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

In the title compound, C(26)H(30)N(2)O(4)S, the thio-morpholine ring adopts a chair conformation whereas the tetra-hydro-pyridine ring is in a half-chair conformation. The dihedral angle between the two phenyl rings is 33.3 (2)°. A strong intra-molecular O-H⋯O hydrogen bond generates an S(6) motif. In the crystal, mol-ecules are linked by inter-molecular C-H⋯O hydrogen bonds, generating a ribbon-like structure propagating along the a axis.

Related literature

For general background to the biological activity of tetra­hydro­pyridine derivatives, see: Aridoss et al. (2008 ▶, 2010 ▶); Chow et al. (1968 ▶). For related structures, see: Subha Nandhini et al. (2003 ▶); Aridoss et al. (2009 ▶); Parkin et al. (2004 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C26H30N2O4S

M = 466.58

Monoclinic,

a = 10.9561 (6) Å

b = 9.5665 (6) Å

c = 22.9011 (12) Å

β = 93.575 (3)°

V = 2395.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.17 mm−1

T = 292 K

0.26 × 0.23 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.957, T max = 0.967

21473 measured reflections

5677 independent reflections

3669 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.217

S = 1.04

5677 reflections

299 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.75 e Å−3

Δρmin = −0.56 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/S1600536810026413/ci5116sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026413/ci5116Isup2.hkl

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

C26H30N2O4S	F(000) = 992
Mr = 466.58	Dx = 1.294 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1201 reflections
a = 10.9561 (6) Å	θ = 1.8–28.2°
b = 9.5665 (6) Å	µ = 0.17 mm−1
c = 22.9011 (12) Å	T = 292 K
β = 93.575 (3)°	Block, colourless
V = 2395.6 (2) Å3	0.26 × 0.23 × 0.20 mm
Z = 4

Bruker SMART APEXII area-detector diffractometer	5677 independent reflections
Radiation source: fine-focus sealed tube	3669 reflections with I > 2σ(I)
graphite	Rint = 0.029
ω and φ scans	θmax = 28.2°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −14→14
Tmin = 0.957, Tmax = 0.967	k = −11→12
21473 measured reflections	l = −29→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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.217	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.1095P)2 + 1.0086P] where P = (Fo2 + 2Fc2)/3
5677 reflections	(Δ/σ)max = 0.001
299 parameters	Δρmax = 0.75 e Å−3
1 restraint	Δρmin = −0.56 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
C1	0.4059 (2)	0.1850 (2)	−0.01465 (10)	0.0453 (5)
H1	0.4343	0.1666	0.0260	0.054*
C2	0.5190 (2)	0.2068 (3)	−0.04884 (11)	0.0513 (6)
H2A	0.5772	0.2644	−0.0260	0.062*
H2B	0.5573	0.1171	−0.0552	0.062*
C3	0.4893 (2)	0.2748 (3)	−0.10615 (10)	0.0490 (6)
C4	0.3873 (2)	0.3516 (3)	−0.11724 (10)	0.0478 (6)
C5	0.2932 (2)	0.3731 (2)	−0.07271 (10)	0.0444 (5)
H5	0.2859	0.4745	−0.0678	0.053*
C6	0.1649 (2)	0.3208 (3)	−0.09247 (10)	0.0459 (5)
C7	0.1448 (2)	0.2216 (3)	−0.13558 (11)	0.0532 (6)
H7	0.2113	0.1804	−0.1522	0.064*
C8	0.0270 (3)	0.1820 (4)	−0.15461 (14)	0.0680 (8)
H8	0.0150	0.1150	−0.1838	0.082*
C9	−0.0707 (3)	0.2415 (4)	−0.13036 (17)	0.0796 (10)
H9	−0.1497	0.2155	−0.1432	0.095*
C10	−0.0529 (3)	0.3394 (4)	−0.08723 (18)	0.0805 (10)
H10	−0.1198	0.3792	−0.0705	0.097*
C11	0.0651 (3)	0.3799 (3)	−0.06812 (14)	0.0634 (7)
H11	0.0766	0.4470	−0.0389	0.076*
C12	0.3253 (2)	0.0626 (2)	−0.03482 (10)	0.0440 (5)
C13	0.3550 (2)	−0.0269 (3)	−0.07933 (11)	0.0544 (6)
H13	0.4231	−0.0085	−0.1004	0.065*
C14	0.2841 (3)	−0.1436 (3)	−0.09264 (15)	0.0699 (8)
H14	0.3051	−0.2032	−0.1225	0.084*
C15	0.1833 (3)	−0.1722 (3)	−0.06235 (16)	0.0722 (9)
H15	0.1365	−0.2514	−0.0713	0.087*
C16	0.1517 (3)	−0.0838 (3)	−0.01875 (15)	0.0698 (8)
H16	0.0827	−0.1023	0.0017	0.084*
C17	0.2222 (2)	0.0330 (3)	−0.00502 (12)	0.0563 (6)
H17	0.2000	0.0926	0.0246	0.068*
C18	0.3700 (2)	0.4250 (3)	−0.17259 (12)	0.0608 (7)
C19	0.2455 (3)	0.5885 (5)	−0.22699 (16)	0.0963 (13)
H19A	0.3047	0.5682	−0.2556	0.116*
H19B	0.2436	0.6888	−0.2209	0.116*
C20	0.1253 (5)	0.5390 (10)	−0.2479 (3)	0.210 (4)
H20A	0.1195	0.4404	−0.2409	0.315*
H20B	0.1132	0.5568	−0.2891	0.315*
H20C	0.0638	0.5871	−0.2276	0.315*
C21	0.3374 (2)	0.4067 (3)	0.03114 (11)	0.0508 (6)
C22	0.3935 (3)	0.3617 (3)	0.09078 (11)	0.0566 (6)
H22A	0.4770	0.3320	0.0863	0.068*
H22B	0.3963	0.4421	0.1167	0.068*
C23	0.2018 (3)	0.2891 (4)	0.12692 (14)	0.0677 (8)
H23A	0.1630	0.3190	0.0898	0.081*
H23B	0.2017	0.3677	0.1536	0.081*
C24	0.1283 (3)	0.1705 (5)	0.15118 (15)	0.0811 (10)
H24A	0.1292	0.0915	0.1246	0.097*
H24B	0.0440	0.2003	0.1531	0.097*
C25	0.3410 (3)	0.0918 (5)	0.20431 (15)	0.0880 (11)
H25A	0.3909	0.0721	0.2398	0.106*
H25B	0.3453	0.0113	0.1788	0.106*
C26	0.3931 (3)	0.2171 (4)	0.17450 (11)	0.0661 (8)
H26A	0.3891	0.2977	0.2000	0.079*
H26B	0.4785	0.1996	0.1682	0.079*
N1	0.33686 (18)	0.3177 (2)	−0.01508 (8)	0.0449 (5)
N2	0.32827 (18)	0.2491 (2)	0.11832 (8)	0.0508 (5)
O1	0.57597 (16)	0.2550 (2)	−0.14448 (8)	0.0655 (5)
H1A	0.5564	0.2960	−0.1751	0.098*
O2	0.4311 (2)	0.4081 (3)	−0.21421 (9)	0.0931 (8)
O3	0.27914 (19)	0.5182 (2)	−0.17266 (9)	0.0733 (6)
O4	0.2948 (2)	0.5239 (2)	0.02621 (9)	0.0703 (6)
S1	0.18591 (8)	0.11578 (13)	0.22245 (4)	0.0894 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0494 (13)	0.0440 (13)	0.0416 (11)	0.0044 (10)	−0.0030 (9)	0.0038 (10)
C2	0.0460 (13)	0.0507 (14)	0.0563 (14)	0.0030 (11)	−0.0027 (11)	0.0048 (11)
C3	0.0409 (12)	0.0581 (15)	0.0481 (12)	−0.0064 (11)	0.0041 (10)	−0.0007 (11)
C4	0.0444 (12)	0.0556 (14)	0.0431 (12)	−0.0040 (11)	0.0004 (9)	0.0086 (11)
C5	0.0494 (13)	0.0414 (12)	0.0422 (11)	0.0047 (10)	0.0009 (9)	0.0064 (10)
C6	0.0476 (13)	0.0462 (13)	0.0440 (11)	0.0069 (10)	0.0036 (10)	0.0127 (10)
C7	0.0455 (13)	0.0633 (16)	0.0511 (13)	0.0012 (11)	0.0045 (10)	0.0004 (12)
C8	0.0566 (16)	0.079 (2)	0.0674 (17)	−0.0105 (15)	−0.0065 (13)	0.0080 (15)
C9	0.0430 (15)	0.096 (3)	0.098 (2)	−0.0052 (16)	−0.0040 (15)	0.027 (2)
C10	0.0493 (17)	0.090 (2)	0.104 (3)	0.0202 (16)	0.0206 (17)	0.014 (2)
C11	0.0561 (16)	0.0626 (17)	0.0726 (18)	0.0134 (13)	0.0131 (13)	0.0026 (14)
C12	0.0491 (13)	0.0402 (12)	0.0422 (11)	0.0059 (10)	−0.0014 (9)	0.0066 (10)
C13	0.0545 (14)	0.0551 (15)	0.0537 (13)	0.0040 (12)	0.0035 (11)	−0.0063 (12)
C14	0.0706 (19)	0.0600 (17)	0.0775 (19)	0.0073 (15)	−0.0081 (15)	−0.0180 (15)
C15	0.0669 (19)	0.0492 (16)	0.098 (2)	−0.0057 (14)	−0.0158 (17)	−0.0008 (16)
C16	0.0587 (17)	0.0653 (18)	0.086 (2)	−0.0083 (14)	0.0083 (15)	0.0139 (17)
C17	0.0602 (16)	0.0533 (15)	0.0562 (14)	0.0028 (12)	0.0096 (12)	0.0024 (12)
C18	0.0461 (14)	0.083 (2)	0.0528 (14)	−0.0113 (14)	−0.0002 (11)	0.0193 (14)
C19	0.090 (2)	0.122 (3)	0.074 (2)	−0.001 (2)	−0.0136 (18)	0.054 (2)
C20	0.161 (6)	0.285 (9)	0.170 (6)	−0.070 (6)	−0.097 (5)	0.132 (6)
C21	0.0545 (14)	0.0468 (14)	0.0512 (13)	−0.0051 (11)	0.0032 (11)	−0.0029 (11)
C22	0.0628 (16)	0.0607 (16)	0.0457 (13)	−0.0097 (13)	−0.0010 (11)	−0.0088 (12)
C23	0.0533 (15)	0.085 (2)	0.0649 (17)	0.0086 (15)	0.0013 (13)	−0.0027 (15)
C24	0.0572 (17)	0.115 (3)	0.0716 (19)	−0.0078 (18)	0.0067 (14)	0.003 (2)
C25	0.075 (2)	0.125 (3)	0.0650 (18)	0.014 (2)	0.0171 (16)	0.027 (2)
C26	0.0517 (15)	0.100 (2)	0.0464 (13)	0.0049 (15)	0.0036 (11)	0.0035 (14)
N1	0.0541 (11)	0.0394 (10)	0.0407 (9)	0.0032 (8)	−0.0006 (8)	0.0025 (8)
N2	0.0490 (11)	0.0620 (13)	0.0415 (10)	−0.0003 (10)	0.0031 (8)	−0.0024 (9)
O1	0.0481 (10)	0.0906 (15)	0.0588 (11)	0.0004 (10)	0.0102 (8)	0.0043 (10)
O2	0.0701 (14)	0.153 (2)	0.0575 (12)	0.0105 (15)	0.0187 (10)	0.0351 (14)
O3	0.0670 (12)	0.0914 (15)	0.0606 (11)	0.0040 (11)	−0.0022 (9)	0.0363 (11)
O4	0.0921 (15)	0.0517 (12)	0.0667 (12)	0.0117 (10)	0.0025 (11)	−0.0090 (9)
S1	0.0735 (6)	0.1382 (9)	0.0589 (5)	−0.0044 (5)	0.0220 (4)	0.0086 (5)

C1—N1	1.477 (3)	C16—C17	1.383 (4)
C1—C2	1.521 (3)	C16—H16	0.93
C1—C12	1.521 (3)	C17—H17	0.93
C1—H1	0.98	C18—O2	1.209 (3)
C2—C3	1.483 (3)	C18—O3	1.336 (4)
C2—H2A	0.97	C19—O3	1.442 (3)
C2—H2B	0.97	C19—C20	1.452 (4)
C3—O1	1.346 (3)	C19—H19A	0.97
C3—C4	1.348 (3)	C19—H19B	0.97
C4—C18	1.451 (3)	C20—H20A	0.96
C4—C5	1.508 (3)	C20—H20B	0.96
C5—N1	1.474 (3)	C20—H20C	0.96
C5—C6	1.533 (3)	C21—O4	1.217 (3)
C5—H5	0.98	C21—N1	1.359 (3)
C6—C7	1.377 (4)	C21—C22	1.524 (4)
C6—C11	1.379 (4)	C22—N2	1.458 (3)
C7—C8	1.389 (4)	C22—H22A	0.97
C7—H7	0.93	C22—H22B	0.97
C8—C9	1.362 (5)	C23—N2	1.462 (3)
C8—H8	0.93	C23—C24	1.517 (5)
C9—C10	1.366 (5)	C23—H23A	0.97
C9—H9	0.93	C23—H23B	0.97
C10—C11	1.394 (5)	C24—S1	1.791 (4)
C10—H10	0.93	C24—H24A	0.97
C11—H11	0.93	C24—H24B	0.97
C12—C13	1.385 (3)	C25—C26	1.509 (5)
C12—C17	1.385 (4)	C25—S1	1.789 (3)
C13—C14	1.383 (4)	C25—H25A	0.97
C13—H13	0.93	C25—H25B	0.97
C14—C15	1.368 (5)	C26—N2	1.463 (3)
C14—H14	0.93	C26—H26A	0.97
C15—C16	1.370 (5)	C26—H26B	0.97
C15—H15	0.93	O1—H1A	0.82
N1—C1—C2	108.19 (19)	C12—C17—H17	119.5
N1—C1—C12	111.88 (19)	O2—C18—O3	122.5 (3)
C2—C1—C12	115.2 (2)	O2—C18—C4	125.1 (3)
N1—C1—H1	107.1	O3—C18—C4	112.4 (2)
C2—C1—H1	107.1	O3—C19—C20	108.1 (3)
C12—C1—H1	107.1	O3—C19—H19A	110.1
C3—C2—C1	111.97 (19)	C20—C19—H19A	110.1
C3—C2—H2A	109.2	O3—C19—H19B	110.1
C1—C2—H2A	109.2	C20—C19—H19B	110.1
C3—C2—H2B	109.2	H19A—C19—H19B	108.4
C1—C2—H2B	109.2	C19—C20—H20A	109.5
H2A—C2—H2B	107.9	C19—C20—H20B	109.5
O1—C3—C4	124.3 (2)	H20A—C20—H20B	109.5
O1—C3—C2	113.0 (2)	C19—C20—H20C	109.5
C4—C3—C2	122.7 (2)	H20A—C20—H20C	109.5
C3—C4—C18	119.3 (2)	H20B—C20—H20C	109.5
C3—C4—C5	122.7 (2)	O4—C21—N1	121.5 (2)
C18—C4—C5	117.8 (2)	O4—C21—C22	118.3 (2)
N1—C5—C4	111.03 (18)	N1—C21—C22	120.2 (2)
N1—C5—C6	112.77 (18)	N2—C22—C21	114.6 (2)
C4—C5—C6	114.10 (19)	N2—C22—H22A	108.6
N1—C5—H5	106.1	C21—C22—H22A	108.6
C4—C5—H5	106.1	N2—C22—H22B	108.6
C6—C5—H5	106.1	C21—C22—H22B	108.6
C7—C6—C11	118.5 (2)	H22A—C22—H22B	107.6
C7—C6—C5	122.6 (2)	N2—C23—C24	112.5 (3)
C11—C6—C5	118.8 (2)	N2—C23—H23A	109.1
C6—C7—C8	121.1 (3)	C24—C23—H23A	109.1
C6—C7—H7	119.4	N2—C23—H23B	109.1
C8—C7—H7	119.4	C24—C23—H23B	109.1
C9—C8—C7	119.8 (3)	H23A—C23—H23B	107.8
C9—C8—H8	120.1	C23—C24—S1	112.8 (2)
C7—C8—H8	120.1	C23—C24—H24A	109.0
C8—C9—C10	120.0 (3)	S1—C24—H24A	109.0
C8—C9—H9	120.0	C23—C24—H24B	109.0
C10—C9—H9	120.0	S1—C24—H24B	109.0
C9—C10—C11	120.4 (3)	H24A—C24—H24B	107.8
C9—C10—H10	119.8	C26—C25—S1	113.3 (3)
C11—C10—H10	119.8	C26—C25—H25A	108.9
C6—C11—C10	120.1 (3)	S1—C25—H25A	108.9
C6—C11—H11	119.9	C26—C25—H25B	108.9
C10—C11—H11	119.9	S1—C25—H25B	108.9
C13—C12—C17	118.2 (2)	H25A—C25—H25B	107.7
C13—C12—C1	122.8 (2)	N2—C26—C25	112.8 (3)
C17—C12—C1	118.9 (2)	N2—C26—H26A	109.0
C14—C13—C12	120.4 (3)	C25—C26—H26A	109.0
C14—C13—H13	119.8	N2—C26—H26B	109.0
C12—C13—H13	119.8	C25—C26—H26B	109.0
C15—C14—C13	120.7 (3)	H26A—C26—H26B	107.8
C15—C14—H14	119.7	C21—N1—C5	117.2 (2)
C13—C14—H14	119.7	C21—N1—C1	123.8 (2)
C14—C15—C16	119.7 (3)	C5—N1—C1	116.92 (18)
C14—C15—H15	120.2	C22—N2—C23	111.0 (2)
C16—C15—H15	120.2	C22—N2—C26	108.1 (2)
C15—C16—C17	120.1 (3)	C23—N2—C26	110.4 (2)
C15—C16—H16	119.9	C3—O1—H1A	109.5
C17—C16—H16	119.9	C18—O3—C19	117.6 (3)
C16—C17—C12	120.9 (3)	C25—S1—C24	96.42 (16)
C16—C17—H17	119.5
N1—C1—C2—C3	−48.5 (3)	C13—C12—C17—C16	1.0 (4)
C12—C1—C2—C3	77.5 (3)	C1—C12—C17—C16	−174.8 (2)
C1—C2—C3—O1	−159.7 (2)	C3—C4—C18—O2	11.3 (5)
C1—C2—C3—C4	22.2 (3)	C5—C4—C18—O2	−172.8 (3)
O1—C3—C4—C18	−3.2 (4)	C3—C4—C18—O3	−167.2 (2)
C2—C3—C4—C18	174.5 (2)	C5—C4—C18—O3	8.8 (3)
O1—C3—C4—C5	−179.0 (2)	O4—C21—C22—N2	114.2 (3)
C2—C3—C4—C5	−1.2 (4)	N1—C21—C22—N2	−66.5 (3)
C3—C4—C5—N1	8.2 (3)	N2—C23—C24—S1	63.1 (3)
C18—C4—C5—N1	−167.6 (2)	S1—C25—C26—N2	−62.4 (3)
C3—C4—C5—C6	−120.6 (3)	O4—C21—N1—C5	5.6 (4)
C18—C4—C5—C6	63.6 (3)	C22—C21—N1—C5	−173.6 (2)
N1—C5—C6—C7	−105.9 (3)	O4—C21—N1—C1	168.7 (2)
C4—C5—C6—C7	22.0 (3)	C22—C21—N1—C1	−10.6 (4)
N1—C5—C6—C11	77.1 (3)	C4—C5—N1—C21	125.2 (2)
C4—C5—C6—C11	−155.0 (2)	C6—C5—N1—C21	−105.3 (2)
C11—C6—C7—C8	0.4 (4)	C4—C5—N1—C1	−39.1 (3)
C5—C6—C7—C8	−176.5 (2)	C6—C5—N1—C1	90.4 (2)
C6—C7—C8—C9	−0.2 (4)	C2—C1—N1—C21	−103.0 (2)
C7—C8—C9—C10	−0.3 (5)	C12—C1—N1—C21	129.1 (2)
C8—C9—C10—C11	0.6 (5)	C2—C1—N1—C5	60.1 (3)
C7—C6—C11—C10	−0.2 (4)	C12—C1—N1—C5	−67.8 (2)
C5—C6—C11—C10	176.9 (3)	C21—C22—N2—C23	−59.2 (3)
C9—C10—C11—C6	−0.3 (5)	C21—C22—N2—C26	179.6 (2)
N1—C1—C12—C13	126.8 (2)	C24—C23—N2—C22	175.6 (2)
C2—C1—C12—C13	2.8 (3)	C24—C23—N2—C26	−64.6 (3)
N1—C1—C12—C17	−57.6 (3)	C25—C26—N2—C22	−174.2 (2)
C2—C1—C12—C17	178.3 (2)	C25—C26—N2—C23	64.2 (3)
C17—C12—C13—C14	−1.1 (4)	O2—C18—O3—C19	7.2 (4)
C1—C12—C13—C14	174.5 (2)	C4—C18—O3—C19	−174.3 (3)
C12—C13—C14—C15	0.3 (4)	C20—C19—O3—C18	110.8 (6)
C13—C14—C15—C16	0.6 (5)	C26—C25—S1—C24	51.6 (3)
C14—C15—C16—C17	−0.7 (5)	C23—C24—S1—C25	−51.8 (3)
C15—C16—C17—C12	−0.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2	0.82	1.92	2.627 (3)	144
C2—H2A···O4i	0.97	2.46	3.306 (3)	145
C10—H10···O4ii	0.93	2.41	3.339 (4)	178

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2	0.82	1.92	2.627 (3)	144
C2—H2A⋯O4i	0.97	2.46	3.306 (3)	145
C10—H10⋯O4ii	0.93	2.41	3.339 (4)	178

Symmetry codes: (i) ; (ii) .