Chloral adduct of N-hydroxy­piperidine

The title compound, N-(2,2,2–tri­chloro-1-hydroxy­ethoxy)­piperidine, C₇H₁₂Cl_3­NO₂, contains a six-membered piperidine ring with a chair conformation. The triclinic unit cell contains two independent pairs of mol­ecules, with the mol­ecules in each pair linked about centres of symmetry by O—H...N hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.043
• wR factor = 0.046
• Data-to-parameter ratio = 11.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1992); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: TEXSAN; software used to prepare material for publication: TEXSAN.

(I)

Crystal data

C7H12Cl3NO2	Z = 4
Mr = 248.54	F(000) = 512
Triclinic, P1	Dx = 1.509 Mg m^−3
a = 10.409 (1) Å	Cu Kα radiation, λ = 1.54178 Å
b = 11.922 (2) Å	Cell parameters from 25 reflections
c = 10.291 (1) Å	θ = 39.6–45.4°
α = 109.78 (1)°	µ = 7.37 mm^−1
β = 94.96 (1)°	T = 294 K
γ = 110.61 (1)°	Block, colourless
V = 1093.8 (3) Å^3	0.40 × 0.35 × 0.30 mm

Data collection

Rigaku AFC-6S diffractometer	2810 reflections with I > 3σ(I)
Radiation source: X-ray tube	Rint = 0.044
Graphite monochromator	θmax = 77.5°, θmin = 0.0°
ω–2θ scans	h = 0→13
Absorption correction: ψ scan (Molecular Structure Corporation, 1992)	k = −14→14
Tmin = 0.076, Tmax = 0.110	l = −12→11
4696 measured reflections	3 standard reflections every 200 reflections
4443 independent reflections	intensity decay: none

Refinement

Refinement on F	0 constraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.043	Weighting scheme based on measured s.u.'s w = 1/σ^2(Fo)
wR(F^2) = 0.046	(Δ/σ)max = 0.0003
S = 1.95	Δρmax = 0.24 e Å^−3
2810 reflections	Δρmin = −0.21 e Å^−3
244 parameters	Extinction correction: Zachariasen (1968), equ(3) Acta Cryst. (1968), A24, p. 213.
0 restraints	Extinction coefficient: 7.2 (4)E-6

Special details

Experimental. The scan width was (0.94 + 0.20tanθ)° with an ω scan speed of 32° per minute (up to 10 scans to achieve I/σ(I) > 40). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

Refinement. H1, H2 refined isotropically (xyzB), other H fixed in calculated sites (H-atom parameters not refined).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.1085 (1)	0.5452 (1)	−0.3419 (1)	0.0707 (4)
Cl2	0.2095 (1)	0.3514 (1)	−0.3397 (1)	0.0646 (4)
Cl3	0.3800 (1)	0.6238 (1)	−0.1717 (1)	0.0746 (4)
Cl4	0.3524 (1)	0.1530 (1)	0.2940 (1)	0.0704 (4)
Cl5	0.3474 (1)	−0.0558 (1)	0.3733 (1)	0.0786 (4)
Cl6	0.1819 (1)	−0.1129 (1)	0.1045 (1)	0.0764 (4)
O1	0.2200 (3)	0.4525 (3)	−0.0350 (2)	0.0552 (8)
O2	0.0007 (3)	0.4033 (3)	−0.1563 (3)	0.0566 (9)
O3	0.0503 (2)	0.0503 (3)	0.2801 (3)	0.0553 (8)
O4	0.1674 (3)	0.0798 (3)	0.4951 (3)	0.0557 (9)
N1	0.2154 (3)	0.4968 (3)	0.1156 (3)	0.0471 (9)
N2	−0.0965 (3)	0.0119 (3)	0.2911 (3)	0.0453 (9)
C1	0.2081 (4)	0.3846 (4)	0.1506 (4)	0.0562 (13)
C2	0.2263 (4)	0.4217 (4)	0.3095 (4)	0.0621 (13)
C3	0.3628 (4)	0.5381 (5)	0.3923 (4)	0.0671 (13)
C4	0.3708 (5)	0.6491 (4)	0.3479 (4)	0.0722 (13)
C5	0.3527 (4)	0.6072 (4)	0.1900 (4)	0.0593 (13)
C6	0.1388 (4)	0.4933 (3)	−0.1085 (4)	0.0453 (10)
C7	0.2071 (3)	0.5002 (4)	−0.2350 (4)	0.0483 (11)
C8	−0.1256 (4)	0.1243 (4)	0.2937 (4)	0.0621 (13)
C9	−0.2828 (5)	0.0929 (5)	0.2853 (5)	0.0760 (13)
C10	−0.3732 (4)	−0.0294 (6)	0.1557 (5)	0.0848 (13)
C11	−0.3331 (4)	−0.1389 (5)	0.1541 (5)	0.0798 (13)
C12	−0.1776 (4)	−0.1014 (4)	0.1597 (4)	0.0613 (13)
C13	0.1194 (3)	−0.0003 (3)	0.3532 (4)	0.0461 (10)
C14	0.2446 (4)	−0.0023 (4)	0.2843 (4)	0.0465 (10)
H1	−0.048 (4)	0.446 (4)	−0.148 (4)	0.063 (13)*
H2	0.142 (5)	0.040 (5)	0.543 (5)	0.101 (13)*
H3	0.2832	0.3581	0.1200	0.067*
H4	0.1161	0.3118	0.1011	0.067*
H5	0.2257	0.3475	0.3309	0.073*
H6	0.1474	0.4427	0.3383	0.073*
H7	0.4426	0.5150	0.3725	0.081*
H8	0.3660	0.5653	0.4941	0.081*
H9	0.4631	0.7221	0.3954	0.087*
H10	0.2961	0.6772	0.3763	0.087*
H11	0.3573	0.6805	0.1646	0.071*
H12	0.4284	0.5807	0.1615	0.071*
H13	0.1447	0.5793	−0.0482	0.054*
H14	−0.0698	0.1997	0.3821	0.075*
H15	−0.0999	0.1448	0.2125	0.075*
H16	−0.3064	0.0798	0.3708	0.091*
H17	−0.3021	0.1662	0.2799	0.091*
H18	−0.4729	−0.0533	0.1585	0.101*
H19	−0.3586	−0.0133	0.0698	0.101*
H20	−0.3543	−0.1591	0.2366	0.096*
H21	−0.3876	−0.2161	0.0668	0.096*
H22	−0.1555	−0.0800	0.0782	0.073*
H23	−0.1535	−0.1744	0.1571	0.073*
H24	0.0566	−0.0888	0.3399	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0691 (7)	0.1014 (9)	0.0654 (7)	0.0438 (6)	0.0143 (5)	0.0512 (7)
Cl2	0.0783 (7)	0.0685 (7)	0.0532 (6)	0.0354 (6)	0.0221 (5)	0.0235 (5)
Cl3	0.0457 (5)	0.0854 (8)	0.0716 (7)	0.0032 (5)	0.0087 (5)	0.0319 (6)
Cl4	0.0494 (6)	0.0676 (7)	0.0923 (8)	0.0096 (5)	0.0187 (5)	0.0431 (6)
Cl5	0.0744 (7)	0.121 (1)	0.0880 (8)	0.0636 (7)	0.0329 (6)	0.0675 (8)
Cl6	0.0794 (8)	0.0818 (8)	0.0519 (6)	0.0197 (6)	0.0191 (5)	0.0200 (6)
O1	0.062 (2)	0.074 (2)	0.042 (1)	0.037 (1)	0.012 (1)	0.027 (1)
O2	0.041 (1)	0.060 (2)	0.066 (2)	0.014 (1)	0.013 (1)	0.028 (1)
O3	0.036 (1)	0.073 (2)	0.071 (2)	0.020 (1)	0.013 (1)	0.047 (2)
O4	0.059 (2)	0.056 (2)	0.048 (2)	0.018 (1)	0.012 (1)	0.022 (1)
N1	0.047 (2)	0.057 (2)	0.038 (2)	0.019 (2)	0.007 (1)	0.021 (2)
N2	0.032 (1)	0.053 (2)	0.048 (2)	0.011 (1)	0.007 (1)	0.024 (2)
C1	0.058 (2)	0.056 (3)	0.056 (2)	0.021 (2)	0.009 (2)	0.026 (2)
C2	0.073 (3)	0.072 (3)	0.058 (3)	0.034 (2)	0.019 (2)	0.040 (2)
C3	0.067 (3)	0.091 (3)	0.049 (2)	0.035 (3)	0.006 (2)	0.033 (2)
C4	0.078 (3)	0.069 (3)	0.051 (3)	0.013 (2)	−0.005 (2)	0.021 (2)
C5	0.058 (2)	0.059 (3)	0.053 (2)	0.012 (2)	0.005 (2)	0.028 (2)
C6	0.044 (2)	0.054 (2)	0.039 (2)	0.020 (2)	0.007 (2)	0.021 (2)
C7	0.039 (2)	0.057 (2)	0.048 (2)	0.017 (2)	0.002 (2)	0.025 (2)
C8	0.058 (2)	0.068 (3)	0.074 (3)	0.028 (2)	0.015 (2)	0.040 (2)
C9	0.062 (3)	0.106 (4)	0.100 (4)	0.048 (3)	0.033 (3)	0.068 (3)
C10	0.042 (2)	0.152 (5)	0.076 (3)	0.035 (3)	0.016 (2)	0.069 (4)
C11	0.045 (2)	0.096 (4)	0.066 (3)	0.004 (2)	−0.001 (2)	0.023 (3)
C12	0.050 (2)	0.069 (3)	0.050 (2)	0.015 (2)	0.004 (2)	0.019 (2)
C13	0.039 (2)	0.047 (2)	0.049 (2)	0.012 (2)	0.006 (2)	0.023 (2)
C14	0.043 (2)	0.057 (2)	0.044 (2)	0.020 (2)	0.011 (2)	0.025 (2)

Geometric parameters (Å, º)

Cl1—C7	1.773 (3)	C3—H7	0.98
Cl2—C7	1.747 (4)	C3—H8	0.98
Cl3—C7	1.765 (3)	C4—C5	1.502 (6)
Cl4—C14	1.758 (4)	C4—H9	0.98
Cl5—C14	1.760 (3)	C4—H10	0.98
Cl6—C14	1.767 (4)	C5—H11	0.98
O1—N1	1.470 (3)	C5—H12	0.98
O1—C6	1.397 (4)	C6—C7	1.549 (6)
O2—C6	1.376 (4)	C6—H13	0.98
O2—H1	0.83 (5)	C8—C9	1.532 (6)
O3—N2	1.459 (4)	C8—H14	0.98
O3—C13	1.402 (6)	C8—H15	0.98
O4—C13	1.374 (4)	C9—C10	1.514 (6)
O4—H2	0.79 (6)	C9—H16	0.98
N1—C1	1.478 (4)	C9—H17	0.98
N1—C5	1.472 (4)	C10—C11	1.500 (7)
N2—C8	1.467 (4)	C10—H18	0.98
N2—C12	1.459 (4)	C10—H19	0.98
C1—C2	1.518 (6)	C11—C12	1.510 (6)
C1—H3	0.98	C11—H20	0.98
C1—H4	0.98	C11—H21	0.98
C2—C3	1.508 (5)	C12—H22	0.98
C2—H5	0.98	C12—H23	0.98
C2—H6	0.98	C13—C14	1.540 (6)
C3—C4	1.518 (6)	C13—H24	0.98
Cl1···Cl1^i	3.390 (2)	O2···C6^vi	3.275 (5)
Cl2···O4^ii	2.952 (3)	O4···N2^vii	2.815 (5)
Cl5···Cl5^iii	3.451 (2)	O4···O4^vii	3.361 (6)
Cl5···C4^iv	3.535 (5)	O4···C12^vii	3.463 (5)
Cl6···O2^v	3.560 (4)	O4···C13^vii	3.473 (5)
O2···N1^vi	2.892 (5)	O4···C11^vii	3.585 (6)
O2···O2^vi	3.268 (6)
N1—O1—C6	110.5 (3)	Cl1—C7—Cl3	107.1 (3)
C6—O2—H1	106 (2)	Cl1—C7—C6	108.3 (3)
N2—O3—C13	110.4 (3)	Cl2—C7—Cl3	110.2 (2)
C13—O4—H2	111 (3)	Cl2—C7—C6	112.5 (3)
O1—N1—C1	103.2 (3)	Cl3—C7—C6	109.8 (2)
O1—N1—C5	104.9 (3)	N2—C8—C9	110.0 (4)
C1—N1—C5	109.9 (3)	N2—C8—H14	109.4
O3—N2—C8	103.1 (3)	N2—C8—H15	109.4
O3—N2—C12	105.4 (3)	C9—C8—H14	109.3
C8—N2—C12	110.4 (3)	C9—C8—H15	109.3
N1—C1—C2	110.2 (3)	H14—C8—H15	109.5
N1—C1—H3	109.3	C8—C9—C10	111.0 (4)
N1—C1—H4	109.3	C8—C9—H16	109.1
C2—C1—H3	109.3	C8—C9—H17	109.1
C2—C1—H4	109.3	C10—C9—H16	109.1
H3—C1—H4	109.5	C10—C9—H17	109.1
C1—C2—C3	111.9 (4)	H16—C9—H17	109.5
C1—C2—H5	108.9	C9—C10—C11	109.7 (4)
C1—C2—H6	108.8	C9—C10—H18	109.5
C3—C2—H5	108.9	C9—C10—H19	109.5
C3—C2—H6	108.9	C11—C10—H18	109.4
H5—C2—H6	109.5	C11—C10—H19	109.4
C2—C3—C4	109.0 (4)	H18—C10—H19	109.4
C2—C3—H7	109.6	C10—C11—C12	110.6 (4)
C2—C3—H8	109.6	C10—C11—H20	109.3
C4—C3—H7	109.6	C10—C11—H21	109.2
C4—C3—H8	109.5	C12—C11—H20	109.1
H7—C3—H8	109.6	C12—C11—H21	109.1
C3—C4—C5	111.1 (3)	H20—C11—H21	109.4
C3—C4—H9	109.0	N2—C12—C11	109.1 (3)
C3—C4—H10	109.1	N2—C12—H22	109.6
C5—C4—H9	109.0	N2—C12—H23	109.5
C5—C4—H10	109.1	C11—C12—H22	109.6
H9—C4—H10	109.5	C11—C12—H23	109.6
N1—C5—C4	110.3 (3)	H22—C12—H23	109.5
N1—C5—H11	109.3	O3—C13—O4	110.6 (3)
N1—C5—H12	109.3	O3—C13—C14	104.0 (3)
C4—C5—H11	109.2	O3—C13—H24	110.6
C4—C5—H12	109.3	O4—C13—C14	110.3 (2)
H11—C5—H12	109.5	O4—C13—H24	110.6
O1—C6—O2	110.3 (3)	C14—C13—H24	110.6
O1—C6—C7	103.7 (3)	Cl4—C14—Cl5	108.6 (2)
O1—C6—H13	110.6	Cl4—C14—Cl6	109.2 (3)
O2—C6—C7	110.6 (3)	Cl4—C14—C13	111.9 (3)
O2—C6—H13	110.7	Cl5—C14—Cl6	108.2 (3)
C7—C6—H13	110.7	Cl5—C14—C13	108.9 (3)
Cl1—C7—Cl2	108.8 (2)	Cl6—C14—C13	110.0 (2)
Cl1—C7—C6—O1	177.7 (2)	N1—O1—C6—C7	154.0 (2)
Cl1—C7—C6—O2	59.4 (4)	N1—C1—C2—C3	−56.9 (5)
Cl2—C7—C6—O1	57.5 (3)	N1—C5—C4—C3	59.3 (5)
Cl2—C7—C6—O2	−60.8 (4)	N2—O3—C13—C14	157.6 (2)
Cl3—C7—C6—O1	−65.6 (3)	N2—C8—C9—C10	−55.5 (6)
Cl3—C7—C6—O2	176.1 (3)	N2—C12—C11—C10	61.0 (5)
Cl4—C14—C13—O3	56.7 (3)	C1—N1—O1—C6	140.8 (3)
Cl4—C14—C13—O4	−61.9 (4)	C1—N1—C5—C4	−61.1 (5)
Cl5—C14—C13—O3	176.8 (2)	C1—C2—C3—C4	53.8 (5)
Cl5—C14—C13—O4	58.2 (4)	C2—C1—N1—C5	59.5 (4)
Cl6—C14—C13—O3	−64.9 (3)	C2—C3—C4—C5	−54.9 (5)
Cl6—C14—C13—O4	176.5 (3)	C5—N1—O1—C6	−104.2 (4)
O1—N1—C1—C2	170.9 (3)	C8—N2—O3—C13	146.5 (3)
O1—N1—C5—C4	−171.4 (4)	C8—N2—C12—C11	−63.0 (5)
O2—C6—O1—N1	−87.5 (3)	C8—C9—C10—C11	53.4 (6)
O3—N2—C8—C9	172.5 (3)	C9—C8—N2—C12	60.4 (4)
O3—N2—C12—C11	−173.6 (4)	C9—C10—C11—C12	−56.1 (5)
O4—C13—O3—N2	−84.0 (3)	C12—N2—O3—C13	−97.8 (4)

Symmetry codes: (i) −x, −y+1, −z−1; (ii) x, y, z−1; (iii) −x+1, −y, −z+1; (iv) x, y−1, z; (v) −x, −y, −z; (vi) −x, −y+1, −z; (vii) −x, −y, −z+1.