Bis{1-[3-(cyclo­hexyl­aminio)propyl­imino­meth­yl]-2-naphtholato}nickel(II) dichloride 1.24-hydrate

The title complex, [Ni(C₂₀H₂₆N₂O)₂]Cl₂·1.24H₂O, is a mononuclear nickel(II) compound. The Ni^II atom, lying on an inversion centre, is four-coordinated in a square-planar geometry by two imine N and two phenolate O atoms from two Schiff bases.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in solvent or counterion
• R factor = 0.043
• wR factor = 0.113
• Data-to-parameter ratio = 18.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms ..          ?
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      31.00 Perc.

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C40 H54.48 Cl2 N4 Ni1 O3.24
            Atom count from _chemical_formula_moiety:H4 O2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

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S1. Comment

Schiff base complexes have been studied extensively, due to their excellent biological activities (Ren et al., 2002; Deschamps et al., 2003; Pal et al., 2003). Nickel(II) complexes are very important in coordination chemistry (Dey et al., 2004; Christensen et al., 1997). The structures of a large number of mono-, di- and polynuclear Schiff base nickel(II) complexes have been reported (Vance et al., 1997; Carbonaro et al., 1999; Rybak-Akimova et al., 1998). In order to investigate the structures of such nickel complexes, the title new nickel(II) complex, (I), is reported here.

Complex (I) is a mononuclear nickel(II) compound, with the Ni^II atom lying on an inversion centre (Fig. 1). The unit cell contains an [Ni(C₂₀H₂₆N₂O)₂]²⁺ cation, two Cl⁻ anions and two water molecules, each with site occupancy of 0.62. The Ni^II atom is four-coordinated in a square-planar geometry by two imine N and two phenolate O atoms from two Schiff bases. All bond angles (Table 1) subtended at the Ni^II centre are comparable with the values observed in other Schiff base nickel(II) complexes (Gomes et al., 2000; Chakraborty et al., 2004).

In the crystal structure, the molecules are linked through intermolecular O—H···Cl and N—H···Cl hydrogen bonds (Table 2), forming layers parallel to the bc plane (Fig. 2).

S2. Experimental

N-Cyclohexyl-1,3-diaminopropane (0.1 mmol, 15.6 mg) and 2-hydroxy-1-naphthaldehyde (0.1 mmol, 8.6 mg) were dissolved in MeOH (10 ml). The mixture was stirred at room temperature for 10 min to give a clear yellow solution, to which was added an aqueous solution (5 ml) of NiCl₂·4H₂O (0.1 mmol, 20.2 mg) with stirring. The mixture was stirred for another 10 min at room temperature and filtered. After keeping the filtrate in air for 9 d, green block crystals of (I) separated. The crystals were isolated, washed three times with MeOH and dried in a vacuum desiccator using anhydrous CaCl₂ (yield 51.3%). Analysis, found: C 60.89, H 7.27, N 7.30%; calculated for C₄₀H_54.49Cl₂N₄NiO_3.245: C 62.16, H 7.11, N 7.25%.

S3. Refinement

Attempts to refine the water O atom (O2) with full occupancy resulted in a high U_iso value, and hence it was refined with partial occupancy. The occupancy was initially refined to 0.623 (8) and later fixed at 0.62. Atoms H2C and H2D were located in a difference Fourier map and refined isotropically, with the O—H and H···H distances restrained to 0.84 (1) and 1.37 (2) Å, respectively, and with a fixed U_iso(H) value of 0.08 Ų. All other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with N—H = 0.90 Å and C—H distances in the range 0.93–0.98 Å, and with U_iso(H) = 1.2–1.5U_eq(C,N).

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. The structure of (I). Displacement ellipsoids are drawn at the 30% probability level. Unlabelled atoms are at the symmetry position (1 − x, −y, 2 − z).
	Fig. 2. The crystal packing of (I), viewed along the b axis. Dashed lines indicate hydrogen bonds. Only the H atoms involved in hydrogen bonding are shown.

Bis{1-[3-(cyclohexylamino)propyliminomethyl]-2-naphtholato}nickel(II) dichloride 1.24 hydrate

Crystal data

[Ni(C20H26N2O)2]Cl2·2(0.62H2O)	F(000) = 820.8
Mr = 772.79	Dx = 1.299 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3936 reflections
a = 11.179 (1) Å	θ = 2.4–26.8°
b = 7.431 (1) Å	µ = 0.67 mm^−1
c = 23.683 (2) Å	T = 298 K
β = 92.53 (1)°	Block, green
V = 1965.5 (4) Å^3	0.20 × 0.13 × 0.12 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	4490 independent reflections
Radiation source: fine-focus sealed tube	3546 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
ω scans	θmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.878, Tmax = 0.924	k = −9→9
16272 measured reflections	l = −29→30

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0602P)^2 + 0.2608P] where P = (Fo^2 + 2Fc^2)/3
4490 reflections	(Δ/σ)max < 0.001
238 parameters	Δρmax = 0.41 e Å^−3
3 restraints	Δρmin = −0.24 e Å^−3

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	Occ. (<1)
Ni1	0.5000	0.0000	1.0000	0.03502 (13)
Cl1	0.44952 (6)	0.58347 (9)	0.80533 (2)	0.05745 (18)
O1	0.62800 (14)	0.1097 (2)	1.03618 (6)	0.0501 (4)
O2	0.3109 (3)	0.3483 (5)	0.71190 (16)	0.0848 (10)	0.62
N1	0.47904 (14)	0.1972 (2)	0.94845 (6)	0.0334 (4)
N2	0.32943 (14)	−0.0553 (2)	0.76477 (6)	0.0357 (4)
H2A	0.3564	−0.1631	0.7771	0.043*
H2B	0.3877	−0.0042	0.7452	0.043*
C1	0.64663 (17)	0.3815 (3)	0.98392 (8)	0.0346 (4)
C2	0.68353 (18)	0.2589 (3)	1.02548 (8)	0.0416 (5)
C3	0.7899 (2)	0.2956 (3)	1.05928 (10)	0.0579 (7)
H3	0.8151	0.2145	1.0873	0.069*
C4	0.8545 (2)	0.4465 (4)	1.05112 (10)	0.0559 (6)
H4	0.9239	0.4661	1.0734	0.067*
C5	0.81959 (19)	0.5751 (3)	1.00986 (9)	0.0443 (5)
C6	0.8886 (2)	0.7322 (3)	1.00214 (11)	0.0584 (6)
H6	0.9585	0.7501	1.0242	0.070*
C7	0.8538 (2)	0.8571 (4)	0.96283 (12)	0.0676 (7)
H7	0.8993	0.9603	0.9581	0.081*
C8	0.7500 (3)	0.8296 (3)	0.92980 (12)	0.0650 (7)
H8	0.7267	0.9152	0.9029	0.078*
C9	0.6810 (2)	0.6793 (3)	0.93593 (10)	0.0491 (5)
H9	0.6114	0.6649	0.9134	0.059*
C10	0.71421 (18)	0.5465 (3)	0.97579 (9)	0.0383 (5)
C11	0.54373 (17)	0.3423 (3)	0.94819 (8)	0.0346 (4)
H11	0.5205	0.4300	0.9219	0.042*
C12	0.38126 (17)	0.1942 (3)	0.90445 (8)	0.0357 (4)
H12A	0.3635	0.3163	0.8922	0.043*
H12B	0.3097	0.1446	0.9202	0.043*
C13	0.41495 (17)	0.0823 (3)	0.85396 (8)	0.0377 (4)
H13A	0.4783	0.1416	0.8343	0.045*
H13B	0.4438	−0.0348	0.8665	0.045*
C14	0.3063 (2)	0.0603 (4)	0.81479 (9)	0.0496 (6)
H14A	0.2422	0.0073	0.8355	0.060*
H14B	0.2798	0.1780	0.8017	0.060*
C15	0.22189 (16)	−0.0842 (3)	0.72576 (8)	0.0353 (4)
H15	0.1887	0.0338	0.7153	0.042*
C16	0.12572 (19)	−0.1910 (3)	0.75417 (9)	0.0489 (5)
H16A	0.1012	−0.1272	0.7875	0.059*
H16B	0.1575	−0.3071	0.7661	0.059*
C17	0.0179 (2)	−0.2179 (4)	0.71328 (11)	0.0600 (7)
H17A	−0.0415	−0.2907	0.7314	0.072*
H17B	−0.0180	−0.1020	0.7043	0.072*
C18	0.0523 (2)	−0.3088 (4)	0.65920 (10)	0.0611 (7)
H18A	−0.0172	−0.3168	0.6333	0.073*
H18B	0.0801	−0.4300	0.6675	0.073*
C19	0.1504 (2)	−0.2032 (3)	0.63174 (9)	0.0497 (6)
H19A	0.1196	−0.0864	0.6200	0.060*
H19B	0.1746	−0.2666	0.5983	0.060*
C20	0.25888 (18)	−0.1776 (3)	0.67225 (8)	0.0423 (5)
H20A	0.2939	−0.2938	0.6817	0.051*
H20B	0.3188	−0.1059	0.6542	0.051*
H2C	0.338 (4)	0.400 (6)	0.7410 (13)	0.080*	0.62
H2D	0.363 (3)	0.281 (6)	0.6992 (18)	0.080*	0.62

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0383 (2)	0.0366 (2)	0.0298 (2)	−0.00794 (15)	−0.00372 (14)	0.00060 (14)
Cl1	0.0630 (4)	0.0543 (4)	0.0553 (4)	0.0185 (3)	0.0058 (3)	0.0102 (3)
O1	0.0543 (9)	0.0500 (9)	0.0443 (8)	−0.0206 (7)	−0.0164 (7)	0.0111 (7)
O2	0.098 (3)	0.066 (2)	0.088 (3)	−0.0054 (19)	−0.017 (2)	−0.0037 (18)
N1	0.0356 (8)	0.0374 (9)	0.0269 (8)	−0.0038 (7)	−0.0020 (6)	−0.0026 (6)
N2	0.0351 (9)	0.0387 (9)	0.0326 (8)	0.0007 (7)	−0.0047 (7)	−0.0011 (7)
C1	0.0367 (10)	0.0369 (10)	0.0303 (9)	−0.0044 (8)	0.0038 (8)	−0.0043 (8)
C2	0.0440 (12)	0.0435 (12)	0.0368 (11)	−0.0096 (9)	−0.0037 (9)	−0.0029 (9)
C3	0.0579 (14)	0.0588 (15)	0.0549 (14)	−0.0182 (12)	−0.0195 (11)	0.0134 (12)
C4	0.0486 (13)	0.0621 (15)	0.0555 (14)	−0.0198 (12)	−0.0151 (11)	0.0021 (12)
C5	0.0453 (12)	0.0433 (12)	0.0446 (12)	−0.0115 (10)	0.0040 (9)	−0.0073 (10)
C6	0.0524 (14)	0.0572 (15)	0.0651 (16)	−0.0205 (12)	−0.0025 (12)	−0.0036 (13)
C7	0.0692 (17)	0.0514 (15)	0.0820 (19)	−0.0274 (13)	0.0008 (14)	0.0079 (14)
C8	0.0778 (18)	0.0480 (14)	0.0682 (17)	−0.0181 (13)	−0.0061 (14)	0.0110 (13)
C9	0.0540 (13)	0.0439 (12)	0.0492 (13)	−0.0083 (10)	−0.0007 (10)	0.0022 (10)
C10	0.0392 (11)	0.0378 (11)	0.0383 (11)	−0.0054 (8)	0.0069 (9)	−0.0071 (8)
C11	0.0415 (11)	0.0334 (10)	0.0291 (9)	−0.0007 (8)	0.0041 (8)	−0.0019 (8)
C12	0.0363 (10)	0.0361 (10)	0.0343 (10)	−0.0003 (8)	−0.0032 (8)	−0.0004 (8)
C13	0.0336 (10)	0.0476 (12)	0.0313 (10)	−0.0010 (9)	−0.0041 (8)	−0.0012 (9)
C14	0.0453 (13)	0.0633 (15)	0.0392 (12)	0.0084 (11)	−0.0108 (9)	−0.0153 (11)
C15	0.0321 (10)	0.0414 (11)	0.0318 (10)	−0.0005 (8)	−0.0064 (8)	−0.0013 (8)
C16	0.0457 (12)	0.0621 (15)	0.0387 (11)	−0.0106 (11)	0.0013 (9)	−0.0028 (10)
C17	0.0408 (13)	0.0804 (19)	0.0591 (15)	−0.0184 (12)	0.0045 (11)	−0.0073 (13)
C18	0.0541 (14)	0.0765 (18)	0.0519 (14)	−0.0234 (13)	−0.0067 (11)	−0.0104 (13)
C19	0.0482 (13)	0.0629 (15)	0.0374 (11)	−0.0126 (11)	−0.0047 (9)	−0.0063 (10)
C20	0.0406 (11)	0.0508 (13)	0.0353 (11)	−0.0037 (9)	−0.0001 (9)	−0.0048 (9)

Geometric parameters (Å, º)

Ni1—O1	1.827 (2)	C9—C10	1.404 (3)
Ni1—O1^i	1.827 (2)	C9—H9	0.93
Ni1—N1	1.915 (2)	C11—H11	0.93
Ni1—N1^i	1.915 (2)	C12—C13	1.518 (3)
O1—C2	1.301 (2)	C12—H12A	0.97
O2—H2C	0.83 (1)	C12—H12B	0.97
O2—H2D	0.84 (1)	C13—C14	1.504 (3)
N1—C11	1.299 (2)	C13—H13A	0.97
N1—C12	1.477 (2)	C13—H13B	0.97
N2—C14	1.495 (3)	C14—H14A	0.97
N2—C15	1.499 (2)	C14—H14B	0.97
N2—H2A	0.90	C15—C16	1.517 (3)
N2—H2B	0.90	C15—C20	1.518 (3)
C1—C2	1.391 (3)	C15—H15	0.98
C1—C11	1.428 (3)	C16—C17	1.526 (3)
C1—C10	1.457 (3)	C16—H16A	0.97
C2—C3	1.431 (3)	C16—H16B	0.97
C3—C4	1.352 (3)	C17—C18	1.512 (3)
C3—H3	0.93	C17—H17A	0.97
C4—C5	1.409 (3)	C17—H17B	0.97
C4—H4	0.93	C18—C19	1.518 (3)
C5—C10	1.414 (3)	C18—H18A	0.97
C5—C6	1.416 (3)	C18—H18B	0.97
C6—C7	1.359 (4)	C19—C20	1.525 (3)
C6—H6	0.93	C19—H19A	0.97
C7—C8	1.386 (4)	C19—H19B	0.97
C7—H7	0.93	C20—H20A	0.97
C8—C9	1.369 (3)	C20—H20B	0.97
C8—H8	0.93
O1—Ni1—O1^i	180	C13—C12—H12A	109.4
O1—Ni1—N1	91.66 (7)	N1—C12—H12B	109.4
O1^i—Ni1—N1	88.34 (7)	C13—C12—H12B	109.4
O1—Ni1—N1^i	88.34 (7)	H12A—C12—H12B	108.0
O1^i—Ni1—N1^i	91.66 (7)	C14—C13—C12	108.90 (16)
N1—Ni1—N1^i	180	C14—C13—H13A	109.9
C2—O1—Ni1	131.26 (13)	C12—C13—H13A	109.9
H2C—O2—H2D	110 (2)	C14—C13—H13B	109.9
C11—N1—C12	113.83 (16)	C12—C13—H13B	109.9
C11—N1—Ni1	125.87 (13)	H13A—C13—H13B	108.3
C12—N1—Ni1	120.29 (12)	N2—C14—C13	112.85 (17)
C14—N2—C15	114.14 (15)	N2—C14—H14A	109.0
C14—N2—H2A	108.7	C13—C14—H14A	109.0
C15—N2—H2A	108.7	N2—C14—H14B	109.0
C14—N2—H2B	108.7	C13—C14—H14B	109.0
C15—N2—H2B	108.7	H14A—C14—H14B	107.8
H2A—N2—H2B	107.6	N2—C15—C16	111.49 (16)
C2—C1—C11	119.44 (18)	N2—C15—C20	109.84 (16)
C2—C1—C10	120.37 (18)	C16—C15—C20	110.83 (17)
C11—C1—C10	120.17 (18)	N2—C15—H15	108.2
O1—C2—C1	124.55 (18)	C16—C15—H15	108.2
O1—C2—C3	116.47 (19)	C20—C15—H15	108.2
C1—C2—C3	118.97 (19)	C15—C16—C17	110.03 (18)
C4—C3—C2	120.9 (2)	C15—C16—H16A	109.7
C4—C3—H3	119.5	C17—C16—H16A	109.7
C2—C3—H3	119.5	C15—C16—H16B	109.7
C3—C4—C5	121.9 (2)	C17—C16—H16B	109.7
C3—C4—H4	119.0	H16A—C16—H16B	108.2
C5—C4—H4	119.0	C18—C17—C16	111.9 (2)
C4—C5—C10	119.4 (2)	C18—C17—H17A	109.2
C4—C5—C6	120.9 (2)	C16—C17—H17A	109.2
C10—C5—C6	119.7 (2)	C18—C17—H17B	109.2
C7—C6—C5	120.7 (2)	C16—C17—H17B	109.2
C7—C6—H6	119.7	H17A—C17—H17B	107.9
C5—C6—H6	119.7	C17—C18—C19	110.4 (2)
C6—C7—C8	119.6 (2)	C17—C18—H18A	109.6
C6—C7—H7	120.2	C19—C18—H18A	109.6
C8—C7—H7	120.2	C17—C18—H18B	109.6
C9—C8—C7	121.5 (2)	C19—C18—H18B	109.6
C9—C8—H8	119.3	H18A—C18—H18B	108.1
C7—C8—H8	119.3	C18—C19—C20	111.38 (19)
C8—C9—C10	120.8 (2)	C18—C19—H19A	109.4
C8—C9—H9	119.6	C20—C19—H19A	109.4
C10—C9—H9	119.6	C18—C19—H19B	109.4
C9—C10—C5	117.8 (2)	C20—C19—H19B	109.4
C9—C10—C1	123.84 (19)	H19A—C19—H19B	108.0
C5—C10—C1	118.4 (2)	C15—C20—C19	110.11 (17)
N1—C11—C1	126.96 (18)	C15—C20—H20A	109.6
N1—C11—H11	116.5	C19—C20—H20A	109.6
C1—C11—H11	116.5	C15—C20—H20B	109.6
N1—C12—C13	111.25 (15)	C19—C20—H20B	109.6
N1—C12—H12A	109.4	H20A—C20—H20B	108.2
N1^i—Ni1—O1—C2	175.6 (2)	C4—C5—C10—C1	−1.4 (3)
O1—Ni1—N1—C11	−0.40 (16)	C6—C5—C10—C1	178.6 (2)
O1^i—Ni1—N1—C11	179.60 (16)	C2—C1—C10—C9	−178.1 (2)
O1—Ni1—N1—C12	−179.45 (14)	C11—C1—C10—C9	3.6 (3)
O1^i—Ni1—N1—C12	0.55 (14)	C2—C1—C10—C5	2.0 (3)
Ni1—O1—C2—C1	6.4 (3)	C11—C1—C10—C5	−176.29 (18)
Ni1—O1—C2—C3	−173.31 (17)	C12—N1—C11—C1	−177.51 (17)
C11—C1—C2—O1	−2.6 (3)	Ni1—N1—C11—C1	3.4 (3)
C10—C1—C2—O1	179.08 (19)	C2—C1—C11—N1	−2.3 (3)
C11—C1—C2—C3	177.1 (2)	C10—C1—C11—N1	176.01 (18)
C10—C1—C2—C3	−1.2 (3)	C11—N1—C12—C13	100.0 (2)
O1—C2—C3—C4	179.5 (2)	Ni1—N1—C12—C13	−80.89 (18)
C1—C2—C3—C4	−0.2 (4)	N1—C12—C13—C14	171.35 (18)
C2—C3—C4—C5	0.9 (4)	C15—N2—C14—C13	178.32 (18)
C3—C4—C5—C10	0.0 (4)	C12—C13—C14—N2	−177.53 (18)
C3—C4—C5—C6	180.0 (3)	C14—N2—C15—C16	−65.6 (2)
C4—C5—C6—C7	−179.1 (3)	C14—N2—C15—C20	171.20 (19)
C10—C5—C6—C7	0.9 (4)	N2—C15—C16—C17	−179.95 (19)
C5—C6—C7—C8	−0.4 (4)	C20—C15—C16—C17	−57.3 (2)
C6—C7—C8—C9	0.2 (4)	C15—C16—C17—C18	56.5 (3)
C7—C8—C9—C10	−0.6 (4)	C16—C17—C18—C19	−55.6 (3)
C8—C9—C10—C5	1.1 (3)	C17—C18—C19—C20	55.8 (3)
C8—C9—C10—C1	−178.8 (2)	N2—C15—C20—C19	−178.59 (18)
C4—C5—C10—C9	178.7 (2)	C16—C15—C20—C19	57.8 (2)
C6—C5—C10—C9	−1.3 (3)	C18—C19—C20—C15	−57.1 (3)

Symmetry code: (i) −x+1, −y, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl1^ii	0.90	2.24	3.133 (2)	172
N2—H2B···Cl1^iii	0.90	2.32	3.208 (2)	171
O2—H2C···Cl1	0.83 (1)	2.36 (2)	3.170 (4)	164 (5)
O2—H2D···Cl1^iii	0.84 (1)	2.56 (2)	3.362 (4)	161 (4)

Symmetry codes: (ii) x, y−1, z; (iii) −x+1, y−1/2, −z+3/2.