Ethyl 4-hy-droxy-2,6-diphenyl-1-[2-(piperidin-1-yl)acet-yl]-1,2,5,6-tetra-hydro-pyridine-3-carboxyl-ate.

In the title compound, C(27)H(32)N(2)O(4), the piperidine and tetra-hydro-pyridine rings adopt chair and half-chair conformations, respectively. The dihedral angle between the two phenyl rings is 32.9 (1)°. The mol-ecular structure is stabilized by a strong intra-molecular O-H⋯O hydrogen bond, generating an S(6) motif. In the crystal, inter-molecular C-H⋯O inter-actions form a ribbon-like structure along the a axis.

Related literature

For the biological activity of piperidines, see: Aridoss et al. (2008 ▶, 2010 ▶). For related structures, see: Subha Nandhini et al. (2003 ▶); Aridoss et al. (2009a ▶,b ▶); Parkin et al. (2004 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C27H32N2O4

M = 448.55

Monoclinic,

a = 10.7936 (6) Å

b = 9.6752 (6) Å

c = 23.2335 (13) Å

β = 93.213 (3)°

V = 2422.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 292 K

0.25 × 0.23 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.979, T max = 0.984

21907 measured reflections

5870 independent reflections

3631 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.193

S = 1.05

5870 reflections

299 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810026619/ci5118sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026619/ci5118Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C27H32N2O4	F(000) = 960
Mr = 448.55	Dx = 1.230 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1525 reflections
a = 10.7936 (6) Å	θ = 1.8–28.3°
b = 9.6752 (6) Å	µ = 0.08 mm−1
c = 23.2335 (13) Å	T = 292 K
β = 93.213 (3)°	Block, colourless
V = 2422.5 (2) Å3	0.25 × 0.23 × 0.20 mm
Z = 4

Bruker SMART APEXII area-detector diffractometer	5870 independent reflections
Radiation source: fine-focus sealed tube	3631 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω and φ scans	θmax = 28.3°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −14→14
Tmin = 0.979, Tmax = 0.984	k = −12→12
21907 measured reflections	l = −30→29

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.193	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0946P)2 + 0.5359P] where P = (Fo2 + 2Fc2)/3
5870 reflections	(Δ/σ)max = 0.001
299 parameters	Δρmax = 0.58 e Å−3
1 restraint	Δρmin = −0.37 e Å−3

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.

	x	y	z	Uiso*/Ueq
C27	0.3740 (4)	−0.0409 (8)	0.2481 (2)	0.206 (3)
H27A	0.4323	−0.0751	0.2218	0.308*
H27B	0.3930	−0.0787	0.2857	0.308*
H27C	0.3791	0.0581	0.2498	0.308*
C1	0.08942 (18)	0.31589 (19)	0.01812 (8)	0.0470 (4)
H1	0.0592	0.3326	−0.0218	0.056*
C2	−0.02445 (18)	0.2987 (2)	0.05340 (9)	0.0539 (5)
H2A	−0.0605	0.3888	0.0600	0.065*
H2B	−0.0859	0.2436	0.0317	0.065*
C3	0.00608 (18)	0.2312 (2)	0.10962 (9)	0.0528 (5)
C4	0.10915 (17)	0.1540 (2)	0.12035 (8)	0.0492 (5)
C5	0.20372 (17)	0.1306 (2)	0.07547 (8)	0.0455 (4)
H5	0.2104	0.0302	0.0711	0.055*
C6	0.33462 (17)	0.1815 (2)	0.09306 (8)	0.0467 (4)
C7	0.35769 (19)	0.2807 (3)	0.13484 (9)	0.0573 (5)
H7	0.2915	0.3222	0.1521	0.069*
C8	0.4785 (2)	0.3197 (3)	0.15163 (11)	0.0733 (7)
H8	0.4926	0.3864	0.1801	0.088*
C9	0.5763 (2)	0.2598 (3)	0.12621 (13)	0.0821 (8)
H9	0.6571	0.2854	0.1374	0.098*
C10	0.5550 (2)	0.1619 (3)	0.08418 (14)	0.0822 (8)
H10	0.6215	0.1217	0.0667	0.099*
C11	0.4350 (2)	0.1225 (3)	0.06762 (11)	0.0645 (6)
H11	0.4215	0.0557	0.0392	0.077*
C12	0.17351 (17)	0.4373 (2)	0.03603 (8)	0.0462 (4)
C13	0.1481 (2)	0.5271 (2)	0.08002 (10)	0.0580 (5)
H13	0.0799	0.5107	0.1018	0.070*
C14	0.2225 (2)	0.6412 (3)	0.09232 (12)	0.0725 (7)
H14	0.2044	0.7001	0.1223	0.087*
C15	0.3227 (3)	0.6673 (3)	0.06033 (13)	0.0771 (7)
H15	0.3720	0.7446	0.0682	0.093*
C16	0.3502 (2)	0.5787 (3)	0.01649 (13)	0.0734 (7)
H16	0.4186	0.5956	−0.0051	0.088*
C17	0.2763 (2)	0.4647 (2)	0.00461 (10)	0.0591 (5)
H17	0.2957	0.4052	−0.0250	0.071*
C18	0.15252 (19)	0.0927 (2)	−0.02602 (9)	0.0522 (5)
C19	0.0955 (2)	0.1375 (2)	−0.08475 (9)	0.0581 (5)
H19A	0.0885	0.0571	−0.1097	0.070*
H19B	0.0122	0.1714	−0.0798	0.070*
C20	0.2914 (2)	0.1989 (3)	−0.12236 (11)	0.0752 (7)
H20A	0.2891	0.1152	−0.1454	0.090*
H20B	0.3334	0.1777	−0.0854	0.090*
C21	0.3637 (3)	0.3090 (4)	−0.15246 (13)	0.0973 (10)
H21A	0.3713	0.3905	−0.1282	0.117*
H21B	0.4466	0.2752	−0.1585	0.117*
C22	0.2998 (3)	0.3470 (4)	−0.20973 (12)	0.0988 (10)
H22A	0.3428	0.4237	−0.2267	0.119*
H22B	0.3018	0.2690	−0.2359	0.119*
C23	0.1672 (3)	0.3868 (4)	−0.20086 (12)	0.0906 (9)
H23A	0.1240	0.4028	−0.2380	0.109*
H23B	0.1658	0.4722	−0.1790	0.109*
C24	0.1010 (2)	0.2751 (3)	−0.16913 (10)	0.0691 (6)
H24A	0.0169	0.3049	−0.1631	0.083*
H24B	0.0964	0.1920	−0.1925	0.083*
C25	0.1255 (2)	0.0802 (3)	0.17438 (9)	0.0638 (6)
C26	0.2522 (3)	−0.0805 (4)	0.22867 (13)	0.1089 (12)
H26A	0.1940	−0.0565	0.2574	0.131*
H26B	0.2487	−0.1797	0.2226	0.131*
N1	0.15713 (15)	0.18363 (16)	0.01878 (6)	0.0461 (4)
N2	0.16459 (16)	0.24368 (19)	−0.11332 (7)	0.0543 (4)
O1	0.19378 (17)	−0.02442 (17)	−0.02074 (7)	0.0726 (5)
O2	−0.08101 (14)	0.2495 (2)	0.14807 (7)	0.0731 (5)
H2	−0.0613	0.2069	0.1777	0.110*
O3	0.05991 (18)	0.0935 (3)	0.21512 (7)	0.0941 (7)
O4	0.21980 (15)	−0.0091 (2)	0.17514 (7)	0.0785 (5)

	U11	U22	U33	U12	U13	U23
C27	0.141 (4)	0.309 (8)	0.158 (4)	−0.045 (4)	−0.073 (3)	0.136 (5)
C1	0.0501 (10)	0.0474 (11)	0.0429 (9)	0.0052 (9)	−0.0033 (8)	0.0027 (8)
C2	0.0427 (10)	0.0555 (12)	0.0628 (12)	0.0028 (9)	−0.0029 (9)	0.0008 (10)
C3	0.0404 (10)	0.0636 (13)	0.0547 (11)	−0.0071 (9)	0.0064 (8)	−0.0044 (9)
C4	0.0434 (10)	0.0597 (12)	0.0447 (10)	−0.0055 (9)	0.0030 (8)	0.0042 (9)
C5	0.0479 (10)	0.0453 (10)	0.0434 (10)	0.0053 (8)	0.0035 (8)	0.0041 (8)
C6	0.0441 (10)	0.0515 (11)	0.0447 (10)	0.0068 (8)	0.0050 (7)	0.0113 (8)
C7	0.0439 (10)	0.0746 (14)	0.0537 (11)	0.0018 (10)	0.0044 (8)	0.0000 (10)
C8	0.0549 (13)	0.0920 (19)	0.0722 (15)	−0.0139 (13)	−0.0054 (11)	0.0022 (13)
C9	0.0409 (12)	0.105 (2)	0.100 (2)	−0.0045 (13)	−0.0010 (12)	0.0259 (18)
C10	0.0473 (13)	0.094 (2)	0.107 (2)	0.0206 (13)	0.0232 (13)	0.0154 (17)
C11	0.0547 (12)	0.0673 (14)	0.0727 (14)	0.0151 (11)	0.0142 (10)	0.0038 (12)
C12	0.0482 (10)	0.0447 (10)	0.0454 (10)	0.0058 (8)	−0.0013 (8)	0.0049 (8)
C13	0.0555 (12)	0.0594 (13)	0.0593 (12)	0.0022 (10)	0.0044 (9)	−0.0082 (10)
C14	0.0709 (15)	0.0628 (15)	0.0828 (16)	0.0013 (13)	−0.0041 (13)	−0.0187 (13)
C15	0.0658 (15)	0.0561 (14)	0.108 (2)	−0.0080 (12)	−0.0114 (14)	−0.0023 (14)
C16	0.0580 (13)	0.0686 (16)	0.0944 (18)	−0.0040 (12)	0.0121 (12)	0.0157 (14)
C17	0.0595 (12)	0.0563 (13)	0.0621 (13)	0.0044 (11)	0.0102 (10)	0.0043 (10)
C18	0.0551 (11)	0.0497 (12)	0.0517 (11)	−0.0046 (10)	0.0037 (9)	−0.0045 (9)
C19	0.0647 (13)	0.0631 (13)	0.0458 (11)	−0.0097 (11)	−0.0023 (9)	−0.0083 (9)
C20	0.0583 (13)	0.100 (2)	0.0676 (15)	0.0072 (13)	0.0038 (11)	−0.0019 (14)
C21	0.0676 (16)	0.146 (3)	0.0796 (18)	−0.0136 (18)	0.0192 (14)	0.0062 (19)
C22	0.091 (2)	0.140 (3)	0.0686 (17)	−0.0126 (19)	0.0291 (15)	0.0074 (18)
C23	0.102 (2)	0.110 (2)	0.0614 (15)	0.0077 (19)	0.0183 (14)	0.0161 (15)
C24	0.0640 (14)	0.0943 (18)	0.0491 (12)	0.0090 (13)	0.0041 (10)	−0.0018 (12)
C25	0.0497 (11)	0.0903 (17)	0.0512 (12)	−0.0120 (12)	0.0019 (9)	0.0152 (11)
C26	0.105 (2)	0.141 (3)	0.0776 (18)	−0.011 (2)	−0.0199 (16)	0.061 (2)
N1	0.0521 (9)	0.0445 (9)	0.0413 (8)	0.0040 (7)	0.0006 (6)	0.0013 (7)
N2	0.0528 (10)	0.0681 (11)	0.0420 (8)	−0.0018 (9)	0.0040 (7)	−0.0044 (8)
O1	0.0955 (12)	0.0527 (9)	0.0690 (10)	0.0110 (9)	−0.0002 (9)	−0.0110 (8)
O2	0.0484 (8)	0.1009 (13)	0.0718 (10)	0.0021 (8)	0.0196 (7)	−0.0005 (9)
O3	0.0797 (12)	0.1485 (19)	0.0562 (10)	−0.0009 (12)	0.0214 (9)	0.0255 (11)
O4	0.0676 (10)	0.1049 (14)	0.0628 (10)	0.0032 (10)	0.0005 (8)	0.0414 (9)

C27—C26	1.418 (4)	C14—H14	0.93
C27—H27A	0.96	C15—C16	1.376 (4)
C27—H27B	0.96	C15—H15	0.93
C27—H27C	0.96	C16—C17	1.379 (3)
C1—N1	1.473 (2)	C16—H16	0.93
C1—C2	1.524 (3)	C17—H17	0.93
C1—C12	1.528 (3)	C18—O1	1.221 (3)
C1—H1	0.98	C18—N1	1.361 (3)
C2—C3	1.481 (3)	C18—C19	1.528 (3)
C2—H2A	0.97	C19—N2	1.452 (3)
C2—H2B	0.97	C19—H19A	0.97
C3—O2	1.344 (2)	C19—H19B	0.97
C3—C4	1.352 (3)	C20—N2	1.463 (3)
C4—C25	1.446 (3)	C20—C21	1.514 (4)
C4—C5	1.516 (3)	C20—H20A	0.97
C5—N1	1.475 (2)	C20—H20B	0.97
C5—C6	1.530 (3)	C21—C22	1.509 (4)
C5—H5	0.98	C21—H21A	0.97
C6—C7	1.378 (3)	C21—H21B	0.97
C6—C11	1.386 (3)	C22—C23	1.508 (4)
C7—C8	1.392 (3)	C22—H22A	0.97
C7—H7	0.93	C22—H22B	0.97
C8—C9	1.367 (4)	C23—C24	1.510 (4)
C8—H8	0.93	C23—H23A	0.97
C9—C10	1.371 (4)	C23—H23B	0.97
C9—H9	0.93	C24—N2	1.465 (3)
C10—C11	1.384 (4)	C24—H24A	0.97
C10—H10	0.93	C24—H24B	0.97
C11—H11	0.93	C25—O3	1.220 (3)
C12—C13	1.381 (3)	C25—O4	1.335 (3)
C12—C17	1.388 (3)	C26—O4	1.448 (3)
C13—C14	1.385 (3)	C26—H26A	0.97
C13—H13	0.93	C26—H26B	0.97
C14—C15	1.369 (4)	O2—H2	0.82
C26—C27—H27A	109.5	C15—C16—H16	120.0
C26—C27—H27B	109.5	C17—C16—H16	120.0
H27A—C27—H27B	109.5	C16—C17—C12	121.2 (2)
C26—C27—H27C	109.5	C16—C17—H17	119.4
H27A—C27—H27C	109.5	C12—C17—H17	119.4
H27B—C27—H27C	109.5	O1—C18—N1	121.68 (19)
N1—C1—C2	108.30 (16)	O1—C18—C19	118.64 (19)
N1—C1—C12	112.21 (15)	N1—C18—C19	119.68 (18)
C2—C1—C12	114.98 (17)	N2—C19—C18	114.65 (17)
N1—C1—H1	107.0	N2—C19—H19A	108.6
C2—C1—H1	107.0	C18—C19—H19A	108.6
C12—C1—H1	107.0	N2—C19—H19B	108.6
C3—C2—C1	112.11 (16)	C18—C19—H19B	108.6
C3—C2—H2A	109.2	H19A—C19—H19B	107.6
C1—C2—H2A	109.2	N2—C20—C21	111.6 (2)
C3—C2—H2B	109.2	N2—C20—H20A	109.3
C1—C2—H2B	109.2	C21—C20—H20A	109.3
H2A—C2—H2B	107.9	N2—C20—H20B	109.3
O2—C3—C4	123.3 (2)	C21—C20—H20B	109.3
O2—C3—C2	113.52 (18)	H20A—C20—H20B	108.0
C4—C3—C2	123.13 (18)	C22—C21—C20	110.9 (3)
C3—C4—C25	119.49 (19)	C22—C21—H21A	109.5
C3—C4—C5	122.28 (17)	C20—C21—H21A	109.5
C25—C4—C5	117.99 (18)	C22—C21—H21B	109.5
N1—C5—C4	110.69 (15)	C20—C21—H21B	109.5
N1—C5—C6	112.96 (15)	H21A—C21—H21B	108.0
C4—C5—C6	114.55 (16)	C23—C22—C21	109.4 (2)
N1—C5—H5	106.0	C23—C22—H22A	109.8
C4—C5—H5	106.0	C21—C22—H22A	109.8
C6—C5—H5	106.0	C23—C22—H22B	109.8
C7—C6—C11	118.2 (2)	C21—C22—H22B	109.8
C7—C6—C5	122.69 (17)	H22A—C22—H22B	108.2
C11—C6—C5	119.04 (19)	C22—C23—C24	111.3 (3)
C6—C7—C8	121.1 (2)	C22—C23—H23A	109.4
C6—C7—H7	119.5	C24—C23—H23A	109.4
C8—C7—H7	119.5	C22—C23—H23B	109.4
C9—C8—C7	119.8 (3)	C24—C23—H23B	109.4
C9—C8—H8	120.1	H23A—C23—H23B	108.0
C7—C8—H8	120.1	N2—C24—C23	111.7 (2)
C8—C9—C10	119.9 (2)	N2—C24—H24A	109.3
C8—C9—H9	120.1	C23—C24—H24A	109.3
C10—C9—H9	120.1	N2—C24—H24B	109.3
C9—C10—C11	120.4 (2)	C23—C24—H24B	109.3
C9—C10—H10	119.8	H24A—C24—H24B	107.9
C11—C10—H10	119.8	O3—C25—O4	122.2 (2)
C10—C11—C6	120.6 (2)	O3—C25—C4	125.0 (2)
C10—C11—H11	119.7	O4—C25—C4	112.78 (19)
C6—C11—H11	119.7	C27—C26—O4	108.6 (3)
C13—C12—C17	117.8 (2)	C27—C26—H26A	110.0
C13—C12—C1	123.09 (18)	O4—C26—H26A	110.0
C17—C12—C1	118.96 (18)	C27—C26—H26B	110.0
C12—C13—C14	121.2 (2)	O4—C26—H26B	110.0
C12—C13—H13	119.4	H26A—C26—H26B	108.4
C14—C13—H13	119.4	C18—N1—C1	123.80 (16)
C15—C14—C13	120.1 (2)	C18—N1—C5	117.01 (16)
C15—C14—H14	120.0	C1—N1—C5	117.08 (14)
C13—C14—H14	120.0	C19—N2—C20	111.43 (19)
C14—C15—C16	119.8 (2)	C19—N2—C24	108.92 (17)
C14—C15—H15	120.1	C20—N2—C24	109.31 (17)
C16—C15—H15	120.1	C3—O2—H2	109.5
C15—C16—C17	120.0 (2)	C25—O4—C26	117.9 (2)
N1—C1—C2—C3	47.4 (2)	C13—C12—C17—C16	−0.6 (3)
C12—C1—C2—C3	−79.0 (2)	C1—C12—C17—C16	175.4 (2)
C1—C2—C3—O2	161.99 (18)	O1—C18—C19—N2	−112.8 (2)
C1—C2—C3—C4	−20.6 (3)	N1—C18—C19—N2	66.8 (3)
O2—C3—C4—C25	3.4 (3)	N2—C20—C21—C22	−57.8 (3)
C2—C3—C4—C25	−173.7 (2)	C20—C21—C22—C23	53.9 (4)
O2—C3—C4—C5	177.68 (19)	C21—C22—C23—C24	−53.7 (4)
C2—C3—C4—C5	0.6 (3)	C22—C23—C24—N2	57.3 (3)
C3—C4—C5—N1	−8.9 (3)	C3—C4—C25—O3	−8.8 (4)
C25—C4—C5—N1	165.46 (18)	C5—C4—C25—O3	176.7 (2)
C3—C4—C5—C6	120.3 (2)	C3—C4—C25—O4	169.4 (2)
C25—C4—C5—C6	−65.4 (2)	C5—C4—C25—O4	−5.0 (3)
N1—C5—C6—C7	106.2 (2)	O1—C18—N1—C1	−168.4 (2)
C4—C5—C6—C7	−21.8 (3)	C19—C18—N1—C1	12.1 (3)
N1—C5—C6—C11	−76.2 (2)	O1—C18—N1—C5	−5.5 (3)
C4—C5—C6—C11	155.77 (19)	C19—C18—N1—C5	175.05 (17)
C11—C6—C7—C8	−0.7 (3)	C2—C1—N1—C18	102.4 (2)
C5—C6—C7—C8	176.9 (2)	C12—C1—N1—C18	−129.59 (19)
C6—C7—C8—C9	0.4 (4)	C2—C1—N1—C5	−60.5 (2)
C7—C8—C9—C10	0.2 (4)	C12—C1—N1—C5	67.5 (2)
C8—C9—C10—C11	−0.5 (4)	C4—C5—N1—C18	−123.85 (19)
C9—C10—C11—C6	0.2 (4)	C6—C5—N1—C18	106.2 (2)
C7—C6—C11—C10	0.4 (3)	C4—C5—N1—C1	40.3 (2)
C5—C6—C11—C10	−177.3 (2)	C6—C5—N1—C1	−89.7 (2)
N1—C1—C12—C13	−125.6 (2)	C18—C19—N2—C20	58.5 (2)
C2—C1—C12—C13	−1.2 (3)	C18—C19—N2—C24	179.17 (19)
N1—C1—C12—C17	58.6 (2)	C21—C20—N2—C19	179.7 (2)
C2—C1—C12—C17	−177.07 (17)	C21—C20—N2—C24	59.2 (3)
C17—C12—C13—C14	0.2 (3)	C23—C24—N2—C19	179.1 (2)
C1—C12—C13—C14	−175.7 (2)	C23—C24—N2—C20	−58.9 (3)
C12—C13—C14—C15	0.6 (4)	O3—C25—O4—C26	−6.9 (4)
C13—C14—C15—C16	−0.9 (4)	C4—C25—O4—C26	174.8 (2)
C14—C15—C16—C17	0.5 (4)	C27—C26—O4—C25	−116.4 (5)
C15—C16—C17—C12	0.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.82	1.88	2.598 (3)	145
C2—H2B···O1i	0.97	2.43	3.286 (3)	148
C10—H10···O1ii	0.93	2.50	3.427 (3)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3	0.82	1.88	2.598 (3)	145
C2—H2B⋯O1i	0.97	2.43	3.286 (3)	148
C10—H10⋯O1ii	0.93	2.50	3.427 (3)	177

Symmetry codes: (i) ; (ii) .