# Electronic Supplementary Material (ESI) for CrystEngComm # 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_crystalstructure_4 #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; 1,3-bis(4-nitrophenyl)urea with tetramethylammonium chloride ; _chemical_formula_moiety 'C13 H10 N4 O5, C4 H12 N, Cl' _chemical_formula_sum 'C17 H22 Cl N5 O5' _chemical_formula_weight 411.85 _chemical_compound_source 'Isabelle Kirby' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6033(2) _cell_length_b 11.4827(3) _cell_length_c 11.8705(4) _cell_angle_alpha 83.1860(10) _cell_angle_beta 71.662(2) _cell_angle_gamma 80.423(2) _cell_volume 967.59(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 25104 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.237 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8708 _exptl_absorpt_correction_T_max 0.9541 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 356257 _diffrn_reflns_av_R_equivalents 0.0457 _diffrn_reflns_av_sigmaI/netI 0.0418 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.58 _diffrn_reflns_theta_max 55.40 _reflns_number_total 25085 _reflns_number_gt 18067 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'EvalCCD Duisenberg, Kroon-Batenberg, Schreurs, 2003' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _diffrn_reflns_reduction_process ; Scaled and merged with Sortav R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #============================================================================== # REFINEMENT DATA _exptl_special_details ; ? ; _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc w1 = 1/[s^2^(Fo)] ; _refine_ls_extinction_method none _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 17926 _refine_ls_number_parameters 793 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.071 _refine_ls_R_factor_gt 0.038 _refine_ls_wR_factor_ref 0.029 _refine_ls_goodness_of_fit_ref 1.396 _refine_ls_shift/su_max 0 _refine_diff_density_max 0.624 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.069 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 54.02 _diffrn_measured_fraction_theta_full 0.996 _computing_structure_refinement 'Volkov et al, (2006)' _computing_molecular_graphics 'Volkov et al, (2006)' _computing_publication_material 'Volkov et al, (2006)' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_symmetry_multiplicity CL(1) 1.203478(11) 0.123194(7) 0.095406(7) 0.017 1 2 O(1) 1.34356(6) 0.52927(3) -0.06467(4) 0.016 1 2 O(2) 0.63508(7) 0.81462(3) 0.38069(4) 0.022 1 2 O(3) 0.52597(6) 0.66087(4) 0.48647(4) 0.021 1 2 O(5) 2.09540(6) 0.31853(4) -0.53876(4) 0.022 1 2 O(4) 2.04065(6) 0.13494(5) -0.51531(5) 0.03 1 2 N(1) 0.63474(4) 0.70624(3) 0.39851(3) 0.014 1 2 N(2) 1.17874(5) 0.40551(3) 0.08539(3) 0.013 1 2 N(3) 1.42209(5) 0.32563(3) -0.06302(3) 0.013 1 2 N(5) 1.35971(5) 0.88271(3) -0.25480(3) 0.013 1 2 N(4) 2.00665(5) 0.23744(3) -0.48366(3) 0.018 1 2 C(1) 0.77089(4) 0.63022(3) 0.31345(3) 0.012 1 2 C(2) 0.78789(5) 0.50783(3) 0.34008(3) 0.014 1 2 C(3) 0.92490(5) 0.43629(3) 0.26150(3) 0.014 1 2 C(4) 1.04396(4) 0.48534(3) 0.15601(3) 0.011 1 2 C(5) 1.02094(5) 0.60871(3) 0.12939(3) 0.013 1 2 C(6) 0.88479(5) 0.68080(3) 0.20887(3) 0.014 1 2 C(7) 1.31752(4) 0.42987(3) -0.01894(3) 0.012 1 2 C(8) 1.56722(4) 0.31150(3) -0.16815(3) 0.012 1 2 C(9) 1.64694(5) 0.19345(3) -0.19230(4) 0.017 1 2 C(10) 1.78925(5) 0.16865(3) -0.29626(4) 0.018 1 2 C(11) 1.85558(5) 0.26322(3) -0.37519(3) 0.015 1 2 C(12) 1.78280(5) 0.38082(3) -0.35239(3) 0.015 1 2 C(13) 1.63664(5) 0.40530(3) -0.24908(3) 0.014 1 2 C(14) 1.29097(7) 0.96433(4) -0.15577(4) 0.02 1 2 C(15) 1.35746(8) 0.75780(4) -0.20219(5) 0.023 1 2 C(16) 1.23560(5) 0.90666(4) -0.33377(4) 0.018 1 2 C(17) 1.55514(5) 0.90030(4) -0.32701(4) 0.019 1 2 H(2) 0.698422 0.467201 0.41987 0.031(3) 1 2 H(3) 0.943693 0.341542 0.28257 0.034(3) 1 2 H(5) 1.108661 0.649923 0.049239 0.034(3) 1 2 H(6) 0.862213 0.775877 0.190721 0.035(3) 1 2 H(9) 1.598624 0.119604 -0.130966 0.029(3) 1 2 H(10) 1.850474 0.078179 -0.314711 0.039(4) 1 2 H(12) 1.841648 0.451615 -0.414253 0.030(3) 1 2 H(13) 1.573603 0.495788 -0.232198 0.034(3) 1 2 H(14A) 1.376856 0.943858 -0.099128 0.044(4) 1 2 H(14B) 1.151136 0.953338 -0.106996 0.044(4) 1 2 H(14C) 1.294855 1.052195 -0.194494 0.042(4) 1 2 H(15A) 1.445653 0.744445 -0.146965 0.042(4) 1 2 H(15B) 1.403395 0.701668 -0.273453 0.045(4) 1 2 H(15C) 1.218964 0.74716 -0.150076 0.045(4) 1 2 H(16A) 1.287195 0.848564 -0.403381 0.044(4) 1 2 H(16B) 1.235115 0.996051 -0.368303 0.041(4) 1 2 H(16C) 1.098712 0.891728 -0.28211 0.038(4) 1 2 H(17A) 1.637439 0.884208 -0.268072 0.033(3) 1 2 H(17B) 1.556742 0.988425 -0.365215 0.044(4) 1 2 H(17C) 1.604031 0.841116 -0.395696 0.048(4) 1 2 H(2A) 1.171069 0.318698 0.108931 0.022(3) 1 2 H(3A) 1.37489 0.250988 -0.018528 0.018(3) 1 2 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 CL(1) 0.01777(4) 0.01198(3) 0.01799(4) -0.00106(2) -0.00055(2) -0.00391(2) O(1) 0.01673(13) 0.01118(12) 0.01663(13) 0.00177(10) -0.00218(11) -0.00134(10) O(2) 0.02937(17) 0.01399(12) 0.01907(14) -0.00230(10) -0.00221(12) 0.00175(12) O(3) 0.01950(13) 0.02185(14) 0.01916(13) -0.00567(11) 0.00267(11) -0.00689(12) O(5) 0.01736(13) 0.02824(18) 0.01705(14) 0.00084(13) -0.00195(11) -0.00007(13) O(4) 0.02053(15) 0.0332(2) 0.0328(2) -0.01865(17) 0.00286(14) -0.00518(14) N(1) 0.01426(9) 0.01495(10) 0.01382(8) -0.00297(9) -0.00338(9) -0.00137(9) N(2) 0.01531(11) 0.01026(10) 0.01323(11) -0.00057(9) -0.00211(9) -0.00178(9) N(3) 0.01314(11) 0.01087(10) 0.01495(11) -0.00067(9) -0.00219(9) -0.00182(9) N(5) 0.01358(11) 0.01103(10) 0.01302(11) -0.00077(8) -0.00342(9) -0.00118(9) N(4) 0.01163(10) 0.02571(17) 0.01730(12) -0.00629(9) -0.00330(10) -0.00076(9) C(1) 0.01280(10) 0.01264(11) 0.01221(10) -0.00115(8) -0.00385(8) -0.00195(9) C(2) 0.01562(11) 0.01311(11) 0.01232(11) -0.00049(9) -0.00275(9) -0.00383(9) C(3) 0.01639(12) 0.01122(10) 0.01261(11) 0.00013(8) -0.00339(9) -0.00332(9) C(4) 0.01259(10) 0.01058(10) 0.01153(10) -0.00020(8) -0.00420(8) -0.00197(8) C(5) 0.01423(11) 0.01111(10) 0.01276(10) 0.00067(8) -0.00298(9) -0.00120(9) C(6) 0.01446(11) 0.01127(11) 0.01402(11) 0.00034(9) -0.00338(9) -0.00061(9) C(7) 0.01227(10) 0.01052(10) 0.01284(10) 0.00014(8) -0.00400(9) -0.00150(8) C(8) 0.01075(10) 0.01181(10) 0.01486(11) -0.00114(9) -0.00369(9) -0.00175(8) C(9) 0.01388(11) 0.01228(11) 0.02133(14) -0.00255(10) -0.00179(11) -0.00214(9) C(10) 0.01339(12) 0.01523(13) 0.02279(15) -0.00553(11) -0.00187(11) -0.00167(10) C(11) 0.01106(10) 0.01882(13) 0.01611(12) -0.00401(10) -0.00374(9) -0.00125(10) C(12) 0.01274(11) 0.01738(13) 0.01425(11) -0.00016(10) -0.00349(9) -0.00145(10) C(13) 0.01285(11) 0.01312(11) 0.01487(11) -0.00015(9) -0.00344(9) -0.00100(9) C(14) 0.02354(16) 0.01786(14) 0.01640(13) -0.00527(11) -0.00138(12) -0.00209(12) C(15) 0.0328(2) 0.01222(13) 0.02677(18) 0.00299(12) -0.01475(17) -0.00514(13) C(16) 0.01482(13) 0.02206(15) 0.01701(13) 0.00114(12) -0.00556(11) -0.00191(11) C(17) 0.01291(12) 0.02364(16) 0.02030(14) -0.00459(13) -0.00265(11) -0.00221(11) #----------------------------------------------------------------------------# # MULTIPOLE PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_rho_multipole_atom_label _atom_rho_multipole_coeff_Pv _atom_rho_multipole_coeff_P00 _atom_rho_multipole_coeff_P11 _atom_rho_multipole_coeff_P1-1 _atom_rho_multipole_coeff_P10 _atom_rho_multipole_coeff_P20 _atom_rho_multipole_coeff_P21 _atom_rho_multipole_coeff_P2-1 _atom_rho_multipole_coeff_P22 _atom_rho_multipole_coeff_P2-2 _atom_rho_multipole_coeff_P30 _atom_rho_multipole_coeff_P31 _atom_rho_multipole_coeff_P3-1 _atom_rho_multipole_coeff_P32 _atom_rho_multipole_coeff_P3-2 _atom_rho_multipole_coeff_P33 _atom_rho_multipole_coeff_P3-3 _atom_rho_multipole_coeff_P40 _atom_rho_multipole_coeff_P41 _atom_rho_multipole_coeff_P4-1 _atom_rho_multipole_coeff_P42 _atom_rho_multipole_coeff_P4-2 _atom_rho_multipole_coeff_P43 _atom_rho_multipole_coeff_P4-3 _atom_rho_multipole_coeff_P44 _atom_rho_multipole_coeff_P4-4 _atom_rho_multipole_kappa _atom_rho_multipole_kappa_prime0 _atom_rho_multipole_kappa_prime1 _atom_rho_multipole_kappa_prime2 _atom_rho_multipole_kappa_prime3 _atom_rho_multipole_kappa_prime4 _atom_rho_multipole_radial_slater_n0 _atom_rho_multipole_radial_slater_zeta0 _atom_rho_multipole_radial_slater_n1 _atom_rho_multipole_radial_slater_zeta1 _atom_rho_multipole_radial_slater_n2 _atom_rho_multipole_radial_slater_zeta2 _atom_rho_multipole_radial_slater_n3 _atom_rho_multipole_radial_slater_zeta3 _atom_rho_multipole_radial_slater_n4 _atom_rho_multipole_radial_slater_zeta4 CL(1) 7.42(5) 0 0.034(12) 0.059(12) 0.042(12) 0.007(13) 0.023(13) 0.042(12) 0.061(13) -0.040(13) -0.014(11) -0.030(10) -0.044(10) 0.009(10) 0.042(10) 0.070(10) 0.032(10) 0.042(12) -0.017(11) -0.018(10) -0.013(11) 0.007(11) 0.012(11) 0.023(11) 0.019(11) -0.032(11) 1.043(3) 1 1 1 1 1 4 4.2587714285714 4 4.2587714285714 4 4.2587714285714 4 4.2587714285714 4 4.2587714285714 O(1) 6.40(4) 0 -0.073(12) 0.000(10) -0.004(11) -0.059(12) 0.023(11) -0.010(11) -0.049(11) -0.005(11) -0.015(9) 0.011(9) 0.014(9) 0.008(8) 0.010(8) 0.027(8) 0.005(8) 0.020(12) 0.017(11) -0.018(11) 0.008(11) 0.000(11) 0.002(10) 0.011(10) -0.011(10) 0.000(10) 0.985(3) 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(2) 6.36(2) 0 -0.044(10) -0.008(9) 0.018(9) -0.056(11) -0.005(9) -0.022(9) -0.087(10) 0.026(9) 0.010(8) 0.001(8) -0.013(7) 0.018(7) -0.007(7) 0.061(7) 0.018(7) 0.009(10) 0.008(9) -0.012(9) -0.009(9) 0.005(9) 0.004(8) 0.001(8) 0.026(8) 0.009(8) 0.9933(18) 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(3) 6.3577 0 -0.0439 -0.0084 0.0182 -0.0563 -0.0045 -0.0221 -0.0874 0.026 0.01 0.0011 -0.0128 0.0179 -0.0072 0.0609 0.0175 0.0085 0.0079 -0.012 -0.0087 0.0052 0.0037 0.0005 0.026 0.0085 0.9933(18) 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(5) 6.3169 0 -0.0104 0.0207 0.0836 -0.0202 0.0008 0.0163 -0.1066 0.0146 -0.0469 0.0838 0.0485 0.0173 0.079 0.0351 0.0281 -0.0113 -0.0273 -0.0025 -0.0015 0.0008 0.0048 0.0054 0.0196 0.0044 0.9933(18) 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(4) 6.32(2) 0 -0.010(12) 0.021(10) 0.084(9) -0.020(12) 0.001(10) 0.016(10) -0.107(11) 0.015(11) -0.047(8) 0.084(8) 0.049(8) 0.017(7) 0.079(7) 0.035(8) 0.028(8) -0.011(11) -0.027(9) -0.003(9) -0.002(10) 0.001(10) 0.005(9) 0.005(9) 0.020(10) 0.004(9) 0.9933(18) 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 N(1) 4.90(4) 0 0 0 0.040(12) 0.061(12) 0 0 -0.140(13) 0 0.191(12) 0 0 0.139(12) 0 0 0 0.036(15) 0 0 0.018(15) 0 0 0 0.014(13) 0 1.007(3) 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(2) 5.34(5) 0 -0.042(12) -0.012(12) 0.004(11) -0.020(12) -0.020(11) -0.002(10) -0.012(11) 0.014(11) -0.002(10) 0.001(10) 0.018(10) -0.007(10) 0.005(10) 0.178(10) 0.045(10) 0.028(13) 0.002(12) 0.018(12) -0.015(12) 0.008(12) 0.005(12) -0.003(12) -0.001(12) -0.002(12) 0.995(3) 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(3) 5.34(5) 0 -0.020(12) -0.022(12) 0.005(11) -0.011(12) -0.030(11) 0.012(10) -0.011(11) 0.018(11) 0.008(10) -0.001(10) 0.001(10) 0.030(10) -0.009(10) 0.181(10) 0.047(9) 0.041(13) -0.017(12) -0.021(12) 0.006(12) 0.009(12) -0.011(12) -0.018(12) -0.015(12) -0.015(12) 0.995(3) 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(5) 5.35(5) 0 0.003(11) 0.010(11) -0.012(10) 0.002(11) 0.007(10) -0.017(10) -0.026(10) -0.009(10) 0.191(10) -0.006(10) 0.003(10) -0.002(10) -0.005(10) 0.000(9) -0.165(9) 0.026(13) 0.004(12) -0.013(12) -0.006(12) -0.008(12) -0.007(12) 0.063(12) 0.009(12) 0.009(11) 0.988(4) 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(4) 5.01(4) 0 0 0 0.006(14) 0.077(13) 0 0 -0.161(15) 0 0.221(13) 0 0 0.163(14) 0 0 0 0.057(17) 0 0 -0.010(17) 0 0 0 0.016(15) 0 1.007(3) 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 C(1) 4.06(3) 0 0.059(14) 0.124(14) -0.013(13) -0.088(13) 0.023(12) 0.015(12) 0.064(13) -0.096(13) -0.012(14) 0.020(13) 0.003(13) -0.004(13) -0.004(13) 0.291(14) 0.022(13) 0 0 0 0 0 0 0 0 0 1.026(2) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(2) 4.05(4) 0 0.027(15) 0.005(16) 0.010(13) -0.182(14) -0.009(13) 0.008(12) 0.017(14) 0.001(14) 0.001(14) 0.014(14) 0.014(13) 0.002(13) 0.000(13) 0.227(14) -0.024(14) 0 0 0 0 0 0 0 0 0 1.026(2) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(3) 4.04(4) 0 0.015(15) 0.022(16) 0.005(13) -0.146(14) 0.000(12) 0.005(12) 0.003(13) -0.016(14) -0.008(14) -0.004(13) 0.025(13) -0.012(13) -0.009(13) 0.227(14) 0.002(14) 0 0 0 0 0 0 0 0 0 1.026(2) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(4) 3.96(4) 0 0.046(14) 0.062(14) -0.017(12) -0.169(13) -0.022(12) -0.002(12) 0.022(13) -0.060(13) 0.011(13) 0.010(13) 0.019(13) 0.007(13) -0.001(13) 0.273(14) 0.024(14) 0 0 0 0 0 0 0 0 0 1.026(2) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(5) 3.97(4) 0 0.033(15) 0.006(16) 0.007(13) -0.157(14) 0.032(12) 0.010(12) 0.028(13) 0.009(14) 0.008(14) 0.014(13) 0.006(13) -0.004(13) 0.003(13) 0.247(14) -0.012(13) 0 0 0 0 0 0 0 0 0 1.026(2) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(6) 4.03(4) 0 -0.008(15) 0.034(16) -0.001(13) -0.180(14) 0.011(12) -0.004(12) 0.002(13) -0.007(14) -0.021(14) -0.009(13) 0.014(13) -0.007(13) 0.023(13) 0.215(14) -0.022(13) 0 0 0 0 0 0 0 0 0 1.026(2) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(7) 3.75(6) 0 -0.005(12) -0.016(14) 0.113(15) 0.227(15) -0.025(12) 0.002(13) -0.105(13) -0.005(12) 0.284(17) -0.002(14) 0.004(15) 0.201(15) -0.009(14) 0.007(13) -0.005(13) 0 0 0 0 0 0 0 0 0 1.036(7) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(8) 3.98(4) 0 0.027(14) 0.065(14) 0.014(13) -0.179(13) -0.014(12) -0.002(12) 0.008(13) -0.064(13) 0.026(14) 0.005(13) 0.012(13) 0.005(14) 0.006(13) 0.283(15) 0.023(14) 0 0 0 0 0 0 0 0 0 1.024(2) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(9) 4.07(4) 0 0.008(16) 0.029(17) -0.007(13) -0.144(15) -0.024(13) -0.001(13) 0.015(14) 0.017(15) 0.008(15) 0.013(14) 0.025(14) 0.004(14) -0.024(14) 0.249(15) 0.017(14) 0 0 0 0 0 0 0 0 0 1.024(2) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(10) 4.03(4) 0 0.041(17) 0.041(17) -0.005(13) -0.193(15) 0.006(14) 0.021(13) 0.014(15) -0.032(16) 0.010(15) 0.020(15) 0.016(14) 0.003(15) 0.006(14) 0.261(16) -0.010(15) 0 0 0 0 0 0 0 0 0 1.024(2) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(11) 4.03(4) 0 0.077(15) 0.059(15) -0.003(13) -0.090(14) 0.014(13) 0.032(12) 0.057(14) -0.109(14) 0.013(14) -0.007(14) 0.038(13) 0.001(14) 0.012(14) 0.232(16) 0.005(15) 0 0 0 0 0 0 0 0 0 1.024(2) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(12) 4.03(4) 0 0.061(15) 0.007(17) 0.007(13) -0.180(14) 0.020(13) 0.002(13) 0.029(14) 0.016(15) 0.020(14) -0.014(14) 0.023(13) 0.021(14) -0.014(14) 0.255(15) 0.005(14) 0 0 0 0 0 0 0 0 0 1.024(2) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(13) 3.98(4) 0 -0.021(15) 0.015(17) 0.005(13) -0.143(14) 0.003(12) -0.026(12) -0.015(14) 0.015(14) -0.006(14) 0.022(13) 0.023(13) 0.004(13) 0.008(13) 0.244(14) -0.013(14) 0 0 0 0 0 0 0 0 0 1.024(2) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(14) 3.66(7) 0 -0.01(2) 0.00(2) -0.062(15) -0.095(15) -0.022(15) 0.006(14) 0.006(16) 0.030(16) 0.219(16) 0.003(14) -0.019(14) -0.002(15) 0.002(15) 0.013(14) -0.094(16) 0 0 0 0 0 0 0 0 0 1.052(6) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(15) 3.62(7) 0 -0.06(2) 0.02(2) -0.043(15) -0.054(15) 0.023(15) 0.017(14) -0.026(18) -0.006(18) 0.197(17) 0.007(15) -0.020(14) -0.002(15) -0.023(16) -0.009(15) -0.023(17) 0 0 0 0 0 0 0 0 0 1.052(6) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(16) 3.71(8) 0 -0.02(2) -0.03(2) -0.061(15) -0.052(14) 0.018(14) -0.015(14) 0.005(15) 0.003(15) 0.206(16) 0.019(14) 0.017(14) -0.012(14) -0.011(14) -0.004(13) -0.112(15) 0 0 0 0 0 0 0 0 0 1.052(6) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(17) 3.67(7) 0 0.06(2) -0.04(2) -0.050(15) -0.103(15) -0.012(14) 0.015(15) 0.029(16) -0.042(16) 0.219(16) 0.010(14) -0.004(14) -0.014(15) 0.010(15) 0.012(14) -0.114(16) 0 0 0 0 0 0 0 0 0 1.052(6) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 H(2) 0.88(4) 0 0 0 0.18(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(3) 0.89(3) 0 0 0 0.18(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(5) 0.87(4) 0 0 0 0.22(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(6) 0.91(4) 0 0 0 0.17(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(9) 0.79(3) 0 0 0 0.18(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(10) 0.88(4) 0 0 0 0.18(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(12) 0.85(4) 0 0 0 0.15(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(13) 0.87(4) 0 0 0 0.20(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(14A) 1.01(4) 0 0 0 0.18(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(14B) 0.99(5) 0 0 0 0.15(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(14C) 0.95(4) 0 0 0 0.17(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(15A) 0.99(4) 0 0 0 0.16(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(15B) 0.99(4) 0 0 0 0.15(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(15C) 1.02(5) 0 0 0 0.21(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(16A) 1.05(4) 0 0 0 0.18(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(16B) 0.99(4) 0 0 0 0.16(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(16C) 0.96(4) 0 0 0 0.17(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(17A) 0.88(4) 0 0 0 0.12(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(17B) 1.03(4) 0 0 0 0.18(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(17C) 1.03(4) 0 0 0 0.20(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(2A) 0.73(3) 0 0 0 0.112(18) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(3A) 0.68(3) 0 0 0 0.124(18) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 loop_ _atom_local_axes_atom_label _atom_local_axes_atom0 _atom_local_axes_ax1 _atom_local_axes_atom1 _atom_local_axes_atom2 _atom_local_axes_ax2 CL(1) H(3A) Z CL(1) H(2A) Y O(1) C(7) X O(1) C(13) Y O(2) N(1) X O(2) O(3) Y O(3) N(1) -X O(3) O(2) Y O(5) N(4) -X O(5) O(4) Y O(4) N(4) X O(4) O(5) Y N(1) C(1) Z N(1) O(2) Y N(2) C(4) X N(2) C(7) Y N(3) C(8) X N(3) C(7) Y N(5) C(15) Z N(5) C(16) Y N(4) C(11) Z N(4) O(4) Y C(1) C(6) X C(1) C(2) Y C(2) C(3) X C(2) C(1) Y C(3) C(4) X C(3) C(2) Y C(4) C(3) X C(4) C(5) Y C(5) C(6) X C(5) C(4) Y C(6) C(1) X C(6) C(5) Y C(7) O(1) Z C(7) N(3) Y C(8) C(9) X C(8) C(13) Y C(9) C(10) X C(9) C(8) Y C(10) C(11) X C(10) C(9) Y C(11) C(12) X C(11) C(10) Y C(12) C(13) X C(12) C(11) Y C(13) C(8) X C(13) C(12) Y C(14) N(5) Z C(14) H(14B) Y C(15) N(5) Z C(15) H(15A) Y C(16) N(5) Z C(16) H(16A) Y C(17) N(5) Z C(17) H(17B) Y H(2) C(2) Z H(2) C(3) Y H(3) C(3) Z H(3) C(2) Y H(5) C(5) Z H(5) C(6) Y H(6) C(6) Z H(6) C(5) Y H(9) C(9) Z H(9) C(10) Y H(10) C(10) Z H(10) C(9) Y H(12) C(12) Z H(12) C(13) Y H(13) C(13) Z H(13) C(12) Y H(14A) C(14) Z H(14A) H(14C) Y H(14B) C(14) Z H(14B) H(14C) Y H(14C) C(14) Z H(14C) H(14A) Y H(15A) C(15) Z H(15A) H(15C) Y H(15B) C(15) Z H(15B) H(15C) Y H(15C) C(15) Z H(15C) H(15A) Y H(16A) C(16) Z H(16A) H(16B) Y H(16B) C(16) Z H(16B) H(16A) Y H(16C) C(16) Z H(16C) H(16B) Y H(17A) C(17) Z H(17A) H(17C) Y H(17B) C(17) Z H(17B) H(17C) Y H(17C) C(17) Z H(17C) H(17B) Y H(2A) N(2) Z H(2A) C(7) Y H(3A) N(3) Z H(3A) C(7) Y #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(1) C(7) 1.2236(5) 1_555 1_555 yes O(2) N(1) 1.2376(5) 1_555 1_555 yes O(3) N(1) 1.2314(5) 1_555 1_555 yes O(5) N(4) 1.2398(6) 1_555 1_555 yes O(4) N(4) 1.2393(6) 1_555 1_555 yes N(1) C(1) 1.4504(5) 1_555 1_555 yes N(2) C(4) 1.3866(4) 1_555 1_555 yes N(2) C(7) 1.3853(4) 1_555 1_555 yes N(2) H(2A) 1.0090(3) 1_555 1_555 yes N(3) C(7) 1.3816(4) 1_555 1_555 yes N(3) C(8) 1.3868(5) 1_555 1_555 yes N(3) H(3A) 1.0090(3) 1_555 1_555 yes N(4) C(11) 1.4531(5) 1_555 1_555 yes C(1) C(2) 1.3969(5) 1_555 1_555 yes C(1) C(6) 1.3958(4) 1_555 1_555 yes C(2) C(3) 1.3841(5) 1_555 1_555 yes C(2) H(2) 1.0830(3) 1_555 1_555 yes C(3) C(4) 1.4120(4) 1_555 1_555 yes C(3) H(3) 1.0830(3) 1_555 1_555 yes C(4) C(5) 1.4083(4) 1_555 1_555 yes C(5) C(6) 1.3902(5) 1_555 1_555 yes C(5) H(5) 1.0830(3) 1_555 1_555 yes C(6) H(6) 1.0830(3) 1_555 1_555 yes C(8) C(9) 1.4130(5) 1_555 1_555 yes C(8) C(13) 1.4093(5) 1_555 1_555 yes C(9) C(10) 1.3840(5) 1_555 1_555 yes C(9) H(9) 1.0830(4) 1_555 1_555 yes C(10) C(11) 1.3982(6) 1_555 1_555 yes C(10) H(10) 1.0830(4) 1_555 1_555 yes C(11) C(12) 1.3952(5) 1_555 1_555 yes C(12) C(13) 1.3922(5) 1_555 1_555 yes C(12) H(12) 1.0830(4) 1_555 1_555 yes C(13) H(13) 1.0830(3) 1_555 1_555 yes C(14) H(14A) 1.0590(5) 1_555 1_555 yes C(14) H(14B) 1.0590(5) 1_555 1_555 yes C(14) H(14C) 1.0590(5) 1_555 1_555 yes C(15) H(15A) 1.0590(5) 1_555 1_555 yes C(15) H(15B) 1.0590(5) 1_555 1_555 yes C(15) H(15C) 1.0590(6) 1_555 1_555 yes C(16) H(16A) 1.0590(4) 1_555 1_555 yes C(16) H(16B) 1.0590(4) 1_555 1_555 yes C(16) H(16C) 1.0590(4) 1_555 1_555 yes C(17) H(17A) 1.0590(5) 1_555 1_555 yes C(17) H(17B) 1.0590(5) 1_555 1_555 yes C(17) H(17C) 1.0590(4) 1_555 1_555 yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O(2) N(1) O(3) 122.54(4) 1_555 1_555 1_555 yes O(2) N(1) C(1) 118.37(3) 1_555 1_555 1_555 yes O(3) N(1) C(1) 119.08(3) 1_555 1_555 1_555 yes C(4) N(2) C(7) 127.87(3) 1_555 1_555 1_555 yes C(4) N(2) H(2A) 116.90(3) 1_555 1_555 1_555 yes C(7) N(2) H(2A) 115.11(3) 1_555 1_555 1_555 yes C(7) N(3) C(8) 127.89(3) 1_555 1_555 1_555 yes C(7) N(3) H(3A) 115.12(3) 1_555 1_555 1_555 yes C(8) N(3) H(3A) 116.43(3) 1_555 1_555 1_555 yes O(5) N(4) O(4) 123.64(5) 1_555 1_555 1_555 yes O(5) N(4) C(11) 118.41(4) 1_555 1_555 1_555 yes O(4) N(4) C(11) 117.95(4) 1_555 1_555 1_555 yes N(1) C(1) C(2) 118.87(3) 1_555 1_555 1_555 yes N(1) C(1) C(6) 119.50(3) 1_555 1_555 1_555 yes C(2) C(1) C(6) 121.62(3) 1_555 1_555 1_555 yes C(1) C(2) C(3) 118.53(3) 1_555 1_555 1_555 yes C(1) C(2) H(2) 122.44(3) 1_555 1_555 1_555 yes C(3) C(2) H(2) 119.03(3) 1_555 1_555 1_555 yes C(2) C(3) C(4) 120.98(3) 1_555 1_555 1_555 yes C(2) C(3) H(3) 119.47(3) 1_555 1_555 1_555 yes C(4) C(3) H(3) 119.53(3) 1_555 1_555 1_555 yes N(2) C(4) C(3) 115.95(3) 1_555 1_555 1_555 yes N(2) C(4) C(5) 124.54(3) 1_555 1_555 1_555 yes C(3) C(4) C(5) 119.51(3) 1_555 1_555 1_555 yes C(4) C(5) C(6) 119.57(3) 1_555 1_555 1_555 yes C(4) C(5) H(5) 121.91(3) 1_555 1_555 1_555 yes C(6) C(5) H(5) 118.51(3) 1_555 1_555 1_555 yes C(1) C(6) C(5) 119.76(3) 1_555 1_555 1_555 yes C(1) C(6) H(6) 118.71(3) 1_555 1_555 1_555 yes C(5) C(6) H(6) 121.51(3) 1_555 1_555 1_555 yes O(1) C(7) N(2) 124.79(3) 1_555 1_555 1_555 yes O(1) C(7) N(3) 125.23(3) 1_555 1_555 1_555 yes N(2) C(7) N(3) 109.98(3) 1_555 1_555 1_555 yes N(3) C(8) C(9) 115.71(3) 1_555 1_555 1_555 yes N(3) C(8) C(13) 124.55(3) 1_555 1_555 1_555 yes C(9) C(8) C(13) 119.75(3) 1_555 1_555 1_555 yes C(8) C(9) C(10) 120.69(3) 1_555 1_555 1_555 yes C(8) C(9) H(9) 121.48(3) 1_555 1_555 1_555 yes C(10) C(9) H(9) 117.83(3) 1_555 1_555 1_555 yes C(9) C(10) C(11) 118.46(3) 1_555 1_555 1_555 yes C(9) C(10) H(10) 120.69(4) 1_555 1_555 1_555 yes C(11) C(10) H(10) 120.83(3) 1_555 1_555 1_555 yes N(4) C(11) C(10) 118.55(3) 1_555 1_555 1_555 yes N(4) C(11) C(12) 119.31(3) 1_555 1_555 1_555 yes C(10) C(11) C(12) 122.14(3) 1_555 1_555 1_555 yes C(11) C(12) C(13) 119.22(3) 1_555 1_555 1_555 yes C(11) C(12) H(12) 119.82(3) 1_555 1_555 1_555 yes C(13) C(12) H(12) 120.95(3) 1_555 1_555 1_555 yes C(8) C(13) C(12) 119.71(3) 1_555 1_555 1_555 yes C(8) C(13) H(13) 120.05(3) 1_555 1_555 1_555 yes C(12) C(13) H(13) 120.22(3) 1_555 1_555 1_555 yes H(14A) C(14) H(14B) 109.79(4) 1_555 1_555 1_555 yes H(14A) C(14) H(14C) 111.63(4) 1_555 1_555 1_555 yes H(14B) C(14) H(14C) 109.19(4) 1_555 1_555 1_555 yes H(15A) C(15) H(15B) 113.30(5) 1_555 1_555 1_555 yes H(15A) C(15) H(15C) 109.59(5) 1_555 1_555 1_555 yes H(15B) C(15) H(15C) 110.53(4) 1_555 1_555 1_555 yes H(16A) C(16) H(16B) 110.78(4) 1_555 1_555 1_555 yes H(16A) C(16) H(16C) 109.90(4) 1_555 1_555 1_555 yes H(16B) C(16) H(16C) 110.06(4) 1_555 1_555 1_555 yes H(17A) C(17) H(17B) 110.04(4) 1_555 1_555 1_555 yes H(17A) C(17) H(17C) 111.54(4) 1_555 1_555 1_555 yes H(17B) C(17) H(17C) 109.25(4) 1_555 1_555 1_555 yes _database_code_depnum_ccdc_archive 'CCDC 953019' ####################################################################### # # 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_crystalstructure_5 #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; 1,3-bis(4-nitrophenyl)urea with tetramethylammonium acetate ; _chemical_formula_moiety 'C13 H10 N4 O5, C4 H12 N, C2 H3 O2' _chemical_formula_sum 'C19 H25 N5 O7' _chemical_formula_weight 435.44 _chemical_compound_source 'Isabelle Kirby' 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' #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.797(2) _cell_length_b 11.214(3) _cell_length_c 12.211(3) _cell_angle_alpha 91.753(5) _cell_angle_beta 104.560(7) _cell_angle_gamma 95.232(13) _cell_volume 1027.5(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8541 _cell_measurement_theta_min 23.4 _cell_measurement_theta_max 61.4 _exptl_crystal_description column _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9577 _exptl_absorpt_correction_T_max 0.9913 _exptl_absorpt_process_details ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _diffrn_reflns_reduction_process ; Scaled and merged with Sortav R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #============================================================================== # REFINEMENT DATA _refine_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_source_power 2.475 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_collimation 'confocal mirrors, HF Varimax' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_device 'four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 (Right)' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support 'MiTeGen MicroLoop' _diffrn_reflns_number 147512 _diffrn_reflns_av_R_equivalents 0.0812 _diffrn_reflns_av_sigmaI/netI 0.0542 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 61.56 _reflns_number_total 31289 _reflns_number_gt 26198 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_structure_refinement 'Volkov et al, (2006)' _computing_molecular_graphics 'Volkov et al, (2006)' _computing_publication_material 'Volkov et al, (2006)' _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc w1 = 1/[s^2^(Fo)] ; _refine_ls_extinction_method none _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 22116 _refine_ls_number_parameters 851 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.08 _refine_ls_R_factor_gt 0.053 _refine_ls_wR_factor_ref 0.061 _refine_ls_goodness_of_fit_ref 1.645 _refine_ls_shift/su_max 0 _refine_diff_density_max 0.354 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.068 _diffrn_measured_fraction_theta_max 0.666 _diffrn_reflns_theta_full 54.71 _diffrn_measured_fraction_theta_full 0.959 #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_symmetry_multiplicity O(1) 0.07620(6) 0.53099(4) 0.37724(4) 0.015 1 2 O(4) 0.81013(9) 0.69740(6) 0.90729(5) 0.027 1 2 O(5) 0.69786(9) 0.84816(5) 0.81891(6) 0.025 1 2 O(3) -0.56579(8) 0.13477(5) -0.08250(5) 0.022 1 2 O(2) -0.58633(8) 0.32563(5) -0.09513(5) 0.023 1 2 O(6) 0.14861(9) 0.10001(5) 0.41463(5) 0.02 1 2 O(7) 0.33297(9) 0.19105(5) 0.57096(5) 0.021 1 2 N(1) -0.51651(5) 0.24010(3) -0.04732(3) 0.014 1 2 N(2) 0.04065(5) 0.32438(3) 0.34850(3) 0.012 1 2 N(3) 0.24771(5) 0.41269(3) 0.50285(3) 0.011 1 2 N(4) 0.70628(6) 0.73949(4) 0.82776(4) 0.016 1 2 N(5) 0.08825(5) 0.82070(4) 0.21065(4) 0.013 1 2 C(1) -0.37017(5) 0.26378(4) 0.05315(3) 0.012 1 2 C(2) -0.29623(6) 0.16742(4) 0.11147(4) 0.013 1 2 C(3) -0.15904(6) 0.19144(4) 0.20867(4) 0.013 1 2 C(4) -0.09499(5) 0.31075(3) 0.24983(3) 0.01 1 2 C(5) -0.17257(5) 0.40610(4) 0.18970(4) 0.013 1 2 C(6) -0.30926(5) 0.38231(4) 0.09170(4) 0.013 1 2 C(7) 0.11847(5) 0.43181(3) 0.40745(3) 0.011 1 2 C(8) 0.35466(5) 0.49930(3) 0.57979(3) 0.011 1 2 C(9) 0.47096(6) 0.45576(4) 0.67520(4) 0.013 1 2 C(10) 0.58707(6) 0.53379(4) 0.75594(4) 0.014 1 2 C(11) 0.58736(5) 0.65699(4) 0.74214(4) 0.012 1 2 C(12) 0.47404(6) 0.70230(4) 0.64950(4) 0.014 1 2 C(13) 0.35712(6) 0.62401(4) 0.56820(4) 0.013 1 2 C(14) -0.02466(7) 0.82087(5) 0.29408(4) 0.017 1 2 C(15) 0.27858(7) 0.85790(7) 0.27090(6) 0.023 1 2 C(16) 0.02674(9) 0.90720(5) 0.12131(5) 0.02 1 2 C(17) 0.07027(8) 0.69736(4) 0.15600(5) 0.018 1 2 C(18) 0.25435(5) 0.09900(4) 0.51167(4) 0.012 1 2 C(19) 0.29064(7) -0.02203(4) 0.56080(4) 0.017 1 2 H(2) -0.34969 0.076693 0.080226 0.034 1 2 H(3) -0.099237 0.11844 0.258122 0.029 1 2 H(5) -0.125515 0.498508 0.224406 0.032 1 2 H(6) -0.374521 0.455584 0.044919 0.03 1 2 H(9) 0.465676 0.358468 0.685695 0.04 1 2 H(10) 0.674916 0.500393 0.829735 0.032 1 2 H(12) 0.478942 0.797363 0.640012 0.025 1 2 H(13) 0.268036 0.658092 0.494806 0.04 1 2 H(14A) -0.161692 0.801343 0.249233 0.036 1 2 H(14B) -0.003885 0.910836 0.337211 0.032 1 2 H(14C) 0.019853 0.751692 0.355404 0.04 1 2 H(15A) 0.325135 0.794599 0.335676 0.044 1 2 H(15B) 0.285493 0.946231 0.310845 0.043 1 2 H(15C) 0.362273 0.859616 0.208669 0.057 1 2 H(16A) 0.105394 0.902094 0.058731 0.045 1 2 H(16B) 0.045618 0.996525 0.161837 0.046 1 2 H(16C) -0.113065 0.881338 0.079921 0.042 1 2 H(17A) 0.148133 0.69965 0.094386 0.039 1 2 H(17B) -0.067513 0.673156 0.114668 0.038 1 2 H(17C) 0.119779 0.636014 0.222578 0.038 1 2 H(19A) 0.371742 -0.067973 0.51517 0.052 1 2 H(19B) 0.167187 -0.079323 0.550845 0.048 1 2 H(19C) 0.358112 -0.012178 0.649387 0.043 1 2 H(2A) 0.085676 0.243774 0.378806 0.023 1 2 H(3A) 0.273639 0.324531 0.52176 0.028 1 2 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 O(1) 0.01575(14) 0.00980(12) 0.01571(14) 0.00117(10) -0.00179(11) 0.00247(11) O(4) 0.0278(2) 0.0280(2) 0.01700(17) -0.00324(16) -0.00546(16) -0.00401(19) O(5) 0.0282(2) 0.01625(16) 0.0273(2) -0.00495(15) 0.00343(19) -0.00775(16) O(3) 0.02286(18) 0.01675(15) 0.02019(17) -0.00298(13) -0.00501(14) -0.00217(14) O(2) 0.02199(17) 0.01884(16) 0.02046(17) 0.00304(14) -0.00742(14) 0.00068(14) O(6) 0.02293(19) 0.01269(14) 0.01832(17) 0.00194(13) -0.00596(15) 0.00278(14) O(7) 0.0263(2) 0.01088(14) 0.01961(18) 0.00028(13) -0.00558(16) 0.00135(15) N(1) 0.01228(10) 0.01444(13) 0.01280(11) 0.00027(8) 0.00007(10) -0.00081(9) N(2) 0.01054(10) 0.00945(10) 0.01334(12) 0.00064(9) -0.00050(9) 0.00125(9) N(3) 0.01046(10) 0.00963(10) 0.01230(11) 0.00030(9) 0.00014(9) 0.00203(9) N(4) 0.01527(11) 0.01736(14) 0.01460(12) -0.00319(12) 0.00354(11) -0.00408(11) N(5) 0.01103(11) 0.01265(12) 0.01404(13) -0.00058(10) 0.00209(10) 0.00066(10) C(1) 0.01026(11) 0.01185(12) 0.01196(12) 0.00030(9) 0.00124(9) 0.00005(9) C(2) 0.01374(12) 0.01071(12) 0.01394(13) -0.00016(10) 0.00047(10) 0.00056(10) C(3) 0.01319(12) 0.00954(11) 0.01399(13) 0.00078(10) 0.00013(10) 0.00115(10) C(4) 0.00880(10) 0.00983(11) 0.01191(11) 0.00102(9) 0.00103(9) 0.00095(9) C(5) 0.01117(11) 0.00991(11) 0.01451(13) 0.00146(10) -0.00042(10) 0.00033(9) C(6) 0.01121(11) 0.01110(12) 0.01429(13) 0.00197(10) -0.00030(10) 0.00093(10) C(7) 0.00953(10) 0.00929(10) 0.01232(11) 0.00078(9) 0.00125(9) 0.00156(9) C(8) 0.00990(10) 0.00972(11) 0.01129(11) 0.00022(9) 0.00144(9) 0.00164(9) C(9) 0.01416(13) 0.01094(12) 0.01261(13) 0.00005(10) -0.00032(10) 0.00244(10) C(10) 0.01368(13) 0.01398(13) 0.01230(13) -0.00051(11) -0.00027(10) 0.00208(11) C(11) 0.01146(11) 0.01253(12) 0.01283(12) -0.00142(10) 0.00271(10) -0.00042(10) C(12) 0.01491(13) 0.01029(12) 0.01494(14) 0.00000(10) 0.00185(11) -0.00038(11) C(13) 0.01376(12) 0.01013(11) 0.01370(13) 0.00098(10) 0.00066(10) 0.00116(10) C(14) 0.01459(14) 0.02063(18) 0.01652(15) -0.00120(14) 0.00470(12) 0.00099(13) C(15) 0.01126(14) 0.0311(3) 0.0244(2) -0.0068(2) 0.00190(14) 0.00003(16) C(16) 0.0239(2) 0.01402(15) 0.02191(19) 0.00434(14) 0.00531(17) 0.00192(15) C(17) 0.02292(19) 0.01267(14) 0.01731(16) -0.00007(12) 0.00516(14) 0.00252(13) C(18) 0.01148(11) 0.01021(11) 0.01398(13) 0.00176(10) 0.00136(10) 0.00198(10) C(19) 0.01866(16) 0.01181(13) 0.01798(16) 0.00404(12) 0.00117(13) 0.00193(12) H(2) 0.05204 0.01335 0.0272 -0.00339 -0.00536 0.00368 H(3) 0.03286 0.02454 0.02306 0.00161 -0.00651 0.01089 H(5) 0.04006 0.01192 0.03582 -0.00124 -0.00078 -0.00285 H(6) 0.03241 0.01444 0.03214 0.00126 -0.01174 0.00263 H(9) 0.06807 0.01556 0.02605 0.00083 -0.0041 0.00198 H(10) 0.03965 0.02959 0.01831 0.00461 -0.01156 0.00533 H(12) 0.01451 0.01709 0.03377 0.00528 -0.011 0.00222 H(13) 0.06162 0.02897 0.02158 0.0083 -0.00207 0.00426 H(14A) 0.02448 0.05137 0.03156 -0.00752 0.01161 -0.00491 H(14B) 0.03786 0.03041 0.02788 -0.01075 0.01332 -0.00696 H(14C) 0.05055 0.03109 0.03385 0.00862 0.00289 -0.00307 H(15A) 0.03284 0.05455 0.03819 -0.00168 -0.00345 0.01197 H(15B) 0.04364 0.04031 0.0409 -0.01838 0.00733 -0.00113 H(15C) 0.04329 0.06649 0.06165 -0.01766 0.02312 -0.01994 H(16A) 0.06442 0.03965 0.04484 0.02044 0.03766 0.01213 H(16B) 0.0671 0.01505 0.05789 0.00453 0.01854 0.00236 H(16C) 0.03545 0.03905 0.04607 0.0203 -0.00191 0.01201 H(17A) 0.05014 0.03828 0.03927 0.00703 0.02747 0.01034 H(17B) 0.04583 0.01854 0.04052 -0.00411 -0.00252 -0.00525 H(17C) 0.05113 0.02646 0.03758 0.00909 0.00752 0.01498 H(19A) 0.06871 0.03808 0.06784 0.02073 0.03644 0.04055 H(19B) 0.03358 0.02688 0.07108 0.01857 -0.00754 -0.00908 H(19C) 0.04809 0.04626 0.02767 0.01529 -0.00684 0.01795 H(2A) 0.02443 0.02297 0.01907 0.00476 0.00071 0.00779 H(3A) 0.0436 0.01179 0.02923 0.00115 0.00885 0.00961 #----------------------------------------------------------------------------# # MULTIPOLE PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_rho_multipole_atom_label _atom_rho_multipole_coeff_Pv _atom_rho_multipole_coeff_P00 _atom_rho_multipole_coeff_P11 _atom_rho_multipole_coeff_P1-1 _atom_rho_multipole_coeff_P10 _atom_rho_multipole_coeff_P20 _atom_rho_multipole_coeff_P21 _atom_rho_multipole_coeff_P2-1 _atom_rho_multipole_coeff_P22 _atom_rho_multipole_coeff_P2-2 _atom_rho_multipole_coeff_P30 _atom_rho_multipole_coeff_P31 _atom_rho_multipole_coeff_P3-1 _atom_rho_multipole_coeff_P32 _atom_rho_multipole_coeff_P3-2 _atom_rho_multipole_coeff_P33 _atom_rho_multipole_coeff_P3-3 _atom_rho_multipole_coeff_P40 _atom_rho_multipole_coeff_P41 _atom_rho_multipole_coeff_P4-1 _atom_rho_multipole_coeff_P42 _atom_rho_multipole_coeff_P4-2 _atom_rho_multipole_coeff_P43 _atom_rho_multipole_coeff_P4-3 _atom_rho_multipole_coeff_P44 _atom_rho_multipole_coeff_P4-4 _atom_rho_multipole_kappa _atom_rho_multipole_kappa_prime0 _atom_rho_multipole_kappa_prime1 _atom_rho_multipole_kappa_prime2 _atom_rho_multipole_kappa_prime3 _atom_rho_multipole_kappa_prime4 _atom_rho_multipole_radial_slater_n0 _atom_rho_multipole_radial_slater_zeta0 _atom_rho_multipole_radial_slater_n1 _atom_rho_multipole_radial_slater_zeta1 _atom_rho_multipole_radial_slater_n2 _atom_rho_multipole_radial_slater_zeta2 _atom_rho_multipole_radial_slater_n3 _atom_rho_multipole_radial_slater_zeta3 _atom_rho_multipole_radial_slater_n4 _atom_rho_multipole_radial_slater_zeta4 O(1) 6.18(3) 0 -0.091(14) 0.002(12) -0.025(13) -0.036(16) 0.023(15) 0.037(14) -0.057(14) 0.024(14) -0.030(14) -0.011(13) -0.011(12) 0.032(13) 0.019(12) 0.012(12) -0.025(12) 0.016(18) -0.028(17) -0.014(16) 0.022(17) 0.053(16) 0.034(15) 0.013(16) -0.008(15) 0.002(14) 0.976373 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(4) 6.18(2) 0 -0.049(13) 0.017(12) 0.000(12) 0.015(16) 0.009(12) -0.033(13) -0.098(13) 0.044(13) -0.028(13) -0.009(13) -0.011(12) 0.004(11) -0.008(11) 0.044(12) 0.045(12) 0.014(18) -0.005(15) -0.016(15) -0.002(16) -0.010(16) -0.020(14) 0.013(13) 0.019(14) 0.013(14) 0.978355 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(5) 6.1822 0 -0.0486 0.0167 -0.0004 0.0146 0.0087 -0.0326 -0.0975 0.0443 -0.0283 -0.0088 -0.0114 0.0041 -0.0079 0.0436 0.0448 0.0142 -0.0054 -0.0161 -0.002 -0.0102 -0.0197 0.0127 0.0194 0.0126 0.978355 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(3) 6.1361 0 -0.0423 0.0243 -0.0174 -0.0015 -0.0088 -0.0052 -0.1388 -0.001 -0.0118 0.0909 -0.0121 0.0015 -0.0009 0.0308 0.0079 0.0003 0.0182 -0.0158 -0.0144 0.0047 -0.0197 0.0079 0.014 0.0013 0.978355 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(2) 6.136(19) 0 -0.042(11) 0.024(10) -0.017(12) -0.002(14) -0.009(12) -0.005(12) -0.139(11) -0.001(12) -0.012(12) 0.091(12) -0.012(11) 0.002(10) -0.001(10) 0.031(10) 0.008(10) 0.000(17) 0.018(14) -0.016(14) -0.014(14) 0.005(15) -0.020(13) 0.008(12) 0.014(12) 0.001(12) 0.978355 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(6) 6.39(3) 0 -0.060(14) -0.006(13) 0.029(16) -0.027(18) -0.020(17) 0.022(16) -0.070(14) -0.023(15) 0.038(17) 0.048(15) 0.046(15) 0.019(14) -0.005(14) 0.033(13) 0.003(13) 0.01(2) 0.03(2) 0.040(19) 0.04(2) -0.021(19) -0.021(17) -0.039(18) 0.040(16) 0.010(15) 0.963 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(7) 6.34(3) 0 -0.001(15) 0.015(13) -0.010(17) -0.068(19) -0.034(17) -0.029(16) -0.089(15) 0.009(15) 0.069(17) 0.070(16) 0.070(16) -0.014(15) -0.017(14) 0.058(13) -0.015(13) 0.00(2) 0.05(2) -0.01(2) -0.05(2) -0.006(19) 0.016(17) -0.033(18) -0.002(16) -0.003(16) 0.963 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 N(1) 5.07(3) 0 0 0 0.042(16) 0.057(16) 0 0 -0.193(16) 0 0.218(17) 0 0 0.176(17) 0 0 0 0.06(2) 0 0 0.00(2) 0 0 0 0.05(2) 0 0.97907 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(2) 5.18(3) 0 -0.069(15) -0.048(15) 0.022(13) -0.038(15) 0.008(14) -0.017(13) -0.031(14) 0.059(15) -0.006(15) 0.001(14) -0.010(14) 0.007(14) -0.010(14) 0.157(14) 0.029(14) 0.04(2) 0.028(18) 0.012(17) -0.009(18) -0.006(18) -0.013(17) -0.033(18) 0.007(18) -0.002(18) 0.980877 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(3) 5.22(3) 0 -0.036(15) -0.095(15) 0.043(13) 0.003(15) -0.028(13) 0.043(13) -0.082(14) 0.003(15) -0.030(15) -0.018(14) 0.042(14) 0.022(14) 0.014(14) 0.174(15) 0.049(14) 0.06(2) 0.043(17) -0.015(18) -0.018(18) -0.018(18) 0.034(17) 0.020(18) -0.024(18) -0.040(18) 0.980877 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(4) 5.03(3) 0 0 0 0.035(17) -0.012(17) 0 0 -0.205(18) 0 0.215(19) 0 0 0.221(19) 0 0 0 0.03(2) 0 0 -0.03(2) 0 0 0 0.00(2) 0 0.97907 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(5) 4.98(3) 0 0.017(14) -0.046(14) -0.005(14) -0.018(15) 0.055(14) -0.038(14) -0.010(15) -0.017(15) 0.200(15) 0.015(15) 0.015(15) 0.012(15) -0.029(15) 0.027(15) -0.177(15) -0.01(2) 0.039(18) -0.062(19) 0.04(2) 0.014(19) 0.010(19) 0.021(19) 0.037(18) -0.007(18) 0.993748 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 C(1) 4.04(4) 0 0.069(19) 0.078(18) 0.010(15) -0.086(17) -0.009(16) 0.012(15) 0.017(18) -0.079(19) -0.01(2) 0.004(18) 0.007(18) 0.024(19) -0.012(19) 0.25(2) 0.00(2) 0 0 0 0 0 0 0 0 0 0.978149 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(2) 4.21(5) 0 0.00(2) -0.05(2) 0.000(17) -0.154(18) -0.024(17) 0.022(16) 0.033(19) -0.08(2) -0.03(2) 0.002(19) 0.040(19) -0.02(2) 0.005(19) 0.22(2) -0.01(2) 0 0 0 0 0 0 0 0 0 0.978149 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(3) 4.22(5) 0 -0.033(19) 0.00(2) -0.001(16) -0.155(18) -0.014(17) -0.011(16) -0.076(18) 0.020(19) 0.00(2) -0.004(19) -0.033(19) -0.013(19) 0.028(19) 0.25(2) -0.05(2) 0 0 0 0 0 0 0 0 0 0.978149 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(4) 4.00(4) 0 0.053(18) 0.019(18) -0.015(16) -0.179(17) 0.017(16) -0.016(16) -0.049(18) -0.051(18) 0.04(2) 0.014(18) -0.007(19) -0.01(2) 0.010(19) 0.29(2) 0.01(2) 0 0 0 0 0 0 0 0 0 0.978149 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(5) 4.16(5) 0 0.031(19) -0.031(19) 0.002(16) -0.157(18) 0.023(16) 0.006(16) 0.022(18) -0.008(19) 0.04(2) -0.016(19) -0.004(18) 0.018(19) 0.039(19) 0.26(2) 0.01(2) 0 0 0 0 0 0 0 0 0 0.978149 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(6) 4.11(5) 0 -0.040(19) -0.013(19) 0.024(16) -0.194(18) 0.031(17) -0.025(16) -0.092(18) 0.046(19) 0.01(2) 0.029(19) 0.024(18) 0.042(19) 0.024(19) 0.24(2) -0.02(2) 0 0 0 0 0 0 0 0 0 0.978149 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(7) 3.97(4) 0 -0.012(16) 0.019(17) 0.079(18) 0.255(19) 0.010(16) -0.031(18) -0.087(17) -0.016(16) 0.35(2) -0.06(2) 0.03(2) 0.25(2) 0.01(2) 0.012(18) -0.010(19) 0 0 0 0 0 0 0 0 0 0.980648 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(8) 3.93(4) 0 0.029(18) 0.027(18) -0.018(15) -0.157(17) -0.053(16) 0.015(16) 0.076(18) -0.036(18) -0.01(2) -0.007(18) -0.019(19) -0.01(2) -0.009(19) 0.27(2) 0.06(2) 0 0 0 0 0 0 0 0 0 0.989938 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(9) 4.21(5) 0 0.003(19) -0.033(19) 0.026(16) -0.119(18) -0.002(17) 0.026(16) -0.011(18) 0.023(19) -0.05(2) 0.026(19) 0.022(19) -0.032(19) -0.002(19) 0.24(2) 0.04(2) 0 0 0 0 0 0 0 0 0 0.989938 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(10) 3.93(5) 0 -0.07(2) 0.01(2) 0.021(16) -0.129(18) 0.026(17) -0.001(16) -0.027(19) 0.05(2) 0.01(2) 0.02(2) 0.005(19) 0.01(2) 0.059(19) 0.21(2) 0.05(2) 0 0 0 0 0 0 0 0 0 0.989938 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(11) 4.00(4) 0 0.023(19) 0.092(18) -0.014(16) -0.080(18) 0.002(17) -0.040(16) 0.107(19) -0.132(19) 0.02(2) 0.018(19) 0.004(19) -0.027(19) 0.004(19) 0.23(2) 0.05(2) 0 0 0 0 0 0 0 0 0 0.989938 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(12) 4.10(5) 0 0.04(2) -0.01(2) -0.017(16) -0.216(18) 0.002(17) -0.018(17) -0.021(19) -0.01(2) 0.01(2) 0.054(19) 0.004(19) -0.010(19) -0.02(2) 0.21(2) -0.04(2) 0 0 0 0 0 0 0 0 0 0.989938 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(13) 4.03(5) 0 -0.043(19) -0.02(2) 0.025(16) -0.128(18) -0.015(16) -0.006(16) -0.036(18) 0.048(19) -0.02(2) 0.030(19) 0.011(18) -0.01(2) 0.024(19) 0.24(2) -0.02(2) 0 0 0 0 0 0 0 0 0 0.989938 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(14) 4.36(5) 0 -0.01(2) -0.01(2) -0.107(18) -0.115(19) -0.019(17) 0.033(18) 0.04(2) 0.020(19) 0.24(2) 0.021(19) 0.025(19) -0.02(2) 0.02(2) -0.050(18) -0.21(2) 0 0 0 0 0 0 0 0 0 0.983624 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(15) 4.25(6) 0 -0.01(2) 0.10(3) -0.077(18) -0.144(19) -0.027(19) -0.10(2) -0.03(2) -0.04(2) 0.28(2) -0.05(2) -0.06(2) 0.04(2) -0.02(2) -0.04(2) -0.25(2) 0 0 0 0 0 0 0 0 0 0.983624 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(16) 4.27(5) 0 -0.11(2) 0.03(2) -0.042(18) -0.109(19) 0.006(19) 0.025(19) -0.03(2) 0.045(19) 0.22(2) 0.03(2) -0.02(2) 0.06(2) 0.04(2) 0.012(19) -0.24(2) 0 0 0 0 0 0 0 0 0 0.983624 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(17) 4.32(5) 0 -0.06(2) -0.03(2) -0.066(17) -0.146(19) 0.008(18) 0.041(18) -0.030(19) 0.031(19) 0.24(2) 0.00(2) -0.04(2) -0.05(2) 0.01(2) 0.001(18) -0.20(2) 0 0 0 0 0 0 0 0 0 0.983624 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(18) 4.03(4) 0 0.005(16) 0.011(18) -0.076(18) 0.098(18) -0.039(16) -0.089(19) -0.194(18) 0.034(17) 0.27(2) 0.010(19) 0.01(2) 0.19(2) -0.05(2) 0.026(19) -0.03(2) 0 0 0 0 0 0 0 0 0 0.978811 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(19) 4.41(5) 0 0.00(2) 0.08(2) -0.026(18) -0.003(19) -0.014(18) 0.023(18) -0.041(18) -0.016(19) 0.27(2) 0.01(2) 0.02(2) 0.04(2) -0.05(2) -0.016(18) -0.23(2) 0 0 0 0 0 0 0 0 0 0.980732 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 H(2) 0.84(3) 0 0 0 0.12(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(3) 0.83(3) 0 0 0 0.12(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(5) 0.82(3) 0 0 0 0.16(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(6) 0.74(3) 0 0 0 0.15(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(9) 0.78(3) 0 0 0 0.09(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(10) 0.84(3) 0 0 0 0.14(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(12) 0.81(3) 0 0 0 0.09(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(13) 0.82(3) 0 0 0 0.17(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(14A) 0.79(3) 0 0 0 0.11(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(14B) 0.79(3) 0 0 0 0.12(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(14C) 0.79(3) 0 0 0 0.07(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(15A) 0.75(3) 0 0 0 0.01(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(15B) 0.90(3) 0 0 0 0.12(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(15C) 0.92(3) 0 0 0 0.19(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(16A) 0.92(3) 0 0 0 0.08(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(16B) 0.76(3) 0 0 0 0.06(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(16C) 0.89(3) 0 0 0 0.19(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(17A) 0.91(3) 0 0 0 0.06(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(17B) 0.84(3) 0 0 0 0.07(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(17C) 0.84(3) 0 0 0 0.10(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(19A) 0.89(3) 0 0 0 0.12(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(19B) 0.80(3) 0 0 0 0.08(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(19C) 0.82(3) 0 0 0 0.02(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(2A) 0.66(2) 0 0 0 0.12(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(3A) 0.66(2) 0 0 0 0.037(19) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 loop_ _atom_local_axes_atom_label _atom_local_axes_atom0 _atom_local_axes_ax1 _atom_local_axes_atom1 _atom_local_axes_atom2 _atom_local_axes_ax2 O(1) C(7) X O(1) C(13) Y O(4) N(4) X O(4) O(5) Y O(5) N(4) -X O(5) O(4) Y O(3) N(1) -X O(3) O(2) Y O(2) N(1) X O(2) O(3) Y O(6) C(18) X O(6) O(7) Y O(7) C(18) X O(7) O(6) Y N(1) C(1) Z N(1) O(2) Y N(2) C(4) X N(2) C(7) Y N(3) C(8) X N(3) C(7) Y N(4) C(11) Z N(4) O(4) Y N(5) C(15) Z N(5) C(16) Y C(1) C(6) X C(1) C(2) Y C(2) C(3) X C(2) C(1) Y C(3) C(4) X C(3) C(2) Y C(4) C(3) X C(4) C(5) Y C(5) C(6) X C(5) C(4) Y C(6) C(1) X C(6) C(5) Y C(7) O(1) Z C(7) N(3) Y C(8) C(9) X C(8) C(13) Y C(9) C(10) X C(9) C(8) Y C(10) C(11) X C(10) C(9) Y C(11) C(12) X C(11) C(10) Y C(12) C(13) X C(12) C(11) Y C(13) C(8) X C(13) C(12) Y C(14) N(5) Z C(14) H(14B) Y C(15) N(5) Z C(15) H(15A) Y C(16) N(5) Z C(16) H(16A) Y C(17) N(5) Z C(17) H(17B) Y C(18) C(19) Z C(18) O(6) Y C(19) C(18) Z C(19) H(19B) Y H(2) C(2) Z H(2) C(3) Y H(3) C(3) Z H(3) C(2) Y H(5) C(5) Z H(5) C(6) Y H(6) C(6) Z H(6) C(5) Y H(9) C(9) Z H(9) C(10) Y H(10) C(10) Z H(10) C(9) Y H(12) C(12) Z H(12) C(13) Y H(13) C(13) Z H(13) C(12) Y H(14A) C(14) Z H(14A) H(14C) Y H(14B) C(14) Z H(14B) H(14C) Y H(14C) C(14) Z H(14C) H(14A) Y H(15A) C(15) Z H(15A) H(15C) Y H(15B) C(15) Z H(15B) H(15C) Y H(15C) C(15) Z H(15C) H(15A) Y H(16A) C(16) Z H(16A) H(16B) Y H(16B) C(16) Z H(16B) H(16A) Y H(16C) C(16) Z H(16C) H(16B) Y H(17A) C(17) Z H(17A) H(17C) Y H(17B) C(17) Z H(17B) H(17C) Y H(17C) C(17) Z H(17C) H(17B) Y H(19A) C(19) Z H(19A) H(19B) Y H(19B) C(19) Z H(19B) H(19A) Y H(19C) C(19) Z H(19C) H(19B) Y H(2A) N(2) Z H(2A) C(7) Y H(3A) N(3) Z H(3A) C(7) Y #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(1) C(7) 1.2299(6) 1_555 1_555 yes O(4) N(4) 1.2344(7) 1_555 1_555 yes O(5) N(4) 1.2330(7) 1_555 1_555 yes O(3) N(1) 1.2372(6) 1_555 1_555 yes O(2) N(1) 1.2357(6) 1_555 1_555 yes O(6) C(18) 1.2631(6) 1_555 1_555 yes O(7) C(18) 1.2574(6) 1_555 1_555 yes N(1) C(1) 1.4486(5) 1_555 1_555 yes N(2) C(4) 1.3827(5) 1_555 1_555 yes N(2) C(7) 1.3898(5) 1_555 1_555 yes N(2) H(2A) 1.0442(4) 1_555 1_555 yes N(3) C(7) 1.3722(5) 1_555 1_555 yes N(3) C(8) 1.3870(5) 1_555 1_555 yes N(3) H(3A) 1.0481(4) 1_555 1_555 yes N(4) C(11) 1.4512(6) 1_555 1_555 yes C(1) C(2) 1.4006(6) 1_555 1_555 yes C(1) C(6) 1.3957(6) 1_555 1_555 yes C(2) C(3) 1.3838(6) 1_555 1_555 yes C(2) H(2) 1.0832(4) 1_555 1_555 yes C(3) C(4) 1.4152(5) 1_555 1_555 yes C(3) H(3) 1.1003(4) 1_555 1_555 yes C(4) C(5) 1.4111(5) 1_555 1_555 yes C(5) C(6) 1.3880(5) 1_555 1_555 yes C(5) H(5) 1.1017(4) 1_555 1_555 yes C(6) H(6) 1.1042(4) 1_555 1_555 yes C(8) C(9) 1.4151(5) 1_555 1_555 yes C(8) C(13) 1.4089(5) 1_555 1_555 yes C(9) C(10) 1.3825(6) 1_555 1_555 yes C(9) H(9) 1.1006(4) 1_555 1_555 yes C(10) C(11) 1.3967(6) 1_555 1_555 yes C(10) H(10) 1.0856(4) 1_555 1_555 yes C(11) C(12) 1.3904(6) 1_555 1_555 yes C(12) C(13) 1.3903(6) 1_555 1_555 yes C(12) H(12) 1.0742(4) 1_555 1_555 yes C(13) H(13) 1.0900(4) 1_555 1_555 yes C(14) H(14A) 1.0701(5) 1_555 1_555 yes C(14) H(14B) 1.1029(5) 1_555 1_555 yes C(14) H(14C) 1.1122(6) 1_555 1_555 yes C(15) H(15A) 1.0947(9) 1_555 1_555 yes C(15) H(15B) 1.0814(7) 1_555 1_555 yes C(15) H(15C) 1.1187(7) 1_555 1_555 yes C(16) H(16A) 1.0967(7) 1_555 1_555 yes C(16) H(16B) 1.0845(6) 1_555 1_555 yes C(16) H(16C) 1.0881(7) 1_555 1_555 yes C(17) H(17A) 1.0785(6) 1_555 1_555 yes C(17) H(17B) 1.0716(6) 1_555 1_555 yes C(17) H(17C) 1.0991(5) 1_555 1_555 yes C(18) C(19) 1.5220(6) 1_555 1_555 yes C(19) H(19A) 1.0930(6) 1_555 1_555 yes C(19) H(19B) 1.0852(5) 1_555 1_555 yes C(19) H(19C) 1.0748(5) 1_555 1_555 yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O(3) N(1) O(2) 122.51(5) 1_555 1_555 1_555 yes O(3) N(1) C(1) 118.58(4) 1_555 1_555 1_555 yes O(2) N(1) C(1) 118.90(4) 1_555 1_555 1_555 yes C(4) N(2) C(7) 126.59(4) 1_555 1_555 1_555 yes C(4) N(2) H(2A) 114.03(3) 1_555 1_555 1_555 yes C(7) N(2) H(2A) 119.37(3) 1_555 1_555 1_555 yes C(7) N(3) C(8) 126.91(4) 1_555 1_555 1_555 yes C(7) N(3) H(3A) 119.05(3) 1_555 1_555 1_555 yes C(8) N(3) H(3A) 114.03(3) 1_555 1_555 1_555 yes O(4) N(4) O(5) 122.86(6) 1_555 1_555 1_555 yes O(4) N(4) C(11) 118.30(5) 1_555 1_555 1_555 yes O(5) N(4) C(11) 118.83(5) 1_555 1_555 1_555 yes N(1) C(1) C(2) 119.39(4) 1_555 1_555 1_555 yes N(1) C(1) C(6) 119.23(4) 1_555 1_555 1_555 yes C(2) C(1) C(6) 121.35(4) 1_555 1_555 1_555 yes C(1) C(2) C(3) 118.74(4) 1_555 1_555 1_555 yes C(1) C(2) H(2) 119.17(4) 1_555 1_555 1_555 yes C(3) C(2) H(2) 122.09(4) 1_555 1_555 1_555 yes C(2) C(3) C(4) 121.10(4) 1_555 1_555 1_555 yes C(2) C(3) H(3) 121.10(4) 1_555 1_555 1_555 yes C(4) C(3) H(3) 117.76(4) 1_555 1_555 1_555 yes N(2) C(4) C(3) 116.26(3) 1_555 1_555 1_555 yes N(2) C(4) C(5) 124.78(4) 1_555 1_555 1_555 yes C(3) C(4) C(5) 118.96(3) 1_555 1_555 1_555 yes C(4) C(5) C(6) 120.08(4) 1_555 1_555 1_555 yes C(4) C(5) H(5) 118.34(4) 1_555 1_555 1_555 yes C(6) C(5) H(5) 121.53(4) 1_555 1_555 1_555 yes C(1) C(6) C(5) 119.77(4) 1_555 1_555 1_555 yes C(1) C(6) H(6) 119.02(4) 1_555 1_555 1_555 yes C(5) C(6) H(6) 121.17(4) 1_555 1_555 1_555 yes O(1) C(7) N(2) 123.93(4) 1_555 1_555 1_555 yes O(1) C(7) N(3) 124.71(4) 1_555 1_555 1_555 yes N(2) C(7) N(3) 111.36(3) 1_555 1_555 1_555 yes N(3) C(8) C(9) 115.80(3) 1_555 1_555 1_555 yes N(3) C(8) C(13) 125.06(4) 1_555 1_555 1_555 yes C(9) C(8) C(13) 119.13(3) 1_555 1_555 1_555 yes C(8) C(9) C(10) 120.87(4) 1_555 1_555 1_555 yes C(8) C(9) H(9) 119.06(4) 1_555 1_555 1_555 yes C(10) C(9) H(9) 120.05(4) 1_555 1_555 1_555 yes C(9) C(10) C(11) 118.84(4) 1_555 1_555 1_555 yes C(9) C(10) H(10) 120.83(4) 1_555 1_555 1_555 yes C(11) C(10) H(10) 120.32(4) 1_555 1_555 1_555 yes N(4) C(11) C(10) 119.13(4) 1_555 1_555 1_555 yes N(4) C(11) C(12) 119.34(4) 1_555 1_555 1_555 yes C(10) C(11) C(12) 121.53(4) 1_555 1_555 1_555 yes C(11) C(12) C(13) 119.75(4) 1_555 1_555 1_555 yes C(11) C(12) H(12) 120.01(4) 1_555 1_555 1_555 yes C(13) C(12) H(12) 120.23(4) 1_555 1_555 1_555 yes C(8) C(13) C(12) 119.89(4) 1_555 1_555 1_555 yes C(8) C(13) H(13) 119.47(4) 1_555 1_555 1_555 yes C(12) C(13) H(13) 120.63(4) 1_555 1_555 1_555 yes H(14A) C(14) H(14B) 109.64(5) 1_555 1_555 1_555 yes H(14A) C(14) H(14C) 111.63(5) 1_555 1_555 1_555 yes H(14B) C(14) H(14C) 111.00(4) 1_555 1_555 1_555 yes H(15A) C(15) H(15B) 109.53(6) 1_555 1_555 1_555 yes H(15A) C(15) H(15C) 109.74(6) 1_555 1_555 1_555 yes H(15B) C(15) H(15C) 110.44(7) 1_555 1_555 1_555 yes H(16A) C(16) H(16B) 110.89(5) 1_555 1_555 1_555 yes H(16A) C(16) H(16C) 109.29(5) 1_555 1_555 1_555 yes H(16B) C(16) H(16C) 111.03(6) 1_555 1_555 1_555 yes H(17A) C(17) H(17B) 109.92(5) 1_555 1_555 1_555 yes H(17A) C(17) H(17C) 111.03(5) 1_555 1_555 1_555 yes H(17B) C(17) H(17C) 111.49(5) 1_555 1_555 1_555 yes O(6) C(18) O(7) 124.72(5) 1_555 1_555 1_555 yes O(6) C(18) C(19) 118.00(4) 1_555 1_555 1_555 yes O(7) C(18) C(19) 117.27(4) 1_555 1_555 1_555 yes C(18) C(19) H(19A) 109.90(4) 1_555 1_555 1_555 yes C(18) C(19) H(19B) 110.74(4) 1_555 1_555 1_555 yes C(18) C(19) H(19C) 111.39(4) 1_555 1_555 1_555 yes H(19A) C(19) H(19B) 106.98(4) 1_555 1_555 1_555 yes H(19A) C(19) H(19C) 109.28(5) 1_555 1_555 1_555 yes H(19B) C(19) H(19C) 108.43(4) 1_555 1_555 1_555 yes _database_code_depnum_ccdc_archive 'CCDC 953020' ####################################################################### # # 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_crystalstructure_6 #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; 1,3-bis(4-nitrophenyl)urea with tetramethylammonium fluoride ; _chemical_formula_moiety '2 (C13 H10 N4 O5), C4 H12 N, F' _chemical_formula_sum 'C30 H32 F N9 O10' _chemical_formula_weight 697.65 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' F F 0.0171 0.0103 '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' #============================================================================== # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c c a' _symmetry_space_group_name_Hall '-P 2a 2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' 'x+1/2, -y, -z+1/2' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' '-x-1/2, y, z-1/2' 'x, -y, z-1/2' _cell_length_a 35.929(6) _cell_length_b 7.0153(11) _cell_length_c 12.624(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3181.9(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8688 _cell_measurement_theta_min 1.7 _cell_measurement_theta_max 31.6 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.456 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9886 _exptl_absorpt_correction_T_max 0.9954 _exptl_absorpt_process_details ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _exptl_special_details ; ? ; #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.68890 _diffrn_source_type 'DLS beamline I19' _diffrn_radiation_source synchrotron _diffrn_radiation_collimation 'confocal mirrors' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku Saturn724 (2x2 bin mode)' _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_device 'four-circle \k diffractometer' _diffrn_measurement_device_type CrystalLogic _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support 'MiTeGen MicroMesh' _diffrn_reflns_number 159791 _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 76 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 49.89 _reflns_number_total 17539 _reflns_number_gt 15592 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; #============================================================================== # REFINEMENT DATA _refine_special_details ; The Uij values for the TMA group were large. Attempts to obtain a very low temperature, high-resolution X-ray diffraction data set were hampered by a phase transition, which occurred below 60 K. This lower temperature structure, with a much larger asymmetric unit and split peaks in the diffraction data was unsuitable for a charge density study. 3m symmetry was applied to the TMA cation however large residual peaks remained (see below) which are associated with the TMA group. PK(1) is 0.39 A from C(15) 0.2226 0.6741 0.1391 0.98 PK(2) is 0.67 A from C(15) 0.2381 0.5801 0.1870 0.60 PK(3) is 0.54 A from C(14) 0.2329 0.4155 -0.0027 0.45 PK(4) is 0.51 A from C(14) 0.2229 0.3369 0.0464 0.43 PK(5) is 0.48 A from N(4) 0.2003 -0.0481 -0.1349 0.28 HL(1) is 0.49 A from H(15A) 0.2169 0.7211 0.1140 -0.85 HL(2) is 0.15 A from C(15) 0.2274 0.6232 0.1556 -0.54 HL(3) is 0.69 A from C(14) 0.2268 0.4818 -0.0003 -0.48 HL(4) is 0.54 A from N(4) 0.1884 -0.0584 -0.2085 -0.34 HL(5) is 0.62 A from O(5) 0.2152 -0.1128 -0.1417 -0.29 ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc w1 = 1/[s^2^(Fo)] ; _refine_ls_extinction_method none _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 12478 _refine_ls_number_parameters 631 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.05 _refine_ls_R_factor_gt 0.035 _refine_ls_wR_factor_ref 0.047 _refine_ls_goodness_of_fit_ref 2.569 _refine_ls_shift/su_max 0 _refine_diff_density_max 0.981 _refine_diff_density_min -0.854 _refine_diff_density_rms 0.041 _diffrn_measured_fraction_theta_max 0.84 _diffrn_reflns_theta_full 40.17 _diffrn_measured_fraction_theta_full 0.93 _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'Volkov et al, (2006)' _computing_molecular_graphics 'Volkov et al, (2006)' _computing_publication_material 'Volkov et al, (2006)' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_symmetry_multiplicity F(1) 0 0.29469(13) -0.25 0.024 1 4 O(1) 0.037359(12) 0.17354(6) 0.07795(3) 0.02 1 8 O(2) -0.132646(12) 0.41314(8) 0.30812(3) 0.026 1 8 O(3) -0.163537(12) 0.47382(7) 0.16462(4) 0.027 1 8 O(4) 0.205209(19) -0.06576(10) -0.26202(7) 0.041 1 8 O(5) 0.213451(16) -0.10689(10) -0.09257(8) 0.04 1 8 N(2) -0.008392(9) 0.27790(5) -0.03860(3) 0.016 1 8 N(3) 0.047671(10) 0.18914(5) -0.10332(3) 0.017 1 8 N(1) -0.134449(9) 0.42899(4) 0.21080(3) 0.018 1 8 N(4) 0.194367(12) -0.05514(5) -0.16904(4) 0.03 1 8 N(5) 0.25 0.5 0.09071(7) 0.032 1 4 C(5) -0.037373(10) 0.29062(5) 0.13863(3) 0.017 1 8 C(4) -0.038228(9) 0.31406(4) 0.02784(3) 0.014 1 8 C(1) -0.101421(9) 0.39177(4) 0.14805(3) 0.016 1 8 C(3) -0.071310(9) 0.37996(4) -0.02103(3) 0.016 1 8 C(6) -0.068972(10) 0.33024(5) 0.19850(3) 0.017 1 8 C(2) -0.102924(10) 0.41739(5) 0.03815(3) 0.016 1 8 C(8) 0.084277(9) 0.13352(4) -0.11220(3) 0.016 1 8 C(7) 0.026582(9) 0.20993(4) -0.01218(3) 0.015 1 8 C(11) 0.157272(11) 0.01762(5) -0.14953(4) 0.022 1 8 C(9) 0.097837(12) 0.11303(5) -0.21698(3) 0.02 1 8 C(13) 0.108418(11) 0.09871(5) -0.02609(3) 0.019 1 8 C(12) 0.144750(12) 0.03985(6) -0.04536(4) 0.022 1 8 C(10) 0.134135(13) 0.05708(6) -0.23593(4) 0.023 1 8 C(15) 0.22939(4) 0.64168(19) 0.15536(11) 0.097 1 8 C(14) 0.22189(2) 0.39875(13) 0.02529(7) 0.052 1 8 H(2A) -0.011298 0.298181 -0.117298 0.028(4) 1 8 H(3A) 0.034071 0.218323 -0.171345 0.034(4) 1 8 H(5) -0.011912 0.238748 0.174368 0.041(4) 1 8 H(3) -0.070469 0.405156 -0.105631 0.031(3) 1 8 H(6) -0.067639 0.310696 0.283516 0.030(3) 1 8 H(2) -0.128498 0.468488 0.002714 0.030(4) 1 8 H(9) 0.079269 0.136256 -0.283314 0.049(4) 1 8 H(13) 0.099457 0.113055 0.055428 0.036(4) 1 8 H(12) 0.163094 0.00622 0.020104 0.043(4) 1 8 H(10) 0.144492 0.036531 -0.31568 0.057(5) 1 8 H(15A) 0.22192 0.779812 0.129042 0.147 1 8 H(15B) 0.248323 0.710469 0.207062 0.147 1 8 H(15C) 0.212427 0.560586 0.207086 0.147 1 8 H(14A) 0.202442 0.332454 0.07645 0.078 1 8 H(14B) 0.234809 0.295012 -0.023304 0.078 1 8 H(14C) 0.208954 0.504966 -0.0216 0.078 1 8 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 F(1) 0.0220(3) 0.0362(3) 0.0138(2) 0 -0.00230(17) 0 O(1) 0.01898(15) 0.02567(14) 0.01411(14) 0.00180(11) -0.00013(10) 0.00229(11) O(2) 0.02216(16) 0.03944(19) 0.01717(15) -0.00181(13) 0.00428(10) 0.00287(13) O(3) 0.01738(14) 0.03877(19) 0.02359(17) -0.00081(14) 0.00136(11) 0.00582(12) O(4) 0.0266(2) 0.0415(3) 0.0545(4) 0.0004(3) 0.0204(2) 0.00458(19) O(5) 0.01811(19) 0.0411(3) 0.0621(4) 0.0050(3) -0.0002(2) 0.00548(16) N(2) 0.01501(12) 0.01955(11) 0.01292(12) -0.00099(8) 0.00026(8) 0.00006(8) N(3) 0.01599(12) 0.01968(11) 0.01400(12) -0.00079(9) 0.00064(8) 0.00199(9) N(1) 0.01645(10) 0.02137(11) 0.01739(12) -0.00172(8) 0.00225(8) 0.00033(7) N(4) 0.01672(13) 0.02533(13) 0.0470(3) 0.00165(13) 0.00822(12) 0.00035(10) N(5) 0.0474(4) 0.0261(2) 0.0213(3) 0 0 -0.0103(3) C(5) 0.01577(12) 0.02144(11) 0.01347(12) 0.00007(9) 0.00000(8) 0.00081(9) C(4) 0.01462(11) 0.01542(9) 0.01313(11) -0.00066(7) 0.00016(7) -0.00104(7) C(1) 0.01573(11) 0.01649(10) 0.01482(12) -0.00051(8) 0.00099(8) -0.00024(8) C(3) 0.01600(12) 0.01813(10) 0.01371(12) 0.00022(8) -0.00024(8) -0.00007(8) C(6) 0.01696(13) 0.02120(11) 0.01339(12) -0.00001(9) 0.00084(8) 0.00068(9) C(2) 0.01556(12) 0.01832(10) 0.01530(12) 0.00002(9) -0.00024(8) 0.00043(8) C(8) 0.01611(12) 0.01562(9) 0.01588(12) 0.00000(8) 0.00127(8) 0.00059(8) C(7) 0.01533(11) 0.01560(9) 0.01347(11) -0.00071(8) 0.00036(8) -0.00026(7) C(11) 0.01641(14) 0.01901(11) 0.02981(19) 0.00152(11) 0.00511(11) -0.00032(9) C(9) 0.02041(14) 0.02285(13) 0.01704(14) 0.00021(10) 0.00380(10) 0.00201(10) C(13) 0.01693(13) 0.02158(12) 0.01849(14) 0.00095(10) -0.00031(9) 0.00174(9) C(12) 0.01664(14) 0.02306(13) 0.02619(18) 0.00266(12) -0.00016(11) 0.00124(10) C(10) 0.02071(16) 0.02404(14) 0.02343(17) 0.00031(12) 0.00725(12) 0.00115(11) C(15) 0.0798(7) 0.1023(8) 0.1088(9) -0.0798(8) 0.0729(7) -0.0633(6) C(14) 0.0405(3) 0.0647(4) 0.0501(4) -0.0285(3) -0.0247(3) 0.0213(3) #----------------------------------------------------------------------------# # MULTIPOLE PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_rho_multipole_atom_label _atom_rho_multipole_coeff_Pv _atom_rho_multipole_coeff_P00 _atom_rho_multipole_coeff_P11 _atom_rho_multipole_coeff_P1-1 _atom_rho_multipole_coeff_P10 _atom_rho_multipole_coeff_P20 _atom_rho_multipole_coeff_P21 _atom_rho_multipole_coeff_P2-1 _atom_rho_multipole_coeff_P22 _atom_rho_multipole_coeff_P2-2 _atom_rho_multipole_coeff_P30 _atom_rho_multipole_coeff_P31 _atom_rho_multipole_coeff_P3-1 _atom_rho_multipole_coeff_P32 _atom_rho_multipole_coeff_P3-2 _atom_rho_multipole_coeff_P33 _atom_rho_multipole_coeff_P3-3 _atom_rho_multipole_coeff_P40 _atom_rho_multipole_coeff_P41 _atom_rho_multipole_coeff_P4-1 _atom_rho_multipole_coeff_P42 _atom_rho_multipole_coeff_P4-2 _atom_rho_multipole_coeff_P43 _atom_rho_multipole_coeff_P4-3 _atom_rho_multipole_coeff_P44 _atom_rho_multipole_coeff_P4-4 _atom_rho_multipole_kappa _atom_rho_multipole_kappa_prime0 _atom_rho_multipole_kappa_prime1 _atom_rho_multipole_kappa_prime2 _atom_rho_multipole_kappa_prime3 _atom_rho_multipole_kappa_prime4 _atom_rho_multipole_radial_slater_n0 _atom_rho_multipole_radial_slater_zeta0 _atom_rho_multipole_radial_slater_n1 _atom_rho_multipole_radial_slater_zeta1 _atom_rho_multipole_radial_slater_n2 _atom_rho_multipole_radial_slater_zeta2 _atom_rho_multipole_radial_slater_n3 _atom_rho_multipole_radial_slater_zeta3 _atom_rho_multipole_radial_slater_n4 _atom_rho_multipole_radial_slater_zeta4 F(1) 3.694(13) 0 0 0 -0.068(10) 0.011(12) 0 0 0.001(9) 0.006(10) -0.037(8) 0 0 0.001(7) -0.002(7) 0 0 0.007(10) 0 0 -0.012(9) -0.023(9) 0 0 0.011(8) 0.003(8) 0.971273 1 1 1 1 1 2 5.1078857142857 2 5.1078857142857 2 5.1078857142857 3 5.1078857142857 4 5.1078857142857 O(1) 6.15(2) 0 -0.035(13) -0.013(11) 0.017(12) -0.051(13) -0.003(12) 0.011(12) -0.057(13) 0.003(12) -0.020(11) 0.025(10) -0.020(10) 0.023(10) -0.009(10) 0.021(10) -0.009(10) 0.039(13) 0.001(13) -0.012(13) -0.025(13) -0.017(13) 0.009(12) -0.030(12) 0.001(12) -0.004(12) 0.984439 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(2) 6.103(16) 0 -0.069(10) -0.014(9) 0.016(10) -0.052(12) -0.004(10) 0.005(10) -0.135(10) 0.004(10) 0.024(9) 0.005(9) 0.003(8) 0.006(8) -0.021(8) 0.024(8) 0.014(8) -0.024(12) 0.005(11) 0.000(11) -0.003(11) 0.007(11) -0.003(10) 0.003(10) -0.001(10) -0.002(10) 0.993279 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(3) 6.1027 0 -0.0689 -0.014 0.0159 -0.0516 -0.0037 0.0049 -0.1348 0.0037 0.0241 0.0049 0.0028 0.0064 -0.0214 0.0239 0.0137 -0.0241 0.0054 0.0001 -0.0032 0.007 -0.0032 0.0034 -0.0006 -0.0018 0.993279 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(4) 6.11(2) 0 -0.027(14) -0.003(13) 0.025(12) -0.004(16) -0.002(14) -0.035(14) -0.113(14) -0.026(14) -0.063(12) 0.047(12) -0.023(11) 0.039(11) 0.053(11) -0.018(12) 0.014(11) 0.005(16) -0.007(14) 0.022(14) 0.017(15) -0.012(15) 0.016(14) -0.043(14) 0.008(15) 0.013(14) 0.993279 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(5) 6.1071 0 -0.0265 -0.0027 0.025 -0.0035 -0.0019 -0.0352 -0.1132 -0.0262 -0.0634 0.0471 -0.0234 0.0385 0.0525 -0.0175 0.0141 0.0052 -0.0065 0.0219 0.0167 -0.0118 0.0156 -0.043 0.008 0.013 0.993279 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 N(2) 5.11(3) 0 -0.054(13) -0.044(14) -0.021(11) -0.007(12) -0.003(11) -0.005(11) -0.013(12) 0.030(13) 0.009(12) 0.005(11) 0.027(11) 0.009(11) -0.011(11) 0.158(12) 0.061(12) 0.022(15) -0.007(14) 0.013(13) 0.016(14) -0.010(14) -0.033(14) 0.001(14) 0.012(14) -0.011(14) 0.983991 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(3) 5.19(3) 0 -0.047(13) -0.027(14) 0.015(11) -0.015(13) 0.001(12) 0.008(11) 0.004(13) 0.004(13) 0.004(12) 0.002(11) 0.014(11) 0.014(11) -0.003(11) 0.181(12) 0.030(12) 0.020(15) -0.011(14) 0.000(14) 0.019(15) -0.006(14) 0.016(14) 0.009(14) -0.010(14) -0.011(15) 0.983991 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(1) 5.03(2) 0 0 0 0.016(11) 0.069(11) 0 0 -0.152(12) 0 0.238(11) 0 0 0.167(11) 0 0 0 0.032(14) 0 0 -0.015(14) 0 0 0 0.023(13) 0 0.989099 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(4) 5.0294 0 0 0 0.016 0.0692 0 0 -0.152 0 0.2381 0 0 0.1665 0 0 0 0.0316 0 0 -0.0145 0 0 0 0.0234 0 0.989099 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(5) 2.44(2) 0 0 0 0.006(9) 0.049(11) 0 0 0.017(12) 0.077(11) -0.024(10) 0 0 -0.173(11) -0.038(10) 0 0 -0.048(14) 0 0 -0.018(14) -0.025(14) 0 0 0.088(14) -0.036(13) 1.036214 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 C(5) 4.03(5) 0 0.026(17) 0.020(18) -0.051(14) -0.142(16) -0.006(14) 0.012(13) 0.009(15) 0.020(17) -0.020(16) 0.031(16) 0.021(15) 0.011(15) -0.001(16) 0.197(17) 0.011(16) 0 0 0 0 0 0 0 0 0 0.992466 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(4) 4.09(4) 0 0.001(16) 0.063(16) -0.004(13) -0.193(14) -0.004(13) 0.018(13) 0.009(15) -0.058(15) 0.000(15) -0.006(14) 0.014(15) -0.002(15) 0.019(15) 0.255(17) 0.025(17) 0 0 0 0 0 0 0 0 0 0.992466 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(1) 4.05(4) 0 0.032(16) 0.069(16) 0.042(14) -0.082(14) -0.005(14) 0.008(13) 0.066(15) -0.087(15) 0.018(15) 0.014(15) 0.010(14) 0.000(15) 0.017(15) 0.195(17) 0.025(16) 0 0 0 0 0 0 0 0 0 0.992466 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(3) 4.06(4) 0 0.018(17) -0.014(18) 0.015(13) -0.139(14) -0.016(14) 0.009(13) -0.008(16) -0.009(16) -0.022(15) 0.015(15) 0.031(15) -0.020(15) 0.010(15) 0.221(17) -0.022(16) 0 0 0 0 0 0 0 0 0 0.992466 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(6) 4.10(5) 0 -0.027(17) -0.007(18) -0.015(14) -0.190(15) -0.007(14) 0.016(13) -0.024(15) -0.008(17) -0.009(16) 0.022(15) 0.010(16) 0.008(16) 0.027(16) 0.278(17) -0.007(17) 0 0 0 0 0 0 0 0 0 0.992466 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(2) 4.08(5) 0 0.012(17) 0.017(18) -0.016(13) -0.178(15) -0.020(13) -0.003(13) 0.017(15) 0.002(16) 0.019(16) 0.002(15) 0.019(15) -0.001(15) -0.016(15) 0.265(17) 0.011(17) 0 0 0 0 0 0 0 0 0 0.992466 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(8) 3.94(4) 0 0.014(16) 0.069(17) -0.002(14) -0.167(14) 0.007(14) 0.041(13) -0.008(16) -0.039(16) -0.011(16) 0.011(15) 0.014(15) 0.018(16) -0.007(16) 0.267(18) 0.004(18) 0 0 0 0 0 0 0 0 0 0.997045 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(7) 4.02(4) 0 0.005(13) -0.020(15) 0.124(16) 0.166(17) 0.003(14) -0.009(15) -0.167(14) 0.032(13) 0.23(2) 0.001(16) -0.011(19) 0.193(17) 0.019(16) 0.011(14) -0.005(15) 0 0 0 0 0 0 0 0 0 0.98616 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(11) 4.00(4) 0 0.149(18) 0.035(18) -0.006(16) -0.071(15) 0.021(16) -0.002(15) 0.076(18) -0.060(17) 0.026(17) -0.013(16) 0.025(16) 0.010(18) 0.055(18) 0.18(2) -0.012(19) 0 0 0 0 0 0 0 0 0 0.997045 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(9) 3.95(5) 0 0.042(19) 0.09(2) -0.058(15) -0.128(16) -0.001(15) -0.017(14) 0.012(17) -0.033(17) 0.002(17) 0.033(16) -0.030(16) 0.001(17) -0.037(16) 0.189(18) 0.047(17) 0 0 0 0 0 0 0 0 0 0.997045 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(13) 4.02(5) 0 -0.018(18) 0.02(2) -0.006(14) -0.135(15) 0.010(14) 0.017(14) -0.031(16) -0.028(18) 0.039(17) 0.013(16) 0.023(15) 0.009(16) -0.022(16) 0.223(18) -0.035(17) 0 0 0 0 0 0 0 0 0 0.997045 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(12) 3.99(5) 0 0.010(19) 0.00(2) 0.013(14) -0.153(17) -0.022(15) -0.006(15) 0.025(18) -0.001(18) 0.081(17) 0.054(16) 0.041(17) 0.027(18) 0.034(18) 0.223(19) 0.011(19) 0 0 0 0 0 0 0 0 0 0.997045 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(10) 3.89(5) 0 0.12(2) 0.09(2) 0.010(15) -0.218(17) 0.046(16) 0.014(14) 0.017(18) -0.056(19) 0.051(18) -0.054(18) 0.005(16) -0.033(18) 0.010(18) 0.32(2) -0.003(19) 0 0 0 0 0 0 0 0 0 0.997045 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(15) 4.6061 0 0 0 -0.1162 -0.1413 0 0 0 0 0.1907 0 0 0 0 0.0404 0 0 0 0 0 0 0 0 0 0 0.972797 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(14) 4.61(5) 0 0 0 -0.116(16) -0.141(16) 0 0 0 0 0.191(19) 0 0 0 0 0.040(19) 0 0 0 0 0 0 0 0 0 0 0.972797 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 H(2A) 0.76(3) 0 0 0 0.09(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(3A) 0.72(4) 0 0 0 0.11(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(5) 0.95(4) 0 0 0 0.21(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(3) 0.86(4) 0 0 0 0.12(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(6) 0.83(4) 0 0 0 0.13(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(2) 0.78(4) 0 0 0 0.15(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(9) 1.03(5) 0 0 0 0.16(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(13) 0.87(4) 0 0 0 0.17(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(12) 0.89(4) 0 0 0 0.15(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(10) 1.05(5) 0 0 0 0.25(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(15A) 0.794 0 0 0 0.0875 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(15B) 0.794 0 0 0 0.0875 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(15C) 0.794 0 0 0 0.0875 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(14A) 0.794(16) 0 0 0 0.088(14) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(14B) 0.794 0 0 0 0.0875 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(14C) 0.794 0 0 0 0.0875 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 loop_ _atom_local_axes_atom_label _atom_local_axes_atom0 _atom_local_axes_ax1 _atom_local_axes_atom1 _atom_local_axes_atom2 _atom_local_axes_ax2 F(1) DUM2 Z F(1) C(15) Y O(1) C(7) X O(1) C(13) Y O(2) N(1) X O(2) O(3) Y O(3) N(1) -X O(3) O(2) Y O(4) N(4) X O(4) O(5) Y O(5) N(4) -X O(5) O(4) Y N(2) C(4) X N(2) C(7) Y N(3) C(8) X N(3) C(7) Y N(1) C(1) Z N(1) O(2) Y N(4) C(11) Z N(4) O(4) Y N(5) DUM1 Z N(5) C(15) Y C(5) C(6) X C(5) C(4) Y C(4) C(3) X C(4) C(5) Y C(1) C(6) X C(1) C(2) Y C(3) C(4) X C(3) C(2) Y C(6) C(1) X C(6) C(5) Y C(2) C(3) X C(2) C(1) Y C(8) C(9) X C(8) C(13) Y C(7) O(1) Z C(7) N(3) Y C(11) C(12) X C(11) C(10) Y C(9) C(10) X C(9) C(8) Y C(13) C(8) X C(13) C(12) Y C(12) C(13) X C(12) C(11) Y C(10) C(11) X C(10) C(9) Y C(15) N(5) Z C(15) H(15A) Y C(14) N(5) Z C(14) H(14A) Y H(2A) N(2) Z H(2A) C(7) Y H(3A) N(3) Z H(3A) C(7) Y H(5) C(5) Z H(5) C(6) Y H(3) C(3) Z H(3) C(2) Y H(6) C(6) Z H(6) C(5) Y H(2) C(2) Z H(2) C(3) Y H(9) C(9) Z H(9) C(10) Y H(13) C(13) Z H(13) C(12) Y H(12) C(12) Z H(12) C(13) Y H(10) C(10) Z H(10) C(9) Y H(15A) C(15) Z H(15A) H(15C) Y H(15B) C(15) Z H(15B) H(15C) Y H(15C) C(15) Z H(15C) H(15A) Y H(14A) C(14) Z H(14A) H(14C) Y H(14B) C(14) Z H(14B) H(14C) Y H(14C) C(14) Z H(14C) H(14A) Y #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(1) C(7) 1.2287(5) 1_555 1_555 yes O(2) N(1) 1.2353(5) 1_555 1_555 yes O(3) N(1) 1.2373(5) 1_555 1_555 yes O(4) N(4) 1.2391(9) 1_555 1_555 yes O(5) N(4) 1.2384(9) 1_555 1_555 yes N(2) C(4) 1.3846(5) 1_555 1_555 yes N(2) C(7) 1.3848(5) 1_555 1_555 yes N(2) H(2A) 1.0090(4) 1_555 1_555 yes N(3) C(8) 1.3764(5) 1_555 1_555 yes N(3) C(7) 1.3853(5) 1_555 1_555 yes N(3) H(3A) 1.0090(4) 1_555 1_555 yes N(1) C(1) 1.4505(5) 1_555 1_555 yes N(4) C(11) 1.4483(6) 1_555 1_555 yes C(5) C(4) 1.4085(5) 1_555 1_555 yes C(5) C(6) 1.3920(5) 1_555 1_555 yes C(5) H(5) 1.0830(4) 1_555 1_555 yes C(4) C(3) 1.4167(5) 1_555 1_555 yes C(1) C(6) 1.3969(5) 1_555 1_555 yes C(1) C(2) 1.4000(5) 1_555 1_555 yes C(3) C(2) 1.3846(5) 1_555 1_555 yes C(3) H(3) 1.0830(3) 1_555 1_555 yes C(6) H(6) 1.0830(4) 1_555 1_555 yes C(2) H(2) 1.0830(4) 1_555 1_555 yes C(8) C(9) 1.4169(5) 1_555 1_555 yes C(8) C(13) 1.4119(5) 1_555 1_555 yes C(11) C(12) 1.3987(7) 1_555 1_555 yes C(11) C(10) 1.3990(7) 1_555 1_555 yes C(9) C(10) 1.3828(6) 1_555 1_555 yes C(9) H(9) 1.0830(5) 1_555 1_555 yes C(13) C(12) 1.3905(5) 1_555 1_555 yes C(13) H(13) 1.0830(4) 1_555 1_555 yes C(12) H(12) 1.0830(5) 1_555 1_555 yes C(10) H(10) 1.0830(5) 1_555 1_555 yes C(15) H(15A) 1.0590(19) 1_555 1_555 yes C(15) H(15B) 1.0590(12) 1_555 1_555 yes C(15) H(15C) 1.0590(10) 1_555 1_555 yes C(14) H(14A) 1.0590(12) 1_555 1_555 yes C(14) H(14B) 1.0590(7) 1_555 1_555 yes C(14) H(14C) 1.0590(8) 1_555 1_555 yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(4) N(2) C(7) 128.30(3) 1_555 1_555 1_555 yes C(4) N(2) H(2A) 119.38(3) 1_555 1_555 1_555 yes C(7) N(2) H(2A) 112.31(3) 1_555 1_555 1_555 yes C(8) N(3) C(7) 128.32(3) 1_555 1_555 1_555 yes C(8) N(3) H(3A) 116.81(3) 1_555 1_555 1_555 yes C(7) N(3) H(3A) 114.87(3) 1_555 1_555 1_555 yes O(2) N(1) O(3) 122.39(4) 1_555 1_555 1_555 yes O(2) N(1) C(1) 118.95(3) 1_555 1_555 1_555 yes O(3) N(1) C(1) 118.65(3) 1_555 1_555 1_555 yes O(4) N(4) O(5) 123.14(7) 1_555 1_555 1_555 yes O(4) N(4) C(11) 118.14(6) 1_555 1_555 1_555 yes O(5) N(4) C(11) 118.71(6) 1_555 1_555 1_555 yes C(4) C(5) C(6) 119.87(3) 1_555 1_555 1_555 yes C(4) C(5) H(5) 118.12(3) 1_555 1_555 1_555 yes C(6) C(5) H(5) 121.99(3) 1_555 1_555 1_555 yes N(2) C(4) C(5) 124.28(3) 1_555 1_555 1_555 yes N(2) C(4) C(3) 116.46(3) 1_555 1_555 1_555 yes C(5) C(4) C(3) 119.26(3) 1_555 1_555 1_555 yes N(1) C(1) C(6) 119.30(3) 1_555 1_555 1_555 yes N(1) C(1) C(2) 119.11(3) 1_555 1_555 1_555 yes C(6) C(1) C(2) 121.58(3) 1_555 1_555 1_555 yes C(4) C(3) C(2) 121.01(3) 1_555 1_555 1_555 yes C(4) C(3) H(3) 117.34(3) 1_555 1_555 1_555 yes C(2) C(3) H(3) 121.60(3) 1_555 1_555 1_555 yes C(5) C(6) C(1) 119.66(3) 1_555 1_555 1_555 yes C(5) C(6) H(6) 118.47(3) 1_555 1_555 1_555 yes C(1) C(6) H(6) 121.86(3) 1_555 1_555 1_555 yes C(1) C(2) C(3) 118.60(3) 1_555 1_555 1_555 yes C(1) C(2) H(2) 118.98(3) 1_555 1_555 1_555 yes C(3) C(2) H(2) 122.41(3) 1_555 1_555 1_555 yes N(3) C(8) C(9) 115.67(3) 1_555 1_555 1_555 yes N(3) C(8) C(13) 124.99(3) 1_555 1_555 1_555 yes C(9) C(8) C(13) 119.33(3) 1_555 1_555 1_555 yes O(1) C(7) N(2) 125.49(4) 1_555 1_555 1_555 yes O(1) C(7) N(3) 125.09(4) 1_555 1_555 1_555 yes N(2) C(7) N(3) 109.42(3) 1_555 1_555 1_555 yes N(4) C(11) C(12) 119.68(5) 1_555 1_555 1_555 yes N(4) C(11) C(10) 118.95(4) 1_555 1_555 1_555 yes C(12) C(11) C(10) 121.32(4) 1_555 1_555 1_555 yes C(8) C(9) C(10) 120.97(4) 1_555 1_555 1_555 yes C(8) C(9) H(9) 119.66(4) 1_555 1_555 1_555 yes C(10) C(9) H(9) 119.33(4) 1_555 1_555 1_555 yes C(8) C(13) C(12) 119.57(4) 1_555 1_555 1_555 yes C(8) C(13) H(13) 122.20(3) 1_555 1_555 1_555 yes C(12) C(13) H(13) 118.22(4) 1_555 1_555 1_555 yes C(11) C(12) C(13) 119.97(4) 1_555 1_555 1_555 yes C(11) C(12) H(12) 119.83(4) 1_555 1_555 1_555 yes C(13) C(12) H(12) 120.17(4) 1_555 1_555 1_555 yes C(11) C(10) C(9) 118.80(4) 1_555 1_555 1_555 yes C(11) C(10) H(10) 119.62(4) 1_555 1_555 1_555 yes C(9) C(10) H(10) 121.51(5) 1_555 1_555 1_555 yes H(15A) C(15) H(15B) 86.52(7) 1_555 1_555 1_555 yes H(15A) C(15) H(15C) 122.63(11) 1_555 1_555 1_555 yes H(15B) C(15) H(15C) 103.56(13) 1_555 1_555 1_555 yes H(14A) C(14) H(14B) 109.92(9) 1_555 1_555 1_555 yes H(14A) C(14) H(14C) 111.13(7) 1_555 1_555 1_555 yes H(14B) C(14) H(14C) 110.62(8) 1_555 1_555 1_555 yes _database_code_depnum_ccdc_archive 'CCDC 953021' ####################################################################### # # 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_crystalstructure_7 #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; 1,3-bis(3-nitrophenyl)urea with tetramethylammonium chloride ; _chemical_formula_moiety 'C13 H10 N4 O5, C4 H12 N, Cl' _chemical_formula_sum 'C17 H22 Cl N5 O5' _chemical_formula_weight 411.85 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0007 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.0777 0.0747 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0018 0.0014 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0040 0.0026 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #============================================================================== # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 6.8211(5) _cell_length_b 14.4139(11) _cell_length_c 19.7918(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1945.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 11299 _cell_measurement_theta_min 1.2 _cell_measurement_theta_max 20.1 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9770 _exptl_absorpt_correction_T_max 0.9935 _exptl_absorpt_process_details ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _diffrn_reflns_reduction_process ; Scaled and merged with Sortav R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.48590 _diffrn_source_type 'DLS beamline I19' _diffrn_source synchrotron _diffrn_radiation_collimation 'confocal mirrors' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku Saturn724 (2x2 bin mode)' _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_device 'four-circle \k diffractometer' _diffrn_measurement_device_type CrystalLogic _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support 'MiTeGen MicroMesh' _diffrn_reflns_number 363541 _diffrn_reflns_av_R_equivalents 0.0186 _diffrn_reflns_av_sigmaI/netI 0.0350 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 41 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 57 _diffrn_reflns_theta_min 1.19 _diffrn_reflns_theta_max 45.18 _reflns_number_total 25557 _reflns_number_gt 19633 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; #============================================================================== # REFINEMENT DATA _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc w1 = 1/[s^2^(Fo)] ; _refine_ls_hydrogen_treatment noref #_refine_ls_abs_structure_details # 'Flack H D (1983), Acta Cryst. A39, 876-881' #_refine_ls_abs_structure_Flack 0.10(3) # values above from standard resolution structure refinement _refine_ls_extinction_method none _refine_ls_number_reflns 37163 _refine_ls_number_parameters 760 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.071 _refine_ls_R_factor_gt 0.038 _refine_ls_wR_factor_ref 0.038 _refine_ls_goodness_of_fit_ref 1.173 _refine_ls_shift/su_max 0 _refine_diff_density_max 0.540 _refine_diff_density_min -0.329 _refine_diff_density_rms 0.061 _diffrn_measured_fraction_theta_max 0.90 _diffrn_reflns_theta_full 44.2 _diffrn_measured_fraction_theta_full 0.98 _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'Volkov et al, (2006)' _computing_molecular_graphics 'Volkov et al, (2006)' _computing_publication_material 'Volkov et al, (2006)' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_symmetry_multiplicity CL(1) 0.598774(11) 1.615353(6) 1.035232 0.017 1 4 O(1) 0.88630(6) 1.51856(2) 0.817270(18) 0.017 1 4 O(2) 0.98486(10) 1.71710(3) 0.65173(2) 0.027 1 4 O(3) 0.97105(11) 1.86657(4) 0.64748(3) 0.032 1 4 O(4) 0.86046(9) 1.10074(3) 0.81589(3) 0.028 1 4 O(5) 0.93155(8) 1.22652(3) 0.76269(2) 0.024 1 4 N(1) 0.95516(5) 1.79302(2) 0.678149(19) 0.019 1 4 N(2) 0.80990(4) 1.63514(2) 0.892289(15) 0.013 1 4 N(3) 0.77630(5) 1.48496(2) 0.924652(16) 0.015 1 4 N(4) 0.87640(4) 1.18511(2) 0.813441(18) 0.016 1 4 N(5) 0.89159(4) 1.42427(2) 0.635598(17) 0.015 1 4 C(1) 0.87791(5) 1.88181(2) 0.78062(2) 0.016 1 4 C(2) 0.83292(5) 1.88248(2) 0.84930(2) 0.017 1 4 C(3) 0.81270(5) 1.79997(2) 0.884798(17) 0.015 1 4 C(4) 0.83534(4) 1.713839(19) 0.852390(15) 0.012 1 4 C(5) 0.88169(4) 1.71155(2) 0.783622(16) 0.013 1 4 C(6) 0.90169(4) 1.79583(2) 0.750046(17) 0.014 1 4 C(7) 0.82833(4) 1.544020(19) 0.872873(15) 0.012 1 4 C(8) 0.78222(4) 1.38842(2) 0.924479(15) 0.013 1 4 C(9) 0.73542(5) 1.34301(2) 0.985257(17) 0.015 1 4 C(10) 0.73570(5) 1.24678(3) 0.989342(19) 0.017 1 4 C(11) 0.78137(5) 1.19285(2) 0.933042(19) 0.016 1 4 C(12) 0.82794(4) 1.23946(2) 0.873811(17) 0.013 1 4 C(13) 0.83089(4) 1.33546(2) 0.867783(16) 0.013 1 4 C(14) 0.87990(9) 1.49831(4) 0.58328(3) 0.027 1 4 C(15) 0.71384(5) 1.42833(4) 0.67963(2) 0.022 1 4 C(16) 0.89900(6) 1.33161(3) 0.60141(3) 0.021 1 4 C(17) 1.07186(6) 1.43674(5) 0.67760(3) 0.027 1 4 H(1) 0.893945 1.94556 0.751869 0.036 1 4 H(2) 0.818166 1.947586 0.874144 0.039 1 4 H(3) 0.784704 1.801857 0.93834 0.03 1 4 H(5) 0.901594 1.64579 0.757214 0.027 1 4 H(9) 0.696353 1.383326 1.028373 0.034 1 4 H(10) 0.699484 1.21407 1.036725 0.035 1 4 H(11) 0.781928 1.11807 0.933891 0.034 1 4 H(13) 0.872559 1.368167 0.820389 0.03 1 4 H(14A) 0.880071 1.565202 0.607663 0.057 1 4 H(14B) 0.744337 1.48799 0.554014 0.042 1 4 H(14C) 1.008101 1.491047 0.549644 0.051 1 4 H(15A) 0.724555 1.372038 0.71592 0.046 1 4 H(15B) 0.585951 1.422001 0.647021 0.036 1 4 H(15C) 0.712147 1.494082 0.705387 0.049 1 4 H(16A) 1.025387 1.329538 0.569051 0.042 1 4 H(16B) 0.765417 1.323241 0.570117 0.042 1 4 H(16C) 0.908267 1.279282 0.639579 0.044 1 4 H(17A) 1.20156 1.433951 0.643192 0.042 1 4 H(17B) 1.079332 1.383301 0.712997 0.054 1 4 H(17C) 1.065515 1.504572 0.701447 0.055 1 4 H(2A) 0.747195 1.645659 0.938688 0.025 1 4 H(3A) 0.713235 1.515762 0.96511 0.026 1 4 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 CL(1) 0.01801(2) 0.01929(3) 0.01294(2) -0.00157(2) 0.003116(18) 0.001663(19) O(1) 0.02693(12) 0.01232(9) 0.01315(8) -0.00135(7) 0.00599(9) -0.00051(9) O(2) 0.0431(2) 0.02219(15) 0.01480(11) -0.00039(10) 0.00371(13) -0.00116(15) O(3) 0.0545(3) 0.02246(16) 0.01954(13) 0.00695(12) 0.00263(16) -0.00818(18) O(4) 0.0441(2) 0.01156(10) 0.02697(16) -0.00346(11) -0.00027(16) -0.00230(12) O(5) 0.03854(18) 0.01604(12) 0.01734(11) -0.00159(9) 0.00510(11) 0.00404(12) N(1) 0.02484(12) 0.01816(13) 0.01388(9) 0.00289(7) -0.00084(7) -0.00381(8) N(2) 0.01701(8) 0.01088(8) 0.01228(7) -0.00072(6) 0.00211(6) 0.00046(7) N(3) 0.02186(10) 0.01155(9) 0.01256(8) -0.00015(7) 0.00396(7) 0.00069(8) N(4) 0.01974(9) 0.01133(8) 0.01731(9) -0.00174(8) -0.00227(7) 0.00107(6) N(5) 0.01412(8) 0.01748(10) 0.01379(8) -0.00313(8) 0.00039(6) -0.00109(7) C(1) 0.01791(10) 0.01176(10) 0.01896(11) 0.00158(8) -0.00170(8) -0.00074(7) C(2) 0.01916(10) 0.01110(10) 0.01991(12) -0.00145(8) -0.00039(9) 0.00028(8) C(3) 0.01703(9) 0.01176(9) 0.01545(10) -0.00207(7) 0.00040(7) 0.00033(7) C(4) 0.01235(7) 0.01079(8) 0.01257(8) -0.00074(6) -0.00026(6) 0.00026(6) C(5) 0.01479(8) 0.01156(9) 0.01242(8) -0.00001(7) -0.00029(6) -0.00041(6) C(6) 0.01511(8) 0.01263(9) 0.01418(9) 0.00143(7) -0.00153(7) -0.00133(7) C(7) 0.01477(7) 0.01096(8) 0.01148(7) -0.00072(6) 0.00146(6) -0.00011(6) C(8) 0.01418(7) 0.01181(8) 0.01185(7) 0.00054(6) 0.00081(6) -0.00021(6) C(9) 0.01742(9) 0.01560(10) 0.01292(8) 0.00199(8) 0.00172(7) -0.00049(8) C(10) 0.01926(10) 0.01606(11) 0.01565(10) 0.00467(9) 0.00092(8) -0.00120(9) C(11) 0.01772(9) 0.01286(10) 0.01806(11) 0.00331(8) -0.00089(8) -0.00130(8) C(12) 0.01432(7) 0.01072(8) 0.01486(9) 0.00052(7) -0.00139(6) -0.00047(6) C(13) 0.01539(8) 0.01081(8) 0.01254(8) 0.00016(6) 0.00041(6) 0.00012(6) C(14) 0.0314(2) 0.01978(17) 0.0285(2) 0.00502(15) 0.00258(16) -0.00374(14) C(15) 0.01523(9) 0.0352(2) 0.01564(11) -0.00416(12) 0.00086(8) 0.00013(11) C(16) 0.02076(12) 0.01680(13) 0.02439(15) -0.00450(11) -0.00117(11) 0.00076(9) C(17) 0.01525(10) 0.0429(3) 0.02138(14) -0.01192(16) -0.00103(10) -0.00224(13) H(1) 0.06034 0.01045 0.03795 0.00767 0.00446 -0.00538 H(2) 0.05839 0.01876 0.03898 -0.00353 -0.00226 0.00166 H(3) 0.05038 0.01953 0.02068 -0.00339 0.00664 0.00659 H(5) 0.04353 0.01864 0.01957 -0.00474 0.00531 0.00199 H(9) 0.05632 0.02442 0.02225 0.00344 0.01208 0.00004 H(10) 0.05973 0.02832 0.01653 0.00237 0.004 -0.00129 H(11) 0.05312 0.01314 0.03447 0.00352 0.00864 -0.00361 H(13) 0.05013 0.02181 0.01922 0.00531 0.00983 -0.00337 H(14A) 0.09274 0.01807 0.06077 -0.00187 0.00615 -0.00379 H(14B) 0.0389 0.04892 0.03703 0.01633 -0.01637 -0.00062 H(14C) 0.04814 0.06188 0.04325 0.01978 0.01471 -0.0129 H(15A) 0.03373 0.07144 0.03426 0.03022 0.00727 0.0001 H(15B) 0.02395 0.06226 0.02286 -0.00673 -0.00362 -0.00192 H(15C) 0.04431 0.06213 0.04065 -0.03586 0.00753 -0.00431 H(16A) 0.03982 0.04354 0.04245 -0.01629 0.01292 0.00735 H(16B) 0.0539 0.03741 0.0347 -0.01517 -0.0143 -0.0017 H(16C) 0.05058 0.03073 0.04922 0.0167 0.00141 0.00256 H(17A) 0.02335 0.06615 0.03798 -0.01028 0.00491 0.0071 H(17B) 0.0421 0.07447 0.04479 0.00416 -0.00901 -0.00457 H(17C) 0.04987 0.05901 0.05648 -0.03805 -0.0081 -0.00499 H(2A) 0.0425 0.01744 0.01652 -0.00418 0.01522 0.00235 H(3A) 0.04411 0.01853 0.01485 -0.00413 0.00309 0.00408 #----------------------------------------------------------------------------# # MULTIPOLE PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_rho_multipole_atom_label _atom_rho_multipole_coeff_Pv _atom_rho_multipole_coeff_P00 _atom_rho_multipole_coeff_P11 _atom_rho_multipole_coeff_P1-1 _atom_rho_multipole_coeff_P10 _atom_rho_multipole_coeff_P20 _atom_rho_multipole_coeff_P21 _atom_rho_multipole_coeff_P2-1 _atom_rho_multipole_coeff_P22 _atom_rho_multipole_coeff_P2-2 _atom_rho_multipole_coeff_P30 _atom_rho_multipole_coeff_P31 _atom_rho_multipole_coeff_P3-1 _atom_rho_multipole_coeff_P32 _atom_rho_multipole_coeff_P3-2 _atom_rho_multipole_coeff_P33 _atom_rho_multipole_coeff_P3-3 _atom_rho_multipole_coeff_P40 _atom_rho_multipole_coeff_P41 _atom_rho_multipole_coeff_P4-1 _atom_rho_multipole_coeff_P42 _atom_rho_multipole_coeff_P4-2 _atom_rho_multipole_coeff_P43 _atom_rho_multipole_coeff_P4-3 _atom_rho_multipole_coeff_P44 _atom_rho_multipole_coeff_P4-4 _atom_rho_multipole_kappa _atom_rho_multipole_kappa_prime0 _atom_rho_multipole_kappa_prime1 _atom_rho_multipole_kappa_prime2 _atom_rho_multipole_kappa_prime3 _atom_rho_multipole_kappa_prime4 _atom_rho_multipole_radial_slater_n0 _atom_rho_multipole_radial_slater_zeta0 _atom_rho_multipole_radial_slater_n1 _atom_rho_multipole_radial_slater_zeta1 _atom_rho_multipole_radial_slater_n2 _atom_rho_multipole_radial_slater_zeta2 _atom_rho_multipole_radial_slater_n3 _atom_rho_multipole_radial_slater_zeta3 _atom_rho_multipole_radial_slater_n4 _atom_rho_multipole_radial_slater_zeta4 CL(1) 7.54(6) 0 0.10(2) 0.04(3) 0.13(3) -0.053(19) -0.061(16) -0.031(16) 0.030(18) -0.031(16) -0.13(2) 0.06(3) 0.08(2) -0.037(14) 0.07(3) -0.01(3) 0.009(17) -0.008(15) -0.008(15) 0.011(14) -0.021(14) -0.012(14) 0.001(14) 0.035(15) 0.027(13) -0.028(14) 0.976996 1 1 1 1 1 4 4.2587714285714 4 4.2587714285714 4 4.2587714285714 4 4.2587714285714 4 4.2587714285714 O(1) 6.16(3) 0 -0.058(15) 0.010(13) -0.021(14) -0.021(14) -0.015(13) -0.016(13) -0.065(11) -0.024(11) -0.011(14) 0.054(12) 0.041(12) -0.008(12) -0.018(11) 0.047(11) 0.005(11) 0.016(16) -0.021(15) -0.010(15) 0.014(14) -0.015(14) -0.014(13) 0.019(13) 0.010(13) -0.013(12) 0.995241 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(2) 6.15(3) 0 -0.054(12) -0.042(14) 0.110(15) -0.018(15) 0.019(13) -0.008(14) -0.112(12) 0.040(11) 0.064(14) 0.108(12) -0.096(14) -0.024(11) -0.006(11) 0.016(12) 0.025(9) 0.015(17) 0.020(14) -0.002(15) 0.018(15) -0.003(15) -0.012(13) 0.003(13) 0.022(12) 0.010(12) 0.992884 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(3) 6.1452 0 -0.0538 -0.042 0.1104 -0.0178 0.0185 -0.0078 -0.1119 0.0399 0.0641 0.1076 -0.0958 -0.0238 -0.0059 0.0162 0.0247 0.0154 0.0195 -0.0018 0.0177 -0.0027 -0.0116 0.0025 0.0223 0.0102 0.992884 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(4) 6.18(2) 0 -0.059(11) -0.015(13) 0.041(13) -0.043(13) 0.005(12) 0.013(12) -0.094(11) 0.024(11) 0.016(13) 0.011(11) -0.052(11) 0.016(10) 0.003(10) 0.053(9) 0.031(9) -0.014(15) 0.004(13) -0.012(13) -0.011(13) -0.009(13) 0.020(12) -0.008(12) 0.049(11) -0.002(11) 0.992884 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(5) 6.1846 0 -0.0588 -0.0153 0.0406 -0.0431 0.005 0.0128 -0.0943 0.0244 0.0159 0.0109 -0.0523 0.0161 0.003 0.0526 0.0305 -0.0136 0.0039 -0.0124 -0.0109 -0.0089 0.0202 -0.0082 0.0485 -0.002 0.992884 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 N(1) 4.95(4) 0 0 0 0.070(18) 0.033(16) 0 0 -0.160(17) 0 0.191(18) 0 0 0.231(19) 0 0 0 0.06(2) 0 0 -0.01(2) 0 0 0 0.064(19) 0 0.998872 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(2) 5.32(4) 0 -0.036(16) -0.003(16) 0.008(15) 0.034(13) -0.008(13) -0.006(13) 0.006(12) -0.011(12) -0.019(15) 0.013(14) 0.024(14) -0.024(13) 0.020(13) 0.190(14) 0.055(12) 0.071(17) 0.005(16) -0.009(16) -0.003(16) -0.003(16) 0.011(16) 0.004(16) 0.007(15) -0.050(15) 0.994475 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(3) 5.20(4) 0 -0.042(14) -0.031(17) -0.002(15) 0.046(15) 0.015(13) 0.049(13) 0.020(13) 0.027(13) 0.008(16) -0.004(14) 0.052(14) -0.005(14) -0.015(13) 0.182(13) 0.057(14) 0.002(19) 0.031(17) -0.041(17) -0.002(17) -0.010(17) 0.025(16) 0.016(16) 0.015(15) -0.039(15) 0.994475 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(4) 4.89(4) 0 0 0 0.054(17) 0.065(15) 0 0 -0.092(14) 0 0.206(16) 0 0 0.111(15) 0 0 0 0.03(2) 0 0 -0.04(2) 0 0 0 0.024(17) 0 0.998872 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(5) 5.04(4) 0 0.054(16) 0.005(15) -0.010(14) -0.005(13) 0.044(13) 0.022(13) -0.001(13) 0.001(14) 0.198(17) -0.012(13) 0.003(13) -0.010(15) 0.028(14) -0.001(14) -0.160(14) 0.018(18) 0.006(17) -0.014(17) 0.022(16) -0.007(16) -0.031(17) 0.054(17) 0.004(16) 0.013(16) 1.003441 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 C(1) 4.16(6) 0 0.00(2) -0.03(2) 0.012(18) -0.183(19) 0.016(16) 0.003(17) 0.014(19) 0.015(19) 0.00(2) 0.015(19) 0.03(2) 0.025(19) -0.02(2) 0.26(2) 0.00(2) 0 0 0 0 0 0 0 0 0 1.017365 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(2) 4.10(6) 0 0.04(2) 0.01(3) 0.00(2) -0.15(2) -0.038(17) 0.005(18) 0.005(19) 0.037(19) 0.03(2) 0.01(2) 0.02(2) 0.00(2) 0.01(2) 0.23(2) 0.019(19) 0 0 0 0 0 0 0 0 0 1.017365 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(3) 4.17(6) 0 0.00(2) 0.02(2) 0.00(2) -0.143(18) 0.013(17) 0.021(18) 0.005(17) -0.016(18) -0.01(2) 0.000(19) 0.05(2) -0.006(19) 0.016(19) 0.23(2) 0.010(19) 0 0 0 0 0 0 0 0 0 1.017365 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(4) 3.84(5) 0 0.02(2) 0.07(2) -0.005(19) -0.146(17) 0.035(15) -0.008(16) 0.044(17) -0.035(17) 0.01(2) 0.014(18) 0.02(2) -0.002(19) 0.011(19) 0.24(2) -0.010(18) 0 0 0 0 0 0 0 0 0 1.017365 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(5) 4.09(6) 0 -0.02(2) -0.01(2) 0.002(18) -0.173(18) 0.002(15) -0.021(15) 0.009(17) 0.068(18) 0.04(2) 0.037(18) 0.02(2) -0.013(18) 0.004(19) 0.24(2) -0.040(19) 0 0 0 0 0 0 0 0 0 1.017365 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(6) 3.88(5) 0 0.03(2) 0.11(2) 0.020(18) -0.115(18) 0.009(15) -0.014(15) 0.099(18) -0.103(18) 0.02(2) 0.035(19) 0.02(2) -0.019(19) 0.026(19) 0.15(2) -0.009(19) 0 0 0 0 0 0 0 0 0 1.017365 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(7) 3.87(5) 0 -0.051(19) -0.01(2) 0.12(2) 0.146(17) 0.018(17) -0.007(17) -0.145(16) -0.029(16) 0.27(2) -0.02(2) 0.01(2) 0.18(2) 0.019(19) -0.010(18) 0.003(18) 0 0 0 0 0 0 0 0 0 1.009819 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(8) 3.90(5) 0 0.01(2) 0.07(2) 0.009(18) -0.141(17) -0.023(16) 0.006(15) 0.025(16) -0.032(17) 0.03(2) 0.02(2) 0.038(18) 0.023(19) -0.01(2) 0.230(19) -0.03(2) 0 0 0 0 0 0 0 0 0 1.01531 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(9) 4.06(6) 0 0.02(2) 0.01(2) 0.01(2) -0.145(18) 0.005(16) 0.027(17) 0.047(17) 0.014(18) 0.01(2) 0.019(19) 0.05(2) -0.01(2) -0.020(19) 0.207(19) 0.00(2) 0 0 0 0 0 0 0 0 0 1.01531 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(10) 3.96(6) 0 0.02(2) 0.01(2) 0.00(2) -0.187(19) 0.006(18) -0.001(16) -0.020(18) -0.015(19) 0.04(2) 0.00(2) 0.04(2) 0.03(2) 0.03(2) 0.22(2) 0.00(2) 0 0 0 0 0 0 0 0 0 1.01531 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(11) 4.12(6) 0 -0.01(2) -0.04(2) 0.003(19) -0.164(19) 0.036(17) -0.034(17) -0.036(18) 0.010(18) -0.02(2) -0.01(2) 0.04(2) 0.02(2) -0.03(2) 0.24(2) -0.01(2) 0 0 0 0 0 0 0 0 0 1.01531 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(12) 3.94(6) 0 0.03(2) 0.11(2) -0.023(19) -0.115(16) 0.048(16) -0.011(16) 0.095(17) -0.096(17) 0.00(2) -0.001(18) 0.00(2) -0.004(19) 0.017(19) 0.22(2) 0.04(2) 0 0 0 0 0 0 0 0 0 1.01531 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(13) 4.05(5) 0 0.02(2) -0.05(2) -0.01(2) -0.145(17) -0.007(16) 0.014(16) -0.021(16) 0.008(16) 0.01(2) 0.02(2) 0.022(18) 0.022(19) 0.008(19) 0.231(19) -0.02(2) 0 0 0 0 0 0 0 0 0 1.01531 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(14) 4.34(7) 0 -0.03(3) -0.02(3) -0.14(2) -0.19(2) 0.02(2) 0.02(2) -0.03(2) 0.02(2) 0.21(3) 0.01(2) 0.00(2) 0.00(2) 0.01(2) 0.03(2) -0.14(3) 0 0 0 0 0 0 0 0 0 1.001636 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(15) 4.25(6) 0 0.05(2) -0.08(3) -0.13(2) -0.128(19) 0.056(17) -0.02(2) -0.06(2) -0.01(2) 0.19(2) -0.02(2) 0.06(2) -0.01(2) -0.05(2) -0.05(2) -0.16(2) 0 0 0 0 0 0 0 0 0 1.001636 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(16) 4.14(7) 0 -0.01(3) 0.00(2) -0.01(2) -0.15(2) -0.045(19) 0.044(18) -0.026(19) 0.02(2) 0.17(2) 0.05(2) 0.00(2) 0.03(2) -0.08(2) -0.010(19) -0.10(3) 0 0 0 0 0 0 0 0 0 1.001636 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(17) 4.21(7) 0 -0.04(2) -0.24(3) -0.09(2) -0.12(2) -0.036(19) 0.02(2) 0.01(2) -0.04(2) 0.19(3) 0.00(2) 0.10(2) -0.08(2) -0.02(2) 0.01(2) -0.11(3) 0 0 0 0 0 0 0 0 0 1.001636 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 H(1) 0.87(3) 0 0 0 0.08(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(2) 0.96(3) 0 0 0 0.08(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(3) 0.84(3) 0 0 0 0.11(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(5) 0.81(3) 0 0 0 0.13(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(9) 0.87(3) 0 0 0 0.08(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(10) 0.90(3) 0 0 0 0.13(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(11) 0.86(3) 0 0 0 0.05(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(13) 0.81(3) 0 0 0 0.17(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(14A) 0.88(4) 0 0 0 0.08(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(14B) 0.81(4) 0 0 0 0.15(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(14C) 0.85(4) 0 0 0 0.08(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(15A) 0.85(4) 0 0 0 0.10(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(15B) 0.94(3) 0 0 0 0.10(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(15C) 0.87(4) 0 0 0 0.07(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(16A) 0.93(3) 0 0 0 0.11(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(16B) 0.90(3) 0 0 0 0.20(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(16C) 0.91(4) 0 0 0 0.08(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(17A) 0.86(3) 0 0 0 0.11(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(17B) 1.03(5) 0 0 0 0.13(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(17C) 0.89(4) 0 0 0 0.11(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(2A) 0.69(3) 0 0 0 0.12(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 H(3A) 0.76(3) 0 0 0 0.11(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2 loop_ _atom_local_axes_atom_label _atom_local_axes_atom0 _atom_local_axes_ax1 _atom_local_axes_atom1 _atom_local_axes_atom2 _atom_local_axes_ax2 CL(1) H(3A) Z CL(1) H(2A) Y O(1) C(7) X O(1) C(13) Y O(2) N(1) X O(2) O(3) Y O(3) N(1) -X O(3) O(2) Y O(4) N(4) X O(4) O(5) Y O(5) N(4) -X O(5) O(4) Y N(1) C(6) Z N(1) O(2) Y N(2) C(4) X N(2) C(7) Y N(3) C(8) X N(3) C(7) Y N(4) C(12) Z N(4) O(4) Y N(5) C(15) Z N(5) C(16) Y C(1) C(6) X C(1) C(2) Y C(2) C(3) X C(2) C(1) Y C(3) C(4) X C(3) C(2) Y C(4) C(3) X C(4) C(5) Y C(5) C(6) X C(5) C(4) Y C(6) C(1) X C(6) C(5) Y C(7) O(1) Z C(7) N(3) Y C(8) C(9) X C(8) C(13) Y C(9) C(10) X C(9) C(8) Y C(10) C(11) X C(10) C(9) Y C(11) C(12) X C(11) C(10) Y C(12) C(13) X C(12) C(11) Y C(13) C(8) X C(13) C(12) Y C(14) N(5) Z C(14) H(14B) Y C(15) N(5) Z C(15) H(15A) Y C(16) N(5) Z C(16) H(16A) Y C(17) N(5) Z C(17) H(17B) Y H(1) C(1) Z H(1) C(6) Y H(2) C(2) Z H(2) C(3) Y H(3) C(3) Z H(3) C(4) Y H(5) C(5) Z H(5) C(6) Y H(9) C(9) Z H(9) C(10) Y H(10) C(10) Z H(10) C(9) Y H(11) C(11) Z H(11) C(12) Y H(13) C(13) Z H(13) C(12) Y H(14A) C(14) Z H(14A) H(14C) Y H(14B) C(14) Z H(14B) H(14C) Y H(14C) C(14) Z H(14C) H(14A) Y H(15A) C(15) Z H(15A) H(15C) Y H(15B) C(15) Z H(15B) H(15C) Y H(15C) C(15) Z H(15C) H(15A) Y H(16A) C(16) Z H(16A) H(16B) Y H(16B) C(16) Z H(16B) H(16A) Y H(16C) C(16) Z H(16C) H(16B) Y H(17A) C(17) Z H(17A) H(17C) Y H(17B) C(17) Z H(17B) H(17C) Y H(17C) C(17) Z H(17C) H(17B) Y H(2A) N(2) Z H(2A) C(7) Y H(3A) N(3) Z H(3A) C(7) Y #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(1) C(7) 1.2256(4) 1_555 1_555 yes O(2) N(1) 1.2295(6) 1_555 1_555 yes O(3) N(1) 1.2265(6) 1_555 1_555 yes O(4) N(4) 1.2219(5) 1_555 1_555 yes O(5) N(4) 1.2275(5) 1_555 1_555 yes N(1) C(6) 1.4695(5) 1_555 1_555 yes N(2) C(4) 1.3930(4) 1_555 1_555 yes N(2) C(7) 1.3743(4) 1_555 1_555 yes N(2) H(2A) 1.0243(3) 1_555 1_555 yes N(3) C(7) 1.3787(4) 1_555 1_555 yes N(3) C(8) 1.3922(4) 1_555 1_555 yes N(3) H(3A) 1.0116(3) 1_555 1_555 yes N(4) C(12) 1.4665(5) 1_555 1_555 yes C(1) C(2) 1.3936(5) 1_555 1_555 yes C(1) C(6) 1.3887(5) 1_555 1_555 yes C(1) H(1) 1.0863(3) 1_555 1_555 yes C(2) C(3) 1.3881(5) 1_555 1_555 yes C(2) H(2) 1.0643(3) 1_555 1_555 yes C(3) C(4) 1.4059(4) 1_555 1_555 yes C(3) H(3) 1.0771(3) 1_555 1_555 yes C(4) C(5) 1.3977(4) 1_555 1_555 yes C(5) C(6) 1.3913(4) 1_555 1_555 yes C(5) H(5) 1.0909(3) 1_555 1_555 yes C(8) C(9) 1.4061(4) 1_555 1_555 yes C(8) C(13) 1.3971(4) 1_555 1_555 yes C(9) C(10) 1.3895(5) 1_555 1_555 yes C(9) H(9) 1.0662(3) 1_555 1_555 yes C(10) C(11) 1.3939(5) 1_555 1_555 yes C(10) H(10) 1.0783(3) 1_555 1_555 yes C(11) C(12) 1.3880(5) 1_555 1_555 yes C(11) H(11) 1.0780(3) 1_555 1_555 yes C(12) C(13) 1.3891(4) 1_555 1_555 yes C(13) H(13) 1.0876(3) 1_555 1_555 yes C(14) H(14A) 1.0782(6) 1_555 1_555 yes C(14) H(14B) 1.1012(6) 1_555 1_555 yes C(14) H(14C) 1.1040(6) 1_555 1_555 yes C(15) H(15A) 1.0860(6) 1_555 1_555 yes C(15) H(15B) 1.0890(4) 1_555 1_555 yes C(15) H(15C) 1.0762(5) 1_555 1_555 yes C(16) H(16A) 1.0744(5) 1_555 1_555 yes C(16) H(16B) 1.1083(4) 1_555 1_555 yes C(16) H(16C) 1.0694(5) 1_555 1_555 yes C(17) H(17A) 1.1172(5) 1_555 1_555 yes C(17) H(17B) 1.0425(8) 1_555 1_555 yes C(17) H(17C) 1.0866(6) 1_555 1_555 yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O(2) N(1) O(3) 122.98(5) 1_555 1_555 1_555 yes O(2) N(1) C(6) 118.50(3) 1_555 1_555 1_555 yes O(3) N(1) C(6) 118.51(4) 1_555 1_555 1_555 yes C(4) N(2) C(7) 127.47(3) 1_555 1_555 1_555 yes C(4) N(2) H(2A) 116.09(3) 1_555 1_555 1_555 yes C(7) N(2) H(2A) 115.49(3) 1_555 1_555 1_555 yes C(7) N(3) C(8) 127.44(3) 1_555 1_555 1_555 yes C(7) N(3) H(3A) 115.27(3) 1_555 1_555 1_555 yes C(8) N(3) H(3A) 116.94(3) 1_555 1_555 1_555 yes O(4) N(4) O(5) 122.94(5) 1_555 1_555 1_555 yes O(4) N(4) C(12) 118.64(4) 1_555 1_555 1_555 yes O(5) N(4) C(12) 118.42(3) 1_555 1_555 1_555 yes C(2) C(1) C(6) 117.18(3) 1_555 1_555 1_555 yes C(2) C(1) H(1) 121.82(3) 1_555 1_555 1_555 yes C(6) C(1) H(1) 121.00(3) 1_555 1_555 1_555 yes C(1) C(2) C(3) 120.64(3) 1_555 1_555 1_555 yes C(1) C(2) H(2) 118.53(3) 1_555 1_555 1_555 yes C(3) C(2) H(2) 120.81(4) 1_555 1_555 1_555 yes C(2) C(3) C(4) 120.98(3) 1_555 1_555 1_555 yes C(2) C(3) H(3) 119.60(3) 1_555 1_555 1_555 yes C(4) C(3) H(3) 119.38(3) 1_555 1_555 1_555 yes N(2) C(4) C(3) 116.54(3) 1_555 1_555 1_555 yes N(2) C(4) C(5) 124.12(3) 1_555 1_555 1_555 yes C(3) C(4) C(5) 119.34(3) 1_555 1_555 1_555 yes C(4) C(5) C(6) 117.82(3) 1_555 1_555 1_555 yes C(4) C(5) H(5) 121.01(3) 1_555 1_555 1_555 yes C(6) C(5) H(5) 121.17(3) 1_555 1_555 1_555 yes N(1) C(6) C(1) 118.39(3) 1_555 1_555 1_555 yes N(1) C(6) C(5) 117.57(3) 1_555 1_555 1_555 yes C(1) C(6) C(5) 124.03(3) 1_555 1_555 1_555 yes O(1) C(7) N(2) 124.52(3) 1_555 1_555 1_555 yes O(1) C(7) N(3) 124.44(3) 1_555 1_555 1_555 yes N(2) C(7) N(3) 111.02(3) 1_555 1_555 1_555 yes N(3) C(8) C(9) 117.16(3) 1_555 1_555 1_555 yes N(3) C(8) C(13) 123.71(3) 1_555 1_555 1_555 yes C(9) C(8) C(13) 119.13(3) 1_555 1_555 1_555 yes C(8) C(9) C(10) 120.94(3) 1_555 1_555 1_555 yes C(8) C(9) H(9) 119.19(3) 1_555 1_555 1_555 yes C(10) C(9) H(9) 119.86(3) 1_555 1_555 1_555 yes C(9) C(10) C(11) 120.70(3) 1_555 1_555 1_555 yes C(9) C(10) H(10) 119.13(3) 1_555 1_555 1_555 yes C(11) C(10) H(10) 120.18(3) 1_555 1_555 1_555 yes C(10) C(11) C(12) 117.16(3) 1_555 1_555 1_555 yes C(10) C(11) H(11) 123.09(3) 1_555 1_555 1_555 yes C(12) C(11) H(11) 119.76(3) 1_555 1_555 1_555 yes N(4) C(12) C(11) 118.76(3) 1_555 1_555 1_555 yes N(4) C(12) C(13) 117.32(3) 1_555 1_555 1_555 yes C(11) C(12) C(13) 123.92(3) 1_555 1_555 1_555 yes C(8) C(13) C(12) 118.15(3) 1_555 1_555 1_555 yes C(8) C(13) H(13) 121.19(3) 1_555 1_555 1_555 yes C(12) C(13) H(13) 120.64(3) 1_555 1_555 1_555 yes H(14A) C(14) H(14B) 110.92(5) 1_555 1_555 1_555 yes H(14A) C(14) H(14C) 110.73(5) 1_555 1_555 1_555 yes H(14B) C(14) H(14C) 109.58(6) 1_555 1_555 1_555 yes H(15A) C(15) H(15B) 112.54(4) 1_555 1_555 1_555 yes H(15A) C(15) H(15C) 110.21(4) 1_555 1_555 1_555 yes H(15B) C(15) H(15C) 110.24(4) 1_555 1_555 1_555 yes H(16A) C(16) H(16B) 108.87(4) 1_555 1_555 1_555 yes H(16A) C(16) H(16C) 110.74(4) 1_555 1_555 1_555 yes H(16B) C(16) H(16C) 111.51(4) 1_555 1_555 1_555 yes H(17A) C(17) H(17B) 110.14(5) 1_555 1_555 1_555 yes H(17A) C(17) H(17C) 109.19(5) 1_555 1_555 1_555 yes H(17B) C(17) H(17C) 112.01(4) 1_555 1_555 1_555 yes _database_code_depnum_ccdc_archive 'CCDC 953022' ####################################################################### # # 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_structure8 _audit_creation_method SHELXL-97 _chemical_compound_source 'Isabelle Kirby' _chemical_name_common '1,3(3-nitro)phenylurea with tma oac' _chemical_melting_point ? _chemical_formula_moiety 'C13 H10 N4 O5, C2 H3 O2, C4 H12 N' _chemical_formula_sum 'C19 H25 N5 O7' _chemical_formula_weight 435.44 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' S S 0.1246 0.1234 '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/n' _symmetry_space_group_name_Hall '-P 2yn' 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 12.5269(3) _cell_length_b 6.6896(2) _cell_length_c 25.2440(9) _cell_angle_alpha 90.00 _cell_angle_beta 93.856(2) _cell_angle_gamma 90.00 _cell_volume 2110.66(11) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 14733 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description fragment _exptl_crystal_colour orange _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9489 _exptl_absorpt_correction_T_max 0.9791 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24432 _diffrn_reflns_av_R_equivalents 0.0751 _diffrn_reflns_av_sigmaI/netI 0.0762 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4847 _reflns_number_gt 2701 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^)+(0.0709P)^2^+0.2521P] 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 4847 _refine_ls_number_parameters 314 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.1257 _refine_ls_R_factor_gt 0.0605 _refine_ls_wR_factor_ref 0.1634 _refine_ls_wR_factor_gt 0.1355 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.056 _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 C7 C 0.41223(17) 0.7624(3) 0.54357(9) 0.0255(5) Uani 1 1 d . . . C4 C 0.31802(17) 0.8013(3) 0.62540(8) 0.0258(5) Uani 1 1 d . . . C5 C 0.40619(18) 0.7808(3) 0.66201(9) 0.0273(5) Uani 1 1 d . . . H5 H 0.4741 0.7426 0.6507 0.033 Uiso 1 1 calc R . . C6 C 0.39240(18) 0.8171(3) 0.71469(9) 0.0297(5) Uani 1 1 d . . . C1 C 0.29711(18) 0.8744(4) 0.73431(9) 0.0351(6) Uani 1 1 d . . . H1 H 0.2913 0.8998 0.7710 0.042 Uiso 1 1 calc R . . C2 C 0.20985(19) 0.8929(4) 0.69761(9) 0.0378(6) Uani 1 1 d . . . H2 H 0.1424 0.9310 0.7094 0.045 Uiso 1 1 calc R . . C3 C 0.21954(18) 0.8570(4) 0.64422(9) 0.0325(6) Uani 1 1 d . . . H3 H 0.1586 0.8703 0.6200 0.039 Uiso 1 1 calc R . . C8 C 0.46322(17) 0.7358(3) 0.45092(9) 0.0252(5) Uani 1 1 d . . . C13 C 0.57391(18) 0.7311(3) 0.46086(9) 0.0306(6) Uani 1 1 d . . . H13 H 0.6039 0.7342 0.4964 0.037 Uiso 1 1 calc R . . C12 C 0.64079(19) 0.7219(3) 0.41927(10) 0.0340(6) Uani 1 1 d . . . H12 H 0.7160 0.7178 0.4270 0.041 Uiso 1 1 calc R . . C11 C 0.60074(19) 0.7187(3) 0.36700(9) 0.0324(6) Uani 1 1 d . . . H11 H 0.6467 0.7136 0.3386 0.039 Uiso 1 1 calc R . . C10 C 0.49110(19) 0.7232(3) 0.35783(9) 0.0290(5) Uani 1 1 d . . . C9 C 0.42198(18) 0.7317(3) 0.39817(8) 0.0258(5) Uani 1 1 d . . . H9 H 0.3468 0.7346 0.3901 0.031 Uiso 1 1 calc R . . C14A C 0.7564(3) 0.7756(5) 0.58245(15) 0.0515(10) Uani 0.756(3) 1 d PD A 1 H14A H 0.7672 0.6549 0.5615 0.077 Uiso 0.756(3) 1 calc PR A 1 H14B H 0.7721 0.8939 0.5615 0.077 Uiso 0.756(3) 1 calc PR A 1 H14C H 0.6819 0.7811 0.5921 0.077 Uiso 0.756(3) 1 calc PR A 1 C15A C 0.8133(4) 0.9570(6) 0.66298(17) 0.0488(12) Uani 0.756(3) 1 d PD A 1 H15A H 0.8350 1.0736 0.6428 0.073 Uiso 0.756(3) 1 calc PR A 1 H15B H 0.8572 0.9491 0.6965 0.073 Uiso 0.756(3) 1 calc PR A 1 H15C H 0.7378 0.9699 0.6703 0.073 Uiso 0.756(3) 1 calc PR A 1 C16A C 0.7986(3) 0.5950(5) 0.66489(13) 0.0404(8) Uani 0.756(3) 1 d PD A 1 H16A H 0.7229 0.6049 0.6722 0.061 Uiso 0.756(3) 1 calc PR A 1 H16B H 0.8427 0.5959 0.6984 0.061 Uiso 0.756(3) 1 calc PR A 1 H16C H 0.8106 0.4703 0.6458 0.061 Uiso 0.756(3) 1 calc PR A 1 C17A C 0.9400(3) 0.7490(5) 0.61930(16) 0.0494(10) Uani 0.756(3) 1 d PD A 1 H17A H 0.9487 0.6256 0.5991 0.074 Uiso 0.756(3) 1 calc PR A 1 H17B H 0.9851 0.7430 0.6525 0.074 Uiso 0.756(3) 1 calc PR A 1 H17C H 0.9613 0.8636 0.5983 0.074 Uiso 0.756(3) 1 calc PR A 1 C14B C 0.7131(6) 0.7696(16) 0.6287(5) 0.0515(10) Uani 0.244(3) 1 d PD A 2 H14D H 0.6865 0.6492 0.6100 0.077 Uiso 0.244(3) 1 calc PR A 2 H14E H 0.6857 0.8884 0.6095 0.077 Uiso 0.244(3) 1 calc PR A 2 H14F H 0.6886 0.7703 0.6647 0.077 Uiso 0.244(3) 1 calc PR A 2 C15B C 0.8755(9) 0.9590(16) 0.6538(5) 0.041(3) Uani 0.244(3) 1 d PD A 2 H15D H 0.8446 1.0735 0.6340 0.062 Uiso 0.244(3) 1 calc PR A 2 H15E H 0.9532 0.9574 0.6511 0.062 Uiso 0.244(3) 1 calc PR A 2 H15F H 0.8597 0.9702 0.6912 0.062 Uiso 0.244(3) 1 calc PR A 2 C16B C 0.8819(8) 0.5946(12) 0.6553(4) 0.0404(8) Uani 0.244(3) 1 d PD A 2 H16D H 0.8670 0.5867 0.6929 0.061 Uiso 0.244(3) 1 calc PR A 2 H16E H 0.9593 0.6055 0.6523 0.061 Uiso 0.244(3) 1 calc PR A 2 H16F H 0.8551 0.4738 0.6369 0.061 Uiso 0.244(3) 1 calc PR A 2 C17B C 0.8611(12) 0.7730(15) 0.5736(3) 0.055(4) Uani 0.244(3) 1 d PD A 2 H17D H 0.8333 0.6531 0.5551 0.082 Uiso 0.244(3) 1 calc PR A 2 H17E H 0.9393 0.7750 0.5734 0.082 Uiso 0.244(3) 1 calc PR A 2 H17F H 0.8316 0.8923 0.5554 0.082 Uiso 0.244(3) 1 calc PR A 2 C18 C 0.10168(18) 0.7454(3) 0.47381(9) 0.0268(5) Uani 1 1 d . . . C19 C -0.01294(18) 0.7397(3) 0.44988(9) 0.0331(6) Uani 1 1 d . . . H19A H -0.0485 0.6192 0.4620 0.050 Uiso 1 1 calc R . . H19C H -0.0129 0.7378 0.4111 0.050 Uiso 1 1 calc R . . H19B H -0.0513 0.8583 0.4611 0.050 Uiso 1 1 calc R . . N2 N 0.32106(15) 0.7720(2) 0.57085(7) 0.0273(4) Uani 1 1 d . . . H2A H 0.2594 0.7584 0.5523 0.033 Uiso 1 1 calc R . . N3 N 0.38896(14) 0.7459(2) 0.48975(7) 0.0268(4) Uani 1 1 d . . . H3A H 0.3209 0.7412 0.4787 0.032 Uiso 1 1 calc R . . N1 N 0.48712(17) 0.7957(3) 0.75256(8) 0.0391(5) Uani 1 1 d . . . N4 N 0.44553(17) 0.7219(3) 0.30302(8) 0.0360(5) Uani 1 1 d . . . N5 N 0.82856(14) 0.7708(3) 0.63120(7) 0.0267(4) Uani 1 1 d D . . O3 O 0.47371(15) 0.8038(3) 0.80014(7) 0.0564(6) Uani 1 1 d . . . O2 O 0.57536(15) 0.7714(3) 0.73507(7) 0.0519(5) Uani 1 1 d . . . O5 O 0.34813(15) 0.7289(3) 0.29451(7) 0.0504(5) Uani 1 1 d . . . O4 O 0.50655(15) 0.7155(3) 0.26671(7) 0.0524(5) Uani 1 1 d . . . O1 O 0.50328(12) 0.7684(2) 0.56491(6) 0.0319(4) Uani 1 1 d . . . O7 O 0.17653(12) 0.7211(2) 0.44370(6) 0.0383(4) Uani 1 1 d . . . O6 O 0.11505(13) 0.7738(3) 0.52271(6) 0.0430(5) 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 C7 0.0254(13) 0.0226(12) 0.0287(12) 0.0003(9) 0.0032(10) 0.0026(10) C4 0.0274(12) 0.0239(12) 0.0265(12) 0.0005(9) 0.0047(10) -0.0010(10) C5 0.0273(12) 0.0271(12) 0.0280(12) 0.0016(9) 0.0052(10) -0.0017(10) C6 0.0338(14) 0.0294(13) 0.0255(12) 0.0028(10) -0.0011(10) -0.0055(11) C1 0.0402(15) 0.0429(15) 0.0227(12) -0.0016(11) 0.0056(11) -0.0047(12) C2 0.0349(14) 0.0438(16) 0.0362(14) -0.0023(12) 0.0129(11) 0.0004(12) C3 0.0282(13) 0.0381(14) 0.0316(13) 0.0008(11) 0.0047(10) 0.0012(11) C8 0.0259(12) 0.0194(11) 0.0311(12) 0.0000(9) 0.0078(10) -0.0005(9) C13 0.0299(13) 0.0286(13) 0.0340(13) 0.0010(10) 0.0070(10) -0.0003(10) C12 0.0287(13) 0.0324(14) 0.0419(15) -0.0003(11) 0.0089(11) -0.0002(10) C11 0.0362(14) 0.0274(13) 0.0354(14) 0.0005(10) 0.0157(11) -0.0014(11) C10 0.0390(14) 0.0228(12) 0.0259(12) 0.0008(9) 0.0080(10) -0.0027(10) C9 0.0285(12) 0.0208(12) 0.0287(12) 0.0013(9) 0.0057(9) -0.0015(10) C14A 0.054(2) 0.047(2) 0.049(2) 0.0027(18) -0.0251(18) -0.0041(18) C15A 0.077(3) 0.028(2) 0.042(2) -0.0075(17) 0.007(3) 0.008(2) C16A 0.051(2) 0.0296(17) 0.0419(19) 0.0056(14) 0.0109(17) -0.0039(17) C17A 0.0289(19) 0.053(2) 0.068(3) 0.0043(19) 0.0145(18) 0.0030(17) C14B 0.054(2) 0.047(2) 0.049(2) 0.0027(18) -0.0251(18) -0.0041(18) C15B 0.056(9) 0.033(6) 0.035(7) -0.005(5) 0.000(7) 0.004(7) C16B 0.051(2) 0.0296(17) 0.0419(19) 0.0056(14) 0.0109(17) -0.0039(17) C17B 0.104(12) 0.029(6) 0.034(6) -0.006(5) 0.022(7) -0.012(6) C18 0.0291(13) 0.0227(12) 0.0290(12) -0.0014(9) 0.0042(10) -0.0003(10) C19 0.0277(13) 0.0384(14) 0.0332(13) -0.0007(11) 0.0014(10) 0.0000(10) N2 0.0241(10) 0.0350(11) 0.0229(10) -0.0026(8) 0.0014(8) 0.0001(8) N3 0.0212(10) 0.0337(11) 0.0257(10) -0.0010(8) 0.0038(8) 0.0016(8) N1 0.0447(14) 0.0413(13) 0.0305(12) 0.0017(9) -0.0038(10) -0.0057(10) N4 0.0425(13) 0.0380(12) 0.0283(11) -0.0009(9) 0.0080(10) -0.0028(10) N5 0.0225(10) 0.0274(10) 0.0296(10) -0.0015(8) -0.0018(8) 0.0007(8) O3 0.0563(13) 0.0865(15) 0.0256(10) 0.0066(9) -0.0032(9) -0.0094(10) O2 0.0351(11) 0.0788(15) 0.0409(11) -0.0008(9) -0.0032(9) 0.0061(9) O5 0.0378(11) 0.0820(15) 0.0312(10) 0.0003(9) 0.0020(8) 0.0014(10) O4 0.0522(12) 0.0775(15) 0.0294(10) -0.0051(9) 0.0179(9) -0.0070(10) O1 0.0265(9) 0.0403(10) 0.0291(9) -0.0010(7) 0.0035(7) 0.0017(7) O7 0.0267(9) 0.0585(12) 0.0302(9) -0.0039(8) 0.0050(7) 0.0006(8) O6 0.0328(10) 0.0692(13) 0.0268(9) -0.0068(8) 0.0016(7) 0.0030(8) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C7 O1 1.229(3) . ? C7 N2 1.374(3) . ? C7 N3 1.375(3) . ? C4 N2 1.394(3) . ? C4 C5 1.398(3) . ? C4 C3 1.402(3) . ? C5 C6 1.374(3) . ? C5 H5 0.9500 . ? C6 C1 1.377(3) . ? C6 N1 1.480(3) . ? C1 C2 1.390(3) . ? C1 H1 0.9500 . ? C2 C3 1.382(3) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C8 C13 1.393(3) . ? C8 C9 1.396(3) . ? C8 N3 1.398(3) . ? C13 C12 1.388(3) . ? C13 H13 0.9500 . ? C12 C11 1.380(3) . ? C12 H12 0.9500 . ? C11 C10 1.378(3) . ? C11 H11 0.9500 . ? C10 C9 1.382(3) . ? C10 N4 1.461(3) . ? C9 H9 0.9500 . ? C14A N5 1.478(4) . ? C14A H14A 0.9800 . ? C14A H14B 0.9800 . ? C14A H14C 0.9800 . ? C15A N5 1.501(4) . ? C15A H15A 0.9800 . ? C15A H15B 0.9800 . ? C15A H15C 0.9800 . ? C16A N5 1.514(3) . ? C16A H16A 0.9800 . ? C16A H16B 0.9800 . ? C16A H16C 0.9800 . ? C17A N5 1.455(3) . ? C17A H17A 0.9800 . ? C17A H17B 0.9800 . ? C17A H17C 0.9800 . ? C14B N5 1.444(8) . ? C14B H14D 0.9800 . ? C14B H14E 0.9800 . ? C14B H14F 0.9800 . ? C15B N5 1.487(8) . ? C15B H15D 0.9800 . ? C15B H15E 0.9800 . ? C15B H15F 0.9800 . ? C16B N5 1.467(7) . ? C16B H16D 0.9800 . ? C16B H16E 0.9800 . ? C16B H16F 0.9800 . ? C17B N5 1.538(7) . ? C17B H17D 0.9800 . ? C17B H17E 0.9800 . ? C17B H17F 0.9800 . ? C18 O6 1.249(3) . ? C18 O7 1.257(3) . ? C18 C19 1.520(3) . ? C19 H19A 0.9800 . ? C19 H19C 0.9800 . ? C19 H19B 0.9800 . ? N2 H2A 0.8800 . ? N3 H3A 0.8800 . ? N1 O3 1.225(2) . ? N1 O2 1.228(3) . ? N4 O5 1.225(3) . ? N4 O4 1.233(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 O1 C7 N2 123.8(2) . . ? O1 C7 N3 124.39(19) . . ? N2 C7 N3 111.76(19) . . ? N2 C4 C5 124.5(2) . . ? N2 C4 C3 117.1(2) . . ? C5 C4 C3 118.4(2) . . ? C6 C5 C4 118.5(2) . . ? C6 C5 H5 120.8 . . ? C4 C5 H5 120.8 . . ? C5 C6 C1 124.5(2) . . ? C5 C6 N1 117.4(2) . . ? C1 C6 N1 118.1(2) . . ? C6 C1 C2 116.6(2) . . ? C6 C1 H1 121.7 . . ? C2 C1 H1 121.7 . . ? C3 C2 C1 121.2(2) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C2 C3 C4 120.9(2) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C13 C8 C9 118.1(2) . . ? C13 C8 N3 125.2(2) . . ? C9 C8 N3 116.68(19) . . ? C12 C13 C8 120.6(2) . . ? C12 C13 H13 119.7 . . ? C8 C13 H13 119.7 . . ? C11 C12 C13 121.7(2) . . ? C11 C12 H12 119.2 . . ? C13 C12 H12 119.2 . . ? C10 C11 C12 117.0(2) . . ? C10 C11 H11 121.5 . . ? C12 C11 H11 121.5 . . ? C11 C10 C9 123.0(2) . . ? C11 C10 N4 118.7(2) . . ? C9 C10 N4 118.3(2) . . ? C10 C9 C8 119.6(2) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? N5 C14A H14A 109.5 . . ? N5 C14A H14B 109.5 . . ? N5 C14A H14C 109.5 . . ? N5 C15A H15A 109.5 . . ? N5 C15A H15B 109.5 . . ? N5 C15A H15C 109.5 . . ? N5 C16A H16A 109.5 . . ? N5 C16A H16B 109.5 . . ? N5 C16A H16C 109.5 . . ? N5 C17A H17A 109.5 . . ? N5 C17A H17B 109.5 . . ? N5 C17A H17C 109.5 . . ? N5 C14B H14D 109.5 . . ? N5 C14B H14E 109.5 . . ? H14D C14B H14E 109.5 . . ? N5 C14B H14F 109.5 . . ? H14D C14B H14F 109.5 . . ? H14E C14B H14F 109.5 . . ? N5 C15B H15D 109.5 . . ? N5 C15B H15E 109.5 . . ? H15D C15B H15E 109.5 . . ? N5 C15B H15F 109.5 . . ? H15D C15B H15F 109.5 . . ? H15E C15B H15F 109.5 . . ? N5 C16B H16D 109.5 . . ? N5 C16B H16E 109.5 . . ? H16D C16B H16E 109.5 . . ? N5 C16B H16F 109.5 . . ? H16D C16B H16F 109.5 . . ? H16E C16B H16F 109.5 . . ? N5 C17B H17D 109.5 . . ? N5 C17B H17E 109.5 . . ? H17D C17B H17E 109.5 . . ? N5 C17B H17F 109.5 . . ? H17D C17B H17F 109.5 . . ? H17E C17B H17F 109.5 . . ? O6 C18 O7 124.2(2) . . ? O6 C18 C19 117.2(2) . . ? O7 C18 C19 118.7(2) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? H19C C19 H19B 109.5 . . ? C7 N2 C4 125.48(19) . . ? C7 N2 H2A 117.3 . . ? C4 N2 H2A 117.3 . . ? C7 N3 C8 126.17(19) . . ? C7 N3 H3A 116.9 . . ? C8 N3 H3A 116.9 . . ? O3 N1 O2 123.0(2) . . ? O3 N1 C6 118.2(2) . . ? O2 N1 C6 118.8(2) . . ? O5 N4 O4 122.0(2) . . ? O5 N4 C10 119.14(19) . . ? O4 N4 C10 118.8(2) . . ? C14B N5 C17A 164.3(5) . . ? C14B N5 C16B 116.2(6) . . ? C17A N5 C16B 65.7(4) . . ? C14B N5 C14A 53.7(5) . . ? C17A N5 C14A 111.8(3) . . ? C16B N5 C14A 126.8(5) . . ? C14B N5 C15B 113.0(7) . . ? C17A N5 C15B 78.7(5) . . ? C16B N5 C15B 111.3(7) . . ? C14A N5 C15B 120.3(6) . . ? C14B N5 C15A 82.3(5) . . ? C17A N5 C15A 110.6(2) . . ? C16B N5 C15A 121.1(5) . . ? C14A N5 C15A 109.5(3) . . ? C15B N5 C15A 32.2(4) . . ? C14B N5 C16A 74.6(5) . . ? C17A N5 C16A 108.4(2) . . ? C16B N5 C16A 42.8(4) . . ? C14A N5 C16A 108.9(2) . . ? C15B N5 C16A 123.3(6) . . ? C15A N5 C16A 107.4(2) . . ? C14B N5 C17B 106.7(7) . . ? C17A N5 C17B 59.1(6) . . ? C16B N5 C17B 104.9(6) . . ? C14A N5 C17B 53.0(6) . . ? C15B N5 C17B 103.4(7) . . ? C15A N5 C17B 123.3(4) . . ? C16A N5 C17B 129.1(4) . . ? 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 H2A O6 0.88 1.91 2.778(3) 167.1 . N3 H3A O7 0.88 1.96 2.836(2) 171.5 . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.321 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.053 _iucr_refine_instructions_details ; TITL p21n CELL 0.71073 12.5269 6.6896 25.2440 90.000 93.856 90.000 ZERR 4.00 0.0003 0.0002 0.0009 0.000 0.002 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N O S UNIT 76 100 20 28 0 MERG 2 OMIT -3.00 55.00 OMIT 0 2 0 OMIT -3 1 13 OMIT 2 0 2 DFIX 1.470 0.010 N5 C14A DFIX 1.470 0.010 N5 C14B DFIX 1.470 0.010 N5 C15A DFIX 1.470 0.010 N5 C15B DFIX 1.470 0.010 N5 C16A DFIX 1.470 0.010 N5 C16B DFIX 1.470 0.010 N5 C17A DFIX 1.470 0.010 N5 C17B EADP C14A C14B EADP C16A C16B HTAB N2 O6 HTAB N3 O7 FMAP 2 PLAN 20 SIZE 0.20 0.30 0.50 ACTA BOND $H L.S. 15 TEMP -153.00 WGHT 0.070900 0.252100 FVAR 0.18477 0.75583 C7 1 0.412231 0.762442 0.543571 11.00000 0.02535 0.02257 = 0.02868 0.00027 0.00323 0.00256 C4 1 0.318020 0.801338 0.625404 11.00000 0.02741 0.02388 = 0.02653 0.00049 0.00466 -0.00099 C5 1 0.406195 0.780810 0.662011 11.00000 0.02734 0.02714 = 0.02801 0.00158 0.00525 -0.00169 AFIX 43 H5 2 0.474088 0.742618 0.650718 11.00000 -1.20000 AFIX 0 C6 1 0.392395 0.817138 0.714690 11.00000 0.03377 0.02940 = 0.02550 0.00284 -0.00111 -0.00546 C1 1 0.297112 0.874356 0.734306 11.00000 0.04025 0.04287 = 0.02268 -0.00156 0.00558 -0.00471 AFIX 43 H1 2 0.291308 0.899827 0.771023 11.00000 -1.20000 AFIX 0 C2 1 0.209848 0.892928 0.697609 11.00000 0.03492 0.04385 = 0.03619 -0.00229 0.01294 0.00037 AFIX 43 H2 2 0.142357 0.930955 0.709431 11.00000 -1.20000 AFIX 0 C3 1 0.219538 0.857046 0.644225 11.00000 0.02816 0.03811 = 0.03162 0.00080 0.00473 0.00116 AFIX 43 H3 2 0.158631 0.870315 0.619955 11.00000 -1.20000 AFIX 0 C8 1 0.463217 0.735770 0.450915 11.00000 0.02591 0.01945 = 0.03110 0.00001 0.00775 -0.00047 C13 1 0.573905 0.731094 0.460861 11.00000 0.02993 0.02862 = 0.03398 0.00099 0.00702 -0.00032 AFIX 43 H13 2 0.603895 0.734213 0.496431 11.00000 -1.20000 AFIX 0 C12 1 0.640790 0.721917 0.419267 11.00000 0.02868 0.03236 = 0.04185 -0.00033 0.00887 -0.00021 AFIX 43 H12 2 0.716037 0.717756 0.426978 11.00000 -1.20000 AFIX 0 C11 1 0.600744 0.718684 0.367003 11.00000 0.03622 0.02743 = 0.03541 0.00050 0.01574 -0.00145 AFIX 43 H11 2 0.646731 0.713553 0.338605 11.00000 -1.20000 AFIX 0 C10 1 0.491101 0.723228 0.357830 11.00000 0.03896 0.02277 = 0.02595 0.00080 0.00799 -0.00272 C9 1 0.421977 0.731663 0.398171 11.00000 0.02850 0.02085 = 0.02870 0.00132 0.00574 -0.00153 AFIX 43 H9 2 0.346832 0.734650 0.390060 11.00000 -1.20000 AFIX 0 PART 1 C14A 1 0.756375 0.775582 0.582453 21.00000 0.05410 0.04707 = 0.04949 0.00270 -0.02512 -0.00409 AFIX 137 H14A 2 0.767160 0.654877 0.561473 21.00000 -1.50000 H14B 2 0.772148 0.893921 0.561470 21.00000 -1.50000 H14C 2 0.681943 0.781126 0.592087 21.00000 -1.50000 AFIX 0 C15A 1 0.813331 0.957018 0.662976 21.00000 0.07732 0.02760 = 0.04193 -0.00755 0.00667 0.00801 AFIX 137 H15A 2 0.835003 1.073633 0.642795 21.00000 -1.50000 H15B 2 0.857225 0.949139 0.696541 21.00000 -1.50000 H15C 2 0.737819 0.969887 0.670339 21.00000 -1.50000 AFIX 0 C16A 1 0.798567 0.594975 0.664892 21.00000 0.05056 0.02965 = 0.04195 0.00557 0.01086 -0.00389 AFIX 137 H16A 2 0.722914 0.604889 0.672225 21.00000 -1.50000 H16B 2 0.842740 0.595946 0.698440 21.00000 -1.50000 H16C 2 0.810625 0.470251 0.645826 21.00000 -1.50000 AFIX 0 C17A 1 0.940023 0.748992 0.619299 21.00000 0.02892 0.05298 = 0.06788 0.00428 0.01455 0.00305 AFIX 137 H17A 2 0.948695 0.625625 0.599098 21.00000 -1.50000 H17B 2 0.985125 0.743031 0.652521 21.00000 -1.50000 H17C 2 0.961312 0.863641 0.598262 21.00000 -1.50000 AFIX 0 PART 2 C14B 1 0.713057 0.769561 0.628652 -21.00000 0.05410 0.04707 = 0.04949 0.00270 -0.02512 -0.00409 AFIX 137 H14D 2 0.686461 0.649177 0.609988 -21.00000 -1.50000 H14E 2 0.685711 0.888394 0.609515 -21.00000 -1.50000 H14F 2 0.688610 0.770277 0.664722 -21.00000 -1.50000 AFIX 0 C15B 1 0.875542 0.959044 0.653798 -21.00000 0.05573 0.03298 = 0.03499 -0.00530 0.00033 0.00398 AFIX 137 H15D 2 0.844643 1.073515 0.633982 -21.00000 -1.50000 H15E 2 0.953221 0.957433 0.651122 -21.00000 -1.50000 H15F 2 0.859712 0.970215 0.691176 -21.00000 -1.50000 AFIX 0 C16B 1 0.881928 0.594567 0.655308 -21.00000 0.05056 0.02965 = 0.04195 0.00557 0.01086 -0.00389 AFIX 137 H16D 2 0.866996 0.586665 0.692863 -21.00000 -1.50000 H16E 2 0.959297 0.605479 0.652290 -21.00000 -1.50000 H16F 2 0.855138 0.473839 0.636875 -21.00000 -1.50000 AFIX 0 C17B 1 0.861141 0.772996 0.573550 -21.00000 0.10439 0.02875 = 0.03382 -0.00598 0.02199 -0.01191 AFIX 137 H17D 2 0.833260 0.653108 0.555093 -21.00000 -1.50000 H17E 2 0.939341 0.774978 0.573377 -21.00000 -1.50000 H17F 2 0.831583 0.892309 0.555440 -21.00000 -1.50000 AFIX 0 PART 0 C18 1 0.101684 0.745432 0.473809 11.00000 0.02908 0.02267 = 0.02902 -0.00141 0.00417 -0.00027 C19 1 -0.012939 0.739678 0.449878 11.00000 0.02770 0.03835 = 0.03319 -0.00067 0.00143 -0.00003 AFIX 137 H19A 2 -0.048484 0.619181 0.462025 11.00000 -1.50000 H19C 2 -0.012873 0.737815 0.411063 11.00000 -1.50000 H19B 2 -0.051345 0.858329 0.461122 11.00000 -1.50000 AFIX 0 N2 3 0.321063 0.771952 0.570848 11.00000 0.02411 0.03496 = 0.02292 -0.00261 0.00139 0.00005 AFIX 43 H2A 2 0.259429 0.758354 0.552328 11.00000 -1.20000 AFIX 0 N3 3 0.388957 0.745860 0.489752 11.00000 0.02119 0.03368 = 0.02573 -0.00103 0.00385 0.00162 AFIX 43 H3A 2 0.320862 0.741151 0.478706 11.00000 -1.20000 AFIX 0 N1 3 0.487121 0.795665 0.752562 11.00000 0.04470 0.04127 = 0.03046 0.00171 -0.00383 -0.00567 N4 3 0.445528 0.721882 0.303022 11.00000 0.04253 0.03805 = 0.02828 -0.00093 0.00796 -0.00275 N5 3 0.828564 0.770791 0.631202 11.00000 0.02250 0.02741 = 0.02959 -0.00153 -0.00179 0.00068 O3 4 0.473714 0.803839 0.800144 11.00000 0.05633 0.08646 = 0.02556 0.00656 -0.00318 -0.00937 O2 4 0.575361 0.771352 0.735071 11.00000 0.03513 0.07879 = 0.04088 -0.00083 -0.00321 0.00608 O5 4 0.348134 0.728879 0.294509 11.00000 0.03780 0.08199 = 0.03124 0.00025 0.00204 0.00143 O4 4 0.506551 0.715545 0.266708 11.00000 0.05215 0.07753 = 0.02943 -0.00505 0.01794 -0.00700 O1 4 0.503279 0.768403 0.564912 11.00000 0.02649 0.04033 = 0.02911 -0.00096 0.00350 0.00173 O7 4 0.176534 0.721133 0.443697 11.00000 0.02672 0.05848 = 0.03018 -0.00385 0.00501 0.00056 O6 4 0.115046 0.773821 0.522710 11.00000 0.03278 0.06922 = 0.02681 -0.00678 0.00164 0.00297 HKLF 4 REM p21n REM R1 = 0.0605 for 2701 Fo > 4sig(Fo) and 0.1257 for all 4847 data REM 314 parameters refined using 8 restraints END WGHT 0.0709 0.2521 REM Highest difference peak 0.321, deepest hole -0.275, 1-sigma level 0.053 Q1 1 0.7051 0.7755 0.6043 11.00000 0.05 0.32 Q2 1 0.8601 0.7610 0.5609 11.00000 0.05 0.30 Q3 1 0.7327 0.7498 0.6503 11.00000 0.05 0.25 Q4 1 0.7957 0.6606 0.3827 11.00000 0.05 0.23 Q5 1 -0.0826 0.7638 0.4755 11.00000 0.05 0.21 Q6 1 0.4376 0.7648 0.4629 11.00000 0.05 0.21 Q7 1 0.7809 0.6675 0.4640 11.00000 0.05 0.20 Q8 1 0.3795 0.8815 0.8293 11.00000 0.05 0.20 Q9 1 0.6206 0.8819 0.4944 11.00000 0.05 0.19 Q10 1 0.2357 0.7125 0.4075 11.00000 0.05 0.19 Q11 1 0.3020 1.0984 0.7878 11.00000 0.05 0.18 Q12 1 0.9487 0.9424 0.6120 11.00000 0.05 0.18 Q13 1 0.5113 0.7831 0.4560 11.00000 0.05 0.18 Q14 1 0.5775 0.7762 0.7880 11.00000 0.05 0.18 Q15 1 0.5801 0.7304 0.4757 11.00000 0.05 0.17 Q16 1 0.3678 0.9319 0.3689 11.00000 0.05 0.17 Q17 1 0.3800 0.7449 0.6882 11.00000 0.05 0.17 Q18 1 0.8772 0.3214 0.6182 11.00000 0.05 0.17 Q19 1 0.6424 0.7831 0.4301 11.00000 0.05 0.17 Q20 1 0.7373 0.7686 0.4716 11.00000 0.05 0.17 ; _database_code_depnum_ccdc_archive 'CCDC 953023' ####################################################################### # # 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_structure9 _audit_creation_method SHELXL-97 _chemical_compound_source 'Isabelle Kirby' _chemical_name_systematic ; 1,3-bis(3,5-dinitrophenyl)urea with tetramethylacetate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H8 N6 O9, C4 H12 N, C2 H3 O2' _chemical_formula_sum 'C19 H23 N7 O11' _chemical_formula_weight 525.44 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.602(3) _cell_length_b 10.807(3) _cell_length_c 12.433(4) _cell_angle_alpha 109.859(5) _cell_angle_beta 96.598(3) _cell_angle_gamma 103.5372(5) _cell_volume 1152.7(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100 _cell_measurement_reflns_used 4163 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 31.5 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.514 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 548 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9850 _exptl_absorpt_correction_T_max 0.9900 _exptl_absorpt_process_details ; Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.68890 _diffrn_source_type 'DLS beamline I19' _diffrn_source synchrotron _diffrn_radiation_collimation 'Confocal mirrors' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku Saturn724 (2x2 bin mode)' _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_device 'four-circle \k diffractometer' _diffrn_measurement_device_type CrystalLogic _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support 'MiTeGen MicroLoop' _diffrn_reflns_number 5728 _diffrn_reflns_av_R_equivalents 0.044 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5728 _reflns_number_gt 5356 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^)+(0.0763P)^2^+0.2372P] 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 SHELXL _refine_ls_extinction_coef 0.013(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5728 _refine_ls_number_parameters 335 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0471 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1275 _refine_ls_wR_factor_gt 0.1179 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _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 -0.23241(11) 0.16504(10) 0.47442(10) 0.0201(2) Uani 1 1 d . . . H1 H -0.3246 0.0964 0.4474 0.024 Uiso 1 1 calc R . . C2 C -0.17471(11) 0.24493(10) 0.59237(10) 0.0185(2) Uani 1 1 d . . . C3 C -0.04053(11) 0.34579(10) 0.63465(9) 0.0170(2) Uani 1 1 d . . . H3 H -0.0060 0.3971 0.7163 0.020 Uiso 1 1 calc R . . C4 C 0.04387(10) 0.37104(10) 0.55483(9) 0.01576(19) Uani 1 1 d . . . C5 C -0.00979(11) 0.29279(10) 0.43474(9) 0.0179(2) Uani 1 1 d . . . H5 H 0.0451 0.3076 0.3791 0.021 Uiso 1 1 calc R . . C6 C -0.14520(11) 0.19315(10) 0.39916(9) 0.0187(2) Uani 1 1 d . . . C7 C 0.27067(10) 0.52114(10) 0.53947(9) 0.01545(19) Uani 1 1 d . . . C8 C 0.50557(10) 0.69828(10) 0.57867(9) 0.01499(19) Uani 1 1 d . . . C9 C 0.61512(10) 0.80487(10) 0.66984(9) 0.01605(19) Uani 1 1 d . . . H9 H 0.6073 0.8256 0.7491 0.019 Uiso 1 1 calc R . . C10 C 0.73402(11) 0.87865(10) 0.64194(9) 0.0164(2) Uani 1 1 d . . . C11 C 0.75150(11) 0.85714(10) 0.52829(9) 0.0173(2) Uani 1 1 d . . . H11 H 0.8342 0.9092 0.5113 0.021 Uiso 1 1 calc R . . C12 C 0.63943(11) 0.75413(10) 0.44149(9) 0.0168(2) Uani 1 1 d . . . C13 C 0.51757(10) 0.67370(10) 0.46229(9) 0.01627(19) Uani 1 1 d . . . H13 H 0.4443 0.6038 0.3992 0.020 Uiso 1 1 calc R . . C14 C 0.20935(13) 0.18270(11) -0.02000(10) 0.0245(2) Uani 1 1 d . . . H14A H 0.3074 0.1793 0.0083 0.037 Uiso 1 1 calc R . . H14B H 0.1930 0.1601 -0.1046 0.037 Uiso 1 1 calc R . . H14C H 0.1356 0.1161 -0.0033 0.037 Uiso 1 1 calc R . . C15 C 0.04855(15) 0.33112(15) -0.00224(14) 0.0400(3) Uani 1 1 d . . . H15A H 0.0320 0.3080 -0.0869 0.060 Uiso 1 1 calc R . . H15B H 0.0417 0.4242 0.0371 0.060 Uiso 1 1 calc R . . H15C H -0.0258 0.2653 0.0149 0.060 Uiso 1 1 calc R . . C16 C 0.22136(15) 0.36002(12) 0.16969(10) 0.0266(2) Uani 1 1 d . . . H16A H 0.3190 0.3562 0.1985 0.040 Uiso 1 1 calc R . . H16B H 0.1469 0.2941 0.1865 0.040 Uiso 1 1 calc R . . H16C H 0.2140 0.4530 0.2087 0.040 Uiso 1 1 calc R . . C17 C 0.31257(16) 0.42549(13) 0.01628(11) 0.0315(3) Uani 1 1 d . . . H17A H 0.4096 0.4200 0.0446 0.047 Uiso 1 1 calc R . . H17B H 0.3065 0.5187 0.0564 0.047 Uiso 1 1 calc R . . H17C H 0.2970 0.4037 -0.0682 0.047 Uiso 1 1 calc R . . C18 C 0.33762(13) 0.70027(12) 0.88975(10) 0.0232(2) Uani 1 1 d . . . C19 C 0.35705(15) 0.80625(16) 1.01152(12) 0.0381(3) Uani 1 1 d . . . H19A H 0.4601 0.8613 1.0405 0.057 Uiso 1 1 calc R . . H19B H 0.3278 0.7595 1.0640 0.057 Uiso 1 1 calc R . . H19C H 0.2958 0.8665 1.0088 0.057 Uiso 1 1 calc R . . N1 N -0.19999(11) 0.11391(10) 0.27175(9) 0.0242(2) Uani 1 1 d . . . N2 N -0.26206(10) 0.22355(10) 0.67789(10) 0.0218(2) Uani 1 1 d . . . N3 N 0.17754(9) 0.47366(9) 0.60273(8) 0.01669(18) Uani 1 1 d . . . H3A H 0.2047 0.5112 0.6795 0.020 Uiso 1 1 calc R . . N4 N 0.39216(9) 0.62459(9) 0.61301(8) 0.01673(18) Uani 1 1 d . . . H4A H 0.3986 0.6460 0.6887 0.020 Uiso 1 1 calc R . . N5 N 0.65083(10) 0.72663(10) 0.31871(8) 0.02114(19) Uani 1 1 d . . . N6 N 0.84906(10) 0.98671(9) 0.73901(8) 0.01969(19) Uani 1 1 d . . . N7 N 0.19727(10) 0.32468(9) 0.04070(8) 0.01834(18) Uani 1 1 d . . . O1 O 0.24875(8) 0.47692(8) 0.43215(7) 0.01920(16) Uani 1 1 d . . . O2 O -0.11368(11) 0.12214(10) 0.20721(8) 0.0313(2) Uani 1 1 d . . . O3 O -0.32876(11) 0.04433(12) 0.23805(10) 0.0415(3) Uani 1 1 d . . . O4 O -0.37557(9) 0.12688(9) 0.64202(9) 0.0289(2) Uani 1 1 d . . . O5 O -0.21689(10) 0.30400(10) 0.78096(8) 0.0292(2) Uani 1 1 d . . . O6 O 0.76386(10) 0.78953(12) 0.30037(9) 0.0360(2) Uani 1 1 d . . . O7 O 0.54770(10) 0.64208(10) 0.24152(8) 0.0313(2) Uani 1 1 d . . . O8 O 0.94483(9) 1.06378(9) 0.71397(8) 0.02700(19) Uani 1 1 d . . . O9 O 0.84375(10) 0.99416(9) 0.83908(8) 0.02726(19) Uani 1 1 d . . . O10 O 0.21245(10) 0.61890(11) 0.83695(8) 0.0342(2) Uani 1 1 d . . . O11 O 0.45021(9) 0.70292(10) 0.84589(7) 0.0275(2) 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 0.0173(4) 0.0153(4) 0.0276(6) 0.0077(4) 0.0042(4) 0.0055(3) C2 0.0174(4) 0.0167(4) 0.0254(5) 0.0103(4) 0.0083(4) 0.0073(3) C3 0.0174(4) 0.0168(4) 0.0194(5) 0.0079(4) 0.0062(3) 0.0068(3) C4 0.0158(4) 0.0144(4) 0.0185(5) 0.0065(3) 0.0048(3) 0.0060(3) C5 0.0186(4) 0.0159(4) 0.0187(5) 0.0054(4) 0.0045(3) 0.0058(3) C6 0.0188(4) 0.0152(4) 0.0198(5) 0.0040(4) 0.0015(4) 0.0059(3) C7 0.0160(4) 0.0147(4) 0.0170(5) 0.0061(3) 0.0049(3) 0.0064(3) C8 0.0151(4) 0.0144(4) 0.0162(5) 0.0056(3) 0.0042(3) 0.0054(3) C9 0.0170(4) 0.0156(4) 0.0157(4) 0.0055(3) 0.0040(3) 0.0056(3) C10 0.0161(4) 0.0139(4) 0.0171(5) 0.0045(3) 0.0015(3) 0.0036(3) C11 0.0172(4) 0.0163(4) 0.0193(5) 0.0078(4) 0.0045(4) 0.0048(3) C12 0.0181(4) 0.0177(4) 0.0157(5) 0.0068(4) 0.0049(3) 0.0060(3) C13 0.0170(4) 0.0161(4) 0.0155(4) 0.0054(3) 0.0041(3) 0.0050(3) C14 0.0296(5) 0.0192(5) 0.0202(5) 0.0024(4) 0.0032(4) 0.0073(4) C15 0.0282(6) 0.0378(7) 0.0440(8) 0.0047(6) -0.0078(5) 0.0153(5) C16 0.0399(6) 0.0249(5) 0.0164(5) 0.0072(4) 0.0099(4) 0.0108(4) C17 0.0422(7) 0.0242(5) 0.0234(6) 0.0078(4) 0.0137(5) -0.0005(5) C18 0.0241(5) 0.0268(5) 0.0169(5) 0.0058(4) 0.0060(4) 0.0073(4) C19 0.0305(6) 0.0449(7) 0.0222(6) -0.0019(5) 0.0104(5) 0.0001(5) N1 0.0251(4) 0.0185(4) 0.0227(5) 0.0024(4) -0.0002(4) 0.0055(3) N2 0.0199(4) 0.0199(4) 0.0312(5) 0.0131(4) 0.0114(4) 0.0080(3) N3 0.0167(4) 0.0169(4) 0.0145(4) 0.0044(3) 0.0043(3) 0.0031(3) N4 0.0170(4) 0.0179(4) 0.0139(4) 0.0053(3) 0.0043(3) 0.0032(3) N5 0.0224(4) 0.0239(4) 0.0167(4) 0.0082(3) 0.0063(3) 0.0044(3) N6 0.0191(4) 0.0176(4) 0.0194(4) 0.0060(3) 0.0018(3) 0.0025(3) N7 0.0194(4) 0.0175(4) 0.0152(4) 0.0039(3) 0.0021(3) 0.0042(3) O1 0.0197(3) 0.0203(3) 0.0152(4) 0.0055(3) 0.0037(3) 0.0033(3) O2 0.0366(5) 0.0282(4) 0.0213(4) 0.0039(3) 0.0055(3) 0.0037(4) O3 0.0250(4) 0.0423(6) 0.0336(5) -0.0033(4) -0.0031(4) -0.0023(4) O4 0.0223(4) 0.0232(4) 0.0434(5) 0.0151(4) 0.0132(4) 0.0036(3) O5 0.0306(4) 0.0301(4) 0.0274(5) 0.0103(4) 0.0141(3) 0.0071(3) O6 0.0288(4) 0.0488(6) 0.0237(5) 0.0157(4) 0.0091(4) -0.0054(4) O7 0.0296(4) 0.0357(5) 0.0164(4) 0.0041(3) 0.0041(3) -0.0033(3) O8 0.0230(4) 0.0244(4) 0.0276(4) 0.0114(3) 0.0010(3) -0.0041(3) O9 0.0273(4) 0.0285(4) 0.0175(4) 0.0046(3) 0.0027(3) -0.0002(3) O10 0.0254(4) 0.0415(5) 0.0220(4) 0.0004(4) 0.0083(3) 0.0007(4) O11 0.0225(4) 0.0397(5) 0.0165(4) 0.0069(3) 0.0055(3) 0.0070(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C6 1.3868(16) . ? C1 C2 1.3900(16) . ? C1 H1 0.9500 . ? C2 C3 1.3863(15) . ? C2 N2 1.4726(15) . ? C3 C4 1.4077(15) . ? C3 H3 0.9500 . ? C4 N3 1.3933(14) . ? C4 C5 1.4040(15) . ? C5 C6 1.3909(15) . ? C5 H5 0.9500 . ? C6 N1 1.4816(15) . ? C7 O1 1.2281(13) . ? C7 N4 1.3772(14) . ? C7 N3 1.3793(14) . ? C8 N4 1.3908(13) . ? C8 C13 1.4032(14) . ? C8 C9 1.4106(15) . ? C9 C10 1.3829(15) . ? C9 H9 0.9500 . ? C10 C11 1.3887(15) . ? C10 N6 1.4740(15) . ? C11 C12 1.3848(15) . ? C11 H11 0.9500 . ? C12 C13 1.3920(14) . ? C12 N5 1.4752(14) . ? C13 H13 0.9500 . ? C14 N7 1.5014(14) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 N7 1.4919(15) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 N7 1.4929(15) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 N7 1.4973(16) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 O10 1.2571(16) . ? C18 O11 1.2644(14) . ? C18 C19 1.5151(17) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? N1 O3 1.2253(15) . ? N1 O2 1.2270(15) . ? N2 O4 1.2317(14) . ? N2 O5 1.2350(15) . ? N3 H3A 0.8800 . ? N4 H4A 0.8800 . ? N5 O7 1.2242(15) . ? N5 O6 1.2283(14) . ? N6 O9 1.2270(14) . ? N6 O8 1.2328(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 C6 C1 C2 114.94(10) . . ? C6 C1 H1 122.5 . . ? C2 C1 H1 122.5 . . ? C3 C2 C1 123.96(11) . . ? C3 C2 N2 117.70(10) . . ? C1 C2 N2 118.33(10) . . ? C2 C3 C4 119.04(10) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? N3 C4 C5 124.62(10) . . ? N3 C4 C3 116.30(10) . . ? C5 C4 C3 119.07(9) . . ? C6 C5 C4 118.48(11) . . ? C6 C5 H5 120.8 . . ? C4 C5 H5 120.8 . . ? C1 C6 C5 124.49(10) . . ? C1 C6 N1 118.29(10) . . ? C5 C6 N1 117.21(11) . . ? O1 C7 N4 124.50(10) . . ? O1 C7 N3 124.70(10) . . ? N4 C7 N3 110.80(9) . . ? N4 C8 C13 124.94(9) . . ? N4 C8 C9 115.98(9) . . ? C13 C8 C9 119.09(10) . . ? C10 C9 C8 118.94(10) . . ? C10 C9 H9 120.5 . . ? C8 C9 H9 120.5 . . ? C9 C10 C11 124.03(10) . . ? C9 C10 N6 117.83(10) . . ? C11 C10 N6 118.14(10) . . ? C12 C11 C10 115.07(10) . . ? C12 C11 H11 122.5 . . ? C10 C11 H11 122.5 . . ? C11 C12 C13 124.43(10) . . ? C11 C12 N5 117.80(10) . . ? C13 C12 N5 117.77(10) . . ? C12 C13 C8 118.41(10) . . ? C12 C13 H13 120.8 . . ? C8 C13 H13 120.8 . . ? N7 C14 H14A 109.5 . . ? N7 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N7 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N7 C15 H15A 109.5 . . ? N7 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N7 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N7 C16 H16A 109.5 . . ? N7 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N7 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N7 C17 H17A 109.5 . . ? N7 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N7 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O10 C18 O11 123.89(11) . . ? O10 C18 C19 119.36(11) . . ? O11 C18 C19 116.71(11) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O3 N1 O2 124.43(11) . . ? O3 N1 C6 117.59(11) . . ? O2 N1 C6 117.98(10) . . ? O4 N2 O5 124.21(11) . . ? O4 N2 C2 117.95(11) . . ? O5 N2 C2 117.84(10) . . ? C7 N3 C4 125.26(9) . . ? C7 N3 H3A 117.4 . . ? C4 N3 H3A 117.4 . . ? C7 N4 C8 125.99(9) . . ? C7 N4 H4A 117.0 . . ? C8 N4 H4A 117.0 . . ? O7 N5 O6 124.09(10) . . ? O7 N5 C12 118.09(10) . . ? O6 N5 C12 117.82(10) . . ? O9 N6 O8 124.25(10) . . ? O9 N6 C10 118.22(10) . . ? O8 N6 C10 117.53(10) . . ? C15 N7 C16 109.06(11) . . ? C15 N7 C17 110.28(11) . . ? C16 N7 C17 108.87(10) . . ? C15 N7 C14 109.87(10) . . ? C16 N7 C14 109.93(9) . . ? C17 N7 C14 108.81(9) . . ? 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 N4 H4A O11 0.88 1.81 2.6746(15) 168.7 . N3 H3A O10 0.88 1.89 2.7350(16) 160.6 . _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.583 _refine_diff_density_min -0.397 _refine_diff_density_rms 0.148 _iucr_refine_instructions_details ; TITL sortav in P-1 CELL 0.68890 9.6020 10.8070 12.4330 109.859 96.598 103.537 ZERR 2.00 0.0019 0.0022 0.0025 0.030 0.030 0.030 LATT 1 SFAC C H N O UNIT 38 46 14 22 MERG 2 OMIT -3.00 55.00 HTAB N4 O11 HTAB N3 O10 FMAP 2 PLAN 20 SIZE 0.08 0.10 0.12 ACTA 55.00 BOND $H L.S. 6 TEMP -173.00 WGHT 0.076300 0.237200 EXTI 0.013243 FVAR 4.59814 C1 1 -0.232409 0.165037 0.474419 11.00000 0.01727 0.01527 = 0.02757 0.00771 0.00422 0.00552 AFIX 43 H1 2 -0.324634 0.096354 0.447401 11.00000 -1.20000 AFIX 0 C2 1 -0.174705 0.244933 0.592366 11.00000 0.01742 0.01673 = 0.02544 0.01028 0.00831 0.00732 C3 1 -0.040535 0.345792 0.634650 11.00000 0.01736 0.01678 = 0.01937 0.00795 0.00616 0.00676 AFIX 43 H3 2 -0.006048 0.397126 0.716322 11.00000 -1.20000 AFIX 0 C4 1 0.043868 0.371044 0.554826 11.00000 0.01576 0.01444 = 0.01852 0.00654 0.00481 0.00604 C5 1 -0.009785 0.292792 0.434736 11.00000 0.01858 0.01594 = 0.01867 0.00544 0.00450 0.00578 AFIX 43 H5 2 0.045144 0.307564 0.379055 11.00000 -1.20000 AFIX 0 C6 1 -0.145199 0.193148 0.399156 11.00000 0.01880 0.01522 = 0.01976 0.00398 0.00153 0.00591 C7 1 0.270672 0.521136 0.539473 11.00000 0.01604 0.01473 = 0.01704 0.00611 0.00488 0.00639 C8 1 0.505572 0.698281 0.578670 11.00000 0.01510 0.01438 = 0.01616 0.00559 0.00424 0.00541 C9 1 0.615122 0.804869 0.669844 11.00000 0.01703 0.01564 = 0.01568 0.00550 0.00396 0.00558 AFIX 43 H9 2 0.607342 0.825632 0.749145 11.00000 -1.20000 AFIX 0 C10 1 0.734023 0.878651 0.641941 11.00000 0.01612 0.01390 = 0.01710 0.00454 0.00148 0.00356 C11 1 0.751495 0.857138 0.528285 11.00000 0.01722 0.01633 = 0.01935 0.00785 0.00446 0.00477 AFIX 43 H11 2 0.834234 0.909246 0.511324 11.00000 -1.20000 AFIX 0 C12 1 0.639428 0.754131 0.441492 11.00000 0.01813 0.01774 = 0.01566 0.00679 0.00489 0.00599 C13 1 0.517567 0.673699 0.462290 11.00000 0.01701 0.01608 = 0.01551 0.00539 0.00413 0.00504 AFIX 43 H13 2 0.444278 0.603840 0.399204 11.00000 -1.20000 AFIX 0 C14 1 0.209353 0.182701 -0.020002 11.00000 0.02958 0.01923 = 0.02016 0.00239 0.00316 0.00728 AFIX 33 H14A 2 0.307414 0.179290 0.008259 11.00000 -1.50000 H14B 2 0.192952 0.160059 -0.104616 11.00000 -1.50000 H14C 2 0.135578 0.116074 -0.003268 11.00000 -1.50000 AFIX 0 C15 1 0.048549 0.331116 -0.002244 11.00000 0.02822 0.03784 = 0.04402 0.00468 -0.00781 0.01527 AFIX 33 H15A 2 0.032027 0.307987 -0.086926 11.00000 -1.50000 H15B 2 0.041708 0.424247 0.037099 11.00000 -1.50000 H15C 2 -0.025783 0.265339 0.014889 11.00000 -1.50000 AFIX 0 C16 1 0.221360 0.360021 0.169694 11.00000 0.03988 0.02492 = 0.01639 0.00724 0.00986 0.01082 AFIX 33 H16A 2 0.319012 0.356172 0.198500 11.00000 -1.50000 H16B 2 0.146863 0.294064 0.186510 11.00000 -1.50000 H16C 2 0.214017 0.453024 0.208749 11.00000 -1.50000 AFIX 0 C17 1 0.312569 0.425486 0.016276 11.00000 0.04216 0.02417 = 0.02340 0.00777 0.01366 -0.00049 AFIX 33 H17A 2 0.409612 0.420003 0.044600 11.00000 -1.50000 H17B 2 0.306526 0.518734 0.056446 11.00000 -1.50000 H17C 2 0.297033 0.403699 -0.068203 11.00000 -1.50000 AFIX 0 C18 1 0.337619 0.700269 0.889752 11.00000 0.02406 0.02676 = 0.01693 0.00577 0.00599 0.00728 C19 1 0.357052 0.806248 1.011521 11.00000 0.03055 0.04491 = 0.02218 -0.00195 0.01039 0.00013 AFIX 33 H19A 2 0.460133 0.861335 1.040540 11.00000 -1.50000 H19B 2 0.327766 0.759460 1.064009 11.00000 -1.50000 H19C 2 0.295828 0.866498 1.008776 11.00000 -1.50000 AFIX 0 N1 3 -0.199992 0.113909 0.271754 11.00000 0.02510 0.01854 = 0.02267 0.00238 -0.00015 0.00550 N2 3 -0.262055 0.223550 0.677886 11.00000 0.01995 0.01986 = 0.03115 0.01307 0.01143 0.00798 N3 3 0.177539 0.473665 0.602729 11.00000 0.01670 0.01689 = 0.01450 0.00444 0.00429 0.00309 AFIX 43 H3A 2 0.204736 0.511216 0.679527 11.00000 -1.20000 AFIX 0 N4 3 0.392163 0.624592 0.613014 11.00000 0.01696 0.01791 = 0.01391 0.00530 0.00427 0.00315 AFIX 43 H4A 2 0.398629 0.646042 0.688685 11.00000 -1.20000 AFIX 0 N5 3 0.650830 0.726631 0.318708 11.00000 0.02240 0.02392 = 0.01675 0.00818 0.00631 0.00442 N6 3 0.849060 0.986707 0.739012 11.00000 0.01914 0.01758 = 0.01938 0.00603 0.00179 0.00251 N7 3 0.197274 0.324684 0.040697 11.00000 0.01937 0.01747 = 0.01522 0.00390 0.00211 0.00416 O1 4 0.248754 0.476915 0.432154 11.00000 0.01968 0.02029 = 0.01521 0.00549 0.00373 0.00330 O2 4 -0.113684 0.122138 0.207206 11.00000 0.03665 0.02821 = 0.02126 0.00388 0.00548 0.00373 O3 4 -0.328763 0.044334 0.238046 11.00000 0.02501 0.04227 = 0.03360 -0.00327 -0.00308 -0.00226 O4 4 -0.375574 0.126882 0.642024 11.00000 0.02230 0.02318 = 0.04337 0.01511 0.01323 0.00360 O5 4 -0.216894 0.304002 0.780963 11.00000 0.03061 0.03013 = 0.02741 0.01034 0.01408 0.00709 O6 4 0.763859 0.789530 0.300373 11.00000 0.02884 0.04878 = 0.02369 0.01566 0.00910 -0.00544 O7 4 0.547702 0.642076 0.241521 11.00000 0.02955 0.03573 = 0.01644 0.00407 0.00414 -0.00331 O8 4 0.944833 1.063777 0.713969 11.00000 0.02298 0.02442 = 0.02765 0.01142 0.00103 -0.00413 O9 4 0.843753 0.994161 0.839082 11.00000 0.02728 0.02851 = 0.01750 0.00464 0.00275 -0.00024 O10 4 0.212454 0.618901 0.836954 11.00000 0.02536 0.04151 = 0.02200 0.00042 0.00835 0.00071 O11 4 0.450212 0.702919 0.845893 11.00000 0.02254 0.03973 = 0.01651 0.00694 0.00555 0.00705 HKLF 4 REM sortav in P-1 REM R1 = 0.0432 for 5356 Fo > 4sig(Fo) and 0.0471 for all 5728 data REM 335 parameters refined using 0 restraints END WGHT 0.0763 0.2372 REM Highest difference peak 0.583, deepest hole -0.397, 1-sigma level 0.148 Q1 1 0.2827 0.7346 1.0030 11.00000 0.05 0.58 Q2 1 0.4382 0.8106 1.0699 11.00000 0.05 0.53 Q3 1 0.2762 0.6434 0.8707 11.00000 0.05 0.52 Q4 1 0.3466 0.7219 0.9481 11.00000 0.05 0.52 Q5 1 0.2247 0.3527 0.0975 11.00000 0.05 0.50 Q6 1 0.6958 0.8016 0.4805 11.00000 0.05 0.50 Q7 1 0.2521 0.3796 0.0394 11.00000 0.05 0.48 Q8 1 0.3868 0.6962 0.8597 11.00000 0.05 0.48 Q9 1 0.7895 0.9221 0.6846 11.00000 0.05 0.46 Q10 1 -0.1063 0.2879 0.6128 11.00000 0.05 0.45 Q11 1 -0.2004 0.2008 0.5377 11.00000 0.05 0.45 Q12 1 0.6763 0.8351 0.6565 11.00000 0.05 0.45 Q13 1 0.5784 0.7158 0.4503 11.00000 0.05 0.43 Q14 1 0.5601 0.7477 0.6191 11.00000 0.05 0.43 Q15 1 0.1396 0.3183 0.0210 11.00000 0.05 0.43 Q16 1 -0.3252 0.1742 0.6493 11.00000 0.05 0.41 Q17 1 0.1997 0.2699 0.0127 11.00000 0.05 0.40 Q18 1 -0.2844 0.0792 0.2428 11.00000 0.05 0.40 Q19 1 0.0008 0.3610 0.5968 11.00000 0.05 0.40 Q20 1 0.3614 0.4033 -0.0366 11.00000 0.05 0.39 ; _database_code_depnum_ccdc_archive 'CCDC 953024' ####################################################################### # # 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_S3freeligand _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3-bis(2-nitrophenyl)urea ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H10 N4 O5' _chemical_formula_sum 'C13 H10 N4 O5' _chemical_formula_weight 302.25 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 c a 21' _symmetry_space_group_name_Hall 'P 2c -2ac' 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 21.8064(19) _cell_length_b 4.6133(3) _cell_length_c 12.5773(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1265.27(18) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 24315 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description slab _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.587 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.125 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9516 _exptl_absorpt_correction_T_max 0.9814 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8408 _diffrn_reflns_av_R_equivalents 0.0521 _diffrn_reflns_av_sigmaI/netI 0.0441 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 27.57 _reflns_number_total 1502 _reflns_number_gt 1347 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0440P)^2^+1.7441P] 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 1502 _refine_ls_number_parameters 210 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0621 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1303 _refine_ls_wR_factor_gt 0.1238 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.097 _refine_ls_shift/su_max 0.009 _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 0.41432(19) -0.0491(10) 0.9347(4) 0.0309(10) Uani 1 1 d . . . H1 H 0.3779 -0.1296 0.9638 0.037(14) Uiso 1 1 calc R . . C2 C 0.4460(2) 0.1617(9) 0.9886(4) 0.0271(9) Uani 1 1 d . . . H2 H 0.4312 0.2297 1.0550 0.024(12) Uiso 1 1 calc R . . C3 C 0.4997(2) 0.2763(8) 0.9467(4) 0.0236(9) Uani 1 1 d . . . C4 C 0.52246(18) 0.1865(8) 0.8473(4) 0.0220(8) Uani 1 1 d . . . C5 C 0.48908(18) -0.0252(9) 0.7933(4) 0.0250(9) Uani 1 1 d . . . H5 H 0.5027 -0.0894 0.7256 0.041(16) Uiso 1 1 calc R . . C6 C 0.43649(19) -0.1432(9) 0.8366(4) 0.0272(10) Uani 1 1 d . . . H6 H 0.4151 -0.2905 0.7990 0.021(12) Uiso 1 1 calc R . . C7 C 0.61984(17) 0.1307(8) 0.7534(3) 0.0205(8) Uani 1 1 d . . . C8 C 0.72350(19) 0.1640(8) 0.6867(3) 0.0198(8) Uani 1 1 d . . . C9 C 0.75967(18) 0.2346(8) 0.5984(4) 0.0214(8) Uani 1 1 d . . . C10 C 0.81597(19) 0.1035(10) 0.5794(4) 0.0270(10) Uani 1 1 d . . . H10 H 0.8390 0.1544 0.5180 0.021(12) Uiso 1 1 calc R . . C11 C 0.83859(19) -0.1008(10) 0.6497(4) 0.0278(9) Uani 1 1 d . . . H11 H 0.8771 -0.1912 0.6372 0.027(13) Uiso 1 1 calc R . . C12 C 0.8036(2) -0.1724(9) 0.7398(4) 0.0287(10) Uani 1 1 d . . . H12 H 0.8186 -0.3121 0.7888 0.045(16) Uiso 1 1 calc R . . C13 C 0.74792(19) -0.0412(8) 0.7574(4) 0.0229(8) Uani 1 1 d . . . H13 H 0.7253 -0.0910 0.8193 0.014(11) Uiso 1 1 calc R . . N1 N 0.53132(17) 0.4945(8) 1.0109(3) 0.0247(8) Uani 1 1 d . . . N2 N 0.57646(15) 0.2987(7) 0.8031(3) 0.0228(8) Uani 1 1 d . . . H2A H 0.5829 0.4866 0.8073 0.031(13) Uiso 1 1 calc R . . N3 N 0.66669(15) 0.2886(7) 0.7091(3) 0.0213(7) Uani 1 1 d . . . H3A H 0.6607 0.4729 0.6944 0.037(15) Uiso 1 1 calc R . . N4 N 0.73929(17) 0.4449(8) 0.5193(3) 0.0252(8) Uani 1 1 d . . . O1 O 0.61717(13) -0.1346(6) 0.7489(3) 0.0254(7) Uani 1 1 d . . . O2 O 0.56919(14) 0.6514(6) 0.9682(3) 0.0274(7) Uani 1 1 d . . . O3 O 0.51821(18) 0.5103(8) 1.1055(3) 0.0408(9) Uani 1 1 d . . . O4 O 0.69661(15) 0.6087(7) 0.5405(3) 0.0312(8) Uani 1 1 d . . . O5 O 0.76611(18) 0.4514(7) 0.4331(3) 0.0405(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0191(19) 0.028(2) 0.045(3) 0.009(2) 0.004(2) -0.0012(17) C2 0.026(2) 0.022(2) 0.033(2) 0.0034(19) 0.0055(19) 0.0045(17) C3 0.0243(19) 0.0159(18) 0.030(2) 0.0026(18) -0.0028(17) 0.0038(15) C4 0.0208(19) 0.0146(18) 0.031(2) 0.0031(17) -0.0016(17) 0.0019(15) C5 0.021(2) 0.0200(19) 0.034(2) 0.0016(18) -0.0045(18) 0.0009(15) C6 0.0196(19) 0.020(2) 0.042(3) 0.0043(19) -0.0063(18) -0.0004(16) C7 0.0202(18) 0.0186(18) 0.023(2) -0.0010(16) -0.0008(17) 0.0008(15) C8 0.023(2) 0.0145(18) 0.022(2) -0.0015(16) -0.0019(15) -0.0020(15) C9 0.022(2) 0.0165(17) 0.025(2) -0.0005(17) 0.0000(17) -0.0033(15) C10 0.0200(19) 0.028(2) 0.032(3) -0.0075(19) 0.0066(18) -0.0050(17) C11 0.020(2) 0.026(2) 0.038(2) -0.004(2) 0.0044(19) 0.0015(17) C12 0.025(2) 0.023(2) 0.038(3) -0.003(2) -0.007(2) 0.0016(16) C13 0.0230(18) 0.0192(18) 0.026(2) 0.0014(17) 0.0002(17) -0.0003(16) N1 0.0258(17) 0.0186(16) 0.030(2) 0.0009(15) -0.0020(15) 0.0042(14) N2 0.0202(17) 0.0134(16) 0.035(2) -0.0004(14) 0.0048(15) -0.0021(13) N3 0.0193(16) 0.0137(15) 0.0310(19) 0.0033(15) -0.0018(15) 0.0000(12) N4 0.0283(19) 0.0187(17) 0.029(2) 0.0038(15) -0.0013(16) -0.0056(14) O1 0.0256(14) 0.0136(13) 0.0372(18) 0.0023(13) 0.0081(14) -0.0011(11) O2 0.0294(15) 0.0232(15) 0.0295(17) -0.0019(13) 0.0009(13) -0.0057(13) O3 0.055(2) 0.0404(19) 0.0267(18) -0.0036(16) 0.0092(17) -0.0094(18) O4 0.0292(17) 0.0251(15) 0.0394(19) 0.0055(15) 0.0001(14) 0.0027(13) O5 0.057(2) 0.0373(19) 0.0273(18) 0.0057(16) 0.0116(17) 0.0040(17) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.372(7) . ? C1 C6 1.394(7) . ? C1 H1 0.9500 . ? C2 C3 1.388(6) . ? C2 H2 0.9500 . ? C3 C4 1.407(6) . ? C3 N1 1.463(6) . ? C4 C5 1.395(6) . ? C4 N2 1.402(5) . ? C5 C6 1.381(6) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O1 1.226(5) . ? C7 N3 1.373(5) . ? C7 N2 1.373(5) . ? C8 N3 1.394(5) . ? C8 C9 1.401(6) . ? C8 C13 1.404(6) . ? C9 C10 1.389(6) . ? C9 N4 1.459(5) . ? C10 C11 1.383(7) . ? C10 H10 0.9500 . ? C11 C12 1.405(7) . ? C11 H11 0.9500 . ? C12 C13 1.375(6) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? N1 O2 1.222(5) . ? N1 O3 1.226(5) . ? N2 H2A 0.8800 . ? N3 H3A 0.8800 . ? N4 O4 1.228(5) . ? N4 O5 1.232(5) . ? 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 C1 C6 118.9(4) . . ? C2 C1 H1 120.6 . . ? C6 C1 H1 120.6 . . ? C1 C2 C3 120.5(4) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C2 C3 C4 121.5(4) . . ? C2 C3 N1 116.7(4) . . ? C4 C3 N1 121.8(4) . . ? C5 C4 N2 120.2(4) . . ? C5 C4 C3 117.1(4) . . ? N2 C4 C3 122.7(4) . . ? C6 C5 C4 121.2(5) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C1 120.9(4) . . ? C5 C6 H6 119.5 . . ? C1 C6 H6 119.5 . . ? O1 C7 N3 123.1(4) . . ? O1 C7 N2 123.5(4) . . ? N3 C7 N2 113.4(3) . . ? N3 C8 C9 124.4(4) . . ? N3 C8 C13 119.2(4) . . ? C9 C8 C13 116.4(4) . . ? C10 C9 C8 122.2(4) . . ? C10 C9 N4 116.2(4) . . ? C8 C9 N4 121.6(4) . . ? C11 C10 C9 120.1(4) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 118.8(4) . . ? C10 C11 H11 120.6 . . ? C12 C11 H11 120.6 . . ? C13 C12 C11 120.4(4) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C8 122.0(4) . . ? C12 C13 H13 119.0 . . ? C8 C13 H13 119.0 . . ? O2 N1 O3 123.3(4) . . ? O2 N1 C3 118.9(4) . . ? O3 N1 C3 117.8(4) . . ? C7 N2 C4 123.4(3) . . ? C7 N2 H2A 118.3 . . ? C4 N2 H2A 118.3 . . ? C7 N3 C8 121.6(3) . . ? C7 N3 H3A 119.2 . . ? C8 N3 H3A 119.2 . . ? O4 N4 O5 122.4(4) . . ? O4 N4 C9 119.4(4) . . ? O5 N4 C9 118.1(4) . . ? 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 H3A O1 0.88 2.16 2.915(4) 144.1 1_565 N3 H3A O4 0.88 2.18 2.665(5) 114.2 . N2 H2A O1 0.88 2.04 2.844(4) 151.8 1_565 N2 H2A O2 0.88 2.18 2.643(5) 112.2 . _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.290 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.068 _iucr_refine_instructions_details ; TITL 2011smk007a in Pca2(1) CELL 0.71073 21.8064 4.6133 12.5773 90.000 90.000 90.000 ZERR 4.00 0.0019 0.0003 0.0011 0.000 0.000 0.000 LATT -1 SYMM - X, - Y, 1/2 + Z SYMM 1/2 + X, - Y, Z SYMM 1/2 - X, Y, 1/2 + Z SFAC C H N O UNIT 52 40 16 20 MERG 3 TWIN -1.00 0.00 0.00 0.00 -1.00 0.00 0.00 0.00 1.00 2 HTAB N3 O1_$1 HTAB N3 O4 HTAB N2 O1_$1 HTAB N2 O2 EQIV $1 x, y+1, z FMAP 2 PLAN 20 SIZE 0.15 0.20 0.40 ACTA 55.00 BOND BOND $H L.S. 6 TEMP -153.00 WGHT 0.044000 1.744100 BASF 7.95630 FVAR 0.66266 C1 1 0.414324 -0.049122 0.934715 11.00000 0.01907 0.02836 = 0.04515 0.00852 0.00391 -0.00121 AFIX 43 H1 2 0.377886 -0.129568 0.963757 11.00000 0.03694 AFIX 0 C2 1 0.446042 0.161654 0.988591 11.00000 0.02586 0.02242 = 0.03303 0.00342 0.00546 0.00448 AFIX 43 H2 2 0.431150 0.229670 1.055045 11.00000 0.02448 AFIX 0 C3 1 0.499735 0.276271 0.946714 11.00000 0.02427 0.01592 = 0.03046 0.00261 -0.00281 0.00378 C4 1 0.522463 0.186472 0.847344 11.00000 0.02078 0.01464 = 0.03055 0.00307 -0.00164 0.00191 C5 1 0.489078 -0.025191 0.793348 11.00000 0.02084 0.02000 = 0.03410 0.00162 -0.00453 0.00095 AFIX 43 H5 2 0.502748 -0.089353 0.725601 11.00000 0.04091 AFIX 0 C6 1 0.436486 -0.143202 0.836625 11.00000 0.01962 0.01974 = 0.04215 0.00430 -0.00630 -0.00038 AFIX 43 H6 2 0.415119 -0.290515 0.799033 11.00000 0.02053 AFIX 0 C7 1 0.619840 0.130693 0.753397 11.00000 0.02015 0.01858 = 0.02284 -0.00102 -0.00081 0.00085 C8 1 0.723502 0.164009 0.686701 11.00000 0.02262 0.01453 = 0.02220 -0.00155 -0.00191 -0.00197 C9 1 0.759674 0.234580 0.598386 11.00000 0.02226 0.01648 = 0.02536 -0.00047 0.00000 -0.00333 C10 1 0.815970 0.103543 0.579390 11.00000 0.02001 0.02845 = 0.03240 -0.00748 0.00659 -0.00496 AFIX 43 H10 2 0.838979 0.154374 0.518021 11.00000 0.02082 AFIX 0 C11 1 0.838589 -0.100808 0.649663 11.00000 0.01962 0.02578 = 0.03809 -0.00383 0.00435 0.00147 AFIX 43 H11 2 0.877072 -0.191180 0.637230 11.00000 0.02715 AFIX 0 C12 1 0.803625 -0.172356 0.739782 11.00000 0.02483 0.02328 = 0.03801 -0.00288 -0.00653 0.00155 AFIX 43 H12 2 0.818563 -0.312135 0.788830 11.00000 0.04467 AFIX 0 C13 1 0.747921 -0.041218 0.757373 11.00000 0.02298 0.01925 = 0.02643 0.00142 0.00023 -0.00026 AFIX 43 H13 2 0.725268 -0.091037 0.819251 11.00000 0.01394 AFIX 0 N1 3 0.531321 0.494525 1.010932 11.00000 0.02577 0.01862 = 0.02965 0.00092 -0.00196 0.00416 N2 3 0.576464 0.298698 0.803069 11.00000 0.02024 0.01339 = 0.03462 -0.00038 0.00479 -0.00215 AFIX 43 H2A 2 0.582905 0.486647 0.807326 11.00000 0.03123 AFIX 0 N3 3 0.666693 0.288579 0.709065 11.00000 0.01934 0.01367 = 0.03101 0.00333 -0.00180 -0.00003 AFIX 43 H3A 2 0.660718 0.472948 0.694406 11.00000 0.03683 AFIX 0 N4 3 0.739293 0.444927 0.519277 11.00000 0.02827 0.01872 = 0.02856 0.00380 -0.00129 -0.00564 O1 4 0.617165 -0.134583 0.748889 11.00000 0.02556 0.01357 = 0.03716 0.00226 0.00812 -0.00107 O2 4 0.569187 0.651376 0.968230 11.00000 0.02940 0.02316 = 0.02952 -0.00195 0.00092 -0.00571 O3 4 0.518212 0.510296 1.105531 11.00000 0.05537 0.04042 = 0.02669 -0.00364 0.00923 -0.00942 O4 4 0.696611 0.608689 0.540516 11.00000 0.02921 0.02509 = 0.03935 0.00555 0.00009 0.00267 O5 4 0.766114 0.451444 0.433125 11.00000 0.05675 0.03732 = 0.02731 0.00569 0.01164 0.00398 HKLF 4 REM 2011smk007a in Pca2(1) REM R1 = 0.0541 for 1347 Fo > 4sig(Fo) and 0.0621 for all 1502 data REM 210 parameters refined using 1 restraints END WGHT 0.0436 1.7366 REM Highest difference peak 0.290, deepest hole -0.240, 1-sigma level 0.068 Q1 1 0.6091 0.5658 0.9557 11.00000 0.05 0.29 Q2 1 0.3499 -0.4259 0.9450 11.00000 0.05 0.28 Q3 1 0.7315 0.1701 0.6196 11.00000 0.05 0.26 Q4 1 0.7726 0.0776 0.5800 11.00000 0.05 0.26 Q5 1 0.6486 0.5632 0.5470 11.00000 0.05 0.25 Q6 1 0.7342 -0.0065 0.6965 11.00000 0.05 0.25 Q7 1 0.6599 -0.1504 0.7414 11.00000 0.05 0.25 Q8 1 0.5671 0.5272 1.1039 11.00000 0.05 0.25 Q9 1 0.8136 0.4058 0.4247 11.00000 0.05 0.25 Q10 1 0.5776 -0.2245 0.7631 11.00000 0.05 0.24 Q11 1 0.5481 0.2430 0.8155 11.00000 0.05 0.22 Q12 1 0.6950 0.4605 0.5184 11.00000 0.05 0.22 Q13 1 0.4787 0.4353 1.1141 11.00000 0.05 0.22 Q14 1 0.7701 0.5185 0.4798 11.00000 0.05 0.22 Q15 1 0.8260 -0.1346 0.7074 11.00000 0.05 0.22 Q16 1 0.5836 0.4840 1.0153 11.00000 0.05 0.22 Q17 1 0.6343 0.2441 0.7011 11.00000 0.05 0.21 Q18 1 0.5261 0.6492 0.9728 11.00000 0.05 0.21 Q19 1 0.3209 -0.3495 0.9035 11.00000 0.05 0.21 Q20 1 0.5375 0.2219 0.9210 11.00000 0.05 0.21 ; _database_code_depnum_ccdc_archive 'CCDC 953025' ####################################################################### # # 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_acli _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3-bis(4-nitrophenyl)urea with tetramethylammonium acetate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H10 N4 O5, C4 H12 N, C2 H3 O2' _chemical_formula_sum 'C19 H25 N5 O7' _chemical_formula_weight 435.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0000 0.0000 '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 7.771(3) _cell_length_b 11.172(4) _cell_length_c 12.177(5) _cell_angle_alpha 91.74(3) _cell_angle_beta 104.56(3) _cell_angle_gamma 95.27(3) _cell_volume 1017.3(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) # see _exptl_special_details _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.422 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 240 _exptl_absorpt_coefficient_mu 0.170 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ; Gaussian integration method applied thought SXD-2001 program ; _exptl_special_details ; For peak integration a local UB matrix refined for each frame, using approximately 30 reflections from each of the 11 detectors. Hence _cell_measurement_reflns_used 330 For final cell dimensions a weighted average of all local cells was calculated. Because of the nature of the experiment, it is not possible to give values of theta_min and theta_max for the cell determination. The same applies for the wavelength used for the experiment. The range of wavelengths used was 0.48--7.0 Angstroms, BUT the bulk of the diffraction information is obtained from wavelengths in the range 0.7--2.5 Angstroms. The data-collection procedures on the SXD instrument used for the single-crystal neutron data collection are most recently summarized in the Appendix to the following paper: Wilson, C.C. (1997). J. Mol. Struct. 405, 207--217 ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_type neutron _diffrn_radiation_wavelength 0.48-7.0 _diffrn_radiation_source 'ISIS neutron spallation source' _diffrn_radiation_monochromator ? _diffrn_measurement_device_type 'SXD beamline' _diffrn_measurement_method 'time-of-flight Laue diffraction' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7332 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.2059 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 8.36 _diffrn_reflns_theta_max 85.50 _reflns_number_total 7332 _reflns_number_gt 6030 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SXD2001 (Gutmann, 2005)' _computing_cell_refinement 'SXD2001 (Gutmann, 2005)' _computing_data_reduction 'SXD2001 (Gutmann, 2005)' _computing_structure_solution n/a _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _diffrn_measured_fraction_theta_max 0.066 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.474 _refine_diff_density_max 1.509 _refine_diff_density_min -1.331 _refine_diff_density_rms 0.315 _refine_special_details ; The variable wavelength nature of the data collection procedure means that sensible values of _diffrn_reflns_theta_min & _diffrn_reflns_theta_max cannot be given. Instead, the following limits are given: _diffrn_reflns_sin(theta)/lambda_min _diffrn_reflns_sin(theta)/lambda_max _refine_diff_density_max/min is given in Fermi per angstrom cubed not electrons per angstrom cubed. Another way to consider the _refine_diff_density_ is as a percentage of the scattering density of a given atom: _refine_diff_density_max = 7% of carbon _refine_diff_density_min = -7% of carbon ; _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^)+(0.0967P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary isomor _atom_sites_solution_secondary isomor _atom_sites_solution_hydrogens isomor # starting atomic positions for all atoms from xray structure determination _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00253(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7332 _refine_ls_number_parameters 517 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0978 _refine_ls_R_factor_gt 0.0868 _refine_ls_wR_factor_ref 0.1944 _refine_ls_wR_factor_gt 0.1840 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.3706(6) 0.2642(3) 0.0532(3) 0.0108(9) Uani 1 1 d . . . C2 C -0.2960(7) 0.1672(4) 0.1116(3) 0.0121(9) Uani 1 1 d . . . C3 C -0.1582(7) 0.1911(3) 0.2090(3) 0.0124(10) Uani 1 1 d . . . C4 C -0.0941(6) 0.3102(3) 0.2499(3) 0.0104(9) Uani 1 1 d . . . C5 C -0.1711(6) 0.4060(3) 0.1901(3) 0.0117(9) Uani 1 1 d . . . C6 C -0.3093(6) 0.3822(3) 0.0913(3) 0.0111(9) Uani 1 1 d . . . C7 C 0.1182(7) 0.4321(3) 0.4075(3) 0.0114(10) Uani 1 1 d . . . C8 C 0.3552(6) 0.4996(3) 0.5801(3) 0.0086(9) Uani 1 1 d . . . C9 C 0.4717(7) 0.4560(3) 0.6756(3) 0.0141(10) Uani 1 1 d . . . C10 C 0.5870(7) 0.5338(3) 0.7555(3) 0.0140(10) Uani 1 1 d . . . C11 C 0.5888(7) 0.6575(3) 0.7430(3) 0.0133(10) Uani 1 1 d . . . C12 C 0.4736(6) 0.7019(3) 0.6492(3) 0.0122(10) Uani 1 1 d . . . C13 C 0.3569(6) 0.6236(3) 0.5683(3) 0.0104(9) Uani 1 1 d . . . C14 C -0.0241(8) 0.8206(4) 0.2939(4) 0.0172(10) Uani 1 1 d . . . C15 C 0.2797(7) 0.8577(4) 0.2715(4) 0.0208(11) Uani 1 1 d . . . C16 C 0.0274(8) 0.9072(4) 0.1215(4) 0.0199(11) Uani 1 1 d . . . C17 C 0.0696(8) 0.6972(4) 0.1558(4) 0.0182(11) Uani 1 1 d . . . C18 C 0.2531(6) 0.0987(3) 0.5116(3) 0.0099(9) Uani 1 1 d . . . C19 C 0.2900(7) -0.0219(4) 0.5607(4) 0.0148(10) Uani 1 1 d . . . N1 N -0.5155(5) 0.2392(3) -0.0472(2) 0.0146(7) Uani 1 1 d . . . N2 N 0.0420(5) 0.3243(2) 0.3486(2) 0.0124(7) Uani 1 1 d . . . N3 N 0.2474(5) 0.4123(2) 0.5032(2) 0.0103(7) Uani 1 1 d . . . N4 N 0.7056(5) 0.7395(3) 0.8277(2) 0.0153(7) Uani 1 1 d . . . N5 N 0.0883(5) 0.8201(2) 0.2108(2) 0.0141(7) Uani 1 1 d . . . O1 O 0.0759(8) 0.5305(4) 0.3768(4) 0.0139(11) Uani 1 1 d . . . O4 O 0.8100(9) 0.6975(5) 0.9075(4) 0.0287(15) Uani 1 1 d . . . O5 O 0.6999(9) 0.8476(4) 0.8193(4) 0.0225(13) Uani 1 1 d . . . O3 O -0.5685(9) 0.1351(4) -0.0829(4) 0.0226(14) Uani 1 1 d . . . O2 O -0.5875(8) 0.3251(5) -0.0947(4) 0.0227(12) Uani 1 1 d U . . O6 O 0.1503(8) 0.1009(4) 0.4153(4) 0.0195(13) Uani 1 1 d . . . O7 O 0.3348(8) 0.1907(4) 0.5711(4) 0.0202(13) Uani 1 1 d . . . H2 H -0.3497(15) 0.0767(8) 0.0802(7) 0.034(3) Uani 1 1 d . . . H3 H -0.0992(14) 0.1184(8) 0.2581(7) 0.029(2) Uani 1 1 d . . . H5 H -0.1255(15) 0.4985(7) 0.2244(8) 0.032(2) Uani 1 1 d . . . H6 H -0.3745(15) 0.4556(7) 0.0449(7) 0.030(2) Uani 1 1 d . . . H9 H 0.4657(17) 0.3585(8) 0.6857(7) 0.040(3) Uani 1 1 d . . . H10 H 0.6749(15) 0.5004(8) 0.8297(7) 0.032(3) Uani 1 1 d . . . H12 H 0.4789(13) 0.7974(7) 0.6400(7) 0.025(2) Uani 1 1 d . . . H13 H 0.2680(17) 0.6581(8) 0.4948(8) 0.040(3) Uani 1 1 d . . . H14A H -0.1617(17) 0.8013(9) 0.2492(9) 0.036(3) Uani 1 1 d . . . H14B H -0.0039(15) 0.9108(8) 0.3372(8) 0.032(2) Uani 1 1 d . . . H14C H 0.0199(16) 0.7517(8) 0.3554(8) 0.040(3) Uani 1 1 d . . . H15A H 0.3251(17) 0.7946(10) 0.3357(9) 0.044(3) Uani 1 1 d . . . H15B H 0.2855(16) 0.9462(9) 0.3108(9) 0.043(3) Uani 1 1 d . . . H15C H 0.3623(19) 0.8596(11) 0.2087(11) 0.057(3) Uani 1 1 d . . . H16A H 0.1054(17) 0.9021(9) 0.0587(9) 0.045(3) Uani 1 1 d . . . H16B H 0.0456(17) 0.9965(8) 0.1618(9) 0.046(3) Uani 1 1 d . . . H16C H -0.1131(18) 0.8813(9) 0.0799(9) 0.042(3) Uani 1 1 d . . . H17A H 0.1481(16) 0.6997(9) 0.0944(9) 0.039(3) Uani 1 1 d . . . H17B H -0.0675(18) 0.6732(8) 0.1147(9) 0.038(3) Uani 1 1 d . . . H17C H 0.1198(16) 0.6360(8) 0.2226(8) 0.038(3) Uani 1 1 d . . . H19A H 0.3717(18) -0.0680(9) 0.5152(10) 0.052(4) Uani 1 1 d . . . H19B H 0.1672(17) -0.0793(9) 0.5508(10) 0.048(3) Uani 1 1 d . . . H19C H 0.3581(17) -0.0122(9) 0.6494(8) 0.043(3) Uani 1 1 d . . . H2A H 0.0857(13) 0.2438(7) 0.3788(6) 0.023(2) Uani 1 1 d . . . H3A H 0.2736(14) 0.3245(7) 0.5218(7) 0.028(2) 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 0.010(3) 0.0135(19) 0.0072(17) 0.0003(14) -0.0018(18) 0.0021(17) C2 0.013(3) 0.0108(18) 0.0114(18) 0.0004(15) 0.0017(19) 0.0010(18) C3 0.017(3) 0.0085(18) 0.0096(18) -0.0011(14) -0.001(2) 0.0025(18) C4 0.012(3) 0.0078(18) 0.0103(17) -0.0003(14) 0.0004(19) 0.0008(17) C5 0.010(3) 0.0070(17) 0.0143(19) 0.0023(14) -0.0032(19) -0.0012(17) C6 0.011(3) 0.0097(18) 0.0100(18) 0.0005(15) -0.0018(19) -0.0005(17) C7 0.019(3) 0.0066(17) 0.0078(18) 0.0033(14) 0.0017(19) 0.0037(17) C8 0.006(3) 0.0071(17) 0.0116(18) 0.0029(14) 0.0001(18) 0.0020(16) C9 0.023(3) 0.0062(17) 0.0142(19) 0.0029(15) 0.005(2) 0.0035(19) C10 0.021(3) 0.0128(19) 0.0067(17) -0.0022(15) 0.000(2) 0.0055(19) C11 0.018(3) 0.0133(19) 0.0073(17) -0.0010(14) 0.0016(19) 0.0019(18) C12 0.013(3) 0.0101(18) 0.0114(19) 0.0009(15) 0.0006(19) -0.0006(18) C13 0.012(3) 0.0075(17) 0.0093(17) 0.0017(14) -0.0019(18) 0.0005(17) C14 0.024(4) 0.017(2) 0.011(2) -0.0009(16) 0.003(2) 0.004(2) C15 0.009(3) 0.030(3) 0.021(2) -0.008(2) 0.002(2) 0.000(2) C16 0.029(4) 0.012(2) 0.017(2) 0.0029(17) 0.004(2) 0.003(2) C17 0.028(4) 0.0116(19) 0.014(2) -0.0026(16) 0.004(2) 0.002(2) C18 0.013(3) 0.0060(16) 0.0104(17) 0.0012(14) 0.0025(18) -0.0001(17) C19 0.016(3) 0.0113(19) 0.014(2) 0.0046(16) -0.001(2) 0.002(2) N1 0.019(2) 0.0130(14) 0.0104(13) -0.0002(11) 0.0014(14) 0.0025(13) N2 0.019(2) 0.0079(13) 0.0097(13) 0.0011(10) 0.0007(14) 0.0035(13) N3 0.011(2) 0.0093(13) 0.0101(13) -0.0002(10) 0.0002(13) 0.0030(12) N4 0.014(2) 0.0163(15) 0.0130(14) -0.0041(11) 0.0008(15) -0.0055(13) N5 0.017(2) 0.0112(12) 0.0132(13) -0.0012(10) 0.0024(14) 0.0012(13) O1 0.013(3) 0.011(2) 0.014(2) 0.0009(17) -0.002(2) 0.000(2) O4 0.031(5) 0.027(3) 0.017(2) -0.006(2) -0.010(3) -0.001(3) O5 0.025(4) 0.016(3) 0.023(3) -0.006(2) 0.004(3) -0.007(2) O3 0.030(4) 0.015(2) 0.017(2) -0.0024(19) -0.001(3) -0.004(2) O2 0.0226(16) 0.0217(14) 0.0220(14) 0.0022(9) 0.0024(10) 0.0020(10) O6 0.021(4) 0.013(2) 0.018(2) 0.0026(18) -0.007(3) 0.006(2) O7 0.025(4) 0.011(2) 0.019(2) 0.0006(19) -0.005(3) 0.001(2) H2 0.052(8) 0.013(4) 0.027(4) -0.003(3) -0.005(5) 0.004(4) H3 0.033(7) 0.025(4) 0.023(4) 0.002(3) -0.007(4) 0.011(4) H5 0.040(8) 0.012(4) 0.036(5) -0.001(3) -0.001(5) -0.003(4) H6 0.032(7) 0.014(4) 0.032(5) 0.001(3) -0.012(5) 0.003(4) H9 0.068(10) 0.016(4) 0.026(5) 0.001(4) -0.004(5) 0.002(5) H10 0.040(8) 0.030(5) 0.018(4) 0.005(4) -0.012(5) 0.005(5) H12 0.015(6) 0.017(4) 0.034(5) 0.005(3) -0.011(4) 0.002(4) H13 0.062(9) 0.029(5) 0.022(5) 0.008(4) -0.002(5) 0.004(5) H14A 0.024(8) 0.051(6) 0.032(5) -0.008(4) 0.012(5) -0.005(5) H14B 0.038(8) 0.030(5) 0.028(4) -0.011(4) 0.013(5) -0.007(5) H14C 0.051(9) 0.031(5) 0.034(5) 0.009(4) 0.003(6) -0.003(5) H15A 0.033(8) 0.055(7) 0.038(5) -0.002(5) -0.003(5) 0.012(6) H15B 0.044(9) 0.040(6) 0.041(5) -0.018(5) 0.007(6) -0.001(5) H15C 0.043(9) 0.066(8) 0.062(8) -0.018(6) 0.023(7) -0.020(7) H16A 0.064(10) 0.040(6) 0.045(6) 0.020(5) 0.038(7) 0.012(6) H16B 0.067(10) 0.015(4) 0.058(6) 0.005(4) 0.019(7) 0.002(5) H16C 0.035(9) 0.039(6) 0.046(6) 0.020(5) -0.002(6) 0.012(6) H17A 0.050(9) 0.038(5) 0.039(5) 0.007(4) 0.027(6) 0.010(5) H17B 0.046(9) 0.019(4) 0.041(5) -0.004(4) -0.003(6) -0.005(5) H17C 0.051(9) 0.026(5) 0.038(5) 0.009(4) 0.008(6) 0.015(5) H19A 0.069(10) 0.038(6) 0.068(7) 0.021(5) 0.036(8) 0.041(6) H19B 0.034(8) 0.027(5) 0.071(7) 0.019(5) -0.008(7) -0.009(5) H19C 0.048(9) 0.046(6) 0.028(5) 0.015(4) -0.007(5) 0.018(6) H2A 0.024(6) 0.023(4) 0.019(4) 0.005(3) 0.001(4) 0.008(4) H3A 0.044(8) 0.012(4) 0.029(4) 0.001(3) 0.009(5) 0.010(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C6 1.384(6) . ? C1 C2 1.403(5) . ? C1 N1 1.439(5) . ? C2 C3 1.384(6) . ? C2 H2 1.078(11) . ? C3 C4 1.407(6) . ? C3 H3 1.090(10) . ? C4 N2 1.381(5) . ? C4 C5 1.407(5) . ? C5 C6 1.396(6) . ? C5 H5 1.095(10) . ? C6 H6 1.100(10) . ? C7 O1 1.219(6) . ? C7 N3 1.372(5) . ? C7 N2 1.385(5) . ? C8 N3 1.388(5) . ? C8 C13 1.396(5) . ? C8 C9 1.413(6) . ? C9 C10 1.368(6) . ? C9 H9 1.098(9) . ? C10 C11 1.394(5) . ? C10 H10 1.086(10) . ? C11 C12 1.398(6) . ? C11 N4 1.430(5) . ? C12 C13 1.383(6) . ? C12 H12 1.074(9) . ? C13 H13 1.089(11) . ? C14 N5 1.494(6) . ? C14 H14A 1.070(16) . ? C14 H14B 1.103(11) . ? C14 H14C 1.107(11) . ? C15 N5 1.499(6) . ? C15 H15A 1.083(13) . ? C15 H15B 1.078(12) . ? C15 H15C 1.114(15) . ? C16 N5 1.498(5) . ? C16 H16A 1.092(13) . ? C16 H16B 1.080(12) . ? C16 H16C 1.089(17) . ? C17 N5 1.488(5) . ? C17 H17A 1.077(12) . ? C17 H17B 1.062(16) . ? C17 H17C 1.097(10) . ? C18 O6 1.244(6) . ? C18 O7 1.260(7) . ? C18 C19 1.513(5) . ? C19 H19A 1.094(12) . ? C19 H19B 1.078(15) . ? C19 H19C 1.073(11) . ? N1 O3 1.226(6) . ? N1 O2 1.240(6) . ? N2 H2A 1.036(9) . ? N3 H3A 1.040(8) . ? N4 O5 1.219(6) . ? N4 O4 1.235(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 C6 C1 C2 121.4(4) . . ? C6 C1 N1 119.9(3) . . ? C2 C1 N1 118.8(4) . . ? C3 C2 C1 118.8(4) . . ? C3 C2 H2 122.2(6) . . ? C1 C2 H2 119.0(6) . . ? C2 C3 C4 121.0(4) . . ? C2 C3 H3 121.1(6) . . ? C4 C3 H3 117.9(6) . . ? N2 C4 C3 116.4(3) . . ? N2 C4 C5 124.4(3) . . ? C3 C4 C5 119.2(4) . . ? C6 C5 C4 119.9(4) . . ? C6 C5 H5 121.0(6) . . ? C4 C5 H5 119.0(6) . . ? C1 C6 C5 119.7(4) . . ? C1 C6 H6 119.1(6) . . ? C5 C6 H6 121.1(6) . . ? O1 C7 N3 125.3(4) . . ? O1 C7 N2 124.0(4) . . ? N3 C7 N2 110.7(3) . . ? N3 C8 C13 125.0(3) . . ? N3 C8 C9 115.7(3) . . ? C13 C8 C9 119.3(4) . . ? C10 C9 C8 120.7(3) . . ? C10 C9 H9 120.5(7) . . ? C8 C9 H9 118.7(7) . . ? C9 C10 C11 119.7(4) . . ? C9 C10 H10 120.8(6) . . ? C11 C10 H10 119.5(6) . . ? C10 C11 C12 120.2(4) . . ? C10 C11 N4 120.0(4) . . ? C12 C11 N4 119.8(3) . . ? C13 C12 C11 120.3(4) . . ? C13 C12 H12 120.6(6) . . ? C11 C12 H12 119.1(6) . . ? C12 C13 C8 119.8(4) . . ? C12 C13 H13 120.3(6) . . ? C8 C13 H13 119.9(6) . . ? N5 C14 H14A 109.2(6) . . ? N5 C14 H14B 108.7(6) . . ? H14A C14 H14B 109.1(9) . . ? N5 C14 H14C 107.4(7) . . ? H14A C14 H14C 111.5(9) . . ? H14B C14 H14C 110.8(8) . . ? N5 C15 H15A 109.3(8) . . ? N5 C15 H15B 107.4(8) . . ? H15A C15 H15B 110.0(9) . . ? N5 C15 H15C 109.1(8) . . ? H15A C15 H15C 110.4(11) . . ? H15B C15 H15C 110.5(10) . . ? N5 C16 H16A 108.8(6) . . ? N5 C16 H16B 108.6(6) . . ? H16A C16 H16B 111.1(9) . . ? N5 C16 H16C 108.5(6) . . ? H16A C16 H16C 109.1(10) . . ? H16B C16 H16C 110.7(10) . . ? N5 C17 H17A 108.0(7) . . ? N5 C17 H17B 108.3(6) . . ? H17A C17 H17B 110.2(9) . . ? N5 C17 H17C 107.6(6) . . ? H17A C17 H17C 110.8(9) . . ? H17B C17 H17C 111.8(9) . . ? O6 C18 O7 124.6(4) . . ? O6 C18 C19 118.8(4) . . ? O7 C18 C19 116.6(4) . . ? C18 C19 H19A 110.0(6) . . ? C18 C19 H19B 110.7(6) . . ? H19A C19 H19B 106.9(10) . . ? C18 C19 H19C 111.6(6) . . ? H19A C19 H19C 108.9(9) . . ? H19B C19 H19C 108.5(9) . . ? O3 N1 O2 121.2(5) . . ? O3 N1 C1 120.4(4) . . ? O2 N1 C1 118.4(4) . . ? C4 N2 C7 126.4(3) . . ? C4 N2 H2A 113.6(6) . . ? C7 N2 H2A 120.0(6) . . ? C7 N3 C8 126.5(3) . . ? C7 N3 H3A 119.3(6) . . ? C8 N3 H3A 114.2(6) . . ? O5 N4 O4 122.1(5) . . ? O5 N4 C11 119.7(4) . . ? O4 N4 C11 118.2(4) . . ? C17 N5 C14 109.3(3) . . ? C17 N5 C16 109.2(3) . . ? C14 N5 C16 109.6(3) . . ? C17 N5 C15 110.4(4) . . ? C14 N5 C15 109.4(3) . . ? C16 N5 C15 108.9(4) . . ? 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 H2A O6 1.036(9) 1.754(9) 2.786(5) 173.9(8) . N3 H3A O7 1.040(8) 1.692(9) 2.725(5) 171.4(9) . _database_code_depnum_ccdc_archive 'CCDC 953026' ####################################################################### # # 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_shelx003 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3-bis(3-nitrophenyl)urea with tetramethylammonium chloride ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H10 N4 O5, C4 H12 N, Cl' _chemical_formula_sum 'C17 H22 Cl N5 O5' _chemical_formula_weight 411.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 6.812(3) _cell_length_b 14.403(5) _cell_length_c 19.790(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1941.5(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) # see _exptl_special_details _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 7.0 _exptl_crystal_size_mid 1.0 _exptl_crystal_size_min 0.8 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.409 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.160 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ; Gaussian integration method applied thought SXD-2001 program ; _exptl_special_details ; For peak integration a local UB matrix refined for each frame, using approximately 30 reflections from each of the 11 detectors. Hence _cell_measurement_reflns_used 330 For final cell dimensions a weighted average of all local cells was calculated. Because of the nature of the experiment, it is not possible to give values of theta_min and theta_max for the cell determination. The same applies for the wavelength used for the experiment. The range of wavelengths used was 0.48--7.0 Angstroms, BUT the bulk of the diffraction information is obtained from wavelengths in the range 0.7--2.5 Angstroms. The data-collection procedures on the SXD instrument used for the single-crystal neutron data collection are most recently summarized in the Appendix to the following paper: Wilson, C.C. (1997). J. Mol. Struct. 405, 207--217 ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_type neutron _diffrn_radiation_wavelength 0.48-7.0 _diffrn_radiation_source 'ISIS neutron spallation source' _diffrn_radiation_monochromator ? _diffrn_measurement_device_type 'SXD beamline' _diffrn_measurement_method 'time-of-flight Laue diffraction' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8718 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0757 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 8.50 _diffrn_reflns_theta_max 84.57 _reflns_number_total 8718 _reflns_number_gt 8718 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SXD2001 (Gutmann, 2005)' _computing_cell_refinement 'SXD2001 (Gutmann, 2005)' _computing_data_reduction 'SXD2001 (Gutmann, 2005)' _computing_structure_solution n/a _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _diffrn_measured_fraction_theta_max 0.027 _diffrn_reflns_theta_full 84.57 _diffrn_measured_fraction_theta_full 0.027 _refine_diff_density_max 1.410 _refine_diff_density_min -1.473 _refine_diff_density_rms 0.307 _refine_special_details ; The variable wavelength nature of the data collection procedure means that sensible values of _diffrn_reflns_theta_min & _diffrn_reflns_theta_max cannot be given. Instead, the following limits are given: _diffrn_reflns_sin(theta)/lambda_min _diffrn_reflns_sin(theta)/lambda_max _refine_diff_density_max/min is given in Fermi per angstrom cubed not electrons per angstrom cubed. Another way to consider the _refine_diff_density_ is as a percentage of the scattering density of a given atom: _refine_diff_density_max = 8% of carbon _refine_diff_density_min = -8% of carbon ; _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^)+(0.1123P)^2^+59.9981P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary isomor _atom_sites_solution_secondary isomor _atom_sites_solution_hydrogens isomor # starting atomic positions for all atoms from xray structure determination _refine_ls_hydrogen_treatment refall _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 10(10) _refine_ls_number_reflns 8718 _refine_ls_number_parameters 457 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0695 _refine_ls_R_factor_gt 0.0695 _refine_ls_wR_factor_ref 0.1783 _refine_ls_wR_factor_gt 0.1783 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8773(8) 0.8816(2) 0.27977(16) 0.0135(9) Uani 1 1 d . . . C2 C 0.8319(7) 0.8829(2) 0.34855(17) 0.0136(10) Uani 1 1 d . . . C3 C 0.8122(7) 0.8002(2) 0.38425(16) 0.0128(9) Uani 1 1 d . . . C4 C 0.8355(6) 0.7138(2) 0.35165(14) 0.0087(8) Uani 1 1 d . . . C5 C 0.8818(7) 0.7120(2) 0.28307(14) 0.0102(8) Uani 1 1 d . . . C6 C 0.9028(7) 0.7955(2) 0.24932(15) 0.0122(8) Uani 1 1 d . . . C7 C 0.8272(7) 0.5440(2) 0.37229(15) 0.0099(9) Uani 1 1 d . . . C8 C 0.7815(7) 0.3883(2) 0.42335(16) 0.0095(8) Uani 1 1 d . . . C9 C 0.7362(7) 0.3435(2) 0.48440(17) 0.0131(10) Uani 1 1 d . . . C10 C 0.7369(7) 0.2469(2) 0.48870(17) 0.0125(10) Uani 1 1 d . . . C11 C 0.7837(7) 0.1930(2) 0.43238(17) 0.0142(9) Uani 1 1 d . . . C12 C 0.8286(7) 0.2394(2) 0.37334(16) 0.0108(9) Uani 1 1 d . . . C13 C 0.8317(7) 0.3360(2) 0.36712(15) 0.0099(9) Uani 1 1 d . . . C14 C 0.8791(10) 0.4985(3) 0.0827(2) 0.0238(12) Uani 1 1 d . . . C15 C 0.7139(8) 0.4287(3) 0.1784(2) 0.0196(10) Uani 1 1 d . . . C16 C 0.8986(9) 0.3318(2) 0.10077(19) 0.0193(10) Uani 1 1 d . . . C17 C 1.0716(8) 0.4368(3) 0.1771(2) 0.0232(11) Uani 1 1 d . . . Cl1 Cl 0.5998(5) 0.61543(17) 0.53480(10) 0.0143(6) Uani 1 1 d . . . N1 N 0.9537(5) 0.79273(17) 0.17750(11) 0.0158(7) Uani 1 1 d . . . N2 N 0.8103(5) 0.63519(16) 0.39175(11) 0.0109(6) Uani 1 1 d . . . N3 N 0.7769(5) 0.48473(15) 0.42378(12) 0.0136(7) Uani 1 1 d . . . N4 N 0.8753(5) 0.18500(16) 0.31276(12) 0.0140(6) Uani 1 1 d . . . N5 N 0.8909(5) 0.42444(17) 0.13485(11) 0.0118(6) Uani 1 1 d . . . O1 O 0.8862(9) 0.5192(2) 0.31667(18) 0.0130(10) Uani 1 1 d . . . O2 O 0.9826(10) 0.7176(3) 0.1511(2) 0.0252(14) Uani 1 1 d . . . O3 O 0.9700(11) 0.8667(3) 0.1471(2) 0.0332(18) Uani 1 1 d . . . O4 O 0.8607(10) 0.1008(2) 0.3151(2) 0.0231(13) Uani 1 1 d . . . O5 O 0.9316(10) 0.2264(3) 0.26206(19) 0.0234(15) Uani 1 1 d . . . H1 H 0.8952(18) 0.9454(5) 0.2522(4) 0.035(3) Uani 1 1 d . . . H2 H 0.8182(18) 0.9474(6) 0.3740(5) 0.035(2) Uani 1 1 d . . . H2A H 0.7482(14) 0.6455(4) 0.4387(3) 0.023(2) Uani 1 1 d . . . H3 H 0.7853(16) 0.8021(5) 0.4385(4) 0.028(2) Uani 1 1 d . . . H3A H 0.7130(16) 0.5156(5) 0.4650(3) 0.023(2) Uani 1 1 d . . . H5 H 0.9018(17) 0.6457(5) 0.2573(3) 0.026(2) Uani 1 1 d . . . H9 H 0.6966(17) 0.3835(5) 0.5282(4) 0.032(2) Uani 1 1 d . . . H10 H 0.6989(17) 0.2140(6) 0.5366(4) 0.033(2) Uani 1 1 d . . . H11 H 0.7828(17) 0.1182(5) 0.4338(4) 0.032(2) Uani 1 1 d . . . H13 H 0.8732(17) 0.3680(5) 0.3203(3) 0.027(2) Uani 1 1 d . . . H14A H 0.881(2) 0.5647(6) 0.1079(5) 0.055(4) Uani 1 1 d . . . H14B H 0.7442(18) 0.4875(7) 0.0539(5) 0.040(3) Uani 1 1 d . . . H14C H 1.008(2) 0.4911(8) 0.0496(5) 0.047(3) Uani 1 1 d . . . H15A H 0.7243(18) 0.3720(7) 0.2156(4) 0.044(3) Uani 1 1 d . . . H15B H 0.5862(17) 0.4224(7) 0.1466(4) 0.035(2) Uani 1 1 d . . . H15C H 0.7129(19) 0.4939(7) 0.2050(5) 0.045(3) Uani 1 1 d . . . H16A H 1.0269(18) 0.3292(6) 0.0691(5) 0.038(3) Uani 1 1 d . . . H16B H 0.7651(19) 0.3234(6) 0.0706(5) 0.041(3) Uani 1 1 d . . . H16C H 0.908(2) 0.2796(6) 0.1397(5) 0.041(3) Uani 1 1 d . . . H17A H 1.2006(18) 0.4336(7) 0.1436(5) 0.040(3) Uani 1 1 d . . . H17B H 1.079(2) 0.3835(8) 0.2127(5) 0.053(3) Uani 1 1 d . . . H17C H 1.066(2) 0.5046(7) 0.2011(5) 0.053(3) 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 0.020(3) 0.0059(14) 0.0150(13) 0.0022(11) -0.0051(16) -0.0012(17) C2 0.020(3) 0.0072(15) 0.0132(13) -0.0003(11) 0.0007(15) 0.0015(16) C3 0.018(3) 0.0089(15) 0.0116(12) -0.0019(12) -0.0017(15) -0.0028(16) C4 0.012(3) 0.0065(13) 0.0078(11) -0.0006(11) -0.0015(13) 0.0040(15) C5 0.014(3) 0.0065(13) 0.0101(12) 0.0006(11) -0.0004(15) 0.0005(17) C6 0.017(3) 0.0100(15) 0.0095(11) 0.0021(11) -0.0016(14) 0.0018(18) C7 0.017(3) 0.0071(13) 0.0056(10) -0.0018(10) 0.0002(15) -0.0003(14) C8 0.011(3) 0.0090(14) 0.0085(11) -0.0024(11) 0.0016(14) -0.0009(15) C9 0.021(3) 0.0090(16) 0.0090(12) 0.0017(11) -0.0004(15) -0.0016(15) C10 0.015(3) 0.0108(16) 0.0116(13) 0.0052(11) 0.0032(16) 0.0017(15) C11 0.020(3) 0.0114(15) 0.0107(12) 0.0050(11) 0.0000(15) -0.0030(16) C12 0.015(3) 0.0064(14) 0.0110(12) 0.0003(10) -0.0001(16) 0.0000(15) C13 0.014(3) 0.0085(15) 0.0072(11) 0.0008(10) -0.0003(14) 0.0021(15) C14 0.034(4) 0.0161(19) 0.0215(18) 0.0049(14) 0.001(3) -0.0017(19) C15 0.015(3) 0.031(2) 0.0133(13) 0.0008(15) 0.0038(19) -0.0013(19) C16 0.025(3) 0.0095(16) 0.0239(17) -0.0059(13) -0.004(2) 0.0003(19) C17 0.010(3) 0.041(3) 0.0192(16) -0.0161(19) 0.000(2) -0.001(2) Cl1 0.020(2) 0.0156(11) 0.0076(8) -0.0034(8) 0.0029(11) 0.0012(12) N1 0.025(2) 0.0129(11) 0.0094(8) 0.0021(9) 0.0015(11) -0.0033(12) N2 0.018(2) 0.0068(9) 0.0074(8) -0.0021(7) 0.0017(10) 0.0001(10) N3 0.027(2) 0.0046(9) 0.0092(9) 0.0004(8) 0.0030(12) 0.0012(11) N4 0.020(2) 0.0085(10) 0.0135(9) -0.0023(8) -0.0016(12) 0.0021(12) N5 0.0104(19) 0.0144(11) 0.0104(9) -0.0027(7) -0.0012(11) -0.0016(12) O1 0.024(3) 0.0070(14) 0.0077(12) -0.0021(13) 0.0077(19) 0.0010(18) O2 0.051(5) 0.013(2) 0.0113(16) -0.0018(14) 0.000(2) -0.001(2) O3 0.065(6) 0.019(2) 0.0156(18) 0.0086(15) 0.004(2) -0.011(3) O4 0.039(4) 0.0059(16) 0.0243(18) -0.0021(16) 0.000(2) -0.004(2) O5 0.048(5) 0.0090(18) 0.0129(17) -0.0048(13) 0.002(2) 0.006(2) H1 0.059(9) 0.009(3) 0.037(4) 0.008(3) 0.004(5) -0.006(4) H2 0.049(8) 0.018(4) 0.038(4) -0.003(3) -0.001(5) 0.002(4) H2A 0.038(7) 0.015(3) 0.017(3) -0.005(2) 0.016(3) 0.003(3) H3 0.043(7) 0.017(3) 0.024(3) -0.004(3) 0.006(4) 0.005(4) H3A 0.037(7) 0.018(3) 0.015(3) -0.002(2) 0.003(3) 0.004(4) H5 0.041(7) 0.017(3) 0.020(3) -0.003(2) 0.006(4) 0.002(4) H9 0.052(8) 0.022(3) 0.023(3) 0.004(3) 0.012(4) 0.000(4) H10 0.051(8) 0.028(4) 0.018(3) 0.001(3) 0.004(4) 0.000(5) H11 0.050(8) 0.013(3) 0.033(4) 0.005(3) 0.007(4) -0.003(4) H13 0.044(7) 0.021(3) 0.017(3) 0.005(3) 0.011(4) -0.004(4) H14A 0.088(12) 0.018(4) 0.058(6) -0.003(4) 0.007(7) -0.005(5) H14B 0.034(9) 0.046(5) 0.039(5) 0.017(4) -0.018(5) -0.003(5) H14C 0.043(9) 0.059(6) 0.040(5) 0.019(4) 0.016(6) -0.009(6) H15A 0.030(8) 0.071(6) 0.032(4) 0.028(4) 0.006(4) 0.001(5) H15B 0.024(7) 0.058(5) 0.022(3) -0.008(3) -0.005(4) -0.002(5) H15C 0.041(9) 0.059(6) 0.037(4) -0.031(4) 0.005(5) -0.004(5) H16A 0.035(8) 0.039(5) 0.041(4) -0.015(4) 0.014(5) 0.006(5) H16B 0.053(10) 0.035(5) 0.035(4) -0.015(3) -0.015(5) -0.003(5) H16C 0.046(9) 0.030(4) 0.048(5) 0.016(4) 0.003(5) 0.001(5) H17A 0.020(8) 0.062(6) 0.039(5) -0.011(4) 0.006(5) 0.006(5) H17B 0.042(10) 0.074(7) 0.044(5) 0.005(6) -0.009(5) -0.007(7) H17C 0.047(10) 0.058(6) 0.054(6) -0.039(5) -0.009(6) -0.004(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C6 1.389(5) . ? C1 C2 1.396(4) . ? C1 H1 1.076(8) . ? C2 C3 1.391(5) . ? C2 H2 1.061(9) . ? C3 C4 1.411(5) . ? C3 H3 1.089(8) . ? C4 N2 1.393(4) . ? C4 C5 1.394(4) . ? C5 C6 1.384(5) . ? C5 H5 1.090(8) . ? C6 N1 1.463(4) . ? C7 O1 1.225(5) . ? C7 N3 1.373(4) . ? C7 N2 1.373(4) . ? C8 C13 1.387(5) . ? C8 N3 1.389(4) . ? C8 C9 1.404(5) . ? C9 C10 1.394(5) . ? C9 H9 1.074(9) . ? C10 C11 1.395(5) . ? C10 H10 1.091(8) . ? C11 C12 1.381(5) . ? C11 H11 1.077(8) . ? C12 C13 1.397(5) . ? C12 N4 1.467(4) . ? C13 H13 1.072(7) . ? C14 N5 1.487(4) . ? C14 H14A 1.075(10) . ? C14 H14B 1.093(15) . ? C14 H14C 1.102(15) . ? C15 N5 1.484(6) . ? C15 H15A 1.101(9) . ? C15 H15B 1.077(12) . ? C15 H15C 1.078(10) . ? C16 N5 1.496(4) . ? C16 H16A 1.075(14) . ? C16 H16B 1.094(14) . ? C16 H16C 1.079(9) . ? C17 N5 1.498(6) . ? C17 H17A 1.102(13) . ? C17 H17B 1.043(14) . ? C17 H17C 1.088(10) . ? N1 O2 1.218(5) . ? N1 O3 1.228(5) . ? N2 H2A 1.032(6) . ? N3 H3A 1.027(8) . ? N4 O4 1.217(4) . ? N4 O5 1.229(5) . ? 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 C6 C1 C2 117.6(3) . . ? C6 C1 H1 121.9(6) . . ? C2 C1 H1 120.6(6) . . ? C3 C2 C1 120.4(3) . . ? C3 C2 H2 120.0(6) . . ? C1 C2 H2 119.6(6) . . ? C2 C3 C4 120.8(3) . . ? C2 C3 H3 119.7(5) . . ? C4 C3 H3 119.5(5) . . ? N2 C4 C5 124.6(3) . . ? N2 C4 C3 116.3(3) . . ? C5 C4 C3 119.2(3) . . ? C6 C5 C4 118.5(3) . . ? C6 C5 H5 121.5(5) . . ? C4 C5 H5 120.0(5) . . ? C5 C6 C1 123.6(3) . . ? C5 C6 N1 118.0(3) . . ? C1 C6 N1 118.4(3) . . ? O1 C7 N3 124.5(3) . . ? O1 C7 N2 124.0(3) . . ? N3 C7 N2 111.5(2) . . ? C13 C8 N3 123.6(3) . . ? C13 C8 C9 119.7(3) . . ? N3 C8 C9 116.7(3) . . ? C10 C9 C8 120.7(3) . . ? C10 C9 H9 119.1(5) . . ? C8 C9 H9 120.2(5) . . ? C9 C10 C11 120.5(3) . . ? C9 C10 H10 119.1(5) . . ? C11 C10 H10 120.4(5) . . ? C12 C11 C10 117.2(3) . . ? C12 C11 H11 120.5(6) . . ? C10 C11 H11 122.3(5) . . ? C11 C12 C13 124.1(3) . . ? C11 C12 N4 118.8(3) . . ? C13 C12 N4 117.2(3) . . ? C8 C13 C12 117.8(3) . . ? C8 C13 H13 121.6(5) . . ? C12 C13 H13 120.6(5) . . ? N5 C14 H14A 108.3(6) . . ? N5 C14 H14B 107.6(6) . . ? H14A C14 H14B 112.2(11) . . ? N5 C14 H14C 107.5(7) . . ? H14A C14 H14C 110.7(11) . . ? H14B C14 H14C 110.4(9) . . ? N5 C15 H15A 107.8(7) . . ? N5 C15 H15B 108.3(6) . . ? H15A C15 H15B 112.4(9) . . ? N5 C15 H15C 109.0(8) . . ? H15A C15 H15C 108.6(9) . . ? H15B C15 H15C 110.7(9) . . ? N5 C16 H16A 108.7(6) . . ? N5 C16 H16B 108.4(6) . . ? H16A C16 H16B 110.7(8) . . ? N5 C16 H16C 107.6(6) . . ? H16A C16 H16C 110.0(10) . . ? H16B C16 H16C 111.3(10) . . ? N5 C17 H17A 108.3(6) . . ? N5 C17 H17B 109.1(8) . . ? H17A C17 H17B 109.8(11) . . ? N5 C17 H17C 108.6(8) . . ? H17A C17 H17C 109.3(10) . . ? H17B C17 H17C 111.5(10) . . ? O2 N1 O3 123.0(3) . . ? O2 N1 C6 118.7(3) . . ? O3 N1 C6 118.3(3) . . ? C7 N2 C4 127.4(2) . . ? C7 N2 H2A 115.2(4) . . ? C4 N2 H2A 116.5(4) . . ? C7 N3 C8 127.7(3) . . ? C7 N3 H3A 115.2(4) . . ? C8 N3 H3A 116.6(4) . . ? O4 N4 O5 122.7(4) . . ? O4 N4 C12 118.9(3) . . ? O5 N4 C12 118.4(3) . . ? C15 N5 C14 109.3(4) . . ? C15 N5 C16 109.1(3) . . ? C14 N5 C16 109.2(2) . . ? C15 N5 C17 109.8(3) . . ? C14 N5 C17 110.3(4) . . ? C16 N5 C17 109.2(3) . . ? 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 H2A Cl1 1.032(6) 2.197(7) 3.186(4) 160.0(5) . N3 H3A Cl1 1.027(8) 2.137(7) 3.135(4) 163.4(6) . _database_code_depnum_ccdc_archive 'CCDC 953027'