#------------------------------------------------------------------------------ #$Date: 2012-08-11 01:29:15 +0300 (Sat, 11 Aug 2012) $ #$Revision: 64093 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/23/56/2235620.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_2235620 loop_ _publ_author_name 'Al-Mehana, Wisam Naji Atiyah' 'Yahya, Rosiyah' 'Sonsudin, Faridah' 'Lo, Kong Mun' _publ_section_title ; (E,E)-1,2-Bis[3-(prop-2-yn-1-yloxy)benzylidene]hydrazine ; _journal_coeditor_code SU2430 _journal_issue 7 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o2087 _journal_volume 68 _journal_year 2012 _chemical_formula_iupac 'C20 H16 N2 O2' _chemical_formula_moiety 'C20 H16 N2 O2' _chemical_formula_sum 'C20 H16 N2 O2' _chemical_formula_weight 316.35 _chemical_melting_point_gt 401 _chemical_melting_point_lt 403 _chemical_name_systematic ; (E,E)-1,2-Bis[3-(prop-2-yn-1-yloxy)benzylidene]hydrazine ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 67.986(7) _cell_angle_beta 77.487(6) _cell_angle_gamma 84.132(6) _cell_formula_units_Z 1 _cell_length_a 4.5700(3) _cell_length_b 9.4947(7) _cell_length_c 9.8920(8) _cell_measurement_reflns_used 1636 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 29.1258 _cell_measurement_theta_min 2.3097 _cell_volume 388.37(5) _computing_cell_refinement 'CrysAlis Pro (Agilent, 2012)' _computing_data_collection 'CrysAlis Pro (Agilent, 2012)' _computing_data_reduction 'CrysAlis Pro (Agilent, 2012)' _computing_molecular_graphics 'X-SEED (Barbour, 2001)' _computing_publication_material 'pubCIF (Westrip, 2010)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.966 _diffrn_measured_fraction_theta_max 0.966 _diffrn_measurement_device_type 'Agilent SuperNova Dual (Cu at zero) Atlas' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator mirror _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0355 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 2956 _diffrn_reflns_theta_full 27.49 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 2.31 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.43985 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(CrysAlis Pro; Agilent, 2012)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 166 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.228 _refine_diff_density_min -0.285 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 109 _refine_ls_number_reflns 1710 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.016 _refine_ls_R_factor_all 0.0478 _refine_ls_R_factor_gt 0.0407 _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^)+(0.0756P)^2^+0.0718P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1141 _refine_ls_wR_factor_ref 0.1217 _reflns_number_gt 1508 _reflns_number_total 1710 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file su2430.cif _[local]_cod_data_source_block I _cod_database_code 2235620 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -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 O1 0.0223(5) 0.0187(4) 0.0173(4) 0.0091(3) -0.0109(3) -0.0080(3) N1 0.0141(5) 0.0152(5) 0.0162(5) 0.0017(4) -0.0086(4) -0.0022(4) C1 0.0254(6) 0.0225(6) 0.0209(6) 0.0061(5) -0.0105(5) -0.0083(5) C2 0.0206(6) 0.0183(6) 0.0204(6) 0.0069(4) -0.0071(4) -0.0061(5) C3 0.0218(6) 0.0209(6) 0.0208(6) 0.0085(5) -0.0101(5) -0.0098(5) C4 0.0146(5) 0.0156(5) 0.0135(5) -0.0005(4) -0.0045(4) -0.0027(4) C5 0.0166(6) 0.0146(5) 0.0184(6) 0.0037(4) -0.0076(4) -0.0021(4) C6 0.0205(6) 0.0132(5) 0.0225(6) 0.0049(4) -0.0069(5) -0.0069(4) C7 0.0194(6) 0.0170(5) 0.0184(5) 0.0014(4) -0.0082(4) -0.0065(4) C8 0.0126(5) 0.0136(5) 0.0175(5) -0.0001(4) -0.0050(4) -0.0028(4) C9 0.0142(5) 0.0128(5) 0.0166(5) 0.0026(4) -0.0044(4) -0.0044(4) C10 0.0150(5) 0.0152(5) 0.0160(5) 0.0000(4) -0.0067(4) -0.0050(4) 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_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy O O1 0.26162(18) 0.81143(9) 0.53750(8) 0.0186(3) Uani d . 1.000 N N1 0.9141(2) 0.53809(10) 0.94457(10) 0.0154(3) Uani d . 1.000 C C1 0.1926(3) 0.64779(13) 0.28726(13) 0.0223(3) Uani d . 1.000 C C2 0.2727(3) 0.67068(13) 0.38360(13) 0.0201(3) Uani d . 1.000 C C3 0.3877(3) 0.68058(13) 0.50670(13) 0.0202(3) Uani d . 1.000 C C4 0.3322(2) 0.82703(12) 0.65948(12) 0.0150(3) Uani d . 1.000 C C5 0.1900(3) 0.94943(13) 0.69477(13) 0.0173(3) Uani d . 1.000 C C6 0.2352(3) 0.97068(12) 0.81942(13) 0.0186(3) Uani d . 1.000 C C7 0.4213(3) 0.87082(13) 0.90930(13) 0.0176(3) Uani d . 1.000 C C8 0.5677(2) 0.75107(12) 0.87209(12) 0.0151(3) Uani d . 1.000 C C9 0.5252(2) 0.72894(12) 0.74544(12) 0.0148(3) Uani d . 1.000 C C10 0.7639(2) 0.65050(12) 0.96900(12) 0.0150(3) Uani d . 1.000 H H1 0.13000 0.62990 0.21190 0.0270 Uiso c R 1.000 H H3A 0.33630 0.59000 0.59440 0.0240 Uiso c R 1.000 H H3B 0.60440 0.68700 0.48080 0.0240 Uiso c R 1.000 H H5 0.06580 1.01620 0.63490 0.0210 Uiso c R 1.000 H H6 0.14090 1.05210 0.84350 0.0220 Uiso c R 1.000 H H7 0.44750 0.88440 0.99420 0.0210 Uiso c R 1.000 H H9 0.62480 0.64970 0.71920 0.0180 Uiso c R 1.000 H H10 0.78030 0.66930 1.05280 0.0180 Uiso c R 1.000 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 _geom_angle_publ_flag C3 O1 C4 . 115.61(9) no N1 N1 C10 2_767 111.29(9) no C1 C2 C3 . 173.13(14) no O1 C3 C2 . 109.82(11) no O1 C4 C5 . 115.01(10) no O1 C4 C9 . 124.05(11) no C5 C4 C9 . 120.93(11) no C4 C5 C6 . 119.44(12) no C5 C6 C7 . 120.38(12) no C6 C7 C8 . 120.04(11) no C7 C8 C9 . 120.09(10) no C7 C8 C10 . 117.97(10) no C9 C8 C10 . 121.94(10) no C4 C9 C8 . 119.08(11) no N1 C10 C8 . 123.54(10) no C2 C1 H1 . 180.00 no O1 C3 H3A . 110.00 no O1 C3 H3B . 110.00 no C2 C3 H3A . 110.00 no C2 C3 H3B . 110.00 no H3A C3 H3B . 108.00 no C4 C5 H5 . 120.00 no C6 C5 H5 . 120.00 no C5 C6 H6 . 120.00 no C7 C6 H6 . 120.00 no C6 C7 H7 . 120.00 no C8 C7 H7 . 120.00 no C4 C9 H9 . 120.00 no C8 C9 H9 . 120.00 no N1 C10 H10 . 118.00 no C8 C10 H10 . 118.00 no 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 C3 . 1.4247(16) no O1 C4 . 1.3763(13) no N1 C10 . 1.2808(15) no N1 N1 2_767 1.4158(13) no C1 C2 . 1.1883(18) no C2 C3 . 1.4632(18) no C4 C5 . 1.3951(18) no C4 C9 . 1.3899(15) no C5 C6 . 1.3817(17) no C6 C7 . 1.3941(18) no C7 C8 . 1.3883(18) no C8 C9 . 1.4009(16) no C8 C10 . 1.4649(15) no C1 H1 . 0.9300 no C3 H3A . 0.9700 no C3 H3B . 0.9700 no C5 H5 . 0.9300 no C6 H6 . 0.9300 no C7 H7 . 0.9300 no C9 H9 . 0.9300 no C10 H10 . 0.9300 no 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 _geom_hbond_publ_flag C5 H5 O1 2_576 0.93 2.52 3.4467(16) 177 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_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C3 O1 C4 C9 . . . 3.31(15) no C4 O1 C3 C2 . . . 174.74(10) no C3 O1 C4 C5 . . . -175.53(10) no C10 N1 N1 C10 . 2_767 2_767 179.98(10) no N1 N1 C10 C8 2_767 . . 179.47(9) no O1 C4 C5 C6 . . . 177.00(11) no C9 C4 C5 C6 . . . -1.88(18) no C5 C4 C9 C8 . . . 2.29(16) no O1 C4 C9 C8 . . . -176.49(10) no C4 C5 C6 C7 . . . 0.0(2) no C5 C6 C7 C8 . . . 1.4(2) no C6 C7 C8 C10 . . . 179.20(11) no C6 C7 C8 C9 . . . -0.97(18) no C7 C8 C9 C4 . . . -0.85(16) no C7 C8 C10 N1 . . . -178.79(11) no C9 C8 C10 N1 . . . 1.38(17) no C10 C8 C9 C4 . . . 178.97(10) no