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Polymorphism is the ability of a solid material to exist in more than one form or crystal structure and this is of interest in the fields of crystal engineering and solid-state chemistry. 2,2'-(Disulfanediyl)dibenzoic acid (also called 2,2'-dithiosalicylic acid, DTSA) is able to form different hydrogen bonds using its carboxyl groups. The central bridging S atoms allow the two terminal arene rings to rotate freely to generate various hydrogen-bonded linking modes. DTSA can act as a potential host molecule with suitable guest molecules to develop new inclusion compounds. We report here the crystal structures of three new polymorphs of the inclusion compound of DTSA and trimethylamine, namely trimethylazanium 2-[(2-carboxyphenyl)disulfanyl]benzoate 2,2'-(disulfanediyl)dibenzoic acid monosolvate, C3H10N+·C14H9O4S2-·C14H10O4S2, (1), tetrakis(trimethylazanium) bis{2-[(2-carboxyphenyl)disulfanyl]benzoate} 2,2'-(disulfanediyl)dibenzoate 2,2'-(disulfanediyl)dibenzoic acid monosolvate, 4C3H10N+·2C14H9O4S2-·C14H8O4S22-·C14H10O4S2, (2), and trimethylazanium 2-[(2-carboxyphenyl)disulfanyl]benzoate, C3H10N+·C14H9O4S2-, (3). In the three polymorphs, DTSA utilizes its carboxyl groups to form conventional O-H
O hydrogen bonds to generate different host lattices. The central N atoms of the guest amine molecules accept H atoms from DTSA molecules to give the corresponding cations, which act as counter-ions to produce the stable crystal structures via N-HO hydrogen bonding between the host acid and the guest molecule. It is noticeable that although these three compounds are composed of the same components, the final crystal structures are totally different due to the various configurations of the host acid, the number of guest molecules and the inducer (i.e. ancillary experimental acid).
O hydrogen bonds to generate different host lattices. The central N atoms of the guest amine molecules accept H atoms from DTSA molecules to give the corresponding cations, which act as counter-ions to produce the stable crystal structures via N-HO hydrogen bonding between the host acid and the guest molecule. It is noticeable that although these three compounds are composed of the same components, the final crystal structures are totally different due to the various configurations of the host acid, the number of guest molecules and the inducer (i.e. ancillary experimental acid).Keywords: polymorphs; 2,2'-dithiosalicylic acid; inclusion compounds; hydrogen bonding; crystal structure; crystal engineering; solid-state chemistry.
Supporting information
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616017861/yo3027sup1.cif |
 | Structure factor file (CIF format) https://doi.org/10.1107/S2053229616017861/yo3027polymorph1sup2.hkl |
| Structure factor file (CIF format) https://doi.org/10.1107/S2053229616017861/yo3027polymorph2sup3.hkl |
| Structure factor file (CIF format) https://doi.org/10.1107/S2053229616017861/yo3027polymorph3sup4.hkl |
CCDC references: 1004469; 748879; 748877
Computing details top
Data collection: SMART (Bruker, 2005) for polymorph1; Bruker SMART for polymorph2, polymorph3. Cell refinement: SMART (Bruker, 2005) for polymorph1; Bruker SMART for polymorph2, polymorph3. Data reduction: SAINT (Bruker, 2005) for polymorph1; Bruker SAINT for polymorph2, polymorph3. Program(s) used to solve structure: SHELXTL (Sheldrick, 2000) for polymorph1; Bruker SHELXTL for polymorph2, polymorph3. Program(s) used to refine structure: SHELXTL (Sheldrick, 2000) for polymorph1; Bruker SHELXTL for polymorph2, polymorph3. Molecular graphics: SHELXTL (Sheldrick, 2000) for polymorph1; Bruker SHELXTL for polymorph2, polymorph3. Software used to prepare material for publication: SHELXTL (Sheldrick, 2000) for polymorph1; Bruker SHELXTL for polymorph2, polymorph3.
(polymorph1) Trimethylazanium 2-[(2-carboxyphenyl)disulfanyl]benzoate
2,2'-(disulfanediyl)dibenzoic acid monosolvate top
Crystal data top
| C3H10N+·C14H9O4S2−·C14H10O4S2 | F(000) = 1400 |
| Mr = 671.79 | Dx = 1.421 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 6998 reflections |
| a = 14.1130 (2) Å | θ = 2.8–27.6° |
| b = 12.2433 (2) Å | µ = 0.35 mm−1 |
| c = 18.8793 (2) Å | T = 296 K |
| β = 105.680 (1)° | Block, yellow |
| V = 3140.75 (8) Å3 | 0.63 × 0.51 × 0.4 mm |
| Z = 4 |
Data collection top
| Bruker SMART CCD area detector diffractometer | 7276 independent reflections |
| Radiation source: fine-focus sealed tube | 5756 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.017 |
| phi and ω scans | θmax = 27.6°, θmin = 2.0° |
| Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −17→18 |
| Tmin = 0.805, Tmax = 0.868 | k = −15→12 |
| 15246 measured reflections | l = −22→24 |
Refinement top
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.148 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.04 | w = 1/[σ2(Fo2) + (0.0738P)2 + 1.6643P] where P = (Fo2 + 2Fc2)/3 |
| 7276 reflections | (Δ/σ)max = 0.026 |
| 409 parameters | Δρmax = 1.18 e Å−3 |
| 6 restraints | Δρmin = −1.29 e Å−3 |
Special details top
Geometry. 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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| C1 | 0.19089 (15) | 1.09681 (17) | 0.10845 (12) | 0.0410 (5) | |
| C6 | 0.14355 (18) | 1.0310 (2) | 0.04979 (14) | 0.0515 (6) | |
| H6A | 0.1345 | 0.9572 | 0.0577 | 0.062* | |
| C5 | 0.1097 (2) | 1.0736 (2) | −0.02011 (15) | 0.0635 (7) | |
| H5A | 0.0779 | 1.0284 | −0.0588 | 0.076* | |
| C4 | 0.1224 (2) | 1.1823 (3) | −0.03316 (16) | 0.0659 (7) | |
| H4A | 0.1011 | 1.2103 | −0.0806 | 0.079* | |
| C3 | 0.16685 (19) | 1.2489 (2) | 0.02467 (16) | 0.0566 (6) | |
| H3A | 0.1748 | 1.3227 | 0.0159 | 0.068* | |
| C2 | 0.20047 (16) | 1.20908 (18) | 0.09623 (13) | 0.0438 (5) | |
| C7 | 0.24510 (18) | 1.28930 (19) | 0.15536 (16) | 0.0517 (6) | |
| C8 | 0.12686 (16) | 0.82806 (18) | 0.19849 (12) | 0.0423 (5) | |
| C9 | 0.10477 (17) | 0.71637 (18) | 0.19427 (12) | 0.0446 (5) | |
| C10 | 0.01893 (19) | 0.6812 (2) | 0.21114 (15) | 0.0553 (6) | |
| H10A | 0.0042 | 0.6071 | 0.2088 | 0.066* | |
| C11 | −0.0437 (2) | 0.7528 (2) | 0.23098 (16) | 0.0644 (7) | |
| H11A | −0.0998 | 0.7276 | 0.2427 | 0.077* | |
| C12 | −0.0224 (2) | 0.8627 (3) | 0.23331 (17) | 0.0653 (7) | |
| H12A | −0.0649 | 0.9122 | 0.2461 | 0.078* | |
| C13 | 0.06118 (19) | 0.8999 (2) | 0.21690 (15) | 0.0554 (6) | |
| H13A | 0.0739 | 0.9745 | 0.2182 | 0.067* | |
| C14 | 0.16946 (19) | 0.63489 (18) | 0.17361 (15) | 0.0509 (6) | |
| C15 | 0.22009 (17) | 0.79602 (19) | 0.40572 (13) | 0.0476 (5) | |
| C20 | 0.1553 (2) | 0.7190 (2) | 0.42018 (18) | 0.0642 (7) | |
| H20A | 0.1684 | 0.6450 | 0.4169 | 0.077* | |
| C19 | 0.0720 (2) | 0.7510 (3) | 0.4393 (2) | 0.0774 (9) | |
| H19A | 0.0298 | 0.6983 | 0.4491 | 0.093* | |
| C18 | 0.0504 (2) | 0.8595 (3) | 0.4441 (2) | 0.0753 (9) | |
| H18A | −0.0058 | 0.8805 | 0.4573 | 0.090* | |
| C17 | 0.1128 (2) | 0.9368 (2) | 0.42915 (17) | 0.0633 (7) | |
| H17A | 0.0978 | 1.0105 | 0.4315 | 0.076* | |
| C16 | 0.19826 (18) | 0.90675 (19) | 0.41047 (13) | 0.0477 (5) | |
| C21 | 0.2650 (2) | 0.99263 (19) | 0.39716 (14) | 0.0502 (5) | |
| C22 | 0.35316 (16) | 0.52534 (19) | 0.44594 (13) | 0.0444 (5) | |
| C27 | 0.37330 (19) | 0.5841 (2) | 0.51108 (14) | 0.0555 (6) | |
| H27A | 0.3657 | 0.6596 | 0.5095 | 0.067* | |
| C26 | 0.4046 (2) | 0.5320 (3) | 0.57845 (15) | 0.0656 (8) | |
| H26A | 0.4179 | 0.5727 | 0.6216 | 0.079* | |
| C25 | 0.4159 (2) | 0.4210 (3) | 0.58189 (17) | 0.0711 (8) | |
| H25A | 0.4366 | 0.3862 | 0.6272 | 0.085* | |
| C24 | 0.3966 (2) | 0.3617 (2) | 0.51850 (17) | 0.0638 (7) | |
| H24A | 0.4044 | 0.2863 | 0.5212 | 0.077* | |
| C23 | 0.36525 (17) | 0.4117 (2) | 0.44952 (14) | 0.0494 (5) | |
| C28 | 0.3464 (2) | 0.3390 (2) | 0.38424 (17) | 0.0573 (6) | |
| C29 | 0.4792 (4) | 0.4589 (5) | 0.1953 (3) | 0.139 (2) | |
| H29A | 0.4538 | 0.3946 | 0.1675 | 0.208* | |
| H29B | 0.4595 | 0.4596 | 0.2401 | 0.208* | |
| H29C | 0.5498 | 0.4587 | 0.2067 | 0.208* | |
| C30 | 0.4178 (3) | 0.5557 (6) | 0.0806 (2) | 0.163 (3) | |
| H30A | 0.3940 | 0.4858 | 0.0604 | 0.245* | |
| H30B | 0.4743 | 0.5757 | 0.0644 | 0.245* | |
| H30C | 0.3671 | 0.6095 | 0.0642 | 0.245* | |
| C31 | 0.4774 (4) | 0.6509 (5) | 0.1954 (3) | 0.147 (2) | |
| H31A | 0.4494 | 0.7129 | 0.1660 | 0.220* | |
| H31B | 0.5479 | 0.6545 | 0.2069 | 0.220* | |
| H31C | 0.4574 | 0.6512 | 0.2402 | 0.220* | |
| N1 | 0.4429 (6) | 0.5502 (4) | 0.1545 (2) | 0.221 (4) | |
| H11 | 0.3837 (12) | 0.546 (2) | 0.1603 (9) | 0.332* | |
| O1 | 0.24995 (16) | 1.38723 (14) | 0.13907 (13) | 0.0714 (6) | |
| O2 | 0.27485 (18) | 1.25191 (15) | 0.21998 (12) | 0.0737 (6) | |
| O3 | 0.13352 (17) | 0.53555 (15) | 0.16631 (17) | 0.0861 (7) | |
| H31 | 0.177 (3) | 0.492 (3) | 0.154 (2) | 0.129* | |
| O4 | 0.24821 (14) | 0.65635 (15) | 0.16387 (13) | 0.0663 (5) | |
| O5 | 0.22751 (18) | 1.09123 (16) | 0.39181 (17) | 0.0871 (7) | |
| H51 | 0.270 (3) | 1.139 (3) | 0.384 (3) | 0.131* | |
| O6 | 0.34661 (15) | 0.97469 (14) | 0.39188 (13) | 0.0673 (5) | |
| O7 | 0.3186 (2) | 0.38491 (16) | 0.32194 (12) | 0.0814 (7) | |
| H71 | 0.310 (3) | 0.337 (3) | 0.2853 (16) | 0.122* | |
| O8 | 0.35964 (19) | 0.23949 (16) | 0.39180 (14) | 0.0831 (7) | |
| S1 | 0.24211 (4) | 1.03984 (4) | 0.19834 (3) | 0.04692 (16) | |
| S2 | 0.23892 (4) | 0.87456 (4) | 0.18104 (4) | 0.04760 (16) | |
| S3 | 0.32943 (5) | 0.75556 (5) | 0.38191 (4) | 0.05253 (17) | |
| S4 | 0.31236 (5) | 0.59289 (5) | 0.35865 (3) | 0.05211 (17) |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0379 (10) | 0.0333 (10) | 0.0535 (12) | 0.0033 (8) | 0.0150 (9) | −0.0005 (9) |
| C6 | 0.0528 (14) | 0.0410 (12) | 0.0571 (14) | 0.0030 (10) | 0.0087 (11) | −0.0045 (10) |
| C5 | 0.0648 (17) | 0.0632 (17) | 0.0557 (15) | 0.0093 (13) | 0.0046 (12) | −0.0068 (13) |
| C4 | 0.0701 (18) | 0.0694 (19) | 0.0582 (15) | 0.0167 (14) | 0.0173 (13) | 0.0127 (14) |
| C3 | 0.0539 (14) | 0.0445 (13) | 0.0773 (17) | 0.0109 (11) | 0.0278 (13) | 0.0145 (12) |
| C2 | 0.0388 (11) | 0.0336 (10) | 0.0642 (13) | 0.0042 (8) | 0.0230 (10) | 0.0016 (10) |
| C7 | 0.0484 (13) | 0.0310 (11) | 0.0827 (18) | 0.0000 (9) | 0.0295 (12) | −0.0053 (11) |
| C8 | 0.0464 (12) | 0.0381 (11) | 0.0428 (11) | −0.0006 (9) | 0.0130 (9) | 0.0004 (9) |
| C9 | 0.0495 (12) | 0.0361 (11) | 0.0497 (12) | 0.0012 (9) | 0.0159 (10) | 0.0043 (9) |
| C10 | 0.0593 (15) | 0.0457 (14) | 0.0663 (15) | −0.0048 (11) | 0.0262 (12) | 0.0075 (11) |
| C11 | 0.0622 (16) | 0.0687 (18) | 0.0729 (17) | −0.0060 (13) | 0.0366 (14) | −0.0014 (14) |
| C12 | 0.0647 (17) | 0.0629 (17) | 0.0785 (18) | 0.0023 (13) | 0.0372 (14) | −0.0146 (14) |
| C13 | 0.0598 (15) | 0.0433 (13) | 0.0681 (15) | −0.0002 (11) | 0.0257 (12) | −0.0104 (11) |
| C14 | 0.0554 (14) | 0.0313 (11) | 0.0681 (15) | −0.0013 (10) | 0.0202 (12) | 0.0046 (10) |
| C15 | 0.0474 (12) | 0.0383 (11) | 0.0563 (13) | −0.0006 (9) | 0.0125 (10) | 0.0031 (10) |
| C20 | 0.0539 (15) | 0.0414 (13) | 0.100 (2) | −0.0022 (11) | 0.0258 (14) | 0.0070 (14) |
| C19 | 0.0568 (17) | 0.0608 (18) | 0.121 (3) | −0.0078 (14) | 0.0351 (17) | 0.0126 (17) |
| C18 | 0.0558 (16) | 0.0652 (19) | 0.115 (3) | 0.0021 (14) | 0.0409 (17) | 0.0013 (18) |
| C17 | 0.0631 (16) | 0.0473 (14) | 0.0839 (19) | 0.0033 (12) | 0.0275 (14) | −0.0049 (13) |
| C16 | 0.0505 (13) | 0.0399 (12) | 0.0527 (13) | −0.0009 (10) | 0.0139 (10) | 0.0005 (10) |
| C21 | 0.0630 (15) | 0.0336 (11) | 0.0574 (14) | −0.0005 (10) | 0.0224 (11) | −0.0031 (10) |
| C22 | 0.0383 (11) | 0.0437 (12) | 0.0525 (12) | −0.0017 (9) | 0.0144 (9) | 0.0043 (9) |
| C27 | 0.0525 (14) | 0.0571 (15) | 0.0586 (14) | −0.0043 (12) | 0.0179 (11) | −0.0029 (12) |
| C26 | 0.0571 (16) | 0.091 (2) | 0.0524 (14) | −0.0065 (14) | 0.0205 (12) | 0.0023 (14) |
| C25 | 0.0581 (16) | 0.098 (2) | 0.0620 (17) | 0.0046 (16) | 0.0235 (13) | 0.0273 (17) |
| C24 | 0.0538 (15) | 0.0611 (16) | 0.083 (2) | 0.0072 (12) | 0.0305 (14) | 0.0267 (15) |
| C23 | 0.0415 (12) | 0.0438 (13) | 0.0675 (15) | −0.0004 (9) | 0.0227 (11) | 0.0094 (11) |
| C28 | 0.0576 (15) | 0.0346 (12) | 0.0851 (19) | −0.0026 (10) | 0.0285 (13) | 0.0020 (12) |
| C29 | 0.100 (3) | 0.175 (6) | 0.133 (4) | −0.004 (3) | 0.018 (3) | 0.060 (4) |
| C30 | 0.091 (3) | 0.333 (10) | 0.063 (2) | 0.032 (4) | 0.017 (2) | 0.020 (4) |
| C31 | 0.110 (4) | 0.170 (6) | 0.148 (5) | −0.003 (4) | 0.014 (3) | −0.033 (4) |
| N1 | 0.412 (10) | 0.124 (4) | 0.077 (2) | 0.120 (5) | −0.021 (4) | 0.000 (2) |
| O1 | 0.0811 (14) | 0.0303 (9) | 0.1102 (17) | −0.0039 (8) | 0.0387 (12) | −0.0016 (9) |
| O2 | 0.1079 (17) | 0.0373 (10) | 0.0714 (13) | −0.0105 (10) | 0.0167 (12) | −0.0137 (9) |
| O3 | 0.0801 (15) | 0.0325 (10) | 0.163 (2) | −0.0064 (9) | 0.0620 (15) | −0.0071 (12) |
| O4 | 0.0600 (11) | 0.0383 (9) | 0.1103 (16) | 0.0002 (8) | 0.0394 (11) | −0.0033 (10) |
| O5 | 0.0946 (17) | 0.0335 (10) | 0.152 (2) | 0.0055 (10) | 0.0660 (16) | 0.0034 (12) |
| O6 | 0.0640 (12) | 0.0371 (9) | 0.1097 (16) | −0.0038 (8) | 0.0385 (11) | 0.0026 (9) |
| O7 | 0.125 (2) | 0.0364 (10) | 0.0711 (13) | −0.0021 (11) | 0.0062 (13) | −0.0112 (9) |
| O8 | 0.1052 (17) | 0.0340 (10) | 0.1196 (19) | 0.0025 (10) | 0.0470 (15) | 0.0057 (11) |
| S1 | 0.0551 (3) | 0.0327 (3) | 0.0509 (3) | −0.0041 (2) | 0.0109 (2) | −0.0019 (2) |
| S2 | 0.0467 (3) | 0.0316 (3) | 0.0665 (4) | 0.0006 (2) | 0.0186 (3) | 0.0027 (2) |
| S3 | 0.0562 (4) | 0.0337 (3) | 0.0724 (4) | −0.0004 (2) | 0.0254 (3) | 0.0017 (3) |
| S4 | 0.0663 (4) | 0.0348 (3) | 0.0526 (3) | 0.0021 (3) | 0.0114 (3) | 0.0006 (2) |
Geometric parameters (Å, º) top
| C1—C6 | 1.387 (3) | C17—C16 | 1.395 (4) |
| C1—C2 | 1.406 (3) | C17—H17A | 0.9300 |
| C1—S1 | 1.796 (2) | C16—C21 | 1.478 (3) |
| C6—C5 | 1.379 (4) | C21—O6 | 1.203 (3) |
| C6—H6A | 0.9300 | C21—O5 | 1.311 (3) |
| C5—C4 | 1.373 (4) | C22—C27 | 1.387 (3) |
| C5—H5A | 0.9300 | C22—C23 | 1.401 (3) |
| C4—C3 | 1.372 (4) | C22—S4 | 1.794 (2) |
| C4—H4A | 0.9300 | C27—C26 | 1.384 (4) |
| C3—C2 | 1.394 (4) | C27—H27A | 0.9300 |
| C3—H3A | 0.9300 | C26—C25 | 1.368 (5) |
| C2—C7 | 1.493 (3) | C26—H26A | 0.9300 |
| C7—O1 | 1.244 (3) | C25—C24 | 1.363 (5) |
| C7—O2 | 1.264 (3) | C25—H25A | 0.9300 |
| C8—C13 | 1.389 (3) | C24—C23 | 1.398 (4) |
| C8—C9 | 1.400 (3) | C24—H24A | 0.9300 |
| C8—S2 | 1.793 (2) | C23—C28 | 1.485 (4) |
| C9—C10 | 1.401 (3) | C28—O8 | 1.235 (3) |
| C9—C14 | 1.474 (3) | C28—O7 | 1.267 (4) |
| C10—C11 | 1.367 (4) | C29—N1 | 1.376 (6) |
| C10—H10A | 0.9300 | C29—H29A | 0.9600 |
| C11—C12 | 1.377 (4) | C29—H29B | 0.9600 |
| C11—H11A | 0.9300 | C29—H29C | 0.9600 |
| C12—C13 | 1.376 (4) | C30—N1 | 1.345 (6) |
| C12—H12A | 0.9300 | C30—H30A | 0.9600 |
| C13—H13A | 0.9300 | C30—H30B | 0.9600 |
| C14—O4 | 1.204 (3) | C30—H30C | 0.9600 |
| C14—O3 | 1.311 (3) | C31—N1 | 1.467 (7) |
| C15—C20 | 1.391 (3) | C31—H31A | 0.9600 |
| C15—C16 | 1.398 (3) | C31—H31B | 0.9600 |
| C15—S3 | 1.790 (2) | C31—H31C | 0.9600 |
| C20—C19 | 1.377 (4) | N1—H11 | 0.874 (10) |
| C20—H20A | 0.9300 | O3—H31 | 0.890 (10) |
| C19—C18 | 1.371 (4) | O5—H51 | 0.885 (10) |
| C19—H19A | 0.9300 | O7—H71 | 0.893 (10) |
| C18—C17 | 1.373 (4) | S1—S2 | 2.0484 (8) |
| C18—H18A | 0.9300 | S3—S4 | 2.0397 (8) |
| C6—C1—C2 | 119.0 (2) | C17—C16—C21 | 119.3 (2) |
| C6—C1—S1 | 120.85 (17) | C15—C16—C21 | 121.2 (2) |
| C2—C1—S1 | 120.17 (17) | O6—C21—O5 | 122.5 (2) |
| C5—C6—C1 | 120.8 (2) | O6—C21—C16 | 123.6 (2) |
| C5—C6—H6A | 119.6 | O5—C21—C16 | 113.9 (2) |
| C1—C6—H6A | 119.6 | C27—C22—C23 | 118.7 (2) |
| C4—C5—C6 | 120.7 (3) | C27—C22—S4 | 120.88 (19) |
| C4—C5—H5A | 119.7 | C23—C22—S4 | 120.45 (19) |
| C6—C5—H5A | 119.7 | C26—C27—C22 | 120.9 (3) |
| C3—C4—C5 | 119.2 (3) | C26—C27—H27A | 119.5 |
| C3—C4—H4A | 120.4 | C22—C27—H27A | 119.5 |
| C5—C4—H4A | 120.4 | C25—C26—C27 | 120.4 (3) |
| C4—C3—C2 | 121.7 (2) | C25—C26—H26A | 119.8 |
| C4—C3—H3A | 119.1 | C27—C26—H26A | 119.8 |
| C2—C3—H3A | 119.1 | C24—C25—C26 | 119.6 (3) |
| C3—C2—C1 | 118.6 (2) | C24—C25—H25A | 120.2 |
| C3—C2—C7 | 117.3 (2) | C26—C25—H25A | 120.2 |
| C1—C2—C7 | 124.1 (2) | C25—C24—C23 | 121.5 (3) |
| O1—C7—O2 | 124.2 (3) | C25—C24—H24A | 119.2 |
| O1—C7—C2 | 119.3 (3) | C23—C24—H24A | 119.2 |
| O2—C7—C2 | 116.5 (2) | C24—C23—C22 | 118.9 (2) |
| C13—C8—C9 | 118.7 (2) | C24—C23—C28 | 116.8 (2) |
| C13—C8—S2 | 121.76 (18) | C22—C23—C28 | 124.3 (2) |
| C9—C8—S2 | 119.57 (17) | O8—C28—O7 | 123.0 (3) |
| C8—C9—C10 | 118.7 (2) | O8—C28—C23 | 120.5 (3) |
| C8—C9—C14 | 122.1 (2) | O7—C28—C23 | 116.5 (2) |
| C10—C9—C14 | 119.2 (2) | N1—C29—H29A | 109.5 |
| C11—C10—C9 | 121.9 (2) | N1—C29—H29B | 109.5 |
| C11—C10—H10A | 119.0 | H29A—C29—H29B | 109.5 |
| C9—C10—H10A | 119.0 | N1—C29—H29C | 109.5 |
| C10—C11—C12 | 118.9 (2) | H29A—C29—H29C | 109.5 |
| C10—C11—H11A | 120.6 | H29B—C29—H29C | 109.5 |
| C12—C11—H11A | 120.6 | N1—C30—H30A | 109.5 |
| C13—C12—C11 | 120.7 (3) | N1—C30—H30B | 109.5 |
| C13—C12—H12A | 119.7 | H30A—C30—H30B | 109.5 |
| C11—C12—H12A | 119.7 | N1—C30—H30C | 109.5 |
| C12—C13—C8 | 121.1 (2) | H30A—C30—H30C | 109.5 |
| C12—C13—H13A | 119.4 | H30B—C30—H30C | 109.5 |
| C8—C13—H13A | 119.4 | N1—C31—H31A | 109.5 |
| O4—C14—O3 | 122.2 (2) | N1—C31—H31B | 109.5 |
| O4—C14—C9 | 123.8 (2) | H31A—C31—H31B | 109.5 |
| O3—C14—C9 | 114.0 (2) | N1—C31—H31C | 109.5 |
| C20—C15—C16 | 118.5 (2) | H31A—C31—H31C | 109.5 |
| C20—C15—S3 | 121.26 (19) | H31B—C31—H31C | 109.5 |
| C16—C15—S3 | 120.28 (18) | C30—N1—C29 | 125.1 (6) |
| C19—C20—C15 | 120.8 (3) | C30—N1—C31 | 117.5 (6) |
| C19—C20—H20A | 119.6 | C29—N1—C31 | 111.6 (5) |
| C15—C20—H20A | 119.6 | C30—N1—H11 | 98.1 (11) |
| C18—C19—C20 | 120.9 (3) | C29—N1—H11 | 96.0 (11) |
| C18—C19—H19A | 119.5 | C31—N1—H11 | 100 (2) |
| C20—C19—H19A | 119.5 | C14—O3—H31 | 108 (3) |
| C19—C18—C17 | 119.2 (3) | C21—O5—H51 | 110 (3) |
| C19—C18—H18A | 120.4 | C28—O7—H71 | 112 (3) |
| C17—C18—H18A | 120.4 | C1—S1—S2 | 104.31 (7) |
| C18—C17—C16 | 121.1 (3) | C8—S2—S1 | 105.47 (8) |
| C18—C17—H17A | 119.5 | C15—S3—S4 | 105.35 (8) |
| C16—C17—H17A | 119.5 | C22—S4—S3 | 105.22 (8) |
| C17—C16—C15 | 119.5 (2) |
(polymorph2) Tetrakis(trimethylazanium) bis{2-[(2-carboxyphenyl)disulfanyl]benzoate}
2,2'-(disulfanediyl)dibenzoate 2,2'-(disulfanediyl)dibenzoic acid monosolvate top
Crystal data top
| 4C3H10N+·2C14H9O4S2−·C14H8O4S22−·C14H10O4S2 | F(000) = 3072 |
| Mr = 1461.89 | Dx = 1.371 Mg m−3 |
| Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -C 2yc | Cell parameters from 8255 reflections |
| a = 31.7088 (10) Å | θ = 2.4–27.8° |
| b = 11.5254 (3) Å | µ = 0.32 mm−1 |
| c = 23.2263 (8) Å | T = 296 K |
| β = 123.430 (3)° | Block, yellow |
| V = 7083.9 (4) Å3 | 0.80 × 0.58 × 0.17 mm |
| Z = 4 |
Data collection top
| CCD area detector diffractometer | 8363 independent reflections |
| Radiation source: fine-focus sealed tube | 5476 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.025 |
| phi and ω scans | θmax = 27.8°, θmin = 1.8° |
| Absorption correction: multi-scan sadabs | h = −41→41 |
| Tmin = 0.800, Tmax = 0.947 | k = −15→15 |
| 28475 measured reflections | l = −23→30 |
Refinement top
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.198 | H-atom parameters constrained |
| S = 1.28 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
| 8363 reflections | (Δ/σ)max = 0.002 |
| 439 parameters | Δρmax = 1.01 e Å−3 |
| 0 restraints | Δρmin = −0.27 e Å−3 |
Special details top
Geometry. 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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| S1 | 0.73703 (2) | 0.58862 (4) | 0.68940 (3) | 0.04411 (17) | |
| O1 | 0.77820 (6) | 0.57334 (14) | 0.54118 (8) | 0.0554 (4) | |
| H1 | 0.7621 | 0.5281 | 0.5065 | 0.066* | |
| C1 | 0.77526 (7) | 0.69357 (17) | 0.68200 (9) | 0.0365 (4) | |
| N1 | 0.63508 (6) | 0.90501 (16) | 0.50403 (9) | 0.0480 (5) | |
| H11 | 0.6625 | 0.9478 | 0.5239 | 0.058* | |
| S2 | 0.76328 (2) | 0.58658 (5) | 0.79201 (3) | 0.04456 (17) | |
| O2 | 0.71748 (6) | 0.54935 (14) | 0.56011 (8) | 0.0538 (4) | |
| C2 | 0.78073 (7) | 0.68858 (17) | 0.62596 (9) | 0.0357 (4) | |
| N2 | 0.61609 (7) | 0.34501 (17) | 0.49854 (9) | 0.0523 (5) | |
| H21 | 0.5888 | 0.3012 | 0.4792 | 0.063* | |
| S3 | 0.51216 (2) | −0.33793 (5) | 0.30109 (3) | 0.04933 (19) | |
| O3 | 0.73854 (7) | 0.58713 (15) | 0.95642 (9) | 0.0618 (5) | |
| C3 | 0.80847 (8) | 0.77396 (19) | 0.61906 (11) | 0.0474 (5) | |
| H3A | 0.8116 | 0.7716 | 0.5815 | 0.057* | |
| O4 | 0.79072 (6) | 0.55696 (15) | 0.92333 (8) | 0.0589 (5) | |
| C4 | 0.83152 (9) | 0.8621 (2) | 0.66659 (13) | 0.0558 (6) | |
| H4A | 0.8499 | 0.9189 | 0.6611 | 0.067* | |
| S4 | 0.51408 (2) | 0.16538 (5) | 0.30152 (3) | 0.04530 (18) | |
| O5 | 0.47388 (6) | −0.33318 (14) | 0.45339 (8) | 0.0589 (5) | |
| H5 | 0.4889 | −0.2811 | 0.4856 | 0.071* | |
| C5 | 0.82712 (8) | 0.8652 (2) | 0.72245 (12) | 0.0541 (6) | |
| H5A | 0.8428 | 0.9240 | 0.7550 | 0.065* | |
| O6 | 0.53161 (6) | −0.29843 (15) | 0.42983 (8) | 0.0563 (4) | |
| C6 | 0.79971 (8) | 0.78182 (18) | 0.73012 (11) | 0.0466 (5) | |
| H6A | 0.7974 | 0.7844 | 0.7684 | 0.056* | |
| C7 | 0.75569 (7) | 0.59604 (17) | 0.57253 (10) | 0.0385 (5) | |
| O7 | 0.48678 (7) | 0.17261 (15) | 0.46160 (9) | 0.0641 (5) | |
| C8 | 0.72681 (7) | 0.69332 (16) | 0.80180 (9) | 0.0344 (4) | |
| O8 | 0.54280 (6) | 0.19030 (16) | 0.43403 (9) | 0.0655 (5) | |
| C9 | 0.72573 (7) | 0.69286 (17) | 0.86151 (10) | 0.0359 (4) | |
| C10 | 0.69850 (8) | 0.77847 (19) | 0.86958 (11) | 0.0443 (5) | |
| H10A | 0.6982 | 0.7793 | 0.9094 | 0.053* | |
| C11 | 0.67196 (8) | 0.8621 (2) | 0.82002 (12) | 0.0511 (6) | |
| H11A | 0.6542 | 0.9191 | 0.8264 | 0.061* | |
| C12 | 0.67212 (8) | 0.8601 (2) | 0.76102 (11) | 0.0500 (6) | |
| H12A | 0.6537 | 0.9155 | 0.7269 | 0.060* | |
| C13 | 0.69912 (8) | 0.77743 (18) | 0.75164 (10) | 0.0439 (5) | |
| H13A | 0.6989 | 0.7777 | 0.7114 | 0.053* | |
| C14 | 0.75392 (8) | 0.60487 (17) | 0.91770 (10) | 0.0389 (5) | |
| C15 | 0.47417 (7) | −0.44382 (17) | 0.30797 (10) | 0.0381 (4) | |
| C16 | 0.46958 (7) | −0.44101 (17) | 0.36492 (10) | 0.0393 (5) | |
| C17 | 0.44209 (8) | −0.5281 (2) | 0.37159 (12) | 0.0500 (6) | |
| H17A | 0.4394 | −0.5273 | 0.4095 | 0.060* | |
| C18 | 0.41870 (9) | −0.6157 (2) | 0.32344 (14) | 0.0586 (6) | |
| H18A | 0.4010 | −0.6739 | 0.3292 | 0.070* | |
| C19 | 0.42199 (8) | −0.6151 (2) | 0.26694 (13) | 0.0556 (6) | |
| H19A | 0.4055 | −0.6724 | 0.2334 | 0.067* | |
| C20 | 0.44936 (8) | −0.53096 (19) | 0.25918 (11) | 0.0481 (5) | |
| H20A | 0.4512 | −0.5325 | 0.2206 | 0.058* | |
| C21 | 0.49481 (8) | −0.35010 (18) | 0.41921 (10) | 0.0412 (5) | |
| C22 | 0.47742 (7) | 0.05897 (17) | 0.31102 (10) | 0.0365 (4) | |
| C23 | 0.47610 (7) | 0.05994 (17) | 0.37017 (10) | 0.0367 (4) | |
| C24 | 0.44880 (8) | −0.02594 (19) | 0.37805 (11) | 0.0460 (5) | |
| H24A | 0.4485 | −0.0268 | 0.4179 | 0.055* | |
| C25 | 0.42222 (9) | −0.1097 (2) | 0.32859 (13) | 0.0511 (6) | |
| H25A | 0.4044 | −0.1666 | 0.3350 | 0.061* | |
| C26 | 0.42245 (8) | −0.10776 (19) | 0.26963 (12) | 0.0508 (6) | |
| H26A | 0.4039 | −0.1627 | 0.2353 | 0.061* | |
| C27 | 0.44991 (8) | −0.02498 (18) | 0.26085 (10) | 0.0458 (5) | |
| H27A | 0.4500 | −0.0253 | 0.2209 | 0.055* | |
| C28 | 0.50426 (8) | 0.14831 (18) | 0.42607 (10) | 0.0411 (5) | |
| C29 | 0.64444 (10) | 0.3122 (3) | 0.46789 (15) | 0.0784 (8) | |
| H29A | 0.6235 | 0.3233 | 0.4188 | 0.118* | |
| H29B | 0.6542 | 0.2322 | 0.4778 | 0.118* | |
| H29C | 0.6741 | 0.3598 | 0.4870 | 0.118* | |
| C30 | 0.64748 (10) | 0.3280 (2) | 0.57376 (13) | 0.0746 (8) | |
| H30A | 0.6283 | 0.3476 | 0.5930 | 0.112* | |
| H30B | 0.6768 | 0.3769 | 0.5936 | 0.112* | |
| H30C | 0.6579 | 0.2483 | 0.5838 | 0.112* | |
| C31 | 0.59688 (11) | 0.4634 (2) | 0.48090 (17) | 0.0916 (10) | |
| H31A | 0.5769 | 0.4722 | 0.4317 | 0.137* | |
| H31B | 0.6247 | 0.5167 | 0.5008 | 0.137* | |
| H31C | 0.5764 | 0.4791 | 0.4987 | 0.137* | |
| C32 | 0.65340 (10) | 0.7857 (2) | 0.52064 (16) | 0.0808 (9) | |
| H32A | 0.6731 | 0.7755 | 0.5698 | 0.121* | |
| H32B | 0.6740 | 0.7697 | 0.5030 | 0.121* | |
| H32C | 0.6252 | 0.7334 | 0.5000 | 0.121* | |
| C33 | 0.60436 (9) | 0.9234 (2) | 0.42925 (12) | 0.0671 (7) | |
| H33A | 0.6238 | 0.9039 | 0.4103 | 0.101* | |
| H33B | 0.5943 | 1.0034 | 0.4197 | 0.101* | |
| H33C | 0.5748 | 0.8751 | 0.4088 | 0.101* | |
| C34 | 0.60660 (10) | 0.9371 (3) | 0.53433 (16) | 0.0791 (9) | |
| H34A | 0.6271 | 0.9236 | 0.5832 | 0.119* | |
| H34B | 0.5765 | 0.8909 | 0.5140 | 0.119* | |
| H34C | 0.5976 | 1.0177 | 0.5256 | 0.119* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0565 (4) | 0.0407 (3) | 0.0423 (3) | −0.0101 (2) | 0.0318 (3) | −0.0085 (2) |
| O1 | 0.0591 (10) | 0.0684 (11) | 0.0566 (10) | −0.0180 (8) | 0.0432 (8) | −0.0225 (8) |
| C1 | 0.0352 (10) | 0.0359 (11) | 0.0329 (10) | 0.0011 (8) | 0.0152 (8) | −0.0009 (7) |
| N1 | 0.0384 (10) | 0.0562 (12) | 0.0489 (11) | −0.0039 (8) | 0.0237 (9) | −0.0002 (8) |
| S2 | 0.0568 (4) | 0.0419 (3) | 0.0430 (3) | 0.0124 (2) | 0.0325 (3) | 0.0076 (2) |
| O2 | 0.0475 (9) | 0.0659 (10) | 0.0574 (10) | −0.0200 (8) | 0.0348 (8) | −0.0253 (8) |
| C2 | 0.0307 (10) | 0.0378 (11) | 0.0346 (10) | −0.0010 (8) | 0.0155 (8) | −0.0018 (8) |
| N2 | 0.0392 (10) | 0.0591 (12) | 0.0552 (12) | −0.0050 (8) | 0.0239 (9) | −0.0019 (9) |
| S3 | 0.0610 (4) | 0.0418 (4) | 0.0537 (3) | −0.0126 (3) | 0.0369 (3) | −0.0094 (2) |
| O3 | 0.0783 (12) | 0.0702 (11) | 0.0630 (11) | 0.0227 (9) | 0.0554 (10) | 0.0233 (8) |
| C3 | 0.0460 (12) | 0.0500 (13) | 0.0486 (12) | −0.0039 (10) | 0.0276 (10) | 0.0023 (10) |
| O4 | 0.0531 (10) | 0.0759 (11) | 0.0569 (10) | 0.0292 (8) | 0.0362 (8) | 0.0325 (8) |
| C4 | 0.0493 (14) | 0.0469 (14) | 0.0664 (15) | −0.0127 (11) | 0.0289 (12) | 0.0002 (11) |
| S4 | 0.0552 (4) | 0.0420 (3) | 0.0466 (3) | −0.0114 (2) | 0.0331 (3) | −0.0093 (2) |
| O5 | 0.0687 (11) | 0.0651 (11) | 0.0602 (10) | −0.0215 (8) | 0.0464 (9) | −0.0188 (8) |
| C5 | 0.0478 (13) | 0.0430 (13) | 0.0560 (14) | −0.0103 (10) | 0.0187 (11) | −0.0126 (10) |
| O6 | 0.0483 (9) | 0.0639 (11) | 0.0627 (10) | −0.0192 (8) | 0.0343 (8) | −0.0234 (8) |
| C6 | 0.0479 (13) | 0.0455 (13) | 0.0398 (11) | −0.0046 (10) | 0.0199 (10) | −0.0086 (9) |
| C7 | 0.0364 (11) | 0.0445 (12) | 0.0341 (10) | −0.0003 (8) | 0.0192 (9) | −0.0008 (8) |
| O7 | 0.0778 (12) | 0.0742 (12) | 0.0622 (10) | −0.0255 (9) | 0.0524 (10) | −0.0255 (8) |
| C8 | 0.0330 (10) | 0.0340 (10) | 0.0336 (10) | −0.0006 (8) | 0.0167 (8) | 0.0002 (7) |
| O8 | 0.0513 (10) | 0.0856 (13) | 0.0661 (11) | −0.0297 (9) | 0.0364 (9) | −0.0364 (9) |
| C9 | 0.0335 (10) | 0.0390 (11) | 0.0356 (10) | −0.0010 (8) | 0.0193 (8) | 0.0002 (8) |
| C10 | 0.0435 (12) | 0.0465 (13) | 0.0481 (12) | 0.0039 (9) | 0.0285 (10) | −0.0017 (9) |
| C11 | 0.0423 (12) | 0.0436 (13) | 0.0641 (15) | 0.0074 (10) | 0.0272 (11) | −0.0023 (10) |
| C12 | 0.0427 (12) | 0.0401 (12) | 0.0487 (13) | 0.0090 (10) | 0.0134 (10) | 0.0081 (9) |
| C13 | 0.0450 (12) | 0.0430 (12) | 0.0345 (10) | 0.0019 (9) | 0.0162 (9) | 0.0039 (8) |
| C14 | 0.0393 (11) | 0.0427 (12) | 0.0353 (10) | 0.0035 (9) | 0.0209 (9) | 0.0042 (8) |
| C15 | 0.0324 (10) | 0.0352 (11) | 0.0399 (10) | 0.0000 (8) | 0.0157 (9) | −0.0009 (8) |
| C16 | 0.0332 (10) | 0.0376 (11) | 0.0410 (11) | −0.0004 (8) | 0.0166 (9) | 0.0005 (8) |
| C17 | 0.0450 (12) | 0.0468 (14) | 0.0572 (13) | −0.0055 (10) | 0.0275 (11) | 0.0027 (10) |
| C18 | 0.0499 (14) | 0.0458 (14) | 0.0744 (17) | −0.0130 (11) | 0.0307 (13) | −0.0007 (11) |
| C19 | 0.0434 (13) | 0.0429 (13) | 0.0620 (15) | −0.0079 (10) | 0.0173 (12) | −0.0131 (10) |
| C20 | 0.0437 (12) | 0.0442 (13) | 0.0466 (12) | −0.0032 (10) | 0.0187 (10) | −0.0077 (9) |
| C21 | 0.0394 (11) | 0.0429 (12) | 0.0377 (10) | 0.0011 (9) | 0.0190 (9) | 0.0012 (8) |
| C22 | 0.0320 (10) | 0.0369 (11) | 0.0363 (10) | 0.0009 (8) | 0.0162 (8) | −0.0005 (8) |
| C23 | 0.0318 (10) | 0.0393 (11) | 0.0362 (10) | −0.0007 (8) | 0.0169 (8) | −0.0015 (8) |
| C24 | 0.0441 (12) | 0.0493 (13) | 0.0467 (12) | −0.0001 (10) | 0.0262 (10) | 0.0043 (9) |
| C25 | 0.0448 (13) | 0.0424 (13) | 0.0612 (14) | −0.0067 (10) | 0.0262 (11) | 0.0041 (10) |
| C26 | 0.0430 (13) | 0.0413 (13) | 0.0514 (13) | −0.0082 (10) | 0.0155 (11) | −0.0082 (9) |
| C27 | 0.0476 (13) | 0.0428 (13) | 0.0388 (11) | −0.0033 (10) | 0.0186 (10) | −0.0048 (9) |
| C28 | 0.0405 (11) | 0.0480 (13) | 0.0342 (10) | −0.0025 (9) | 0.0202 (9) | −0.0028 (8) |
| C29 | 0.0656 (18) | 0.096 (2) | 0.092 (2) | −0.0081 (15) | 0.0551 (17) | −0.0134 (17) |
| C30 | 0.0605 (16) | 0.087 (2) | 0.0653 (17) | −0.0010 (14) | 0.0276 (14) | 0.0026 (14) |
| C31 | 0.0704 (19) | 0.066 (2) | 0.131 (3) | 0.0207 (15) | 0.051 (2) | 0.0254 (19) |
| C32 | 0.0715 (18) | 0.0649 (19) | 0.100 (2) | 0.0154 (14) | 0.0436 (18) | 0.0206 (16) |
| C33 | 0.0531 (15) | 0.0836 (19) | 0.0532 (15) | 0.0025 (13) | 0.0221 (12) | 0.0093 (12) |
| C34 | 0.0673 (18) | 0.102 (2) | 0.089 (2) | −0.0045 (16) | 0.0570 (17) | −0.0132 (17) |
Geometric parameters (Å, º) top
| S1—C1 | 1.786 (2) | C12—C13 | 1.376 (3) |
| S1—S2 | 2.0464 (8) | C12—H12A | 0.9300 |
| O1—C7 | 1.297 (2) | C13—H13A | 0.9300 |
| O1—H1 | 0.8534 | C15—C20 | 1.389 (3) |
| C1—C6 | 1.389 (3) | C15—C16 | 1.408 (3) |
| C1—C2 | 1.406 (3) | C16—C17 | 1.393 (3) |
| N1—C32 | 1.460 (3) | C16—C21 | 1.489 (3) |
| N1—C33 | 1.465 (3) | C17—C18 | 1.380 (3) |
| N1—C34 | 1.466 (3) | C17—H17A | 0.9300 |
| N1—H11 | 0.8775 | C18—C19 | 1.373 (4) |
| S2—C8 | 1.7869 (19) | C18—H18A | 0.9300 |
| O2—C7 | 1.206 (2) | C19—C20 | 1.378 (3) |
| C2—C3 | 1.387 (3) | C19—H19A | 0.9300 |
| C2—C7 | 1.491 (3) | C20—H20A | 0.9300 |
| N2—C31 | 1.458 (3) | C22—C27 | 1.391 (3) |
| N2—C29 | 1.471 (3) | C22—C23 | 1.397 (3) |
| N2—C30 | 1.472 (3) | C23—C24 | 1.392 (3) |
| N2—H21 | 0.8816 | C23—C28 | 1.498 (3) |
| S3—C15 | 1.783 (2) | C24—C25 | 1.376 (3) |
| S3—S3i | 2.0518 (11) | C24—H24A | 0.9300 |
| O3—C14 | 1.253 (2) | C25—C26 | 1.374 (3) |
| C3—C4 | 1.377 (3) | C25—H25A | 0.9300 |
| C3—H3A | 0.9300 | C26—C27 | 1.380 (3) |
| O4—C14 | 1.231 (2) | C26—H26A | 0.9300 |
| C4—C5 | 1.380 (3) | C27—H27A | 0.9300 |
| C4—H4A | 0.9300 | C29—H29A | 0.9600 |
| S4—C22 | 1.785 (2) | C29—H29B | 0.9600 |
| S4—S4i | 2.0420 (10) | C29—H29C | 0.9600 |
| O5—C21 | 1.300 (2) | C30—H30A | 0.9600 |
| O5—H5 | 0.8685 | C30—H30B | 0.9600 |
| C5—C6 | 1.371 (3) | C30—H30C | 0.9600 |
| C5—H5A | 0.9300 | C31—H31A | 0.9600 |
| O6—C21 | 1.208 (2) | C31—H31B | 0.9600 |
| C6—H6A | 0.9300 | C31—H31C | 0.9600 |
| O7—C28 | 1.253 (2) | C32—H32A | 0.9600 |
| C8—C13 | 1.393 (3) | C32—H32B | 0.9600 |
| C8—C9 | 1.406 (3) | C32—H32C | 0.9600 |
| O8—C28 | 1.230 (2) | C33—H33A | 0.9600 |
| C9—C10 | 1.390 (3) | C33—H33B | 0.9600 |
| C9—C14 | 1.498 (3) | C33—H33C | 0.9600 |
| C10—C11 | 1.376 (3) | C34—H34A | 0.9600 |
| C10—H10A | 0.9300 | C34—H34B | 0.9600 |
| C11—C12 | 1.373 (3) | C34—H34C | 0.9600 |
| C11—H11A | 0.9300 | ||
| C1—S1—S2 | 104.93 (6) | C19—C18—C17 | 118.8 (2) |
| C7—O1—H1 | 115.2 | C19—C18—H18A | 120.6 |
| C6—C1—C2 | 118.42 (19) | C17—C18—H18A | 120.6 |
| C6—C1—S1 | 121.73 (16) | C18—C19—C20 | 120.9 (2) |
| C2—C1—S1 | 119.85 (14) | C18—C19—H19A | 119.6 |
| C32—N1—C33 | 111.0 (2) | C20—C19—H19A | 119.6 |
| C32—N1—C34 | 111.8 (2) | C19—C20—C15 | 121.1 (2) |
| C33—N1—C34 | 110.5 (2) | C19—C20—H20A | 119.4 |
| C32—N1—H11 | 104.8 | C15—C20—H20A | 119.4 |
| C33—N1—H11 | 111.2 | O6—C21—O5 | 124.20 (19) |
| C34—N1—H11 | 107.5 | O6—C21—C16 | 121.85 (19) |
| C8—S2—S1 | 105.30 (6) | O5—C21—C16 | 113.96 (18) |
| C3—C2—C1 | 119.18 (18) | C27—C22—C23 | 118.98 (18) |
| C3—C2—C7 | 119.49 (18) | C27—C22—S4 | 121.66 (16) |
| C1—C2—C7 | 121.28 (17) | C23—C22—S4 | 119.36 (15) |
| C31—N2—C29 | 112.1 (2) | C24—C23—C22 | 118.77 (18) |
| C31—N2—C30 | 111.3 (2) | C24—C23—C28 | 119.13 (18) |
| C29—N2—C30 | 110.3 (2) | C22—C23—C28 | 122.08 (18) |
| C31—N2—H21 | 104.6 | C25—C24—C23 | 121.9 (2) |
| C29—N2—H21 | 107.2 | C25—C24—H24A | 119.1 |
| C30—N2—H21 | 111.1 | C23—C24—H24A | 119.1 |
| C15—S3—S3i | 105.17 (7) | C26—C25—C24 | 118.9 (2) |
| C4—C3—C2 | 121.4 (2) | C26—C25—H25A | 120.5 |
| C4—C3—H3A | 119.3 | C24—C25—H25A | 120.5 |
| C2—C3—H3A | 119.3 | C25—C26—C27 | 120.6 (2) |
| C3—C4—C5 | 119.3 (2) | C25—C26—H26A | 119.7 |
| C3—C4—H4A | 120.4 | C27—C26—H26A | 119.7 |
| C5—C4—H4A | 120.4 | C26—C27—C22 | 120.8 (2) |
| C22—S4—S4i | 104.53 (7) | C26—C27—H27A | 119.6 |
| C21—O5—H5 | 114.1 | C22—C27—H27A | 119.6 |
| C6—C5—C4 | 120.2 (2) | O8—C28—O7 | 125.2 (2) |
| C6—C5—H5A | 119.9 | O8—C28—C23 | 117.81 (18) |
| C4—C5—H5A | 119.9 | O7—C28—C23 | 116.99 (18) |
| C5—C6—C1 | 121.4 (2) | N2—C29—H29A | 109.5 |
| C5—C6—H6A | 119.3 | N2—C29—H29B | 109.5 |
| C1—C6—H6A | 119.3 | H29A—C29—H29B | 109.5 |
| O2—C7—O1 | 124.53 (18) | N2—C29—H29C | 109.5 |
| O2—C7—C2 | 121.49 (18) | H29A—C29—H29C | 109.5 |
| O1—C7—C2 | 113.98 (17) | H29B—C29—H29C | 109.5 |
| C13—C8—C9 | 118.76 (18) | N2—C30—H30A | 109.5 |
| C13—C8—S2 | 121.76 (15) | N2—C30—H30B | 109.5 |
| C9—C8—S2 | 119.48 (14) | H30A—C30—H30B | 109.5 |
| C10—C9—C8 | 119.00 (18) | N2—C30—H30C | 109.5 |
| C10—C9—C14 | 118.65 (17) | H30A—C30—H30C | 109.5 |
| C8—C9—C14 | 122.34 (17) | H30B—C30—H30C | 109.5 |
| C11—C10—C9 | 121.5 (2) | N2—C31—H31A | 109.5 |
| C11—C10—H10A | 119.2 | N2—C31—H31B | 109.5 |
| C9—C10—H10A | 119.2 | H31A—C31—H31B | 109.5 |
| C12—C11—C10 | 119.1 (2) | N2—C31—H31C | 109.5 |
| C12—C11—H11A | 120.4 | H31A—C31—H31C | 109.5 |
| C10—C11—H11A | 120.4 | H31B—C31—H31C | 109.5 |
| C11—C12—C13 | 120.9 (2) | N1—C32—H32A | 109.5 |
| C11—C12—H12A | 119.5 | N1—C32—H32B | 109.5 |
| C13—C12—H12A | 119.5 | H32A—C32—H32B | 109.5 |
| C12—C13—C8 | 120.6 (2) | N1—C32—H32C | 109.5 |
| C12—C13—H13A | 119.7 | H32A—C32—H32C | 109.5 |
| C8—C13—H13A | 119.7 | H32B—C32—H32C | 109.5 |
| O4—C14—O3 | 124.83 (19) | N1—C33—H33A | 109.5 |
| O4—C14—C9 | 118.13 (17) | N1—C33—H33B | 109.5 |
| O3—C14—C9 | 117.02 (18) | H33A—C33—H33B | 109.5 |
| C20—C15—C16 | 118.52 (19) | N1—C33—H33C | 109.5 |
| C20—C15—S3 | 121.94 (17) | H33A—C33—H33C | 109.5 |
| C16—C15—S3 | 119.53 (15) | H33B—C33—H33C | 109.5 |
| C17—C16—C15 | 118.86 (19) | N1—C34—H34A | 109.5 |
| C17—C16—C21 | 119.35 (19) | N1—C34—H34B | 109.5 |
| C15—C16—C21 | 121.76 (18) | H34A—C34—H34B | 109.5 |
| C18—C17—C16 | 121.8 (2) | N1—C34—H34C | 109.5 |
| C18—C17—H17A | 119.1 | H34A—C34—H34C | 109.5 |
| C16—C17—H17A | 119.1 | H34B—C34—H34C | 109.5 |
| Symmetry code: (i) −x+1, y, −z+1/2. |
(polymorph3) Trimethylazanium 2-[(2-carboxyphenyl)disulfanyl]benzoate top
Crystal data top
| C3H10N+·C14H9O4S2− | F(000) = 1536 |
| Mr = 365.45 | Dx = 1.348 Mg m−3 |
| Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -C 2yc | Cell parameters from 1906 reflections |
| a = 13.5363 (4) Å | θ = 2.4–24.5° |
| b = 12.1071 (3) Å | µ = 0.32 mm−1 |
| c = 22.1248 (6) Å | T = 296 K |
| β = 96.532 (2)° | Block, yellow |
| V = 3602.39 (17) Å3 | 0.14 × 0.14 × 0.09 mm |
| Z = 8 |
Data collection top
| CCD area detector diffractometer | 3998 independent reflections |
| Radiation source: fine-focus sealed tube | 2737 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.032 |
| phi and ω scans | θmax = 27.2°, θmin = 2.3° |
| Absorption correction: multi-scan sadabs | h = −17→17 |
| Tmin = 0.957, Tmax = 0.972 | k = −15→15 |
| 8993 measured reflections | l = −22→28 |
Refinement top
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.01 | w = 1/[σ2(Fo2) + (0.0545P)2 + 0.8819P] where P = (Fo2 + 2Fc2)/3 |
| 3998 reflections | (Δ/σ)max < 0.001 |
| 253 parameters | Δρmax = 0.22 e Å−3 |
| 2 restraints | Δρmin = −0.19 e Å−3 |
Special details top
Geometry. 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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | Occ. (<1) | |
| S1 | 0.08870 (4) | 0.20518 (4) | 0.35282 (3) | 0.04802 (18) | |
| C1 | 0.00578 (14) | 0.12021 (16) | 0.38976 (9) | 0.0358 (4) | |
| N1 | 0.19701 (17) | −0.2371 (2) | 0.26506 (10) | 0.0660 (6) | |
| H1 | 0.1545 (18) | −0.214 (2) | 0.2927 (11) | 0.099* | |
| O1 | 0.13769 (12) | 0.00789 (13) | 0.31991 (8) | 0.0606 (5) | |
| S2 | 0.04589 (4) | 0.36573 (5) | 0.36501 (3) | 0.04893 (18) | |
| C2 | 0.01072 (14) | 0.00486 (16) | 0.38430 (9) | 0.0357 (4) | |
| O2 | 0.08259 (13) | −0.15481 (12) | 0.34535 (8) | 0.0614 (5) | |
| C3 | −0.05380 (16) | −0.05919 (17) | 0.41453 (10) | 0.0446 (5) | |
| H3A | −0.0511 | −0.1357 | 0.4115 | 0.054* | |
| O3 | 0.03715 (16) | 0.58828 (14) | 0.36307 (9) | 0.0739 (6) | |
| C4 | −0.12131 (16) | −0.01229 (19) | 0.44874 (11) | 0.0499 (6) | |
| H4A | −0.1638 | −0.0566 | 0.4683 | 0.060* | |
| O4 | 0.10917 (15) | 0.70275 (13) | 0.43247 (8) | 0.0649 (5) | |
| H4 | 0.097 (2) | 0.748 (2) | 0.4026 (10) | 0.097* | |
| C5 | −0.12542 (16) | 0.10050 (18) | 0.45372 (11) | 0.0484 (6) | |
| H5A | −0.1711 | 0.1328 | 0.4767 | 0.058* | |
| C6 | −0.06248 (15) | 0.16584 (17) | 0.42495 (10) | 0.0432 (5) | |
| H6A | −0.0656 | 0.2422 | 0.4291 | 0.052* | |
| C7 | 0.08295 (16) | −0.04951 (17) | 0.34713 (9) | 0.0415 (5) | |
| C8 | 0.09865 (14) | 0.40280 (17) | 0.44019 (9) | 0.0391 (5) | |
| C9 | 0.10886 (14) | 0.51434 (16) | 0.45698 (9) | 0.0392 (5) | |
| C10 | 0.14795 (16) | 0.54076 (19) | 0.51613 (10) | 0.0478 (5) | |
| H10A | 0.1551 | 0.6146 | 0.5273 | 0.057* | |
| C11 | 0.17620 (17) | 0.4604 (2) | 0.55825 (11) | 0.0538 (6) | |
| H11A | 0.2013 | 0.4795 | 0.5977 | 0.065* | |
| C12 | 0.16697 (17) | 0.3512 (2) | 0.54137 (11) | 0.0524 (6) | |
| H12A | 0.1868 | 0.2963 | 0.5696 | 0.063* | |
| C13 | 0.12893 (16) | 0.32234 (18) | 0.48339 (11) | 0.0464 (5) | |
| H13A | 0.1233 | 0.2481 | 0.4728 | 0.056* | |
| C14 | 0.08048 (17) | 0.60388 (17) | 0.41273 (12) | 0.0472 (6) | |
| C15 | 0.2802 (7) | −0.2822 (18) | 0.2976 (3) | 0.116 (6) | 0.55 (2) |
| H15A | 0.2687 | −0.3591 | 0.3049 | 0.174* | 0.55 (2) |
| H15B | 0.2938 | −0.2443 | 0.3357 | 0.174* | 0.55 (2) |
| H15C | 0.3360 | −0.2748 | 0.2748 | 0.174* | 0.55 (2) |
| C15' | 0.3014 (6) | −0.1863 (17) | 0.2884 (6) | 0.093 (5) | 0.45 (2) |
| H15D | 0.3262 | −0.2251 | 0.3249 | 0.139* | 0.45 (2) |
| H15E | 0.3470 | −0.1949 | 0.2586 | 0.139* | 0.45 (2) |
| H15F | 0.2945 | −0.1093 | 0.2974 | 0.139* | 0.45 (2) |
| C16 | 0.1326 (10) | −0.3178 (15) | 0.2279 (5) | 0.114 (6) | 0.52 (2) |
| H16A | 0.0640 | −0.3002 | 0.2302 | 0.171* | 0.52 (2) |
| H16B | 0.1461 | −0.3911 | 0.2433 | 0.171* | 0.52 (2) |
| H16F | 0.1462 | −0.3142 | 0.1863 | 0.171* | 0.52 (2) |
| C16' | 0.202 (2) | −0.3568 (8) | 0.2673 (13) | 0.166 (13) | 0.48 (2) |
| H16C | 0.1384 | −0.3870 | 0.2518 | 0.249* | 0.48 (2) |
| H16D | 0.2188 | −0.3803 | 0.3086 | 0.249* | 0.48 (2) |
| H16E | 0.2516 | −0.3822 | 0.2429 | 0.249* | 0.48 (2) |
| C17 | 0.1717 (15) | −0.1791 (16) | 0.2106 (3) | 0.141 (6) | 0.65 (3) |
| H17A | 0.1081 | −0.2040 | 0.1918 | 0.211* | 0.65 (3) |
| H17B | 0.2211 | −0.1922 | 0.1835 | 0.211* | 0.65 (3) |
| H17C | 0.1684 | −0.1016 | 0.2191 | 0.211* | 0.65 (3) |
| C17' | 0.2306 (19) | −0.1447 (11) | 0.2269 (12) | 0.089 (7) | 0.35 (3) |
| H17D | 0.1820 | −0.1305 | 0.1928 | 0.134* | 0.35 (3) |
| H17E | 0.2400 | −0.0794 | 0.2515 | 0.134* | 0.35 (3) |
| H17F | 0.2925 | −0.1650 | 0.2127 | 0.134* | 0.35 (3) |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0589 (4) | 0.0323 (3) | 0.0571 (4) | −0.0050 (2) | 0.0254 (3) | −0.0007 (2) |
| C1 | 0.0378 (10) | 0.0314 (10) | 0.0389 (11) | −0.0022 (8) | 0.0078 (8) | 0.0002 (8) |
| N1 | 0.0673 (15) | 0.0783 (17) | 0.0559 (14) | 0.0196 (12) | 0.0217 (11) | −0.0089 (12) |
| O1 | 0.0693 (11) | 0.0432 (9) | 0.0767 (12) | −0.0025 (8) | 0.0411 (9) | −0.0036 (8) |
| S2 | 0.0650 (4) | 0.0311 (3) | 0.0506 (3) | −0.0018 (2) | 0.0062 (3) | 0.0028 (2) |
| C2 | 0.0401 (11) | 0.0309 (10) | 0.0370 (11) | −0.0011 (8) | 0.0089 (8) | −0.0024 (8) |
| O2 | 0.0906 (12) | 0.0306 (8) | 0.0701 (11) | 0.0060 (8) | 0.0405 (10) | −0.0026 (8) |
| C3 | 0.0514 (12) | 0.0321 (11) | 0.0518 (13) | −0.0053 (9) | 0.0120 (10) | 0.0000 (9) |
| O3 | 0.1126 (16) | 0.0390 (10) | 0.0657 (12) | 0.0008 (10) | −0.0097 (11) | 0.0083 (9) |
| C4 | 0.0469 (12) | 0.0479 (13) | 0.0584 (14) | −0.0087 (10) | 0.0208 (11) | 0.0009 (11) |
| O4 | 0.0965 (14) | 0.0294 (9) | 0.0691 (12) | −0.0009 (8) | 0.0108 (10) | −0.0007 (8) |
| C5 | 0.0428 (12) | 0.0492 (13) | 0.0567 (14) | −0.0002 (10) | 0.0203 (10) | −0.0061 (11) |
| C6 | 0.0430 (11) | 0.0343 (11) | 0.0538 (13) | 0.0020 (9) | 0.0127 (10) | −0.0046 (10) |
| C7 | 0.0500 (12) | 0.0329 (11) | 0.0429 (12) | 0.0020 (9) | 0.0113 (10) | −0.0031 (9) |
| C8 | 0.0361 (11) | 0.0345 (11) | 0.0484 (12) | −0.0004 (8) | 0.0129 (9) | 0.0020 (9) |
| C9 | 0.0374 (11) | 0.0329 (11) | 0.0501 (13) | 0.0008 (8) | 0.0172 (9) | −0.0003 (9) |
| C10 | 0.0492 (12) | 0.0426 (13) | 0.0551 (14) | −0.0014 (10) | 0.0210 (11) | −0.0075 (11) |
| C11 | 0.0534 (14) | 0.0636 (16) | 0.0455 (13) | −0.0029 (12) | 0.0112 (11) | −0.0022 (12) |
| C12 | 0.0511 (13) | 0.0547 (15) | 0.0518 (14) | 0.0009 (11) | 0.0086 (11) | 0.0122 (12) |
| C13 | 0.0478 (12) | 0.0366 (12) | 0.0560 (14) | 0.0002 (9) | 0.0112 (11) | 0.0088 (10) |
| C14 | 0.0545 (13) | 0.0339 (12) | 0.0562 (15) | 0.0042 (10) | 0.0196 (12) | 0.0017 (10) |
| C15 | 0.077 (5) | 0.190 (18) | 0.079 (5) | 0.049 (8) | 0.001 (4) | 0.014 (6) |
| C15' | 0.056 (4) | 0.131 (12) | 0.091 (7) | 0.021 (5) | 0.007 (4) | −0.033 (8) |
| C16 | 0.118 (8) | 0.137 (13) | 0.091 (7) | −0.024 (7) | 0.025 (6) | −0.054 (7) |
| C16' | 0.22 (2) | 0.069 (6) | 0.24 (2) | 0.030 (8) | 0.15 (2) | −0.006 (8) |
| C17 | 0.147 (11) | 0.227 (14) | 0.049 (4) | 0.094 (10) | 0.015 (5) | 0.011 (5) |
| C17' | 0.105 (12) | 0.075 (8) | 0.100 (13) | 0.031 (7) | 0.060 (11) | 0.022 (7) |
Geometric parameters (Å, º) top
| S1—C1 | 1.7874 (19) | C9—C14 | 1.482 (3) |
| S1—S2 | 2.0548 (8) | C10—C11 | 1.371 (3) |
| C1—C6 | 1.389 (3) | C10—H10A | 0.9300 |
| C1—C2 | 1.404 (3) | C11—C12 | 1.375 (3) |
| N1—C15 | 1.378 (7) | C11—H11A | 0.9300 |
| N1—C17 | 1.403 (9) | C12—C13 | 1.372 (3) |
| N1—C16' | 1.450 (9) | C12—H12A | 0.9300 |
| N1—C16 | 1.492 (8) | C13—H13A | 0.9300 |
| N1—C17' | 1.503 (12) | C15—H15A | 0.9600 |
| N1—C15' | 1.573 (11) | C15—H15B | 0.9600 |
| N1—H1 | 0.930 (10) | C15—H15C | 0.9600 |
| O1—C7 | 1.223 (2) | C15—H15D | 1.0705 |
| S2—C8 | 1.791 (2) | C15'—C17' | 1.65 (3) |
| C2—C3 | 1.394 (3) | C15'—H15D | 0.9600 |
| C2—C7 | 1.499 (3) | C15'—H15E | 0.9599 |
| O2—C7 | 1.275 (2) | C15'—H15F | 0.9599 |
| C3—C4 | 1.374 (3) | C16—H16A | 0.9600 |
| C3—H3A | 0.9300 | C16—H16B | 0.9600 |
| O3—C14 | 1.200 (3) | C16—H16F | 0.9600 |
| C4—C5 | 1.372 (3) | C16'—H16C | 0.9600 |
| C4—H4A | 0.9300 | C16'—H16D | 0.9600 |
| O4—C14 | 1.317 (3) | C16'—H16E | 0.9600 |
| O4—H4 | 0.856 (10) | C17—H17A | 0.9600 |
| C5—C6 | 1.371 (3) | C17—H17B | 0.9600 |
| C5—H5A | 0.9300 | C17—H17C | 0.9600 |
| C6—H6A | 0.9300 | C17—H17D | 0.7311 |
| C8—C13 | 1.393 (3) | C17'—H17D | 0.9600 |
| C8—C9 | 1.403 (3) | C17'—H17E | 0.9600 |
| C9—C10 | 1.392 (3) | C17'—H17F | 0.9599 |
| C1—S1—S2 | 106.46 (7) | C11—C12—H12A | 119.6 |
| C6—C1—C2 | 119.03 (18) | C12—C13—C8 | 120.9 (2) |
| C6—C1—S1 | 121.32 (15) | C12—C13—H13A | 119.6 |
| C2—C1—S1 | 119.64 (14) | C8—C13—H13A | 119.6 |
| C15—N1—C17 | 138.8 (10) | O3—C14—O4 | 122.8 (2) |
| C15—N1—C16' | 63.6 (17) | O3—C14—C9 | 123.5 (2) |
| C17—N1—C16' | 122.3 (14) | O4—C14—C9 | 113.7 (2) |
| C15—N1—C16 | 114.8 (13) | N1—C15—H15A | 109.5 |
| C17—N1—C16 | 77.5 (12) | N1—C15—H15B | 109.5 |
| C16'—N1—C16 | 52.1 (8) | H15A—C15—H15B | 109.5 |
| C15—N1—C17' | 107.8 (14) | N1—C15—H15C | 109.5 |
| C17—N1—C17' | 37.4 (6) | H15A—C15—H15C | 109.5 |
| C16'—N1—C17' | 138.3 (7) | H15B—C15—H15C | 109.5 |
| C16—N1—C17' | 112.0 (14) | N1—C15—H15D | 115.3 |
| C15—N1—C15' | 48.2 (5) | H15A—C15—H15D | 128.8 |
| C17—N1—C15' | 102.1 (14) | H15B—C15—H15D | 32.2 |
| C16'—N1—C15' | 110.1 (15) | H15C—C15—H15D | 78.1 |
| C16—N1—C15' | 152.1 (7) | N1—C15'—C17' | 55.5 (7) |
| C17'—N1—C15' | 64.9 (15) | N1—C15'—H15D | 107.5 |
| C15—N1—H1 | 108 (2) | C17'—C15'—H15D | 163.0 |
| C17—N1—H1 | 108 (2) | N1—C15'—H15E | 110.8 |
| C16'—N1—H1 | 108 (2) | C17'—C15'—H15E | 79.9 |
| C16—N1—H1 | 101.3 (19) | H15D—C15'—H15E | 109.5 |
| C17'—N1—H1 | 113 (2) | N1—C15'—H15F | 110.1 |
| C15'—N1—H1 | 105.3 (19) | C17'—C15'—H15F | 79.2 |
| C8—S2—S1 | 105.68 (7) | H15D—C15'—H15F | 109.5 |
| C3—C2—C1 | 118.25 (18) | H15E—C15'—H15F | 109.5 |
| C3—C2—C7 | 120.13 (18) | N1—C16—H16A | 109.5 |
| C1—C2—C7 | 121.62 (17) | N1—C16—H16B | 109.5 |
| C4—C3—C2 | 121.8 (2) | H16A—C16—H16B | 109.5 |
| C4—C3—H3A | 119.1 | N1—C16—H16F | 109.5 |
| C2—C3—H3A | 119.1 | H16A—C16—H16F | 109.5 |
| C5—C4—C3 | 119.4 (2) | H16B—C16—H16F | 109.5 |
| C5—C4—H4A | 120.3 | N1—C16'—H16C | 109.5 |
| C3—C4—H4A | 120.3 | N1—C16'—H16D | 109.5 |
| C14—O4—H4 | 107 (2) | H16C—C16'—H16D | 109.5 |
| C6—C5—C4 | 120.27 (19) | N1—C16'—H16E | 109.5 |
| C6—C5—H5A | 119.9 | H16C—C16'—H16E | 109.5 |
| C4—C5—H5A | 119.9 | H16D—C16'—H16E | 109.5 |
| C5—C6—C1 | 121.26 (19) | N1—C17—H17A | 109.5 |
| C5—C6—H6A | 119.4 | N1—C17—H17B | 109.5 |
| C1—C6—H6A | 119.4 | H17A—C17—H17B | 109.5 |
| O1—C7—O2 | 123.57 (19) | N1—C17—H17C | 109.5 |
| O1—C7—C2 | 119.33 (18) | H17A—C17—H17C | 109.5 |
| O2—C7—C2 | 117.09 (18) | H17B—C17—H17C | 109.5 |
| C13—C8—C9 | 118.6 (2) | N1—C17—H17D | 145.4 |
| C13—C8—S2 | 121.13 (17) | H17A—C17—H17D | 103.7 |
| C9—C8—S2 | 120.26 (16) | H17B—C17—H17D | 66.9 |
| C10—C9—C8 | 119.0 (2) | H17C—C17—H17D | 48.1 |
| C10—C9—C14 | 119.7 (2) | N1—C17'—C15' | 59.6 (10) |
| C8—C9—C14 | 121.3 (2) | N1—C17'—H17D | 110.5 |
| C11—C10—C9 | 121.5 (2) | C15'—C17'—H17D | 170.2 |
| C11—C10—H10A | 119.2 | N1—C17'—H17E | 108.9 |
| C9—C10—H10A | 119.2 | C15'—C17'—H17E | 76.0 |
| C10—C11—C12 | 119.2 (2) | H17D—C17'—H17E | 109.5 |
| C10—C11—H11A | 120.4 | N1—C17'—H17F | 109.0 |
| C12—C11—H11A | 120.4 | C15'—C17'—H17F | 75.3 |
| C13—C12—C11 | 120.8 (2) | H17D—C17'—H17F | 109.5 |
| C13—C12—H12A | 119.6 | H17E—C17'—H17F | 109.5 |
| S2—S1—C1—C6 | −7.28 (19) | C13—C8—C9—C14 | 178.41 (18) |
| S2—S1—C1—C2 | 174.03 (15) | S2—C8—C9—C14 | −2.6 (3) |
| C1—S1—S2—C8 | 80.51 (10) | C8—C9—C10—C11 | −0.3 (3) |
| C6—C1—C2—C3 | 0.2 (3) | C14—C9—C10—C11 | −179.2 (2) |
| S1—C1—C2—C3 | 178.90 (16) | C9—C10—C11—C12 | 0.9 (3) |
| C6—C1—C2—C7 | −179.84 (19) | C10—C11—C12—C13 | −0.8 (3) |
| S1—C1—C2—C7 | −1.1 (3) | C11—C12—C13—C8 | 0.0 (3) |
| C1—C2—C3—C4 | 0.3 (3) | C9—C8—C13—C12 | 0.7 (3) |
| C7—C2—C3—C4 | −179.7 (2) | S2—C8—C13—C12 | −178.34 (16) |
| C2—C3—C4—C5 | −0.3 (4) | C10—C9—C14—O3 | −172.1 (2) |
| C3—C4—C5—C6 | −0.2 (4) | C8—C9—C14—O3 | 9.0 (3) |
| C4—C5—C6—C1 | 0.7 (4) | C10—C9—C14—O4 | 9.3 (3) |
| C2—C1—C6—C5 | −0.7 (3) | C8—C9—C14—O4 | −169.68 (18) |
| S1—C1—C6—C5 | −179.40 (17) | C15—N1—C15'—C17' | 150.8 (9) |
| C3—C2—C7—O1 | 178.6 (2) | C17—N1—C15'—C17' | 3.7 (9) |
| C1—C2—C7—O1 | −1.4 (3) | C16'—N1—C15'—C17' | 135.0 (10) |
| C3—C2—C7—O2 | −0.7 (3) | C16—N1—C15'—C17' | 90 (2) |
| C1—C2—C7—O2 | 179.4 (2) | C15—N1—C17'—C15' | −22.4 (8) |
| S1—S2—C8—C13 | −19.60 (17) | C17—N1—C17'—C15' | −174.1 (13) |
| S1—S2—C8—C9 | 161.40 (14) | C16'—N1—C17'—C15' | −93 (3) |
| C13—C8—C9—C10 | −0.5 (3) | C16—N1—C17'—C15' | −149.7 (9) |
| S2—C8—C9—C10 | 178.51 (14) |
