Three isomeric forms of hydroxyphenyl-2-oxazoline: 2-(2-hydroxyphenyl)-2-oxazoline, 2-(3-hydroxyphenyl)-2-oxazoline and 2-(4-hydroxyphenyl)-2-oxazoline

Crystal structures are reported for three isomeric compounds, namely 2-(2-hydroxy­phenyl)-2-oxazoline, (I), 2-(3-hydroxy­phenyl)-2-oxazoline, (II), and 2-(4-hydroxy­phenyl)-2-oxazoline, (III), all C₉H₉NO₂ [systematic names: 2-(4,5-dihydro-1,3-oxazol-2-yl)phenol, (I), 3-(4,5-dihydro-1,3-oxazol-2-yl)phenol, (II), and 4-(4,5-dihydro-1,3-oxazol-2-yl)phenol, (III)]. In these compounds, the deviation from coplanarity of the oxazoline and benzene rings is dependent on the position of the hydroxy group on the benzene ring. The coplanar arrangement in (I) is stabilized by a strong intra­molecular O—H...N hydrogen bond. Surprisingly, the 2-oxazoline ring in mol­ecule B of (II) adopts a ³T₄ (^C2T_C3) conformation, while the 2-oxazoline ring in mol­ecule A, as well as that in (I) and (III), is nearly planar, as expected. Tetra­mers of mol­ecules of (II) are formed and they are bound together via weak C—H...N hydrogen bonds. In (III), strong inter­molecular O—H...N hydrogen bonds and weak intra­molecular C—H...O hydrogen bonds lead to the formation of an infinite chain of mol­ecules perpendicular to the b direction. This paper also reports a theoretical investigation of hydrogen bonds, based on density functional theory (DFT) employing periodic boundary conditions.

S1. Comment

Cyclic imino ethers, among them 2-oxazolines, are important intermediates in organic synthesis. The title compounds, (I)–(III), were prepared in the course of our research focused on cyclic imino ethers and their utilization in polymer chemistry (Kronek et al., 1998), as hydroxyphenyl-2-oxazolines are known to produce poly(ether-amides) on heating of the monomer (Wörner et al., 1995). Although the syntheses of these compounds have already been reported [for (I), Cwik et al., 2002; Black & Wade, 1972; Peterson et al., 1980; for (II), Kalle, 1969; for (III), Nonnenmacher & Plieninger, 1982], their crystal structures have not been published until now. Among 87 matches from the Cambridge Structural Database (CSD, February 2005 update, version 5.26; Allen, 2002) for (I), only 15 structures were relevant (i.e. having a 4,5-unsubstituted 2-oxazoline ring and a 3',4',5',6'-unsubstituted 2'-hydroxyphenyl moiety), but in all these compounds the [Text missing?]. 2-(2'-Hydroxyphenyl)-2-oxazoline has been reported as a ligand in several complexes with metals such as Fe, Mn, Ni, V, Zn, Al, In and Re (e.g. Qian et al., 2004; Kooijman et al., 2002; Miller et al., 1999; Melchior et al., 1999). For compounds (II) and (III), a CSD search revealed only one and 13 similar structures, respectively, but none of them had a relevant hydroxyl group in the meta or para position of the benzene ring.

Selected geometric parameters for (I), (II) and (III) are listed in Table 1. The numbering schemes, together with the corresponding atomic displacement ellipsoid plots, are shown in Figs. 1–3, respectively. The crystal packings of (I) and (II) are depicted in Figs. 4 and 5, respectively. The hydrogen-bonding schemes for (II) and (III) are shown in Figs. 6 and 7, respectively. The hydrogen-bonding geometries for (I), (II) and (III) are listed in Table 2. The theoretical investigation of hydrogen bonds was performed using the Vienna ab initio simulation package VASP (Kresse & Furthmüller, 1996; Kresse & Hafner, 1993). The calculations were based on density functional theory (DFT) with periodic boundary conditions (Jones & Gunnarsson, 1989).

The 2-oxazoline ring in (I) and (III) is nearly planar. Surprisingly, in the case of compound (II), with two molecules, A and B, in the asymmetric unit, the values of the relevant dihedral angles (Table 1) and puckering parameters (Cremer & Pople, 1975), Q = 0.108 (3) Å and ϕ = 310.3 (17)°, indicate that this ring in molecule B deviates significantly from planarity (twisting about the C3B—C2B bond) and adopts a ³T₄ (^C2T_C3) conformation, while the 2-oxazoline ring in molecule A is again nearly planar. This difference may be due to the arrangement of molecule B in the tetramer, as well as hydrogen bonding.

As seen from the values of the acute angles between the planes of the oxazolinyl and phenyl rings [0.74 (4)° for (I), 4.75 (16) and 3.49 (17)° for molecules A and B of (II), respectively, and 11.22 (6)° for (III)], the mutual position of these rings reflects the location (ortho, meta or para, respectively) of the hydroxyl group on the phenyl ring. In this respect, the coplanarity of both rings in the o-hydroxy derivative, (I) (Fig. 1), and the most evident deviation from coplanarity in the p-hydroxy derivative, (III), is observed. We assume that the coplanar arrangement of the rings and the syn-periplanar orientation of atom O2 (ortho-hydroxyl group) with respect to the C10—N1 bond in (I) is stabilized by the strong intramolecular O2—H2···N1 hydrogen bond (Table 2). In this regard, free rotation about the sp²–sp² C1—C4 bond could be sufficiently restricted, leading to possible atropisomerism, and this is probably responsible for the chirality because, although there is no chiral atom in (I), optical activity of [α]²⁰_D = 3.0 (c = 1, CHCl₃) was observed for this compound. The syn-periplanar arrangement of atom N1 relative to the C4—C5 bond, with atom N1 directed slightly below the phenyl ring plane, is observed for both molecules A and B of the m-hydroxy derivative, (II) (Fig. 2). In the case of molecule A, similar to the C5—O2 and C1—N1 bonds in (I), the C6—O2 and C1—N1 bonds are oriented cis with respect to the plane perpendicular to the plane of the phenyl and oxazoline rings across the C1—C4 bond. In contrast, the orientation of the C6—O2 and C1—N1 bonds is trans in the case of molecule B. For the p-hydroxy derivative, (III), shown in Fig. 3, the C1—N1 and C4—C5 bonds are oriented antiperiplanar, with atom N1 directed slightly above the plane of the phenyl ring.

The C1—C4 bond in compounds (I)–(III) is significantly shorter than the usual single C—C bond (Table 1; Reference for standard value?), indicating a weak conjugation between the 2-oxazoline ring substituted at the C-2 position (C1) and the phenyl group.

The hydrogen-bonding patterns can be described using graph theory (Bernstein et al., 1995; Grell et al., 1999). For (I), there is just one intramolecular hydrogen bond of the O—H···N type, which is, on the first-level graph-set, described as an S(6) string. For (II), there are two strong hydrogen bonds of the O—H···N type, two weak intramolecular bonds of the C—H···O type and one weak intermolecular interaction of the C—H···N type. On the first-level graph-set, the hydrogen-bonding pattern can be classified as D(2) for hydrogen bonds (IIa) and (IIb), S(5) for (IIc) and (IIe), and as a C(7) chain for hydrogen bond (IId) (Table 2). On the second-level graph-set, the above-mentioned tetramer is described as an R₄⁴(28) ring formed by hydrogen bonds (IIa) and (IIb), apart from D₃³(14) and D₂³(10) for bonds (IIa) and (IId), and (IIb) and (IId), respectively. The first-level graph-set descriptors for (III) are C(8) for the strong hydrogen bond (IIIa) and S(5) for the weak intramolecular hydrogen bond (IIIb). The molecules thus form an infinite chain perpendicular to the b direction, diagonal in the ab plane. The assignment of graph-set descriptors was performed using PLUTO, as described by Motherwell et al. (1999), and the notation of the hydrogen bonds here is that given in Table 2.

S2. Experimental

Compound (I) was prepared according to the procedure of Kobayashi et al. (1984). In the first step, 2-hydroxybenzoic acid methyl ester was reacted with an excess of ethanolamine at 413 K to give the corresponding hydroxyamide. This, in the next step upon treatment with thionyl chloride, afforded the required compound, (I). Compounds (II) and (III) were prepared analogously starting from the 3-hydroxy- or 4-hydroxybenzoic acid methyl ester, respectively. The analytical data of all three title compounds were in accordance with those published previously. Colourless single crystals of adequate quality for diffraction analysis [with the exception of (II)] were obtained by slow crystallization from nearly saturated solutions in ethanol under moderate cooling in a refrigerator.

S3. Refinement

The sample of (II) used for data collection was not a single-crystal. Nevertheless, it was possible to resolve one set of diffractions from one domain. As a result, there were overlapping reflections: 118 reflections were omitted from the data set due to severe F_o/F_c discrepancies (F_o >> F_c). H atoms for all compounds were refined isotropically and constrained to the ideal geometry using an appropriate riding model. For aromatic H atoms, the C—H distance was kept fixed at 0.95 Å, and for secondary H atoms, C—H = 0.99 Å. For the hydroxyl groups, the O—H distances (0.84 Å) and C—O—H angles (109.5°) were kept fixed, while the torsion angles were allowed to refine, with the starting position based on the circular Fourier synthesis.

Computing details

For all compounds, data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT and SADABS (Sheldrick, 2002); program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. The numbering scheme for (I), with atomic displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The numbering scheme for (II), with atomic displacement ellipsoids drawn at the 50% probability level.
	Fig. 3. The numbering scheme for (III), with atomic displacement ellipsoids drawn at the 50% probability level.
	Fig. 4. The unit-cell contents of (I) in projection along the a axis. H atoms not involved in hydrogen bonding have been omitted for clarity.
	Fig. 5. A projection of the structure of (II) along the a axis. The tetramers are bound together via the weak hydrogen bonds shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.
	Fig. 6. A tetramer of molecules of (II) formed via hydrogen bonds shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.
	Fig. 7. The hydrogen-bonding pattern in the crystal lattice of (III). H atoms not involved in hydrogen bonding have been omitted for clarity.

(I) 2-(4,5-dihydro-1,3-oxazol-2-yl)phenol

Crystal data

C9H9NO2	F(000) = 344
Mr = 163.17	Dx = 1.394 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8192 reflections
a = 5.7562 (1) Å	θ = 2.5–33.0°
b = 11.2464 (1) Å	µ = 0.10 mm^−1
c = 12.1365 (1) Å	T = 173 K
β = 98.162 (1)°	Block, colourless
V = 777.72 (2) Å^3	0.80 × 0.42 × 0.40 mm
Z = 4

Data collection

Siemens SMART CCD area-detector diffractometer	2785 independent reflections
Radiation source: fine-focus sealed tube	2451 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ω scans	θmax = 33.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −8→8
Tmin = 0.724, Tmax = 0.961	k = −16→17
13125 measured reflections	l = −18→17

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)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.119	w = 1/[σ^2(Fo^2) + (0.0707P)^2 + 0.1146P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
2785 reflections	Δρmax = 0.36 e Å^−3
120 parameters	Δρmin = −0.20 e Å^−3
0 restraints	Extinction correction: SHELXTL (Bruker, 2001), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.051 (7)

Special details

Experimental. Data were collected at low temperature using a Siemens SMART CCD diffractometer equiped with an LT-2 device. A full sphere of reciprocal space was scanned by 0.3° steps in ω with a crystal-to-detector distance of 3.97 cm, 10 s per frame. The preliminary orientation matrix was obtained from the first 100 frames using SMART (Siemens, 1995). The collected frames were integrated using the preliminary orientation matrix, which was updated every 100 frames. Final cell parameters were obtained by refinement on the position of 8192 reflections with I > 10σ(I) after integration of all the frames data using SAINT (Siemens, 1995).

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	−0.31502 (11)	0.53523 (5)	0.92298 (5)	0.03030 (15)
O2	0.22761 (12)	0.67838 (6)	0.76625 (5)	0.03624 (17)
H2	0.1385	0.6207	0.7469	0.067 (5)*
N1	−0.10084 (12)	0.51985 (6)	0.78128 (5)	0.02756 (15)
C1	−0.14136 (12)	0.57529 (6)	0.86899 (6)	0.02236 (15)
C2	−0.26962 (16)	0.42099 (7)	0.76396 (7)	0.03023 (18)
H2A	−0.1873	0.3435	0.7685	0.030 (3)*
H2B	−0.3684	0.4275	0.6905	0.041 (3)*
C3	−0.41902 (15)	0.43393 (7)	0.85872 (7)	0.02926 (17)
H3A	−0.5853	0.4497	0.8289	0.034 (3)*
H3B	−0.4102	0.3612	0.9050	0.033 (3)*
C4	−0.01057 (12)	0.67954 (6)	0.91529 (6)	0.02151 (15)
C5	0.17266 (13)	0.72529 (7)	0.86198 (6)	0.02536 (16)
C6	0.30083 (15)	0.82308 (8)	0.90818 (7)	0.03128 (18)
H6	0.4265	0.8535	0.8736	0.054 (4)*
C7	0.24526 (15)	0.87594 (8)	1.00426 (7)	0.03189 (18)
H7	0.3333	0.9425	1.0350	0.046 (3)*
C8	0.06187 (15)	0.83266 (7)	1.05639 (7)	0.02959 (17)
H8	0.0239	0.8698	1.1218	0.045 (3)*
C9	−0.06450 (13)	0.73495 (7)	1.01192 (6)	0.02515 (16)
H9	−0.1894	0.7051	1.0474	0.043 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0328 (3)	0.0291 (3)	0.0312 (3)	−0.0091 (2)	0.0123 (2)	−0.0052 (2)
O2	0.0395 (3)	0.0433 (4)	0.0294 (3)	−0.0078 (3)	0.0170 (3)	−0.0050 (2)
N1	0.0320 (3)	0.0279 (3)	0.0231 (3)	−0.0025 (2)	0.0051 (2)	−0.0019 (2)
C1	0.0234 (3)	0.0224 (3)	0.0213 (3)	0.0008 (2)	0.0031 (2)	0.0028 (2)
C2	0.0388 (4)	0.0259 (4)	0.0255 (3)	−0.0045 (3)	0.0030 (3)	−0.0012 (3)
C3	0.0292 (4)	0.0256 (3)	0.0328 (4)	−0.0046 (3)	0.0037 (3)	−0.0020 (3)
C4	0.0217 (3)	0.0219 (3)	0.0212 (3)	0.0003 (2)	0.0039 (2)	0.0021 (2)
C5	0.0256 (3)	0.0285 (4)	0.0231 (3)	−0.0005 (3)	0.0071 (2)	0.0027 (2)
C6	0.0287 (4)	0.0334 (4)	0.0331 (4)	−0.0073 (3)	0.0091 (3)	0.0021 (3)
C7	0.0331 (4)	0.0289 (4)	0.0338 (4)	−0.0083 (3)	0.0054 (3)	−0.0018 (3)
C8	0.0336 (4)	0.0270 (4)	0.0292 (4)	−0.0034 (3)	0.0079 (3)	−0.0040 (3)
C9	0.0262 (3)	0.0251 (3)	0.0254 (3)	−0.0019 (2)	0.0078 (2)	−0.0010 (2)

Geometric parameters (Å, º)

O1—C1	1.3481 (9)	C3—H3B	0.9900
O1—C3	1.4601 (10)	C4—C9	1.4012 (10)
O2—C5	1.3537 (9)	C4—C5	1.4104 (10)
O2—H2	0.8400	C5—C6	1.3968 (11)
N1—C1	1.2832 (10)	C6—C7	1.3861 (12)
N1—C2	1.4718 (11)	C6—H6	0.9500
C1—C4	1.4619 (10)	C7—C8	1.3932 (11)
C2—C3	1.5376 (12)	C7—H7	0.9500
C2—H2A	0.9900	C8—C9	1.3843 (11)
C2—H2B	0.9900	C8—H8	0.9500
C3—H3A	0.9900	C9—H9	0.9500
C1—O1—C3	106.10 (6)	C9—C4—C5	119.38 (7)
C5—O2—H2	109.5	C9—C4—C1	121.01 (6)
C1—N1—C2	106.95 (7)	C5—C4—C1	119.61 (6)
N1—C1—O1	118.38 (7)	O2—C5—C6	118.48 (7)
N1—C1—C4	124.35 (7)	O2—C5—C4	122.18 (7)
O1—C1—C4	117.27 (6)	C6—C5—C4	119.33 (7)
N1—C2—C3	104.45 (6)	C7—C6—C5	120.23 (7)
N1—C2—H2A	110.9	C7—C6—H6	119.9
C3—C2—H2A	110.9	C5—C6—H6	119.9
N1—C2—H2B	110.9	C6—C7—C8	120.82 (7)
C3—C2—H2B	110.9	C6—C7—H7	119.6
H2A—C2—H2B	108.9	C8—C7—H7	119.6
O1—C3—C2	104.06 (6)	C9—C8—C7	119.37 (7)
O1—C3—H3A	110.9	C9—C8—H8	120.3
C2—C3—H3A	110.9	C7—C8—H8	120.3
O1—C3—H3B	110.9	C8—C9—C4	120.84 (7)
C2—C3—H3B	110.9	C8—C9—H9	119.6
H3A—C3—H3B	109.0	C4—C9—H9	119.6
C2—N1—C1—O1	0.07 (10)	C9—C4—C5—O2	−177.58 (7)
C2—N1—C1—C4	179.78 (7)	C1—C4—C5—O2	2.37 (11)
C3—O1—C1—N1	−1.64 (10)	C9—C4—C5—C6	1.65 (11)
C3—O1—C1—C4	178.64 (6)	C1—C4—C5—C6	−178.40 (7)
C1—N1—C2—C3	1.43 (8)	O2—C5—C6—C7	178.02 (8)
C1—O1—C3—C2	2.32 (8)	C4—C5—C6—C7	−1.24 (12)
N1—C2—C3—O1	−2.27 (8)	C5—C6—C7—C8	0.11 (13)
N1—C1—C4—C9	−179.65 (7)	C6—C7—C8—C9	0.60 (13)
O1—C1—C4—C9	0.06 (10)	C7—C8—C9—C4	−0.17 (12)
N1—C1—C4—C5	0.40 (11)	C5—C4—C9—C8	−0.96 (11)
O1—C1—C4—C5	−179.89 (6)	C1—C4—C9—C8	179.10 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.84	1.88	2.6238 (9)	148

(II) 3-(4,5-dihydro-1,3-oxazol-2-yl)phenol

Crystal data

C9H9NO2	F(000) = 688
Mr = 163.17	Dx = 1.360 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8192 reflections
a = 11.3650 (2) Å	θ = 2.4–25.0°
b = 12.5867 (1) Å	µ = 0.10 mm^−1
c = 11.2966 (2) Å	T = 173 K
β = 99.534 (1)°	Needle, colourless
V = 1593.63 (4) Å^3	0.58 × 0.18 × 0.16 mm
Z = 8

Data collection

Siemens SMART CCD area-detector diffractometer	2663 independent reflections
Radiation source: fine-focus sealed tube	2167 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −13→13
Tmin = 0.816, Tmax = 0.985	k = −14→14
14444 measured reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.175	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.079P)^2 + 2.9545P] where P = (Fo^2 + 2Fc^2)/3
2663 reflections	(Δ/σ)max < 0.001
237 parameters	Δρmax = 0.39 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

Experimental. The sample used was not a single-crystal. Nevertheless, it was possible to resolve one set of diffractions from one domain. As a result, there were overlapping reflections; 118 reflections were omitted from the data set due to severe F_o/F_c discrepancies (F_o >> F_c). Data were collected at low temperature using a Siemens SMART CCD diffractometer equiped with an LT-2 device. A full sphere of reciprocal space was scanned by 0.3° steps in ω with a crystal-to-detector distance of 3.97 cm, 30 s per frame. The preliminary orientation matrix was obtained from the first 100 frames using SMART (Siemens, 1995). The collected frames were integrated using the preliminary orientation matrix, which was updated every 100 frames. Final cell parameters were obtained by refinement on the position of 8192 reflections with I > 10σ(I) after integration of all the frames data using SAINT (Siemens, 1995).

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 (Ų)

	x	y	z	Uiso*/Ueq
O1A	0.40833 (18)	0.30148 (17)	0.02099 (19)	0.0298 (5)
O2A	0.6332 (2)	0.5838 (2)	−0.3143 (2)	0.0374 (6)
H2A	0.7006	0.5612	−0.2821	0.10 (2)*
N1A	0.6025 (2)	0.2864 (2)	0.0037 (2)	0.0258 (6)
C1A	0.5023 (2)	0.3329 (2)	−0.0302 (2)	0.0217 (6)
C2A	0.5856 (3)	0.2091 (3)	0.0989 (3)	0.0286 (7)
H2A1	0.6327	0.2300	0.1772	0.041 (10)*
H2A2	0.6096	0.1368	0.0782	0.028 (8)*
C3A	0.4508 (3)	0.2139 (3)	0.1028 (3)	0.0351 (8)
H3A1	0.4112	0.1463	0.0747	0.043 (10)*
H3A2	0.4360	0.2289	0.1851	0.046 (11)*
C4A	0.4774 (2)	0.4158 (2)	−0.1222 (3)	0.0221 (6)
C5A	0.5708 (2)	0.4592 (2)	−0.1727 (3)	0.0227 (6)
H5A	0.6503	0.4357	−0.1470	0.031 (9)*
C6A	0.5470 (3)	0.5371 (2)	−0.2610 (3)	0.0249 (7)
C7A	0.4300 (3)	0.5723 (3)	−0.2977 (3)	0.0297 (7)
H7A	0.4136	0.6255	−0.3578	0.041 (10)*
C8A	0.3378 (3)	0.5294 (3)	−0.2463 (3)	0.0295 (7)
H8A	0.2586	0.5541	−0.2714	0.037 (9)*
C9A	0.3594 (3)	0.4516 (2)	−0.1593 (3)	0.0265 (7)
H9A	0.2957	0.4225	−0.1249	0.053 (11)*
O1B	0.94268 (18)	0.51245 (18)	0.2167 (2)	0.0308 (5)
O2B	0.79400 (19)	0.24456 (19)	−0.1031 (2)	0.0350 (6)
H2B	0.7408	0.2658	−0.0652	0.040 (11)*
N1B	1.1424 (2)	0.4989 (2)	0.2554 (2)	0.0286 (6)
C1B	1.0449 (2)	0.4678 (2)	0.1923 (3)	0.0222 (6)
C2B	1.1129 (3)	0.5829 (3)	0.3369 (3)	0.0351 (8)
H2B1	1.1418	0.6529	0.3142	0.024 (8)*
H2B2	1.1488	0.5672	0.4211	0.037 (9)*
C3B	0.9764 (3)	0.5809 (3)	0.3210 (3)	0.0330 (8)
H3B1	0.9489	0.5509	0.3928	0.031 (9)*
H3B2	0.9427	0.6531	0.3058	0.050 (11)*
C4B	1.0302 (2)	0.3875 (2)	0.0969 (3)	0.0224 (6)
C5B	0.9157 (3)	0.3550 (2)	0.0437 (3)	0.0239 (6)
H5B	0.8473	0.3848	0.0694	0.028 (8)*
C6B	0.9024 (3)	0.2791 (2)	−0.0469 (3)	0.0252 (7)
C7B	1.0028 (3)	0.2351 (3)	−0.0846 (3)	0.0304 (7)
H7B	0.9935	0.1830	−0.1463	0.031 (9)*
C8B	1.1161 (3)	0.2675 (3)	−0.0319 (3)	0.0293 (7)
H8B	1.1842	0.2377	−0.0581	0.020 (8)*
C9B	1.1310 (3)	0.3435 (2)	0.0590 (3)	0.0278 (7)
H9B	1.2088	0.3652	0.0951	0.040 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0215 (11)	0.0321 (12)	0.0376 (12)	0.0037 (9)	0.0100 (9)	0.0086 (10)
O2A	0.0249 (12)	0.0423 (14)	0.0463 (14)	−0.0004 (10)	0.0096 (11)	0.0148 (12)
N1A	0.0220 (13)	0.0253 (13)	0.0305 (14)	0.0023 (10)	0.0061 (10)	0.0045 (11)
C1A	0.0208 (14)	0.0209 (15)	0.0240 (15)	−0.0021 (11)	0.0058 (12)	−0.0040 (12)
C2A	0.0286 (17)	0.0264 (16)	0.0320 (17)	0.0072 (13)	0.0088 (13)	0.0053 (13)
C3A	0.0320 (18)	0.0320 (18)	0.043 (2)	0.0042 (14)	0.0106 (15)	0.0159 (15)
C4A	0.0220 (15)	0.0210 (15)	0.0232 (14)	0.0010 (11)	0.0036 (11)	−0.0046 (12)
C5A	0.0192 (14)	0.0242 (15)	0.0241 (15)	0.0023 (11)	0.0018 (12)	−0.0033 (12)
C6A	0.0224 (15)	0.0277 (16)	0.0253 (15)	−0.0016 (12)	0.0059 (12)	0.0030 (13)
C7A	0.0304 (17)	0.0302 (17)	0.0277 (16)	0.0037 (13)	0.0027 (13)	0.0055 (14)
C8A	0.0228 (15)	0.0318 (17)	0.0332 (17)	0.0068 (13)	0.0028 (13)	0.0015 (14)
C9A	0.0215 (15)	0.0279 (16)	0.0302 (16)	0.0031 (12)	0.0050 (12)	−0.0023 (13)
O1B	0.0184 (10)	0.0365 (13)	0.0379 (12)	0.0007 (9)	0.0055 (9)	−0.0137 (10)
O2B	0.0222 (11)	0.0422 (14)	0.0415 (13)	−0.0051 (10)	0.0077 (10)	−0.0133 (11)
N1B	0.0223 (13)	0.0308 (14)	0.0334 (14)	−0.0027 (11)	0.0070 (11)	−0.0039 (12)
C1B	0.0172 (14)	0.0235 (15)	0.0277 (15)	0.0000 (11)	0.0089 (12)	0.0043 (12)
C2B	0.0303 (17)	0.0389 (19)	0.0360 (18)	−0.0038 (14)	0.0047 (14)	−0.0109 (15)
C3B	0.0307 (17)	0.0359 (18)	0.0340 (17)	−0.0006 (14)	0.0101 (14)	−0.0132 (15)
C4B	0.0209 (14)	0.0208 (15)	0.0258 (15)	−0.0007 (12)	0.0052 (11)	0.0036 (12)
C5B	0.0189 (14)	0.0257 (15)	0.0280 (15)	0.0019 (12)	0.0063 (12)	0.0007 (13)
C6B	0.0236 (15)	0.0239 (15)	0.0288 (16)	−0.0033 (12)	0.0063 (12)	0.0010 (13)
C7B	0.0360 (18)	0.0265 (16)	0.0306 (16)	0.0007 (13)	0.0108 (14)	−0.0055 (14)
C8B	0.0217 (15)	0.0324 (17)	0.0360 (17)	0.0047 (13)	0.0113 (13)	−0.0022 (14)
C9B	0.0211 (15)	0.0293 (17)	0.0340 (17)	−0.0016 (12)	0.0077 (13)	−0.0028 (13)

Geometric parameters (Å, º)

O1A—C1A	1.356 (3)	O1B—C1B	1.359 (3)
O1A—C3A	1.468 (4)	O1B—C3B	1.459 (4)
O2A—C6A	1.364 (4)	O2B—C6B	1.360 (4)
O2A—H2A	0.8400	O2B—H2B	0.8400
N1A—C1A	1.281 (4)	N1B—C1B	1.276 (4)
N1A—C2A	1.486 (4)	N1B—C2B	1.476 (4)
C1A—C4A	1.466 (4)	C1B—C4B	1.467 (4)
C2A—C3A	1.540 (4)	C2B—C3B	1.533 (4)
C2A—H2A1	0.9900	C2B—H2B1	0.9900
C2A—H2A2	0.9900	C2B—H2B2	0.9900
C3A—H3A1	0.9900	C3B—H3B1	0.9900
C3A—H3A2	0.9900	C3B—H3B2	0.9900
C4A—C9A	1.411 (4)	C4B—C9B	1.402 (4)
C4A—C5A	1.398 (4)	C4B—C5B	1.402 (4)
C5A—C6A	1.393 (4)	C5B—C6B	1.390 (4)
C5A—H5A	0.9500	C5B—H5B	0.9500
C6A—C7A	1.398 (4)	C6B—C7B	1.397 (4)
C7A—C8A	1.389 (4)	C7B—C8B	1.388 (4)
C7A—H7A	0.9500	C7B—H7B	0.9500
C8A—C9A	1.380 (4)	C8B—C9B	1.393 (4)
C8A—H8A	0.9500	C8B—H8B	0.9500
C9A—H9A	0.9500	C9B—H9B	0.9500
C1A—O1A—C3A	106.7 (2)	C1B—O1B—C3B	106.8 (2)
C6A—O2A—H2A	109.5	C6B—O2B—H2B	109.5
C1A—N1A—C2A	107.5 (2)	C1B—N1B—C2B	107.6 (2)
N1A—C1A—O1A	117.6 (3)	N1B—C1B—O1B	116.9 (3)
N1A—C1A—C4A	126.5 (3)	N1B—C1B—C4B	127.2 (3)
O1A—C1A—C4A	115.9 (2)	O1B—C1B—C4B	115.9 (2)
N1A—C2A—C3A	104.1 (2)	N1B—C2B—C3B	104.2 (2)
N1A—C2A—H2A1	110.9	N1B—C2B—H2B1	110.9
C3A—C2A—H2A1	110.9	C3B—C2B—H2B1	110.9
N1A—C2A—H2A2	110.9	N1B—C2B—H2B2	110.9
C3A—C2A—H2A2	110.9	C3B—C2B—H2B2	110.9
H2A1—C2A—H2A2	109.0	H2B1—C2B—H2B2	108.9
O1A—C3A—C2A	103.7 (2)	O1B—C3B—C2B	103.3 (2)
O1A—C3A—H3A1	111.0	O1B—C3B—H3B1	111.1
C2A—C3A—H3A1	111.0	C2B—C3B—H3B1	111.1
O1A—C3A—H3A2	111.0	O1B—C3B—H3B2	111.1
C2A—C3A—H3A2	111.0	C2B—C3B—H3B2	111.1
H3A1—C3A—H3A2	109.0	H3B1—C3B—H3B2	109.1
C9A—C4A—C5A	120.2 (3)	C9B—C4B—C5B	120.1 (3)
C9A—C4A—C1A	120.1 (3)	C9B—C4B—C1B	119.8 (3)
C5A—C4A—C1A	119.8 (3)	C5B—C4B—C1B	120.0 (3)
C6A—C5A—C4A	119.9 (3)	C6B—C5B—C4B	119.7 (3)
C6A—C5A—H5A	120.1	C6B—C5B—H5B	120.1
C4A—C5A—H5A	120.1	C4B—C5B—H5B	120.1
O2A—C6A—C5A	123.4 (3)	O2B—C6B—C5B	122.8 (3)
O2A—C6A—C7A	116.8 (3)	O2B—C6B—C7B	117.0 (3)
C5A—C6A—C7A	119.8 (3)	C5B—C6B—C7B	120.2 (3)
C8A—C7A—C6A	120.0 (3)	C8B—C7B—C6B	120.0 (3)
C8A—C7A—H7A	120.0	C8B—C7B—H7B	120.0
C6A—C7A—H7A	120.0	C6B—C7B—H7B	120.0
C7A—C8A—C9A	121.0 (3)	C7B—C8B—C9B	120.6 (3)
C7A—C8A—H8A	119.5	C7B—C8B—H8B	119.7
C9A—C8A—H8A	119.5	C9B—C8B—H8B	119.7
C4A—C9A—C8A	119.1 (3)	C8B—C9B—C4B	119.4 (3)
C4A—C9A—H9A	120.4	C8B—C9B—H9B	120.3
C8A—C9A—H9A	120.4	C4B—C9B—H9B	120.3
C2A—N1A—C1A—O1A	−2.1 (4)	C2B—N1B—C1B—O1B	−2.8 (4)
C2A—N1A—C1A—C4A	179.6 (3)	C2B—N1B—C1B—C4B	178.3 (3)
C3A—O1A—C1A—N1A	−2.4 (4)	C3B—O1B—C1B—N1B	−4.7 (4)
C3A—O1A—C1A—C4A	176.0 (2)	C3B—O1B—C1B—C4B	174.3 (2)
C1A—N1A—C2A—C3A	5.5 (3)	C1B—N1B—C2B—C3B	8.7 (3)
C1A—O1A—C3A—C2A	5.6 (3)	C1B—O1B—C3B—C2B	9.5 (3)
N1A—C2A—C3A—O1A	−6.6 (3)	N1B—C2B—C3B—O1B	−10.9 (3)
N1A—C1A—C4A—C9A	173.1 (3)	N1B—C1B—C4B—C9B	−6.2 (5)
O1A—C1A—C4A—C9A	−5.2 (4)	O1B—C1B—C4B—C9B	174.9 (3)
N1A—C1A—C4A—C5A	−6.9 (4)	N1B—C1B—C4B—C5B	173.9 (3)
O1A—C1A—C4A—C5A	174.8 (2)	O1B—C1B—C4B—C5B	−5.0 (4)
C9A—C4A—C5A—C6A	−0.7 (4)	C9B—C4B—C5B—C6B	−0.1 (4)
C1A—C4A—C5A—C6A	179.3 (3)	C1B—C4B—C5B—C6B	179.8 (3)
C4A—C5A—C6A—O2A	179.6 (3)	C4B—C5B—C6B—O2B	−179.5 (3)
C4A—C5A—C6A—C7A	0.7 (4)	C4B—C5B—C6B—C7B	0.2 (4)
O2A—C6A—C7A—C8A	−179.2 (3)	O2B—C6B—C7B—C8B	179.4 (3)
C5A—C6A—C7A—C8A	−0.1 (5)	C5B—C6B—C7B—C8B	−0.3 (5)
C6A—C7A—C8A—C9A	−0.4 (5)	C6B—C7B—C8B—C9B	0.3 (5)
C5A—C4A—C9A—C8A	0.3 (4)	C7B—C8B—C9B—C4B	−0.3 (5)
C1A—C4A—C9A—C8A	−179.7 (3)	C5B—C4B—C9B—C8B	0.2 (4)
C7A—C8A—C9A—C4A	0.3 (5)	C1B—C4B—C9B—C8B	−179.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2A—H2A···N1B^i	0.84	1.92	2.732 (3)	164
O2B—H2B···N1A	0.84	1.88	2.709 (3)	167
C5B—H5B···O1B	0.95	2.43	2.764 (4)	100
C7A—H7A···N1A^ii	0.95	2.60	3.540 (4)	171
C9A—H9A···O1A	0.95	2.45	2.767 (4)	100

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

(III) 4-(4,5-dihydro-1,3-oxazol-2-yl)phenol

Crystal data

C9H9NO2	F(000) = 344
Mr = 163.17	Dx = 1.394 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6730 reflections
a = 4.7778 (1) Å	θ = 2.3–33.1°
b = 14.9883 (2) Å	µ = 0.10 mm^−1
c = 10.9194 (1) Å	T = 173 K
β = 95.945 (1)°	Plate, colourless
V = 777.74 (2) Å^3	0.60 × 0.32 × 0.06 mm
Z = 4

Data collection

Siemens SMART CCD area-detector diffractometer	2784 independent reflections
Radiation source: fine-focus sealed tube	2064 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
ω scans	θmax = 33.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −7→7
Tmin = 0.710, Tmax = 0.994	k = −22→22
13219 measured reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.133	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0613P)^2 + 0.2076P] where P = (Fo^2 + 2Fc^2)/3
2784 reflections	(Δ/σ)max < 0.001
119 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

Experimental. Data were collected at low temperature using a Siemens SMART CCD diffractometer equiped with an LT-2 device. A full sphere of reciprocal space was scanned by 0.3° steps in ω with a crystal-to-detector distance of 3.97 cm, 10 s per frame. The preliminary orientation matrix was obtained from the first 100 frames using SMART (Siemens, 1995). The collected frames were integrated using the preliminary orientation matrix, which was updated every 100 frames. Final cell parameters were obtained by refinement on the position of 6730 reflections with I > 10σ(I) after integration of all the frames data using SAINT (Siemens, 1995).

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.8194 (2)	0.53816 (6)	0.60741 (8)	0.0375 (2)
O2	0.04190 (19)	0.88041 (6)	0.51369 (8)	0.0319 (2)
H2	0.0943	0.8987	0.4470	0.068 (6)*
N1	0.7108 (2)	0.55667 (7)	0.80165 (9)	0.0294 (2)
C1	0.6770 (2)	0.58270 (7)	0.68969 (10)	0.0259 (2)
C2	0.9168 (3)	0.48288 (8)	0.80957 (12)	0.0343 (3)
H2A	0.8371	0.4286	0.8443	0.046 (4)*
H2B	1.0910	0.4998	0.8614	0.045 (4)*
C3	0.9756 (3)	0.46749 (9)	0.67567 (12)	0.0348 (3)
H3A	1.1794	0.4722	0.6672	0.040 (4)*
H3B	0.9081	0.4080	0.6464	0.047 (4)*
C4	0.5040 (2)	0.65798 (7)	0.64100 (10)	0.0254 (2)
C5	0.5233 (3)	0.68982 (8)	0.52173 (10)	0.0307 (3)
H5	0.6436	0.6606	0.4705	0.050 (5)*
C6	0.3699 (3)	0.76319 (8)	0.47749 (10)	0.0300 (2)
H6	0.3851	0.7838	0.3962	0.041 (4)*
C7	0.1922 (2)	0.80737 (7)	0.55155 (10)	0.0253 (2)
C8	0.1695 (2)	0.77513 (8)	0.67048 (10)	0.0306 (2)
H8	0.0473	0.8039	0.7213	0.042 (4)*
C9	0.3237 (2)	0.70175 (8)	0.71444 (10)	0.0292 (2)
H9	0.3070	0.6807	0.7955	0.038 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0452 (5)	0.0399 (5)	0.0288 (4)	0.0132 (4)	0.0105 (4)	−0.0020 (4)
O2	0.0359 (5)	0.0342 (5)	0.0266 (4)	0.0060 (3)	0.0090 (3)	0.0026 (3)
N1	0.0328 (5)	0.0287 (5)	0.0272 (5)	0.0015 (4)	0.0060 (4)	0.0001 (4)
C1	0.0250 (5)	0.0272 (5)	0.0259 (5)	−0.0025 (4)	0.0051 (4)	−0.0042 (4)
C2	0.0356 (6)	0.0322 (6)	0.0359 (6)	0.0042 (5)	0.0070 (5)	0.0033 (5)
C3	0.0356 (6)	0.0303 (6)	0.0390 (7)	0.0050 (5)	0.0057 (5)	−0.0028 (5)
C4	0.0248 (5)	0.0287 (5)	0.0233 (5)	−0.0016 (4)	0.0048 (4)	−0.0024 (4)
C5	0.0343 (6)	0.0363 (6)	0.0229 (5)	0.0044 (5)	0.0091 (4)	−0.0024 (4)
C6	0.0346 (6)	0.0357 (6)	0.0209 (5)	0.0023 (5)	0.0091 (4)	0.0006 (4)
C7	0.0253 (5)	0.0280 (5)	0.0229 (5)	−0.0014 (4)	0.0045 (4)	−0.0015 (4)
C8	0.0315 (6)	0.0381 (6)	0.0237 (5)	0.0046 (5)	0.0102 (4)	0.0005 (4)
C9	0.0309 (6)	0.0346 (6)	0.0232 (5)	0.0021 (4)	0.0085 (4)	0.0021 (4)

Geometric parameters (Å, º)

O1—C1	1.3575 (13)	C3—H3B	0.9900
O1—C3	1.4559 (16)	C4—C5	1.3989 (15)
O2—C7	1.3505 (14)	C4—C9	1.3998 (15)
O2—H2	0.8400	C5—C6	1.3809 (17)
N1—C1	1.2775 (14)	C5—H5	0.9500
N1—C2	1.4769 (15)	C6—C7	1.3982 (15)
C1—C4	1.4654 (16)	C6—H6	0.9500
C2—C3	1.5347 (18)	C7—C8	1.4003 (15)
C2—H2A	0.9900	C8—C9	1.3818 (16)
C2—H2B	0.9900	C8—H8	0.9500
C3—H3A	0.9900	C9—H9	0.9500
C1—O1—C3	106.53 (9)	C5—C4—C9	118.51 (11)
C7—O2—H2	109.5	C5—C4—C1	120.76 (10)
C1—N1—C2	107.60 (9)	C9—C4—C1	120.68 (10)
N1—C1—O1	117.43 (10)	C6—C5—C4	120.91 (10)
N1—C1—C4	126.39 (10)	C6—C5—H5	119.5
O1—C1—C4	116.16 (10)	C4—C5—H5	119.5
N1—C2—C3	104.09 (10)	C5—C6—C7	120.45 (10)
N1—C2—H2A	110.9	C5—C6—H6	119.8
C3—C2—H2A	110.9	C7—C6—H6	119.8
N1—C2—H2B	110.9	O2—C7—C8	118.29 (10)
C3—C2—H2B	110.9	O2—C7—C6	122.83 (10)
H2A—C2—H2B	109.0	C8—C7—C6	118.88 (10)
O1—C3—C2	104.10 (9)	C9—C8—C7	120.47 (10)
O1—C3—H3A	110.9	C9—C8—H8	119.8
C2—C3—H3A	110.9	C7—C8—H8	119.8
O1—C3—H3B	110.9	C8—C9—C4	120.77 (10)
C2—C3—H3B	110.9	C8—C9—H9	119.6
H3A—C3—H3B	109.0	C4—C9—H9	119.6
C2—N1—C1—O1	2.11 (14)	C9—C4—C5—C6	0.52 (18)
C2—N1—C1—C4	−176.15 (11)	C1—C4—C5—C6	−177.13 (11)
C3—O1—C1—N1	1.25 (14)	C4—C5—C6—C7	0.18 (19)
C3—O1—C1—C4	179.69 (10)	C5—C6—C7—O2	178.66 (11)
C1—N1—C2—C3	−4.32 (13)	C5—C6—C7—C8	−0.95 (18)
C1—O1—C3—C2	−3.83 (13)	O2—C7—C8—C9	−178.61 (11)
N1—C2—C3—O1	4.86 (13)	C6—C7—C8—C9	1.02 (18)
N1—C1—C4—C5	168.38 (12)	C7—C8—C9—C4	−0.32 (18)
O1—C1—C4—C5	−9.90 (16)	C5—C4—C9—C8	−0.45 (18)
N1—C1—C4—C9	−9.22 (18)	C1—C4—C9—C8	177.20 (11)
O1—C1—C4—C9	172.50 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1^i	0.84	1.86	2.6997 (13)	178
C5—H5···O1	0.95	2.46	2.7874 (15)	100

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