# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 1145/158 data_nprna _audit_creation_method SHELXL-97 _chemical_name_systematic N-Propyl-4-nitroaniline _chemical_name_common ? _chemical_formula_moiety 'C9 H12 N2 O2' _chemical_formula_sum 'C9 H12 N2 O2' _chemical_formula_weight 180.21 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 (-p_1)' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.076(2) _cell_length_b 13.123(16) _cell_length_c 15.190(5) _cell_angle_alpha 71.90(7) _cell_angle_beta 81.91(4) _cell_angle_gamma 80.04(7) _cell_volume 943.1(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 25.0 _exptl_crystal_description Prismatic _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.84mm _exptl_crystal_size_mid 0.60mm _exptl_crystal_size_min 0.24mm _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.269 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 MACH3' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3311 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0250 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 25.08 _reflns_number_total 3311 _reflns_number_gt 1873 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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 w=1/[\s^2^(Fo^2^)+(0.2000P)^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 SHELXL _refine_ls_extinction_coef 0.013(8) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3311 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0769 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.2487 _refine_ls_wR_factor_gt 0.1564 _refine_ls_goodness_of_fit_ref 0.914 _refine_ls_restrained_S_all 0.914 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N5 N 0.1972(4) 0.64574(18) 0.75937(16) 0.0612(6) Uani 1 d . . . N7 N 1.0071(4) 0.31384(17) 0.89423(15) 0.0582(6) Uani 1 d . . . H7 H 1.0387 0.2622 0.8690 0.070 Uiso 1 calc R . . O2 O 0.1229(4) 0.71420(17) 0.80008(15) 0.0776(7) Uani 1 d . . . O1 O 0.0892(4) 0.64404(18) 0.69215(14) 0.0787(7) Uani 1 d . . . N8 N 1.6193(5) -0.20764(19) 0.60057(16) 0.0641(6) Uani 1 d . . . H8 H 1.7620 -0.2419 0.6265 0.077 Uiso 1 calc R . . N6 N 1.0487(6) 0.1146(2) 0.74263(19) 0.0816(8) Uani 1 d . . . O4 O 1.1279(7) 0.1294(2) 0.80990(19) 0.1154(10) Uani 1 d . . . O3 O 0.8483(6) 0.1684(2) 0.7071(2) 0.1184(11) Uani 1 d . . . C9 C 0.4149(5) 0.56288(19) 0.79193(16) 0.0516(6) Uani 1 d . . . C10 C 0.5522(5) 0.5665(2) 0.86257(18) 0.0550(6) Uani 1 d . . . H10 H 0.5087 0.6244 0.8875 0.066 Uiso 1 calc R . . C11 C 0.7526(5) 0.4851(2) 0.89604(17) 0.0542(6) Uani 1 d . . . H11 H 0.8457 0.4884 0.9434 0.065 Uiso 1 calc R . . C12 C 0.8196(5) 0.39719(19) 0.86018(16) 0.0509(6) Uani 1 d . . . C13 C 0.6798(5) 0.3970(2) 0.78647(18) 0.0593(7) Uani 1 d . . . H13 H 0.7247 0.3405 0.7599 0.071 Uiso 1 calc R . . C14 C 0.4801(5) 0.4781(2) 0.75349(18) 0.0591(7) Uani 1 d . . . H14 H 0.3878 0.4766 0.7053 0.071 Uiso 1 calc R . . C15 C 1.1952(6) 0.0315(2) 0.70541(19) 0.0625(7) Uani 1 d . . . C16 C 1.4189(6) -0.0298(2) 0.74538(19) 0.0686(8) Uani 1 d . . . H16 H 1.4758 -0.0170 0.7961 0.082 Uiso 1 calc R . . C17 C 1.5567(6) -0.1091(2) 0.71059(19) 0.0659(7) Uani 1 d . . . H17 H 1.7072 -0.1511 0.7383 0.079 Uiso 1 calc R . . C18 C 1.4764(5) -0.1287(2) 0.63402(17) 0.0562(6) Uani 1 d . . . C19 C 1.2477(6) -0.0648(3) 0.5948(2) 0.0708(8) Uani 1 d . . . H19 H 1.1897 -0.0762 0.5436 0.085 Uiso 1 calc R . . C20 C 1.1099(6) 0.0135(2) 0.6306(2) 0.0736(8) Uani 1 d . . . H20 H 0.9569 0.0551 0.6044 0.088 Uiso 1 calc R . . C21 C 1.1610(5) 0.3046(2) 0.97091(18) 0.0601(7) Uani 1 d . . . H21A H 1.0388 0.3145 1.0237 0.072 Uiso 1 calc R . . H21B H 1.2751 0.3612 0.9524 0.072 Uiso 1 calc R . . C22 C 1.3311(6) 0.1966(3) 0.9991(2) 0.0746(8) Uani 1 d . . . H22A H 1.4527 0.1980 1.0425 0.089 Uiso 1 calc R . . H22B H 1.4391 0.1839 0.9446 0.089 Uiso 1 calc R . . C23 C 1.1704(8) 0.1044(3) 1.0436(3) 0.0962(11) Uani 1 d . . . H23A H 1.0739 0.1134 1.1004 0.144 Uiso 1 calc R . . H23B H 1.2893 0.0373 1.0569 0.144 Uiso 1 calc R . . H23C H 1.0454 0.1038 1.0019 0.144 Uiso 1 calc R . . C24 C 1.5501(6) -0.2389(3) 0.5244(2) 0.0683(8) Uani 1 d . . . H24A H 1.5388 -0.1765 0.4696 0.082 Uiso 1 calc R . . H24B H 1.3753 -0.2635 0.5404 0.082 Uiso 1 calc R . . C25 C 1.7522(7) -0.3265(3) 0.5031(3) 0.0891(10) Uani 1 d . . . H25A H 1.7674 -0.3878 0.5587 0.107 Uiso 1 calc R . . H25B H 1.9257 -0.3009 0.4858 0.107 Uiso 1 calc R . . C26 C 1.6831(9) -0.3638(4) 0.4258(3) 0.1061(13) Uani 1 d . . . H26A H 1.5112 -0.3891 0.4423 0.159 Uiso 1 calc R . . H26B H 1.8175 -0.4215 0.4162 0.159 Uiso 1 calc R . . H26C H 1.6767 -0.3045 0.3696 0.159 Uiso 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 N5 0.0599(13) 0.0602(13) 0.0594(13) -0.0155(10) -0.0050(10) -0.0017(10) N7 0.0628(13) 0.0558(12) 0.0613(13) -0.0258(10) -0.0157(10) 0.0021(10) O2 0.0809(14) 0.0637(12) 0.0835(15) -0.0247(11) -0.0122(11) 0.0117(10) O1 0.0776(13) 0.0860(15) 0.0686(13) -0.0175(11) -0.0291(11) 0.0073(11) N8 0.0661(14) 0.0686(14) 0.0664(14) -0.0333(11) -0.0201(11) 0.0041(10) N6 0.105(2) 0.0616(15) 0.0771(17) -0.0270(13) -0.0069(15) 0.0019(14) O4 0.170(3) 0.0938(18) 0.0959(18) -0.0588(15) -0.0282(18) 0.0168(17) O3 0.121(2) 0.0962(19) 0.145(3) -0.0634(19) -0.031(2) 0.0340(17) C9 0.0501(13) 0.0529(13) 0.0508(13) -0.0153(10) -0.0062(10) -0.0035(10) C10 0.0595(15) 0.0508(13) 0.0599(14) -0.0249(11) -0.0057(11) -0.0058(11) C11 0.0581(14) 0.0591(14) 0.0533(14) -0.0249(11) -0.0117(11) -0.0089(11) C12 0.0504(13) 0.0539(13) 0.0503(13) -0.0190(10) -0.0047(10) -0.0059(10) C13 0.0687(16) 0.0586(14) 0.0562(14) -0.0262(12) -0.0124(12) -0.0009(12) C14 0.0653(15) 0.0677(16) 0.0501(14) -0.0232(12) -0.0166(12) -0.0045(12) C15 0.0764(17) 0.0521(14) 0.0597(15) -0.0199(12) -0.0058(13) -0.0048(12) C16 0.086(2) 0.0676(17) 0.0585(16) -0.0242(13) -0.0208(14) -0.0043(14) C17 0.0727(17) 0.0661(16) 0.0629(16) -0.0231(13) -0.0239(13) 0.0017(13) C18 0.0604(15) 0.0556(14) 0.0543(14) -0.0174(11) -0.0097(11) -0.0071(11) C19 0.0752(18) 0.0784(19) 0.0637(16) -0.0306(15) -0.0262(14) 0.0102(15) C20 0.0775(19) 0.0718(18) 0.0709(18) -0.0254(14) -0.0240(15) 0.0137(14) C21 0.0609(15) 0.0631(16) 0.0599(14) -0.0216(12) -0.0157(12) -0.0034(12) C22 0.0673(18) 0.0747(19) 0.0823(19) -0.0224(15) -0.0247(15) 0.0021(14) C23 0.124(3) 0.071(2) 0.092(2) -0.0102(17) -0.040(2) -0.0120(19) C24 0.0731(18) 0.0768(19) 0.0606(16) -0.0295(14) -0.0085(13) -0.0058(14) C25 0.096(2) 0.099(2) 0.087(2) -0.0554(19) -0.0202(19) 0.0084(19) C26 0.124(3) 0.114(3) 0.104(3) -0.071(2) -0.016(2) -0.002(3) _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 N5 O2 1.222(3) . ? N5 O1 1.233(3) . ? N5 C9 1.432(4) . ? N7 C12 1.340(3) . ? N7 C21 1.455(3) . ? N8 C18 1.350(4) . ? N8 C24 1.445(3) . ? N6 O3 1.222(4) . ? N6 O4 1.229(4) . ? N6 C15 1.430(4) . ? C9 C14 1.381(4) . ? C9 C10 1.376(3) . ? C10 C11 1.366(4) . ? C11 C12 1.396(4) . ? C12 C13 1.408(3) . ? C13 C14 1.360(4) . ? C15 C16 1.371(4) . ? C15 C20 1.370(4) . ? C16 C17 1.356(4) . ? C17 C18 1.393(4) . ? C18 C19 1.397(4) . ? C19 C20 1.354(4) . ? C21 C22 1.497(4) . ? C22 C23 1.505(5) . ? C24 C25 1.487(5) . ? C25 C26 1.508(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 O2 N5 O1 122.6(2) . . ? O2 N5 C9 118.9(2) . . ? O1 N5 C9 118.5(2) . . ? C12 N7 C21 124.6(2) . . ? C18 N8 C24 124.8(2) . . ? O3 N6 O4 121.9(3) . . ? O3 N6 C15 119.3(3) . . ? O4 N6 C15 118.8(3) . . ? C14 C9 C10 120.6(2) . . ? C14 C9 N5 119.3(2) . . ? C10 C9 N5 120.0(2) . . ? C11 C10 C9 119.9(2) . . ? C10 C11 C12 121.0(2) . . ? N7 C12 C11 122.4(2) . . ? N7 C12 C13 119.9(2) . . ? C11 C12 C13 117.8(2) . . ? C14 C13 C12 121.0(2) . . ? C13 C14 C9 119.7(2) . . ? C16 C15 C20 120.6(3) . . ? C16 C15 N6 119.6(3) . . ? C20 C15 N6 119.8(3) . . ? C17 C16 C15 119.7(3) . . ? C16 C17 C18 121.0(3) . . ? N8 C18 C17 119.6(2) . . ? N8 C18 C19 122.4(2) . . ? C17 C18 C19 118.0(3) . . ? C20 C19 C18 120.5(3) . . ? C19 C20 C15 120.2(3) . . ? N7 C21 C22 111.4(2) . . ? C21 C22 C23 113.3(3) . . ? N8 C24 C25 111.5(3) . . ? C24 C25 C26 113.2(3) . . ? 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 O2 N5 C9 C14 172.5(2) . . . . ? O1 N5 C9 C14 -6.3(4) . . . . ? O2 N5 C9 C10 -5.7(4) . . . . ? O1 N5 C9 C10 175.5(2) . . . . ? C14 C9 C10 C11 -0.8(4) . . . . ? N5 C9 C10 C11 177.4(2) . . . . ? C9 C10 C11 C12 -0.6(4) . . . . ? C21 N7 C12 C11 0.0(4) . . . . ? C21 N7 C12 C13 -179.1(2) . . . . ? C10 C11 C12 N7 -177.0(2) . . . . ? C10 C11 C12 C13 2.0(4) . . . . ? N7 C12 C13 C14 176.9(2) . . . . ? C11 C12 C13 C14 -2.1(4) . . . . ? C12 C13 C14 C9 0.8(4) . . . . ? C10 C9 C14 C13 0.7(4) . . . . ? N5 C9 C14 C13 -177.5(2) . . . . ? O3 N6 C15 C16 -179.4(3) . . . . ? O4 N6 C15 C16 0.2(4) . . . . ? O3 N6 C15 C20 0.1(5) . . . . ? O4 N6 C15 C20 179.8(3) . . . . ? C20 C15 C16 C17 -0.1(5) . . . . ? N6 C15 C16 C17 179.5(3) . . . . ? C15 C16 C17 C18 0.7(5) . . . . ? C24 N8 C18 C17 177.1(3) . . . . ? C24 N8 C18 C19 -2.7(4) . . . . ? C16 C17 C18 N8 179.4(3) . . . . ? C16 C17 C18 C19 -0.7(4) . . . . ? N8 C18 C19 C20 179.9(3) . . . . ? C17 C18 C19 C20 0.0(5) . . . . ? C18 C19 C20 C15 0.6(5) . . . . ? C16 C15 C20 C19 -0.6(5) . . . . ? N6 C15 C20 C19 179.8(3) . . . . ? C12 N7 C21 C22 173.6(2) . . . . ? N7 C21 C22 C23 -68.4(3) . . . . ? C18 N8 C24 C25 178.5(3) . . . . ? N8 C24 C25 C26 178.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.08 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.21 _refine_diff_density_min -0.12 _refine_diff_density_rms 0.035 #==END data_nbna _audit_creation_method SHELXL-97 _chemical_name_systematic N-Butyl-4-nitroaniline _chemical_name_common ? _chemical_formula_moiety 'C10 H14 N2 O2' _chemical_formula_sum 'C10 H14 N2 O2' _chemical_formula_weight 194.23 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M ' p_21_21_21 (p_2ac_2ab)' 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' _cell_length_a 7.468 _cell_length_b 15.348(18) _cell_length_c 18.528 _cell_angle_alpha 90.00(5) _cell_angle_beta 90.00 _cell_angle_gamma 90.000(10) _cell_volume 2123(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 24 _cell_measurement_theta_min 1.50 _cell_measurement_theta_max 25.0 _exptl_crystal_description Cuboid _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.82mm _exptl_crystal_size_mid 0.64mm _exptl_crystal_size_min 0.28mm _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.215 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 MACH3' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3497 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0321 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 29.98 _reflns_number_total 3497 _reflns_number_gt 1415 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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 w=1/[\s^2^(Fo^2^)+(0.0686P)^2^+0.2025P] 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 0.00 _refine_ls_number_reflns 3497 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1394 _refine_ls_R_factor_gt 0.0551 _refine_ls_wR_factor_ref 0.1778 _refine_ls_wR_factor_gt 0.1232 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.0325 0.46953(19) 0.13032(18) 0.1059(12) Uani 1 d . . . O2 O 0.1662(5) 0.41453(19) 0.22070(17) 0.1022(11) Uani 1 d . . . O3 O 0.1330(5) 0.9107(2) 0.11446(18) 0.1031(11) Uani 1 d . . . O4 O 0.2648(6) 0.96854(19) 0.20483(19) 0.1154(12) Uani 1 d . . . N5 N 0.0999(5) 0.4085(2) 0.16042(18) 0.0736(9) Uani 1 d . . . N6 N 0.2020(5) 0.9056(2) 0.1741(2) 0.0806(10) Uani 1 d . . . N7 N 0.0975(5) 0.08310(18) 0.03061(15) 0.0722(9) Uani 1 d . . . H7 H 0.1391 0.0409 0.0562 0.087 Uiso 1 calc R . . N8 N 0.2413(5) 0.58088(19) 0.30492(16) 0.0703(8) Uani 1 d . . . H8 H 0.1877 0.5385 0.2835 0.084 Uiso 1 calc R . . C9 C 0.0992(5) 0.3242(2) 0.12597(19) 0.0582(8) Uani 1 d . . . C10 C 0.1708(5) 0.2534(2) 0.16214(19) 0.0634(9) Uani 1 d . . . H10 H 0.2197 0.2604 0.2079 0.076 Uiso 1 calc R . . C11 C 0.1693(5) 0.1744(2) 0.13057(19) 0.0637(10) Uani 1 d . . . H11 H 0.2176 0.1268 0.1548 0.076 Uiso 1 calc R . . C12 C 0.0953(5) 0.1627(2) 0.06090(18) 0.0578(9) Uani 1 d . . . C13 C 0.0238(5) 0.2356(2) 0.02611(18) 0.0631(9) Uani 1 d . . . H13 H -0.0252 0.2297 -0.0198 0.076 Uiso 1 calc R . . C14 C 0.0250(5) 0.3148(2) 0.05855(19) 0.0640(10) Uani 1 d . . . H14 H -0.0244 0.3628 0.0352 0.077 Uiso 1 calc R . . C15 C 0.2126(5) 0.8213(2) 0.20807(19) 0.0641(9) Uani 1 d . . . C16 C 0.3015(6) 0.8135(2) 0.27261(19) 0.0722(11) Uani 1 d . . . H16 H 0.3551 0.8619 0.2937 0.087 Uiso 1 calc R . . C17 C 0.3106(5) 0.7336(2) 0.3058(2) 0.0671(10) Uani 1 d . . . H17 H 0.3701 0.7283 0.3496 0.081 Uiso 1 calc R . . C18 C 0.2316(5) 0.6601(2) 0.27440(19) 0.0601(9) Uani 1 d . . . C19 C 0.1426(5) 0.6716(2) 0.2081(2) 0.0697(10) Uani 1 d . . . H19 H 0.0903 0.6239 0.1856 0.084 Uiso 1 calc R . . C20 C 0.1319(6) 0.7508(3) 0.1767(2) 0.0727(11) Uani 1 d . . . H20 H 0.0695 0.7574 0.1337 0.087 Uiso 1 calc R . . C21 C 0.0363(7) 0.0627(2) -0.0408(2) 0.0826(12) Uani 1 d . . . H21A H 0.0827 0.1054 -0.0746 0.099 Uiso 1 calc R . . H21B H -0.0934 0.0655 -0.0422 0.099 Uiso 1 calc R . . C22 C 0.0975(7) -0.0277(3) -0.0632(2) 0.0899(14) Uani 1 d . . . H22A H 0.2270 -0.0304 -0.0598 0.108 Uiso 1 calc R . . H22B H 0.0488 -0.0698 -0.0295 0.108 Uiso 1 calc R . . C23 C 0.0449(8) -0.0523(3) -0.1355(2) 0.1007(15) Uani 1 d . . . H23A H 0.0830 -0.0072 -0.1689 0.121 Uiso 1 calc R . . H23B H -0.0847 -0.0557 -0.1377 0.121 Uiso 1 calc R . . C24 C 0.1220(8) -0.1381(3) -0.1595(3) 0.1168(19) Uani 1 d . . . H24A H 0.2429 -0.1431 -0.1424 0.175 Uiso 1 calc R . . H24B H 0.1210 -0.1410 -0.2113 0.175 Uiso 1 calc R . . H24C H 0.0513 -0.1848 -0.1402 0.175 Uiso 1 calc R . . C25 C 0.3347(6) 0.5619(2) 0.3708(2) 0.0708(10) Uani 1 d . . . H25A H 0.2822 0.5952 0.4100 0.085 Uiso 1 calc R . . H25B H 0.4591 0.5793 0.3661 0.085 Uiso 1 calc R . . C26 C 0.3253(6) 0.4659(2) 0.3886(2) 0.0760(11) Uani 1 d . . . H26A H 0.2008 0.4485 0.3924 0.091 Uiso 1 calc R . . H26B H 0.3789 0.4329 0.3495 0.091 Uiso 1 calc R . . C27 C 0.4198(8) 0.4444(3) 0.4577(2) 0.0934(14) Uani 1 d . . . H27A H 0.3623 0.4758 0.4968 0.112 Uiso 1 calc R . . H27B H 0.5424 0.4649 0.4545 0.112 Uiso 1 calc R . . C28 C 0.4217(11) 0.3492(3) 0.4757(3) 0.145(2) Uani 1 d . . . H28A H 0.3010 0.3277 0.4773 0.218 Uiso 1 calc R . . H28B H 0.4773 0.3408 0.5219 0.218 Uiso 1 calc R . . H28C H 0.4879 0.3181 0.4395 0.218 Uiso 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.159(3) 0.0591(15) 0.100(2) -0.0066(15) -0.011(3) 0.013(2) O2 0.148(3) 0.0771(18) 0.0815(19) -0.0129(15) -0.021(2) -0.015(2) O3 0.118(3) 0.101(2) 0.090(2) 0.0278(19) -0.008(2) 0.013(2) O4 0.160(3) 0.0641(17) 0.122(3) 0.0126(18) -0.015(3) -0.005(2) N5 0.094(3) 0.0586(19) 0.068(2) -0.0010(17) 0.005(2) -0.013(2) N6 0.088(3) 0.068(2) 0.086(2) 0.007(2) 0.007(2) 0.009(2) N7 0.098(2) 0.0575(16) 0.0614(17) -0.0027(14) -0.0011(18) 0.0080(18) N8 0.080(2) 0.0552(16) 0.0754(19) -0.0025(15) -0.0144(18) -0.0056(17) C9 0.061(2) 0.0537(18) 0.0595(19) 0.0007(16) 0.0050(18) -0.0054(18) C10 0.064(2) 0.072(2) 0.0547(19) 0.0013(18) -0.0042(19) -0.0054(19) C11 0.070(2) 0.059(2) 0.062(2) 0.0069(17) -0.006(2) 0.004(2) C12 0.061(2) 0.0521(18) 0.061(2) 0.0000(16) 0.0119(19) 0.0012(17) C13 0.078(3) 0.060(2) 0.0517(18) 0.0031(16) -0.0011(19) 0.001(2) C14 0.076(3) 0.0536(19) 0.063(2) 0.0082(16) 0.002(2) 0.0018(18) C15 0.068(2) 0.059(2) 0.065(2) 0.0013(17) 0.008(2) 0.006(2) C16 0.093(3) 0.056(2) 0.068(2) -0.0070(17) -0.003(2) -0.004(2) C17 0.078(3) 0.064(2) 0.059(2) -0.0029(18) -0.008(2) 0.003(2) C18 0.063(2) 0.0544(19) 0.063(2) -0.0033(17) 0.0028(19) 0.0042(19) C19 0.077(3) 0.060(2) 0.072(2) -0.0097(18) -0.007(2) 0.002(2) C20 0.077(3) 0.078(3) 0.063(2) -0.003(2) -0.008(2) 0.007(2) C21 0.115(3) 0.064(2) 0.068(2) -0.0061(19) 0.001(3) 0.000(2) C22 0.117(4) 0.077(3) 0.075(3) -0.008(2) -0.013(3) -0.003(3) C23 0.125(4) 0.088(3) 0.089(3) -0.020(3) -0.003(3) -0.002(3) C24 0.118(4) 0.104(4) 0.128(4) -0.046(3) 0.005(4) 0.011(4) C25 0.075(3) 0.070(2) 0.068(2) 0.0015(19) -0.008(2) -0.001(2) C26 0.079(3) 0.074(2) 0.075(2) 0.005(2) -0.005(2) -0.003(2) C27 0.114(4) 0.093(3) 0.074(3) 0.012(2) -0.009(3) 0.005(3) C28 0.213(7) 0.089(3) 0.133(4) 0.039(3) -0.031(5) 0.001(5) _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 O1 N5 1.201(4) . ? O2 N5 1.225(4) . ? O3 N6 1.222(4) . ? O4 N6 1.216(5) . ? N5 C9 1.443(5) . ? N6 C15 1.440(5) . ? N7 C12 1.345(4) . ? N7 C21 1.434(5) . ? N8 C18 1.343(4) . ? N8 C25 1.436(4) . ? C9 C14 1.374(5) . ? C9 C10 1.384(5) . ? C10 C11 1.347(5) . ? C11 C12 1.416(5) . ? C12 C13 1.397(5) . ? C13 C14 1.357(5) . ? C15 C20 1.368(5) . ? C15 C16 1.373(5) . ? C16 C17 1.373(5) . ? C17 C18 1.399(5) . ? C18 C19 1.407(5) . ? C19 C20 1.349(5) . ? C21 C22 1.519(5) . ? C22 C23 1.447(6) . ? C23 C24 1.504(6) . ? C25 C26 1.512(5) . ? C26 C27 1.499(6) . ? C27 C28 1.499(6) . ? 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 O1 N5 O2 122.3(3) . . ? O1 N5 C9 119.5(3) . . ? O2 N5 C9 118.2(3) . . ? O4 N6 O3 122.4(4) . . ? O4 N6 C15 119.2(4) . . ? O3 N6 C15 118.4(4) . . ? C12 N7 C21 125.4(3) . . ? C18 N8 C25 124.6(3) . . ? C14 C9 C10 120.9(3) . . ? C14 C9 N5 119.8(3) . . ? C10 C9 N5 119.2(3) . . ? C11 C10 C9 119.6(3) . . ? C10 C11 C12 120.9(3) . . ? N7 C12 C13 122.7(3) . . ? N7 C12 C11 119.4(3) . . ? C13 C12 C11 118.0(3) . . ? C14 C13 C12 120.7(3) . . ? C13 C14 C9 119.9(3) . . ? C20 C15 C16 120.9(3) . . ? C20 C15 N6 120.1(4) . . ? C16 C15 N6 119.0(4) . . ? C17 C16 C15 119.4(3) . . ? C16 C17 C18 120.9(3) . . ? N8 C18 C17 122.2(3) . . ? N8 C18 C19 120.4(3) . . ? C17 C18 C19 117.4(3) . . ? C20 C19 C18 121.1(3) . . ? C19 C20 C15 120.2(4) . . ? N7 C21 C22 110.8(3) . . ? C23 C22 C21 114.2(4) . . ? C22 C23 C24 113.5(5) . . ? N8 C25 C26 111.1(3) . . ? C27 C26 C25 112.2(3) . . ? C26 C27 C28 114.2(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 29.98 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.13 _refine_diff_density_min -0.12 _refine_diff_density_rms 0.031 data_npna _audit_creation_method SHELXL-97 _chemical_name_systematic N-Pentyl-4-nitroaniline _chemical_name_common ? _chemical_formula_moiety 'C11 H16 N2 O2' _chemical_formula_sum 'C11 H16 N2 O2' _chemical_formula_weight 208.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'p_21/c ( -p_2ybc)' 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 6.192(3) _cell_length_b 15.61(7) _cell_length_c 11.851(6) _cell_angle_alpha 90.00(13) _cell_angle_beta 97.52(4) _cell_angle_gamma 90.00(13) _cell_volume 1136(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 24 _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 25.0 _exptl_crystal_description Prismatic _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.84mm _exptl_crystal_size_mid 0.64mm _exptl_crystal_size_min 0.60mm _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.218 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 MACH3' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2725 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0230 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 27.99 _reflns_number_total 2725 _reflns_number_gt 1627 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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 w=1/[\s^2^(Fo^2^)+(0.0800P)^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 2725 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0753 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_ref 0.1627 _refine_ls_wR_factor_gt 0.1338 _refine_ls_goodness_of_fit_ref 1.259 _refine_ls_restrained_S_all 1.259 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1691(2) 0.05483(9) 0.20815(13) 0.0612(4) Uani 1 d . . . H1 H 0.2553 0.1019 0.2317 0.073 Uiso 1 calc R . . N2 N 0.2027(2) -0.18014(8) 0.22232(12) 0.0696(4) Uani 1 d . . . O3 O 0.0849(2) -0.24196(7) 0.19778(12) 0.0919(4) Uani 1 d . . . C4 C -0.0401(2) 0.06792(8) 0.15084(12) 0.0553(4) Uani 1 d . . . N5 N -0.1144(2) 0.14823(7) 0.12837(12) 0.0665(4) Uani 1 d . . . H5 H -0.0279 0.1898 0.1502 0.080 Uiso 1 calc R . . C6 C -0.3268(2) 0.16997(9) 0.07083(14) 0.0629(4) Uani 1 d . . . H6A H -0.4376 0.1508 0.1158 0.076 Uiso 1 calc R . . H6B H -0.3506 0.1410 -0.0021 0.076 Uiso 1 calc R . . C7 C 0.1192(2) -0.09553(8) 0.19687(12) 0.0574(4) Uani 1 d . . . O8 O 0.3910(2) -0.18806(8) 0.26884(14) 0.0953(4) Uani 1 d . . . C9 C -0.1694(2) -0.00453(10) 0.11825(13) 0.0631(4) Uani 1 d . . . H9 H -0.3100 0.0024 0.0809 0.076 Uiso 1 calc R . . C10 C -0.0883(3) -0.08495(9) 0.14157(13) 0.0639(4) Uani 1 d . . . H10 H -0.1738 -0.1326 0.1199 0.077 Uiso 1 calc R . . C11 C -0.3460(3) 0.26569(9) 0.05277(14) 0.0645(4) Uani 1 d . . . H11A H -0.2321 0.2844 0.0095 0.077 Uiso 1 calc R . . H11B H -0.3229 0.2940 0.1262 0.077 Uiso 1 calc R . . C12 C 0.2494(2) -0.02543(9) 0.23023(13) 0.0618(4) Uani 1 d . . . H12 H 0.3899 -0.0331 0.2673 0.074 Uiso 1 calc R . . C13 C -0.5640(3) 0.29289(9) -0.00902(14) 0.0644(4) Uani 1 d . . . H13A H -0.6786 0.2713 0.0318 0.077 Uiso 1 calc R . . H13B H -0.5835 0.2674 -0.0843 0.077 Uiso 1 calc R . . C14 C -0.5858(3) 0.38915(10) -0.02042(14) 0.0688(4) Uani 1 d . . . H14A H -0.5601 0.4145 0.0549 0.083 Uiso 1 calc R . . H14B H -0.4738 0.4102 -0.0634 0.083 Uiso 1 calc R . . C15 C -0.8037(3) 0.41853(12) -0.07769(19) 0.0912(6) Uani 1 d . . . H15A H -0.8321 0.3929 -0.1518 0.137 Uiso 1 calc R . . H15B H -0.8034 0.4798 -0.0851 0.137 Uiso 1 calc R . . H15C H -0.9148 0.4017 -0.0328 0.137 Uiso 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 0.0630(8) 0.0411(7) 0.0781(10) -0.0036(6) 0.0039(7) -0.0077(6) N2 0.0864(10) 0.0454(7) 0.0765(9) 0.0024(6) 0.0089(7) 0.0081(6) O3 0.1158(10) 0.0396(6) 0.1179(10) 0.0000(6) 0.0061(8) -0.0021(6) C4 0.0633(8) 0.0369(6) 0.0658(8) 0.0000(6) 0.0089(6) -0.0031(6) N5 0.0672(8) 0.0367(6) 0.0931(9) 0.0006(6) 0.0008(6) -0.0037(5) C6 0.0646(9) 0.0422(7) 0.0812(10) 0.0041(6) 0.0067(7) -0.0010(6) C7 0.0700(9) 0.0387(7) 0.0632(8) -0.0003(6) 0.0074(7) 0.0021(6) O8 0.0910(9) 0.0617(8) 0.1271(11) 0.0099(7) -0.0081(7) 0.0207(6) C9 0.0628(8) 0.0434(7) 0.0798(10) 0.0012(6) -0.0029(7) -0.0043(6) C10 0.0726(9) 0.0390(7) 0.0776(10) -0.0034(6) 0.0003(7) -0.0079(6) C11 0.0689(9) 0.0419(7) 0.0823(10) 0.0032(7) 0.0081(7) -0.0001(6) C12 0.0589(8) 0.0506(8) 0.0740(9) 0.0002(6) 0.0018(7) -0.0010(6) C13 0.0723(9) 0.0436(8) 0.0764(10) 0.0011(6) 0.0064(7) -0.0004(6) C14 0.0787(10) 0.0473(8) 0.0778(10) 0.0056(7) 0.0005(8) 0.0027(7) C15 0.0875(12) 0.0612(10) 0.1188(16) 0.0072(10) -0.0090(11) 0.0119(9) _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 C12 1.361(5) . ? C1 C4 1.397(2) . ? N2 O3 1.222(4) . ? N2 O8 1.2290(19) . ? N2 C7 1.436(6) . ? C4 N5 1.350(5) . ? C4 C9 1.410(5) . ? N5 C6 1.440(2) . ? C6 C11 1.512(7) . ? C7 C10 1.374(2) . ? C7 C12 1.386(4) . ? C9 C10 1.367(5) . ? C11 C13 1.510(3) . ? C13 C14 1.513(7) . ? C14 C15 1.500(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 C12 C1 C4 121.36(18) . . ? O3 N2 O8 122.0(2) . . ? O3 N2 C7 119.3(2) . . ? O8 N2 C7 118.75(19) . . ? N5 C4 C1 120.16(18) . . ? N5 C4 C9 121.6(2) . . ? C1 C4 C9 118.2(2) . . ? C4 N5 C6 125.37(17) . . ? N5 C6 C11 110.47(18) . . ? C10 C7 C12 120.9(2) . . ? C10 C7 N2 119.95(18) . . ? C12 C7 N2 119.1(2) . . ? C10 C9 C4 120.0(2) . . ? C9 C10 C7 120.19(18) . . ? C6 C11 C13 113.28(18) . . ? C1 C12 C7 119.2(2) . . ? C11 C13 C14 112.72(18) . . ? C15 C14 C13 114.10(19) . . ? _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.15 _refine_diff_density_min -0.17 _refine_diff_density_rms 0.033