# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email tullio.pilati@istm.cnr.it _publ_contact_author_name 'Tullio Pilati ' loop_ _publ_author_name 'Franco Cozzi' 'Tullio Pilati' data_cz21 _database_code_depnum_ccdc_archive 'CCDC 810505' #TrackingRef 'BrMa.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H Br2 N O2' _chemical_formula_sum 'C4 H Br2 N O2' _chemical_formula_weight 254.88 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' Br Br -0.2901 2.4595 '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 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 10.2396(10) _cell_length_b 8.1042(8) _cell_length_c 7.8045(8) _cell_angle_alpha 90.00 _cell_angle_beta 100.031(10) _cell_angle_gamma 90.00 _cell_volume 637.75(11) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4025 _cell_measurement_theta_min 3.040 _cell_measurement_theta_max 29.63 _exptl_crystal_description table _exptl_crystal_colour 'pale orange' _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.655 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 12.626 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.' _exptl_absorpt_correction_T_min 0.1519 _exptl_absorpt_correction_T_max 0.2656 _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 APEX-II CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 7770 _diffrn_reflns_av_R_equivalents 0.0350 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 30.52 _reflns_number_total 1775 _reflns_number_gt 1397 _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457 ; _computing_publication_material 'SHELXL-97 (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 'w=1/[\s^2^(Fo^2^)+(0.0223P)^2^+0.2314P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1775 _refine_ls_number_parameters 82 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0378 _refine_ls_R_factor_gt 0.0243 _refine_ls_wR_factor_ref 0.0577 _refine_ls_wR_factor_gt 0.0534 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 Br1 Br 0.45321(3) 0.43872(3) 0.22688(4) 0.05137(10) Uani 1 1 d . . . Br2 Br 0.23262(3) 0.74996(3) -0.01357(4) 0.04719(10) Uani 1 1 d . . . O2 O 0.01404(19) 0.4978(2) -0.2251(2) 0.0528(5) Uani 1 1 d . . . O1 O 0.2797(2) 0.1113(2) 0.0813(3) 0.0514(5) Uani 1 1 d . . . N1 N 0.1261(2) 0.2715(2) -0.0960(3) 0.0419(5) Uani 1 1 d . . . H1 H 0.0746 0.1949 -0.1450 0.050 Uiso 1 1 calc R . . C1 C 0.2387(3) 0.2437(3) 0.0249(3) 0.0371(5) Uani 1 1 d . . . C2 C 0.2984(2) 0.4107(3) 0.0706(3) 0.0346(5) Uani 1 1 d . . . C3 C 0.2199(2) 0.5234(3) -0.0175(3) 0.0341(5) Uani 1 1 d . . . C4 C 0.1060(3) 0.4376(3) -0.1289(3) 0.0379(5) Uani 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 Br1 0.03884(17) 0.05716(17) 0.05157(18) -0.00087(12) -0.01031(13) -0.00047(13) Br2 0.0558(2) 0.02833(12) 0.05375(18) 0.00141(10) -0.00071(14) -0.00207(10) O2 0.0405(11) 0.0452(10) 0.0640(13) 0.0047(9) -0.0152(10) 0.0032(9) O1 0.0519(12) 0.0318(8) 0.0675(13) 0.0044(8) 0.0018(10) 0.0054(8) N1 0.0374(13) 0.0300(9) 0.0530(13) -0.0007(8) -0.0065(10) -0.0048(8) C1 0.0353(14) 0.0321(11) 0.0427(14) 0.0007(9) 0.0036(11) 0.0030(9) C2 0.0307(12) 0.0331(10) 0.0374(13) -0.0013(9) -0.0015(10) -0.0010(9) C3 0.0324(14) 0.0277(10) 0.0408(13) -0.0004(8) 0.0022(11) -0.0001(9) C4 0.0334(14) 0.0346(10) 0.0434(14) 0.0005(10) -0.0001(11) 0.0009(10) _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 Br1 C2 1.838(2) . ? Br2 C3 1.840(2) . ? O2 C4 1.201(3) . ? O1 C1 1.207(3) . ? N1 C1 1.376(3) . ? N1 C4 1.378(3) . ? C1 C2 1.503(3) . ? C2 C3 1.327(3) . ? C3 C4 1.499(3) . ? 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 C1 N1 C4 111.6(2) . . ? O1 C1 N1 126.4(2) . . ? O1 C1 C2 127.8(2) . . ? N1 C1 C2 105.83(18) . . ? C3 C2 C1 108.2(2) . . ? C3 C2 Br1 129.29(18) . . ? C1 C2 Br1 122.48(17) . . ? C2 C3 C4 108.70(19) . . ? C2 C3 Br2 130.1(2) . . ? C4 C3 Br2 121.22(17) . . ? O2 C4 N1 126.0(2) . . ? O2 C4 C3 128.3(2) . . ? N1 C4 C3 105.6(2) . . ? _diffrn_measured_fraction_theta_max 0.908 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.477 _refine_diff_density_min -0.403 _refine_diff_density_rms 0.074 # Attachment 'BrMaClPy.CIF' data_cz17 _database_code_depnum_ccdc_archive 'CCDC 810506' #TrackingRef 'BrMaClPy.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C5 H5 Cl2 N3, C4 H1 Br2 N O2' _chemical_formula_sum 'C9 H6 Br2 Cl2 N4 O2' _chemical_formula_weight 432.90 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9498(8) _cell_length_b 8.5107(11) _cell_length_c 11.2025(12) _cell_angle_alpha 100.225(12) _cell_angle_beta 98.246(11) _cell_angle_gamma 95.329(11) _cell_volume 640.56(13) _cell_formula_units_Z 2 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 5457 _cell_measurement_theta_min 2.98 _cell_measurement_theta_max 32.23 _exptl_crystal_description table _exptl_crystal_colour red-orange _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.244 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 6.746 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.' _exptl_absorpt_correction_T_min 0.2712 _exptl_absorpt_correction_T_max 0.3836 _exptl_special_details ; Bruker KRYOFLEX low temperature device. ; _diffrn_ambient_temperature 103(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 APEX-II CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 12200 _diffrn_reflns_av_R_equivalents 0.0250 _diffrn_reflns_av_sigmaI/netI 0.0287 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 32.81 _reflns_number_total 4151 _reflns_number_gt 3477 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457 ; _computing_publication_material 'SHELXL-97 (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. Chemically equivalent N-H distance were restraint to have similar value ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0260P)^2^+0.1672P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4151 _refine_ls_number_parameters 196 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0340 _refine_ls_R_factor_gt 0.0233 _refine_ls_wR_factor_ref 0.0546 _refine_ls_wR_factor_gt 0.0513 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 0.84598(6) 0.03186(5) 0.10171(4) 0.01568(9) Uani 1 1 d . . . Cl2 Cl 0.14952(6) -0.27199(5) 0.14641(4) 0.01511(9) Uani 1 1 d . . . N1 N 0.5103(2) 0.08865(18) 0.36195(13) 0.0132(3) Uani 1 1 d . . . N2 N 0.8157(2) 0.2163(2) 0.35238(17) 0.0178(3) Uani 1 1 d D . . H2A H 0.811(3) 0.279(2) 0.4178(18) 0.016(6) Uiso 1 1 d D . . H2B H 0.904(4) 0.225(3) 0.309(2) 0.042(8) Uiso 1 1 d D . . N3 N 0.2074(2) -0.0321(2) 0.38187(17) 0.0173(3) Uani 1 1 d D . . H3A H 0.214(3) 0.036(2) 0.4465(18) 0.014(6) Uiso 1 1 d D . . H3B H 0.108(3) -0.097(3) 0.349(2) 0.030(7) Uiso 1 1 d D . . C1 C 0.6609(2) 0.1044(2) 0.29946(17) 0.0131(3) Uani 1 1 d . . . C2 C 0.6553(2) 0.0071(2) 0.18331(16) 0.0127(3) Uani 1 1 d . . . C3 C 0.4985(2) -0.1087(2) 0.13462(17) 0.0129(3) Uani 1 1 d . . . H3 H 0.492(3) -0.176(3) 0.056(2) 0.016(5) Uiso 1 1 d . . . C4 C 0.3483(2) -0.1252(2) 0.20120(17) 0.0125(3) Uani 1 1 d . . . C5 C 0.3544(2) -0.0226(2) 0.31491(16) 0.0125(3) Uani 1 1 d . . . Br1 Br 0.74777(2) 0.70166(2) 0.839229(18) 0.01704(5) Uani 1 1 d . . . Br2 Br 0.27004(3) 0.51793(2) 0.869352(18) 0.01820(5) Uani 1 1 d . . . O1 O 0.80079(19) 0.47170(17) 0.58145(13) 0.0187(3) Uani 1 1 d . . . O2 O 0.20426(18) 0.22939(16) 0.61834(13) 0.0169(3) Uani 1 1 d . . . N4 N 0.4994(2) 0.32332(19) 0.56916(15) 0.0143(3) Uani 1 1 d . . . H4 H 0.503(3) 0.247(3) 0.503(2) 0.027(6) Uiso 1 1 d . . . C6 C 0.6508(3) 0.4437(2) 0.62134(17) 0.0140(3) Uani 1 1 d . . . C7 C 0.5898(2) 0.5319(2) 0.73533(17) 0.0133(3) Uani 1 1 d . . . C8 C 0.4146(2) 0.4626(2) 0.74581(17) 0.0137(3) Uani 1 1 d . . . C9 C 0.3512(2) 0.3238(2) 0.63943(17) 0.0137(3) Uani 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 Cl1 0.01284(18) 0.0182(2) 0.0147(2) -0.00190(17) 0.00684(15) -0.00185(15) Cl2 0.01236(17) 0.01391(19) 0.0169(2) -0.00108(16) 0.00319(15) -0.00296(14) N1 0.0115(6) 0.0157(7) 0.0112(7) -0.0006(6) 0.0029(5) -0.0005(5) N2 0.0140(7) 0.0206(8) 0.0143(8) -0.0066(7) 0.0052(6) -0.0053(6) N3 0.0131(7) 0.0226(8) 0.0135(8) -0.0038(7) 0.0055(6) -0.0036(6) C1 0.0105(7) 0.0146(8) 0.0135(9) 0.0015(7) 0.0021(6) 0.0002(6) C2 0.0125(7) 0.0141(8) 0.0115(8) 0.0007(7) 0.0045(6) 0.0010(6) C3 0.0129(7) 0.0126(8) 0.0118(9) -0.0003(7) 0.0017(6) 0.0003(6) C4 0.0107(7) 0.0116(7) 0.0138(9) 0.0007(7) 0.0014(6) -0.0007(6) C5 0.0117(7) 0.0143(8) 0.0118(8) 0.0024(7) 0.0030(6) 0.0014(6) Br1 0.01486(8) 0.01250(9) 0.02033(10) -0.00235(7) 0.00154(7) -0.00329(6) Br2 0.01556(9) 0.01836(9) 0.01853(10) -0.00442(7) 0.00855(7) -0.00247(6) O1 0.0166(6) 0.0205(7) 0.0190(7) 0.0013(6) 0.0079(5) -0.0007(5) O2 0.0141(6) 0.0167(6) 0.0177(7) -0.0007(5) 0.0033(5) -0.0031(5) N4 0.0145(7) 0.0133(7) 0.0131(8) -0.0028(6) 0.0041(6) -0.0007(5) C6 0.0150(8) 0.0120(8) 0.0144(9) 0.0011(7) 0.0026(6) 0.0009(6) C7 0.0138(7) 0.0109(7) 0.0137(8) -0.0005(7) 0.0018(6) 0.0004(6) C8 0.0128(7) 0.0135(8) 0.0142(9) -0.0005(7) 0.0039(6) 0.0014(6) C9 0.0135(7) 0.0135(8) 0.0135(9) 0.0004(7) 0.0030(6) 0.0024(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 Cl1 C2 1.7323(17) . ? Cl2 C4 1.7350(18) . ? N1 C5 1.348(2) . ? N1 C1 1.349(2) . ? N2 C1 1.357(2) . ? N2 H2A 0.832(19) . ? N2 H2B 0.84(2) . ? N3 C5 1.356(2) . ? N3 H3A 0.836(19) . ? N3 H3B 0.84(2) . ? C1 C2 1.406(3) . ? C2 C3 1.377(2) . ? C3 C4 1.378(2) . ? C3 H3 0.95(2) . ? C4 C5 1.403(3) . ? Br1 C7 1.8410(18) . ? Br2 C8 1.8446(18) . ? O1 C6 1.212(2) . ? O2 C9 1.206(2) . ? N4 C6 1.382(2) . ? N4 C9 1.383(2) . ? N4 H4 0.90(3) . ? C6 C7 1.499(3) . ? C7 C8 1.333(2) . ? C8 C9 1.504(3) . ? 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 C5 N1 C1 120.43(16) . . ? C1 N2 H2A 120.2(16) . . ? C1 N2 H2B 115(2) . . ? H2A N2 H2B 124(2) . . ? C5 N3 H3A 118.2(15) . . ? C5 N3 H3B 116.2(18) . . ? H3A N3 H3B 125(2) . . ? N1 C1 N2 117.85(17) . . ? N1 C1 C2 120.38(16) . . ? N2 C1 C2 121.76(16) . . ? C3 C2 C1 119.97(16) . . ? C3 C2 Cl1 119.90(14) . . ? C1 C2 Cl1 120.13(13) . . ? C2 C3 C4 118.67(17) . . ? C2 C3 H3 121.2(13) . . ? C4 C3 H3 120.2(13) . . ? C3 C4 C5 120.13(16) . . ? C3 C4 Cl2 120.86(15) . . ? C5 C4 Cl2 119.02(13) . . ? N1 C5 N3 117.66(17) . . ? N1 C5 C4 120.35(15) . . ? N3 C5 C4 121.98(16) . . ? C6 N4 C9 111.42(16) . . ? C6 N4 H4 124.3(16) . . ? C9 N4 H4 123.9(16) . . ? O1 C6 N4 126.43(18) . . ? O1 C6 C7 127.64(17) . . ? N4 C6 C7 105.92(15) . . ? C8 C7 C6 108.49(16) . . ? C8 C7 Br1 129.23(15) . . ? C6 C7 Br1 122.25(12) . . ? C7 C8 C9 108.47(15) . . ? C7 C8 Br2 127.61(15) . . ? C9 C8 Br2 123.90(12) . . ? O2 C9 N4 125.90(18) . . ? O2 C9 C8 128.41(16) . . ? N4 C9 C8 105.68(14) . . ? 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 C5 N1 C1 N2 -178.75(16) . . . . ? C5 N1 C1 C2 1.3(2) . . . . ? N1 C1 C2 C3 -2.2(2) . . . . ? N2 C1 C2 C3 177.79(16) . . . . ? N1 C1 C2 Cl1 178.19(13) . . . . ? N2 C1 C2 Cl1 -1.8(2) . . . . ? C1 C2 C3 C4 0.8(2) . . . . ? Cl1 C2 C3 C4 -179.62(13) . . . . ? C2 C3 C4 C5 1.5(2) . . . . ? C2 C3 C4 Cl2 -178.51(13) . . . . ? C1 N1 C5 N3 -179.74(16) . . . . ? C1 N1 C5 C4 1.1(2) . . . . ? C3 C4 C5 N1 -2.5(2) . . . . ? Cl2 C4 C5 N1 177.52(12) . . . . ? C3 C4 C5 N3 178.35(17) . . . . ? Cl2 C4 C5 N3 -1.6(2) . . . . ? C9 N4 C6 O1 179.26(18) . . . . ? C9 N4 C6 C7 -1.33(19) . . . . ? O1 C6 C7 C8 179.91(18) . . . . ? N4 C6 C7 C8 0.52(19) . . . . ? O1 C6 C7 Br1 -2.0(3) . . . . ? N4 C6 C7 Br1 178.60(12) . . . . ? C6 C7 C8 C9 0.41(19) . . . . ? Br1 C7 C8 C9 -177.49(12) . . . . ? C6 C7 C8 Br2 178.85(12) . . . . ? Br1 C7 C8 Br2 1.0(3) . . . . ? C6 N4 C9 O2 -177.48(17) . . . . ? C6 N4 C9 C8 1.56(18) . . . . ? C7 C8 C9 O2 177.81(18) . . . . ? Br2 C8 C9 O2 -0.7(3) . . . . ? C7 C8 C9 N4 -1.20(19) . . . . ? Br2 C8 C9 N4 -179.71(12) . . . . ? _diffrn_measured_fraction_theta_max 0.875 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.609 _refine_diff_density_min -0.754 _refine_diff_density_rms 0.098 # Attachment 'BrMaHPy.CIF' data_cz24 _database_code_depnum_ccdc_archive 'CCDC 810507' #TrackingRef 'BrMaHPy.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C5 H8 N3 1+, C4 Br2 N O2 1-' _chemical_formula_sum 'C9 H8 Br2 N4 O2' _chemical_formula_weight 364.01 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' Br Br -0.2901 2.4595 '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 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 3.8217(6) _cell_length_b 22.432(3) _cell_length_c 13.711(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.809(12) _cell_angle_gamma 90.00 _cell_volume 1164.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 3693 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 28.62 _exptl_crystal_description neeedle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.076 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 6.956 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.' _exptl_absorpt_correction_T_min 0.1935 _exptl_absorpt_correction_T_max 0.2661 _exptl_special_details ; The crystal are long and thin needles, very fragile and difficult to cut without breaking. Th data collection was carried on at low temperature using a Bruker KRYOFLEX low temperature device. ; _diffrn_ambient_temperature 103(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 12949 _diffrn_reflns_av_R_equivalents 0.0499 _diffrn_reflns_av_sigmaI/netI 0.0530 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 29.13 _reflns_number_total 3047 _reflns_number_gt 2306 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.) ; _computing_structure_refinement 'SHELXL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457 ; _computing_publication_material SHELXTL _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. H atoms bonded to N atoms were refined with soft restraints: their Uiso were set nearly equal to that of their bonded N atoms. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0524P)^2^] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3047 _refine_ls_number_parameters 186 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0628 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.0982 _refine_ls_wR_factor_gt 0.0893 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.062 _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 Br1 Br 0.81342(10) 0.292408(17) 0.67155(3) 0.02179(12) Uani 1 1 d . . . Br2 Br 0.70588(10) 0.304444(17) 0.93691(3) 0.02207(12) Uani 1 1 d . . . O1 O 0.5077(7) 0.42437(12) 0.60500(17) 0.0220(6) Uani 1 1 d . . . O2 O 0.3146(7) 0.43421(12) 0.92359(17) 0.0214(6) Uani 1 1 d . . . N4 N 0.3689(8) 0.44659(14) 0.7595(2) 0.0187(7) Uani 1 1 d . . . C6 C 0.4997(10) 0.41175(17) 0.6919(3) 0.0178(8) Uani 1 1 d . . . C7 C 0.6372(9) 0.35395(16) 0.7400(2) 0.0157(7) Uani 1 1 d . . . C8 C 0.5910(9) 0.35798(16) 0.8346(2) 0.0157(7) Uani 1 1 d . . . C9 C 0.4139(9) 0.41694(16) 0.8464(2) 0.0159(7) Uani 1 1 d . . . N1 N 0.0444(8) 0.55691(14) 0.7296(2) 0.0140(6) Uani 1 1 d U . . H1 H 0.129(10) 0.5239(19) 0.737(3) 0.015(3) Uiso 1 1 d U . . N2 N 0.1854(9) 0.54986(15) 0.5729(2) 0.0195(7) Uani 1 1 d U . . H2A H 0.289(11) 0.514(2) 0.584(3) 0.025(4) Uiso 1 1 d U . . H2B H 0.234(11) 0.5618(19) 0.520(3) 0.027(4) Uiso 1 1 d U . . N3 N -0.0634(9) 0.55361(15) 0.8912(2) 0.0222(7) Uani 1 1 d U . . H3A H 0.035(11) 0.519(2) 0.892(3) 0.025(4) Uiso 1 1 d U . . H3B H -0.156(11) 0.5683(19) 0.943(3) 0.026(4) Uiso 1 1 d U . . C1 C 0.0443(10) 0.58209(16) 0.6400(2) 0.0156(7) Uani 1 1 d . . . C2 C -0.0980(10) 0.63881(17) 0.6241(3) 0.0189(8) Uani 1 1 d . . . H2 H -0.120(11) 0.654(2) 0.569(3) 0.025(12) Uiso 1 1 d . . . C3 C -0.2327(10) 0.66672(18) 0.7004(3) 0.0193(8) Uani 1 1 d . . . H3 H -0.325(11) 0.7019(17) 0.691(3) 0.019(11) Uiso 1 1 d . . . C4 C -0.2277(10) 0.64102(18) 0.7914(3) 0.0185(8) Uani 1 1 d . . . H4 H -0.314(10) 0.6583(19) 0.840(3) 0.022(11) Uiso 1 1 d . . . C5 C -0.0828(10) 0.58451(16) 0.8066(2) 0.0164(7) Uani 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 Br1 0.0156(2) 0.0238(2) 0.0265(2) -0.00797(15) 0.00496(15) 0.00300(15) Br2 0.0206(2) 0.0238(2) 0.0211(2) 0.00675(15) 0.00064(15) 0.00112(15) O1 0.0229(15) 0.0303(16) 0.0142(12) 0.0011(11) 0.0076(11) 0.0032(12) O2 0.0277(15) 0.0240(15) 0.0140(12) -0.0013(10) 0.0081(11) 0.0003(12) N4 0.0216(17) 0.0195(17) 0.0158(14) -0.0015(12) 0.0060(12) 0.0013(13) C6 0.0142(19) 0.022(2) 0.0176(17) -0.0020(14) 0.0045(14) -0.0024(15) C7 0.0094(18) 0.0185(19) 0.0197(17) -0.0040(14) 0.0036(14) -0.0002(14) C8 0.0103(17) 0.0176(18) 0.0195(16) 0.0027(14) 0.0031(14) -0.0018(14) C9 0.0130(18) 0.0187(19) 0.0163(16) -0.0018(13) 0.0034(14) -0.0030(14) N1 0.0142(15) 0.0138(15) 0.0147(13) -0.0003(11) 0.0040(11) 0.0010(12) N2 0.0249(18) 0.0220(17) 0.0130(14) 0.0017(12) 0.0078(13) -0.0013(14) N3 0.0294(19) 0.0215(18) 0.0175(15) 0.0005(13) 0.0091(14) 0.0054(15) C1 0.0123(18) 0.0204(19) 0.0143(15) -0.0015(14) 0.0019(13) -0.0030(14) C2 0.021(2) 0.0196(19) 0.0155(17) 0.0032(15) -0.0002(15) -0.0043(16) C3 0.016(2) 0.014(2) 0.0268(19) -0.0021(15) -0.0003(15) -0.0005(15) C4 0.016(2) 0.019(2) 0.0206(18) -0.0049(15) 0.0051(15) -0.0008(15) C5 0.0107(18) 0.023(2) 0.0172(16) -0.0025(14) 0.0070(13) -0.0021(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 Br1 C7 1.847(4) . ? Br2 C8 1.853(3) . ? O1 C6 1.229(4) . ? O2 C9 1.234(4) . ? N4 C9 1.355(4) . ? N4 C6 1.359(4) . ? C6 C7 1.516(5) . ? C7 C8 1.336(5) . ? C8 C9 1.504(5) . ? N1 C1 1.352(4) . ? N1 C5 1.369(4) . ? N1 H1 0.81(4) . ? N2 C1 1.340(5) . ? N2 H2A 0.89(4) . ? N2 H2B 0.82(4) . ? N3 C5 1.345(5) . ? N3 H3A 0.86(5) . ? N3 H3B 0.90(4) . ? C1 C2 1.389(5) . ? C2 C3 1.378(5) . ? C2 H2 0.83(4) . ? C3 C4 1.372(5) . ? C3 H3 0.87(4) . ? C4 C5 1.388(5) . ? C4 H4 0.88(4) . ? 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 C9 N4 C6 107.6(3) . . ? O1 C6 N4 126.1(4) . . ? O1 C6 C7 124.5(3) . . ? N4 C6 C7 109.5(3) . . ? C8 C7 C6 106.3(3) . . ? C8 C7 Br1 130.5(3) . . ? C6 C7 Br1 123.1(2) . . ? C7 C8 C9 106.5(3) . . ? C7 C8 Br2 129.9(3) . . ? C9 C8 Br2 123.5(2) . . ? O2 C9 N4 125.6(3) . . ? O2 C9 C8 124.3(3) . . ? N4 C9 C8 110.0(3) . . ? C1 N1 C5 123.7(3) . . ? C1 N1 H1 117(3) . . ? C5 N1 H1 120(3) . . ? C1 N2 H2A 125(3) . . ? C1 N2 H2B 126(3) . . ? H2A N2 H2B 107(4) . . ? C5 N3 H3A 117(3) . . ? C5 N3 H3B 121(3) . . ? H3A N3 H3B 122(4) . . ? N2 C1 N1 116.6(3) . . ? N2 C1 C2 124.9(3) . . ? N1 C1 C2 118.5(3) . . ? C3 C2 C1 118.4(3) . . ? C3 C2 H2 120(3) . . ? C1 C2 H2 121(3) . . ? C4 C3 C2 122.6(4) . . ? C4 C3 H3 118(3) . . ? C2 C3 H3 119(3) . . ? C3 C4 C5 118.4(3) . . ? C3 C4 H4 123(3) . . ? C5 C4 H4 118(3) . . ? N3 C5 N1 116.6(3) . . ? N3 C5 C4 125.1(3) . . ? N1 C5 C4 118.3(3) . . ? 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 C9 N4 C6 O1 -179.2(4) . . . . ? C9 N4 C6 C7 0.8(4) . . . . ? O1 C6 C7 C8 178.2(4) . . . . ? N4 C6 C7 C8 -1.8(4) . . . . ? O1 C6 C7 Br1 -3.7(5) . . . . ? N4 C6 C7 Br1 176.3(2) . . . . ? C6 C7 C8 C9 1.9(4) . . . . ? Br1 C7 C8 C9 -176.0(3) . . . . ? C6 C7 C8 Br2 -178.8(3) . . . . ? Br1 C7 C8 Br2 3.3(6) . . . . ? C6 N4 C9 O2 -177.2(4) . . . . ? C6 N4 C9 C8 0.4(4) . . . . ? C7 C8 C9 O2 176.1(4) . . . . ? Br2 C8 C9 O2 -3.3(5) . . . . ? C7 C8 C9 N4 -1.5(4) . . . . ? Br2 C8 C9 N4 179.1(3) . . . . ? C5 N1 C1 N2 178.6(3) . . . . ? C5 N1 C1 C2 -1.1(5) . . . . ? N2 C1 C2 C3 -179.7(4) . . . . ? N1 C1 C2 C3 0.0(5) . . . . ? C1 C2 C3 C4 0.8(6) . . . . ? C2 C3 C4 C5 -0.4(6) . . . . ? C1 N1 C5 N3 -179.8(3) . . . . ? C1 N1 C5 C4 1.5(5) . . . . ? C3 C4 C5 N3 -179.2(4) . . . . ? C3 C4 C5 N1 -0.7(5) . . . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.188 _refine_diff_density_min -0.943 _refine_diff_density_rms 0.145 data_cz20 _database_code_depnum_ccdc_archive 'CCDC 810508' #TrackingRef 'BrPy.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,3-diamino-3,5-dibromopyridine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C5 H5 Br2 N3' _chemical_formula_sum 'C5 H5 Br2 N3' _chemical_formula_weight 266.94 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' Br Br -0.2901 2.4595 '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 b c n' _symmetry_space_group_name_Hall '-P 2n 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 12.267(2) _cell_length_b 11.930(2) _cell_length_c 4.9664(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 726.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1295 _cell_measurement_theta_min 3.32 _cell_measurement_theta_max 30.48 _exptl_crystal_description table _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.440 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 11.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.' _exptl_absorpt_correction_T_min 0.1234 _exptl_absorpt_correction_T_max 0.2407 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 APEX-II CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 4644 _diffrn_reflns_av_R_equivalents 0.0331 _diffrn_reflns_av_sigmaI/netI 0.0303 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 32.90 _reflns_number_total 1227 _reflns_number_gt 982 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457 ; _computing_publication_material 'SHELXL-97 (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 'w=1/[\s^2^(Fo^2^)+(0.0185P)^2^+0.3190P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1227 _refine_ls_number_parameters 56 _refine_ls_number_restraints 21 _refine_ls_R_factor_all 0.0341 _refine_ls_R_factor_gt 0.0228 _refine_ls_wR_factor_ref 0.0544 _refine_ls_wR_factor_gt 0.0506 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.020 _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 Br1 Br 0.667267(18) 0.135788(19) 0.35451(4) 0.03623(8) Uani 1 1 d . . . N1 N 0.5000 0.38588(18) 0.7500 0.0264(4) Uani 1 2 d S . . C1 C 0.56591(15) 0.32931(16) 0.5815(3) 0.0249(4) Uani 1 1 d . . . C2 C 0.56966(15) 0.21292(15) 0.5844(3) 0.0255(4) Uani 1 1 d . . . C3 C 0.5000 0.1543(2) 0.7500 0.0282(5) Uani 1 2 d SU . . H3 H 0.5000 0.078(3) 0.7500 0.034 Uiso 1 2 d SU . . N2 N 0.62965(16) 0.39402(16) 0.4184(4) 0.0342(4) Uani 1 1 d DU . . H2A H 0.6042(19) 0.4583(12) 0.385(4) 0.037(5) Uiso 1 1 d DU . . H2B H 0.6651(19) 0.357(2) 0.303(5) 0.045(6) Uiso 1 1 d DU . . 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 Br1 0.03521(14) 0.03508(13) 0.03839(12) -0.00626(8) 0.00418(8) 0.00827(8) N1 0.0296(11) 0.0213(10) 0.0284(9) 0.000 0.0021(9) 0.000 C1 0.0242(9) 0.0258(8) 0.0248(7) 0.0016(7) -0.0012(6) 0.0003(7) C2 0.0258(9) 0.0234(9) 0.0273(7) -0.0018(7) -0.0006(6) 0.0034(7) C3 0.0313(14) 0.0209(12) 0.0324(12) 0.000 -0.0034(11) 0.000 N2 0.0367(9) 0.0283(8) 0.0376(8) 0.0061(7) 0.0094(7) 0.0024(8) _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. N-H distances were restrained to be about equal. ; 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 Br1 C2 1.8931(18) . ? N1 C1 1.345(2) . ? N1 C1 1.345(2) 4_656 ? C1 N2 1.365(3) . ? C1 C2 1.389(3) . ? C2 C3 1.377(2) . ? C3 C2 1.377(2) 4_656 ? C3 H3 0.91(3) . ? N2 H2A 0.844(10) . ? N2 H2B 0.842(10) . ? 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 C1 N1 C1 119.8(2) . 4_656 ? N1 C1 N2 115.45(18) . . ? N1 C1 C2 120.98(17) . . ? N2 C1 C2 123.53(18) . . ? C3 C2 C1 119.56(17) . . ? C3 C2 Br1 120.39(15) . . ? C1 C2 Br1 120.03(14) . . ? C2 C3 C2 118.9(2) 4_656 . ? C2 C3 H3 120.53(12) 4_656 . ? C2 C3 H3 120.53(12) . . ? C1 N2 H2A 114.7(17) . . ? C1 N2 H2B 114(2) . . ? H2A N2 H2B 122(3) . . ? 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 C1 N1 C1 N2 179.98(19) 4_656 . . . ? C1 N1 C1 C2 -2.07(12) 4_656 . . . ? N1 C1 C2 C3 4.1(2) . . . . ? N2 C1 C2 C3 -178.09(16) . . . . ? N1 C1 C2 Br1 -177.58(10) . . . . ? N2 C1 C2 Br1 0.2(3) . . . . ? C1 C2 C3 C2 -2.00(12) . . . 4_656 ? Br1 C2 C3 C2 179.72(15) . . . 4_656 ? _diffrn_measured_fraction_theta_max 0.900 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.370 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.081 # Attachment 'ClMA_alpha.CIF' data_cz18 _database_code_depnum_ccdc_archive 'CCDC 810509' #TrackingRef 'ClMA_alpha.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H Cl2 N O2' _chemical_formula_sum 'C4 H Cl2 N O2' _chemical_formula_weight 165.96 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' 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 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 7.274(3) _cell_length_b 8.086(3) _cell_length_c 10.350(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.35(2) _cell_angle_gamma 90.00 _cell_volume 596.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 9345 _cell_measurement_theta_min 2.86 _cell_measurement_theta_max 28.14 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.847 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.997 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.' _exptl_absorpt_correction_T_min 0.5823 _exptl_absorpt_correction_T_max 0.7465 _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 APEX-II CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 23252 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_sigmaI/netI 0.0277 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 32.77 _reflns_number_total 2008 _reflns_number_gt 1251 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457 ; _computing_publication_material 'SHELXL-97 (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 'w=1/[\s^2^(Fo^2^)+(0.0486P)^2^+0.0765P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2008 _refine_ls_number_parameters 82 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0742 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0979 _refine_ls_wR_factor_gt 0.0853 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 0.02822(6) 0.23287(6) -0.20288(4) 0.05970(17) Uani 1 1 d . . . Cl2 Cl 0.25760(6) 0.52962(5) 0.01260(5) 0.06186(18) Uani 1 1 d . . . N1 N 0.36052(19) 0.06923(15) 0.11417(13) 0.0465(3) Uani 1 1 d . . . H1 H 0.4145 -0.0073 0.1657 0.056 Uiso 1 1 calc R . . C1 C 0.2369(2) 0.0400(2) -0.00305(14) 0.0418(3) Uani 1 1 d . . . C2 C 0.1801(2) 0.20755(17) -0.05912(15) 0.0400(3) Uani 1 1 d . . . C3 C 0.2679(2) 0.3218(2) 0.02322(15) 0.0414(3) Uani 1 1 d . . . C4 C 0.3866(2) 0.2355(2) 0.13843(16) 0.0432(4) Uani 1 1 d . . . O1 O 0.18728(18) -0.09177(15) -0.04903(12) 0.0589(3) Uani 1 1 d . . . O2 O 0.48412(19) 0.29611(15) 0.23385(14) 0.0610(3) Uani 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 Cl1 0.0592(3) 0.0743(3) 0.0391(2) 0.00768(19) -0.00634(18) 0.0075(2) Cl2 0.0588(3) 0.0334(2) 0.0914(4) 0.0050(2) 0.0100(2) 0.00108(17) N1 0.0562(8) 0.0327(6) 0.0422(7) 0.0025(5) -0.0108(6) 0.0017(5) C1 0.0470(8) 0.0372(8) 0.0384(8) -0.0038(6) 0.0018(6) -0.0019(6) C2 0.0424(8) 0.0396(8) 0.0356(7) 0.0037(6) 0.0016(6) 0.0024(6) C3 0.0410(8) 0.0360(8) 0.0463(8) 0.0031(6) 0.0066(7) 0.0012(6) C4 0.0437(8) 0.0383(8) 0.0437(8) -0.0029(6) -0.0007(7) -0.0020(6) O1 0.0734(8) 0.0411(7) 0.0550(7) -0.0097(5) -0.0048(6) -0.0050(6) O2 0.0647(8) 0.0522(8) 0.0559(7) -0.0117(6) -0.0130(6) -0.0065(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 Cl1 C2 1.6819(16) . ? Cl2 C3 1.6849(18) . ? N1 C4 1.374(2) . ? N1 C1 1.3807(19) . ? N1 H1 0.8600 . ? C1 O1 1.194(2) . ? C1 C2 1.500(2) . ? C2 C3 1.332(2) . ? C3 C4 1.500(2) . ? C4 O2 1.201(2) . ? 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 C4 N1 C1 111.76(13) . . ? C4 N1 H1 124.1 . . ? C1 N1 H1 124.1 . . ? O1 C1 N1 126.63(15) . . ? O1 C1 C2 127.83(15) . . ? N1 C1 C2 105.54(12) . . ? C3 C2 C1 108.53(14) . . ? C3 C2 Cl1 129.09(13) . . ? C1 C2 Cl1 122.38(11) . . ? C2 C3 C4 108.35(15) . . ? C2 C3 Cl2 129.82(13) . . ? C4 C3 Cl2 121.82(12) . . ? O2 C4 N1 125.98(15) . . ? O2 C4 C3 128.19(16) . . ? N1 C4 C3 105.82(13) . . ? 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 C4 N1 C1 O1 -179.70(17) . . . . ? C4 N1 C1 C2 0.41(17) . . . . ? O1 C1 C2 C3 -179.92(16) . . . . ? N1 C1 C2 C3 -0.03(17) . . . . ? O1 C1 C2 Cl1 0.4(2) . . . . ? N1 C1 C2 Cl1 -179.73(11) . . . . ? C1 C2 C3 C4 -0.32(17) . . . . ? Cl1 C2 C3 C4 179.35(12) . . . . ? C1 C2 C3 Cl2 -179.53(11) . . . . ? Cl1 C2 C3 Cl2 0.1(2) . . . . ? C1 N1 C4 O2 178.79(17) . . . . ? C1 N1 C4 C3 -0.59(18) . . . . ? C2 C3 C4 O2 -178.80(18) . . . . ? Cl2 C3 C4 O2 0.5(2) . . . . ? C2 C3 C4 N1 0.57(18) . . . . ? Cl2 C3 C4 N1 179.85(11) . . . . ? _diffrn_measured_fraction_theta_max 0.910 _diffrn_reflns_theta_full 28.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.285 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.053 # Attachment 'ClMaClPY.CIF' data_cz14lt _database_code_depnum_ccdc_archive 'CCDC 810510' #TrackingRef 'ClMaClPY.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C5 H5 cL2 N3, C4 H Cl2 N O2' _chemical_formula_sum 'C9 H6 Cl4 N4 O2' _chemical_formula_weight 343.98 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' Cl Cl 0.1484 0.1585 '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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.1818(6) _cell_length_b 7.8344(7) _cell_length_c 11.6453(15) _cell_angle_alpha 101.979(11) _cell_angle_beta 101.519(11) _cell_angle_gamma 97.213(10) _cell_volume 618.44(11) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 4665 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 34.10 _exptl_crystal_description table _exptl_crystal_colour red-orange _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.847 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.958 _exptl_absorpt_correction_type none _exptl_special_details ; OXFORD low temperature device. ; _diffrn_ambient_temperature 123(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, APEX 2000, CCD area detector' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 10015 _diffrn_reflns_av_R_equivalents 0.0887 _diffrn_reflns_av_sigmaI/netI 0.0796 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 34.36 _reflns_number_total 4801 _reflns_number_gt 3871 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457 ; _computing_publication_material 'SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)' _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 'w=1/[\s^2^(Fo^2^)+(0.0307P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4801 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0460 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0964 _refine_ls_wR_factor_gt 0.0911 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 0.14126(5) -0.27696(4) 0.12998(3) 0.01915(8) Uani 1 1 d . . . Cl2 Cl 0.84661(5) 0.07390(4) 0.14271(3) 0.02078(8) Uani 1 1 d . . . N1 N 0.50352(15) 0.12000(13) 0.37200(9) 0.0166(2) Uani 1 1 d . . . N2 N 0.20640(18) -0.03131(17) 0.37419(11) 0.0212(2) Uani 1 1 d . . . H2A H 0.212(3) 0.041(2) 0.4372(16) 0.032(5) Uiso 1 1 d . . . H2B H 0.096(3) -0.094(3) 0.3405(18) 0.058(7) Uiso 1 1 d . . . N3 N 0.80392(18) 0.27631(16) 0.38142(11) 0.0211(2) Uani 1 1 d . . . H3A H 0.810(3) 0.323(2) 0.4471(17) 0.041(6) Uiso 1 1 d . . . H3B H 0.915(3) 0.295(3) 0.3522(17) 0.047(6) Uiso 1 1 d . . . C1 C 0.34867(18) -0.00836(16) 0.31600(11) 0.0153(2) Uani 1 1 d . . . C2 C 0.34163(18) -0.11457(15) 0.20128(11) 0.0154(2) Uani 1 1 d . . . C3 C 0.49288(19) -0.08973(16) 0.14666(11) 0.0156(2) Uani 1 1 d . . . H3 H 0.489(3) -0.159(2) 0.0720(15) 0.031(5) Uiso 1 1 d . . . C4 C 0.65135(18) 0.04023(16) 0.20619(11) 0.0156(2) Uani 1 1 d . . . C5 C 0.65385(18) 0.14419(16) 0.32070(11) 0.0156(2) Uani 1 1 d . . . Cl3 Cl 0.73834(5) 0.72247(4) 0.88489(3) 0.01855(8) Uani 1 1 d . . . Cl4 Cl 0.28804(5) 0.50117(4) 0.87129(3) 0.02285(8) Uani 1 1 d . . . O1 O 0.20696(15) 0.22914(13) 0.61509(9) 0.0211(2) Uani 1 1 d . . . O2 O 0.80264(15) 0.52764(13) 0.62912(9) 0.0210(2) Uani 1 1 d . . . N4 N 0.50177(16) 0.35318(14) 0.59035(10) 0.0169(2) Uani 1 1 d . . . H4 H 0.503(3) 0.286(2) 0.5263(15) 0.031(5) Uiso 1 1 d . . . C6 C 0.35584(19) 0.33525(16) 0.65022(11) 0.0164(2) Uani 1 1 d . . . C7 C 0.42173(18) 0.47234(15) 0.76771(11) 0.0152(2) Uani 1 1 d . . . C8 C 0.59661(18) 0.55841(15) 0.77228(11) 0.0150(2) Uani 1 1 d . . . C9 C 0.65395(19) 0.48383(16) 0.65765(11) 0.0158(2) Uani 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 Cl1 0.01374(14) 0.01585(13) 0.02296(15) -0.00015(11) 0.00140(11) -0.00293(10) Cl2 0.01539(14) 0.02222(15) 0.02337(15) 0.00114(12) 0.00811(12) -0.00033(11) N1 0.0131(5) 0.0181(5) 0.0155(5) 0.0016(4) 0.0022(4) -0.0026(4) N2 0.0143(5) 0.0262(6) 0.0185(5) -0.0001(4) 0.0046(4) -0.0055(4) N3 0.0145(5) 0.0245(6) 0.0182(5) -0.0022(4) 0.0034(4) -0.0066(4) C1 0.0128(5) 0.0161(5) 0.0161(5) 0.0044(4) 0.0023(4) -0.0003(4) C2 0.0129(5) 0.0131(5) 0.0169(5) 0.0021(4) -0.0003(4) -0.0014(4) C3 0.0149(6) 0.0149(5) 0.0160(5) 0.0016(4) 0.0031(4) 0.0028(4) C4 0.0134(5) 0.0163(5) 0.0167(5) 0.0029(4) 0.0043(4) 0.0015(4) C5 0.0127(5) 0.0163(5) 0.0165(5) 0.0031(4) 0.0027(4) -0.0002(4) Cl3 0.01632(15) 0.01552(13) 0.01953(14) -0.00039(10) 0.00284(11) -0.00320(11) Cl4 0.01880(16) 0.02409(16) 0.02439(16) 0.00046(12) 0.01108(13) -0.00175(12) O1 0.0152(4) 0.0205(4) 0.0231(4) 0.0019(4) 0.0025(4) -0.0054(4) O2 0.0153(4) 0.0239(5) 0.0218(4) 0.0031(4) 0.0061(4) -0.0026(4) N4 0.0143(5) 0.0185(5) 0.0151(4) -0.0007(4) 0.0048(4) -0.0019(4) C6 0.0141(5) 0.0160(5) 0.0182(5) 0.0049(4) 0.0029(5) -0.0004(4) C7 0.0137(5) 0.0149(5) 0.0161(5) 0.0021(4) 0.0044(4) 0.0007(4) C8 0.0140(5) 0.0126(5) 0.0168(5) 0.0027(4) 0.0022(4) -0.0002(4) C9 0.0128(5) 0.0155(5) 0.0178(5) 0.0040(4) 0.0020(5) 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 1.7330(12) . ? Cl2 C4 1.7276(13) . ? N1 C5 1.3460(16) . ? N1 C1 1.3530(15) . ? N2 C1 1.3478(17) . ? N2 H2A 0.818(18) . ? N2 H2B 0.85(2) . ? N3 C5 1.3582(16) . ? N3 H3A 0.766(19) . ? N3 H3B 0.94(2) . ? C1 C2 1.4073(17) . ? C2 C3 1.3772(18) . ? C3 C4 1.3833(17) . ? C3 H3 0.916(17) . ? C4 C5 1.4063(17) . ? Cl3 C8 1.6871(12) . ? Cl4 C7 1.6827(13) . ? O1 C6 1.2093(16) . ? O2 C9 1.2106(16) . ? N4 C6 1.3783(17) . ? N4 C9 1.3786(16) . ? N4 H4 0.820(17) . ? C6 C7 1.5011(17) . ? C7 C8 1.3345(17) . ? C8 C9 1.4997(18) . ? 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 C5 N1 C1 120.71(11) . . ? C1 N2 H2A 117.9(13) . . ? C1 N2 H2B 123.6(15) . . ? H2A N2 H2B 116(2) . . ? C5 N3 H3A 120.0(16) . . ? C5 N3 H3B 121.3(12) . . ? H3A N3 H3B 117.2(19) . . ? N2 C1 N1 117.98(11) . . ? N2 C1 C2 122.19(11) . . ? N1 C1 C2 119.82(12) . . ? C3 C2 C1 120.20(11) . . ? C3 C2 Cl1 120.49(9) . . ? C1 C2 Cl1 119.31(10) . . ? C2 C3 C4 119.13(11) . . ? C2 C3 H3 120.3(12) . . ? C4 C3 H3 120.6(12) . . ? C3 C4 C5 119.26(12) . . ? C3 C4 Cl2 120.90(10) . . ? C5 C4 Cl2 119.83(9) . . ? N1 C5 N3 117.63(11) . . ? N1 C5 C4 120.85(11) . . ? N3 C5 C4 121.48(12) . . ? C6 N4 C9 111.69(11) . . ? C6 N4 H4 123.7(13) . . ? C9 N4 H4 124.2(13) . . ? O1 C6 N4 126.67(12) . . ? O1 C6 C7 127.57(13) . . ? N4 C6 C7 105.75(10) . . ? C8 C7 C6 108.34(11) . . ? C8 C7 Cl4 128.81(10) . . ? C6 C7 Cl4 122.84(9) . . ? C7 C8 C9 108.44(11) . . ? C7 C8 Cl3 128.08(11) . . ? C9 C8 Cl3 123.47(9) . . ? O2 C9 N4 126.55(12) . . ? O2 C9 C8 127.70(11) . . ? N4 C9 C8 105.76(11) . . ? 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 C5 N1 C1 N2 177.13(12) . . . . ? C5 N1 C1 C2 -1.89(18) . . . . ? N2 C1 C2 C3 -178.13(12) . . . . ? N1 C1 C2 C3 0.84(19) . . . . ? N2 C1 C2 Cl1 1.68(18) . . . . ? N1 C1 C2 Cl1 -179.34(9) . . . . ? C1 C2 C3 C4 0.21(19) . . . . ? Cl1 C2 C3 C4 -179.60(9) . . . . ? C2 C3 C4 C5 -0.25(18) . . . . ? C2 C3 C4 Cl2 178.82(10) . . . . ? C1 N1 C5 N3 179.51(12) . . . . ? C1 N1 C5 C4 1.87(19) . . . . ? C3 C4 C5 N1 -0.78(19) . . . . ? Cl2 C4 C5 N1 -179.86(10) . . . . ? C3 C4 C5 N3 -178.33(12) . . . . ? Cl2 C4 C5 N3 2.59(18) . . . . ? C9 N4 C6 O1 -178.11(14) . . . . ? C9 N4 C6 C7 1.13(14) . . . . ? O1 C6 C7 C8 178.19(14) . . . . ? N4 C6 C7 C8 -1.04(14) . . . . ? O1 C6 C7 Cl4 -1.2(2) . . . . ? N4 C6 C7 Cl4 179.53(9) . . . . ? C6 C7 C8 C9 0.57(14) . . . . ? Cl4 C7 C8 C9 179.95(10) . . . . ? C6 C7 C8 Cl3 -178.82(9) . . . . ? Cl4 C7 C8 Cl3 0.6(2) . . . . ? C6 N4 C9 O2 179.04(14) . . . . ? C6 N4 C9 C8 -0.79(14) . . . . ? C7 C8 C9 O2 -179.74(14) . . . . ? Cl3 C8 C9 O2 -0.3(2) . . . . ? C7 C8 C9 N4 0.09(14) . . . . ? Cl3 C8 C9 N4 179.52(9) . . . . ? _diffrn_measured_fraction_theta_max 0.924 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.558 _refine_diff_density_min -0.487 _refine_diff_density_rms 0.097 # Attachment 'ClMaHPy.CIF' data_cz13 _database_code_depnum_ccdc_archive 'CCDC 810511' #TrackingRef 'ClMaHPy.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C5 H8 N3 1+, C4 Cl2 O2 1-' _chemical_formula_sum 'C9 H8 Cl2 N4 O2' _chemical_formula_weight 275.09 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' Cl Cl 0.1484 0.1585 '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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 3.7835(18) _cell_length_b 11.450(6) _cell_length_c 13.799(7) _cell_angle_alpha 97.018(18) _cell_angle_beta 96.799(18) _cell_angle_gamma 96.993(17) _cell_volume 583.5(5) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3192 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 27.43 _exptl_crystal_description needle _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.566 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_absorpt_coefficient_mu 0.551 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.' _exptl_absorpt_correction_T_min 0.5806 _exptl_absorpt_correction_T_max 0.7459 _exptl_special_details ; The crystals were sheafs of very small needles nearly parallel and very difficult to cut perpendicularly to their main axis. The crystal chosen for the data collection was the largest one. We preferred this one because it was at least ten times bigger than than all the others, although it had bad terminations which were impossible to cut away. ; _diffrn_ambient_temperature 296(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 APEX-II CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 6856 _diffrn_reflns_av_R_equivalents 0.0280 _diffrn_reflns_av_sigmaI/netI 0.0372 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 29.75 _reflns_number_total 2874 _reflns_number_gt 2011 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457 ; _computing_publication_material 'SHELXL-97 (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 'w=1/[\s^2^(Fo^2^)+(0.0439P)^2^+0.1711P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2874 _refine_ls_number_parameters 186 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0650 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.1093 _refine_ls_wR_factor_gt 0.0952 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 N1 N 0.3846(4) 0.38910(14) 0.25301(11) 0.0387(4) Uani 1 1 d . . . H1 H 0.322(6) 0.463(2) 0.2513(15) 0.054(6) Uiso 1 1 d . . . N2 N 0.4903(6) 0.3967(2) 0.09346(15) 0.0636(6) Uani 1 1 d . . . H2A H 0.421(7) 0.463(3) 0.096(2) 0.076(9) Uiso 1 1 d . . . H2B H 0.553(6) 0.365(2) 0.040(2) 0.064(7) Uiso 1 1 d . . . N3 N 0.2625(6) 0.4022(2) 0.41227(14) 0.0538(5) Uani 1 1 d . . . H3A H 0.210(6) 0.469(2) 0.4083(17) 0.053(7) Uiso 1 1 d . . . H3B H 0.228(7) 0.372(2) 0.463(2) 0.071(8) Uiso 1 1 d . . . C1 C 0.4814(5) 0.33445(18) 0.16843(14) 0.0429(4) Uani 1 1 d . . . C2 C 0.5642(6) 0.2199(2) 0.16743(18) 0.0537(6) Uani 1 1 d . . . H2 H 0.628(6) 0.1835(19) 0.1117(16) 0.052(6) Uiso 1 1 d . . . C3 C 0.5468(6) 0.1673(2) 0.2512(2) 0.0582(6) Uani 1 1 d . . . H3 H 0.613(6) 0.089(2) 0.2510(17) 0.066(7) Uiso 1 1 d . . . C4 C 0.4458(6) 0.2231(2) 0.33543(19) 0.0538(5) Uani 1 1 d . . . H4 H 0.449(6) 0.189(2) 0.3888(18) 0.064(7) Uiso 1 1 d . . . C5 C 0.3615(5) 0.33753(17) 0.33572(14) 0.0409(4) Uani 1 1 d . . . Cl1 Cl -0.01625(18) 0.89440(6) 0.12661(5) 0.0690(2) Uani 1 1 d . . . Cl2 Cl -0.12140(17) 0.90876(5) 0.37791(5) 0.0663(2) Uani 1 1 d . . . O1 O 0.2414(4) 0.64324(14) 0.09471(10) 0.0605(4) Uani 1 1 d . . . O2 O 0.0566(5) 0.65554(15) 0.41313(11) 0.0649(5) Uani 1 1 d . . . N4 N 0.1761(5) 0.61362(14) 0.25374(12) 0.0470(4) Uani 1 1 d . . . C6 C 0.1623(5) 0.67489(17) 0.17598(14) 0.0419(4) Uani 1 1 d . . . C7 C 0.0388(5) 0.79327(17) 0.20545(15) 0.0424(4) Uani 1 1 d . . . C8 C -0.0062(5) 0.79794(17) 0.29867(15) 0.0423(4) Uani 1 1 d . . . C9 C 0.0771(5) 0.68171(18) 0.33089(14) 0.0440(5) Uani 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 N1 0.0423(9) 0.0385(9) 0.0368(9) 0.0037(7) 0.0103(7) 0.0077(7) N2 0.0928(16) 0.0659(14) 0.0398(11) 0.0065(10) 0.0289(11) 0.0234(12) N3 0.0727(13) 0.0573(13) 0.0358(10) 0.0126(9) 0.0174(9) 0.0113(10) C1 0.0404(10) 0.0507(11) 0.0371(10) -0.0013(8) 0.0101(8) 0.0068(8) C2 0.0501(13) 0.0522(13) 0.0574(14) -0.0076(11) 0.0107(10) 0.0128(10) C3 0.0532(13) 0.0427(12) 0.0772(17) 0.0035(11) 0.0001(11) 0.0135(10) C4 0.0577(14) 0.0489(12) 0.0561(14) 0.0186(11) 0.0018(11) 0.0064(10) C5 0.0377(10) 0.0479(11) 0.0367(10) 0.0082(8) 0.0042(8) 0.0020(8) Cl1 0.0776(4) 0.0641(4) 0.0735(4) 0.0329(3) 0.0130(3) 0.0169(3) Cl2 0.0680(4) 0.0628(4) 0.0672(4) -0.0139(3) 0.0146(3) 0.0227(3) O1 0.0797(11) 0.0687(10) 0.0376(8) 0.0042(7) 0.0249(8) 0.0147(8) O2 0.0841(12) 0.0809(11) 0.0406(9) 0.0199(8) 0.0253(8) 0.0271(9) N4 0.0618(11) 0.0453(9) 0.0398(9) 0.0082(7) 0.0186(8) 0.0173(8) C6 0.0438(11) 0.0450(10) 0.0374(10) 0.0043(8) 0.0099(8) 0.0051(8) C7 0.0384(10) 0.0436(10) 0.0455(11) 0.0076(8) 0.0068(8) 0.0041(8) C8 0.0373(10) 0.0449(10) 0.0444(11) 0.0002(8) 0.0083(8) 0.0082(8) C9 0.0453(11) 0.0520(11) 0.0375(11) 0.0077(9) 0.0116(8) 0.0104(9) _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 N1 C5 1.354(2) . ? N1 C1 1.366(2) . ? N1 H1 0.91(2) . ? N2 C1 1.328(3) . ? N2 H2A 0.83(3) . ? N2 H2B 0.85(3) . ? N3 C5 1.332(3) . ? N3 H3A 0.81(2) . ? N3 H3B 0.84(3) . ? C1 C2 1.384(3) . ? C2 C3 1.371(4) . ? C2 H2 0.90(2) . ? C3 C4 1.374(3) . ? C3 H3 0.96(2) . ? C4 C5 1.386(3) . ? C4 H4 0.87(2) . ? Cl1 C7 1.697(2) . ? Cl2 C8 1.704(2) . ? O1 C6 1.219(2) . ? O2 C9 1.217(2) . ? N4 C6 1.351(3) . ? N4 C9 1.358(2) . ? C6 C7 1.512(3) . ? C7 C8 1.313(3) . ? C8 C9 1.510(3) . ? 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 C5 N1 C1 123.95(18) . . ? C5 N1 H1 119.3(14) . . ? C1 N1 H1 116.7(14) . . ? C1 N2 H2A 121.3(19) . . ? C1 N2 H2B 118.4(17) . . ? H2A N2 H2B 120(3) . . ? C5 N3 H3A 121.1(16) . . ? C5 N3 H3B 120.5(18) . . ? H3A N3 H3B 118(2) . . ? N2 C1 N1 116.74(19) . . ? N2 C1 C2 125.2(2) . . ? N1 C1 C2 118.07(19) . . ? C3 C2 C1 118.5(2) . . ? C3 C2 H2 123.2(14) . . ? C1 C2 H2 118.3(14) . . ? C2 C3 C4 122.7(2) . . ? C2 C3 H3 118.3(14) . . ? C4 C3 H3 119.0(14) . . ? C3 C4 C5 118.4(2) . . ? C3 C4 H4 120.9(16) . . ? C5 C4 H4 120.5(17) . . ? N3 C5 N1 116.90(19) . . ? N3 C5 C4 124.8(2) . . ? N1 C5 C4 118.29(19) . . ? C6 N4 C9 108.06(16) . . ? O1 C6 N4 126.75(19) . . ? O1 C6 C7 123.99(18) . . ? N4 C6 C7 109.24(16) . . ? C8 C7 C6 106.69(17) . . ? C8 C7 Cl1 130.32(16) . . ? C6 C7 Cl1 122.98(15) . . ? C7 C8 C9 107.15(17) . . ? C7 C8 Cl2 130.72(17) . . ? C9 C8 Cl2 122.11(15) . . ? O2 C9 N4 126.71(19) . . ? O2 C9 C8 124.46(18) . . ? N4 C9 C8 108.84(17) . . ? 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 C5 N1 C1 N2 179.76(19) . . . . ? C5 N1 C1 C2 -0.7(3) . . . . ? N2 C1 C2 C3 179.2(2) . . . . ? N1 C1 C2 C3 -0.3(3) . . . . ? C1 C2 C3 C4 0.9(4) . . . . ? C2 C3 C4 C5 -0.6(4) . . . . ? C1 N1 C5 N3 -179.83(19) . . . . ? C1 N1 C5 C4 1.0(3) . . . . ? C3 C4 C5 N3 -179.5(2) . . . . ? C3 C4 C5 N1 -0.3(3) . . . . ? C9 N4 C6 O1 178.1(2) . . . . ? C9 N4 C6 C7 -0.7(2) . . . . ? O1 C6 C7 C8 -177.3(2) . . . . ? N4 C6 C7 C8 1.5(2) . . . . ? O1 C6 C7 Cl1 2.0(3) . . . . ? N4 C6 C7 Cl1 -179.26(14) . . . . ? C6 C7 C8 C9 -1.5(2) . . . . ? Cl1 C7 C8 C9 179.27(15) . . . . ? C6 C7 C8 Cl2 176.60(15) . . . . ? Cl1 C7 C8 Cl2 -2.6(3) . . . . ? C6 N4 C9 O2 179.7(2) . . . . ? C6 N4 C9 C8 -0.2(2) . . . . ? C7 C8 C9 O2 -178.8(2) . . . . ? Cl2 C8 C9 O2 2.9(3) . . . . ? C7 C8 C9 N4 1.2(2) . . . . ? Cl2 C8 C9 N4 -177.11(15) . . . . ? _diffrn_measured_fraction_theta_max 0.864 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.262 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.044 # Attachment 'ClMa_beta.CIF' data_cz19 _database_code_depnum_ccdc_archive 'CCDC 810512' #TrackingRef 'ClMa_beta.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H Cl2 N O2' _chemical_formula_sum 'C4 H Cl2 N O2' _chemical_formula_weight 165.96 _chemical_absolute_configuration ad 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'P 43 21 2' _symmetry_space_group_name_Hall 'P 4nw 2abw' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y+1/2, x+1/2, z+3/4' 'y+1/2, -x+1/2, z+1/4' '-x+1/2, y+1/2, -z+3/4' 'x+1/2, -y+1/2, -z+1/4' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 5.5503(2) _cell_length_b 5.5503(2) _cell_length_c 38.4073(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1183.2(2) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 5966 _cell_measurement_theta_min 3.71 _cell_measurement_theta_max 30.02 _exptl_crystal_description block _exptl_crystal_colour 'pale orange' _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.863 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 1.006 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.' _exptl_absorpt_correction_T_min 0.7888 _exptl_absorpt_correction_T_max 0.8622 _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 APEX-II CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 8018 _diffrn_reflns_av_R_equivalents 0.0273 _diffrn_reflns_av_sigmaI/netI 0.0178 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -46 _diffrn_reflns_limit_l_max 54 _diffrn_reflns_theta_min 3.71 _diffrn_reflns_theta_max 30.45 _reflns_number_total 1557 _reflns_number_gt 1511 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457 ; _computing_publication_material 'SHELXL-97 (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 'w=1/[\s^2^(Fo^2^)+(0.0328P)^2^+0.2802P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0057(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(8) _refine_ls_number_reflns 1557 _refine_ls_number_parameters 87 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0292 _refine_ls_R_factor_gt 0.0265 _refine_ls_wR_factor_ref 0.0696 _refine_ls_wR_factor_gt 0.0691 _refine_ls_goodness_of_fit_ref 1.168 _refine_ls_restrained_S_all 1.168 _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 0.88177(9) 0.95600(8) 0.066975(13) 0.04513(14) Uani 1 1 d . . . Cl2 Cl 0.39720(10) 0.85083(10) 0.013503(11) 0.04823(15) Uani 1 1 d . . . O1 O 0.8286(3) 0.5222(3) 0.11979(3) 0.0447(3) Uani 1 1 d . . . O2 O 0.1674(3) 0.3954(3) 0.05183(4) 0.0537(4) Uani 1 1 d . . . N1 N 0.4786(3) 0.4073(3) 0.09190(4) 0.0392(3) Uani 1 1 d . . . C1 C 0.6777(3) 0.5474(3) 0.09749(4) 0.0328(3) Uani 1 1 d . . . C2 C 0.6719(3) 0.7368(3) 0.06970(4) 0.0315(3) Uani 1 1 d . . . C3 C 0.4833(3) 0.6984(3) 0.04941(4) 0.0324(3) Uani 1 1 d . . . C4 C 0.3488(3) 0.4830(3) 0.06288(4) 0.0358(4) Uani 1 1 d . . . H1 H 0.433(4) 0.295(4) 0.1037(6) 0.042(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 Cl1 0.0402(2) 0.0389(2) 0.0563(3) 0.00830(19) 0.0008(2) -0.01082(19) Cl2 0.0543(3) 0.0546(3) 0.0357(2) 0.01620(19) -0.00365(18) 0.0044(2) O1 0.0462(7) 0.0460(8) 0.0418(6) 0.0117(6) -0.0079(6) 0.0022(6) O2 0.0503(8) 0.0514(8) 0.0595(8) 0.0061(7) -0.0121(7) -0.0171(7) N1 0.0444(8) 0.0341(8) 0.0390(7) 0.0142(6) -0.0009(6) -0.0059(6) C1 0.0366(8) 0.0304(8) 0.0313(7) 0.0050(6) 0.0025(6) 0.0019(7) C2 0.0341(8) 0.0271(7) 0.0332(7) 0.0039(6) 0.0044(7) -0.0016(6) C3 0.0374(9) 0.0315(8) 0.0283(7) 0.0067(6) 0.0030(6) 0.0002(7) C4 0.0384(9) 0.0330(8) 0.0360(8) 0.0025(7) 0.0018(7) -0.0037(7) _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 1.6873(16) . ? Cl2 C3 1.6871(16) . ? O1 C1 1.206(2) . ? O2 C4 1.196(2) . ? N1 C1 1.368(2) . ? N1 C4 1.392(2) . ? N1 H1 0.81(2) . ? C1 C2 1.499(2) . ? C2 C3 1.323(2) . ? C3 C4 1.501(2) . ? 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 C1 N1 C4 111.82(14) . . ? C1 N1 H1 127.0(16) . . ? C4 N1 H1 121.1(16) . . ? O1 C1 N1 127.34(16) . . ? O1 C1 C2 126.99(17) . . ? N1 C1 C2 105.67(14) . . ? C3 C2 C1 108.85(14) . . ? C3 C2 Cl1 128.78(13) . . ? C1 C2 Cl1 122.37(13) . . ? C2 C3 C4 108.62(14) . . ? C2 C3 Cl2 128.67(14) . . ? C4 C3 Cl2 122.70(13) . . ? O2 C4 N1 126.62(17) . . ? O2 C4 C3 128.34(16) . . ? N1 C4 C3 105.02(14) . . ? 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 C4 N1 C1 O1 -177.48(18) . . . . ? C4 N1 C1 C2 1.6(2) . . . . ? O1 C1 C2 C3 177.43(18) . . . . ? N1 C1 C2 C3 -1.6(2) . . . . ? O1 C1 C2 Cl1 -2.4(3) . . . . ? N1 C1 C2 Cl1 178.52(13) . . . . ? C1 C2 C3 C4 1.03(19) . . . . ? Cl1 C2 C3 C4 -179.11(13) . . . . ? C1 C2 C3 Cl2 -177.61(13) . . . . ? Cl1 C2 C3 Cl2 2.3(3) . . . . ? C1 N1 C4 O2 -179.82(19) . . . . ? C1 N1 C4 C3 -1.0(2) . . . . ? C2 C3 C4 O2 178.7(2) . . . . ? Cl2 C3 C4 O2 -2.5(3) . . . . ? C2 C3 C4 N1 -0.1(2) . . . . ? Cl2 C3 C4 N1 178.62(13) . . . . ? _diffrn_measured_fraction_theta_max 0.889 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.256 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.070 # Attachment 'ClPy.CIF' data_cz16 _database_code_depnum_ccdc_archive 'CCDC 810513' #TrackingRef 'ClPy.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C5 H5 Cl2 N3' _chemical_formula_sum 'C5 H5 Cl2 N3' _chemical_formula_weight 178.02 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'I b a 2' _symmetry_space_group_name_Hall 'I 2 -2c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'x+1, -y+1, z+1/2' '-x+1, y+1, z+1/2' _cell_length_a 11.5523(12) _cell_length_b 23.163(2) _cell_length_c 4.9721(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1330.5(2) _cell_formula_units_Z 8 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 6242 _cell_measurement_theta_min 3.17 _cell_measurement_theta_max 35.97 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.777 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.887 _exptl_absorpt_correction_type none _exptl_special_details ; Bruker KRYOFLEX low temperature device. ; _diffrn_ambient_temperature 103(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 APEX-II CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 8090 _diffrn_reflns_av_R_equivalents 0.0201 _diffrn_reflns_av_sigmaI/netI 0.0226 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 36.94 _reflns_number_total 2648 _reflns_number_gt 2551 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457 ; _computing_publication_material 'SHELXL-97 (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^)+(0.0323P)^2^+0.3800P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _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 -0.01(4) _refine_ls_number_reflns 2648 _refine_ls_number_parameters 111 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0232 _refine_ls_R_factor_gt 0.0218 _refine_ls_wR_factor_ref 0.0591 _refine_ls_wR_factor_gt 0.0578 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 0.14081(2) 0.213771(11) 0.64087(6) 0.01323(6) Uani 1 1 d . . . Cl2 Cl 0.12557(2) 0.051828(11) 1.42759(6) 0.01415(6) Uani 1 1 d . . . N1 N 0.38095(8) 0.11415(4) 0.97785(19) 0.01092(16) Uani 1 1 d . . . C1 C 0.32708(9) 0.15301(5) 0.8196(2) 0.00984(17) Uani 1 1 d . . . C2 C 0.20834(10) 0.16356(4) 0.8483(2) 0.01062(17) Uani 1 1 d . . . C3 C 0.14489(9) 0.13254(5) 1.0339(3) 0.01098(17) Uani 1 1 d . . . H3 H 0.0633(14) 0.1395(6) 1.053(4) 0.014(4) Uiso 1 1 d . . . C4 C 0.20096(9) 0.09204(4) 1.1911(2) 0.01090(18) Uani 1 1 d . . . C5 C 0.32071(9) 0.08415(4) 1.1614(2) 0.01078(16) Uani 1 1 d . . . N2 N 0.39544(8) 0.18232(4) 0.6424(2) 0.01392(16) Uani 1 1 d . . . H2A H 0.4629(13) 0.1661(6) 0.600(4) 0.016(4) Uiso 1 1 d . . . H2B H 0.3663(16) 0.2054(9) 0.525(5) 0.039(7) Uiso 1 1 d . . . N3 N 0.38229(9) 0.04462(5) 1.3101(2) 0.01392(18) Uani 1 1 d . . . H3A H 0.4547(13) 0.0546(6) 1.337(4) 0.012(4) Uiso 1 1 d . . . H3B H 0.3525(15) 0.0354(9) 1.456(4) 0.026(5) 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 Cl1 0.01365(10) 0.01134(10) 0.01471(11) 0.00089(9) -0.00227(10) 0.00243(8) Cl2 0.01537(11) 0.01324(11) 0.01385(11) 0.00074(9) 0.00392(10) -0.00310(8) N1 0.0103(4) 0.0109(4) 0.0115(4) 0.0010(3) 0.0003(3) 0.0002(3) C1 0.0100(4) 0.0093(4) 0.0103(4) -0.0005(3) -0.0002(3) -0.0003(3) C2 0.0112(4) 0.0092(4) 0.0115(4) -0.0009(3) -0.0012(3) 0.0012(3) C3 0.0089(4) 0.0111(4) 0.0129(4) -0.0016(3) -0.0003(4) 0.0003(3) C4 0.0113(4) 0.0101(4) 0.0113(4) -0.0006(3) 0.0019(3) -0.0023(3) C5 0.0113(4) 0.0098(4) 0.0112(4) -0.0006(4) 0.0001(3) 0.0002(3) N2 0.0123(4) 0.0145(4) 0.0149(4) 0.0046(4) 0.0021(4) 0.0002(3) N3 0.0147(4) 0.0143(4) 0.0128(4) 0.0034(3) 0.0002(3) 0.0025(3) _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 1.7391(11) . ? Cl2 C4 1.7344(10) . ? N1 C5 1.3419(14) . ? N1 C1 1.3477(14) . ? C1 N2 1.3642(14) . ? C1 C2 1.4006(16) . ? C2 C3 1.3803(16) . ? C3 C4 1.3825(16) . ? C3 H3 0.960(16) . ? C4 C5 1.4031(15) . ? C5 N3 1.3749(15) . ? N2 H2A 0.890(15) . ? N2 H2B 0.86(2) . ? N3 H3A 0.878(15) . ? N3 H3B 0.83(2) . ? 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 C5 N1 C1 120.24(9) . . ? N1 C1 N2 116.24(9) . . ? N1 C1 C2 120.62(10) . . ? N2 C1 C2 123.08(10) . . ? C3 C2 C1 119.82(10) . . ? C3 C2 Cl1 120.42(9) . . ? C1 C2 Cl1 119.72(9) . . ? C2 C3 C4 118.85(9) . . ? C2 C3 H3 119.9(10) . . ? C4 C3 H3 121.2(10) . . ? C3 C4 C5 119.40(10) . . ? C3 C4 Cl2 120.83(8) . . ? C5 C4 Cl2 119.76(8) . . ? N1 C5 N3 116.24(9) . . ? N1 C5 C4 121.02(10) . . ? N3 C5 C4 122.71(10) . . ? C1 N2 H2A 116.7(10) . . ? C1 N2 H2B 121.5(13) . . ? H2A N2 H2B 116.3(18) . . ? C5 N3 H3A 113.5(10) . . ? C5 N3 H3B 115.2(13) . . ? H3A N3 H3B 109.3(18) . . ? 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 C5 N1 C1 N2 178.76(10) . . . . ? C5 N1 C1 C2 1.43(16) . . . . ? N1 C1 C2 C3 -2.22(16) . . . . ? N2 C1 C2 C3 -179.37(10) . . . . ? N1 C1 C2 Cl1 -179.81(8) . . . . ? N2 C1 C2 Cl1 3.04(15) . . . . ? C1 C2 C3 C4 0.96(16) . . . . ? Cl1 C2 C3 C4 178.53(8) . . . . ? C2 C3 C4 C5 0.99(16) . . . . ? C2 C3 C4 Cl2 179.99(8) . . . . ? C1 N1 C5 N3 178.71(10) . . . . ? C1 N1 C5 C4 0.59(16) . . . . ? C3 C4 C5 N1 -1.82(16) . . . . ? Cl2 C4 C5 N1 179.17(8) . . . . ? C3 C4 C5 N3 -179.81(10) . . . . ? Cl2 C4 C5 N3 1.18(15) . . . . ? _diffrn_measured_fraction_theta_max 0.912 _diffrn_reflns_theta_full 31.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.489 _refine_diff_density_min -0.388 _refine_diff_density_rms 0.091 # Attachment 'HMaClPy.CIF' data_cz22 _database_code_depnum_ccdc_archive 'CCDC 810514' #TrackingRef 'HMaClPy.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C5 H5 Cl2 N3, C4 H3 N O2' _chemical_formula_sum 'C9 H8 Cl2 N4 O2' _chemical_formula_weight 275.09 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' Cl Cl 0.1484 0.1585 '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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.8874(8) _cell_length_b 7.5131(10) _cell_length_c 11.0277(16) _cell_angle_alpha 78.312(8) _cell_angle_beta 83.145(10) _cell_angle_gamma 83.916(10) _cell_volume 552.84(13) _cell_formula_units_Z 2 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 2802 _cell_measurement_theta_min 2.78 _cell_measurement_theta_max 30.33 _exptl_crystal_description table _exptl_crystal_colour 'intense yellow' _exptl_crystal_size_min 0.02 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.653 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_absorpt_coefficient_mu 0.582 _exptl_absorpt_correction_type none _exptl_special_details ; The crystal were all thin and small rhombic plates. Due to the smallness of the crystal used, the data collection was made at low temperature, to increase the number of observed data. The temperature was controlled by a Bruker KRYOFLEX low temperature device. ; _diffrn_ambient_temperature 103(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 13273 _diffrn_reflns_av_R_equivalents 0.0563 _diffrn_reflns_av_sigmaI/netI 0.0597 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 30.57 _reflns_number_total 3374 _reflns_number_gt 2345 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.) ; _computing_structure_refinement 'SHELXL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457 ; _computing_publication_material SHELXTL _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. The distances of chemically equivalent aminne N-H bonds were restraint to have similar values. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0577P)^2^+0.5492P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3374 _refine_ls_number_parameters 186 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0866 _refine_ls_R_factor_gt 0.0515 _refine_ls_wR_factor_ref 0.1316 _refine_ls_wR_factor_gt 0.1165 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 0.19018(9) 1.01924(9) 0.88637(6) 0.01739(16) Uani 1 1 d . . . Cl2 Cl 0.90547(9) 0.64238(9) 0.88092(6) 0.01888(16) Uani 1 1 d . . . N1 N 0.5235(3) 0.7951(3) 0.62729(19) 0.0139(4) Uani 1 1 d . . . N2 N 0.2150(3) 0.9471(3) 0.6257(2) 0.0174(5) Uani 1 1 d D . . H2A H 0.212(4) 0.929(4) 0.557(2) 0.011(7) Uiso 1 1 d D . . H2B H 0.108(4) 0.996(5) 0.659(3) 0.031(10) Uiso 1 1 d D . . N3 N 0.8326(3) 0.6435(3) 0.6171(2) 0.0181(5) Uani 1 1 d D . . H3A H 0.825(5) 0.639(4) 0.546(2) 0.016(8) Uiso 1 1 d D . . H3B H 0.941(4) 0.597(4) 0.647(3) 0.021(8) Uiso 1 1 d D . . C1 C 0.3722(3) 0.8809(3) 0.6881(2) 0.0124(5) Uani 1 1 d . . . C2 C 0.3831(4) 0.9029(3) 0.8106(2) 0.0141(5) Uani 1 1 d . . . C3 C 0.5483(4) 0.8326(3) 0.8696(2) 0.0131(5) Uani 1 1 d . . . H3 H 0.557(5) 0.838(4) 0.955(3) 0.022(8) Uiso 1 1 d . . . C4 C 0.7008(3) 0.7435(4) 0.8065(2) 0.0140(5) Uani 1 1 d . . . C5 C 0.6875(3) 0.7285(3) 0.6832(2) 0.0130(5) Uani 1 1 d . . . O1 O 0.1747(3) 0.8581(3) 0.36449(18) 0.0187(4) Uani 1 1 d . . . O2 O 0.7817(3) 0.5539(3) 0.35807(18) 0.0200(4) Uani 1 1 d . . . N4 N 0.4796(3) 0.7067(3) 0.3937(2) 0.0152(4) Uani 1 1 d . . . H4 H 0.498(5) 0.727(5) 0.459(3) 0.024(9) Uiso 1 1 d . . . C6 C 0.3195(3) 0.7686(3) 0.3283(2) 0.0133(5) Uani 1 1 d . . . C7 C 0.3648(4) 0.7063(4) 0.2061(2) 0.0163(5) Uani 1 1 d . . . H7 H 0.264(4) 0.733(4) 0.137(3) 0.014(7) Uiso 1 1 d . . . C8 C 0.5419(4) 0.6182(4) 0.2039(2) 0.0164(5) Uani 1 1 d . . . H8 H 0.622(5) 0.556(4) 0.134(3) 0.019(8) Uiso 1 1 d . . . C9 C 0.6223(4) 0.6182(3) 0.3251(2) 0.0145(5) Uani 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 Cl1 0.0119(3) 0.0209(3) 0.0195(3) -0.0085(2) 0.0026(2) 0.0022(2) Cl2 0.0137(3) 0.0226(3) 0.0201(3) -0.0038(2) -0.0070(2) 0.0048(2) N1 0.0087(9) 0.0162(11) 0.0163(10) -0.0041(8) -0.0011(7) 0.0033(8) N2 0.0088(10) 0.0259(13) 0.0178(11) -0.0083(9) -0.0021(8) 0.0067(9) N3 0.0105(10) 0.0267(13) 0.0173(11) -0.0085(10) -0.0030(8) 0.0087(9) C1 0.0078(10) 0.0132(12) 0.0149(11) -0.0019(9) 0.0002(8) 0.0018(8) C2 0.0105(11) 0.0133(12) 0.0174(12) -0.0041(9) 0.0016(9) 0.0023(9) C3 0.0126(11) 0.0138(11) 0.0132(11) -0.0034(9) -0.0011(8) -0.0010(9) C4 0.0096(11) 0.0158(12) 0.0160(11) -0.0022(9) -0.0028(8) 0.0020(9) C5 0.0082(10) 0.0137(12) 0.0160(11) -0.0028(9) 0.0007(8) 0.0018(9) O1 0.0099(8) 0.0201(10) 0.0250(10) -0.0057(8) -0.0015(7) 0.0061(7) O2 0.0111(9) 0.0234(10) 0.0240(10) -0.0048(8) -0.0016(7) 0.0054(7) N4 0.0093(9) 0.0208(12) 0.0154(10) -0.0060(9) -0.0028(8) 0.0058(8) C6 0.0096(10) 0.0130(12) 0.0172(11) -0.0026(9) -0.0027(8) 0.0012(9) C7 0.0160(12) 0.0168(13) 0.0158(12) -0.0025(10) -0.0017(9) -0.0015(10) C8 0.0181(12) 0.0157(12) 0.0149(12) -0.0031(9) 0.0000(9) -0.0013(10) C9 0.0106(11) 0.0143(12) 0.0177(12) -0.0037(9) 0.0020(9) 0.0004(9) _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 1.736(3) . ? Cl2 C4 1.742(2) . ? N1 C1 1.348(3) . ? N1 C5 1.352(3) . ? N2 C1 1.349(3) . ? N2 H2A 0.80(2) . ? N2 H2B 0.86(3) . ? N3 C5 1.348(3) . ? N3 H3A 0.80(2) . ? N3 H3B 0.86(3) . ? C1 C2 1.405(3) . ? C2 C3 1.381(3) . ? C3 C4 1.379(4) . ? C3 H3 0.96(3) . ? C4 C5 1.401(3) . ? O1 C6 1.216(3) . ? O2 C9 1.218(3) . ? N4 C9 1.367(3) . ? N4 C6 1.378(3) . ? N4 H4 0.79(4) . ? C6 C7 1.503(4) . ? C7 C8 1.325(4) . ? C7 H7 1.07(3) . ? C8 C9 1.507(4) . ? C8 H8 1.05(3) . ? 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 C1 N1 C5 120.6(2) . . ? C1 N2 H2A 120(2) . . ? C1 N2 H2B 124(2) . . ? H2A N2 H2B 116(3) . . ? C5 N3 H3A 121(2) . . ? C5 N3 H3B 123(2) . . ? H3A N3 H3B 116(3) . . ? N1 C1 N2 117.3(2) . . ? N1 C1 C2 120.4(2) . . ? N2 C1 C2 122.3(2) . . ? C3 C2 C1 119.6(2) . . ? C3 C2 Cl1 120.41(19) . . ? C1 C2 Cl1 119.95(18) . . ? C4 C3 C2 119.2(2) . . ? C4 C3 H3 119(2) . . ? C2 C3 H3 122(2) . . ? C3 C4 C5 119.7(2) . . ? C3 C4 Cl2 120.40(19) . . ? C5 C4 Cl2 119.88(19) . . ? N3 C5 N1 117.4(2) . . ? N3 C5 C4 122.1(2) . . ? N1 C5 C4 120.5(2) . . ? C9 N4 C6 111.2(2) . . ? C9 N4 H4 121(2) . . ? C6 N4 H4 127(2) . . ? O1 C6 N4 125.4(2) . . ? O1 C6 C7 128.5(2) . . ? N4 C6 C7 106.1(2) . . ? C8 C7 C6 108.3(2) . . ? C8 C7 H7 129.2(16) . . ? C6 C7 H7 122.5(16) . . ? C7 C8 C9 108.0(2) . . ? C7 C8 H8 129.7(17) . . ? C9 C8 H8 122.2(17) . . ? O2 C9 N4 125.4(2) . . ? O2 C9 C8 128.2(2) . . ? N4 C9 C8 106.4(2) . . ? 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 C5 N1 C1 N2 178.7(2) . . . . ? C5 N1 C1 C2 0.2(4) . . . . ? N1 C1 C2 C3 -1.4(4) . . . . ? N2 C1 C2 C3 -179.8(2) . . . . ? N1 C1 C2 Cl1 178.21(19) . . . . ? N2 C1 C2 Cl1 -0.2(4) . . . . ? C1 C2 C3 C4 0.7(4) . . . . ? Cl1 C2 C3 C4 -178.9(2) . . . . ? C2 C3 C4 C5 1.2(4) . . . . ? C2 C3 C4 Cl2 -176.51(19) . . . . ? C1 N1 C5 N3 179.7(2) . . . . ? C1 N1 C5 C4 1.7(4) . . . . ? C3 C4 C5 N3 179.7(2) . . . . ? Cl2 C4 C5 N3 -2.6(4) . . . . ? C3 C4 C5 N1 -2.4(4) . . . . ? Cl2 C4 C5 N1 175.32(19) . . . . ? C9 N4 C6 O1 -176.9(2) . . . . ? C9 N4 C6 C7 2.0(3) . . . . ? O1 C6 C7 C8 177.7(3) . . . . ? N4 C6 C7 C8 -1.2(3) . . . . ? C6 C7 C8 C9 0.0(3) . . . . ? C6 N4 C9 O2 177.8(2) . . . . ? C6 N4 C9 C8 -2.0(3) . . . . ? C7 C8 C9 O2 -178.6(3) . . . . ? C7 C8 C9 N4 1.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 30.57 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.718 _refine_diff_density_min -0.493 _refine_diff_density_rms 0.098 data_cz15 _database_code_depnum_ccdc_archive 'CCDC 810515' #TrackingRef 'HMaHPy.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C5 H7 N3, C4 H3 N O2' _chemical_formula_sum 'C9 H10 N4 O2' _chemical_formula_weight 206.21 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 monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 14.1686(15) _cell_length_b 20.559(2) _cell_length_c 6.9270(6) _cell_angle_alpha 90.00 _cell_angle_beta 99.575(11) _cell_angle_gamma 90.00 _cell_volume 1989.7(3) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9847 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 24.56 _exptl_crystal_description table _exptl_crystal_colour orange _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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, APEX 2000, CCD area detector' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 45823 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0142 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3923 _reflns_number_gt 2930 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457 ; _computing_publication_material 'SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)' _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 'w=1/[\s^2^(Fo^2^)+(0.0392P)^2^+0.4264P] 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 SHELXL _refine_ls_extinction_coef 0.0028(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3923 _refine_ls_number_parameters 342 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0533 _refine_ls_R_factor_gt 0.0348 _refine_ls_wR_factor_ref 0.0987 _refine_ls_wR_factor_gt 0.0834 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 N1 N 0.09079(8) 0.13898(6) 0.29192(17) 0.0463(3) Uani 1 1 d . . . N2 N 0.25201(10) 0.15236(9) 0.2941(3) 0.0751(5) Uani 1 1 d . . . H1N2 H 0.2609(13) 0.1396(10) 0.424(3) 0.087(6) Uiso 1 1 d . . . H2N2 H 0.2980(13) 0.1731(9) 0.251(3) 0.078(6) Uiso 1 1 d . . . N3 N -0.06876(10) 0.12535(8) 0.3087(2) 0.0647(4) Uani 1 1 d . . . H1N3 H -0.0491(14) 0.0965(10) 0.416(3) 0.089(6) Uiso 1 1 d . . . H2N3 H -0.1254(14) 0.1230(9) 0.251(3) 0.072(5) Uiso 1 1 d . . . C1 C 0.16040(11) 0.16210(7) 0.2008(2) 0.0523(4) Uani 1 1 d . . . C2 C 0.14089(14) 0.19246(8) 0.0195(3) 0.0664(5) Uani 1 1 d . . . H2 H 0.1935(14) 0.2073(9) -0.031(3) 0.080 Uiso 1 1 d . . . C3 C 0.04760(15) 0.19768(8) -0.0687(3) 0.0688(5) Uani 1 1 d . . . H3 H 0.0315(13) 0.2176(9) -0.196(3) 0.083 Uiso 1 1 d . . . C4 C -0.02514(13) 0.17454(8) 0.0210(2) 0.0615(4) Uani 1 1 d . . . H4 H -0.0906(13) 0.1779(9) -0.038(3) 0.074 Uiso 1 1 d . . . C5 C -0.00057(10) 0.14606(7) 0.2040(2) 0.0481(3) Uani 1 1 d . . . O1 O -0.01744(7) 0.04216(6) 0.68920(16) 0.0658(3) Uani 1 1 d . . . O2 O 0.29829(8) 0.07868(7) 0.70642(18) 0.0785(4) Uani 1 1 d . . . N4 N 0.13511(8) 0.06823(7) 0.64667(18) 0.0508(3) Uani 1 1 d . . . H1N4 H 0.1208(11) 0.0911(8) 0.534(3) 0.065(5) Uiso 1 1 d . . . C6 C 0.06772(10) 0.04207(7) 0.7456(2) 0.0490(3) Uani 1 1 d . . . C7 C 0.12115(11) 0.01434(9) 0.9299(2) 0.0593(4) Uani 1 1 d . . . H7 H 0.0899(12) -0.0080(8) 1.022(2) 0.071 Uiso 1 1 d . . . C8 C 0.21177(12) 0.02461(9) 0.9324(2) 0.0647(5) Uani 1 1 d . . . H8 H 0.2641(13) 0.0147(9) 1.029(3) 0.078 Uiso 1 1 d . . . C9 C 0.22425(10) 0.06031(8) 0.7531(2) 0.0549(4) Uani 1 1 d . . . N5 N 0.62846(8) 0.17201(6) 0.60465(16) 0.0477(3) Uani 1 1 d . . . N6 N 0.78161(11) 0.20236(10) 0.5808(3) 0.0755(5) Uani 1 1 d . . . H1N6 H 0.7609(16) 0.2464(12) 0.571(3) 0.102(8) Uiso 1 1 d . . . H2N6 H 0.8356(15) 0.1917(10) 0.550(3) 0.087(6) Uiso 1 1 d . . . N7 N 0.47321(10) 0.14689(10) 0.6303(3) 0.0743(5) Uani 1 1 d . . . H1N7 H 0.4579(14) 0.1916(11) 0.627(3) 0.091(7) Uiso 1 1 d . . . H2N7 H 0.4288(15) 0.1191(10) 0.653(3) 0.088(6) Uiso 1 1 d . . . C10 C 0.71809(11) 0.15363(8) 0.5950(2) 0.0545(4) Uani 1 1 d . . . C11 C 0.74556(15) 0.08855(10) 0.6017(3) 0.0716(5) Uani 1 1 d . . . H11 H 0.8085(14) 0.0796(10) 0.593(3) 0.086 Uiso 1 1 d . . . C12 C 0.67821(17) 0.04270(10) 0.6212(2) 0.0728(5) Uani 1 1 d . . . H12 H 0.6948(13) -0.0026(10) 0.625(3) 0.087 Uiso 1 1 d . . . C13 C 0.58660(15) 0.06010(9) 0.6362(2) 0.0640(4) Uani 1 1 d . . . H13 H 0.5376(13) 0.0295(9) 0.647(3) 0.077 Uiso 1 1 d . . . C14 C 0.56358(10) 0.12596(8) 0.6253(2) 0.0515(4) Uani 1 1 d . . . O3 O 0.72109(8) 0.35435(6) 0.59681(18) 0.0726(3) Uani 1 1 d . . . O4 O 0.41843(8) 0.28909(6) 0.6190(2) 0.0777(4) Uani 1 1 d . . . N8 N 0.57650(8) 0.30484(7) 0.59866(19) 0.0529(3) Uani 1 1 d . . . H1N8 H 0.5946(12) 0.2628(9) 0.597(2) 0.063(5) Uiso 1 1 d . . . C15 C 0.63676(11) 0.35728(8) 0.6058(2) 0.0540(4) Uani 1 1 d . . . C16 C 0.57691(14) 0.41557(9) 0.6265(2) 0.0652(4) Uani 1 1 d . . . H16 H 0.6032(13) 0.4572(10) 0.635(3) 0.078 Uiso 1 1 d . . . C17 C 0.48961(14) 0.39645(9) 0.6301(3) 0.0670(5) Uani 1 1 d . . . H17 H 0.4341(13) 0.4203(9) 0.650(3) 0.080 Uiso 1 1 d . . . C18 C 0.48627(11) 0.32462(8) 0.6151(2) 0.0561(4) Uani 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 N1 0.0403(6) 0.0474(7) 0.0523(7) 0.0049(5) 0.0110(5) 0.0011(5) N2 0.0441(8) 0.0983(12) 0.0865(11) 0.0280(9) 0.0218(8) -0.0067(8) N3 0.0354(7) 0.0799(10) 0.0766(10) 0.0136(8) 0.0034(7) -0.0018(7) C1 0.0515(9) 0.0476(8) 0.0609(9) 0.0056(7) 0.0186(7) 0.0015(7) C2 0.0801(13) 0.0565(10) 0.0685(11) 0.0138(8) 0.0297(9) 0.0000(9) C3 0.0970(14) 0.0539(10) 0.0542(10) 0.0120(8) 0.0091(9) 0.0102(9) C4 0.0663(10) 0.0541(9) 0.0593(9) 0.0027(8) -0.0038(8) 0.0062(8) C5 0.0465(8) 0.0411(8) 0.0549(8) -0.0015(6) 0.0033(6) 0.0026(6) O1 0.0376(6) 0.0898(8) 0.0724(7) 0.0129(6) 0.0165(5) 0.0000(5) O2 0.0418(6) 0.1160(11) 0.0791(8) 0.0138(7) 0.0141(5) -0.0192(6) N4 0.0380(6) 0.0688(8) 0.0472(7) 0.0085(6) 0.0117(5) -0.0037(6) C6 0.0401(8) 0.0568(9) 0.0537(8) 0.0006(7) 0.0180(6) -0.0007(6) C7 0.0528(9) 0.0735(11) 0.0549(9) 0.0127(8) 0.0183(7) -0.0004(8) C8 0.0504(10) 0.0893(13) 0.0531(9) 0.0131(9) 0.0051(7) -0.0007(9) C9 0.0413(8) 0.0712(10) 0.0535(8) -0.0005(7) 0.0112(6) -0.0073(7) N5 0.0401(6) 0.0553(7) 0.0477(6) 0.0037(5) 0.0069(5) -0.0011(5) N6 0.0449(8) 0.0854(12) 0.1023(12) 0.0051(9) 0.0300(8) 0.0014(8) N7 0.0396(8) 0.0753(11) 0.1053(12) 0.0207(9) 0.0042(7) -0.0130(8) C10 0.0473(8) 0.0706(11) 0.0471(8) 0.0047(7) 0.0126(6) 0.0078(8) C11 0.0757(12) 0.0819(13) 0.0618(10) 0.0137(9) 0.0253(9) 0.0290(11) C12 0.1133(17) 0.0598(11) 0.0473(9) 0.0099(8) 0.0189(9) 0.0190(11) C13 0.0843(13) 0.0580(10) 0.0468(8) 0.0069(7) 0.0027(8) -0.0103(9) C14 0.0502(9) 0.0596(10) 0.0416(7) 0.0064(6) -0.0013(6) -0.0078(7) O3 0.0468(7) 0.0914(9) 0.0767(8) -0.0004(6) 0.0020(5) -0.0136(6) O4 0.0509(7) 0.0775(8) 0.1121(10) -0.0091(7) 0.0352(7) -0.0002(6) N8 0.0409(7) 0.0554(8) 0.0636(8) -0.0043(6) 0.0116(5) 0.0005(6) C15 0.0476(9) 0.0678(10) 0.0443(8) -0.0013(7) 0.0005(6) -0.0072(7) C16 0.0806(13) 0.0567(10) 0.0565(9) -0.0084(8) 0.0064(8) -0.0054(9) C17 0.0700(12) 0.0642(11) 0.0690(11) -0.0096(8) 0.0176(9) 0.0115(9) C18 0.0468(9) 0.0656(10) 0.0585(9) -0.0065(8) 0.0161(7) 0.0038(8) _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 N1 C1 1.3433(17) . ? N1 C5 1.3438(17) . ? N2 C1 1.365(2) . ? N2 H1N2 0.92(2) . ? N2 H2N2 0.87(2) . ? N3 C5 1.369(2) . ? N3 H1N3 0.96(2) . ? N3 H2N3 0.837(19) . ? C1 C2 1.388(2) . ? C2 C3 1.365(3) . ? C2 H2 0.927(19) . ? C3 C4 1.374(3) . ? C3 H3 0.961(19) . ? C4 C5 1.387(2) . ? C4 H4 0.953(18) . ? O1 C6 1.2049(16) . ? O2 C9 1.2085(17) . ? N4 C9 1.3622(19) . ? N4 C6 1.3742(17) . ? N4 H1N4 0.907(18) . ? C6 C7 1.485(2) . ? C7 C8 1.299(2) . ? C7 H7 0.951(17) . ? C8 C9 1.478(2) . ? C8 H8 0.936(18) . ? N5 C10 1.3372(18) . ? N5 C14 1.3438(18) . ? N6 C10 1.361(2) . ? N6 H1N6 0.95(2) . ? N6 H2N6 0.86(2) . ? N7 C14 1.357(2) . ? N7 H1N7 0.94(2) . ? N7 H2N7 0.88(2) . ? C10 C11 1.392(2) . ? C11 C12 1.364(3) . ? C11 H11 0.92(2) . ? C12 C13 1.367(3) . ? C12 H12 0.96(2) . ? C13 C14 1.392(2) . ? C13 H13 0.950(18) . ? O3 C15 1.2083(18) . ? O4 C18 1.2111(19) . ? N8 C18 1.3642(19) . ? N8 C15 1.371(2) . ? N8 H1N8 0.902(18) . ? C15 C16 1.489(2) . ? C16 C17 1.302(3) . ? C16 H16 0.931(19) . ? C17 C18 1.481(2) . ? C17 H17 0.956(19) . ? 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 C1 N1 C5 118.42(13) . . ? C1 N2 H1N2 117.8(12) . . ? C1 N2 H2N2 118.1(12) . . ? H1N2 N2 H2N2 118.9(17) . . ? C5 N3 H1N3 117.7(11) . . ? C5 N3 H2N3 118.0(13) . . ? H1N3 N3 H2N3 117.9(17) . . ? N1 C1 N2 116.11(14) . . ? N1 C1 C2 122.21(15) . . ? N2 C1 C2 121.65(15) . . ? C3 C2 C1 118.21(16) . . ? C3 C2 H2 125.7(12) . . ? C1 C2 H2 116.1(12) . . ? C2 C3 C4 120.89(16) . . ? C2 C3 H3 120.5(11) . . ? C4 C3 H3 118.6(11) . . ? C3 C4 C5 117.81(16) . . ? C3 C4 H4 122.0(11) . . ? C5 C4 H4 120.2(11) . . ? N1 C5 N3 115.96(13) . . ? N1 C5 C4 122.43(14) . . ? N3 C5 C4 121.58(15) . . ? C9 N4 C6 109.99(13) . . ? C9 N4 H1N4 125.7(10) . . ? C6 N4 H1N4 124.0(10) . . ? O1 C6 N4 125.38(14) . . ? O1 C6 C7 128.26(13) . . ? N4 C6 C7 106.37(12) . . ? C8 C7 C6 108.10(14) . . ? C8 C7 H7 129.7(10) . . ? C6 C7 H7 122.1(10) . . ? C7 C8 C9 109.00(14) . . ? C7 C8 H8 129.6(11) . . ? C9 C8 H8 121.3(11) . . ? O2 C9 N4 125.87(14) . . ? O2 C9 C8 127.61(15) . . ? N4 C9 C8 106.52(12) . . ? C10 N5 C14 118.58(14) . . ? C10 N6 H1N6 120.5(13) . . ? C10 N6 H2N6 117.3(14) . . ? H1N6 N6 H2N6 120.2(19) . . ? C14 N7 H1N7 121.5(12) . . ? C14 N7 H2N7 120.2(13) . . ? H1N7 N7 H2N7 117.8(18) . . ? N5 C10 N6 116.13(15) . . ? N5 C10 C11 122.18(16) . . ? N6 C10 C11 121.68(16) . . ? C12 C11 C10 118.11(17) . . ? C12 C11 H11 124.6(13) . . ? C10 C11 H11 117.3(13) . . ? C11 C12 C13 121.03(18) . . ? C11 C12 H12 120.1(12) . . ? C13 C12 H12 118.8(12) . . ? C12 C13 C14 117.87(17) . . ? C12 C13 H13 123.3(11) . . ? C14 C13 H13 118.7(11) . . ? N5 C14 N7 116.39(15) . . ? N5 C14 C13 122.20(15) . . ? N7 C14 C13 121.39(16) . . ? C18 N8 C15 110.43(14) . . ? C18 N8 H1N8 124.0(10) . . ? C15 N8 H1N8 125.2(10) . . ? O3 C15 N8 125.04(15) . . ? O3 C15 C16 128.97(16) . . ? N8 C15 C16 105.99(14) . . ? C17 C16 C15 108.47(16) . . ? C17 C16 H16 130.4(12) . . ? C15 C16 H16 121.2(12) . . ? C16 C17 C18 108.61(16) . . ? C16 C17 H17 130.9(11) . . ? C18 C17 H17 120.3(11) . . ? O4 C18 N8 125.47(15) . . ? O4 C18 C17 128.03(15) . . ? N8 C18 C17 106.49(14) . . ? 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 C5 N1 C1 N2 -178.56(14) . . . . ? C5 N1 C1 C2 -0.4(2) . . . . ? N1 C1 C2 C3 -1.1(3) . . . . ? N2 C1 C2 C3 176.94(17) . . . . ? C1 C2 C3 C4 1.1(3) . . . . ? C2 C3 C4 C5 0.3(3) . . . . ? C1 N1 C5 N3 -176.01(13) . . . . ? C1 N1 C5 C4 1.9(2) . . . . ? C3 C4 C5 N1 -1.9(2) . . . . ? C3 C4 C5 N3 175.96(15) . . . . ? C9 N4 C6 O1 179.32(15) . . . . ? C9 N4 C6 C7 -1.02(17) . . . . ? O1 C6 C7 C8 179.74(17) . . . . ? N4 C6 C7 C8 0.10(19) . . . . ? C6 C7 C8 C9 0.8(2) . . . . ? C6 N4 C9 O2 -179.22(16) . . . . ? C6 N4 C9 C8 1.48(18) . . . . ? C7 C8 C9 O2 179.29(18) . . . . ? C7 C8 C9 N4 -1.4(2) . . . . ? C14 N5 C10 N6 -177.83(13) . . . . ? C14 N5 C10 C11 1.3(2) . . . . ? N5 C10 C11 C12 -0.8(2) . . . . ? N6 C10 C11 C12 178.29(16) . . . . ? C10 C11 C12 C13 -0.8(3) . . . . ? C11 C12 C13 C14 1.8(2) . . . . ? C10 N5 C14 N7 -178.69(14) . . . . ? C10 N5 C14 C13 -0.2(2) . . . . ? C12 C13 C14 N5 -1.3(2) . . . . ? C12 C13 C14 N7 177.07(15) . . . . ? C18 N8 C15 O3 179.22(14) . . . . ? C18 N8 C15 C16 -0.73(16) . . . . ? O3 C15 C16 C17 179.97(16) . . . . ? N8 C15 C16 C17 -0.08(18) . . . . ? C15 C16 C17 C18 0.79(19) . . . . ? C15 N8 C18 O4 -177.84(16) . . . . ? C15 N8 C18 C17 1.19(17) . . . . ? C16 C17 C18 O4 177.76(17) . . . . ? C16 C17 C18 N8 -1.24(19) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.136 _refine_diff_density_min -0.123 _refine_diff_density_rms 0.026