# Supplementary Material (ESI) for PCCP # This journal is (c) the Owner Societies 2009 data_global _journal_name_full Phys.Chem.Chem.Phys.(PCCP) _journal_coden_Cambridge 1326 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Tetsuo Asaji' 'Daiki Amino' 'Kazuma Gotoh' 'Hiroyuki Ishida' 'Akiko Konnai' 'Janez Seliger' 'Veselko Zagar' _publ_contact_author_name 'Tetsuo Asaji' _publ_contact_author_email ASAJI@CHS.NIHON-U.AC.JP _publ_section_title ; Hydrogen bonding in 1,2-diazine-chloranilic acid (2/1) studied by 14N nuclear quadrupole coupling tensor and multi-temperature X-ray diffraction ; # Attachment '144K.cif' # Asaji et al. #Hydrogen bonding in 1,2-diazine--chloranilic acid (2/1) #studied ny ^14^N nuclear quadrupole coupling tensor #and multi-temperature X-ray diffraction data_144K _database_code_depnum_ccdc_archive 'CCDC 706680' _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl2 N4 O4' _chemical_formula_sum 'C14 H10 Cl2 N4 O4' _chemical_formula_weight 369.16 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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' _cell_length_a 3.73872(14) _cell_length_b 20.1285(5) _cell_length_c 9.6317(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.9799(12) _cell_angle_gamma 90.00 _cell_volume 715.95(4) _cell_formula_units_Z 2 _cell_measurement_temperature 144(1) _cell_measurement_reflns_used 10633 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 30.0 _exptl_crystal_description platelet _exptl_crystal_colour brown _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.712 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.484 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Higashi, T. (1999). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.875 _exptl_absorpt_correction_T_max 0.953 _exptl_special_details ; ? ; _diffrn_ambient_temperature 144(1) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11660 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_sigmaI/netI 0.0166 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.72 _diffrn_reflns_theta_max 29.97 _reflns_number_total 2083 _reflns_number_gt 1874 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku/MSC, 2004)' _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'CrystalStructure and PLATON (Spek, 2003)' _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^)+(0.0605P)^2^+0.1374P] 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 2083 _refine_ls_number_parameters 116 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0353 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0955 _refine_ls_wR_factor_gt 0.0942 _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_restrained_S_all 1.116 _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 Cl1 Cl 0.57641(8) 0.497316(12) 0.18752(3) 0.01888(11) Uani 1 1 d . . . O1 O 0.7159(3) 0.61239(4) 0.38164(9) 0.0251(2) Uani 1 1 d . . . O2 O 0.9052(3) 0.38241(4) 0.35802(9) 0.0214(2) Uani 1 1 d . . . H2 H 0.983(14) 0.353(3) 0.404(5) 0.026 Uiso 0.34(3) 1 d P . . N1 N 1.0488(3) 0.26557(5) 0.45650(10) 0.0179(2) Uani 1 1 d . . . H1 H 1.024(7) 0.3090(14) 0.431(3) 0.021 Uiso 0.66(3) 1 d P . . N2 N 0.8671(3) 0.22714(5) 0.35517(10) 0.0192(2) Uani 1 1 d . . . C1 C 0.8454(3) 0.55949(5) 0.43121(11) 0.0163(2) Uani 1 1 d . . . C2 C 0.8081(3) 0.49749(5) 0.35838(12) 0.0155(2) Uani 1 1 d . . . C3 C 0.9428(3) 0.43874(5) 0.41898(11) 0.0161(2) Uani 1 1 d . . . C4 C 0.8797(3) 0.16204(6) 0.37753(12) 0.0195(2) Uani 1 1 d . . . H4 H 0.7550 0.1337 0.3072 0.023 Uiso 1 1 calc R . . C5 C 1.0681(3) 0.13293(6) 0.50007(12) 0.0196(2) Uani 1 1 d . . . H5 H 1.0667 0.0861 0.5129 0.024 Uiso 1 1 calc R . . C6 C 1.2542(3) 0.17354(6) 0.60077(12) 0.0194(2) Uani 1 1 d . . . H6 H 1.3884 0.1561 0.6847 0.023 Uiso 1 1 calc R . . C7 C 1.2373(3) 0.24188(6) 0.57406(11) 0.0185(2) Uani 1 1 d . . . H7 H 1.3626 0.2717 0.6411 0.022 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 Cl1 0.02314(17) 0.01817(16) 0.01285(16) -0.00008(8) -0.00490(11) 0.00048(9) O1 0.0350(5) 0.0156(4) 0.0205(4) 0.0006(3) -0.0085(4) 0.0048(3) O2 0.0304(5) 0.0148(4) 0.0164(4) -0.0018(3) -0.0050(3) 0.0023(3) N1 0.0205(5) 0.0160(4) 0.0159(4) -0.0016(3) -0.0013(3) 0.0004(3) N2 0.0222(5) 0.0188(5) 0.0145(4) -0.0012(3) -0.0034(3) 0.0000(3) C1 0.0181(5) 0.0155(5) 0.0142(5) 0.0003(4) -0.0010(4) 0.0005(4) C2 0.0182(5) 0.0158(5) 0.0111(5) 0.0000(3) -0.0022(4) 0.0003(3) C3 0.0173(5) 0.0164(5) 0.0134(5) 0.0004(4) -0.0012(4) 0.0009(4) C4 0.0215(5) 0.0175(5) 0.0178(5) -0.0019(4) -0.0015(4) -0.0010(4) C5 0.0211(5) 0.0163(5) 0.0209(6) 0.0016(4) 0.0013(4) 0.0007(4) C6 0.0210(5) 0.0199(5) 0.0162(5) 0.0024(4) -0.0005(4) 0.0026(4) C7 0.0206(5) 0.0191(5) 0.0144(5) -0.0026(4) -0.0017(4) 0.0002(4) _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 Cl1 C2 1.7359(12) . ? O1 C1 1.2343(13) . ? O2 C3 1.2745(13) . ? O2 H2 0.77(6) . ? N1 C7 1.3256(14) . ? N1 N2 1.3435(13) . ? N1 H1 0.91(3) . ? N2 C4 1.3277(14) . ? C1 C2 1.4278(15) . ? C1 C3 1.5342(16) 3_766 ? C2 C3 1.3788(14) . ? C3 C1 1.5342(16) 3_766 ? C4 C5 1.4047(15) . ? C4 H4 0.9500 . ? C5 C6 1.3721(16) . ? C5 H5 0.9500 . ? C6 C7 1.3991(15) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? 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 C3 O2 H2 114(4) . . ? C7 N1 N2 123.68(10) . . ? C7 N1 H1 126.3(16) . . ? N2 N1 H1 110.0(16) . . ? C4 N2 N1 116.70(10) . . ? O1 C1 C2 124.17(10) . . ? O1 C1 C3 117.22(9) . 3_766 ? C2 C1 C3 118.61(9) . 3_766 ? C3 C2 C1 122.72(11) . . ? C3 C2 Cl1 119.66(8) . . ? C1 C2 Cl1 117.61(8) . . ? O2 C3 C2 124.14(10) . . ? O2 C3 C1 117.23(9) . 3_766 ? C2 C3 C1 118.62(9) . 3_766 ? N2 C4 C5 123.26(11) . . ? N2 C4 H4 118.4 . . ? C5 C4 H4 118.4 . . ? C6 C5 C4 118.55(11) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? C5 C6 C7 116.90(10) . . ? C5 C6 H6 121.6 . . ? C7 C6 H6 121.6 . . ? N1 C7 C6 120.90(10) . . ? N1 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? 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 C7 N1 N2 C4 0.58(17) . . . . ? O1 C1 C2 C3 -177.13(12) . . . . ? C3 C1 C2 C3 2.51(19) 3_766 . . . ? O1 C1 C2 Cl1 1.86(17) . . . . ? C3 C1 C2 Cl1 -178.50(8) 3_766 . . . ? C1 C2 C3 O2 177.99(12) . . . . ? Cl1 C2 C3 O2 -0.98(17) . . . . ? C1 C2 C3 C1 -2.51(19) . . . 3_766 ? Cl1 C2 C3 C1 178.52(8) . . . 3_766 ? N1 N2 C4 C5 0.48(18) . . . . ? N2 C4 C5 C6 -1.23(19) . . . . ? C4 C5 C6 C7 0.91(17) . . . . ? N2 N1 C7 C6 -0.87(18) . . . . ? C5 C6 C7 N1 0.07(17) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 29.97 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.528 _refine_diff_density_min -0.345 _refine_diff_density_rms 0.083 # Attachment '177K.cif' # Asaji et al. #Hydrogen bonding in 1,2-diazine--chloranilic acid (2/1) #studied ny ^14^N nuclear quadrupole coupling tensor #and multi-temperature X-ray diffraction data_177K _database_code_depnum_ccdc_archive 'CCDC 706681' _chemical_name_systematic ; ? ; _chemical_name_common ; 1,2-diazine--chloranilic acid (2/1) ; _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl2 N4 O4' _chemical_formula_sum 'C14 H10 Cl2 N4 O4' _chemical_formula_weight 369.16 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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' _cell_length_a 3.75092(13) _cell_length_b 20.1711(5) _cell_length_c 9.6437(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.1239(12) _cell_angle_gamma 90.00 _cell_volume 720.41(4) _cell_formula_units_Z 2 _cell_measurement_temperature 177(1) _cell_measurement_reflns_used 10707 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 30.0 _exptl_crystal_description platelet _exptl_crystal_colour brown _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.702 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.481 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Higashi, T. (1999). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.874 _exptl_absorpt_correction_T_max 0.953 _exptl_special_details ; ? ; _diffrn_ambient_temperature 177(1) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9542 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0144 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.71 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1640 _reflns_number_gt 1484 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku/MSC, 2004)' _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'CrystalStructure and PLATON (Spek, 2003)' _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^)+(0.0473P)^2^+0.1807P] 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 1640 _refine_ls_number_parameters 116 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0314 _refine_ls_R_factor_gt 0.0291 _refine_ls_wR_factor_ref 0.0803 _refine_ls_wR_factor_gt 0.0793 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _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 Cl1 Cl 0.57614(8) 0.497336(13) 0.18779(3) 0.02372(13) Uani 1 1 d . . . O1 O 0.7197(3) 0.61218(4) 0.38142(10) 0.0312(2) Uani 1 1 d . . . O2 O 0.9020(3) 0.38262(5) 0.35835(10) 0.0268(2) Uani 1 1 d . . . H2 H 0.981(13) 0.356(3) 0.401(5) 0.032 Uiso 0.38(3) 1 d P . . N1 N 1.0463(3) 0.26565(5) 0.45697(11) 0.0225(2) Uani 1 1 d . . . H1 H 1.020(7) 0.3088(15) 0.438(3) 0.027 Uiso 0.62(3) 1 d P . . N2 N 0.8647(3) 0.22727(5) 0.35576(11) 0.0240(2) Uani 1 1 d . . . C1 C 0.8468(3) 0.55945(6) 0.43096(12) 0.0203(3) Uani 1 1 d . . . C2 C 0.8083(3) 0.49747(5) 0.35856(13) 0.0194(3) Uani 1 1 d . . . C3 C 0.9413(3) 0.43890(6) 0.41924(12) 0.0201(3) Uani 1 1 d . . . C4 C 0.8782(3) 0.16246(6) 0.37807(13) 0.0242(3) Uani 1 1 d . . . H4 H 0.7539 0.1342 0.3077 0.029 Uiso 1 1 calc R . . C5 C 1.0665(4) 0.13348(6) 0.50016(13) 0.0244(3) Uani 1 1 d . . . H5 H 1.0658 0.0868 0.5128 0.029 Uiso 1 1 calc R . . C6 C 1.2516(4) 0.17383(6) 0.60079(13) 0.0242(3) Uani 1 1 d . . . H6 H 1.3854 0.1564 0.6847 0.029 Uiso 1 1 calc R . . C7 C 1.2342(3) 0.24191(6) 0.57418(13) 0.0229(3) Uani 1 1 d . . . H7 H 1.3593 0.2716 0.6413 0.028 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 Cl1 0.0287(2) 0.02312(19) 0.01616(18) -0.00013(10) -0.00606(12) 0.00071(10) O1 0.0432(6) 0.0200(4) 0.0251(5) 0.0000(4) -0.0109(4) 0.0058(4) O2 0.0378(6) 0.0186(4) 0.0205(5) -0.0017(4) -0.0064(4) 0.0031(4) N1 0.0255(5) 0.0204(5) 0.0200(5) -0.0019(4) -0.0013(4) 0.0005(4) N2 0.0271(6) 0.0240(5) 0.0184(5) -0.0009(4) -0.0038(4) -0.0001(4) C1 0.0213(6) 0.0204(6) 0.0179(6) 0.0015(4) -0.0008(4) 0.0005(4) C2 0.0213(6) 0.0214(6) 0.0136(6) 0.0002(4) -0.0029(5) 0.0008(4) C3 0.0208(6) 0.0212(6) 0.0171(5) -0.0001(4) -0.0002(4) 0.0007(4) C4 0.0256(6) 0.0227(6) 0.0225(6) -0.0038(5) -0.0011(5) -0.0020(5) C5 0.0260(6) 0.0201(6) 0.0265(7) 0.0020(5) 0.0023(5) 0.0009(5) C6 0.0254(6) 0.0266(6) 0.0195(6) 0.0034(5) -0.0001(5) 0.0037(5) C7 0.0243(6) 0.0243(6) 0.0184(6) -0.0032(5) -0.0020(5) 0.0010(5) _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 Cl1 C2 1.7367(13) . ? O1 C1 1.2308(15) . ? O2 C3 1.2760(15) . ? O2 H2 0.72(5) . ? N1 C7 1.3233(16) . ? N1 N2 1.3435(14) . ? N1 H1 0.89(3) . ? N2 C4 1.3247(16) . ? C1 C2 1.4281(16) . ? C1 C3 1.5348(17) 3_766 ? C2 C3 1.3763(16) . ? C3 C1 1.5348(17) 3_766 ? C4 C5 1.4011(17) . ? C4 H4 0.9500 . ? C5 C6 1.3682(18) . ? C5 H5 0.9500 . ? C6 C7 1.3967(17) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? 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 C3 O2 H2 114(4) . . ? C7 N1 N2 123.50(11) . . ? C7 N1 H1 123.7(18) . . ? N2 N1 H1 112.8(17) . . ? C4 N2 N1 116.67(10) . . ? O1 C1 C2 124.33(11) . . ? O1 C1 C3 117.23(10) . 3_766 ? C2 C1 C3 118.44(10) . 3_766 ? C3 C2 C1 122.81(12) . . ? C3 C2 Cl1 119.69(9) . . ? C1 C2 Cl1 117.49(9) . . ? O2 C3 C2 124.08(11) . . ? O2 C3 C1 117.21(10) . 3_766 ? C2 C3 C1 118.70(10) . 3_766 ? N2 C4 C5 123.33(11) . . ? N2 C4 H4 118.3 . . ? C5 C4 H4 118.3 . . ? C6 C5 C4 118.64(12) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? C5 C6 C7 116.80(11) . . ? C5 C6 H6 121.6 . . ? C7 C6 H6 121.6 . . ? N1 C7 C6 121.05(11) . . ? N1 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? 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 C7 N1 N2 C4 0.40(18) . . . . ? O1 C1 C2 C3 -177.24(13) . . . . ? C3 C1 C2 C3 2.5(2) 3_766 . . . ? O1 C1 C2 Cl1 1.70(19) . . . . ? C3 C1 C2 Cl1 -178.58(9) 3_766 . . . ? C1 C2 C3 O2 177.95(12) . . . . ? Cl1 C2 C3 O2 -0.96(19) . . . . ? C1 C2 C3 C1 -2.5(2) . . . 3_766 ? Cl1 C2 C3 C1 178.60(9) . . . 3_766 ? N1 N2 C4 C5 0.57(19) . . . . ? N2 C4 C5 C6 -1.2(2) . . . . ? C4 C5 C6 C7 0.77(19) . . . . ? N2 N1 C7 C6 -0.8(2) . . . . ? C5 C6 C7 N1 0.13(19) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.471 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.067 # Attachment '185K.cif' # Asaji et al. #Hydrogen bonding in 1,2-diazine--chloranilic acid (2/1) #studied ny ^14^N nuclear quadrupole coupling tensor #and multi-temperature X-ray diffraction data_185K _database_code_depnum_ccdc_archive 'CCDC 706682' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl2 N4 O4' _chemical_formula_sum 'C14 H10 Cl2 N4 O4' _chemical_formula_weight 369.16 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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' _cell_length_a 3.7572(2) _cell_length_b 20.1855(12) _cell_length_c 9.6392(6) _cell_angle_alpha 90.00 _cell_angle_beta 99.189(2) _cell_angle_gamma 90.00 _cell_volume 721.66(8) _cell_formula_units_Z 2 _cell_measurement_temperature 185(1) _cell_measurement_reflns_used 15381 _cell_measurement_theta_min 3.7 _cell_measurement_theta_max 29.9 _exptl_crystal_description platelet _exptl_crystal_colour brown _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.699 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.480 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Higashi, T. (1999). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.916 _exptl_absorpt_correction_T_max 0.976 _exptl_special_details ; ? ; _diffrn_ambient_temperature 185(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17877 _diffrn_reflns_av_R_equivalents 0.0217 _diffrn_reflns_av_sigmaI/netI 0.0111 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.71 _diffrn_reflns_theta_max 29.94 _reflns_number_total 2098 _reflns_number_gt 1871 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku/MSC, 2004)' _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'CrystalStructure and PLATON (Spek, 2003)' _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^)+(0.0456P)^2^+0.1359P] 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 2098 _refine_ls_number_parameters 116 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0312 _refine_ls_R_factor_gt 0.0278 _refine_ls_wR_factor_ref 0.0779 _refine_ls_wR_factor_gt 0.0754 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _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 Cl1 Cl 0.57609(7) 0.497345(11) 0.18784(2) 0.02399(9) Uani 1 1 d . . . O1 O 0.7200(2) 0.61211(4) 0.38131(8) 0.0314(2) Uani 1 1 d . . . O2 O 0.9018(2) 0.38264(4) 0.35850(8) 0.02711(18) Uani 1 1 d . . . H2 H 0.970(11) 0.354(2) 0.405(4) 0.033 Uiso 0.38(2) 1 d P . . N1 N 1.0456(2) 0.26563(4) 0.45703(9) 0.02250(18) Uani 1 1 d . . . H1 H 1.016(6) 0.3081(13) 0.436(2) 0.027 Uiso 0.62(2) 1 d P . . N2 N 0.8644(3) 0.22733(4) 0.35584(9) 0.02426(19) Uani 1 1 d . . . C1 C 0.8471(3) 0.55940(5) 0.43093(10) 0.02020(19) Uani 1 1 d . . . C2 C 0.8078(3) 0.49748(4) 0.35849(10) 0.01916(19) Uani 1 1 d . . . C3 C 0.9411(3) 0.43896(5) 0.41938(10) 0.02000(19) Uani 1 1 d . . . C4 C 0.8779(3) 0.16246(5) 0.37818(11) 0.0244(2) Uani 1 1 d . . . H4 H 0.7535 0.1342 0.3078 0.029 Uiso 1 1 calc R . . C5 C 1.0660(3) 0.13348(5) 0.50015(11) 0.0246(2) Uani 1 1 d . . . H5 H 1.0651 0.0868 0.5129 0.029 Uiso 1 1 calc R . . C6 C 1.2514(3) 0.17391(5) 0.60080(11) 0.0242(2) Uani 1 1 d . . . H6 H 1.3856 0.1565 0.6847 0.029 Uiso 1 1 calc R . . C7 C 1.2338(3) 0.24194(5) 0.57423(10) 0.0235(2) Uani 1 1 d . . . H7 H 1.3589 0.2717 0.6414 0.028 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 Cl1 0.02924(15) 0.02333(14) 0.01613(14) -0.00002(8) -0.00639(9) 0.00071(8) O1 0.0438(5) 0.0195(3) 0.0253(4) 0.0004(3) -0.0118(3) 0.0061(3) O2 0.0391(5) 0.0183(3) 0.0199(4) -0.0022(3) -0.0075(3) 0.0031(3) N1 0.0263(4) 0.0200(4) 0.0194(4) -0.0019(3) -0.0021(3) 0.0007(3) N2 0.0277(4) 0.0237(4) 0.0187(4) -0.0014(3) -0.0044(3) -0.0003(3) C1 0.0222(4) 0.0196(4) 0.0172(4) 0.0007(3) -0.0018(3) 0.0007(3) C2 0.0218(4) 0.0201(4) 0.0138(4) 0.0000(3) -0.0029(3) 0.0006(3) C3 0.0215(4) 0.0207(4) 0.0164(4) 0.0002(3) -0.0013(3) 0.0011(3) C4 0.0264(5) 0.0224(5) 0.0224(5) -0.0026(4) -0.0017(4) -0.0015(4) C5 0.0271(5) 0.0199(4) 0.0259(5) 0.0021(4) 0.0017(4) 0.0010(4) C6 0.0262(5) 0.0255(5) 0.0195(4) 0.0032(4) -0.0008(4) 0.0029(4) C7 0.0251(5) 0.0245(5) 0.0189(5) -0.0029(3) -0.0026(4) 0.0007(4) _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 Cl1 C2 1.7339(10) . ? O1 C1 1.2314(12) . ? O2 C3 1.2770(12) . ? O2 H2 0.76(5) . ? N1 C7 1.3229(13) . ? N1 N2 1.3418(11) . ? N1 H1 0.89(3) . ? N2 C4 1.3267(13) . ? C1 C2 1.4278(13) . ? C1 C3 1.5327(14) 3_766 ? C2 C3 1.3773(13) . ? C3 C1 1.5327(14) 3_766 ? C4 C5 1.3994(14) . ? C4 H4 0.9500 . ? C5 C6 1.3700(14) . ? C5 H5 0.9500 . ? C6 C7 1.3964(14) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? 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 C3 O2 H2 114(3) . . ? C7 N1 N2 123.53(9) . . ? C7 N1 H1 125.4(15) . . ? N2 N1 H1 111.0(15) . . ? C4 N2 N1 116.68(9) . . ? O1 C1 C2 124.26(9) . . ? O1 C1 C3 117.24(8) . 3_766 ? C2 C1 C3 118.49(8) . 3_766 ? C3 C2 C1 122.69(9) . . ? C3 C2 Cl1 119.75(7) . . ? C1 C2 Cl1 117.55(7) . . ? O2 C3 C2 124.06(9) . . ? O2 C3 C1 117.16(8) . 3_766 ? C2 C3 C1 118.77(8) . 3_766 ? N2 C4 C5 123.37(10) . . ? N2 C4 H4 118.3 . . ? C5 C4 H4 118.3 . . ? C6 C5 C4 118.51(10) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? C5 C6 C7 116.88(9) . . ? C5 C6 H6 121.6 . . ? C7 C6 H6 121.6 . . ? N1 C7 C6 121.02(9) . . ? N1 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? 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 C7 N1 N2 C4 0.53(15) . . . . ? O1 C1 C2 C3 -177.26(11) . . . . ? C3 C1 C2 C3 2.36(17) 3_766 . . . ? O1 C1 C2 Cl1 1.84(15) . . . . ? C3 C1 C2 Cl1 -178.54(7) 3_766 . . . ? C1 C2 C3 O2 178.06(10) . . . . ? Cl1 C2 C3 O2 -1.02(15) . . . . ? C1 C2 C3 C1 -2.37(17) . . . 3_766 ? Cl1 C2 C3 C1 178.55(7) . . . 3_766 ? N1 N2 C4 C5 0.50(16) . . . . ? N2 C4 C5 C6 -1.21(17) . . . . ? C4 C5 C6 C7 0.86(16) . . . . ? N2 N1 C7 C6 -0.83(16) . . . . ? C5 C6 C7 N1 0.08(16) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 29.94 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.430 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.055 # Attachment '212K.cif' # Asaji et al. #Hydrogen bonding in 1,2-diazine--chloranilic acid (2/1) #studied ny ^14^N nuclear quadrupole coupling tensor #and multi-temperature X-ray diffraction data_212K _database_code_depnum_ccdc_archive 'CCDC 706683' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl2 N4 O4' _chemical_formula_sum 'C14 H10 Cl2 N4 O4' _chemical_formula_weight 369.16 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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' _cell_length_a 3.76378(15) _cell_length_b 20.2105(5) _cell_length_c 9.6548(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.2919(13) _cell_angle_gamma 90.00 _cell_volume 724.78(4) _cell_formula_units_Z 2 _cell_measurement_temperature 212(1) _cell_measurement_reflns_used 10147 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 30.0 _exptl_crystal_description platelet _exptl_crystal_colour brown _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.692 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.478 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Higashi, T. (1999). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.874 _exptl_absorpt_correction_T_max 0.953 _exptl_special_details ; ? ; _diffrn_ambient_temperature 212(1) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11560 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0164 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.70 _diffrn_reflns_theta_max 29.98 _reflns_number_total 2116 _reflns_number_gt 1869 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku/MSC, 2004)' _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'CrystalStructure and PLATON (Spek, 2003)' _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^)+(0.0499P)^2^+0.1500P] 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 2116 _refine_ls_number_parameters 116 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0352 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0896 _refine_ls_wR_factor_gt 0.0877 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _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 Cl1 Cl 0.57590(8) 0.497341(12) 0.18804(3) 0.02777(11) Uani 1 1 d . . . O1 O 0.7232(3) 0.61203(4) 0.38099(9) 0.0364(2) Uani 1 1 d . . . O2 O 0.8987(3) 0.38279(4) 0.35887(9) 0.0313(2) Uani 1 1 d . . . H2 H 0.976(12) 0.356(2) 0.401(5) 0.038 Uiso 0.40(3) 1 d P . . N1 N 1.0427(3) 0.26571(5) 0.45741(11) 0.0258(2) Uani 1 1 d . . . H1 H 1.022(7) 0.3087(15) 0.435(3) 0.031 Uiso 0.60(3) 1 d P . . N2 N 0.8618(3) 0.22742(5) 0.35641(10) 0.0278(2) Uani 1 1 d . . . C1 C 0.8489(3) 0.55935(5) 0.43084(11) 0.0232(2) Uani 1 1 d . . . C2 C 0.8079(3) 0.49746(5) 0.35852(12) 0.0218(2) Uani 1 1 d . . . C3 C 0.9396(3) 0.43903(5) 0.41958(11) 0.0231(2) Uani 1 1 d . . . C4 C 0.8761(3) 0.16274(6) 0.37859(13) 0.0281(2) Uani 1 1 d . . . H4 H 0.7533 0.1348 0.3089 0.034 Uiso 1 1 calc R . . C5 C 1.0644(3) 0.13379(6) 0.50030(12) 0.0284(2) Uani 1 1 d . . . H5 H 1.0642 0.0877 0.5127 0.034 Uiso 1 1 calc R . . C6 C 1.2490(3) 0.17412(6) 0.60088(12) 0.0278(2) Uani 1 1 d . . . H6 H 1.3819 0.1569 0.6838 0.033 Uiso 1 1 calc R . . C7 C 1.2307(3) 0.24201(6) 0.57457(12) 0.0269(2) Uani 1 1 d . . . H7 H 1.3538 0.2714 0.6411 0.032 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 Cl1 0.03396(17) 0.02663(16) 0.01878(16) -0.00005(9) -0.00761(11) 0.00082(10) O1 0.0511(6) 0.0224(4) 0.0291(5) 0.0000(3) -0.0135(4) 0.0073(4) O2 0.0444(5) 0.0210(4) 0.0238(4) -0.0026(3) -0.0086(4) 0.0039(3) N1 0.0301(5) 0.0226(4) 0.0225(5) -0.0019(4) -0.0026(4) 0.0006(3) N2 0.0320(5) 0.0270(5) 0.0211(5) -0.0011(4) -0.0055(4) 0.0001(4) C1 0.0255(5) 0.0222(5) 0.0197(5) 0.0010(4) -0.0028(4) 0.0009(4) C2 0.0250(5) 0.0224(5) 0.0158(5) 0.0001(4) -0.0036(4) 0.0007(4) C3 0.0251(5) 0.0234(5) 0.0190(5) 0.0003(4) -0.0018(4) 0.0017(4) C4 0.0308(6) 0.0251(5) 0.0258(5) -0.0037(4) -0.0027(4) -0.0019(4) C5 0.0310(6) 0.0227(5) 0.0304(6) 0.0026(4) 0.0013(5) 0.0014(4) C6 0.0302(6) 0.0288(5) 0.0224(5) 0.0042(4) -0.0017(4) 0.0042(4) C7 0.0297(6) 0.0274(5) 0.0211(5) -0.0033(4) -0.0031(4) 0.0009(4) _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 Cl1 C2 1.7342(12) . ? O1 C1 1.2311(13) . ? O2 C3 1.2768(13) . ? O2 H2 0.71(5) . ? N1 C7 1.3234(14) . ? N1 N2 1.3412(13) . ? N1 H1 0.90(3) . ? N2 C4 1.3243(15) . ? C1 C2 1.4286(14) . ? C1 C3 1.5326(16) 3_766 ? C2 C3 1.3761(14) . ? C3 C1 1.5326(16) 3_766 ? C4 C5 1.3988(16) . ? C4 H4 0.9400 . ? C5 C6 1.3682(17) . ? C5 H5 0.9400 . ? C6 C7 1.3951(16) . ? C6 H6 0.9400 . ? C7 H7 0.9400 . ? 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 C3 O2 H2 114(4) . . ? C7 N1 N2 123.45(10) . . ? C7 N1 H1 125.0(17) . . ? N2 N1 H1 111.5(17) . . ? C4 N2 N1 116.71(10) . . ? O1 C1 C2 124.18(10) . . ? O1 C1 C3 117.26(9) . 3_766 ? C2 C1 C3 118.56(9) . 3_766 ? C3 C2 C1 122.61(11) . . ? C3 C2 Cl1 119.79(8) . . ? C1 C2 Cl1 117.59(8) . . ? O2 C3 C2 123.98(10) . . ? O2 C3 C1 117.23(9) . 3_766 ? C2 C3 C1 118.79(9) . 3_766 ? N2 C4 C5 123.40(11) . . ? N2 C4 H4 118.3 . . ? C5 C4 H4 118.3 . . ? C6 C5 C4 118.52(11) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? C5 C6 C7 116.88(10) . . ? C5 C6 H6 121.6 . . ? C7 C6 H6 121.6 . . ? N1 C7 C6 121.03(10) . . ? N1 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? 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 C7 N1 N2 C4 0.34(18) . . . . ? O1 C1 C2 C3 -177.28(12) . . . . ? C3 C1 C2 C3 2.36(19) 3_766 . . . ? O1 C1 C2 Cl1 1.73(17) . . . . ? C3 C1 C2 Cl1 -178.62(8) 3_766 . . . ? C1 C2 C3 O2 178.05(12) . . . . ? Cl1 C2 C3 O2 -0.95(17) . . . . ? C1 C2 C3 C1 -2.37(19) . . . 3_766 ? Cl1 C2 C3 C1 178.64(8) . . . 3_766 ? N1 N2 C4 C5 0.57(19) . . . . ? N2 C4 C5 C6 -1.2(2) . . . . ? C4 C5 C6 C7 0.82(18) . . . . ? N2 N1 C7 C6 -0.64(19) . . . . ? C5 C6 C7 N1 0.01(18) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 29.98 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.439 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.054 # Attachment '220K.cif' # Asaji et al. #Hydrogen bonding in 1,2-diazine--chloranilic acid (2/1) #studied ny ^14^N nuclear quadrupole coupling tensor #and multi-temperature X-ray diffraction data_220K _database_code_depnum_ccdc_archive 'CCDC 706684' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl2 N4 O4' _chemical_formula_sum 'C14 H10 Cl2 N4 O4' _chemical_formula_weight 369.16 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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' _cell_length_a 3.7657(3) _cell_length_b 20.2197(15) _cell_length_c 9.6515(7) _cell_angle_alpha 90.00 _cell_angle_beta 99.334(2) _cell_angle_gamma 90.00 _cell_volume 725.16(9) _cell_formula_units_Z 2 _cell_measurement_temperature 220(1) _cell_measurement_reflns_used 14000 _cell_measurement_theta_min 3.7 _cell_measurement_theta_max 29.9 _exptl_crystal_description platelet _exptl_crystal_colour brown _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.691 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.478 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Higashi, T. (1999). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.906 _exptl_absorpt_correction_T_max 0.976 _exptl_special_details ; ? ; _diffrn_ambient_temperature 220(1) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16510 _diffrn_reflns_av_R_equivalents 0.0236 _diffrn_reflns_av_sigmaI/netI 0.0126 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.70 _diffrn_reflns_theta_max 29.95 _reflns_number_total 2110 _reflns_number_gt 1843 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku/MSC, 2004)' _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'CrystalStructure and PLATON (Spek, 2003)' _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^)+(0.0481P)^2^+0.1175P] 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 2110 _refine_ls_number_parameters 116 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0344 _refine_ls_R_factor_gt 0.0298 _refine_ls_wR_factor_ref 0.0831 _refine_ls_wR_factor_gt 0.0805 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _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 Cl1 Cl 0.57591(7) 0.497326(12) 0.18810(3) 0.02869(10) Uani 1 1 d . . . O1 O 0.7237(3) 0.61198(4) 0.38085(9) 0.0374(2) Uani 1 1 d . . . O2 O 0.8982(3) 0.38280(4) 0.35893(9) 0.0322(2) Uani 1 1 d . . . H2 H 0.985(10) 0.354(2) 0.402(4) 0.039 Uiso 0.41(2) 1 d P . . N1 N 1.0423(3) 0.26569(5) 0.45756(10) 0.0265(2) Uani 1 1 d . . . H1 H 1.011(7) 0.3077(14) 0.438(3) 0.032 Uiso 0.59(2) 1 d P . . N2 N 0.8617(3) 0.22744(4) 0.35642(10) 0.0284(2) Uani 1 1 d . . . C1 C 0.8490(3) 0.55935(5) 0.43080(10) 0.0240(2) Uani 1 1 d . . . C2 C 0.8077(3) 0.49747(5) 0.35856(11) 0.0227(2) Uani 1 1 d . . . C3 C 0.9394(3) 0.43907(5) 0.41970(10) 0.0236(2) Uani 1 1 d . . . C4 C 0.8759(3) 0.16283(5) 0.37854(12) 0.0286(2) Uani 1 1 d . . . H4 H 0.7532 0.1349 0.3088 0.034 Uiso 1 1 calc R . . C5 C 1.0640(3) 0.13388(6) 0.50039(12) 0.0292(2) Uani 1 1 d . . . H5 H 1.0638 0.0878 0.5128 0.035 Uiso 1 1 calc R . . C6 C 1.2483(3) 0.17417(6) 0.60096(12) 0.0286(2) Uani 1 1 d . . . H6 H 1.3811 0.1570 0.6840 0.034 Uiso 1 1 calc R . . C7 C 1.2301(3) 0.24200(5) 0.57448(11) 0.0277(2) Uani 1 1 d . . . H7 H 1.3536 0.2713 0.6410 0.033 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 Cl1 0.03519(17) 0.02760(15) 0.01923(15) -0.00001(8) -0.00773(10) 0.00076(9) O1 0.0524(5) 0.0230(4) 0.0297(4) 0.0001(3) -0.0141(4) 0.0073(4) O2 0.0465(5) 0.0216(4) 0.0235(4) -0.0025(3) -0.0094(3) 0.0042(3) N1 0.0315(5) 0.0232(4) 0.0225(4) -0.0023(3) -0.0026(4) 0.0009(3) N2 0.0327(5) 0.0276(4) 0.0214(4) -0.0009(3) -0.0055(4) 0.0002(4) C1 0.0270(5) 0.0229(5) 0.0200(5) 0.0011(3) -0.0027(4) 0.0012(4) C2 0.0260(5) 0.0234(5) 0.0163(4) 0.0000(3) -0.0034(4) 0.0007(4) C3 0.0257(5) 0.0242(5) 0.0193(4) 0.0000(4) -0.0014(4) 0.0013(4) C4 0.0310(5) 0.0261(5) 0.0265(5) -0.0033(4) -0.0022(4) -0.0019(4) C5 0.0328(5) 0.0231(5) 0.0306(6) 0.0026(4) 0.0017(4) 0.0011(4) C6 0.0309(5) 0.0303(5) 0.0229(5) 0.0038(4) -0.0012(4) 0.0038(4) C7 0.0307(5) 0.0283(5) 0.0219(5) -0.0030(4) -0.0026(4) 0.0011(4) _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 Cl1 C2 1.7328(11) . ? O1 C1 1.2303(13) . ? O2 C3 1.2779(12) . ? O2 H2 0.75(4) . ? N1 C7 1.3207(13) . ? N1 N2 1.3411(12) . ? N1 H1 0.87(3) . ? N2 C4 1.3234(14) . ? C1 C2 1.4286(14) . ? C1 C3 1.5313(15) 3_766 ? C2 C3 1.3760(14) . ? C3 C1 1.5313(15) 3_766 ? C4 C5 1.3991(15) . ? C4 H4 0.9400 . ? C5 C6 1.3670(16) . ? C5 H5 0.9400 . ? C6 C7 1.3947(15) . ? C6 H6 0.9400 . ? C7 H7 0.9400 . ? 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 C3 O2 H2 115(3) . . ? C7 N1 N2 123.42(10) . . ? C7 N1 H1 125.0(17) . . ? N2 N1 H1 111.5(17) . . ? C4 N2 N1 116.71(9) . . ? O1 C1 C2 124.18(10) . . ? O1 C1 C3 117.33(9) . 3_766 ? C2 C1 C3 118.49(8) . 3_766 ? C3 C2 C1 122.63(10) . . ? C3 C2 Cl1 119.79(8) . . ? C1 C2 Cl1 117.58(7) . . ? O2 C3 C2 123.96(10) . . ? O2 C3 C1 117.19(9) . 3_766 ? C2 C3 C1 118.85(9) . 3_766 ? N2 C4 C5 123.38(10) . . ? N2 C4 H4 118.3 . . ? C5 C4 H4 118.3 . . ? C6 C5 C4 118.50(10) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? C5 C6 C7 116.85(10) . . ? C5 C6 H6 121.6 . . ? C7 C6 H6 121.6 . . ? N1 C7 C6 121.12(10) . . ? N1 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? 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 C7 N1 N2 C4 0.46(17) . . . . ? O1 C1 C2 C3 -177.36(11) . . . . ? C3 C1 C2 C3 2.33(18) 3_766 . . . ? O1 C1 C2 Cl1 1.74(16) . . . . ? C3 C1 C2 Cl1 -178.57(8) 3_766 . . . ? C1 C2 C3 O2 178.08(11) . . . . ? Cl1 C2 C3 O2 -1.00(16) . . . . ? C1 C2 C3 C1 -2.34(18) . . . 3_766 ? Cl1 C2 C3 C1 178.59(8) . . . 3_766 ? N1 N2 C4 C5 0.56(17) . . . . ? N2 C4 C5 C6 -1.19(18) . . . . ? C4 C5 C6 C7 0.80(17) . . . . ? N2 N1 C7 C6 -0.82(17) . . . . ? C5 C6 C7 N1 0.14(17) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 29.95 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.430 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.053 # Attachment '258K.cif' # Asaji et al. #Hydrogen bonding in 1,2-diazine--chloranilic acid (2/1) #studied ny ^14^N nuclear quadrupole coupling tensor #and multi-temperature X-ray diffraction data_258K _database_code_depnum_ccdc_archive 'CCDC 706685' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl2 N4 O4' _chemical_formula_sum 'C14 H10 Cl2 N4 O4' _chemical_formula_weight 369.16 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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' _cell_length_a 3.7825(2) _cell_length_b 20.2466(13) _cell_length_c 9.6556(6) _cell_angle_alpha 90.00 _cell_angle_beta 99.515(2) _cell_angle_gamma 90.00 _cell_volume 729.28(8) _cell_formula_units_Z 2 _cell_measurement_temperature 258(1) _cell_measurement_reflns_used 17903 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 29.9 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.681 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.475 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Higashi, T. (1999). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.902 _exptl_absorpt_correction_T_max 0.977 _exptl_special_details ; ? ; _diffrn_ambient_temperature 258(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22018 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0097 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.70 _diffrn_reflns_theta_max 29.95 _reflns_number_total 2127 _reflns_number_gt 1836 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku/MSC, 2004)' _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'CrystalStructure and PLATON (Spek, 2003)' _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^)+(0.0496P)^2^+0.0976P] 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 2127 _refine_ls_number_parameters 116 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0356 _refine_ls_R_factor_gt 0.0306 _refine_ls_wR_factor_ref 0.0857 _refine_ls_wR_factor_gt 0.0830 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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 Cl1 Cl 0.57555(8) 0.497310(12) 0.18836(3) 0.03480(11) Uani 1 1 d . . . O1 O 0.7289(3) 0.61180(4) 0.38023(9) 0.0449(2) Uani 1 1 d . . . O2 O 0.8938(3) 0.38299(4) 0.35964(9) 0.0389(2) Uani 1 1 d . . . H2 H 0.973(10) 0.356(2) 0.407(4) 0.047 Uiso 0.42(2) 1 d P . . N1 N 1.0380(3) 0.26579(5) 0.45827(10) 0.0320(2) Uani 1 1 d . . . H1 H 1.009(7) 0.3093(15) 0.436(3) 0.038 Uiso 0.58(2) 1 d P . . N2 N 0.8578(3) 0.22761(5) 0.35725(10) 0.0344(2) Uani 1 1 d . . . C1 C 0.8513(3) 0.55926(5) 0.43038(11) 0.0288(2) Uani 1 1 d . . . C2 C 0.8078(3) 0.49742(5) 0.35890(11) 0.0273(2) Uani 1 1 d . . . C3 C 0.9370(3) 0.43918(5) 0.42000(10) 0.0286(2) Uani 1 1 d . . . C4 C 0.8731(3) 0.16306(5) 0.37923(12) 0.0349(2) Uani 1 1 d . . . H4 H 0.7518 0.1355 0.3102 0.042 Uiso 1 1 calc R . . C5 C 1.0617(3) 0.13423(6) 0.50062(12) 0.0352(2) Uani 1 1 d . . . H5 H 1.0626 0.0887 0.5127 0.042 Uiso 1 1 calc R . . C6 C 1.2447(3) 0.17442(6) 0.60112(12) 0.0350(2) Uani 1 1 d . . . H6 H 1.3761 0.1574 0.6833 0.042 Uiso 1 1 calc R . . C7 C 1.2255(3) 0.24201(5) 0.57484(11) 0.0333(2) Uani 1 1 d . . . H7 H 1.3474 0.2710 0.6408 0.040 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 Cl1 0.04305(18) 0.03306(16) 0.02331(15) -0.00011(9) -0.00915(11) 0.00086(10) O1 0.0637(6) 0.0271(4) 0.0352(4) 0.0002(3) -0.0170(4) 0.0083(4) O2 0.0561(5) 0.0260(4) 0.0284(4) -0.0031(3) -0.0111(4) 0.0042(3) N1 0.0383(5) 0.0275(4) 0.0273(4) -0.0023(3) -0.0035(4) 0.0010(4) N2 0.0405(5) 0.0322(5) 0.0263(5) -0.0011(3) -0.0065(4) 0.0004(4) C1 0.0326(5) 0.0271(5) 0.0240(5) 0.0008(3) -0.0035(4) 0.0012(4) C2 0.0313(5) 0.0280(5) 0.0196(5) -0.0003(3) -0.0044(4) 0.0007(4) C3 0.0318(5) 0.0286(5) 0.0232(5) -0.0001(4) -0.0020(4) 0.0020(4) C4 0.0395(6) 0.0306(5) 0.0314(5) -0.0035(4) -0.0033(4) -0.0026(4) C5 0.0397(6) 0.0272(5) 0.0372(6) 0.0029(4) 0.0018(5) 0.0014(4) C6 0.0385(6) 0.0361(5) 0.0279(5) 0.0050(4) -0.0016(4) 0.0052(4) C7 0.0371(6) 0.0334(5) 0.0263(5) -0.0038(4) -0.0037(4) 0.0014(4) _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 Cl1 C2 1.7335(11) . ? O1 C1 1.2273(12) . ? O2 C3 1.2763(13) . ? O2 H2 0.74(4) . ? N1 C7 1.3182(13) . ? N1 N2 1.3393(12) . ? N1 H1 0.91(3) . ? N2 C4 1.3237(14) . ? C1 C2 1.4259(13) . ? C1 C3 1.5319(15) 3_766 ? C2 C3 1.3720(13) . ? C3 C1 1.5319(15) 3_766 ? C4 C5 1.3954(15) . ? C4 H4 0.9300 . ? C5 C6 1.3642(16) . ? C5 H5 0.9300 . ? C6 C7 1.3915(15) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? 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 C3 O2 H2 111(3) . . ? C7 N1 N2 123.25(10) . . ? C7 N1 H1 125.4(17) . . ? N2 N1 H1 111.3(16) . . ? C4 N2 N1 116.72(9) . . ? O1 C1 C2 124.34(10) . . ? O1 C1 C3 117.28(9) . 3_766 ? C2 C1 C3 118.37(8) . 3_766 ? C3 C2 C1 122.83(10) . . ? C3 C2 Cl1 119.73(8) . . ? C1 C2 Cl1 117.44(7) . . ? O2 C3 C2 124.06(10) . . ? O2 C3 C1 117.17(9) . 3_766 ? C2 C3 C1 118.76(8) . 3_766 ? N2 C4 C5 123.40(10) . . ? N2 C4 H4 118.3 . . ? C5 C4 H4 118.3 . . ? C6 C5 C4 118.47(11) . . ? C6 C5 H5 120.8 . . ? C4 C5 H5 120.8 . . ? C5 C6 C7 116.87(10) . . ? C5 C6 H6 121.6 . . ? C7 C6 H6 121.6 . . ? N1 C7 C6 121.28(10) . . ? N1 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? 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 C7 N1 N2 C4 0.35(17) . . . . ? O1 C1 C2 C3 -177.53(12) . . . . ? C3 C1 C2 C3 2.18(18) 3_766 . . . ? O1 C1 C2 Cl1 1.66(17) . . . . ? C3 C1 C2 Cl1 -178.63(8) 3_766 . . . ? C1 C2 C3 O2 178.14(11) . . . . ? Cl1 C2 C3 O2 -1.03(17) . . . . ? C1 C2 C3 C1 -2.19(18) . . . 3_766 ? Cl1 C2 C3 C1 178.64(8) . . . 3_766 ? N1 N2 C4 C5 0.54(18) . . . . ? N2 C4 C5 C6 -1.04(19) . . . . ? C4 C5 C6 C7 0.64(17) . . . . ? N2 N1 C7 C6 -0.73(18) . . . . ? C5 C6 C7 N1 0.19(18) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 29.95 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.413 _refine_diff_density_min -0.160 _refine_diff_density_rms 0.050