data_HA_CR _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P21' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,-Z _cell_length_a 4.62530(10) _cell_length_b 14.89280(2) _cell_length_c 8.9896(2) _cell_angle_alpha 90 _cell_angle_beta 90.4660(10) _cell_angle_gamma 90 _cell_volume 619.216(19) # Refinement details _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_number_restraints 1 _refine_ls_R_factor_gt 0.004 _refine_ls_R_factor_all 0.004 _refine_ls_R_Fsqd_factor 0.007 _refine_ls_wR_factor_ref 0.005 _refine_ls_hydrogen_treatment ? _refine_ls_number_reflns 9146 _refine_ls_number_parameters 293 _refine_ls_goodness_of_fit_ref 0.046 _refine_ls_weighting_scheme unit _refine_ls_shift/su_max 0.00007 _refine_ls_extinction_method none _refine_special_details ; refinement based on theoretical structure factors generated with the use of CRYSTAL06 ; _computing_structure_refinement 'Volkov et al, (2006)' _computing_molecular_graphics 'Volkov et al, (2006)' _computing_publication_material 'Volkov et al, (2006)' _publ_section_references ;Volkov, A.; Macchi, P.; Farrugia, L. J.; Gatti, C.; Mallinson, P. R.; Richter, T. and Koritsanszky, T. (2006) XD2006 - a computer program for multipole refinement, topological analysis and evaluation of intermolecular energies from experimental and theoretical structure factors. ; loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_U_iso_or_equiv O(3) 0.567273 0.814423 -0.164317 1 2 0.000 O(4) 0.298963 0.591227 -0.041246 1 2 0.000 O(5) 0.532207 0.475963 -0.147199 1 2 0.000 O(1W) 0.622049 0.077449 0.744811 1 2 0.000 O(2W) 0.109105 -0.019981 0.739851 1 2 0.000 N(1) 0.969733 0.898338 0.011643 1 2 0.000 N(2) 0.815892 0.680635 -0.157813 1 2 0.000 N(3) 1.229441 0.744447 0.360556 1 2 0.000 N(4) 1.111488 0.859172 0.505973 1 2 0.000 C(1) 0.966967 0.798409 0.009227 1 2 0.000 C(2) 0.765468 0.766108 -0.116071 1 2 0.000 C(3) 0.60995 0.627283 -0.244688 1 2 0.000 C(4) 0.471328 0.558484 -0.137107 1 2 0.000 C(5) 0.850201 0.75951 0.156826 1 2 0.000 C(6) 0.998017 0.789977 0.296889 1 2 0.000 C(7) 0.9235 0.861334 0.386804 1 2 0.000 C(8) 1.290996 0.788471 0.485652 1 2 0.000 C(9) 0.749758 0.586212 -0.381724 1 2 0.000 H(5) 1.131179 0.921551 0.082764 1 2 0.000 H(6) 0.772127 0.924235 0.047368 1 2 0.000 H(7) 1.018481 0.925242 -0.093164 1 2 0.000 H(8) 0.99386 0.648672 -0.112643 1 2 0.000 H(9) 1.114572 0.902402 0.596708 1 2 0.000 H(10) 1.187953 0.776349 -0.011448 1 2 0.000 H(11) 0.436521 0.673313 -0.276744 1 2 0.000 H(12) 0.620633 0.776137 0.165352 1 2 0.000 H(13) 0.864653 0.686402 0.149133 1 2 0.000 H(14) 0.75296 0.910265 0.373825 1 2 0.000 H(15) 1.460843 0.772947 0.564592 1 2 0.000 H(16) 0.591237 0.548628 -0.447785 1 2 0.000 H(17) 0.920798 0.539185 -0.349909 1 2 0.000 H(18) 0.842134 0.639032 -0.451593 1 2 0.000 H(1W) 0.649861 0.139297 0.703006 1 2 0.000 H(2W) 0.643536 0.083327 0.854213 1 2 0.000 H(3W) -0.057812 0.021065 0.723385 1 2 0.000 H(4W) 0.291083 0.015074 0.736358 1 2 0.000 DUM0 0 0 0 0 1 0 DUM1 0.663517 0.133831 0.801103 0 1 0 DUM2 0.133475 0.044855 0.723655 0 1 0 DUM3 1.011888 0.803204 0.150372 0 1 0 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(3) C(2) 1.24086 1_555 1_555 yes O(4) C(4) 1.27560 1_555 1_555 yes O(5) C(4) 1.26423 1_555 1_555 yes O(1W) H(1W) 1.00348 1_555 1_555 yes O(1W) H(2W) 0.99155 1_555 1_555 yes O(2W) H(3W) 0.99487 1_555 1_555 yes O(2W) H(4W) 0.99117 1_555 1_555 yes N(1) H(5) 1.03832 1_555 1_555 yes N(1) H(6) 1.04500 1_555 1_555 yes N(1) H(7) 1.05001 1_555 1_555 yes N(2) C(2) 1.34795 1_555 1_555 yes N(2) C(3) 1.46166 1_555 1_555 yes N(2) H(8) 1.03132 1_555 1_555 yes N(3) C(6) 1.38677 1_555 1_555 yes N(3) C(8) 1.33054 1_555 1_555 yes N(4) C(7) 1.37461 1_555 1_555 yes N(4) C(8) 1.35420 1_555 1_555 yes N(4) H(9) 1.03914 1_555 1_555 yes C(1) C(2) 1.53351 1_555 1_555 yes C(1) H(10) 1.09101 1_555 1_555 yes C(3) C(9) 1.52408 1_555 1_555 yes C(3) H(11) 1.09209 1_555 1_555 yes C(5) C(6) 1.49822 1_555 1_555 yes C(5) H(12) 1.09360 1_555 1_555 yes C(5) H(13) 1.09305 1_555 1_555 yes C(6) C(7) 1.38058 1_555 1_555 yes C(7) H(14) 1.07951 1_555 1_555 yes C(8) H(15) 1.07941 1_555 1_555 yes C(9) H(16) 1.09383 1_555 1_555 yes C(9) H(17) 1.09292 1_555 1_555 yes C(9) H(18) 1.09554 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 H(1W) O(1W) H(2W) 106.158 1_555 1_555 1_555 yes H(3W) O(2W) H(4W) 109.257 1_555 1_555 1_555 yes H(5) N(1) H(6) 108.319 1_555 1_555 1_555 yes H(5) N(1) H(7) 105.477 1_555 1_555 1_555 yes H(6) N(1) H(7) 109.248 1_555 1_555 1_555 yes C(2) N(2) C(3) 123.271 1_555 1_555 1_555 yes C(2) N(2) H(8) 117.750 1_555 1_555 1_555 yes C(3) N(2) H(8) 118.297 1_555 1_555 1_555 yes C(6) N(3) C(8) 105.487 1_555 1_555 1_555 yes C(7) N(4) C(8) 107.320 1_555 1_555 1_555 yes C(7) N(4) H(9) 126.997 1_555 1_555 1_555 yes C(8) N(4) H(9) 125.668 1_555 1_555 1_555 yes C(2) C(1) H(10) 110.183 1_555 1_555 1_555 yes O(3) C(2) N(2) 125.401 1_555 1_555 1_555 yes O(3) C(2) C(1) 121.176 1_555 1_555 1_555 yes N(2) C(2) C(1) 113.278 1_555 1_555 1_555 yes N(2) C(3) C(9) 111.782 1_555 1_555 1_555 yes N(2) C(3) H(11) 105.893 1_555 1_555 1_555 yes C(9) C(3) H(11) 110.744 1_555 1_555 1_555 yes O(4) C(4) O(5) 124.116 1_555 1_555 1_555 yes C(6) C(5) H(12) 108.012 1_555 1_555 1_555 yes C(6) C(5) H(13) 109.093 1_555 1_555 1_555 yes H(12) C(5) H(13) 106.851 1_555 1_555 1_555 yes N(3) C(6) C(5) 122.969 1_555 1_555 1_555 yes N(3) C(6) C(7) 109.285 1_555 1_555 1_555 yes C(5) C(6) C(7) 127.644 1_555 1_555 1_555 yes N(4) C(7) C(6) 106.194 1_555 1_555 1_555 yes N(4) C(7) H(14) 123.852 1_555 1_555 1_555 yes C(6) C(7) H(14) 129.942 1_555 1_555 1_555 yes N(3) C(8) N(4) 111.711 1_555 1_555 1_555 yes N(3) C(8) H(15) 126.848 1_555 1_555 1_555 yes N(4) C(8) H(15) 121.439 1_555 1_555 1_555 yes C(3) C(9) H(16) 110.932 1_555 1_555 1_555 yes C(3) C(9) H(17) 110.893 1_555 1_555 1_555 yes C(3) C(9) H(18) 110.197 1_555 1_555 1_555 yes H(16) C(9) H(17) 107.141 1_555 1_555 1_555 yes H(16) C(9) H(18) 108.601 1_555 1_555 1_555 yes H(17) C(9) H(18) 108.984 1_555 1_555 1_555 yes 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(3) 6.1577 0 0 0 -0.093(3) -0.051(2) 0 0 -0.080(2) 0 0.024(3) 0 0 0.007(2) 0 0 0 0.002(3) 0 0 0.005(3) 0 0 0 -0.002(3) 0 0.9953(6) 1.155(5) 1.38(5) 1.382692 1.382692 1.382692 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(4) 6.2424 0 -0.084(2) -0.002(2) 0 -0.030(2) 0 0 -0.087(2) -0.002(2) 0 -0.010(2) 0.000(3) 0 0 0.023(3) 0.002(2) 0.002(3) 0 0 -0.001(3) -0.003(3) 0 0 0.006(3) 0.001(3) 0.9923(4) 1.161(6) 1.03(3) 1.034108 1.034108 1.034108 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(5) 6.2216 0 -0.088(3) -0.001(2) 0 -0.044(2) 0 0 -0.086(2) 0.004(2) 0 -0.010(3) -0.003(2) 0 0 0.025(3) 0.001(2) 0.003(3) 0 0 0.001(3) -0.003(3) 0 0 0.008(3) 0.001(3) 0.9923(4) 1.161(6) 1.03(3) 1.034108 1.034108 1.034108 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(1W) 6.2354 0 0 0 -0.088(3) -0.005(2) 0 0 0.085(2) 0 -0.025(3) 0 0 -0.058(3) 0 0 0 -0.010(4) 0 0 -0.017(4) 0 0 0 0.003(3) 0 0.9933(4) 1.143(3) 1.18(2) 1.175482 1.175482 1.175482 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(2W) 6.2354 0 0 0 -0.089(3) -0.002(2) 0 0 0.092(2) 0 -0.033(3) 0 0 -0.057(3) 0 0 0 -0.011(4) 0 0 -0.016(3) 0 0 0 0.002(3) 0 0.9933(4) 1.143(3) 1.18(2) 1.175482 1.175482 1.175482 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 N(1) 5.0103 0 0 0 -0.022(6) -0.049(5) 0 0 0 0 0.231(9) 0 0 0 0 0.009(5) -0.197(8) 0.029(7) 0 0 0 0 -0.018(6) 0.094(8) 0 0 1.0028(10) 1.103(2) 1.358(13) 1.357822 1.357822 1.357822 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(2) 5.0467 0 -0.012(4) -0.025(4) 0 0.062(3) 0 0 -0.006(3) 0.030(3) 0 0.023(4) -0.003(4) 0 0 0.137(4) 0.012(4) 0.013(5) 0 0 0.003(5) 0.004(5) 0 0 -0.003(5) -0.001(5) 1.0020(10) 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(3) 5.1365 0 -0.067(4) -0.094(5) 0 -0.075(4) 0 0 -0.030(3) 0.077(3) 0 -0.017(4) -0.015(4) 0 0 0.086(5) -0.036(4) -0.003(5) 0 0 -0.002(5) 0.001(5) 0 0 0.021(5) 0.014(5) 0.9897(9) 0.992(13) 0.991666 0.991666 0.991666 0.991666 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(4) 5.0306 0 0.011(6) -0.005(5) 0 -0.005(4) 0 0 0.044(5) 0.006(4) 0 -0.026(5) -0.005(5) 0 0 0.185(10) 0.002(6) 0.001(7) 0 0 -0.021(7) 0.008(6) 0 0 -0.005(7) -0.003(7) 1.0009(10) 0.883(18) 0.882897 0.882897 0.882897 0.882897 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 C(1) 3.9688 0 0.054(6) -0.062(7) 0 0.025(5) 0 0 0.106(5) 0.044(5) 0 -0.168(7) -0.194(8) 0 0 0.206(8) -0.070(6) 0.042(9) 0 0 -0.023(9) 0.083(9) 0 0 0.065(8) 0.025(8) 0.9977(12) 0.901(9) 0.900641 0.900641 0.900641 0.900641 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(2) 4.1602 0 -0.030(7) -0.084(6) 0 -0.302(8) 0 0 -0.012(6) 0.103(6) 0 0.018(7) 0.001(7) 0 0 0.398(11) -0.077(8) 0.035(10) 0 0 0.012(9) -0.006(10) 0 0 0.032(10) 0.034(10) 0.9886(14) 0.833(8) 0.833393 0.833393 0.833393 0.833393 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(3) 4.0085 0 0.059(6) -0.034(6) 0 -0.004(5) 0 0 0.079(5) 0.034(5) 0 -0.152(7) -0.220(8) 0 0 0.207(8) -0.077(6) 0.048(9) 0 0 -0.037(8) 0.085(9) 0 0 0.057(8) 0.040(8) 0.9977(12) 0.901(9) 0.900641 0.900641 0.900641 0.900641 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(4) 4.1573 0 0.026(6) 0.059(6) 0 -0.323(7) 0 0 0.015(6) -0.066(6) 0 -0.005(7) 0.020(7) 0 0 0.433(10) 0.078(7) 0.032(9) 0 0 -0.001(9) -0.007(9) 0 0 0.003(9) -0.030(9) 0.9835(13) 0.830(7) 0.829595 0.829595 0.829595 0.829595 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(5) 4.0846 0 0 0 -0.063(6) -0.009(5) 0 0 0.057(5) 0 0.005(8) 0 0 -0.372(13) 0 0 0 -0.101(10) 0 0 0.032(9) 0 0 0 0.056(9) 0 0.9929(19) 0.874(12) 0.874306 0.874306 0.874306 0.874306 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(6) 4.074 0 -0.053(8) -0.005(8) 0 -0.137(7) 0 0 0.025(6) 0.031(6) 0 -0.020(7) -0.029(7) 0 0 0.323(13) -0.015(8) 0.021(10) 0 0 -0.037(10) 0.007(9) 0 0 -0.007(11) 0.028(10) 0.9949(17) 0.849(13) 0.849319 0.849319 0.849319 0.849319 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(7) 4.2123 0 -0.045(7) 0.031(8) 0 -0.137(7) 0 0 -0.079(6) 0.020(6) 0 -0.029(7) 0.028(7) 0 0 0.278(12) -0.089(9) 0.040(10) 0 0 -0.005(9) -0.015(9) 0 0 0.040(10) -0.002(10) 0.9944(18) 0.880(13) 0.880268 0.880268 0.880268 0.880268 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(8) 4.1827 0 -0.028(7) 0.037(7) 0 -0.170(7) 0 0 0.048(6) -0.052(6) 0 -0.022(7) 0.011(7) 0 0 0.341(12) 0.046(8) 0.056(9) 0 0 -0.034(9) -0.020(9) 0 0 -0.007(10) -0.021(10) 0.9962(17) 0.874(11) 0.87378 0.87378 0.87378 0.87378 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(9) 4.1686 0 0 0 -0.037(6) -0.034(5) 0 0 0 0 0.298(11) 0 0 0 0 -0.006(6) -0.242(10) 0.052(9) 0 0 0 0 -0.009(8) 0.117(10) 0 0 0.9882(18) 0.877(12) 0.876761 0.876761 0.876761 0.876761 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 H(5) 0.7851 0 0 0 0.145(5) 0.070(7) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.149(4) 1.248(17) 1.247724 1.247724 1.247724 1.247724 0 2 1 2 2 2 3 2 4 2 H(6) 0.7692 0 0 0 0.141(5) 0.100(7) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.149(4) 1.248(17) 1.247724 1.247724 1.247724 1.247724 0 2 1 2 2 2 3 2 4 2 H(7) 0.7802 0 0 0 0.144(5) 0.111(7) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.149(4) 1.248(17) 1.247724 1.247724 1.247724 1.247724 0 2 1 2 2 2 3 2 4 2 H(8) 0.8103 0 0 0 0.112(6) 0.062(6) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.177(5) 1.49(4) 1.486334 1.486334 1.486334 1.486334 0 2 1 2 2 2 3 2 4 2 H(9) 0.7911 0 0 0 0.115(7) 0.088(9) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.154(6) 1.35(4) 1.351276 1.351276 1.351276 1.351276 0 2 1 2 2 2 3 2 4 2 H(10) 0.8877 0 0 0 0.147(8) 0.063(8) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.156(4) 1.17(3) 1.169739 1.169739 1.169739 1.169739 0 2 1 2 2 2 3 2 4 2 H(11) 0.9141 0 0 0 0.145(8) 0.044(8) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.156(4) 1.17(3) 1.169739 1.169739 1.169739 1.169739 0 2 1 2 2 2 3 2 4 2 H(12) 0.9086 0 0 0 0.157(8) 0.050(7) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.157(4) 1.15(3) 1.147857 1.147857 1.147857 1.147857 0 2 1 2 2 2 3 2 4 2 H(13) 0.9234 0 0 0 0.147(7) 0.027(8) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.157(4) 1.15(3) 1.147857 1.147857 1.147857 1.147857 0 2 1 2 2 2 3 2 4 2 H(14) 0.9003 0 0 0 0.106(8) 0.034(7) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.155(5) 1.38(5) 1.382692 1.382692 1.382692 0(4) 0 2 1 2 2 2 3 2 4 2 H(15) 0.8742 0 0 0 0.226(12) 0.094(11) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.161(6) 1.03(3) 1.034108 1.034108 1.034108 0(4) 0 2 1 2 2 2 3 2 4 2 H(16) 0.937 0 0 0 0.137(6) 0.029(7) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.143(3) 1.18(2) 1.175482 1.175482 1.175482 1(4) 0 2 1 2 2 2 3 2 4 2 H(17) 0.9352 0 0 0 0.139(6) 0.063(8) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.143(3) 1.18(2) 1.175482 1.175482 1.175482 1(4) 0 2 1 2 2 2 3 2 4 2 H(18) 0.9201 0 0 0 0.133(6) 0.034(8) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.143(3) 1.18(2) 1.175482 1.175482 1.175482 1(4) 0 2 1 2 2 2 3 2 4 2 H(1W) 0.8822 0 0 0 0.145(3) 0.093(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.103(2) 1.358(13) 1.357822 1.357822 1.357822 1(4) 0 2 1 2 2 2 3 2 4 2 H(2W) 0.8822 0 0 0 0.1446 0.0934 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.103(2) 1.358(13) 1.357822 1.357822 1.357822 1(4) 0 2 1 2 2 2 3 2 4 2 H(3W) 0.8822 0 0 0 0.1446 0.0934 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.103(2) 1.358(13) 1.357822 1.357822 1.357822 1(4) 0 2 1 2 2 2 3 2 4 2 H(4W) 0.8822 0 0 0 0.1446 0.0934 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.103(2) 1.358(13) 1.357822 1.357822 1.357822 1(4) 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(3) C(2) Z O(3) N(2) Y O(4) C(4) X O(4) O(5) Y O(5) C(4) X O(5) O(4) Y O(1W) DUM1 Z O(1W) H(1W) Y O(2W) DUM2 Z O(2W) H(3W) Y N(1) C(1) Z N(1) H(5) Y N(2) C(2) X N(2) C(3) Y N(3) C(6) X N(3) C(8) Y N(4) H(9) X N(4) C(7) Y C(1) H(10) X C(1) N(1) Y C(2) N(2) X C(2) C(1) Y C(3) H(11) X C(3) N(2) Y C(4) O(4) X C(4) O(5) Y C(5) DUM3 Z C(5) C(1) Y C(6) C(5) X C(6) N(3) Y C(7) N(4) X C(7) C(6) Y C(8) H(15) X C(8) N(3) Y C(9) C(3) Z C(9) H(16) Y H(5) N(1) Z H(5) C(1) Y H(6) N(1) Z H(6) C(1) Y H(7) N(1) Z H(7) C(1) Y H(8) N(2) Z H(8) C(2) Y H(9) N(4) Z H(9) C(7) Y H(10) C(1) Z H(10) N(1) Y H(11) C(3) Z H(11) N(2) Y H(12) C(5) Z H(12) C(1) Y H(13) C(5) Z H(13) C(1) Y H(14) C(7) Z H(14) N(4) Y H(15) C(8) Z H(15) N(3) Y H(16) C(9) Z H(16) C(3) Y H(17) C(9) Z H(17) C(3) Y H(18) C(9) Z H(18) C(3) Y H(1W) O(1W) Z H(1W) H(2W) Y H(2W) O(1W) Z H(2W) H(1W) Y H(3W) O(2W) Z H(3W) H(4W) Y H(4W) O(2W) Z H(4W) H(3W) Y data_ALA_CR _symmetry_cell_setting 'orthorombic' _symmetry_space_group_name_H-M 'P21/c' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 +X,+Y,+Z 2 1/2-X,-Y,1/2+Z 3 1/2+X,1/2-Y,-Z 4 -X,1/2+Y,1/2-Z _cell_length_a 5.928 _cell_length_b 12.26 _cell_length_c 5.794 _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 421.0921 _cell_formula_units_Z ? _exptl_crystal_density_diffrn ? # Refinement details _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.005 _refine_ls_R_factor_all 0.005 _refine_ls_R_Fsqd_factor 0.006 _refine_ls_wR_factor_ref 0.005 _refine_ls_hydrogen_treatment ? _refine_ls_number_reflns 2668 _refine_ls_number_parameters 116 _refine_ls_goodness_of_fit_ref 0.043 _refine_ls_weighting_scheme calc _refine_ls_weighting_details unit _refine_ls_shift/su_max 0 _refine_ls_extinction_method none _refine_special_details ; refinement based on theoretical structure factors generated with the use of CRYSTAL06 ; _computing_structure_refinement 'Volkov et al, (2006)' _computing_molecular_graphics 'Volkov et al, (2006)' _computing_publication_material 'Volkov et al, (2006)' _publ_section_references ;Volkov, A.; Macchi, P.; Farrugia, L. J.; Gatti, C.; Mallinson, P. R.; Richter, T. and Koritsanszky, T. (2006) XD2006 - a computer program for multipole refinement, topological analysis and evaluation of intermolecular energies from experimental and theoretical structure factors. ; loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_U_iso_or_equiv O(1) 0.729722 0.08119 0.618253 1 4 0.000 O(2) 0.446211 0.182488 0.760847 1 4 0.000 N(1) 0.650272 0.140552 0.18065 1 4 0.000 C(1) 0.556856 0.139048 0.596472 1 4 0.000 C(2) 0.466712 0.1605 0.351727 1 4 0.000 C(3) 0.260995 0.090041 0.296193 1 4 0.000 H(2) 0.777349 0.197123 0.211808 1 4 0.000 H(3) 0.587449 0.152347 0.012722 1 4 0.000 H(1) 0.713184 0.062041 0.194047 1 4 0.000 H(4) 0.423771 0.246854 0.337436 1 4 0.000 H(5) 0.197144 0.110582 0.124872 1 4 0.000 H(6) 0.127546 0.104171 0.42225 1 4 0.000 H(7) 0.304635 0.003485 0.298751 1 4 0.000 DUM0 0 0 0 0 1 0 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(1) 1.252677489462 1_555 1_555 yes O(2) C(1) 1.273141750677 1_555 1_555 yes N(1) H(2) 1.0397574809379 1_555 1_555 yes N(1) H(3) 1.0518001910952 1_555 1_555 yes N(1) H(1) 1.0351832374849 1_555 1_555 yes C(1) C(2) 1.5380499453138 1_555 1_555 yes C(2) C(3) 1.5286871000337 1_555 1_555 yes C(2) H(4) 1.0920166036096 1_555 1_555 yes C(3) H(5) 1.0917923399476 1_555 1_555 yes C(3) H(6) 1.0905383172167 1_555 1_555 yes C(3) H(7) 1.092355411958 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 H(2) N(1) H(3) 108.99190223576 1_555 1_555 1_555 yes H(2) N(1) H(1) 110.25499914714 1_555 1_555 1_555 yes H(3) N(1) H(1) 108.95126745024 1_555 1_555 1_555 yes O(1) C(1) O(2) 125.65889077277 1_555 1_555 1_555 yes O(1) C(1) C(2) 118.28976812377 1_555 1_555 1_555 yes O(2) C(1) C(2) 116.05120693087 1_555 1_555 1_555 yes C(1) C(2) C(3) 111.99941813092 1_555 1_555 1_555 yes C(1) C(2) H(4) 108.46217361699 1_555 1_555 1_555 yes C(3) C(2) H(4) 110.23803921839 1_555 1_555 1_555 yes C(2) C(3) H(5) 109.7300966207 1_555 1_555 1_555 yes C(2) C(3) H(6) 110.36216660817 1_555 1_555 1_555 yes C(2) C(3) H(7) 110.92637495893 1_555 1_555 1_555 yes H(5) C(3) H(6) 108.7101899354 1_555 1_555 1_555 yes H(5) C(3) H(7) 108.57324511521 1_555 1_555 1_555 yes H(6) C(3) H(7) 108.48317620534 1_555 1_555 1_555 yes 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) 6.350(13) 0 -0.080(3) -0.002(2) 0 -0.048(2) 0 0 -0.079(2) 0.000(2) 0 -0.010(2) -0.004(3) 0 0 0.022(2) 0.003(3) -0.002(3) 0 0 0.000(3) -0.002(3) 0 0 0.012(3) 0.002(3) 0.9744(8) 1.156(16) 1.155631 1.155631 1.155631 1.155631 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(2) 6.424(12) 0 -0.071(3) 0.0000(19) 0 -0.0199(19) 0 0 -0.072(3) -0.0009(17) 0 -0.007(3) -0.002(2) 0 0 0.024(2) -0.002(2) 0.000(3) 0 0 -0.004(3) 0.001(3) 0 0 0.006(3) 0.001(3) 0.9716(8) 1.18(2) 1.178265 1.178265 1.178265 1.178265 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 N(1) 5.23(5) 0 0 0 -0.016(6) -0.048(5) 0 0 0 0 0.234(9) 0 0 0 0 -0.011(5) -0.195(8) 0.046(8) 0 0 0 0 -0.006(5) 0.086(7) 0 0 0.984(2) 0.821(11) 0.820831 0.820831 0.820831 0.820831 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 C(1) 3.93(2) 0 0.026(6) -0.004(6) 0 -0.267(8) 0 0 0.044(5) -0.036(6) 0 -0.009(5) 0.008(7) 0 0 0.355(11) 0.055(7) 0.056(8) 0 0 -0.010(7) 0.003(8) 0 0 -0.028(8) -0.014(8) 1.001(2) 0.895(10) 0.894982 0.894982 0.894982 0.894982 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(2) 3.77(4) 0 0.015(7) -0.053(5) 0 0.047(5) 0 0 0.082(5) 0.056(5) 0 -0.144(9) -0.175(9) 0 0 0.163(9) -0.052(5) 0.038(7) 0 0 -0.014(7) 0.069(8) 0 0 0.048(7) 0.042(7) 1.010(3) 0.953(15) 0.952702 0.952702 0.952702 0.952702 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(3) 3.49(5) 0 0 0 0.040(7) -0.011(5) 0 0 0 0 0.237(10) 0 0 0 0 -0.005(5) -0.183(8) 0.045(8) 0 0 0 0 -0.004(6) 0.071(8) 0 0 1.023(3) 0.916(13) 0.9159 0.9159 0.9159 0.9159 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 H(2) 0.790(16) 0 0 0 0.108(7) 0.068(7) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.141(10) 1.41(3) 1.413635 1.413635 1.413635 1.413635 0 2 1 2 2 2 3 2 4 2 H(3) 0.773(16) 0 0 0 0.106(7) 0.080(7) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.141(10) 1.41(3) 1.413635 1.413635 1.413635 1.413635 0 2 1 2 2 2 3 2 4 2 H(1) 0.781(16) 0 0 0 0.116(7) 0.060(6) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.141(10) 1.41(3) 1.413635 1.413635 1.413635 1.413635 0 2 1 2 2 2 3 2 4 2 H(4) 1.03(3) 0 0 0 0.184(12) 0.099(11) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.107(12) 1.12(3) 1.120169 1.120169 1.120169 1.120169 0 2 1 2 2 2 3 2 4 2 H(5) 1.155(17) 0 0 0 0.210(9) 0.098(8) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.065(6) 1.124(14) 1.124024 1.124024 1.124024 1.124024 0 2 1 2 2 2 3 2 4 2 H(6) 1.130(16) 0 0 0 0.219(9) 0.096(9) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.065(6) 1.124(14) 1.124024 1.124024 1.124024 1.124024 0 2 1 2 2 2 3 2 4 2 H(7) 1.153(16) 0 0 0 0.203(8) 0.112(8) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.065(6) 1.124(14) 1.124024 1.124024 1.124024 1.124024 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(1) X O(1) O(2) Y O(2) C(1) X O(2) O(1) Y N(1) C(2) Z N(1) H(2) Y C(1) O(1) X C(1) O(2) Y C(2) H(4) X C(2) N(1) Y C(3) C(2) Z C(3) H(5) Y H(2) N(1) Z H(2) C(2) Y H(3) N(1) Z H(3) C(2) Y H(1) N(1) Z H(1) C(2) Y H(4) C(2) Z H(4) N(1) Y H(5) C(3) Z H(5) C(2) Y H(6) C(3) Z H(6) C(2) Y H(7) C(3) Z H(7) C(2) Y data_GH_CR _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P21' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,-Z _cell_length_a 6.0342 _cell_length_b 7.2600 _cell_length_c 12.9244 _cell_angle_alpha 90.000 _cell_angle_beta 99.974 _cell_angle_gamma 90.000 _cell_volume 557.639 _cell_formula_units_Z ? _exptl_crystal_density_diffrn ? # Refinement details _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.006 _refine_ls_R_factor_all 0.006 _refine_ls_R_Fsqd_factor 0.008 _refine_ls_wR_factor_ref 0.006 _refine_ls_hydrogen_treatment ? _refine_ls_number_reflns 8439 _refine_ls_number_parameters 326 _refine_ls_goodness_of_fit_ref 0.052 _refine_ls_weighting_scheme calc _refine_ls_weighting_details unit _refine_ls_shift/su_max 0.01078 _refine_ls_extinction_method none _refine_special_details ; refinement based on theoretical structure factors generated with the use of CRYSTAL06 ; _computing_structure_refinement 'Volkov et al, (2006)' _computing_molecular_graphics 'Volkov et al, (2006)' _computing_publication_material 'Volkov et al, (2006)' _publ_section_references ;Volkov, A.; Macchi, P.; Farrugia, L. J.; Gatti, C.; Mallinson, P. R.; Richter, T. and Koritsanszky, T. (2006) XD2006 - a computer program for multipole refinement, topological analysis and evaluation of intermolecular energies from experimental and theoretical structure factors. ; loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_U_iso_or_equiv O(1) 0.950043 0.293811 0.746136 1 2 0.000 O(2) 1.282447 0.713786 0.904155 1 2 0.000 O(3) 1.441391 0.790018 0.765974 1 2 0.000 O(1W) 0.889407 0.000137 0.962918 1 2 0.000 O(2W) 0.297665 0.186226 0.976035 1 2 0.000 N(1) 0.552861 0.18606 0.811798 1 2 0.000 N(2) 0.886269 0.599237 0.778008 1 2 0.000 N(3) 0.577673 0.75411 0.573104 1 2 0.000 N(4) 0.592725 0.718808 0.404065 1 2 0.000 C(1) 0.646132 0.371854 0.83805 1 2 0.000 C(2) 0.841925 0.416483 0.78171 1 2 0.000 C(3) 1.064249 0.674512 0.72794 1 2 0.000 C(4) 1.277297 0.732776 0.806298 1 2 0.000 C(5) 0.979109 0.837001 0.65388 1 2 0.000 C(6) 0.799076 0.785979 0.563332 1 2 0.000 C(7) 0.804456 0.763997 0.457505 1 2 0.000 C(8) 0.461224 0.714662 0.47643 1 2 0.000 H(1) 0.493939 0.176939 0.729396 1 2 0.000 H(2) 0.421902 0.167802 0.853677 1 2 0.000 H(3) 0.672371 0.087214 0.838443 1 2 0.000 H(4) 0.7037 0.380655 0.922758 1 2 0.000 H(5) 0.511743 0.47169 0.817327 1 2 0.000 H(6) 0.775234 0.688583 0.802258 1 2 0.000 H(7) 1.119502 0.56294 0.681378 1 2 0.000 H(8) 0.922037 0.949364 0.699761 1 2 0.000 H(9) 1.122239 0.892094 0.622536 1 2 0.000 H(10) 0.944156 0.777197 0.415791 1 2 0.000 H(11) 0.283679 0.68283 0.461787 1 2 0.000 H(12) 0.512661 0.763676 0.642025 1 2 0.000 H(1W) 0.852837 0.084552 1.017929 1 2 0.000 H(2W) 1.046224 0.029734 0.958473 1 2 0.000 H(3W) 0.216505 0.297025 0.99397 1 2 0.000 H(4W) 0.444257 0.195227 1.024155 1 2 0.000 DUM0 0 0 0 0 1 0 DUM1 1.01229 0.115379 1.01384 0 1 0 DUM2 0.363537 0.307231 1.04269 0 1 0 DUM3 0.913936 0.698105 0.64126 0 1 0 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(2) 1.2385866926139 1_555 1_555 yes O(2) C(4) 1.2672542912558 1_555 1_555 yes O(3) C(4) 1.2663030506364 1_555 1_555 yes O(1W) H(1W) 0.99203367460941 1_555 1_555 yes O(1W) H(2W) 0.98169240292638 1_555 1_555 yes O(2W) H(3W) 0.98992755442832 1_555 1_555 yes O(2W) H(4W) 0.99143622660773 1_555 1_555 yes N(1) H(1) 1.0648228891084 1_555 1_555 yes N(1) H(2) 1.0407527172808 1_555 1_555 yes N(1) H(3) 1.0332473716667 1_555 1_555 yes N(2) C(2) 1.3559887741283 1_555 1_555 yes N(2) C(3) 1.4531131592761 1_555 1_555 yes N(2) H(6) 1.0201134755235 1_555 1_555 yes N(3) C(6) 1.383040427832 1_555 1_555 yes N(3) C(8) 1.3538015977728 1_555 1_555 yes N(3) H(12) 1.0359656905815 1_555 1_555 yes N(4) C(7) 1.3825059651846 1_555 1_555 yes N(4) C(8) 1.3275438792402 1_555 1_555 yes C(1) C(2) 1.5261190074726 1_555 1_555 yes C(1) H(4) 1.0916043616118 1_555 1_555 yes C(1) H(5) 1.0860270753533 1_555 1_555 yes C(3) H(7) 1.0949565159445 1_555 1_555 yes C(5) C(6) 1.4988437157791 1_555 1_555 yes C(5) H(8) 1.0983751375239 1_555 1_555 yes C(5) H(9) 1.0914307867744 1_555 1_555 yes C(6) C(7) 1.3829840949708 1_555 1_555 yes C(7) H(10) 1.080687745448 1_555 1_555 yes C(8) H(11) 1.0801677632159 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 H(1W) O(1W) H(2W) 104.06634264388 1_555 1_555 1_555 yes H(3W) O(2W) H(4W) 102.90772689025 1_555 1_555 1_555 yes H(1) N(1) H(2) 111.10987883445 1_555 1_555 1_555 yes H(1) N(1) H(3) 112.52078944323 1_555 1_555 1_555 yes H(2) N(1) H(3) 106.68965673417 1_555 1_555 1_555 yes C(2) N(2) C(3) 123.31790095986 1_555 1_555 1_555 yes C(2) N(2) H(6) 117.85330608009 1_555 1_555 1_555 yes C(3) N(2) H(6) 118.23525246077 1_555 1_555 1_555 yes C(6) N(3) C(8) 107.83561727419 1_555 1_555 1_555 yes C(6) N(3) H(12) 125.65806693572 1_555 1_555 1_555 yes C(8) N(3) H(12) 126.47207853189 1_555 1_555 1_555 yes C(7) N(4) C(8) 105.47631180909 1_555 1_555 1_555 yes C(2) C(1) H(4) 109.14290352234 1_555 1_555 1_555 yes C(2) C(1) H(5) 110.32441584041 1_555 1_555 1_555 yes H(4) C(1) H(5) 107.61331300661 1_555 1_555 1_555 yes O(1) C(2) N(2) 124.79326568173 1_555 1_555 1_555 yes O(1) C(2) C(1) 121.70418651131 1_555 1_555 1_555 yes N(2) C(2) C(1) 113.47674526118 1_555 1_555 1_555 yes N(2) C(3) H(7) 106.58367478464 1_555 1_555 1_555 yes O(2) C(4) O(3) 124.10378177624 1_555 1_555 1_555 yes C(6) C(5) H(8) 110.63716761784 1_555 1_555 1_555 yes C(6) C(5) H(9) 108.29407034471 1_555 1_555 1_555 yes H(8) C(5) H(9) 105.69234739344 1_555 1_555 1_555 yes N(3) C(6) C(5) 123.43643594304 1_555 1_555 1_555 yes N(3) C(6) C(7) 105.04169083798 1_555 1_555 1_555 yes C(5) C(6) C(7) 131.50709292591 1_555 1_555 1_555 yes N(4) C(7) C(6) 110.09052044586 1_555 1_555 1_555 yes N(4) C(7) H(10) 120.33340722745 1_555 1_555 1_555 yes C(6) C(7) H(10) 129.57607648681 1_555 1_555 1_555 yes N(3) C(8) N(4) 111.55450622943 1_555 1_555 1_555 yes N(3) C(8) H(11) 123.19316307288 1_555 1_555 1_555 yes N(4) C(8) H(11) 125.24981444731 1_555 1_555 1_555 yes 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) 6.26(2) 0 0 0 -0.083(4) -0.046(3) 0 0 -0.078(3) 0 0.025(3) 0 0 0.006(3) 0 0 0 0.002(4) 0 0 0.004(3) 0 0 0 -0.002(3) 0 0.9815(11) 0.989(13) 0.96(2) 0.964681 0.964681 0.964681 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(2) 6.373(14) 0 -0.069(3) 0.000(2) 0 -0.026(2) 0 0 -0.072(2) -0.001(2) 0 -0.010(3) -0.003(3) 0 0 0.025(2) 0.000(2) 0.002(4) 0 0 -0.006(3) 0.003(4) 0 0 0.007(3) 0.002(3) 0.9760(7) 0.998(14) 1.04(3) 1.035105 1.035105 1.035105 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(3) 6.365(15) 0 -0.071(3) -0.001(2) 0 -0.028(2) 0 0 -0.075(2) 0.000(2) 0 -0.008(3) -0.000(3) 0 0 0.027(2) 0.001(2) -0.001(4) 0 0 -0.001(4) -0.003(4) 0 0 0.004(3) 0.004(3) 0.9760(7) 0.998(14) 1.04(3) 1.035105 1.035105 1.035105 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(1W) 6.15(2) 0 0 0 -0.103(4) -0.005(3) 0 0 0.099(3) 0 -0.035(4) 0 0 -0.063(4) 0 0 0 -0.014(4) 0 0 -0.015(4) 0 0 0 0.007(4) 0 0.9873(11) 1.081(7) 1.308(19) 1.307696 1.307696 1.307696 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(2W) 6.13(2) 0 0 0 -0.098(4) -0.006(3) 0 0 0.100(3) 0 -0.033(4) 0 0 -0.056(3) 0 0 0 -0.011(4) 0 0 -0.017(4) 0 0 0 0.003(4) 0 0.9873(11) 1.081(7) 1.308(19) 1.307696 1.307696 1.307696 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 N(1) 5.01(5) 0 0 0 -0.019(7) -0.051(6) 0 0 0 0 0.217(11) 0 0 0 0 -0.012(5) -0.174(9) 0.038(9) 0 0 0 0 0.008(7) 0.071(9) 0 0 0.998(3) 0.844(15) 0.844277 0.844277 0.844277 0.844277 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(2) 4.85(3) 0 0.007(5) 0.009(4) 0 0.073(4) 0 0 0.004(3) 0.006(4) 0 0.019(5) 0.000(4) 0 0 0.113(7) 0.013(4) 0.008(5) 0 0 0.003(5) 0.001(5) 0 0 -0.006(5) 0.001(5) 1.002(2) 1.07(2) 1.066975 1.066975 1.066975 1.066975 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(3) 4.94(3) 0 0.017(8) 0.026(9) 0 -0.013(6) 0 0 -0.014(5) 0.026(6) 0 -0.004(7) 0.012(7) 0 0 0.202(13) -0.068(7) 0.005(9) 0 0 0.007(9) -0.033(9) 0 0 -0.002(8) 0.007(8) 0.998(2) 0.830(19) 0.829568 0.829568 0.829568 0.829568 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(4) 5.14(3) 0 -0.052(4) -0.075(5) 0 -0.074(4) 0 0 -0.022(3) 0.069(3) 0 -0.022(4) -0.018(4) 0 0 0.082(4) -0.032(4) -0.009(6) 0 0 -0.006(5) 0.007(5) 0 0 0.020(5) 0.009(5) 0.9838(16) 1.045(16) 1.045027 1.045027 1.045027 1.045027 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 C(1) 3.27(5) 0 -0.009(7) 0.015(7) -0.016(7) -0.083(7) 0.004(5) 0.011(5) 0.017(5) 0.008(5) 0.205(13) -0.006(6) 0.009(7) -0.002(7) -0.008(7) -0.007(6) -0.153(11) 0.044(10) 0.005(8) -0.021(8) 0.005(8) 0.025(8) 0.006(8) 0.067(10) 0.000(7) -0.010(7) 1.042(4) 0.97(2) 0.9743 0.9743 0.9743 0.9743 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(2) 4.05(3) 0 -0.032(9) -0.027(8) 0 -0.284(11) 0 0 -0.019(7) 0.060(8) 0 0.011(9) -0.008(8) 0 0 0.370(17) -0.076(9) 0.036(11) 0 0 0.014(10) 0.027(11) 0 0 0.052(12) 0.026(12) 0.998(3) 0.861(12) 0.861166 0.861166 0.861166 0.861166 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(3) 3.63(5) 0 -0.048(13) -0.057(8) 0 0.028(7) 0 0 0.022(8) 0.040(6) 0 -0.153(11) -0.245(13) 0 0 0.213(11) -0.082(9) 0.044(11) 0 0 -0.020(10) 0.085(12) 0 0 0.080(11) 0.046(10) 1.014(3) 0.874(15) 0.87402 0.87402 0.87402 0.87402 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(4) 3.88(3) 0 -0.004(6) 0.008(7) 0 -0.271(10) 0 0 0.027(5) -0.042(6) 0 0.003(8) -0.017(8) 0 0 0.337(14) 0.036(6) 0.009(11) 0 0 -0.001(10) 0.001(10) 0 0 0.008(8) -0.009(9) 1.002(3) 0.894(12) 0.894057 0.894057 0.894057 0.894057 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(5) 3.26(6) 0 0 0 0.055(10) -0.030(6) 0 0 0.014(6) 0 -0.021(8) 0 0 -0.283(16) 0 0 0 -0.078(12) 0 0 0.009(10) 0 0 0 0.035(9) 0 1.033(4) 0.924(19) 0.924347 0.924347 0.924347 0.924347 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(6) 4.04(4) 0 -0.008(10) -0.063(9) 0 -0.118(8) 0 0 0.042(7) 0.069(7) 0 -0.026(8) -0.041(8) 0 0 0.271(15) -0.025(8) 0.014(11) 0 0 -0.002(11) 0.033(11) 0 0 -0.016(11) 0.029(10) 0.995(3) 0.898(16) 0.898154 0.898154 0.898154 0.898154 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(7) 3.71(5) 0 0.029(9) 0.127(14) 0 -0.121(9) 0 0 -0.032(7) 0.004(7) 0 -0.008(8) 0.015(8) 0 0 0.273(15) -0.058(8) 0.012(11) 0 0 0.001(10) -0.040(10) 0 0 0.022(9) -0.002(10) 1.014(3) 0.886(16) 0.8864 0.8864 0.8864 0.8864 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(8) 3.67(4) 0 -0.118(15) -0.059(8) 0 -0.140(9) 0 0 0.011(8) 0.068(7) 0 0.009(9) -0.012(9) 0 0 0.324(17) -0.029(8) 0.035(11) 0 0 -0.026(11) 0.004(11) 0 0 -0.046(12) 0.011(11) 1.022(3) 0.868(15) 0.868363 0.868363 0.868363 0.868363 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 H(1) 0.812(19) 0 0 0 0.122(8) 0.104(10) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.104(10) 1.32(3) 1.315969 1.315969 1.315969 1.315969 0 2 1 2 2 2 3 2 4 2 H(2) 0.849(19) 0 0 0 0.127(8) 0.079(9) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.104(10) 1.32(3) 1.315969 1.315969 1.315969 1.315969 0 2 1 2 2 2 3 2 4 2 H(3) 0.853(19) 0 0 0 0.144(9) 0.082(9) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.104(10) 1.32(3) 1.315969 1.315969 1.315969 1.315969 0 2 1 2 2 2 3 2 4 2 H(4) 1.24(3) 0 0 0 0.245(14) 0.137(14) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.023(9) 1.06(2) 1.060442 1.060442 1.060442 1.060442 0 2 1 2 2 2 3 2 4 2 H(5) 1.25(3) 0 0 0 0.266(16) 0.136(15) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.023(9) 1.06(2) 1.060442 1.060442 1.060442 1.060442 0 2 1 2 2 2 3 2 4 2 H(6) 1.08(2) 0 0 0 0.198(12) 0.113(12) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.051(10) 1.24(3) 1.235519 1.235519 1.235519 1.235519 0 2 1 2 2 2 3 2 4 2 H(7) 1.29(4) 0 0 0 0.32(3) 0.17(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0.984(14) 1.00(3) 0.996569 0.996569 0.996569 0.996569 0 2 1 2 2 2 3 2 4 2 H(8) 1.32(3) 0 0 0 0.291(17) 0.150(16) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0.996(9) 1.02(2) 1.024637 1.024637 1.024637 1.024637 0 2 1 2 2 2 3 2 4 2 H(9) 1.29(3) 0 0 0 0.297(16) 0.149(16) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0.996(9) 1.02(2) 1.024637 1.024637 1.024637 1.024637 0 2 1 2 2 2 3 2 4 2 H(10) 1.30(4) 0 0 0 0.36(2) 0.20(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0.989(13) 0.96(2) 0.964681 0.964681 0.964681 0(4) 0 2 1 2 2 2 3 2 4 2 H(11) 1.30(4) 0 0 0 0.29(2) 0.18(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0.998(14) 1.04(3) 1.035105 1.035105 1.035105 0(4) 0 2 1 2 2 2 3 2 4 2 H(12) 0.97(2) 0 0 0 0.166(11) 0.137(12) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.051(10) 1.24(3) 1.235519 1.235519 1.235519 1.235519 0 2 1 2 2 2 3 2 4 2 H(1W) 0.917(13) 0 0 0 0.174(7) 0.129(9) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.081(7) 1.308(19) 1.307696 1.307696 1.307696 1(4) 0 2 1 2 2 2 3 2 4 2 H(2W) 0.936(13) 0 0 0 0.165(7) 0.086(8) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.081(7) 1.308(19) 1.307696 1.307696 1.307696 1(4) 0 2 1 2 2 2 3 2 4 2 H(3W) 0.934(13) 0 0 0 0.173(8) 0.117(9) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.081(7) 1.308(19) 1.307696 1.307696 1.307696 1(4) 0 2 1 2 2 2 3 2 4 2 H(4W) 0.941(13) 0 0 0 0.161(7) 0.120(8) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.081(7) 1.308(19) 1.307696 1.307696 1.307696 1(4) 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(2) Z O(1) N(2) Y O(2) C(4) X O(2) O(3) Y O(3) C(4) X O(3) O(2) Y O(1W) DUM1 Z O(1W) H(1W) Y O(2W) DUM2 Z O(2W) H(3W) Y N(1) C(1) Z N(1) H(1) Y N(2) C(2) X N(2) C(3) Y N(3) C(6) X N(3) C(8) Y N(4) C(7) X N(4) C(8) Y C(1) N(1) Z C(1) C(2) Y C(2) N(2) X C(2) C(1) Y C(3) H(7) X C(3) N(2) Y C(4) O(2) X C(4) O(3) Y C(5) DUM3 Z C(5) C(3) Y C(6) C(5) X C(6) N(3) Y C(7) N(4) X C(7) C(6) Y C(8) H(11) X C(8) N(3) Y H(1) N(1) Z H(1) C(1) Y H(2) N(1) Z H(2) C(1) Y H(3) N(1) Z H(3) C(1) Y H(4) C(1) Z H(4) N(1) Y H(5) C(1) Z H(5) N(1) Y H(6) N(2) Z H(6) C(2) Y H(7) C(3) Z H(7) N(2) Y H(8) C(5) Z H(8) C(3) Y H(9) C(5) Z H(9) C(3) Y H(10) C(7) Z H(10) N(4) Y H(11) C(8) Z H(11) N(3) Y H(12) N(3) Z H(12) C(6) Y H(1W) O(1W) Z H(1W) H(2W) Y H(2W) O(1W) Z H(2W) H(1W) Y H(3W) O(2W) Z H(3W) H(4W) Y H(4W) O(2W) Z H(4W) H(3W) Y data_HIS_CR _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P21/c' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 +X,1/2-Y,1/2+Z _cell_length_a 8.9886 _cell_length_b 7.9447 _cell_length_c 9.3861 _cell_angle_alpha 90 _cell_angle_beta 97.367 _cell_angle_gamma 90 _cell_volume 664.744559 _cell_formula_units_Z ? _exptl_crystal_density_diffrn ? # Refinement details _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.007 _refine_ls_R_factor_all 0.007 _refine_ls_R_Fsqd_factor 0.01 _refine_ls_wR_factor_ref 0.007 _refine_ls_hydrogen_treatment ? _refine_ls_number_reflns 9151 _refine_ls_number_parameters 195 _refine_ls_goodness_of_fit_ref 0.072 _refine_ls_weighting_scheme unit _refine_ls_shift/su_max 0.00107 _refine_ls_extinction_method none _refine_special_details ; refinement based on theoretical structure factors generated with the use of CRYSTAL06 ; _computing_structure_refinement 'Volkov et al, (2006)' _computing_molecular_graphics 'Volkov et al, (2006)' _computing_publication_material 'Volkov et al, (2006)' _publ_section_references ;Volkov, A.; Macchi, P.; Farrugia, L. J.; Gatti, C.; Mallinson, P. R.; Richter, T. and Koritsanszky, T. (2006) XD2006 - a computer program for multipole refinement, topological analysis and evaluation of intermolecular energies from experimental and theoretical structure factors. ; loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_U_iso_or_equiv O(1) -0.123778 0.41172 0.136386 1 4 0.000 O(2) -0.061043 0.337527 0.367635 1 4 0.000 N(1) 0.149687 0.333052 0.061556 1 4 0.000 N(2) 0.417201 0.25717 0.453048 1 4 0.000 N(3) 0.635474 0.331 0.385195 1 4 0.000 C(1) -0.031912 0.361887 0.239901 1 4 0.000 C(2) 0.131775 0.326519 0.216694 1 4 0.000 C(3) 0.239039 0.450979 0.304916 1 4 0.000 C(4) 0.393068 0.382528 0.349773 1 4 0.000 C(5) 0.564366 0.230188 0.471393 1 4 0.000 C(6) 0.528175 0.42925 0.307295 1 4 0.000 H(2) 0.130367 0.451611 0.016226 1 4 0.000 H(3) 0.071598 0.255591 0.000414 1 4 0.000 H(4) 0.259009 0.29987 0.039813 1 4 0.000 H(8) 0.750356 0.335337 0.379912 1 4 0.000 H(1) 0.157835 0.19748 0.252583 1 4 0.000 H(5) 0.244798 0.56755 0.244001 1 4 0.000 H(6) 0.18811 0.484976 0.40071 1 4 0.000 H(7) 0.624942 0.143502 0.546299 1 4 0.000 H(9) 0.554692 0.523498 0.231738 1 4 0.000 DUM0 0 0 0 0 1 0 DUM1 0.26617 0.335482 0.28509 0 1 0 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(1) 1.2557321827321 1_555 1_555 yes O(2) C(1) 1.2743416369956 1_555 1_555 yes N(1) H(2) 1.0389617584108 1_555 1_555 yes N(1) H(3) 1.0475886331314 1_555 1_555 yes N(1) H(4) 1.0621577611061 1_555 1_555 yes N(2) C(4) 1.3873177121249 1_555 1_555 yes N(2) C(5) 1.3292885858154 1_555 1_555 yes N(3) C(5) 1.3554339061205 1_555 1_555 yes N(3) C(6) 1.3759565892458 1_555 1_555 yes N(3) H(8) 1.0407203212447 1_555 1_555 yes C(2) H(1) 1.0950315873328 1_555 1_555 yes C(3) C(4) 1.4967887412203 1_555 1_555 yes C(3) H(5) 1.0931032332307 1_555 1_555 yes C(3) H(6) 1.0938506556562 1_555 1_555 yes C(4) C(6) 1.3768592791779 1_555 1_555 yes C(5) H(7) 1.0802381811873 1_555 1_555 yes C(6) H(9) 1.0787791015654 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 H(2) N(1) H(3) 104.07361569732 1_555 1_555 1_555 yes H(2) N(1) H(4) 104.86257332193 1_555 1_555 1_555 yes H(3) N(1) H(4) 108.68321483065 1_555 1_555 1_555 yes C(4) N(2) C(5) 105.67143765145 1_555 1_555 1_555 yes C(5) N(3) C(6) 107.47868499664 1_555 1_555 1_555 yes C(5) N(3) H(8) 126.49236090087 1_555 1_555 1_555 yes C(6) N(3) H(8) 126.01993199188 1_555 1_555 1_555 yes O(1) C(1) O(2) 125.57473281788 1_555 1_555 1_555 yes C(4) C(3) H(5) 110.53765355538 1_555 1_555 1_555 yes C(4) C(3) H(6) 109.14761575074 1_555 1_555 1_555 yes H(5) C(3) H(6) 105.87991987777 1_555 1_555 1_555 yes N(2) C(4) C(3) 120.89650635172 1_555 1_555 1_555 yes N(2) C(4) C(6) 109.33995348704 1_555 1_555 1_555 yes C(3) C(4) C(6) 129.71615992166 1_555 1_555 1_555 yes N(2) C(5) N(3) 111.4063063377 1_555 1_555 1_555 yes N(2) C(5) H(7) 126.67606174919 1_555 1_555 1_555 yes N(3) C(5) H(7) 121.89093402403 1_555 1_555 1_555 yes N(3) C(6) C(4) 106.102687648 1_555 1_555 1_555 yes N(3) C(6) H(9) 122.96926588383 1_555 1_555 1_555 yes C(4) C(6) H(9) 130.91358150511 1_555 1_555 1_555 yes 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) 6.314(9) 0 -0.076(2) 0.0005(15) 0 -0.0405(15) 0 0 -0.0754(17) -0.0005(14) 0 -0.0076(18) -0.0006(18) 0 0 0.0236(17) 0.0014(17) -0.001(2) 0 0 0.000(2) -0.001(2) 0 0 0.007(2) 0.001(2) 0.9794(5) 1.169(10) 1.169291 1.169291 1.169291 1.169291 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(2) 6.332(9) 0 -0.072(2) 0.0002(15) 0 -0.0217(15) 0 0 -0.0738(17) 0.0011(14) 0 -0.0074(18) -0.0003(18) 0 0 0.0273(17) 0.0010(17) -0.001(2) 0 0 -0.002(2) -0.001(2) 0 0 0.008(2) 0.002(2) 0.9794(5) 1.169(10) 1.169291 1.169291 1.169291 1.169291 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 N(1) 5.03(3) 0 0 0 -0.013(4) -0.041(3) 0 0 0 0 0.224(7) 0 0 0 0 -0.006(3) -0.171(6) 0.023(5) 0 0 0 0 0.001(4) 0.077(6) 0 0 0.9957(17) 0.846(9) 0.846344 0.846344 0.846344 0.846344 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(2) 5.187(15) 0 -0.062(3) -0.077(3) 0 -0.073(3) 0 0 -0.034(2) 0.069(3) 0 -0.019(3) -0.015(3) 0 0 0.083(3) -0.033(3) -0.000(4) 0 0 -0.006(4) 0.000(4) 0 0 0.020(4) 0.013(4) 0.9821(10) 1.017(11) 1.017084 1.017084 1.017084 1.017084 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(3) 5.16(3) 0 -0.014(6) 0.010(4) 0 -0.023(4) 0 0 0.035(4) -0.001(3) 0 -0.015(4) 0.007(4) 0 0 0.221(9) -0.000(4) 0.016(5) 0 0 -0.023(5) -0.001(5) 0 0 -0.008(6) 0.002(5) 0.9888(14) 0.844(12) 0.843541 0.843541 0.843541 0.843541 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 C(1) 3.973(18) 0 0.018(4) 0.003(4) 0 -0.273(6) 0 0 0.044(4) -0.046(4) 0 0.004(5) 0.008(5) 0 0 0.348(9) 0.046(5) 0.032(7) 0 0 0.002(6) -0.008(6) 0 0 -0.018(6) -0.026(6) 0.9959(18) 0.882(8) 0.881779 0.881779 0.881779 0.881779 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(2) 3.68(3) 0 -0.014(6) -0.068(5) 0 0.045(4) 0 0 0.068(4) 0.043(3) 0 -0.133(6) -0.188(7) 0 0 0.166(6) -0.057(4) 0.025(6) 0 0 -0.020(6) 0.062(6) 0 0 0.045(6) 0.027(5) 1.012(2) 0.938(11) 0.938371 0.938371 0.938371 0.938371 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(3) 3.49(4) 0 0 0 0.043(6) -0.012(3) 0 0 0.014(4) 0 -0.021(5) 0 0 -0.286(10) 0 0 0 -0.066(7) 0 0 0.006(6) 0 0 0 0.042(6) 0 1.022(2) 0.915(12) 0.91456 0.91456 0.91456 0.91456 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(4) 4.14(2) 0 -0.044(6) -0.047(6) 0 -0.133(6) 0 0 0.032(4) 0.039(5) 0 -0.023(5) -0.030(5) 0 0 0.313(11) -0.050(6) 0.019(7) 0 0 -0.022(7) 0.028(7) 0 0 -0.019(8) 0.029(7) 0.9965(17) 0.876(10) 0.87608 0.87608 0.87608 0.87608 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(5) 3.82(3) 0 -0.040(7) 0.046(5) 0 -0.131(5) 0 0 0.037(4) -0.050(4) 0 -0.009(5) 0.007(5) 0 0 0.274(11) 0.031(5) 0.034(6) 0 0 -0.032(6) -0.004(6) 0 0 -0.019(7) -0.004(7) 1.014(2) 0.923(12) 0.922912 0.922912 0.922912 0.922912 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(6) 3.72(3) 0 -0.025(6) 0.074(8) 0 -0.102(5) 0 0 -0.071(5) 0.003(5) 0 -0.013(5) 0.030(5) 0 0 0.232(11) -0.065(6) 0.029(7) 0 0 -0.004(6) -0.028(6) 0 0 0.014(7) -0.018(7) 1.014(2) 0.918(13) 0.918315 0.918315 0.918315 0.918315 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 H(2) 0.861(13) 0 0 0 0.135(6) 0.081(6) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.098(7) 1.30(2) 1.303269 1.303269 1.303269 1.303269 0 2 1 2 2 2 3 2 4 2 H(3) 0.856(12) 0 0 0 0.128(6) 0.088(6) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.098(7) 1.30(2) 1.303269 1.303269 1.303269 1.303269 0 2 1 2 2 2 3 2 4 2 H(4) 0.844(12) 0 0 0 0.122(6) 0.098(6) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.098(7) 1.30(2) 1.303269 1.303269 1.303269 1.303269 0 2 1 2 2 2 3 2 4 2 H(8) 0.81(2) 0 0 0 0.126(9) 0.095(9) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.118(12) 1.31(4) 1.310415 1.310415 1.310415 1.310415 0 2 1 2 2 2 3 2 4 2 H(1) 1.16(2) 0 0 0 0.241(14) 0.142(12) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.050(9) 1.05(2) 1.045247 1.045247 1.045247 1.045247 0 2 1 2 2 2 3 2 4 2 H(5) 1.198(16) 0 0 0 0.233(9) 0.122(9) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.043(6) 1.088(15) 1.087506 1.087506 1.087506 1.087506 0 2 1 2 2 2 3 2 4 2 H(6) 1.192(16) 0 0 0 0.229(9) 0.126(8) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.043(6) 1.088(15) 1.087506 1.087506 1.087506 1.087506 0 2 1 2 2 2 3 2 4 2 H(7) 1.09(2) 0 0 0 0.217(13) 0.105(11) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.064(10) 1.12(3) 1.12039 1.12039 1.12039 1.12039 0 2 1 2 2 2 3 2 4 2 H(9) 1.14(2) 0 0 0 0.253(14) 0.119(12) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.049(10) 1.06(2) 1.056179 1.056179 1.056179 1.056179 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(1) X O(1) O(2) Y O(2) C(1) X O(2) O(1) Y N(1) C(2) Z N(1) H(2) Y N(2) C(4) X N(2) C(5) Y N(3) H(8) X N(3) C(5) Y C(1) O(1) X C(1) O(2) Y C(2) H(1) X C(2) N(1) Y C(3) DUM1 Z C(3) C(2) Y C(4) C(3) X C(4) N(2) Y C(5) H(7) X C(5) N(2) Y C(6) N(3) X C(6) C(4) Y H(2) N(1) Z H(2) C(2) Y H(3) N(1) Z H(3) C(2) Y H(4) N(1) Z H(4) C(2) Y H(8) N(3) Z H(8) C(5) Y H(1) C(2) Z H(1) N(1) Y H(5) C(3) Z H(5) C(2) Y H(6) C(3) Z H(6) C(2) Y H(7) C(5) Z H(7) N(2) Y H(9) C(6) Z H(9) N(3) Y