# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_myself-twin _database_code_depnum_ccdc_archive 'CCDC 894545' #TrackingRef 'myself-twin.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3-Bis(cyanoxime)benzene, monohydrate ; _chemical_name_common '1,3-Bis(cyanoxime)benzene, monohydrate' _chemical_melting_point ? _chemical_formula_moiety '2(C10 H6 N4 O2) x H2O' _chemical_formula_sum 'C10 H7 N4 O2.5' _chemical_formula_weight 223.20 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'F d d 2' _symmetry_space_group_name_Hall '-F 2 -2d' _symmetry_Int_Tables_number 43 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/4, y+1/4, z+1/4' 'x+1/4, -y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' '-x+1/4, y+3/4, z+3/4' 'x+1/4, -y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' '-x+3/4, y+1/4, z+3/4' 'x+3/4, -y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' '-x+3/4, y+3/4, z+1/4' 'x+3/4, -y+3/4, z+1/4' _cell_length_a 33.748(13) _cell_length_b 34.172(14) _cell_length_c 3.7629(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4339(3) _cell_formula_units_Z 16 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 340 _cell_measurement_theta_min 2.11 _cell_measurement_theta_max 54.43 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1840 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.961 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS (Bruker AXS, 2005)' _exptl_special_details ; Data were corrected for decay and absorption using the program SADABS (Sheldrick, G.M. (2003). SADABS. Version 2.10. University of Gottingen, Germany) ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX2 CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11902 _diffrn_reflns_av_R_equivalents 0.0602 _diffrn_reflns_av_sigmaI/netI 0.0528 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min -42 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 27.13 _reflns_number_total 2394 _reflns_number_gt 1786 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0810P)^2^+5.0686P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -2(3) _refine_ls_number_reflns 2394 _refine_ls_number_parameters 174 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0872 _refine_ls_R_factor_gt 0.0600 _refine_ls_wR_factor_ref 0.1582 _refine_ls_wR_factor_gt 0.1413 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.38359(11) 0.97052(11) 0.8535(10) 0.0348(8) Uani 1 1 d . A 1 C2 C 0.35624(13) 1.00314(11) 0.8488(12) 0.0442(10) Uani 1 1 d . A 1 C3 C 0.36983(10) 0.93294(10) 0.7063(9) 0.0302(8) Uani 1 1 d . A 1 C4 C 0.39639(11) 0.90178(11) 0.6850(11) 0.0365(9) Uani 1 1 d . A 1 H4 H 0.4230 0.9050 0.7611 0.044 Uiso 1 1 calc R A 1 C5 C 0.38392(12) 0.86650(11) 0.5537(12) 0.0382(9) Uani 1 1 d . A 1 C6 C 0.34490(11) 0.86142(11) 0.4368(10) 0.0341(8) Uani 1 1 d . A 1 C7 C 0.31870(10) 0.89203(10) 0.4546(10) 0.0305(8) Uani 1 1 d . A 1 C8 C 0.33142(11) 0.92826(11) 0.5899(10) 0.0304(8) Uani 1 1 d . A 1 C9 C 0.27748(11) 0.88802(10) 0.3308(10) 0.0337(8) Uani 1 1 d . A 1 C10 C 0.26628(11) 0.85077(12) 0.1695(11) 0.0385(9) Uani 1 1 d . A 1 H6 H 0.3377(12) 0.8357(12) 0.375(13) 0.039(11) Uiso 1 1 d . B 1 H8 H 0.3133(9) 0.9469(10) 0.620(10) 0.019(8) Uiso 1 1 d . C 1 H1S H 0.2482(13) 0.7671(11) 0.753(13) 0.031(13) Uiso 1 1 d . D 1 N1 N 0.41941(10) 0.97371(10) 0.9912(9) 0.0445(9) Uani 1 1 d . A 1 N2 N 0.33513(12) 1.02853(11) 0.8474(13) 0.0600(11) Uani 1 1 d . A 1 N3 N 0.25209(11) 0.91546(12) 0.3595(11) 0.0519(10) Uani 1 1 d . A 1 N4 N 0.25713(11) 0.82240(10) 0.0387(10) 0.0458(9) Uani 1 1 d . A 1 O1 O 0.42666(8) 1.00966(8) 1.1131(9) 0.0471(8) Uani 1 1 d . A 1 H1 H 0.4499 1.0107 1.1929 0.071 Uiso 1 1 calc R A 1 O2 O 0.21689(10) 0.90756(9) 0.2353(11) 0.0502(11) Uani 0.859(5) 1 d P A 1 H2 H 0.2018 0.9268 0.2699 0.075 Uiso 0.859(5) 1 calc PR A 1 O3S O 0.2500 0.7500 0.6679(12) 0.0343(9) Uani 1 2 d S . . H5 H 0.4024(11) 0.8451(11) 0.542(11) 0.030(10) Uiso 1 1 d . . . O2A O 0.2475(5) 0.9448(5) 0.475(5) 0.0305(8) Uani 0.141(5) 1 d P A 1 H2A H 0.2242 0.9466 0.5506 0.046 Uiso 0.141(5) 1 calc PR A 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.037(2) 0.038(2) 0.029(2) 0.0004(17) 0.0030(17) -0.0049(15) C2 0.050(3) 0.035(2) 0.047(3) -0.005(2) -0.004(2) -0.006(2) C3 0.0334(18) 0.0330(19) 0.0242(18) -0.0011(15) 0.0029(15) -0.0047(14) C4 0.0314(19) 0.041(2) 0.038(2) -0.0007(18) -0.0042(17) -0.0014(16) C5 0.037(2) 0.038(2) 0.039(2) -0.0069(18) -0.0009(17) 0.0105(17) C6 0.036(2) 0.0315(19) 0.034(2) -0.0035(16) -0.0008(17) -0.0031(16) C7 0.0310(18) 0.0360(18) 0.0247(17) 0.0041(15) 0.0007(15) -0.0016(14) C8 0.0324(19) 0.0316(19) 0.0273(19) 0.0046(17) 0.0031(15) 0.0056(16) C9 0.038(2) 0.0335(19) 0.0296(19) 0.0027(17) -0.0005(16) -0.0015(16) C10 0.033(2) 0.046(2) 0.037(2) 0.0065(19) -0.0036(17) -0.0048(16) N1 0.052(2) 0.046(2) 0.0354(19) -0.0021(15) 0.0027(16) -0.0176(16) N2 0.061(2) 0.0399(19) 0.079(3) -0.006(2) -0.014(2) 0.0085(18) N3 0.045(2) 0.062(2) 0.048(2) 0.009(2) 0.0018(18) 0.0090(18) N4 0.055(2) 0.0375(18) 0.045(2) -0.0079(17) 0.0034(17) -0.0062(16) O1 0.0417(15) 0.0459(16) 0.0537(19) -0.0017(15) -0.0083(14) -0.0067(12) O2 0.0347(18) 0.0446(19) 0.071(3) -0.0059(18) -0.0057(18) 0.0025(14) O3S 0.037(2) 0.029(2) 0.037(2) 0.000 0.000 0.0030(19) O2A 0.0310(18) 0.0360(18) 0.0247(17) 0.0041(15) 0.0007(15) -0.0016(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.320(5) . ? C1 C2 1.447(6) . ? C1 C3 1.474(5) . ? C2 N2 1.122(5) . ? C3 C8 1.378(5) . ? C3 C4 1.394(5) . ? C4 C5 1.369(6) . ? C4 H4 0.9500 . ? C5 C6 1.399(5) . ? C5 H5 0.96(4) . ? C6 C7 1.371(5) . ? C6 H6 0.94(4) . ? C7 C8 1.406(5) . ? C7 C9 1.473(5) . ? C8 H8 0.89(3) . ? C9 N3 1.275(5) . ? C9 C10 1.460(6) . ? C10 N4 1.130(5) . ? N1 O1 1.334(4) . ? N3 O2A 1.103(18) . ? N3 O2 1.305(5) . ? O1 H1 0.8400 . ? O2 H2 0.8400 . ? O3S H1S 0.67(4) . ? O2A H2A 0.8400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 121.7(4) . . ? N1 C1 C3 120.5(3) . . ? C2 C1 C3 117.7(3) . . ? N2 C2 C1 179.5(5) . . ? C8 C3 C4 119.9(3) . . ? C8 C3 C1 121.1(3) . . ? C4 C3 C1 119.0(3) . . ? C5 C4 C3 119.7(3) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 120.8(3) . . ? C4 C5 H5 119(2) . . ? C6 C5 H5 120(2) . . ? C7 C6 C5 119.8(3) . . ? C7 C6 H6 124(2) . . ? C5 C6 H6 116(2) . . ? C6 C7 C8 119.5(3) . . ? C6 C7 C9 121.5(3) . . ? C8 C7 C9 119.0(3) . . ? C3 C8 C7 120.3(3) . . ? C3 C8 H8 122(2) . . ? C7 C8 H8 118(2) . . ? N3 C9 C10 120.2(4) . . ? N3 C9 C7 122.6(3) . . ? C10 C9 C7 117.2(3) . . ? N4 C10 C9 178.4(4) . . ? C1 N1 O1 112.3(3) . . ? O2A N3 C9 142.8(10) . . ? O2A N3 O2 101.6(9) . . ? C9 N3 O2 115.4(4) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 -34(61) . . . . ? C3 C1 C2 N2 144(61) . . . . ? N1 C1 C3 C8 174.3(3) . . . . ? C2 C1 C3 C8 -4.2(5) . . . . ? N1 C1 C3 C4 -5.8(5) . . . . ? C2 C1 C3 C4 175.6(4) . . . . ? C8 C3 C4 C5 -1.1(6) . . . . ? C1 C3 C4 C5 179.1(4) . . . . ? C3 C4 C5 C6 0.7(7) . . . . ? C4 C5 C6 C7 -0.2(6) . . . . ? C5 C6 C7 C8 0.1(6) . . . . ? C5 C6 C7 C9 179.4(4) . . . . ? C4 C3 C8 C7 1.0(5) . . . . ? C1 C3 C8 C7 -179.2(3) . . . . ? C6 C7 C8 C3 -0.5(5) . . . . ? C9 C7 C8 C3 -179.8(3) . . . . ? C6 C7 C9 N3 176.7(4) . . . . ? C8 C7 C9 N3 -4.0(5) . . . . ? C6 C7 C9 C10 -3.4(5) . . . . ? C8 C7 C9 C10 175.8(4) . . . . ? C2 C1 N1 O1 -1.1(5) . . . . ? C3 C1 N1 O1 -179.6(3) . . . . ? C10 C9 N3 O2A 172.9(16) . . . . ? C7 C9 N3 O2A -7.2(18) . . . . ? C10 C9 N3 O2 -0.3(6) . . . . ? C7 C9 N3 O2 179.5(4) . . . . ? 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_site_symmetry_A O1 H1 O3S 0.84 1.93 2.748(3) 165.5 11 O3S H1S N4 0.67(4) 2.20(4) 2.851(4) 167(5) 1_556 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.13 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.297 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.055 data_22-att-dis1 _database_code_depnum_ccdc_archive 'CCDC 894546' #TrackingRef '22-att-dis1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3-bis-cyanoxime(benzene), DMF solvate ; _chemical_name_common '1,3-bis-cyanoxime(benzene), DMF solvate' _chemical_melting_point 'decomposes upon heating to 78 C' _chemical_formula_moiety 'C10, H6 N4 O2, C3 H7 N O' _chemical_formula_sum 'C13 H13 N5 O3' _chemical_formula_weight 287.28 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P bcm' _symmetry_space_group_name_Hall '-P 2c 2b' _symmetry_Int_Tables_number 57 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, z+1/2' '-x, -y, -z' '-x, y-1/2, z' 'x, -y-1/2, z-1/2' 'x, y, -z-1/2' _cell_length_a 7.9182(10) _cell_length_b 13.0263(16) _cell_length_c 13.5001(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1392.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 41 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 54.17 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9534 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS (Bruker AXS, 2005)' _exptl_special_details ; Small clear prismatic crystal was placed into the Cryoloop in parathon oil, centered and used for data collection at 150 K with the use of Kryoflex system. Data were corrected for decay and absorption using the program SADABS (Sheldrick, G.M. (2003). SADABS. Version 2.10. University of Gottingen, Germany) ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX2 CCD area detector' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 21181 _diffrn_reflns_av_R_equivalents 0.0492 _diffrn_reflns_av_sigmaI/netI 0.0159 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1284 _reflns_number_gt 967 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. There is disordered solvent molecule - DMF - in this structure. The molecule of DMF occupies a special position on a mirror plane. The disorder scheme was rather complex, and it was possible to model it using the idealized geometries from a "bank" of idealized solvents structures stored on collection of Dr. Ilia Guzei, Director of Crystallographic Center of the University of Wisconsin - Madison. He also helped in modeling and successfull resolution of this complicated disorder. The OLEX 2 program was used for final refinement of the structure and preparation data for publication. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0942P)^2^+1.6724P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1284 _refine_ls_number_parameters 103 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0835 _refine_ls_R_factor_gt 0.0665 _refine_ls_wR_factor_ref 0.1991 _refine_ls_wR_factor_gt 0.1848 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0311(3) 0.37367(17) 0.56545(18) 0.0247(6) Uani 1 1 d . . 1 C2 C -0.1512(4) 0.3727(2) 0.56853(19) 0.0293(7) Uani 1 1 d . . 1 C3 C 0.1254(3) 0.37091(17) 0.66017(18) 0.0238(6) Uani 1 1 d . . 1 C4 C 0.3014(3) 0.36626(18) 0.66064(19) 0.0272(7) Uani 1 1 d . . 1 H4 H 0.3622 0.3645 0.6000 0.033 Uiso 1 1 calc R . 1 C5 C 0.3868(5) 0.3642(3) 0.7500 0.0317(9) Uani 1 2 d S . 1 H5 H 0.5067 0.3612 0.7500 0.038 Uiso 1 2 calc SR . 1 C6 C 0.0381(5) 0.3733(2) 0.7500 0.0225(8) Uani 1 2 d S . 1 H6 H -0.0817 0.3766 0.7500 0.027 Uiso 1 2 calc SR . 1 N1 N 0.1132(3) 0.37704(15) 0.48317(17) 0.0309(6) Uani 1 1 d . . 1 N2 N -0.2949(3) 0.3721(2) 0.57343(19) 0.0462(8) Uani 1 1 d . . 1 O1 O 0.0077(2) 0.37874(13) 0.40212(14) 0.0354(6) Uani 1 1 d . . 1 H1 H 0.0658 0.3808 0.3501 0.053 Uiso 1 1 calc R . 1 O1S O 0.2196(2) 0.3987(2) 0.2500 0.0326(6) Uani 1 2 d SG . 1 C2S C 0.3582(3) 0.38863(19) 0.21255(10) 0.0311(12) Uani 0.50 1 d PG . 1 H2S H 0.3752 0.3844 0.1314 0.037 Uiso 0.50 1 d PG . 1 N4S N 0.5075(2) 0.38137(16) 0.2634(2) 0.0326(6) Uani 0.50 1 d PG . 1 C5S C 0.5121(3) 0.3853(4) 0.3696(2) 0.0396(14) Uani 0.50 1 d PG . 1 H5SA H 0.3836 0.3943 0.3968 0.059 Uiso 0.50 1 d PG . 1 H5SB H 0.5659 0.3146 0.3999 0.059 Uiso 0.50 1 d PG . 1 H5SC H 0.5886 0.4502 0.3949 0.059 Uiso 0.50 1 d PG . 1 C9S C 0.6670(3) 0.3695(3) 0.2103(3) 0.0412(15) Uani 0.50 1 d PG . 1 H9SC H 0.7525 0.4333 0.2267 0.062 Uiso 0.50 1 d PG . 1 H9SA H 0.6451 0.3677 0.1305 0.062 Uiso 0.50 1 d PG . 1 H9SB H 0.7299 0.2979 0.2317 0.062 Uiso 0.50 1 d PG . 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0276(14) 0.0235(13) 0.0230(14) -0.0004(9) 0.0033(11) 0.0000(10) C2 0.0304(16) 0.0396(15) 0.0180(13) -0.0007(10) -0.0027(11) -0.0020(11) C3 0.0257(14) 0.0215(12) 0.0243(14) -0.0001(9) 0.0004(11) 0.0001(10) C4 0.0244(14) 0.0307(14) 0.0265(14) 0.0014(10) 0.0049(11) 0.0016(10) C5 0.023(2) 0.038(2) 0.034(2) 0.000 0.000 0.0023(16) C6 0.0205(18) 0.0231(17) 0.0239(19) 0.000 0.000 -0.0004(14) N1 0.0352(14) 0.0335(13) 0.0241(13) 0.0004(8) -0.0002(10) 0.0021(10) N2 0.0293(15) 0.071(2) 0.0381(15) 0.0004(12) 0.0002(11) -0.0033(12) O1 0.0385(12) 0.0481(13) 0.0195(10) 0.0003(7) -0.0020(8) 0.0021(9) O1S 0.0276(13) 0.0438(13) 0.0265(13) 0.000 0.000 0.0017(9) C2S 0.038(3) 0.038(3) 0.017(2) -0.0016(19) -0.002(2) 0.002(2) N4S 0.0276(13) 0.0438(13) 0.0265(13) 0.000 0.000 0.0017(9) C5S 0.042(3) 0.049(3) 0.029(3) 0.003(2) -0.002(3) -0.003(3) C9S 0.027(3) 0.046(3) 0.051(3) -0.006(2) 0.006(3) 0.000(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.288(3) . ? C1 C2 1.444(4) . ? C1 C3 1.481(3) . ? C2 N2 1.140(4) . ? C3 C4 1.395(4) . ? C3 C6 1.396(3) . ? C4 C5 1.383(3) . ? C4 H4 0.9500 . ? C5 C4 1.383(3) 8_557 ? C5 H5 0.9500 . ? C6 C3 1.396(3) 8_557 ? C6 H6 0.9500 . ? N1 O1 1.377(3) . ? O1 H1 0.8400 . ? O1S C2S 1.2157(11) 8_556 ? O1S C2S 1.2158 . ? C2S C2S 1.011(3) 8_556 ? C2S N4S 1.2296(14) 8_556 ? C2S N4S 1.3701 . ? C2S C5S 1.648(4) 8_556 ? C2S H2S 1.1057 . ? N4S N4S 0.361(5) 8_556 ? N4S C2S 1.2296 8_556 ? N4S C9S 1.321(2) 8_556 ? N4S C5S 1.4354 . ? N4S C9S 1.4602 . ? N4S C5S 1.796(5) 8_556 ? C5S C9S 1.647(6) 8_556 ? C5S C2S 1.6478(18) 8_556 ? C5S N4S 1.796(5) 8_556 ? C5S H5SA 1.0881 . ? C5S H5SB 1.0953 . ? C5S H5SC 1.0948 . ? C9S C9S 1.072(8) 8_556 ? C9S N4S 1.3210(15) 8_556 ? C9S C5S 1.647(4) 8_556 ? C9S H9SC 1.0953 . ? C9S H9SA 1.0908 . ? C9S H9SB 1.0950 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 122.0(2) . . ? N1 C1 C3 119.4(2) . . ? C2 C1 C3 118.6(2) . . ? N2 C2 C1 178.3(3) . . ? C4 C3 C6 119.4(3) . . ? C4 C3 C1 120.6(2) . . ? C6 C3 C1 120.0(3) . . ? C5 C4 C3 119.6(3) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C4 121.4(4) . 8_557 ? C4 C5 H5 119.3 . . ? C4 C5 H5 119.3 8_557 . ? C3 C6 C3 120.6(3) . 8_557 ? C3 C6 H6 119.7 . . ? C3 C6 H6 119.7 8_557 . ? C1 N1 O1 112.3(2) . . ? N1 O1 H1 109.5 . . ? C2S O1S C2S 49.15(11) 8_556 . ? C2S C2S O1S 65.4 8_556 . ? C2S C2S N4S 74.7(2) 8_556 8_556 ? O1S C2S N4S 140.0(2) . 8_556 ? C2S C2S N4S 59.9 8_556 . ? O1S C2S N4S 125.3 . . ? N4S C2S N4S 14.7(2) 8_556 . ? C2S C2S C5S 132.30(14) 8_556 8_556 ? O1S C2S C5S 161.84(14) . 8_556 ? N4S C2S C5S 57.68(10) 8_556 8_556 ? N4S C2S C5S 72.39(14) . 8_556 ? N4S N4S C2S 105.33(12) 8_556 8_556 ? N4S N4S C9S 105.6(4) 8_556 8_556 ? C2S N4S C9S 149.0(5) 8_556 8_556 ? N4S N4S C2S 59.9 8_556 . ? C2S N4S C2S 45.38(12) 8_556 . ? C9S N4S C2S 165.4(3) 8_556 . ? N4S N4S C5S 177.5 8_556 . ? C2S N4S C5S 75.95(12) 8_556 . ? C9S N4S C5S 73.2(4) 8_556 . ? C2S N4S C5S 121.3 . . ? N4S N4S C9S 60.6 8_556 . ? C2S N4S C9S 165.76(12) 8_556 . ? C9S N4S C9S 45.0(4) 8_556 . ? C2S N4S C9S 120.5 . . ? C5S N4S C9S 118.2 . . ? N4S N4S C5S 2.0 8_556 8_556 ? C2S N4S C5S 106.33(12) 8_556 8_556 ? C9S N4S C5S 104.7(3) 8_556 8_556 ? C2S N4S C5S 61.0 . 8_556 ? C5S N4S C5S 175.5 . 8_556 ? C9S N4S C5S 59.7 . 8_556 ? N4S C5S C9S 50.2(2) . 8_556 ? N4S C5S C2S 46.38(7) . 8_556 ? C9S C5S C2S 96.5(3) 8_556 8_556 ? N4S C5S N4S 0.5 . 8_556 ? C9S C5S N4S 50.0(2) 8_556 8_556 ? C2S C5S N4S 46.64(6) 8_556 8_556 ? C9S C9S N4S 74.4(2) 8_556 8_556 ? C9S C9S N4S 60.6 8_556 . ? N4S C9S N4S 13.8(2) 8_556 . ? C9S C9S C5S 130.92(14) 8_556 8_556 ? N4S C9S C5S 56.58(8) 8_556 8_556 ? N4S C9S C5S 70.35(14) . 8_556 ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 -175(100) . . . . ? N1 C1 C3 C4 -3.5(3) . . . . ? C2 C1 C3 C4 176.6(2) . . . . ? N1 C1 C3 C6 176.3(2) . . . . ? C2 C1 C3 C6 -3.6(3) . . . . ? C6 C3 C4 C5 -0.1(4) . . . . ? C1 C3 C4 C5 179.8(2) . . . . ? C3 C4 C5 C4 0.2(5) . . . 8_557 ? C4 C3 C6 C3 -0.1(4) . . . 8_557 ? C1 C3 C6 C3 -179.89(18) . . . 8_557 ? C2 C1 N1 O1 -0.4(3) . . . . ? C3 C1 N1 O1 179.71(19) . . . . ? C2S O1S C2S N4S -3.3 8_556 . . 8_556 ? C2S O1S C2S N4S -2.3 8_556 . . . ? C2S O1S C2S C5S -168.63(11) 8_556 . . 8_556 ? C2S C2S N4S N4S -180.0 8_556 . . 8_556 ? O1S C2S N4S N4S -177.5 . . . 8_556 ? C5S C2S N4S N4S -2.0 8_556 . . 8_556 ? O1S C2S N4S C2S 2.5 . . . 8_556 ? N4S C2S N4S C2S 180.0 8_556 . . 8_556 ? C5S C2S N4S C2S 178.0 8_556 . . 8_556 ? C2S C2S N4S C9S 170.7(2) 8_556 . . 8_556 ? O1S C2S N4S C9S 173.1(2) . . . 8_556 ? N4S C2S N4S C9S -9.3(2) 8_556 . . 8_556 ? C5S C2S N4S C9S -11.3(2) 8_556 . . 8_556 ? C2S C2S N4S C5S -2.5 8_556 . . . ? O1S C2S N4S C5S -0.1 . . . . ? N4S C2S N4S C5S 177.5 8_556 . . . ? C5S C2S N4S C5S 175.5 8_556 . . . ? C2S C2S N4S C9S 177.5 8_556 . . . ? O1S C2S N4S C9S -180.0 . . . . ? N4S C2S N4S C9S -2.5 8_556 . . . ? C5S C2S N4S C9S -4.4 8_556 . . . ? C2S C2S N4S C5S -178.0 8_556 . . 8_556 ? O1S C2S N4S C5S -175.6 . . . 8_556 ? N4S C2S N4S C5S 2.0 8_556 . . 8_556 ? C2S N4S C5S C9S 176.4 8_556 . . 8_556 ? C2S N4S C5S C9S 178.2 . . . 8_556 ? C9S N4S C5S C9S -1.9 . . . 8_556 ? C9S N4S C5S C2S -176.4 8_556 . . 8_556 ? C2S N4S C5S C2S 1.9 . . . 8_556 ? C9S N4S C5S C2S -178.2 . . . 8_556 ? C2S N4S C5S N4S -120.7(6) 8_556 . . 8_556 ? C9S N4S C5S N4S 63.0(6) 8_556 . . 8_556 ? C2S N4S C5S N4S -118.8(6) . . . 8_556 ? C9S N4S C5S N4S 61.1(6) . . . 8_556 ? N4S N4S C9S C9S 180.0 8_556 . . 8_556 ? C2S N4S C9S C9S -170.43(7) 8_556 . . 8_556 ? C2S N4S C9S C9S -177.6 . . . 8_556 ? C5S N4S C9S C9S 2.5 . . . 8_556 ? C5S N4S C9S C9S 177.9 8_556 . . 8_556 ? C2S N4S C9S N4S 9.58(7) 8_556 . . 8_556 ? C9S N4S C9S N4S -180.0 8_556 . . 8_556 ? C2S N4S C9S N4S 2.4 . . . 8_556 ? C5S N4S C9S N4S -177.5 . . . 8_556 ? C5S N4S C9S N4S -2.0 8_556 . . 8_556 ? N4S N4S C9S C5S 2.0 8_556 . . 8_556 ? C2S N4S C9S C5S 11.62(8) 8_556 . . 8_556 ? C9S N4S C9S C5S -177.9 8_556 . . 8_556 ? C2S N4S C9S C5S 4.5 . . . 8_556 ? C5S N4S C9S C5S -175.4 . . . 8_556 ? 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_site_symmetry_A O1 H1 O1S 0.84 1.83 2.664(2) 169.7 . O1 H1 O1S 0.84 1.83 2.664(2) 169.7 8_556 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.905 _refine_diff_density_min -0.749 _refine_diff_density_rms 0.070 data_new-1 _database_code_depnum_ccdc_archive 'CCDC 894547' #TrackingRef 'new-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,4-bis(cyanoxime)benzene ; _chemical_name_common 1,4-bis(cyanoxime)benzene _chemical_melting_point ? _chemical_formula_moiety 'C10 H6 N4 O2' _chemical_formula_sum 'C10 H6 N4 O2' _chemical_formula_weight 214.19 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P bca' _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_Int_Tables_number 61 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 5.1519(9) _cell_length_b 11.244(2) _cell_length_c 16.370(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 948.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 23 _cell_measurement_theta_min 2.06 _cell_measurement_theta_max 27.54 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.500 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9676 _exptl_absorpt_correction_T_max 0.9782 _exptl_absorpt_process_details 'SADABS (Bruker AXS, 2005)' _exptl_special_details ; Small clear prismatic crystal was placed into the Cryoloop in parathon oil, centered and used for data collection at ~150 K with the use of Kryoflex system. Data were corrected for decay and absorption using the program SADABS (Sheldrick, G.M. (2003). SADABS. Version 2.10. University of Gottingen, Germany) ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX2 CCD area detector' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 21292 _diffrn_reflns_av_R_equivalents 0.0677 _diffrn_reflns_av_sigmaI/netI 0.0293 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.62 _diffrn_reflns_theta_max 30.48 _reflns_number_total 1441 _reflns_number_gt 975 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1182P)^2^+0.0975P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.015(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1441 _refine_ls_number_parameters 75 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0934 _refine_ls_R_factor_gt 0.0635 _refine_ls_wR_factor_ref 0.2028 _refine_ls_wR_factor_gt 0.1809 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C2 C 0.0311(4) -0.10329(17) 0.66194(11) 0.0332(4) Uani 1 1 d . . . C1 C 0.1007(4) 0.00790(15) 0.62302(11) 0.0317(5) Uani 1 1 d . . . C3 C 0.3066(3) 0.00482(14) 0.56002(10) 0.0282(4) Uani 1 1 d . . . C4 C 0.5331(4) 0.09558(14) 0.44708(11) 0.0306(4) Uani 1 1 d . . . H4 H 0.5554 0.1608 0.4109 0.037 Uiso 1 1 calc R . . C5 C 0.3420(4) 0.09982(14) 0.50684(12) 0.0318(4) Uani 1 1 d . . . H5 H 0.2346 0.1682 0.5114 0.038 Uiso 1 1 calc R . . N2 N -0.0249(3) -0.19368(15) 0.68897(11) 0.0415(5) Uani 1 1 d . . . N1 N -0.0285(3) 0.10393(15) 0.63722(10) 0.0372(5) Uani 1 1 d . . . O1 O -0.2170(3) 0.08600(12) 0.69587(9) 0.0429(4) Uani 1 1 d . . . H1 H -0.3027 0.1489 0.7023 0.064 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.0346(9) 0.0298(10) 0.0352(9) -0.0006(7) -0.0004(8) 0.0008(7) C1 0.0347(9) 0.0267(9) 0.0336(9) 0.0003(7) -0.0026(7) -0.0029(7) C3 0.0312(9) 0.0241(8) 0.0294(8) -0.0013(6) -0.0032(6) -0.0023(6) C4 0.0363(9) 0.0222(8) 0.0333(9) 0.0024(6) -0.0030(7) -0.0015(6) C5 0.0349(9) 0.0223(8) 0.0381(10) -0.0002(6) -0.0024(7) 0.0008(7) N2 0.0419(10) 0.0331(9) 0.0494(11) 0.0066(7) 0.0026(7) -0.0014(7) N1 0.0404(9) 0.0340(9) 0.0372(8) -0.0014(6) 0.0015(7) -0.0009(7) O1 0.0465(9) 0.0363(8) 0.0459(8) 0.0017(6) 0.0084(6) 0.0054(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2 N2 1.145(2) . ? C2 C1 1.448(3) . ? C1 N1 1.289(2) . ? C1 C3 1.480(3) . ? C3 C5 1.390(2) . ? C3 C4 1.404(2) 5_656 ? C4 C5 1.389(3) . ? C4 C3 1.404(2) 5_656 ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? N1 O1 1.380(2) . ? O1 H1 0.8400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C2 C1 176.6(2) . . ? N1 C1 C2 121.06(17) . . ? N1 C1 C3 121.01(16) . . ? C2 C1 C3 117.63(15) . . ? C5 C3 C4 119.26(16) . 5_656 ? C5 C3 C1 120.84(16) . . ? C4 C3 C1 119.89(15) 5_656 . ? C5 C4 C3 120.21(15) . 5_656 ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 5_656 . ? C4 C5 C3 120.52(16) . . ? C4 C5 H5 119.7 . . ? C3 C5 H5 119.7 . . ? C1 N1 O1 111.48(16) . . ? N1 O1 H1 109.5 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 C2 C1 N1 124(4) . . . . ? N2 C2 C1 C3 -50(4) . . . . ? N1 C1 C3 C5 -9.0(3) . . . . ? C2 C1 C3 C5 164.67(17) . . . . ? N1 C1 C3 C4 171.73(17) . . . 5_656 ? C2 C1 C3 C4 -14.6(2) . . . 5_656 ? C3 C4 C5 C3 -0.2(3) 5_656 . . . ? C4 C3 C5 C4 0.2(3) 5_656 . . . ? C1 C3 C5 C4 -179.05(16) . . . . ? C2 C1 N1 O1 4.2(2) . . . . ? C3 C1 N1 O1 177.69(15) . . . . ? 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_site_symmetry_A O1 H1 N2 0.84 1.99 2.814(2) 165.6 6_565 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.326 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.068 data_o-chiral-1 _database_code_depnum_ccdc_archive 'CCDC 894548' #TrackingRef 'O-chiral-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,4-bis(cyanoxime)benzene, DMSO solvate ; _chemical_name_common '1,4-bis(cyanoxime)benzene, DMSO solvate' _chemical_melting_point ? _chemical_formula_moiety 'C10 H6 N4 O2, 2(C2 H6 S O)' _chemical_formula_sum 'C14 H18 N4 O4 S2' _chemical_formula_weight 370.48 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.2397(4) _cell_length_b 7.8663(5) _cell_length_c 9.6240(6) _cell_angle_alpha 81.3740(10) _cell_angle_beta 80.6960(10) _cell_angle_gamma 72.0250(10) _cell_volume 440.88(5) _cell_formula_units_Z 1 _cell_measurement_temperature 129(2) _cell_measurement_reflns_used 140 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 27.54 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 194 _exptl_absorpt_coefficient_mu 0.328 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.897 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details 'SADABS (Bruker AXS, 2005)' _exptl_special_details ; Data were corrected for decay and absorption using the program SADABS (Sheldrick, G.M. (2003). SADABS. Version 2.10. University of Gottingen, Germany) ; _diffrn_ambient_temperature 129(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX2 CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 5053 _diffrn_reflns_av_R_equivalents 0.0152 _diffrn_reflns_av_sigmaI/netI 0.0177 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 27.00 _reflns_number_total 1904 _reflns_number_gt 1722 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0365P)^2^+0.1621P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1904 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0305 _refine_ls_R_factor_gt 0.0269 _refine_ls_wR_factor_ref 0.0738 _refine_ls_wR_factor_gt 0.0706 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.22022(16) 0.64808(13) 0.74345(11) 0.0264(2) Uani 1 1 d . . . O1S O 0.54175(17) 0.78158(13) 0.61380(10) 0.0274(2) Uani 1 1 d . . . C1 C 0.8769(2) 0.74608(16) 0.85917(13) 0.0182(3) Uani 1 1 d . . . C2 C 0.8634(2) 0.56598(17) 0.85450(13) 0.0214(3) Uani 1 1 d . . . C3 C 0.6836(2) 0.87637(16) 0.93155(12) 0.0170(2) Uani 1 1 d . . . C4 C 0.4791(2) 0.83597(17) 0.97747(13) 0.0189(3) Uani 1 1 d . . . H4 H 0.4651 0.7236 0.9620 0.023 Uiso 1 1 calc R . . C5 C 0.2969(2) 0.95782(17) 1.04523(13) 0.0191(3) Uani 1 1 d . . . C1S C 0.9010(2) 0.8156(2) 0.44283(15) 0.0297(3) Uani 1 1 d . . . H1SA H 0.9966 0.7955 0.5186 0.045 Uiso 1 1 calc R . . H1SB H 0.8198 0.9439 0.4274 0.045 Uiso 1 1 calc R . . H1SC H 0.9964 0.7764 0.3554 0.045 Uiso 1 1 calc R . . C2S C 0.5538(2) 0.7646(2) 0.34005(15) 0.0294(3) Uani 1 1 d . . . H2SA H 0.4923 0.8958 0.3316 0.044 Uiso 1 1 calc R . . H2SB H 0.4293 0.7107 0.3498 0.044 Uiso 1 1 calc R . . H2SC H 0.6589 0.7280 0.2552 0.044 Uiso 1 1 calc R . . H5 H 0.153(3) 0.928(2) 1.0765(16) 0.020(4) Uiso 1 1 d . . . N1 N 1.05670(18) 0.78979(14) 0.80192(11) 0.0212(2) Uani 1 1 d . . . N2 N 0.8561(2) 0.42336(16) 0.85036(14) 0.0317(3) Uani 1 1 d . . . S1 S 0.70124(5) 0.69044(4) 0.49219(3) 0.02160(11) Uani 1 1 d . . . H1 H 1.337(4) 0.694(3) 0.702(2) 0.053(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0217(5) 0.0235(5) 0.0317(5) -0.0096(4) 0.0065(4) -0.0051(4) O1S 0.0273(5) 0.0288(5) 0.0241(5) -0.0060(4) 0.0074(4) -0.0091(4) C1 0.0200(6) 0.0176(6) 0.0166(6) -0.0010(4) -0.0029(5) -0.0050(5) C2 0.0190(6) 0.0222(7) 0.0210(6) -0.0043(5) 0.0027(5) -0.0047(5) C3 0.0187(6) 0.0176(6) 0.0145(5) -0.0013(4) -0.0026(4) -0.0046(5) C4 0.0215(6) 0.0168(6) 0.0202(6) -0.0033(5) -0.0026(5) -0.0075(5) C5 0.0182(6) 0.0204(6) 0.0202(6) -0.0021(5) -0.0016(5) -0.0082(5) C1S 0.0222(7) 0.0409(8) 0.0274(7) -0.0075(6) 0.0023(5) -0.0121(6) C2S 0.0254(7) 0.0337(8) 0.0284(7) -0.0077(6) -0.0066(6) -0.0038(6) N1 0.0199(5) 0.0218(5) 0.0205(5) -0.0052(4) 0.0004(4) -0.0039(4) N2 0.0333(7) 0.0226(6) 0.0382(7) -0.0083(5) 0.0059(5) -0.0093(5) S1 0.02136(18) 0.01954(18) 0.02081(18) -0.00271(12) 0.00020(12) -0.00263(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.3787(13) . ? O1 H1 0.92(2) . ? O1S S1 1.5195(10) . ? C1 N1 1.2892(17) . ? C1 C2 1.4526(18) . ? C1 C3 1.4732(17) . ? C2 N2 1.1437(18) . ? C3 C4 1.3961(17) . ? C3 C5 1.4003(17) 2_677 ? C4 C5 1.3829(17) . ? C4 H4 0.9500 . ? C5 C3 1.4003(17) 2_677 ? C5 H5 0.984(15) . ? C1S S1 1.7819(15) . ? C1S H1SA 0.9800 . ? C1S H1SB 0.9800 . ? C1S H1SC 0.9800 . ? C2S S1 1.7827(14) . ? C2S H2SA 0.9800 . ? C2S H2SB 0.9800 . ? C2S H2SC 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 O1 H1 105.1(13) . . ? N1 C1 C2 120.21(11) . . ? N1 C1 C3 120.82(11) . . ? C2 C1 C3 118.97(11) . . ? N2 C2 C1 179.02(14) . . ? C4 C3 C5 119.36(11) . 2_677 ? C4 C3 C1 120.40(11) . . ? C5 C3 C1 120.24(11) 2_677 . ? C5 C4 C3 120.68(11) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C3 119.95(11) . 2_677 ? C4 C5 H5 119.9(9) . . ? C3 C5 H5 120.2(9) 2_677 . ? S1 C1S H1SA 109.5 . . ? S1 C1S H1SB 109.5 . . ? H1SA C1S H1SB 109.5 . . ? S1 C1S H1SC 109.5 . . ? H1SA C1S H1SC 109.5 . . ? H1SB C1S H1SC 109.5 . . ? S1 C2S H2SA 109.5 . . ? S1 C2S H2SB 109.5 . . ? H2SA C2S H2SB 109.5 . . ? S1 C2S H2SC 109.5 . . ? H2SA C2S H2SC 109.5 . . ? H2SB C2S H2SC 109.5 . . ? C1 N1 O1 111.93(11) . . ? O1S S1 C1S 104.61(6) . . ? O1S S1 C2S 106.21(6) . . ? C1S S1 C2S 97.49(7) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 17(8) . . . . ? C3 C1 C2 N2 -162(8) . . . . ? N1 C1 C3 C4 171.88(11) . . . . ? C2 C1 C3 C4 -8.83(17) . . . . ? N1 C1 C3 C5 -8.04(18) . . . 2_677 ? C2 C1 C3 C5 171.25(11) . . . 2_677 ? C5 C3 C4 C5 0.1(2) 2_677 . . . ? C1 C3 C4 C5 -179.87(11) . . . . ? C3 C4 C5 C3 -0.1(2) . . . 2_677 ? C2 C1 N1 O1 -1.09(17) . . . . ? C3 C1 N1 O1 178.19(10) . . . . ? 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_site_symmetry_A O1 H1 O1S 0.92(2) 1.68(2) 2.6044(14) 176(2) 1_655 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.327 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.043