#------------------------------------------------------------------------------ #$Date: 2016-02-25 04:31:00 +0200 (Thu, 25 Feb 2016) $ #$Revision: 176878 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/10/02/1100265.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_1100265 loop_ _publ_author_name 'Reichardt, Christian' 'Erfurt, Hans-Peter' 'Harms, Klaus' 'Sch\"afer, Gerhard' _publ_section_title ; Syntheses, Absolute Configurations, and UV/Vis Spectroscopic Properties of New Chiral Tri- and Pentamethinium Streptocyanine Dyes with 4-Aminophenyl 4-Methylphenyl Sulfoxide Endgroups ; _journal_coden_ASTM EJOCFK _journal_issue 3 _journal_name_full 'European Journal of Organic Chemistry' _journal_page_first 439 _journal_page_last 452 _journal_paper_doi 10.1002/1099-0690(20022)2002:3<439::AID-EJOC439>3.0.CO;2-B _journal_volume 2002 _journal_year 2002 _chemical_formula_moiety 'C29 H27 N2 O2 S2 1+,Br1 1-,3(H2 O1)' _chemical_formula_sum 'C29 H33 Br N2 O5 S2' _chemical_melting_point 488.15 _chemical_name_systematic ; (-)-(S,S)-1,3-bis(4-(4-Methylphenylsulfinyl)phenylamino)trimethinium bromide trihydrate ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _cell_angle_alpha 90 _cell_angle_beta 91.40(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.4024(4) _cell_length_b 16.4819(13) _cell_length_c 33.130(18) _cell_volume 2949.075 _diffrn_ambient_temperature 193 _exptl_crystal_colour colorless. _exptl_crystal_density_diffrn 1.427 _exptl_crystal_description 'narrow plate' _exptl_crystal_preparation 'ethanol/petroleum ether(40-60)' _refine_ls_R_factor_gt 4.78 _refine_ls_wR_factor_gt 4.78 _cod_original_sg_symbol_H-M 'P 21' _cod_original_formula_sum 'C29 H33 Br1 N2 O5 S2' _cod_database_code 1100265 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,-z loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z S1 S -0.0757(3) 0.83082(14) 0.34916(5) O1 O -0.0830(9) 0.9194(3) 0.35924(12) N1 N 0.6442(9) 0.6667(3) 0.46042(15) H1 H 0.60(1) 0.624(2) 0.4643(17) C1 C 0.8350(9) 0.6963(3) 0.48123(14) H2 H 0.87160 0.75230 0.47800 S2 S 0.0586(3) 0.58035(13) 1.15727(5) O2 O 0.0620(9) 0.6691(3) 1.14669(13) N2 N -0.6272(9) 0.4130(3) 1.04151(14) H3 H -0.588(9) 0.369(2) 1.0417(16) C2 C -0.8211(9) 0.4404(3) 1.02173(14) H4 H -0.86570 0.49540 1.02610 Br1 Br -0.0009(2) 0.90629(3) 0.50629(2) S3 S 2.1006(3) 0.80434(11) 0.66155(4) O3 O 2.1492(8) 0.8894(3) 0.64941(11) N3 N 1.3268(8) 0.6577(3) 0.55372(14) H5 H 1.304(9) 0.614(2) 0.5592(14) C3 C 0.9845(8) 0.6523(4) 0.50713(13) H6 H 0.95870 0.59570 0.51070 S4 S -2.1072(3) 0.54915(11) 0.84582(5) O4 O -2.1592(7) 0.6334(3) 0.85904(12) N4 N -1.3110(9) 0.4011(3) 0.94866(12) H7 H -1.297(9) 0.3574(19) 0.9430(14) C4 C -0.9665(9) 0.3963(4) 0.99508(13) H8 H -0.93390 0.34040 0.99050 Br2 Br 0.97126(11) 0.65068(3) 0.99904(4) C5 C 1.1708(9) 0.6914(3) 0.52765(14) H9 H 1.18960 0.74780 0.52270 C6 C -1.1587(9) 0.4343(3) 0.97522(14) H10 H -1.18410 0.49000 0.98130 C7 C 0.1448(10) 0.7859(4) 0.38368(15) C8 C -0.1547(10) 0.5336(4) 1.12231(16) C9 C 0.1427(10) 0.7027(4) 0.38649(16) H11 H 0.02500 0.67190 0.37120 C10 C -0.1354(10) 0.4511(4) 1.11698(16) H12 H -0.01280 0.42100 1.13160 C11 C 0.3127(9) 0.6643(4) 0.41169(16) H13 H 0.31580 0.60680 0.41330 C12 C -0.2944(9) 0.4126(4) 1.09045(14) H14 H -0.28190 0.35570 1.08670 C13 C 0.4798(9) 0.7102(3) 0.43478(14) C14 C -0.4729(9) 0.4560(3) 1.06903(14) C15 C 0.4755(10) 0.7945(3) 0.43208(16) H15 H 0.58870 0.82620 0.44780 C16 C -0.4881(10) 0.5397(3) 1.07380(16) H16 H -0.60810 0.57030 1.05890 C17 C 0.3070(11) 0.8312(4) 0.40670(16) H17 H 0.30240 0.88870 0.40500 C18 C -0.3266(10) 0.5772(3) 1.10041(17) H18 H -0.33430 0.63440 1.10370 C19 C 0.0977(10) 0.8258(3) 0.30412(15) C20 C -0.1139(9) 0.5749(3) 1.20227(15) C21 C -0.0022(10) 0.7829(4) 0.27181(16) H19 H -0.15030 0.75260 0.27470 C22 C -0.0151(10) 0.5309(4) 1.23476(17) H20 H 0.13160 0.50000 1.23170 C23 C 0.1154(10) 0.7842(4) 0.23509(16) H21 H 0.04740 0.75460 0.21290 C24 C -0.130(1) 0.5324(3) 1.27114(17) H22 H -0.06210 0.50190 1.29310 C25 C 0.3304(10) 0.8282(3) 0.23051(16) C26 C -0.3411(10) 0.5771(3) 1.27668(17) C27 C 0.4314(10) 0.8696(3) 0.26363(17) H23 H 0.58180 0.89870 0.26090 C28 C -0.4431(10) 0.6190(4) 1.24395(17) H24 H -0.59230 0.64860 1.24710 C29 C 0.3167(10) 0.8691(4) 0.30059(16) H25 H 0.38630 0.89770 0.32300 C30 C -0.3303(9) 0.6185(4) 1.20664(17) H26 H -0.40090 0.64770 1.18450 C31 C 0.4538(11) 0.8335(4) 0.19033(18) H27 H 0.36190 0.80050 0.17050 H28 H 0.62410 0.81340 0.19310 H29 H 0.45580 0.89010 0.18130 C32 C -0.4648(12) 0.5807(5) 1.31686(19) H30 H -0.37160 0.54750 1.33650 H31 H -0.63420 0.55990 1.31400 H32 H -0.46900 0.63700 1.32630 C33 C 1.8751(9) 0.7640(3) 0.62685(15) C34 C -1.8782(9) 0.5073(3) 0.87979(14) C35 C 1.8565(9) 0.6806(4) 0.62361(16) H33 H 1.96790 0.64670 0.63850 C36 C -1.8484(10) 0.4239(3) 0.88001(15) H34 H -1.95540 0.39040 0.86410 C37 C 1.6756(9) 0.6466(4) 0.59872(15) H35 H 1.66450 0.58930 0.59630 C38 C -1.6618(10) 0.3899(4) 0.90361(14) H36 H -1.64090 0.33270 0.90420 C39 C 1.5112(9) 0.6951(3) 0.57732(14) C40 C -1.5028(8) 0.4398(3) 0.92671(13) C41 C 1.5339(10) 0.7798(3) 0.57978(15) H37 H 1.42330 0.81370 0.56480 C42 C -1.5395(10) 0.5226(3) 0.92726(15) H38 H -1.43530 0.55640 0.94350 C43 C 1.7168(10) 0.8134(4) 0.60397(16) H39 H 1.73540 0.87070 0.60510 C44 C -1.7292(10) 0.5563(3) 0.90394(15) H40 H -1.75700 0.61320 0.90450 C45 C 1.9138(9) 0.8107(3) 0.70554(15) C46 C -1.9178(9) 0.5588(3) 0.80241(16) C47 C 2.0041(10) 0.7726(4) 0.74002(17) H41 H 2.15010 0.74060 0.73930 C48 C -2.0057(10) 0.5226(3) 0.76708(17) H42 H -2.15190 0.49060 0.76690 C49 C 1.8773(10) 0.7820(4) 0.77590(16) H43 H 1.93780 0.75590 0.79970 C50 C -1.8754(10) 0.5342(3) 0.73193(17) H44 H -1.93460 0.51000 0.70750 C51 C 1.6658(10) 0.8285(4) 0.77744(16) C52 C -1.6619(9) 0.5801(3) 0.73173(16) C53 C 1.5771(10) 0.8648(4) 0.74214(19) H45 H 1.42900 0.89580 0.74270 C54 C -1.5765(9) 0.6141(3) 0.76765(17) H46 H -1.42820 0.64510 0.76790 C55 C 1.7006(9) 0.8567(3) 0.70594(16) H47 H 1.63930 0.88230 0.68200 C56 C -1.7023(9) 0.6040(3) 0.80317(16) H48 H -1.64170 0.62770 0.82760 C57 C 1.5298(12) 0.8406(5) 0.81613(19) H49 H 1.61700 0.81190 0.83810 H50 H 1.36120 0.81920 0.81300 H51 H 1.52280 0.89870 0.82240 C58 C -1.5250(11) 0.5935(4) 0.69321(18) H52 H -1.61120 0.56520 0.67100 H53 H -1.35620 0.57230 0.69630 H54 H -1.51860 0.65170 0.68730 O5 O 0.7752(10) 0.2421(3) 0.92207(14) O6 O 0.5248(8) 0.2582(3) 1.0200(2) O7 O 0.2557(11) 0.4957(3) 0.57435(15) O8 O -0.5023(12) 0.5138(4) 0.4808(3) O9 O -0.0917(14) 0.7656(4) 0.9079(2) O10 O 0.0723(14) 1.0162(4) 0.5965(2) H55 H 0.848(13) 0.200(3) 0.935(2) H56 H 0.924(8) 0.264(5) 0.918(2) H57 H 0.396(10) 0.243(5) 1.0048(19) H58 H 0.676(7) 0.239(4) 1.016(2) H59 H 0.193(14) 0.471(4) 0.5523(15) H60 H 0.093(6) 0.503(5) 0.577(3) H61 H -0.398(12) 0.479(4) 0.493(2) H62 H -0.486(17) 0.494(5) 0.4556(14) loop_ _atom_type_symbol _atom_type_radius_bond C 0.68 H 0.23 Br 1.21 N 0.68 O 0.68 S 1.02