3-Ethyl-2,6-diphenyl­piperidin-4-ol

In the title mol­ecule, C₁₉H₂₃NO, the piperidine ring adopts a chair conformation. The two phenyl rings, and the hydr­oxy and ethyl groups attached to the piperidine ring, have equatorial orientations. The dihedral angle between the two phenyl rings is 54.5 (1)°. The hydr­oxy and amino H atoms are each disordered over two positions, with approximately equal site occupancies. Inter­molecular O—H...O, O—H...N and N—H...O hydrogen bonds contribute to the stability of the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 160 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.075
• wR factor = 0.193
• Data-to-parameter ratio = 22.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -  >H1B    ...          ?

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C2     = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C3     = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C4     = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C6     = ...          R
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          4

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

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
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   0 ALERT type 5 Informative message, check

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S1. Comment

The conformation of (I) was established by ¹H and ¹³C NMR sepectroscopy by Manimekalai & Rajarajan, 1996; Pandiarajan, et al., 2000. Balamurugan et al., 2006, 2007 have reported crystal structures of di-2-furylpiperidin-4-one derivatives, wherein the piperidine ring adopts a chair and a twist-boat conformations respectively. In the title compound,(I), (Fig. 1), piperidine ring adopts a chair coformation. The hydroxy group in the 4 position, the ethyl group at position 3 and the phenyl rings at positions 2 and 6 have equatorial orientations. The dihedral angle between the two phenyl rings is 54.5 (1)°. The hydroxy and amino H atoms are disordered between two positions each, providing an existence of intermolecular O–H···O, O–H···N and N–H···O hydrogen bonds, which contribute to the stability of crystal packing.

Related literature

The conformation of the title molecule was established by ¹H and ¹³C NMR spectroscopy by Manimekalai & Rajarajan (1996). Pandiarajan et al. (2000) and Balamurugan et al. (2006, 2007) have reported the crystal structures of di-2-furylpiperidin-4-one derivatives, wherein the piperidine ring adopts a chair and a twist-boat conformations, respectively.

S2. Experimental

The title compound was prepared from t(3)-ethyl-r(2),c(6)-diphenylpiperidin-4-one by sodium/alcohol reduction, followed by chromatographic separation over neutral alumina, and its conformation was established by ¹H and ¹³C NMR sepectroscopy (Manimekalai & Rajarajan, 1996; Pandiarajan et al., 2000). The compound was recrystallized from petroleum-ether (333–353 K).

S3. Refinement

The C-bound H atoms were positioned geometrically and allowed to ride on their parent atoms with C—H = 0.95–1.00 Å and U_iso(H) = 1.2–1.5U_eq (parent atom). The H atoms attached to N1 and O4 were treated as disordered between two positions each, with the positions located in a difference map, and refined with bond restraints O—H = 0.85 (4) Å, N—H = 0.86 (4) Å, and with U_iso(H) = 1.5Ueq(N, O). The refined occupancies were 0.48 (4) and 0.52 (4) for atoms H1A and H1B [N1], respectively, and 0.57 (4) and 0.43 (4) for atoms H4A and H4B [O4], respectively.

Computing details

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Figures

	Fig. 1. View of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms attached to N1 and O4 are disordered.
	Fig. 2. The molecular packing of (I), viewed down the a axis, showing the hydrogen bonds (dashed lines).

3-Ethyl-2,6-diphenylpiperidin-4-ol

Crystal data

C19H23NO	F(000) = 608
Mr = 281.38	Dx = 1.202 Mg m^−3
Monoclinic, P21/c	Melting point: 394(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.6611 (3) Å	Cell parameters from 4693 reflections
b = 12.4948 (4) Å	θ = 2.0–30.0°
c = 12.0089 (3) Å	µ = 0.07 mm^−1
β = 117.308 (1)°	T = 160 K
V = 1554.73 (7) Å^3	Needles, colourless
Z = 4	0.25 × 0.23 × 0.08 mm

Data collection

Nonius KappaCCD area-detector diffractometer	3412 reflections with I > 2σ(I)
Radiation source: Nonius FR590 sealed tube generator	Rint = 0.090
Horizontally mounted graphite crystal monochromator	θmax = 30.0°, θmin = 2.5°
Detector resolution: 9 pixels mm^-1	h = −16→16
φ and ω scans with κ offsets	k = −17→17
42996 measured reflections	l = −16→15
4522 independent reflections

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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.193	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ^2(Fo^2) + (0.0635P)^2 + 1.6386P] where P = (Fo^2 + 2Fc^2)/3
4522 reflections	(Δ/σ)max < 0.001
205 parameters	Δρmax = 0.45 e Å^−3
4 restraints	Δρmin = −0.27 e Å^−3

Special details

Experimental. Solvent used: petroleumether/benzene mixture Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.532 (2) Frames collected: 362 Seconds exposure per frame: 80 Degrees rotation per frame: 2.0 Crystal-Detector distance (mm): 30.0

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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)
O4	0.50486 (15)	0.52095 (11)	0.11834 (14)	0.0221 (4)
N1	0.51515 (17)	0.20190 (14)	0.23352 (16)	0.0201 (5)
C2	0.38754 (18)	0.24572 (15)	0.14651 (17)	0.0160 (5)
C3	0.39891 (18)	0.34789 (15)	0.07940 (17)	0.0150 (5)
C4	0.48487 (19)	0.42896 (15)	0.17787 (17)	0.0175 (5)
C5	0.61368 (19)	0.38079 (15)	0.26871 (18)	0.0177 (5)
C6	0.59507 (18)	0.27918 (15)	0.33003 (17)	0.0164 (5)
C21	0.30935 (18)	0.15937 (16)	0.05442 (17)	0.0168 (5)
C22	0.3612 (2)	0.10140 (17)	−0.01094 (19)	0.0209 (6)
C23	0.2893 (2)	0.02414 (19)	−0.0986 (2)	0.0271 (6)
C24	0.1628 (2)	0.00416 (19)	−0.1225 (2)	0.0294 (7)
C25	0.1097 (2)	0.0617 (2)	−0.0590 (2)	0.0288 (6)
C26	0.18262 (19)	0.13811 (18)	0.02957 (19)	0.0225 (6)
C31	0.26640 (19)	0.39729 (18)	−0.00634 (19)	0.0227 (6)
C32	0.2082 (2)	0.3631 (2)	−0.1436 (2)	0.0301 (7)
C61	0.72247 (19)	0.22879 (15)	0.41831 (17)	0.0172 (5)
C62	0.7642 (2)	0.22886 (18)	0.54673 (19)	0.0252 (6)
C63	0.8835 (2)	0.1862 (2)	0.6285 (2)	0.0310 (7)
C64	0.9625 (2)	0.14282 (19)	0.5829 (2)	0.0287 (6)
C65	0.9210 (2)	0.1400 (2)	0.4550 (2)	0.0284 (7)
C66	0.8020 (2)	0.18294 (18)	0.37324 (19)	0.0239 (6)
H1B	0.555 (4)	0.178 (4)	0.194 (4)	0.0302*	0.52 (4)
H2	0.34194	0.26543	0.19666	0.0192*
H3	0.44155	0.32815	0.02657	0.0180*
H4	0.43928	0.45239	0.22678	0.0209*
H4A	0.499 (5)	0.511 (4)	0.045 (3)	0.0331*	0.57 (4)
H5A	0.66340	0.43388	0.33451	0.0211*
H5B	0.66391	0.36334	0.22335	0.0211*
H6	0.54875	0.29914	0.37943	0.0196*
H22	0.44749	0.11495	0.00469	0.0251*
H23	0.32642	−0.01483	−0.14189	0.0326*
H24	0.11311	−0.04866	−0.18203	0.0353*
H25	0.02292	0.04897	−0.07596	0.0345*
H26	0.14553	0.17620	0.07356	0.0271*
H31A	0.20547	0.37772	0.02665	0.0273*
H31B	0.27507	0.47620	−0.00217	0.0273*
H32A	0.26873	0.37997	−0.17687	0.0451*
H32B	0.12698	0.40145	−0.19204	0.0451*
H32C	0.19170	0.28586	−0.14992	0.0451*
H62	0.71058	0.25846	0.57910	0.0303*
H63	0.91086	0.18686	0.71622	0.0371*
H64	1.04482	0.11510	0.63896	0.0344*
H65	0.97405	0.10851	0.42304	0.0342*
H66	0.77455	0.18108	0.28555	0.0287*
H1A	0.508 (5)	0.149 (3)	0.277 (4)	0.0302*	0.48 (4)
H4B	0.500 (6)	0.575 (3)	0.162 (5)	0.0331*	0.43 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O4	0.0360 (9)	0.0117 (7)	0.0198 (7)	−0.0005 (6)	0.0139 (7)	0.0003 (5)
N1	0.0201 (8)	0.0135 (8)	0.0193 (8)	0.0015 (7)	0.0026 (7)	−0.0004 (6)
C2	0.0159 (9)	0.0172 (9)	0.0148 (8)	0.0005 (7)	0.0070 (7)	0.0007 (7)
C3	0.0167 (9)	0.0154 (9)	0.0140 (8)	0.0017 (7)	0.0079 (7)	0.0015 (7)
C4	0.0257 (10)	0.0119 (9)	0.0157 (9)	0.0020 (7)	0.0103 (8)	0.0014 (7)
C5	0.0204 (9)	0.0143 (9)	0.0159 (9)	−0.0020 (7)	0.0063 (8)	−0.0008 (7)
C6	0.0193 (9)	0.0159 (9)	0.0138 (8)	−0.0008 (7)	0.0075 (7)	−0.0007 (7)
C21	0.0173 (9)	0.0164 (9)	0.0156 (9)	−0.0006 (7)	0.0065 (7)	0.0040 (7)
C22	0.0197 (9)	0.0211 (10)	0.0215 (10)	−0.0015 (8)	0.0090 (8)	−0.0005 (8)
C23	0.0286 (11)	0.0278 (12)	0.0225 (10)	−0.0029 (9)	0.0096 (9)	−0.0044 (9)
C24	0.0306 (12)	0.0267 (12)	0.0214 (10)	−0.0096 (9)	0.0038 (9)	−0.0013 (9)
C25	0.0178 (10)	0.0369 (13)	0.0245 (10)	−0.0074 (9)	0.0036 (8)	0.0066 (9)
C26	0.0176 (9)	0.0273 (11)	0.0212 (10)	0.0008 (8)	0.0076 (8)	0.0048 (8)
C31	0.0184 (9)	0.0238 (11)	0.0219 (10)	0.0040 (8)	0.0057 (8)	0.0054 (8)
C32	0.0223 (11)	0.0370 (13)	0.0211 (10)	0.0014 (9)	0.0015 (9)	0.0065 (9)
C61	0.0196 (9)	0.0144 (9)	0.0152 (9)	−0.0032 (7)	0.0059 (7)	0.0000 (7)
C62	0.0290 (11)	0.0275 (11)	0.0156 (9)	0.0040 (9)	0.0072 (8)	−0.0001 (8)
C63	0.0313 (12)	0.0383 (13)	0.0138 (9)	0.0041 (10)	0.0022 (9)	0.0010 (9)
C64	0.0214 (10)	0.0321 (12)	0.0223 (10)	0.0032 (9)	0.0013 (9)	0.0053 (9)
C65	0.0214 (10)	0.0371 (13)	0.0264 (11)	0.0043 (9)	0.0106 (9)	0.0025 (9)
C66	0.0233 (10)	0.0326 (12)	0.0162 (9)	0.0023 (9)	0.0094 (8)	0.0023 (8)

Geometric parameters (Å, º)

O4—C4	1.428 (2)	C63—C64	1.380 (4)
O4—H4A	0.86 (4)	C64—C65	1.383 (3)
O4—H4B	0.87 (5)	C65—C66	1.388 (3)
N1—C6	1.467 (3)	C2—H2	1.0000
N1—C2	1.476 (3)	C3—H3	1.0000
N1—H1A	0.87 (4)	C4—H4	1.0000
N1—H1B	0.86 (5)	C5—H5A	0.9900
C2—C3	1.548 (3)	C5—H5B	0.9900
C2—C21	1.514 (3)	C6—H6	1.0000
C3—C31	1.539 (3)	C22—H22	0.9500
C3—C4	1.530 (3)	C23—H23	0.9500
C4—C5	1.518 (3)	C24—H24	0.9500
C5—C6	1.532 (3)	C25—H25	0.9500
C6—C61	1.511 (3)	C26—H26	0.9500
C21—C26	1.392 (3)	C31—H31A	0.9900
C21—C22	1.394 (3)	C31—H31B	0.9900
C22—C23	1.390 (3)	C32—H32A	0.9800
C23—C24	1.390 (4)	C32—H32B	0.9800
C24—C25	1.384 (3)	C32—H32C	0.9800
C25—C26	1.391 (3)	C62—H62	0.9500
C31—C32	1.528 (3)	C63—H63	0.9500
C61—C62	1.388 (3)	C64—H64	0.9500
C61—C66	1.394 (3)	C65—H65	0.9500
C62—C63	1.389 (3)	C66—H66	0.9500
O4···O4^i	2.841 (2)	H4···H23^vi	2.5900
O4···N1^ii	2.952 (2)	H4···H31B	2.5500
O4···H1A^ii	2.08 (4)	H4···H1A^ii	2.5400
O4···H31B	2.4600	H4···H2	2.5500
O4···H3^i	2.8200	H4A···O4^i	1.98 (4)
O4···H4A^i	1.98 (4)	H4A···C3^i	2.90 (5)
O4···H32A^i	2.7000	H4A···C4^i	2.87 (4)
N1···O4^iii	2.952 (2)	H4A···H3^i	2.4100
N1···H22	2.7100	H4A···C31	2.87 (6)
N1···H66	2.8100	H4A···H3	2.3600
N1···H4B^iii	2.08 (5)	H4A···H31B	2.4400
C21···C32	3.309 (3)	H4A···H4A^i	1.13 (6)
C24···C62^iii	3.560 (3)	H4B···N1^ii	2.08 (5)
C26···C32	3.590 (3)	H4B···C2^ii	2.97 (5)
C26···C31	3.466 (3)	H4B···C61^ii	3.01 (6)
C31···C26	3.466 (3)	H4B···H1B^ii	2.47 (8)
C32···C21	3.309 (3)	H4B···C6^ii	2.80 (5)
C32···C26	3.590 (3)	H5A···C21^ii	3.0700
C62···C24^ii	3.560 (3)	H5A···C22^ii	3.0800
C2···H4B^iii	2.97 (5)	H5B···C66	2.8700
C3···H4A^i	2.90 (5)	H5B···H1B	2.5900
C4···H1A^ii	2.80 (4)	H5B···H66	2.5500
C4···H4A^i	2.87 (4)	H5B···C62^viii	3.0800
C5···H66	3.0700	H5B···H62^viii	2.5500
C6···H4B^iii	2.80 (5)	H6···H4	2.5500
C21···H5A^iii	3.0700	H6···H62	2.3300
C21···H32C	2.7000	H6···H22^vi	2.5400
C21···H31A	2.9400	H6···H2	2.4400
C22···H32C	3.0000	H22···H1B	2.1800
C22···H3	2.9500	H22···H6^viii	2.5400
C22···H5A^iii	3.0800	H22···N1	2.7100
C22···H1B	2.64 (5)	H23···H4^viii	2.5900
C24···H64^iv	2.9000	H24···H32B^ix	2.5700
C25···H25^v	3.0400	H25···C25^v	3.0400
C25···H63^iv	3.0600	H25···H25^v	2.4500
C26···H32C	2.8800	H26···H2	2.3600
C26···H31A	3.0100	H31A···C65^x	3.0300
C31···H4A	2.87 (6)	H31A···C21	2.9400
C61···H4B^iii	3.01 (6)	H31A···C26	3.0100
C62···H5B^vi	3.0800	H31A···H65^x	2.4000
C62···H66^vi	3.0300	H31A···H2	2.3800
C65···H31A^vii	3.0300	H31B···H4	2.5500
C66···H1B	2.69 (5)	H31B···H4A	2.4400
C66···H5B	2.8700	H31B···O4	2.4600
H1A···O4^iii	2.08 (4)	H32A···O4^i	2.7000
H1A···C4^iii	2.80 (4)	H32A···H3	2.4400
H1A···H4^iii	2.5400	H32B···H24^xi	2.5700
H1B···C22	2.64 (5)	H32C···C21	2.7000
H1B···C66	2.69 (5)	H32C···C22	3.0000
H1B···H5B	2.5900	H32C···C26	2.8800
H1B···H4B^iii	2.47 (8)	H62···H6	2.3300
H1B···H22	2.1800	H62···H5B^vi	2.5500
H1B···H66	2.2800	H62···H66^vi	2.3600
H2···H4	2.5500	H63···C25^xii	3.0600
H2···H6	2.4400	H64···C24^xii	2.9000
H2···H26	2.3600	H65···H31A^vii	2.4000
H2···H31A	2.3800	H66···C5	3.0700
H3···O4^i	2.8200	H66···H1B	2.2800
H3···H4A^i	2.4100	H66···N1	2.8100
H3···H32A	2.4400	H66···C62^viii	3.0300
H3···C22	2.9500	H66···H62^viii	2.3600
H3···H4A	2.3600	H66···H5B	2.5500
H4···H6	2.5500
C4—O4—H4A	116 (3)	O4—C4—H4	108.00
C4—O4—H4B	105 (4)	C3—C4—H4	108.00
C2—N1—C6	112.56 (16)	C5—C4—H4	108.00
C2—N1—H1A	111 (4)	C4—C5—H5A	109.00
C6—N1—H1B	111 (3)	C4—C5—H5B	109.00
C6—N1—H1A	103 (3)	C6—C5—H5A	109.00
C2—N1—H1B	111 (3)	C6—C5—H5B	109.00
N1—C2—C3	112.04 (18)	H5A—C5—H5B	108.00
N1—C2—C21	109.05 (16)	N1—C6—H6	108.00
C3—C2—C21	111.97 (15)	C5—C6—H6	108.00
C2—C3—C31	112.31 (18)	C61—C6—H6	108.00
C4—C3—C31	110.62 (16)	C21—C22—H22	119.00
C2—C3—C4	109.02 (15)	C23—C22—H22	119.00
O4—C4—C5	110.11 (18)	C22—C23—H23	120.00
O4—C4—C3	110.21 (15)	C24—C23—H23	120.00
C3—C4—C5	111.98 (16)	C23—C24—H24	120.00
C4—C5—C6	111.24 (18)	C25—C24—H24	120.00
N1—C6—C5	110.14 (15)	C24—C25—H25	120.00
N1—C6—C61	110.11 (16)	C26—C25—H25	120.00
C5—C6—C61	111.84 (18)	C21—C26—H26	120.00
C2—C21—C26	121.11 (19)	C25—C26—H26	120.00
C2—C21—C22	120.7 (2)	C3—C31—H31A	109.00
C22—C21—C26	118.18 (19)	C3—C31—H31B	109.00
C21—C22—C23	121.4 (2)	C32—C31—H31A	109.00
C22—C23—C24	119.7 (2)	C32—C31—H31B	109.00
C23—C24—C25	119.6 (2)	H31A—C31—H31B	108.00
C24—C25—C26	120.4 (2)	C31—C32—H32A	109.00
C21—C26—C25	120.7 (2)	C31—C32—H32B	110.00
C3—C31—C32	114.99 (19)	C31—C32—H32C	109.00
C6—C61—C62	120.7 (2)	H32A—C32—H32B	109.00
C6—C61—C66	120.95 (17)	H32A—C32—H32C	109.00
C62—C61—C66	118.4 (2)	H32B—C32—H32C	109.00
C61—C62—C63	120.8 (2)	C61—C62—H62	120.00
C62—C63—C64	120.3 (2)	C63—C62—H62	120.00
C63—C64—C65	119.6 (2)	C62—C63—H63	120.00
C64—C65—C66	120.2 (2)	C64—C63—H63	120.00
C61—C66—C65	120.77 (19)	C63—C64—H64	120.00
N1—C2—H2	108.00	C65—C64—H64	120.00
C3—C2—H2	108.00	C64—C65—H65	120.00
C21—C2—H2	108.00	C66—C65—H65	120.00
C2—C3—H3	108.00	C61—C66—H66	120.00
C4—C3—H3	108.00	C65—C66—H66	120.00
C31—C3—H3	108.00
C6—N1—C2—C3	58.2 (2)	C4—C5—C6—N1	55.8 (2)
C6—N1—C2—C21	−177.24 (17)	N1—C6—C61—C62	−126.0 (2)
C2—N1—C6—C5	−57.9 (2)	N1—C6—C61—C66	55.2 (3)
C2—N1—C6—C61	178.29 (17)	C5—C6—C61—C62	111.2 (2)
C21—C2—C3—C4	−176.98 (18)	C5—C6—C61—C66	−67.6 (2)
N1—C2—C3—C4	−54.1 (2)	C2—C21—C22—C23	−178.01 (19)
N1—C2—C3—C31	−177.06 (16)	C26—C21—C22—C23	−0.1 (3)
N1—C2—C21—C26	131.7 (2)	C2—C21—C26—C25	177.32 (19)
C3—C2—C21—C22	74.1 (2)	C22—C21—C26—C25	−0.6 (3)
C3—C2—C21—C26	−103.7 (2)	C21—C22—C23—C24	0.3 (3)
C21—C2—C3—C31	60.1 (2)	C22—C23—C24—C25	0.2 (3)
N1—C2—C21—C22	−50.5 (2)	C23—C24—C25—C26	−0.9 (3)
C31—C3—C4—O4	−60.3 (2)	C24—C25—C26—C21	1.1 (3)
C2—C3—C4—O4	175.72 (18)	C6—C61—C62—C63	−177.6 (2)
C2—C3—C4—C5	52.8 (2)	C66—C61—C62—C63	1.3 (3)
C4—C3—C31—C32	143.22 (19)	C6—C61—C66—C65	177.8 (2)
C31—C3—C4—C5	176.75 (18)	C62—C61—C66—C65	−1.1 (3)
C2—C3—C31—C32	−94.7 (2)	C61—C62—C63—C64	−0.1 (4)
O4—C4—C5—C6	−177.68 (15)	C62—C63—C64—C65	−1.4 (4)
C3—C4—C5—C6	−54.7 (2)	C63—C64—C65—C66	1.6 (4)
C4—C5—C6—C61	178.59 (16)	C64—C65—C66—C61	−0.4 (4)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+1, y−1/2, −z+1/2; (iv) x−1, y, z−1; (v) −x, −y, −z; (vi) x, −y+1/2, z+1/2; (vii) x+1, −y+1/2, z+1/2; (viii) x, −y+1/2, z−1/2; (ix) −x, y−1/2, −z−1/2; (x) x−1, −y+1/2, z−1/2; (xi) −x, y+1/2, −z−1/2; (xii) x+1, y, z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O4^i	0.86 (4)	1.98 (4)	2.841 (2)	176 (4)
O4—H4B···N1^ii	0.87 (6)	2.08 (6)	2.952 (3)	179 (4)
N1—H1A···O4^iii	0.89 (5)	2.09 (5)	2.952 (3)	179 (4)

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