t-3-Benzyl-r-2,c-6-di-2-furylpiperidin-4-one

In the title mol­ecule, C₂₀H₁₉NO₃, the piperidine ring adopts a chair conformation. The phenyl and furyl rings have equatorial orientations. Mol­ecules are linked by C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 160 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.071
• wR factor = 0.226
• Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT220_ALERT_2_A Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       5.82 Ratio

Author Response: ... atom disorder

PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...      10.00 Ratio

Author Response: ... atom disorder

PLAT241_ALERT_2_A Check High      Ueq as Compared to Neighbors for        C64

Author Response: ... atom disorder

Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        O62

Author Response: ... atom disorder

PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C63
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for       C65A
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for       C65B
PLAT366_ALERT_2_B Short? C(sp?)-C(sp?) Bond  C63    -   C64    ...       1.28 Ang.
PLAT411_ALERT_2_B Short Inter H...H Contact  H6     ..  H65A    ..       2.05 Ang.
PLAT415_ALERT_2_B Short Inter D-H..H-X       H1     ..  H65B    ..       1.98 Ang.

Alert level C
PLAT153_ALERT_1_C The su's on the Cell Axes   are Equal (x 100000)        500 Ang.
PLAT301_ALERT_3_C Main Residue  Disorder .........................       4.00 Perc.
PLAT353_ALERT_3_C Long    N-H Bond (0.87A)   N1     -   H1     ...       1.02 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1     ...          ?

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C2     = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C3     = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C6     = ...          S

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  10 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

Piperidine heterocycles play an important role in the field of medicinal Chemistry (Balamurugan et al., 2006,2007). In the title compound, (I), N1 shows a pyramidal geometry (Fig. 1). The piperidine ring adopts a chair conformation. The phenyl group at C3 and the furyl rings at C2 and C6 are in equatorial positions. In the solid state, the symmetry-related molecules are linked by C23—H23···O4 (x + 1, -y + 1/2, z - 1/2) hydrogen bonds to form chains along the c axis (Fig. 2).

Related literature

For related literature, see: Balamurugan et al. (2006, 2007).

S2. Experimental

A mixture of ammonium acetate (38.5 g, 0.5 mol), furfuraldehyde (82.84 ml, 1 mol) and benzyl acetone (38.5 ml, 0.5 mol) in distilled ethanol was heated first to boiling. After cooling, the viscous liquid obtained was dissolved in ether (200 ml) and shaken with 10 ml of concentrated hydrochloric acid. The precipitated hydrochloride of 3-benzyl-2,6-di-furylpiperidin-4-one was removed by filtration and washed first with 40 ml mixture of ethanol and ether (1:1) and then with ether to remove most of the coloured impurities. The base was liberated from an alcoholic solution by adding aqueous ammonia and then diluted with water. It was recrystallized from mixture of petroleum ether. The yield of the compound was 70%.

S3. Refinement

Atom H1 at N1 was located in a difference Fourier map and refined isotropically. Remaining H atoms were positioned geometrically and allowed to ride on their parent atoms with C–H = 0.93–1.00 Å and U_iso = 1.2U_eq(parent atom). The furyl ring at position 6 is disordered. The site occupancy of the two atom positions C65A and C65B were refined (0.604:0.396).

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.
	Fig. 2. The molecular packing of (I), viewed down the a axis showing the C–H···O(dashed lines) interactions.

t-3-Benzyl-r-2,c-6-di-2-furylpiperidin-4-one

Crystal data

C20H19NO3	F(000) = 680
Mr = 321.36	Dx = 1.297 Mg m^−3
Monoclinic, P21/c	Melting point: 463 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.443 (5) Å	Cell parameters from 3346 reflections
b = 21.437 (5) Å	θ = 2.0–26.0°
c = 14.108 (5) Å	µ = 0.09 mm^−1
β = 91.037 (5)°	T = 160 K
V = 1645.9 (17) Å^3	Platelike, light-brown
Z = 4	0.25 × 0.25 × 0.13 mm

Data collection

Nonius KappaCCD area-detector diffractometer	2182 reflections with I > 2σ(I)
Radiation source: Nonius FR590 sealed tube generator	Rint = 0.086
Horizontally mounted graphite crystal monochromator	θmax = 26.0°, θmin = 2.4°
Detector resolution: 9 pixels mm^-1	h = −6→6
φ and ω scans with κ offsets	k = −26→26
30100 measured reflections	l = −17→17
3254 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.071	H-atom parameters constrained
wR(F^2) = 0.226	w = 1/[σ^2(Fo^2) + (0.1215P)^2 + 1.0322P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
3254 reflections	Δρmax = 0.49 e Å^−3
225 parameters	Δρmin = −0.50 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.040 (6)

Special details

Experimental. Solvent used: petroleum ether Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.421 (1) Frames collected: 637 Seconds exposure per frame: 15 Degrees rotation per frame: 1.0 Crystal-Detector distance (mm): 35.0

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	−0.3321 (4)	0.26535 (11)	0.53493 (16)	0.0545 (9)
O22	0.2807 (3)	0.31977 (9)	0.25411 (13)	0.0342 (7)
O62	0.4497 (5)	0.40526 (14)	0.6315 (2)	0.0796 (11)
N1	0.1558 (4)	0.38238 (11)	0.43396 (16)	0.0326 (8)
C2	−0.0170 (5)	0.34803 (13)	0.37281 (19)	0.0309 (9)
C3	−0.0465 (5)	0.27982 (13)	0.40998 (19)	0.0318 (9)
C4	−0.1353 (6)	0.28604 (14)	0.5105 (2)	0.0384 (10)
C5	0.0277 (6)	0.32360 (15)	0.5754 (2)	0.0437 (10)
C6	0.0689 (5)	0.38847 (14)	0.53178 (19)	0.0337 (9)
C21	0.0650 (5)	0.34981 (13)	0.27285 (19)	0.0290 (8)
C23	0.3166 (5)	0.32621 (14)	0.1585 (2)	0.0348 (9)
C24	0.1344 (5)	0.35883 (14)	0.11844 (19)	0.0350 (9)
C25	−0.0293 (5)	0.37395 (14)	0.1926 (2)	0.0359 (10)
C31	−0.2129 (5)	0.23934 (14)	0.3473 (2)	0.0351 (9)
C61	0.2441 (5)	0.42625 (17)	0.5899 (2)	0.0410 (12)
C63	0.5666 (6)	0.45457 (16)	0.6754 (2)	0.0424 (10)
C64	0.4392 (7)	0.50353 (18)	0.6585 (4)	0.085 (2)
C65A	0.2486 (2)	0.48141 (5)	0.57868 (8)	0.0265 (17)	0.604 (11)
C311	−0.1902 (2)	0.17066 (5)	0.36974 (8)	0.0291 (8)
C312	0.0109 (2)	0.13637 (5)	0.33918 (8)	0.0325 (9)
C313	0.0333 (2)	0.07361 (5)	0.35848 (8)	0.0387 (10)
C314	−0.1458 (2)	0.04334 (5)	0.40948 (8)	0.0424 (11)
C315	−0.3433 (2)	0.07662 (5)	0.44198 (8)	0.0419 (11)
C316	−0.3665 (2)	0.13937 (5)	0.42228 (8)	0.0360 (9)
C65B	0.2195 (2)	0.49251 (5)	0.62338 (8)	0.0146 (19)	0.396 (11)
H1	0.19817	0.42561	0.40918	0.14 (2)*
H3	0.12038	0.25992	0.41242	0.043 (8)*
H5A	−0.04851	0.32791	0.63815	0.042 (8)*
H2	−0.18116	0.36889	0.37523	0.026 (7)*
H6	−0.09249	0.41072	0.52994	0.046 (9)*
H23	0.45350	0.30988	0.12556	0.060 (10)*
H24	0.11708	0.36973	0.05344	0.041 (9)*
H25	−0.17804	0.39655	0.18610	0.055 (10)*
H31A	−0.17119	0.24592	0.28005	0.044 (9)*
H31B	−0.38559	0.25222	0.35555	0.038 (8)*
H63	0.71196	0.45263	0.71091	0.0511*
H64	0.45432	0.54271	0.68633	0.1024*
H65A	0.16234	0.50540	0.53437	0.29 (9)*	0.604 (11)
H312	0.13517	0.15671	0.30425	0.044 (9)*
H313	0.17167	0.05110	0.33673	0.049 (9)*
H314	−0.13247	−0.00008	0.42201	0.050 (10)*
H315	−0.46468	0.05620	0.47832	0.053 (10)*
H316	−0.50465	0.16163	0.44485	0.045 (9)*
H5B	0.18809	0.30210	0.58442	0.054 (10)*
H65B	0.08362	0.51877	0.61995	0.019 (16)*	0.396 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O4	0.0649 (16)	0.0520 (14)	0.0476 (15)	−0.0018 (12)	0.0306 (12)	0.0033 (11)
O22	0.0327 (11)	0.0453 (12)	0.0247 (11)	0.0100 (9)	0.0041 (8)	0.0015 (9)
O62	0.0713 (19)	0.0724 (19)	0.094 (2)	0.0224 (15)	−0.0269 (16)	−0.0344 (16)
N1	0.0429 (14)	0.0321 (13)	0.0230 (12)	0.0010 (10)	0.0083 (10)	0.0038 (10)
C2	0.0322 (15)	0.0348 (16)	0.0259 (15)	0.0072 (12)	0.0064 (12)	0.0055 (12)
C3	0.0361 (15)	0.0335 (15)	0.0261 (15)	0.0085 (12)	0.0056 (12)	0.0072 (12)
C4	0.0517 (19)	0.0335 (16)	0.0305 (17)	0.0105 (14)	0.0155 (14)	0.0087 (13)
C5	0.065 (2)	0.0458 (19)	0.0206 (15)	0.0083 (16)	0.0096 (14)	0.0061 (13)
C6	0.0369 (16)	0.0420 (17)	0.0225 (15)	0.0067 (13)	0.0059 (12)	0.0040 (12)
C21	0.0281 (14)	0.0330 (15)	0.0262 (15)	0.0054 (11)	0.0072 (11)	0.0040 (12)
C23	0.0375 (16)	0.0439 (18)	0.0234 (15)	−0.0011 (13)	0.0088 (12)	−0.0045 (12)
C24	0.0419 (17)	0.0415 (17)	0.0217 (15)	−0.0032 (13)	0.0028 (12)	0.0023 (12)
C25	0.0341 (16)	0.0457 (18)	0.0279 (16)	0.0047 (13)	0.0027 (12)	0.0073 (13)
C31	0.0354 (16)	0.0421 (17)	0.0279 (15)	0.0070 (13)	0.0026 (12)	0.0111 (13)
C61	0.0250 (15)	0.076 (3)	0.0220 (15)	0.0042 (15)	0.0013 (12)	0.0074 (15)
C63	0.0353 (16)	0.056 (2)	0.0358 (18)	−0.0001 (15)	−0.0048 (13)	−0.0097 (15)
C64	0.047 (2)	0.036 (2)	0.173 (6)	−0.0051 (17)	0.005 (3)	0.004 (3)
C65A	0.029 (3)	0.014 (3)	0.036 (3)	0.0025 (18)	−0.011 (2)	−0.003 (2)
C311	0.0268 (14)	0.0384 (16)	0.0221 (14)	0.0012 (11)	−0.0026 (11)	0.0024 (12)
C312	0.0315 (15)	0.0425 (17)	0.0233 (14)	−0.0001 (12)	−0.0019 (12)	−0.0007 (12)
C313	0.0393 (17)	0.0424 (18)	0.0339 (17)	0.0089 (14)	−0.0119 (13)	−0.0063 (13)
C314	0.052 (2)	0.0369 (18)	0.0376 (18)	−0.0052 (14)	−0.0155 (15)	0.0016 (13)
C315	0.0428 (18)	0.0457 (19)	0.0371 (18)	−0.0079 (14)	−0.0024 (14)	0.0074 (14)
C316	0.0304 (15)	0.0434 (18)	0.0341 (16)	−0.0007 (13)	0.0004 (12)	0.0033 (13)
C65B	0.015 (3)	0.011 (3)	0.018 (4)	−0.001 (2)	0.007 (3)	−0.002 (2)

Geometric parameters (Å, º)

O4—C4	1.215 (4)	C3—H3	1.0000
O22—C21	1.369 (3)	C5—H5A	0.9900
O22—C23	1.373 (4)	C5—H5B	0.9900
O62—C61	1.333 (4)	C6—H6	1.0000
O62—C63	1.375 (5)	C23—H23	0.9500
N1—C2	1.464 (4)	C24—H24	0.9500
N1—C6	1.473 (4)	C25—H25	0.9500
N1—H1	1.0200	C31—H31B	0.9900
C2—C21	1.487 (4)	C31—H31A	0.9900
C2—C3	1.563 (4)	C63—H63	0.9300
C3—C4	1.512 (4)	C64—H64	0.9300
C3—C31	1.525 (4)	C65A—H65A	0.9300
C4—C5	1.498 (5)	C65B—H65B	0.9300
C5—C6	1.539 (5)	C311—C312	1.393 (2)
C6—C61	1.486 (4)	C311—C316	1.395 (2)
C21—C25	1.339 (4)	C312—C313	1.378 (2)
C23—C24	1.331 (4)	C313—C314	1.384 (2)
C24—C25	1.424 (4)	C314—C315	1.376 (2)
C31—C311	1.511 (3)	C315—C316	1.379 (2)
C61—C65A	1.193 (4)	C312—H312	0.9500
C61—C65B	1.504 (4)	C313—H313	0.9500
C63—C64	1.278 (5)	C314—H314	0.9500
C64—C65A	1.590 (5)	C315—H315	0.9500
C64—C65B	1.308 (4)	C316—H316	0.9500
C2—H2	1.0000
O4···C311	3.196 (4)	H1···H65A^iv	2.5900
O4···C316	3.137 (4)	H1···C64^viii	2.6800
O4···C23^i	3.266 (5)	H1···C65B^iv	2.9000
O22···N1	2.960 (4)	H2···H6	2.4000
O62···N1	3.226 (5)	H2···H64^iv	2.5500
O4···H5B^ii	2.8300	H2···C65B^iv	2.9800
O4···H23^i	2.3800	H2···H65B^iv	2.4700
O4···H316	2.7200	H3···C312	2.9000
O4···H31B	2.5600	H3···O22	2.7300
O22···H3	2.7300	H5A···H312^x	2.5500
O22···H31B^iii	2.7100	H5A···C312^x	2.9500
O62···H5B	2.7100	H5B···O4^iii	2.8300
O62···H6^iii	2.9000	H5B···O62	2.7100
N1···O22	2.960 (4)	H5B···C23^x	3.0200
N1···O62	3.226 (5)	H6···C65A^iv	2.8900
N1···H65B^iv	2.5900	H6···H65A^iv	2.0500
C2···C65B^iv	3.592 (4)	H6···H65A	2.4600
C23···O4^v	3.266 (5)	H6···O62^ii	2.9000
C65A···C65A^iv	3.560 (4)	H6···C63^ii	2.9500
C65B···C2^iv	3.592 (4)	H6···H2	2.4000
C2···H65B^iv	2.8800	H6···C65B^iv	3.0700
C6···H65B^iv	3.0300	H23···O4^v	2.3800
C6···H65A^iv	2.7500	H24···C313^vi	3.0300
C21···H31A	2.5700	H24···C314^vi	3.0900
C23···H5B^vi	3.0200	H24···C312^vi	3.0700
C24···H314^vii	3.0800	H31A···H312	2.5600
C63···H6^iii	2.9500	H31A···C21	2.5700
C64···H1^viii	2.6800	H31B···O4	2.5600
C65A···H6^iv	2.8900	H31B···O22^ii	2.7100
C65A···H65A^iv	2.7400	H31B···H316	2.4100
C65A···H1	2.6800	H63···C312^xii	3.0800
C65B···H1^iv	2.9000	H63···C313^xii	2.7500
C65B···H2^iv	2.9800	H63···C314^xii	2.8900
C65B···H6^iv	3.0700	H64···H2^iv	2.5500
C311···O4	3.196 (4)	H64···H1^viii	2.4400
C312···C316^iii	3.566 (4)	H65A···H1	2.4700
C313···C315^iii	3.572 (4)	H65A···H6^iv	2.0500
C314···C314^ix	3.514 (4)	H65A···H65A^iv	2.0100
C315···C313^ii	3.572 (4)	H65A···C6^iv	2.7500
C316···C312^ii	3.566 (4)	H65A···C65A^iv	2.7400
C316···O4	3.137 (4)	H65A···H6	2.4600
C312···H5A^vi	2.9500	H65A···H1^iv	2.5900
C312···H24^x	3.0700	H65B···C6^iv	3.0300
C312···H316^iii	3.0500	H65B···H1^iv	1.9800
C312···H3	2.9000	H65B···N1^iv	2.5900
C312···H63^xi	3.0800	H65B···C2^iv	2.8800
C313···H63^xi	2.7500	H65B···H2^iv	2.4700
C313···H24^x	3.0300	H312···H31A	2.5600
C314···H63^xi	2.8900	H312···H5A^vi	2.5500
C314···H314^ix	2.9500	H313···C315^iii	3.0500
C314···H24^x	3.0900	H314···C314^ix	2.9500
C315···H313^ii	3.0500	H314···C24^xiii	3.0800
H1···C65A	2.6800	H315···H315^xiv	2.5200
H1···H65A	2.4700	H316···H31B	2.4100
H1···H65B^iv	1.9800	H316···O4	2.7200
H1···H64^viii	2.4400	H316···C312^ii	3.0500
C21—O22—C23	106.3 (2)	C6—C5—H5B	110.00
C61—O62—C63	108.5 (3)	H5A—C5—H5B	108.00
C2—N1—C6	112.5 (2)	N1—C6—H6	108.00
C2—N1—H1	114.00	C5—C6—H6	108.00
C6—N1—H1	109.00	C61—C6—H6	108.00
C3—C2—C21	112.1 (2)	O22—C23—H23	125.00
N1—C2—C3	110.0 (2)	C24—C23—H23	125.00
N1—C2—C21	110.2 (2)	C25—C24—H24	127.00
C2—C3—C4	105.6 (2)	C23—C24—H24	127.00
C2—C3—C31	113.7 (2)	C24—C25—H25	126.00
C4—C3—C31	113.4 (2)	C21—C25—H25	126.00
O4—C4—C3	122.2 (3)	C3—C31—H31B	109.00
C3—C4—C5	115.1 (3)	C311—C31—H31A	109.00
O4—C4—C5	122.6 (3)	C311—C31—H31B	109.00
C4—C5—C6	109.3 (2)	H31A—C31—H31B	108.00
N1—C6—C61	110.6 (2)	C3—C31—H31A	109.00
C5—C6—C61	111.6 (2)	C64—C63—H63	126.00
N1—C6—C5	110.3 (2)	O62—C63—H63	126.00
C2—C21—C25	134.0 (3)	C63—C64—H64	128.00
O22—C21—C2	116.4 (2)	C65A—C64—H64	128.00
O22—C21—C25	109.6 (2)	C65B—C64—H64	113.00
O22—C23—C24	110.6 (2)	C61—C65A—H65A	129.00
C23—C24—C25	106.2 (2)	C64—C65A—H65A	129.00
C21—C25—C24	107.3 (2)	C61—C65B—H65B	129.00
C3—C31—C311	112.8 (2)	C64—C65B—H65B	129.00
O62—C61—C65B	105.0 (2)	C31—C311—C316	121.71 (14)
O62—C61—C6	125.8 (3)	C31—C311—C312	120.74 (14)
O62—C61—C65A	112.0 (3)	C312—C311—C316	117.55 (10)
C6—C61—C65B	128.9 (2)	C311—C312—C313	121.42 (10)
C6—C61—C65A	118.8 (3)	C312—C313—C314	120.01 (10)
O62—C63—C64	107.6 (3)	C313—C314—C315	119.49 (10)
C63—C64—C65B	114.3 (3)	C314—C315—C316	120.53 (10)
C63—C64—C65A	103.4 (3)	C311—C316—C315	120.99 (10)
C61—C65A—C64	102.5 (2)	C311—C312—H312	119.00
C61—C65B—C64	101.8 (2)	C313—C312—H312	119.00
C21—C2—H2	108.00	C312—C313—H313	120.00
N1—C2—H2	109.00	C314—C313—H313	120.00
C3—C2—H2	108.00	C315—C314—H314	120.00
C4—C3—H3	108.00	C313—C314—H314	120.00
C2—C3—H3	108.00	C314—C315—H315	120.00
C31—C3—H3	108.00	C316—C315—H315	120.00
C4—C5—H5A	110.00	C315—C316—H316	119.00
C4—C5—H5B	110.00	C311—C316—H316	120.00
C6—C5—H5A	110.00
C23—O22—C21—C2	178.7 (2)	C31—C3—C4—C5	177.9 (2)
C23—O22—C21—C25	−0.1 (3)	C2—C3—C31—C311	165.7 (2)
C21—O22—C23—C24	0.3 (3)	C4—C3—C31—C311	−73.6 (3)
C63—O62—C61—C6	177.6 (3)	O4—C4—C5—C6	−120.3 (3)
C63—O62—C61—C65A	19.2 (3)	C3—C4—C5—C6	55.3 (3)
C61—O62—C63—C64	−1.7 (4)	C4—C5—C6—N1	−52.6 (3)
C6—N1—C2—C3	−62.6 (3)	C4—C5—C6—C61	−175.9 (2)
C6—N1—C2—C21	173.3 (2)	N1—C6—C61—O62	−82.1 (4)
C2—N1—C6—C5	58.8 (3)	N1—C6—C61—C65A	74.9 (3)
C2—N1—C6—C61	−177.2 (2)	C5—C6—C61—O62	41.0 (4)
N1—C2—C3—C4	58.3 (3)	C5—C6—C61—C65A	−161.9 (2)
N1—C2—C3—C31	−176.8 (2)	O22—C21—C25—C24	−0.2 (3)
C21—C2—C3—C4	−178.7 (2)	C2—C21—C25—C24	−178.6 (3)
C21—C2—C3—C31	−53.8 (3)	O22—C23—C24—C25	−0.4 (3)
N1—C2—C21—O22	65.6 (3)	C23—C24—C25—C21	0.3 (3)
N1—C2—C21—C25	−116.1 (4)	C3—C31—C311—C312	−76.9 (2)
C3—C2—C21—O22	−57.3 (3)	C3—C31—C311—C316	102.4 (2)
C3—C2—C21—C25	121.1 (3)	O62—C61—C65A—C64	−24.5 (3)
C2—C3—C4—O4	118.6 (3)	C6—C61—C65A—C64	175.5 (3)
C2—C3—C4—C5	−57.0 (3)	O62—C63—C64—C65A	−11.4 (4)
C31—C3—C4—O4	−6.5 (4)	C63—C64—C65A—C61	22.7 (4)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···O4^v	0.95	2.38	3.266 (5)	155

Symmetry code: (v) x+1, −y+1/2, z−1/2.