#------------------------------------------------------------------------------ #$Date: 2016-02-21 00:03:34 +0000 (Sun, 21 Feb 2016) $ #$Revision: 176798 $ #$URL: svn://www.crystallography.net/cod/cif/2/23/90/2239033.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_2239033 loop_ _publ_author_name 'Yamin, Bohari M.' 'Kamalulazmy, Nurul A.' 'Hassan, Nurul I.' _publ_section_title ; 4,4'-({[(Pyridine-2,6-diyl)bis(methylene)]bis(oxy)}bis(methylene))dibenzonitrile ; _journal_coeditor_code HG5373 _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o132 _journal_paper_doi 10.1107/S1600536814000245 _journal_volume 70 _journal_year 2014 _chemical_formula_iupac 'C23 H19 N3 O2' _chemical_formula_moiety 'C23 H19 N3 O2' _chemical_formula_sum 'C23 H19 N3 O2' _chemical_formula_weight 369.41 _chemical_name_systematic 4,4'-({[(Pyridine-2,6-diyl)bis(methylene)]bis(oxy)}bis(methylene))dibenzonitrile _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/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 107.837(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 14.1838(7) _cell_length_b 7.5493(4) _cell_length_c 18.4619(12) _cell_measurement_reflns_used 8925 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 26.0 _cell_measurement_theta_min 3.0 _cell_volume 1881.83(18) _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_collection 'SMART (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material ; SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009) ; _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 296(2) _diffrn_detector_area_resol_mean 83.66 _diffrn_measured_fraction_theta_full 0.99 _diffrn_measured_fraction_theta_max 0.99 _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 0.0404 _diffrn_reflns_av_sigmaI/netI 0.0171 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 21611 _diffrn_reflns_theta_full 26.0 _diffrn_reflns_theta_max 26.00 _diffrn_reflns_theta_min 3.09 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_T_max 0.9717 _exptl_absorpt_correction_T_min 0.9595 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2009)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 776 _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.34 _refine_diff_density_max 0.10 _refine_diff_density_min -0.12 _refine_ls_extinction_coef 0.0196(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 2008)' _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 129 _refine_ls_number_reflns 1846 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.052 _refine_ls_R_factor_all 0.0494 _refine_ls_R_factor_gt 0.0387 _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^)+(0.0485P)^2^+0.9538P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0981 _refine_ls_wR_factor_ref 0.1061 _reflns_number_gt 1519 _reflns_number_total 1846 _reflns_threshold_expression I>2sigma(I) _iucr_refine_instructions_details ; TITL a in C2/c CELL 0.71073 14.1838 7.5493 18.4619 90.000 107.837 90.000 ZERR 4.00 0.0007 0.0004 0.0012 0.000 0.002 0.000 LATT 7 SYMM -x, y, -z+1/2 SFAC C H N O UNIT 92 76 12 8 L.S. 20 ACTA OMIT -3 52 BOND $H FMAP 2 2 6 PLAN 5 SIZE 0.340 0.440 0.490 HTAB CONF TEMP 23.00 WGHT 0.048500 0.953800 EXTI 0.019633 FVAR 0.18501 O1 4 0.733552 0.395544 0.184879 11.00000 0.02824 0.08348 = 0.04905 -0.01564 0.00695 -0.00472 N1 3 1.000000 0.461505 0.250000 10.50000 0.02928 0.05500 = 0.03692 0.00000 0.00501 0.00000 N2 3 0.251635 0.085100 -0.085744 11.00000 0.04474 0.07012 = 0.08593 -0.01361 0.00353 -0.00807 C1 1 1.000000 0.094635 0.250000 10.50000 0.05543 0.05020 = 0.05115 0.00000 0.01298 0.00000 AFIX 43 H1 2 1.000000 -0.028556 0.250003 10.50000 -1.20000 AFIX 0 C2 1 0.912056 0.186629 0.234188 11.00000 0.03932 0.06235 = 0.04456 -0.00475 0.00946 -0.01133 AFIX 43 H2 2 0.851947 0.126911 0.223005 11.00000 -1.20000 AFIX 0 C3 1 0.915234 0.369663 0.235333 11.00000 0.03021 0.05917 = 0.03291 -0.00706 0.00633 -0.00293 C4 1 0.823793 0.481257 0.224709 11.00000 0.02966 0.07363 = 0.05986 -0.02201 0.00653 -0.00046 AFIX 23 H4A 2 0.820574 0.516853 0.274381 11.00000 -1.20000 H4B 2 0.830026 0.587957 0.197261 11.00000 -1.20000 AFIX 0 C5 1 0.717449 0.388193 0.105754 11.00000 0.03271 0.05424 = 0.04978 -0.00159 0.00947 0.00180 AFIX 23 H5A 2 0.765903 0.310218 0.095064 11.00000 -1.20000 H5B 2 0.725670 0.505393 0.087011 11.00000 -1.20000 AFIX 0 C6 1 0.615101 0.321394 0.065752 11.00000 0.03023 0.03418 = 0.04420 -0.00034 0.00840 0.00664 C7 1 0.581636 0.321837 -0.013202 11.00000 0.04029 0.04666 = 0.04413 -0.00013 0.01636 0.00137 AFIX 43 H7 2 0.622531 0.364538 -0.040159 11.00000 -1.20000 AFIX 0 C8 1 0.488715 0.259873 -0.052036 11.00000 0.04690 0.04854 = 0.03679 -0.00301 0.00796 0.00276 AFIX 43 H8 2 0.467246 0.259940 -0.104953 11.00000 -1.20000 AFIX 0 C9 1 0.427031 0.197253 -0.012172 11.00000 0.03431 0.03443 = 0.04782 -0.00134 0.00606 0.00305 C10 1 0.459423 0.197482 0.066617 11.00000 0.03676 0.04688 = 0.05000 0.00733 0.01425 0.00095 AFIX 43 H10 2 0.418190 0.156161 0.093557 11.00000 -1.20000 AFIX 0 C11 1 0.553000 0.259130 0.105116 11.00000 0.03812 0.04798 = 0.03758 0.00403 0.00713 0.00465 AFIX 43 H11 2 0.574552 0.258839 0.158032 11.00000 -1.20000 AFIX 0 C12 1 0.329499 0.133139 -0.052693 11.00000 0.04189 0.04323 = 0.05876 -0.00394 0.00800 0.00249 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM a in C2/c REM R1 = 0.0387 for 1519 Fo > 4sig(Fo) and 0.0494 for all 1846 data REM 129 parameters refined using 0 restraints END WGHT 0.0485 0.9549 REM Highest difference peak 0.107, deepest hole -0.123, 1-sigma level 0.028 Q1 1 0.8226 0.4445 0.2930 11.00000 0.05 0.11 Q2 1 0.7272 0.4793 0.1549 11.00000 0.05 0.09 Q3 1 0.9619 0.4303 0.2409 11.00000 0.05 0.09 Q4 1 0.7466 0.4377 0.0665 11.00000 0.05 0.07 Q5 1 0.7039 0.5623 0.1114 11.00000 0.05 0.07 ; _cod_data_source_file hg5373sup1.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2239033 _cod_database_fobs_code 2239033 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -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 0.73355(7) 0.39554(16) 0.18488(6) 0.0547(3) Uani d . 1 1 N N1 1.0000 0.4615(2) 0.2500 0.0416(4) Uani d S 1 2 N N2 0.25164(10) 0.0851(2) -0.08574(9) 0.0706(5) Uani d . 1 1 C C1 1.0000 0.0946(3) 0.2500 0.0530(6) Uani d S 1 2 H H1 1.0000 -0.0286 0.2500 0.064 Uiso calc SR 1 2 C C2 0.91206(10) 0.1866(2) 0.23419(8) 0.0495(4) Uani d . 1 1 H H2 0.8519 0.1269 0.2230 0.059 Uiso calc R 1 1 C C3 0.91523(9) 0.3697(2) 0.23533(7) 0.0415(4) Uani d . 1 1 C C4 0.82379(10) 0.4813(2) 0.22471(10) 0.0560(4) Uani d . 1 1 H H4A 0.8206 0.5169 0.2744 0.067 Uiso calc R 1 1 H H4B 0.8300 0.5880 0.1973 0.067 Uiso calc R 1 1 C C5 0.71745(10) 0.3882(2) 0.10575(8) 0.0463(4) Uani d . 1 1 H H5A 0.7659 0.3102 0.0951 0.056 Uiso calc R 1 1 H H5B 0.7257 0.5054 0.0870 0.056 Uiso calc R 1 1 C C6 0.61510(9) 0.32139(17) 0.06575(8) 0.0369(3) Uani d . 1 1 C C7 0.58164(10) 0.3218(2) -0.01320(8) 0.0429(4) Uani d . 1 1 H H7 0.6225 0.3645 -0.0402 0.052 Uiso calc R 1 1 C C8 0.48871(11) 0.2599(2) -0.05204(8) 0.0452(4) Uani d . 1 1 H H8 0.4672 0.2599 -0.1050 0.054 Uiso calc R 1 1 C C9 0.42703(10) 0.19725(18) -0.01217(8) 0.0403(3) Uani d . 1 1 C C10 0.45942(10) 0.19748(19) 0.06662(8) 0.0443(4) Uani d . 1 1 H H10 0.4182 0.1562 0.0936 0.053 Uiso calc R 1 1 C C11 0.55300(10) 0.25913(19) 0.10512(8) 0.0422(4) Uani d . 1 1 H H11 0.5746 0.2588 0.1580 0.051 Uiso calc R 1 1 C C12 0.32950(11) 0.1331(2) -0.05269(9) 0.0496(4) Uani d . 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 0.0282(5) 0.0835(9) 0.0491(6) -0.0047(5) 0.0069(4) -0.0156(5) N1 0.0293(8) 0.0550(10) 0.0369(8) 0.000 0.0050(6) 0.000 N2 0.0447(8) 0.0701(10) 0.0859(11) -0.0081(7) 0.0035(7) -0.0136(8) C1 0.0554(13) 0.0502(13) 0.0511(12) 0.000 0.0130(10) 0.000 C2 0.0393(8) 0.0624(10) 0.0446(8) -0.0113(7) 0.0095(6) -0.0047(7) C3 0.0302(7) 0.0592(9) 0.0329(7) -0.0029(6) 0.0063(5) -0.0071(6) C4 0.0297(7) 0.0736(11) 0.0599(9) -0.0005(7) 0.0065(6) -0.0220(8) C5 0.0327(7) 0.0542(9) 0.0498(8) 0.0018(6) 0.0095(6) -0.0016(7) C6 0.0302(6) 0.0342(7) 0.0442(7) 0.0066(5) 0.0084(5) -0.0003(6) C7 0.0403(7) 0.0467(8) 0.0441(8) 0.0014(6) 0.0164(6) -0.0001(6) C8 0.0469(8) 0.0485(8) 0.0368(7) 0.0028(7) 0.0080(6) -0.0030(6) C9 0.0343(7) 0.0344(7) 0.0478(8) 0.0030(5) 0.0061(6) -0.0013(6) C10 0.0368(7) 0.0469(8) 0.0500(8) 0.0009(6) 0.0142(6) 0.0073(6) C11 0.0381(7) 0.0480(8) 0.0376(7) 0.0046(6) 0.0071(6) 0.0040(6) C12 0.0419(8) 0.0432(8) 0.0588(9) 0.0025(7) 0.0080(7) -0.0039(7) 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 C5 O1 C4 . . 112.87(12) C3 N1 C3 2_755 . 117.77(18) C2 C1 C2 . 2_755 119.5(2) C2 C1 H1 . . 120.3 C2 C1 H1 2_755 . 120.3 C1 C2 C3 . . 118.50(14) C1 C2 H2 . . 120.8 C3 C2 H2 . . 120.8 N1 C3 C2 . . 122.86(14) N1 C3 C4 . . 114.79(14) C2 C3 C4 . . 122.25(13) O1 C4 C3 . . 114.53(13) O1 C4 H4A . . 108.6 C3 C4 H4A . . 108.6 O1 C4 H4B . . 108.6 C3 C4 H4B . . 108.6 H4A C4 H4B . . 107.6 O1 C5 C6 . . 110.41(11) O1 C5 H5A . . 109.6 C6 C5 H5A . . 109.6 O1 C5 H5B . . 109.6 C6 C5 H5B . . 109.6 H5A C5 H5B . . 108.1 C11 C6 C7 . . 118.96(12) C11 C6 C5 . . 122.07(12) C7 C6 C5 . . 118.97(12) C8 C7 C6 . . 120.77(13) C8 C7 H7 . . 119.6 C6 C7 H7 . . 119.6 C7 C8 C9 . . 119.92(13) C7 C8 H8 . . 120.0 C9 C8 H8 . . 120.0 C10 C9 C8 . . 119.77(12) C10 C9 C12 . . 120.20(13) C8 C9 C12 . . 120.03(13) C11 C10 C9 . . 119.91(13) C11 C10 H10 . . 120.0 C9 C10 H10 . . 120.0 C10 C11 C6 . . 120.67(13) C10 C11 H11 . . 119.7 C6 C11 H11 . . 119.7 N2 C12 C9 . . 178.67(19) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance O1 C5 . 1.4088(18) O1 C4 . 1.4217(17) N1 C3 2_755 1.3417(16) N1 C3 . 1.3417(16) N2 C12 . 1.1449(19) C1 C2 . 1.3786(19) C1 C2 2_755 1.3786(19) C1 H1 . 0.9300 C2 C3 . 1.382(2) C2 H2 . 0.9300 C3 C4 . 1.508(2) C4 H4A . 0.9700 C4 H4B . 0.9700 C5 C6 . 1.5001(18) C5 H5A . 0.9700 C5 H5B . 0.9700 C6 C11 . 1.3846(19) C6 C7 . 1.3879(19) C7 C8 . 1.3751(19) C7 H7 . 0.9300 C8 C9 . 1.387(2) C8 H8 . 0.9300 C9 C10 . 1.3847(19) C9 C12 . 1.4400(19) C10 C11 . 1.3804(19) C10 H10 . 0.9300 C11 H11 . 0.9300 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 C11 H11 O1 1_555 0.93 2.39 2.735(2) 102 no C8 H8 Cg 7_655 0.93 2.87 3.7180(15) 152 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 C2 C1 C2 C3 2_755 -0.50(9) C3 N1 C3 C2 2_755 -0.54(10) C3 N1 C3 C4 2_755 175.99(14) C1 C2 C3 N1 . 1.1(2) C1 C2 C3 C4 . -175.22(11) C5 O1 C4 C3 . -76.99(18) N1 C3 C4 O1 . 159.71(12) C2 C3 C4 O1 . -23.7(2) C4 O1 C5 C6 . -171.60(12) O1 C5 C6 C11 . -6.58(19) O1 C5 C6 C7 . 173.49(12) C11 C6 C7 C8 . -0.7(2) C5 C6 C7 C8 . 179.27(13) C6 C7 C8 C9 . 0.5(2) C7 C8 C9 C10 . 0.0(2) C7 C8 C9 C12 . 179.68(14) C8 C9 C10 C11 . -0.3(2) C12 C9 C10 C11 . 180.00(13) C9 C10 C11 C6 . 0.1(2) C7 C6 C11 C10 . 0.3(2) C5 C6 C11 C10 . -179.59(13)