[(2S,5R)-1-Methyl-5-phenyl-pyrrolidin-2-yl]diphenyl-methanol.

In the title compound, C(24)H(25)NO, the phenyl and diphenyl-methanol substituents are syn to each other. The pyrrolidine ring has an envelope conformation with the flap atom being the C atom bearing the phenyl substituent. The hy-droxy group forms an intra-molecular hydrogen bond with the pyrrolidine N atom, and the phenyl rings lie to same side of the mol-ecule. The crystal packing features C-H⋯π inter-actions. Two slightly displaced co-planar orientations were found for one of the phenyl rings; the major component had a site-occupancy factor of 0.782 (15).

Related literature

For background to the highly enanti­oselective addition of aryl­zinc reagents to aldehydes, see: Yoon & Jacobsen (2003 ▶), Taylor, et al. (2011 ▶). For related structures, see: Moro et al. (2010 ▶); Shabbir et al. (2009 ▶). For details of the synthetic protocols, see: Walsh & Kozlowski (2008 ▶); Paixão, et al. (2008 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C24H25NO

M = 343.45

Orthorhombic,

a = 9.9672 (2) Å

b = 13.3376 (2) Å

c = 14.4369 (2) Å

V = 1919.22 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 100 K

0.22 × 0.15 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

24972 measured reflections

2262 independent reflections

1979 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.092

S = 1.05

2262 reflections

255 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: MarvinSketch (Chemaxon, 2010 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811023403/hg5054sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023403/hg5054Isup2.hkl

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

C24H25NO	F(000) = 736
Mr = 343.45	Dx = 1.189 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7679 reflections
a = 9.9672 (2) Å	θ = 2.5–25.5°
b = 13.3376 (2) Å	µ = 0.07 mm−1
c = 14.4369 (2) Å	T = 100 K
V = 1919.22 (5) Å3	Irregular, colourless
Z = 4	0.22 × 0.15 × 0.15 mm

Bruker APEXII CCD diffractometer	1979 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.039
graphite	θmax = 26.5°, θmin = 2.1°
φ and ω scans	h = −12→12
24972 measured reflections	k = −16→16
2262 independent reflections	l = −18→18

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038	H-atom parameters constrained
wR(F2) = 0.092	w = 1/[σ2(Fo2) + (0.0477P)2 + 0.2712P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2262 reflections	Δρmax = 0.17 e Å−3
255 parameters	Δρmin = −0.19 e Å−3
0 restraints	Absolute structure: nd
Primary atom site location: structure-invariant direct methods

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	Occ. (<1)
O	0.11866 (14)	0.86869 (11)	0.21128 (12)	0.0486 (4)
H1o	0.1387	0.8166	0.1816	0.073*
N	0.30995 (17)	0.77434 (11)	0.11848 (11)	0.0360 (4)
C1	0.3091 (2)	0.74937 (15)	0.01898 (13)	0.0364 (4)
H1	0.4023	0.7558	−0.0058	0.044*
C2	0.2230 (2)	0.83278 (15)	−0.02138 (14)	0.0422 (5)
H2A	0.2437	0.8432	−0.0877	0.051*
H2B	0.1264	0.8169	−0.0149	0.051*
C3	0.2595 (2)	0.92449 (15)	0.03493 (14)	0.0409 (5)
H3A	0.1786	0.9652	0.0481	0.049*
H3B	0.3250	0.9665	0.0010	0.049*
C4	0.3212 (2)	0.88486 (13)	0.12565 (12)	0.0327 (4)
H4	0.4177	0.9050	0.1300	0.039*
C5	0.4120 (2)	0.71912 (17)	0.16989 (15)	0.0510 (6)
H5A	0.3976	0.6470	0.1619	0.076*
H5B	0.4059	0.7362	0.2358	0.076*
H5C	0.5011	0.7371	0.1465	0.076*
C12	0.24357 (19)	0.92007 (13)	0.21337 (13)	0.0333 (4)
C25	0.2101 (7)	1.0299 (5)	0.2126 (5)	0.0299 (10)	0.782 (15)
C26	0.0798 (6)	1.0643 (6)	0.2313 (5)	0.0443 (11)	0.782 (15)
H26	0.0112	1.0168	0.2439	0.053*	0.782 (15)
C27	0.0485 (7)	1.1642 (4)	0.2320 (3)	0.0504 (12)	0.782 (15)
H27	−0.0405	1.1847	0.2458	0.060*	0.782 (15)
C28	0.1454 (8)	1.2356 (3)	0.2127 (3)	0.0462 (14)	0.782 (15)
H28	0.1232	1.3049	0.2128	0.055*	0.782 (15)
C29	0.2743 (7)	1.2049 (4)	0.1933 (3)	0.0441 (15)	0.782 (15)
H29	0.3421	1.2532	0.1810	0.053*	0.782 (15)
C30	0.3055 (7)	1.1029 (6)	0.1918 (5)	0.0383 (11)	0.782 (15)
H30	0.3940	1.0827	0.1762	0.046*	0.782 (15)
C13	0.3186 (2)	0.89712 (14)	0.30368 (13)	0.0396 (5)
C14	0.2559 (3)	0.84209 (16)	0.37346 (15)	0.0563 (7)
H14	0.1668	0.8185	0.3648	0.068*
C15	0.3229 (5)	0.8218 (2)	0.45513 (17)	0.0781 (10)
H15	0.2799	0.7831	0.5017	0.094*
C16	0.4509 (4)	0.8566 (2)	0.46997 (18)	0.0800 (11)
H16	0.4959	0.8426	0.5265	0.096*
C17	0.5129 (3)	0.91177 (18)	0.40224 (18)	0.0656 (8)
H17	0.6011	0.9366	0.4121	0.079*
C18	0.4475 (2)	0.93152 (15)	0.31956 (16)	0.0479 (5)
H18	0.4920	0.9693	0.2730	0.057*
C6	0.2582 (2)	0.64512 (15)	−0.00095 (14)	0.0399 (5)
C7	0.3065 (3)	0.59257 (18)	−0.07668 (16)	0.0548 (6)
H7	0.3759	0.6207	−0.1136	0.066*
C8	0.2548 (4)	0.4995 (2)	−0.0990 (2)	0.0711 (8)
H8	0.2877	0.4650	−0.1519	0.085*
C9	0.1568 (3)	0.45654 (19)	−0.0460 (2)	0.0705 (8)
H9	0.1223	0.3923	−0.0616	0.085*
C10	0.1091 (3)	0.50665 (18)	0.0295 (2)	0.0645 (7)
H10	0.0417	0.4768	0.0670	0.077*
C11	0.1583 (3)	0.60091 (17)	0.05168 (18)	0.0544 (6)
H11	0.1230	0.6356	0.1037	0.065*
C19	0.235 (3)	1.043 (2)	0.204 (2)	0.0299 (10)	0.218 (15)
C20	0.116 (2)	1.072 (3)	0.238 (2)	0.0443 (11)	0.218 (15)
H20	0.0495	1.0280	0.2623	0.053*	0.218 (15)
C21	0.101 (3)	1.1852 (17)	0.2343 (15)	0.0504 (12)	0.218 (15)
H21	0.0187	1.2167	0.2509	0.060*	0.218 (15)
C22	0.207 (3)	1.2397 (15)	0.2064 (13)	0.0462 (14)	0.218 (15)
H22	0.1991	1.3107	0.2057	0.055*	0.218 (15)
C23	0.323 (2)	1.1984 (16)	0.1794 (14)	0.0441 (15)	0.218 (15)
H23	0.3949	1.2404	0.1602	0.053*	0.218 (15)
C24	0.340 (2)	1.098 (2)	0.179 (2)	0.0383 (11)	0.218 (15)
H24	0.4225	1.0679	0.1620	0.046*	0.218 (15)

	U11	U22	U33	U12	U13	U23
O	0.0386 (8)	0.0402 (8)	0.0671 (10)	−0.0100 (7)	0.0144 (7)	−0.0061 (7)
N	0.0446 (9)	0.0298 (8)	0.0337 (8)	0.0063 (8)	−0.0033 (8)	−0.0016 (6)
C1	0.0357 (10)	0.0407 (10)	0.0327 (10)	0.0019 (9)	0.0008 (8)	−0.0048 (8)
C2	0.0501 (12)	0.0411 (11)	0.0355 (10)	−0.0006 (10)	−0.0064 (9)	0.0013 (9)
C3	0.0459 (12)	0.0377 (10)	0.0392 (11)	−0.0011 (10)	−0.0040 (9)	0.0025 (8)
C4	0.0331 (10)	0.0304 (9)	0.0344 (9)	−0.0005 (8)	−0.0009 (8)	0.0012 (7)
C5	0.0668 (15)	0.0439 (12)	0.0423 (12)	0.0218 (11)	−0.0111 (11)	−0.0075 (9)
C12	0.0318 (9)	0.0277 (9)	0.0405 (10)	−0.0023 (8)	0.0049 (8)	−0.0005 (8)
C25	0.034 (3)	0.026 (2)	0.0295 (18)	−0.0063 (17)	0.0048 (17)	0.0031 (14)
C26	0.042 (3)	0.0436 (18)	0.047 (2)	0.008 (3)	0.005 (3)	−0.0021 (14)
C27	0.055 (3)	0.042 (2)	0.0541 (15)	0.013 (2)	0.011 (2)	−0.0058 (15)
C28	0.068 (4)	0.0304 (12)	0.0402 (14)	0.012 (2)	0.002 (2)	−0.0049 (11)
C29	0.059 (4)	0.0318 (14)	0.042 (2)	−0.005 (3)	−0.006 (2)	0.0003 (14)
C30	0.035 (3)	0.0340 (13)	0.046 (2)	−0.003 (2)	−0.002 (2)	0.0041 (16)
C13	0.0591 (13)	0.0253 (9)	0.0344 (10)	0.0074 (9)	0.0060 (9)	−0.0043 (7)
C14	0.0913 (18)	0.0380 (11)	0.0395 (12)	0.0125 (13)	0.0202 (12)	0.0008 (9)
C15	0.151 (3)	0.0489 (15)	0.0343 (13)	0.030 (2)	0.0228 (17)	0.0036 (11)
C16	0.149 (3)	0.0556 (16)	0.0352 (13)	0.042 (2)	−0.0182 (17)	−0.0086 (12)
C17	0.091 (2)	0.0513 (13)	0.0544 (15)	0.0220 (15)	−0.0274 (14)	−0.0158 (12)
C18	0.0645 (14)	0.0357 (11)	0.0434 (12)	0.0060 (11)	−0.0100 (11)	−0.0020 (9)
C6	0.0434 (11)	0.0362 (10)	0.0401 (11)	0.0066 (9)	−0.0071 (9)	−0.0035 (8)
C7	0.0678 (15)	0.0495 (13)	0.0473 (12)	0.0054 (13)	−0.0030 (12)	−0.0123 (10)
C8	0.090 (2)	0.0554 (14)	0.0674 (17)	0.0117 (15)	−0.0144 (17)	−0.0271 (13)
C9	0.0798 (19)	0.0372 (12)	0.094 (2)	0.0030 (13)	−0.0359 (18)	−0.0136 (14)
C10	0.0615 (15)	0.0442 (13)	0.088 (2)	−0.0066 (12)	−0.0111 (15)	0.0042 (14)
C11	0.0562 (14)	0.0433 (12)	0.0637 (15)	−0.0025 (11)	0.0020 (12)	−0.0047 (11)
C19	0.034 (3)	0.026 (2)	0.0295 (18)	−0.0063 (17)	0.0048 (17)	0.0031 (14)
C20	0.042 (3)	0.0436 (18)	0.047 (2)	0.008 (3)	0.005 (3)	−0.0021 (14)
C21	0.055 (3)	0.042 (2)	0.0541 (15)	0.013 (2)	0.011 (2)	−0.0058 (15)
C22	0.068 (4)	0.0304 (12)	0.0402 (14)	0.012 (2)	0.002 (2)	−0.0049 (11)
C23	0.059 (4)	0.0318 (14)	0.042 (2)	−0.005 (3)	−0.006 (2)	0.0003 (14)
C24	0.035 (3)	0.0340 (13)	0.046 (2)	−0.003 (2)	−0.002 (2)	0.0041 (16)

O—C12	1.421 (2)	C13—C18	1.383 (3)
O—H1o	0.8401	C13—C14	1.394 (3)
N—C5	1.459 (3)	C14—C15	1.382 (4)
N—C1	1.475 (2)	C14—H14	0.9500
N—C4	1.482 (2)	C15—C16	1.374 (5)
C1—C6	1.508 (3)	C15—H15	0.9500
C1—C2	1.521 (3)	C16—C17	1.371 (4)
C1—H1	1.0000	C16—H16	0.9500
C2—C3	1.513 (3)	C17—C18	1.385 (3)
C2—H2A	0.9900	C17—H17	0.9500
C2—H2B	0.9900	C18—H18	0.9500
C3—C4	1.541 (3)	C6—C11	1.384 (3)
C3—H3A	0.9900	C6—C7	1.385 (3)
C3—H3B	0.9900	C7—C8	1.383 (4)
C4—C12	1.557 (3)	C7—H7	0.9500
C4—H4	1.0000	C8—C9	1.366 (5)
C5—H5A	0.9800	C8—H8	0.9500
C5—H5B	0.9800	C9—C10	1.364 (4)
C5—H5C	0.9800	C9—H9	0.9500
C12—C25	1.503 (7)	C10—C11	1.387 (3)
C12—C13	1.534 (3)	C10—H10	0.9500
C12—C19	1.65 (3)	C11—H11	0.9500
C25—C30	1.394 (7)	C19—C24	1.32 (3)
C25—C26	1.403 (9)	C19—C20	1.34 (4)
C26—C27	1.368 (9)	C20—C21	1.51 (4)
C26—H26	0.9500	C20—H20	0.9500
C27—C28	1.385 (6)	C21—C22	1.34 (2)
C27—H27	0.9500	C21—H21	0.9500
C28—C29	1.378 (5)	C22—C23	1.34 (2)
C28—H28	0.9500	C22—H22	0.9500
C29—C30	1.395 (9)	C23—C24	1.35 (4)
C29—H29	0.9500	C23—H23	0.9500
C30—H30	0.9500	C24—H24	0.9500
C12—O—H1o	101.6	C25—C30—C29	121.7 (5)
C5—N—C1	112.69 (16)	C25—C30—H30	119.1
C5—N—C4	114.43 (16)	C29—C30—H30	119.1
C1—N—C4	107.05 (14)	C18—C13—C14	118.1 (2)
N—C1—C6	113.34 (16)	C18—C13—C12	121.84 (18)
N—C1—C2	102.20 (16)	C14—C13—C12	120.0 (2)
C6—C1—C2	114.29 (17)	C15—C14—C13	120.2 (3)
N—C1—H1	108.9	C15—C14—H14	119.9
C6—C1—H1	108.9	C13—C14—H14	119.9
C2—C1—H1	108.9	C16—C15—C14	121.0 (3)
C3—C2—C1	104.46 (16)	C16—C15—H15	119.5
C3—C2—H2A	110.9	C14—C15—H15	119.5
C1—C2—H2A	110.9	C17—C16—C15	119.3 (3)
C3—C2—H2B	110.9	C17—C16—H16	120.4
C1—C2—H2B	110.9	C15—C16—H16	120.4
H2A—C2—H2B	108.9	C16—C17—C18	120.3 (3)
C2—C3—C4	105.99 (16)	C16—C17—H17	119.8
C2—C3—H3A	110.5	C18—C17—H17	119.8
C4—C3—H3A	110.5	C13—C18—C17	121.1 (2)
C2—C3—H3B	110.5	C13—C18—H18	119.5
C4—C3—H3B	110.5	C17—C18—H18	119.5
H3A—C3—H3B	108.7	C11—C6—C7	117.9 (2)
N—C4—C3	104.56 (15)	C11—C6—C1	122.02 (19)
N—C4—C12	108.61 (15)	C7—C6—C1	120.0 (2)
C3—C4—C12	112.90 (15)	C8—C7—C6	120.6 (3)
N—C4—H4	110.2	C8—C7—H7	119.7
C3—C4—H4	110.2	C6—C7—H7	119.7
C12—C4—H4	110.2	C9—C8—C7	120.8 (3)
N—C5—H5A	109.5	C9—C8—H8	119.6
N—C5—H5B	109.5	C7—C8—H8	119.6
H5A—C5—H5B	109.5	C10—C9—C8	119.4 (3)
N—C5—H5C	109.5	C10—C9—H9	120.3
H5A—C5—H5C	109.5	C8—C9—H9	120.3
H5B—C5—H5C	109.5	C9—C10—C11	120.3 (3)
O—C12—C25	106.0 (3)	C9—C10—H10	119.8
O—C12—C13	110.43 (16)	C11—C10—H10	119.8
C25—C12—C13	108.0 (3)	C6—C11—C10	120.9 (2)
O—C12—C4	105.84 (15)	C6—C11—H11	119.5
C25—C12—C4	113.5 (3)	C10—C11—H11	119.5
C13—C12—C4	112.86 (15)	C24—C19—C20	130 (3)
O—C12—C19	115.5 (11)	C24—C19—C12	122 (2)
C13—C12—C19	107.2 (12)	C20—C19—C12	108 (2)
C4—C12—C19	105.0 (10)	C19—C20—C21	111 (2)
C30—C25—C26	116.4 (6)	C19—C20—H20	124.5
C30—C25—C12	122.1 (5)	C21—C20—H20	124.5
C26—C25—C12	121.5 (5)	C22—C21—C20	118.2 (18)
C27—C26—C25	122.1 (5)	C22—C21—H21	120.9
C27—C26—H26	119.0	C20—C21—H21	120.9
C25—C26—H26	119.0	C23—C22—C21	123.0 (18)
C26—C27—C28	120.6 (4)	C23—C22—H22	118.5
C26—C27—H27	119.7	C21—C22—H22	118.5
C28—C27—H27	119.7	C22—C23—C24	121 (2)
C29—C28—C27	119.1 (4)	C22—C23—H23	119.5
C29—C28—H28	120.4	C24—C23—H23	119.5
C27—C28—H28	120.4	C19—C24—C23	117 (2)
C28—C29—C30	120.0 (4)	C19—C24—H24	121.7
C28—C29—H29	120.0	C23—C24—H24	121.7
C30—C29—H29	120.0
C5—N—C1—C6	70.2 (2)	O—C12—C13—C14	−6.8 (2)
C4—N—C1—C6	−163.11 (17)	C25—C12—C13—C14	108.7 (3)
C5—N—C1—C2	−166.29 (18)	C4—C12—C13—C14	−124.99 (18)
C4—N—C1—C2	−39.6 (2)	C19—C12—C13—C14	119.8 (10)
N—C1—C2—C3	36.6 (2)	C18—C13—C14—C15	−1.0 (3)
C6—C1—C2—C3	159.41 (17)	C12—C13—C14—C15	−179.62 (19)
C1—C2—C3—C4	−20.7 (2)	C13—C14—C15—C16	1.2 (4)
C5—N—C4—C3	152.32 (17)	C14—C15—C16—C17	−0.4 (4)
C1—N—C4—C3	26.7 (2)	C15—C16—C17—C18	−0.4 (4)
C5—N—C4—C12	−86.9 (2)	C14—C13—C18—C17	0.2 (3)
C1—N—C4—C12	147.48 (16)	C12—C13—C18—C17	178.72 (19)
C2—C3—C4—N	−3.0 (2)	C16—C17—C18—C13	0.6 (3)
C2—C3—C4—C12	−120.85 (18)	N—C1—C6—C11	34.1 (3)
N—C4—C12—O	−45.89 (19)	C2—C1—C6—C11	−82.4 (2)
C3—C4—C12—O	69.60 (19)	N—C1—C6—C7	−149.2 (2)
N—C4—C12—C25	−161.7 (3)	C2—C1—C6—C7	94.2 (2)
C3—C4—C12—C25	−46.2 (4)	C11—C6—C7—C8	0.8 (3)
N—C4—C12—C13	75.00 (19)	C1—C6—C7—C8	−176.0 (2)
C3—C4—C12—C13	−169.51 (16)	C6—C7—C8—C9	−1.3 (4)
N—C4—C12—C19	−168.5 (12)	C7—C8—C9—C10	0.5 (4)
C3—C4—C12—C19	−53.1 (12)	C8—C9—C10—C11	0.7 (4)
O—C12—C25—C30	−164.1 (6)	C7—C6—C11—C10	0.4 (3)
C13—C12—C25—C30	77.5 (7)	C1—C6—C11—C10	177.2 (2)
C4—C12—C25—C30	−48.4 (8)	C9—C10—C11—C6	−1.2 (4)
C19—C12—C25—C30	−10 (7)	O—C12—C19—C24	−161 (3)
O—C12—C25—C26	14.7 (7)	C25—C12—C19—C24	172 (10)
C13—C12—C25—C26	−103.7 (7)	C13—C12—C19—C24	76 (3)
C4—C12—C25—C26	130.4 (6)	C4—C12—C19—C24	−45 (3)
C19—C12—C25—C26	169 (8)	O—C12—C19—C20	28 (3)
C30—C25—C26—C27	−2.0 (11)	C25—C12—C19—C20	1(6)
C12—C25—C26—C27	179.2 (6)	C13—C12—C19—C20	−95 (2)
C25—C26—C27—C28	0.9 (10)	C4—C12—C19—C20	144 (2)
C26—C27—C28—C29	−0.4 (7)	C24—C19—C20—C21	9(5)
C27—C28—C29—C30	1.0 (7)	C12—C19—C20—C21	179 (2)
C26—C25—C30—C29	2.6 (11)	C19—C20—C21—C22	−6(4)
C12—C25—C30—C29	−178.5 (5)	C20—C21—C22—C23	2(4)
C28—C29—C30—C25	−2.2 (9)	C21—C22—C23—C24	0(4)
O—C12—C13—C18	174.73 (17)	C20—C19—C24—C23	−7(5)
C25—C12—C13—C18	−69.8 (3)	C12—C19—C24—C23	−176 (2)
C4—C12—C13—C18	56.5 (2)	C22—C23—C24—C19	2(4)
C19—C12—C13—C18	−58.7 (10)

Cg is the centroid of the C6–C11 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O—H1O···N	0.84	2.02	2.648 (2)	132
C28—H28···Oi	0.95	2.78	3.359 (7)	120
C17—H17···Cgii	0.95	2.92	3.776 (3)	150

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C6–C11 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O—H1O⋯N	0.84	2.02	2.648 (2)	132
C28—H28⋯Oi	0.95	2.78	3.359 (7)	120
C17—H17⋯Cgii	0.95	2.92	3.776 (3)	150

Symmetry codes: (i) ; (ii) .