#------------------------------------------------------------------------------ #$Date: 2016-01-21 09:38:23 +0200 (Thu, 21 Jan 2016) $ #$Revision: 174676 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/39/7223949.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7223949 loop_ _publ_author_name 'Tyagi, Adish' 'Kedarnath, G.' 'Wadawale, Amey' 'Shah, Alpa Y.' 'Jain, Vimal K.' 'Vishwanadh, B.' _publ_section_title ; Diorganotin(iv) 4,6-dimethyl-2-pyrimidyl selenolates: synthesis, structures and their utility as molecular precursors for the preparation of SnSe2nano-sheets and thin films ; _journal_issue 10 _journal_name_full 'RSC Adv.' _journal_page_first 8367 _journal_paper_doi 10.1039/C5RA20578F _journal_volume 6 _journal_year 2016 _chemical_formula_sum 'C20 H32 N4 Se2 Sn' _chemical_formula_weight 605.10 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/6 _audit_update_record ; 2015-08-26 deposited with the CCDC. 2016-01-13 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 95.420(17) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 14.800(4) _cell_length_b 7.7490(7) _cell_length_c 21.526(4) _cell_measurement_reflns_used 25 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 12.2 _cell_measurement_theta_min 9.1 _cell_volume 2457.7(8) _computing_cell_refinement WinAFC _computing_data_collection WInAFC _computing_data_reduction 'Crystal Structure' _computing_molecular_graphics Ortep3 _computing_publication_material 'WinGX 2014.1' _computing_structure_refinement 'SHELXL-2014/6 (Sheldrick, 2014)' _computing_structure_solution SIR-92 _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Rigaku AFC7S' _diffrn_measurement_method \w _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_unetI/netI 0.0424 _diffrn_reflns_laue_measured_fraction_full 1.000 _diffrn_reflns_laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 3359 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.240 _diffrn_reflns_theta_max 27.488 _diffrn_reflns_theta_min 2.765 _exptl_absorpt_coefficient_mu 4.013 _exptl_absorpt_correction_T_max 0.669 _exptl_absorpt_correction_T_min 0.296 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.635 _exptl_crystal_description block _exptl_crystal_F_000 1192 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.860 _refine_diff_density_min -0.644 _refine_diff_density_rms 0.096 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 128 _refine_ls_number_reflns 2813 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.044 _refine_ls_R_factor_all 0.0636 _refine_ls_R_factor_gt 0.0342 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0429P)^2^+1.6674P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0823 _refine_ls_wR_factor_ref 0.0922 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2067 _reflns_number_total 2813 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c5ra20578f2.cif _cod_data_source_block shelx _cod_database_code 7223949 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.501 _shelx_estimated_absorpt_t_max 0.690 _shelxl_version_number 2014/6 _shelx_res_file ; TITL AT-1 CELL 0.71069 14.8000 7.7490 21.5263 90.000 95.420 90.000 ZERR 4.00 0.0036 0.0007 0.0035 0.000 0.017 0.000 LATT 7 SYMM - X, Y, 1/2 - Z SFAC C H N SE SN UNIT 80 128 16 8 4 MERG 2 BOND N1 SN1 BIND N1 SN1 FMAP 2 PLAN 25 SIZE 0.100 0.200 0.200 ACTA BOND $H CONF LIST 4 L.S. 10 TEMP 25.00 WGHT 0.042900 1.667400 FVAR 0.09619 C1 1 0.415468 0.316278 0.101201 11.00000 0.05482 0.03851 = 0.04200 0.00292 0.00305 0.00636 C2 1 0.393573 0.055033 0.054869 11.00000 0.06035 0.04736 = 0.05459 -0.00550 0.00646 0.00287 C3 1 0.372143 0.137661 -0.000538 11.00000 0.07491 0.05730 = 0.04583 -0.01124 -0.00406 -0.00017 AFIX 43 H3 2 0.356387 0.074496 -0.036677 11.00000 -1.20000 AFIX 0 C4 1 0.374011 0.315597 -0.002578 11.00000 0.06202 0.06070 = 0.03648 0.00184 0.00538 0.00366 C5 1 0.391780 -0.138622 0.061016 11.00000 0.09827 0.04068 = 0.09026 -0.00933 -0.00312 -0.00044 AFIX 137 H5A 2 0.449731 -0.184955 0.053060 11.00000 -1.50000 H5B 2 0.345578 -0.185186 0.031410 11.00000 -1.50000 H5C 2 0.378889 -0.169096 0.102495 11.00000 -1.50000 AFIX 0 C6 1 0.354189 0.416899 -0.061129 11.00000 0.10239 0.08224 = 0.03734 0.00797 0.00243 0.00888 AFIX 137 H6A 2 0.328978 0.526741 -0.051469 11.00000 -1.50000 H6B 2 0.311500 0.354942 -0.089153 11.00000 -1.50000 H6C 2 0.409320 0.434267 -0.080480 11.00000 -1.50000 AFIX 0 C7 1 0.380846 0.080222 0.282946 11.00000 0.04866 0.05157 = 0.04889 0.00796 0.00221 -0.00385 C8 1 0.405944 -0.104625 0.301101 11.00000 0.07867 0.05776 = 0.11427 0.03059 -0.00678 -0.01987 AFIX 137 H8A 2 0.458259 -0.104471 0.331081 11.00000 -1.50000 H8B 2 0.419385 -0.167614 0.264690 11.00000 -1.50000 H8C 2 0.356023 -0.158420 0.318986 11.00000 -1.50000 AFIX 0 C9 1 0.351809 0.178650 0.338476 11.00000 0.06799 0.11196 = 0.06177 -0.00366 0.01735 -0.00800 AFIX 137 H9A 2 0.295156 0.133419 0.349633 11.00000 -1.50000 H9B 2 0.344656 0.298538 0.327895 11.00000 -1.50000 H9C 2 0.397204 0.166403 0.373110 11.00000 -1.50000 AFIX 0 C10 1 0.303936 0.081327 0.230513 11.00000 0.05332 0.09546 = 0.05966 0.01346 -0.00030 -0.01294 AFIX 137 H10A 2 0.249897 0.035584 0.245703 11.00000 -1.50000 H10B 2 0.320568 0.011559 0.196543 11.00000 -1.50000 H10C 2 0.292940 0.197532 0.216295 11.00000 -1.50000 AFIX 0 N1 3 0.417077 0.144392 0.107562 11.00000 0.06115 0.03879 = 0.04869 0.00309 0.00237 0.00033 N2 3 0.395005 0.406794 0.049467 11.00000 0.06845 0.04192 = 0.03446 0.00649 -0.00070 0.00406 SE1 4 0.443024 0.453353 0.174300 11.00000 0.09082 0.03614 = 0.03765 0.00198 -0.00611 0.00594 SN1 5 0.500000 0.210227 0.250000 10.50000 0.04920 0.03048 = 0.03563 0.00000 -0.00004 0.00000 HKLF 4 REM AT-1 REM R1 = 0.0342 for 2067 Fo > 4sig(Fo) and 0.0636 for all 2813 data REM 128 parameters refined using 0 restraints END WGHT 0.0429 1.6595 REM Highest difference peak 0.860, deepest hole -0.644, 1-sigma level 0.096 Q1 1 0.5000 0.3355 0.2500 10.50000 0.05 0.86 Q2 1 0.5000 0.0831 0.2500 10.50000 0.05 0.70 Q3 1 0.5054 0.4262 0.1763 11.00000 0.05 0.58 Q4 1 0.4396 0.5816 0.1738 11.00000 0.05 0.53 Q5 1 0.4388 0.1976 0.2586 11.00000 0.05 0.42 Q6 1 0.5572 0.2849 0.2615 11.00000 0.05 0.41 Q7 1 0.3983 0.3811 0.1680 11.00000 0.05 0.41 Q8 1 0.5000 -0.0229 0.2500 10.50000 0.05 0.41 Q9 1 0.3179 0.3681 0.3167 11.00000 0.05 0.30 Q10 1 0.3214 0.3147 0.2495 11.00000 0.05 0.29 Q11 1 0.3058 -0.0260 -0.0009 11.00000 0.05 0.27 Q12 1 0.3027 0.1686 0.3408 11.00000 0.05 0.27 Q13 1 0.1982 0.0551 0.2674 11.00000 0.05 0.27 Q14 1 0.3557 0.1322 0.1710 11.00000 0.05 0.26 Q15 1 0.3975 0.3801 -0.0901 11.00000 0.05 0.26 Q16 1 0.3425 -0.2107 0.2809 11.00000 0.05 0.25 Q17 1 0.3874 -0.2217 0.0397 11.00000 0.05 0.25 Q18 1 0.4151 -0.1468 0.0219 11.00000 0.05 0.25 Q19 1 0.3841 0.4770 -0.1520 11.00000 0.05 0.25 Q20 1 0.3467 0.6114 -0.0519 11.00000 0.05 0.24 Q21 1 0.3187 0.1039 0.3498 11.00000 0.05 0.24 Q22 1 0.3408 0.0495 0.2700 11.00000 0.05 0.24 Q23 1 0.4759 0.3304 0.3001 11.00000 0.05 0.24 Q24 1 0.2533 0.2010 0.2705 11.00000 0.05 0.24 Q25 1 0.3839 -0.0928 0.1925 11.00000 0.05 0.24 ; _shelx_res_checksum 62967 loop_ _space_group_symop_operation_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' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy C1 C 0.4155(3) 0.3163(5) 0.1012(2) 0.0452(9) Uani 1 1 d . . . C2 C 0.3936(3) 0.0550(6) 0.0549(2) 0.0540(11) Uani 1 1 d . . . C3 C 0.3721(3) 0.1377(6) -0.0005(2) 0.0600(12) Uani 1 1 d . . . H3 H 0.3564 0.0745 -0.0367 0.072 Uiso 1 1 calc R U . C4 C 0.3740(3) 0.3156(6) -0.0026(2) 0.0530(11) Uani 1 1 d . . . C5 C 0.3918(4) -0.1386(6) 0.0610(3) 0.0772(16) Uani 1 1 d . . . H5A H 0.4497 -0.1850 0.0531 0.116 Uiso 1 1 calc R U . H5B H 0.3456 -0.1852 0.0314 0.116 Uiso 1 1 calc R U . H5C H 0.3789 -0.1691 0.1025 0.116 Uiso 1 1 calc R U . C6 C 0.3542(4) 0.4169(7) -0.0611(2) 0.0743(16) Uani 1 1 d . . . H6A H 0.3290 0.5267 -0.0515 0.111 Uiso 1 1 calc R U . H6B H 0.3115 0.3549 -0.0892 0.111 Uiso 1 1 calc R U . H6C H 0.4093 0.4343 -0.0805 0.111 Uiso 1 1 calc R U . C7 C 0.3808(3) 0.0802(6) 0.2829(2) 0.0499(10) Uani 1 1 d . . . C8 C 0.4059(4) -0.1046(6) 0.3011(3) 0.0846(18) Uani 1 1 d . . . H8A H 0.4583 -0.1045 0.3311 0.127 Uiso 1 1 calc R U . H8B H 0.4194 -0.1676 0.2647 0.127 Uiso 1 1 calc R U . H8C H 0.3560 -0.1584 0.3190 0.127 Uiso 1 1 calc R U . C9 C 0.3518(4) 0.1787(8) 0.3385(3) 0.0799(17) Uani 1 1 d . . . H9A H 0.2952 0.1334 0.3496 0.120 Uiso 1 1 calc R U . H9B H 0.3447 0.2985 0.3279 0.120 Uiso 1 1 calc R U . H9C H 0.3972 0.1664 0.3731 0.120 Uiso 1 1 calc R U . C10 C 0.3039(3) 0.0813(7) 0.2305(2) 0.0698(15) Uani 1 1 d . . . H10A H 0.2499 0.0356 0.2457 0.105 Uiso 1 1 calc R U . H10B H 0.3206 0.0116 0.1965 0.105 Uiso 1 1 calc R U . H10C H 0.2929 0.1975 0.2163 0.105 Uiso 1 1 calc R U . N1 N 0.4171(2) 0.1444(4) 0.10756(17) 0.0497(9) Uani 1 1 d . . . N2 N 0.3950(3) 0.4068(4) 0.04947(16) 0.0486(9) Uani 1 1 d . . . Se1 Se 0.44302(4) 0.45335(6) 0.17430(2) 0.05564(16) Uani 1 1 d . . . Sn1 Sn 0.5000 0.21023(5) 0.2500 0.03869(13) Uani 1 2 d S T P 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 C1 0.055(2) 0.039(2) 0.042(2) 0.0029(17) 0.0031(19) 0.0064(18) C2 0.060(3) 0.047(2) 0.055(3) -0.006(2) 0.006(2) 0.003(2) C3 0.075(3) 0.057(3) 0.046(3) -0.011(2) -0.004(2) 0.000(3) C4 0.062(3) 0.061(3) 0.036(2) 0.002(2) 0.005(2) 0.004(2) C5 0.098(4) 0.041(3) 0.090(4) -0.009(3) -0.003(3) 0.000(3) C6 0.102(4) 0.082(4) 0.037(3) 0.008(2) 0.002(3) 0.009(3) C7 0.049(2) 0.052(2) 0.049(2) 0.0080(19) 0.0022(19) -0.0038(19) C8 0.079(4) 0.058(3) 0.114(5) 0.031(3) -0.007(3) -0.020(3) C9 0.068(3) 0.112(5) 0.062(3) -0.004(3) 0.017(3) -0.008(3) C10 0.053(3) 0.095(4) 0.060(3) 0.013(3) 0.000(2) -0.013(3) N1 0.061(2) 0.0388(18) 0.049(2) 0.0031(16) 0.0024(17) 0.0003(17) N2 0.068(2) 0.0419(19) 0.0345(18) 0.0065(15) -0.0007(16) 0.0041(17) Se1 0.0908(4) 0.0361(2) 0.0376(3) 0.00198(16) -0.0061(2) 0.0059(2) Sn1 0.0492(2) 0.0305(2) 0.0356(2) 0.000 -0.00004(15) 0.000 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' Se Se -0.0929 2.2259 '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' 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 N2 C1 N1 127.7(4) . . N2 C1 Se1 114.3(3) . . N1 C1 Se1 117.9(3) . . N1 C2 C3 121.0(4) . . N1 C2 C5 116.3(5) . . C3 C2 C5 122.7(5) . . C2 C3 C4 119.5(4) . . C2 C3 H3 120.2 . . C4 C3 H3 120.2 . . N2 C4 C3 120.4(4) . . N2 C4 C6 116.2(4) . . C3 C4 C6 123.4(5) . . C2 C5 H5A 109.5 . . C2 C5 H5B 109.5 . . H5A C5 H5B 109.5 . . C2 C5 H5C 109.5 . . H5A C5 H5C 109.5 . . H5B C5 H5C 109.5 . . C4 C6 H6A 109.5 . . C4 C6 H6B 109.5 . . H6A C6 H6B 109.5 . . C4 C6 H6C 109.5 . . H6A C6 H6C 109.5 . . H6B C6 H6C 109.5 . . C9 C7 C8 110.6(4) . . C9 C7 C10 109.5(4) . . C8 C7 C10 110.0(4) . . C9 C7 Sn1 108.6(3) . . C8 C7 Sn1 109.2(3) . . C10 C7 Sn1 108.8(3) . . C7 C8 H8A 109.5 . . C7 C8 H8B 109.5 . . H8A C8 H8B 109.5 . . C7 C8 H8C 109.5 . . H8A C8 H8C 109.5 . . H8B C8 H8C 109.5 . . C7 C9 H9A 109.5 . . C7 C9 H9B 109.5 . . H9A C9 H9B 109.5 . . C7 C9 H9C 109.5 . . H9A C9 H9C 109.5 . . H9B C9 H9C 109.5 . . C7 C10 H10A 109.5 . . C7 C10 H10B 109.5 . . H10A C10 H10B 109.5 . . C7 C10 H10C 109.5 . . H10A C10 H10C 109.5 . . H10B C10 H10C 109.5 . . C1 N1 C2 115.1(4) . . C1 N1 Sn1 86.6(2) . . C2 N1 Sn1 157.6(3) . . C1 N2 C4 116.2(4) . . C1 Se1 Sn1 98.39(12) . . C7 Sn1 C7 125.6(2) . 2_655 C7 Sn1 Se1 110.73(12) . 2_655 C7 Sn1 Se1 108.24(11) 2_655 2_655 C7 Sn1 Se1 108.25(11) . . C7 Sn1 Se1 110.73(12) 2_655 . Se1 Sn1 Se1 86.19(3) 2_655 . C7 Sn1 N1 89.40(14) . . C7 Sn1 N1 82.32(14) 2_655 . Se1 Sn1 N1 141.83(6) 2_655 . Se1 Sn1 N1 56.23(6) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C1 N2 1.327(5) . C1 N1 1.339(5) . C1 Se1 1.910(4) . C2 N1 1.346(6) . C2 C3 1.364(7) . C2 C5 1.507(6) . C3 C4 1.380(6) . C3 H3 0.9300 . C4 N2 1.336(6) . C4 C6 1.490(6) . C5 H5A 0.9600 . C5 H5B 0.9600 . C5 H5C 0.9600 . C6 H6A 0.9600 . C6 H6B 0.9600 . C6 H6C 0.9600 . C7 C9 1.514(7) . C7 C8 1.522(6) . C7 C10 1.525(6) . C7 Sn1 2.205(4) . C8 H8A 0.9600 . C8 H8B 0.9600 . C8 H8C 0.9600 . C9 H9A 0.9600 . C9 H9B 0.9600 . C9 H9C 0.9600 . C10 H10A 0.9600 . C10 H10B 0.9600 . C10 H10C 0.9600 . N1 Sn1 3.234(4) . Se1 Sn1 2.5800(6) . Sn1 C7 2.205(4) 2_655 Sn1 Se1 2.5800(6) 2_655 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 N1 C2 C3 C4 -0.4(8) C5 C2 C3 C4 179.1(5) C2 C3 C4 N2 -1.2(8) C2 C3 C4 C6 178.3(5) N2 C1 N1 C2 -1.1(7) Se1 C1 N1 C2 177.5(3) N2 C1 N1 Sn1 173.6(5) Se1 C1 N1 Sn1 -7.8(3) C3 C2 N1 C1 1.5(7) C5 C2 N1 C1 -178.1(4) C3 C2 N1 Sn1 -164.5(5) C5 C2 N1 Sn1 16.0(11) N1 C1 N2 C4 -0.4(7) Se1 C1 N2 C4 -179.1(3) C3 C4 N2 C1 1.6(7) C6 C4 N2 C1 -177.9(4)