#------------------------------------------------------------------------------ #$Date: 2014-03-11 16:05:41 +0000 (Tue, 11 Mar 2014) $ #$Revision: 104878 $ #$URL: svn://www.crystallography.net/cod/cif/2/23/90/2239037.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_2239037 loop_ _publ_author_name 'Taha, Muhammad' 'Shah, Syed Adnan Ali' 'Sultan, Sadia' 'Ismail, Nor Hadiani' 'Yousuf, Sammer' _publ_section_title ; 2-{[2-(2-Hydroxy-5-methoxybenzylidene)hydrazin-1-ylidene]methyl}-4-methoxyphenol ; _journal_coeditor_code RZ5090 _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o131 _journal_paper_doi 10.1107/S1600536813034636 _journal_volume 70 _journal_year 2014 _chemical_formula_iupac 'C16 H16 N2 O4' _chemical_formula_moiety 'C16 H16 N2 O4' _chemical_formula_sum 'C16 H16 N2 O4' _chemical_formula_weight 300.31 _chemical_name_common 2-{[2-(2-Hydroxy-5-methoxybenzylidene)hydrazin-1-ylidene]methyl}-4-methoxyphenol _chemical_name_systematic ; 2,2'-[Hydrazine-1,2-diylidenebis(methan-1-yl-1-ylidene)]bis(4-methoxyphenol) ; _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 _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 91.192(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 6.7132(4) _cell_length_b 15.9369(10) _cell_length_c 6.8022(4) _cell_measurement_reflns_used 1747 _cell_measurement_temperature 273(2) _cell_measurement_theta_max 27.02 _cell_measurement_theta_min 2.56 _cell_volume 727.59(8) _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_collection 'SMART (Bruker, 2000)' _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material ; SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009) ; _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 273(2) _diffrn_measured_fraction_theta_full 0.977 _diffrn_measured_fraction_theta_max 0.977 _diffrn_measurement_device_type ; Bruker SMART APEX CCD area-detector ; _diffrn_measurement_method '\w scan' _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 0.0155 _diffrn_reflns_av_sigmaI/netI 0.0165 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 4243 _diffrn_reflns_theta_full 25.49 _diffrn_reflns_theta_max 25.49 _diffrn_reflns_theta_min 2.56 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_T_max 0.9832 _exptl_absorpt_correction_T_min 0.9444 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2000)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 316 _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.17 _refine_diff_density_max 0.136 _refine_diff_density_min -0.124 _refine_ls_extinction_coef 0.031(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXTL (Sheldrick, 2008)' _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 106 _refine_ls_number_reflns 1327 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.061 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0344 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0505P)^2^+0.0718P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0935 _refine_ls_wR_factor_ref 0.1011 _reflns_number_gt 1093 _reflns_number_total 1327 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL a in P2(1)/c CELL 0.71073 6.7132 15.9369 6.8022 90.000 91.192 90.000 ZERR 2.00 0.0004 0.0010 0.0004 0.000 0.002 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H O N UNIT 32 32 8 4 TEMP 0 ACTA CONF OMIT -3 51 SIZE 0.58 0.22 0.17 L.S. 20 BOND $H FMAP 2 1 60 PLAN 10 WGHT 0.050500 0.071800 EXTI 0.031068 FVAR 1.01795 O1 3 0.457220 0.626970 -0.270866 11.00000 0.07215 0.09808 = 0.08988 0.03230 0.01780 0.01077 O2 3 -0.219471 0.625244 0.175054 11.00000 0.05933 0.08921 = 0.08181 0.00187 0.00522 0.01706 H2 2 -0.199347 0.590273 0.283675 11.00000 0.11760 N1 4 -0.017751 0.526078 0.419229 11.00000 0.06243 0.05240 = 0.06138 0.00119 -0.00147 -0.00253 C1 1 0.115700 0.674155 -0.220709 11.00000 0.07409 0.05260 = 0.06073 0.00254 -0.01040 0.00408 AFIX 43 H1C 2 0.113632 0.705479 -0.336088 11.00000 -1.20000 AFIX 0 C2 1 -0.050058 0.671579 -0.105017 11.00000 0.06332 0.05897 = 0.06785 -0.00336 -0.01351 0.01472 AFIX 43 H2B 2 -0.163190 0.701505 -0.143616 11.00000 -1.20000 AFIX 0 C3 1 -0.052240 0.625713 0.066562 11.00000 0.05286 0.05089 = 0.06466 -0.00893 -0.00510 0.00387 C4 1 0.120033 0.580876 0.125298 11.00000 0.05280 0.04274 = 0.05970 -0.00275 -0.00489 -0.00124 C5 1 0.286033 0.584745 0.007000 11.00000 0.05238 0.05193 = 0.07112 0.00628 -0.00376 0.00513 AFIX 43 H5A 2 0.400769 0.555856 0.045341 11.00000 -1.20000 AFIX 0 C6 1 0.285695 0.630026 -0.165097 11.00000 0.05907 0.05351 = 0.06543 0.00392 -0.00100 -0.00066 C7 1 0.476172 0.682022 -0.431753 11.00000 0.09418 0.09088 = 0.06785 0.01405 0.00866 -0.00962 AFIX 137 H7A 2 0.606495 0.676177 -0.485602 11.00000 -1.50000 H7B 2 0.457668 0.738764 -0.388415 11.00000 -1.50000 H7C 2 0.377253 0.668594 -0.530747 11.00000 -1.50000 AFIX 0 C8 1 0.128636 0.530657 0.301892 11.00000 0.05491 0.04734 = 0.06663 -0.00061 -0.00454 -0.00039 AFIX 43 H8A 2 0.244241 0.500649 0.331434 11.00000 -1.20000 HKLF 4 REM a in P2(1)/c REM R1 = 0.0344 for 1093 Fo > 4sig(Fo) and 0.0418 for all 1327 data REM 106 parameters refined using 0 restraints END WGHT 0.0505 0.0717 REM Highest difference peak 0.136, deepest hole -0.124, 1-sigma level 0.025 Q1 1 0.0408 0.6017 0.0979 11.00000 0.05 0.14 Q2 1 -0.1109 0.5576 0.4344 11.00000 0.05 0.10 Q3 1 -0.1314 0.5396 0.4001 11.00000 0.05 0.09 Q4 1 0.1744 0.5607 0.0358 11.00000 0.05 0.09 Q5 1 0.2589 0.5802 -0.1353 11.00000 0.05 0.09 Q6 1 0.1853 0.6342 -0.2165 11.00000 0.05 0.08 Q7 1 -0.0655 0.6234 -0.0552 11.00000 0.05 0.08 Q8 1 0.1517 0.5780 0.0747 11.00000 0.05 0.08 Q9 1 0.0045 0.6446 -0.2004 11.00000 0.05 0.07 Q10 1 0.0878 0.5385 0.1695 11.00000 0.05 0.07 ; _[local]_cod_data_source_file rz5090sup1.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2239037 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_symmetry_multiplicity O O1 0.45722(17) 0.62697(7) -0.27087(17) 0.0865(4) Uani d . 1 1 O O2 -0.21947(15) 0.62524(8) 0.17505(19) 0.0767(4) Uani d . 1 1 H H2 -0.199(3) 0.5903(15) 0.284(3) 0.118(8) Uiso d . 1 1 N N1 -0.01775(16) 0.52608(7) 0.41923(16) 0.0588(3) Uani d . 1 1 C C1 0.1157(2) 0.67416(8) -0.2207(2) 0.0626(4) Uani d . 1 1 H H1C 0.1136 0.7055 -0.3361 0.075 Uiso calc R 1 1 C C2 -0.0501(2) 0.67158(9) -0.1050(2) 0.0636(4) Uani d . 1 1 H H2B -0.1632 0.7015 -0.1436 0.076 Uiso calc R 1 1 C C3 -0.0522(2) 0.62571(8) 0.0666(2) 0.0562(4) Uani d . 1 1 C C4 0.12003(18) 0.58088(7) 0.12530(19) 0.0518(3) Uani d . 1 1 C C5 0.28603(19) 0.58474(8) 0.0070(2) 0.0585(4) Uani d . 1 1 H H5A 0.4008 0.5559 0.0453 0.070 Uiso calc R 1 1 C C6 0.2857(2) 0.63003(8) -0.1651(2) 0.0594(4) Uani d . 1 1 C C7 0.4762(3) 0.68202(11) -0.4318(2) 0.0842(5) Uani d . 1 1 H H7A 0.6065 0.6762 -0.4856 0.126 Uiso calc R 1 1 H H7B 0.4577 0.7388 -0.3884 0.126 Uiso calc R 1 1 H H7C 0.3773 0.6686 -0.5307 0.126 Uiso calc R 1 1 C C8 0.12864(19) 0.53066(8) 0.3019(2) 0.0564(4) Uani d . 1 1 H H8A 0.2442 0.5006 0.3314 0.068 Uiso calc R 1 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 0.0721(7) 0.0981(9) 0.0899(8) 0.0108(6) 0.0178(6) 0.0323(6) O2 0.0593(6) 0.0892(8) 0.0818(8) 0.0171(5) 0.0052(5) 0.0019(6) N1 0.0624(7) 0.0524(6) 0.0614(7) -0.0025(5) -0.0015(5) 0.0012(5) C1 0.0741(9) 0.0526(8) 0.0607(9) 0.0041(6) -0.0104(7) 0.0025(6) C2 0.0633(8) 0.0590(8) 0.0678(9) 0.0147(6) -0.0135(7) -0.0034(6) C3 0.0529(7) 0.0509(7) 0.0647(9) 0.0039(5) -0.0051(6) -0.0089(6) C4 0.0528(7) 0.0427(6) 0.0597(8) -0.0012(5) -0.0049(6) -0.0028(5) C5 0.0524(7) 0.0519(7) 0.0711(9) 0.0051(5) -0.0038(6) 0.0063(6) C6 0.0591(8) 0.0535(7) 0.0654(9) -0.0007(6) -0.0010(6) 0.0039(6) C7 0.0942(12) 0.0909(12) 0.0679(10) -0.0096(9) 0.0087(9) 0.0141(8) C8 0.0549(7) 0.0473(7) 0.0666(9) -0.0004(5) -0.0045(6) -0.0006(6) 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' O O 0.0106 0.0060 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle C6 O1 C7 . 118.38(12) C3 O2 H2 . 109.0(13) C8 N1 N1 3_566 113.84(13) C2 C1 C6 . 119.96(14) C2 C1 H1C . 120.0 C6 C1 H1C . 120.0 C1 C2 C3 . 121.54(12) C1 C2 H2B . 119.2 C3 C2 H2B . 119.2 O2 C3 C2 . 119.17(12) O2 C3 C4 . 121.76(13) C2 C3 C4 . 119.07(13) C5 C4 C3 . 118.45(12) C5 C4 C8 . 119.20(11) C3 C4 C8 . 122.35(12) C6 C5 C4 . 121.95(12) C6 C5 H5A . 119.0 C4 C5 H5A . 119.0 O1 C6 C5 . 116.20(12) O1 C6 C1 . 124.77(13) C5 C6 C1 . 119.03(13) O1 C7 H7A . 109.5 O1 C7 H7B . 109.5 H7A C7 H7B . 109.5 O1 C7 H7C . 109.5 H7A C7 H7C . 109.5 H7B C7 H7C . 109.5 N1 C8 C4 . 122.15(12) N1 C8 H8A . 118.9 C4 C8 H8A . 118.9 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance O1 C6 . 1.3713(17) O1 C7 . 1.4105(18) O2 C3 . 1.3563(16) O2 H2 . 0.93(2) N1 C8 . 1.2809(15) N1 N1 3_566 1.394(2) C1 C2 . 1.377(2) C1 C6 . 1.386(2) C1 H1C . 0.9300 C2 C3 . 1.377(2) C2 H2B . 0.9300 C3 C4 . 1.4101(18) C4 C5 . 1.3894(17) C4 C8 . 1.4436(18) C5 C6 . 1.3752(19) C5 H5A . 0.9300 C7 H7A . 0.9600 C7 H7B . 0.9600 C7 H7C . 0.9600 C8 H8A . 0.9300 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O2 H2 N1 0.94(2) 1.82(2) 2.6451(16) 145.0(18) 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 C6 C1 C2 C3 . -0.1(2) C1 C2 C3 O2 . -179.95(12) C1 C2 C3 C4 . 0.4(2) O2 C3 C4 C5 . -179.65(11) C2 C3 C4 C5 . -0.03(18) O2 C3 C4 C8 . 1.09(19) C2 C3 C4 C8 . -179.29(12) C3 C4 C5 C6 . -0.68(19) C8 C4 C5 C6 . 178.60(12) C7 O1 C6 C5 . -170.46(14) C7 O1 C6 C1 . 10.2(2) C4 C5 C6 O1 . -178.37(12) C4 C5 C6 C1 . 1.0(2) C2 C1 C6 O1 . 178.72(13) C2 C1 C6 C5 . -0.6(2) N1 N1 C8 C4 3_566 179.45(12) C5 C4 C8 N1 . 178.39(12) C3 C4 C8 N1 . -2.36(19) _cod_database_fobs_code 2239037