# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Prof Gautam Desiraju' _publ_contact_author_address ; School of Chemistry University of Hyderabad PO Central University Hyderabad AP 500046 INDIA ; _publ_contact_author_email 'gautam desiraju@yahoo.com' _publ_contact_author_phone 914023134828 _publ_contact_author_fax 914023010567 _publ_section_title ; Sorting of polymorphs based on mechanical properties. Trimorphs of 6-chloro-2,4-dinitroaniline ; loop_ _publ_author_name _publ_author_address 'C. Malla Reddy' ; School of Chemistry University of Hyderabad 500046 Hyderabad, India ; 'Srinivas Basavoju' ; School of Chemistry University of Hyderabad 500046 Hyderabad, India ; 'Gautam.Desiraju R' ; School of Chemistry University of Hyderabad 500046 Hyderabad, India ; data_Form-I _database_code_depnum_ccdc_archive 'CCDC 260455' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6-chloro-2,4-dinitroaniline ; _chemical_name_common 6-chloro-2,4-dinitroaniline _chemical_melting_point 434(1) _chemical_formula_moiety 'C6 H4 Cl N3 O4' _chemical_formula_sum 'C6 H4 Cl N3 O4' _chemical_formula_weight 217.57 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' Cl Cl 0.1484 0.1585 '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 11.285(3) _cell_length_b 18.220(3) _cell_length_c 7.886(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.44(4) _cell_angle_gamma 90.00 _cell_volume 1621.4(17) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.40 _cell_measurement_theta_max 10.72 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.782 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.463 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.881 _exptl_absorpt_correction_T_max 0.913 _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius MACH-3' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time 90 _diffrn_standards_decay_% ? _diffrn_reflns_number 3079 _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_av_sigmaI/netI 0.0518 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 24.98 _reflns_number_total 2853 _reflns_number_gt 1569 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 data collection software' _computing_cell_refinement 'CAD4 data collection software' _computing_data_reduction ' WinGX v1.64.05, (2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0424P)^2^+0.3265P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2853 _refine_ls_number_parameters 261 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1146 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1097 _refine_ls_wR_factor_gt 0.0875 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 0.996 _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 -0.21738(10) 0.87616(6) -0.01043(14) 0.0630(4) Uani 1 1 d . . . O1 O 0.2188(2) 0.95908(14) 0.4394(4) 0.0683(9) Uani 1 1 d . . . O2 O 0.0833(3) 1.03513(14) 0.3674(4) 0.0717(10) Uani 1 1 d . . . O3 O 0.1753(3) 0.70477(14) 0.3781(4) 0.0662(9) Uani 1 1 d . . . O4 O 0.0412(3) 0.66059(13) 0.2123(4) 0.0677(9) Uani 1 1 d . . . N1 N -0.0929(3) 0.99306(17) 0.1683(4) 0.0525(9) Uani 1 1 d . . . H1A H -0.0620 1.0316 0.2134 0.091(18) Uiso 1 1 d R . . H1B H -0.1558 0.9968 0.1066 0.067(14) Uiso 1 1 d R . . N2 N 0.1245(3) 0.97344(17) 0.3713(4) 0.0484(9) Uani 1 1 d . . . N3 N 0.0913(3) 0.71212(16) 0.2822(4) 0.0463(8) Uani 1 1 d . . . C1 C -0.0434(3) 0.92773(18) 0.1939(4) 0.0389(9) Uani 1 1 d . . . C2 C 0.0594(3) 0.91347(18) 0.2919(4) 0.0378(9) Uani 1 1 d . . . C3 C 0.1032(3) 0.84396(18) 0.3201(5) 0.0400(9) Uani 1 1 d . . . H3 H 0.1705 0.8371 0.3869 0.040(10) Uiso 1 1 d R . . C4 C 0.0467(3) 0.78554(18) 0.2490(5) 0.0395(9) Uani 1 1 d . . . C5 C -0.0523(3) 0.79514(19) 0.1460(5) 0.0417(10) Uani 1 1 d . . . H5 H -0.0895 0.7549 0.0964 0.053(11) Uiso 1 1 d R . . C6 C -0.0942(3) 0.86370(19) 0.1184(5) 0.0408(9) Uani 1 1 d . . . Cl2 Cl 0.72603(9) 0.64735(5) 0.99049(14) 0.0571(3) Uani 1 1 d . . . O5 O 0.4121(3) 0.48583(14) 0.6441(4) 0.0865(12) Uani 1 1 d . . . O6 O 0.2894(2) 0.56281(14) 0.5408(4) 0.0638(9) Uani 1 1 d . . . O7 O 0.3408(3) 0.81778(13) 0.5843(4) 0.0633(9) Uani 1 1 d . . . O8 O 0.4724(3) 0.86196(13) 0.7550(4) 0.0671(9) Uani 1 1 d . . . N4 N 0.5905(3) 0.52909(16) 0.8363(4) 0.0505(9) Uani 1 1 d . . . H4A H 0.5564 0.4901 0.7984 0.072(14) Uiso 1 1 d R . . H4B H 0.6525 0.5255 0.8997 0.053(12) Uiso 1 1 d R . . N5 N 0.3789(3) 0.54837(16) 0.6219(4) 0.0503(9) Uani 1 1 d . . . N6 N 0.4222(3) 0.81059(16) 0.6850(4) 0.0451(8) Uani 1 1 d . . . C7 C 0.5471(3) 0.59493(18) 0.7970(4) 0.0374(9) Uani 1 1 d . . . C8 C 0.4466(3) 0.60833(17) 0.6947(5) 0.0384(9) Uani 1 1 d . . . C9 C 0.4052(3) 0.67790(17) 0.6581(4) 0.0378(9) Uani 1 1 d . . . H9 H 0.3382 0.6843 0.5904 0.041(10) Uiso 1 1 d R . . C10 C 0.4644(3) 0.73720(17) 0.7229(5) 0.0366(9) Uani 1 1 d . . . C11 C 0.5641(3) 0.72787(19) 0.8249(5) 0.0416(10) Uani 1 1 d . . . H11 H 0.6039 0.7686 0.8681 0.057(12) Uiso 1 1 d R . . C12 C 0.6033(3) 0.65929(18) 0.8612(5) 0.0394(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0521(7) 0.0584(7) 0.0778(8) 0.0010(6) -0.0356(6) 0.0009(5) O1 0.0586(19) 0.0505(17) 0.095(2) -0.0101(16) -0.0443(18) 0.0037(14) O2 0.068(2) 0.0339(16) 0.113(3) -0.0045(16) -0.0407(19) 0.0039(14) O3 0.066(2) 0.0506(17) 0.081(2) -0.0029(15) -0.0335(18) 0.0145(15) O4 0.083(2) 0.0328(15) 0.087(2) -0.0069(15) -0.0267(19) -0.0041(14) N1 0.050(2) 0.040(2) 0.068(2) 0.0040(17) -0.023(2) 0.0045(16) N2 0.042(2) 0.0389(19) 0.064(2) -0.0022(17) -0.0202(18) 0.0002(15) N3 0.050(2) 0.0349(18) 0.054(2) 0.0009(16) -0.0075(18) 0.0045(15) C1 0.039(2) 0.037(2) 0.040(2) 0.0044(17) -0.0087(18) 0.0009(17) C2 0.038(2) 0.032(2) 0.044(2) -0.0035(17) -0.0112(19) -0.0042(16) C3 0.035(2) 0.040(2) 0.044(2) -0.0004(18) -0.0112(19) 0.0033(17) C4 0.047(2) 0.032(2) 0.040(2) -0.0009(17) -0.006(2) 0.0003(17) C5 0.045(2) 0.036(2) 0.044(2) -0.0057(18) -0.009(2) -0.0040(17) C6 0.036(2) 0.042(2) 0.045(2) -0.0012(18) -0.0112(19) -0.0002(17) Cl2 0.0476(6) 0.0507(6) 0.0726(8) -0.0005(5) -0.0316(6) 0.0000(5) O5 0.083(2) 0.0296(16) 0.146(3) -0.0063(18) -0.065(2) 0.0050(15) O6 0.0579(18) 0.0443(16) 0.088(2) -0.0029(15) -0.0401(18) -0.0030(13) O7 0.071(2) 0.0448(16) 0.074(2) 0.0048(15) -0.0284(18) 0.0122(14) O8 0.081(2) 0.0299(15) 0.090(2) -0.0057(15) -0.0255(18) -0.0012(14) N4 0.051(2) 0.0312(18) 0.069(2) 0.0053(16) -0.028(2) 0.0009(15) N5 0.045(2) 0.0356(19) 0.070(2) -0.0043(17) -0.0235(19) 0.0007(15) N6 0.050(2) 0.0324(18) 0.053(2) 0.0012(16) -0.0076(19) 0.0041(15) C7 0.035(2) 0.036(2) 0.042(2) 0.0037(17) -0.0095(18) 0.0005(16) C8 0.037(2) 0.028(2) 0.050(2) -0.0018(17) -0.0113(19) -0.0021(15) C9 0.036(2) 0.038(2) 0.039(2) 0.0022(18) -0.0094(19) -0.0007(17) C10 0.040(2) 0.0279(19) 0.042(2) 0.0028(17) -0.0089(18) 0.0006(16) C11 0.043(2) 0.034(2) 0.047(2) -0.0048(18) -0.009(2) -0.0052(17) C12 0.033(2) 0.038(2) 0.047(2) -0.0001(18) -0.0146(19) -0.0011(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C6 1.731(4) . ? O1 N2 1.217(4) . ? O2 N2 1.217(4) . ? O3 N3 1.216(4) . ? O4 N3 1.225(4) . ? N1 C1 1.330(4) . ? N1 H1A 0.8601 . ? N1 H1B 0.8602 . ? N2 C2 1.456(4) . ? N3 C4 1.452(4) . ? C1 C2 1.413(5) . ? C1 C6 1.428(5) . ? C2 C3 1.377(4) . ? C3 C4 1.360(5) . ? C3 H3 0.9294 . ? C4 C5 1.387(5) . ? C5 C6 1.352(5) . ? C5 H5 0.9299 . ? Cl2 C12 1.728(4) . ? O5 N5 1.212(4) . ? O6 N5 1.220(3) . ? O7 N6 1.217(4) . ? O8 N6 1.223(4) . ? N4 C7 1.332(4) . ? N4 H4A 0.8604 . ? N4 H4B 0.8593 . ? N5 C8 1.449(4) . ? N6 C10 1.450(4) . ? C7 C8 1.408(5) . ? C7 C12 1.424(5) . ? C8 C9 1.380(4) . ? C9 C10 1.368(4) . ? C9 H9 0.9296 . ? C10 C11 1.388(5) . ? C11 C12 1.355(5) . ? C11 H11 0.9307 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 H1A 120.0 . . ? C1 N1 H1B 120.1 . . ? H1A N1 H1B 119.9 . . ? O1 N2 O2 122.9(3) . . ? O1 N2 C2 117.7(3) . . ? O2 N2 C2 119.4(3) . . ? O3 N3 O4 123.4(3) . . ? O3 N3 C4 118.8(3) . . ? O4 N3 C4 117.8(3) . . ? N1 C1 C2 126.2(3) . . ? N1 C1 C6 120.1(3) . . ? C2 C1 C6 113.8(3) . . ? C3 C2 C1 123.4(3) . . ? C3 C2 N2 116.2(3) . . ? C1 C2 N2 120.5(3) . . ? C4 C3 C2 119.1(3) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 121.1(3) . . ? C3 C4 N3 119.1(3) . . ? C5 C4 N3 119.9(3) . . ? C6 C5 C4 119.3(3) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.4 . . ? C5 C6 C1 123.3(3) . . ? C5 C6 Cl1 119.6(3) . . ? C1 C6 Cl1 117.1(3) . . ? C7 N4 H4A 120.0 . . ? C7 N4 H4B 120.1 . . ? H4A N4 H4B 119.9 . . ? O5 N5 O6 122.2(3) . . ? O5 N5 C8 119.4(3) . . ? O6 N5 C8 118.5(3) . . ? O7 N6 O8 123.8(3) . . ? O7 N6 C10 118.6(3) . . ? O8 N6 C10 117.5(3) . . ? N4 C7 C8 125.7(3) . . ? N4 C7 C12 119.8(3) . . ? C8 C7 C12 114.5(3) . . ? C9 C8 C7 123.3(3) . . ? C9 C8 N5 115.7(3) . . ? C7 C8 N5 121.1(3) . . ? C10 C9 C8 118.9(3) . . ? C10 C9 H9 120.6 . . ? C8 C9 H9 120.5 . . ? C9 C10 C11 120.7(3) . . ? C9 C10 N6 119.5(3) . . ? C11 C10 N6 119.7(3) . . ? C12 C11 C10 119.8(3) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C11 C12 C7 122.7(3) . . ? C11 C12 Cl2 120.0(3) . . ? C7 C12 Cl2 117.3(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.215 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.057 data_Form-II _database_code_depnum_ccdc_archive 'CCDC 260456' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6-Chloro-2,4-dinitroanilene ; _chemical_name_common 6-Chloro-2,4-dinitroanilene _chemical_melting_point 432(1) _chemical_formula_moiety 'C6 H4 Cl N3 O4' _chemical_formula_sum 'C6 H4 Cl N3 O4' _chemical_formula_weight 217.57 _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.1619(18) _cell_length_b 3.6646(8) _cell_length_c 13.278(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.310(3) _cell_angle_gamma 90.00 _cell_volume 397.04(15) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4276 _cell_measurement_theta_min 2.90 _cell_measurement_theta_max 28.12 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.83 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.820 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 220 _exptl_absorpt_coefficient_mu 0.473 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6951 _exptl_absorpt_correction_T_max 0.9860 _exptl_absorpt_process_details ; SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6858 _diffrn_reflns_av_R_equivalents 0.0450 _diffrn_reflns_av_sigmaI/netI 0.0353 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 26.33 _reflns_number_total 1608 _reflns_number_gt 1569 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0540P)^2^+0.1399P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.08(8) _refine_ls_number_reflns 1608 _refine_ls_number_parameters 135 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0393 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.0949 _refine_ls_wR_factor_gt 0.0945 _refine_ls_goodness_of_fit_ref 1.137 _refine_ls_restrained_S_all 1.136 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8357(3) 0.8047(7) 0.7116(2) 0.0164(5) Uani 1 1 d . . . C2 C 0.7135(3) 0.6519(7) 0.6466(2) 0.0165(5) Uani 1 1 d . . . C3 C 0.5638(3) 0.5344(7) 0.68156(19) 0.0165(5) Uani 1 1 d . . . C4 C 0.5320(3) 0.5651(6) 0.7808(2) 0.0170(6) Uani 1 1 d . . . C5 C 0.6467(3) 0.7065(8) 0.8494(2) 0.0176(5) Uani 1 1 d . . . C6 C 0.7937(3) 0.8201(7) 0.8147(2) 0.0167(5) Uani 1 1 d . . . Cl1 Cl 0.93843(7) 0.99266(17) 0.89833(4) 0.02067(18) Uani 1 1 d . . . N1 N 0.9809(3) 0.9268(7) 0.68336(19) 0.0196(5) Uani 1 1 d . . . N2 N 0.7409(3) 0.6038(6) 0.54078(17) 0.0171(5) Uani 1 1 d . . . N3 N 0.3760(3) 0.4395(7) 0.81747(16) 0.0219(5) Uani 1 1 d . . . O1 O 0.8620(2) 0.7495(6) 0.50430(15) 0.0271(5) Uani 1 1 d . . . O2 O 0.6451(2) 0.4201(6) 0.49102(14) 0.0275(5) Uani 1 1 d . . . O3 O 0.2800(2) 0.2969(7) 0.75642(16) 0.0326(5) Uani 1 1 d . . . O4 O 0.3476(2) 0.4736(9) 0.90674(14) 0.0373(5) Uani 1 1 d . . . H1A H 1.048(3) 0.996(11) 0.731(2) 0.024(8) Uiso 1 1 d . . . H1B H 1.006(4) 0.911(10) 0.619(2) 0.024(8) Uiso 1 1 d . . . H3 H 0.4860 0.4355 0.6372 0.020 Uiso 1 1 calc R . . H5 H 0.6233 0.7230 0.9175 0.021 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 C1 0.0119(11) 0.0135(12) 0.0237(14) 0.0025(10) -0.0002(10) 0.0017(10) C2 0.0166(12) 0.0109(11) 0.0220(13) 0.0002(10) 0.0011(10) 0.0025(10) C3 0.0122(11) 0.0113(12) 0.0259(12) 0.0009(10) -0.0038(9) -0.0002(10) C4 0.0113(11) 0.0104(13) 0.0292(14) 0.0017(10) -0.0006(10) 0.0007(9) C5 0.0185(12) 0.0170(12) 0.0173(13) 0.0033(10) 0.0021(10) 0.0012(10) C6 0.0132(12) 0.0118(11) 0.0247(14) 0.0011(10) -0.0060(10) 0.0000(10) Cl1 0.0187(3) 0.0184(3) 0.0247(3) 0.0003(3) -0.0055(2) -0.0047(3) N1 0.0114(10) 0.0229(14) 0.0247(12) -0.0019(10) 0.0012(9) -0.0013(9) N2 0.0129(10) 0.0149(10) 0.0236(11) -0.0008(8) 0.0004(9) 0.0037(8) N3 0.0181(10) 0.0198(12) 0.0279(12) 0.0055(11) 0.0013(9) -0.0027(10) O1 0.0196(10) 0.0339(12) 0.0279(11) -0.0011(9) 0.0058(8) -0.0022(9) O2 0.0281(10) 0.0284(12) 0.0260(10) -0.0084(8) -0.0038(8) -0.0038(9) O3 0.0179(10) 0.0427(13) 0.0370(12) -0.0031(10) 0.0012(9) -0.0138(10) O4 0.0250(10) 0.0573(15) 0.0299(11) 0.0059(13) 0.0084(8) -0.0136(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.418(4) . ? C1 C6 1.421(4) . ? C5 H5 0.9300 . ? C3 C2 1.385(4) . ? C3 C4 1.353(4) . ? C3 H3 0.9300 . ? C5 C6 1.360(4) . ? C5 C4 1.391(4) . ? Cl1 C6 1.723(3) . ? N1 C1 1.329(3) . ? N1 H1A 0.86(3) . ? N1 H1B 0.89(3) . ? N2 C2 1.439(3) . ? N3 C4 1.449(3) . ? O1 N2 1.233(3) . ? O2 N2 1.215(3) . ? O3 N3 1.231(3) . ? O4 N3 1.219(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 C2 N2 121.3(2) . . ? C1 C6 Cl1 117.28(19) . . ? C1 N1 H1A 117(2) . . ? C1 N1 H1B 118(2) . . ? C2 C1 C6 114.8(2) . . ? C2 C3 H3 120.3 . . ? C3 C2 C1 122.2(2) . . ? C3 C2 N2 116.5(2) . . ? C3 C4 C5 121.8(2) . . ? C3 C4 N3 119.4(2) . . ? C4 C5 H5 120.7 . . ? C4 C3 C2 119.4(2) . . ? C4 C3 H3 120.3 . . ? C5 C6 C1 123.3(2) . . ? C5 C6 Cl1 119.5(2) . . ? C5 C4 N3 118.8(2) . . ? C6 C5 C4 118.6(2) . . ? C6 C5 H5 120.7 . . ? N1 C1 C2 125.5(2) . . ? N1 C1 C6 119.7(2) . . ? O1 N2 C2 118.3(2) . . ? O2 N2 O1 122.6(2) . . ? O2 N2 C2 119.1(2) . . ? O3 N3 C4 117.7(2) . . ? O4 N3 O3 123.5(2) . . ? O4 N3 C4 118.8(2) . . ? H1A N1 H1B 125(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.33 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.515 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.093 data_Form-III _database_code_depnum_ccdc_archive 'CCDC 260457' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6-Chloro-2,4-dinitroanilene ; _chemical_name_common 6-Chloro-2,4-dinitroanilene _chemical_melting_point 436(1) _chemical_formula_moiety 'C6 H4 Cl N3 O4' _chemical_formula_sum 'C6 H4 Cl N3 O4' _chemical_formula_weight 217.57 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' Cl Cl 0.1484 0.1585 '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 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 7.9465(12) _cell_length_b 8.917(3) _cell_length_c 12.980(4) _cell_angle_alpha 89.35(3) _cell_angle_beta 85.575(19) _cell_angle_gamma 63.978(15) _cell_volume 823.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 1.57 _cell_measurement_theta_max 25 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.754 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.456 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.893 _exptl_absorpt_correction_T_max 0.915 _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius MACH-3' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time 90 _diffrn_standards_decay_% ? _diffrn_reflns_number 3132 _diffrn_reflns_av_R_equivalents 0.0102 _diffrn_reflns_av_sigmaI/netI 0.0169 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2901 _reflns_number_gt 2362 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 data collection software' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0449P)^2^+0.3464P] 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 2901 _refine_ls_number_parameters 285 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.0937 _refine_ls_wR_factor_gt 0.0860 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.0112(3) 0.7405(3) 0.00577(16) 0.0360(5) Uani 1 1 d . . . C2 C 0.9272(3) 0.7565(3) 0.10887(16) 0.0382(5) Uani 1 1 d . . . C3 C 0.7675(3) 0.8911(3) 0.14401(17) 0.0390(5) Uani 1 1 d . . . C4 C 0.6781(3) 1.0180(3) 0.07722(17) 0.0379(5) Uani 1 1 d . . . C5 C 0.7482(3) 1.0108(3) -0.02276(17) 0.0368(5) Uani 1 1 d . . . C6 C 0.9113(3) 0.8747(3) -0.05752(15) 0.0343(5) Uani 1 1 d . . . Cl1 Cl 1.03881(10) 0.59752(9) 0.19136(5) 0.0631(2) Uani 1 1 d . . . N1 N 1.1707(3) 0.6076(3) -0.0220(2) 0.0530(6) Uani 1 1 d . . . N2 N 0.5065(3) 1.1612(2) 0.11374(17) 0.0485(5) Uani 1 1 d . . . N3 N 0.9801(3) 0.8782(3) -0.16393(15) 0.0472(5) Uani 1 1 d . . . O1 O 0.4453(3) 1.1634(2) 0.20298(16) 0.0693(6) Uani 1 1 d . . . O2 O 0.4300(3) 1.2708(2) 0.05310(16) 0.0693(6) Uani 1 1 d . . . O3 O 0.8901(3) 0.9952(3) -0.21570(15) 0.0838(7) Uani 1 1 d . . . O4 O 1.1303(3) 0.7669(3) -0.19640(14) 0.0772(6) Uani 1 1 d . . . C7 C 0.3135(3) 0.5806(2) 0.41406(15) 0.0314(4) Uani 1 1 d . . . C8 C 0.2273(3) 0.6521(3) 0.51302(15) 0.0340(5) Uani 1 1 d . . . C9 C 0.2072(3) 0.8025(3) 0.54684(17) 0.0368(5) Uani 1 1 d . . . C10 C 0.2730(3) 0.8922(2) 0.48204(16) 0.0353(5) Uani 1 1 d . . . C11 C 0.3590(3) 0.8326(3) 0.38586(17) 0.0359(5) Uani 1 1 d . . . C12 C 0.3788(3) 0.6789(2) 0.35329(15) 0.0329(5) Uani 1 1 d . . . Cl2 Cl 0.14781(9) 0.53674(8) 0.59309(4) 0.05043(19) Uani 1 1 d . . . N4 N 0.3293(3) 0.4320(2) 0.38607(19) 0.0441(5) Uani 1 1 d . . . N5 N 0.2537(3) 1.0535(2) 0.51656(16) 0.0476(5) Uani 1 1 d . . . N6 N 0.4751(3) 0.6207(2) 0.25145(14) 0.0419(4) Uani 1 1 d . . . O5 O 0.1821(3) 1.1043(2) 0.60296(15) 0.0751(6) Uani 1 1 d . . . O6 O 0.3095(3) 1.1312(2) 0.45699(16) 0.0692(6) Uani 1 1 d . . . O7 O 0.5346(3) 0.7072(2) 0.20318(14) 0.0656(5) Uani 1 1 d . . . O8 O 0.4954(3) 0.4869(2) 0.21737(15) 0.0664(5) Uani 1 1 d . . . H1A H 1.219(4) 0.529(4) 0.028(2) 0.082(10) Uiso 1 1 d . . . H1B H 1.216(4) 0.604(4) -0.078(3) 0.068(10) Uiso 1 1 d . . . H3 H 0.718(3) 0.898(3) 0.214(2) 0.052(7) Uiso 1 1 d . . . H5 H 0.687(3) 1.094(3) -0.0627(18) 0.043(6) Uiso 1 1 d . . . H4A H 0.290(4) 0.383(3) 0.427(2) 0.054(8) Uiso 1 1 d . . . H4B H 0.385(4) 0.388(4) 0.326(2) 0.067(9) Uiso 1 1 d . . . H9 H 0.152(3) 0.841(3) 0.6106(18) 0.041(6) Uiso 1 1 d . . . H11 H 0.408(3) 0.890(3) 0.3425(19) 0.049(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0334(11) 0.0348(11) 0.0366(11) -0.0023(9) -0.0028(9) -0.0121(9) C2 0.0393(12) 0.0386(12) 0.0353(11) 0.0047(9) -0.0055(9) -0.0156(10) C3 0.0406(12) 0.0438(13) 0.0325(12) -0.0043(9) 0.0014(10) -0.0191(10) C4 0.0343(11) 0.0341(11) 0.0428(12) -0.0052(9) -0.0018(9) -0.0128(9) C5 0.0371(12) 0.0320(11) 0.0409(12) 0.0029(10) -0.0095(10) -0.0139(10) C6 0.0366(11) 0.0385(11) 0.0282(10) -0.0005(9) -0.0014(9) -0.0170(10) Cl1 0.0605(4) 0.0592(4) 0.0497(4) 0.0206(3) -0.0057(3) -0.0083(3) N1 0.0462(12) 0.0462(13) 0.0454(13) 0.0018(10) 0.0059(11) -0.0025(10) N2 0.0433(11) 0.0387(11) 0.0578(13) -0.0121(10) 0.0024(10) -0.0135(9) N3 0.0463(12) 0.0558(12) 0.0366(10) 0.0053(9) -0.0023(9) -0.0202(10) O1 0.0687(13) 0.0569(12) 0.0656(13) -0.0166(10) 0.0246(10) -0.0165(10) O2 0.0609(12) 0.0409(10) 0.0768(13) -0.0021(10) -0.0114(10) 0.0056(9) O3 0.0717(14) 0.1011(17) 0.0528(12) 0.0360(12) -0.0045(10) -0.0153(13) O4 0.0795(14) 0.0749(14) 0.0437(10) -0.0009(9) 0.0191(10) -0.0069(12) C7 0.0284(10) 0.0273(10) 0.0368(11) 0.0041(8) -0.0073(8) -0.0100(8) C8 0.0345(11) 0.0369(11) 0.0335(11) 0.0106(9) -0.0064(9) -0.0180(9) C9 0.0413(12) 0.0397(12) 0.0284(11) 0.0006(9) -0.0044(9) -0.0167(10) C10 0.0399(12) 0.0279(10) 0.0373(11) 0.0018(8) -0.0063(9) -0.0135(9) C11 0.0373(12) 0.0337(11) 0.0380(12) 0.0083(9) -0.0046(9) -0.0166(10) C12 0.0327(11) 0.0322(11) 0.0315(10) 0.0011(8) -0.0008(8) -0.0124(9) Cl2 0.0618(4) 0.0579(4) 0.0441(3) 0.0142(3) -0.0027(3) -0.0382(3) N4 0.0527(13) 0.0339(11) 0.0479(12) 0.0003(9) -0.0007(10) -0.0215(10) N5 0.0604(13) 0.0342(10) 0.0491(12) -0.0014(9) -0.0114(10) -0.0204(10) N6 0.0388(10) 0.0452(11) 0.0397(10) -0.0023(9) 0.0042(8) -0.0175(9) O5 0.1150(18) 0.0596(12) 0.0541(12) -0.0204(10) 0.0064(11) -0.0430(12) O6 0.1034(16) 0.0402(10) 0.0739(13) 0.0040(9) 0.0024(11) -0.0423(11) O7 0.0819(14) 0.0726(13) 0.0489(10) 0.0004(9) 0.0191(9) -0.0438(11) O8 0.0777(13) 0.0610(12) 0.0615(12) -0.0270(10) 0.0253(10) -0.0357(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.328(3) . ? C1 C6 1.408(3) . ? C1 C2 1.428(3) . ? C2 C3 1.358(3) . ? C2 Cl1 1.718(2) . ? C3 C4 1.380(3) . ? C3 H3 0.95(3) . ? C4 C5 1.363(3) . ? C4 N2 1.449(3) . ? C5 C6 1.378(3) . ? C5 H5 0.88(2) . ? C6 N3 1.451(3) . ? N1 H1A 0.92(3) . ? N1 H1B 0.78(3) . ? N2 O2 1.217(3) . ? N2 O1 1.218(3) . ? N3 O3 1.206(3) . ? N3 O4 1.216(3) . ? C7 N4 1.327(3) . ? C7 C12 1.407(3) . ? C7 C8 1.423(3) . ? C8 C9 1.353(3) . ? C8 Cl2 1.727(2) . ? C9 C10 1.380(3) . ? C9 H9 0.90(2) . ? C10 C11 1.368(3) . ? C10 N5 1.450(3) . ? C11 C12 1.377(3) . ? C11 H11 0.93(3) . ? C12 N6 1.454(3) . ? N4 H4A 0.81(3) . ? N4 H4B 0.88(3) . ? N5 O5 1.214(3) . ? N5 O6 1.217(3) . ? N6 O7 1.215(2) . ? N6 O8 1.215(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C6 126.1(2) . . ? N1 C1 C2 119.8(2) . . ? C6 C1 C2 114.13(19) . . ? C3 C2 C1 123.2(2) . . ? C3 C2 Cl1 119.48(17) . . ? C1 C2 Cl1 117.31(17) . . ? C2 C3 C4 119.2(2) . . ? C2 C3 H3 120.6(15) . . ? C4 C3 H3 120.2(15) . . ? C5 C4 C3 121.1(2) . . ? C5 C4 N2 119.4(2) . . ? C3 C4 N2 119.5(2) . . ? C4 C5 C6 119.4(2) . . ? C4 C5 H5 118.3(15) . . ? C6 C5 H5 122.3(15) . . ? C5 C6 C1 123.0(2) . . ? C5 C6 N3 116.2(2) . . ? C1 C6 N3 120.78(19) . . ? C1 N1 H1A 116(2) . . ? C1 N1 H1B 118(2) . . ? H1A N1 H1B 126(3) . . ? O2 N2 O1 123.7(2) . . ? O2 N2 C4 118.2(2) . . ? O1 N2 C4 118.1(2) . . ? O3 N3 O4 122.3(2) . . ? O3 N3 C6 118.8(2) . . ? O4 N3 C6 118.9(2) . . ? N4 C7 C12 125.2(2) . . ? N4 C7 C8 120.4(2) . . ? C12 C7 C8 114.44(18) . . ? C9 C8 C7 123.55(19) . . ? C9 C8 Cl2 119.35(17) . . ? C7 C8 Cl2 117.09(16) . . ? C8 C9 C10 118.5(2) . . ? C8 C9 H9 119.5(15) . . ? C10 C9 H9 122.0(15) . . ? C11 C10 C9 122.0(2) . . ? C11 C10 N5 118.5(2) . . ? C9 C10 N5 119.6(2) . . ? C10 C11 C12 118.6(2) . . ? C10 C11 H11 122.6(15) . . ? C12 C11 H11 118.8(15) . . ? C11 C12 C7 123.02(19) . . ? C11 C12 N6 115.97(19) . . ? C7 C12 N6 121.00(18) . . ? C7 N4 H4A 118.0(19) . . ? C7 N4 H4B 120(2) . . ? H4A N4 H4B 122(3) . . ? O5 N5 O6 123.4(2) . . ? O5 N5 C10 118.5(2) . . ? O6 N5 C10 118.1(2) . . ? O7 N6 O8 121.9(2) . . ? O7 N6 C12 118.70(19) . . ? O8 N6 C12 119.42(19) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.255 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.044 # end