# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_(4-H) data_shelx1 #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H14 N4 O2' _chemical_formula_sum 'C12 H14 N4 O2' _chemical_formula_weight 246.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c a 21 ' _symmetry_space_group_name_Hall 'P 2c -2ac ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 22.1366(6) _cell_length_b 10.4274(3) _cell_length_c 10.7186(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2474.14(12) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3137 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 27.5 _exptl_crystal_description lath _exptl_crystal_colour brown _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.683 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10 cm confocal mirrors' _diffrn_measurement_device_type 'Enraf Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 19967 _diffrn_reflns_av_R_equivalents 0.060 _diffrn_reflns_av_sigmaI/netI 0.039 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.3 _diffrn_reflns_theta_max 27.5 _reflns_number_total 2976 _reflns_number_gt 2461 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT' _computing_data_reduction 'DENZO & COLLECT' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006)' _computing_publication_material 'publCIF (Westrip, 2010)' _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^ > 2\s(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^)+(0.0500P)^2^+0.2888P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details nd _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2976 _refine_ls_number_parameters 335 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.054 _refine_ls_R_factor_gt 0.039 _refine_ls_wR_factor_ref 0.092 _refine_ls_wR_factor_gt 0.085 _refine_ls_goodness_of_fit_ref 1.04 _refine_ls_restrained_S_all 1.04 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.99724(9) -0.28921(18) 1.12163(19) 0.0320(4) Uani 1 1 d . . . O2 O 1.04429(7) -0.17406(16) 0.97325(16) 0.0255(4) Uani 1 1 d . . . N1 N 0.90221(8) 0.07313(18) 1.02311(18) 0.0191(4) Uani 1 1 d . . . N2 N 0.87461(10) 0.00673(18) 1.11690(19) 0.0222(4) Uani 1 1 d . . . N3 N 0.90674(9) -0.09717(18) 1.13168(19) 0.0209(4) Uani 1 1 d . . . N4 N 0.88272(9) 0.19339(18) 0.9881(2) 0.0211(4) Uani 1 1 d D . . H4N H 0.8898(13) 0.2544(19) 1.043(2) 0.025 Uiso 1 1 d D . . C1 C 0.95160(10) 0.0135(2) 0.9789(2) 0.0175(5) Uani 1 1 d . . . C2 C 0.95397(10) -0.0958(2) 1.0493(2) 0.0181(5) Uani 1 1 d . . . C3 C 0.98964(12) 0.0672(2) 0.8786(2) 0.0254(6) Uani 1 1 d . . . H3A H 0.9667 0.1320 0.8324 0.038 Uiso 1 1 calc R . . H3B H 1.0018 -0.0017 0.8217 0.038 Uiso 1 1 calc R . . H3C H 1.0257 0.1068 0.9151 0.038 Uiso 1 1 calc R . . C4 C 0.99954(11) -0.1982(2) 1.0539(2) 0.0207(5) Uani 1 1 d . . . C5 C 1.09669(12) -0.2571(3) 0.9801(3) 0.0293(6) Uani 1 1 d . . . H5A H 1.1164 -0.2615 0.8973 0.035 Uiso 1 1 calc R . . H5B H 1.0839 -0.3448 1.0035 0.035 Uiso 1 1 calc R . . C6 C 1.14053(13) -0.2074(3) 1.0744(3) 0.0407(7) Uani 1 1 d . . . H6A H 1.1501 -0.1176 1.0558 0.061 Uiso 1 1 calc R . . H6B H 1.1776 -0.2586 1.0715 0.061 Uiso 1 1 calc R . . H6C H 1.1226 -0.2133 1.1579 0.061 Uiso 1 1 calc R . . C7 C 0.82889(10) 0.2028(2) 0.9204(2) 0.0191(5) Uani 1 1 d . . . C8 C 0.80124(11) 0.0981(2) 0.8656(2) 0.0222(5) Uani 1 1 d . . . H8 H 0.8167 0.0143 0.8794 0.027 Uiso 1 1 calc R . . C9 C 0.75080(12) 0.1156(2) 0.7905(3) 0.0271(6) Uani 1 1 d . . . H9 H 0.7320 0.0434 0.7528 0.033 Uiso 1 1 calc R . . C10 C 0.72779(11) 0.2363(3) 0.7702(2) 0.0288(6) Uani 1 1 d . . . H10 H 0.6936 0.2480 0.7179 0.035 Uiso 1 1 calc R . . C11 C 0.75510(13) 0.3407(2) 0.8270(3) 0.0293(6) Uani 1 1 d . . . H11 H 0.7391 0.4242 0.8139 0.035 Uiso 1 1 calc R . . C12 C 0.80488(11) 0.3252(2) 0.9018(2) 0.0241(5) Uani 1 1 d . . . H12 H 0.8229 0.3974 0.9409 0.029 Uiso 1 1 calc R . . O3 O 0.00351(8) 0.78428(17) 0.65101(17) 0.0284(4) Uani 1 1 d . . . O4 O -0.05384(7) 0.66811(15) 0.78114(16) 0.0243(4) Uani 1 1 d . . . N5 N 0.08988(9) 0.42148(18) 0.78293(18) 0.0195(4) Uani 1 1 d . . . N6 N 0.12427(9) 0.48670(19) 0.6987(2) 0.0226(4) Uani 1 1 d . . . N7 N 0.09367(9) 0.58924(19) 0.66998(18) 0.0210(5) Uani 1 1 d . . . N8 N 0.10577(10) 0.30149(19) 0.8249(2) 0.0219(5) Uani 1 1 d D . . H8N H 0.1021(12) 0.2422(19) 0.7664(19) 0.026 Uiso 1 1 d D . . C13 C 0.03723(11) 0.4808(2) 0.8074(2) 0.0191(5) Uani 1 1 d . . . C14 C 0.04043(10) 0.5890(2) 0.7347(2) 0.0183(5) Uani 1 1 d . . . C15 C -0.00850(11) 0.4300(2) 0.8950(2) 0.0257(6) Uani 1 1 d . . . H15A H -0.0446 0.4040 0.8484 0.039 Uiso 1 1 calc R . . H15B H -0.0193 0.4966 0.9555 0.039 Uiso 1 1 calc R . . H15C H 0.0081 0.3556 0.9392 0.039 Uiso 1 1 calc R . . C16 C -0.00374(11) 0.6918(2) 0.7170(2) 0.0195(5) Uani 1 1 d . . . C17 C -0.10403(11) 0.7568(2) 0.7642(2) 0.0239(5) Uani 1 1 d . . . H17A H -0.1188 0.7543 0.6771 0.029 Uiso 1 1 calc R . . H17B H -0.0914 0.8456 0.7841 0.029 Uiso 1 1 calc R . . C18 C -0.15242(12) 0.7129(3) 0.8525(3) 0.0314(6) Uani 1 1 d . . . H18A H -0.1657 0.6265 0.8291 0.047 Uiso 1 1 calc R . . H18B H -0.1868 0.7720 0.8483 0.047 Uiso 1 1 calc R . . H18C H -0.1364 0.7115 0.9377 0.047 Uiso 1 1 calc R . . C19 C 0.15364(11) 0.2916(2) 0.9110(2) 0.0199(5) Uani 1 1 d . . . C20 C 0.17713(11) 0.3962(2) 0.9743(2) 0.0244(5) Uani 1 1 d . . . H20 H 0.1621 0.4799 0.9579 0.029 Uiso 1 1 calc R . . C21 C 0.22250(11) 0.3788(3) 1.0614(2) 0.0290(6) Uani 1 1 d . . . H21 H 0.2390 0.4509 1.1035 0.035 Uiso 1 1 calc R . . C22 C 0.24403(13) 0.2579(3) 1.0877(3) 0.0318(6) Uani 1 1 d . . . H22 H 0.2750 0.2465 1.1480 0.038 Uiso 1 1 calc R . . C23 C 0.22026(11) 0.1537(3) 1.0259(3) 0.0298(6) Uani 1 1 d . . . H23 H 0.2348 0.0701 1.0443 0.036 Uiso 1 1 calc R . . C24 C 0.17533(11) 0.1696(2) 0.9371(2) 0.0246(5) Uani 1 1 d . . . H24 H 0.1595 0.0973 0.8942 0.029 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0340(11) 0.0262(9) 0.0358(11) 0.0091(9) 0.0065(9) 0.0073(8) O2 0.0211(9) 0.0329(9) 0.0225(9) 0.0008(8) 0.0026(8) 0.0025(7) N1 0.0189(10) 0.0196(10) 0.0187(10) 0.0015(8) -0.0001(8) -0.0002(8) N2 0.0221(10) 0.0246(10) 0.0199(10) 0.0017(9) 0.0015(9) 0.0001(8) N3 0.0210(10) 0.0225(10) 0.0192(10) -0.0007(8) 0.0021(9) 0.0004(8) N4 0.0253(11) 0.0148(10) 0.0231(11) -0.0027(9) -0.0060(9) 0.0007(8) C1 0.0167(11) 0.0194(11) 0.0163(11) -0.0006(10) -0.0015(9) -0.0031(9) C2 0.0189(12) 0.0206(12) 0.0150(11) -0.0002(9) -0.0016(9) -0.0019(9) C3 0.0285(14) 0.0252(13) 0.0226(13) 0.0032(11) 0.0038(11) -0.0015(10) C4 0.0217(13) 0.0231(13) 0.0175(12) -0.0023(11) -0.0003(10) -0.0020(10) C5 0.0206(13) 0.0380(15) 0.0292(13) -0.0071(12) -0.0008(11) 0.0081(11) C6 0.0323(16) 0.0520(18) 0.0378(17) -0.0103(14) -0.0088(14) 0.0014(14) C7 0.0166(11) 0.0244(12) 0.0162(11) 0.0012(10) 0.0031(10) 0.0009(9) C8 0.0222(12) 0.0223(12) 0.0221(13) 0.0003(10) 0.0003(10) -0.0023(9) C9 0.0225(12) 0.0365(14) 0.0222(13) -0.0016(11) 0.0008(11) -0.0064(11) C10 0.0188(12) 0.0479(16) 0.0198(13) 0.0035(12) -0.0006(11) 0.0049(11) C11 0.0280(14) 0.0319(13) 0.0281(14) 0.0056(11) 0.0041(12) 0.0111(12) C12 0.0261(13) 0.0240(13) 0.0222(13) -0.0012(11) 0.0009(11) 0.0029(10) O3 0.0318(10) 0.0245(9) 0.0288(10) 0.0088(8) 0.0058(8) -0.0005(8) O4 0.0200(9) 0.0248(9) 0.0280(10) 0.0064(8) 0.0028(8) 0.0023(7) N5 0.0223(10) 0.0182(10) 0.0179(10) 0.0018(8) -0.0010(9) -0.0011(8) N6 0.0205(10) 0.0242(10) 0.0231(11) 0.0028(9) 0.0005(9) -0.0034(8) N7 0.0187(11) 0.0236(11) 0.0207(10) 0.0024(9) -0.0007(8) -0.0017(8) N8 0.0254(11) 0.0173(10) 0.0230(11) -0.0008(9) -0.0053(9) -0.0010(8) C13 0.0205(12) 0.0207(12) 0.0162(11) -0.0030(9) -0.0009(9) -0.0029(9) C14 0.0195(12) 0.0210(11) 0.0143(11) -0.0017(9) -0.0011(9) -0.0041(9) C15 0.0285(13) 0.0234(12) 0.0253(13) 0.0060(11) 0.0078(11) 0.0007(10) C16 0.0207(12) 0.0232(12) 0.0146(12) -0.0004(10) 0.0003(10) -0.0053(9) C17 0.0214(13) 0.0235(12) 0.0269(14) -0.0013(11) -0.0012(11) 0.0036(9) C18 0.0230(13) 0.0430(16) 0.0281(14) -0.0040(13) 0.0034(12) 0.0016(11) C19 0.0211(11) 0.0228(12) 0.0159(11) 0.0017(9) 0.0029(10) 0.0003(10) C20 0.0263(13) 0.0251(12) 0.0217(12) -0.0003(11) -0.0003(11) -0.0008(10) C21 0.0266(14) 0.0388(16) 0.0217(13) -0.0033(12) -0.0005(11) -0.0072(11) C22 0.0235(13) 0.0498(17) 0.0221(13) 0.0023(12) -0.0003(11) 0.0037(13) C23 0.0253(13) 0.0332(14) 0.0308(14) 0.0059(12) 0.0039(12) 0.0094(11) C24 0.0262(13) 0.0242(12) 0.0233(13) -0.0024(10) 0.0049(11) 0.0014(10) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C4 1.196(3) . ? O2 C4 1.339(3) . ? O2 C5 1.450(3) . ? N1 C1 1.344(3) . ? N1 N2 1.365(3) . ? N1 N4 1.378(3) . ? N2 N3 1.306(3) . ? N3 C2 1.368(3) . ? N4 C7 1.399(3) . ? N4 H4N 0.880(10) . ? C1 C2 1.368(3) . ? C1 C3 1.476(3) . ? C2 C4 1.470(3) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C5 C6 1.495(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.382(3) . ? C7 C12 1.396(3) . ? C8 C9 1.389(4) . ? C8 H8 0.9500 . ? C9 C10 1.376(3) . ? C9 H9 0.9500 . ? C10 C11 1.385(4) . ? C10 H10 0.9500 . ? C11 C12 1.373(4) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? O3 C16 1.207(3) . ? O4 C16 1.328(3) . ? O4 C17 1.457(3) . ? N5 C13 1.345(3) . ? N5 N6 1.363(3) . ? N5 N8 1.375(3) . ? N6 N7 1.303(3) . ? N7 C14 1.367(3) . ? N8 C19 1.409(3) . ? N8 H8N 0.884(10) . ? C13 C14 1.373(3) . ? C13 C15 1.479(3) . ? C14 C16 1.463(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C17 C18 1.501(4) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.386(3) . ? C19 C24 1.388(3) . ? C20 C21 1.383(4) . ? C20 H20 0.9500 . ? C21 C22 1.377(4) . ? C21 H21 0.9500 . ? C22 C23 1.377(4) . ? C22 H22 0.9500 . ? C23 C24 1.387(4) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O2 C5 116.6(2) . . ? C1 N1 N2 112.91(19) . . ? C1 N1 N4 125.4(2) . . ? N2 N1 N4 121.46(19) . . ? N3 N2 N1 105.45(19) . . ? N2 N3 C2 109.21(19) . . ? N1 N4 C7 118.15(19) . . ? N1 N4 H4N 114.9(18) . . ? C7 N4 H4N 116.5(18) . . ? N1 C1 C2 102.82(19) . . ? N1 C1 C3 123.1(2) . . ? C2 C1 C3 134.1(2) . . ? C1 C2 N3 109.6(2) . . ? C1 C2 C4 130.5(2) . . ? N3 C2 C4 119.7(2) . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? O1 C4 O2 124.9(2) . . ? O1 C4 C2 124.6(2) . . ? O2 C4 C2 110.5(2) . . ? O2 C5 C6 110.3(2) . . ? O2 C5 H5A 109.6 . . ? C6 C5 H5A 109.6 . . ? O2 C5 H5B 109.6 . . ? C6 C5 H5B 109.6 . . ? H5A C5 H5B 108.1 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C12 119.5(2) . . ? C8 C7 N4 122.8(2) . . ? C12 C7 N4 117.5(2) . . ? C7 C8 C9 119.9(2) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C10 C9 C8 120.6(2) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C11 119.2(2) . . ? C9 C10 H10 120.4 . . ? C11 C10 H10 120.4 . . ? C12 C11 C10 121.0(2) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C11 C12 C7 119.8(2) . . ? C11 C12 H12 120.1 . . ? C7 C12 H12 120.1 . . ? C16 O4 C17 117.03(18) . . ? C13 N5 N6 112.56(19) . . ? C13 N5 N8 125.2(2) . . ? N6 N5 N8 121.86(19) . . ? N7 N6 N5 105.99(19) . . ? N6 N7 C14 109.08(18) . . ? N5 N8 C19 118.26(19) . . ? N5 N8 H8N 112.4(18) . . ? C19 N8 H8N 118.8(18) . . ? N5 C13 C14 102.9(2) . . ? N5 C13 C15 123.5(2) . . ? C14 C13 C15 133.6(2) . . ? N7 C14 C13 109.5(2) . . ? N7 C14 C16 120.6(2) . . ? C13 C14 C16 129.8(2) . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O3 C16 O4 124.3(2) . . ? O3 C16 C14 124.9(2) . . ? O4 C16 C14 110.81(19) . . ? O4 C17 C18 105.8(2) . . ? O4 C17 H17A 110.6 . . ? C18 C17 H17A 110.6 . . ? O4 C17 H17B 110.6 . . ? C18 C17 H17B 110.6 . . ? H17A C17 H17B 108.7 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C24 119.6(2) . . ? C20 C19 N8 123.0(2) . . ? C24 C19 N8 117.3(2) . . ? C21 C20 C19 120.0(2) . . ? C21 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C22 C21 C20 120.7(2) . . ? C22 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C23 C22 C21 119.4(2) . . ? C23 C22 H22 120.3 . . ? C21 C22 H22 120.3 . . ? C22 C23 C24 120.7(2) . . ? C22 C23 H23 119.7 . . ? C24 C23 H23 119.7 . . ? C23 C24 C19 119.7(2) . . ? C23 C24 H24 120.1 . . ? C19 C24 H24 120.1 . . ? 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 N2 N3 -0.5(3) . . . . ? N4 N1 N2 N3 -175.39(19) . . . . ? N1 N2 N3 C2 0.4(2) . . . . ? C1 N1 N4 C7 112.0(3) . . . . ? N2 N1 N4 C7 -73.8(3) . . . . ? N2 N1 C1 C2 0.4(2) . . . . ? N4 N1 C1 C2 175.0(2) . . . . ? N2 N1 C1 C3 -179.1(2) . . . . ? N4 N1 C1 C3 -4.5(4) . . . . ? N1 C1 C2 N3 -0.1(2) . . . . ? C3 C1 C2 N3 179.3(2) . . . . ? N1 C1 C2 C4 -175.1(2) . . . . ? C3 C1 C2 C4 4.3(4) . . . . ? N2 N3 C2 C1 -0.2(3) . . . . ? N2 N3 C2 C4 175.4(2) . . . . ? C5 O2 C4 O1 -7.5(4) . . . . ? C5 O2 C4 C2 171.5(2) . . . . ? C1 C2 C4 O1 178.6(3) . . . . ? N3 C2 C4 O1 4.0(4) . . . . ? C1 C2 C4 O2 -0.4(4) . . . . ? N3 C2 C4 O2 -175.0(2) . . . . ? C4 O2 C5 C6 -86.8(3) . . . . ? N1 N4 C7 C8 -13.6(3) . . . . ? N1 N4 C7 C12 170.5(2) . . . . ? C12 C7 C8 C9 1.5(4) . . . . ? N4 C7 C8 C9 -174.3(2) . . . . ? C7 C8 C9 C10 -0.2(4) . . . . ? C8 C9 C10 C11 -0.8(4) . . . . ? C9 C10 C11 C12 0.6(4) . . . . ? C10 C11 C12 C7 0.6(4) . . . . ? C8 C7 C12 C11 -1.7(4) . . . . ? N4 C7 C12 C11 174.4(2) . . . . ? C13 N5 N6 N7 0.6(3) . . . . ? N8 N5 N6 N7 173.71(19) . . . . ? N5 N6 N7 C14 -0.2(2) . . . . ? C13 N5 N8 C19 -113.3(3) . . . . ? N6 N5 N8 C19 74.5(3) . . . . ? N6 N5 C13 C14 -0.7(3) . . . . ? N8 N5 C13 C14 -173.5(2) . . . . ? N6 N5 C13 C15 179.7(2) . . . . ? N8 N5 C13 C15 6.9(4) . . . . ? N6 N7 C14 C13 -0.2(3) . . . . ? N6 N7 C14 C16 -178.1(2) . . . . ? N5 C13 C14 N7 0.6(2) . . . . ? C15 C13 C14 N7 -179.9(2) . . . . ? N5 C13 C14 C16 178.2(2) . . . . ? C15 C13 C14 C16 -2.3(4) . . . . ? C17 O4 C16 O3 3.5(4) . . . . ? C17 O4 C16 C14 -174.9(2) . . . . ? N7 C14 C16 O3 -3.1(4) . . . . ? C13 C14 C16 O3 179.5(2) . . . . ? N7 C14 C16 O4 175.2(2) . . . . ? C13 C14 C16 O4 -2.1(3) . . . . ? C16 O4 C17 C18 -176.4(2) . . . . ? N5 N8 C19 C20 13.6(3) . . . . ? N5 N8 C19 C24 -170.0(2) . . . . ? C24 C19 C20 C21 0.9(4) . . . . ? N8 C19 C20 C21 177.3(2) . . . . ? C19 C20 C21 C22 -1.1(4) . . . . ? C20 C21 C22 C23 0.4(4) . . . . ? C21 C22 C23 C24 0.5(4) . . . . ? C22 C23 C24 C19 -0.7(4) . . . . ? C20 C19 C24 C23 -0.1(4) . . . . ? N8 C19 C24 C23 -176.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.18 _refine_diff_density_min -0.25 _refine_diff_density_rms 0.051 _database_code_depnum_ccdc_archive 'CCDC 845654' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_(4-F) data_shelx2 #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H13 F N4 O2 ' _chemical_formula_sum 'C12 H13 F N4 O2 ' _chemical_formula_weight 264.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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' F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0100 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 10.057(3) _cell_length_b 17.510(4) _cell_length_c 14.102(4) _cell_angle_alpha 90 _cell_angle_beta 95.722(3) _cell_angle_gamma 90 _cell_volume 2471.0(12) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8525 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 30.1 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.421 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.6911 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury SRS station 9.8' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'fine-slice \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 5 _diffrn_reflns_number 21852 _diffrn_reflns_av_R_equivalents 0.047 _diffrn_reflns_av_sigmaI/netI 0.042 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.6 _diffrn_reflns_theta_max 27.5 _reflns_number_total 6059 _reflns_number_gt 4711 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'SAINT (Bruker, 2004)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006) ; _computing_publication_material 'publCIF (Westrip, 2010)' _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^ > 2\s(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^)+(0.0939P)^2^+1.3685P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6056 _refine_ls_number_parameters 353 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.081 _refine_ls_R_factor_gt 0.064 _refine_ls_wR_factor_ref 0.187 _refine_ls_wR_factor_gt 0.174 _refine_ls_goodness_of_fit_ref 1.11 _refine_ls_restrained_S_all 1.11 _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 F1 F 0.35080(14) 0.07103(9) 1.36600(9) 0.0423(3) Uani 1 1 d . . . O1 O 0.21531(15) 0.16960(10) 0.66198(11) 0.0367(4) Uani 1 1 d . . . O2 O 0.40311(15) 0.09964(10) 0.68869(11) 0.0355(4) Uani 1 1 d . . . N1 N 0.41998(16) 0.19577(11) 0.95470(12) 0.0300(4) Uani 1 1 d . . . N2 N 0.30438(18) 0.23695(11) 0.93948(13) 0.0328(4) Uani 1 1 d . . . N3 N 0.25443(17) 0.21994(11) 0.85323(13) 0.0316(4) Uani 1 1 d . . . N4 N 0.50087(19) 0.20070(13) 1.03889(13) 0.0364(4) Uani 1 1 d D . . H4N H 0.549(3) 0.2429(10) 1.041(2) 0.044 Uiso 1 1 d D . . C1 C 0.44309(19) 0.15294(13) 0.87946(15) 0.0292(4) Uani 1 1 d . . . C2 C 0.33664(19) 0.16970(12) 0.81405(15) 0.0286(4) Uani 1 1 d . . . C3 C 0.5601(2) 0.10181(14) 0.87861(17) 0.0376(5) Uani 1 1 d . . . H3A H 0.6145 0.1179 0.8283 0.056 Uiso 1 1 calc R . . H3B H 0.5294 0.0493 0.8665 0.056 Uiso 1 1 calc R . . H3C H 0.6138 0.1044 0.9405 0.056 Uiso 1 1 calc R . . C4 C 0.30917(19) 0.14713(12) 0.71421(14) 0.0289(4) Uani 1 1 d . . . C5 C 0.3902(2) 0.07477(15) 0.59021(16) 0.0367(5) Uani 1 1 d . . . H5A H 0.4796 0.0625 0.5707 0.044 Uiso 1 1 calc R . . H5B H 0.3516 0.1165 0.5489 0.044 Uiso 1 1 calc R . . C6 C 0.3020(2) 0.00559(14) 0.57785(17) 0.0395(5) Uani 1 1 d . . . H6A H 0.3382 -0.0349 0.6209 0.059 Uiso 1 1 calc R . . H6B H 0.2985 -0.0123 0.5118 0.059 Uiso 1 1 calc R . . H6C H 0.2117 0.0189 0.5927 0.059 Uiso 1 1 calc R . . C7 C 0.45487(19) 0.17007(12) 1.12056(14) 0.0287(4) Uani 1 1 d . . . C8 C 0.3546(2) 0.11542(13) 1.11612(15) 0.0328(5) Uani 1 1 d . . . H8 H 0.3105 0.1006 1.0562 0.039 Uiso 1 1 calc R . . C9 C 0.3188(2) 0.08256(13) 1.19914(16) 0.0338(5) Uani 1 1 d . . . H9 H 0.2494 0.0456 1.1969 0.041 Uiso 1 1 calc R . . C10 C 0.3846(2) 0.10401(13) 1.28445(15) 0.0317(4) Uani 1 1 d . . . C11 C 0.4844(2) 0.15808(13) 1.29098(15) 0.0315(4) Uani 1 1 d . . . H11 H 0.5288 0.1718 1.3512 0.038 Uiso 1 1 calc R . . C12 C 0.5189(2) 0.19186(13) 1.20880(15) 0.0299(4) Uani 1 1 d . . . H12 H 0.5863 0.2300 1.2121 0.036 Uiso 1 1 calc R . . F2 F 0.85298(14) 0.03486(9) -0.03513(10) 0.0471(4) Uani 1 1 d . . . O3 O 0.68173(15) 0.17240(10) 0.58972(12) 0.0363(4) Uani 1 1 d . . . O4 O 0.88441(14) 0.11776(9) 0.60420(10) 0.0307(3) Uani 1 1 d . . . N5 N 0.91161(16) 0.22457(11) 0.34389(12) 0.0295(4) Uani 1 1 d . . . N6 N 0.79478(17) 0.26389(11) 0.34511(13) 0.0316(4) Uani 1 1 d . . . N7 N 0.74357(17) 0.24310(11) 0.42180(13) 0.0304(4) Uani 1 1 d . . . N8 N 0.97986(17) 0.23234(11) 0.26494(13) 0.0317(4) Uani 1 1 d D . . H8N H 1.0646(12) 0.2443(15) 0.2788(18) 0.038 Uiso 1 1 d D . . C13 C 0.93537(19) 0.17838(12) 0.42067(14) 0.0276(4) Uani 1 1 d . . . C14 C 0.82657(19) 0.19165(12) 0.47030(14) 0.0283(4) Uani 1 1 d . . . C15 C 1.0547(2) 0.12939(14) 0.43726(16) 0.0340(5) Uani 1 1 d . . . H15A H 1.0995 0.1264 0.3788 0.051 Uiso 1 1 calc R . . H15B H 1.0278 0.0781 0.4555 0.051 Uiso 1 1 calc R . . H15C H 1.1161 0.1512 0.4885 0.051 Uiso 1 1 calc R . . C16 C 0.7890(2) 0.16076(12) 0.55996(15) 0.0287(4) Uani 1 1 d . . . C17 C 0.8544(2) 0.08558(14) 0.69461(15) 0.0326(4) Uani 1 1 d . . . H17A H 0.7837 0.0463 0.6839 0.039 Uiso 1 1 calc R . . H17B H 0.8224 0.1261 0.7357 0.039 Uiso 1 1 calc R . . C18 C 0.9798(2) 0.05059(16) 0.74139(17) 0.0409(5) Uani 1 1 d . . . H18A H 1.0120 0.0116 0.6993 0.061 Uiso 1 1 calc R . . H18B H 0.9615 0.0269 0.8017 0.061 Uiso 1 1 calc R . . H18C H 1.0481 0.0903 0.7538 0.061 Uiso 1 1 calc R . . C19 C 0.94763(19) 0.17898(12) 0.19098(14) 0.0284(4) Uani 1 1 d . . . C20 C 0.8406(2) 0.12936(13) 0.19147(16) 0.0328(5) Uani 1 1 d . . . H20 H 0.7892 0.1284 0.2444 0.039 Uiso 1 1 calc R . . C21 C 0.8083(2) 0.08089(14) 0.11473(17) 0.0370(5) Uani 1 1 d . . . H21 H 0.7346 0.0469 0.1144 0.044 Uiso 1 1 calc R . . C22 C 0.8846(2) 0.08294(14) 0.03951(16) 0.0362(5) Uani 1 1 d . . . C23 C 0.9912(2) 0.13161(14) 0.03714(16) 0.0358(5) Uani 1 1 d . . . H23 H 1.0425 0.1318 -0.0159 0.043 Uiso 1 1 calc R . . C24 C 1.0226(2) 0.18020(14) 0.11302(16) 0.0335(5) Uani 1 1 d . . . H24 H 1.0955 0.2146 0.1121 0.040 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0413(8) 0.0586(9) 0.0267(6) 0.0052(6) 0.0026(5) -0.0077(6) O1 0.0264(8) 0.0521(10) 0.0298(8) 0.0004(7) -0.0060(6) 0.0034(6) O2 0.0220(7) 0.0544(10) 0.0292(8) -0.0078(7) -0.0017(6) 0.0036(6) N1 0.0190(8) 0.0474(10) 0.0228(8) 0.0006(7) -0.0025(6) -0.0026(7) N2 0.0230(8) 0.0474(11) 0.0279(9) -0.0016(7) 0.0015(7) -0.0004(7) N3 0.0213(8) 0.0451(10) 0.0283(9) -0.0005(7) 0.0013(7) 0.0000(7) N4 0.0269(9) 0.0576(12) 0.0230(8) 0.0014(8) -0.0054(7) -0.0123(8) C1 0.0188(9) 0.0412(11) 0.0269(10) 0.0014(8) -0.0010(7) -0.0029(8) C2 0.0192(9) 0.0395(11) 0.0265(10) 0.0002(8) -0.0002(7) -0.0014(7) C3 0.0218(10) 0.0503(13) 0.0392(12) -0.0006(10) -0.0048(9) 0.0038(9) C4 0.0194(9) 0.0397(11) 0.0275(10) 0.0000(8) 0.0015(7) -0.0027(7) C5 0.0287(11) 0.0541(14) 0.0272(10) -0.0064(9) 0.0020(8) -0.0024(9) C6 0.0361(12) 0.0474(13) 0.0344(12) -0.0035(10) 0.0006(9) -0.0028(10) C7 0.0185(9) 0.0414(11) 0.0256(10) -0.0002(8) -0.0007(7) -0.0001(7) C8 0.0239(10) 0.0463(12) 0.0268(10) -0.0013(9) -0.0045(8) -0.0039(8) C9 0.0253(10) 0.0434(12) 0.0320(11) 0.0012(9) -0.0011(8) -0.0061(8) C10 0.0275(10) 0.0416(11) 0.0261(10) 0.0027(8) 0.0026(8) 0.0008(8) C11 0.0233(9) 0.0443(12) 0.0257(10) -0.0031(8) -0.0023(7) 0.0012(8) C12 0.0190(9) 0.0416(11) 0.0282(10) -0.0032(8) -0.0023(7) 0.0003(8) F2 0.0359(7) 0.0615(9) 0.0417(8) -0.0191(7) -0.0069(6) 0.0051(6) O3 0.0225(7) 0.0498(9) 0.0369(8) 0.0025(7) 0.0047(6) 0.0032(6) O4 0.0237(7) 0.0427(8) 0.0257(7) 0.0030(6) 0.0017(5) 0.0016(6) N5 0.0199(8) 0.0417(10) 0.0261(8) 0.0000(7) -0.0019(6) 0.0004(7) N6 0.0201(8) 0.0455(10) 0.0280(9) -0.0006(7) -0.0028(6) 0.0030(7) N7 0.0209(8) 0.0423(10) 0.0269(8) 0.0005(7) -0.0025(6) 0.0007(7) N8 0.0201(8) 0.0487(11) 0.0260(9) 0.0001(7) 0.0002(6) -0.0042(7) C13 0.0199(9) 0.0383(10) 0.0236(9) -0.0008(8) -0.0034(7) -0.0023(7) C14 0.0191(9) 0.0391(11) 0.0256(9) -0.0026(8) -0.0038(7) 0.0001(7) C15 0.0228(10) 0.0466(12) 0.0318(11) 0.0019(9) -0.0012(8) 0.0039(8) C16 0.0219(9) 0.0356(10) 0.0279(10) -0.0023(8) -0.0013(7) -0.0016(7) C17 0.0264(10) 0.0447(12) 0.0267(10) 0.0031(8) 0.0032(8) -0.0030(8) C18 0.0296(11) 0.0595(15) 0.0333(11) 0.0116(10) 0.0016(9) 0.0017(10) C19 0.0196(9) 0.0389(11) 0.0256(9) 0.0027(8) -0.0038(7) 0.0036(7) C20 0.0207(9) 0.0457(12) 0.0311(10) 0.0002(9) -0.0009(8) 0.0002(8) C21 0.0223(10) 0.0469(13) 0.0401(12) -0.0037(10) -0.0047(8) 0.0000(9) C22 0.0272(10) 0.0466(13) 0.0327(11) -0.0071(9) -0.0071(8) 0.0084(9) C23 0.0260(10) 0.0498(13) 0.0311(11) -0.0012(9) -0.0003(8) 0.0070(9) C24 0.0237(10) 0.0435(12) 0.0328(11) 0.0025(9) 0.0002(8) 0.0024(8) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 F1 C10 1.360(2) . ? O1 C4 1.204(3) . ? O2 C4 1.335(3) . ? O2 C5 1.449(3) . ? N1 C1 1.338(3) . ? N1 N2 1.367(3) . ? N1 N4 1.373(2) . ? N2 N3 1.303(3) . ? N3 C2 1.361(3) . ? N4 C7 1.391(3) . ? N4 H4N 0.882(10) . ? C1 C2 1.373(3) . ? C1 C3 1.479(3) . ? C2 C4 1.462(3) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C5 C6 1.501(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.387(3) . ? C7 C12 1.396(3) . ? C8 C9 1.384(3) . ? C8 H8 0.9500 . ? C9 C10 1.367(3) . ? C9 H9 0.9500 . ? C10 C11 1.376(3) . ? C11 C12 1.376(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? F2 C22 1.360(3) . ? O3 C16 1.213(3) . ? O4 C16 1.326(2) . ? O4 C17 1.453(2) . ? N5 C13 1.354(3) . ? N5 N6 1.363(2) . ? N5 N8 1.372(2) . ? N6 N7 1.296(2) . ? N7 C14 1.365(3) . ? N8 C19 1.414(3) . ? N8 H8N 0.880(10) . ? C13 C14 1.376(3) . ? C13 C15 1.475(3) . ? C14 C16 1.459(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C17 C18 1.495(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.384(3) . ? C19 C24 1.394(3) . ? C20 C21 1.388(3) . ? C20 H20 0.9500 . ? C21 C22 1.370(3) . ? C21 H21 0.9500 . ? C22 C23 1.373(3) . ? C23 C24 1.379(3) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O2 C5 116.58(17) . . ? C1 N1 N2 112.54(16) . . ? C1 N1 N4 125.87(18) . . ? N2 N1 N4 121.59(18) . . ? N3 N2 N1 105.59(17) . . ? N2 N3 C2 109.46(17) . . ? N1 N4 C7 118.32(17) . . ? N1 N4 H4N 110.8(19) . . ? C7 N4 H4N 121.7(19) . . ? N1 C1 C2 103.14(18) . . ? N1 C1 C3 123.13(18) . . ? C2 C1 C3 133.7(2) . . ? N3 C2 C1 109.25(19) . . ? N3 C2 C4 120.09(18) . . ? C1 C2 C4 130.5(2) . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? O1 C4 O2 124.9(2) . . ? O1 C4 C2 124.2(2) . . ? O2 C4 C2 110.93(17) . . ? O2 C5 C6 110.45(19) . . ? O2 C5 H5A 109.6 . . ? C6 C5 H5A 109.6 . . ? O2 C5 H5B 109.6 . . ? C6 C5 H5B 109.6 . . ? H5A C5 H5B 108.1 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 N4 121.93(19) . . ? C8 C7 C12 119.8(2) . . ? N4 C7 C12 118.09(19) . . ? C9 C8 C7 119.85(19) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C10 C9 C8 119.1(2) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? F1 C10 C9 119.2(2) . . ? F1 C10 C11 118.53(19) . . ? C9 C10 C11 122.3(2) . . ? C12 C11 C10 118.85(19) . . ? C12 C11 H11 120.6 . . ? C10 C11 H11 120.6 . . ? C11 C12 C7 120.1(2) . . ? C11 C12 H12 120.0 . . ? C7 C12 H12 120.0 . . ? C16 O4 C17 115.43(16) . . ? C13 N5 N6 112.05(17) . . ? C13 N5 N8 130.23(18) . . ? N6 N5 N8 117.49(17) . . ? N7 N6 N5 106.46(16) . . ? N6 N7 C14 109.25(17) . . ? N5 N8 C19 115.90(17) . . ? N5 N8 H8N 113.3(17) . . ? C19 N8 H8N 117.8(17) . . ? N5 C13 C14 102.71(18) . . ? N5 C13 C15 123.39(19) . . ? C14 C13 C15 133.9(2) . . ? N7 C14 C13 109.53(19) . . ? N7 C14 C16 118.72(18) . . ? C13 C14 C16 131.75(19) . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O3 C16 O4 124.0(2) . . ? O3 C16 C14 123.62(19) . . ? O4 C16 C14 112.35(17) . . ? O4 C17 C18 107.85(17) . . ? O4 C17 H17A 110.1 . . ? C18 C17 H17A 110.1 . . ? O4 C17 H17B 110.1 . . ? C18 C17 H17B 110.1 . . ? H17A C17 H17B 108.5 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C24 119.7(2) . . ? C20 C19 N8 122.18(19) . . ? C24 C19 N8 118.01(19) . . ? C19 C20 C21 120.1(2) . . ? C19 C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? C22 C21 C20 118.8(2) . . ? C22 C21 H21 120.6 . . ? C20 C21 H21 120.6 . . ? F2 C22 C21 118.5(2) . . ? F2 C22 C23 119.2(2) . . ? C21 C22 C23 122.3(2) . . ? C22 C23 C24 118.9(2) . . ? C22 C23 H23 120.6 . . ? C24 C23 H23 120.6 . . ? C23 C24 C19 120.2(2) . . ? C23 C24 H24 119.9 . . ? C19 C24 H24 119.9 . . ? 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 N2 N3 -0.2(2) . . . . ? N4 N1 N2 N3 178.94(18) . . . . ? N1 N2 N3 C2 -0.5(2) . . . . ? C1 N1 N4 C7 -111.5(2) . . . . ? N2 N1 N4 C7 69.5(3) . . . . ? N2 N1 C1 C2 0.9(2) . . . . ? N4 N1 C1 C2 -178.27(19) . . . . ? N2 N1 C1 C3 -178.6(2) . . . . ? N4 N1 C1 C3 2.3(3) . . . . ? N2 N3 C2 C1 1.1(2) . . . . ? N2 N3 C2 C4 -174.29(19) . . . . ? N1 C1 C2 N3 -1.2(2) . . . . ? C3 C1 C2 N3 178.2(2) . . . . ? N1 C1 C2 C4 173.6(2) . . . . ? C3 C1 C2 C4 -7.0(4) . . . . ? C5 O2 C4 O1 0.8(3) . . . . ? C5 O2 C4 C2 -178.03(18) . . . . ? N3 C2 C4 O1 -0.8(3) . . . . ? C1 C2 C4 O1 -175.1(2) . . . . ? N3 C2 C4 O2 178.04(18) . . . . ? C1 C2 C4 O2 3.8(3) . . . . ? C4 O2 C5 C6 -86.7(2) . . . . ? N1 N4 C7 C8 20.7(3) . . . . ? N1 N4 C7 C12 -163.6(2) . . . . ? N4 C7 C8 C9 175.3(2) . . . . ? C12 C7 C8 C9 -0.3(3) . . . . ? C7 C8 C9 C10 -0.8(3) . . . . ? C8 C9 C10 F1 -179.1(2) . . . . ? C8 C9 C10 C11 0.9(4) . . . . ? F1 C10 C11 C12 -179.80(19) . . . . ? C9 C10 C11 C12 0.2(3) . . . . ? C10 C11 C12 C7 -1.3(3) . . . . ? C8 C7 C12 C11 1.3(3) . . . . ? N4 C7 C12 C11 -174.4(2) . . . . ? C13 N5 N6 N7 -0.2(2) . . . . ? N8 N5 N6 N7 174.91(17) . . . . ? N5 N6 N7 C14 0.6(2) . . . . ? C13 N5 N8 C19 83.5(3) . . . . ? N6 N5 N8 C19 -90.5(2) . . . . ? N6 N5 C13 C14 -0.4(2) . . . . ? N8 N5 C13 C14 -174.6(2) . . . . ? N6 N5 C13 C15 -179.99(19) . . . . ? N8 N5 C13 C15 5.8(3) . . . . ? N6 N7 C14 C13 -0.9(2) . . . . ? N6 N7 C14 C16 179.53(18) . . . . ? N5 C13 C14 N7 0.8(2) . . . . ? C15 C13 C14 N7 -179.7(2) . . . . ? N5 C13 C14 C16 -179.8(2) . . . . ? C15 C13 C14 C16 -0.2(4) . . . . ? C17 O4 C16 O3 -1.5(3) . . . . ? C17 O4 C16 C14 179.44(17) . . . . ? N7 C14 C16 O3 7.4(3) . . . . ? C13 C14 C16 O3 -172.0(2) . . . . ? N7 C14 C16 O4 -173.51(18) . . . . ? C13 C14 C16 O4 7.1(3) . . . . ? C16 O4 C17 C18 -170.55(19) . . . . ? N5 N8 C19 C20 9.3(3) . . . . ? N5 N8 C19 C24 -174.38(18) . . . . ? C24 C19 C20 C21 0.1(3) . . . . ? N8 C19 C20 C21 176.4(2) . . . . ? C19 C20 C21 C22 0.5(3) . . . . ? C20 C21 C22 F2 179.5(2) . . . . ? C20 C21 C22 C23 -0.5(3) . . . . ? F2 C22 C23 C24 180.0(2) . . . . ? C21 C22 C23 C24 -0.1(3) . . . . ? C22 C23 C24 C19 0.7(3) . . . . ? C20 C19 C24 C23 -0.7(3) . . . . ? N8 C19 C24 C23 -177.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.36 _refine_diff_density_min -0.25 _refine_diff_density_rms 0.062 _database_code_depnum_ccdc_archive 'CCDC 845655' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_(4-Cl) data_shelx3 #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H13 Cl N4 O2' _chemical_formula_sum 'C12 H13 Cl N4 O2' _chemical_formula_weight 280.71 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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' Cl Cl 0.1480 0.1590 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 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 12.6207(7) _cell_length_b 9.8187(5) _cell_length_c 11.0587(7) _cell_angle_alpha 90.00 _cell_angle_beta 105.846(3) _cell_angle_gamma 90.00 _cell_volume 1318.31(13) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3137 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.294 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.774 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10 cm confocal mirrors' _diffrn_measurement_device_type 'Enraf Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 14912 _diffrn_reflns_av_R_equivalents 0.063 _diffrn_reflns_av_sigmaI/netI 0.056 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.0 _diffrn_reflns_theta_max 27.5 _reflns_number_total 3031 _reflns_number_gt 2127 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT' _computing_data_reduction 'DENZO & COLLECT' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006)' _computing_publication_material 'publCIF (Westrip, 2010)' _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^ > 2\s(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^)+(0.0714P)^2^+0.2703P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3031 _refine_ls_number_parameters 177 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.080 _refine_ls_R_factor_gt 0.047 _refine_ls_wR_factor_ref 0.134 _refine_ls_wR_factor_gt 0.117 _refine_ls_goodness_of_fit_ref 1.03 _refine_ls_restrained_S_all 1.03 _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 -0.03341(5) 0.19116(5) -0.13164(5) 0.0360(2) Uani 1 1 d . . . O1 O 0.60053(12) -0.15637(14) 0.60765(13) 0.0298(4) Uani 1 1 d . . . O2 O 0.69730(11) -0.06712(15) 0.48329(13) 0.0281(3) Uani 1 1 d . . . N1 N 0.41780(13) -0.13478(16) 0.20037(15) 0.0218(4) Uani 1 1 d . . . N2 N 0.35707(14) -0.18980(16) 0.27279(16) 0.0245(4) Uani 1 1 d . . . N3 N 0.42097(14) -0.18935(16) 0.38724(16) 0.0235(4) Uani 1 1 d . . . N4 N 0.37578(14) -0.12147(17) 0.07204(15) 0.0243(4) Uani 1 1 d D . . H4N H 0.3823(18) -0.1946(15) 0.0284(19) 0.029 Uiso 1 1 d D . . C1 C 0.51972(16) -0.09980(19) 0.26722(18) 0.0210(4) Uani 1 1 d . . . C2 C 0.52068(16) -0.13698(18) 0.38778(18) 0.0217(4) Uani 1 1 d . . . C3 C 0.60095(18) -0.0374(2) 0.2102(2) 0.0287(5) Uani 1 1 d . . . H3A H 0.6555 -0.1059 0.2033 0.043 Uiso 1 1 calc R . . H3B H 0.6381 0.0380 0.2631 0.043 Uiso 1 1 calc R . . H3C H 0.5632 -0.0030 0.1263 0.043 Uiso 1 1 calc R . . C4 C 0.60827(17) -0.12285(19) 0.50566(19) 0.0243(5) Uani 1 1 d . . . C5 C 0.79052(17) -0.0403(2) 0.5893(2) 0.0302(5) Uani 1 1 d . . . H5A H 0.8252 -0.1264 0.6270 0.036 Uiso 1 1 calc R . . H5B H 0.7681 0.0127 0.6544 0.036 Uiso 1 1 calc R . . C6 C 0.8678(2) 0.0401(3) 0.5361(2) 0.0453(6) Uani 1 1 d . . . H6A H 0.8913 -0.0155 0.4744 0.068 Uiso 1 1 calc R . . H6B H 0.9324 0.0664 0.6040 0.068 Uiso 1 1 calc R . . H6C H 0.8304 0.1221 0.4950 0.068 Uiso 1 1 calc R . . C7 C 0.27665(17) -0.04899(19) 0.02817(18) 0.0217(4) Uani 1 1 d . . . C8 C 0.25440(18) 0.0644(2) 0.09205(19) 0.0251(5) Uani 1 1 d . . . H8 H 0.3047 0.0917 0.1689 0.030 Uiso 1 1 calc R . . C9 C 0.15793(18) 0.1377(2) 0.0429(2) 0.0276(5) Uani 1 1 d . . . H9 H 0.1411 0.2143 0.0868 0.033 Uiso 1 1 calc R . . C10 C 0.08703(17) 0.0985(2) -0.0697(2) 0.0268(5) Uani 1 1 d . . . C11 C 0.10934(17) -0.0132(2) -0.13407(19) 0.0277(5) Uani 1 1 d . . . H11 H 0.0599 -0.0389 -0.2120 0.033 Uiso 1 1 calc R . . C12 C 0.20363(17) -0.0873(2) -0.08465(19) 0.0248(5) Uani 1 1 d . . . H12 H 0.2188 -0.1652 -0.1281 0.030 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0360(3) 0.0344(3) 0.0361(3) 0.0042(2) 0.0074(2) 0.0092(2) O1 0.0427(9) 0.0291(7) 0.0193(7) 0.0016(6) 0.0115(7) -0.0013(7) O2 0.0298(8) 0.0334(8) 0.0215(7) -0.0011(6) 0.0076(6) -0.0013(6) N1 0.0291(9) 0.0202(8) 0.0184(8) 0.0017(7) 0.0103(7) 0.0012(7) N2 0.0297(9) 0.0240(9) 0.0223(9) 0.0029(7) 0.0114(7) 0.0011(7) N3 0.0294(9) 0.0223(8) 0.0202(9) 0.0021(7) 0.0092(7) 0.0008(7) N4 0.0319(10) 0.0268(9) 0.0147(8) -0.0017(7) 0.0069(7) 0.0039(7) C1 0.0266(11) 0.0175(9) 0.0203(10) -0.0015(8) 0.0087(8) 0.0020(8) C2 0.0303(11) 0.0173(9) 0.0206(10) 0.0015(8) 0.0124(8) 0.0011(8) C3 0.0347(12) 0.0315(11) 0.0221(11) 0.0021(9) 0.0117(9) -0.0055(9) C4 0.0332(12) 0.0187(9) 0.0231(11) -0.0018(8) 0.0111(9) 0.0038(8) C5 0.0290(12) 0.0354(12) 0.0248(11) -0.0049(9) 0.0052(9) 0.0022(9) C6 0.0399(14) 0.0543(15) 0.0404(14) -0.0075(12) 0.0085(12) -0.0048(12) C7 0.0280(11) 0.0208(9) 0.0184(10) 0.0020(8) 0.0099(8) -0.0024(8) C8 0.0347(12) 0.0224(10) 0.0188(10) 0.0000(8) 0.0086(9) -0.0020(9) C9 0.0388(12) 0.0205(10) 0.0263(11) 0.0005(8) 0.0138(10) 0.0029(9) C10 0.0294(11) 0.0263(10) 0.0262(11) 0.0051(9) 0.0102(9) 0.0019(9) C11 0.0308(12) 0.0305(11) 0.0218(10) -0.0028(9) 0.0071(9) -0.0036(9) C12 0.0305(11) 0.0231(10) 0.0230(10) -0.0033(8) 0.0107(9) -0.0009(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C10 1.743(2) . ? O1 C4 1.204(2) . ? O2 C4 1.332(2) . ? O2 C5 1.440(3) . ? N1 C1 1.342(3) . ? N1 N2 1.362(2) . ? N1 N4 1.379(2) . ? N2 N3 1.302(2) . ? N3 C2 1.358(3) . ? N4 C7 1.406(3) . ? N4 H4N 0.882(9) . ? C1 C2 1.379(3) . ? C1 C3 1.476(3) . ? C2 C4 1.468(3) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C5 C6 1.494(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C12 1.386(3) . ? C7 C8 1.387(3) . ? C8 C9 1.391(3) . ? C8 H8 0.9500 . ? C9 C10 1.376(3) . ? C9 H9 0.9500 . ? C10 C11 1.378(3) . ? C11 C12 1.374(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O2 C5 117.84(16) . . ? C1 N1 N2 112.72(16) . . ? C1 N1 N4 125.75(16) . . ? N2 N1 N4 121.51(16) . . ? N3 N2 N1 105.76(16) . . ? N2 N3 C2 109.45(16) . . ? N1 N4 C7 117.33(16) . . ? N1 N4 H4N 114.8(15) . . ? C7 N4 H4N 115.5(15) . . ? N1 C1 C2 102.64(17) . . ? N1 C1 C3 122.98(18) . . ? C2 C1 C3 134.38(19) . . ? N3 C2 C1 109.42(18) . . ? N3 C2 C4 120.81(17) . . ? C1 C2 C4 129.74(18) . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? O1 C4 O2 125.06(19) . . ? O1 C4 C2 124.89(19) . . ? O2 C4 C2 110.05(17) . . ? O2 C5 C6 104.61(18) . . ? O2 C5 H5A 110.8 . . ? C6 C5 H5A 110.8 . . ? O2 C5 H5B 110.8 . . ? C6 C5 H5B 110.8 . . ? H5A C5 H5B 108.9 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C12 C7 C8 119.94(19) . . ? C12 C7 N4 118.92(17) . . ? C8 C7 N4 121.02(18) . . ? C7 C8 C9 119.6(2) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C10 C9 C8 119.49(19) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C9 C10 C11 121.1(2) . . ? C9 C10 Cl1 119.43(16) . . ? C11 C10 Cl1 119.48(17) . . ? C12 C11 C10 119.5(2) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C11 C12 C7 120.33(18) . . ? C11 C12 H12 119.8 . . ? C7 C12 H12 119.8 . . ? 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 N2 N3 0.3(2) . . . . ? N4 N1 N2 N3 178.96(15) . . . . ? N1 N2 N3 C2 -0.80(19) . . . . ? C1 N1 N4 C7 -125.8(2) . . . . ? N2 N1 N4 C7 55.7(2) . . . . ? N2 N1 C1 C2 0.4(2) . . . . ? N4 N1 C1 C2 -178.27(16) . . . . ? N2 N1 C1 C3 -179.62(17) . . . . ? N4 N1 C1 C3 1.7(3) . . . . ? N2 N3 C2 C1 1.1(2) . . . . ? N2 N3 C2 C4 179.10(16) . . . . ? N1 C1 C2 N3 -0.9(2) . . . . ? C3 C1 C2 N3 179.1(2) . . . . ? N1 C1 C2 C4 -178.65(18) . . . . ? C3 C1 C2 C4 1.3(4) . . . . ? C5 O2 C4 O1 -2.3(3) . . . . ? C5 O2 C4 C2 177.53(16) . . . . ? N3 C2 C4 O1 0.9(3) . . . . ? C1 C2 C4 O1 178.51(19) . . . . ? N3 C2 C4 O2 -178.86(16) . . . . ? C1 C2 C4 O2 -1.3(3) . . . . ? C4 O2 C5 C6 -171.53(18) . . . . ? N1 N4 C7 C12 -147.16(18) . . . . ? N1 N4 C7 C8 36.7(3) . . . . ? C12 C7 C8 C9 0.8(3) . . . . ? N4 C7 C8 C9 176.91(18) . . . . ? C7 C8 C9 C10 -1.4(3) . . . . ? C8 C9 C10 C11 0.8(3) . . . . ? C8 C9 C10 Cl1 -179.62(15) . . . . ? C9 C10 C11 C12 0.4(3) . . . . ? Cl1 C10 C11 C12 -179.24(15) . . . . ? C10 C11 C12 C7 -0.9(3) . . . . ? C8 C7 C12 C11 0.3(3) . . . . ? N4 C7 C12 C11 -175.85(18) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.23 _refine_diff_density_min -0.41 _refine_diff_density_rms 0.069 _database_code_depnum_ccdc_archive 'CCDC 845656' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_(4-Br) data_1093 #TrackingRef '4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H13 Br N4 O2' _chemical_formula_sum 'C12 H13 Br N4 O2' _chemical_formula_weight 325.17 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' Br Br -0.2901 2.4595 '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 12.7435(3) _cell_length_b 9.9927(2) _cell_length_c 11.1150(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.3049(13) _cell_angle_gamma 90.00 _cell_volume 1365.17(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3306 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour light-brown _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.582 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 3.015 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.727 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10 cm confocal mirrors' _diffrn_measurement_device_type 'Enraf Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 20395 _diffrn_reflns_av_R_equivalents 0.047 _diffrn_reflns_av_sigmaI/netI 0.029 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.8 _diffrn_reflns_theta_max 27.5 _reflns_number_total 3126 _reflns_number_gt 2583 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT' _computing_data_reduction 'DENZO & COLLECT' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006)' _computing_publication_material 'publCIF (Westrip, 2010)' _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^ > 2\s(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^)+(0.0359P)^2^+0.6692P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3126 _refine_ls_number_parameters 177 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.041 _refine_ls_R_factor_gt 0.028 _refine_ls_wR_factor_ref 0.071 _refine_ls_wR_factor_gt 0.066 _refine_ls_goodness_of_fit_ref 1.02 _refine_ls_restrained_S_all 1.02 _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 0.463339(18) -0.19594(2) 0.36752(2) 0.03058(9) Uani 1 1 d . . . O1 O 1.09506(13) 0.15841(15) 1.10667(13) 0.0263(3) Uani 1 1 d . . . O2 O 1.19335(11) 0.07073(14) 0.98360(12) 0.0242(3) Uani 1 1 d . . . N1 N 0.91861(13) 0.13520(15) 0.70082(14) 0.0176(3) Uani 1 1 d . . . N2 N 0.85771(14) 0.19102(16) 0.77185(15) 0.0209(3) Uani 1 1 d . . . N3 N 0.91996(14) 0.19067(15) 0.88615(15) 0.0209(3) Uani 1 1 d . . . N4 N 0.87846(14) 0.12177(17) 0.57279(14) 0.0208(4) Uani 1 1 d D . . H4N H 0.8888(19) 0.1940(15) 0.5335(19) 0.025 Uiso 1 1 d D . . C1 C 1.01889(16) 0.10036(18) 0.76792(17) 0.0181(4) Uani 1 1 d . . . C2 C 1.01876(16) 0.13758(18) 0.88788(17) 0.0184(4) Uani 1 1 d . . . C3 C 1.10050(17) 0.0374(2) 0.71176(19) 0.0254(4) Uani 1 1 d . . . H3A H 1.0647 0.0076 0.6268 0.038 Uiso 1 1 calc R . . H3B H 1.1334 -0.0397 0.7623 0.038 Uiso 1 1 calc R . . H3C H 1.1572 0.1027 0.7091 0.038 Uiso 1 1 calc R . . C4 C 1.10424(16) 0.12520(18) 1.00502(18) 0.0201(4) Uani 1 1 d . . . C5 C 1.28557(17) 0.0463(2) 1.08981(19) 0.0262(4) Uani 1 1 d . . . H5A H 1.2635 -0.0066 1.1544 0.031 Uiso 1 1 calc R . . H5B H 1.3181 0.1316 1.1271 0.031 Uiso 1 1 calc R . . C6 C 1.3645(2) -0.0309(3) 1.0371(2) 0.0404(6) Uani 1 1 d . . . H6A H 1.3302 -0.1140 0.9994 0.061 Uiso 1 1 calc R . . H6B H 1.4295 -0.0521 1.1042 0.061 Uiso 1 1 calc R . . H6C H 1.3852 0.0232 0.9735 0.061 Uiso 1 1 calc R . . C7 C 0.78099(16) 0.04918(19) 0.52988(17) 0.0185(4) Uani 1 1 d . . . C8 C 0.70862(16) 0.0870(2) 0.41745(18) 0.0218(4) Uani 1 1 d . . . H8 H 0.7234 0.1638 0.3742 0.026 Uiso 1 1 calc R . . C9 C 0.61543(17) 0.0130(2) 0.36897(19) 0.0237(4) Uani 1 1 d . . . H9 H 0.5666 0.0379 0.2919 0.028 Uiso 1 1 calc R . . C10 C 0.59352(17) -0.0979(2) 0.43332(18) 0.0230(4) Uani 1 1 d . . . C11 C 0.66483(18) -0.1364(2) 0.54499(18) 0.0237(4) Uani 1 1 d . . . H11 H 0.6491 -0.2124 0.5885 0.028 Uiso 1 1 calc R . . C12 C 0.75892(17) -0.06389(19) 0.59287(18) 0.0213(4) Uani 1 1 d . . . H12 H 0.8086 -0.0910 0.6687 0.026 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.02888(13) 0.02893(13) 0.03189(14) -0.00515(9) 0.00445(9) -0.00708(9) O1 0.0345(8) 0.0278(7) 0.0169(7) -0.0031(6) 0.0075(6) -0.0005(6) O2 0.0233(7) 0.0316(8) 0.0169(7) -0.0008(6) 0.0039(6) 0.0010(6) N1 0.0222(8) 0.0180(8) 0.0133(7) -0.0001(6) 0.0061(6) -0.0003(6) N2 0.0230(9) 0.0222(8) 0.0195(8) -0.0032(7) 0.0090(7) -0.0006(7) N3 0.0244(9) 0.0209(8) 0.0190(8) -0.0032(7) 0.0088(7) -0.0014(7) N4 0.0267(9) 0.0240(9) 0.0120(8) 0.0017(6) 0.0056(7) -0.0032(7) C1 0.0224(10) 0.0146(8) 0.0179(9) 0.0003(7) 0.0065(8) -0.0011(7) C2 0.0233(10) 0.0161(9) 0.0173(9) -0.0015(7) 0.0080(8) -0.0026(8) C3 0.0281(11) 0.0304(11) 0.0193(10) -0.0028(8) 0.0094(9) 0.0062(9) C4 0.0254(10) 0.0168(9) 0.0189(10) 0.0000(7) 0.0072(8) -0.0034(8) C5 0.0228(11) 0.0323(11) 0.0215(10) 0.0041(9) 0.0021(8) -0.0012(9) C6 0.0334(13) 0.0480(15) 0.0387(14) 0.0057(12) 0.0076(11) 0.0073(11) C7 0.0206(10) 0.0201(9) 0.0161(9) -0.0022(7) 0.0068(8) 0.0009(8) C8 0.0246(10) 0.0228(10) 0.0186(9) 0.0029(8) 0.0071(8) 0.0011(8) C9 0.0243(10) 0.0281(10) 0.0178(10) 0.0009(8) 0.0040(8) 0.0026(8) C10 0.0260(11) 0.0213(9) 0.0216(10) -0.0054(8) 0.0062(8) -0.0009(8) C11 0.0338(12) 0.0176(9) 0.0202(10) -0.0001(8) 0.0081(9) -0.0023(8) C12 0.0277(11) 0.0212(9) 0.0148(9) 0.0007(8) 0.0053(8) 0.0018(8) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C10 1.899(2) . ? O1 C4 1.213(2) . ? O2 C4 1.336(2) . ? O2 C5 1.450(2) . ? N1 C1 1.344(2) . ? N1 N2 1.364(2) . ? N1 N4 1.386(2) . ? N2 N3 1.308(2) . ? N3 C2 1.362(3) . ? N4 C7 1.408(3) . ? N4 H4N 0.872(9) . ? C1 C2 1.385(3) . ? C1 C3 1.487(3) . ? C2 C4 1.466(3) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C5 C6 1.503(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.395(3) . ? C7 C12 1.396(3) . ? C8 C9 1.382(3) . ? C8 H8 0.9500 . ? C9 C10 1.387(3) . ? C9 H9 0.9500 . ? C10 C11 1.385(3) . ? C11 C12 1.382(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O2 C5 117.89(15) . . ? C1 N1 N2 112.81(15) . . ? C1 N1 N4 125.71(16) . . ? N2 N1 N4 121.45(16) . . ? N3 N2 N1 105.62(15) . . ? N2 N3 C2 109.64(15) . . ? N1 N4 C7 116.82(15) . . ? N1 N4 H4N 111.8(16) . . ? C7 N4 H4N 119.6(16) . . ? N1 C1 C2 102.83(16) . . ? N1 C1 C3 123.00(17) . . ? C2 C1 C3 134.17(18) . . ? N3 C2 C1 109.10(17) . . ? N3 C2 C4 120.86(16) . . ? C1 C2 C4 130.03(18) . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? O1 C4 O2 124.98(19) . . ? O1 C4 C2 124.94(18) . . ? O2 C4 C2 110.08(16) . . ? O2 C5 C6 104.54(17) . . ? O2 C5 H5A 110.8 . . ? C6 C5 H5A 110.8 . . ? O2 C5 H5B 110.8 . . ? C6 C5 H5B 110.8 . . ? H5A C5 H5B 108.9 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C12 119.70(18) . . ? C8 C7 N4 118.62(17) . . ? C12 C7 N4 121.56(18) . . ? C9 C8 C7 120.04(18) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C10 119.74(19) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C11 C10 C9 120.68(19) . . ? C11 C10 Br1 120.11(15) . . ? C9 C10 Br1 119.20(16) . . ? C12 C11 C10 119.79(19) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C11 C12 C7 120.03(19) . . ? C11 C12 H12 120.0 . . ? C7 C12 H12 120.0 . . ? 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 N2 N3 -0.5(2) . . . . ? N4 N1 N2 N3 -178.77(15) . . . . ? N1 N2 N3 C2 0.80(19) . . . . ? C1 N1 N4 C7 125.0(2) . . . . ? N2 N1 N4 C7 -57.0(2) . . . . ? N2 N1 C1 C2 0.0(2) . . . . ? N4 N1 C1 C2 178.18(16) . . . . ? N2 N1 C1 C3 179.89(17) . . . . ? N4 N1 C1 C3 -1.9(3) . . . . ? N2 N3 C2 C1 -0.8(2) . . . . ? N2 N3 C2 C4 -179.90(16) . . . . ? N1 C1 C2 N3 0.5(2) . . . . ? C3 C1 C2 N3 -179.4(2) . . . . ? N1 C1 C2 C4 179.43(18) . . . . ? C3 C1 C2 C4 -0.4(4) . . . . ? C5 O2 C4 O1 1.5(3) . . . . ? C5 O2 C4 C2 -177.86(16) . . . . ? N3 C2 C4 O1 0.7(3) . . . . ? C1 C2 C4 O1 -178.18(19) . . . . ? N3 C2 C4 O2 -179.97(16) . . . . ? C1 C2 C4 O2 1.2(3) . . . . ? C4 O2 C5 C6 172.61(17) . . . . ? N1 N4 C7 C8 146.72(17) . . . . ? N1 N4 C7 C12 -37.4(2) . . . . ? C12 C7 C8 C9 0.2(3) . . . . ? N4 C7 C8 C9 176.09(17) . . . . ? C7 C8 C9 C10 0.8(3) . . . . ? C8 C9 C10 C11 -0.9(3) . . . . ? C8 C9 C10 Br1 178.44(15) . . . . ? C9 C10 C11 C12 -0.1(3) . . . . ? Br1 C10 C11 C12 -179.42(15) . . . . ? C10 C11 C12 C7 1.1(3) . . . . ? C8 C7 C12 C11 -1.1(3) . . . . ? N4 C7 C12 C11 -176.95(18) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.28 _refine_diff_density_min -0.54 _refine_diff_density_rms 0.065 _database_code_depnum_ccdc_archive 'CCDC 845657' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_(4-I) data_ssg1271 #TrackingRef '5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H13 I N4 O2' _chemical_formula_sum 'C12 H13 I N4 O2' _chemical_formula_weight 372.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' I I -0.4742 1.8119 '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 c a 21 ' _symmetry_space_group_name_Hall 'P 2c -2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 11.033(2) _cell_length_b 10.411(2) _cell_length_c 24.957(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2866.7(10) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 980 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 22.3 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_diffrn 1.725 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 2.238 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.774 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.6893 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury SRS station 9.8' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'fine-slice \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 5 _diffrn_reflns_number 20053 _diffrn_reflns_av_R_equivalents 0.049 _diffrn_reflns_av_sigmaI/netI 0.043 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_theta_max 24.2 _reflns_number_total 5041 _reflns_number_gt 4113 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'SAINT (Bruker, 2004)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006), Qmol (Gans & Shalloway, 2001) ; _computing_publication_material 'publCIF (Westrip, 2010)' _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^ > 2\s(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^)+(0.028P)^2^+2.9719P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack (1983), 2449 Friedel pairs' _refine_ls_abs_structure_Flack 0.10(3) _refine_ls_number_reflns 5041 _refine_ls_number_parameters 353 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.050 _refine_ls_R_factor_gt 0.036 _refine_ls_wR_factor_ref 0.079 _refine_ls_wR_factor_gt 0.074 _refine_ls_goodness_of_fit_ref 1.01 _refine_ls_restrained_S_all 1.01 _refine_ls_shift/su_max 0.002 _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 I1 I 0.62221(4) 1.02081(4) 0.599225(16) 0.05165(15) Uani 1 1 d . . . O1 O 1.1804(4) 0.5608(4) 0.88979(18) 0.0446(11) Uani 1 1 d . . . O2 O 1.0412(3) 0.6573(4) 0.94230(17) 0.0368(10) Uani 1 1 d . . . N1 N 0.8220(4) 0.6160(4) 0.81032(19) 0.0287(11) Uani 1 1 d . . . N2 N 0.8997(4) 0.5434(4) 0.7808(2) 0.0338(11) Uani 1 1 d . . . N3 N 0.9974(4) 0.5336(4) 0.8093(2) 0.0350(11) Uani 1 1 d . . . N4 N 0.7066(4) 0.6441(4) 0.7922(2) 0.0330(11) Uani 1 1 d D . . H4N H 0.660(4) 0.576(3) 0.796(2) 0.040 Uiso 1 1 d D . . C1 C 0.8681(5) 0.6522(5) 0.8583(3) 0.0306(14) Uani 1 1 d . . . C2 C 0.9821(5) 0.5970(5) 0.8572(2) 0.0307(13) Uani 1 1 d . . . C3 C 0.8012(5) 0.7319(6) 0.8968(3) 0.0428(16) Uani 1 1 d . . . H3A H 0.7283 0.7665 0.8796 0.064 Uiso 1 1 calc R . . H3B H 0.8528 0.8029 0.9088 0.064 Uiso 1 1 calc R . . H3C H 0.7777 0.6795 0.9277 0.064 Uiso 1 1 calc R . . C4 C 1.0794(6) 0.6022(5) 0.8973(3) 0.0332(14) Uani 1 1 d . . . C5 C 1.1292(6) 0.6753(6) 0.9844(3) 0.0458(16) Uani 1 1 d . . . H5A H 1.2035 0.7159 0.9700 0.055 Uiso 1 1 calc R . . H5B H 1.1513 0.5917 1.0006 0.055 Uiso 1 1 calc R . . C6 C 1.0716(7) 0.7599(7) 1.0249(3) 0.056(2) Uani 1 1 d . . . H6A H 1.0395 0.8369 1.0073 0.084 Uiso 1 1 calc R . . H6B H 1.1319 0.7851 1.0518 0.084 Uiso 1 1 calc R . . H6C H 1.0052 0.7137 1.0425 0.084 Uiso 1 1 calc R . . C7 C 0.6937(5) 0.7250(5) 0.7478(2) 0.0314(13) Uani 1 1 d . . . C8 C 0.5981(6) 0.7067(6) 0.7124(3) 0.0400(16) Uani 1 1 d . . . H8 H 0.5464 0.6346 0.7168 0.048 Uiso 1 1 calc R . . C9 C 0.5771(6) 0.7903(6) 0.6713(3) 0.0395(15) Uani 1 1 d . . . H9 H 0.5101 0.7774 0.6480 0.047 Uiso 1 1 calc R . . C10 C 0.6543(5) 0.8946(6) 0.6636(3) 0.0406(14) Uani 1 1 d . . . C11 C 0.7516(5) 0.9126(5) 0.6977(3) 0.0398(14) Uani 1 1 d . . . H11 H 0.8057 0.9823 0.6919 0.048 Uiso 1 1 calc R . . C12 C 0.7708(5) 0.8297(5) 0.7402(3) 0.0316(13) Uani 1 1 d . . . H12 H 0.8363 0.8440 0.7641 0.038 Uiso 1 1 calc R . . I2 I 1.12427(5) 0.46570(4) 1.130296(15) 0.05873(17) Uani 1 1 d . . . O3 O 0.5358(3) 0.0905(4) 0.82698(19) 0.0393(10) Uani 1 1 d . . . O4 O 0.6858(3) 0.1859(4) 0.77995(17) 0.0363(9) Uani 1 1 d . . . N5 N 0.8963(4) 0.1127(4) 0.9106(2) 0.0316(11) Uani 1 1 d . . . N6 N 0.8071(4) 0.0562(4) 0.94146(19) 0.0333(11) Uani 1 1 d . . . N7 N 0.7099(4) 0.0570(4) 0.9122(2) 0.0330(11) Uani 1 1 d . . . N8 N 1.0136(4) 0.1266(5) 0.9288(2) 0.0359(12) Uani 1 1 d D . . H8N H 1.050(5) 0.052(3) 0.928(3) 0.043 Uiso 1 1 d D . . C13 C 0.8534(5) 0.1477(5) 0.8627(3) 0.0315(15) Uani 1 1 d . . . C14 C 0.7358(5) 0.1123(5) 0.8640(2) 0.0305(13) Uani 1 1 d . . . C15 C 0.9350(5) 0.2088(6) 0.8216(3) 0.0404(15) Uani 1 1 d . . . H15A H 0.9653 0.1427 0.7970 0.061 Uiso 1 1 calc R . . H15B H 1.0036 0.2500 0.8397 0.061 Uiso 1 1 calc R . . H15C H 0.8894 0.2733 0.8013 0.061 Uiso 1 1 calc R . . C16 C 0.6403(5) 0.1264(5) 0.8223(2) 0.0323(13) Uani 1 1 d . . . C17 C 0.6041(6) 0.2130(6) 0.7348(2) 0.0394(15) Uani 1 1 d . . . H17A H 0.5298 0.2567 0.7474 0.047 Uiso 1 1 calc R . . H17B H 0.5808 0.1324 0.7164 0.047 Uiso 1 1 calc R . . C18 C 0.6745(7) 0.2984(6) 0.6979(3) 0.0531(19) Uani 1 1 d . . . H18A H 0.6939 0.3790 0.7163 0.080 Uiso 1 1 calc R . . H18B H 0.6260 0.3168 0.6659 0.080 Uiso 1 1 calc R . . H18C H 0.7498 0.2553 0.6873 0.080 Uiso 1 1 calc R . . C19 C 1.0330(5) 0.2014(5) 0.9757(2) 0.0320(13) Uani 1 1 d . . . C20 C 1.1275(6) 0.1719(6) 1.0089(2) 0.0356(14) Uani 1 1 d . . . H20 H 1.1753 0.0979 1.0020 0.043 Uiso 1 1 calc R . . C21 C 1.1539(6) 0.2485(6) 1.0521(2) 0.0392(15) Uani 1 1 d . . . H21 H 1.2210 0.2289 1.0745 0.047 Uiso 1 1 calc R . . C22 C 1.0815(5) 0.3550(6) 1.0629(2) 0.0367(14) Uani 1 1 d . . . C23 C 0.9877(5) 0.3855(6) 1.0300(3) 0.0436(16) Uani 1 1 d . . . H23 H 0.9394 0.4590 1.0373 0.052 Uiso 1 1 calc R . . C24 C 0.9621(5) 0.3094(6) 0.9855(3) 0.0419(16) Uani 1 1 d . . . H24 H 0.8972 0.3309 0.9622 0.050 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0726(4) 0.0422(2) 0.0402(2) 0.0029(2) -0.0077(3) 0.0106(2) O1 0.035(2) 0.046(3) 0.053(3) 0.003(2) 0.008(2) 0.012(2) O2 0.035(2) 0.036(2) 0.040(3) -0.0020(19) 0.001(2) 0.0022(17) N1 0.027(3) 0.023(2) 0.037(3) -0.001(2) 0.009(2) 0.000(2) N2 0.038(3) 0.026(2) 0.038(3) 0.005(2) 0.007(2) 0.004(2) N3 0.039(3) 0.035(3) 0.031(3) 0.006(2) 0.007(2) 0.009(2) N4 0.029(3) 0.031(3) 0.039(3) -0.001(2) 0.000(2) -0.0048(19) C1 0.026(3) 0.024(3) 0.041(4) 0.003(3) 0.010(3) -0.003(2) C2 0.036(3) 0.018(3) 0.037(4) 0.003(2) 0.007(3) 0.005(2) C3 0.032(3) 0.042(4) 0.054(4) -0.014(3) 0.000(3) 0.003(3) C4 0.038(3) 0.021(3) 0.040(4) 0.001(3) 0.011(3) -0.002(3) C5 0.043(4) 0.052(4) 0.042(4) 0.009(3) -0.003(3) -0.010(3) C6 0.057(5) 0.067(5) 0.043(5) -0.010(4) -0.011(4) -0.011(4) C7 0.031(3) 0.031(3) 0.033(3) 0.000(2) 0.001(3) 0.001(2) C8 0.038(4) 0.046(4) 0.036(4) -0.009(3) 0.003(3) -0.010(3) C9 0.043(4) 0.041(4) 0.035(4) -0.010(3) -0.004(3) -0.002(3) C10 0.042(4) 0.042(4) 0.037(3) 0.005(3) 0.008(3) 0.008(3) C11 0.040(3) 0.030(3) 0.048(4) 0.000(3) 0.002(3) 0.003(3) C12 0.027(3) 0.027(3) 0.041(4) 0.000(3) 0.003(3) -0.001(2) I2 0.0685(4) 0.0530(3) 0.0546(3) -0.0198(2) -0.0107(3) 0.0077(2) O3 0.028(2) 0.034(2) 0.055(3) -0.001(2) 0.004(2) -0.0079(18) O4 0.031(2) 0.039(2) 0.039(2) 0.0026(19) 0.0044(19) -0.0003(17) N5 0.024(2) 0.026(2) 0.044(3) 0.002(2) -0.002(2) -0.0016(19) N6 0.039(3) 0.032(3) 0.028(3) -0.003(2) 0.009(2) -0.007(2) N7 0.032(3) 0.028(2) 0.039(3) -0.003(2) 0.001(2) -0.005(2) N8 0.030(3) 0.031(3) 0.046(3) -0.008(2) 0.003(2) 0.004(2) C13 0.034(4) 0.021(3) 0.040(4) 0.003(3) 0.010(3) 0.001(2) C14 0.036(3) 0.023(3) 0.032(3) -0.002(2) 0.003(3) -0.001(2) C15 0.034(3) 0.045(4) 0.042(4) 0.014(3) 0.006(3) -0.002(3) C16 0.034(3) 0.023(3) 0.040(4) -0.007(2) -0.005(3) 0.007(3) C17 0.038(3) 0.038(3) 0.042(4) -0.007(3) -0.002(3) 0.011(3) C18 0.061(4) 0.041(4) 0.057(5) 0.013(3) -0.004(4) -0.005(3) C19 0.032(3) 0.031(3) 0.033(4) 0.002(2) 0.005(3) -0.002(2) C20 0.040(4) 0.036(3) 0.030(3) 0.004(3) 0.005(3) 0.002(3) C21 0.046(4) 0.040(3) 0.032(4) 0.006(3) -0.003(3) -0.002(3) C22 0.039(3) 0.037(3) 0.034(3) -0.007(3) 0.002(3) -0.005(3) C23 0.028(3) 0.036(3) 0.067(5) -0.016(3) 0.001(3) 0.000(3) C24 0.030(3) 0.040(3) 0.056(4) -0.014(3) -0.007(3) 0.002(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 I1 C10 2.105(6) . ? O1 C4 1.209(7) . ? O2 C4 1.329(7) . ? O2 C5 1.443(7) . ? N1 C1 1.354(8) . ? N1 N2 1.359(6) . ? N1 N4 1.382(6) . ? N2 N3 1.296(7) . ? N3 C2 1.376(7) . ? N4 C7 1.400(7) . ? N4 H4N 0.88(4) . ? C1 C2 1.383(7) . ? C1 C3 1.470(8) . ? C2 C4 1.469(8) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C5 C6 1.484(10) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.389(8) . ? C7 C12 1.396(8) . ? C8 C9 1.364(9) . ? C8 H8 0.9500 . ? C9 C10 1.393(9) . ? C9 H9 0.9500 . ? C10 C11 1.383(8) . ? C11 C12 1.384(8) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? I2 C22 2.092(6) . ? O3 C16 1.217(6) . ? O4 C16 1.324(7) . ? O4 C17 1.471(7) . ? N5 C13 1.336(8) . ? N5 N8 1.380(6) . ? N5 N6 1.381(6) . ? N6 N7 1.298(6) . ? N7 C14 1.363(7) . ? N8 C19 1.422(7) . ? N8 H8N 0.88(4) . ? C13 C14 1.350(8) . ? C13 C15 1.505(8) . ? C14 C16 1.489(8) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C17 C18 1.498(9) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.366(8) . ? C19 C24 1.391(8) . ? C20 C21 1.373(9) . ? C20 H20 0.9500 . ? C21 C22 1.393(8) . ? C21 H21 0.9500 . ? C22 C23 1.360(8) . ? C23 C24 1.393(8) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O2 C5 117.2(5) . . ? C1 N1 N2 113.3(5) . . ? C1 N1 N4 125.2(5) . . ? N2 N1 N4 121.4(5) . . ? N3 N2 N1 105.8(5) . . ? N2 N3 C2 109.6(5) . . ? N1 N4 C7 118.7(4) . . ? N1 N4 H4N 110(4) . . ? C7 N4 H4N 120(4) . . ? N1 C1 C2 102.1(5) . . ? N1 C1 C3 123.1(5) . . ? C2 C1 C3 134.8(6) . . ? N3 C2 C1 109.2(5) . . ? N3 C2 C4 121.3(5) . . ? C1 C2 C4 129.5(5) . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? O1 C4 O2 125.3(6) . . ? O1 C4 C2 123.7(6) . . ? O2 C4 C2 111.0(5) . . ? O2 C5 C6 106.6(5) . . ? O2 C5 H5A 110.4 . . ? C6 C5 H5A 110.4 . . ? O2 C5 H5B 110.4 . . ? C6 C5 H5B 110.4 . . ? H5A C5 H5B 108.6 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C12 118.9(6) . . ? C8 C7 N4 120.0(5) . . ? C12 C7 N4 121.0(5) . . ? C9 C8 C7 121.4(6) . . ? C9 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C8 C9 C10 119.8(6) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C11 C10 C9 119.7(6) . . ? C11 C10 I1 121.0(5) . . ? C9 C10 I1 119.3(5) . . ? C10 C11 C12 120.4(6) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C11 C12 C7 119.9(6) . . ? C11 C12 H12 120.1 . . ? C7 C12 H12 120.1 . . ? C16 O4 C17 118.0(4) . . ? C13 N5 N8 126.7(5) . . ? C13 N5 N6 111.3(5) . . ? N8 N5 N6 121.9(5) . . ? N7 N6 N5 105.8(5) . . ? N6 N7 C14 109.0(5) . . ? N5 N8 C19 118.0(5) . . ? N5 N8 H8N 109(4) . . ? C19 N8 H8N 116(4) . . ? N5 C13 C14 104.1(5) . . ? N5 C13 C15 120.8(5) . . ? C14 C13 C15 135.0(6) . . ? C13 C14 N7 109.8(5) . . ? C13 C14 C16 129.5(6) . . ? N7 C14 C16 120.7(5) . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O3 C16 O4 125.4(6) . . ? O3 C16 C14 125.0(6) . . ? O4 C16 C14 109.6(5) . . ? O4 C17 C18 105.5(5) . . ? O4 C17 H17A 110.6 . . ? C18 C17 H17A 110.6 . . ? O4 C17 H17B 110.6 . . ? C18 C17 H17B 110.6 . . ? H17A C17 H17B 108.8 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C24 120.3(6) . . ? C20 C19 N8 119.4(5) . . ? C24 C19 N8 120.1(5) . . ? C19 C20 C21 120.5(6) . . ? C19 C20 H20 119.7 . . ? C21 C20 H20 119.7 . . ? C20 C21 C22 119.5(6) . . ? C20 C21 H21 120.2 . . ? C22 C21 H21 120.2 . . ? C23 C22 C21 120.3(6) . . ? C23 C22 I2 121.9(5) . . ? C21 C22 I2 117.7(5) . . ? C22 C23 C24 120.2(6) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C19 C24 C23 119.1(6) . . ? C19 C24 H24 120.5 . . ? C23 C24 H24 120.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 N2 N3 -0.8(6) . . . . ? N4 N1 N2 N3 -178.8(4) . . . . ? N1 N2 N3 C2 1.2(6) . . . . ? C1 N1 N4 C7 114.3(6) . . . . ? N2 N1 N4 C7 -68.0(6) . . . . ? N2 N1 C1 C2 0.0(6) . . . . ? N4 N1 C1 C2 177.9(5) . . . . ? N2 N1 C1 C3 179.5(5) . . . . ? N4 N1 C1 C3 -2.6(8) . . . . ? N2 N3 C2 C1 -1.3(6) . . . . ? N2 N3 C2 C4 -179.5(5) . . . . ? N1 C1 C2 N3 0.7(6) . . . . ? C3 C1 C2 N3 -178.7(6) . . . . ? N1 C1 C2 C4 178.8(5) . . . . ? C3 C1 C2 C4 -0.6(11) . . . . ? C5 O2 C4 O1 3.6(8) . . . . ? C5 O2 C4 C2 -176.8(4) . . . . ? N3 C2 C4 O1 5.7(8) . . . . ? C1 C2 C4 O1 -172.2(6) . . . . ? N3 C2 C4 O2 -174.0(5) . . . . ? C1 C2 C4 O2 8.1(8) . . . . ? C4 O2 C5 C6 169.1(5) . . . . ? N1 N4 C7 C8 147.2(5) . . . . ? N1 N4 C7 C12 -37.1(8) . . . . ? C12 C7 C8 C9 -1.4(9) . . . . ? N4 C7 C8 C9 174.4(6) . . . . ? C7 C8 C9 C10 1.6(10) . . . . ? C8 C9 C10 C11 0.0(9) . . . . ? C8 C9 C10 I1 179.0(5) . . . . ? C9 C10 C11 C12 -1.8(9) . . . . ? I1 C10 C11 C12 179.3(4) . . . . ? C10 C11 C12 C7 2.0(9) . . . . ? C8 C7 C12 C11 -0.4(8) . . . . ? N4 C7 C12 C11 -176.1(5) . . . . ? C13 N5 N6 N7 0.0(6) . . . . ? N8 N5 N6 N7 -179.0(4) . . . . ? N5 N6 N7 C14 -0.1(5) . . . . ? C13 N5 N8 C19 120.5(6) . . . . ? N6 N5 N8 C19 -60.6(7) . . . . ? N8 N5 C13 C14 179.1(5) . . . . ? N6 N5 C13 C14 0.1(6) . . . . ? N8 N5 C13 C15 0.3(9) . . . . ? N6 N5 C13 C15 -178.6(5) . . . . ? N5 C13 C14 N7 -0.1(6) . . . . ? C15 C13 C14 N7 178.3(6) . . . . ? N5 C13 C14 C16 179.8(5) . . . . ? C15 C13 C14 C16 -1.7(11) . . . . ? N6 N7 C14 C13 0.1(6) . . . . ? N6 N7 C14 C16 -179.8(5) . . . . ? C17 O4 C16 O3 0.8(8) . . . . ? C17 O4 C16 C14 -178.0(4) . . . . ? C13 C14 C16 O3 179.4(6) . . . . ? N7 C14 C16 O3 -0.6(8) . . . . ? C13 C14 C16 O4 -1.8(8) . . . . ? N7 C14 C16 O4 178.2(5) . . . . ? C16 O4 C17 C18 170.8(5) . . . . ? N5 N8 C19 C20 149.3(5) . . . . ? N5 N8 C19 C24 -35.6(8) . . . . ? C24 C19 C20 C21 -0.2(9) . . . . ? N8 C19 C20 C21 174.9(5) . . . . ? C19 C20 C21 C22 1.7(9) . . . . ? C20 C21 C22 C23 -2.1(9) . . . . ? C20 C21 C22 I2 178.8(4) . . . . ? C21 C22 C23 C24 0.9(10) . . . . ? I2 C22 C23 C24 180.0(5) . . . . ? C20 C19 C24 C23 -1.0(9) . . . . ? N8 C19 C24 C23 -176.1(6) . . . . ? C22 C23 C24 C19 0.7(10) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 24.2 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.55 _refine_diff_density_min -0.52 _refine_diff_density_rms 0.068 _database_code_depnum_ccdc_archive 'CCDC 845658' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_(4-OMe) data_ome #TrackingRef '6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H16 N4 O3' _chemical_formula_sum 'C13 H16 N4 O3' _chemical_formula_weight 276.30 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 8.965(4) _cell_length_b 9.911(4) _cell_length_c 15.067(7) _cell_angle_alpha 90 _cell_angle_beta 96.587(14) _cell_angle_gamma 90 _cell_volume 1329.9(10) _cell_formula_units_Z 4 _cell_measurement_temperature 98(2) _cell_measurement_reflns_used 4132 _cell_measurement_theta_min 2.1 _cell_measurement_theta_max 30.4 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.380 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.711 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 98(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC12\K/SATURN724 _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% '< 1' _diffrn_reflns_number 13169 _diffrn_reflns_av_R_equivalents 0.040 _diffrn_reflns_av_sigmaI/netI 0.030 _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 -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.3 _diffrn_reflns_theta_max 26.5 _reflns_number_total 2753 _reflns_number_gt 2427 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'CrystalClear (Molecular Structure Corporation & Rigaku, 2005)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)' _computing_publication_material 'publCIF (Westrip, 2010)' _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^ > 2\s(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^)+(0.0471P)^2^+0.7432P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2753 _refine_ls_number_parameters 187 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.066 _refine_ls_R_factor_gt 0.056 _refine_ls_wR_factor_ref 0.129 _refine_ls_wR_factor_gt 0.123 _refine_ls_goodness_of_fit_ref 1.17 _refine_ls_restrained_S_all 1.17 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.03665(15) -0.25530(14) 0.55301(9) 0.0300(3) Uani 1 1 d . . . O2 O 0.84505(15) -0.14201(13) 0.47560(9) 0.0258(3) Uani 1 1 d . . . O3 O 0.28581(15) 0.10090(14) 0.94554(10) 0.0298(4) Uani 1 1 d . . . N1 N 0.84061(17) 0.06274(16) 0.71533(10) 0.0228(4) Uani 1 1 d . . . N2 N 0.94650(18) -0.01469(17) 0.76318(11) 0.0283(4) Uani 1 1 d . . . N3 N 0.98733(18) -0.10476(17) 0.70684(11) 0.0269(4) Uani 1 1 d . . . N4 N 0.77526(18) 0.17355(17) 0.75196(11) 0.0253(4) Uani 1 1 d . . . H4n H 0.850(3) 0.230(2) 0.7775(15) 0.030 Uiso 1 1 d . . . C1 C 0.8114(2) 0.02168(19) 0.62920(12) 0.0221(4) Uani 1 1 d . . . C2 C 0.9071(2) -0.08586(19) 0.62503(13) 0.0225(4) Uani 1 1 d . . . C3 C 0.6995(2) 0.0907(2) 0.56448(13) 0.0273(4) Uani 1 1 d . . . H3A H 0.6184 0.1267 0.5959 0.041 Uiso 1 1 calc R . . H3B H 0.6580 0.0261 0.5189 0.041 Uiso 1 1 calc R . . H3C H 0.7483 0.1648 0.5358 0.041 Uiso 1 1 calc R . . C4 C 0.9380(2) -0.17150(19) 0.54926(13) 0.0240(4) Uani 1 1 d . . . C5 C 0.8600(2) -0.2246(2) 0.39699(13) 0.0271(4) Uani 1 1 d . . . H5A H 0.8343 -0.3197 0.4084 0.033 Uiso 1 1 calc R . . H5B H 0.9643 -0.2211 0.3816 0.033 Uiso 1 1 calc R . . C6 C 0.7536(2) -0.1678(2) 0.32239(14) 0.0331(5) Uani 1 1 d . . . H6A H 0.6505 -0.1754 0.3375 0.050 Uiso 1 1 calc R . . H6B H 0.7631 -0.2182 0.2674 0.050 Uiso 1 1 calc R . . H6C H 0.7776 -0.0726 0.3135 0.050 Uiso 1 1 calc R . . C7 C 0.6553(2) 0.14462(19) 0.80391(12) 0.0225(4) Uani 1 1 d . . . C8 C 0.5888(2) 0.0193(2) 0.80663(13) 0.0255(4) Uani 1 1 d . . . H8 H 0.6274 -0.0544 0.7760 0.031 Uiso 1 1 calc R . . C9 C 0.4653(2) -0.0004(2) 0.85398(13) 0.0252(4) Uani 1 1 d . . . H9 H 0.4206 -0.0871 0.8555 0.030 Uiso 1 1 calc R . . C10 C 0.4079(2) 0.1066(2) 0.89869(13) 0.0239(4) Uani 1 1 d . . . C11 C 0.4757(2) 0.23304(19) 0.89599(13) 0.0255(4) Uani 1 1 d . . . H11 H 0.4374 0.3068 0.9266 0.031 Uiso 1 1 calc R . . C12 C 0.5980(2) 0.25209(19) 0.84912(12) 0.0242(4) Uani 1 1 d . . . H12 H 0.6431 0.3387 0.8478 0.029 Uiso 1 1 calc R . . C13 C 0.2174(2) -0.0279(2) 0.95383(15) 0.0299(5) Uani 1 1 d . . . H13A H 0.1813 -0.0626 0.8943 0.045 Uiso 1 1 calc R . . H13B H 0.1328 -0.0189 0.9892 0.045 Uiso 1 1 calc R . . H13C H 0.2914 -0.0907 0.9837 0.045 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0267(7) 0.0305(8) 0.0327(8) -0.0002(6) 0.0034(6) 0.0065(6) O2 0.0286(7) 0.0264(7) 0.0220(7) -0.0014(6) 0.0016(5) 0.0030(5) O3 0.0268(7) 0.0234(7) 0.0410(9) -0.0008(6) 0.0112(6) -0.0009(6) N1 0.0227(8) 0.0230(8) 0.0224(8) -0.0002(6) 0.0017(6) 0.0002(6) N2 0.0268(9) 0.0315(9) 0.0256(9) 0.0020(7) -0.0007(7) 0.0011(7) N3 0.0263(8) 0.0298(9) 0.0245(9) 0.0016(7) 0.0020(7) 0.0018(7) N4 0.0270(9) 0.0233(9) 0.0261(9) -0.0038(7) 0.0046(7) -0.0042(7) C1 0.0218(9) 0.0235(10) 0.0214(9) 0.0014(8) 0.0037(7) -0.0036(7) C2 0.0209(9) 0.0238(10) 0.0227(10) 0.0019(8) 0.0020(7) -0.0016(7) C3 0.0290(10) 0.0265(11) 0.0258(10) 0.0016(8) 0.0006(8) 0.0032(8) C4 0.0217(9) 0.0239(10) 0.0267(10) 0.0029(8) 0.0033(8) -0.0028(8) C5 0.0307(10) 0.0267(10) 0.0250(10) -0.0044(8) 0.0075(8) 0.0002(8) C6 0.0391(12) 0.0311(11) 0.0286(11) -0.0015(9) 0.0009(9) -0.0010(9) C7 0.0226(9) 0.0251(10) 0.0192(9) -0.0009(8) -0.0002(7) -0.0020(7) C8 0.0282(10) 0.0237(10) 0.0246(10) -0.0031(8) 0.0024(8) 0.0029(8) C9 0.0261(10) 0.0226(10) 0.0266(10) 0.0005(8) 0.0019(8) -0.0022(8) C10 0.0215(9) 0.0265(10) 0.0235(10) 0.0022(8) 0.0021(7) 0.0007(7) C11 0.0258(10) 0.0214(10) 0.0285(10) -0.0036(8) -0.0002(8) 0.0030(7) C12 0.0271(10) 0.0207(9) 0.0238(10) 0.0003(8) -0.0012(8) -0.0026(8) C13 0.0273(10) 0.0257(10) 0.0375(12) 0.0021(9) 0.0069(9) -0.0027(8) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C4 1.210(2) . ? O2 C4 1.342(2) . ? O2 C5 1.458(2) . ? O3 C10 1.370(2) . ? O3 C13 1.428(2) . ? N1 C1 1.357(2) . ? N1 N2 1.361(2) . ? N1 N4 1.389(2) . ? N2 N3 1.312(2) . ? N3 C2 1.367(3) . ? N4 C7 1.430(2) . ? N4 H4n 0.92(2) . ? C1 C2 1.374(3) . ? C1 C3 1.483(3) . ? C2 C4 1.474(3) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C5 C6 1.498(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.380(3) . ? C7 C12 1.394(3) . ? C8 C9 1.398(3) . ? C8 H8 0.9500 . ? C9 C10 1.386(3) . ? C9 H9 0.9500 . ? C10 C11 1.395(3) . ? C11 C12 1.384(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O2 C5 116.33(15) . . ? C10 O3 C13 117.27(15) . . ? C1 N1 N2 112.58(16) . . ? C1 N1 N4 124.99(16) . . ? N2 N1 N4 122.40(15) . . ? N3 N2 N1 105.67(15) . . ? N2 N3 C2 109.46(16) . . ? N1 N4 C7 115.92(15) . . ? N1 N4 H4N 109.0(14) . . ? C7 N4 H4N 116.6(14) . . ? N1 C1 C2 102.91(16) . . ? N1 C1 C3 122.17(17) . . ? C2 C1 C3 134.92(18) . . ? N3 C2 C1 109.38(17) . . ? N3 C2 C4 119.55(16) . . ? C1 C2 C4 130.98(17) . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? O1 C4 O2 124.73(18) . . ? O1 C4 C2 124.09(17) . . ? O2 C4 C2 111.16(16) . . ? O2 C5 C6 106.77(16) . . ? O2 C5 H5A 110.4 . . ? C6 C5 H5A 110.4 . . ? O2 C5 H5B 110.4 . . ? C6 C5 H5B 110.4 . . ? H5A C5 H5B 108.6 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C12 119.25(18) . . ? C8 C7 N4 123.44(17) . . ? C12 C7 N4 117.18(17) . . ? C7 C8 C9 120.68(18) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C10 C9 C8 120.10(18) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? O3 C10 C9 125.59(17) . . ? O3 C10 C11 115.36(17) . . ? C9 C10 C11 119.04(18) . . ? C12 C11 C10 120.71(18) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C11 C12 C7 120.21(17) . . ? C11 C12 H12 119.9 . . ? C7 C12 H12 119.9 . . ? O3 C13 H13A 109.5 . . ? O3 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O3 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 N2 N3 1.0(2) . . . . ? N4 N1 N2 N3 -177.08(16) . . . . ? N1 N2 N3 C2 -0.8(2) . . . . ? C1 N1 N4 C7 100.8(2) . . . . ? N2 N1 N4 C7 -81.3(2) . . . . ? N2 N1 C1 C2 -0.8(2) . . . . ? N4 N1 C1 C2 177.28(16) . . . . ? N2 N1 C1 C3 179.82(16) . . . . ? N4 N1 C1 C3 -2.1(3) . . . . ? N2 N3 C2 C1 0.4(2) . . . . ? N2 N3 C2 C4 177.30(16) . . . . ? N1 C1 C2 N3 0.2(2) . . . . ? C3 C1 C2 N3 179.5(2) . . . . ? N1 C1 C2 C4 -176.20(18) . . . . ? C3 C1 C2 C4 3.1(4) . . . . ? C5 O2 C4 O1 4.2(3) . . . . ? C5 O2 C4 C2 -177.21(15) . . . . ? N3 C2 C4 O1 -3.8(3) . . . . ? C1 C2 C4 O1 172.4(2) . . . . ? N3 C2 C4 O2 177.65(16) . . . . ? C1 C2 C4 O2 -6.2(3) . . . . ? C4 O2 C5 C6 -176.25(16) . . . . ? N1 N4 C7 C8 -10.7(3) . . . . ? N1 N4 C7 C12 173.50(16) . . . . ? C12 C7 C8 C9 0.1(3) . . . . ? N4 C7 C8 C9 -175.67(18) . . . . ? C7 C8 C9 C10 0.1(3) . . . . ? C13 O3 C10 C9 4.2(3) . . . . ? C13 O3 C10 C11 -176.97(17) . . . . ? C8 C9 C10 O3 178.46(17) . . . . ? C8 C9 C10 C11 -0.3(3) . . . . ? O3 C10 C11 C12 -178.63(17) . . . . ? C9 C10 C11 C12 0.3(3) . . . . ? C10 C11 C12 C7 0.0(3) . . . . ? C8 C7 C12 C11 -0.1(3) . . . . ? N4 C7 C12 C11 175.88(17) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.5 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.24 _refine_diff_density_min -0.23 _refine_diff_density_rms 0.048 _database_code_depnum_ccdc_archive 'CCDC 845659' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_(4-NO2) data_no2 #TrackingRef '7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H13 N5 O4' _chemical_formula_sum 'C12 H13 N5 O4' _chemical_formula_weight 291.27 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 10.1622(19) _cell_length_b 17.127(3) _cell_length_c 15.487(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.476(7) _cell_angle_gamma 90.00 _cell_volume 2693.0(9) _cell_formula_units_Z 8 _cell_measurement_temperature 98(2) _cell_measurement_reflns_used 9055 _cell_measurement_theta_min 1.8 _cell_measurement_theta_max 30.3 _exptl_crystal_description Prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.570 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 98(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC12\K/SATURN724 _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% '< 1' _diffrn_reflns_number 21138 _diffrn_reflns_av_R_equivalents 0.063 _diffrn_reflns_av_sigmaI/netI 0.045 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.0 _diffrn_reflns_theta_max 25.0 _reflns_number_total 4750 _reflns_number_gt 3964 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'CrystalClear (Molecular Structure Corporation & Rigaku, 2005)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)' _computing_publication_material 'publCIF (Westrip, 2010)' _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^ > 2\s(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^)+(0.0638P)^2^+1.6427P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4750 _refine_ls_number_parameters 389 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.088 _refine_ls_R_factor_gt 0.070 _refine_ls_wR_factor_ref 0.159 _refine_ls_wR_factor_gt 0.150 _refine_ls_goodness_of_fit_ref 1.18 _refine_ls_restrained_S_all 1.18 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.69036(19) 0.18601(13) 1.10273(13) 0.0337(5) Uani 1 1 d . . . O2 O 0.88596(18) 0.12530(11) 1.11678(13) 0.0283(5) Uani 1 1 d . . . O3 O 0.7599(2) -0.01516(13) 0.52302(15) 0.0421(6) Uani 1 1 d . . . O4 O 0.8946(2) 0.04799(14) 0.44343(15) 0.0422(6) Uani 1 1 d . . . N1 N 0.9340(2) 0.21586(15) 0.87149(15) 0.0272(6) Uani 1 1 d . . . N2 N 0.8198(2) 0.25899(15) 0.86893(16) 0.0319(6) Uani 1 1 d . . . N3 N 0.7634(2) 0.24486(15) 0.94140(16) 0.0303(6) Uani 1 1 d . . . N4 N 1.0104(2) 0.21285(16) 0.80028(16) 0.0323(6) Uani 1 1 d D . . H4n H 1.066(3) 0.2520(13) 0.793(2) 0.039 Uiso 1 1 d D . . N5 N 0.8429(2) 0.03626(15) 0.51261(17) 0.0333(6) Uani 1 1 d . . . C1 C 0.9500(3) 0.17429(17) 0.94563(19) 0.0267(7) Uani 1 1 d . . . C2 C 0.8395(3) 0.19343(17) 0.98959(19) 0.0267(7) Uani 1 1 d . . . C3 C 1.0652(3) 0.12287(19) 0.9647(2) 0.0331(7) Uani 1 1 d . . . H3A H 1.1221 0.1465 1.0102 0.050 Uiso 1 1 calc R . . H3B H 1.1149 0.1163 0.9123 0.050 Uiso 1 1 calc R . . H3C H 1.0347 0.0718 0.9841 0.050 Uiso 1 1 calc R . . C4 C 0.7966(3) 0.16838(17) 1.07444(19) 0.0273(7) Uani 1 1 d . . . C5 C 0.8513(3) 0.10035(18) 1.20331(18) 0.0300(7) Uani 1 1 d . . . H5A H 0.7620 0.0772 1.2015 0.036 Uiso 1 1 calc R . . H5B H 0.8526 0.1455 1.2433 0.036 Uiso 1 1 calc R . . C6 C 0.9513(3) 0.04103(19) 1.2331(2) 0.0345(7) Uani 1 1 d . . . H6A H 0.9489 -0.0034 1.1932 0.052 Uiso 1 1 calc R . . H6B H 0.9314 0.0229 1.2912 0.052 Uiso 1 1 calc R . . H6C H 1.0392 0.0646 1.2346 0.052 Uiso 1 1 calc R . . C7 C 0.9618(3) 0.17296(16) 0.72779(19) 0.0248(6) Uani 1 1 d . . . C8 C 0.8522(3) 0.12388(17) 0.7318(2) 0.0287(7) Uani 1 1 d . . . H8 H 0.8048 0.1210 0.7832 0.034 Uiso 1 1 calc R . . C9 C 0.8132(3) 0.07953(17) 0.6607(2) 0.0292(7) Uani 1 1 d . . . H9 H 0.7399 0.0453 0.6631 0.035 Uiso 1 1 calc R . . C10 C 0.8822(3) 0.08569(17) 0.58593(19) 0.0288(7) Uani 1 1 d . . . C11 C 0.9883(3) 0.13580(17) 0.5798(2) 0.0288(7) Uani 1 1 d . . . H11 H 1.0329 0.1400 0.5273 0.035 Uiso 1 1 calc R . . C12 C 1.0284(3) 0.17961(17) 0.65102(19) 0.0281(7) Uani 1 1 d . . . H12 H 1.1011 0.2142 0.6479 0.034 Uiso 1 1 calc R . . O5 O 0.20217(19) 0.32329(12) -0.26021(13) 0.0313(5) Uani 1 1 d . . . O6 O 0.39636(18) 0.38716(12) -0.25452(13) 0.0305(5) Uani 1 1 d . . . O7 O 0.3202(2) 0.47226(13) 0.40373(14) 0.0401(6) Uani 1 1 d . . . O8 O 0.4534(2) 0.38544(14) 0.46018(14) 0.0434(6) Uani 1 1 d . . . N6 N 0.4117(2) 0.31071(14) -0.00197(15) 0.0268(6) Uani 1 1 d . . . N7 N 0.2938(2) 0.27207(15) -0.00606(17) 0.0318(6) Uani 1 1 d . . . N8 N 0.2432(2) 0.28513(15) -0.08328(16) 0.0297(6) Uani 1 1 d . . . N9 N 0.4988(2) 0.30253(16) 0.06871(16) 0.0318(6) Uani 1 1 d D . . H9n H 0.551(3) 0.2612(12) 0.067(2) 0.038 Uiso 1 1 d D . . N10 N 0.3947(2) 0.41584(15) 0.39751(17) 0.0320(6) Uani 1 1 d . . . C13 C 0.4369(3) 0.34786(17) -0.07606(19) 0.0273(7) Uani 1 1 d . . . C14 C 0.3282(3) 0.33009(16) -0.12837(19) 0.0248(6) Uani 1 1 d . . . C15 C 0.5568(3) 0.3961(2) -0.0872(2) 0.0363(8) Uani 1 1 d . . . H15A H 0.6158 0.3691 -0.1257 0.054 Uiso 1 1 calc R . . H15B H 0.6022 0.4044 -0.0308 0.054 Uiso 1 1 calc R . . H15C H 0.5313 0.4467 -0.1124 0.054 Uiso 1 1 calc R . . C16 C 0.2999(3) 0.34594(17) -0.2202(2) 0.0279(7) Uani 1 1 d . . . C17 C 0.3864(3) 0.40160(18) -0.34792(18) 0.0300(7) Uani 1 1 d . . . H17A H 0.3404 0.3574 -0.3772 0.036 Uiso 1 1 calc R . . H17B H 0.4758 0.4054 -0.3705 0.036 Uiso 1 1 calc R . . C18 C 0.3121(3) 0.47600(18) -0.3672(2) 0.0326(7) Uani 1 1 d . . . H18A H 0.3540 0.5191 -0.3348 0.049 Uiso 1 1 calc R . . H18B H 0.2208 0.4702 -0.3501 0.049 Uiso 1 1 calc R . . H18C H 0.3129 0.4871 -0.4292 0.049 Uiso 1 1 calc R . . C19 C 0.4633(3) 0.32825(17) 0.14931(19) 0.0262(7) Uani 1 1 d . . . C20 C 0.3666(3) 0.38536(17) 0.15950(19) 0.0282(7) Uani 1 1 d . . . H20 H 0.3171 0.4046 0.1106 0.034 Uiso 1 1 calc R . . C21 C 0.3437(3) 0.41332(18) 0.2406(2) 0.0305(7) Uani 1 1 d . . . H21 H 0.2792 0.4527 0.2479 0.037 Uiso 1 1 calc R . . C22 C 0.4150(3) 0.38405(17) 0.31193(19) 0.0271(7) Uani 1 1 d . . . C23 C 0.5083(3) 0.32621(17) 0.30316(19) 0.0272(7) Uani 1 1 d . . . H23 H 0.5551 0.3059 0.3526 0.033 Uiso 1 1 calc R . . C24 C 0.5326(3) 0.29842(18) 0.22232(19) 0.0292(7) Uani 1 1 d . . . H24 H 0.5968 0.2588 0.2158 0.035 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0288(11) 0.0416(13) 0.0314(13) 0.0009(10) 0.0082(9) 0.0064(10) O2 0.0265(10) 0.0340(11) 0.0246(12) 0.0036(9) 0.0049(8) 0.0041(9) O3 0.0461(13) 0.0348(12) 0.0447(15) -0.0049(11) -0.0048(11) -0.0045(12) O4 0.0458(13) 0.0520(15) 0.0288(14) -0.0047(11) 0.0007(11) 0.0067(12) N1 0.0242(12) 0.0342(14) 0.0234(14) 0.0005(11) 0.0030(10) -0.0027(11) N2 0.0306(13) 0.0365(15) 0.0286(15) 0.0004(11) 0.0017(11) 0.0001(12) N3 0.0306(13) 0.0336(14) 0.0268(15) -0.0003(11) 0.0017(11) -0.0013(12) N4 0.0339(14) 0.0420(15) 0.0216(14) -0.0006(12) 0.0074(11) -0.0121(12) N5 0.0342(14) 0.0339(15) 0.0313(17) -0.0031(12) -0.0032(12) 0.0075(13) C1 0.0279(15) 0.0282(15) 0.0242(17) -0.0016(12) 0.0012(12) -0.0031(13) C2 0.0233(14) 0.0291(15) 0.0275(17) -0.0008(13) -0.0015(12) -0.0013(13) C3 0.0274(15) 0.0372(17) 0.0350(19) -0.0004(14) 0.0060(13) 0.0007(14) C4 0.0257(15) 0.0274(16) 0.0288(17) -0.0037(12) 0.0014(12) -0.0017(13) C5 0.0310(15) 0.0363(17) 0.0230(17) 0.0007(13) 0.0053(12) -0.0027(14) C6 0.0283(15) 0.0441(19) 0.0310(19) 0.0081(14) 0.0016(13) -0.0026(15) C7 0.0233(14) 0.0254(15) 0.0256(17) 0.0018(12) -0.0014(12) 0.0003(12) C8 0.0258(14) 0.0312(16) 0.0293(18) 0.0015(13) 0.0041(12) -0.0010(13) C9 0.0254(14) 0.0271(15) 0.0351(18) 0.0015(13) 0.0009(12) 0.0023(13) C10 0.0302(15) 0.0265(15) 0.0293(18) -0.0010(13) -0.0040(13) 0.0042(13) C11 0.0270(15) 0.0327(16) 0.0271(17) 0.0014(13) 0.0056(12) 0.0038(13) C12 0.0234(14) 0.0302(16) 0.0309(18) 0.0009(13) 0.0033(12) -0.0002(13) O5 0.0278(11) 0.0387(12) 0.0271(12) 0.0034(9) -0.0018(9) -0.0058(9) O6 0.0270(10) 0.0404(12) 0.0245(12) 0.0019(9) 0.0032(8) -0.0075(9) O7 0.0425(12) 0.0415(13) 0.0367(14) -0.0057(10) 0.0085(10) 0.0078(12) O8 0.0455(13) 0.0606(16) 0.0243(13) 0.0037(11) 0.0025(10) 0.0067(12) N6 0.0227(12) 0.0341(14) 0.0236(14) -0.0009(11) -0.0006(10) 0.0009(11) N7 0.0301(13) 0.0367(15) 0.0289(15) 0.0008(11) 0.0039(11) -0.0004(12) N8 0.0285(13) 0.0334(14) 0.0274(15) 0.0007(11) 0.0029(11) -0.0020(11) N9 0.0285(13) 0.0412(15) 0.0256(15) -0.0002(12) -0.0019(11) 0.0090(12) N10 0.0301(13) 0.0374(15) 0.0287(15) 0.0015(12) 0.0044(11) -0.0050(13) C13 0.0289(15) 0.0283(15) 0.0251(17) -0.0012(13) 0.0036(12) 0.0042(13) C14 0.0245(14) 0.0239(15) 0.0260(17) -0.0028(12) 0.0029(12) 0.0000(12) C15 0.0287(15) 0.0430(19) 0.0366(19) 0.0040(15) -0.0038(13) -0.0063(15) C16 0.0274(15) 0.0266(15) 0.0301(18) -0.0019(13) 0.0054(13) -0.0003(13) C17 0.0298(15) 0.0390(17) 0.0218(16) -0.0009(13) 0.0072(12) -0.0011(14) C18 0.0333(16) 0.0354(17) 0.0297(18) 0.0003(13) 0.0088(13) -0.0025(14) C19 0.0227(14) 0.0323(16) 0.0238(17) 0.0010(12) 0.0024(12) -0.0030(13) C20 0.0254(14) 0.0337(16) 0.0252(17) 0.0014(13) -0.0024(12) 0.0025(13) C21 0.0280(15) 0.0312(16) 0.0324(18) -0.0015(13) 0.0031(13) 0.0048(13) C22 0.0267(14) 0.0305(16) 0.0241(17) -0.0001(12) 0.0031(12) -0.0029(13) C23 0.0252(14) 0.0311(16) 0.0250(17) 0.0064(13) -0.0004(12) -0.0035(13) C24 0.0246(14) 0.0307(16) 0.0325(19) 0.0045(13) 0.0032(12) 0.0014(13) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C4 1.220(3) . ? O2 C4 1.322(3) . ? O2 C5 1.464(3) . ? O3 N5 1.235(3) . ? O4 N5 1.230(3) . ? N1 C1 1.355(4) . ? N1 N2 1.375(3) . ? N1 N4 1.377(3) . ? N2 N3 1.305(3) . ? N3 C2 1.371(4) . ? N4 C7 1.387(4) . ? N4 H4n 0.89(3) . ? N5 C10 1.458(4) . ? C1 C2 1.378(4) . ? C1 C3 1.485(4) . ? C2 C4 1.467(4) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C5 C6 1.496(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C12 1.398(4) . ? C7 C8 1.399(4) . ? C8 C9 1.381(4) . ? C8 H8 0.9500 . ? C9 C10 1.383(4) . ? C9 H9 0.9500 . ? C10 C11 1.384(4) . ? C11 C12 1.381(4) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? O5 C16 1.211(3) . ? O6 C16 1.337(3) . ? O6 C17 1.467(3) . ? O7 N10 1.234(3) . ? O8 N10 1.232(3) . ? N6 C13 1.346(4) . ? N6 N7 1.368(3) . ? N6 N9 1.385(3) . ? N7 N8 1.300(3) . ? N8 C14 1.371(4) . ? N9 C19 1.386(4) . ? N9 H9n 0.89(2) . ? N10 C22 1.456(4) . ? C13 C14 1.375(4) . ? C13 C15 1.489(4) . ? C14 C16 1.464(4) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C17 C18 1.504(4) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.401(4) . ? C19 C24 1.403(4) . ? C20 C21 1.374(4) . ? C20 H20 0.9500 . ? C21 C22 1.388(4) . ? C21 H21 0.9500 . ? C22 C23 1.382(4) . ? C23 C24 1.372(4) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O2 C5 115.4(2) . . ? C1 N1 N2 112.1(2) . . ? C1 N1 N4 127.5(2) . . ? N2 N1 N4 120.1(2) . . ? N3 N2 N1 106.1(2) . . ? N2 N3 C2 109.2(2) . . ? N1 N4 C7 118.3(2) . . ? N1 N4 H4n 117(2) . . ? C7 N4 H4n 119(2) . . ? O4 N5 O3 123.4(3) . . ? O4 N5 C10 118.1(3) . . ? O3 N5 C10 118.6(3) . . ? N1 C1 C2 102.9(2) . . ? N1 C1 C3 123.0(3) . . ? C2 C1 C3 134.1(3) . . ? N3 C2 C1 109.6(3) . . ? N3 C2 C4 119.5(2) . . ? C1 C2 C4 130.8(3) . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? O1 C4 O2 124.0(3) . . ? O1 C4 C2 123.5(3) . . ? O2 C4 C2 112.5(2) . . ? O2 C5 C6 107.1(2) . . ? O2 C5 H5A 110.3 . . ? C6 C5 H5A 110.3 . . ? O2 C5 H5B 110.3 . . ? C6 C5 H5B 110.3 . . ? H5A C5 H5B 108.6 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N4 C7 C12 118.7(3) . . ? N4 C7 C8 121.1(3) . . ? C12 C7 C8 120.1(3) . . ? C9 C8 C7 119.8(3) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C10 119.1(3) . . ? C8 C9 H9 120.5 . . ? C10 C9 H9 120.5 . . ? C9 C10 C11 122.0(3) . . ? C9 C10 N5 118.4(3) . . ? C11 C10 N5 119.6(3) . . ? C12 C11 C10 119.0(3) . . ? C12 C11 H11 120.5 . . ? C10 C11 H11 120.5 . . ? C11 C12 C7 119.9(3) . . ? C11 C12 H12 120.0 . . ? C7 C12 H12 120.0 . . ? C16 O6 C17 117.4(2) . . ? C13 N6 N7 112.8(2) . . ? C13 N6 N9 125.7(2) . . ? N7 N6 N9 121.1(2) . . ? N8 N7 N6 105.7(2) . . ? N7 N8 C14 109.4(2) . . ? N6 N9 C19 119.9(2) . . ? N6 N9 H9n 115(2) . . ? C19 N9 H9n 118(2) . . ? O8 N10 O7 123.2(3) . . ? O8 N10 C22 118.4(3) . . ? O7 N10 C22 118.4(2) . . ? N6 C13 C14 102.7(2) . . ? N6 C13 C15 123.2(3) . . ? C14 C13 C15 134.0(3) . . ? N8 C14 C13 109.4(3) . . ? N8 C14 C16 119.8(2) . . ? C13 C14 C16 130.6(3) . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O5 C16 O6 124.4(3) . . ? O5 C16 C14 124.1(3) . . ? O6 C16 C14 111.6(2) . . ? O6 C17 C18 110.6(2) . . ? O6 C17 H17A 109.5 . . ? C18 C17 H17A 109.5 . . ? O6 C17 H17B 109.5 . . ? C18 C17 H17B 109.5 . . ? H17A C17 H17B 108.1 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N9 C19 C20 122.3(3) . . ? N9 C19 C24 118.0(3) . . ? C20 C19 C24 119.6(3) . . ? C21 C20 C19 119.6(3) . . ? C21 C20 H20 120.2 . . ? C19 C20 H20 120.2 . . ? C20 C21 C22 119.9(3) . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C23 C22 C21 121.2(3) . . ? C23 C22 N10 118.8(3) . . ? C21 C22 N10 120.0(3) . . ? C24 C23 C22 119.3(3) . . ? C24 C23 H23 120.3 . . ? C22 C23 H23 120.3 . . ? C23 C24 C19 120.3(3) . . ? C23 C24 H24 119.8 . . ? C19 C24 H24 119.8 . . ? 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 N2 N3 0.0(3) . . . . ? N4 N1 N2 N3 174.2(2) . . . . ? N1 N2 N3 C2 -0.2(3) . . . . ? C1 N1 N4 C7 103.6(3) . . . . ? N2 N1 N4 C7 -69.5(4) . . . . ? N2 N1 C1 C2 0.1(3) . . . . ? N4 N1 C1 C2 -173.5(3) . . . . ? N2 N1 C1 C3 -180.0(3) . . . . ? N4 N1 C1 C3 6.4(4) . . . . ? N2 N3 C2 C1 0.3(3) . . . . ? N2 N3 C2 C4 180.0(3) . . . . ? N1 C1 C2 N3 -0.3(3) . . . . ? C3 C1 C2 N3 179.9(3) . . . . ? N1 C1 C2 C4 -179.9(3) . . . . ? C3 C1 C2 C4 0.2(6) . . . . ? C5 O2 C4 O1 -1.4(4) . . . . ? C5 O2 C4 C2 178.1(2) . . . . ? N3 C2 C4 O1 6.0(4) . . . . ? C1 C2 C4 O1 -174.5(3) . . . . ? N3 C2 C4 O2 -173.5(2) . . . . ? C1 C2 C4 O2 6.0(4) . . . . ? C4 O2 C5 C6 169.6(2) . . . . ? N1 N4 C7 C12 170.2(3) . . . . ? N1 N4 C7 C8 -12.9(4) . . . . ? N4 C7 C8 C9 -174.2(3) . . . . ? C12 C7 C8 C9 2.7(4) . . . . ? C7 C8 C9 C10 -1.2(4) . . . . ? C8 C9 C10 C11 -0.9(4) . . . . ? C8 C9 C10 N5 177.7(3) . . . . ? O4 N5 C10 C9 172.1(3) . . . . ? O3 N5 C10 C9 -8.1(4) . . . . ? O4 N5 C10 C11 -9.3(4) . . . . ? O3 N5 C10 C11 170.5(3) . . . . ? C9 C10 C11 C12 1.6(4) . . . . ? N5 C10 C11 C12 -177.0(3) . . . . ? C10 C11 C12 C7 -0.1(4) . . . . ? N4 C7 C12 C11 175.0(3) . . . . ? C8 C7 C12 C11 -2.0(4) . . . . ? C13 N6 N7 N8 -0.4(3) . . . . ? N9 N6 N7 N8 -173.1(2) . . . . ? N6 N7 N8 C14 1.1(3) . . . . ? C13 N6 N9 C19 124.0(3) . . . . ? N7 N6 N9 C19 -64.2(4) . . . . ? N7 N6 C13 C14 -0.5(3) . . . . ? N9 N6 C13 C14 171.9(3) . . . . ? N7 N6 C13 C15 178.0(3) . . . . ? N9 N6 C13 C15 -9.6(4) . . . . ? N7 N8 C14 C13 -1.5(3) . . . . ? N7 N8 C14 C16 173.6(2) . . . . ? N6 C13 C14 N8 1.2(3) . . . . ? C15 C13 C14 N8 -177.1(3) . . . . ? N6 C13 C14 C16 -173.2(3) . . . . ? C15 C13 C14 C16 8.6(6) . . . . ? C17 O6 C16 O5 -3.9(4) . . . . ? C17 O6 C16 C14 175.0(2) . . . . ? N8 C14 C16 O5 2.0(4) . . . . ? C13 C14 C16 O5 175.9(3) . . . . ? N8 C14 C16 O6 -176.8(2) . . . . ? C13 C14 C16 O6 -3.0(4) . . . . ? C16 O6 C17 C18 89.6(3) . . . . ? N6 N9 C19 C20 -22.9(4) . . . . ? N6 N9 C19 C24 160.6(3) . . . . ? N9 C19 C20 C21 -174.4(3) . . . . ? C24 C19 C20 C21 2.1(4) . . . . ? C19 C20 C21 C22 -1.0(4) . . . . ? C20 C21 C22 C23 -0.8(4) . . . . ? C20 C21 C22 N10 177.5(3) . . . . ? O8 N10 C22 C23 -6.1(4) . . . . ? O7 N10 C22 C23 173.4(3) . . . . ? O8 N10 C22 C21 175.6(3) . . . . ? O7 N10 C22 C21 -4.9(4) . . . . ? C21 C22 C23 C24 1.3(4) . . . . ? N10 C22 C23 C24 -176.9(3) . . . . ? C22 C23 C24 C19 -0.2(4) . . . . ? N9 C19 C24 C23 175.1(3) . . . . ? C20 C19 C24 C23 -1.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.0 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.27 _refine_diff_density_min -0.27 _refine_diff_density_rms 0.056 _database_code_depnum_ccdc_archive 'CCDC 845660' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_(Cl2) data_cl2 #TrackingRef '8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H12 Cl2 N4 O2' _chemical_formula_sum 'C12 H12 Cl2 N4 O2' _chemical_formula_weight 315.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 7.2818(11) _cell_length_b 11.242(3) _cell_length_c 16.916(4) _cell_angle_alpha 87.87(2) _cell_angle_beta 88.86(4) _cell_angle_gamma 88.29(2) _cell_volume 1383.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 990 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 27.4 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.02 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.514 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.476 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.6893 _diffrn_radiation_type Synchrotron _diffrn_radiation_source 'Daresbury SRS station 9.8' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'fine-slice \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11827 _diffrn_reflns_av_R_equivalents 0.038 _diffrn_reflns_av_sigmaI/netI 0.056 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.2 _diffrn_reflns_theta_max 26.5 _reflns_number_total 6043 _reflns_number_gt 5182 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'SAINT (Bruker, 2004)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006), Qmol (Gans & Shalloway, 2001) ; _computing_publication_material 'publCIF (Westrip, 2010)' _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^ > 2\s(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^)+(0.0392P)^2^+1.8560P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6043 _refine_ls_number_parameters 371 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.059 _refine_ls_R_factor_gt 0.051 _refine_ls_wR_factor_ref 0.136 _refine_ls_wR_factor_gt 0.131 _refine_ls_goodness_of_fit_ref 1.11 _refine_ls_restrained_S_all 1.11 _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 0.31824(9) 0.58670(6) 0.91291(4) 0.02885(16) Uani 1 1 d . . . Cl2 Cl 0.25835(11) 0.07559(6) 1.06156(4) 0.03659(18) Uani 1 1 d . . . O1 O 0.8313(3) -0.04349(18) 0.70872(12) 0.0344(5) Uani 1 1 d . . . O2 O 1.0236(2) 0.02284(16) 0.79903(11) 0.0268(4) Uani 1 1 d . . . N1 N 0.6147(3) 0.28326(19) 0.82510(13) 0.0237(4) Uani 1 1 d . . . N2 N 0.5098(3) 0.2472(2) 0.76510(14) 0.0311(5) Uani 1 1 d . . . N3 N 0.5945(3) 0.1547(2) 0.73574(14) 0.0316(5) Uani 1 1 d . . . N4 N 0.5566(3) 0.37771(19) 0.86975(14) 0.0267(5) Uani 1 1 d D . . H4N H 0.561(4) 0.4473(15) 0.8442(17) 0.032 Uiso 1 1 d D . . C1 C 0.7675(3) 0.2131(2) 0.83532(15) 0.0221(5) Uani 1 1 d . . . C2 C 0.7526(3) 0.1312(2) 0.77734(15) 0.0240(5) Uani 1 1 d . . . C3 C 0.9018(4) 0.2307(2) 0.89871(15) 0.0255(5) Uani 1 1 d . . . H3A H 1.0077 0.2729 0.8763 0.038 Uiso 1 1 calc R . . H3B H 0.9429 0.1531 0.9212 0.038 Uiso 1 1 calc R . . H3C H 0.8431 0.2778 0.9403 0.038 Uiso 1 1 calc R . . C4 C 0.8701(4) 0.0279(2) 0.75727(15) 0.0250(5) Uani 1 1 d . . . C5 C 1.1422(4) -0.0835(2) 0.78949(17) 0.0311(6) Uani 1 1 d . . . H5A H 1.1948 -0.0847 0.7351 0.037 Uiso 1 1 calc R . . H5B H 1.0712 -0.1564 0.7995 0.037 Uiso 1 1 calc R . . C6 C 1.2911(5) -0.0770(3) 0.8482(2) 0.0491(9) Uani 1 1 d . . . H6A H 1.3623 -0.0057 0.8366 0.074 Uiso 1 1 calc R . . H6B H 1.3721 -0.1480 0.8452 0.074 Uiso 1 1 calc R . . H6C H 1.2367 -0.0732 0.9016 0.074 Uiso 1 1 calc R . . C7 C 0.4226(3) 0.3533(2) 0.92738(15) 0.0232(5) Uani 1 1 d . . . C8 C 0.3127(3) 0.4457(2) 0.95848(16) 0.0242(5) Uani 1 1 d . . . C9 C 0.2000(4) 0.4261(2) 1.02363(16) 0.0268(5) Uani 1 1 d . . . H9 H 0.1324 0.4908 1.0457 0.032 Uiso 1 1 calc R . . C10 C 0.1845(4) 0.3122(2) 1.05738(16) 0.0277(5) Uani 1 1 d . . . H10 H 0.1073 0.2981 1.1025 0.033 Uiso 1 1 calc R . . C11 C 0.2844(4) 0.2199(2) 1.02365(15) 0.0258(5) Uani 1 1 d . . . C12 C 0.4031(3) 0.2383(2) 0.96020(15) 0.0248(5) Uani 1 1 d . . . H12 H 0.4713 0.1733 0.9389 0.030 Uiso 1 1 calc R . . Cl3 Cl 0.31033(9) 1.06321(5) 0.59170(4) 0.02652(15) Uani 1 1 d . . . Cl4 Cl 0.29406(10) 0.57485(6) 0.43144(5) 0.03717(19) Uani 1 1 d . . . O3 O 0.9379(3) 0.44436(19) 0.78246(14) 0.0425(5) Uani 1 1 d . . . O4 O 1.0787(2) 0.54229(16) 0.68144(11) 0.0282(4) Uani 1 1 d . . . N5 N 0.5984(3) 0.74707(18) 0.68201(12) 0.0209(4) Uani 1 1 d . . . N6 N 0.5164(3) 0.68751(19) 0.74370(13) 0.0245(4) Uani 1 1 d . . . N7 N 0.6313(3) 0.60178(19) 0.76499(13) 0.0249(4) Uani 1 1 d . . . N8 N 0.5067(3) 0.84558(18) 0.64885(13) 0.0242(4) Uani 1 1 d D . . H8N H 0.552(4) 0.9148(15) 0.6586(18) 0.029 Uiso 1 1 d D . . C13 C 0.7666(3) 0.7006(2) 0.66314(14) 0.0203(5) Uani 1 1 d . . . C14 C 0.7856(3) 0.6074(2) 0.71783(14) 0.0221(5) Uani 1 1 d . . . C15 C 0.8822(4) 0.7456(2) 0.59649(15) 0.0249(5) Uani 1 1 d . . . H15A H 0.8053 0.7917 0.5588 0.037 Uiso 1 1 calc R . . H15B H 0.9417 0.6783 0.5699 0.037 Uiso 1 1 calc R . . H15C H 0.9762 0.7967 0.6165 0.037 Uiso 1 1 calc R . . C16 C 0.9400(4) 0.5216(2) 0.73165(15) 0.0250(5) Uani 1 1 d . . . C17 C 1.2368(4) 0.4594(2) 0.68585(18) 0.0311(6) Uani 1 1 d . . . H17A H 1.2520 0.4296 0.7412 0.037 Uiso 1 1 calc R . . H17B H 1.3495 0.5013 0.6691 0.037 Uiso 1 1 calc R . . C18 C 1.2111(5) 0.3573(3) 0.6340(2) 0.0488(9) Uani 1 1 d . . . H18A H 1.1098 0.3094 0.6551 0.073 Uiso 1 1 calc R . . H18B H 1.3242 0.3080 0.6324 0.073 Uiso 1 1 calc R . . H18C H 1.1822 0.3874 0.5805 0.073 Uiso 1 1 calc R . . C19 C 0.4099(3) 0.8304(2) 0.57943(14) 0.0204(5) Uani 1 1 d . . . C20 C 0.3104(3) 0.9277(2) 0.54588(15) 0.0212(5) Uani 1 1 d . . . C21 C 0.2126(3) 0.9171(2) 0.47746(15) 0.0239(5) Uani 1 1 d . . . H21 H 0.1484 0.9847 0.4551 0.029 Uiso 1 1 calc R . . C22 C 0.2073(3) 0.8086(2) 0.44107(15) 0.0247(5) Uani 1 1 d . . . H22 H 0.1407 0.8008 0.3939 0.030 Uiso 1 1 calc R . . C23 C 0.3020(3) 0.7120(2) 0.47553(16) 0.0248(5) Uani 1 1 d . . . C24 C 0.4032(3) 0.7211(2) 0.54348(15) 0.0228(5) Uani 1 1 d . . . H24 H 0.4675 0.6533 0.5654 0.027 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0267(3) 0.0230(3) 0.0361(3) 0.0050(2) -0.0012(2) 0.0062(2) Cl2 0.0411(4) 0.0292(3) 0.0385(4) 0.0104(3) 0.0050(3) -0.0035(3) O1 0.0405(11) 0.0293(10) 0.0338(11) -0.0068(8) -0.0049(9) 0.0011(9) O2 0.0245(9) 0.0246(9) 0.0312(10) -0.0030(7) -0.0004(7) 0.0049(7) N1 0.0232(10) 0.0231(10) 0.0243(10) 0.0036(8) -0.0011(8) 0.0042(8) N2 0.0269(12) 0.0386(13) 0.0274(12) 0.0021(10) -0.0051(9) 0.0049(10) N3 0.0289(12) 0.0396(13) 0.0262(11) -0.0007(10) -0.0054(9) 0.0017(10) N4 0.0285(11) 0.0188(10) 0.0316(12) 0.0050(9) 0.0048(9) 0.0063(9) C1 0.0208(11) 0.0217(12) 0.0232(12) 0.0059(9) -0.0006(9) 0.0011(9) C2 0.0222(12) 0.0270(13) 0.0223(12) 0.0028(10) -0.0004(9) 0.0008(10) C3 0.0275(13) 0.0211(12) 0.0278(13) -0.0002(10) -0.0082(10) 0.0042(10) C4 0.0267(13) 0.0247(12) 0.0235(12) 0.0011(10) 0.0022(10) -0.0013(10) C5 0.0328(14) 0.0246(13) 0.0353(15) -0.0006(11) 0.0036(11) 0.0086(11) C6 0.0452(19) 0.0445(19) 0.058(2) -0.0118(16) -0.0156(16) 0.0197(15) C7 0.0205(12) 0.0236(12) 0.0252(12) 0.0027(10) -0.0030(9) 0.0030(9) C8 0.0207(12) 0.0213(12) 0.0303(13) 0.0020(10) -0.0051(10) 0.0038(9) C9 0.0222(12) 0.0283(13) 0.0298(13) -0.0027(10) -0.0028(10) 0.0038(10) C10 0.0226(12) 0.0350(14) 0.0253(13) 0.0013(11) 0.0006(10) 0.0014(10) C11 0.0244(12) 0.0257(13) 0.0270(13) 0.0058(10) -0.0042(10) -0.0018(10) C12 0.0226(12) 0.0227(12) 0.0289(13) 0.0027(10) -0.0020(10) 0.0014(9) Cl3 0.0301(3) 0.0180(3) 0.0311(3) 0.0004(2) -0.0040(2) 0.0046(2) Cl4 0.0377(4) 0.0272(3) 0.0476(4) -0.0126(3) -0.0153(3) 0.0061(3) O3 0.0341(11) 0.0373(12) 0.0536(13) 0.0234(10) 0.0014(10) 0.0100(9) O4 0.0239(9) 0.0245(9) 0.0354(10) 0.0052(8) -0.0022(8) 0.0086(7) N5 0.0211(10) 0.0190(10) 0.0222(10) 0.0018(8) -0.0032(8) 0.0047(8) N6 0.0238(11) 0.0255(11) 0.0239(10) 0.0029(8) -0.0007(8) 0.0015(8) N7 0.0233(10) 0.0248(11) 0.0260(11) 0.0037(8) -0.0022(8) 0.0020(8) N8 0.0256(11) 0.0163(10) 0.0304(11) 0.0010(8) -0.0097(9) 0.0079(8) C13 0.0198(11) 0.0182(11) 0.0230(12) -0.0018(9) -0.0048(9) 0.0032(9) C14 0.0218(12) 0.0219(12) 0.0224(12) 0.0018(9) -0.0029(9) 0.0011(9) C15 0.0261(12) 0.0217(12) 0.0263(12) 0.0030(10) 0.0012(10) 0.0033(10) C16 0.0255(12) 0.0202(12) 0.0291(13) 0.0039(10) -0.0065(10) 0.0018(10) C17 0.0217(12) 0.0260(13) 0.0451(16) 0.0000(12) -0.0069(11) 0.0091(10) C18 0.0389(17) 0.0422(18) 0.066(2) -0.0214(17) -0.0220(16) 0.0173(14) C19 0.0180(11) 0.0209(11) 0.0218(11) 0.0027(9) 0.0001(9) 0.0021(9) C20 0.0206(11) 0.0176(11) 0.0249(12) 0.0019(9) 0.0009(9) 0.0020(9) C21 0.0218(12) 0.0232(12) 0.0262(12) 0.0051(10) -0.0030(9) 0.0015(9) C22 0.0217(12) 0.0274(13) 0.0248(12) 0.0015(10) -0.0034(9) 0.0001(10) C23 0.0229(12) 0.0221(12) 0.0296(13) -0.0035(10) -0.0021(10) 0.0014(9) C24 0.0208(12) 0.0196(11) 0.0277(13) 0.0010(9) -0.0021(9) 0.0033(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C8 1.738(3) . ? Cl2 C11 1.737(3) . ? O1 C4 1.212(3) . ? O2 C4 1.333(3) . ? O2 C5 1.465(3) . ? N1 C1 1.355(3) . ? N1 N2 1.363(3) . ? N1 N4 1.377(3) . ? N2 N3 1.302(3) . ? N3 C2 1.375(3) . ? N4 C7 1.391(3) . ? N4 H4N 0.881(10) . ? C1 C2 1.377(4) . ? C1 C3 1.488(3) . ? C2 C4 1.468(4) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C5 C6 1.491(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C12 1.398(3) . ? C7 C8 1.404(4) . ? C8 C9 1.376(4) . ? C9 C10 1.389(4) . ? C9 H9 0.9500 . ? C10 C11 1.383(4) . ? C10 H10 0.9500 . ? C11 C12 1.378(4) . ? C12 H12 0.9500 . ? Cl3 C20 1.735(3) . ? Cl4 C23 1.741(3) . ? O3 C16 1.199(3) . ? O4 C16 1.327(3) . ? O4 C17 1.461(3) . ? N5 C13 1.354(3) . ? N5 N6 1.357(3) . ? N5 N8 1.383(3) . ? N6 N7 1.303(3) . ? N7 C14 1.367(3) . ? N8 C19 1.400(3) . ? N8 H8N 0.878(10) . ? C13 C14 1.377(3) . ? C13 C15 1.476(4) . ? C14 C16 1.475(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C17 C18 1.488(4) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C24 1.393(3) . ? C19 C20 1.402(3) . ? C20 C21 1.382(3) . ? C21 C22 1.389(4) . ? C21 H21 0.9500 . ? C22 C23 1.385(4) . ? C22 H22 0.9500 . ? C23 C24 1.386(4) . ? C24 H24 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O2 C5 116.0(2) . . ? C1 N1 N2 112.2(2) . . ? C1 N1 N4 127.4(2) . . ? N2 N1 N4 120.3(2) . . ? N3 N2 N1 106.8(2) . . ? N2 N3 C2 108.6(2) . . ? N1 N4 C7 115.9(2) . . ? N1 N4 H4N 114(2) . . ? C7 N4 H4N 122(2) . . ? N1 C1 C2 102.7(2) . . ? N1 C1 C3 123.0(2) . . ? C2 C1 C3 134.4(2) . . ? N3 C2 C1 109.8(2) . . ? N3 C2 C4 119.2(2) . . ? C1 C2 C4 131.0(2) . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? O1 C4 O2 124.7(2) . . ? O1 C4 C2 123.9(2) . . ? O2 C4 C2 111.5(2) . . ? O2 C5 C6 106.5(2) . . ? O2 C5 H5A 110.4 . . ? C6 C5 H5A 110.4 . . ? O2 C5 H5B 110.4 . . ? C6 C5 H5B 110.4 . . ? H5A C5 H5B 108.6 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N4 C7 C12 121.2(2) . . ? N4 C7 C8 120.5(2) . . ? C12 C7 C8 118.1(2) . . ? C9 C8 C7 121.2(2) . . ? C9 C8 Cl1 119.8(2) . . ? C7 C8 Cl1 119.1(2) . . ? C8 C9 C10 120.4(2) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C11 C10 C9 118.3(2) . . ? C11 C10 H10 120.9 . . ? C9 C10 H10 120.9 . . ? C12 C11 C10 122.2(2) . . ? C12 C11 Cl2 118.6(2) . . ? C10 C11 Cl2 119.2(2) . . ? C11 C12 C7 119.6(2) . . ? C11 C12 H12 120.2 . . ? C7 C12 H12 120.2 . . ? C16 O4 C17 116.8(2) . . ? C13 N5 N6 112.8(2) . . ? C13 N5 N8 129.0(2) . . ? N6 N5 N8 118.1(2) . . ? N7 N6 N5 106.0(2) . . ? N6 N7 C14 109.2(2) . . ? N5 N8 C19 117.7(2) . . ? N5 N8 H8N 116(2) . . ? C19 N8 H8N 121(2) . . ? N5 C13 C14 102.3(2) . . ? N5 C13 C15 123.9(2) . . ? C14 C13 C15 133.8(2) . . ? N7 C14 C13 109.6(2) . . ? N7 C14 C16 119.8(2) . . ? C13 C14 C16 130.6(2) . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O3 C16 O4 125.4(2) . . ? O3 C16 C14 123.4(3) . . ? O4 C16 C14 111.2(2) . . ? O4 C17 C18 110.5(2) . . ? O4 C17 H17A 109.6 . . ? C18 C17 H17A 109.6 . . ? O4 C17 H17B 109.6 . . ? C18 C17 H17B 109.6 . . ? H17A C17 H17B 108.1 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C24 C19 N8 122.6(2) . . ? C24 C19 C20 118.3(2) . . ? N8 C19 C20 119.0(2) . . ? C21 C20 C19 121.2(2) . . ? C21 C20 Cl3 119.74(19) . . ? C19 C20 Cl3 119.07(19) . . ? C20 C21 C22 120.5(2) . . ? C20 C21 H21 119.7 . . ? C22 C21 H21 119.7 . . ? C23 C22 C21 118.1(2) . . ? C23 C22 H22 121.0 . . ? C21 C22 H22 121.0 . . ? C22 C23 C24 122.3(2) . . ? C22 C23 Cl4 118.6(2) . . ? C24 C23 Cl4 119.1(2) . . ? C23 C24 C19 119.6(2) . . ? C23 C24 H24 120.2 . . ? C19 C24 H24 120.2 . . ? 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 C1 N1 N2 N3 -0.6(3) . . . . ? N4 N1 N2 N3 -177.7(2) . . . . ? N1 N2 N3 C2 0.5(3) . . . . ? C1 N1 N4 C7 -98.5(3) . . . . ? N2 N1 N4 C7 78.1(3) . . . . ? N2 N1 C1 C2 0.5(3) . . . . ? N4 N1 C1 C2 177.3(2) . . . . ? N2 N1 C1 C3 -177.8(2) . . . . ? N4 N1 C1 C3 -1.1(4) . . . . ? N2 N3 C2 C1 -0.1(3) . . . . ? N2 N3 C2 C4 177.9(2) . . . . ? N1 C1 C2 N3 -0.2(3) . . . . ? C3 C1 C2 N3 177.8(3) . . . . ? N1 C1 C2 C4 -178.0(3) . . . . ? C3 C1 C2 C4 0.1(5) . . . . ? C5 O2 C4 O1 -5.9(4) . . . . ? C5 O2 C4 C2 174.1(2) . . . . ? N3 C2 C4 O1 -4.5(4) . . . . ? C1 C2 C4 O1 173.0(3) . . . . ? N3 C2 C4 O2 175.5(2) . . . . ? C1 C2 C4 O2 -7.0(4) . . . . ? C4 O2 C5 C6 -173.2(3) . . . . ? N1 N4 C7 C12 25.3(3) . . . . ? N1 N4 C7 C8 -159.6(2) . . . . ? N4 C7 C8 C9 -169.8(2) . . . . ? C12 C7 C8 C9 5.3(4) . . . . ? N4 C7 C8 Cl1 10.8(3) . . . . ? C12 C7 C8 Cl1 -174.01(19) . . . . ? C7 C8 C9 C10 -3.8(4) . . . . ? Cl1 C8 C9 C10 175.6(2) . . . . ? C8 C9 C10 C11 -0.2(4) . . . . ? C9 C10 C11 C12 2.7(4) . . . . ? C9 C10 C11 Cl2 -176.7(2) . . . . ? C10 C11 C12 C7 -1.0(4) . . . . ? Cl2 C11 C12 C7 178.3(2) . . . . ? N4 C7 C12 C11 172.2(2) . . . . ? C8 C7 C12 C11 -2.9(4) . . . . ? C13 N5 N6 N7 -0.1(3) . . . . ? N8 N5 N6 N7 -178.4(2) . . . . ? N5 N6 N7 C14 0.6(3) . . . . ? C13 N5 N8 C19 82.9(3) . . . . ? N6 N5 N8 C19 -99.1(3) . . . . ? N6 N5 C13 C14 -0.3(3) . . . . ? N8 N5 C13 C14 177.7(2) . . . . ? N6 N5 C13 C15 177.6(2) . . . . ? N8 N5 C13 C15 -4.4(4) . . . . ? N6 N7 C14 C13 -0.8(3) . . . . ? N6 N7 C14 C16 178.1(2) . . . . ? N5 C13 C14 N7 0.7(3) . . . . ? C15 C13 C14 N7 -176.9(3) . . . . ? N5 C13 C14 C16 -178.1(3) . . . . ? C15 C13 C14 C16 4.3(5) . . . . ? C17 O4 C16 O3 3.8(4) . . . . ? C17 O4 C16 C14 -176.7(2) . . . . ? N7 C14 C16 O3 0.8(4) . . . . ? C13 C14 C16 O3 179.5(3) . . . . ? N7 C14 C16 O4 -178.6(2) . . . . ? C13 C14 C16 O4 0.0(4) . . . . ? C16 O4 C17 C18 88.4(3) . . . . ? N5 N8 C19 C24 0.1(4) . . . . ? N5 N8 C19 C20 177.8(2) . . . . ? C24 C19 C20 C21 -2.1(4) . . . . ? N8 C19 C20 C21 -179.9(2) . . . . ? C24 C19 C20 Cl3 177.75(18) . . . . ? N8 C19 C20 Cl3 -0.1(3) . . . . ? C19 C20 C21 C22 1.4(4) . . . . ? Cl3 C20 C21 C22 -178.4(2) . . . . ? C20 C21 C22 C23 0.2(4) . . . . ? C21 C22 C23 C24 -1.2(4) . . . . ? C21 C22 C23 Cl4 179.07(19) . . . . ? C22 C23 C24 C19 0.5(4) . . . . ? Cl4 C23 C24 C19 -179.74(19) . . . . ? N8 C19 C24 C23 178.9(2) . . . . ? C20 C19 C24 C23 1.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 26.5 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.47 _refine_diff_density_min -0.30 _refine_diff_density_rms 0.068 _database_code_depnum_ccdc_archive 'CCDC 672062'