(R)-4-(4-Fluoro­phenyl)-1-[2-hydroxy-2-(3-methyl-1-benzo­furan-2-yl)­ethyl]­piperazinium chloride propan-1-ol solvate

The title compound, C₂₁H₂₄FN₂O₂⁺·Cl⁻·C₃H₈O, is a potential drug designed as a hybrid compound with antihypertensive, antioxidant and β-adrenolytic activity. The cation contains nearly planar benzo­furan and fluoro­phenyl ring systems, as well as a piperazine ring adopting an almost perfect chair conformation. The benzo­furan and piperazine moieties are connected by an ethyl chain, the moieties forming a dihedral angle of 163.12 (13)°. In the crystal structure, ions and propanol solvent mol­ecules are linked via N—H...Cl and O—H...Cl bonds into linear (010) chains.

S1. Comment

Increased blood pressure is one of the major diseases of the cardiovascular system, leading to various organ disfunctions, i.e. left ventricular hypertrophy, ischemic heart disease, renal failure and cerebrovascular damage (Pinkey & Yudkin, 1994). The title organic salt [(I), in pharmacological literature labeled as (4/1)] was designed and synthesized as a potential antihypertensive drug combining β-adrenolytic, vasodilating and antioxidant activities. It belongs to a group of heteroarylaminoethanol derivatives that are known as drugs affecting the sympathetic nervous system (Ruffolo et al., 1995). Structurally, (I) is also an analogue of aryloxypropanolamines (Mokrý et al., 2003) in which the oxymethylene group of the linking moiety becomes a part of the furan ring. Although this modification is assumed to decrease? β-adrenolytic activity (Tumová et al., 1996), the arylpiperazine substitution gives rise to a vasodilating effect of the substance. As revealed in recent years, the reactive oxygen species (ROS) could play an important role in pathogenesis of hypertension (Friedman et al., 2003). Active compounds that, besides the direct hypotensive effect, also have the ability to scavenge ROS should be more effective and useful in long-term antihypertensive therapy. The complete pharmacological evaluation of the title compound has not yet been completed, but the preliminary findings show promising vasodilating and β-adrenolytic activity and significant antioxidant potency (Kurfürst et al., 2004).

The structure of the (4/1) cation in (I) (Fig. 1 and Table 1) is similar to that in fluorophenylpiperazinmethylbenzoxazolines (Köysal et al., 2004). The cation in (I) contains a nearly planar benzofuran ring system, with deviations from the planes of six-membered ring A and five-membered ring B of up to 0.005 and 0.008 Å, respectively. Methyl atom C21 lies almost in the plane of ring B [the deviation from the plane is 0.048 (2) Å]. The interplanar angle between aromatic rings A and B is 2.06 (6)°. The benzofuran moiety is connected by an almost linear methyl chain [the C1—C9—C10—N1 torsion angle is −163.12 (14) °] to the piperazine ring, C, adopting an almost perfect chair conformation [the Cremer & Pople (1975) puckering parameters for ring C are Q = 0.572 (2) Å, Θ = 177.5 (2)° and ϕ₂ =104 (4)°]. The second piperazine N atom, N2, is bonded to the fluorophenyl ring, D. The planarity of ring D is deformed by atom F; the deviations of atoms F and C18 from the plane of the remaining five ring atoms are 0.0501 (13) and 0.0223 (19) Å, respectively, while the out-of-plane deviations of the remaining five atoms are up to 0.006 Å. The plane through the C atoms of ring C makes dihedral angles with rings B and D of 81.92 (6) and 32.43 (6)°, respectively.

The positive charge of the (4/1) cation is compensated by the Cl⁻ anion, which creates N—H···Cl and O—H···Cl bonds (Table 2) connecting the Cl⁻ ion with two neighbouring cations and a propanol molecule. In the crystal structure of (I), ions and propanol molecules thus form linear (010) chains (Fig. 2). Two weaker C—H···O interactions involving the ethanol O—H moiety (O3) further link the molecular network.

S2. Experimental

Compound (I) was prepared by the reduction of 2-[4-(4-fluorophenyl)piperazin-1-yl]-1-(3-methylbenzofuran-2-yl)ethanone with NaBH₄ in methanol. The methanol was evaporated, and the residue was dissolved in chloroform, washed three times with water and dried over K₂CO₃. The chloroform was evaporated and the solid residue was recrystallized from propan-2-ol. The recrystallized product was dissolved in CHCl₃ and etheric HCl solution was added to obtain the HCl salt. White well developed crystals were obtained by recrystallization of the hydrochloride salt (1.1 g) from propan-1-ol (100 ml). Analysis (Carlo-Erba 1180 instrument) calculated for C₂₄H₃₂ClFN₂O₃: C 63.92, H 7.15, N 6.21%; found: C 63.80, H 7.20, N 6.28%.

S3. Refinement

Friedel pairs were not merged but were used for determination of the chemical absolute configuration. H atoms attached to C and N atoms were positioned geometrically, with an N—H distance of 0.93 Å and C–H distances in the range 0.95–0.99 Å, and with U_iso(H) values derived from the U_eq values of the corresponding C or N atoms. The parameters of H atoms attached to O atoms were refined with the O—H distances restrained to 0.95 (2) Å.

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2004); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Johnson & Burnett, 1996); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Figures

	Fig. 1. : A view of the title dimer. Non-H atoms are drawn as 50% probability displacement ellipsoids and H atoms as small spheres of arbitrary radii.
	Fig. 2. : Part of the crystal structure of (I), showing the formation of a chain of N—H···Cl- and O—H···Cl-bonded (4/1) cations, Cl anions and propanol molecules. H atoms not involved in hydrogen bonding have been omitted for clarity. [Symmetry codes: (i) 1 − x, y + 1/2, −z; (ii) 1 − x, y − 1/2, −z.]

(R)-4-(4-Fluorophenyl)1-[2-hydroxy-2-(3-methyl-1-benzofuran-2- yl)ethyl]piperazinium chloride propan-1-ol solvate

Crystal data

C21H24FN2O2^+·Cl^−·C3H8O	F(000) = 480
Mr = 450.97	Dx = 1.298 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4744 reflections
a = 10.6052 (6) Å	θ = 2.6–29.0°
b = 8.3553 (6) Å	µ = 0.20 mm^−1
c = 13.0588 (10) Å	T = 120 K
β = 94.167 (6)°	Prism, white
V = 1154.08 (14) Å^3	0.50 × 0.40 × 0.30 mm
Z = 2

Data collection

Kuma KM4-Plus CCD diffractometer	3194 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Enhance (Oxford Diffraction) monochromator	θmax = 25.0°, θmin = 3.1°
Detector resolution: 16.3 pixels mm^-1	h = −12→12
ω scans	k = −7→9
7674 measured reflections	l = −15→15
3317 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.025	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.066	w = 1/[σ^2(Fo^2) + (0.045P)^2 + 0.05P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
3317 reflections	Δρmax = 0.15 e Å^−3
290 parameters	Δρmin = −0.14 e Å^−3
3 restraints	Absolute structure: (Flack, 1983), 1144 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.05 (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
Cl	0.24134 (3)	0.00002 (6)	0.00677 (3)	0.02609 (11)
F	−0.22049 (9)	0.06734 (15)	−0.59824 (8)	0.0374 (3)
O1	0.41258 (10)	0.66893 (15)	0.15241 (8)	0.0210 (3)
O2	0.46705 (9)	0.50715 (18)	−0.03824 (8)	0.0246 (3)
N1	0.20335 (11)	0.35194 (17)	−0.05875 (10)	0.0173 (3)
H1	0.2207	0.2467	−0.0393	0.021*
N2	0.05046 (11)	0.28818 (18)	−0.24676 (10)	0.0182 (3)
C1	0.44704 (13)	0.5094 (2)	0.14433 (11)	0.0186 (3)
C2	0.51393 (14)	0.4556 (2)	0.22955 (13)	0.0209 (4)
C3	0.52349 (14)	0.5903 (2)	0.29887 (12)	0.0212 (4)
C4	0.58142 (14)	0.6178 (2)	0.39764 (12)	0.0250 (4)
H4	0.6239	0.5341	0.4354	0.030*
C5	0.57491 (15)	0.7699 (3)	0.43825 (13)	0.0293 (4)
H5	0.6135	0.7904	0.5049	0.035*
C6	0.51304 (16)	0.8940 (3)	0.38390 (13)	0.0292 (4)
H6	0.5108	0.9971	0.4143	0.035*
C7	0.45454 (16)	0.8706 (2)	0.28620 (13)	0.0250 (4)
H7	0.4125	0.9548	0.2486	0.030*
C8	0.46147 (14)	0.7175 (2)	0.24728 (12)	0.0203 (4)
C9	0.40589 (14)	0.4347 (2)	0.04324 (12)	0.0199 (4)
H9	0.4253	0.3176	0.0456	0.024*
C10	0.26305 (14)	0.4592 (2)	0.02248 (12)	0.0195 (4)
H10A	0.2218	0.4408	0.0871	0.023*
H10B	0.2472	0.5718	0.0018	0.023*
C11	0.06218 (13)	0.3737 (2)	−0.06585 (12)	0.0193 (3)
H11A	0.0415	0.4864	−0.0833	0.023*
H11B	0.0295	0.3500	0.0016	0.023*
C12	−0.00107 (14)	0.2650 (2)	−0.14628 (12)	0.0199 (4)
H12A	0.0113	0.1522	−0.1246	0.024*
H12B	−0.0931	0.2869	−0.1525	0.024*
C13	0.18716 (14)	0.2639 (2)	−0.23978 (12)	0.0207 (4)
H13A	0.2199	0.2818	−0.3079	0.025*
H13B	0.2066	0.1521	−0.2189	0.025*
C14	0.25143 (13)	0.3774 (2)	−0.16260 (12)	0.0215 (4)
H14A	0.3439	0.3594	−0.1589	0.026*
H14B	0.2349	0.4892	−0.1849	0.026*
C15	−0.01808 (14)	0.2225 (2)	−0.33333 (12)	0.0184 (3)
C16	−0.14840 (15)	0.2518 (2)	−0.34994 (13)	0.0235 (4)
H16	−0.1907	0.3092	−0.2998	0.028*
C17	−0.21642 (15)	0.1987 (2)	−0.43788 (14)	0.0275 (4)
H17	−0.3047	0.2181	−0.4480	0.033*
C18	−0.15383 (15)	0.1171 (2)	−0.51035 (13)	0.0249 (4)
C19	−0.02738 (15)	0.0829 (2)	−0.49694 (13)	0.0247 (4)
H19	0.0132	0.0241	−0.5474	0.030*
C20	0.04045 (14)	0.1353 (2)	−0.40857 (13)	0.0216 (4)
H20	0.1281	0.1117	−0.3987	0.026*
C21	0.57023 (17)	0.2937 (3)	0.24891 (14)	0.0304 (4)
H21A	0.5496	0.2249	0.1893	0.046*
H21B	0.5359	0.2466	0.3097	0.046*
H21C	0.6623	0.3034	0.2605	0.046*
H2O	0.5536 (14)	0.496 (3)	−0.0271 (15)	0.038 (5)*
O3	0.10812 (13)	−0.25574 (17)	−0.14227 (10)	0.0359 (3)
C22	0.02280 (19)	−0.1939 (3)	−0.22189 (15)	0.0340 (4)
H22A	0.0676	−0.1788	−0.2851	0.041*
H22B	−0.0096	−0.0886	−0.2011	0.041*
C23	−0.08516 (17)	−0.3076 (3)	−0.24263 (14)	0.0333 (5)
H23A	−0.1245	−0.3294	−0.1776	0.040*
H23B	−0.0523	−0.4101	−0.2678	0.040*
C24	−0.1857 (2)	−0.2435 (3)	−0.32131 (16)	0.0429 (5)
H24A	−0.2249	−0.1480	−0.2938	0.064*
H24B	−0.2505	−0.3256	−0.3361	0.064*
H24C	−0.1465	−0.2157	−0.3846	0.064*
H3O	0.152 (3)	−0.170 (3)	−0.110 (2)	0.088 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.02023 (17)	0.0237 (2)	0.0343 (2)	0.00081 (17)	0.00160 (14)	0.00331 (19)
F	0.0332 (5)	0.0499 (8)	0.0280 (5)	−0.0053 (5)	−0.0061 (4)	−0.0118 (5)
O1	0.0234 (5)	0.0190 (6)	0.0203 (6)	0.0009 (5)	0.0002 (4)	−0.0002 (5)
O2	0.0182 (5)	0.0342 (7)	0.0215 (5)	−0.0045 (6)	0.0024 (4)	0.0016 (6)
N1	0.0167 (6)	0.0175 (8)	0.0180 (7)	0.0004 (5)	0.0032 (5)	−0.0004 (6)
N2	0.0146 (6)	0.0233 (8)	0.0170 (7)	−0.0004 (6)	0.0037 (5)	−0.0028 (6)
C1	0.0179 (6)	0.0160 (8)	0.0223 (8)	−0.0005 (7)	0.0028 (5)	0.0002 (7)
C2	0.0177 (7)	0.0235 (10)	0.0217 (8)	−0.0017 (6)	0.0023 (6)	0.0011 (7)
C3	0.0168 (7)	0.0271 (10)	0.0202 (8)	−0.0053 (7)	0.0053 (6)	0.0027 (7)
C4	0.0193 (7)	0.0361 (11)	0.0199 (8)	−0.0054 (7)	0.0036 (6)	0.0028 (8)
C5	0.0247 (8)	0.0458 (13)	0.0181 (8)	−0.0118 (8)	0.0057 (6)	−0.0036 (8)
C6	0.0320 (9)	0.0320 (11)	0.0254 (9)	−0.0123 (8)	0.0141 (7)	−0.0093 (8)
C7	0.0266 (8)	0.0232 (10)	0.0262 (9)	−0.0037 (7)	0.0093 (6)	−0.0014 (8)
C8	0.0182 (7)	0.0250 (10)	0.0183 (8)	−0.0044 (7)	0.0053 (6)	−0.0008 (7)
C9	0.0200 (7)	0.0208 (9)	0.0188 (8)	0.0000 (6)	0.0019 (6)	−0.0003 (7)
C10	0.0187 (7)	0.0209 (10)	0.0194 (8)	−0.0013 (6)	0.0037 (6)	−0.0027 (7)
C11	0.0148 (7)	0.0248 (9)	0.0187 (8)	0.0008 (7)	0.0043 (5)	0.0011 (7)
C12	0.0179 (7)	0.0227 (10)	0.0197 (8)	−0.0010 (6)	0.0052 (6)	0.0005 (7)
C13	0.0155 (7)	0.0271 (10)	0.0201 (8)	0.0015 (6)	0.0050 (6)	−0.0024 (7)
C14	0.0168 (7)	0.0292 (10)	0.0191 (8)	−0.0021 (7)	0.0061 (6)	−0.0014 (7)
C15	0.0212 (7)	0.0150 (8)	0.0191 (7)	−0.0010 (6)	0.0033 (6)	0.0012 (7)
C16	0.0210 (8)	0.0232 (10)	0.0263 (9)	0.0016 (7)	0.0021 (6)	−0.0023 (7)
C17	0.0208 (8)	0.0297 (12)	0.0315 (10)	0.0003 (7)	−0.0009 (7)	−0.0010 (8)
C18	0.0262 (8)	0.0267 (10)	0.0211 (8)	−0.0071 (7)	−0.0024 (6)	−0.0016 (7)
C19	0.0295 (8)	0.0243 (10)	0.0210 (8)	−0.0023 (7)	0.0060 (7)	−0.0046 (8)
C20	0.0197 (7)	0.0235 (10)	0.0222 (8)	0.0015 (7)	0.0043 (6)	−0.0005 (7)
C21	0.0352 (9)	0.0258 (11)	0.0295 (10)	0.0039 (8)	−0.0021 (7)	0.0038 (8)
O3	0.0489 (8)	0.0238 (8)	0.0344 (8)	−0.0048 (6)	−0.0019 (6)	−0.0001 (6)
C22	0.0491 (11)	0.0214 (10)	0.0323 (10)	0.0010 (9)	0.0069 (8)	0.0036 (9)
C23	0.0405 (10)	0.0318 (12)	0.0280 (10)	0.0016 (9)	0.0053 (8)	0.0037 (9)
C24	0.0445 (11)	0.0432 (14)	0.0410 (12)	0.0078 (10)	0.0040 (9)	0.0066 (10)

Geometric parameters (Å, º)

F—C18	1.3682 (19)	C11—H11B	0.9900
O1—C8	1.3693 (19)	C12—H12A	0.9900
O1—C1	1.388 (2)	C12—H12B	0.9900
O2—C9	1.421 (2)	C13—C14	1.510 (2)
O2—H2O	0.923 (15)	C13—H13A	0.9900
N1—C10	1.494 (2)	C13—H13B	0.9900
N1—C14	1.4983 (19)	C14—H14A	0.9900
N1—C11	1.5043 (17)	C14—H14B	0.9900
N1—H1	0.9300	C15—C20	1.404 (2)
N2—C15	1.410 (2)	C15—C16	1.405 (2)
N2—C13	1.4602 (18)	C16—C17	1.384 (2)
N2—C12	1.4704 (19)	C16—H16	0.9500
C1—C2	1.352 (2)	C17—C18	1.375 (3)
C1—C9	1.496 (2)	C17—H17	0.9500
C2—C3	1.443 (3)	C18—C19	1.370 (2)
C2—C21	1.492 (3)	C19—C20	1.386 (2)
C3—C8	1.397 (3)	C19—H19	0.9500
C3—C4	1.407 (2)	C20—H20	0.9500
C4—C5	1.380 (3)	C21—H21A	0.9800
C4—H4	0.9500	C21—H21B	0.9800
C5—C6	1.394 (3)	C21—H21C	0.9800
C5—H5	0.9500	O3—C22	1.425 (2)
C6—C7	1.391 (2)	O3—H3O	0.937 (18)
C6—H6	0.9500	C22—C23	1.497 (3)
C7—C8	1.381 (3)	C22—H22A	0.9900
C7—H7	0.9500	C22—H22B	0.9900
C9—C10	1.533 (2)	C23—C24	1.523 (3)
C9—H9	1.0000	C23—H23A	0.9900
C10—H10A	0.9900	C23—H23B	0.9900
C10—H10B	0.9900	C24—H24A	0.9800
C11—C12	1.509 (2)	C24—H24B	0.9800
C11—H11A	0.9900	C24—H24C	0.9800
C8—O1—C1	105.60 (13)	C11—C12—H12B	109.3
C9—O2—H2O	110.1 (13)	H12A—C12—H12B	108.0
C10—N1—C14	113.77 (12)	N2—C13—C14	110.62 (13)
C10—N1—C11	109.87 (12)	N2—C13—H13A	109.5
C14—N1—C11	109.25 (11)	C14—C13—H13A	109.5
C10—N1—H1	107.9	N2—C13—H13B	109.5
C14—N1—H1	107.9	C14—C13—H13B	109.5
C11—N1—H1	107.9	H13A—C13—H13B	108.1
C15—N2—C13	116.59 (12)	N1—C14—C13	110.38 (13)
C15—N2—C12	117.44 (12)	N1—C14—H14A	109.6
C13—N2—C12	110.96 (12)	C13—C14—H14A	109.6
C2—C1—O1	112.45 (14)	N1—C14—H14B	109.6
C2—C1—C9	133.57 (16)	C13—C14—H14B	109.6
O1—C1—C9	113.95 (13)	H14A—C14—H14B	108.1
C1—C2—C3	105.40 (15)	C20—C15—C16	117.55 (15)
C1—C2—C21	128.32 (16)	C20—C15—N2	122.33 (13)
C3—C2—C21	126.26 (15)	C16—C15—N2	120.01 (14)
C8—C3—C4	118.47 (18)	C17—C16—C15	121.32 (16)
C8—C3—C2	106.37 (14)	C17—C16—H16	119.3
C4—C3—C2	135.12 (17)	C15—C16—H16	119.3
C5—C4—C3	118.17 (18)	C18—C17—C16	118.77 (15)
C5—C4—H4	120.9	C18—C17—H17	120.6
C3—C4—H4	120.9	C16—C17—H17	120.6
C4—C5—C6	121.61 (16)	F—C18—C19	119.01 (15)
C4—C5—H5	119.2	F—C18—C17	118.82 (15)
C6—C5—H5	119.2	C19—C18—C17	122.17 (15)
C7—C6—C5	121.64 (19)	C18—C19—C20	118.99 (16)
C7—C6—H6	119.2	C18—C19—H19	120.5
C5—C6—H6	119.2	C20—C19—H19	120.5
C8—C7—C6	115.81 (18)	C19—C20—C15	121.18 (15)
C8—C7—H7	122.1	C19—C20—H20	119.4
C6—C7—H7	122.1	C15—C20—H20	119.4
O1—C8—C7	125.51 (16)	C2—C21—H21A	109.5
O1—C8—C3	110.18 (16)	C2—C21—H21B	109.5
C7—C8—C3	124.28 (16)	H21A—C21—H21B	109.5
O2—C9—C1	111.29 (13)	C2—C21—H21C	109.5
O2—C9—C10	108.04 (13)	H21A—C21—H21C	109.5
C1—C9—C10	108.75 (12)	H21B—C21—H21C	109.5
O2—C9—H9	109.6	C22—O3—H3O	108 (2)
C1—C9—H9	109.6	O3—C22—C23	109.82 (16)
C10—C9—H9	109.6	O3—C22—H22A	109.7
N1—C10—C9	114.08 (12)	C23—C22—H22A	109.7
N1—C10—H10A	108.7	O3—C22—H22B	109.7
C9—C10—H10A	108.7	C23—C22—H22B	109.7
N1—C10—H10B	108.7	H22A—C22—H22B	108.2
C9—C10—H10B	108.7	C22—C23—C24	112.84 (18)
H10A—C10—H10B	107.6	C22—C23—H23A	109.0
N1—C11—C12	111.12 (13)	C24—C23—H23A	109.0
N1—C11—H11A	109.4	C22—C23—H23B	109.0
C12—C11—H11A	109.4	C24—C23—H23B	109.0
N1—C11—H11B	109.4	H23A—C23—H23B	107.8
C12—C11—H11B	109.4	C23—C24—H24A	109.5
H11A—C11—H11B	108.0	C23—C24—H24B	109.5
N2—C12—C11	111.50 (12)	H24A—C24—H24B	109.5
N2—C12—H12A	109.3	C23—C24—H24C	109.5
C11—C12—H12A	109.3	H24A—C24—H24C	109.5
N2—C12—H12B	109.3	H24B—C24—H24C	109.5
C1—C9—C10—N1	−163.04 (14)	C2—C1—C9—C10	127.83 (18)
C9—C10—N1—C11	174.39 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl	0.93	2.15	3.0806 (15)	174
O3—H3O···Cl	0.94 (2)	2.25 (2)	3.1546 (15)	163 (3)
O2—H2O···Cl^i	0.92 (2)	2.17 (2)	3.0906 (11)	173 (2)

Symmetry code: (i) −x+1, y+1/2, −z.