In the title compound, C
19H
20N
4S
2·2H
2O, the two 1
H-benzimidazole groups are bridged by a propane chain; the dihedral angle between the benzimidazole ring systems is 74.61 (3)°. The organic molecules and solvent water molecules form O—H
N hydrogen bonds. There are also O—H
O, C—H
S, C—H
π and π–π interactions in the crystal structure.
Supporting information
CCDC reference: 633976
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.042
- wR factor = 0.119
- Data-to-parameter ratio = 17.4
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D H2W .. H2W .. 1.32 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D H3W .. H3W .. 1.72 Ang.
Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 600 Deg.
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 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
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
1,1'-(Propane-1,3-diyl)bis[2-(methylsulfanyl)-1
H-benzimidazole] dihydrate
top
Crystal data top
C19H20N4S2·2H2O | Z = 2 |
Mr = 404.56 | F(000) = 428 |
Triclinic, P1 | Dx = 1.329 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.2655 (7) Å | Cell parameters from 22161 reflections |
b = 9.9754 (7) Å | θ = 2.2–27.3° |
c = 11.2980 (8) Å | µ = 0.29 mm−1 |
α = 102.125 (6)° | T = 296 K |
β = 93.415 (6)° | Prism, colourless |
γ = 96.443 (6)° | 0.57 × 0.36 × 0.18 mm |
V = 1010.78 (13) Å3 | |
Data collection top
Stoe IPDS2 area-detector diffractometer | 4506 independent reflections |
Radiation source: fine-focus sealed tube | 3322 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.062 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.3°, θmin = 2.2° |
ω scans | h = −11→11 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −12→12 |
Tmin = 0.880, Tmax = 0.958 | l = −14→14 |
19069 measured reflections | |
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) = 0.119 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.065P)2 + 0.0747P] where P = (Fo2 + 2Fc2)/3 |
4506 reflections | (Δ/σ)max = 0.002 |
259 parameters | Δρmax = 0.19 e Å−3 |
36 restraints | Δρmin = −0.55 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 | |
O1 | 0.4529 (2) | 0.0915 (2) | 0.42512 (18) | 0.0869 (5) | |
O2 | 0.4618 (2) | 0.3775 (2) | 0.4019 (3) | 0.0944 (6) | |
H1W | 0.442 (4) | 0.052 (4) | 0.3532 (12) | 0.124 (13)* | |
H2W | 0.466 (10) | 0.033 (4) | 0.464 (3) | 0.28 (4)* | |
H3W | 0.467 (5) | 0.414 (5) | 0.4750 (14) | 0.19 (2)* | |
H4W | 0.381 (3) | 0.388 (6) | 0.372 (4) | 0.20 (2)* | |
S1 | 0.84215 (5) | 0.07328 (6) | −0.05759 (5) | 0.05896 (16) | |
S2 | 1.11505 (7) | 0.57734 (6) | 0.19554 (5) | 0.06907 (19) | |
N1 | 0.57034 (17) | 0.05746 (16) | −0.17307 (13) | 0.0480 (4) | |
N2 | 0.60376 (16) | 0.18331 (15) | 0.01783 (13) | 0.0454 (3) | |
N3 | 0.92954 (16) | 0.42951 (15) | 0.30848 (13) | 0.0445 (3) | |
N4 | 1.16333 (17) | 0.40514 (17) | 0.34857 (15) | 0.0522 (4) | |
C1 | 0.66194 (19) | 0.10179 (18) | −0.07519 (16) | 0.0447 (4) | |
C2 | 0.44436 (19) | 0.11602 (18) | −0.14296 (16) | 0.0448 (4) | |
C3 | 0.46356 (19) | 0.19520 (18) | −0.02460 (16) | 0.0456 (4) | |
C4 | 0.3569 (2) | 0.2676 (2) | 0.02938 (19) | 0.0567 (5) | |
H4 | 0.3712 | 0.3189 | 0.1089 | 0.068* | |
C5 | 0.2275 (2) | 0.2594 (2) | −0.0418 (2) | 0.0635 (5) | |
H5 | 0.1531 | 0.3071 | −0.0096 | 0.076* | |
C6 | 0.2071 (2) | 0.1817 (2) | −0.1595 (2) | 0.0624 (5) | |
H6 | 0.1189 | 0.1785 | −0.2044 | 0.075* | |
C7 | 0.3129 (2) | 0.1090 (2) | −0.21222 (19) | 0.0574 (5) | |
H7 | 0.2974 | 0.0569 | −0.2915 | 0.069* | |
C8 | 0.6755 (2) | 0.25330 (19) | 0.13645 (16) | 0.0480 (4) | |
H8A | 0.7531 | 0.2026 | 0.1577 | 0.058* | |
H8B | 0.6057 | 0.2543 | 0.1972 | 0.058* | |
C9 | 0.7386 (2) | 0.40036 (19) | 0.13712 (17) | 0.0523 (4) | |
H9A | 0.6626 | 0.4476 | 0.1077 | 0.063* | |
H9B | 0.8146 | 0.3983 | 0.0816 | 0.063* | |
C10 | 0.8018 (2) | 0.48182 (19) | 0.26241 (18) | 0.0514 (4) | |
H10A | 0.8282 | 0.5776 | 0.2586 | 0.062* | |
H10B | 0.7273 | 0.4791 | 0.3190 | 0.062* | |
C11 | 1.0715 (2) | 0.46466 (19) | 0.29005 (16) | 0.0483 (4) | |
C12 | 0.93011 (19) | 0.33930 (17) | 0.38618 (15) | 0.0446 (4) | |
C13 | 1.07584 (19) | 0.32544 (18) | 0.41071 (16) | 0.0457 (4) | |
C14 | 1.1137 (2) | 0.2398 (2) | 0.48696 (18) | 0.0557 (5) | |
H14 | 1.2106 | 0.2296 | 0.5050 | 0.067* | |
C15 | 1.0022 (3) | 0.1708 (2) | 0.53473 (19) | 0.0604 (5) | |
H15 | 1.0248 | 0.1138 | 0.5867 | 0.073* | |
C16 | 0.8577 (3) | 0.1839 (2) | 0.50775 (19) | 0.0624 (5) | |
H16 | 0.7855 | 0.1338 | 0.5404 | 0.075* | |
C17 | 0.8185 (2) | 0.2685 (2) | 0.43435 (17) | 0.0526 (4) | |
H17 | 0.7213 | 0.2784 | 0.4173 | 0.063* | |
C18 | 0.8560 (3) | −0.0451 (3) | −0.1983 (2) | 0.0703 (6) | |
H18A | 0.9530 | −0.0701 | −0.2009 | 0.105* | |
H18B | 0.8349 | −0.0020 | −0.2647 | 0.105* | |
H18C | 0.7875 | −0.1265 | −0.2048 | 0.105* | |
C19 | 1.3073 (3) | 0.6187 (3) | 0.2361 (3) | 0.0854 (8) | |
H19A | 1.3476 | 0.6820 | 0.1898 | 0.128* | |
H19B | 1.3529 | 0.5358 | 0.2190 | 0.128* | |
H19C | 1.3243 | 0.6606 | 0.3211 | 0.128* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0923 (13) | 0.1047 (14) | 0.0568 (10) | 0.0233 (11) | −0.0061 (9) | 0.0001 (10) |
O2 | 0.063 | 0.0904 (14) | 0.1220 (18) | 0.0127 (10) | 0.0002 (11) | 0.0070 (13) |
S1 | 0.0526 (3) | 0.0644 (3) | 0.0547 (3) | 0.0123 (2) | −0.0078 (2) | 0.0021 (2) |
S2 | 0.0860 (4) | 0.0635 (3) | 0.0601 (3) | 0.0010 (3) | 0.0106 (3) | 0.0221 (3) |
N1 | 0.0541 (8) | 0.0462 (8) | 0.0401 (7) | 0.0032 (7) | −0.0046 (6) | 0.0052 (6) |
N2 | 0.0491 (8) | 0.0440 (8) | 0.0388 (7) | 0.0017 (6) | −0.0062 (6) | 0.0047 (6) |
N3 | 0.0473 (8) | 0.0433 (8) | 0.0399 (7) | 0.0040 (6) | −0.0041 (6) | 0.0057 (6) |
N4 | 0.0476 (8) | 0.0519 (9) | 0.0543 (9) | 0.0050 (7) | 0.0022 (7) | 0.0071 (7) |
C1 | 0.0504 (9) | 0.0398 (8) | 0.0413 (9) | 0.0025 (7) | −0.0037 (7) | 0.0069 (7) |
C2 | 0.0496 (9) | 0.0404 (8) | 0.0421 (9) | 0.0003 (7) | −0.0052 (7) | 0.0094 (7) |
C3 | 0.0482 (9) | 0.0417 (9) | 0.0446 (9) | −0.0003 (7) | −0.0037 (7) | 0.0098 (7) |
C4 | 0.0583 (11) | 0.0527 (11) | 0.0549 (11) | 0.0061 (9) | 0.0021 (9) | 0.0035 (9) |
C5 | 0.0533 (11) | 0.0588 (12) | 0.0774 (15) | 0.0104 (9) | 0.0039 (10) | 0.0117 (11) |
C6 | 0.0503 (10) | 0.0638 (12) | 0.0719 (14) | 0.0047 (9) | −0.0116 (10) | 0.0178 (11) |
C7 | 0.0585 (11) | 0.0567 (11) | 0.0520 (11) | −0.0013 (9) | −0.0144 (9) | 0.0106 (9) |
C8 | 0.0547 (10) | 0.0490 (10) | 0.0359 (8) | 0.0008 (8) | −0.0062 (7) | 0.0052 (7) |
C9 | 0.0604 (11) | 0.0470 (10) | 0.0454 (10) | 0.0026 (8) | −0.0121 (8) | 0.0081 (8) |
C10 | 0.0562 (10) | 0.0425 (9) | 0.0501 (10) | 0.0075 (8) | −0.0103 (8) | 0.0017 (8) |
C11 | 0.0538 (10) | 0.0443 (9) | 0.0426 (9) | 0.0025 (8) | 0.0020 (7) | 0.0029 (7) |
C12 | 0.0521 (9) | 0.0403 (9) | 0.0366 (8) | 0.0032 (7) | −0.0034 (7) | 0.0012 (7) |
C13 | 0.0516 (9) | 0.0411 (9) | 0.0407 (9) | 0.0051 (7) | −0.0004 (7) | 0.0018 (7) |
C14 | 0.0615 (11) | 0.0516 (10) | 0.0507 (11) | 0.0128 (9) | −0.0065 (9) | 0.0044 (8) |
C15 | 0.0882 (15) | 0.0471 (10) | 0.0445 (10) | 0.0056 (10) | −0.0035 (10) | 0.0106 (8) |
C16 | 0.0748 (13) | 0.0589 (12) | 0.0499 (11) | −0.0061 (10) | 0.0073 (10) | 0.0107 (9) |
C17 | 0.0534 (10) | 0.0566 (11) | 0.0434 (9) | −0.0044 (8) | 0.0016 (8) | 0.0075 (8) |
C18 | 0.0652 (13) | 0.0780 (15) | 0.0628 (13) | 0.0158 (11) | 0.0066 (10) | 0.0005 (11) |
C19 | 0.0812 (16) | 0.0642 (14) | 0.113 (2) | −0.0046 (12) | 0.0397 (15) | 0.0232 (14) |
Geometric parameters (Å, º) top
O1—H1W | 0.820 (16) | C6—H6 | 0.9300 |
O1—H2W | 0.82 (4) | C7—H7 | 0.9300 |
O2—H3W | 0.825 (12) | C8—C9 | 1.515 (3) |
O2—H4W | 0.83 (3) | C8—H8A | 0.9700 |
S1—C1 | 1.7319 (19) | C8—H8B | 0.9700 |
S1—C18 | 1.791 (2) | C9—C10 | 1.523 (2) |
S2—C11 | 1.738 (2) | C9—H9A | 0.9700 |
S2—C19 | 1.792 (3) | C9—H9B | 0.9700 |
N1—C1 | 1.318 (2) | C10—H10A | 0.9700 |
N1—C2 | 1.392 (2) | C10—H10B | 0.9700 |
N2—C1 | 1.365 (2) | C12—C17 | 1.389 (3) |
N2—C3 | 1.384 (2) | C12—C13 | 1.390 (3) |
N2—C8 | 1.457 (2) | C13—C14 | 1.391 (3) |
N3—C11 | 1.363 (2) | C14—C15 | 1.376 (3) |
N3—C12 | 1.383 (2) | C14—H14 | 0.9300 |
N3—C10 | 1.457 (2) | C15—C16 | 1.382 (3) |
N4—C11 | 1.313 (3) | C15—H15 | 0.9300 |
N4—C13 | 1.393 (2) | C16—C17 | 1.364 (3) |
C2—C3 | 1.393 (2) | C16—H16 | 0.9300 |
C2—C7 | 1.394 (2) | C17—H17 | 0.9300 |
C3—C4 | 1.385 (3) | C18—H18A | 0.9600 |
C4—C5 | 1.388 (3) | C18—H18B | 0.9600 |
C4—H4 | 0.9300 | C18—H18C | 0.9600 |
C5—C6 | 1.382 (3) | C19—H19A | 0.9600 |
C5—H5 | 0.9300 | C19—H19B | 0.9600 |
C6—C7 | 1.375 (3) | C19—H19C | 0.9600 |
| | | |
H1W—O1—H2W | 107 (4) | C8—C9—H9B | 108.9 |
H4W—O2—H3W | 107 (5) | C10—C9—H9B | 108.9 |
C1—S1—C18 | 100.59 (10) | H9A—C9—H9B | 107.8 |
C11—S2—C19 | 99.93 (11) | N3—C10—C9 | 113.39 (15) |
C1—N1—C2 | 104.57 (15) | N3—C10—H10A | 108.9 |
C1—N2—C3 | 106.62 (14) | C9—C10—H10A | 108.9 |
C1—N2—C8 | 127.76 (15) | N3—C10—H10B | 108.9 |
C3—N2—C8 | 125.50 (15) | C9—C10—H10B | 108.9 |
C11—N3—C12 | 106.37 (15) | H10A—C10—H10B | 107.7 |
C11—N3—C10 | 127.51 (16) | N4—C11—N3 | 113.43 (17) |
C12—N3—C10 | 126.02 (16) | N4—C11—S2 | 126.64 (15) |
C11—N4—C13 | 104.66 (15) | N3—C11—S2 | 119.93 (14) |
N1—C1—N2 | 113.22 (16) | N3—C12—C17 | 132.20 (18) |
N1—C1—S1 | 127.30 (15) | N3—C12—C13 | 105.64 (15) |
N2—C1—S1 | 119.42 (12) | C17—C12—C13 | 122.15 (18) |
N1—C2—C3 | 110.20 (15) | C12—C13—C14 | 119.94 (17) |
N1—C2—C7 | 130.35 (17) | C12—C13—N4 | 109.89 (16) |
C3—C2—C7 | 119.42 (19) | C14—C13—N4 | 130.17 (18) |
N2—C3—C4 | 131.59 (17) | C15—C14—C13 | 117.42 (19) |
N2—C3—C2 | 105.37 (16) | C15—C14—H14 | 121.3 |
C4—C3—C2 | 123.04 (17) | C13—C14—H14 | 121.3 |
C3—C4—C5 | 116.3 (2) | C14—C15—C16 | 121.9 (2) |
C3—C4—H4 | 121.8 | C14—C15—H15 | 119.0 |
C5—C4—H4 | 121.8 | C16—C15—H15 | 119.0 |
C6—C5—C4 | 121.3 (2) | C17—C16—C15 | 121.5 (2) |
C6—C5—H5 | 119.4 | C17—C16—H16 | 119.2 |
C4—C5—H5 | 119.4 | C15—C16—H16 | 119.2 |
C7—C6—C5 | 122.13 (19) | C16—C17—C12 | 117.03 (19) |
C7—C6—H6 | 118.9 | C16—C17—H17 | 121.5 |
C5—C6—H6 | 118.9 | C12—C17—H17 | 121.5 |
C6—C7—C2 | 117.79 (19) | S1—C18—H18A | 109.5 |
C6—C7—H7 | 121.1 | S1—C18—H18B | 109.5 |
C2—C7—H7 | 121.1 | H18A—C18—H18B | 109.5 |
N2—C8—C9 | 111.43 (15) | S1—C18—H18C | 109.5 |
N2—C8—H8A | 109.3 | H18A—C18—H18C | 109.5 |
C9—C8—H8A | 109.3 | H18B—C18—H18C | 109.5 |
N2—C8—H8B | 109.3 | S2—C19—H19A | 109.5 |
C9—C8—H8B | 109.3 | S2—C19—H19B | 109.5 |
H8A—C8—H8B | 108.0 | H19A—C19—H19B | 109.5 |
C8—C9—C10 | 113.18 (16) | S2—C19—H19C | 109.5 |
C8—C9—H9A | 108.9 | H19A—C19—H19C | 109.5 |
C10—C9—H9A | 108.9 | H19B—C19—H19C | 109.5 |
| | | |
C2—N1—C1—N2 | 1.1 (2) | C11—N3—C10—C9 | 87.9 (2) |
C2—N1—C1—S1 | −175.98 (14) | C12—N3—C10—C9 | −96.2 (2) |
C3—N2—C1—N1 | −1.4 (2) | C8—C9—C10—N3 | 66.1 (2) |
C8—N2—C1—N1 | −177.57 (16) | C13—N4—C11—N3 | −0.3 (2) |
C3—N2—C1—S1 | 175.94 (13) | C13—N4—C11—S2 | −179.86 (14) |
C8—N2—C1—S1 | −0.2 (2) | C12—N3—C11—N4 | 0.1 (2) |
C18—S1—C1—N1 | −6.5 (2) | C10—N3—C11—N4 | 176.71 (16) |
C18—S1—C1—N2 | 176.58 (16) | C12—N3—C11—S2 | 179.69 (12) |
C1—N1—C2—C3 | −0.42 (19) | C10—N3—C11—S2 | −3.7 (2) |
C1—N1—C2—C7 | 177.70 (19) | C19—S2—C11—N4 | −14.5 (2) |
C1—N2—C3—C4 | −178.2 (2) | C19—S2—C11—N3 | 165.96 (16) |
C8—N2—C3—C4 | −2.0 (3) | C11—N3—C12—C17 | −178.62 (19) |
C1—N2—C3—C2 | 1.07 (19) | C10—N3—C12—C17 | 4.7 (3) |
C8—N2—C3—C2 | 177.30 (15) | C11—N3—C12—C13 | 0.14 (18) |
N1—C2—C3—N2 | −0.42 (19) | C10—N3—C12—C13 | −176.51 (15) |
C7—C2—C3—N2 | −178.77 (16) | N3—C12—C13—C14 | −179.76 (16) |
N1—C2—C3—C4 | 178.97 (17) | C17—C12—C13—C14 | −0.8 (3) |
C7—C2—C3—C4 | 0.6 (3) | N3—C12—C13—N4 | −0.34 (19) |
N2—C3—C4—C5 | 178.30 (19) | C17—C12—C13—N4 | 178.57 (16) |
C2—C3—C4—C5 | −0.9 (3) | C11—N4—C13—C12 | 0.41 (19) |
C3—C4—C5—C6 | 0.6 (3) | C11—N4—C13—C14 | 179.75 (19) |
C4—C5—C6—C7 | −0.1 (3) | C12—C13—C14—C15 | 0.5 (3) |
C5—C6—C7—C2 | −0.2 (3) | N4—C13—C14—C15 | −178.84 (18) |
N1—C2—C7—C6 | −177.99 (19) | C13—C14—C15—C16 | 0.7 (3) |
C3—C2—C7—C6 | 0.0 (3) | C14—C15—C16—C17 | −1.5 (3) |
C1—N2—C8—C9 | 93.7 (2) | C15—C16—C17—C12 | 1.1 (3) |
C3—N2—C8—C9 | −81.8 (2) | N3—C12—C17—C16 | 178.68 (18) |
N2—C8—C9—C10 | 174.45 (16) | C13—C12—C17—C16 | 0.1 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H4W···N4i | 0.83 (3) | 2.05 (3) | 2.851 (3) | 162 (5) |
O1—H1W···N1ii | 0.82 (2) | 2.09 (2) | 2.905 (2) | 175 (3) |
O1—H2W···O1iii | 0.82 (4) | 2.10 (5) | 2.905 (3) | 167 (7) |
O2—H3W···O2iv | 0.83 (2) | 2.25 (4) | 2.922 (4) | 139 (4) |
C8—H8A···S1 | 0.97 | 2.72 | 3.1284 (19) | 106 |
C10—H10A···S2 | 0.97 | 2.79 | 3.138 (2) | 102 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y, −z; (iii) −x+1, −y, −z+1; (iv) −x+1, −y+1, −z+1. |