# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 1145/157 data_datam _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C2 H6 N O4 P Sn' _chemical_formula_weight 257.74 _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' 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' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Sn' 'Sn' -0.6537 1.4246 '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 18.0967(13) _cell_length_b 7.8886(6) _cell_length_c 9.1507(7) _cell_angle_alpha 90.00 _cell_angle_beta 111.838(2) _cell_angle_gamma 90.00 _cell_volume 1212.6(2) _cell_formula_units_Z 6 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.118 _exptl_crystal_density_method ? _exptl_crystal_F_000 732 _exptl_absorpt_coefficient_mu 3.313 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2412 _diffrn_reflns_av_R_equivalents 0.0414 _diffrn_reflns_av_sigmaI/netI 0.0358 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 23.26 _reflns_number_total 873 _reflns_number_observed 791 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _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^)+(0.0197P)^2^+10.2010P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0022(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 873 _refine_ls_number_parameters 83 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0325 _refine_ls_R_factor_obs 0.0263 _refine_ls_wR_factor_all 0.0611 _refine_ls_wR_factor_obs 0.0588 _refine_ls_goodness_of_fit_all 1.112 _refine_ls_goodness_of_fit_obs 1.131 _refine_ls_restrained_S_all 1.112 _refine_ls_restrained_S_obs 1.131 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Sn1 Sn 0.26115(2) -0.51360(5) -0.03807(4) 0.0175(2) Uani 1 d . . P1 P 0.34484(9) -0.2684(2) 0.2613(2) 0.0148(4) Uani 1 d . . O1 O 0.3544(2) -0.3652(5) 0.1203(4) 0.0219(9) Uani 1 d . . O2 O 0.3510(2) -0.3974(5) 0.3902(5) 0.0216(9) Uani 1 d . . O3 O 0.2598(2) -0.1918(5) 0.1996(4) 0.0236(10) Uani 1 d . . O4 O 0.4076(2) -0.1332(5) 0.3184(5) 0.0241(10) Uani 1 d . . N1 N 0.5564(3) -0.1981(6) 0.5420(6) 0.0263(12) Uani 1 d . . H1 H 0.5777(3) -0.2645(6) 0.4894(6) 0.039 Uiso 1 calc R . H2 H 0.5912(3) -0.1179(6) 0.5923(6) 0.039 Uiso 1 calc R . H3 H 0.5124(3) -0.1500(6) 0.4748(6) 0.039 Uiso 1 calc R . C1 C 0.5363(4) -0.3017(8) 0.6585(7) 0.030(2) Uani 1 d . . H4 H 0.5842(4) -0.3554(8) 0.7308(7) 0.035 Uiso 1 calc R . H5 H 0.4990(4) -0.3901(8) 0.6039(7) 0.035 Uiso 1 calc R . C2 C 0.5000 -0.1924(12) 0.7500 0.029(2) Uani 1 d S . H6 H 0.5439(43) -0.1329(95) 0.8149(91) 0.051(23) 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 Sn1 0.0204(3) 0.0163(3) 0.0170(3) 0.0006(2) 0.0082(2) -0.0009(2) P1 0.0190(8) 0.0134(7) 0.0114(7) 0.0008(6) 0.0048(6) -0.0012(6) O1 0.021(2) 0.031(2) 0.015(2) -0.004(2) 0.007(2) -0.004(2) O2 0.024(2) 0.020(2) 0.022(2) 0.006(2) 0.010(2) -0.001(2) O3 0.026(2) 0.030(2) 0.016(2) 0.008(2) 0.009(2) 0.001(2) O4 0.025(2) 0.021(2) 0.023(2) -0.004(2) 0.006(2) -0.006(2) N1 0.030(3) 0.024(3) 0.025(3) -0.005(2) 0.011(2) 0.002(2) C1 0.032(4) 0.025(3) 0.033(4) 0.004(3) 0.015(3) 0.004(3) C2 0.036(6) 0.028(5) 0.027(5) 0.000 0.015(5) 0.000 _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 Sn1 O2 2.088(4) 6_545 ? Sn1 O1 2.122(4) . ? Sn1 O3 2.130(4) 7_545 ? P1 O4 1.503(4) . ? P1 O2 1.530(4) . ? P1 O3 1.551(4) . ? P1 O1 1.563(4) . ? O2 Sn1 2.088(4) 6_546 ? O3 Sn1 2.130(4) 7_545 ? N1 C1 1.492(8) . ? C1 C2 1.512(8) . ? C2 C1 1.512(8) 2_656 ? 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 O2 Sn1 O1 83.43(15) 6_545 . ? O2 Sn1 O3 89.77(15) 6_545 7_545 ? O1 Sn1 O3 86.86(15) . 7_545 ? O4 P1 O2 112.0(2) . . ? O4 P1 O3 111.7(2) . . ? O2 P1 O3 108.5(2) . . ? O4 P1 O1 109.4(2) . . ? O2 P1 O1 108.2(2) . . ? O3 P1 O1 106.8(2) . . ? P1 O1 Sn1 121.9(2) . . ? P1 O2 Sn1 128.6(2) . 6_546 ? P1 O3 Sn1 116.4(2) . 7_545 ? N1 C1 C2 110.8(5) . . ? C1 C2 C1 110.5(8) . 2_656 ? _refine_diff_density_max 0.656 _refine_diff_density_min -0.575 _refine_diff_density_rms 0.142 data_sad _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C2 H6 N O4 P Sn' _chemical_formula_weight 257.74 _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' 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' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Sn' 'Sn' -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? 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 18.1327(13) _cell_length_b 7.8581(6) _cell_length_c 9.3441(7) _cell_angle_alpha 90.00 _cell_angle_beta 111.300(2) _cell_angle_gamma 90.00 _cell_volume 1240.5(2) _cell_formula_units_Z 6 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.070 _exptl_crystal_density_method ? _exptl_crystal_F_000 732 _exptl_absorpt_coefficient_mu 3.239 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2549 _diffrn_reflns_av_R_equivalents 0.0481 _diffrn_reflns_av_sigmaI/netI 0.0518 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 23.28 _reflns_number_total 898 _reflns_number_observed 867 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0619P)^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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0121(9) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 898 _refine_ls_number_parameters 89 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0403 _refine_ls_R_factor_obs 0.0394 _refine_ls_wR_factor_all 0.1094 _refine_ls_wR_factor_obs 0.1087 _refine_ls_goodness_of_fit_all 1.277 _refine_ls_goodness_of_fit_obs 1.292 _refine_ls_restrained_S_all 1.277 _refine_ls_restrained_S_obs 1.292 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Sn1 Sn 0.26303(2) -0.51647(6) -0.04299(4) 0.0195(4) Uani 1 d . . P1 P 0.34568(8) -0.2745(2) 0.2517(2) 0.0165(5) Uani 1 d . . O1 O 0.3552(2) -0.3698(5) 0.1126(4) 0.0245(9) Uani 1 d . . O2 O 0.3503(2) -0.4079(5) 0.3749(4) 0.0229(10) Uani 1 d . . O3 O 0.2617(2) -0.1960(5) 0.1949(5) 0.0267(11) Uani 1 d . . O4 O 0.4094(2) -0.1419(6) 0.3098(5) 0.0294(10) Uani 1 d . . O10 O 0.5601(5) -0.1005(11) 0.8467(9) 0.041(3) Uani 0.58(2) d P . H7 H 0.5780(5) -0.0382(11) 0.7968(9) 0.061 Uiso 0.58(2) calc PR . N1 N 0.5535(3) -0.2017(7) 0.5422(6) 0.0300(13) Uani 1 d . . H3 H 0.5725(3) -0.2687(7) 0.4868(6) 0.045 Uiso 1 calc R . H2 H 0.5900(3) -0.1254(7) 0.5924(6) 0.045 Uiso 1 calc R . H1 H 0.5105(3) -0.1482(7) 0.4802(6) 0.045 Uiso 1 calc R . C1 C 0.5323(4) -0.3080(10) 0.6559(8) 0.031(2) Uani 1 d . . H5 H 0.5789(4) -0.3675(10) 0.7231(8) 0.038 Uiso 1 calc R . H4 H 0.4928(4) -0.3921(10) 0.6018(8) 0.038 Uiso 1 calc R . C2 C 0.5000 -0.1937(12) 0.7500 0.023(2) Uani 1 d S . 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 Sn1 0.0237(5) 0.0180(5) 0.0187(5) 0.00055(13) 0.0099(3) -0.00166(13) P1 0.0186(9) 0.0165(9) 0.0130(8) 0.0008(6) 0.0042(6) -0.0019(6) O1 0.023(2) 0.033(2) 0.017(2) -0.003(2) 0.008(2) -0.001(2) O2 0.026(2) 0.023(2) 0.021(2) 0.005(2) 0.010(2) -0.002(2) O3 0.028(2) 0.030(2) 0.024(2) 0.009(2) 0.013(2) 0.007(2) O4 0.029(2) 0.025(2) 0.030(2) -0.002(2) 0.005(2) -0.013(2) O10 0.054(6) 0.044(6) 0.026(5) 0.000(4) 0.017(4) -0.018(4) N1 0.027(3) 0.040(4) 0.024(3) 0.002(2) 0.011(2) 0.009(3) C1 0.038(4) 0.025(4) 0.034(4) 0.010(3) 0.016(3) 0.014(3) C2 0.022(4) 0.023(5) 0.021(5) 0.000 0.005(4) 0.000 _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 Sn1 O2 2.081(4) 6_545 ? Sn1 O1 2.114(4) . ? Sn1 O3 2.131(4) 7_545 ? P1 O4 1.503(4) . ? P1 O2 1.536(4) . ? P1 O3 1.548(4) . ? P1 O1 1.564(4) . ? O2 Sn1 2.081(4) 6_546 ? O3 Sn1 2.131(4) 7_545 ? O10 C2 1.351(10) . ? O10 H7 0.82 . ? N1 C1 1.507(9) . ? N1 H3 0.89 . ? N1 H2 0.89 . ? N1 H1 0.89 . ? C1 C2 1.516(10) . ? C1 H5 0.97 . ? C1 H4 0.97 . ? C2 O10 1.351(9) 2_656 ? C2 C1 1.516(10) 2_656 ? 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 O2 Sn1 O1 83.8(2) 6_545 . ? O2 Sn1 O3 89.0(2) 6_545 7_545 ? O1 Sn1 O3 87.3(2) . 7_545 ? O4 P1 O2 112.1(2) . . ? O4 P1 O3 112.3(3) . . ? O2 P1 O3 107.9(2) . . ? O4 P1 O1 109.3(2) . . ? O2 P1 O1 107.7(2) . . ? O3 P1 O1 107.4(2) . . ? P1 O1 Sn1 122.3(2) . . ? P1 O2 Sn1 129.0(2) . 6_546 ? P1 O3 Sn1 118.9(2) . 7_545 ? C2 O10 H7 109.5(4) . . ? C1 N1 H3 109.5(4) . . ? C1 N1 H2 109.5(4) . . ? H3 N1 H2 109.5 . . ? C1 N1 H1 109.5(3) . . ? H3 N1 H1 109.5 . . ? H2 N1 H1 109.5 . . ? N1 C1 C2 109.4(7) . . ? N1 C1 H5 109.8(3) . . ? C2 C1 H5 109.8(3) . . ? N1 C1 H4 109.8(4) . . ? C2 C1 H4 109.8(4) . . ? H5 C1 H4 108.2 . . ? O10 C2 O10 114.4(10) . 2_656 ? O10 C2 C1 108.7(4) . 2_656 ? O10 C2 C1 108.8(5) 2_656 2_656 ? O10 C2 C1 108.8(5) . . ? O10 C2 C1 108.7(4) 2_656 . ? C1 C2 C1 107.3(9) 2_656 . ? _refine_diff_density_max 1.442 _refine_diff_density_min -1.093 _refine_diff_density_rms 0.363