1,3-Bis(4-methoxy-phen-yl)imidazolidium chloride monohydrate.

The asymmetric unit of the title compound, C(17)H(17)N(2)O(2) (+)·Cl(-)·H(2)O, contains one-half of the cation, one-half of a water mol-ecule and a chloride anion. The complete cation is generated by crystallographic two-fold symmetry, with one C atom lying on the rotation axis. The O and Cl atoms have site symmetry 2. The imidazolidium ring is oriented at a dihedral angle of 4.15 (3)° with respect to the 4-methoxy-phenyl ring and an intramolecular C-H⋯O interaction occurs. In the crystal structure, inter-molecular O-H⋯Cl and C-H⋯Cl hydrogen bonds link the mol-ecules. There is a π-π contact between the imidazolidium and 4-methoxy-phenyl rings [centroid-to-centroid distance = 3.625(3 Å]. There is also a C-H⋯π contact between the methyl group and the 4-methoxy-phenyl ring.

Related literature

For general background, see: Lin & Vasam (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H17N2O2 +·Cl−·H2O

M = 334.79

Monoclinic,

a = 15.6706 (19) Å

b = 9.4198 (9) Å

c = 5.4026 (4) Å

β = 90.156 (1)°

V = 797.50 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 298 (2) K

0.20 × 0.11 × 0.09 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.951, T max = 0.977

2026 measured reflections

749 independent reflections

688 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.076

S = 1.01

749 reflections

107 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808033965/hk2542sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808033965/hk2542Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H17N2O2+·Cl−·H2O	F(000) = 352
Mr = 334.79	Dx = 1.394 Mg m−3
Monoclinic, C2	Melting point = 492–494 K
Hall symbol: -C 2y	Mo Kα radiation, λ = 0.71073 Å
a = 15.6706 (19) Å	Cell parameters from 1340 reflections
b = 9.4198 (9) Å	θ = 2.5–28.3°
c = 5.4026 (4) Å	µ = 0.26 mm−1
β = 90.156 (1)°	T = 298 K
V = 797.50 (14) Å3	Block, colourless
Z = 2	0.20 × 0.11 × 0.09 mm

Bruker SMART CCD area-detector diffractometer	749 independent reflections
Radiation source: fine-focus sealed tube	688 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→13
Tmin = 0.951, Tmax = 0.977	k = −9→11
2026 measured reflections	l = −6→6

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0503P)2 + 0.1521P] where P = (Fo2 + 2Fc2)/3
749 reflections	(Δ/σ)max < 0.001
107 parameters	Δρmax = 0.11 e Å−3
1 restraint	Δρmin = −0.22 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cl1	0.5000	0.84927 (12)	0.5000	0.0800 (5)
O1	0.24434 (13)	0.4740 (2)	0.9080 (3)	0.0519 (5)
O2	0.5000	0.6808 (3)	0.0000	0.0567 (8)
H2	0.5000	0.7335	0.1277	0.068*
N1	0.45802 (12)	0.27396 (19)	0.1594 (3)	0.0334 (5)
C1	0.5000	0.3560 (4)	0.0000	0.0350 (7)
H1	0.5000	0.4547	0.0000	0.042*
C2	0.47435 (17)	0.1342 (3)	0.0983 (5)	0.0444 (6)
H2A	0.4534	0.0545	0.1795	0.053*
C3	0.40340 (14)	0.3225 (3)	0.3567 (4)	0.0335 (5)
C4	0.39574 (17)	0.4670 (3)	0.4036 (5)	0.0420 (6)
H4	0.4262	0.5322	0.3094	0.050*
C5	0.34270 (17)	0.5135 (3)	0.5903 (5)	0.0449 (6)
H5	0.3378	0.6101	0.6225	0.054*
C6	0.29642 (15)	0.4164 (3)	0.7309 (5)	0.0386 (6)
C7	0.30558 (17)	0.2728 (3)	0.6859 (5)	0.0446 (6)
H7	0.2758	0.2073	0.7812	0.054*
C8	0.35934 (16)	0.2262 (3)	0.4979 (5)	0.0440 (6)
H8	0.3654	0.1296	0.4678	0.053*
C9	0.19340 (19)	0.3780 (4)	1.0497 (5)	0.0580 (8)
H9A	0.1588	0.3219	0.9402	0.087*
H9B	0.1573	0.4309	1.1594	0.087*
H9C	0.2299	0.3168	1.1447	0.087*

	U11	U22	U33	U12	U13	U23
Cl1	0.1591 (13)	0.0423 (5)	0.0387 (5)	0.000	0.0069 (6)	0.000
O1	0.0545 (11)	0.0522 (12)	0.0491 (11)	0.0011 (9)	0.0158 (9)	0.0059 (9)
O2	0.092 (2)	0.0344 (15)	0.0434 (14)	0.000	0.0109 (14)	0.000
N1	0.0365 (11)	0.0278 (10)	0.0358 (10)	−0.0015 (8)	−0.0027 (8)	0.0024 (8)
C1	0.0400 (18)	0.0271 (15)	0.0379 (15)	0.000	0.0009 (14)	0.000
C2	0.0572 (16)	0.0300 (13)	0.0461 (13)	−0.0031 (11)	0.0030 (11)	0.0012 (11)
C3	0.0319 (12)	0.0362 (13)	0.0323 (10)	−0.0010 (10)	−0.0018 (9)	0.0024 (10)
C4	0.0473 (15)	0.0333 (14)	0.0455 (14)	−0.0024 (11)	0.0086 (11)	0.0080 (11)
C5	0.0510 (15)	0.0339 (13)	0.0499 (14)	0.0029 (12)	0.0085 (11)	0.0012 (12)
C6	0.0356 (14)	0.0442 (15)	0.0360 (12)	−0.0008 (11)	0.0001 (11)	0.0027 (11)
C7	0.0480 (15)	0.0421 (16)	0.0438 (14)	−0.0081 (12)	0.0045 (11)	0.0072 (12)
C8	0.0518 (16)	0.0319 (13)	0.0484 (15)	−0.0044 (12)	0.0012 (13)	0.0019 (12)
C9	0.0485 (16)	0.069 (2)	0.0566 (16)	−0.0036 (14)	0.0137 (13)	0.0109 (15)

O1—C6	1.371 (3)	C4—C5	1.380 (4)
O1—C9	1.430 (3)	C4—H4	0.9300
O2—H2	0.8500	C5—C6	1.394 (4)
N1—C1	1.332 (3)	C5—H5	0.9300
N1—C2	1.382 (3)	C6—C7	1.382 (4)
N1—C3	1.443 (3)	C7—C8	1.392 (4)
C1—N1i	1.332 (3)	C7—H7	0.9300
C1—H1	0.9300	C8—H8	0.9300
C2—C2i	1.334 (5)	C9—H9A	0.9600
C2—H2A	0.9300	C9—H9B	0.9600
C3—C8	1.372 (3)	C9—H9C	0.9600
C3—C4	1.390 (4)
C6—O1—C9	117.2 (2)	C4—C5—H5	119.8
C1—N1—C2	107.8 (2)	C6—C5—H5	119.8
C1—N1—C3	126.1 (2)	O1—C6—C7	124.9 (2)
C2—N1—C3	126.1 (2)	O1—C6—C5	115.6 (2)
N1i—C1—N1	109.1 (3)	C7—C6—C5	119.5 (2)
N1i—C1—H1	125.5	C6—C7—C8	120.0 (2)
N1—C1—H1	125.5	C6—C7—H7	120.0
C2i—C2—N1	107.63 (14)	C8—C7—H7	120.0
C2i—C2—H2A	126.2	C3—C8—C7	120.2 (2)
N1—C2—H2A	126.2	C3—C8—H8	119.9
C8—C3—C4	120.1 (2)	C7—C8—H8	119.9
C8—C3—N1	120.1 (2)	O1—C9—H9A	109.5
C4—C3—N1	119.8 (2)	O1—C9—H9B	109.5
C5—C4—C3	119.8 (2)	H9A—C9—H9B	109.5
C5—C4—H4	120.1	O1—C9—H9C	109.5
C3—C4—H4	120.1	H9A—C9—H9C	109.5
C4—C5—C6	120.4 (2)	H9B—C9—H9C	109.5
C2—N1—C1—N1i	0.12 (13)	C3—C4—C5—C6	−0.4 (4)
C3—N1—C1—N1i	−178.4 (2)	C9—O1—C6—C7	−2.5 (4)
C1—N1—C2—C2i	−0.3 (3)	C9—O1—C6—C5	177.7 (2)
C3—N1—C2—C2i	178.2 (2)	C4—C5—C6—O1	−178.7 (2)
C1—N1—C3—C8	175.65 (18)	C4—C5—C6—C7	1.5 (4)
C2—N1—C3—C8	−2.6 (3)	O1—C6—C7—C8	178.9 (2)
C1—N1—C3—C4	−4.5 (3)	C5—C6—C7—C8	−1.3 (4)
C2—N1—C3—C4	177.3 (2)	C4—C3—C8—C7	1.1 (3)
C8—C3—C4—C5	−0.9 (4)	N1—C3—C8—C7	−179.0 (2)
N1—C3—C4—C5	179.2 (2)	C6—C7—C8—C3	0.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···Cl1	0.85	2.29	3.133 (3)	173
C1—H1···O2	0.93	2.13	3.060 (3)	180
C2—H2A···Cl1ii	0.93	2.69	3.474 (3)	142
C4—H4···O2	0.93	2.47	3.391 (3)	170
C9—H9C···Cg2iii	0.96	2.91	3.629 (3)	133

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C3–C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯Cl1	0.85	2.29	3.133 (3)	173
C1—H1⋯O2	0.93	2.13	3.060 (3)	180
C2—H2A⋯Cl1i	0.93	2.69	3.474 (3)	142
C4—H4⋯O2	0.93	2.47	3.391 (3)	170
C9—H9C⋯Cg2ii	0.96	2.91	3.629 (3)	133

Symmetry codes: (i) ; (ii) .