Carboxylate molecular crystals have been of interest due to the presence of hydrogen bonding, which plays a significant role in chemical and crystal engineering, as well as in supramolecular chemistry. Acid-base adducts possess hydrogen bonds which increase the thermal and mechanical stability of the crystal. 2,2'-Thiodiacetic acid (Tda) is a versatile ligand that has been widely explored, employing its multidendate and chelating coordination abilities with many metals; however, charge-transfer complexes of thiodiacetic acid have not been reported. Two salts, namely ethylenediaminium 2,2'-thiodiacetate, C2H10N22+·C4H4O4S22-, denoted Tdaen, and 2-aminoanilinium 2-(carboxymethylsulfanyl)acetate, C6H9N2+·C4H5O4S-, denoted Tdaophen, were synthesized and characterized by IR, 1H and 13C NMR spectroscopies, and single-crystal X-ray diffraction. In these salts, Tda reacts with the aliphatic (ethylenediamine) and aromatic (o-phenylenediamine) diamines, and deprotonates them to form anions with different valencies and different supramolecular networks. In Tdaen, the divalent Tda2- anions form one-dimensional linear supramolecular chains and these are extended into a three-dimensional sandwich-type supramolecular network by interaction with the ethylenediaminium cations. However, in Tdaophen, the monovalent Tda- anions form one-dimensional zigzag supramolecular chains, which are extended into a three-dimensional supramolecular network by interaction with the 2-aminoanilinium cations. Thus, both three-dimensional structures display different ring motifs. The structures of these diamines, which are influenced by hydrogen-bonded assemblies in the molecular crystals, are discussed in detail.
Supporting information
CCDC references: 1401983; 1001490
For both compounds, data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1992); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).
(TDAEN) Ethylenediaminium 2,2'-thiodiacetate
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Crystal data top
C2H10N22+·C4H4O4S22− | F(000) = 448 |
Mr = 210.25 | Dx = 1.417 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.9626 (5) Å | Cell parameters from 6743 reflections |
b = 10.2601 (4) Å | θ = 2.7–30.3° |
c = 8.7673 (4) Å | µ = 0.32 mm−1 |
β = 91.421 (2)° | T = 293 K |
V = 985.82 (7) Å3 | Needle, colourless |
Z = 4 | 0.35 × 0.30 × 0.30 mm |
Data collection top
Bruker Kappa APEXII CCD diffractometer | 1733 independent reflections |
Radiation source: fine-focus sealed tube | 1535 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
ω and φ scan | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −13→13 |
Tmin = 0.895, Tmax = 0.928 | k = −12→12 |
12561 measured reflections | l = −10→10 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.026 | H-atom parameters constrained |
wR(F2) = 0.071 | w = 1/[σ2(Fo2) + (0.0287P)2 + 0.5534P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
1733 reflections | Δρmax = 0.17 e Å−3 |
118 parameters | Δρmin = −0.17 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.23116 (13) | 0.12791 (14) | −0.17964 (17) | 0.0229 (3) | |
C2 | 0.31284 (14) | 0.11575 (17) | −0.03784 (18) | 0.0308 (4) | |
H2A | 0.3496 | 0.2002 | −0.0176 | 0.037* | |
H2B | 0.3784 | 0.0559 | −0.0604 | 0.037* | |
C3 | 0.18176 (14) | −0.09258 (15) | 0.07206 (19) | 0.0298 (4) | |
H3A | 0.1400 | −0.1308 | 0.1575 | 0.036* | |
H3B | 0.1206 | −0.0759 | −0.0073 | 0.036* | |
C4 | 0.26946 (13) | −0.19425 (15) | 0.01197 (17) | 0.0270 (3) | |
C5 | 0.53945 (14) | −0.00265 (16) | −0.42869 (17) | 0.0291 (4) | |
H5A | 0.5145 | −0.0751 | −0.3655 | 0.035* | |
H5B | 0.6239 | −0.0160 | −0.4552 | 0.035* | |
C6 | 0.03364 (15) | 0.05300 (16) | 0.45917 (18) | 0.0305 (4) | |
H6A | 0.1190 | 0.0295 | 0.4520 | 0.037* | |
H6B | −0.0001 | 0.0628 | 0.3565 | 0.037* | |
N1 | 0.52765 (11) | 0.12046 (13) | −0.34380 (14) | 0.0273 (3) | |
H1A | 0.5743 | 0.1173 | −0.2594 | 0.041* | |
H1B | 0.5513 | 0.1865 | −0.4019 | 0.041* | |
H1C | 0.4502 | 0.1319 | −0.3189 | 0.041* | |
N2 | 0.02281 (11) | 0.17710 (13) | 0.54231 (14) | 0.0271 (3) | |
H2C | 0.0628 | 0.2392 | 0.4933 | 0.041* | |
H2D | −0.0555 | 0.1989 | 0.5477 | 0.041* | |
H2E | 0.0546 | 0.1682 | 0.6361 | 0.041* | |
O1 | 0.11916 (9) | 0.14597 (11) | −0.16515 (12) | 0.0294 (3) | |
O2 | 0.28221 (10) | 0.12164 (13) | −0.30456 (13) | 0.0377 (3) | |
O3 | 0.22187 (10) | −0.28269 (13) | −0.06647 (16) | 0.0449 (3) | |
O4 | 0.38094 (10) | −0.18605 (12) | 0.04327 (14) | 0.0362 (3) | |
S1 | 0.24260 (4) | 0.06144 (4) | 0.13324 (4) | 0.02889 (13) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0221 (7) | 0.0215 (7) | 0.0252 (8) | 0.0003 (6) | 0.0014 (6) | 0.0007 (6) |
C2 | 0.0225 (8) | 0.0405 (9) | 0.0294 (8) | −0.0066 (7) | −0.0020 (6) | 0.0052 (7) |
C3 | 0.0238 (8) | 0.0288 (8) | 0.0369 (9) | −0.0002 (6) | 0.0056 (7) | 0.0010 (7) |
C4 | 0.0230 (8) | 0.0302 (8) | 0.0279 (8) | −0.0005 (6) | 0.0011 (6) | 0.0000 (7) |
C5 | 0.0259 (8) | 0.0334 (9) | 0.0278 (8) | 0.0025 (7) | −0.0046 (7) | −0.0020 (7) |
C6 | 0.0307 (8) | 0.0341 (9) | 0.0271 (8) | −0.0038 (7) | 0.0055 (6) | 0.0018 (7) |
N1 | 0.0214 (6) | 0.0358 (7) | 0.0245 (7) | −0.0034 (5) | 0.0005 (5) | −0.0028 (6) |
N2 | 0.0221 (6) | 0.0300 (7) | 0.0291 (7) | −0.0013 (5) | −0.0017 (5) | 0.0057 (6) |
O1 | 0.0204 (5) | 0.0426 (7) | 0.0252 (6) | 0.0052 (5) | 0.0003 (4) | −0.0008 (5) |
O2 | 0.0275 (6) | 0.0601 (8) | 0.0257 (6) | 0.0075 (5) | 0.0053 (5) | 0.0004 (6) |
O3 | 0.0252 (6) | 0.0491 (8) | 0.0603 (8) | −0.0019 (5) | 0.0012 (6) | −0.0261 (7) |
O4 | 0.0208 (6) | 0.0413 (7) | 0.0462 (7) | 0.0034 (5) | −0.0028 (5) | −0.0116 (6) |
S1 | 0.0345 (2) | 0.0309 (2) | 0.0212 (2) | 0.00052 (17) | 0.00005 (16) | −0.00186 (16) |
Geometric parameters (Å, º) top
C1—O2 | 1.2439 (18) | C5—C5i | 1.504 (3) |
C1—O1 | 1.2514 (17) | C5—H5A | 0.9700 |
C1—C2 | 1.519 (2) | C5—H5B | 0.9700 |
C2—S1 | 1.7918 (16) | C6—N2 | 1.473 (2) |
C2—H2A | 0.9700 | C6—C6ii | 1.505 (3) |
C2—H2B | 0.9700 | C6—H6A | 0.9700 |
C3—C4 | 1.522 (2) | C6—H6B | 0.9700 |
C3—S1 | 1.7923 (16) | N1—H1A | 0.8900 |
C3—H3A | 0.9700 | N1—H1B | 0.8900 |
C3—H3B | 0.9700 | N1—H1C | 0.8900 |
C4—O3 | 1.2453 (19) | N2—H2C | 0.8900 |
C4—O4 | 1.2488 (18) | N2—H2D | 0.8900 |
C5—N1 | 1.473 (2) | N2—H2E | 0.8900 |
| | | |
O2—C1—O1 | 124.13 (14) | C5i—C5—H5B | 109.8 |
O2—C1—C2 | 116.58 (13) | H5A—C5—H5B | 108.2 |
O1—C1—C2 | 119.28 (13) | N2—C6—C6ii | 110.04 (16) |
C1—C2—S1 | 116.99 (11) | N2—C6—H6A | 109.7 |
C1—C2—H2A | 108.1 | C6ii—C6—H6A | 109.7 |
S1—C2—H2A | 108.1 | N2—C6—H6B | 109.7 |
C1—C2—H2B | 108.1 | C6ii—C6—H6B | 109.7 |
S1—C2—H2B | 108.1 | H6A—C6—H6B | 108.2 |
H2A—C2—H2B | 107.3 | C5—N1—H1A | 109.5 |
C4—C3—S1 | 118.33 (11) | C5—N1—H1B | 109.5 |
C4—C3—H3A | 107.7 | H1A—N1—H1B | 109.5 |
S1—C3—H3A | 107.7 | C5—N1—H1C | 109.5 |
C4—C3—H3B | 107.7 | H1A—N1—H1C | 109.5 |
S1—C3—H3B | 107.7 | H1B—N1—H1C | 109.5 |
H3A—C3—H3B | 107.1 | C6—N2—H2C | 109.5 |
O3—C4—O4 | 124.39 (15) | C6—N2—H2D | 109.5 |
O3—C4—C3 | 115.54 (13) | H2C—N2—H2D | 109.5 |
O4—C4—C3 | 120.07 (14) | C6—N2—H2E | 109.5 |
N1—C5—C5i | 109.46 (16) | H2C—N2—H2E | 109.5 |
N1—C5—H5A | 109.8 | H2D—N2—H2E | 109.5 |
C5i—C5—H5A | 109.8 | C2—S1—C3 | 100.85 (8) |
N1—C5—H5B | 109.8 | | |
| | | |
O2—C1—C2—S1 | −156.35 (13) | S1—C3—C4—O4 | 19.6 (2) |
O1—C1—C2—S1 | 25.1 (2) | C1—C2—S1—C3 | 57.88 (14) |
S1—C3—C4—O3 | −160.99 (13) | C4—C3—S1—C2 | 58.30 (14) |
Symmetry codes: (i) −x+1, −y, −z−1; (ii) −x, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2B···O4 | 0.97 | 2.64 | 3.260 (2) | 122 |
C5—H5B···O2i | 0.97 | 2.60 | 3.3180 (19) | 131 |
N1—H1A···O4iii | 0.89 | 2.07 | 2.8755 (17) | 150 |
N1—H1A···S1iii | 0.89 | 2.92 | 3.6062 (14) | 136 |
N1—H1C···O2 | 0.89 | 1.85 | 2.7211 (16) | 165 |
N1—H1B···O3iv | 0.89 | 2.53 | 3.0420 (17) | 117 |
N1—H1B···O4iv | 0.89 | 1.96 | 2.8444 (17) | 172 |
N2—H2C···O1v | 0.89 | 1.93 | 2.7954 (17) | 162 |
N2—H2E···O1vi | 0.89 | 1.88 | 2.7680 (16) | 179 |
N2—H2E···O2vi | 0.89 | 2.58 | 3.1660 (16) | 124 |
N2—H2D···O3vii | 0.89 | 1.84 | 2.7273 (17) | 171 |
Symmetry codes: (i) −x+1, −y, −z−1; (iii) −x+1, −y, −z; (iv) −x+1, y+1/2, −z−1/2; (v) x, −y+1/2, z+1/2; (vi) x, y, z+1; (vii) −x, y+1/2, −z+1/2. |
(TDAOPHEN) 2-Aminoanilinium 2-(carboxymethylsulfanyl)acetate
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Crystal data top
C6H9N2+·C4H5O4S− | F(000) = 544 |
Mr = 258.29 | Dx = 1.423 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 4.9006 (4) Å | Cell parameters from 2643 reflections |
b = 12.9808 (10) Å | θ = 3.1–27.0° |
c = 18.9837 (15) Å | µ = 0.27 mm−1 |
β = 92.978 (8)° | T = 293 K |
V = 1205.99 (17) Å3 | Needle, brown |
Z = 4 | 0.35 × 0.30 × 0.25 mm |
Data collection top
Bruker Kappa APEXII CCD diffractometer | 2084 independent reflections |
Radiation source: fine-focus sealed tube | 1323 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.072 |
ω and φ scan | θmax = 25.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −5→5 |
Tmin = 0.603, Tmax = 0.745 | k = −15→15 |
11771 measured reflections | l = −22→21 |
Refinement top
Refinement on F2 | 9 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.046 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.099 | w = 1/[σ2(Fo2) + (0.0376P)2 + 0.6293P] where P = (Fo2 + 2Fc2)/3 |
S = 0.95 | (Δ/σ)max < 0.001 |
2084 reflections | Δρmax = 0.18 e Å−3 |
184 parameters | 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 0.4270 (5) | 0.2595 (2) | −0.44536 (13) | 0.0322 (6) | |
C2 | 0.2612 (6) | 0.1776 (2) | −0.46332 (15) | 0.0447 (8) | |
H2 | 0.1160 | 0.1857 | −0.4964 | 0.054* | |
C3 | 0.3116 (7) | 0.0830 (3) | −0.43184 (19) | 0.0627 (10) | |
H3 | 0.2036 | 0.0262 | −0.4442 | 0.075* | |
C4 | 0.5243 (7) | 0.0740 (3) | −0.38192 (19) | 0.0650 (10) | |
H4 | 0.5572 | 0.0109 | −0.3599 | 0.078* | |
C5 | 0.6878 (6) | 0.1562 (3) | −0.36415 (16) | 0.0535 (9) | |
H5 | 0.8307 | 0.1480 | −0.3304 | 0.064* | |
C6 | 0.6441 (5) | 0.2523 (2) | −0.39574 (13) | 0.0386 (7) | |
C7 | 0.3832 (6) | 0.3690 (2) | −0.22095 (15) | 0.0449 (8) | |
C8 | 0.4834 (6) | 0.3290 (2) | −0.15022 (15) | 0.0461 (8) | |
H8A | 0.3281 | 0.3098 | −0.1234 | 0.055* | |
H8B | 0.5819 | 0.3833 | −0.1246 | 0.055* | |
C9 | 0.4590 (5) | 0.1192 (2) | −0.17664 (14) | 0.0400 (7) | |
H9A | 0.3272 | 0.1445 | −0.2124 | 0.048* | |
H9B | 0.5532 | 0.0615 | −0.1969 | 0.048* | |
C10 | 0.3033 (5) | 0.07922 (19) | −0.11553 (14) | 0.0304 (6) | |
N1 | 0.3744 (5) | 0.35989 (18) | −0.47911 (12) | 0.0345 (6) | |
N2 | 0.8170 (5) | 0.3352 (2) | −0.38089 (14) | 0.0524 (7) | |
O1A | 0.147 (7) | 0.358 (4) | −0.242 (2) | 0.051 (9) | 0.25 (6) |
O1B | 0.229 (4) | 0.3189 (18) | −0.2612 (9) | 0.068 (5) | 0.75 (6) |
O2 | 0.5116 (4) | 0.45136 (15) | −0.24055 (10) | 0.0538 (6) | |
H2A | 0.4492 | 0.4698 | −0.2794 | 0.081* | |
O3 | 0.1229 (4) | 0.01163 (14) | −0.13035 (9) | 0.0424 (5) | |
O4 | 0.3524 (3) | 0.11206 (14) | −0.05435 (9) | 0.0406 (5) | |
S1 | 0.70436 (15) | 0.21916 (6) | −0.15780 (4) | 0.0483 (3) | |
H1A | 0.517 (4) | 0.3779 (19) | −0.5045 (11) | 0.041 (9)* | |
H1B | 0.352 (5) | 0.4090 (18) | −0.4459 (10) | 0.052 (9)* | |
H1C | 0.218 (4) | 0.358 (2) | −0.5075 (12) | 0.059 (9)* | |
H2B | 0.939 (5) | 0.330 (2) | −0.3454 (13) | 0.068 (10)* | |
H2C | 0.748 (6) | 0.3980 (16) | −0.3851 (17) | 0.078 (12)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0353 (16) | 0.0359 (16) | 0.0253 (14) | 0.0075 (13) | 0.0024 (12) | 0.0031 (12) |
C2 | 0.0438 (18) | 0.0455 (19) | 0.0449 (18) | 0.0021 (15) | 0.0025 (14) | −0.0006 (15) |
C3 | 0.069 (2) | 0.042 (2) | 0.078 (3) | −0.0025 (17) | 0.014 (2) | 0.0046 (18) |
C4 | 0.072 (3) | 0.051 (2) | 0.074 (3) | 0.022 (2) | 0.021 (2) | 0.0260 (19) |
C5 | 0.050 (2) | 0.068 (2) | 0.0436 (19) | 0.0233 (18) | 0.0033 (15) | 0.0173 (17) |
C6 | 0.0356 (17) | 0.0507 (19) | 0.0295 (16) | 0.0161 (14) | 0.0022 (13) | 0.0011 (14) |
C7 | 0.045 (2) | 0.046 (2) | 0.0420 (19) | −0.0062 (16) | −0.0057 (15) | 0.0115 (16) |
C8 | 0.0553 (19) | 0.0410 (17) | 0.0405 (17) | −0.0133 (15) | −0.0114 (15) | 0.0107 (14) |
C9 | 0.0455 (18) | 0.0418 (17) | 0.0330 (16) | −0.0010 (14) | 0.0046 (13) | −0.0003 (13) |
C10 | 0.0276 (15) | 0.0309 (15) | 0.0326 (16) | 0.0046 (12) | −0.0003 (12) | 0.0027 (13) |
N1 | 0.0348 (15) | 0.0402 (16) | 0.0281 (13) | 0.0036 (12) | −0.0030 (12) | −0.0007 (12) |
N2 | 0.0459 (17) | 0.063 (2) | 0.0458 (16) | 0.0093 (15) | −0.0187 (14) | −0.0055 (15) |
O1A | 0.038 (11) | 0.056 (15) | 0.056 (10) | −0.017 (8) | −0.014 (8) | 0.010 (10) |
O1B | 0.065 (6) | 0.077 (7) | 0.058 (5) | −0.026 (6) | −0.031 (4) | 0.018 (5) |
O2 | 0.0727 (15) | 0.0451 (13) | 0.0416 (12) | −0.0112 (11) | −0.0156 (11) | 0.0120 (10) |
O3 | 0.0525 (12) | 0.0382 (11) | 0.0360 (11) | −0.0159 (10) | −0.0019 (9) | −0.0033 (9) |
O4 | 0.0397 (12) | 0.0549 (13) | 0.0270 (11) | −0.0091 (9) | −0.0004 (8) | −0.0066 (9) |
S1 | 0.0325 (4) | 0.0575 (5) | 0.0544 (5) | −0.0060 (4) | −0.0030 (4) | 0.0168 (4) |
Geometric parameters (Å, º) top
C1—C2 | 1.370 (4) | C8—S1 | 1.801 (3) |
C1—C6 | 1.387 (4) | C8—H8A | 0.9700 |
C1—N1 | 1.469 (3) | C8—H8B | 0.9700 |
C2—C3 | 1.383 (4) | C9—C10 | 1.513 (4) |
C2—H2 | 0.9300 | C9—S1 | 1.793 (3) |
C3—C4 | 1.377 (5) | C9—H9A | 0.9700 |
C3—H3 | 0.9300 | C9—H9B | 0.9700 |
C4—C5 | 1.366 (5) | C10—O4 | 1.249 (3) |
C4—H4 | 0.9300 | C10—O3 | 1.267 (3) |
C5—C6 | 1.395 (4) | N1—H1A | 0.899 (15) |
C5—H5 | 0.9300 | N1—H1B | 0.906 (15) |
C6—N2 | 1.390 (4) | N1—H1C | 0.914 (15) |
C7—O1A | 1.21 (2) | N2—H2B | 0.881 (17) |
C7—O1B | 1.232 (12) | N2—H2C | 0.883 (17) |
C7—O2 | 1.304 (3) | O2—H2A | 0.8200 |
C7—C8 | 1.498 (4) | | |
| | | |
C2—C1—C6 | 122.7 (3) | S1—C8—H8A | 109.2 |
C2—C1—N1 | 119.4 (2) | C7—C8—H8B | 109.2 |
C6—C1—N1 | 117.8 (2) | S1—C8—H8B | 109.2 |
C1—C2—C3 | 119.4 (3) | H8A—C8—H8B | 107.9 |
C1—C2—H2 | 120.3 | C10—C9—S1 | 117.07 (19) |
C3—C2—H2 | 120.3 | C10—C9—H9A | 108.0 |
C4—C3—C2 | 119.0 (3) | S1—C9—H9A | 108.0 |
C4—C3—H3 | 120.5 | C10—C9—H9B | 108.0 |
C2—C3—H3 | 120.5 | S1—C9—H9B | 108.0 |
C5—C4—C3 | 121.2 (3) | H9A—C9—H9B | 107.3 |
C5—C4—H4 | 119.4 | O4—C10—O3 | 122.8 (2) |
C3—C4—H4 | 119.4 | O4—C10—C9 | 121.0 (2) |
C4—C5—C6 | 121.1 (3) | O3—C10—C9 | 116.2 (2) |
C4—C5—H5 | 119.4 | C1—N1—H1A | 109.9 (16) |
C6—C5—H5 | 119.4 | C1—N1—H1B | 110.2 (17) |
C1—C6—N2 | 121.6 (3) | H1A—N1—H1B | 108.4 (18) |
C1—C6—C5 | 116.6 (3) | C1—N1—H1C | 110.5 (17) |
N2—C6—C5 | 121.8 (3) | H1A—N1—H1C | 110.0 (19) |
O1A—C7—O2 | 118.2 (14) | H1B—N1—H1C | 107.7 (18) |
O1B—C7—O2 | 123.0 (4) | C6—N2—H2B | 118.4 (19) |
O1A—C7—C8 | 120.8 (12) | C6—N2—H2C | 118 (2) |
O1B—C7—C8 | 122.4 (5) | H2B—N2—H2C | 113 (2) |
O2—C7—C8 | 113.5 (2) | C7—O2—H2A | 109.5 |
C7—C8—S1 | 111.9 (2) | C9—S1—C8 | 100.91 (13) |
C7—C8—H8A | 109.2 | | |
| | | |
C6—C1—C2—C3 | −0.9 (4) | C4—C5—C6—C1 | 0.3 (4) |
N1—C1—C2—C3 | 179.6 (3) | C4—C5—C6—N2 | −176.7 (3) |
C1—C2—C3—C4 | 1.5 (5) | O1A—C7—C8—S1 | 109 (4) |
C2—C3—C4—C5 | −1.2 (5) | O1B—C7—C8—S1 | 66.3 (19) |
C3—C4—C5—C6 | 0.3 (5) | O2—C7—C8—S1 | −102.0 (3) |
C2—C1—C6—N2 | 176.9 (3) | S1—C9—C10—O4 | −2.7 (3) |
N1—C1—C6—N2 | −3.5 (4) | S1—C9—C10—O3 | 177.19 (18) |
C2—C1—C6—C5 | 0.0 (4) | C10—C9—S1—C8 | −76.4 (2) |
N1—C1—C6—C5 | 179.5 (2) | C7—C8—S1—C9 | −78.4 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9A···O1B | 0.97 | 2.49 | 3.225 (17) | 133 |
O2—H2A···O3i | 0.82 | 1.81 | 2.624 (2) | 169 |
N1—H1A···O4ii | 0.90 (2) | 1.94 (2) | 2.830 (3) | 168 (2) |
N1—H1B···O3i | 0.91 (2) | 1.97 (2) | 2.864 (3) | 169 (2) |
N1—H1C···O4iii | 0.92 (2) | 1.99 (2) | 2.887 (3) | 164 (2) |
N1—H1C···S1iii | 0.92 (2) | 3.01 (2) | 3.600 (2) | 123 (2) |
N2—H2B···O1Aiv | 0.88 (2) | 2.20 (4) | 3.04 (3) | 159 (3) |
N2—H2B···O1Biv | 0.88 (2) | 2.08 (2) | 2.966 (7) | 179 (3) |
N2—H2C···O3i | 0.88 (2) | 2.38 (2) | 3.161 (3) | 147 (3) |
Symmetry codes: (i) −x+1/2, y+1/2, −z−1/2; (ii) x+1/2, −y+1/2, z−1/2; (iii) x−1/2, −y+1/2, z−1/2; (iv) x+1, y, z. |