A functionalized enol lactone containing a protected α-amino acid.

The crystal structure of N-(3,9-dimethyl-4-phenyl-2,5-dioxo-3,4-dihydro-2H,5H-pyrano[3,2-c]chromen-3-yl)-N-methylbenzamide methanol monosolvate, C(28)H(23)NO(5)·CH(3)OH, has been determined at room temperature by X-ray diffraction. Structural parameters are discussed with reference to ab initio calculations.

Related literature

For structures containing enol lactone fragments, see: Murray et al. (1982 ▶); Harborne & Baxter (1999 ▶); Qabaja et al. (2000 ▶). For related structures containing a coumarin fragment, see: Yu et al. (2003 ▶). For a phenyl­furo[3,2-c]chromen-4-one structure, see: Bruno et al. (2001 ▶). For related furan-5-one structures, see: Grassi et al. (2002 ▶). For the Cambridge Structural Database, see: Allen (2002 ▶). For the GAUSSIAN98 software used for the ab initio calculations, see: Frisch et al. (1998 ▶). For the synthetic process used, see: Grassi et al. (2003 ▶). For background to O—C—O bond-angle asymmetry, see: Kokila et al. (1996 ▶).

Experimental

Crystal data

C28H23NO5·CH4O

M = 485.52

Monoclinic,

a = 10.7435 (14) Å

b = 9.9056 (17) Å

c = 23.298 (3) Å

β = 94.817 (7)°

V = 2470.7 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.58 × 0.38 × 0.36 mm

Data collection

Siemens P4 diffractometer

Absorption correction: ψ scan (Kopfmann & Huber, 1968 ▶) T min = 0.870, T max = 0.968

9535 measured reflections

4347 independent reflections

2843 reflections with I > 2σ(I)

R int = 0.036

3 standard reflections every 197 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.132

S = 1.01

4347 reflections

331 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.31 e Å−3

Data collection: XSCANS (Bruker, 1999 ▶); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 2008 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XPW (Siemens, 1996 ▶); software used to prepare material for publication: PARST97 (Nardelli, 1995 ▶) and SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810043709/jh2217sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043709/jh2217Isup2.hkl

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

C28H23NO5·CH4O	F(000) = 1024
Mr = 485.52	Dx = 1.305 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 59 reflections
a = 10.7435 (14) Å	θ = 7.7–17.5°
b = 9.9056 (17) Å	µ = 0.09 mm−1
c = 23.298 (3) Å	T = 298 K
β = 94.817 (7)°	Irregular, colourless
V = 2470.7 (6) Å3	0.58 × 0.38 × 0.36 mm
Z = 4

Siemens P4 diffractometer	2843 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.036
graphite	θmax = 25.0°, θmin = 2.0°
ω scans	h = −12→12
Absorption correction: ψ scan (Kopfmann & Huber, 1968)	k = −1→11
Tmin = 0.870, Tmax = 0.968	l = −27→27
9535 measured reflections	3 standard reflections every 197 reflections
4347 independent reflections	intensity decay: none

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)] = 0.049	H-atom parameters constrained
wR(F2) = 0.132	w = 1/[σ2(Fo2) + (0.0533P)2 + 0.7913P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
4347 reflections	Δρmax = 0.18 e Å−3
331 parameters	Δρmin = −0.31 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0036 (8)

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	Occ. (<1)
O1	0.50718 (15)	0.77955 (19)	0.49310 (6)	0.0560 (5)
C2	0.6021 (2)	0.8610 (3)	0.51636 (10)	0.0490 (6)
C3	0.64762 (19)	0.8378 (2)	0.57594 (9)	0.0440 (6)
C4	0.5962 (2)	0.7392 (2)	0.60580 (9)	0.0456 (6)
C5	0.4958 (2)	0.6556 (3)	0.58143 (10)	0.0483 (6)
C6	0.4409 (2)	0.5503 (3)	0.61028 (12)	0.0588 (7)
H6	0.4684	0.5327	0.6485	0.071*
C7	0.3471 (2)	0.4720 (3)	0.58354 (14)	0.0675 (8)
C8	0.3087 (2)	0.5014 (3)	0.52619 (15)	0.0735 (9)
H8	0.2451	0.4500	0.5075	0.088*
C9	0.3612 (2)	0.6034 (3)	0.49630 (12)	0.0655 (8)
H9	0.3340	0.6203	0.4580	0.079*
C10	0.4550 (2)	0.6802 (3)	0.52418 (10)	0.0512 (6)
O11	0.64195 (16)	0.9454 (2)	0.48534 (7)	0.0649 (5)
C12	0.75139 (19)	0.9241 (3)	0.60261 (9)	0.0442 (6)
H12	0.7380	1.0154	0.5872	0.053*
C13	0.7374 (2)	0.9318 (3)	0.66888 (9)	0.0447 (6)
C14	0.7351 (2)	0.7859 (3)	0.68848 (9)	0.0491 (6)
O15	0.64021 (15)	0.70590 (17)	0.66098 (6)	0.0538 (4)
C16	0.2891 (3)	0.3579 (3)	0.61477 (16)	0.0964 (11)
H16A	0.2461	0.2984	0.5873	0.145*	0.50
H16B	0.2310	0.3938	0.6399	0.145*	0.50
H16C	0.3533	0.3087	0.6370	0.145*	0.50
H16D	0.3075	0.3689	0.6555	0.145*	0.50
H16E	0.3226	0.2735	0.6029	0.145*	0.50
H16F	0.2003	0.3585	0.6058	0.145*	0.50
C17	0.8802 (2)	0.8790 (3)	0.58752 (9)	0.0493 (6)
C18	0.9676 (2)	0.9762 (3)	0.57662 (11)	0.0684 (8)
H18	0.9468	1.0670	0.5789	0.082*
C19	1.0865 (3)	0.9398 (4)	0.56224 (12)	0.0835 (10)
H19	1.1443	1.0064	0.5552	0.100*
C20	1.1177 (3)	0.8095 (5)	0.55848 (13)	0.0848 (11)
H20	1.1971	0.7857	0.5490	0.102*
C21	1.0328 (3)	0.7111 (4)	0.56862 (13)	0.0832 (10)
H21	1.0546	0.6207	0.5658	0.100*
C22	0.9136 (2)	0.7461 (3)	0.58313 (11)	0.0633 (7)
H22	0.8563	0.6787	0.5899	0.076*
C23	0.8437 (2)	1.0061 (3)	0.70278 (10)	0.0583 (7)
H23A	0.8475	1.0973	0.6891	0.087*
H23B	0.9212	0.9613	0.6977	0.087*
H23C	0.8294	1.0067	0.7429	0.087*
N24	0.61573 (15)	0.9977 (2)	0.67699 (7)	0.0444 (5)
C25	0.5853 (2)	1.1225 (3)	0.64515 (11)	0.0613 (7)
H25A	0.6605	1.1728	0.6412	0.092*
H25B	0.5290	1.1756	0.6657	0.092*
H25C	0.5467	1.1007	0.6076	0.092*
C26	0.5548 (2)	0.9634 (3)	0.72315 (10)	0.0490 (6)
O27	0.59794 (16)	0.8770 (2)	0.75754 (7)	0.0659 (5)
C28	0.4305 (2)	1.0259 (3)	0.73030 (10)	0.0502 (6)
C29	0.3308 (2)	1.0086 (3)	0.68954 (12)	0.0716 (8)
H29	0.3414	0.9615	0.6558	0.086*
C30	0.2151 (2)	1.0614 (4)	0.69901 (14)	0.0843 (10)
H30	0.1477	1.0472	0.6719	0.101*
C31	0.1984 (3)	1.1333 (4)	0.74701 (14)	0.0807 (9)
H31	0.1206	1.1700	0.7526	0.097*
C32	0.2965 (3)	1.1516 (4)	0.78720 (13)	0.0806 (9)
H32	0.2856	1.2013	0.8203	0.097*
C33	0.4116 (2)	1.0973 (3)	0.77930 (11)	0.0657 (8)
H33	0.4773	1.1091	0.8075	0.079*
O34	0.81109 (15)	0.7302 (2)	0.72014 (7)	0.0637 (5)
C34	0.5741 (5)	0.8527 (5)	0.8947 (2)	0.1397 (17)
H34A	0.5325	0.7866	0.8698	0.210*
H34B	0.5214	0.9305	0.8969	0.210*
H34C	0.5915	0.8150	0.9325	0.210*
O35	0.6784 (3)	0.8881 (7)	0.87417 (13)	0.208 (2)
H35	0.6675	0.8947	0.8390	0.312*

	U11	U22	U33	U12	U13	U23
O1	0.0512 (9)	0.0702 (12)	0.0453 (9)	0.0038 (9)	−0.0040 (7)	−0.0002 (9)
C2	0.0414 (12)	0.0628 (17)	0.0433 (12)	0.0088 (12)	0.0060 (10)	−0.0008 (13)
C3	0.0388 (11)	0.0561 (15)	0.0378 (11)	0.0061 (11)	0.0068 (9)	0.0007 (11)
C4	0.0450 (12)	0.0535 (15)	0.0383 (11)	0.0068 (12)	0.0044 (9)	−0.0019 (11)
C5	0.0400 (12)	0.0528 (15)	0.0533 (14)	0.0048 (11)	0.0110 (10)	−0.0051 (12)
C6	0.0509 (14)	0.0589 (17)	0.0680 (16)	0.0005 (13)	0.0135 (12)	−0.0055 (14)
C7	0.0489 (15)	0.0576 (18)	0.099 (2)	−0.0006 (14)	0.0214 (15)	−0.0127 (17)
C8	0.0433 (14)	0.074 (2)	0.102 (2)	−0.0026 (15)	0.0015 (15)	−0.0291 (19)
C9	0.0494 (15)	0.076 (2)	0.0696 (17)	0.0070 (15)	−0.0045 (13)	−0.0197 (16)
C10	0.0397 (12)	0.0585 (17)	0.0553 (14)	0.0072 (12)	0.0041 (11)	−0.0069 (13)
O11	0.0640 (11)	0.0864 (14)	0.0446 (9)	−0.0029 (10)	0.0072 (8)	0.0148 (10)
C12	0.0405 (12)	0.0535 (15)	0.0390 (11)	0.0011 (11)	0.0058 (9)	0.0027 (11)
C13	0.0387 (12)	0.0575 (16)	0.0382 (11)	0.0040 (11)	0.0043 (9)	−0.0002 (11)
C14	0.0447 (12)	0.0655 (17)	0.0373 (11)	0.0055 (13)	0.0060 (10)	0.0006 (12)
O15	0.0619 (10)	0.0573 (11)	0.0417 (8)	−0.0035 (9)	0.0011 (7)	0.0069 (8)
C16	0.076 (2)	0.076 (2)	0.141 (3)	−0.0171 (18)	0.029 (2)	−0.003 (2)
C17	0.0421 (12)	0.0686 (18)	0.0378 (12)	−0.0006 (13)	0.0079 (10)	−0.0013 (12)
C18	0.0584 (16)	0.086 (2)	0.0632 (16)	−0.0079 (16)	0.0182 (13)	−0.0048 (16)
C19	0.0550 (17)	0.129 (3)	0.0698 (19)	−0.015 (2)	0.0224 (14)	−0.009 (2)
C20	0.0500 (16)	0.138 (3)	0.0687 (19)	0.014 (2)	0.0170 (14)	−0.014 (2)
C21	0.0671 (19)	0.103 (3)	0.081 (2)	0.027 (2)	0.0170 (16)	−0.0044 (19)
C22	0.0546 (15)	0.073 (2)	0.0631 (16)	0.0080 (15)	0.0110 (12)	−0.0009 (14)
C23	0.0463 (13)	0.0765 (19)	0.0518 (13)	−0.0025 (14)	0.0015 (11)	−0.0070 (14)
N24	0.0397 (10)	0.0542 (12)	0.0397 (9)	0.0036 (9)	0.0068 (8)	0.0038 (9)
C25	0.0583 (15)	0.0686 (19)	0.0586 (15)	0.0116 (14)	0.0158 (12)	0.0123 (14)
C26	0.0455 (13)	0.0591 (16)	0.0427 (12)	0.0009 (12)	0.0049 (10)	−0.0023 (12)
O27	0.0669 (11)	0.0826 (14)	0.0501 (10)	0.0178 (11)	0.0156 (8)	0.0156 (10)
C28	0.0417 (12)	0.0607 (16)	0.0490 (13)	−0.0030 (12)	0.0091 (10)	0.0024 (12)
C29	0.0502 (15)	0.100 (2)	0.0642 (16)	−0.0008 (16)	0.0047 (12)	−0.0214 (17)
C30	0.0403 (15)	0.128 (3)	0.084 (2)	−0.0023 (17)	−0.0005 (14)	−0.011 (2)
C31	0.0505 (16)	0.113 (3)	0.081 (2)	0.0139 (17)	0.0204 (15)	−0.002 (2)
C32	0.0637 (18)	0.107 (3)	0.0732 (19)	0.0124 (18)	0.0176 (15)	−0.0207 (18)
C33	0.0503 (14)	0.091 (2)	0.0564 (15)	0.0016 (15)	0.0070 (12)	−0.0154 (15)
O34	0.0554 (10)	0.0799 (13)	0.0549 (10)	0.0163 (10)	−0.0014 (8)	0.0164 (10)
C34	0.159 (4)	0.135 (4)	0.128 (4)	0.009 (4)	0.024 (3)	0.029 (3)
O35	0.140 (3)	0.398 (7)	0.0822 (19)	0.048 (4)	−0.0186 (19)	0.013 (3)

O1—C10	1.369 (3)	C18—H18	0.9300
O1—C2	1.376 (3)	C19—C20	1.339 (5)
C2—O11	1.206 (3)	C19—H19	0.9300
C2—C3	1.451 (3)	C20—C21	1.369 (5)
C3—C4	1.344 (3)	C20—H20	0.9300
C3—C12	1.498 (3)	C21—C22	1.395 (4)
C4—O15	1.372 (3)	C21—H21	0.9300
C4—C5	1.438 (3)	C22—H22	0.9300
C5—C10	1.390 (3)	C23—H23A	0.9600
C5—C6	1.398 (3)	C23—H23B	0.9600
C6—C7	1.379 (4)	C23—H23C	0.9600
C6—H6	0.9300	N24—C26	1.349 (3)
C7—C8	1.396 (4)	N24—C25	1.464 (3)
C7—C16	1.507 (4)	C25—H25A	0.9600
C8—C9	1.375 (4)	C25—H25B	0.9600
C8—H8	0.9300	C25—H25C	0.9600
C9—C10	1.381 (4)	C26—O27	1.236 (3)
C9—H9	0.9300	C26—C28	1.493 (3)
C12—C17	1.524 (3)	C28—C33	1.373 (3)
C12—C13	1.566 (3)	C28—C29	1.382 (3)
C12—H12	0.9800	C29—C30	1.383 (4)
C13—N24	1.488 (3)	C29—H29	0.9300
C13—C14	1.516 (4)	C30—C31	1.351 (4)
C13—C23	1.523 (3)	C30—H30	0.9300
C14—O34	1.189 (3)	C31—C32	1.362 (4)
C14—O15	1.403 (3)	C31—H31	0.9300
C16—H16A	0.9600	C32—C33	1.374 (4)
C16—H16B	0.9600	C32—H32	0.9300
C16—H16C	0.9600	C33—H33	0.9300
C16—H16D	0.9600	C34—O35	1.302 (5)
C16—H16E	0.9600	C34—H34A	0.9600
C16—H16F	0.9600	C34—H34B	0.9600
C17—C22	1.371 (4)	C34—H34C	0.9600
C17—C18	1.382 (4)	O35—H35	0.8200
C18—C19	1.395 (4)
C10—O1—C2	122.43 (19)	H16D—C16—H16F	109.5
O11—C2—O1	117.3 (2)	H16E—C16—H16F	109.5
O11—C2—C3	125.1 (2)	C22—C17—C18	118.0 (2)
O1—C2—C3	117.6 (2)	C22—C17—C12	123.1 (2)
C4—C3—C2	119.4 (2)	C18—C17—C12	118.8 (2)
C4—C3—C12	121.6 (2)	C17—C18—C19	120.9 (3)
C2—C3—C12	119.0 (2)	C17—C18—H18	119.5
C3—C4—O15	122.4 (2)	C19—C18—H18	119.5
C3—C4—C5	122.8 (2)	C20—C19—C18	120.3 (3)
O15—C4—C5	114.8 (2)	C20—C19—H19	119.9
C10—C5—C6	118.7 (2)	C18—C19—H19	119.9
C10—C5—C4	116.3 (2)	C19—C20—C21	120.1 (3)
C6—C5—C4	124.9 (2)	C19—C20—H20	120.0
C7—C6—C5	121.6 (3)	C21—C20—H20	120.0
C7—C6—H6	119.2	C20—C21—C22	120.3 (3)
C5—C6—H6	119.2	C20—C21—H21	119.9
C6—C7—C8	117.5 (3)	C22—C21—H21	119.9
C6—C7—C16	121.4 (3)	C17—C22—C21	120.5 (3)
C8—C7—C16	121.2 (3)	C17—C22—H22	119.8
C9—C8—C7	122.5 (3)	C21—C22—H22	119.8
C9—C8—H8	118.8	C13—C23—H23A	109.5
C7—C8—H8	118.8	C13—C23—H23B	109.5
C8—C9—C10	118.8 (3)	H23A—C23—H23B	109.5
C8—C9—H9	120.6	C13—C23—H23C	109.5
C10—C9—H9	120.6	H23A—C23—H23C	109.5
O1—C10—C9	117.6 (2)	H23B—C23—H23C	109.5
O1—C10—C5	121.5 (2)	C26—N24—C25	121.0 (2)
C9—C10—C5	120.9 (3)	C26—N24—C13	118.76 (19)
C3—C12—C17	113.34 (19)	C25—N24—C13	117.86 (18)
C3—C12—C13	107.90 (17)	N24—C25—H25A	109.5
C17—C12—C13	113.96 (17)	N24—C25—H25B	109.5
C3—C12—H12	107.1	H25A—C25—H25B	109.5
C17—C12—H12	107.1	N24—C25—H25C	109.5
C13—C12—H12	107.1	H25A—C25—H25C	109.5
N24—C13—C14	110.10 (18)	H25B—C25—H25C	109.5
N24—C13—C23	110.53 (19)	O27—C26—N24	120.7 (2)
C14—C13—C23	109.6 (2)	O27—C26—C28	120.3 (2)
N24—C13—C12	107.74 (16)	N24—C26—C28	118.9 (2)
C14—C13—C12	104.82 (19)	C33—C28—C29	118.3 (2)
C23—C13—C12	113.90 (18)	C33—C28—C26	120.2 (2)
O34—C14—O15	117.1 (2)	C29—C28—C26	121.4 (2)
O34—C14—C13	127.0 (2)	C28—C29—C30	119.9 (3)
O15—C14—C13	115.49 (19)	C28—C29—H29	120.0
C4—O15—C14	118.16 (18)	C30—C29—H29	120.0
C7—C16—H16A	109.5	C31—C30—C29	121.0 (3)
C7—C16—H16B	109.5	C31—C30—H30	119.5
H16A—C16—H16B	109.5	C29—C30—H30	119.5
C7—C16—H16C	109.5	C30—C31—C32	119.4 (3)
H16A—C16—H16C	109.5	C30—C31—H31	120.3
H16B—C16—H16C	109.5	C32—C31—H31	120.3
C7—C16—H16D	109.5	C31—C32—C33	120.6 (3)
H16A—C16—H16D	141.1	C31—C32—H32	119.7
H16B—C16—H16D	56.3	C33—C32—H32	119.7
H16C—C16—H16D	56.3	C28—C33—C32	120.7 (3)
C7—C16—H16E	109.5	C28—C33—H33	119.6
H16A—C16—H16E	56.3	C32—C33—H33	119.6
H16B—C16—H16E	141.1	O35—C34—H34A	109.5
H16C—C16—H16E	56.3	O35—C34—H34B	109.5
H16D—C16—H16E	109.5	H34A—C34—H34B	109.5
C7—C16—H16F	109.5	O35—C34—H34C	109.5
H16A—C16—H16F	56.3	H34A—C34—H34C	109.5
H16B—C16—H16F	56.3	H34B—C34—H34C	109.5
H16C—C16—H16F	141.1	C34—O35—H35	109.5
C10—O1—C2—O11	179.8 (2)	N24—C13—C14—O15	57.6 (2)
C10—O1—C2—C3	0.6 (3)	C23—C13—C14—O15	179.33 (17)
O11—C2—C3—C4	−179.2 (2)	C12—C13—C14—O15	−58.1 (2)
O1—C2—C3—C4	−0.1 (3)	C3—C4—O15—C14	5.6 (3)
O11—C2—C3—C12	0.5 (3)	C5—C4—O15—C14	−177.71 (18)
O1—C2—C3—C12	179.67 (19)	O34—C14—O15—C4	−144.9 (2)
C2—C3—C4—O15	175.6 (2)	C13—C14—O15—C4	28.2 (3)
C12—C3—C4—O15	−4.2 (3)	C3—C12—C17—C22	−38.0 (3)
C2—C3—C4—C5	−0.8 (3)	C13—C12—C17—C22	85.9 (3)
C12—C3—C4—C5	179.5 (2)	C3—C12—C17—C18	140.8 (2)
C3—C4—C5—C10	1.1 (3)	C13—C12—C17—C18	−95.3 (3)
O15—C4—C5—C10	−175.52 (19)	C22—C17—C18—C19	−0.7 (4)
C3—C4—C5—C6	178.7 (2)	C12—C17—C18—C19	−179.5 (2)
O15—C4—C5—C6	2.0 (3)	C17—C18—C19—C20	0.3 (5)
C10—C5—C6—C7	−0.7 (4)	C18—C19—C20—C21	0.1 (5)
C4—C5—C6—C7	−178.2 (2)	C19—C20—C21—C22	−0.2 (5)
C5—C6—C7—C8	0.1 (4)	C18—C17—C22—C21	0.6 (4)
C5—C6—C7—C16	179.5 (2)	C12—C17—C22—C21	179.4 (2)
C6—C7—C8—C9	0.4 (4)	C20—C21—C22—C17	−0.1 (4)
C16—C7—C8—C9	−178.9 (3)	C14—C13—N24—C26	35.9 (3)
C7—C8—C9—C10	−0.4 (4)	C23—C13—N24—C26	−85.3 (3)
C2—O1—C10—C9	−179.3 (2)	C12—C13—N24—C26	149.6 (2)
C2—O1—C10—C5	−0.3 (3)	C14—C13—N24—C25	−161.6 (2)
C8—C9—C10—O1	178.8 (2)	C23—C13—N24—C25	77.2 (2)
C8—C9—C10—C5	−0.1 (4)	C12—C13—N24—C25	−47.8 (3)
C6—C5—C10—O1	−178.3 (2)	C25—N24—C26—O27	−163.2 (2)
C4—C5—C10—O1	−0.6 (3)	C13—N24—C26—O27	−1.3 (3)
C6—C5—C10—C9	0.7 (3)	C25—N24—C26—C28	20.1 (3)
C4—C5—C10—C9	178.4 (2)	C13—N24—C26—C28	−177.9 (2)
C4—C3—C12—C17	98.8 (2)	O27—C26—C28—C33	61.0 (4)
C2—C3—C12—C17	−80.9 (3)	N24—C26—C28—C33	−122.4 (3)
C4—C3—C12—C13	−28.3 (3)	O27—C26—C28—C29	−116.1 (3)
C2—C3—C12—C13	151.9 (2)	N24—C26—C28—C29	60.5 (3)
C3—C12—C13—N24	−62.3 (2)	C33—C28—C29—C30	−0.8 (4)
C17—C12—C13—N24	170.9 (2)	C26—C28—C29—C30	176.3 (3)
C3—C12—C13—C14	55.0 (2)	C28—C29—C30—C31	1.9 (5)
C17—C12—C13—C14	−71.8 (2)	C29—C30—C31—C32	−1.4 (5)
C3—C12—C13—C23	174.7 (2)	C30—C31—C32—C33	−0.2 (5)
C17—C12—C13—C23	47.9 (3)	C29—C28—C33—C32	−0.8 (4)
N24—C13—C14—O34	−130.1 (2)	C26—C28—C33—C32	−177.9 (3)
C23—C13—C14—O34	−8.3 (3)	C31—C32—C33—C28	1.3 (5)
C12—C13—C14—O34	114.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O35—H35···O27	0.82	1.99	2.784 (3)	163
C9—H9···O35i	0.93	2.46	3.320 (4)	153
C19—H19···O11ii	0.93	2.60	3.403 (3)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O35—H35⋯O27	0.82	1.99	2.784 (3)	163
C9—H9⋯O35i	0.93	2.46	3.320 (4)	153
C19—H19⋯O11ii	0.93	2.60	3.403 (3)	144

Symmetry codes: (i) ; (ii) .