This journal is (c) The Owner Societies 1999 # CCDC Number: 1326/1 data_SQ2 _audit_creation_method SHELXL _chemical_name_systematic ; 1,3-bis(dimethylamino)-2,4-dihydroxy-cyclobutendiylium dihydroxide, bis(inner salt), dihydrate ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C8 H16 N2 O4' _chemical_formula_weight 204.23 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' .0106 .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 P2(1)/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 8.0254(11) _cell_length_b 7.4851(14) _cell_length_c 17.7967(33) _cell_angle_alpha 90.00 _cell_angle_beta 90.98(2) _cell_angle_gamma 90.00 _cell_volume 1068.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 96 _cell_measurement_theta_min 11.232 _cell_measurement_theta_max 13.965 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.269 _exptl_crystal_density_method ? _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; crystal sample sealed into a Lindemann glass capillary ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoKa _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 3.15 _diffrn_reflns_number 9820 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.51 _reflns_number_total 2456 _reflns_number_observed 1402 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'local program CELLA' _computing_data_reduction 'Siemens XSCANS' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL-93 (Sheldrick, 1993)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[s^2^(Fo^2^)+( 0.0555P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0439(34) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^l^3^/sin(2q)]^-1/4^' _refine_ls_number_reflns 2456 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0706 _refine_ls_R_factor_obs 0.0359 _refine_ls_wR_factor_all 0.0970 _refine_ls_wR_factor_obs 0.0879 _refine_ls_goodness_of_fit_all 0.877 _refine_ls_goodness_of_fit_obs 1.084 _refine_ls_restrained_S_all 0.877 _refine_ls_restrained_S_obs 1.084 _refine_ls_shift/esd_max 0.024 _refine_ls_shift/esd_mean 0.003 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1A O 0.22860(13) 0.1283(2) -0.05123(6) 0.0592(3) Uani 1 d . . N1A N 0.1157(2) 0.0520(2) 0.11946(6) 0.0477(3) Uani 1 d . . C1A C 0.1036(2) 0.0592(2) -0.02386(8) 0.0414(3) Uani 1 d . . C2A C 0.0498(2) 0.0223(2) 0.05232(7) 0.0397(3) Uani 1 d . . C3A C 0.2760(2) 0.1426(3) 0.12827(13) 0.0663(5) Uani 1 d . . C4A C 0.0352(3) -0.0083(4) 0.18777(10) 0.0677(6) Uani 1 d . . O1B O 0.92989(13) 0.4434(2) -0.12196(6) 0.0607(3) Uani 1 d . . N1B N 0.74971(15) 0.3743(2) 0.03917(7) 0.0459(3) Uani 1 d . . C1B C 0.9673(2) 0.4738(2) -0.05560(8) 0.0434(4) Uani 1 d . . C2B C 0.8906(2) 0.4454(2) 0.01687(8) 0.0409(3) Uani 1 d . . C3B C 0.6314(2) 0.2922(3) -0.01353(11) 0.0531(4) Uani 1 d . . C4B C 0.7095(3) 0.3642(3) 0.11890(10) 0.0655(5) Uani 1 d . . OW1 O 0.6459(2) 0.3803(2) -0.21052(8) 0.0756(4) Uani 1 d . . OW2 O 0.3836(2) 0.1558(2) -0.19022(9) 0.0886(5) Uani 1 d . . H3A1 H 0.3197(23) 0.1729(25) 0.0770(12) 0.083(6) Uiso 1 d . . H3A2 H 0.3557(30) 0.0562(30) 0.1486(13) 0.104(7) Uiso 1 d . . H3A3 H 0.2630(27) 0.2419(30) 0.1601(13) 0.102(8) Uiso 1 d . . H4A1 H 0.1072(28) -0.0872(30) 0.2162(13) 0.103(7) Uiso 1 d . . H4A2 H -0.0789(30) -0.0725(29) 0.1769(13) 0.113(8) Uiso 1 d . . H4A3 H 0.0132(27) 0.0896(34) 0.2198(14) 0.104(8) Uiso 1 d . . H3B1 H 0.6142(23) 0.1677(27) -0.0010(11) 0.081(6) Uiso 1 d . . H3B2 H 0.6656(24) 0.3034(26) -0.0660(12) 0.086(6) Uiso 1 d . . H3B3 H 0.5241(23) 0.3406(24) -0.0079(10) 0.069(5) Uiso 1 d . . H4B1 H 0.6967(26) 0.2461(29) 0.1343(12) 0.094(8) Uiso 1 d . . H4B2 H 0.7984(26) 0.4247(25) 0.1475(11) 0.084(6) Uiso 1 d . . H4B3 H 0.6002(30) 0.4307(29) 0.1267(12) 0.105(8) Uiso 1 d . . H1W1 H 0.6376(27) 0.4627(31) -0.2423(14) 0.094(8) Uiso 1 d . . H2W1 H 0.7338(31) 0.4029(30) -0.1797(13) 0.108(8) Uiso 1 d . . H1W2 H 0.4672(31) 0.2275(33) -0.1919(12) 0.106(9) Uiso 1 d . . H2W2 H 0.3442(29) 0.1563(31) -0.1480(15) 0.104(9) Uiso 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 O1A 0.0495(6) 0.0787(8) 0.0493(7) 0.0051(6) 0.0032(5) -0.0118(6) N1A 0.0473(7) 0.0589(8) 0.0366(7) -0.0056(6) -0.0044(5) 0.0026(6) C1A 0.0407(8) 0.0448(9) 0.0386(8) -0.0009(6) 0.0000(6) 0.0058(7) C2A 0.0416(8) 0.0416(8) 0.0359(7) -0.0029(6) -0.0012(6) 0.0073(6) C3A 0.0588(11) 0.0802(15) 0.0596(12) -0.0118(11) -0.0133(9) -0.0072(10) C4A 0.0703(13) 0.099(2) 0.0341(9) -0.0004(10) 0.0008(8) 0.0041(11) O1B 0.0588(7) 0.0849(9) 0.0381(6) -0.0056(6) -0.0071(5) -0.0070(6) N1B 0.0441(7) 0.0526(8) 0.0408(7) -0.0001(6) 0.0002(5) 0.0000(6) C1B 0.0448(8) 0.0455(9) 0.0396(8) -0.0001(6) -0.0044(6) 0.0044(6) C2B 0.0403(7) 0.0404(8) 0.0417(8) 0.0002(6) -0.0029(6) 0.0044(6) C3B 0.0443(10) 0.0578(11) 0.0570(11) -0.0038(9) -0.0029(8) -0.0030(8) C4B 0.0607(12) 0.088(2) 0.0481(10) 0.0034(10) 0.0054(9) -0.0079(11) OW1 0.0659(9) 0.0957(11) 0.0646(9) 0.0187(8) -0.0134(7) -0.0273(8) OW2 0.0940(11) 0.1118(13) 0.0606(9) -0.0218(9) 0.0204(8) -0.0458(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 O1A C1A 1.236(2) . ? N1A C2A 1.317(2) . ? N1A C4A 1.458(2) . ? N1A C3A 1.460(2) . ? C1A C2A 1.456(2) . ? C1A C2A 1.457(2) 3 ? C2A C1A 1.457(2) 3 ? C3A H3A1 1.01(2) . ? C3A H3A2 0.97(2) . ? C3A H3A3 0.94(2) . ? C4A H4A1 0.96(2) . ? C4A H4A2 1.05(2) . ? C4A H4A3 0.95(3) . ? O1B C1B 1.234(2) . ? N1B C2B 1.317(2) . ? N1B C3B 1.459(2) . ? N1B C4B 1.462(2) . ? C1B C2B 1.454(2) . ? C1B C2B 1.455(2) 3_765 ? C2B C1B 1.455(2) 3_765 ? C2B C2B 2.037(3) 3_765 ? C3B H3B1 0.97(2) . ? C3B H3B2 0.98(2) . ? C3B H3B3 0.94(2) . ? C4B H4B1 0.93(2) . ? C4B H4B2 0.98(2) . ? C4B H4B3 1.02(2) . ? OW1 H1W1 0.84(2) . ? OW1 H2W1 0.90(3) . ? OW2 H1W2 0.86(3) . ? OW2 H2W2 0.82(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 C2A N1A C4A 121.83(14) . . ? C2A N1A C3A 120.98(15) . . ? C4A N1A C3A 117.16(15) . . ? O1A C1A C2A 134.56(13) . . ? O1A C1A C2A 136.45(13) . 3 ? C2A C1A C2A 88.98(11) . 3 ? N1A C2A C1A 133.79(14) . . ? N1A C2A C1A 135.19(13) . 3 ? C1A C2A C1A 91.02(11) . 3 ? N1A C3A H3A1 109.1(11) . . ? N1A C3A H3A2 107.6(13) . . ? H3A1 C3A H3A2 104.4(16) . . ? N1A C3A H3A3 109.0(14) . . ? H3A1 C3A H3A3 114.3(18) . . ? H3A2 C3A H3A3 112.3(19) . . ? N1A C4A H4A1 110.9(13) . . ? N1A C4A H4A2 112.7(12) . . ? H4A1 C4A H4A2 109.3(19) . . ? N1A C4A H4A3 110.6(14) . . ? H4A1 C4A H4A3 105.9(19) . . ? H4A2 C4A H4A3 107.2(18) . . ? C2B N1B C3B 121.93(13) . . ? C2B N1B C4B 121.21(14) . . ? C3B N1B C4B 116.75(14) . . ? O1B C1B C2B 136.22(14) . . ? O1B C1B C2B 134.87(14) . 3_765 ? C2B C1B C2B 88.91(11) . 3_765 ? N1B C2B C1B 134.83(13) . . ? N1B C2B C1B 134.08(13) . 3_765 ? C1B C2B C1B 91.09(11) . 3_765 ? N1B C2B C2B 179.53(14) . 3_765 ? C1B C2B C2B 45.56(8) . 3_765 ? C1B C2B C2B 45.53(8) 3_765 3_765 ? N1B C3B H3B1 110.6(12) . . ? N1B C3B H3B2 112.7(11) . . ? H3B1 C3B H3B2 110.1(17) . . ? N1B C3B H3B3 110.8(11) . . ? H3B1 C3B H3B3 102.2(15) . . ? H3B2 C3B H3B3 109.9(15) . . ? N1B C4B H4B1 111.3(13) . . ? N1B C4B H4B2 108.0(12) . . ? H4B1 C4B H4B2 111.6(18) . . ? N1B C4B H4B3 108.1(13) . . ? H4B1 C4B H4B3 108.9(18) . . ? H4B2 C4B H4B3 108.9(17) . . ? H1W1 OW1 H2W1 108.9(20) . . ? H1W2 OW2 H2W2 110.0(21) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4A N1A C2A C1A -177.0(2) . . . . ? C3A N1A C2A C1A 1.1(3) . . . . ? C4A N1A C2A C1A 2.9(3) . . . 3 ? C3A N1A C2A C1A -179.0(2) . . . 3 ? O1A C1A C2A N1A 0.9(3) . . . . ? C2A C1A C2A N1A 180.0(2) 3 . . . ? O1A C1A C2A C1A -179.1(2) . . . 3 ? C2A C1A C2A C1A 0.0 3 . . 3 ? C3B N1B C2B C1B 3.1(3) . . . . ? C4B N1B C2B C1B 179.3(2) . . . . ? C3B N1B C2B C1B -176.4(2) . . . 3_765 ? C4B N1B C2B C1B -0.2(3) . . . 3_765 ? C3B N1B C2B C2B -143.0(203) . . . 3_765 ? C4B N1B C2B C2B 33.1(204) . . . 3_765 ? O1B C1B C2B N1B 0.4(3) . . . . ? C2B C1B C2B N1B -179.6(2) 3_765 . . . ? O1B C1B C2B C1B -180.0(2) . . . 3_765 ? C2B C1B C2B C1B 0.000(2) 3_765 . . 3_765 ? O1B C1B C2B C2B -180.0(2) . . . 3_765 ? C2B C1B C2B C2B 0.0 3_765 . . 3_765 ? _refine_diff_density_max .152 _refine_diff_density_min -.114 _refine_diff_density_rms .027 #=END data_SQ4 _audit_creation_method SHELXL _chemical_name_systematic ; 1,3-bis(dimethylamino)-2,4-dihydroxy-cyclobutendiylium dihydroxide, bis(inner salt), tetrahydrate. ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C4 H10 N O3' _chemical_formula_weight 120.13 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 21.6397(33) _cell_length_b 8.3029(10) _cell_length_c 7.1004(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1275.7(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 96 _cell_measurement_theta_min 8.921 _cell_measurement_theta_max 17.725 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_method ? _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; crystal sample with mother liquor sealed into a Lindemann glass capillary. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoKa _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 4.36 _diffrn_reflns_number 10332 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_sigmaI/netI 0.0118 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 24.98 _reflns_number_total 1123 _reflns_number_observed 923 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'local (Milano) program CELLA' _computing_data_reduction 'Siemens XSCANS' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL-93 (Sheldrick, 1993)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[s^2^(Fo^2^)+( 0.0647P)^2^+0.1306P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0699(60) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^l^3^/sin(2q)]^-1/4^' _refine_ls_number_reflns 1123 _refine_ls_number_parameters 114 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0460 _refine_ls_R_factor_obs 0.0372 _refine_ls_wR_factor_all 0.1052 _refine_ls_wR_factor_obs 0.0971 _refine_ls_goodness_of_fit_all 1.072 _refine_ls_goodness_of_fit_obs 1.103 _refine_ls_restrained_S_all 1.072 _refine_ls_restrained_S_obs 1.103 _refine_ls_shift/esd_max -0.009 _refine_ls_shift/esd_mean 0.001 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group OW1 O 0.31483(6) 0.8061(2) 0.1405(2) 0.0579(4) Uani 1 d . . H1W1 H 0.2916(10) 0.7278(26) 0.1916(29) 0.076(6) Uiso 1 d . . H2W1 H 0.3534(13) 0.7732(28) 0.1248(28) 0.086(7) Uiso 1 d . . OW2 O 0.24121(6) 0.5788(2) 0.3057(2) 0.0673(4) Uani 1 d . . H1W2 H 0.2223(10) 0.6081(25) 0.3998(34) 0.071(6) Uiso 1 d . . H2W2 H 0.2162(11) 0.5020(30) 0.2573(35) 0.089(7) Uiso 1 d . . O1 O 0.43753(5) 0.71157(13) 0.0742(2) 0.0551(4) Uani 1 d . . N1 N 0.42127(5) 0.3191(2) 0.0769(2) 0.0461(4) Uani 1 d . . C1 C 0.47120(6) 0.5962(2) 0.0345(2) 0.0396(4) Uani 1 d . . C2 C 0.46542(6) 0.4211(2) 0.0335(2) 0.0384(4) Uani 1 d . . C3 C 0.36182(7) 0.3758(3) 0.1476(3) 0.0592(5) Uani 1 d . . H31 H 0.3292(14) 0.3477(36) 0.0696(40) 0.120(9) Uiso 1 d . . H32 H 0.3528(13) 0.3206(33) 0.2591(41) 0.111(8) Uiso 1 d . . H33 H 0.3612(13) 0.4929(37) 0.1735(36) 0.118(9) Uiso 1 d . . C4 C 0.42980(10) 0.1463(2) 0.0573(4) 0.0675(5) Uani 1 d . . H41 H 0.4253(11) 0.0970(30) 0.1744(36) 0.093(8) Uiso 1 d . . H42 H 0.4703(12) 0.1249(29) 0.0019(31) 0.095(7) Uiso 1 d . . H43 H 0.3975(14) 0.0993(31) -0.0201(37) 0.110(8) Uiso 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 OW1 0.0484(7) 0.0529(7) 0.0724(8) 0.0036(6) 0.0039(6) 0.0092(5) OW2 0.0601(8) 0.0670(9) 0.0749(9) -0.0142(7) 0.0129(7) -0.0087(6) O1 0.0429(6) 0.0485(7) 0.0738(8) -0.0048(5) 0.0072(5) 0.0091(5) N1 0.0368(6) 0.0467(7) 0.0547(7) 0.0044(6) 0.0028(5) -0.0021(5) C1 0.0339(7) 0.0455(8) 0.0394(7) 0.0006(6) -0.0008(5) 0.0024(6) C2 0.0330(7) 0.0461(8) 0.0360(7) 0.0024(6) -0.0019(5) 0.0013(5) C3 0.0354(8) 0.0724(12) 0.0698(11) 0.0101(10) 0.0083(7) -0.0029(8) C4 0.0595(11) 0.0468(10) 0.096(2) 0.0040(10) 0.0043(11) -0.0059(8) _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 OW1 H1W1 0.90(2) . ? OW1 H2W1 0.88(3) . ? OW2 H1W2 0.82(2) . ? OW2 H2W2 0.90(3) . ? O1 C1 1.237(2) . ? N1 C2 1.314(2) . ? N1 C4 1.453(2) . ? N1 C3 1.459(2) . ? C1 C2 1.459(2) . ? C1 C2 1.461(2) 5_665 ? C2 C1 1.461(2) 5_665 ? C3 H31 0.93(3) . ? C3 H32 0.94(3) . ? C3 H33 0.99(3) . ? C4 H41 0.93(3) . ? C4 H42 0.98(2) . ? C4 H43 0.97(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 H1W1 OW1 H2W1 110.8(19) . . ? H1W2 OW2 H2W2 102.8(22) . . ? C2 N1 C4 121.46(14) . . ? C2 N1 C3 120.91(14) . . ? C4 N1 C3 117.62(15) . . ? O1 C1 C2 136.27(13) . . ? O1 C1 C2 134.81(13) . 5_665 ? C2 C1 C2 88.91(11) . 5_665 ? N1 C2 C1 134.74(13) . . ? N1 C2 C1 134.17(13) . 5_665 ? C1 C2 C1 91.09(11) . 5_665 ? N1 C3 H31 112.6(18) . . ? N1 C3 H32 108.5(17) . . ? H31 C3 H32 102.9(24) . . ? N1 C3 H33 113.1(17) . . ? H31 C3 H33 110.4(23) . . ? H32 C3 H33 108.7(22) . . ? N1 C4 H41 109.5(15) . . ? N1 C4 H42 109.4(14) . . ? H41 C4 H42 111.9(20) . . ? N1 C4 H43 111.1(15) . . ? H41 C4 H43 104.7(22) . . ? H42 C4 H43 110.1(22) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 C2 C1 179.0(2) . . . . ? C3 N1 C2 C1 -1.3(2) . . . . ? C4 N1 C2 C1 -1.4(3) . . . 5_665 ? C3 N1 C2 C1 178.3(2) . . . 5_665 ? O1 C1 C2 N1 -0.6(3) . . . . ? C2 C1 C2 N1 179.7(2) 5_665 . . . ? O1 C1 C2 C1 179.7(2) . . . 5_665 ? C2 C1 C2 C1 0.0 5_665 . . 5_665 ? _refine_diff_density_max .162 _refine_diff_density_min -.161 _refine_diff_density_rms .039