#------------------------------------------------------------------------------ #$Date: 2013-08-29 16:37:19 +0100 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/28/2012847.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2012847 loop_ _publ_author_name 'Xu, Li' 'Zhou, Jian-Hao' 'Chen, Xue-Tai' 'You, Xiao-Zeng' _publ_section_title ; Dibenzyl 2,2'-(ethane-1,2-diylidene)dihydrazinecarbodithioate bis(dimethylformamide) solvate ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o513 _journal_page_last o514 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C18 H18 N4 S4 , 2C3 H7 N O' _chemical_formula_sum 'C24 H32 N6 O2 S4' _chemical_formula_weight 564.84 _chemical_name_systematic ; Dibenzyl 2,2'-(ethane-1,2-diylidene)dihydrazinecarbodithioate dimethylformamide disolvate ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 94.863(3) _cell_angle_beta 94.078(3) _cell_angle_gamma 99.867(3) _cell_formula_units_Z 1 _cell_length_a 6.1040(10) _cell_length_b 10.3202(18) _cell_length_c 11.960(2) _cell_measurement_reflns_used 1445 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 25.93 _cell_measurement_theta_min 2.77 _cell_volume 736.8(2) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full 0.897 _diffrn_measured_fraction_theta_max 0.897 _diffrn_measurement_device_type 'Siemens SMART CCD area-detector' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.013 _diffrn_reflns_av_sigmaI/netI 0.040 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 4486 _diffrn_reflns_theta_full 27.91 _diffrn_reflns_theta_max 27.91 _diffrn_reflns_theta_min 1.72 _diffrn_standards_decay_% none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _exptl_absorpt_coefficient_mu 0.354 _exptl_absorpt_correction_T_max 0.942 _exptl_absorpt_correction_T_min 0.913 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 298 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.17 _refine_diff_density_max 0.41 _refine_diff_density_min -0.28 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 168 _refine_ls_number_reflns 3156 _refine_ls_number_restraints 38 _refine_ls_restrained_S_all 1.162 _refine_ls_R_factor_all 0.074 _refine_ls_R_factor_gt 0.048 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.063P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.123 _refine_ls_wR_factor_ref 0.130 _reflns_number_gt 1900 _reflns_number_total 3156 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bj1039.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M P-1 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2012847 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol S1 0.06846(11) 0.48333(7) 0.73835(6) 0.0675(3) Uani d . 1 . . S S2 0.29519(12) 0.76296(7) 0.71832(7) 0.0838(3) Uani d . 1 . . S N1 -0.0813(3) 0.64299(19) 0.61019(18) 0.0619(6) Uani d . 1 . . N H1A -0.0847 0.7140 0.5778 0.074 Uiso calc R 1 . . H N2 -0.2509(3) 0.53704(19) 0.58523(18) 0.0567(6) Uani d . 1 . . N N3 0.0951(4) 0.9085(2) 0.3510(2) 0.0713(7) Uani d . 1 . . N O1 -0.1690(3) 0.83568(18) 0.46605(19) 0.0757(6) Uani d . 1 . . O C1 0.4482(7) 0.2978(4) 0.8648(3) 0.1134(13) Uani d DU 1 . . C H1B 0.5463 0.3161 0.8098 0.136 Uiso calc R 1 . . H C2 0.4449(8) 0.1843(4) 0.9171(4) 0.1406(17) Uani d DU 1 . . C H2B 0.5403 0.1267 0.8970 0.169 Uiso calc R 1 . . H C3 0.3044(8) 0.1555(4) 0.9974(4) 0.1126(13) Uani d U 1 . . C H3A 0.3022 0.0781 1.0323 0.135 Uiso calc R 1 . . H C4 0.1715(7) 0.2374(4) 1.0257(3) 0.1089(12) Uani d U 1 . . C H4A 0.0744 0.2189 1.0811 0.131 Uiso calc R 1 . . H C5 0.1766(6) 0.3509(3) 0.9729(3) 0.0969(11) Uani d U 1 . . C H5A 0.0817 0.4084 0.9943 0.116 Uiso calc R 1 . . H C6 0.3124(5) 0.3830(3) 0.8917(2) 0.0632(7) Uani d D 1 . . C C7 0.3178(5) 0.5079(3) 0.8359(3) 0.0770(9) Uani d . 1 . . C H7A 0.4506 0.5257 0.7957 0.092 Uiso calc R 1 . . H H7B 0.3184 0.5820 0.8915 0.092 Uiso calc R 1 . . H C8 0.0897(4) 0.6368(2) 0.6846(2) 0.0571(7) Uani d . 1 . . C C9 -0.4083(4) 0.5536(2) 0.5149(2) 0.0579(7) Uani d . 1 . . C H9A -0.4042 0.6333 0.4835 0.069 Uiso calc R 1 . . H C10 0.1541(7) 0.9937(4) 0.2642(4) 0.1284(15) Uani d U 1 . . C H10A 0.0258 1.0284 0.2379 0.193 Uiso calc R 1 . . H H10B 0.2048 0.9441 0.2027 0.193 Uiso calc R 1 . . H H10C 0.2710 1.0652 0.2943 0.193 Uiso calc R 1 . . H C11 0.2628(5) 0.8451(4) 0.4030(3) 0.0967(11) Uani d . 1 . . C H11A 0.1986 0.7915 0.4584 0.145 Uiso calc R 1 . . H H11B 0.3833 0.9110 0.4387 0.145 Uiso calc R 1 . . H H11C 0.3183 0.7903 0.3467 0.145 Uiso calc R 1 . . H C12 -0.1032(5) 0.8977(3) 0.3898(3) 0.0715(9) Uani d . 1 . . C H12 -0.187(5) 0.946(3) 0.352(2) 0.076(9) Uiso d . 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 0.0620(4) 0.0629(5) 0.0737(5) 0.0001(3) -0.0164(3) 0.0251(4) S2 0.0667(5) 0.0697(5) 0.1040(7) -0.0127(4) -0.0280(4) 0.0272(4) N1 0.0522(12) 0.0534(12) 0.0758(15) -0.0025(10) -0.0143(11) 0.0237(10) N2 0.0462(11) 0.0546(12) 0.0669(14) 0.0009(10) -0.0077(10) 0.0189(10) N3 0.0601(15) 0.0716(16) 0.0831(18) 0.0076(12) 0.0130(13) 0.0151(12) O1 0.0609(11) 0.0695(12) 0.1010(15) 0.0067(9) 0.0080(10) 0.0424(11) C1 0.138(3) 0.118(3) 0.103(3) 0.056(2) 0.034(2) 0.036(2) C2 0.164(3) 0.129(3) 0.153(3) 0.079(2) 0.032(3) 0.027(2) C3 0.150(3) 0.094(3) 0.104(3) 0.040(2) 0.012(2) 0.033(2) C4 0.123(3) 0.115(3) 0.101(3) 0.032(2) 0.027(2) 0.043(2) C5 0.104(2) 0.094(2) 0.111(3) 0.0469(19) 0.031(2) 0.039(2) C6 0.0631(17) 0.0722(18) 0.0554(17) 0.0174(14) -0.0079(13) 0.0132(13) C7 0.0692(18) 0.082(2) 0.077(2) 0.0052(15) -0.0204(15) 0.0262(15) C8 0.0511(14) 0.0589(15) 0.0606(16) 0.0068(12) -0.0033(12) 0.0151(12) C9 0.0485(14) 0.0537(15) 0.0712(18) 0.0046(11) -0.0044(12) 0.0227(13) C10 0.127(3) 0.141(3) 0.128(3) 0.018(3) 0.056(2) 0.051(3) C11 0.0622(19) 0.123(3) 0.105(3) 0.021(2) 0.0022(18) 0.005(2) C12 0.0624(19) 0.0604(18) 0.093(2) 0.0111(15) -0.0023(17) 0.0249(16) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 C8 . 1.746(2) yes S1 C7 . 1.818(3) yes S2 C8 . 1.647(3) yes N1 C8 . 1.337(3) yes N1 N2 . 1.367(3) yes N1 H1A . 0.8600 no N2 C9 . 1.275(3) yes N3 C12 . 1.317(4) yes N3 C11 . 1.439(4) yes N3 C10 . 1.442(4) yes O1 C12 . 1.211(3) yes C1 C6 . 1.343(3) yes C1 C2 . 1.371(3) yes C1 H1B . 0.9300 no C2 C3 . 1.351(5) yes C2 H2B . 0.9300 no C3 C4 . 1.309(5) yes C3 H3A . 0.9300 no C4 C5 . 1.374(5) yes C4 H4A . 0.9300 no C5 C6 . 1.347(4) yes C5 H5A . 0.9300 no C6 C7 . 1.498(4) yes C7 H7A . 0.9700 no C7 H7B . 0.9700 no C9 C9 2_466 1.434(5) yes C9 H9A . 0.9300 no C10 H10A . 0.9600 no C10 H10B . 0.9600 no C10 H10C . 0.9600 no C11 H11A . 0.9600 no C11 H11B . 0.9600 no C11 H11C . 0.9600 no C12 H12 . 0.89(3) no 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' S S 0.1246 0.1234 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C8 S1 C7 . . 101.86(12) yes C8 N1 N2 . . 120.34(19) yes C8 N1 H1A . . 119.8 no N2 N1 H1A . . 119.8 no C9 N2 N1 . . 115.60(19) yes C12 N3 C11 . . 119.8(3) yes C12 N3 C10 . . 120.8(3) yes C11 N3 C10 . . 119.1(3) yes C6 C1 C2 . . 121.2(4) yes C6 C1 H1B . . 119.4 no C2 C1 H1B . . 119.4 no C3 C2 C1 . . 120.6(4) yes C3 C2 H2B . . 119.7 no C1 C2 H2B . . 119.7 no C4 C3 C2 . . 119.4(4) yes C4 C3 H3A . . 120.3 no C2 C3 H3A . . 120.3 no C3 C4 C5 . . 119.4(4) yes C3 C4 H4A . . 120.3 no C5 C4 H4A . . 120.3 no C6 C5 C4 . . 123.2(3) yes C6 C5 H5A . . 118.4 no C4 C5 H5A . . 118.4 no C1 C6 C5 . . 116.2(3) yes C1 C6 C7 . . 121.3(3) yes C5 C6 C7 . . 122.5(3) yes C6 C7 S1 . . 106.70(19) yes C6 C7 H7A . . 110.4 no S1 C7 H7A . . 110.4 no C6 C7 H7B . . 110.4 no S1 C7 H7B . . 110.4 no H7A C7 H7B . . 108.6 no N1 C8 S2 . . 121.78(18) yes N1 C8 S1 . . 112.77(18) yes S2 C8 S1 . . 125.44(15) yes N2 C9 C9 . 2_466 118.5(3) yes N2 C9 H9A . . 120.8 no C9 C9 H9A 2_466 . 120.8 no N3 C10 H10A . . 109.5 no N3 C10 H10B . . 109.5 no H10A C10 H10B . . 109.5 no N3 C10 H10C . . 109.5 no H10A C10 H10C . . 109.5 no H10B C10 H10C . . 109.5 no N3 C11 H11A . . 109.5 no N3 C11 H11B . . 109.5 no H11A C11 H11B . . 109.5 no N3 C11 H11C . . 109.5 no H11A C11 H11C . . 109.5 no H11B C11 H11C . . 109.5 ? O1 C12 N3 . . 127.3(3) yes O1 C12 H12 . . 122.6(18) no N3 C12 H12 . . 110.1(18) no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C9 H9A O1 1_555 0.930 2.357 3.147(3) 143 yes N1 H1A O1 1_555 0.860 2.009 2.833(2) 160 yes _cod_database_fobs_code 2012847