# 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_murea _database_code_depnum_ccdc_archive 'CCDC 910360' #TrackingRef '15454_web_deposit_cif_file_0_LiliannaChecinska_1353002603.murea_ChemPhysChem.cif' _audit_creation_method XD2006 _chemical_name_systematic ; N-methylurea ; _chemical_name_common N-methylurea _chemical_melting_point ? _chemical_formula_moiety 'C2 H6 N2 O' _chemical_formula_sum 'C2 H6 N2 O' _chemical_formula_weight 74.09 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_Int_Tables_number 19 _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 +X,+Y,+Z 2 1/2-X,-Y,1/2+Z 3 -X,1/2+Y,1/2-Z 4 1/2+X,1/2-Y,-Z _cell_length_a 6.741(1) _cell_length_b 6.743(1) _cell_length_c 8.580(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 390.00(12) _cell_formula_units_Z 4 _cell_measurement_temperature 8(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 160 _exptl_absorpt_coefficient_mu 0.062 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ? _diffrn_ambient_temperature 8(2) _diffrn_radiation_wavelength 0.5166 _diffrn_radiation_type synchrotron _diffrn_radiation_source synchrotron _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Huber diffractometer' _diffrn_detector_type 'MarCCD detector' _diffrn_measurement_method '\f scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18822 _diffrn_reflns_av_R_equivalents 0.0829 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 31.94 _reflns_number_total 1985 _reflns_number_gt 1920 _reflns_threshold_expression >2\s(I) _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 31.94 _diffrn_measured_fraction_theta_full 0.989 _computing_data_collection 'MarCCD (Paulmann & Morgenroth, 2006)' _computing_cell_refinement 'XDS (Kabsch, 1993; 2010)' _computing_data_reduction 'XDS (Kabsch, 1993; 2010)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'Volkov et al, (2006)' # Multipole refinement details _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.027 _refine_ls_R_factor_all 0.027 _refine_ls_R_Fsqd_factor 0.051 _refine_ls_wR_factor_ref 0.058 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 1971 _refine_ls_number_parameters 130 _refine_ls_goodness_of_fit_ref 1.485 _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc w2 = 1/[s^2^(Fo^2^)] ; _refine_ls_shift/su_max 0 _refine_ls_extinction_method none _refine_special_details ? _refine_diff_density_max 0.202 _refine_diff_density_min -0.373 _refine_diff_density_rms 0.054 # Atomic coordinates 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) 0.37477(6) 0.45323(6) 0.19580(5) 1 4 0.006 N(1) 0.20093(5) 0.34040(6) 0.40523(5) 1 4 0.007 N(2) 0.33986(5) 0.65183(6) 0.40862(5) 1 4 0.008 C(1) 0.30810(5) 0.48052(5) 0.33079(4) 1 4 0.005 C(11) 0.14256(6) 0.15878(6) 0.32753(5) 1 4 0.009 H(1) 0.145272 0.378126 0.510382 1 4 0.026 H(2A) 0.282358 0.663272 0.51693 1 4 0.027 H(2B) 0.431948 0.752446 0.360145 1 4 0.020 H(11A) 0.084332 0.06202 0.414586 1 4 0.032 H(11B) 0.036694 0.183991 0.237348 1 4 0.032 H(11C) 0.27057 0.087462 0.280738 1 4 0.031 # Anisotropic displacement parameters loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.00715(14) 0.00728(14) 0.00434(13) -0.00006(11) 0.00115(10) -0.00033(10) N(1) 0.00914(13) 0.00680(13) 0.00628(13) -0.00274(10) 0.00234(10) -0.00049(10) N(2) 0.00956(13) 0.00633(13) 0.00688(14) -0.00219(10) 0.00179(10) -0.00148(11) C(1) 0.00538(13) 0.00521(13) 0.00436(13) -0.00043(8) 0.00036(9) -0.00018(8) C(11) 0.00929(14) 0.00719(13) 0.01078(15) -0.00261(10) 0.00109(10) -0.00139(11) H(1) 0.035901 0.025319 0.017289 -0.01012 0.013461 -0.006208 H(2A) 0.03797 0.025952 0.016328 -0.009186 0.011855 -0.007061 H(2B) 0.02122 0.016641 0.021698 -0.006858 0.003867 0.001489 H(11A) 0.044942 0.024305 0.027873 -0.014207 0.008366 0.004699 H(11B) 0.033305 0.028247 0.034088 -0.001479 -0.017293 -0.002042 H(11C) 0.021598 0.0262 0.044802 0.001766 0.007929 -0.012386 # 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(1) 1.2559(5) 1_555 1_555 yes N(1) C(1) 1.3500(5) 1_555 1_555 yes N(1) C(11) 1.4488(6) 1_555 1_555 yes N(1) H(1) 1.0097 1_555 1_555 yes N(2) C(1) 1.3513(5) 1_555 1_555 yes N(2) H(2A) 1.0098 1_555 1_555 yes N(2) H(2B) 1.009 1_555 1_555 yes C(11) H(11A) 1.0666 1_555 1_555 yes C(11) H(11B) 1.0663 1_555 1_555 yes C(11) H(11C) 1.0663 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(1) N(1) C(11) 121.28(4) 1_555 1_555 1_555 yes C(1) N(1) H(1) 116.44 1_555 1_555 1_555 yes C(11) N(1) H(1) 121.55 1_555 1_555 1_555 yes C(1) N(2) H(2A) 117.34 1_555 1_555 1_555 yes C(1) N(2) H(2B) 117.93 1_555 1_555 1_555 yes H(2A) N(2) H(2B) 124.33 1_555 1_555 1_555 yes O(1) C(1) N(1) 121.68(4) 1_555 1_555 1_555 yes O(1) C(1) N(2) 121.62(4) 1_555 1_555 1_555 yes N(1) C(1) N(2) 116.70(4) 1_555 1_555 1_555 yes N(1) C(11) H(11A) 107.14 1_555 1_555 1_555 yes N(1) C(11) H(11B) 112.39 1_555 1_555 1_555 yes N(1) C(11) H(11C) 109.55 1_555 1_555 1_555 yes H(11A) C(11) H(11B) 111.06 1_555 1_555 1_555 yes H(11A) C(11) H(11C) 106.59 1_555 1_555 1_555 yes H(11B) C(11) H(11C) 109.89 1_555 1_555 1_555 yes # 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) 6.29(5) 0 0.002(11) 0.014(11) -0.035(14) 0.014(14) -0.025(11) 0.003(12) -0.057(13) 0.002(12) 0.061(11) -0.009(10) 0.020(10) 0.011(12) -0.013(11) -0.002(10) -0.008(10) 0.059(14) -0.013(12) -0.007(12) -0.011(13) -0.014(12) -0.003(12) -0.001(12) -0.000(12) -0.008(11) 0.983(4) 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 N(1) 5.07(7) 0 0.038(15) -0.010(16) 0 0.006(15) 0 0 -0.008(14) 0.033(14) 0 0.010(14) -0.003(13) 0 0 0.157(14) 0.023(12) 0.026(18) 0 0 0.012(16) 0.010(17) 0 0 0.010(15) -0.036(15) 0.994(5) 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(2) 5.22(5) 0 -0.030(15) 0.006(15) 0 -0.008(15) 0 0 -0.021(14) -0.006(14) 0 0.016(13) -0.011(13) 0 0 0.168(14) -0.012(12) 0.003(18) 0 0 -0.020(18) 0.026(17) 0 0 -0.027(15) 0.011(15) 0.981326 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 C(1) 3.75(9) 0 0 0 0.02(2) 0.168(19) 0 0 -0.204(17) 0 0.22(2) 0 0 0.22(2) 0 0 0 -0.05(3) 0 0 -0.03(2) 0 0 0 -0.06(2) 0 1.001(11) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(11) 3.88(12) 0 0 0 -0.068(19) -0.041(19) 0 0 0 0 0.27(2) 0 0 0 0 0.035(16) -0.15(2) 0.04(2) 0 0 0 0 0.02(2) 0.09(2) 0 0 1.003(12) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 H(1) 0.97(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 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(2A) 0.90(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 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(2B) 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 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(11A) 1.03(3) 0 0 0 0.118(16) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(11B) 1.027 0 0 0 0.1184 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(11C) 1.027 0 0 0 0.1184 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 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) Z O(1) N(1) Y N(1) C(1) X N(1) C(11) Y N(2) C(1) X N(2) H(2A) Y C(1) O(1) Z C(1) N(2) Y C(11) N(1) Z C(11) H(11A) Y H(1) N(1) Z H(1) C(1) Y H(2A) N(2) Z H(2A) C(1) Y H(2B) N(2) Z H(2B) C(1) Y H(11A) C(11) Z H(11A) H(11C) Y H(11B) C(11) Z H(11B) H(11A) Y H(11C) C(11) Z H(11C) H(11B) Y data_phurea _database_code_depnum_ccdc_archive 'CCDC 910361' #TrackingRef '15455_web_deposit_cif_file_1_LiliannaChecinska_1353002603.phurea_ChemPhysChem.cif' _audit_creation_method XD2006 _chemical_name_systematic ; N-phenylurea ; _chemical_name_common N-phenylurea _chemical_melting_point ? _chemical_formula_moiety 'C7 H8 N2 O' _chemical_formula_sum 'C7 H8 N2 O' _chemical_formula_weight 136.15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2(1)' _symmetry_Int_Tables_number 4 _symmetry_space_group_name_Hall 'P 2yb' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,-Z _cell_length_a 4.634(1) _cell_length_b 5.292(1) _cell_length_c 13.943(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.57(3) _cell_angle_gamma 90.00 _cell_volume 340.31(12) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 144 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ? _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.60000 _diffrn_radiation_type synchrotron _diffrn_radiation_source synchrotron _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Huber diffractometer' _diffrn_detector_type 'MarCCD detector' _diffrn_measurement_method '\f scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 38147 _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_av_sigmaI/netI 0.0152 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 47.03 _reflns_number_total 5336 _reflns_number_gt 5095 _reflns_threshold_expression >2\s(I) _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 47.03 _diffrn_measured_fraction_theta_full 0.977 _computing_data_collection 'MarCCD (Paulmann & Morgenroth, 2006)' _computing_cell_refinement 'XDS (Kabsch, 1993; 2010)' _computing_data_reduction 'XDS (Kabsch, 1993; 2010)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'Volkov et al, (2006)' # Multipole refinement details _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.02 _refine_ls_R_factor_all 0.021 _refine_ls_R_Fsqd_factor 0.028 _refine_ls_wR_factor_ref 0.04 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 5294 _refine_ls_number_parameters 229 _refine_ls_goodness_of_fit_ref 2.072 _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc w2 = 1/[s^2^(Fo^2^)] ; _refine_ls_shift/su_max 0 _refine_ls_extinction_method none _refine_special_details ? _refine_diff_density_max 0.131 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.031 # Atomic coordinates 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) -0.06246(4) 0.011193 0.102448(15) 1 2 0.013 N(1) 0.38385(4) 0.12734(7) 0.175346(14) 1 2 0.013 N(2) 0.34648(4) -0.14327(7) 0.045857(16) 1 2 0.016 C(1) 0.20829(4) -0.00186(6) 0.107787(12) 1 2 0.010 C(11) 0.28349(4) 0.28253(7) 0.248083(15) 1 2 0.012 C(12) 0.06737(5) 0.46492(7) 0.227086(18) 1 2 0.016 C(13) -0.01542(6) 0.62063(8) 0.30047(2) 1 2 0.021 C(14) 0.11824(7) 0.59857(8) 0.39463(2) 1 2 0.021 C(15) 0.33441(7) 0.41758(8) 0.415017(19) 1 2 0.020 C(16) 0.41594(5) 0.25922(8) 0.342222(17) 1 2 0.017 H(1) 0.596964 0.102406 0.168848 1 2 0.034 H(2A) 0.564734 -0.155156 0.051348 1 2 0.036 H(2B) 0.224673 -0.258677 0.000817 1 2 0.029 H(12) -0.026616 0.49115 0.153718 1 2 0.034 H(13) -0.176808 0.765645 0.282853 1 2 0.047 H(14) 0.056443 0.71016 0.454377 1 2 0.042 H(15) 0.438473 0.410615 0.48771 1 2 0.043 H(16) 0.573727 0.111549 0.359713 1 2 0.040 # Anisotropic displacement parameters loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.00598(4) 0.01662(8) 0.01520(6) 0.00055(5) 0.00060(4) -0.00035(6) N(1) 0.00706(5) 0.01794(8) 0.01362(5) 0.00020(4) 0.00071(4) -0.00468(6) N(2) 0.00819(5) 0.02133(9) 0.01715(6) -0.00097(5) 0.00201(4) -0.00795(7) C(1) 0.00609(4) 0.01296(6) 0.01119(5) 0.00007(4) 0.00068(3) -0.00048(5) C(11) 0.00996(5) 0.01303(7) 0.01203(6) 0.00020(5) 0.00179(4) -0.00104(5) C(12) 0.01743(7) 0.01407(8) 0.01624(7) 0.00428(6) 0.00166(6) -0.00020(6) C(13) 0.02403(10) 0.01669(9) 0.02258(10) 0.00696(8) 0.00393(8) -0.00329(8) C(14) 0.02391(10) 0.01959(11) 0.01928(9) 0.00147(9) 0.00665(8) -0.00597(8) C(15) 0.02393(10) 0.02375(11) 0.01341(7) 0.00243(9) 0.00201(7) -0.00447(7) C(16) 0.01785(8) 0.02084(10) 0.01292(7) 0.00450(7) -0.00070(5) -0.00291(6) H(1) 0.01217 0.051085 0.037603 0.000322 0.002741 -0.019337 H(2A) 0.013022 0.0523 0.042437 0.00071 0.002835 -0.020847 H(2B) 0.021214 0.033853 0.030836 -0.004976 -0.000133 -0.013093 H(12) 0.044643 0.032115 0.024354 0.012479 -0.005616 0.001721 H(13) 0.053172 0.037437 0.049236 0.027344 -0.002102 -0.008457 H(14) 0.050309 0.042761 0.033577 0.007015 0.01361 -0.01652 H(15) 0.054138 0.051518 0.020382 0.008 -0.005419 -0.008282 H(16) 0.041151 0.044104 0.032035 0.022206 -0.011142 -0.00704 # 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(1) 1.2515(2) 1_555 1_555 yes N(1) C(1) 1.3667(3) 1_555 1_555 yes N(1) C(11) 1.4180(3) 1_555 1_555 yes N(1) H(1) 1.00912 1_555 1_555 yes N(2) C(1) 1.3502(3) 1_555 1_555 yes N(2) H(2A) 1.0088 1_555 1_555 yes N(2) H(2B) 1.0085 1_555 1_555 yes C(11) C(12) 1.4012(3) 1_555 1_555 yes C(11) C(16) 1.3994(3) 1_555 1_555 yes C(12) C(13) 1.3962(4) 1_555 1_555 yes C(12) H(12) 1.0812 1_555 1_555 yes C(13) C(14) 1.4012(5) 1_555 1_555 yes C(13) H(13) 1.0830 1_555 1_555 yes C(14) C(15) 1.3951(5) 1_555 1_555 yes C(14) H(14) 1.0821 1_555 1_555 yes C(15) C(16) 1.3963(4) 1_555 1_555 yes C(15) H(15) 1.0800 1_555 1_555 yes C(16) H(16) 1.0817 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(1) N(1) C(11) 124.62(4) 1_555 1_555 1_555 yes C(1) N(1) H(1) 113.26 1_555 1_555 1_555 yes C(11) N(1) H(1) 122.12 1_555 1_555 1_555 yes C(1) N(2) H(2A) 121.35 1_555 1_555 1_555 yes C(1) N(2) H(2B) 117.539 1_555 1_555 1_555 yes H(2A) N(2) H(2B) 120.39 1_555 1_555 1_555 yes O(1) C(1) N(1) 122.66(4) 1_555 1_555 1_555 yes O(1) C(1) N(2) 121.84(4) 1_555 1_555 1_555 yes N(1) C(1) N(2) 115.50(4) 1_555 1_555 1_555 yes N(1) C(11) C(12) 121.80(4) 1_555 1_555 1_555 yes N(1) C(11) C(16) 118.38(4) 1_555 1_555 1_555 yes C(12) C(11) C(16) 119.75(2) 1_555 1_555 1_555 yes C(11) C(12) C(13) 119.68(2) 1_555 1_555 1_555 yes C(11) C(12) H(12) 120.02 1_555 1_555 1_555 yes C(13) C(12) H(12) 120.23 1_555 1_555 1_555 yes C(12) C(13) C(14) 120.64(3) 1_555 1_555 1_555 yes C(12) C(13) H(13) 119.00 1_555 1_555 1_555 yes C(14) C(13) H(13) 120.28 1_555 1_555 1_555 yes C(13) C(14) C(15) 119.44(3) 1_555 1_555 1_555 yes C(13) C(14) H(14) 123.36 1_555 1_555 1_555 yes C(15) C(14) H(14) 117.15 1_555 1_555 1_555 yes C(14) C(15) C(16) 120.24(3) 1_555 1_555 1_555 yes C(14) C(15) H(15) 117.45 1_555 1_555 1_555 yes C(16) C(15) H(15) 122.28 1_555 1_555 1_555 yes C(11) C(16) C(15) 120.26(2) 1_555 1_555 1_555 yes C(11) C(16) H(16) 120.03 1_555 1_555 1_555 yes C(15) C(16) H(16) 119.63 1_555 1_555 1_555 yes # 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) 6.31(3) 0 -0.005(7) 0.001(7) -0.077(6) -0.100(6) -0.014(6) -0.008(5) -0.030(8) 0.008(6) 0.038(6) -0.001(6) -0.014(6) 0.019(8) 0.008(5) -0.012(6) -0.008(7) 0.041(7) 0.015(7) -0.034(6) 0.016(8) 0.033(7) -0.002(7) 0.024(8) 0.007(7) -0.007(8) 0.991(2) 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 N(1) 5.31(4) 0 -0.036(8) -0.011(8) 0 0.044(8) 0 0 0.015(7) -0.040(7) 0 0.043(8) -0.007(8) 0 0 0.175(8) -0.002(7) 0.040(11) 0 0 -0.003(9) -0.030(10) 0 0 -0.024(9) -0.019(9) 0.996(3) 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(2) 5.27(4) 0 0.007(8) 0.018(8) 0 0.030(9) 0 0 -0.017(7) 0.065(7) 0 0.028(9) 0.003(9) 0 0 0.187(8) 0.008(7) 0.031(11) 0 0 -0.034(9) 0.028(10) 0 0 -0.032(8) 0.006(8) 0.997(3) 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 C(1) 3.67(4) 0 0 0 0.038(10) 0.102(9) 0 0 -0.155(10) 0 0.270(11) 0 0 0.190(13) 0 0 0 0.038(14) 0 0 -0.060(15) 0 0 0 -0.005(11) 0 1.031(5) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(11) 3.90(6) 0 0.086(10) 0.149(10) 0 -0.186(10) 0 0 0.014(9) -0.063(9) 0 0.029(9) -0.003(10) 0 0 0.189(13) -0.019(10) 0.039(14) 0 0 0.008(11) 0.032(13) 0 0 -0.008(11) 0.021(14) 1.029(5) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(12) 3.95(4) 0 0.039(10) 0.083(9) 0 -0.149(8) 0 0 0.030(8) -0.010(8) 0 -0.014(9) 0.043(8) 0 0 0.215(10) 0.020(8) 0.025(11) 0 0 -0.029(10) -0.002(10) 0 0 -0.034(10) -0.008(10) 1.029(4) 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 0.103(11) 0.051(10) 0 -0.165(10) 0 0 0.011(9) -0.016(9) 0 0.022(9) 0.051(9) 0 0 0.238(10) 0.022(9) 0.031(13) 0 0 -0.017(11) 0.021(11) 0 0 -0.030(11) 0.000(11) 1.019(4) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(14) 3.91(6) 0 0.012(12) 0.049(13) 0 -0.150(13) 0 0 -0.004(10) -0.017(12) 0 0.012(11) 0.041(11) 0 0 0.192(15) -0.015(11) 0.025(17) 0 0 -0.039(14) -0.024(16) 0 0 -0.044(12) -0.014(15) 1.035(6) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(15) 3.9784 0 0.1028 0.0505 0 -0.1646 0 0 0.0107 -0.0164 0 0.0224 0.0507 0 0 0.238 0.0218 0.0311 0 0 -0.0166 0.0213 0 0 -0.0297 0.0003 1.019(4) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(16) 3.9547 0 0.0385 0.0828 0 -0.1494 0 0 0.0298 -0.01 0 -0.0139 0.0433 0 0 0.2146 0.0202 0.0246 0 0 -0.0285 -0.0019 0 0 -0.034 -0.0076 1.029(4) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 H(1) 0.714(15) 0 0 0 0.128(9) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(2A) 0.721(16) 0 0 0 0.124(9) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(2B) 0.771(17) 0 0 0 0.119(10) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(12) 1.111(11) 0 0 0 0.174(6) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(13) 1.1109 0 0 0 0.1736 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(14) 1.1109 0 0 0 0.1736 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(15) 1.1109 0 0 0 0.1736 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(16) 1.1109 0 0 0 0.1736 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 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) Z O(1) N(1) Y N(1) C(1) X N(1) C(11) Y N(2) C(1) X N(2) H(2A) Y C(1) O(1) Z C(1) N(2) Y C(11) C(12) X C(11) C(16) Y C(12) C(13) X C(12) C(11) Y C(13) C(14) X C(13) C(12) Y C(14) C(15) X C(14) C(13) Y C(15) C(14) -X C(15) C(16) Y C(16) C(15) -X C(16) C(11) Y H(1) N(1) Z H(1) C(1) Y H(2A) N(2) Z H(2A) C(1) Y H(2B) N(2) Z H(2B) C(1) Y H(12) C(12) Z H(12) C(13) Y H(13) C(13) Z H(13) C(14) Y H(14) C(14) Z H(14) C(15) Y H(15) C(15) -Z H(15) C(14) Y H(16) C(16) -Z H(16) C(15) Y data_dphurea _database_code_depnum_ccdc_archive 'CCDC 910362' #TrackingRef '15456_web_deposit_cif_file_2_LiliannaChecinska_1353002603.dphurea_ChemPhysChem.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-diphenylurea ; _chemical_name_common N,N'-diphenylurea _chemical_melting_point ? _chemical_formula_moiety 'C13 H12 N2 O' _chemical_formula_sum 'C13 H12 N2 O' _chemical_formula_weight 212.25 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pna21 _symmetry_Int_Tables_number 33 _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 +X,+Y,+Z 2 -X,-Y,1/2+Z 3 1/2+X,1/2-Y,+Z 4 1/2-X,1/2+Y,1/2+Z _cell_length_a 9.090(2) _cell_length_b 10.372(2) _cell_length_c 11.770(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1109.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.270 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ? _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.60000 _diffrn_radiation_type synchrotron _diffrn_radiation_source synchrotron _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Huber diffractometer' _diffrn_detector_type 'MarCCD detector' _diffrn_measurement_method '\f scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 96205 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_sigmaI/netI 0.0142 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 48.60 _reflns_number_total 9267 _reflns_number_gt 8892 _reflns_threshold_expression >2\s(I) _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 48.60 _diffrn_measured_fraction_theta_full 0.995 _computing_data_collection 'MarCCD (Paulmann & Morgenroth, 2006)' _computing_cell_refinement 'XDS (Kabsch, 1993; 2010)' _computing_data_reduction 'XDS (Kabsch, 1993; 2010)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'Volkov et al, (2006)' # Multipole refinement details _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.02 _refine_ls_R_factor_all 0.021 _refine_ls_R_Fsqd_factor 0.054 _refine_ls_wR_factor_ref 0.044 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 9205 _refine_ls_number_parameters 343 _refine_ls_goodness_of_fit_ref 2.348 _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc w2 = 1/[s^2^(Fo^2^)] ; _refine_ls_shift/su_max 0 _refine_ls_extinction_method none _refine_special_details ? _refine_diff_density_max 0.210 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.063 # Atomic coordinates 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) 0.376211(19) 0.27769(3) 0.404488 1 4 0.017 N(1) 0.59175(2) 0.216972(19) 0.49097(3) 1 4 0.014 N(2) 0.595365(19) 0.299545(18) 0.31010(3) 1 4 0.014 C(1) 0.512074(18) 0.266165(17) 0.40284(3) 1 4 0.012 C(11) 0.53217(2) 0.175888(19) 0.59602(3) 1 4 0.013 C(12) 0.42408(2) 0.24711(2) 0.65334(3) 1 4 0.016 C(13) 0.37241(3) 0.20473(3) 0.75870(3) 1 4 0.021 C(14) 0.43015(4) 0.09371(4) 0.80910(4) 1 4 0.026 C(15) 0.54009(4) 0.02392(3) 0.75247(4) 1 4 0.026 C(16) 0.58956(3) 0.06392(2) 0.64565(3) 1 4 0.020 C(21) 0.53692(2) 0.345423(18) 0.20613(3) 1 4 0.013 C(22) 0.41586(2) 0.42925(2) 0.20152(3) 1 4 0.016 C(23) 0.36300(3) 0.47128(2) 0.09608(3) 1 4 0.019 C(24) 0.43090(3) 0.43243(3) -0.00467(3) 1 4 0.021 C(25) 0.55399(4) 0.35192(3) 0.00052(3) 1 4 0.023 C(26) 0.60698(3) 0.30807(2) 0.10516(3) 1 4 0.019 H(1) 0.69931 0.201264 0.475345 1 4 0.032 H(2) 0.699831 0.267222 0.309597 1 4 0.032 H(12) 0.386003 0.338322 0.619759 1 4 0.033 H(13) 0.289269 0.257814 0.804991 1 4 0.044 H(14) 0.399247 0.064626 0.893986 1 4 0.044 H(15) 0.585175 -0.062279 0.790832 1 4 0.044 H(16) 0.674577 0.011134 0.601643 1 4 0.039 H(22) 0.363532 0.46393 0.278282 1 4 0.031 H(23) 0.271263 0.537872 0.09211 1 4 0.040 H(24) 0.392899 0.458339 -0.088597 1 4 0.039 H(25) 0.609183 0.328687 -0.078314 1 4 0.043 H(26) 0.70047 0.244644 0.114692 1 4 0.039 # Anisotropic displacement parameters loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.00648(5) 0.03077(10) 0.01514(7) -0.00050(5) 0.00136(4) 0.00076(7) N(1) 0.00799(5) 0.02079(7) 0.01411(6) 0.00028(4) 0.00168(4) 0.00212(5) N(2) 0.00768(5) 0.02028(7) 0.01314(6) 0.00068(3) 0.00200(4) 0.00074(4) C(1) 0.00663(4) 0.01701(6) 0.01260(5) -0.00085(3) 0.00136(4) -0.00075(4) C(11) 0.01058(5) 0.01566(6) 0.01422(6) -0.00188(4) 0.00131(4) 0.00101(5) C(12) 0.01317(6) 0.01972(7) 0.01387(6) -0.00143(5) 0.00291(5) -0.00045(5) C(13) 0.02070(9) 0.02890(10) 0.01484(8) -0.00416(8) 0.00556(6) 0.00017(7) C(14) 0.02830(12) 0.03226(13) 0.01892(10) -0.00699(11) 0.00415(9) 0.00806(9) C(15) 0.02810(12) 0.02432(10) 0.02628(12) -0.00329(9) 0.00155(9) 0.01172(9) C(16) 0.01909(8) 0.01740(7) 0.02322(9) -0.00000(6) 0.00191(7) 0.00513(6) C(21) 0.01020(5) 0.01479(5) 0.01324(6) 0.00007(4) 0.00150(4) -0.00058(4) C(22) 0.01389(6) 0.01667(6) 0.01703(7) 0.00291(4) 0.00061(5) -0.00029(5) C(23) 0.01877(8) 0.01665(6) 0.02081(9) 0.00188(5) -0.00219(6) 0.00294(6) C(24) 0.02571(10) 0.02001(8) 0.01707(9) -0.00050(7) -0.00246(7) 0.00367(6) C(25) 0.02744(11) 0.02692(10) 0.01372(8) 0.00389(8) 0.00298(7) 0.00098(7) C(26) 0.01859(8) 0.02302(8) 0.01421(7) 0.00495(6) 0.00396(6) -0.00003(6) H(1) 0.014483 0.048767 0.03163 0.006603 0.004061 0.009061 H(2) 0.015419 0.048281 0.03181 0.009024 0.005791 0.008808 H(12) 0.036373 0.031811 0.030555 0.008459 0.007422 0.004292 H(13) 0.042507 0.058188 0.032745 0.009675 0.018217 0.002925 H(14) 0.051813 0.053782 0.025635 -0.008136 0.009182 0.012044 H(15) 0.058336 0.037291 0.036413 0.005091 -0.001176 0.015075 H(16) 0.041262 0.041171 0.035576 0.016574 0.00703 0.006718 H(22) 0.031856 0.036484 0.02488 0.011289 0.004413 -0.002462 H(23) 0.038026 0.043908 0.036737 0.018845 -0.004267 0.004843 H(24) 0.049391 0.04526 0.022619 0.003722 -0.008119 0.005031 H(25) 0.052932 0.053034 0.021954 0.011089 0.010593 0.000017 H(26) 0.0351 0.051159 0.031871 0.020931 0.008516 0.004256 # 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(1) 1.2409(2) 1_555 1_555 yes N(1) C(1) 1.3641(3) 1_555 1_555 yes N(1) C(11) 1.4155(3) 1_555 1_555 yes N(1) H(1) 1.00816 1_555 1_555 yes N(2) C(1) 1.3728(3) 1_555 1_555 yes N(2) C(21) 1.4164(3) 1_555 1_555 yes N(2) H(2) 1.00706 1_555 1_555 yes C(11) C(12) 1.4022(3) 1_555 1_555 yes C(11) C(16) 1.4007(3) 1_555 1_555 yes C(12) C(13) 1.3970(3) 1_555 1_555 yes C(12) H(12) 1.0822 1_555 1_555 yes C(13) C(14) 1.3976(5) 1_555 1_555 yes C(13) H(13) 1.0822 1_555 1_555 yes C(14) C(15) 1.4025(6) 1_555 1_555 yes C(14) H(14) 1.0808 1_555 1_555 yes C(15) C(16) 1.3983(4) 1_555 1_555 yes C(15) H(15) 1.0822 1_555 1_555 yes C(16) H(16) 1.0795 1_555 1_555 yes C(21) C(22) 1.4035(3) 1_555 1_555 yes C(21) C(26) 1.4029(3) 1_555 1_555 yes C(22) C(23) 1.4004(4) 1_555 1_555 yes C(22) H(22) 1.0826 1_555 1_555 yes C(23) C(24) 1.3962(4) 1_555 1_555 yes C(23) H(23) 1.0838 1_555 1_555 yes C(24) C(25) 1.3975(4) 1_555 1_555 yes C(24) H(24) 1.0805 1_555 1_555 yes C(25) C(26) 1.3985(4) 1_555 1_555 yes C(25) H(25) 1.0820 1_555 1_555 yes C(26) H(26) 1.0805 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(1) N(1) C(11) 125.008(17) 1_555 1_555 1_555 yes C(1) N(1) H(1) 115.89 1_555 1_555 1_555 yes C(11) N(1) H(1) 118.80 1_555 1_555 1_555 yes C(1) N(2) C(21) 124.391(16) 1_555 1_555 1_555 yes C(1) N(2) H(2) 116.15 1_555 1_555 1_555 yes C(21) N(2) H(2) 117.42 1_555 1_555 1_555 yes O(1) C(1) N(1) 123.54(2) 1_555 1_555 1_555 yes O(1) C(1) N(2) 122.48(2) 1_555 1_555 1_555 yes N(1) C(1) N(2) 113.964(16) 1_555 1_555 1_555 yes N(1) C(11) C(12) 121.990(19) 1_555 1_555 1_555 yes N(1) C(11) C(16) 118.12(2) 1_555 1_555 1_555 yes C(12) C(11) C(16) 119.81(2) 1_555 1_555 1_555 yes C(11) C(12) C(13) 119.80(2) 1_555 1_555 1_555 yes C(11) C(12) H(12) 120.59 1_555 1_555 1_555 yes C(13) C(12) H(12) 119.45 1_555 1_555 1_555 yes C(12) C(13) C(14) 120.64(3) 1_555 1_555 1_555 yes C(12) C(13) H(13) 121.44 1_555 1_555 1_555 yes C(14) C(13) H(13) 117.89 1_555 1_555 1_555 yes C(13) C(14) C(15) 119.42(3) 1_555 1_555 1_555 yes C(13) C(14) H(14) 121.65 1_555 1_555 1_555 yes C(15) C(14) H(14) 118.72 1_555 1_555 1_555 yes C(14) C(15) C(16) 120.22(3) 1_555 1_555 1_555 yes C(14) C(15) H(15) 119.87 1_555 1_555 1_555 yes C(16) C(15) H(15) 119.90 1_555 1_555 1_555 yes C(11) C(16) C(15) 120.08(3) 1_555 1_555 1_555 yes C(11) C(16) H(16) 119.15 1_555 1_555 1_555 yes C(15) C(16) H(16) 120.74 1_555 1_555 1_555 yes N(2) C(21) C(22) 122.385(19) 1_555 1_555 1_555 yes N(2) C(21) C(26) 117.956(18) 1_555 1_555 1_555 yes C(22) C(21) C(26) 119.63(2) 1_555 1_555 1_555 yes C(21) C(22) C(23) 119.74(2) 1_555 1_555 1_555 yes C(21) C(22) H(22) 121.20 1_555 1_555 1_555 yes C(23) C(22) H(22) 119.04 1_555 1_555 1_555 yes C(22) C(23) C(24) 120.74(2) 1_555 1_555 1_555 yes C(22) C(23) H(23) 120.04 1_555 1_555 1_555 yes C(24) C(23) H(23) 119.18 1_555 1_555 1_555 yes C(23) C(24) C(25) 119.30(3) 1_555 1_555 1_555 yes C(23) C(24) H(24) 124.29 1_555 1_555 1_555 yes C(25) C(24) H(24) 116.39 1_555 1_555 1_555 yes C(24) C(25) C(26) 120.57(2) 1_555 1_555 1_555 yes C(24) C(25) H(25) 117.83 1_555 1_555 1_555 yes C(26) C(25) H(25) 121.54 1_555 1_555 1_555 yes C(21) C(26) C(25) 119.99(2) 1_555 1_555 1_555 yes C(21) C(26) H(26) 115.93 1_555 1_555 1_555 yes C(25) C(26) H(26) 124.08 1_555 1_555 1_555 yes # 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) 6.30(3) 0 0.028(8) -0.001(9) -0.052(7) -0.039(7) 0.003(6) 0.018(6) -0.083(7) 0.023(7) 0.035(7) -0.008(6) -0.009(7) -0.001(7) 0.006(6) 0.033(8) 0.035(7) 0.014(8) 0.001(7) -0.019(8) -0.030(8) -0.006(8) -0.009(8) 0.009(7) 0.001(8) 0.017(7) 0.998(2) 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 N(1) 5.23(4) 0 0.017(9) -0.019(8) 0 0.010(8) 0 0 0.007(7) 0.016(7) 0 0.041(8) 0.003(8) 0 0 0.166(8) 0.021(8) 0.008(10) 0 0 -0.012(9) 0.010(9) 0 0 0.015(9) 0.009(9) 1.002(3) 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(2) 5.17(4) 0 -0.020(9) 0.018(9) 0 0.008(7) 0 0 -0.031(7) -0.016(7) 0 0.006(7) 0.002(7) 0 0 0.144(8) 0.001(8) 0.058(10) 0 0 -0.024(9) -0.006(9) 0 0 0.007(9) -0.008(9) 1.008(3) 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 C(1) 3.72(4) 0 0 0 0.040(11) 0.137(9) 0 0 -0.145(9) 0 0.257(12) 0 0 0.140(11) 0 0 0 -0.072(15) 0 0 -0.070(14) 0 0 0 -0.043(12) 0 1.040(5) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(11) 3.91(4) 0 0.043(10) 0.053(12) 0 -0.159(9) 0 0 0.037(9) -0.059(9) 0 0.062(9) 0.020(10) 0 0 0.173(12) 0.005(9) 0.037(14) 0 0 -0.024(11) -0.025(13) 0 0 0.016(12) 0.014(14) 1.033(3) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(12) 3.98(3) 0 0.000(11) 0.053(9) 0 -0.155(7) 0 0 0.011(8) -0.004(8) 0 0.006(8) 0.028(7) 0 0 0.178(9) 0.001(8) -0.010(10) 0 0 0.007(10) -0.001(9) 0 0 -0.017(10) -0.014(10) 1.031(3) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(13) 3.93(3) 0 0.043(12) 0.067(11) 0 -0.149(9) 0 0 -0.005(9) -0.031(9) 0 0.024(9) 0.029(8) 0 0 0.224(11) -0.005(9) 0.023(12) 0 0 -0.005(11) 0.027(11) 0 0 -0.038(12) -0.014(11) 1.032(3) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(14) 4.06(5) 0 0.081(13) 0.052(15) 0 -0.174(13) 0 0 0.019(11) -0.050(12) 0 0.021(11) -0.004(11) 0 0 0.250(16) -0.017(10) -0.057(17) 0 0 -0.001(14) -0.018(15) 0 0 0.013(14) 0.054(16) 1.019(4) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(15) 3.9329 0 0.0434 0.0668 0 -0.1485 0 0 -0.0054 -0.031 0 0.0236 0.0285 0 0 0.2236 -0.005 0.0232 0 0 -0.0051 0.0268 0 0 -0.0381 -0.0136 1.032(3) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(16) 3.9809 0 0.0003 0.0533 0 -0.1545 0 0 0.0105 -0.0037 0 0.0062 0.028 0 0 0.1783 0.0006 -0.0099 0 0 0.0066 -0.0013 0 0 -0.0169 -0.0141 1.031(3) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(21) 3.93(4) 0 0.056(9) 0.098(13) 0 -0.165(9) 0 0 0.020(8) -0.052(10) 0 0.048(10) 0.004(11) 0 0 0.197(11) 0.021(10) -0.006(14) 0 0 -0.012(11) 0.006(13) 0 0 -0.030(12) -0.011(15) 1.033(3) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(22) 3.95(3) 0 0.033(11) 0.051(8) 0 -0.140(7) 0 0 0.011(8) -0.003(7) 0 -0.003(9) 0.032(7) 0 0 0.188(9) 0.029(8) -0.022(10) 0 0 0.023(10) -0.018(10) 0 0 0.010(11) -0.024(10) 1.031(3) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(23) 3.90(3) 0 -0.021(11) 0.063(10) 0 -0.156(8) 0 0 0.002(9) 0.000(8) 0 0.010(9) 0.023(9) 0 0 0.208(9) 0.001(9) -0.006(11) 0 0 -0.014(10) -0.010(11) 0 0 -0.028(11) -0.029(10) 1.032(3) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(24) 4.18(5) 0 -0.015(10) 0.079(14) 0 -0.173(11) 0 0 0.019(10) -0.013(11) 0 0.002(10) 0.022(11) 0 0 0.275(14) 0.002(11) 0.003(15) 0 0 -0.012(12) -0.006(15) 0 0 -0.043(13) -0.038(15) 1.019(4) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(25) 3.8964 0 -0.021 0.0632 0 -0.1556 0 0 0.0022 0.0001 0 0.0095 0.023 0 0 0.2079 0.0012 -0.0055 0 0 -0.0138 -0.0101 0 0 -0.0277 -0.0287 1.032(3) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(26) 3.9509 0 0.0327 0.0514 0 -0.1401 0 0 0.0107 -0.003 0 -0.0034 0.0317 0 0 0.1879 0.0291 -0.0224 0 0 0.0225 -0.0175 0 0 0.0095 -0.0239 1.031(3) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 H(1) 0.782(15) 0 0 0 0.119(9) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(2) 0.786(16) 0 0 0 0.124(9) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(12) 1.070(10) 0 0 0 0.139(6) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(13) 1.0698 0 0 0 0.1385 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(14) 1.0698 0 0 0 0.1385 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(15) 1.0698 0 0 0 0.1385 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(16) 1.0698 0 0 0 0.1385 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(22) 1.013(9) 0 0 0 0.135(6) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(23) 1.0128 0 0 0 0.1352 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(24) 1.0128 0 0 0 0.1352 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(25) 1.0128 0 0 0 0.1352 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(26) 1.0128 0 0 0 0.1352 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 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) Z O(1) N(1) Y N(1) C(1) X N(1) C(11) Y N(2) C(1) X N(2) C(21) Y C(1) O(1) Z C(1) N(2) Y C(11) C(12) X C(11) C(16) Y C(12) C(13) X C(12) C(11) Y C(13) C(14) X C(13) C(12) Y C(14) C(15) X C(14) C(13) Y C(15) C(14) -X C(15) C(16) Y C(16) C(15) -X C(16) C(11) Y C(21) C(22) X C(21) C(26) Y C(22) C(23) X C(22) C(21) Y C(23) C(24) X C(23) C(22) Y C(24) C(25) X C(24) C(23) Y C(25) C(24) -X C(25) C(26) Y C(26) C(25) -X C(26) C(21) Y H(1) N(1) Z H(1) C(1) Y H(2) N(2) Z H(2) C(1) Y H(12) C(12) Z H(12) C(13) Y H(13) C(13) Z H(13) C(14) Y H(14) C(14) Z H(14) C(15) Y H(15) C(15) -Z H(15) C(14) Y H(16) C(16) -Z H(16) C(15) Y H(22) C(22) Z H(22) C(23) Y H(23) C(23) Z H(23) C(24) Y H(24) C(24) Z H(24) C(25) Y H(25) C(25) -Z H(25) C(24) Y H(26) C(26) -Z H(26) C(25) Y