1,1'-Dimethyl-2,2'-[p-phenyl­enebis(methyl­enethio)]di-1H-imidazole monohydrate

In the title compound, C₁₆H₁₈N₄S₂·H₂O, a crystallographic twofold axis runs perpendicular to the benzene ring; the solvent water oxygen atom also sits on a twofold axis. The terminal (1-methyl­imidazole-2-yl)-sulfanyl groups adopt a trans configuration with respect to the benzene ring and the dihedral angle between the two imidazole rings is 81.9 (3)°.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.036
• wR factor = 0.110
• Data-to-parameter ratio = 17.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.65 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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


checkCIF publication errors

Alert level A
PUBL023_ALERT_1_A There is a mismatched ^ on line 418
                Refinement of F2^ against ALL reflections.  The weighted R-factor wR and
              If you require a ^ then it should be escaped
              with a \, i.e. \^
              Otherwise there must be a matching closing ~, e.g. ^12^C
PUBL023_ALERT_1_A There is a mismatched ^ on line 419
                goodness of fit S are based on F2^, conventional R-factors R are based
              If you require a ^ then it should be escaped
              with a \, i.e. \^
              Otherwise there must be a matching closing ~, e.g. ^12^C
PUBL023_ALERT_1_A There is a mismatched ^ on line 420
                on F, with F set to zero for negative F2^. The threshold expression of
              If you require a ^ then it should be escaped
              with a \, i.e. \^
              Otherwise there must be a matching closing ~, e.g. ^12^C
PUBL023_ALERT_1_A There is a mismatched ^ on line 423
                on F2^ are statistically about twice as large as those based on F, and R-
              If you require a ^ then it should be escaped
              with a \, i.e. \^
              Otherwise there must be a matching closing ~, e.g. ^12^C

   4 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

2,2'-[(p-Phenylenedimethylene)dithio]-bis- (1-methyl-1H-imidazol)

Crystal data

C16H18N4S2·H2O	Dx = 1.286 Mg m^−3
Mr = 348.48	Melting point: 341 K
Orthorhombic, Ibca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -I 2b 2c	Cell parameters from 3069 reflections
a = 13.1962 (19) Å	θ = 2.3–25.9°
b = 15.049 (2) Å	µ = 0.31 mm^−1
c = 18.124 (4) Å	T = 294 K
V = 3599.4 (10) Å^3	Block, colourless
Z = 8	0.22 × 0.16 × 0.10 mm
F(000) = 1472

Data collection

Bruker SMART 1000 CCD area detector diffractometer	1854 independent reflections
Radiation source: fine-focus sealed tube	1288 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
φ and ω scans	θmax = 26.4°, θmin = 2.3°
Absorption correction: multi-scan SADABS (Sheldrick, 1996)	h = −16→16
Tmin = 0.943, Tmax = 0.970	k = −7→18
9524 measured reflections	l = −22→21

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.0286P)^2 + 3.8597P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
1854 reflections	Δρmax = 0.22 e Å^−3
107 parameters	Δρmin = −0.23 e Å^−3
6 restraints	Extinction correction: SHELXL
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0045 (4)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.77641 (5)	0.09813 (4)	0.19800 (3)	0.0614 (3)
N1	0.98241 (17)	0.10901 (15)	0.19662 (12)	0.0760 (7)
N2	0.92289 (17)	0.00531 (13)	0.12365 (11)	0.0647 (5)
C1	0.89959 (18)	0.07043 (14)	0.17195 (12)	0.0537 (6)
C2	1.0604 (2)	0.0668 (2)	0.1621 (2)	0.0957 (10)
H2	1.1285	0.0807	0.1683	0.115*
C3	1.0253 (2)	0.0029 (2)	0.11812 (17)	0.0858 (9)
H3	1.0636	−0.0357	0.0893	0.103*
C4	0.8524 (3)	−0.0538 (2)	0.0870 (2)	0.1133 (13)
H4A	0.8291	−0.0979	0.1213	0.170*
H4B	0.8858	−0.0825	0.0464	0.170*
H4C	0.7957	−0.0203	0.0690	0.170*
C5	0.76744 (18)	0.20992 (15)	0.15946 (11)	0.0537 (6)
H5A	0.7088	0.2395	0.1804	0.064*
H5B	0.8271	0.2434	0.1737	0.064*
C6	0.75863 (15)	0.21055 (12)	0.07691 (10)	0.0427 (5)
C7	0.66450 (16)	0.21048 (14)	0.04337 (11)	0.0486 (5)
H7	0.6063	0.2103	0.0723	0.058*
C8	0.84423 (15)	0.21073 (14)	0.03260 (11)	0.0491 (5)
H8	0.9081	0.2110	0.0542	0.059*
O1	0.5000	0.2500	0.19450 (12)	0.0769 (7)
H1A	0.5031	0.2942	0.2262	0.092*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0688 (4)	0.0675 (4)	0.0479 (3)	0.0007 (3)	0.0066 (3)	0.0147 (3)
N1	0.0692 (14)	0.0690 (14)	0.0898 (16)	0.0101 (11)	−0.0242 (12)	−0.0179 (12)
N2	0.0797 (14)	0.0530 (11)	0.0615 (12)	−0.0064 (10)	0.0029 (10)	−0.0065 (10)
C1	0.0684 (15)	0.0446 (11)	0.0479 (12)	0.0030 (10)	−0.0077 (11)	0.0051 (9)
C2	0.0625 (18)	0.090 (2)	0.134 (3)	0.0176 (16)	−0.0169 (18)	−0.020 (2)
C3	0.077 (2)	0.0713 (18)	0.109 (2)	0.0174 (15)	0.0094 (17)	−0.0136 (17)
C4	0.126 (3)	0.107 (2)	0.107 (2)	−0.046 (2)	0.022 (2)	−0.050 (2)
C5	0.0671 (14)	0.0539 (12)	0.0400 (11)	0.0107 (11)	0.0001 (10)	−0.0049 (9)
C6	0.0554 (12)	0.0356 (10)	0.0372 (10)	0.0064 (9)	−0.0010 (9)	−0.0015 (8)
C7	0.0506 (11)	0.0524 (12)	0.0429 (12)	0.0062 (10)	0.0080 (9)	−0.0024 (9)
C8	0.0471 (11)	0.0546 (12)	0.0457 (11)	−0.0040 (10)	−0.0039 (9)	0.0009 (9)
O1	0.0963 (18)	0.0828 (17)	0.0516 (13)	0.0023 (15)	0.000	0.000

Geometric parameters (Å, º)

S1—C1	1.743 (2)	C4—H4C	0.9600
S1—C5	1.825 (2)	C5—C6	1.501 (3)
N1—C1	1.316 (3)	C5—H5A	0.9700
N1—C2	1.362 (4)	C5—H5B	0.9700
N2—C1	1.350 (3)	C6—C7	1.383 (3)
N2—C3	1.356 (3)	C6—C8	1.386 (3)
N2—C4	1.448 (3)	C7—C8^i	1.382 (3)
C2—C3	1.331 (4)	C7—H7	0.9300
C2—H2	0.9300	C8—C7^i	1.382 (3)
C3—H3	0.9300	C8—H8	0.9300
C4—H4A	0.9600	O1—H1A	0.8794
C4—H4B	0.9600
C1—S1—C5	100.21 (10)	H4A—C4—H4C	109.5
C1—N1—C2	105.4 (2)	H4B—C4—H4C	109.5
C1—N2—C3	107.1 (2)	C6—C5—S1	113.10 (14)
C1—N2—C4	126.7 (2)	C6—C5—H5A	109.0
C3—N2—C4	126.1 (3)	S1—C5—H5A	109.0
N1—C1—N2	110.6 (2)	C6—C5—H5B	109.0
N1—C1—S1	125.24 (18)	S1—C5—H5B	109.0
N2—C1—S1	124.17 (18)	H5A—C5—H5B	107.8
C3—C2—N1	110.5 (3)	C7—C6—C8	118.51 (18)
C3—C2—H2	124.8	C7—C6—C5	120.52 (19)
N1—C2—H2	124.8	C8—C6—C5	120.97 (19)
C2—C3—N2	106.4 (3)	C8^i—C7—C6	120.86 (19)
C2—C3—H3	126.8	C8^i—C7—H7	119.6
N2—C3—H3	126.8	C6—C7—H7	119.6
N2—C4—H4A	109.5	C7^i—C8—C6	120.63 (19)
N2—C4—H4B	109.5	C7^i—C8—H8	119.7
H4A—C4—H4B	109.5	C6—C8—H8	119.7
N2—C4—H4C	109.5
C2—N1—C1—N2	0.4 (3)	C1—N2—C3—C2	−0.8 (3)
C2—N1—C1—S1	179.9 (2)	C4—N2—C3—C2	−178.2 (3)
C3—N2—C1—N1	0.3 (3)	C1—S1—C5—C6	72.93 (18)
C4—N2—C1—N1	177.7 (3)	S1—C5—C6—C7	91.9 (2)
C3—N2—C1—S1	−179.29 (19)	S1—C5—C6—C8	−87.7 (2)
C4—N2—C1—S1	−1.9 (4)	C8—C6—C7—C8^i	−0.1 (3)
C5—S1—C1—N1	66.1 (2)	C5—C6—C7—C8^i	−179.76 (19)
C5—S1—C1—N2	−114.4 (2)	C7—C6—C8—C7^i	−0.3 (3)
C1—N1—C2—C3	−0.9 (4)	C5—C6—C8—C7^i	179.40 (19)
N1—C2—C3—N2	1.1 (4)

Symmetry code: (i) −x+3/2, y, −z.