# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_coanp _audit_contact_author 'M.Bonin* & K.Schenk**' _chemical_name_systematic ; 2-(Cyclo-octylamino)-5-nitropyridine ; _chemical_name_common coanp _chemical_melting_point unknown _chemical_formula_moiety 'C13 H19 N3 O2' _chemical_formula_sum 'C13 H19 N3 O2' _chemical_formula_weight 249.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c a 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 26.010(5) _cell_length_b 6.6360(13) _cell_length_c 7.5136(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1296.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 17159 _cell_measurement_theta_min 1.70 _cell_measurement_theta_max 64.94 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.712 _exptl_absorpt_correction_type 'numerical on indexed faces' _exptl_absorpt_correction_details 'STOE X-RED' _exptl_absorpt_correction_T_min 0.8152 _exptl_absorpt_correction_T_max 0.9641 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 0 0.0180 -1 0 0 0.0330 -2 1 0 0.1270 -1 1 -1 0.1650 4 -1 0 0.0990 4 1 0 0.1100 -2 0 1 0.1380 -2 -1 0 0.1180 1 -1 -1 0.1660 2 0 1 0.1470 _exptl_special_details ; In order to improve the thermal stability of our experiment,we have placed the nozzle cooler device very near to our sample. Due to the nozzle's shadow on the image plate,integration was done with a mask,implying rejection of some reflections. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS 2T' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean 6.6 _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 9096 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0209 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.40 _diffrn_reflns_theta_max 64.72 _reflns_number_total 2055 _reflns_number_gt 1924 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA' _computing_data_reduction 'STOE X-RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SXGRAPH in WinGx 1.80.04' _computing_publication_material 'WinGx 1.80.04' _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^)+(0.0568P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(2) _refine_ls_number_reflns 2055 _refine_ls_number_parameters 175 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0325 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_ref 0.0814 _refine_ls_wR_factor_gt 0.0808 _refine_ls_goodness_of_fit_ref 1.165 _refine_ls_restrained_S_all 1.164 _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 C1 C 0.67464(6) 0.3919(3) 0.8275(2) 0.0140(4) Uani 1 1 d . . . C2 C 0.72815(6) 0.3949(3) 0.7906(2) 0.0141(4) Uani 1 1 d . . . H2 H 0.7480(4) 0.502(2) 0.8258(8) 0.017 Uiso 1 1 calc R . . C3 C 0.74946(7) 0.2378(2) 0.7026(2) 0.0151(4) Uani 1 1 d . . . H3 H 0.7829(8) 0.2345(2) 0.6799(5) 0.018 Uiso 1 1 calc R . . C4 C 0.71713(6) 0.0805(3) 0.6484(2) 0.0148(4) Uani 1 1 d . . . C5 C 0.66516(6) 0.0897(3) 0.6857(2) 0.0157(4) Uani 1 1 d . . . H5 H 0.6440(5) -0.017(2) 0.6458(9) 0.019 Uiso 1 1 calc R . . C6 C 0.60081(6) 0.5495(2) 0.9867(2) 0.0143(4) Uani 1 1 d . . . H6 H 0.5787(5) 0.5032(10) 0.8951(19) 0.017 Uiso 1 1 calc R . . C7 C 0.58841(6) 0.7703(3) 1.0234(2) 0.0197(4) Uani 1 1 d . . . H7A H 0.6127(4) 0.8196(8) 1.1158(14) 0.024 Uiso 1 1 calc R . . H7B H 0.59551(13) 0.8479(12) 0.9127(16) 0.024 Uiso 1 1 calc R . . C8 C 0.53404(6) 0.8217(3) 1.0843(2) 0.0229(4) Uani 1 1 d . . . H8A H 0.5101(4) 0.7683(8) 0.9958(14) 0.027 Uiso 1 1 calc R . . H8B H 0.53054(9) 0.968(2) 1.0830(2) 0.027 Uiso 1 1 calc R . . C9 C 0.51677(6) 0.7463(3) 1.2678(3) 0.0251(4) Uani 1 1 d . . . H9A H 0.50680(16) 0.604(2) 1.2572(3) 0.030 Uiso 1 1 calc R . . H9B H 0.4862(4) 0.8221(10) 1.3038(6) 0.030 Uiso 1 1 calc R . . C10 C 0.55749(7) 0.7649(3) 1.4161(3) 0.0273(5) Uani 1 1 d . . . H10A H 0.5822(4) 0.8682(17) 1.3811(6) 0.033 Uiso 1 1 calc R . . H10B H 0.5404(3) 0.8117(8) 1.5240(17) 0.033 Uiso 1 1 calc R . . C11 C 0.58702(7) 0.5734(3) 1.4603(2) 0.0266(5) Uani 1 1 d . . . H11A H 0.5612(4) 0.4679(18) 1.4966(6) 0.032 Uiso 1 1 calc R . . H11B H 0.6090(4) 0.6023(5) 1.5679(18) 0.032 Uiso 1 1 calc R . . C12 C 0.62181(6) 0.4801(3) 1.3180(2) 0.0209(4) Uani 1 1 d . . . H12A H 0.6401(3) 0.3634(16) 1.3720(8) 0.025 Uiso 1 1 calc R . . H12B H 0.6483(4) 0.5814(14) 1.2847(5) 0.025 Uiso 1 1 calc R . . C13 C 0.59537(6) 0.4074(3) 1.1467(2) 0.0185(4) Uani 1 1 d . . . H13A H 0.6095(2) 0.2773(19) 1.1146(5) 0.022 Uiso 1 1 calc R . . H13B H 0.5591(5) 0.3885(4) 1.1711(4) 0.022 Uiso 1 1 calc R . . N1 N 0.64343(5) 0.2398(2) 0.77469(18) 0.0164(3) Uani 1 1 d . . . N2 N 0.65364(5) 0.5442(2) 0.92037(17) 0.0152(3) Uani 1 1 d . . . H2A H 0.6728(4) 0.647(2) 0.9426(5) 0.018 Uiso 1 1 calc R . . N3 N 0.73801(5) -0.0916(2) 0.56015(19) 0.0189(3) Uani 1 1 d . . . O1 O 0.78527(4) -0.10379(19) 0.54566(18) 0.0268(3) Uani 1 1 d . . . O2 O 0.70882(5) -0.2205(2) 0.5011(2) 0.0355(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 C1 0.0175(9) 0.0160(10) 0.0084(8) 0.0027(7) -0.0019(6) -0.0023(7) C2 0.0162(8) 0.0136(10) 0.0127(8) -0.0005(7) -0.0008(6) -0.0025(7) C3 0.0123(7) 0.0218(10) 0.0111(8) 0.0029(7) 0.0032(6) -0.0007(7) C4 0.0189(9) 0.0164(10) 0.0090(8) 0.0017(6) 0.0015(6) 0.0019(6) C5 0.0211(9) 0.0149(10) 0.0111(8) -0.0013(7) -0.0014(7) -0.0031(7) C6 0.0114(7) 0.0163(10) 0.0153(8) -0.0036(7) -0.0001(6) -0.0024(6) C7 0.0196(9) 0.0202(11) 0.0193(9) 0.0031(7) 0.0018(7) -0.0006(7) C8 0.0183(8) 0.0234(11) 0.0270(9) 0.0010(8) -0.0028(7) 0.0053(7) C9 0.0155(9) 0.0333(13) 0.0263(9) -0.0049(7) 0.0043(8) 0.0076(8) C10 0.0242(9) 0.0390(12) 0.0187(9) -0.0099(8) 0.0044(7) 0.0118(8) C11 0.0250(9) 0.0403(13) 0.0144(9) -0.0016(8) 0.0014(7) 0.0028(8) C12 0.0209(9) 0.0233(11) 0.0184(8) 0.0037(8) 0.0024(7) 0.0082(7) C13 0.0169(9) 0.0155(10) 0.0232(9) -0.0025(7) 0.0053(7) 0.0009(6) N1 0.0169(7) 0.0185(9) 0.0138(7) -0.0017(5) 0.0002(6) -0.0007(6) N2 0.0149(7) 0.0145(8) 0.0162(7) -0.0053(6) 0.0021(6) -0.0035(6) N3 0.0251(8) 0.0175(9) 0.0141(6) -0.0008(6) 0.0040(6) 0.0027(6) O1 0.0225(7) 0.0253(8) 0.0326(7) -0.0050(6) 0.0063(5) 0.0080(5) O2 0.0329(7) 0.0279(8) 0.0457(9) -0.0215(7) 0.0027(6) -0.0027(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 C1 N2 1.344(2) . ? C1 N1 1.355(2) . ? C1 C2 1.419(2) . ? C2 C3 1.353(2) . ? C3 C4 1.401(2) . ? C4 C5 1.382(2) . ? C4 N3 1.428(2) . ? C5 N1 1.326(2) . ? C6 N2 1.462(2) . ? C6 C7 1.526(2) . ? C6 C13 1.534(2) . ? C7 C8 1.525(2) . ? C8 C9 1.535(3) . ? C9 C10 1.542(3) . ? C10 C11 1.522(3) . ? C11 C12 1.532(2) . ? C12 C13 1.537(2) . ? N3 O2 1.2266(18) . ? N3 O1 1.2369(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 N1 117.96(14) . . ? N2 C1 C2 119.31(14) . . ? N1 C1 C2 122.73(15) . . ? C3 C2 C1 119.11(16) . . ? C2 C3 C4 118.06(16) . . ? C5 C4 C3 119.67(15) . . ? C5 C4 N3 120.11(14) . . ? C3 C4 N3 120.19(14) . . ? N1 C5 C4 123.53(15) . . ? N2 C6 C7 106.44(12) . . ? N2 C6 C13 109.83(13) . . ? C7 C6 C13 115.42(14) . . ? C8 C7 C6 117.71(14) . . ? C7 C8 C9 117.92(15) . . ? C8 C9 C10 114.96(15) . . ? C11 C10 C9 115.95(16) . . ? C10 C11 C12 118.90(15) . . ? C11 C12 C13 116.56(14) . . ? C6 C13 C12 114.97(15) . . ? C5 N1 C1 116.88(13) . . ? C1 N2 C6 125.22(13) . . ? O2 N3 O1 122.54(14) . . ? O2 N3 C4 119.36(13) . . ? O1 N3 C4 118.10(14) . . ? _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 64.72 _diffrn_measured_fraction_theta_full 0.945 _refine_diff_density_max 0.200 _refine_diff_density_min -0.177 _refine_diff_density_rms 0.039 _database_code_depnum_ccdc_archive 'CCDC 942520'