# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics # This journal is © The Owner Societies 2012 ####################################################################### # # 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_SP60011 _database_code_depnum_ccdc_archive 'CCDC 299405' #TrackingRef '- EtNH3NO3.cif' _audit_creation_date 06-01-10 _audit_creation_method CRYSTALS_ver_12.82 _chemical_compound_source 'Wesley Henderson, USNA' _oxford_structure_analysis_title '[EtNH3][NO3] in P2(1)/c at 260 K' _exptl_crystal_recrystallization_method ; A crystal was grown in a capillary by laser-assisted zone-refinement at 260 K. Data were first collected at 260 K. ; _chemical_name_systematic ? _chemical_melting_point '287 K' _cell_length_a 9.9045(7) _cell_length_b 11.5287(8) _cell_length_c 9.9746(7) _cell_angle_alpha 90 _cell_angle_beta 112.701(4) _cell_angle_gamma 90 _cell_volume 1050.73(13) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 8 # Given Formula = C2 H8 N2 O3 # Dc = 1.37 Fooo = 464.00 Mu = 1.25 M = 216.19 # Found Formula = C2 H8 N2 O3 # Dc = 1.37 FOOO = 464.00 Mu = 1.25 M = 216.19 _chemical_formula_sum 'C2 H8 N2 O3' _chemical_formula_moiety 'C2 H8 N, N O3' _chemical_formula_weight 108.10 _cell_measurement_reflns_used 1436 _cell_measurement_theta_min 2 _cell_measurement_theta_max 23 _cell_measurement_temperature 260 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_min 0.32 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_max 4.00 _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.125 # Sheldrick geometric approximatio 0.96 0.96 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.64 _exptl_absorpt_correction_T_max 0.96 _diffrn_measurement_device_type Unknown _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w _computing_data_collection SMART _computing_data_reduction SAINT _computing_cell_refinement SAINT _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material ; CRYSTALS (Betteridge et al., 2003), XCIF, PLATON ; _computing_molecular_graphics 'CAMERON (Watkin et al., 1996),XP' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 260 _diffrn_reflns_number 8674 _reflns_number_total 2298 _diffrn_reflns_av_R_equivalents 0.040 # Number of reflections with Friedels Law is 2298 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2305 _diffrn_reflns_reduction_process; ; Merged with SORTAV R.H. Blessing, (1997) J. Appl Cryst. (1997), 30, 421-426. ; _diffrn_reflns_theta_min 2.229 _diffrn_reflns_theta_max 27.047 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.506 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _reflns_limit_h_min -12 _reflns_limit_h_max 11 _reflns_limit_k_min 0 _reflns_limit_k_max 14 _reflns_limit_l_min 0 _reflns_limit_l_max 12 _oxford_diffrn_Wilson_B_factor 3.95 _oxford_diffrn_Wilson_scale 0.20 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap/geom _refine_diff_density_min -0.13 _refine_diff_density_max 0.25 _refine_ls_number_reflns 2297 _refine_ls_number_restraints 50 _refine_ls_number_parameters 185 #_refine_ls_R_factor_ref 0.0764 _refine_ls_wR_factor_ref 0.1215 _refine_ls_goodness_of_fit_ref 0.9793 #_reflns_number_all 2297 _refine_ls_R_factor_all 0.0764 _refine_ls_wR_factor_all 0.1215 # No actual I/u(I) cutoff was used for refinement. The # threshold below is used for "_gt" information ONLY: _reflns_threshold_expression I>2.00u(I) _reflns_number_gt 1409 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_gt 0.1044 _refine_ls_shift/su_max 0.002633 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.31P] where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens N11 N 0.83771(19) 0.64001(15) 0.00562(19) 0.0471 1.0000 Uani D . . . . . C11 C 0.7002(2) 0.69984(19) -0.0856(2) 0.0574 1.0000 Uani D . . . . . C21 C 0.5998(3) 0.7142(3) -0.0099(3) 0.0816 1.0000 Uani D . . . . . N12 N 0.80991(19) 0.13068(14) 0.02129(19) 0.0424 1.0000 Uani D . . . . . C12 C 0.6738(2) 0.07481(18) -0.0810(2) 0.0511 1.0000 Uani D . . . . . C22 C 0.6934(2) 0.02693(18) -0.2119(2) 0.0546 1.0000 Uani D . . . . . N13 N 0.95612(16) 0.88187(13) 0.22355(17) 0.0421 1.0000 Uani . . . . . . O13 O 0.97709(18) 0.96713(13) 0.30370(17) 0.0676 1.0000 Uani . . . . . . O23 O 0.94034(16) 0.78387(11) 0.26974(14) 0.0537 1.0000 Uani . . . . . . O33 O 0.94761(16) 0.89281(11) 0.09658(15) 0.0533 1.0000 Uani . . . . . . N14 N 0.71723(18) 0.38589(13) -0.17652(18) 0.0469 1.0000 Uani . . . . . . O14 O 0.7162(2) 0.39559(13) -0.05359(17) 0.0773 1.0000 Uani . . . . . . O24 O 0.7856(2) 0.30437(12) -0.20322(18) 0.0694 1.0000 Uani . . . . . . O34 O 0.65346(19) 0.45651(15) -0.27213(17) 0.0764 1.0000 Uani . . . . . . H11 H 0.8841(17) 0.6758(13) 0.0865(11) 0.063(7) 1.0000 Uiso D . . . . . H21 H 0.8957(17) 0.6342(18) -0.0388(18) 0.067(8) 1.0000 Uiso D . . . . . H31 H 0.821(3) 0.5700(11) 0.0269(17) 0.079(8) 1.0000 Uiso D . . . . . H12 H 0.836(2) 0.1890(11) -0.0178(18) 0.063(7) 1.0000 Uiso D . . . . . H22 H 0.800(2) 0.1560(13) 0.0994(16) 0.060(7) 1.0000 Uiso D . . . . . H32 H 0.882(2) 0.0823(18) 0.046(2) 0.051(6) 1.0000 Uiso D . . . . . H111 H 0.7298(13) 0.7759(7) -0.1098(13) 0.079(5) 1.0000 Uiso D . . . . . H112 H 0.6568(12) 0.6536(10) -0.1751(10) 0.079(5) 1.0000 Uiso D . . . . . H211 H 0.5130(12) 0.7540(15) -0.0727(13) 0.124(7) 1.0000 Uiso D . . . . . H212 H 0.6468(14) 0.7585(14) 0.0777(13) 0.124(7) 1.0000 Uiso D . . . . . H213 H 0.5737(18) 0.6388(8) 0.0141(19) 0.124(7) 1.0000 Uiso D . . . . . H121 H 0.5990(12) 0.1352(9) -0.1074(12) 0.069(5) 1.0000 Uiso D . . . . . H122 H 0.6493(13) 0.0151(9) -0.0251(12) 0.069(5) 1.0000 Uiso D . . . . . H221 H 0.6037(11) -0.0102(11) -0.2735(12) 0.071(4) 1.0000 Uiso D . . . . . H222 H 0.7163(15) 0.0885(9) -0.2643(13) 0.071(4) 1.0000 Uiso D . . . . . H223 H 0.7719(13) -0.0292(10) -0.1817(12) 0.071(4) 1.0000 Uiso D . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0555(10) 0.0433(9) 0.0411(10) 0.0007(7) 0.0170(9) 0.0060(8) C11 0.0628(13) 0.0550(12) 0.0468(12) 0.0008(9) 0.0129(10) -0.0001(10) C21 0.0610(15) 0.113(2) 0.0669(17) -0.0039(15) 0.0206(13) 0.0142(15) N12 0.0436(9) 0.0402(8) 0.0429(10) -0.0013(7) 0.0161(8) -0.0019(8) C12 0.0442(11) 0.0584(12) 0.0497(12) -0.0076(10) 0.0172(9) -0.0075(9) C22 0.0567(13) 0.0553(12) 0.0482(12) -0.0083(10) 0.0164(10) -0.0087(10) N13 0.0337(8) 0.0465(9) 0.0438(9) -0.0044(7) 0.0123(7) 0.0027(6) O13 0.0695(10) 0.0592(9) 0.0690(10) -0.0251(8) 0.0211(8) -0.0039(7) O23 0.0624(9) 0.0499(8) 0.0501(8) 0.0067(6) 0.0232(7) 0.0018(6) O33 0.0588(9) 0.0569(8) 0.0470(8) 0.0064(6) 0.0236(7) 0.0032(7) N14 0.0518(10) 0.0423(8) 0.0484(10) -0.0039(8) 0.0213(8) -0.0034(7) O14 0.1202(15) 0.0691(11) 0.0531(10) -0.0012(8) 0.0451(10) 0.0038(10) O24 0.1015(13) 0.0421(7) 0.0875(12) 0.0090(7) 0.0619(11) 0.0137(8) O34 0.0818(12) 0.0865(11) 0.0577(10) 0.0155(9) 0.0232(9) 0.0372(9) _refine_ls_extinction_method None _oxford_refine_ls_scale 2.39(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N11 . C11 . 1.484(3) yes N11 . H11 . 0.863(7) no N11 . H21 . 0.852(9) no N11 . H31 . 0.866(9) no C11 . C21 . 1.471(3) yes C11 . H111 . 0.984(7) no C11 . H112 . 0.985(7) no C21 . H211 . 0.962(7) no C21 . H212 . 0.963(7) no C21 . H213 . 0.963(7) no N12 . C12 . 1.487(2) yes N12 . H12 . 0.864(9) no N12 . H22 . 0.873(9) no N12 . H32 . 0.86(2) no C12 . C22 . 1.497(3) yes C12 . H121 . 0.976(9) no C12 . H122 . 0.974(9) no C22 . H221 . 0.963(9) no C22 . H222 . 0.959(9) no C22 . H223 . 0.966(9) no N13 . O13 . 1.2329(19) yes N13 . O23 . 1.2525(19) yes N13 . O33 . 1.2428(19) yes N14 . O14 . 1.235(2) yes N14 . O24 . 1.246(2) yes N14 . O34 . 1.227(2) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C11 . N11 . H11 . 112.5(12) no C11 . N11 . H21 . 111.2(14) no H11 . N11 . H21 . 107.43(10) no C11 . N11 . H31 . 111.7(16) no H11 . N11 . H31 . 107.42(10) no H21 . N11 . H31 . 106(2) no N11 . C11 . C21 . 112.33(18) yes N11 . C11 . H111 . 105.9(7) no C21 . C11 . H111 . 110.5(7) no N11 . C11 . H112 . 106.2(7) no C21 . C11 . H112 . 112.4(7) no H111 . C11 . H112 . 109.12(7) no C11 . C21 . H211 . 109.3(7) no C11 . C21 . H212 . 109.9(7) no H211 . C21 . H212 . 109.57(7) no C11 . C21 . H213 . 109.0(7) no H211 . C21 . H213 . 109.57(7) no H212 . C21 . H213 . 109.57(7) no C12 . N12 . H12 . 112.0(14) no C12 . N12 . H22 . 111.7(14) no H12 . N12 . H22 . 107.43(10) no C12 . N12 . H32 . 110.1(14) no H12 . N12 . H32 . 106.0(20) no H22 . N12 . H32 . 109.4(20) no N12 . C12 . C22 . 111.72(17) yes N12 . C12 . H121 . 105.6(7) no C22 . C12 . H121 . 111.6(7) no N12 . C12 . H122 . 105.9(7) no C22 . C12 . H122 . 112.5(7) no H121 . C12 . H122 . 109.12(10) no C12 . C22 . H221 . 108.7(7) no C12 . C22 . H222 . 109.9(7) no H221 . C22 . H222 . 109.56(10) no C12 . C22 . H223 . 109.5(7) no H221 . C22 . H223 . 109.57(10) no H222 . C22 . H223 . 109.54(10) no O13 . N13 . O23 . 119.62(16) yes O13 . N13 . O33 . 120.54(16) yes O23 . N13 . O33 . 119.82(15) yes O14 . N14 . O24 . 119.60(17) yes O14 . N14 . O34 . 120.82(17) yes O24 . N14 . O34 . 119.57(17) yes data_SP60012 _database_code_depnum_ccdc_archive 'CCDC 299406' #TrackingRef '- EtNH3NO3.cif' _audit_creation_date 06-01-10 _audit_creation_method CRYSTALS_ver_12.82 _chemical_compound_source 'Wesley Henderson, USNA' _oxford_structure_analysis_title '[EtNH3][NO3] in P2(1)/c at 150 K' _exptl_crystal_recrystallization_method ; A crystal was grown in a capillary by laser-assisted zone-refinement at 260 K. Data were first collected at 260 K and then at 150K. ; _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 9.8294(3) _cell_length_b 11.4347(4) _cell_length_c 9.8981(3) _cell_angle_alpha 90 _cell_angle_beta 113.007(2) _cell_angle_gamma 90 _cell_volume 1024.02(6) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 8 # Given Formula = C2 H8 N2 O3 # Dc = 1.40 Fooo = 464.00 Mu = 1.29 M = 216.19 # Found Formula = C2 H8 N2 O3 # Dc = 1.40 FOOO = 464.00 Mu = 1.29 M = 216.19 _chemical_formula_sum 'C2 H8 N2 O3' _chemical_formula_moiety 'C2 H8 N, N O3' _chemical_formula_weight 108.10 _cell_measurement_reflns_used 7909 _cell_measurement_theta_min 2 _cell_measurement_theta_max 29 _cell_measurement_temperature 150 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_min 0.32 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_max 4.00 _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.129 # Sheldrick geometric approximatio 0.96 0.96 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.73 _exptl_absorpt_correction_T_max 0.96 _diffrn_measurement_device_type 'Bruker SMART' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'SMART (Siemens, 1993)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 19105 _reflns_number_total 2747 _diffrn_reflns_av_R_equivalents 0.026 # Number of reflections with Friedels Law is 2747 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2903 _diffrn_reflns_reduction_process; ; Merged with SORTAV R.H. Blessing, (1997) J. Appl Cryst. (1997), 30, 421-426. ; _diffrn_reflns_theta_min 2.251 _diffrn_reflns_theta_max 29.688 _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 28.204 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _reflns_limit_h_min -13 _reflns_limit_h_max 12 _reflns_limit_k_min 0 _reflns_limit_k_max 15 _reflns_limit_l_min 0 _reflns_limit_l_max 13 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.28 _refine_diff_density_max 0.23 _refine_ls_number_reflns 2747 _refine_ls_number_restraints 50 _refine_ls_number_parameters 185 #_refine_ls_R_factor_ref 0.0443 _refine_ls_wR_factor_ref 0.0910 _refine_ls_goodness_of_fit_ref 1.0144 #_reflns_number_all 2747 _refine_ls_R_factor_all 0.0443 _refine_ls_wR_factor_all 0.0910 # No actual I/u(I) cutoff was used for refinement. The # threshold below is used for "_gt" information ONLY: _reflns_threshold_expression I>2.00u(I) _reflns_number_gt 2218 _refine_ls_R_factor_gt 0.0340 _refine_ls_wR_factor_gt 0.0851 _refine_ls_shift/su_max 0.006954 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.13P] where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens N11 N 0.83355(9) 0.63884(7) 0.00582(9) 0.0254 1.0000 Uani D . . . . . C11 C 0.69718(11) 0.70259(9) -0.08820(10) 0.0270 1.0000 Uani D . . . . . C21 C 0.59438(12) 0.72051(12) -0.01068(12) 0.0408 1.0000 Uani D . . . . . N12 N 0.81213(8) 0.12908(7) 0.02188(9) 0.0217 1.0000 Uani D . . . . . C12 C 0.67352(10) 0.07488(9) -0.08425(10) 0.0280 1.0000 Uani D . . . . . C22 C 0.69384(11) 0.02688(9) -0.21703(10) 0.0287 1.0000 Uani D . . . . . N13 N 0.95531(8) 0.88071(6) 0.22562(8) 0.0222 1.0000 Uani . . . . . . O13 O 0.97636(8) 0.96691(6) 0.30796(8) 0.0351 1.0000 Uani . . . . . . O23 O 0.93968(7) 0.78076(6) 0.27137(7) 0.0282 1.0000 Uani . . . . . . O33 O 0.94669(8) 0.89267(6) 0.09703(7) 0.0281 1.0000 Uani . . . . . . N14 N 0.71721(8) 0.38748(6) -0.17576(9) 0.0238 1.0000 Uani . . . . . . O14 O 0.71339(9) 0.39726(7) -0.05183(8) 0.0363 1.0000 Uani . . . . . . O24 O 0.78912(9) 0.30475(6) -0.20040(8) 0.0351 1.0000 Uani . . . . . . O34 O 0.65140(8) 0.45780(7) -0.27529(8) 0.0389 1.0000 Uani . . . . . . H11 H 0.8782(9) 0.6747(7) 0.0887(8) 0.029(3) 1.0000 Uiso D . . . . . H21 H 0.8948(10) 0.6326(11) -0.0365(11) 0.045(4) 1.0000 Uiso D . . . . . H31 H 0.8114(13) 0.5688(8) 0.0248(9) 0.033(3) 1.0000 Uiso D . . . . . H12 H 0.8382(13) 0.1881(7) -0.0180(11) 0.035(3) 1.0000 Uiso D . . . . . H22 H 0.8018(12) 0.1544(8) 0.1013(10) 0.027(3) 1.0000 Uiso D . . . . . H32 H 0.8820(14) 0.0779(11) 0.0457(13) 0.028(3) 1.0000 Uiso D . . . . . H111 H 0.7293(10) 0.7765(6) -0.1141(8) 0.036(2) 1.0000 Uiso D . . . . . H112 H 0.6514(10) 0.6554(7) -0.1764(8) 0.036(2) 1.0000 Uiso D . . . . . H211 H 0.5077(8) 0.7645(7) -0.0740(9) 0.053(2) 1.0000 Uiso D . . . . . H212 H 0.6463(9) 0.7648(7) 0.0800(8) 0.053(2) 1.0000 Uiso D . . . . . H213 H 0.5631(9) 0.6457(6) 0.0135(9) 0.053(2) 1.0000 Uiso D . . . . . H121 H 0.5995(9) 0.1358(7) -0.1112(10) 0.040(2) 1.0000 Uiso D . . . . . H122 H 0.6464(9) 0.0141(7) -0.0308(10) 0.040(2) 1.0000 Uiso D . . . . . H221 H 0.6011(9) -0.0111(7) -0.2805(9) 0.0383(19) 1.0000 Uiso D . . . . . H222 H 0.7174(9) 0.0894(7) -0.2714(9) 0.0383(19) 1.0000 Uiso D . . . . . H223 H 0.7737(9) -0.0309(7) -0.1862(9) 0.0383(19) 1.0000 Uiso D . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0301(4) 0.0243(4) 0.0224(4) -0.0004(3) 0.0109(3) 0.0028(3) C11 0.0301(5) 0.0277(5) 0.0205(4) 0.0035(3) 0.0069(3) 0.0012(4) C21 0.0302(5) 0.0608(8) 0.0305(5) 0.0029(5) 0.0109(4) 0.0103(5) N12 0.0237(4) 0.0216(4) 0.0208(4) -0.0008(3) 0.0097(3) -0.0012(3) C12 0.0239(4) 0.0354(5) 0.0252(5) -0.0056(4) 0.0102(3) -0.0054(4) C22 0.0332(5) 0.0300(5) 0.0232(4) -0.0048(4) 0.0114(4) -0.0046(4) N13 0.0171(3) 0.0256(4) 0.0228(4) -0.0020(3) 0.0067(3) 0.0019(3) O13 0.0345(4) 0.0325(4) 0.0356(4) -0.0138(3) 0.0108(3) -0.0011(3) O23 0.0324(4) 0.0278(4) 0.0259(3) 0.0036(3) 0.0130(3) 0.0007(3) O33 0.0320(4) 0.0300(4) 0.0243(3) 0.0030(3) 0.0134(3) 0.0020(3) N14 0.0250(4) 0.0234(4) 0.0243(4) -0.0029(3) 0.0110(3) -0.0035(3) O14 0.0542(5) 0.0348(4) 0.0267(4) -0.0035(3) 0.0230(3) -0.0025(3) O24 0.0516(4) 0.0230(3) 0.0427(4) 0.0051(3) 0.0313(4) 0.0085(3) O34 0.0406(4) 0.0459(5) 0.0287(4) 0.0074(3) 0.0120(3) 0.0182(3) _refine_ls_extinction_method None _oxford_refine_ls_scale 2.50(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N11 . C11 . 1.4896(12) yes N11 . H11 . 0.867(6) no N11 . H21 . 0.860(8) no N11 . H31 . 0.869(8) no C11 . C21 . 1.5026(15) yes C11 . H111 . 0.971(6) no C11 . H112 . 0.974(6) no C21 . H211 . 0.977(6) no C21 . H212 . 0.982(6) no C21 . H213 . 0.970(6) no N12 . C12 . 1.4916(12) yes N12 . H12 . 0.869(8) no N12 . H22 . 0.880(8) no N12 . H32 . 0.862(13) no C12 . C22 . 1.5078(13) yes C12 . H121 . 0.966(8) no C12 . H122 . 0.972(8) no C22 . H221 . 0.984(8) no C22 . H222 . 0.976(8) no C22 . H223 . 0.979(8) no N13 . O13 . 1.2437(10) yes N13 . O23 . 1.2607(10) yes N13 . O33 . 1.2497(10) yes N14 . O14 . 1.2469(10) yes N14 . O24 . 1.2604(10) yes N14 . O34 . 1.2399(10) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C11 . N11 . H11 . 111.0(6) no C11 . N11 . H21 . 111.5(8) no H11 . N11 . H21 . 107.93(10) no C11 . N11 . H31 . 110.2(8) no H11 . N11 . H31 . 107.92(10) no H21 . N11 . H31 . 108.1(11) no N11 . C11 . C21 . 111.60(8) yes N11 . C11 . H111 . 106.6(5) no C21 . C11 . H111 . 111.6(5) no N11 . C11 . H112 . 106.1(5) no C21 . C11 . H112 . 111.5(5) no H111 . C11 . H112 . 109.21(7) no C11 . C21 . H211 . 109.6(5) no C11 . C21 . H212 . 108.9(5) no H211 . C21 . H212 . 109.35(7) no C11 . C21 . H213 . 110.3(5) no H211 . C21 . H213 . 109.36(7) no H212 . C21 . H213 . 109.34(7) no C12 . N12 . H12 . 110.7(7) no C12 . N12 . H22 . 111.9(7) no H12 . N12 . H22 . 107.92(10) no C12 . N12 . H32 . 108.8(8) no H12 . N12 . H32 . 107.8(11) no H22 . N12 . H32 . 109.7(10) no N12 . C12 . C22 . 111.68(8) yes N12 . C12 . H121 . 106.1(6) no C22 . C12 . H121 . 111.3(5) no N12 . C12 . H122 . 106.4(5) no C22 . C12 . H122 . 111.9(5) no H121 . C12 . H122 . 109.19(10) no C12 . C22 . H221 . 108.2(5) no C12 . C22 . H222 . 110.8(5) no H221 . C22 . H222 . 109.38(10) no C12 . C22 . H223 . 109.7(5) no H221 . C22 . H223 . 109.34(10) no H222 . C22 . H223 . 109.34(10) no O13 . N13 . O23 . 119.71(8) yes O13 . N13 . O33 . 120.56(8) yes O23 . N13 . O33 . 119.71(7) yes O14 . N14 . O24 . 119.50(8) yes O14 . N14 . O34 . 121.10(8) yes O24 . N14 . O34 . 119.40(8) yes data_SP60013 _database_code_depnum_ccdc_archive 'CCDC 299407' #TrackingRef '- EtNH3NO3.cif' _audit_creation_date 06-01-10 _audit_creation_method CRYSTALS_ver_12.82 _chemical_compound_source 'Wesley Henderson, USNA' _oxford_structure_analysis_title '[EtNH3][NO3] in P2(1)/c at 100 K' _exptl_crystal_recrystallization_method ; A crystal was grown in a capillary by laser-assisted zone-refinement at 260 K. Data were first collected at 260 K and then at 150 and 100 K. ; _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 9.7872(3) _cell_length_b 11.4041(4) _cell_length_c 9.8847(3) _cell_angle_alpha 90 _cell_angle_beta 113.110(2) _cell_angle_gamma 90 _cell_volume 1014.74(6) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 8 # Given Formula = C2 H8 N2 O3 # Dc = 1.42 Fooo = 464.00 Mu = 1.30 M = 216.19 # Found Formula = C2 H8 N2 O3 # Dc = 1.42 FOOO = 464.00 Mu = 1.30 M = 216.19 _chemical_formula_sum 'C2 H8 N2 O3' _chemical_formula_moiety 'C2 H8 N, N O3' _chemical_formula_weight 108.10 _cell_measurement_reflns_used 3943 _cell_measurement_theta_min 3 _cell_measurement_theta_max 34 _cell_measurement_temperature 100 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_min 0.32 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_max 4.00 _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.130 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_absorpt_correction_T_min 0.78 _exptl_absorpt_correction_T_max 0.96 _diffrn_measurement_device_type 'Bruker SMART' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w _computing_data_collection 'SMART (Siemens, 1993)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS, XCIF, PLATON' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996) & XP' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 100 _diffrn_reflns_number 18275 _reflns_number_total 4463 _diffrn_reflns_av_R_equivalents 0.037 # Number of reflections with Friedels Law is 4463 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 4471 _diffrn_reflns_reduction_process; ; Merged with SORTAV R.H. Blessing, (1997) J. Appl Cryst. (1997), 30, 421-426. ; _diffrn_reflns_theta_min 2.262 _diffrn_reflns_theta_max 35.008 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 35.008 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _reflns_limit_h_min -15 _reflns_limit_h_max 14 _reflns_limit_k_min 0 _reflns_limit_k_max 18 _reflns_limit_l_min 0 _reflns_limit_l_max 15 _oxford_diffrn_Wilson_B_factor 1.49 _oxford_diffrn_Wilson_scale 0.17 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom/difmap _refine_diff_density_min -0.26 _refine_diff_density_max 0.42 _refine_ls_number_reflns 4461 _refine_ls_number_restraints 50 _refine_ls_number_parameters 185 #_refine_ls_R_factor_ref 0.0528 _refine_ls_wR_factor_ref 0.0938 _refine_ls_goodness_of_fit_ref 0.9832 #_reflns_number_all 4461 _refine_ls_R_factor_all 0.0528 _refine_ls_wR_factor_all 0.0938 # No actual I/u(I) cutoff was used for refinement. The # threshold below is used for "_gt" information ONLY: _reflns_threshold_expression I>2.00u(I) _reflns_number_gt 3343 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_gt 0.0838 _refine_ls_shift/su_max 0.007083 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.09P] where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens N11 N 0.83255(7) 0.63834(5) 0.00608(7) 0.0184 1.0000 Uani D . . . . . C11 C 0.69637(8) 0.70337(6) -0.08909(7) 0.0191 1.0000 Uani D . . . . . C21 C 0.59317(9) 0.72318(9) -0.01138(9) 0.0291 1.0000 Uani D . . . . . N12 N 0.81310(6) 0.12856(5) 0.02209(6) 0.0158 1.0000 Uani D . . . . . C12 C 0.67336(8) 0.07500(7) -0.08488(8) 0.0205 1.0000 Uani D . . . . . C22 C 0.69350(8) 0.02730(7) -0.21880(8) 0.0211 1.0000 Uani D . . . . . N13 N 0.95511(6) 0.88021(5) 0.22637(6) 0.0160 1.0000 Uani . . . . . . O13 O 0.97661(6) 0.96662(5) 0.30944(6) 0.0251 1.0000 Uani . . . . . . O23 O 0.93966(6) 0.77978(5) 0.27211(6) 0.0203 1.0000 Uani . . . . . . O33 O 0.94649(6) 0.89246(5) 0.09697(6) 0.0203 1.0000 Uani . . . . . . N14 N 0.71739(7) 0.38773(5) -0.17557(7) 0.0170 1.0000 Uani . . . . . . O14 O 0.71203(7) 0.39716(5) -0.05140(6) 0.0257 1.0000 Uani . . . . . . O24 O 0.79083(7) 0.30491(5) -0.19922(6) 0.0246 1.0000 Uani . . . . . . O34 O 0.65137(7) 0.45840(6) -0.27576(6) 0.0273 1.0000 Uani . . . . . . H11 H 0.8770(9) 0.6747(7) 0.0883(7) 0.023(3) 1.0000 Uiso D . . . . . H21 H 0.8933(10) 0.6323(11) -0.0372(10) 0.042(4) 1.0000 Uiso D . . . . . H31 H 0.8088(12) 0.5685(7) 0.0250(9) 0.025(3) 1.0000 Uiso D . . . . . H12 H 0.8394(12) 0.1867(7) -0.0184(10) 0.025(3) 1.0000 Uiso D . . . . . H22 H 0.8027(12) 0.1544(7) 0.1011(10) 0.024(3) 1.0000 Uiso D . . . . . H32 H 0.8818(13) 0.0770(10) 0.0472(12) 0.024(3) 1.0000 Uiso D . . . . . H111 H 0.7293(9) 0.7763(6) -0.1146(8) 0.0256(18) 1.0000 Uiso D . . . . . H112 H 0.6503(9) 0.6568(6) -0.1764(7) 0.0256(18) 1.0000 Uiso D . . . . . H211 H 0.5068(8) 0.7684(7) -0.0750(9) 0.043(2) 1.0000 Uiso D . . . . . H212 H 0.6449(9) 0.7670(7) 0.0804(8) 0.043(2) 1.0000 Uiso D . . . . . H213 H 0.5595(9) 0.6483(6) 0.0119(9) 0.043(2) 1.0000 Uiso D . . . . . H121 H 0.5999(9) 0.1358(7) -0.1117(9) 0.029(2) 1.0000 Uiso D . . . . . H122 H 0.6458(9) 0.0141(7) -0.0318(9) 0.029(2) 1.0000 Uiso D . . . . . H221 H 0.6002(9) -0.0109(7) -0.2828(8) 0.0307(16) 1.0000 Uiso D . . . . . H222 H 0.7164(8) 0.0900(7) -0.2732(8) 0.0307(16) 1.0000 Uiso D . . . . . H223 H 0.7745(9) -0.0311(7) -0.1893(9) 0.0307(16) 1.0000 Uiso D . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0218(3) 0.0177(3) 0.0163(2) 0.00002(19) 0.0080(2) 0.0024(2) C11 0.0211(3) 0.0199(3) 0.0146(3) 0.0025(2) 0.0054(2) 0.0015(2) C21 0.0216(3) 0.0435(5) 0.0225(3) 0.0030(3) 0.0088(3) 0.0081(3) N12 0.0174(2) 0.0158(2) 0.0148(2) -0.00045(18) 0.00702(18) -0.00110(19) C12 0.0179(3) 0.0268(3) 0.0176(3) -0.0049(2) 0.0078(2) -0.0046(2) C22 0.0251(3) 0.0223(3) 0.0164(3) -0.0039(2) 0.0088(2) -0.0035(3) N13 0.0130(2) 0.0183(3) 0.0165(2) -0.00155(19) 0.00551(17) 0.00108(18) O13 0.0251(2) 0.0233(3) 0.0249(3) -0.0101(2) 0.0078(2) -0.0005(2) O23 0.0235(2) 0.0197(2) 0.0187(2) 0.00311(18) 0.00942(18) 0.00045(18) O33 0.0241(2) 0.0215(2) 0.0170(2) 0.00211(17) 0.00999(18) 0.00126(19) N14 0.0185(2) 0.0165(2) 0.0173(2) -0.00205(19) 0.00832(19) -0.00227(19) O14 0.0374(3) 0.0256(3) 0.0189(2) -0.00280(19) 0.0162(2) -0.0018(2) O24 0.0360(3) 0.0166(2) 0.0292(3) 0.00353(19) 0.0212(2) 0.0062(2) O34 0.0292(3) 0.0313(3) 0.0205(2) 0.0053(2) 0.0088(2) 0.0122(2) _refine_ls_extinction_method None _oxford_refine_ls_scale 2.514(19) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N11 . C11 . 1.4923(9) yes N11 . H11 . 0.862(6) no N11 . H21 . 0.860(8) no N11 . H31 . 0.870(8) no C11 . C21 . 1.5068(11) yes C11 . H111 . 0.961(6) no C11 . H112 . 0.961(6) no C21 . H211 . 0.980(6) no C21 . H212 . 0.984(6) no C21 . H213 . 0.975(6) no N12 . C12 . 1.4921(9) yes N12 . H12 . 0.864(8) no N12 . H22 . 0.878(8) no N12 . H32 . 0.853(12) no C12 . C22 . 1.5139(10) yes C12 . H121 . 0.958(8) no C12 . H122 . 0.970(8) no C22 . H221 . 0.985(8) no C22 . H222 . 0.972(8) no C22 . H223 . 0.987(8) no N13 . O13 . 1.2466(8) yes N13 . O23 . 1.2620(8) yes N13 . O33 . 1.2562(8) yes N14 . O14 . 1.2535(8) yes N14 . O24 . 1.2630(8) yes N14 . O34 . 1.2431(8) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C11 . N11 . H11 . 110.5(6) no C11 . N11 . H21 . 110.3(8) no H11 . N11 . H21 . 108.41(10) no C11 . N11 . H31 . 110.0(7) no H11 . N11 . H31 . 108.38(10) no H21 . N11 . H31 . 109.2(10) no N11 . C11 . C21 . 111.39(6) yes N11 . C11 . H111 . 106.7(5) no C21 . C11 . H111 . 111.4(5) no N11 . C11 . H112 . 106.2(5) no C21 . C11 . H112 . 111.6(5) no H111 . C11 . H112 . 109.25(7) no C11 . C21 . H211 . 109.5(5) no C11 . C21 . H212 . 110.0(5) no H211 . C21 . H212 . 109.05(7) no C11 . C21 . H213 . 110.2(5) no H211 . C21 . H213 . 109.05(7) no H212 . C21 . H213 . 109.04(7) no C12 . N12 . H12 . 110.0(7) no C12 . N12 . H22 . 111.9(7) no H12 . N12 . H22 . 108.39(10) no C12 . N12 . H32 . 108.8(8) no H12 . N12 . H32 . 108.6(10) no H22 . N12 . H32 . 109.0(10) no N12 . C12 . C22 . 111.66(6) yes N12 . C12 . H121 . 106.2(5) no C22 . C12 . H121 . 111.0(5) no N12 . C12 . H122 . 106.4(5) no C22 . C12 . H122 . 112.0(5) no H121 . C12 . H122 . 109.23(10) no C12 . C22 . H221 . 108.3(5) no C12 . C22 . H222 . 110.9(5) no H221 . C22 . H222 . 109.07(10) no C12 . C22 . H223 . 110.4(5) no H221 . C22 . H223 . 109.04(10) no H222 . C22 . H223 . 109.04(10) no O13 . N13 . O23 . 119.63(6) yes O13 . N13 . O33 . 120.62(6) yes O23 . N13 . O33 . 119.74(6) yes O14 . N14 . O24 . 119.40(6) yes O14 . N14 . O34 . 121.06(6) yes O24 . N14 . O34 . 119.53(6) yes #===END