In the title compound, C14H10O4S2·2C3H7NO, the dithiodisalicylic acid is hydrogen bonded to dimethylformamide solvent molecules. Within the dithiodisalicylic acid, the two benzene rings are nearly perpendicular to each other, with a dihedral angle of 77.77 (10)°.
Supporting information
CCDC reference: 298706
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.045
- wR factor = 0.133
- Data-to-parameter ratio = 14.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.62
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N1
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N2
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3
C3 H7 N O
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.
2,2'-Dithiodisalicylic acid dimethylformamide disolvate
top
Crystal data top
C14H10O4S2·2C3H7NO | Z = 2 |
Mr = 452.53 | F(000) = 476 |
Triclinic, P1 | Dx = 1.309 Mg m−3 |
Hall symbol: -P 1 | Melting point = 409–411 K |
a = 7.554 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.710 (3) Å | Cell parameters from 4617 reflections |
c = 20.046 (8) Å | θ = 2.1–25.1° |
α = 83.486 (7)° | µ = 0.27 mm−1 |
β = 84.933 (6)° | T = 293 K |
γ = 83.057 (7)° | Prism, brown |
V = 1148.1 (8) Å3 | 0.28 × 0.22 × 0.18 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3085 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.020 |
Graphite monochromator | θmax = 25.2°, θmin = 2.1° |
φ and ω scans | h = −9→9 |
8419 measured reflections | k = −9→9 |
4103 independent reflections | l = −24→23 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0692P)2 + 0.3654P] where P = (Fo2 + 2Fc2)/3 |
4103 reflections | (Δ/σ)max = 0.002 |
275 parameters | Δρmax = 0.47 e Å−3 |
0 restraints | Δρmin = −0.13 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 >
σ(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 | 0.55494 (9) | 0.30509 (8) | 0.27805 (3) | 0.0569 (2) | |
S2 | 0.56883 (8) | 0.32781 (9) | 0.17529 (3) | 0.0524 (2) | |
N1 | 0.8517 (4) | −0.1218 (4) | 0.58705 (13) | 0.0842 (8) | |
N2 | 0.9288 (3) | 0.0813 (3) | −0.12538 (10) | 0.0584 (5) | |
O1 | 0.8061 (4) | 0.1648 (5) | 0.55465 (13) | 0.1217 (10) | |
O2 | 0.6306 (3) | 0.1490 (3) | −0.10636 (9) | 0.0706 (5) | |
O3 | 0.6111 (3) | 0.2443 (3) | 0.41015 (10) | 0.0807 (6) | |
O4 | 0.7084 (4) | 0.4275 (3) | 0.47101 (11) | 0.0971 (8) | |
H4D | 0.7347 | 0.3461 | 0.5013 | 0.117* | |
O5 | 0.3823 (2) | 0.2445 (3) | −0.01627 (9) | 0.0712 (6) | |
H5D | 0.4697 | 0.2195 | −0.0480 | 0.085* | |
O6 | 0.6012 (2) | 0.2939 (3) | 0.04367 (9) | 0.0643 (5) | |
C1 | 0.7925 (5) | 0.0084 (7) | 0.54591 (18) | 0.0970 (11) | |
H1 | 0.7379 | −0.0141 | 0.5085 | 0.116* | |
C2 | 0.9295 (6) | −0.0965 (6) | 0.64718 (19) | 0.1145 (14) | |
H2A | 0.9511 | 0.0241 | 0.6458 | 0.172* | |
H2B | 1.0406 | −0.1708 | 0.6505 | 0.172* | |
H2C | 0.8492 | −0.1257 | 0.6855 | 0.172* | |
C3 | 0.8371 (6) | −0.3025 (6) | 0.5754 (2) | 0.1130 (13) | |
H3A | 0.7878 | −0.3036 | 0.5329 | 0.169* | |
H3B | 0.7603 | −0.3548 | 0.6108 | 0.169* | |
H3C | 0.9535 | −0.3681 | 0.5747 | 0.169* | |
C4 | 0.7838 (4) | 0.1350 (3) | −0.08900 (13) | 0.0606 (7) | |
H4 | 0.7984 | 0.1649 | −0.0463 | 0.073* | |
C5 | 0.9173 (5) | 0.0343 (4) | −0.19222 (15) | 0.0795 (9) | |
H5A | 0.7939 | 0.0363 | −0.2007 | 0.119* | |
H5B | 0.9776 | −0.0815 | −0.1960 | 0.119* | |
H5C | 0.9727 | 0.1168 | −0.2245 | 0.119* | |
C6 | 1.1051 (4) | 0.0697 (5) | −0.10084 (17) | 0.0844 (9) | |
H6A | 1.0949 | 0.1088 | −0.0567 | 0.127* | |
H6B | 1.1781 | 0.1426 | −0.1308 | 0.127* | |
H6C | 1.1590 | −0.0499 | −0.0987 | 0.127* | |
C11 | 0.6438 (4) | 0.3885 (4) | 0.41714 (13) | 0.0620 (7) | |
C12 | 0.6145 (4) | 0.5404 (3) | 0.36529 (13) | 0.0568 (6) | |
C13 | 0.5725 (3) | 0.5197 (3) | 0.29997 (12) | 0.0488 (6) | |
C14 | 0.5459 (3) | 0.6658 (3) | 0.25371 (13) | 0.0564 (6) | |
H14 | 0.5176 | 0.6527 | 0.2105 | 0.068* | |
C15 | 0.5611 (4) | 0.8311 (4) | 0.27136 (16) | 0.0720 (8) | |
H15 | 0.5433 | 0.9288 | 0.2399 | 0.086* | |
C16 | 0.6024 (5) | 0.8518 (4) | 0.33509 (18) | 0.0916 (11) | |
H16 | 0.6126 | 0.9632 | 0.3469 | 0.110* | |
C17 | 0.6283 (5) | 0.7083 (4) | 0.38099 (17) | 0.0843 (10) | |
H17 | 0.6560 | 0.7236 | 0.4241 | 0.101* | |
C21 | 0.4434 (3) | 0.2941 (3) | 0.03704 (12) | 0.0502 (6) | |
C22 | 0.3029 (3) | 0.3543 (3) | 0.08821 (12) | 0.0468 (5) | |
C23 | 0.3428 (3) | 0.3782 (3) | 0.15285 (12) | 0.0442 (5) | |
C24 | 0.2073 (3) | 0.4402 (3) | 0.19802 (13) | 0.0529 (6) | |
H24 | 0.2331 | 0.4579 | 0.2411 | 0.063* | |
C25 | 0.0334 (3) | 0.4760 (4) | 0.17951 (16) | 0.0653 (7) | |
H25 | −0.0568 | 0.5171 | 0.2103 | 0.078* | |
C26 | −0.0075 (3) | 0.4513 (4) | 0.11580 (15) | 0.0677 (8) | |
H26 | −0.1244 | 0.4762 | 0.1034 | 0.081* | |
C27 | 0.1260 (3) | 0.3900 (3) | 0.07120 (14) | 0.0590 (7) | |
H27 | 0.0984 | 0.3716 | 0.0284 | 0.071* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0753 (5) | 0.0448 (4) | 0.0525 (4) | −0.0026 (3) | −0.0208 (3) | −0.0047 (3) |
S2 | 0.0447 (3) | 0.0612 (4) | 0.0526 (4) | 0.0020 (3) | −0.0130 (3) | −0.0131 (3) |
N1 | 0.0817 (18) | 0.118 (2) | 0.0533 (15) | −0.0104 (16) | −0.0137 (13) | −0.0068 (15) |
N2 | 0.0700 (14) | 0.0550 (13) | 0.0507 (12) | 0.0018 (10) | −0.0095 (11) | −0.0137 (10) |
O1 | 0.157 (3) | 0.133 (3) | 0.0736 (17) | −0.006 (2) | −0.0363 (17) | 0.0084 (17) |
O2 | 0.0674 (12) | 0.0932 (15) | 0.0531 (11) | −0.0020 (10) | −0.0146 (9) | −0.0152 (10) |
O3 | 0.1251 (19) | 0.0580 (13) | 0.0631 (13) | −0.0135 (12) | −0.0355 (12) | 0.0025 (10) |
O4 | 0.150 (2) | 0.0847 (16) | 0.0636 (13) | −0.0135 (14) | −0.0496 (14) | −0.0038 (11) |
O5 | 0.0556 (11) | 0.1059 (16) | 0.0574 (11) | −0.0067 (10) | −0.0150 (9) | −0.0256 (11) |
O6 | 0.0449 (10) | 0.0941 (14) | 0.0566 (11) | −0.0014 (9) | −0.0090 (8) | −0.0218 (10) |
C1 | 0.106 (3) | 0.131 (4) | 0.056 (2) | −0.014 (3) | −0.0188 (18) | −0.006 (2) |
C2 | 0.139 (4) | 0.134 (4) | 0.075 (2) | −0.008 (3) | −0.048 (2) | −0.005 (2) |
C3 | 0.118 (3) | 0.114 (3) | 0.111 (3) | −0.016 (3) | −0.012 (3) | −0.026 (3) |
C4 | 0.079 (2) | 0.0590 (16) | 0.0440 (14) | 0.0015 (14) | −0.0155 (13) | −0.0092 (12) |
C5 | 0.096 (2) | 0.086 (2) | 0.0595 (18) | −0.0055 (17) | −0.0033 (16) | −0.0280 (16) |
C6 | 0.072 (2) | 0.097 (2) | 0.084 (2) | 0.0132 (17) | −0.0220 (17) | −0.0215 (18) |
C11 | 0.0717 (18) | 0.0662 (18) | 0.0496 (16) | −0.0044 (14) | −0.0172 (13) | −0.0060 (13) |
C12 | 0.0650 (16) | 0.0511 (15) | 0.0570 (15) | −0.0077 (12) | −0.0147 (12) | −0.0076 (12) |
C13 | 0.0486 (13) | 0.0472 (13) | 0.0518 (14) | −0.0050 (10) | −0.0100 (11) | −0.0058 (11) |
C14 | 0.0617 (16) | 0.0519 (15) | 0.0561 (15) | −0.0078 (12) | −0.0114 (12) | −0.0015 (12) |
C15 | 0.091 (2) | 0.0479 (16) | 0.078 (2) | −0.0125 (14) | −0.0188 (16) | 0.0017 (14) |
C16 | 0.140 (3) | 0.0472 (17) | 0.096 (3) | −0.0210 (18) | −0.040 (2) | −0.0112 (17) |
C17 | 0.125 (3) | 0.0636 (19) | 0.072 (2) | −0.0138 (18) | −0.040 (2) | −0.0150 (16) |
C21 | 0.0484 (14) | 0.0541 (15) | 0.0491 (14) | −0.0051 (11) | −0.0119 (11) | −0.0035 (11) |
C22 | 0.0417 (12) | 0.0465 (13) | 0.0523 (14) | −0.0063 (10) | −0.0091 (10) | 0.0005 (10) |
C23 | 0.0411 (12) | 0.0396 (12) | 0.0517 (14) | −0.0054 (9) | −0.0065 (10) | −0.0013 (10) |
C24 | 0.0508 (14) | 0.0521 (14) | 0.0551 (15) | −0.0063 (11) | −0.0016 (11) | −0.0034 (11) |
C25 | 0.0450 (14) | 0.0655 (17) | 0.080 (2) | −0.0001 (12) | 0.0111 (13) | −0.0006 (14) |
C26 | 0.0411 (14) | 0.080 (2) | 0.079 (2) | −0.0017 (13) | −0.0102 (13) | 0.0045 (16) |
C27 | 0.0450 (14) | 0.0674 (17) | 0.0647 (17) | −0.0055 (12) | −0.0151 (12) | 0.0001 (13) |
Geometric parameters (Å, º) top
S1—S2 | 2.0419 (12) | C5—H5C | 0.9600 |
S1—C13 | 1.783 (2) | C6—H6A | 0.9600 |
S2—C23 | 1.790 (2) | C6—H6B | 0.9600 |
N1—C1 | 1.287 (5) | C6—H6C | 0.9600 |
N1—C2 | 1.429 (4) | C11—C12 | 1.484 (4) |
N1—C3 | 1.457 (5) | C12—C17 | 1.384 (4) |
N2—C4 | 1.312 (3) | C12—C13 | 1.405 (3) |
N2—C5 | 1.440 (3) | C13—C14 | 1.382 (3) |
N2—C6 | 1.449 (4) | C14—C15 | 1.382 (4) |
O1—C1 | 1.255 (5) | C14—H14 | 0.9300 |
O2—C4 | 1.226 (3) | C15—C16 | 1.372 (4) |
O3—C11 | 1.194 (3) | C15—H15 | 0.9300 |
O4—C11 | 1.302 (3) | C16—C17 | 1.363 (4) |
O4—H4D | 0.8405 | C16—H16 | 0.9300 |
O5—C21 | 1.313 (3) | C17—H17 | 0.9300 |
O5—H5D | 0.8943 | C21—C22 | 1.480 (3) |
O6—C21 | 1.211 (3) | C22—C23 | 1.393 (3) |
C1—H1 | 0.9300 | C22—C27 | 1.396 (3) |
C2—H2A | 0.9600 | C23—C24 | 1.383 (3) |
C2—H2B | 0.9600 | C24—C25 | 1.383 (4) |
C2—H2C | 0.9600 | C24—H24 | 0.9300 |
C3—H3A | 0.9600 | C25—C26 | 1.379 (4) |
C3—H3B | 0.9600 | C25—H25 | 0.9300 |
C3—H3C | 0.9600 | C26—C27 | 1.364 (4) |
C4—H4 | 0.9300 | C26—H26 | 0.9300 |
C5—H5A | 0.9600 | C27—H27 | 0.9300 |
C5—H5B | 0.9600 | | |
| | | |
C13—S1—S2 | 105.55 (9) | O3—C11—C12 | 123.1 (2) |
C23—S2—S1 | 105.73 (8) | O4—C11—C12 | 113.7 (3) |
C1—N1—C2 | 121.9 (4) | C17—C12—C13 | 118.3 (2) |
C1—N1—C3 | 121.3 (3) | C17—C12—C11 | 119.7 (2) |
C2—N1—C3 | 116.8 (3) | C13—C12—C11 | 122.0 (2) |
C4—N2—C5 | 120.4 (2) | C14—C13—C12 | 119.6 (2) |
C4—N2—C6 | 121.9 (2) | C14—C13—S1 | 121.03 (19) |
C5—N2—C6 | 117.6 (2) | C12—C13—S1 | 119.38 (18) |
C11—O4—H4D | 118.5 | C15—C14—C13 | 120.3 (3) |
C21—O5—H5D | 112.1 | C15—C14—H14 | 119.8 |
O1—C1—N1 | 122.2 (4) | C13—C14—H14 | 119.8 |
O1—C1—H1 | 118.9 | C16—C15—C14 | 120.3 (3) |
N1—C1—H1 | 118.9 | C16—C15—H15 | 119.9 |
N1—C2—H2A | 109.5 | C14—C15—H15 | 119.9 |
N1—C2—H2B | 109.5 | C17—C16—C15 | 119.7 (3) |
H2A—C2—H2B | 109.5 | C17—C16—H16 | 120.2 |
N1—C2—H2C | 109.5 | C15—C16—H16 | 120.2 |
H2A—C2—H2C | 109.5 | C16—C17—C12 | 121.9 (3) |
H2B—C2—H2C | 109.5 | C16—C17—H17 | 119.1 |
N1—C3—H3A | 109.5 | C12—C17—H17 | 119.1 |
N1—C3—H3B | 109.5 | O6—C21—O5 | 123.2 (2) |
H3A—C3—H3B | 109.5 | O6—C21—C22 | 122.4 (2) |
N1—C3—H3C | 109.5 | O5—C21—C22 | 114.4 (2) |
H3A—C3—H3C | 109.5 | C23—C22—C27 | 119.0 (2) |
H3B—C3—H3C | 109.5 | C23—C22—C21 | 121.7 (2) |
O2—C4—N2 | 125.7 (2) | C27—C22—C21 | 119.3 (2) |
O2—C4—H4 | 117.2 | C24—C23—C22 | 119.3 (2) |
N2—C4—H4 | 117.2 | C24—C23—S2 | 121.67 (19) |
N2—C5—H5A | 109.5 | C22—C23—S2 | 119.02 (17) |
N2—C5—H5B | 109.5 | C23—C24—C25 | 120.4 (2) |
H5A—C5—H5B | 109.5 | C23—C24—H24 | 119.8 |
N2—C5—H5C | 109.5 | C25—C24—H24 | 119.8 |
H5A—C5—H5C | 109.5 | C26—C25—C24 | 120.7 (2) |
H5B—C5—H5C | 109.5 | C26—C25—H25 | 119.7 |
N2—C6—H6A | 109.5 | C24—C25—H25 | 119.7 |
N2—C6—H6B | 109.5 | C27—C26—C25 | 119.0 (2) |
H6A—C6—H6B | 109.5 | C27—C26—H26 | 120.5 |
N2—C6—H6C | 109.5 | C25—C26—H26 | 120.5 |
H6A—C6—H6C | 109.5 | C26—C27—C22 | 121.6 (3) |
H6B—C6—H6C | 109.5 | C26—C27—H27 | 119.2 |
O3—C11—O4 | 123.2 (3) | C22—C27—H27 | 119.2 |
| | | |
C13—S1—S2—C23 | −90.42 (11) | C13—C12—C17—C16 | 0.0 (5) |
C2—N1—C1—O1 | 3.0 (6) | C11—C12—C17—C16 | −179.9 (3) |
C3—N1—C1—O1 | −179.0 (4) | O6—C21—C22—C23 | −14.0 (4) |
C5—N2—C4—O2 | 0.6 (4) | O5—C21—C22—C23 | 167.1 (2) |
C6—N2—C4—O2 | 179.6 (3) | O6—C21—C22—C27 | 165.2 (2) |
O3—C11—C12—C17 | 169.7 (3) | O5—C21—C22—C27 | −13.7 (3) |
O4—C11—C12—C17 | −10.2 (4) | C27—C22—C23—C24 | −1.4 (3) |
O3—C11—C12—C13 | −10.2 (4) | C21—C22—C23—C24 | 177.9 (2) |
O4—C11—C12—C13 | 169.9 (3) | C27—C22—C23—S2 | 178.66 (18) |
C17—C12—C13—C14 | −0.2 (4) | C21—C22—C23—S2 | −2.1 (3) |
C11—C12—C13—C14 | 179.7 (2) | S1—S2—C23—C24 | 17.6 (2) |
C17—C12—C13—S1 | 179.7 (2) | S1—S2—C23—C22 | −162.43 (17) |
C11—C12—C13—S1 | −0.4 (4) | C22—C23—C24—C25 | 0.8 (4) |
S2—S1—C13—C14 | 16.5 (2) | S2—C23—C24—C25 | −179.22 (19) |
S2—S1—C13—C12 | −163.34 (19) | C23—C24—C25—C26 | −0.3 (4) |
C12—C13—C14—C15 | 0.3 (4) | C24—C25—C26—C27 | 0.4 (4) |
S1—C13—C14—C15 | −179.6 (2) | C25—C26—C27—C22 | −1.0 (4) |
C13—C14—C15—C16 | −0.2 (5) | C23—C22—C27—C26 | 1.5 (4) |
C14—C15—C16—C17 | 0.0 (5) | C21—C22—C27—C26 | −177.8 (2) |
C15—C16—C17—C12 | 0.1 (6) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4D···O1 | 0.84 | 1.72 | 2.558 (4) | 172 |
O5—H5D···O2 | 0.89 | 1.70 | 2.587 (3) | 174 |