Methyl 3-benzoyl-8-hydroxy-5-methoxy­indolizine-1-carboxyl­ate

Usman, A.; Li, Y.; Zhang, Y.; Fun, H.-K.; Xu, J.-H.

doi:10.1107/S1600536802021165

Buy article online - an online subscription or single-article purchase is required to access this article.

Methyl 3-benzoyl-8-hydroxy-5-methoxyindolizine-1-carboxylate

A. Usman, Y. Li, Y. Zhang, H.-K. Fun and J.-H. Xu

In the title compound, C₁₈H₁₅NO₅, the methoxycarbonyl substituent, disregarding H atoms, is almost coplanar with the indolizine ring system in each of the two crystallographically independent molecules in the asymmetric unit. In the crystal structure, symmetry-related molecules form molecular dimers, held together by two C—H

O hydrogen bonds, and are interconnected into a three-dimensional network by another C—H

O hydrogen bond.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802021165/wn6127sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536802021165/wn6127Isup2.hkl Contains datablock I

CCDC reference: 202352

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R factor = 0.041
wR factor = 0.119
Data-to-parameter ratio = 12.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

Comment top

Photoinduced oxygenation reactions of indolizine derivatives have been intensively investigated (Tian et al., 2001). In continuation of this work, we prepared the title compound, (I), by photoinduced oxygenation of 1,3-dibenzoylindolizine. As part of this work, we report here the crystal structure of (I).

The asymmetric unit of (I) consists of two crystallographically independent molecules, A and B. These are related by a local twofold axis, coupled with a shift of 2.15 Å parallel to this axis. The bond lengths and angles in the two molecules (Fig. 1) are in good agreement with each other, and the values are within normal ranges (Allen et al., 1987).

In both molecules, A and B, the methoxycarbonyl groups (O3/O4/C9/C10) are almost coplanar with the indolizine ring system. The plane of the methoxycarbonyl group is twisted about the C8—C9 bond by an angle of 5.8 (1)° in molecule A and by an angle of 5.1 (1)° in molecule B. Coplanarity is maintained by an intramolecular O1—H1A···O3 hydrogen bond, linking the methoxycarbonyl and hydroxyl group (Fig. 1). The methoxy group (O2/C11), attached at atom C3, is slightly twisted out of the plane of the indolizine system, with a similar orientation in both molecules. The C4—C3—O2—C11 torsion angles are 24.3 (2) and 18.7 (3)° in molecules A and B, respectively, indicating that the methoxy group tends to deviate from coplanarity with the attached aromatic ring, as commonly observed in anisoles (Domiano et al., 1979).

The relative configuration of the benzoyl substituent (O5/C12–C18) with respect to the indolizine is influenced by the sp² hybridization of atom C12. In molecule A, the C2—C12—C13 angle is 121.3 (1)°, while the dihedral angle between the aromatic rings of the benzoyl group and the indolizine system is 64.6 (1)°. In molecule B, the corresponding values are 119.9 (1) and 61.8 (1)°, respectively. In the benzoyl substituent, atom O5 is out of the plane of the aromatic ring, such that the O5/C2/C12/C13 plane is twisted from the plane of the aromatic ring by an angle of 34.5 (1)° in molecule A and by an angle of 26.4 (1)° in molecule B.

In the crystal structure, two symmetry-related A molecules and two symmetry-related B molecules form molecular dimers (Fig. 2), by intermolecular C18—H18···O3 hydrogen bonds (Table 2). The dimers are interconnected into a three-dimensional network by C11A—H11A···O1Bⁱ hydrogen bonds [symmetry code: (i) 2 − x, 1 − y, −z].

Experimental top

The title compound was isolated from the reaction mixture of the photooxygenation of 1,3-dibenzoylindolizine in methanol by column chromatography on silica gel. Single crystals, suitable for X-ray crystallographic measurements, were prepared by slow evaporation of the solvent from a petroleum ether–acetone solution (1:1 v/v).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT and SADABS (Sheldrick, 1996); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Figures top

	Fig. 1. The structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. Packing diagram of the title compound, showing the formation of dimers.

Methyl 3-benzoyl-8-hydroxy-5-methoxyindolizine-1-carboxylate top

Crystal data top

C₁₈H₁₅NO₅	F(000) = 680
M_r = 325.31	D_x = 1.397 Mg m⁻³
Triclinic, P1	Melting point: 446(1) K
a = 9.0670 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.3774 (5) Å	Cell parameters from 5941 reflections
c = 15.9752 (8) Å	θ = 2.3–28.3°
α = 75.294 (1)°	µ = 0.10 mm⁻¹
β = 76.127 (1)°	T = 293 K
γ = 87.458 (1)°	Block, yellow
V = 1547.26 (12) Å³	0.50 × 0.50 × 0.42 mm
Z = 4

Data collection top

Siemens SMART CCD area-detector diffractometer	5445 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.012
Graphite monochromator	θ_max = 27.0°, θ_min = 2.3°
Detector resolution: 8.33 pixels mm^-1	h = −11→11
ω scans	k = −14→11
9032 measured reflections	l = −20→11
6518 independent reflections

Refinement top

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0611P)² + 0.333P] where P = (F_o² + 2F_c²)/3
6518 reflections	(Δ/σ)_max < 0.001
509 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₈H₁₅NO₅	γ = 87.458 (1)°
M_r = 325.31	V = 1547.26 (12) Å³
Triclinic, P1	Z = 4
a = 9.0670 (4) Å	Mo Kα radiation
b = 11.3774 (5) Å	µ = 0.10 mm⁻¹
c = 15.9752 (8) Å	T = 293 K
α = 75.294 (1)°	0.50 × 0.50 × 0.42 mm
β = 76.127 (1)°

Data collection top

Siemens SMART CCD area-detector diffractometer	5445 reflections with I > 2σ(I)
9032 measured reflections	R_int = 0.012
6518 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.19 e Å⁻³
6518 reflections	Δρ_min = −0.21 e Å⁻³
509 parameters

Special details top

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 30 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was −35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1A	0.40511 (13)	0.25829 (12)	0.49940 (8)	0.0600 (3)
O2A	0.81376 (11)	0.27401 (9)	0.18198 (6)	0.0455 (2)
O3A	0.24979 (12)	0.05678 (11)	0.52680 (7)	0.0561 (3)
O4A	0.24084 (11)	−0.08342 (10)	0.45174 (7)	0.0545 (3)
O5A	0.67879 (14)	−0.01823 (12)	0.14909 (8)	0.0655 (3)
N1A	0.63465 (11)	0.17527 (9)	0.30086 (7)	0.0346 (2)
C1A	0.49692 (15)	0.00860 (13)	0.32084 (9)	0.0425 (3)
C2A	0.62220 (15)	0.07478 (12)	0.26653 (9)	0.0393 (3)
C3A	0.72840 (14)	0.27676 (12)	0.26266 (8)	0.0374 (3)
C4A	0.71922 (16)	0.36652 (13)	0.30566 (10)	0.0438 (3)
C5A	0.61147 (17)	0.35781 (14)	0.38692 (10)	0.0468 (3)
C6A	0.51081 (15)	0.26222 (13)	0.42228 (9)	0.0422 (3)
C7A	0.51886 (13)	0.16816 (12)	0.37771 (8)	0.0363 (3)
C8A	0.43227 (14)	0.06225 (12)	0.39039 (9)	0.0394 (3)
C9A	0.30154 (14)	0.01486 (13)	0.46273 (9)	0.0420 (3)
C10A	0.11289 (17)	−0.14345 (16)	0.52085 (11)	0.0586 (4)
H10A	0.0547	−0.1885	0.4962	0.088*
H10B	0.0499	−0.0837	0.5443	0.088*
H10C	0.1494	−0.1979	0.5678	0.088*
C11A	0.94853 (18)	0.34901 (16)	0.14813 (12)	0.0627 (4)
H11A	1.0040	0.3333	0.0929	0.094*
H11B	1.0108	0.3309	0.1905	0.094*
H11C	0.9210	0.4330	0.1383	0.094*
C12A	0.73010 (16)	0.03326 (12)	0.19489 (9)	0.0432 (3)
C13A	0.89764 (15)	0.04004 (12)	0.18490 (9)	0.0418 (3)
C14A	0.99417 (18)	0.05440 (15)	0.10049 (10)	0.0526 (4)
C15A	1.1498 (2)	0.05698 (16)	0.08989 (12)	0.0623 (4)
C16A	1.2110 (2)	0.04199 (17)	0.16283 (13)	0.0642 (5)
C17A	1.1162 (2)	0.02676 (19)	0.24659 (13)	0.0642 (4)
C18A	0.95967 (18)	0.02666 (15)	0.25780 (10)	0.0503 (3)
O1B	0.77318 (15)	0.58630 (16)	0.01989 (9)	0.0806 (4)
O2B	0.35899 (12)	0.57639 (10)	0.33382 (7)	0.0525 (3)
O3B	0.70867 (14)	0.38586 (13)	−0.01647 (8)	0.0728 (4)
O4B	0.53552 (16)	0.23558 (12)	0.04263 (8)	0.0709 (4)
O5B	0.15484 (14)	0.29508 (10)	0.35090 (8)	0.0673 (3)
N1B	0.44456 (12)	0.50866 (10)	0.20964 (7)	0.0398 (2)
C1B	0.38548 (16)	0.33855 (13)	0.17854 (9)	0.0439 (3)
C2B	0.34037 (14)	0.41109 (12)	0.23625 (9)	0.0400 (3)
C3B	0.45944 (16)	0.59487 (13)	0.25457 (10)	0.0461 (3)
C4B	0.5712 (2)	0.68069 (16)	0.21808 (13)	0.0603 (4)
C5B	0.6745 (2)	0.67844 (18)	0.13718 (13)	0.0673 (5)
C6B	0.66914 (17)	0.58868 (16)	0.09596 (11)	0.0576 (4)
C7B	0.55252 (15)	0.49747 (14)	0.13363 (9)	0.0445 (3)
C8B	0.51550 (15)	0.39065 (14)	0.11372 (9)	0.0455 (3)
C9B	0.59658 (18)	0.34023 (16)	0.04094 (10)	0.0537 (4)
C10B	0.6099 (3)	0.1762 (2)	−0.02584 (13)	0.0879 (7)
H10D	0.5600	0.0996	−0.0162	0.132*
H10E	0.7143	0.1629	−0.0236	0.132*
H10F	0.6047	0.2267	−0.0832	0.132*
C11B	0.3357 (3)	0.6743 (2)	0.37604 (15)	0.0874 (7)
H11D	0.2526	0.6542	0.4277	0.131*
H11E	0.3126	0.7465	0.3352	0.131*
H11F	0.4262	0.6881	0.3937	0.131*
C12B	0.19506 (15)	0.39620 (12)	0.30476 (9)	0.0422 (3)
C13B	0.09178 (14)	0.50204 (13)	0.30917 (9)	0.0413 (3)
C14B	−0.01349 (17)	0.50072 (15)	0.38901 (10)	0.0505 (3)
C15B	−0.11147 (19)	0.59676 (17)	0.39531 (13)	0.0635 (5)
C16B	−0.1062 (2)	0.69337 (19)	0.32258 (15)	0.0714 (5)
C17B	−0.0040 (2)	0.69460 (18)	0.24290 (14)	0.0683 (5)
C18B	0.09525 (18)	0.59895 (15)	0.23580 (11)	0.0521 (4)
H1AA	0.345 (2)	0.190 (2)	0.5100 (14)	0.077 (6)*
H1A	0.4643 (17)	−0.0680 (15)	0.3130 (10)	0.046 (4)*
H4A	0.7844 (19)	0.4366 (15)	0.2812 (11)	0.052 (4)*
H5A	0.603 (2)	0.4230 (17)	0.4174 (12)	0.061 (5)*
H14A	0.949 (2)	0.0637 (17)	0.0503 (13)	0.071 (6)*
H15A	1.215 (2)	0.0693 (18)	0.0290 (14)	0.081 (6)*
H16A	1.319 (2)	0.0439 (18)	0.1563 (13)	0.072 (6)*
H17A	1.159 (2)	0.017 (2)	0.2960 (15)	0.086 (7)*
H18A	0.8932 (19)	0.0163 (15)	0.3142 (11)	0.055 (4)*
H1BA	0.766 (3)	0.515 (2)	0.0001 (15)	0.089 (8)*
H1B	0.3329 (18)	0.2634 (16)	0.1813 (11)	0.052 (4)*
H4B	0.581 (2)	0.7450 (19)	0.2470 (13)	0.074 (6)*
H5B	0.751 (2)	0.7409 (19)	0.1123 (14)	0.080 (6)*
H14B	−0.014 (2)	0.4302 (17)	0.4407 (12)	0.065 (5)*
H15B	−0.184 (2)	0.5973 (18)	0.4533 (14)	0.077 (6)*
H16B	−0.173 (3)	0.765 (2)	0.3260 (15)	0.092 (7)*
H17B	−0.004 (2)	0.757 (2)	0.1933 (15)	0.088 (7)*
H18B	0.1628 (19)	0.5977 (15)	0.1804 (11)	0.052 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0520 (6)	0.0747 (8)	0.0515 (6)	−0.0025 (6)	0.0100 (5)	−0.0327 (6)
O2A	0.0401 (5)	0.0459 (5)	0.0413 (5)	−0.0070 (4)	0.0077 (4)	−0.0093 (4)
O3A	0.0444 (6)	0.0728 (7)	0.0422 (5)	−0.0054 (5)	0.0086 (4)	−0.0151 (5)
O4A	0.0431 (5)	0.0593 (6)	0.0497 (6)	−0.0157 (5)	0.0084 (4)	−0.0089 (5)
O5A	0.0620 (7)	0.0813 (8)	0.0600 (7)	−0.0120 (6)	−0.0011 (5)	−0.0404 (6)
N1A	0.0301 (5)	0.0382 (5)	0.0324 (5)	0.0002 (4)	−0.0008 (4)	−0.0095 (4)
C1A	0.0378 (7)	0.0437 (7)	0.0420 (7)	−0.0060 (6)	0.0001 (5)	−0.0113 (6)
C2A	0.0367 (6)	0.0413 (7)	0.0373 (6)	−0.0036 (5)	−0.0007 (5)	−0.0121 (5)
C3A	0.0315 (6)	0.0390 (6)	0.0372 (6)	−0.0003 (5)	−0.0024 (5)	−0.0068 (5)
C4A	0.0409 (7)	0.0403 (7)	0.0485 (8)	−0.0027 (6)	−0.0068 (6)	−0.0111 (6)
C5A	0.0474 (8)	0.0465 (8)	0.0499 (8)	0.0038 (6)	−0.0095 (6)	−0.0206 (6)
C6A	0.0362 (6)	0.0525 (8)	0.0376 (7)	0.0064 (6)	−0.0036 (5)	−0.0168 (6)
C7A	0.0286 (5)	0.0446 (7)	0.0323 (6)	0.0030 (5)	−0.0022 (5)	−0.0088 (5)
C8A	0.0314 (6)	0.0461 (7)	0.0355 (6)	−0.0008 (5)	0.0000 (5)	−0.0080 (5)
C9A	0.0303 (6)	0.0526 (8)	0.0360 (7)	0.0013 (5)	−0.0020 (5)	−0.0039 (6)
C10A	0.0395 (7)	0.0600 (9)	0.0587 (9)	−0.0099 (7)	0.0067 (7)	0.0013 (7)
C11A	0.0467 (8)	0.0603 (10)	0.0657 (10)	−0.0157 (7)	0.0143 (7)	−0.0113 (8)
C12A	0.0472 (7)	0.0431 (7)	0.0364 (7)	−0.0035 (6)	0.0014 (6)	−0.0145 (5)
C13A	0.0439 (7)	0.0398 (7)	0.0373 (7)	0.0015 (5)	0.0039 (5)	−0.0142 (5)
C14A	0.0534 (8)	0.0599 (9)	0.0390 (8)	0.0073 (7)	0.0047 (6)	−0.0185 (7)
C15A	0.0528 (9)	0.0644 (10)	0.0554 (9)	0.0053 (8)	0.0161 (8)	−0.0173 (8)
C16A	0.0430 (8)	0.0673 (11)	0.0777 (12)	0.0055 (8)	0.0001 (8)	−0.0239 (9)
C17A	0.0541 (9)	0.0791 (12)	0.0611 (10)	0.0086 (8)	−0.0134 (8)	−0.0224 (9)
C18A	0.0495 (8)	0.0576 (9)	0.0388 (7)	0.0035 (7)	0.0008 (6)	−0.0143 (6)
O1B	0.0573 (7)	0.0986 (11)	0.0610 (8)	−0.0164 (7)	0.0228 (6)	−0.0068 (7)
O2B	0.0513 (6)	0.0558 (6)	0.0504 (6)	−0.0096 (5)	0.0002 (5)	−0.0229 (5)
O3B	0.0628 (7)	0.0970 (10)	0.0437 (6)	0.0111 (7)	0.0127 (5)	−0.0167 (6)
O4B	0.0816 (8)	0.0676 (8)	0.0551 (7)	0.0158 (7)	0.0102 (6)	−0.0279 (6)
O5B	0.0597 (7)	0.0470 (6)	0.0710 (8)	−0.0050 (5)	0.0201 (6)	−0.0038 (5)
N1B	0.0329 (5)	0.0434 (6)	0.0379 (6)	−0.0022 (4)	−0.0014 (4)	−0.0071 (5)
C1B	0.0406 (7)	0.0451 (7)	0.0412 (7)	0.0039 (6)	0.0001 (5)	−0.0122 (6)
C2B	0.0351 (6)	0.0409 (7)	0.0390 (7)	−0.0013 (5)	0.0006 (5)	−0.0096 (5)
C3B	0.0412 (7)	0.0474 (8)	0.0481 (8)	−0.0040 (6)	−0.0068 (6)	−0.0117 (6)
C4B	0.0540 (9)	0.0569 (9)	0.0669 (10)	−0.0142 (7)	−0.0078 (8)	−0.0133 (8)
C5B	0.0533 (9)	0.0656 (11)	0.0698 (11)	−0.0223 (8)	−0.0011 (8)	−0.0023 (9)
C6B	0.0399 (7)	0.0690 (10)	0.0478 (8)	−0.0062 (7)	0.0044 (6)	0.0014 (7)
C7B	0.0333 (6)	0.0542 (8)	0.0365 (7)	0.0037 (6)	0.0001 (5)	−0.0030 (6)
C8B	0.0385 (7)	0.0541 (8)	0.0367 (7)	0.0091 (6)	0.0002 (5)	−0.0086 (6)
C9B	0.0499 (8)	0.0665 (10)	0.0370 (7)	0.0181 (7)	−0.0018 (6)	−0.0100 (7)
C10B	0.1119 (17)	0.0869 (14)	0.0597 (11)	0.0324 (13)	0.0035 (11)	−0.0365 (10)
C11B	0.1004 (16)	0.0875 (14)	0.0773 (13)	−0.0275 (12)	0.0108 (11)	−0.0510 (12)
C12B	0.0384 (7)	0.0441 (7)	0.0394 (7)	−0.0057 (5)	0.0029 (5)	−0.0125 (6)
C13B	0.0341 (6)	0.0465 (7)	0.0422 (7)	−0.0045 (5)	0.0007 (5)	−0.0173 (6)
C14B	0.0438 (7)	0.0568 (9)	0.0468 (8)	−0.0046 (6)	0.0056 (6)	−0.0199 (7)
C15B	0.0489 (9)	0.0712 (11)	0.0699 (11)	0.0023 (8)	0.0074 (8)	−0.0372 (9)
C16B	0.0552 (10)	0.0660 (11)	0.0932 (14)	0.0163 (9)	−0.0075 (10)	−0.0322 (11)
C17B	0.0652 (11)	0.0609 (10)	0.0716 (12)	0.0130 (9)	−0.0122 (9)	−0.0091 (9)
C18B	0.0463 (8)	0.0572 (9)	0.0476 (8)	0.0017 (7)	−0.0016 (6)	−0.0127 (7)

Geometric parameters (Å, º) top

O1A—C6A	1.3594 (16)	O1B—C6B	1.3536 (19)
O1A—H1AA	0.93 (2)	O1B—H1BA	0.95 (2)
O2A—C3A	1.3420 (15)	O2B—C3B	1.3437 (17)
O2A—C11A	1.4335 (17)	O2B—C11B	1.426 (2)
O3A—C9A	1.2218 (17)	O3B—C9B	1.2254 (19)
O4A—C9A	1.3358 (18)	O4B—C9B	1.327 (2)
O4A—C10A	1.4507 (16)	O4B—C10B	1.445 (2)
O5A—C12A	1.2247 (17)	O5B—C12B	1.2156 (17)
N1A—C3A	1.3816 (16)	N1B—C3B	1.3825 (18)
N1A—C7A	1.3983 (14)	N1B—C7B	1.3951 (17)
N1A—C2A	1.4071 (16)	N1B—C2B	1.4021 (17)
C1A—C2A	1.3717 (18)	C1B—C2B	1.3690 (19)
C1A—C8A	1.3967 (19)	C1B—C8B	1.4066 (19)
C1A—H1A	0.979 (16)	C1B—H1B	0.984 (17)
C2A—C12A	1.4788 (18)	C2B—C12B	1.4821 (17)
C3A—C4A	1.3576 (19)	C3B—C4B	1.355 (2)
C4A—C5A	1.409 (2)	C4B—C5B	1.408 (3)
C4A—H4A	0.954 (17)	C4B—H4B	0.98 (2)
C5A—C6A	1.365 (2)	C5B—C6B	1.356 (3)
C5A—H5A	0.977 (19)	C5B—H5B	0.96 (2)
C6A—C7A	1.4186 (19)	C6B—C7B	1.426 (2)
C7A—C8A	1.4118 (19)	C7B—C8B	1.405 (2)
C8A—C9A	1.4542 (17)	C8B—C9B	1.453 (2)
C10A—H10A	0.9600	C10B—H10D	0.9600
C10A—H10B	0.9600	C10B—H10E	0.9600
C10A—H10C	0.9600	C10B—H10F	0.9600
C11A—H11A	0.9600	C11B—H11D	0.9600
C11A—H11B	0.9600	C11B—H11E	0.9600
C11A—H11C	0.9600	C11B—H11F	0.9600
C12A—C13A	1.492 (2)	C12B—C13B	1.4977 (19)
C13A—C18A	1.383 (2)	C13B—C18B	1.386 (2)
C13A—C14A	1.3949 (18)	C13B—C14B	1.3949 (18)
C14A—C15A	1.381 (2)	C14B—C15B	1.386 (2)
C14A—H14A	0.967 (19)	C14B—H14B	0.993 (18)
C15A—C16A	1.377 (3)	C15B—C16B	1.375 (3)
C15A—H15A	0.99 (2)	C15B—H15B	1.00 (2)
C16A—C17A	1.380 (3)	C16B—C17B	1.380 (3)
C16A—H16A	0.96 (2)	C16B—H16B	1.00 (2)
C17A—C18A	1.387 (2)	C17B—C18B	1.390 (2)
C17A—H17A	0.94 (2)	C17B—H17B	0.92 (2)
C18A—H18A	0.939 (17)	C18B—H18B	0.951 (17)

C6A—O1A—H1AA	106.2 (13)	C6B—O1B—H1BA	113.3 (14)
C3A—O2A—C11A	117.58 (12)	C3B—O2B—C11B	117.33 (13)
C9A—O4A—C10A	117.77 (12)	C9B—O4B—C10B	116.58 (15)
C3A—N1A—C7A	121.71 (11)	C3B—N1B—C7B	121.89 (12)
C3A—N1A—C2A	128.46 (10)	C3B—N1B—C2B	128.40 (11)
C7A—N1A—C2A	109.26 (10)	C7B—N1B—C2B	109.07 (11)
C2A—C1A—C8A	110.04 (12)	C2B—C1B—C8B	109.14 (13)
C2A—C1A—H1A	123.5 (9)	C2B—C1B—H1B	125.0 (10)
C8A—C1A—H1A	126.3 (9)	C8B—C1B—H1B	125.8 (10)
C1A—C2A—N1A	106.66 (11)	C1B—C2B—N1B	107.39 (11)
C1A—C2A—C12A	123.77 (12)	C1B—C2B—C12B	124.66 (12)
N1A—C2A—C12A	129.03 (11)	N1B—C2B—C12B	127.36 (12)
O2A—C3A—C4A	128.45 (12)	O2B—C3B—C4B	128.58 (15)
O2A—C3A—N1A	112.11 (11)	O2B—C3B—N1B	112.14 (11)
C4A—C3A—N1A	119.33 (12)	C4B—C3B—N1B	119.22 (14)
C3A—C4A—C5A	120.14 (13)	C3B—C4B—C5B	120.06 (17)
C3A—C4A—H4A	120.8 (10)	C3B—C4B—H4B	120.7 (12)
C5A—C4A—H4A	119.1 (10)	C5B—C4B—H4B	119.3 (12)
C6A—C5A—C4A	121.15 (13)	C6B—C5B—C4B	121.42 (15)
C6A—C5A—H5A	118.2 (11)	C6B—C5B—H5B	120.2 (13)
C4A—C5A—H5A	120.5 (11)	C4B—C5B—H5B	118.4 (13)
O1A—C6A—C5A	119.76 (13)	O1B—C6B—C5B	120.22 (16)
O1A—C6A—C7A	121.07 (13)	O1B—C6B—C7B	120.60 (17)
C5A—C6A—C7A	119.16 (12)	C5B—C6B—C7B	119.17 (15)
N1A—C7A—C8A	106.70 (11)	N1B—C7B—C8B	106.89 (11)
N1A—C7A—C6A	118.05 (11)	N1B—C7B—C6B	117.66 (14)
C8A—C7A—C6A	135.23 (12)	C8B—C7B—C6B	135.45 (14)
C1A—C8A—C7A	107.30 (11)	C7B—C8B—C1B	107.49 (12)
C1A—C8A—C9A	125.53 (13)	C7B—C8B—C9B	127.09 (13)
C7A—C8A—C9A	127.16 (12)	C1B—C8B—C9B	125.41 (15)
O3A—C9A—O4A	122.21 (12)	O3B—C9B—O4B	122.06 (15)
O3A—C9A—C8A	126.11 (14)	O3B—C9B—C8B	125.81 (17)
O4A—C9A—C8A	111.68 (12)	O4B—C9B—C8B	112.13 (13)
O4A—C10A—H10A	109.5	O4B—C10B—H10D	109.5
O4A—C10A—H10B	109.5	O4B—C10B—H10E	109.5
H10A—C10A—H10B	109.5	H10D—C10B—H10E	109.5
O4A—C10A—H10C	109.5	O4B—C10B—H10F	109.5
H10A—C10A—H10C	109.5	H10D—C10B—H10F	109.5
H10B—C10A—H10C	109.5	H10E—C10B—H10F	109.5
O2A—C11A—H11A	109.5	O2B—C11B—H11D	109.5
O2A—C11A—H11B	109.5	O2B—C11B—H11E	109.5
H11A—C11A—H11B	109.5	H11D—C11B—H11E	109.5
O2A—C11A—H11C	109.5	O2B—C11B—H11F	109.5
H11A—C11A—H11C	109.5	H11D—C11B—H11F	109.5
H11B—C11A—H11C	109.5	H11E—C11B—H11F	109.5
O5A—C12A—C2A	118.25 (13)	O5B—C12B—C2B	118.95 (13)
O5A—C12A—C13A	120.06 (12)	O5B—C12B—C13B	120.74 (12)
C2A—C12A—C13A	121.29 (12)	C2B—C12B—C13B	119.92 (11)
C18A—C13A—C14A	119.23 (14)	C18B—C13B—C14B	119.40 (14)
C18A—C13A—C12A	121.56 (12)	C18B—C13B—C12B	121.90 (12)
C14A—C13A—C12A	119.14 (13)	C14B—C13B—C12B	118.68 (13)
C15A—C14A—C13A	120.26 (16)	C15B—C14B—C13B	120.23 (16)
C15A—C14A—H14A	121.6 (11)	C15B—C14B—H14B	121.7 (11)
C13A—C14A—H14A	118.1 (11)	C13B—C14B—H14B	118.0 (11)
C16A—C15A—C14A	120.26 (15)	C16B—C15B—C14B	120.09 (16)
C16A—C15A—H15A	121.6 (12)	C16B—C15B—H15B	119.6 (12)
C14A—C15A—H15A	118.2 (12)	C14B—C15B—H15B	120.3 (12)
C15A—C16A—C17A	119.75 (16)	C15B—C16B—C17B	120.10 (17)
C15A—C16A—H16A	121.0 (12)	C15B—C16B—H16B	121.7 (13)
C17A—C16A—H16A	119.3 (12)	C17B—C16B—H16B	118.2 (13)
C16A—C17A—C18A	120.47 (17)	C16B—C17B—C18B	120.36 (18)
C16A—C17A—H17A	119.4 (13)	C16B—C17B—H17B	120.3 (14)
C18A—C17A—H17A	120.2 (13)	C18B—C17B—H17B	119.2 (14)
C13A—C18A—C17A	120.00 (14)	C13B—C18B—C17B	119.81 (15)
C13A—C18A—H18A	118.2 (10)	C13B—C18B—H18B	119.5 (10)
C17A—C18A—H18A	121.8 (10)	C17B—C18B—H18B	120.6 (10)

C8A—C1A—C2A—N1A	−1.88 (16)	C8B—C1B—C2B—N1B	−1.56 (16)
C8A—C1A—C2A—C12A	170.38 (13)	C8B—C1B—C2B—C12B	170.16 (13)
C3A—N1A—C2A—C1A	−169.76 (12)	C3B—N1B—C2B—C1B	−169.45 (13)
C7A—N1A—C2A—C1A	1.62 (14)	C7B—N1B—C2B—C1B	1.42 (15)
C3A—N1A—C2A—C12A	18.5 (2)	C3B—N1B—C2B—C12B	19.1 (2)
C7A—N1A—C2A—C12A	−170.10 (13)	C7B—N1B—C2B—C12B	−170.01 (13)
C11A—O2A—C3A—C4A	24.3 (2)	C11B—O2B—C3B—C4B	18.7 (3)
C11A—O2A—C3A—N1A	−159.55 (12)	C11B—O2B—C3B—N1B	−164.27 (16)
C7A—N1A—C3A—O2A	−169.35 (10)	C7B—N1B—C3B—O2B	−168.90 (12)
C2A—N1A—C3A—O2A	1.07 (18)	C2B—N1B—C3B—O2B	0.9 (2)
C7A—N1A—C3A—C4A	7.21 (18)	C7B—N1B—C3B—C4B	8.4 (2)
C2A—N1A—C3A—C4A	177.63 (12)	C2B—N1B—C3B—C4B	178.25 (14)
O2A—C3A—C4A—C5A	173.80 (13)	O2B—C3B—C4B—C5B	174.14 (16)
N1A—C3A—C4A—C5A	−2.1 (2)	N1B—C3B—C4B—C5B	−2.7 (3)
C3A—C4A—C5A—C6A	−2.6 (2)	C3B—C4B—C5B—C6B	−2.7 (3)
C4A—C5A—C6A—O1A	−177.96 (13)	C4B—C5B—C6B—O1B	−177.66 (17)
C4A—C5A—C6A—C7A	2.2 (2)	C4B—C5B—C6B—C7B	2.5 (3)
C3A—N1A—C7A—C8A	171.32 (11)	C3B—N1B—C7B—C8B	170.85 (12)
C2A—N1A—C7A—C8A	−0.74 (14)	C2B—N1B—C7B—C8B	−0.73 (15)
C3A—N1A—C7A—C6A	−7.42 (17)	C3B—N1B—C7B—C6B	−8.5 (2)
C2A—N1A—C7A—C6A	−179.49 (11)	C2B—N1B—C7B—C6B	179.95 (12)
O1A—C6A—C7A—N1A	−177.19 (12)	O1B—C6B—C7B—N1B	−176.89 (14)
C5A—C6A—C7A—N1A	2.63 (19)	C5B—C6B—C7B—N1B	2.9 (2)
O1A—C6A—C7A—C8A	4.5 (2)	O1B—C6B—C7B—C8B	4.0 (3)
C5A—C6A—C7A—C8A	−175.67 (15)	C5B—C6B—C7B—C8B	−176.17 (17)
C2A—C1A—C8A—C7A	1.44 (16)	N1B—C7B—C8B—C1B	−0.22 (15)
C2A—C1A—C8A—C9A	−177.52 (13)	C6B—C7B—C8B—C1B	178.92 (16)
N1A—C7A—C8A—C1A	−0.40 (14)	N1B—C7B—C8B—C9B	−179.14 (13)
C6A—C7A—C8A—C1A	178.02 (14)	C6B—C7B—C8B—C9B	0.0 (3)
N1A—C7A—C8A—C9A	178.54 (12)	C2B—C1B—C8B—C7B	1.12 (16)
C6A—C7A—C8A—C9A	−3.0 (2)	C2B—C1B—C8B—C9B	−179.94 (13)
C10A—O4A—C9A—O3A	−2.4 (2)	C10B—O4B—C9B—O3B	1.3 (2)
C10A—O4A—C9A—C8A	177.60 (12)	C10B—O4B—C9B—C8B	−178.59 (15)
C1A—C8A—C9A—O3A	175.15 (14)	C7B—C8B—C9B—O3B	−2.3 (3)
C7A—C8A—C9A—O3A	−3.6 (2)	C1B—C8B—C9B—O3B	178.96 (15)
C1A—C8A—C9A—O4A	−4.86 (19)	C7B—C8B—C9B—O4B	177.55 (14)
C7A—C8A—C9A—O4A	176.38 (13)	C1B—C8B—C9B—O4B	−1.2 (2)
C1A—C2A—C12A—O5A	40.5 (2)	C1B—C2B—C12B—O5B	45.5 (2)
N1A—C2A—C12A—O5A	−149.04 (14)	N1B—C2B—C12B—O5B	−144.44 (15)
C1A—C2A—C12A—C13A	−132.30 (15)	C1B—C2B—C12B—C13B	−127.35 (15)
N1A—C2A—C12A—C13A	38.1 (2)	N1B—C2B—C12B—C13B	42.7 (2)
O5A—C12A—C13A—C18A	−140.62 (16)	O5B—C12B—C13B—C18B	−148.85 (16)
C2A—C12A—C13A—C18A	32.1 (2)	C2B—C12B—C13B—C18B	23.9 (2)
O5A—C12A—C13A—C14A	36.3 (2)	O5B—C12B—C13B—C14B	29.3 (2)
C2A—C12A—C13A—C14A	−151.04 (14)	C2B—C12B—C13B—C14B	−157.92 (13)
C18A—C13A—C14A—C15A	−0.9 (2)	C18B—C13B—C14B—C15B	−1.4 (2)
C12A—C13A—C14A—C15A	−177.90 (14)	C12B—C13B—C14B—C15B	−179.59 (14)
C13A—C14A—C15A—C16A	1.8 (3)	C13B—C14B—C15B—C16B	0.6 (3)
C14A—C15A—C16A—C17A	−1.3 (3)	C14B—C15B—C16B—C17B	0.4 (3)
C15A—C16A—C17A—C18A	−0.1 (3)	C15B—C16B—C17B—C18B	−0.6 (3)
C14A—C13A—C18A—C17A	−0.4 (2)	C14B—C13B—C18B—C17B	1.2 (2)
C12A—C13A—C18A—C17A	176.43 (15)	C12B—C13B—C18B—C17B	179.33 (15)
C16A—C17A—C18A—C13A	1.0 (3)	C16B—C17B—C18B—C13B	−0.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1AA···O3A	0.93 (2)	1.71 (2)	2.629 (2)	175 (2)
O1B—H1BA···O3B	0.95 (2)	1.68 (2)	2.614 (2)	165 (2)
C11A—H11A···O1Bⁱ	0.96	2.40	3.167 (2)	137
C18A—H18A···O3Aⁱⁱ	0.94 (2)	2.50 (2)	3.423 (2)	166 (2)
C18B—H18B···O3Bⁱⁱⁱ	0.95 (2)	2.56 (2)	3.493 (2)	167 (2)

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+1, −y, −z+1; (iii) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₅NO₅
M_r	325.31
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.0670 (4), 11.3774 (5), 15.9752 (8)
α, β, γ (°)	75.294 (1), 76.127 (1), 87.458 (1)
V (Å³)	1547.26 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.50 × 0.50 × 0.42

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9032, 6518, 5445
R_int	0.012
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.120, 1.03
No. of reflections	6518
No. of parameters	509
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.21

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT and SADABS (Sheldrick, 1996), SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Selected bond lengths (Å) top

O1A—C6A	1.3594 (16)	O1B—C6B	1.3536 (19)
N1A—C3A	1.3816 (16)	N1B—C3B	1.3825 (18)
N1A—C7A	1.3983 (14)	N1B—C7B	1.3951 (17)
N1A—C2A	1.4071 (16)	N1B—C2B	1.4021 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1AA···O3A	0.93 (2)	1.71 (2)	2.629 (2)	175 (2)
O1B—H1BA···O3B	0.95 (2)	1.68 (2)	2.614 (2)	165 (2)
C11A—H11A···O1Bⁱ	0.96	2.40	3.167 (2)	137
C18A—H18A···O3Aⁱⁱ	0.94 (2)	2.50 (2)	3.423 (2)	166 (2)
C18B—H18B···O3Bⁱⁱⁱ	0.95 (2)	2.56 (2)	3.493 (2)	167 (2)

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+1, −y, −z+1; (iii) −x+1, −y+1, −z.

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.

E-mail address*
Repeat e-mail address* (for error checking)

Format*	PDF (US $40)
	HTML (US $40)
	PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number (non-UK EC countries only)
Country*

Terms and conditions of use
Contact us

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page