2-Ethyl­phenyl acridine-9-carboxyl­ate and 2,5-dimethyl­phenyl acridine-9-carboxyl­ate

The title compounds, 2-ethyl­phenyl acridine-9-carboxyl­ate, C₂₂H₁₇NO₂, (I), and 2,5-dimethyl­phenyl acridine-9-carboxyl­ate, C₂₂H₁₇NO₂, (II), form triclinic and monoclinic crystals, respectively. Related by a centre of symmetry, adjacent molecules of (I) are linked in the lattice via a network of C—H...π and non-specific dispersive interactions. As a result, acridine moieties and independent phenyl moieties of (I) are parallel in the lattice. The molecules of (II), arranged in a `head-to-tail' manner and related by a centre of symmetry, form pairs stabilized via C—H...π interactions. These are linked in the crystal via dispersive interactions. Acridine and independent phenyl moieties lie parallel within the pairs, while adjacent pairs are perpendicular, forming a herring-bone pattern.

S1. Comment

Phenyl esters of acridine-9-carboxylic acids are precursors of practically important chemi-luminescent indicators and chemi-luminogenic fragments of chemi-luminescent labels (Dodeigne et al., 2000; Zomer & Jacquemijns, 2001). This is because 9-carboxy-10-methylacridinium phenyl esters react efficiently with hydrogen peroxide in alkaline media, which leads to electronically excited 10-methyl-9-acridinones emitting radiation (Rak et al., 1999). Among other things, this effect is utilized in quantitative assays of macromolecules present in living matter, that is, in immunological, medical, environmental and biochemical analyses (Adamczyk et al., 1999; Dodeigne et al., 2000; Razawi & McCapra, 2002; Smith et al., 2000; Zomer & Jacquemijns, 2001). Despite the long-standing interest shown in this group of compounds, there is only one publication to date -our own - on the crystallography of 2-methylphenyl 2-methoxyacridine-9-carboxylate (Meszko et al., 2002). It is thus important to extend investigations of further representatives of this group, especially since information on the structure, crystal packing and other features may help in the design of very stable compounds that are nevertheless highly reactive towards oxidizing agents (hydrogen peroxide). This paper presents the crystal structure of two isomers, (I) and (II), alkyl-substituted in the phenyl ester group, of phenylacridine-9-carboxylate.

The acridine and phenyl moieties in (I), with average deviations from planarity of 0.0123 and 0.0033 Å, respectively, are oriented at an angle of 62.1 (2)° (defined as γ, the angle between the mean planes delineated by all the non-H atoms of the acridine and phenyl nuclei; Fig. 1, Table 1). The carboxyl group is twisted relative to the acridine skeleton, at an angle of 67.3 (2)° (defined as δ, the angle between the mean planes delineated by all the non-H atoms of the acridine nucleus and atoms C15, O16 and O17).

In the crystalline phase, adjacent molecules of (I), related by a centre of symmetry, are linked via a network of C—H···π interactions and non-specific dispersive interactions (Fig. 2, Table 2). As a result, the acridine moieties and independent phenyl moieties are parallel in the lattice.

The planes of the acridine and phenyl moieties in (II), with average deviations from planarity of 0.0013 and 0.0056 Å, respectively, have a γ angle of 35.7 (2)° (Fig.3, Table 3). The carboxyl group is twisted relative to the acridine skeleton, with a δ angle of 68.1 (2)°.

Arranged in a `head-to-tail' manner, the molecules of (II) form pairs stabilized through C—H···π interactions (Table 4). These pairs of molecules, related by a centre of symmetry, are linked in the crystal via dispersive interactions. The acridine moieties and independent phenyl moieties within the pairs are parallel, while adjacent pairs, which form a herring-bone pattern in the crystal, lie perpendicular to each other (Fig. 4).

S2. Experimental

Compounds (I) and (II) were synthesized by conversion of commercially available acridine-9-carboxylic acid to acid chloride, and by the reaction of the latter with 2-ethylphenol for (I) or 2,5-dimethylphenol for (II) (Sato, 1996). The crude products were purified chromatographically (SiO₂, cyclohexane/ethyl acetate, 3:2 (v/v). Elemental analyses (% found/calculated): for (I): C 81.07/80.71, H 5.07/5.23, N 4.34/4.28; for (II): C 80.49/80.71, H 5.09/5.23, N 4.22/4.28. In both cases, pale-yellow crystals suitable for X-ray investigations were grown from cyclohexane [m.p. 387–389 K for (I) and 452–454 K for (II)].

S3. Refinement

All H atoms were placed geometrically and refined using a riding model, with C—H distances of 0.96 Å and with U_iso(H) = 1.2U_eq(C). Please check added text.

Computing details

For both compounds, data collection: KM-4 Software (Kuma Diffraction, 1989); cell refinement: KM-4 Software; data reduction: KM-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The molecular structure of (I), showing the atom-labelling scheme and 50% probability displacement ellipsoids. H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The arrangement of the molecules of (I) in the unit cell, viewed along the c axis. H atoms not involved in C—H···π interactions have been omitted. C—H···π interactions are represented by dashed lines. Symmetry codes for these interactions are given in Table 2.
	Fig. 3. The molecular structure of (II), showing the atom-labelling scheme and 50% probability displacement ellipsoids. H atoms are shown as small spheres of arbitrary radii.
	Fig. 4. Part of the crystal structure of (II) in the unit cell, viewed along the c axis, showing the centrosymmetric linking of the molecules by pairs of C—H···π interactions (dashed lines). H atoms not involved in C—H···π interactions have been omitted. Symmetry codes for these interactions are given in Table 4.

(I) 2-ethylphenyl acridine-9-carboxylate

Crystal data

C22H17NO2	Z = 2
Mr = 327.37	F(000) = 344
Triclinic, P1	Dx = 1.278 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.995 (2) Å	Cell parameters from 50 reflections
b = 9.465 (2) Å	θ = 2.3–26°
c = 11.899 (2) Å	µ = 0.08 mm^−1
α = 92.12 (3)°	T = 293 K
β = 98.96 (3)°	Prism, yellow
γ = 106.28 (3)°	0.5 × 0.4 × 0.3 mm
V = 850.7 (4) Å^3

Data collection

Kuma KM-4 diffractometer	Rint = 0.017
Radiation source: fine-focus sealed tube	θmax = 26.0°, θmin = 2.3°
Graphite monochromator	h = −9→9
θ/2θ scans	k = −11→11
3507 measured reflections	l = −14→0
3337 independent reflections	3 standard reflections every 200 reflections
1788 reflections with I > 2σ(I)	intensity decay: 1.3%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.125	w = 1/[σ^2(Fo^2) + (0.0568P)^2 + 0.1515P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
3337 reflections	Δρmax = 0.20 e Å^−3
227 parameters	Δρmin = −0.18 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.027 (4)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.5133 (3)	0.6084 (2)	1.18451 (18)	0.0511 (5)
H1A	0.4984	0.5760	1.1052	0.061*
C2	0.6438 (3)	0.5833 (3)	1.2593 (2)	0.0650 (6)
H2A	0.7216	0.5336	1.2329	0.078*
C3	0.6677 (4)	0.6299 (3)	1.3758 (2)	0.0781 (8)
H3A	0.7606	0.6097	1.4282	0.094*
C4	0.5649 (4)	0.7033 (3)	1.41436 (19)	0.0718 (7)
H4A	0.5815	0.7319	1.4945	0.086*
C5	0.1004 (4)	0.9242 (3)	1.3584 (2)	0.0677 (7)
H5A	0.1289	0.9556	1.4385	0.081*
C6	−0.0342 (4)	0.9571 (3)	1.2926 (2)	0.0741 (7)
H6A	−0.0949	1.0188	1.3246	0.089*
C7	−0.0827 (3)	0.9057 (3)	1.1765 (2)	0.0663 (6)
H7A	−0.1807	0.9283	1.1311	0.080*
C8	0.0062 (3)	0.8253 (2)	1.12776 (18)	0.0519 (5)
H8A	−0.0302	0.7904	1.0485	0.062*
C9	0.2568 (2)	0.71311 (19)	1.14893 (15)	0.0380 (4)
N10	0.3295 (3)	0.8110 (2)	1.38188 (14)	0.0561 (5)
C11	0.3964 (3)	0.6831 (2)	1.22095 (15)	0.0411 (5)
C12	0.4262 (3)	0.7344 (2)	1.33895 (16)	0.0499 (5)
C13	0.1528 (3)	0.7912 (2)	1.19268 (15)	0.0409 (5)
C14	0.1980 (3)	0.8399 (2)	1.31147 (16)	0.0489 (5)
C15	0.2216 (2)	0.6582 (2)	1.02595 (15)	0.0392 (4)
O16	0.21642 (18)	0.76849 (14)	0.95782 (10)	0.0460 (4)
O17	0.2048 (2)	0.53417 (16)	0.99104 (11)	0.0538 (4)
C18	0.1779 (3)	0.7319 (2)	0.83844 (14)	0.0400 (5)
C19	0.3075 (3)	0.7949 (2)	0.77632 (15)	0.0426 (5)
C20	0.2640 (3)	0.7638 (2)	0.65900 (16)	0.0497 (5)
H20A	0.3517	0.8043	0.6129	0.060*
C21	0.1011 (3)	0.6749 (2)	0.60717 (17)	0.0550 (6)
H21A	0.0735	0.6555	0.5256	0.066*
C22	−0.0254 (3)	0.6152 (3)	0.67261 (18)	0.0577 (6)
H22A	−0.1396	0.5528	0.6369	0.069*
C23	0.0126 (3)	0.6446 (2)	0.78953 (17)	0.0492 (5)
H23A	−0.0751	0.6052	0.8357	0.059*
C24	0.4866 (3)	0.8924 (3)	0.8307 (2)	0.0627 (6)
H24A	0.4754	0.9458	0.8979	0.075*
H24B	0.5298	0.9631	0.7785	0.075*
C25	0.6199 (4)	0.8113 (4)	0.8629 (3)	0.1151 (13)
H25A	0.7319	0.8805	0.8946	0.173*
H25B	0.6318	0.7570	0.7963	0.173*
H25C	0.5817	0.7440	0.9185	0.173*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0537 (13)	0.0556 (13)	0.0470 (12)	0.0211 (11)	0.0086 (10)	0.0037 (9)
C2	0.0603 (15)	0.0770 (16)	0.0652 (15)	0.0337 (13)	0.0072 (12)	0.0088 (12)
C3	0.0671 (17)	0.108 (2)	0.0622 (16)	0.0403 (16)	−0.0077 (13)	0.0105 (15)
C4	0.0790 (18)	0.096 (2)	0.0389 (12)	0.0316 (15)	−0.0045 (12)	0.0036 (12)
C5	0.096 (2)	0.0703 (16)	0.0491 (13)	0.0354 (15)	0.0301 (13)	0.0013 (11)
C6	0.095 (2)	0.0757 (17)	0.0726 (17)	0.0476 (16)	0.0359 (15)	0.0065 (13)
C7	0.0666 (16)	0.0717 (16)	0.0717 (17)	0.0345 (13)	0.0177 (12)	0.0090 (12)
C8	0.0515 (13)	0.0570 (13)	0.0512 (12)	0.0198 (11)	0.0128 (10)	0.0072 (10)
C9	0.0429 (11)	0.0364 (10)	0.0332 (9)	0.0072 (8)	0.0096 (8)	0.0049 (8)
N10	0.0706 (13)	0.0671 (12)	0.0331 (9)	0.0224 (10)	0.0124 (8)	0.0022 (8)
C11	0.0466 (12)	0.0410 (10)	0.0352 (10)	0.0100 (9)	0.0096 (8)	0.0065 (8)
C12	0.0553 (13)	0.0566 (13)	0.0360 (11)	0.0130 (10)	0.0080 (9)	0.0066 (9)
C13	0.0476 (12)	0.0389 (10)	0.0372 (10)	0.0098 (9)	0.0148 (8)	0.0062 (8)
C14	0.0603 (14)	0.0495 (12)	0.0399 (11)	0.0142 (11)	0.0197 (10)	0.0062 (9)
C15	0.0407 (11)	0.0408 (11)	0.0360 (10)	0.0108 (9)	0.0079 (8)	0.0031 (8)
O16	0.0640 (9)	0.0415 (7)	0.0316 (7)	0.0132 (7)	0.0091 (6)	0.0045 (6)
O17	0.0732 (10)	0.0464 (9)	0.0422 (8)	0.0214 (7)	0.0044 (7)	−0.0006 (6)
C18	0.0492 (12)	0.0415 (11)	0.0299 (9)	0.0151 (9)	0.0054 (8)	0.0035 (8)
C19	0.0475 (12)	0.0429 (11)	0.0384 (11)	0.0139 (9)	0.0085 (9)	0.0050 (9)
C20	0.0584 (14)	0.0566 (13)	0.0392 (11)	0.0204 (11)	0.0156 (10)	0.0081 (9)
C21	0.0665 (16)	0.0617 (14)	0.0348 (11)	0.0200 (12)	0.0005 (10)	0.0010 (10)
C22	0.0517 (14)	0.0632 (14)	0.0475 (13)	0.0071 (11)	−0.0056 (10)	0.0032 (10)
C23	0.0480 (13)	0.0549 (13)	0.0422 (11)	0.0095 (10)	0.0095 (9)	0.0096 (9)
C24	0.0570 (15)	0.0631 (15)	0.0562 (14)	−0.0018 (12)	0.0098 (11)	0.0058 (11)
C25	0.0541 (18)	0.100 (2)	0.170 (3)	0.0069 (17)	−0.0213 (19)	0.028 (2)

Geometric parameters (Å, º)

C1—C2	1.343 (3)	C11—C12	1.430 (3)
C1—C11	1.426 (3)	C13—C14	1.429 (3)
C1—H1A	0.96	C15—O16	1.351 (2)
C2—C3	1.406 (3)	C15—O17	1.195 (2)
C2—H2A	0.96	O16—C18	1.414 (2)
C3—C4	1.335 (4)	C18—C23	1.371 (3)
C3—H3A	0.96	C18—C19	1.379 (3)
C4—C12	1.419 (3)	C19—C20	1.385 (3)
C4—H4A	0.96	C19—C24	1.499 (3)
C5—C6	1.346 (4)	C20—C21	1.372 (3)
C5—C14	1.417 (3)	C20—H20A	0.96
C5—H5A	0.96	C21—C22	1.380 (3)
C6—C7	1.404 (3)	C21—H21A	0.96
C6—H6A	0.96	C22—C23	1.377 (3)
C7—C8	1.349 (3)	C22—H22A	0.96
C7—H7A	0.96	C23—H23A	0.96
C8—C13	1.423 (3)	C24—C25	1.491 (4)
C8—H8A	0.96	C24—H24A	0.96
C9—C13	1.400 (3)	C24—H24B	0.96
C9—C11	1.400 (3)	C25—H25A	0.96
C9—C15	1.491 (2)	C25—H25B	0.96
N10—C14	1.337 (3)	C25—H25C	0.96
N10—C12	1.339 (3)
C2—C1—C11	121.0 (2)	N10—C14—C13	123.4 (2)
C2—C1—H1A	119.6	C5—C14—C13	119.1 (2)
C11—C1—H1A	119.4	C9—C15—O16	111.19 (16)
C1—C2—C3	120.5 (2)	C9—C15—O17	125.0 (2)
C1—C2—H2A	119.7	C11—C9—C15	118.22 (17)
C3—C2—H2A	119.8	C15—O16—C18	117.60 (14)
C4—C3—C2	121.1 (2)	O16—C15—O17	123.74 (17)
C4—C3—H3A	119.5	O16—C18—C19	117.20 (17)
C2—C3—H3A	119.3	C18—C19—C24	122.8 (2)
C3—C4—C12	120.8 (2)	C23—C18—C19	123.34 (17)
C3—C4—H4A	119.8	C23—C18—O16	119.32 (17)
C12—C4—H4A	119.4	C18—C19—C20	116.3 (2)
C6—C5—C14	120.7 (2)	C20—C19—C24	120.8 (2)
C6—C5—H5A	119.9	C21—C20—C19	122.0 (2)
C14—C5—H5A	119.4	C21—C20—H20A	119.2
C5—C6—C7	120.5 (2)	C19—C20—H20A	118.8
C5—C6—H6A	119.7	C20—C21—C22	119.7 (2)
C7—C6—H6a	119.7	C20—C21—H21A	120.5
C8—C7—C6	121.1 (2)	C22—C21—H21A	119.7
C8—C7—H7A	119.5	C23—C22—C21	120.0 (2)
C6—C7—H7A	119.5	C23—C22—H22A	119.9
C7—C8—C13	120.7 (2)	C21—C22—H22A	120.1
C7—C8—H8A	119.6	C18—C23—C22	118.6 (2)
C13—C8—H8A	119.6	C18—C23—H23A	120.7
C13—C9—C11	120.25 (16)	C22—C23—H23A	120.7
C13—C9—C15	121.52 (17)	C25—C24—C19	114.0 (2)
C14—N10—C12	118.59 (17)	C25—C24—H24A	108.8
C9—C11—C1	124.70 (17)	C19—C24—H24A	109.0
C9—C11—C12	117.4 (2)	C25—C24—H24B	108.5
C1—C11—C12	117.9 (2)	C19—C24—H24B	108.7
N10—C12—C4	118.3 (2)	H24A—C24—H24B	107.7
N10—C12—C11	123.1 (2)	C24—C25—H25A	109.5
C4—C12—C11	118.6 (2)	C24—C25—H25B	109.4
C9—C13—C8	124.89 (17)	H25A—C25—H25B	109.5
C9—C13—C14	117.2 (2)	C24—C25—H25C	109.5
C8—C13—C14	117.8 (2)	H25A—C25—H25C	109.5
N10—C14—C5	117.5 (2)	H25B—C25—H25C	109.5
C11—C1—C2—C3	0.2 (4)	C6—C5—C14—C13	0.6 (4)
C1—C2—C3—C4	−1.8 (4)	C9—C13—C14—N10	−1.9 (3)
C2—C3—C4—C12	1.1 (5)	C8—C13—C14—N10	178.0 (2)
C14—C5—C6—C7	1.4 (4)	C9—C13—C14—C5	177.6 (2)
C5—C6—C7—C8	−1.5 (4)	C8—C13—C14—C5	−2.4 (3)
C6—C7—C8—C13	−0.5 (4)	C13—C9—C15—O17	−128.4 (2)
C13—C9—C11—C1	−178.0 (2)	C13—C9—C15—O16	53.5 (2)
C15—C9—C11—C1	2.7 (3)	C9—C15—O16—C18	−177.82 (16)
C13—C9—C11—C12	0.3 (3)	C11—C9—C13—C14	1.2 (3)
C15—C9—C11—C12	−179.0 (2)	C11—C9—C15—O16	−127.2 (2)
C2—C1—C11—C9	−179.7 (2)	C11—C9—C15—O17	50.8 (3)
C2—C1—C11—C12	2.0 (3)	C15—O16—C18—C19	−116.7 (2)
C14—N10—C12—C4	−179.6 (2)	O16—C18—C19—C24	3.1 (3)
C14—N10—C12—C11	0.5 (3)	O17—C15—O16—C18	4.1 (3)
C3—C4—C12—N10	−178.7 (2)	C15—O16—C18—C23	67.3 (2)
C3—C4—C12—C11	1.2 (4)	C23—C18—C19—C20	−1.0 (3)
C9—C11—C12—N10	−1.2 (3)	O16—C18—C19—C20	−176.74 (17)
C1—C11—C12—N10	177.2 (2)	C23—C18—C19—C24	178.8 (2)
C9—C11—C12—C4	178.9 (2)	C18—C19—C20—C21	−0.2 (3)
C1—C11—C12—C4	−2.6 (3)	C24—C19—C20—C21	180.0 (2)
C11—C9—C13—C8	−178.8 (2)	C19—C20—C21—C22	0.8 (3)
C15—C9—C13—C8	0.4 (3)	C20—C21—C22—C23	−0.3 (3)
C15—C9—C13—C14	−179.59 (17)	C19—C18—C23—C22	1.5 (3)
C7—C8—C13—C9	−177.7 (2)	O16—C18—C23—C22	177.2 (2)
C7—C8—C13—C14	2.3 (3)	C21—C22—C23—C18	−0.8 (3)
C12—N10—C14—C5	−178.5 (2)	C18—C19—C24—C25	89.5 (3)
C12—N10—C14—C13	1.1 (3)	C20—C19—C24—C25	−90.7 (3)
C6—C5—C14—N10	−179.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···CgA^i	0.96	2.81	3.608 (3)	142
C6—H6A···CgA^ii	0.96	2.81	3.540 (3)	133
C24—H24A···CgB^iii	0.96	2.70	3.576 (3)	151

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

(II) 2,5-dimethylphenyl acridine-9-carboxylate

Crystal data

C22H17NO2	F(000) = 688
Mr = 327.37	Dx = 1.309 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 50 reflections
a = 11.769 (2) Å	θ = 2.3–26°
b = 15.404 (3) Å	µ = 0.08 mm^−1
c = 10.125 (2) Å	T = 293 K
β = 115.18 (3)°	Prism, yellow
V = 1661.1 (7) Å^3	0.5 × 0.4 × 0.3 mm
Z = 4

Data collection

Kuma KM-4 diffractometer	Rint = 0.019
Radiation source: fine-focus sealed tube	θmax = 26.0°, θmin = 2.3°
Graphite monochromator	h = 0→14
θ/2θ scans	k = −19→0
3424 measured reflections	l = −12→11
3267 independent reflections	3 standard reflections every 200 reflections
1619 reflections with I > 2σ(I)	intensity decay: 0.6%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.0582P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.92	(Δ/σ)max = 0.001
3267 reflections	Δρmax = 0.17 e Å^−3
227 parameters	Δρmin = −0.15 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0155 (17)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.20927 (15)	0.47340 (11)	−0.09760 (19)	0.0516 (4)
H1A	0.2748	0.4306	−0.0665	0.062*
C2	0.14294 (17)	0.49015 (12)	−0.24163 (19)	0.0602 (5)
H2A	0.1621	0.4594	−0.3121	0.072*
C3	0.04734 (17)	0.55282 (13)	−0.2900 (2)	0.0624 (5)
H3A	0.0007	0.5637	−0.3925	0.075*
C4	0.01969 (16)	0.59823 (11)	−0.19379 (19)	0.0539 (5)
H4A	−0.0465	0.6405	−0.2281	0.065*
C5	0.08440 (18)	0.66635 (11)	0.2897 (2)	0.0618 (5)
H5A	0.0183	0.7086	0.2510	0.074*
C6	0.1444 (2)	0.65547 (13)	0.4348 (2)	0.0713 (6)
H6A	0.1220	0.6895	0.4996	0.086*
C7	0.24110 (19)	0.59421 (13)	0.4949 (2)	0.0669 (5)
H7A	0.2837	0.5880	0.5990	0.080*
C8	0.27579 (16)	0.54401 (11)	0.40834 (19)	0.0557 (5)
H8A	0.3419	0.5023	0.4522	0.067*
C9	0.24516 (13)	0.50435 (9)	0.15759 (17)	0.0409 (4)
N10	0.05513 (12)	0.63085 (8)	0.04906 (15)	0.0490 (3)
C11	0.18284 (14)	0.51921 (9)	0.00771 (16)	0.0414 (4)
C12	0.08646 (14)	0.58377 (9)	−0.04112 (17)	0.0435 (4)
C13	0.21465 (14)	0.55312 (10)	0.25398 (17)	0.0432 (4)
C14	0.11726 (15)	0.61638 (10)	0.19307 (19)	0.0469 (4)
C15	0.34256 (15)	0.43544 (10)	0.21445 (17)	0.0468 (4)
O16	0.29415 (10)	0.36404 (7)	0.24412 (13)	0.0534 (3)
O17	0.44758 (12)	0.44111 (9)	0.2296 (2)	0.0927 (6)
C18	0.36886 (14)	0.28859 (10)	0.29262 (18)	0.0448 (4)
C19	0.33351 (14)	0.21791 (10)	0.20007 (18)	0.0489 (4)
C20	0.40315 (16)	0.14305 (11)	0.2551 (2)	0.0575 (5)
H20A	0.3847	0.0922	0.1946	0.069*
C21	0.49853 (16)	0.13915 (11)	0.3931 (2)	0.0581 (5)
H21A	0.5435	0.0858	0.4283	0.070*
C22	0.53092 (15)	0.21036 (11)	0.4839 (2)	0.0523 (4)
C23	0.46436 (14)	0.28639 (10)	0.43039 (18)	0.0484 (4)
H23A	0.4860	0.3378	0.4897	0.058*
C24	0.22563 (17)	0.22178 (13)	0.0514 (2)	0.0693 (6)
H24A	0.1517	0.2414	0.0601	0.104*
H24B	0.2108	0.1650	0.0081	0.104*
H24C	0.2454	0.2613	−0.0091	0.104*
C25	0.63114 (18)	0.20648 (13)	0.6379 (2)	0.0746 (6)
H25A	0.7032	0.1765	0.6394	0.112*
H25B	0.5996	0.1761	0.6981	0.112*
H25C	0.6546	0.2644	0.6745	0.112*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0512 (10)	0.0517 (10)	0.0548 (11)	0.0016 (8)	0.0253 (9)	0.0000 (8)
C2	0.0645 (12)	0.0692 (12)	0.0489 (11)	−0.0080 (10)	0.0260 (10)	−0.0057 (10)
C3	0.0592 (11)	0.0749 (13)	0.0463 (11)	−0.0058 (10)	0.0159 (9)	0.0091 (9)
C4	0.0448 (9)	0.0539 (10)	0.0525 (11)	0.0000 (8)	0.0107 (8)	0.0133 (9)
C5	0.0689 (12)	0.0490 (10)	0.0772 (14)	0.0000 (9)	0.0403 (11)	−0.0090 (10)
C6	0.0914 (15)	0.0606 (12)	0.0767 (15)	−0.0106 (12)	0.0499 (13)	−0.0233 (11)
C7	0.0820 (14)	0.0676 (12)	0.0512 (11)	−0.0154 (11)	0.0283 (10)	−0.0128 (10)
C8	0.0598 (11)	0.0534 (10)	0.0483 (11)	−0.0031 (9)	0.0175 (9)	−0.0003 (8)
C9	0.0379 (8)	0.0348 (8)	0.0481 (10)	0.0004 (7)	0.0164 (8)	0.0051 (7)
N10	0.0469 (7)	0.0413 (8)	0.0559 (9)	0.0047 (6)	0.0189 (7)	0.0042 (7)
C11	0.0396 (8)	0.0377 (8)	0.0463 (10)	−0.0031 (7)	0.0176 (8)	0.0022 (7)
C12	0.0404 (9)	0.0381 (9)	0.0498 (10)	−0.0023 (7)	0.0172 (7)	0.0063 (7)
C13	0.0438 (9)	0.0399 (8)	0.0442 (10)	−0.0053 (7)	0.0172 (8)	0.0000 (7)
C14	0.0487 (9)	0.0366 (9)	0.0571 (11)	−0.0035 (8)	0.0242 (8)	−0.0035 (8)
C15	0.0451 (10)	0.0470 (9)	0.0488 (10)	0.0035 (8)	0.0204 (8)	0.0071 (8)
O16	0.0431 (6)	0.0401 (6)	0.0743 (8)	0.0074 (5)	0.0225 (6)	0.0141 (6)
O17	0.0520 (8)	0.0727 (9)	0.1609 (16)	0.0177 (7)	0.0525 (9)	0.0526 (9)
C18	0.0405 (8)	0.0404 (9)	0.0557 (11)	0.0069 (7)	0.0225 (8)	0.0111 (8)
C19	0.0467 (9)	0.0505 (10)	0.0512 (11)	0.0004 (8)	0.0223 (8)	0.0024 (8)
C20	0.0600 (11)	0.0454 (10)	0.0727 (13)	0.0024 (9)	0.0335 (10)	−0.0031 (9)
C21	0.0569 (11)	0.0440 (10)	0.0770 (14)	0.0124 (9)	0.0318 (10)	0.0145 (9)
C22	0.0426 (9)	0.0564 (10)	0.0582 (11)	0.0039 (9)	0.0218 (8)	0.0149 (9)
C23	0.0456 (9)	0.0439 (9)	0.0546 (11)	−0.0015 (8)	0.0201 (8)	0.0004 (8)
C24	0.0626 (12)	0.0763 (14)	0.0617 (12)	0.0016 (10)	0.0193 (10)	−0.0047 (10)
C25	0.0585 (11)	0.0825 (14)	0.0696 (14)	0.0043 (11)	0.0146 (10)	0.0279 (11)

Geometric parameters (Å, º)

C1—C2	1.354 (2)	C11—C12	1.429 (2)
C1—C11	1.419 (2)	C13—C14	1.429 (2)
C1—H1A	0.96	C15—O16	1.330 (2)
C2—C3	1.403 (3)	C15—O17	1.182 (2)
C2—H2A	0.96	O16—C18	1.413 (2)
C3—C4	1.347 (2)	C18—C23	1.370 (2)
C3—H3A	0.96	C18—C19	1.380 (2)
C4—C12	1.422 (2)	C19—C20	1.387 (2)
C4—H4A	0.96	C19—C24	1.502 (2)
C5—C6	1.343 (3)	C20—C21	1.372 (2)
C5—C14	1.421 (2)	C20—H20A	0.96
C5—H5A	0.96	C21—C22	1.377 (2)
C6—C7	1.402 (3)	C21—H21A	0.96
C6—H6A	0.96	C22—C23	1.385 (2)
C7—C8	1.356 (3)	C22—C25	1.503 (2)
C7—H7A	0.96	C23—H23A	0.96
C8—C13	1.422 (2)	C24—H24A	0.96
C8—H8A	0.96	C24—H24B	0.96
C9—C13	1.394 (2)	C24—H24C	0.96
C9—C11	1.395 (2)	C25—H25A	0.96
C9—C15	1.487 (2)	C25—H25B	0.96
N10—C12	1.335 (2)	C25—H25C	0.96
N10—C14	1.343 (2)
C2—C1—C11	120.27 (16)	N10—C14—C13	123.23 (15)
C2—C1—H1A	119.9	C5—C14—C13	118.38 (16)
C11—C1—H1A	119.8	C9—C15—O16	110.12 (13)
C1—C2—C3	121.09 (17)	C9—C15—O17	126.07 (15)
C1—C2—H2A	119.7	C11—C9—C15	120.01 (14)
C3—C2—H2A	119.2	C15—O16—C18	119.69 (12)
C4—C3—C2	120.62 (17)	O16—C15—O17	123.80 (15)
C4—C3—H3A	119.2	O16—C18—C19	116.71 (14)
C2—C3—H3A	120.2	C18—C19—C24	122.10 (15)
C3—C4—C12	120.87 (17)	C23—C18—C19	123.48 (15)
C3—C4—H4A	120.0	C23—C18—O16	119.59 (15)
C12—C4—H4A	119.2	C18—C19—C20	115.30 (15)
C6—C5—C14	121.0 (2)	C20—C19—C24	122.59 (16)
C6—C5—H5A	119.2	C21—C20—C19	122.22 (17)
C14—C5—H5A	119.8	C21—C20—H20A	118.6
C5—C6—C7	120.7 (2)	C19—C20—H20A	119.1
C5—C6—H6A	120.7	C20—C21—C22	121.29 (16)
C7—C6—H6A	118.6	C20—C21—H21A	119.9
C8—C7—C6	121.0 (2)	C22—C21—H21A	118.8
C8—C7—H7A	119.5	C21—C22—C23	117.56 (17)
C6—C7—H7A	119.5	C21—C22—C25	122.19 (17)
C7—C8—C13	120.2 (2)	C23—C22—C25	120.21 (17)
C7—C8—H8A	119.4	C18—C23—C22	120.13 (16)
C13—C8—H8A	120.4	C18—C23—H23A	120.0
C13—C9—C11	120.02 (13)	C22—C23—H23A	119.8
C13—C9—C15	119.96 (14)	C19—C24—H24A	109.5
C12—N10—C14	118.11 (14)	C19—C24—H24B	109.5
C9—C11—C1	123.64 (14)	H24A—C24—H24B	109.5
C9—C11—C12	117.58 (14)	C19—C24—H24C	109.5
C1—C11—C12	118.78 (14)	H24A—C24—H24C	109.5
N10—C12—C4	118.20 (15)	H24B—C24—H24C	109.5
N10—C12—C11	123.43 (15)	C22—C25—H25A	109.5
C4—C12—C11	118.36 (15)	C22—C25—H25B	109.5
C9—C13—C8	123.74 (15)	H25A—C25—H25B	109.5
C9—C13—C14	117.61 (14)	C22—C25—H25C	109.5
C8—C13—C14	118.65 (15)	H25A—C25—H25C	109.5
N10—C14—C5	118.38 (16)	H25B—C25—H25C	109.5
C11—C1—C2—C3	0.1 (3)	O17—C15—O16—C18	−2.0 (3)
C1—C2—C3—C4	0.3 (3)	C15—O16—C18—C19	−113.59 (16)
C2—C3—C4—C12	−0.1 (3)	C15—C9—C13—C14	−177.82 (13)
C14—C5—C6—C7	−0.2 (3)	C7—C8—C13—C9	179.68 (16)
C5—C6—C7—C8	−0.5 (3)	C7—C8—C13—C14	0.4 (2)
C6—C7—C8—C13	0.4 (3)	C12—N10—C14—C5	179.95 (15)
C13—C9—C11—C1	179.11 (15)	C12—N10—C14—C13	−0.2 (2)
C15—C9—C11—C1	−2.0 (2)	C6—C5—C14—N10	−179.15 (16)
C13—C9—C11—C12	−1.5 (2)	C6—C5—C14—C13	1.0 (3)
C15—C9—C11—C12	177.43 (13)	C9—C13—C14—N10	−0.3 (2)
C2—C1—C11—C9	178.60 (15)	C8—C13—C14—N10	179.02 (15)
C2—C1—C11—C12	−0.8 (2)	C9—C13—C14—C5	179.64 (15)
C14—N10—C12—C4	179.22 (14)	C8—C13—C14—C5	−1.1 (2)
C14—N10—C12—C11	−0.3 (2)	C13—C9—C15—O17	−101.7 (2)
C3—C4—C12—N10	179.86 (16)	C13—C9—C15—O16	79.59 (18)
C3—C4—C12—C11	−0.6 (2)	C23—C18—C19—C20	−1.0 (2)
C9—C11—C12—N10	1.1 (2)	O16—C18—C19—C20	−175.58 (13)
C1—C11—C12—N10	−179.47 (14)	C23—C18—C19—C24	178.01 (16)
C9—C11—C12—C4	−178.40 (13)	C18—C19—C20—C21	1.5 (2)
C1—C11—C12—C4	1.0 (2)	C24—C19—C20—C21	−177.49 (17)
C11—C9—C13—C8	−178.14 (14)	C19—C20—C21—C22	−0.8 (3)
C15—C9—C13—C8	2.9 (2)	C20—C21—C22—C23	−0.5 (3)
C9—C15—O16—C18	176.78 (13)	C20—C21—C22—C25	177.19 (17)
C11—C9—C13—C14	1.1 (2)	C19—C18—C23—C22	−0.3 (2)
C11—C9—C15—O16	−99.33 (16)	O16—C18—C23—C22	174.20 (14)
C11—C9—C15—O17	79.4 (2)	C21—C22—C23—C18	1.0 (2)
C15—O16—C18—C23	71.6 (2)	C25—C22—C23—C18	−176.73 (15)
O16—C18—C19—C24	3.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25C···CgC^i	0.96	2.87	3.622 (2)	136

Symmetry code: (i) −x+1, y+3/2, −z+3/2.