# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'David Turner' _publ_contact_author_email DAVID.TURNER@SCI.MONASH.EDU.AU _publ_section_title ; Ammonium Salts of Carbamoyldicyanomethanide, C(CN)2(CONH2) -. A Comparison of Hydrogen Bond Rich vs. Hydrogen Bond Poor Cations. ; loop_ _publ_author_name 'David Turner' 'Stuart Batten' 'Wan Teng Lee.' 'Rose MacDonald' # Attachment 'Ammonium.CIF' data_1 _database_code_depnum_ccdc_archive 'CCDC 701912' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Ammonium carbamoyldicyanomethanide ; _chemical_name_common NH4cdm _chemical_melting_point ? _chemical_formula_moiety 'C4 H2 N3 O, H4 N' _chemical_formula_sum 'C4 H6 N4 O' _chemical_formula_weight 126.13 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.0491(7) _cell_length_b 13.3890(16) _cell_length_c 8.5840(11) _cell_angle_alpha 90.00 _cell_angle_beta 97.249(4) _cell_angle_gamma 90.00 _cell_volume 575.66(13) _cell_formula_units_Z 4 _cell_measurement_temperature 123(1) _cell_measurement_reflns_used 1614 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 24.99 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.455 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9737 _exptl_absorpt_correction_T_max 0.9911 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 Apex II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1614 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0464 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 24.99 _reflns_number_total 895 _reflns_number_gt 663 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker)' _computing_cell_refinement 'Bruker SMART (Bruker)' _computing_data_reduction 'Bruker SAINT (Bruker)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_extinction_expression ? _refine_ls_number_reflns 895 _refine_ls_number_parameters 106 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0620 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1071 _refine_ls_wR_factor_gt 0.0964 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N4 N 0.7607(4) 0.40369(18) -0.4400(3) 0.0165(5) Uani 1 1 d . . . N1 N 1.3050(4) 0.27782(15) 0.1882(3) 0.0190(5) Uani 1 1 d . . . N2 N 0.7907(4) 0.31479(14) -0.1214(2) 0.0187(5) Uani 1 1 d . . . N3 N 0.6761(4) 0.53329(15) 0.2580(2) 0.0204(5) Uani 1 1 d . . . O1 O 1.2229(3) 0.37837(11) 0.38776(18) 0.0154(4) Uani 1 1 d . . . C3 C 0.8565(4) 0.35236(16) -0.0019(3) 0.0145(6) Uani 1 1 d . . . C2 C 1.1627(4) 0.34974(16) 0.2460(3) 0.0132(6) Uani 1 1 d . . . C4 C 0.7938(5) 0.47048(17) 0.2047(3) 0.0150(6) Uani 1 1 d . . . C1 C 0.9424(5) 0.39318(16) 0.1463(3) 0.0139(6) Uani 1 1 d . . . H4A H 0.784(5) 0.3698(17) -0.343(4) 0.029(7) Uiso 1 1 d . . . H1B H 1.268(5) 0.2567(18) 0.104(3) 0.016(7) Uiso 1 1 d . . . H4B H 0.766(6) 0.472(2) -0.421(4) 0.054(10) Uiso 1 1 d . . . H1A H 1.438(6) 0.246(2) 0.265(3) 0.043(9) Uiso 1 1 d . . . H4C H 0.590(7) 0.380(2) -0.502(4) 0.048(9) Uiso 1 1 d . . . H4D H 0.901(6) 0.3865(19) -0.497(3) 0.042(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N4 0.0164(12) 0.0176(14) 0.0153(11) 0.0004(10) 0.0008(10) -0.0008(9) N1 0.0181(12) 0.0247(14) 0.0127(13) -0.0055(10) -0.0031(10) 0.0056(9) N2 0.0197(12) 0.0197(13) 0.0153(11) -0.0022(9) -0.0026(9) 0.0032(8) N3 0.0165(11) 0.0249(13) 0.0190(12) -0.0008(9) -0.0005(9) 0.0039(9) O1 0.0145(9) 0.0171(10) 0.0134(9) -0.0022(7) -0.0026(7) -0.0003(7) C3 0.0118(12) 0.0116(14) 0.0197(14) 0.0047(10) 0.0008(10) 0.0024(9) C2 0.0121(12) 0.0134(14) 0.0140(13) 0.0001(9) 0.0014(10) -0.0048(9) C4 0.0109(12) 0.0202(15) 0.0128(12) 0.0016(11) -0.0025(10) -0.0022(10) C1 0.0130(12) 0.0163(14) 0.0118(12) -0.0009(10) -0.0013(9) 0.0005(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N4 H4A 0.94(3) . ? N4 H4B 0.93(3) . ? N4 H4C 1.00(3) . ? N4 H4D 0.94(3) . ? N1 C2 1.334(3) . ? N1 H1B 0.78(3) . ? N1 H1A 0.98(3) . ? N2 C3 1.153(3) . ? N3 C4 1.157(3) . ? O1 C2 1.275(3) . ? C3 C1 1.402(3) . ? C2 C1 1.438(3) . ? C4 C1 1.407(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag H4A N4 H4B 109(2) . . ? H4A N4 H4C 109(2) . . ? H4B N4 H4C 114(3) . . ? H4A N4 H4D 109(2) . . ? H4B N4 H4D 109(3) . . ? H4C N4 H4D 107(2) . . ? C2 N1 H1B 122(2) . . ? C2 N1 H1A 114.8(16) . . ? H1B N1 H1A 122(2) . . ? N2 C3 C1 176.9(2) . . ? O1 C2 N1 119.8(2) . . ? O1 C2 C1 121.3(2) . . ? N1 C2 C1 118.9(2) . . ? N3 C4 C1 177.6(3) . . ? C3 C1 C4 119.5(2) . . ? C3 C1 C2 120.7(2) . . ? C4 C1 C2 119.5(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1B O1 0.78(3) 2.58(3) 3.306(3) 156(2) 4_565 N1 H1A N2 0.98(3) 2.08(3) 3.035(3) 164(2) 4_666 N4 H4A N2 0.94(3) 2.04(3) 2.969(3) 170(2) . N4 H4B O1 0.93(3) 2.02(3) 2.952(3) 178(3) 3_765 N4 H4C O1 1.00(3) 1.97(3) 2.943(3) 162(2) 1_454 N4 H4D O1 0.94(3) 2.01(3) 2.935(3) 169(2) 1_554 _diffrn_measured_fraction_theta_max 0.892 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.892 _refine_diff_density_max 0.176 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.052 data_2 _database_code_depnum_ccdc_archive 'CCDC 701913' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Methylammonium carbamoyldicyanomethanide ; _chemical_name_common MeH3cdm _chemical_melting_point ? _chemical_formula_moiety 'C4 H2 N3 O, C N H6' _chemical_formula_sum 'C5 H8 N4 O' _chemical_formula_weight 140.15 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.8451(3) _cell_length_b 12.8144(6) _cell_length_c 9.5395(5) _cell_angle_alpha 90.00 _cell_angle_beta 103.573(4) _cell_angle_gamma 90.00 _cell_volume 694.57(6) _cell_formula_units_Z 4 _cell_measurement_temperature 123(1) _cell_measurement_reflns_used 3840 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 27.49 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9764 _exptl_absorpt_correction_T_max 0.9803 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 Apex II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3840 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0570 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1539 _reflns_number_gt 1286 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker)' _computing_cell_refinement 'Bruker SMART (Bruker)' _computing_data_reduction 'Bruker SAINT (Bruker)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_extinction_expression ? _refine_ls_number_reflns 1539 _refine_ls_number_parameters 112 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0695 _refine_ls_R_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.1279 _refine_ls_wR_factor_gt 0.1185 _refine_ls_goodness_of_fit_ref 1.137 _refine_ls_restrained_S_all 1.137 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.0843(2) 0.24353(11) 0.29627(13) 0.0202(4) Uani 1 1 d . . . N1 N 0.1441(3) 0.28654(15) 0.51399(18) 0.0234(4) Uani 1 1 d . . . N2 N 0.6644(3) 0.13170(14) 0.55674(17) 0.0257(4) Uani 1 1 d . . . N3 N 0.2254(3) 0.08370(14) 0.11181(16) 0.0236(4) Uani 1 1 d . . . N4 N 0.0801(3) 0.10446(14) 0.78881(17) 0.0187(4) Uani 1 1 d . . . C1 C 0.2930(3) 0.17009(15) 0.36010(18) 0.0167(4) Uani 1 1 d . . . C2 C 0.1071(3) 0.23485(15) 0.38839(19) 0.0170(4) Uani 1 1 d . . . C3 C 0.4996(3) 0.14818(15) 0.46649(19) 0.0184(4) Uani 1 1 d . . . C4 C 0.2571(3) 0.12242(15) 0.22429(19) 0.0181(4) Uani 1 1 d . . . C5 C 0.2101(4) 0.02524(17) 0.7258(3) 0.0325(5) Uani 1 1 d . . . H5B H 0.2177 0.0468 0.6285 0.049 Uiso 1 1 calc R . . H5C H 0.1288 -0.0420 0.7210 0.049 Uiso 1 1 calc R . . H5A H 0.3700 0.0184 0.7862 0.049 Uiso 1 1 calc R . . H1A H 0.015(4) 0.3222(18) 0.533(2) 0.029(6) Uiso 1 1 d . . . H1B H 0.262(4) 0.2775(18) 0.576(2) 0.023(6) Uiso 1 1 d . . . H4A H -0.070(5) 0.118(2) 0.725(3) 0.049(8) Uiso 1 1 d . . . H4B H 0.176(4) 0.1648(19) 0.804(2) 0.034(7) Uiso 1 1 d . . . H4C H 0.065(4) 0.0880(19) 0.882(3) 0.043(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0174(7) 0.0257(8) 0.0146(6) 0.0007(6) -0.0021(5) 0.0044(6) N1 0.0201(9) 0.0307(11) 0.0157(8) -0.0050(8) -0.0030(7) 0.0069(8) N2 0.0199(9) 0.0330(11) 0.0212(8) -0.0017(8) -0.0012(7) 0.0041(8) N3 0.0243(10) 0.0270(10) 0.0187(8) -0.0005(7) 0.0036(7) 0.0010(8) N4 0.0173(9) 0.0213(10) 0.0154(8) -0.0002(7) -0.0002(6) -0.0002(7) C1 0.0161(9) 0.0194(11) 0.0132(8) 0.0007(7) 0.0005(7) 0.0008(8) C2 0.0179(9) 0.0162(10) 0.0154(8) 0.0012(7) 0.0006(7) -0.0006(8) C3 0.0188(10) 0.0188(11) 0.0184(9) -0.0018(8) 0.0061(8) 0.0001(8) C4 0.0153(9) 0.0191(11) 0.0191(9) 0.0036(8) 0.0025(7) 0.0008(8) C5 0.0269(12) 0.0226(12) 0.0515(14) -0.0025(11) 0.0164(10) 0.0020(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.255(2) . ? N1 C2 1.341(2) . ? N1 H1A 0.94(2) . ? N1 H1B 0.80(2) . ? N2 C3 1.151(2) . ? N3 C4 1.157(2) . ? N4 C5 1.478(3) . ? N4 H4A 0.96(3) . ? N4 H4B 0.95(3) . ? N4 H4C 0.94(3) . ? C1 C4 1.403(2) . ? C1 C3 1.411(3) . ? C1 C2 1.442(3) . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C5 H5A 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 H1A 116.5(14) . . ? C2 N1 H1B 121.0(16) . . ? H1A N1 H1B 121(2) . . ? C5 N4 H4A 110.0(16) . . ? C5 N4 H4B 106.2(15) . . ? H4A N4 H4B 112(2) . . ? C5 N4 H4C 113.9(16) . . ? H4A N4 H4C 111(2) . . ? H4B N4 H4C 103(2) . . ? C4 C1 C3 119.64(17) . . ? C4 C1 C2 117.89(17) . . ? C3 C1 C2 122.34(16) . . ? O1 C2 N1 120.80(18) . . ? O1 C2 C1 120.47(16) . . ? N1 C2 C1 118.73(17) . . ? N2 C3 C1 177.64(19) . . ? N3 C4 C1 179.3(2) . . ? N4 C5 H5B 109.5 . . ? N4 C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N4 C5 H5A 109.5 . . ? H5B C5 H5A 109.5 . . ? H5C C5 H5A 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A N3 0.94(2) 2.34(2) 3.271(2) 172.2(19) 4_566 N1 H1B O1 0.80(2) 2.10(2) 2.813(2) 148(2) 4_666 N4 H4A N2 0.96(3) 1.96(3) 2.899(2) 165(2) 1_455 N4 H4B O1 0.95(3) 1.84(3) 2.753(2) 161(2) 4_666 N4 H4C N3 0.94(3) 2.17(3) 3.010(2) 148(2) 1_556 _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.225 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.055 data_3 _database_code_depnum_ccdc_archive 'CCDC 701914' _audit_creation_method SHELXL-97 _chemical_name_systematic ; dimethylammonium carbamoyldicyanomethanide ; _chemical_name_common '[Me2H2N](cdm)' _chemical_melting_point ? _chemical_formula_moiety 'C4 H2 N3 O, C2 H8 N' _chemical_formula_sum 'C6 H10 N4 O' _chemical_formula_weight 154.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.1880(18) _cell_length_b 8.2151(21) _cell_length_c 8.5656(23) _cell_angle_alpha 71.608(8) _cell_angle_beta 65.906(8) _cell_angle_gamma 75.772(8) _cell_volume 434.13(19) _cell_formula_units_Z 2 _cell_measurement_temperature 123(1) _cell_measurement_reflns_used 1969 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 24.98 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.179 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 164 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9831 _exptl_absorpt_correction_T_max 0.9873 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 Apex II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1969 _diffrn_reflns_av_R_equivalents 0.0259 _diffrn_reflns_av_sigmaI/netI 0.0499 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 24.98 _reflns_number_total 1340 _reflns_number_gt 1186 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker)' _computing_cell_refinement 'Bruker SMART (Bruker)' _computing_data_reduction 'Bruker SAINT (Bruker)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.103(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1340 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0817 _refine_ls_R_factor_gt 0.0710 _refine_ls_wR_factor_ref 0.1662 _refine_ls_wR_factor_gt 0.1602 _refine_ls_goodness_of_fit_ref 1.174 _refine_ls_restrained_S_all 1.174 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.2003(3) 0.0733(2) 0.0500(3) 0.0243(6) Uani 1 1 d . . . N1 N -0.1367(4) 0.1799(4) 0.1031(4) 0.0289(7) Uani 1 1 d . . . N2 N -0.2315(4) 0.5518(3) 0.2759(4) 0.0348(8) Uani 1 1 d . . . N3 N 0.4163(5) 0.3016(4) 0.2006(4) 0.0400(9) Uani 1 1 d . . . N4 N 0.4174(4) 0.8313(3) 0.2455(3) 0.0251(7) Uani 1 1 d . . . C1 C 0.0650(5) 0.3079(4) 0.1858(4) 0.0225(8) Uani 1 1 d . . . C2 C 0.0449(5) 0.1827(4) 0.1099(4) 0.0226(7) Uani 1 1 d . . . C3 C -0.0964(5) 0.4430(4) 0.2350(4) 0.0248(8) Uani 1 1 d . . . C4 C 0.2562(6) 0.3071(4) 0.1935(4) 0.0265(8) Uani 1 1 d . . . C5 C 0.3027(6) 0.6870(4) 0.2841(5) 0.0402(10) Uani 1 1 d . . . H5A H 0.3543 0.5836 0.3584 0.060 Uiso 1 1 calc R . . H5B H 0.3221 0.6622 0.1734 0.060 Uiso 1 1 calc R . . H5C H 0.1560 0.7200 0.3461 0.060 Uiso 1 1 calc R . . C6 C 0.4085(6) 0.8697(4) 0.4075(4) 0.0352(9) Uani 1 1 d . . . H6A H 0.2648 0.9009 0.4791 0.053 Uiso 1 1 calc R . . H6B H 0.4854 0.9663 0.3739 0.053 Uiso 1 1 calc R . . H6C H 0.4693 0.7672 0.4758 0.053 Uiso 1 1 calc R . . H1A H -0.147(5) 0.103(5) 0.053(5) 0.033(10) Uiso 1 1 d . . . H4A H 0.367(6) 0.932(6) 0.169(5) 0.050(11) Uiso 1 1 d . . . H4B H 0.565(7) 0.811(6) 0.169(6) 0.066(13) Uiso 1 1 d . . . H1B H -0.247(6) 0.252(5) 0.146(5) 0.044(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0198(12) 0.0212(11) 0.0309(12) -0.0125(9) -0.0086(9) 0.0059(8) N1 0.0191(17) 0.0308(15) 0.0411(17) -0.0202(13) -0.0119(13) 0.0059(12) N2 0.0327(17) 0.0290(15) 0.0355(16) -0.0128(13) -0.0083(13) 0.0078(13) N3 0.0279(19) 0.0321(16) 0.068(2) -0.0303(15) -0.0188(16) 0.0086(13) N4 0.0212(16) 0.0251(14) 0.0264(14) -0.0092(12) -0.0086(12) 0.0052(11) C1 0.0181(19) 0.0203(15) 0.0280(16) -0.0100(13) -0.0070(13) 0.0023(12) C2 0.0184(18) 0.0217(15) 0.0249(16) -0.0064(12) -0.0068(13) 0.0018(12) C3 0.0233(18) 0.0245(16) 0.0253(16) -0.0070(13) -0.0094(14) 0.0011(13) C4 0.023(2) 0.0189(15) 0.0369(18) -0.0153(13) -0.0078(15) 0.0036(12) C5 0.057(3) 0.0263(18) 0.045(2) -0.0080(15) -0.0265(19) -0.0044(17) C6 0.043(2) 0.0339(18) 0.0328(18) -0.0155(15) -0.0155(16) 0.0015(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.284(4) . ? N1 C2 1.336(4) . ? N1 H1A 0.90(4) . ? N1 H1B 0.89(4) . ? N2 C3 1.165(4) . ? N3 C4 1.166(4) . ? N4 C5 1.485(4) . ? N4 C6 1.490(4) . ? N4 H4A 0.97(4) . ? N4 H4B 1.00(5) . ? C1 C4 1.401(5) . ? C1 C3 1.420(4) . ? C1 C2 1.440(4) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 H1A 119(2) . . ? C2 N1 H1B 122(2) . . ? H1A N1 H1B 119(3) . . ? C5 N4 C6 113.1(3) . . ? C5 N4 H4A 109(2) . . ? C6 N4 H4A 112(2) . . ? C5 N4 H4B 113(3) . . ? C6 N4 H4B 108(3) . . ? H4A N4 H4B 101(3) . . ? C4 C1 C3 119.2(3) . . ? C4 C1 C2 118.8(3) . . ? C3 C1 C2 121.7(3) . . ? O1 C2 N1 120.0(3) . . ? O1 C2 C1 120.2(3) . . ? N1 C2 C1 119.7(3) . . ? N2 C3 C1 178.7(3) . . ? N3 C4 C1 178.1(3) . . ? N4 C5 H5A 109.5 . . ? N4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N4 C6 H6A 109.5 . . ? N4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O1 0.90(4) 2.09(4) 2.989(3) 175(3) 2 N4 H4A O1 0.97(4) 1.84(4) 2.775(3) 159(3) 1_565 N4 H4B O1 1.00(5) 2.08(5) 2.950(3) 144(4) 2_665 N4 H4B N2 1.00(5) 2.42(5) 3.003(4) 117(3) 1_655 N1 H1B N3 0.89(4) 2.22(4) 2.963(4) 141(3) 1_455 _diffrn_measured_fraction_theta_max 0.877 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.877 _refine_diff_density_max 0.212 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.057 data_4 _database_code_depnum_ccdc_archive 'CCDC 701915' _audit_creation_method SHELXL-97 _chemical_name_systematic ; trimethylammonium carbamoyldicyanomethanide ; _chemical_name_common '[Me3HN](cdm)' _chemical_melting_point ? _chemical_formula_moiety 'C4 H2 N3 O, (C3 H10 N)' _chemical_formula_sum 'C7 H12 N4 O' _chemical_formula_weight 168.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.6961(12) _cell_length_b 7.0629(4) _cell_length_c 16.3887(9) _cell_angle_alpha 90.00 _cell_angle_beta 125.203(3) _cell_angle_gamma 90.00 _cell_volume 1862.90(19) _cell_formula_units_Z 8 _cell_measurement_temperature 123(1) _cell_measurement_reflns_used 5317 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 27.49 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.199 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9765 _exptl_absorpt_correction_T_max 0.9831 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 Apex II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5317 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0384 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2130 _reflns_number_gt 1882 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker)' _computing_cell_refinement 'Bruker SMART (Bruker)' _computing_data_reduction 'Bruker SAINT (Bruker)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_extinction_expression ? _refine_ls_number_reflns 2130 _refine_ls_number_parameters 124 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0574 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1087 _refine_ls_wR_factor_gt 0.1034 _refine_ls_goodness_of_fit_ref 1.128 _refine_ls_restrained_S_all 1.128 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.02971(6) 0.24169(14) 0.06086(7) 0.0195(2) Uani 1 1 d . . . N1 N 0.04946(9) -0.04455(18) 0.13221(10) 0.0222(3) Uani 1 1 d . . . N2 N 0.13631(9) 0.05171(18) 0.39250(10) 0.0266(3) Uani 1 1 d . . . N3 N 0.10872(10) 0.59259(18) 0.24564(10) 0.0326(4) Uani 1 1 d . . . N4 N 0.14416(8) 0.43580(18) 0.05124(9) 0.0219(3) Uani 1 1 d . . . C1 C 0.08922(9) 0.23329(19) 0.23284(10) 0.0174(3) Uani 1 1 d . . . C2 C 0.05441(9) 0.14404(19) 0.13805(10) 0.0164(3) Uani 1 1 d . . . C3 C 0.11428(9) 0.13294(19) 0.32027(11) 0.0179(3) Uani 1 1 d . . . C4 C 0.09940(10) 0.4306(2) 0.23951(10) 0.0210(3) Uani 1 1 d . . . C5 C 0.21202(12) 0.3007(3) 0.11698(15) 0.0415(5) Uani 1 1 d . . . H5A H 0.2607 0.3309 0.1173 0.062 Uiso 1 1 calc R . . H5B H 0.1935 0.1715 0.0921 0.062 Uiso 1 1 calc R . . H5C H 0.2267 0.3104 0.1850 0.062 Uiso 1 1 calc R . . C6 C 0.11907(11) 0.4200(2) -0.05261(12) 0.0299(4) Uani 1 1 d . . . H6A H 0.1024 0.2893 -0.0758 0.045 Uiso 1 1 calc R . . H6B H 0.1659 0.4550 -0.0552 0.045 Uiso 1 1 calc R . . H6C H 0.0722 0.5052 -0.0956 0.045 Uiso 1 1 calc R . . C7 C 0.16779(11) 0.6337(2) 0.08726(13) 0.0308(4) Uani 1 1 d . . . H7A H 0.1215 0.7186 0.0420 0.046 Uiso 1 1 calc R . . H7B H 0.2167 0.6696 0.0891 0.046 Uiso 1 1 calc R . . H7C H 0.1807 0.6436 0.1545 0.046 Uiso 1 1 calc R . . H1N H 0.0661(13) -0.117(3) 0.1849(16) 0.039(5) Uiso 1 1 d . . . H2N H 0.0274(12) -0.098(3) 0.0759(15) 0.033(5) Uiso 1 1 d . . . H3N H 0.1010(12) 0.399(2) 0.0544(13) 0.029(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0224(5) 0.0184(5) 0.0164(5) 0.0009(4) 0.0105(5) -0.0023(4) N1 0.0318(8) 0.0153(6) 0.0185(7) -0.0016(5) 0.0139(6) -0.0009(5) N2 0.0345(8) 0.0237(7) 0.0241(7) 0.0030(5) 0.0182(6) 0.0016(6) N3 0.0505(10) 0.0198(7) 0.0208(7) 0.0000(5) 0.0167(7) -0.0027(6) N4 0.0193(6) 0.0269(7) 0.0214(6) 0.0040(5) 0.0128(6) 0.0014(5) C1 0.0197(7) 0.0152(7) 0.0180(7) 0.0001(5) 0.0113(6) -0.0014(5) C2 0.0146(7) 0.0171(7) 0.0197(7) 0.0004(5) 0.0112(6) -0.0005(5) C3 0.0192(7) 0.0160(7) 0.0208(7) -0.0029(5) 0.0129(6) -0.0015(5) C4 0.0252(8) 0.0213(8) 0.0136(7) 0.0001(6) 0.0096(6) -0.0010(6) C5 0.0305(10) 0.0450(11) 0.0476(11) 0.0250(9) 0.0218(9) 0.0131(8) C6 0.0343(9) 0.0347(9) 0.0241(8) -0.0040(7) 0.0188(8) -0.0028(7) C7 0.0268(9) 0.0344(9) 0.0306(9) -0.0104(7) 0.0162(8) -0.0043(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.2661(16) . ? N1 C2 1.3349(18) . ? N1 H1N 0.89(2) . ? N1 H2N 0.85(2) . ? N2 C3 1.1518(19) . ? N3 C4 1.1540(19) . ? N4 C6 1.478(2) . ? N4 C5 1.482(2) . ? N4 C7 1.484(2) . ? N4 H3N 0.92(2) . ? C1 C4 1.4031(19) . ? C1 C3 1.4083(19) . ? C1 C2 1.4328(19) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 H1N 122.3(12) . . ? C2 N1 H2N 119.3(13) . . ? H1N N1 H2N 118.3(17) . . ? C6 N4 C5 110.57(14) . . ? C6 N4 C7 110.45(12) . . ? C5 N4 C7 111.87(14) . . ? C6 N4 H3N 109.7(11) . . ? C5 N4 H3N 104.5(11) . . ? C7 N4 H3N 109.5(11) . . ? C4 C1 C3 118.04(13) . . ? C4 C1 C2 118.62(13) . . ? C3 C1 C2 123.34(12) . . ? O1 C2 N1 120.12(13) . . ? O1 C2 C1 120.78(12) . . ? N1 C2 C1 119.10(13) . . ? N2 C3 C1 178.71(16) . . ? N3 C4 C1 179.24(17) . . ? N4 C5 H5A 109.5 . . ? N4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N4 C6 H6A 109.5 . . ? N4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N4 C7 H7A 109.5 . . ? N4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N N3 0.89(2) 2.22(2) 2.9807(19) 143.2(17) 1_545 N1 H2N O1 0.85(2) 2.10(2) 2.9485(17) 176.7(18) 5 N4 H3N O1 0.92(2) 1.84(2) 2.7197(17) 159.5(16) . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.227 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.046 data_5 _database_code_depnum_ccdc_archive 'CCDC 701916' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Tetramethylammonium carbamoyldicyanomethanide ; _chemical_name_common Me4Ncdm _chemical_melting_point ? _chemical_formula_moiety 'C4 H2 N3 O, C4 H12 N' _chemical_formula_sum 'C8 H14 N4 O' _chemical_formula_weight 182.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.9167(3) _cell_length_b 8.8432(3) _cell_length_c 13.5613(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.897(2) _cell_angle_gamma 90.00 _cell_volume 1065.43(6) _cell_formula_units_Z 4 _cell_measurement_temperature 123(1) _cell_measurement_reflns_used 7650 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 27.49 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.136 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9835 _exptl_absorpt_correction_T_max 0.9890 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 Apex II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7650 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0292 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2435 _reflns_number_gt 2073 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker)' _computing_cell_refinement 'Bruker SMART (Bruker)' _computing_data_reduction 'Bruker SAINT (Bruker)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_extinction_expression ? _refine_ls_number_reflns 2435 _refine_ls_number_parameters 130 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0490 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.0978 _refine_ls_wR_factor_gt 0.0933 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.44190(9) 0.12428(9) 0.10202(5) 0.0222(2) Uani 1 1 d . . . N1 N 0.34442(13) 0.10812(13) -0.05693(7) 0.0246(2) Uani 1 1 d . . . N2 N 0.22744(12) 0.37712(13) 0.23075(7) 0.0272(3) Uani 1 1 d . . . N3 N 0.02299(12) 0.34555(12) -0.07962(7) 0.0275(3) Uani 1 1 d . . . N4 N 0.74554(11) 0.36199(11) 0.22528(7) 0.0209(2) Uani 1 1 d . . . C1 C 0.23056(12) 0.27439(12) 0.05448(8) 0.0169(2) Uani 1 1 d . . . C2 C 0.34489(12) 0.16575(12) 0.03484(8) 0.0174(2) Uani 1 1 d . . . C3 C 0.22868(12) 0.33238(13) 0.15118(8) 0.0186(2) Uani 1 1 d . . . C4 C 0.11547(13) 0.31490(12) -0.01788(8) 0.0179(2) Uani 1 1 d . . . C5 C 0.81276(17) 0.26303(16) 0.15189(11) 0.0377(3) Uani 1 1 d . . . H5A H 0.8639 0.3257 0.1054 0.057 Uiso 1 1 calc R . . H5B H 0.7331 0.2041 0.1155 0.057 Uiso 1 1 calc R . . H5C H 0.8856 0.1942 0.1865 0.057 Uiso 1 1 calc R . . C6 C 0.86674(14) 0.45307(14) 0.28000(10) 0.0275(3) Uani 1 1 d . . . H6A H 0.9159 0.5168 0.2332 0.041 Uiso 1 1 calc R . . H6B H 0.9412 0.3850 0.3138 0.041 Uiso 1 1 calc R . . H6C H 0.8227 0.5171 0.3289 0.041 Uiso 1 1 calc R . . C7 C 0.66884(15) 0.26636(16) 0.29661(10) 0.0337(3) Uani 1 1 d . . . H7A H 0.7423 0.1979 0.3310 0.051 Uiso 1 1 calc R . . H7B H 0.5891 0.2070 0.2606 0.051 Uiso 1 1 calc R . . H7C H 0.6248 0.3314 0.3450 0.051 Uiso 1 1 calc R . . C8 C 0.63269(15) 0.46541(16) 0.17346(10) 0.0325(3) Uani 1 1 d . . . H8A H 0.5521 0.4056 0.1387 0.049 Uiso 1 1 calc R . . H8B H 0.6817 0.5273 0.1256 0.049 Uiso 1 1 calc R . . H8C H 0.5900 0.5313 0.2220 0.049 Uiso 1 1 calc R . . H1A H 0.4141(17) 0.0414(17) -0.0678(10) 0.028(4) Uiso 1 1 d . . . H1B H 0.2790(18) 0.1359(17) -0.1043(11) 0.034(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0219(4) 0.0282(5) 0.0156(4) -0.0027(3) -0.0034(3) 0.0070(3) N1 0.0261(5) 0.0321(6) 0.0148(5) -0.0045(4) -0.0030(4) 0.0131(5) N2 0.0291(6) 0.0341(6) 0.0180(5) -0.0053(4) -0.0013(4) 0.0075(5) N3 0.0293(6) 0.0304(6) 0.0216(5) -0.0030(4) -0.0052(4) 0.0081(5) N4 0.0172(5) 0.0183(5) 0.0273(5) -0.0014(4) 0.0027(4) -0.0002(4) C1 0.0179(5) 0.0190(5) 0.0134(5) -0.0004(4) -0.0006(4) 0.0017(4) C2 0.0174(5) 0.0194(6) 0.0153(5) 0.0005(4) 0.0007(4) -0.0014(4) C3 0.0170(5) 0.0192(6) 0.0193(6) 0.0014(4) -0.0001(4) 0.0028(4) C4 0.0213(6) 0.0168(5) 0.0157(5) -0.0022(4) 0.0026(4) 0.0016(4) C5 0.0355(8) 0.0353(8) 0.0435(8) -0.0146(6) 0.0109(6) 0.0027(6) C6 0.0238(6) 0.0244(6) 0.0334(7) -0.0003(5) -0.0024(5) -0.0044(5) C7 0.0306(7) 0.0343(7) 0.0367(7) 0.0067(6) 0.0052(6) -0.0097(6) C8 0.0232(6) 0.0337(7) 0.0399(8) 0.0067(6) -0.0023(5) 0.0050(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.2563(13) . ? N1 C2 1.3445(14) . ? N1 H1A 0.878(16) . ? N1 H1B 0.866(16) . ? N2 C3 1.1503(14) . ? N3 C4 1.1561(15) . ? N4 C5 1.4891(15) . ? N4 C8 1.4906(15) . ? N4 C6 1.4934(15) . ? N4 C7 1.4939(15) . ? C1 C4 1.4044(15) . ? C1 C3 1.4096(15) . ? C1 C2 1.4421(15) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 H1A 117.6(9) . . ? C2 N1 H1B 121.9(10) . . ? H1A N1 H1B 120.5(13) . . ? C5 N4 C8 109.85(10) . . ? C5 N4 C6 109.49(10) . . ? C8 N4 C6 109.52(10) . . ? C5 N4 C7 109.44(10) . . ? C8 N4 C7 108.94(10) . . ? C6 N4 C7 109.60(10) . . ? C4 C1 C3 119.42(10) . . ? C4 C1 C2 121.79(9) . . ? C3 C1 C2 118.62(9) . . ? O1 C2 N1 120.54(10) . . ? O1 C2 C1 120.96(10) . . ? N1 C2 C1 118.50(10) . . ? N2 C3 C1 178.77(12) . . ? N3 C4 C1 177.82(12) . . ? N4 C5 H5A 109.5 . . ? N4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N4 C6 H6A 109.5 . . ? N4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N4 C7 H7A 109.5 . . ? N4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N4 C8 H8A 109.5 . . ? N4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O1 0.878(16) 2.028(16) 2.9029(13) 174.0(13) 3_655 N1 H1B N2 0.866(16) 2.247(16) 2.9803(14) 142.4(13) 4_565 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.259 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.039 data_6 _database_code_depnum_ccdc_archive 'CCDC 701917' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Triethylmethylammonium carbamoyldicyanomethanide ; _chemical_name_common 'Triethylmethylammonium carbamoyldicyanomethanide' _chemical_melting_point ? _chemical_formula_moiety 'C7 H18 N, C4 H2 N3 O' _chemical_formula_sum 'C11 H20 N4 O' _chemical_formula_weight 224.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 19.1746(18) _cell_length_b 9.5707(8) _cell_length_c 13.9859(18) _cell_angle_alpha 90.00 _cell_angle_beta 93.109(4) _cell_angle_gamma 90.00 _cell_volume 2562.8(5) _cell_formula_units_Z 8 _cell_measurement_temperature 123(1) _cell_measurement_reflns_used 7784 _cell_measurement_theta_min 1.06 _cell_measurement_theta_max 24.99 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.163 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9770 _exptl_absorpt_correction_T_max 0.9922 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 Apex II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7784 _diffrn_reflns_av_R_equivalents 0.0377 _diffrn_reflns_av_sigmaI/netI 0.0728 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.06 _diffrn_reflns_theta_max 24.99 _reflns_number_total 4020 _reflns_number_gt 3203 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker)' _computing_cell_refinement 'Bruker SMART (Bruker)' _computing_data_reduction 'Bruker SAINT (Bruker)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_extinction_expression ? _refine_ls_number_reflns 4020 _refine_ls_number_parameters 313 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1346 _refine_ls_R_factor_gt 0.1091 _refine_ls_wR_factor_ref 0.2425 _refine_ls_wR_factor_gt 0.2274 _refine_ls_goodness_of_fit_ref 1.207 _refine_ls_restrained_S_all 1.207 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.28058(13) 0.5938(3) 0.1566(2) 0.0174(8) Uani 1 1 d . . . O2 O 0.22384(14) 0.3984(3) 0.3613(2) 0.0201(8) Uani 1 1 d . . . N1 N 0.3122(2) 0.6286(5) 0.3118(3) 0.0227(10) Uani 1 1 d . . . N2 N 0.4541(2) 0.8729(5) 0.3155(4) 0.0342(12) Uani 1 1 d . . . N3 N 0.37530(19) 0.8213(4) 0.0151(4) 0.0250(10) Uani 1 1 d . . . N4 N 0.1955(2) 0.3548(5) 0.2051(3) 0.0202(10) Uani 1 1 d . . . N5 N 0.05635(19) 0.1057(4) 0.2019(3) 0.0289(11) Uani 1 1 d . . . N6 N 0.12018(19) 0.1885(4) 0.5042(3) 0.0244(10) Uani 1 1 d . . . N7 N 0.11931(17) 0.6876(4) 0.5077(3) 0.0197(9) Uani 1 1 d . . . N8 N 0.38301(16) 0.1679(4) 0.4783(3) 0.0195(10) Uani 1 1 d . . . C1 C 0.3694(2) 0.7564(4) 0.1926(4) 0.0144(10) Uani 1 1 d . . . C2 C 0.31851(19) 0.6547(4) 0.2194(4) 0.0148(10) Uani 1 1 d . . . C3 C 0.4163(2) 0.8207(4) 0.2596(4) 0.0186(11) Uani 1 1 d . . . C4 C 0.37320(19) 0.7924(4) 0.0950(4) 0.0181(11) Uani 1 1 d . . . C5 C 0.1334(2) 0.2396(4) 0.3265(4) 0.0154(10) Uani 1 1 d . . . C6 C 0.1863(2) 0.3364(4) 0.2990(4) 0.0155(10) Uani 1 1 d . . . C7 C 0.0906(2) 0.1660(4) 0.2588(4) 0.0155(10) Uani 1 1 d . . . C8 C 0.1264(2) 0.2116(4) 0.4236(4) 0.0177(11) Uani 1 1 d . . . C9 C 0.0880(3) 0.5585(5) 0.4594(5) 0.0361(15) Uani 1 1 d . . . H9A H 0.1177 0.5281 0.4085 0.054 Uiso 1 1 calc R . . H9B H 0.0412 0.5804 0.4318 0.054 Uiso 1 1 calc R . . H9C H 0.0848 0.4836 0.5067 0.054 Uiso 1 1 calc R . . C10 C 0.1936(2) 0.6581(5) 0.5395(5) 0.0326(14) Uani 1 1 d . . . H10A H 0.2145 0.7448 0.5669 0.039 Uiso 1 1 calc R . . H10B H 0.2195 0.6333 0.4825 0.039 Uiso 1 1 calc R . . C11 C 0.2036(2) 0.5426(6) 0.6125(5) 0.0373(15) Uani 1 1 d . . . H11A H 0.1808 0.5684 0.6710 0.056 Uiso 1 1 calc R . . H11B H 0.2536 0.5283 0.6273 0.056 Uiso 1 1 calc R . . H11C H 0.1829 0.4560 0.5865 0.056 Uiso 1 1 calc R . . C12 C 0.0737(2) 0.7223(5) 0.5896(4) 0.0279(13) Uani 1 1 d . . . H12A H 0.0253 0.7377 0.5637 0.034 Uiso 1 1 calc R . . H12B H 0.0732 0.6412 0.6336 0.034 Uiso 1 1 calc R . . C13 C 0.0974(3) 0.8485(6) 0.6452(5) 0.0429(16) Uani 1 1 d . . . H13A H 0.1434 0.8305 0.6768 0.064 Uiso 1 1 calc R . . H13B H 0.0639 0.8697 0.6936 0.064 Uiso 1 1 calc R . . H13C H 0.1006 0.9282 0.6016 0.064 Uiso 1 1 calc R . . C14 C 0.1203(3) 0.8044(5) 0.4347(5) 0.0375(15) Uani 1 1 d . . . H14A H 0.1475 0.8831 0.4636 0.045 Uiso 1 1 calc R . . H14B H 0.1455 0.7708 0.3792 0.045 Uiso 1 1 calc R . . C15 C 0.0507(3) 0.8590(6) 0.3986(5) 0.0471(18) Uani 1 1 d . . . H15A H 0.0212 0.7811 0.3756 0.071 Uiso 1 1 calc R . . H15B H 0.0570 0.9246 0.3459 0.071 Uiso 1 1 calc R . . H15C H 0.0283 0.9072 0.4506 0.071 Uiso 1 1 calc R . . C16 C 0.4062(2) 0.0389(4) 0.5302(4) 0.0209(11) Uani 1 1 d . . . H16A H 0.3665 -0.0029 0.5609 0.031 Uiso 1 1 calc R . . H16B H 0.4428 0.0626 0.5792 0.031 Uiso 1 1 calc R . . H16C H 0.4246 -0.0279 0.4849 0.031 Uiso 1 1 calc R . . C17 C 0.3398(3) 0.2580(6) 0.5385(4) 0.0342(14) Uani 1 1 d . . . H17A H 0.2987 0.2038 0.5574 0.041 Uiso 1 1 calc R . . H17B H 0.3223 0.3385 0.4997 0.041 Uiso 1 1 calc R . . C18 C 0.3785(3) 0.3123(6) 0.6279(5) 0.0450(16) Uani 1 1 d . . . H18A H 0.4207 0.3617 0.6103 0.067 Uiso 1 1 calc R . . H18B H 0.3916 0.2338 0.6701 0.067 Uiso 1 1 calc R . . H18C H 0.3483 0.3767 0.6612 0.067 Uiso 1 1 calc R . . C19 C 0.4474(2) 0.2406(5) 0.4471(5) 0.0312(14) Uani 1 1 d . . . H19A H 0.4719 0.1773 0.4042 0.037 Uiso 1 1 calc R . . H19B H 0.4789 0.2577 0.5043 0.037 Uiso 1 1 calc R . . C20 C 0.4341(3) 0.3787(5) 0.3956(5) 0.0423(17) Uani 1 1 d . . . H20A H 0.4132 0.4451 0.4391 0.063 Uiso 1 1 calc R . . H20B H 0.4021 0.3637 0.3395 0.063 Uiso 1 1 calc R . . H20C H 0.4784 0.4164 0.3751 0.063 Uiso 1 1 calc R . . C21 C 0.3391(3) 0.1275(6) 0.3876(5) 0.0371(15) Uani 1 1 d . . . H21A H 0.3170 0.2130 0.3600 0.045 Uiso 1 1 calc R . . H21B H 0.3707 0.0900 0.3401 0.045 Uiso 1 1 calc R . . C22 C 0.2832(3) 0.0220(6) 0.4025(5) 0.0460(18) Uani 1 1 d . . . H22A H 0.2534 0.0548 0.4526 0.069 Uiso 1 1 calc R . . H22B H 0.3047 -0.0672 0.4220 0.069 Uiso 1 1 calc R . . H22C H 0.2549 0.0092 0.3427 0.069 Uiso 1 1 calc R . . H1N H 0.284(3) 0.555(6) 0.320(4) 0.030(15) Uiso 1 1 d . . . H2N H 0.335(3) 0.660(7) 0.353(6) 0.06(2) Uiso 1 1 d . . . H3N H 0.219(2) 0.422(5) 0.197(4) 0.009(12) Uiso 1 1 d . . . H4N H 0.169(2) 0.324(5) 0.163(4) 0.015(13) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0183(14) 0.0263(17) 0.007(2) -0.0010(13) -0.0049(13) -0.0072(13) O2 0.0208(14) 0.0308(18) 0.008(2) 0.0007(14) -0.0033(13) -0.0065(13) N1 0.028(2) 0.026(2) 0.013(3) 0.0001(18) -0.0018(18) -0.0097(19) N2 0.028(2) 0.050(3) 0.024(3) -0.015(2) -0.0002(19) -0.014(2) N3 0.028(2) 0.032(2) 0.016(3) 0.008(2) 0.0016(17) -0.0088(17) N4 0.025(2) 0.027(2) 0.009(3) -0.0039(18) 0.0018(18) -0.0117(19) N5 0.030(2) 0.033(2) 0.024(3) 0.000(2) -0.0004(19) -0.0129(19) N6 0.035(2) 0.027(2) 0.011(3) 0.0021(18) 0.0021(18) -0.0036(17) N7 0.0202(17) 0.0189(19) 0.020(3) 0.0000(17) 0.0004(16) -0.0006(15) N8 0.0143(16) 0.022(2) 0.022(3) 0.0029(17) -0.0027(15) 0.0054(15) C1 0.0181(19) 0.017(2) 0.008(3) 0.0030(18) -0.0008(17) 0.0003(17) C2 0.0163(19) 0.020(2) 0.008(3) -0.0003(19) 0.0018(17) 0.0023(17) C3 0.022(2) 0.019(2) 0.015(3) 0.0012(19) 0.0040(19) -0.0022(18) C4 0.0105(18) 0.017(2) 0.027(4) -0.001(2) -0.0036(18) -0.0032(16) C5 0.0176(19) 0.023(2) 0.005(3) 0.0025(19) 0.0019(17) 0.0004(17) C6 0.0192(19) 0.017(2) 0.010(3) 0.0013(18) 0.0018(18) 0.0042(17) C7 0.021(2) 0.021(2) 0.006(3) 0.0047(19) 0.0069(18) 0.0023(18) C8 0.020(2) 0.014(2) 0.018(4) -0.0006(19) -0.0010(19) -0.0057(17) C9 0.033(3) 0.022(3) 0.053(5) -0.007(3) -0.004(3) -0.001(2) C10 0.014(2) 0.034(3) 0.050(5) -0.013(3) 0.003(2) -0.004(2) C11 0.021(2) 0.039(3) 0.050(5) 0.006(3) -0.007(2) 0.005(2) C12 0.020(2) 0.027(3) 0.037(4) 0.008(2) 0.003(2) 0.000(2) C13 0.036(3) 0.046(3) 0.047(5) -0.011(3) 0.004(3) 0.008(3) C14 0.052(3) 0.023(3) 0.038(5) -0.001(2) 0.002(3) -0.010(2) C15 0.062(4) 0.036(3) 0.041(5) 0.015(3) -0.012(3) -0.006(3) C16 0.020(2) 0.018(2) 0.024(3) 0.004(2) -0.0046(19) -0.0008(18) C17 0.034(3) 0.044(3) 0.026(4) 0.006(3) 0.011(2) 0.013(2) C18 0.060(4) 0.042(3) 0.033(5) -0.002(3) 0.003(3) 0.027(3) C19 0.030(2) 0.027(3) 0.039(4) 0.004(2) 0.021(2) 0.005(2) C20 0.053(3) 0.029(3) 0.048(5) 0.013(3) 0.025(3) 0.013(3) C21 0.038(3) 0.043(3) 0.029(4) 0.001(3) -0.005(2) 0.011(2) C22 0.031(3) 0.044(3) 0.060(5) -0.013(3) -0.022(3) 0.004(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.254(5) . ? O2 C6 1.249(5) . ? N1 C2 1.328(7) . ? N1 H1N 0.90(6) . ? N1 H2N 0.76(8) . ? N2 C3 1.151(6) . ? N3 C4 1.154(6) . ? N4 C6 1.346(7) . ? N4 H3N 0.80(5) . ? N4 H4N 0.81(5) . ? N5 C7 1.159(6) . ? N6 C8 1.162(6) . ? N7 C10 1.495(5) . ? N7 C14 1.514(7) . ? N7 C12 1.515(7) . ? N7 C9 1.516(6) . ? N8 C16 1.488(5) . ? N8 C17 1.489(7) . ? N8 C19 1.502(6) . ? N8 C21 1.533(7) . ? C1 C3 1.405(6) . ? C1 C4 1.413(7) . ? C1 C2 1.442(6) . ? C5 C8 1.397(7) . ? C5 C7 1.408(6) . ? C5 C6 1.442(6) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.510(8) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.494(7) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.496(7) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.511(8) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.520(7) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.495(8) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 H1N 111(4) . . ? C2 N1 H2N 126(6) . . ? H1N N1 H2N 122(7) . . ? C6 N4 H3N 110(4) . . ? C6 N4 H4N 124(4) . . ? H3N N4 H4N 122(5) . . ? C10 N7 C14 107.0(4) . . ? C10 N7 C12 113.3(4) . . ? C14 N7 C12 112.1(4) . . ? C10 N7 C9 109.1(3) . . ? C14 N7 C9 108.7(4) . . ? C12 N7 C9 106.5(4) . . ? C16 N8 C17 111.4(4) . . ? C16 N8 C19 107.3(3) . . ? C17 N8 C19 112.8(4) . . ? C16 N8 C21 109.3(4) . . ? C17 N8 C21 108.5(4) . . ? C19 N8 C21 107.4(4) . . ? C3 C1 C4 118.2(4) . . ? C3 C1 C2 122.7(5) . . ? C4 C1 C2 119.1(4) . . ? O1 C2 N1 121.0(4) . . ? O1 C2 C1 120.4(5) . . ? N1 C2 C1 118.6(4) . . ? N2 C3 C1 179.0(6) . . ? N3 C4 C1 179.0(4) . . ? C8 C5 C7 118.3(4) . . ? C8 C5 C6 119.3(4) . . ? C7 C5 C6 122.3(5) . . ? O2 C6 N4 121.2(4) . . ? O2 C6 C5 120.4(5) . . ? N4 C6 C5 118.4(4) . . ? N5 C7 C5 178.8(5) . . ? N6 C8 C5 179.7(5) . . ? N7 C9 H9A 109.5 . . ? N7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N7 C10 C11 115.1(4) . . ? N7 C10 H10A 108.5 . . ? C11 C10 H10A 108.5 . . ? N7 C10 H10B 108.5 . . ? C11 C10 H10B 108.5 . . ? H10A C10 H10B 107.5 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 N7 113.5(4) . . ? C13 C12 H12A 108.9 . . ? N7 C12 H12A 108.9 . . ? C13 C12 H12B 108.9 . . ? N7 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 N7 116.2(5) . . ? C15 C14 H14A 108.2 . . ? N7 C14 H14A 108.2 . . ? C15 C14 H14B 108.2 . . ? N7 C14 H14B 108.2 . . ? H14A C14 H14B 107.4 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N8 C16 H16A 109.5 . . ? N8 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N8 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N8 C17 C18 113.8(4) . . ? N8 C17 H17A 108.8 . . ? C18 C17 H17A 108.8 . . ? N8 C17 H17B 108.8 . . ? C18 C17 H17B 108.8 . . ? H17A C17 H17B 107.7 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N8 C19 C20 114.9(4) . . ? N8 C19 H19A 108.5 . . ? C20 C19 H19A 108.5 . . ? N8 C19 H19B 108.5 . . ? C20 C19 H19B 108.5 . . ? H19A C19 H19B 107.5 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 C21 N8 114.9(5) . . ? C22 C21 H21A 108.6 . . ? N8 C21 H21A 108.6 . . ? C22 C21 H21B 108.6 . . ? N8 C21 H21B 108.6 . . ? H21A C21 H21B 107.5 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O2 0.90(6) 2.00(6) 2.886(5) 171(5) . N4 H3N O1 0.80(5) 2.12(5) 2.912(5) 172(5) . N4 H4N N6 0.81(5) 2.36(6) 3.115(6) 154(5) 4_565 N1 H2N N3 0.76(8) 2.36(8) 3.067(7) 154(7) 4_576 _diffrn_measured_fraction_theta_max 0.891 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.891 _refine_diff_density_max 0.469 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.069 data_7 _database_code_depnum_ccdc_archive 'CCDC 701918' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Benzyltrimethylammonium Carbamoyldicyanomethanide ; _chemical_name_common BzMe3N(cdm) _chemical_melting_point ? _chemical_formula_moiety 'C10 H16 N, C4 H2 N3 O' _chemical_formula_sum 'C14 H18 N4 O' _chemical_formula_weight 258.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.4203(19) _cell_length_b 17.1223(36) _cell_length_c 9.8809(23) _cell_angle_alpha 90.00 _cell_angle_beta 116.939(7) _cell_angle_gamma 90.00 _cell_volume 1420.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 123(1) _cell_measurement_reflns_used 6809 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 27.49 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.208 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9811 _exptl_absorpt_correction_T_max 0.9811 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 Apex II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6809 _diffrn_reflns_av_R_equivalents 0.0570 _diffrn_reflns_av_sigmaI/netI 0.0795 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3528 _reflns_number_gt 3155 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker)' _computing_cell_refinement 'Bruker SMART (Bruker)' _computing_data_reduction 'Bruker SAINT (Bruker)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Compound refined as a racemic twin. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_extinction_expression ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(0) _refine_ls_number_reflns 3528 _refine_ls_number_parameters 365 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0614 _refine_ls_R_factor_gt 0.0549 _refine_ls_wR_factor_ref 0.1295 _refine_ls_wR_factor_gt 0.1225 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.0351(3) 0.23712(14) 0.3229(3) 0.0269(6) Uani 1 1 d . . . O2 O 0.9360(3) 0.03489(13) 0.2887(3) 0.0255(6) Uani 1 1 d . . . N1 N 0.1963(5) 0.13878(17) 0.3281(4) 0.0262(7) Uani 1 1 d . . . N2 N 0.5685(4) 0.22732(18) 0.3981(4) 0.0348(9) Uani 1 1 d . . . N3 N 0.2347(4) 0.41767(19) 0.3351(4) 0.0343(8) Uani 1 1 d . . . N4 N 0.8217(5) 0.12915(17) 0.3669(4) 0.0261(7) Uani 1 1 d . . . N5 N 0.4839(4) 0.03840(17) 0.3813(4) 0.0271(7) Uani 1 1 d . . . N6 N 0.6652(4) -0.12719(19) 0.1592(5) 0.0406(9) Uani 1 1 d . . . N7 N 0.2436(4) 0.60423(17) 0.1278(3) 0.0234(7) Uani 1 1 d . . . N8 N 0.7897(4) 0.41179(17) 0.3603(4) 0.0257(7) Uani 1 1 d . . . C1 C 0.2915(4) 0.2705(2) 0.3581(4) 0.0228(8) Uani 1 1 d . . . C2 C 0.1681(5) 0.21519(19) 0.3367(4) 0.0216(8) Uani 1 1 d . . . C3 C 0.4431(5) 0.24741(19) 0.3795(4) 0.0236(8) Uani 1 1 d . . . C4 C 0.2579(4) 0.3520(2) 0.3460(5) 0.0255(8) Uani 1 1 d . . . C5 C 0.6991(4) 0.00313(19) 0.2990(4) 0.0212(7) Uani 1 1 d . . . C6 C 0.8240(4) 0.05596(19) 0.3167(4) 0.0235(8) Uani 1 1 d . . . C7 C 0.5812(4) 0.02184(19) 0.3447(4) 0.0229(8) Uani 1 1 d . . . C8 C 0.6829(5) -0.06915(19) 0.2248(5) 0.0276(8) Uani 1 1 d . . . C9 C 0.0865(5) 0.5836(2) 0.1212(6) 0.0411(12) Uani 1 1 d . . . H9A H 0.0103 0.5713 0.0162 0.062 Uiso 1 1 calc R . . H9B H 0.0469 0.6279 0.1572 0.062 Uiso 1 1 calc R . . H9C H 0.0992 0.5381 0.1858 0.062 Uiso 1 1 calc R . . C10 C 0.3007(5) 0.5344(2) 0.0749(4) 0.0318(9) Uani 1 1 d . . . H10A H 0.3130 0.4900 0.1420 0.048 Uiso 1 1 calc R . . H10B H 0.4035 0.5464 0.0771 0.048 Uiso 1 1 calc R . . H10C H 0.2230 0.5212 -0.0290 0.048 Uiso 1 1 calc R . . C11 C 0.3617(5) 0.6224(2) 0.2881(5) 0.0408(11) Uani 1 1 d . . . H11A H 0.3227 0.6663 0.3257 0.061 Uiso 1 1 calc R . . H11B H 0.4641 0.6364 0.2912 0.061 Uiso 1 1 calc R . . H11C H 0.3757 0.5765 0.3521 0.061 Uiso 1 1 calc R . . C12 C 0.2257(5) 0.67214(19) 0.0220(4) 0.0260(8) Uani 1 1 d . . . H12A H 0.3273 0.6790 0.0166 0.031 Uiso 1 1 calc R . . H12B H 0.1429 0.6587 -0.0811 0.031 Uiso 1 1 calc R . . C13 C 0.1816(5) 0.7487(2) 0.0689(4) 0.0261(8) Uani 1 1 d . . . C14 C 0.0237(5) 0.7658(2) 0.0293(4) 0.0293(9) Uani 1 1 d . . . H14 H -0.0579 0.7294 -0.0272 0.035 Uiso 1 1 calc R . . C15 C -0.0142(6) 0.8377(2) 0.0737(5) 0.0399(11) Uani 1 1 d . . . H15 H -0.1221 0.8499 0.0470 0.048 Uiso 1 1 calc R . . C16 C 0.1042(7) 0.8906(2) 0.1558(5) 0.0447(12) Uani 1 1 d . . . H16 H 0.0781 0.9389 0.1866 0.054 Uiso 1 1 calc R . . C17 C 0.2598(7) 0.8734(2) 0.1929(5) 0.0465(12) Uani 1 1 d . . . H17 H 0.3411 0.9102 0.2482 0.056 Uiso 1 1 calc R . . C18 C 0.2995(6) 0.8026(2) 0.1502(5) 0.0358(10) Uani 1 1 d . . . H18 H 0.4076 0.7910 0.1768 0.043 Uiso 1 1 calc R . . C19 C 0.6885(5) 0.4503(2) 0.4227(5) 0.0319(9) Uani 1 1 d . . . H19A H 0.6125 0.4857 0.3464 0.048 Uiso 1 1 calc R . . H19B H 0.7567 0.4800 0.5141 0.048 Uiso 1 1 calc R . . H19C H 0.6304 0.4103 0.4485 0.048 Uiso 1 1 calc R . . C20 C 0.6877(6) 0.3666(3) 0.2202(5) 0.0418(11) Uani 1 1 d . . . H20A H 0.6246 0.3283 0.2434 0.063 Uiso 1 1 calc R . . H20B H 0.7555 0.3394 0.1839 0.063 Uiso 1 1 calc R . . H20C H 0.6163 0.4025 0.1415 0.063 Uiso 1 1 calc R . . C21 C 0.9027(5) 0.3572(2) 0.4792(5) 0.0342(9) Uani 1 1 d . . . H21A H 0.8421 0.3163 0.4998 0.051 Uiso 1 1 calc R . . H21B H 0.9663 0.3864 0.5727 0.051 Uiso 1 1 calc R . . H21C H 0.9735 0.3331 0.4428 0.051 Uiso 1 1 calc R . . C22 C 0.8894(5) 0.4716(2) 0.3269(5) 0.0278(9) Uani 1 1 d . . . H22A H 0.9748 0.4903 0.4248 0.033 Uiso 1 1 calc R . . H22B H 0.9413 0.4450 0.2721 0.033 Uiso 1 1 calc R . . C23 C 0.8009(4) 0.5416(2) 0.2353(4) 0.0237(8) Uani 1 1 d . . . C24 C 0.7264(5) 0.5419(2) 0.0768(4) 0.0309(9) Uani 1 1 d . . . H24 H 0.7212 0.4951 0.0230 0.037 Uiso 1 1 calc R . . C25 C 0.6601(5) 0.6098(2) -0.0025(5) 0.0345(10) Uani 1 1 d . . . H25 H 0.6092 0.6092 -0.1103 0.041 Uiso 1 1 calc R . . C26 C 0.6670(5) 0.6784(2) 0.0731(5) 0.0335(9) Uani 1 1 d . . . H26 H 0.6224 0.7249 0.0174 0.040 Uiso 1 1 calc R . . C27 C 0.7389(5) 0.6797(2) 0.2305(5) 0.0338(9) Uani 1 1 d . . . H27 H 0.7427 0.7266 0.2832 0.041 Uiso 1 1 calc R . . C28 C 0.8058(5) 0.6110(2) 0.3105(5) 0.0301(9) Uani 1 1 d . . . H28 H 0.8556 0.6118 0.4184 0.036 Uiso 1 1 calc R . . H1A H 0.290(5) 0.123(2) 0.350(5) 0.029(12) Uiso 1 1 d . . . H1B H 0.123(5) 0.111(3) 0.323(5) 0.036(13) Uiso 1 1 d . . . H4A H 0.738(5) 0.146(2) 0.372(4) 0.020(10) Uiso 1 1 d . . . H4B H 0.898(5) 0.164(2) 0.369(5) 0.030(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0241(16) 0.0243(12) 0.0368(15) -0.0014(11) 0.0178(12) 0.0002(11) O2 0.0217(14) 0.0243(12) 0.0352(14) -0.0022(11) 0.0170(12) 0.0015(11) N1 0.022(2) 0.0197(15) 0.041(2) 0.0046(13) 0.0179(16) 0.0031(15) N2 0.028(2) 0.0238(16) 0.059(3) 0.0054(15) 0.0248(18) -0.0010(15) N3 0.029(2) 0.0249(15) 0.052(2) 0.0002(15) 0.0215(17) 0.0002(15) N4 0.0169(19) 0.0238(15) 0.044(2) -0.0097(13) 0.0196(16) -0.0043(14) N5 0.0297(19) 0.0226(14) 0.0322(17) -0.0028(13) 0.0168(15) -0.0013(14) N6 0.045(2) 0.0256(16) 0.067(3) -0.0097(17) 0.040(2) -0.0072(17) N7 0.0214(18) 0.0257(15) 0.0285(17) 0.0035(13) 0.0159(14) 0.0031(13) N8 0.0261(18) 0.0244(14) 0.0324(18) -0.0024(13) 0.0183(15) -0.0033(14) C1 0.018(2) 0.0208(16) 0.031(2) 0.0026(14) 0.0123(16) -0.0009(15) C2 0.023(2) 0.0212(16) 0.0252(19) 0.0002(14) 0.0145(16) 0.0022(15) C3 0.023(2) 0.0199(16) 0.032(2) 0.0015(14) 0.0162(17) -0.0029(16) C4 0.018(2) 0.0226(17) 0.039(2) -0.0013(15) 0.0160(17) -0.0054(16) C5 0.0154(19) 0.0187(15) 0.033(2) 0.0014(14) 0.0141(15) 0.0009(14) C6 0.021(2) 0.0241(17) 0.0238(18) 0.0025(14) 0.0087(16) 0.0018(16) C7 0.025(2) 0.0170(15) 0.0276(19) 0.0032(13) 0.0125(16) -0.0018(15) C8 0.026(2) 0.0209(17) 0.043(2) -0.0003(15) 0.0227(18) -0.0015(16) C9 0.034(3) 0.029(2) 0.073(3) 0.018(2) 0.036(2) 0.0071(19) C10 0.035(2) 0.0268(17) 0.038(2) 0.0002(17) 0.0205(19) 0.0083(18) C11 0.051(3) 0.039(2) 0.026(2) 0.0026(17) 0.013(2) 0.007(2) C12 0.029(2) 0.0246(17) 0.0256(19) 0.0022(15) 0.0135(16) 0.0010(17) C13 0.032(2) 0.0216(16) 0.028(2) 0.0000(14) 0.0169(17) -0.0009(16) C14 0.035(3) 0.0274(17) 0.029(2) 0.0033(15) 0.0183(18) 0.0037(18) C15 0.047(3) 0.037(2) 0.041(2) 0.0059(19) 0.025(2) 0.017(2) C16 0.081(4) 0.0237(19) 0.042(3) -0.0005(17) 0.039(3) 0.006(2) C17 0.071(4) 0.029(2) 0.046(3) -0.0089(19) 0.033(3) -0.017(2) C18 0.041(3) 0.0324(19) 0.042(2) -0.0025(18) 0.026(2) -0.011(2) C19 0.031(2) 0.0322(19) 0.042(2) 0.0047(17) 0.0255(19) 0.0083(18) C20 0.052(3) 0.040(2) 0.036(2) -0.0109(18) 0.022(2) -0.019(2) C21 0.037(3) 0.0306(19) 0.041(2) 0.0025(17) 0.023(2) 0.0072(19) C22 0.023(2) 0.0250(17) 0.040(2) -0.0023(15) 0.0187(18) -0.0033(16) C23 0.021(2) 0.0273(17) 0.0277(18) -0.0019(15) 0.0151(15) -0.0047(15) C24 0.033(2) 0.0340(19) 0.034(2) -0.0073(17) 0.0230(18) -0.0126(18) C25 0.032(2) 0.045(2) 0.028(2) 0.0013(18) 0.0152(18) -0.010(2) C26 0.030(2) 0.0324(19) 0.039(2) 0.0040(17) 0.0155(19) -0.0059(19) C27 0.039(3) 0.0243(17) 0.042(2) -0.0046(17) 0.022(2) -0.0022(19) C28 0.035(3) 0.0312(19) 0.028(2) -0.0028(16) 0.0172(18) -0.0018(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.255(4) . ? O2 C6 1.259(4) . ? N1 C2 1.345(4) . ? N1 H1A 0.85(4) . ? N1 H1B 0.82(4) . ? N2 C3 1.162(5) . ? N3 C4 1.141(5) . ? N4 C6 1.352(4) . ? N4 H4A 0.86(4) . ? N4 H4B 0.93(4) . ? N5 C7 1.163(4) . ? N6 C8 1.156(5) . ? N7 C9 1.494(5) . ? N7 C11 1.499(5) . ? N7 C10 1.499(4) . ? N7 C12 1.521(4) . ? N8 C20 1.494(5) . ? N8 C21 1.502(5) . ? N8 C19 1.502(5) . ? N8 C22 1.524(4) . ? C1 C3 1.403(5) . ? C1 C4 1.424(5) . ? C1 C2 1.439(5) . ? C5 C8 1.411(5) . ? C5 C7 1.412(5) . ? C5 C6 1.431(5) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.510(5) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C18 1.385(5) . ? C13 C14 1.387(5) . ? C14 C15 1.405(5) . ? C14 H14 0.9500 . ? C15 C16 1.380(6) . ? C15 H15 0.9500 . ? C16 C17 1.373(7) . ? C16 H16 0.9500 . ? C17 C18 1.390(6) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C23 1.506(5) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C28 1.391(5) . ? C23 C24 1.396(5) . ? C24 C25 1.384(6) . ? C24 H24 0.9500 . ? C25 C26 1.378(6) . ? C25 H25 0.9500 . ? C26 C27 1.386(6) . ? C26 H26 0.9500 . ? C27 C28 1.397(5) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 H1A 120(3) . . ? C2 N1 H1B 113(3) . . ? H1A N1 H1B 125(4) . . ? C6 N4 H4A 120(2) . . ? C6 N4 H4B 117(2) . . ? H4A N4 H4B 120(3) . . ? C9 N7 C11 110.0(3) . . ? C9 N7 C10 107.5(3) . . ? C11 N7 C10 108.8(3) . . ? C9 N7 C12 110.6(3) . . ? C11 N7 C12 111.4(3) . . ? C10 N7 C12 108.4(3) . . ? C20 N8 C21 109.4(3) . . ? C20 N8 C19 110.3(3) . . ? C21 N8 C19 108.0(3) . . ? C20 N8 C22 110.4(3) . . ? C21 N8 C22 107.5(3) . . ? C19 N8 C22 111.2(3) . . ? C3 C1 C4 117.5(3) . . ? C3 C1 C2 122.4(3) . . ? C4 C1 C2 119.9(3) . . ? O1 C2 N1 120.0(4) . . ? O1 C2 C1 121.3(3) . . ? N1 C2 C1 118.7(3) . . ? N2 C3 C1 179.1(4) . . ? N3 C4 C1 177.9(4) . . ? C8 C5 C7 116.7(3) . . ? C8 C5 C6 120.5(3) . . ? C7 C5 C6 122.7(3) . . ? O2 C6 N4 120.1(3) . . ? O2 C6 C5 121.1(3) . . ? N4 C6 C5 118.8(3) . . ? N5 C7 C5 178.9(4) . . ? N6 C8 C5 177.5(5) . . ? N7 C9 H9A 109.5 . . ? N7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N7 C10 H10A 109.5 . . ? N7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N7 C11 H11A 109.5 . . ? N7 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N7 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 N7 114.4(3) . . ? C13 C12 H12A 108.7 . . ? N7 C12 H12A 108.7 . . ? C13 C12 H12B 108.7 . . ? N7 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? C18 C13 C14 119.9(4) . . ? C18 C13 C12 119.7(4) . . ? C14 C13 C12 120.4(3) . . ? C13 C14 C15 119.3(4) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? C16 C15 C14 120.4(4) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C17 C16 C15 119.8(4) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 C18 120.5(4) . . ? C16 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? C13 C18 C17 120.1(4) . . ? C13 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? N8 C19 H19A 109.5 . . ? N8 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N8 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N8 C20 H20A 109.5 . . ? N8 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N8 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N8 C21 H21A 109.5 . . ? N8 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N8 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 C22 N8 116.0(3) . . ? C23 C22 H22A 108.3 . . ? N8 C22 H22A 108.3 . . ? C23 C22 H22B 108.3 . . ? N8 C22 H22B 108.3 . . ? H22A C22 H22B 107.4 . . ? C28 C23 C24 118.4(3) . . ? C28 C23 C22 118.9(3) . . ? C24 C23 C22 122.5(3) . . ? C25 C24 C23 120.4(4) . . ? C25 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? C26 C25 C24 120.8(4) . . ? C26 C25 H25 119.6 . . ? C24 C25 H25 119.6 . . ? C25 C26 C27 120.0(4) . . ? C25 C26 H26 120.0 . . ? C27 C26 H26 120.0 . . ? C26 C27 C28 119.2(4) . . ? C26 C27 H27 120.4 . . ? C28 C27 H27 120.4 . . ? C23 C28 C27 121.2(4) . . ? C23 C28 H28 119.4 . . ? C27 C28 H28 119.4 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4B O1 0.93(4) 1.99(4) 2.906(4) 167(4) 1_655 N4 H4A N2 0.86(4) 2.22(4) 3.045(5) 160(3) . N1 H1B O2 0.82(4) 2.09(5) 2.909(5) 174(4) 1_455 N1 H1A N5 0.85(4) 2.24(4) 3.047(5) 157(4) . _diffrn_measured_fraction_theta_max 0.870 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.870 _refine_diff_density_max 0.208 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.052