# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Anne Petitjean' _publ_contact_author_email ANNE.PETITJEAN@CHEM.QUEENSU.CA _publ_section_title ; Functional formamidines: pyridine substituents make an exception in the usual doubly hydrogen-bonded formamidine dimer. ; loop_ _publ_author_name 'Anne Petitjean' 'Ruiyao Wang.' 'Liyan Xing.' # Attachment 'ap04t.cif' data_ap04t _database_code_depnum_ccdc_archive 'CCDC 714104' #TrackingRef 'ap04t.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H10 N4' _chemical_formula_weight 198.23 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/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 10.9881(19) _cell_length_b 4.3351(7) _cell_length_c 20.561(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.561(3) _cell_angle_gamma 90.00 _cell_volume 968.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 3649 _cell_measurement_theta_min 3.30 _cell_measurement_theta_max 28.29 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.360 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9701 _exptl_absorpt_correction_T_max 0.9870 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 5802 _diffrn_reflns_av_R_equivalents 0.0399 _diffrn_reflns_av_sigmaI/netI 0.0331 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 25.99 _reflns_number_total 1911 _reflns_number_gt 1503 _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^)+(0.0559P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1911 _refine_ls_number_parameters 176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0893 _refine_ls_wR_factor_gt 0.0843 _refine_ls_goodness_of_fit_ref 0.973 _refine_ls_restrained_S_all 0.973 _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 0.21824(9) -0.0867(2) 0.39925(5) 0.0342(3) Uani 1 1 d . . . N2 N 0.08838(9) 0.2169(2) 0.45294(5) 0.0315(3) Uani 1 1 d . . . H2N H 0.0160(13) 0.287(3) 0.4526(6) 0.043(4) Uiso 1 1 d . . . N3 N 0.16555(8) 0.5298(2) 0.54018(5) 0.0321(3) Uani 1 1 d . . . N4 N 0.26050(9) 0.7000(2) 0.64219(5) 0.0386(3) Uani 1 1 d . . . C1 C 0.23093(12) -0.2904(3) 0.35164(6) 0.0368(3) Uani 1 1 d . . . H1 H 0.3146(13) -0.357(3) 0.3482(6) 0.044(3) Uiso 1 1 d . . . C2 C 0.13487(12) -0.4103(3) 0.30884(6) 0.0394(3) Uani 1 1 d . . . H2 H 0.1504(11) -0.559(3) 0.2748(6) 0.042(3) Uiso 1 1 d . . . C3 C 0.01654(12) -0.3168(3) 0.31564(6) 0.0386(3) Uani 1 1 d . . . H3 H -0.0545(13) -0.389(3) 0.2875(7) 0.048(4) Uiso 1 1 d . . . C4 C 0.00016(11) -0.1087(3) 0.36371(6) 0.0346(3) Uani 1 1 d . . . H4 H -0.0764(12) -0.036(3) 0.3689(6) 0.040(3) Uiso 1 1 d . . . C5 C 0.10351(10) 0.0017(2) 0.40434(5) 0.0300(3) Uani 1 1 d . . . C6 C 0.18197(11) 0.3301(2) 0.49616(6) 0.0305(3) Uani 1 1 d . . . H6 H 0.2607(10) 0.243(2) 0.4911(5) 0.027(3) Uiso 1 1 d . . . C7 C 0.27268(10) 0.6418(2) 0.57957(6) 0.0317(3) Uani 1 1 d . . . C8 C 0.38148(11) 0.7037(3) 0.55424(6) 0.0357(3) Uani 1 1 d . . . H8 H 0.3825(10) 0.676(3) 0.5082(6) 0.034(3) Uiso 1 1 d . . . C9 C 0.48061(12) 0.8221(3) 0.59573(7) 0.0410(3) Uani 1 1 d . . . H9 H 0.5544(12) 0.871(3) 0.5782(6) 0.044(4) Uiso 1 1 d . . . C10 C 0.46936(12) 0.8790(3) 0.66039(7) 0.0426(3) Uani 1 1 d . . . H10 H 0.5354(12) 0.957(3) 0.6906(6) 0.050(4) Uiso 1 1 d . . . C11 C 0.35859(12) 0.8164(3) 0.68104(7) 0.0432(3) Uani 1 1 d . . . H11 H 0.3469(12) 0.853(3) 0.7276(7) 0.044(3) 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 N1 0.0280(5) 0.0359(5) 0.0395(6) 0.0034(4) 0.0076(4) 0.0014(4) N2 0.0235(5) 0.0344(5) 0.0366(6) 0.0007(4) 0.0048(4) 0.0025(4) N3 0.0250(5) 0.0368(5) 0.0344(5) 0.0018(4) 0.0043(4) 0.0008(4) N4 0.0305(6) 0.0476(6) 0.0373(6) -0.0017(5) 0.0036(4) 0.0024(4) C1 0.0341(7) 0.0369(6) 0.0415(7) 0.0019(5) 0.0121(6) 0.0021(5) C2 0.0470(8) 0.0348(6) 0.0380(7) 0.0005(6) 0.0119(6) -0.0015(6) C3 0.0374(7) 0.0377(7) 0.0396(7) 0.0025(6) 0.0020(6) -0.0055(5) C4 0.0277(7) 0.0347(6) 0.0413(7) 0.0030(5) 0.0048(5) 0.0006(5) C5 0.0286(6) 0.0287(5) 0.0334(6) 0.0065(5) 0.0065(5) 0.0003(5) C6 0.0247(6) 0.0326(6) 0.0349(6) 0.0058(5) 0.0067(5) 0.0020(5) C7 0.0255(6) 0.0324(6) 0.0366(6) 0.0033(5) 0.0028(5) 0.0045(5) C8 0.0298(6) 0.0418(7) 0.0356(7) 0.0019(6) 0.0050(5) 0.0013(5) C9 0.0273(7) 0.0470(7) 0.0490(8) 0.0023(6) 0.0062(6) -0.0011(5) C10 0.0308(7) 0.0492(8) 0.0450(8) -0.0033(6) -0.0037(6) -0.0021(6) C11 0.0369(7) 0.0538(8) 0.0376(7) -0.0043(6) 0.0010(6) 0.0029(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C5 1.3365(14) . ? N1 C1 1.3408(16) . ? N2 C6 1.3476(15) . ? N2 C5 1.3950(15) . ? N2 H2N 0.850(14) . ? N3 C6 1.2847(15) . ? N3 C7 1.4119(14) . ? N4 C7 1.3383(15) . ? N4 C11 1.3409(16) . ? C1 C2 1.3720(18) . ? C1 H1 0.976(14) . ? C2 C3 1.3888(18) . ? C2 H2 0.984(13) . ? C3 C4 1.3697(17) . ? C3 H3 0.952(14) . ? C4 C5 1.3907(16) . ? C4 H4 0.919(13) . ? C6 H6 0.964(11) . ? C7 C8 1.3992(16) . ? C8 C9 1.3787(17) . ? C8 H8 0.956(12) . ? C9 C10 1.3757(18) . ? C9 H9 0.959(13) . ? C10 C11 1.3744(18) . ? C10 H10 0.945(14) . ? C11 H11 0.998(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N1 C1 116.60(10) . . ? C6 N2 C5 123.72(10) . . ? C6 N2 H2N 119.8(9) . . ? C5 N2 H2N 116.3(9) . . ? C6 N3 C7 116.31(10) . . ? C7 N4 C11 117.22(11) . . ? N1 C1 C2 124.35(12) . . ? N1 C1 H1 116.7(7) . . ? C2 C1 H1 119.0(7) . . ? C1 C2 C3 117.85(12) . . ? C1 C2 H2 120.4(7) . . ? C3 C2 H2 121.8(7) . . ? C4 C3 C2 119.38(12) . . ? C4 C3 H3 118.0(8) . . ? C2 C3 H3 122.6(8) . . ? C3 C4 C5 118.47(11) . . ? C3 C4 H4 122.1(8) . . ? C5 C4 H4 119.4(8) . . ? N1 C5 C4 123.35(11) . . ? N1 C5 N2 117.53(10) . . ? C4 C5 N2 119.11(10) . . ? N3 C6 N2 122.45(11) . . ? N3 C6 H6 124.3(6) . . ? N2 C6 H6 113.2(6) . . ? N4 C7 C8 122.37(11) . . ? N4 C7 N3 114.99(10) . . ? C8 C7 N3 122.56(11) . . ? C9 C8 C7 118.77(12) . . ? C9 C8 H8 122.3(7) . . ? C7 C8 H8 118.8(7) . . ? C10 C9 C8 119.23(12) . . ? C10 C9 H9 121.7(8) . . ? C8 C9 H9 119.0(8) . . ? C11 C10 C9 118.31(12) . . ? C11 C10 H10 119.8(8) . . ? C9 C10 H10 121.9(8) . . ? N4 C11 C10 124.09(12) . . ? N4 C11 H11 115.2(8) . . ? C10 C11 H11 120.8(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 C5 N1 C1 C2 0.01(17) . . . . ? N1 C1 C2 C3 -0.60(18) . . . . ? C1 C2 C3 C4 0.64(17) . . . . ? C2 C3 C4 C5 -0.12(17) . . . . ? C1 N1 C5 C4 0.57(16) . . . . ? C1 N1 C5 N2 -179.08(10) . . . . ? C3 C4 C5 N1 -0.51(17) . . . . ? C3 C4 C5 N2 179.13(10) . . . . ? C6 N2 C5 N1 -2.64(16) . . . . ? C6 N2 C5 C4 177.70(10) . . . . ? C7 N3 C6 N2 -176.32(10) . . . . ? C5 N2 C6 N3 179.54(10) . . . . ? C11 N4 C7 C8 -1.27(17) . . . . ? C11 N4 C7 N3 -177.86(10) . . . . ? C6 N3 C7 N4 -144.63(10) . . . . ? C6 N3 C7 C8 38.79(15) . . . . ? N4 C7 C8 C9 1.60(18) . . . . ? N3 C7 C8 C9 177.93(11) . . . . ? C7 C8 C9 C10 -0.74(19) . . . . ? C8 C9 C10 C11 -0.3(2) . . . . ? C7 N4 C11 C10 0.11(19) . . . . ? C9 C10 C11 N4 0.7(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2N N3 0.850(14) 2.173(15) 3.0212(14) 175.6(12) 3_566 C4 H4 N4 0.919(13) 2.475(14) 3.3545(16) 160.2(10) 3_566 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.143 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.031 # Attachment 'ap11.cif' data_ap11 _database_code_depnum_ccdc_archive 'CCDC 753174' #TrackingRef 'ap11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H10 N4' _chemical_formula_weight 198.23 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 Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 11.7861(5) _cell_length_b 7.2290(3) _cell_length_c 23.2069(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1977.27(14) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 3781 _cell_measurement_theta_min 3.42 _cell_measurement_theta_max 27.14 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9790 _exptl_absorpt_correction_T_max 0.9831 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6973 _diffrn_reflns_av_R_equivalents 0.0156 _diffrn_reflns_av_sigmaI/netI 0.0142 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 25.99 _reflns_number_total 1938 _reflns_number_gt 1764 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0488P)^2^+0.4557P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0100(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1938 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0357 _refine_ls_R_factor_gt 0.0322 _refine_ls_wR_factor_ref 0.0893 _refine_ls_wR_factor_gt 0.0855 _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 N1 N 0.37841(8) 0.20243(14) 0.50825(4) 0.0293(2) Uani 1 1 d . . . N2 N -0.15911(8) -0.14648(14) 0.19459(4) 0.0304(3) Uani 1 1 d . . . N3 N 0.06184(8) 0.11757(14) 0.43019(4) 0.0260(2) Uani 1 1 d . . . H3N H 0.0038(12) 0.167(2) 0.4502(5) 0.037(4) Uiso 1 1 d . . . N4 N -0.06573(8) 0.03481(14) 0.36089(4) 0.0278(2) Uani 1 1 d . . . C1 C 0.27986(9) 0.23706(16) 0.53486(4) 0.0276(3) Uani 1 1 d . . . H1A H 0.2825 0.2863 0.5728 0.033 Uiso 1 1 calc R . . C2 C 0.17520(9) 0.20576(16) 0.51074(4) 0.0256(3) Uani 1 1 d . . . H2A H 0.1080 0.2297 0.5321 0.031 Uiso 1 1 calc R . . C3 C 0.16863(9) 0.13829(15) 0.45442(4) 0.0227(2) Uani 1 1 d . . . C4 C 0.27018(9) 0.09892(16) 0.42624(4) 0.0263(3) Uani 1 1 d . . . H4A H 0.2703 0.0505 0.3882 0.032 Uiso 1 1 calc R . . C5 C 0.37029(10) 0.13187(16) 0.45491(5) 0.0295(3) Uani 1 1 d . . . H5A H 0.4389 0.1024 0.4355 0.035 Uiso 1 1 calc R . . C6 C -0.22343(9) -0.17399(16) 0.24133(5) 0.0289(3) Uani 1 1 d . . . H6A H -0.2942 -0.2346 0.2363 0.035 Uiso 1 1 calc R . . C7 C -0.19374(9) -0.12008(16) 0.29639(5) 0.0275(3) Uani 1 1 d . . . H7A H -0.2436 -0.1430 0.3278 0.033 Uiso 1 1 calc R . . C8 C -0.09004(9) -0.03174(15) 0.30568(4) 0.0235(2) Uani 1 1 d . . . C9 C -0.02133(9) -0.00417(15) 0.25719(4) 0.0247(3) Uani 1 1 d . . . H9A H 0.0505 0.0542 0.2608 0.030 Uiso 1 1 calc R . . C10 C -0.05953(10) -0.06307(16) 0.20398(5) 0.0290(3) Uani 1 1 d . . . H10A H -0.0115 -0.0428 0.1717 0.035 Uiso 1 1 calc R . . C11 C 0.03741(9) 0.04107(15) 0.37838(4) 0.0237(2) Uani 1 1 d . . . H11A H 0.0965 -0.0078 0.3551 0.028 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0245(5) 0.0346(6) 0.0287(5) -0.0034(4) -0.0031(4) -0.0017(4) N2 0.0364(6) 0.0291(5) 0.0257(5) -0.0010(4) -0.0084(4) 0.0007(4) N3 0.0208(5) 0.0361(5) 0.0210(4) -0.0043(4) -0.0005(4) 0.0013(4) N4 0.0240(5) 0.0376(6) 0.0219(4) -0.0039(4) -0.0009(4) -0.0013(4) C1 0.0291(6) 0.0324(6) 0.0214(5) -0.0022(4) -0.0023(4) -0.0016(5) C2 0.0249(6) 0.0312(6) 0.0206(5) -0.0014(4) 0.0021(4) -0.0001(4) C3 0.0229(5) 0.0238(5) 0.0214(5) 0.0011(4) -0.0012(4) -0.0005(4) C4 0.0258(6) 0.0302(6) 0.0228(5) -0.0044(4) 0.0007(4) 0.0000(4) C5 0.0235(6) 0.0342(6) 0.0307(6) -0.0048(5) 0.0012(4) 0.0012(5) C6 0.0267(6) 0.0259(5) 0.0343(6) 0.0004(5) -0.0086(4) -0.0010(4) C7 0.0238(5) 0.0315(6) 0.0273(5) 0.0022(5) -0.0008(4) -0.0009(5) C8 0.0231(5) 0.0250(5) 0.0224(5) -0.0004(4) -0.0032(4) 0.0028(4) C9 0.0232(5) 0.0246(5) 0.0262(5) -0.0003(4) -0.0016(4) -0.0002(4) C10 0.0348(6) 0.0294(6) 0.0228(5) 0.0010(4) 0.0003(4) 0.0009(5) C11 0.0246(5) 0.0270(6) 0.0196(5) -0.0001(4) 0.0008(4) -0.0007(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.3390(14) . ? N1 C5 1.3422(14) . ? N2 C10 1.3374(15) . ? N2 C6 1.3383(15) . ? N3 C11 1.3544(13) . ? N3 C3 1.3867(13) . ? N3 H3N 0.900(14) . ? N4 C11 1.2824(14) . ? N4 C8 1.3983(13) . ? C1 C2 1.3734(15) . ? C1 H1A 0.9500 . ? C2 C3 1.3972(14) . ? C2 H2A 0.9500 . ? C3 C4 1.3932(15) . ? C4 C5 1.3753(15) . ? C4 H4A 0.9500 . ? C5 H5A 0.9500 . ? C6 C7 1.3811(15) . ? C6 H6A 0.9500 . ? C7 C8 1.3958(15) . ? C7 H7A 0.9500 . ? C8 C9 1.4006(15) . ? C9 C10 1.3817(15) . ? C9 H9A 0.9500 . ? C10 H10A 0.9500 . ? C11 H11A 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 C1 N1 C5 115.75(9) . . ? C10 N2 C6 115.59(9) . . ? C11 N3 C3 126.65(9) . . ? C11 N3 H3N 117.2(9) . . ? C3 N3 H3N 116.0(9) . . ? C11 N4 C8 119.76(9) . . ? N1 C1 C2 124.08(10) . . ? N1 C1 H1A 118.0 . . ? C2 C1 H1A 118.0 . . ? C1 C2 C3 119.24(10) . . ? C1 C2 H2A 120.4 . . ? C3 C2 H2A 120.4 . . ? N3 C3 C4 124.57(9) . . ? N3 C3 C2 117.86(9) . . ? C4 C3 C2 117.56(10) . . ? C5 C4 C3 118.33(10) . . ? C5 C4 H4A 120.8 . . ? C3 C4 H4A 120.8 . . ? N1 C5 C4 124.97(10) . . ? N1 C5 H5A 117.5 . . ? C4 C5 H5A 117.5 . . ? N2 C6 C7 124.37(10) . . ? N2 C6 H6A 117.8 . . ? C7 C6 H6A 117.8 . . ? C6 C7 C8 119.59(10) . . ? C6 C7 H7A 120.2 . . ? C8 C7 H7A 120.2 . . ? C7 C8 N4 118.57(10) . . ? C7 C8 C9 116.57(9) . . ? N4 C8 C9 124.67(10) . . ? C10 C9 C8 119.07(10) . . ? C10 C9 H9A 120.5 . . ? C8 C9 H9A 120.5 . . ? N2 C10 C9 124.79(10) . . ? N2 C10 H10A 117.6 . . ? C9 C10 H10A 117.6 . . ? N4 C11 N3 119.79(10) . . ? N4 C11 H11A 120.1 . . ? N3 C11 H11A 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 C5 N1 C1 C2 -0.39(17) . . . . ? N1 C1 C2 C3 -1.80(18) . . . . ? C11 N3 C3 C4 6.61(18) . . . . ? C11 N3 C3 C2 -174.32(10) . . . . ? C1 C2 C3 N3 -176.59(10) . . . . ? C1 C2 C3 C4 2.54(16) . . . . ? N3 C3 C4 C5 177.86(11) . . . . ? C2 C3 C4 C5 -1.21(16) . . . . ? C1 N1 C5 C4 1.88(18) . . . . ? C3 C4 C5 N1 -1.07(18) . . . . ? C10 N2 C6 C7 0.95(17) . . . . ? N2 C6 C7 C8 -0.46(18) . . . . ? C6 C7 C8 N4 174.94(10) . . . . ? C6 C7 C8 C9 -0.33(16) . . . . ? C11 N4 C8 C7 149.62(11) . . . . ? C11 N4 C8 C9 -35.52(16) . . . . ? C7 C8 C9 C10 0.56(15) . . . . ? N4 C8 C9 C10 -174.39(10) . . . . ? C6 N2 C10 C9 -0.69(17) . . . . ? C8 C9 C10 N2 -0.05(17) . . . . ? C8 N4 C11 N3 175.33(10) . . . . ? C3 N3 C11 N4 -178.47(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3N N1 0.900(14) 2.001(15) 2.8996(13) 175.2(13) 2_456 C4 H4A N2 0.95 2.53 3.4212(14) 155.9 8_656 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.183 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.037