiso calc R 1 . . C C2 0.4129(3) 0.4858(3) 0.66828(16) 0.0489(7) Uani d . 1 . . C C3 0.4698(3) 0.4235(4) 0.75059(18) 0.0602(8) Uani d . 1 . . H H3 0.5638 0.3624 0.7625 0.072 Uiso calc R 1 . . C C4 0.3937(3) 0.4480(4) 0.81492(18) 0.0653(9) Uani d . 1 . . H H4 0.4360 0.4031 0.8688 0.078 Uiso calc R 1 . . C C5 0.2503(3) 0.5418(4) 0.79966(18) 0.0575(7) Uani d . 1 . . C C6 0.1898(3) 0.5998(4) 0.71712(17) 0.0558(7) Uani d . 1 . . H H6 0.0939 0.6573 0.7048 0.067 Uiso calc R 1 . . C C7 0.2678(3) 0.5745(4) 0.65257(17) 0.0537(7) Uani d . 1 . . C C8 0.2343(5) 0.5030(6) 0.9510(2) 0.0878(11) Uani d . 1 . . H H8A 0.3481 0.5128 0.9679 0.105 Uiso calc R 1 . . H H8B 0.1906 0.5672 0.9915 0.105 Uiso calc R 1 . . C C9 0.1893(5) 0.3226(6) 0.9530(3) 0.1028(14) Uani d . 1 . . H H9A 0.0770 0.3142 0.9441 0.154 Uiso calc R 1 . . H H9B 0.2387 0.2742 1.0074 0.154 Uiso calc R 1 . . H H9C 0.2226 0.2614 0.9086 0.154 Uiso calc R 1 . . C C10 0.0357(4) 0.6857(5) 0.8511(2) 0.0735(9) Uani d . 1 . . H H10A 0.0461 0.7776 0.8123 0.088 Uiso calc R 1 . . H H10B 0.0312 0.7373 0.9052 0.088 Uiso calc R 1 . . C C11 -0.1157(4) 0.5939(5) 0.8161(2) 0.0858(11) Uani d . 1 . . H H11A -0.1144 0.5460 0.7615 0.129 Uiso calc R 1 . . H H11B -0.2018 0.6729 0.8100 0.129 Uiso calc R 1 . . H H11C -0.1283 0.5038 0.8545 0.129 Uiso calc R 1 . . N N1 0.4511(3) 0.5198(3) 0.52728(15) 0.0589(7) Uani d . 1 . . N N2 0.1766(3) 0.5765(4) 0.86429(15) 0.0752(8) Uani d . 1 . . 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 0.0839(14) 0.1066(19) 0.0616(13) 0.0420(13) 0.0362(11) 0.0333(12) C1 0.0554(15) 0.0532(17) 0.0651(18) 0.0019(13) 0.0280(13) 0.0001(13) C2 0.0482(14) 0.0504(16) 0.0521(15) -0.0016(12) 0.0197(11) 0.0012(12) C3 0.0454(14) 0.076(2) 0.0619(18) 0.0117(13) 0.0182(13) 0.0085(15) C4 0.0519(15) 0.097(2) 0.0484(16) 0.0105(16) 0.0142(12) 0.0101(15) C5 0.0505(14) 0.0707(19) 0.0569(17) 0.0039(13) 0.0242(13) 0.0042(14) C6 0.0525(14) 0.0620(18) 0.0581(16) 0.0110(13) 0.0235(13) 0.0091(14) C7 0.0560(15) 0.0550(17) 0.0549(16) 0.0075(13) 0.0227(13) 0.0111(13) C8 0.084(2) 0.115(3) 0.074(2) 0.002(2) 0.0365(19) -0.009(2) C9 0.101(3) 0.114(4) 0.103(3) 0.019(3) 0.043(2) 0.009(2) C10 0.075(2) 0.083(2) 0.072(2) 0.0104(18) 0.0374(17) -0.0018(17) C11 0.079(2) 0.091(3) 0.094(3) 0.009(2) 0.0336(19) 0.007(2) N1 0.0643(14) 0.0606(15) 0.0616(15) 0.0027(12) 0.0345(11) 0.0032(12) N2 0.0708(16) 0.108(2) 0.0548(15) 0.0222(15) 0.0301(12) 0.0097(14) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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_3 _geom_angle _geom_angle_publ_flag C7 O1 H1 . . 107.9 ? N1 C1 C2 . . 122.6(3) ? N1 C1 H1A . . 118.7 ? C2 C1 H1A . . 118.7 ? C3 C2 C7 . . 116.6(2) ? C3 C2 C1 . . 121.1(2) ? C7 C2 C1 . . 122.3(2) ? C4 C3 C2 . . 123.0(3) ? C4 C3 H3 . . 118.5 ? C2 C3 H3 . . 118.5 ? C3 C4 C5 . . 120.3(3) ? C3 C4 H4 . . 119.8 ? C5 C4 H4 . . 119.8 ? N2 C5 C6 . . 121.5(2) ? N2 C5 C4 . . 121.4(3) ? C6 C5 C4 . . 117.1(2) ? C7 C6 C5 . . 122.0(2) ? C7 C6 H6 . . 119.0 ? C5 C6 H6 . . 119.0 ? O1 C7 C6 . . 117.9(2) ? O1 C7 C2 . . 121.2(2) ? C6 C7 C2 . . 120.9(2) ? C9 C8 N2 . . 111.0(3) ? C9 C8 H8A . . 109.4 ? N2 C8 H8A . . 109.4 ? C9 C8 H8B . . 109.4 ? N2 C8 H8B . . 109.4 ? H8A C8 H8B . . 108.0 ? C8 C9 H9A . . 109.5 ? C8 C9 H9B . . 109.5 ? H9A C9 H9B . . 109.5 ? C8 C9 H9C . . 109.5 ? H9A C9 H9C . . 109.5 ? H9B C9 H9C . . 109.5 ? N2 C10 C11 . . 114.4(3) ? N2 C10 H10A . . 108.7 ? C11 C10 H10A . . 108.7 ? N2 C10 H10B . . 108.7 ? C11 C10 H10B . . 108.7 ? H10A C10 H10B . . 107.6 ? C10 C11 H11A . . 109.5 ? C10 C11 H11B . . 109.5 ? H11A C11 H11B . . 109.5 ? C10 C11 H11C . . 109.5 ? H11A C11 H11C . . 109.5 ? H11B C11 H11C . . 109.5 ? C1 N1 N1 . 3_666 114.3(3) ? C5 N2 C10 . . 122.0(2) ? C5 N2 C8 . . 121.4(3) ? C10 N2 C8 . . 116.6(2) ? 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 O1 C7 . 1.351(3) ? O1 H1 . 0.8461 ? C1 N1 . 1.284(4) ? C1 C2 . 1.438(4) ? C1 H1A . 0.9300 ? C2 C3 . 1.391(4) ? C2 C7 . 1.414(4) ? C3 C4 . 1.371(4) ? C3 H3 . 0.9300 ? C4 C5 . 1.422(4) ? C4 H4 . 0.9300 ? C5 N2 . 1.374(3) ? C5 C6 . 1.387(4) ? C6 C7 . 1.386(3) ? C6 H6 . 0.9300 ? C8 C9 . 1.465(6) ? C8 N2 . 1.486(4) ? C8 H8A . 0.9700 ? C8 H8B . 0.9700 ? C9 H9A . 0.9600 ? C9 H9B . 0.9600 ? C9 H9C . 0.9600 ? C10 N2 . 1.471(4) ? C10 C11 . 1.494(5) ? C10 H10A . 0.9700 ? C10 H10B . 0.9700 ? C11 H11A . 0.9600 ? C11 H11B . 0.9600 ? C11 H11C . 0.9600 ? N1 N1 3_666 1.397(4) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA C8 H8B O1 4_576 0.97 2.64 3.481(5) 145 O1 H1 N1 . 0.85 1.88 2.640(3) 149