# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2011 data_global _journal_coden_Cambridge 440 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Drab, David' 'Smiglak, Marcin' 'Shamshina, Julia' 'Kelley, Steven' 'Schneider, Stefan' 'Hawkins, Tommy' 'Rogers, Robin' _publ_contact_author_name 'Drab, David' _publ_contact_author_email rdrogers@as.ua.edu _publ_section_title ; Synthesis of N-cyanoalkyl-functionalized imidazolium nitrate and dicyanamide ionic liquids with a comparison of their thermal properties for energetic applications ; # Attachment 'Drab-Rogers-New-J-Chem-cif-11-10-10.txt' data_5[Br] _database_code_depnum_ccdc_archive 'CCDC 801102' #TrackingRef 'Drab-Rogers-New-J-Chem-cif-11-10-10.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H10 Br N3' _chemical_formula_weight 216.09 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 9.5124(7) _cell_length_b 11.5501(8) _cell_length_c 16.6392(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1828.1(2) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6703 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 28.33 _exptl_crystal_description fragement _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.570 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 4.440 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.69940 _exptl_absorpt_correction_T_max 0.898 _exptl_absorpt_process_details 'SADABS, Sheldrick, 2002' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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_reflns_number 11642 _diffrn_reflns_av_R_equivalents 0.0292 _diffrn_reflns_av_sigmaI/netI 0.0192 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 28.33 _reflns_number_total 2173 _reflns_number_gt 1856 _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, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0265P)^2^+0.6058P] 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 2173 _refine_ls_number_parameters 101 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0284 _refine_ls_R_factor_gt 0.0214 _refine_ls_wR_factor_ref 0.0549 _refine_ls_wR_factor_gt 0.0526 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _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 Br Br 0.176771(18) 0.381528(13) 0.331692(9) 0.02697(7) Uani 1 1 d . . . N1 N 0.04609(14) 0.57641(11) 0.14233(8) 0.0219(3) Uani 1 1 d . . . N3 N 0.19721(14) 0.50610(11) 0.05875(8) 0.0236(3) Uani 1 1 d . . . N9 N -0.07813(19) 0.71571(15) 0.40624(10) 0.0439(4) Uani 1 1 d . . . C2 C 0.14403(17) 0.49518(14) 0.13221(10) 0.0242(3) Uani 1 1 d . . . H2A H 0.1712 0.4390 0.1709 0.029 Uiso 1 1 calc R . . C4 C 0.13080(19) 0.59666(13) 0.02061(10) 0.0259(3) Uani 1 1 d . . . H4A H 0.1481 0.6230 -0.0326 0.031 Uiso 1 1 calc R . . C5 C 0.03647(19) 0.64101(13) 0.07286(10) 0.0254(3) Uani 1 1 d . . . H5A H -0.0248 0.7046 0.0635 0.030 Uiso 1 1 calc R . . C6 C -0.03235(17) 0.59695(14) 0.21685(9) 0.0240(3) Uani 1 1 d . . . H6A H -0.0544 0.5221 0.2430 0.029 Uiso 1 1 calc R . . H6B H -0.1220 0.6366 0.2045 0.029 Uiso 1 1 calc R . . C7 C 0.05509(17) 0.67137(15) 0.27341(10) 0.0274(3) Uani 1 1 d . . . H7A H 0.1438 0.6305 0.2863 0.033 Uiso 1 1 calc R . . H7B H 0.0795 0.7449 0.2462 0.033 Uiso 1 1 calc R . . C8 C -0.02026(19) 0.69675(14) 0.34778(10) 0.0293(4) Uani 1 1 d . . . C10 C 0.30828(18) 0.43300(16) 0.02436(11) 0.0332(4) Uani 1 1 d . . . H10A H 0.3864 0.4270 0.0625 0.050 Uiso 1 1 calc R . . H10B H 0.3420 0.4676 -0.0258 0.050 Uiso 1 1 calc R . . H10C H 0.2706 0.3556 0.0134 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 Br 0.03442(11) 0.02545(10) 0.02104(10) 0.00098(5) -0.00271(6) -0.00144(6) N1 0.0236(7) 0.0219(6) 0.0204(6) -0.0003(5) 0.0012(5) -0.0019(5) N3 0.0264(7) 0.0223(6) 0.0220(6) 0.0005(5) 0.0032(5) 0.0004(5) N9 0.0528(11) 0.0444(9) 0.0344(9) -0.0100(7) 0.0099(8) -0.0040(8) C2 0.0269(8) 0.0237(8) 0.0221(8) 0.0022(6) -0.0002(6) -0.0002(6) C4 0.0326(8) 0.0229(7) 0.0221(8) 0.0027(6) 0.0017(7) -0.0003(7) C5 0.0288(8) 0.0218(7) 0.0255(8) 0.0033(6) -0.0018(7) -0.0003(7) C6 0.0217(7) 0.0279(8) 0.0224(7) -0.0023(6) 0.0035(7) -0.0031(6) C7 0.0232(8) 0.0314(9) 0.0275(8) -0.0061(6) 0.0021(6) -0.0028(6) C8 0.0330(9) 0.0256(8) 0.0293(9) -0.0025(6) 0.0003(8) -0.0007(7) C10 0.0340(9) 0.0321(9) 0.0334(9) 0.0011(7) 0.0095(8) 0.0084(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.333(2) . ? N1 C5 1.379(2) . ? N1 C6 1.467(2) . ? N3 C2 1.329(2) . ? N3 C4 1.377(2) . ? N3 C10 1.469(2) . ? N9 C8 1.139(2) . ? C4 C5 1.350(2) . ? C6 C7 1.522(2) . ? C7 C8 1.460(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C5 108.75(13) . . ? C2 N1 C6 125.19(13) . . ? C5 N1 C6 125.98(13) . . ? C2 N3 C4 108.75(13) . . ? C2 N3 C10 125.29(14) . . ? C4 N3 C10 125.96(14) . . ? N3 C2 N1 108.39(14) . . ? C5 C4 N3 107.23(14) . . ? C4 C5 N1 106.88(14) . . ? N1 C6 C7 109.64(13) . . ? C8 C7 C6 111.67(14) . . ? N9 C8 C7 179.3(2) . . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 25.30 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.220 _refine_diff_density_min -0.514 _refine_diff_density_rms 0.073 data_(10[Br]) _database_code_depnum_ccdc_archive 'CCDC 801103' #TrackingRef 'Drab-Rogers-New-J-Chem-cif-11-10-10.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H10 Br N3' _chemical_formula_weight 216.09 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.5721(11) _cell_length_b 11.2151(16) _cell_length_c 10.5200(15) _cell_angle_alpha 90.00 _cell_angle_beta 91.133(2) _cell_angle_gamma 90.00 _cell_volume 893.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3932 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 28.30 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.607 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 4.543 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.69940 _exptl_absorpt_correction_T_max 0.898 _exptl_absorpt_process_details 'SADABS, Sheldrick, 2002' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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_reflns_number 6054 _diffrn_reflns_av_R_equivalents 0.0377 _diffrn_reflns_av_sigmaI/netI 0.0376 _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 -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 28.30 _reflns_number_total 2095 _reflns_number_gt 1813 _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, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0572P)^2^+0.0000P] 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 2095 _refine_ls_number_parameters 102 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0397 _refine_ls_R_factor_gt 0.0328 _refine_ls_wR_factor_ref 0.0867 _refine_ls_wR_factor_gt 0.0826 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 Br Br 0.18893(3) 0.150717(19) 0.02500(2) 0.02600(11) Uani 1 1 d . . . N1 N 0.4057(2) -0.05686(17) -0.24271(18) 0.0222(4) Uani 1 1 d . . . N3 N 0.6374(2) 0.05497(17) -0.24903(18) 0.0221(4) Uani 1 1 d . . . N9 N 0.2889(4) -0.3163(2) -0.0973(3) 0.0487(7) Uani 1 1 d . . . C2 C 0.4931(3) 0.0312(2) -0.1837(2) 0.0234(5) Uani 1 1 d . . . H2A H 0.4581 0.0701 -0.1081 0.028 Uiso 1 1 calc R . . C4 C 0.6438(3) -0.0215(2) -0.3513(2) 0.0250(5) Uani 1 1 d . . . H4A H 0.7336 -0.0244 -0.4130 0.030 Uiso 1 1 calc R . . C5 C 0.4986(3) -0.0918(2) -0.3477(2) 0.0244(5) Uani 1 1 d . . . H5A H 0.4670 -0.1531 -0.4061 0.029 Uiso 1 1 calc R . . C6 C 0.2353(3) -0.1054(2) -0.2002(2) 0.0252(5) Uani 1 1 d . . . H6A H 0.1893 -0.0520 -0.1324 0.030 Uiso 1 1 calc R . . C7 C 0.0989(3) -0.1106(3) -0.3078(3) 0.0320(5) Uani 1 1 d . . . H7A H 0.0836 -0.0310 -0.3447 0.048 Uiso 1 1 calc R . . H7B H -0.0140 -0.1385 -0.2749 0.048 Uiso 1 1 calc R . . H7C H 0.1391 -0.1658 -0.3734 0.048 Uiso 1 1 calc R . . C8 C 0.2673(3) -0.2253(2) -0.1439(2) 0.0303(5) Uani 1 1 d . . . C10 C 0.7759(4) 0.1394(2) -0.2089(3) 0.0298(6) Uani 1 1 d . . . H10A H 0.7281 0.1953 -0.1467 0.045 Uiso 1 1 calc R . . H10B H 0.8169 0.1837 -0.2830 0.045 Uiso 1 1 calc R . . H10C H 0.8752 0.0956 -0.1701 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 Br 0.03005(17) 0.02652(16) 0.02165(16) 0.00123(8) 0.00620(10) 0.00374(9) N1 0.0222(9) 0.0225(9) 0.0220(9) 0.0006(7) 0.0029(7) 0.0017(8) N3 0.0224(9) 0.0226(9) 0.0213(9) 0.0026(7) 0.0003(7) 0.0015(8) N9 0.0594(17) 0.0368(12) 0.0505(16) 0.0103(13) 0.0165(14) 0.0030(12) C2 0.0249(11) 0.0222(11) 0.0231(11) 0.0014(8) 0.0039(9) 0.0026(9) C4 0.0252(11) 0.0299(12) 0.0200(11) 0.0013(9) 0.0024(9) 0.0033(9) C5 0.0252(11) 0.0281(12) 0.0199(11) -0.0033(9) 0.0017(9) 0.0039(9) C6 0.0248(11) 0.0254(11) 0.0257(12) 0.0000(9) 0.0102(9) -0.0011(9) C7 0.0226(12) 0.0380(14) 0.0357(14) 0.0012(12) 0.0047(10) 0.0001(11) C8 0.0328(13) 0.0278(12) 0.0308(13) 0.0012(10) 0.0092(10) -0.0043(10) C10 0.0280(13) 0.0281(13) 0.0333(14) 0.0014(10) -0.0030(11) -0.0046(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 N1 C2 1.334(3) . ? N1 C5 1.378(3) . ? N1 C6 1.478(3) . ? N3 C2 1.330(3) . ? N3 C4 1.377(3) . ? N3 C10 1.469(3) . ? N9 C8 1.143(4) . ? C4 C5 1.354(3) . ? C6 C8 1.487(3) . ? C6 C7 1.518(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C5 109.09(18) . . ? C2 N1 C6 124.03(18) . . ? C5 N1 C6 126.9(2) . . ? C2 N3 C4 108.68(19) . . ? C2 N3 C10 124.8(2) . . ? C4 N3 C10 126.18(19) . . ? N3 C2 N1 108.3(2) . . ? C5 C4 N3 107.45(19) . . ? C4 C5 N1 106.5(2) . . ? N1 C6 C8 108.50(19) . . ? N1 C6 C7 111.94(19) . . ? C8 C6 C7 111.4(2) . . ? N9 C8 C6 177.8(3) . . ? _diffrn_measured_fraction_theta_max 0.948 _diffrn_reflns_theta_full 25.30 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.110 _refine_diff_density_min -1.090 _refine_diff_density_rms 0.104 data_4[N(CN)2] _database_code_depnum_ccdc_archive 'CCDC 801104' #TrackingRef 'Drab-Rogers-New-J-Chem-cif-11-10-10.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H8 N6' _chemical_formula_weight 188.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.8154(11) _cell_length_b 18.401(3) _cell_length_c 7.0641(10) _cell_angle_alpha 90.00 _cell_angle_beta 112.283(2) _cell_angle_gamma 90.00 _cell_volume 940.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2674 _cell_measurement_theta_min 2.82 _cell_measurement_theta_max 23.20 _exptl_crystal_description fragment _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8855833 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS, Sheldrick 2002' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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_reflns_number 4233 _diffrn_reflns_av_R_equivalents 0.0221 _diffrn_reflns_av_sigmaI/netI 0.0202 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 23.21 _reflns_number_total 1338 _reflns_number_gt 1200 _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, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0526P)^2^+0.3177P] 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 1338 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0416 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.0961 _refine_ls_wR_factor_gt 0.0925 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.37109(17) 0.35248(7) 0.51989(19) 0.0256(4) Uani 1 1 d . . . N3 N 0.08385(17) 0.37520(7) 0.34814(19) 0.0289(4) Uani 1 1 d . . . N8 N 0.7012(2) 0.26088(10) 0.9029(2) 0.0459(4) Uani 1 1 d . . . N10 N 0.6805(2) 0.61065(8) 1.0418(2) 0.0409(4) Uani 1 1 d . . . N12 N 1.0173(3) 0.60143(11) 1.2192(3) 0.0620(6) Uani 1 1 d . . . N14 N 0.4906(2) 0.53357(8) 0.7537(2) 0.0373(4) Uani 1 1 d . . . C2 C 0.2442(2) 0.40448(9) 0.4636(2) 0.0277(4) Uani 1 1 d . . . H2A H 0.2648 0.4543 0.5000 0.033 Uiso 1 1 calc R . . C4 C 0.1085(2) 0.30186(9) 0.3309(3) 0.0323(4) Uani 1 1 d . . . H4A H 0.0160 0.2677 0.2575 0.039 Uiso 1 1 calc R . . C5 C 0.2886(2) 0.28762(9) 0.4378(3) 0.0309(4) Uani 1 1 d . . . H5A H 0.3474 0.2416 0.4536 0.037 Uiso 1 1 calc R . . C6 C 0.5674(2) 0.36521(9) 0.6401(2) 0.0304(4) Uani 1 1 d . . . H6A H 0.6360 0.3674 0.5477 0.036 Uiso 1 1 calc R . . H6B H 0.5828 0.4124 0.7120 0.036 Uiso 1 1 calc R . . C7 C 0.6426(2) 0.30706(10) 0.7892(3) 0.0314(4) Uani 1 1 d . . . C9 C -0.0934(2) 0.41374(11) 0.2606(3) 0.0441(5) Uani 1 1 d . . . H9A H -0.0770 0.4642 0.3085 0.066 Uiso 1 1 calc R . . H9B H -0.1846 0.3898 0.3039 0.066 Uiso 1 1 calc R . . H9C H -0.1369 0.4129 0.1110 0.066 Uiso 1 1 calc R . . C11 C 0.8601(3) 0.60313(10) 1.1297(3) 0.0382(5) Uani 1 1 d . . . C13 C 0.5865(2) 0.56777(9) 0.8902(3) 0.0287(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0227(7) 0.0264(7) 0.0265(7) 0.0000(6) 0.0081(6) -0.0011(6) N3 0.0244(8) 0.0316(8) 0.0291(8) -0.0004(6) 0.0085(6) 0.0027(6) N8 0.0364(9) 0.0558(11) 0.0414(9) 0.0129(9) 0.0101(7) 0.0014(8) N10 0.0383(10) 0.0330(9) 0.0482(10) -0.0131(7) 0.0129(8) -0.0054(7) N12 0.0398(12) 0.0822(15) 0.0544(11) -0.0112(10) 0.0072(9) -0.0172(10) N14 0.0350(9) 0.0390(9) 0.0355(9) -0.0021(7) 0.0108(7) -0.0009(7) C2 0.0288(10) 0.0268(9) 0.0283(9) -0.0021(7) 0.0117(7) 0.0004(7) C4 0.0280(10) 0.0295(10) 0.0365(10) -0.0042(8) 0.0089(8) -0.0044(7) C5 0.0307(10) 0.0237(9) 0.0366(10) -0.0015(7) 0.0107(8) -0.0007(7) C6 0.0242(9) 0.0303(9) 0.0330(9) -0.0007(7) 0.0067(7) -0.0021(7) C7 0.0242(9) 0.0388(10) 0.0293(9) -0.0034(9) 0.0080(7) -0.0034(8) C9 0.0293(10) 0.0497(12) 0.0466(11) -0.0004(9) 0.0068(8) 0.0111(9) C11 0.0441(14) 0.0371(11) 0.0342(10) -0.0067(8) 0.0158(10) -0.0136(8) C13 0.0300(9) 0.0256(9) 0.0330(10) 0.0042(8) 0.0150(8) 0.0022(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.326(2) . ? N1 C5 1.376(2) . ? N1 C6 1.463(2) . ? N3 C2 1.323(2) . ? N3 C4 1.375(2) . ? N3 C9 1.468(2) . ? N8 C7 1.139(2) . ? N10 C13 1.309(2) . ? N10 C11 1.309(2) . ? N12 C11 1.149(2) . ? N14 C13 1.157(2) . ? C4 C5 1.347(2) . ? C6 C7 1.460(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C5 108.78(13) . . ? C2 N1 C6 123.98(13) . . ? C5 N1 C6 127.16(13) . . ? C2 N3 C4 108.83(13) . . ? C2 N3 C9 125.79(15) . . ? C4 N3 C9 125.33(15) . . ? C13 N10 C11 119.50(15) . . ? N3 C2 N1 108.47(14) . . ? C5 C4 N3 107.03(14) . . ? C4 C5 N1 106.89(14) . . ? C7 C6 N1 110.38(13) . . ? N8 C7 C6 178.80(18) . . ? N12 C11 N10 173.7(2) . . ? N14 C13 N10 174.21(17) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 23.21 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.221 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.037 data_4[NO3] _database_code_depnum_ccdc_archive 'CCDC 801105' #TrackingRef 'Drab-Rogers-New-J-Chem-cif-11-10-10.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H8 N4 O3' _chemical_formula_weight 184.16 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7192(13) _cell_length_b 9.8611(14) _cell_length_c 11.1363(16) _cell_angle_alpha 93.588(3) _cell_angle_beta 108.321(2) _cell_angle_gamma 112.598(2) _cell_volume 820.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3116 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 27.85 _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.64 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.491 _exptl_crystal_density_method none _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.69940 _exptl_absorpt_correction_T_max 0.898 _exptl_absorpt_process_details 'SADABS, Sheldrick, 2002' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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_reflns_number 5693 _diffrn_reflns_av_R_equivalents 0.0196 _diffrn_reflns_av_sigmaI/netI 0.0331 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 28.31 _reflns_number_total 3666 _reflns_number_gt 2956 _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, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1372P)^2^+1.1817P] 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 3666 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0648 _refine_ls_R_factor_gt 0.0514 _refine_ls_wR_factor_ref 0.1742 _refine_ls_wR_factor_gt 0.1594 _refine_ls_goodness_of_fit_ref 0.769 _refine_ls_restrained_S_all 0.769 _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 O1B O 0.7187(2) 0.2900(2) -0.06307(17) 0.0359(4) Uani 1 1 d . . . O2B O 0.9805(2) 0.3054(2) -0.04217(18) 0.0383(4) Uani 1 1 d . . . O3B O 0.8474(2) 0.18969(19) 0.08110(15) 0.0326(4) Uani 1 1 d . . . O1A O 0.7311(2) 0.4983(2) 0.21665(18) 0.0401(4) Uani 1 1 d . . . O2A O 0.5073(2) 0.53011(19) 0.23450(16) 0.0338(4) Uani 1 1 d . . . O3A O 0.6209(2) 0.40361(17) 0.35766(14) 0.0294(4) Uani 1 1 d . . . N1B N 0.3358(2) 0.19277(18) 0.05073(15) 0.0206(4) Uani 1 1 d . . . N1A N 0.1182(2) 0.41996(18) 0.33743(16) 0.0201(4) Uani 1 1 d . . . N3B N 0.4434(2) 0.07446(18) 0.18491(16) 0.0209(4) Uani 1 1 d . . . N3A N 0.2050(2) 0.27347(19) 0.44750(16) 0.0221(4) Uani 1 1 d . . . N8B N 0.0924(3) 0.1003(2) -0.27078(19) 0.0350(5) Uani 1 1 d . . . N8A N 0.2566(3) 0.7989(2) 0.39455(19) 0.0333(4) Uani 1 1 d . . . N9B N 0.8491(2) 0.26200(19) -0.00815(16) 0.0230(4) Uani 1 1 d . . . N9A N 0.6208(2) 0.47795(18) 0.27030(16) 0.0220(4) Uani 1 1 d . . . C2B C 0.4732(3) 0.1568(2) 0.09801(19) 0.0214(4) Uani 1 1 d . . . H2BA H 0.5745 0.1854 0.0736 0.026 Uiso 1 1 calc R . . C2A C 0.2448(3) 0.3700(2) 0.37190(19) 0.0214(4) Uani 1 1 d . . . H2AA H 0.3455 0.3985 0.3468 0.026 Uiso 1 1 calc R . . C4B C 0.2822(3) 0.0564(2) 0.19343(19) 0.0230(4) Uani 1 1 d . . . H4BA H 0.2289 0.0022 0.2482 0.028 Uiso 1 1 calc R . . C4A C 0.0500(3) 0.2627(2) 0.46247(19) 0.0234(4) Uani 1 1 d . . . H4AA H -0.0075 0.2020 0.5122 0.028 Uiso 1 1 calc R . . C5B C 0.2145(3) 0.1304(2) 0.10915(19) 0.0216(4) Uani 1 1 d . . . H5BA H 0.1047 0.1379 0.0933 0.026 Uiso 1 1 calc R . . C5A C -0.0052(3) 0.3539(2) 0.39368(19) 0.0225(4) Uani 1 1 d . . . H5AA H -0.1085 0.3698 0.3854 0.027 Uiso 1 1 calc R . . C6B C 0.3194(3) 0.2809(2) -0.04914(19) 0.0247(4) Uani 1 1 d . . . H6BA H 0.4374 0.3354 -0.0558 0.030 Uiso 1 1 calc R . . H6BB H 0.2784 0.3558 -0.0257 0.030 Uiso 1 1 calc R . . C6A C 0.1146(3) 0.5277(2) 0.25327(19) 0.0242(4) Uani 1 1 d . . . H6AA H -0.0103 0.5008 0.1964 0.029 Uiso 1 1 calc R . . H6AB H 0.1827 0.5241 0.1978 0.029 Uiso 1 1 calc R . . C7B C 0.1902(3) 0.1808(2) -0.1751(2) 0.0258(4) Uani 1 1 d . . . C7A C 0.1936(3) 0.6813(2) 0.3320(2) 0.0243(4) Uani 1 1 d . . . C9B C 0.5672(3) 0.0194(3) 0.2634(2) 0.0313(5) Uani 1 1 d . . . H9BA H 0.6717 0.0481 0.2383 0.047 Uiso 1 1 calc R . . H9BB H 0.5074 -0.0902 0.2495 0.047 Uiso 1 1 calc R . . H9BC H 0.6055 0.0636 0.3550 0.047 Uiso 1 1 calc R . . C9A C 0.3122(3) 0.1944(3) 0.5062(2) 0.0296(5) Uani 1 1 d . . . H9AA H 0.4148 0.2217 0.4789 0.044 Uiso 1 1 calc R . . H9AB H 0.2389 0.0857 0.4782 0.044 Uiso 1 1 calc R . . H9AC H 0.3547 0.2229 0.6006 0.044 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 O1B 0.0278(8) 0.0493(10) 0.0394(9) 0.0205(8) 0.0148(7) 0.0217(8) O2B 0.0325(9) 0.0465(10) 0.0514(10) 0.0239(8) 0.0277(8) 0.0205(8) O3B 0.0360(9) 0.0426(9) 0.0265(8) 0.0160(7) 0.0159(7) 0.0193(7) O1A 0.0410(10) 0.0528(11) 0.0539(11) 0.0300(9) 0.0356(9) 0.0304(9) O2A 0.0333(9) 0.0417(9) 0.0429(9) 0.0212(8) 0.0211(7) 0.0252(7) O3A 0.0317(8) 0.0309(8) 0.0276(8) 0.0136(6) 0.0127(7) 0.0127(7) N1B 0.0208(8) 0.0214(8) 0.0196(8) 0.0067(6) 0.0083(6) 0.0078(6) N1A 0.0233(8) 0.0187(7) 0.0199(8) 0.0063(6) 0.0088(6) 0.0096(6) N3B 0.0206(8) 0.0206(8) 0.0201(8) 0.0046(6) 0.0051(6) 0.0092(6) N3A 0.0246(8) 0.0208(8) 0.0222(8) 0.0055(6) 0.0082(7) 0.0111(7) N8B 0.0374(11) 0.0407(11) 0.0253(10) 0.0104(8) 0.0084(8) 0.0170(9) N8A 0.0413(11) 0.0274(10) 0.0341(10) 0.0102(8) 0.0161(9) 0.0153(8) N9B 0.0237(8) 0.0239(8) 0.0213(8) 0.0030(6) 0.0094(7) 0.0094(7) N9A 0.0213(8) 0.0203(8) 0.0251(8) 0.0049(6) 0.0100(7) 0.0082(6) C2B 0.0210(9) 0.0212(9) 0.0218(9) 0.0049(7) 0.0094(7) 0.0075(7) C2A 0.0226(9) 0.0213(9) 0.0230(9) 0.0045(7) 0.0100(7) 0.0109(7) C4B 0.0243(10) 0.0228(9) 0.0206(9) 0.0062(7) 0.0100(8) 0.0073(8) C4A 0.0225(9) 0.0252(10) 0.0257(10) 0.0086(8) 0.0123(8) 0.0102(8) C5B 0.0192(9) 0.0234(9) 0.0222(9) 0.0053(7) 0.0096(7) 0.0075(7) C5A 0.0219(9) 0.0238(9) 0.0241(9) 0.0074(7) 0.0110(8) 0.0098(8) C6B 0.0279(10) 0.0245(10) 0.0230(10) 0.0122(8) 0.0105(8) 0.0106(8) C6A 0.0288(10) 0.0248(10) 0.0227(9) 0.0108(8) 0.0120(8) 0.0123(8) C7B 0.0283(10) 0.0314(11) 0.0240(10) 0.0137(9) 0.0126(9) 0.0154(9) C7A 0.0262(10) 0.0259(10) 0.0275(10) 0.0125(8) 0.0138(8) 0.0136(8) C9B 0.0295(11) 0.0329(11) 0.0297(11) 0.0105(9) 0.0042(9) 0.0163(9) C9A 0.0360(12) 0.0323(11) 0.0279(10) 0.0108(9) 0.0091(9) 0.0234(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 O1B N9B 1.253(2) . ? O2B N9B 1.247(2) . ? O3B N9B 1.260(2) . ? O1A N9A 1.245(2) . ? O2A N9A 1.254(2) . ? O3A N9A 1.254(2) . ? N1B C2B 1.339(3) . ? N1B C5B 1.379(2) . ? N1B C6B 1.459(2) . ? N1A C2A 1.335(3) . ? N1A C5A 1.382(3) . ? N1A C6A 1.463(2) . ? N3B C2B 1.326(3) . ? N3B C4B 1.382(3) . ? N3B C9B 1.463(3) . ? N3A C2A 1.329(3) . ? N3A C4A 1.378(3) . ? N3A C9A 1.466(3) . ? N8B C7B 1.138(3) . ? N8A C7A 1.141(3) . ? C4B C5B 1.353(3) . ? C4A C5A 1.347(3) . ? C6B C7B 1.479(3) . ? C6A C7A 1.480(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 C2B N1B C5B 109.06(16) . . ? C2B N1B C6B 124.08(17) . . ? C5B N1B C6B 126.84(17) . . ? C2A N1A C5A 109.17(16) . . ? C2A N1A C6A 124.29(17) . . ? C5A N1A C6A 126.54(17) . . ? C2B N3B C4B 109.00(16) . . ? C2B N3B C9B 124.87(18) . . ? C4B N3B C9B 126.05(18) . . ? C2A N3A C4A 108.90(17) . . ? C2A N3A C9A 124.72(18) . . ? C4A N3A C9A 126.37(18) . . ? O2B N9B O1B 119.94(17) . . ? O2B N9B O3B 120.02(18) . . ? O1B N9B O3B 120.04(17) . . ? O1A N9A O2A 119.38(17) . . ? O1A N9A O3A 120.40(17) . . ? O2A N9A O3A 120.20(17) . . ? N3B C2B N1B 108.08(17) . . ? N3A C2A N1A 107.92(17) . . ? C5B C4B N3B 107.21(17) . . ? C5A C4A N3A 107.54(18) . . ? C4B C5B N1B 106.65(17) . . ? C4A C5A N1A 106.47(18) . . ? N1B C6B C7B 109.92(16) . . ? N1A C6A C7A 110.13(16) . . ? N8B C7B C6B 177.9(2) . . ? N8A C7A C6A 178.7(2) . . ? _diffrn_measured_fraction_theta_max 0.895 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.895 _refine_diff_density_max 0.443 _refine_diff_density_min -0.328 _refine_diff_density_rms 0.070