(7-Dimethylamino-1-hydroxy-3-naphthyl)(morpholino)methanone

Kim, M.-H.; Seo, J.-S.; Kim, C.-H.; Ryu, J.-W.; Lee, K.-H.

doi:10.1107/S1600536809051848

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o66

doi:10.1107/S1600536809051848

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(7-Dimethylamino-1-hydroxy-3-naphthyl)(morpholino)methanone

Moon-Hwan Kim,^a Ji-Su Seo,^a Chong-Hyeak Kim,^b ^* Jae-Wook Ryu ^a and Ki-Hwan Lee ^c

^aBiomaterial Research Center, Korea Research Institute of Chemical Technology, PO Box 107, Yuseong, Daejeon 305-600, Republic of Korea, ^bCenter for Chemical Analysis, Korea Research Institute of Chemical Technology, PO Box 107, Yuseong, Daejeon 305-600, Republic of Korea, and ^cDepartment of Chemistry, Kongju National University, Kongju 314-701, Republic of Korea
^*Correspondence e-mail: chkim@krict.re.kr

(Received 16 November 2009; accepted 2 December 2009; online 9 December 2009)

In the title compound, C₁₇H₂₀N₂O₃, the morpholine ring is in a slightly distorted chair form. The crystal structure is stabilized by an intermolecular O—H⋯O hydrogen bond between the H atom of the hydroxyl group and the O atom of a neighbouring carbonyl group. A weak intermolecular C—H⋯π interaction is also present.

Related literature

For the synthesis and applications of organic photochromic dyes, see: Gabbutt et al. (2003 , 2004 ); Kumar et al. (1995 ); Gemert & Selvig (2000 ); Nelson et al. (2002 ). For their potential use as variable optical transmission materials and in optical storage, see; Crano & Guglielmetti (1999 ).

Experimental

Crystal data

C₁₇H₂₀N₂O₃
M_r = 300.35
Orthorhombic, P c a 2₁
a = 12.6250 (5) Å
b = 13.9634 (6) Å
c = 8.8369 (3) Å
V = 1557.84 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.41 × 0.18 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
8069 measured reflections
2044 independent reflections
1475 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.115
S = 1.04
2044 reflections
200 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.82	1.82	2.631 (3)	172
C17—H17C⋯Cgⁱⁱ	0.96	2.80	3.533 (2)	134
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y, z-{\script{1\over 2}}]$ ; (ii) $[-x+1, -y+1, z-{\script{1\over 2}}]$ . Cg is the centroid of the C5–C10 benzene ring.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809051848/lx2129sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809051848/lx2129Isup2.hkl

checkCIF report

Comment top

The synthesis of organic photochromic dyes and their application has become of great interest recently (Gabbutt et al., 2003, 2004; Kumar et al., 1995; Gemert & Selvig, 2000; Nelson et al., 2002. Because they may be useful such as variable optical transmission materials (ophthalmic glasses and lenses) or in potential use such as optical storage (optical disks or memories) (Crano & Guglielmetti, 1999). Here we report the crystal structure of the title compound (Fig. 1). In the title compound, the conformation of the morpholine ring is in a slightly distorted chair form. The crystal packing (Fig. 2) is stabilized by an intermolecular O—H···O hydrogen bond between the H atom of the hydroxyl group and the O atom of a neighbouring C═O unit, with a O1—H1···O2ⁱ (Table 1). The molecular packing (Fig. 2) is further stabilized by a intermolecular C—H···π interaction between a methyl H atom of the dimethylamino group and the N-bonded benzene ring, with a C17—H17C···Cgⁱⁱ (Table 1; Cg is the centroid of the C5–C10 benzene ring).

Related literature top

For the synthesis and applications of organic photochromic dyes, see: Gabbutt et al. (2003, 2004); Kumar et al. (1995); Gemert & Selvig (2000); Nelson et al. (2002). For their potential use as variable optical transmission

materials and in optical storage, see; Crano & Guglielmetti (1999). Cg is the centroid of the C5–C10 benzene ring.

Experimental top

The title compound was synthesized from the reaction of 1-hydroxy-7-dimethylamino-3-naphthonic acid (116 g, 0.5 mol) and morpholine (48 g, 1.2 mol) in anhydrous CH₂Cl₂ for 24 h at room temperature. The reaction was quenched by the addition of water and the organic layer separated, dried over anhydrous MgSO₄, filtered and concentrated to give the title compound (120 g, yield 81%). Single crystals suitable for X-ray diffraction were prepared by evaporation of a solution of the title compound in ethyl acetate at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. O—H···O and C—H···π interactions (dotted lines) in the crystal structure of the title compound. Cg denotes the ring centroid. [Symmetry codes: (i) - x + 3/2, y, z -1/2; (ii) - x + 1, - y + 1, z - 1/2; (iii) - x + 3/2, y, z + 1/2; (iv) - x + 1, - y + 1, z + 1/2.]

(7-Dimethylamino-1-hydroxy-3-naphthyl)(morpholino)methanone top

Crystal data top

C₁₇H₂₀N₂O₃	F(000) = 640
M_r = 300.35	D_x = 1.281 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2694 reflections
a = 12.6250 (5) Å	θ = 2.9–22.0°
b = 13.9634 (6) Å	µ = 0.09 mm⁻¹
c = 8.8369 (3) Å	T = 296 K
V = 1557.84 (11) Å³	Block, silver
Z = 4	0.41 × 0.18 × 0.08 mm

Data collection top

Bruker APEXII CCD diffractometer	1475 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.025
Graphite monochromator	θ_max = 28.3°, θ_min = 1.5°
Detector resolution: 10 pixels mm^-1	h = −16→11
ϕ and ω scans	k = −9→18
8069 measured reflections	l = −9→11
2044 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.115	w = 1/[σ²(F_o²) + (0.0628P)² + 0.0129P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2044 reflections	Δρ_max = 0.19 e Å⁻³
200 parameters	Δρ_min = −0.15 e Å⁻³
1 restraint	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.009 (2)

Crystal data top

C₁₇H₂₀N₂O₃	V = 1557.84 (11) Å³
M_r = 300.35	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 12.6250 (5) Å	µ = 0.09 mm⁻¹
b = 13.9634 (6) Å	T = 296 K
c = 8.8369 (3) Å	0.41 × 0.18 × 0.08 mm

Data collection top

Bruker APEXII CCD diffractometer	1475 reflections with I > 2σ(I)
8069 measured reflections	R_int = 0.025
2044 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	1 restraint
wR(F²) = 0.115	H-atom parameters constrained
S = 1.04	Δρ_max = 0.19 e Å⁻³
2044 reflections	Δρ_min = −0.15 e Å⁻³
200 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	0.67137 (15)	0.76538 (16)	0.3748 (2)	0.0597 (6)
H1	0.7257	0.7921	0.4033	0.090*
O2	0.64658 (15)	0.84718 (18)	0.9402 (3)	0.0682 (6)
O3	0.31381 (16)	0.94813 (16)	1.1678 (2)	0.0583 (6)
N1	0.38830 (19)	0.55244 (19)	0.1665 (3)	0.0600 (8)
N2	0.47850 (17)	0.89337 (17)	0.9690 (3)	0.0475 (6)
C1	0.4410 (2)	0.76093 (18)	0.7082 (3)	0.0432 (6)
H1A	0.3886	0.7595	0.7821	0.052*
C2	0.53284 (19)	0.81050 (16)	0.7348 (3)	0.0387 (6)
C3	0.6131 (2)	0.81177 (19)	0.6231 (3)	0.0397 (6)
H3A	0.6762	0.8439	0.6422	0.048*
C4	0.59920 (19)	0.76642 (18)	0.4873 (3)	0.0389 (6)
C5	0.50466 (19)	0.71367 (16)	0.4583 (3)	0.0362 (5)
C6	0.4919 (2)	0.66117 (17)	0.3236 (3)	0.0412 (6)
H6A	0.5446	0.6634	0.2501	0.049*
C7	0.4022 (2)	0.60611 (19)	0.2982 (3)	0.0465 (7)
C8	0.3216 (2)	0.6086 (2)	0.4082 (4)	0.0514 (8)
H8A	0.2593	0.5746	0.3911	0.062*
C9	0.3321 (2)	0.65914 (19)	0.5389 (4)	0.0483 (7)
H9A	0.2772	0.6589	0.6090	0.058*
C10	0.4249 (2)	0.71200 (17)	0.5702 (3)	0.0383 (6)
C11	0.5567 (2)	0.8524 (2)	0.8856 (3)	0.0448 (6)
C12	0.38259 (19)	0.94019 (19)	0.9127 (3)	0.0429 (6)
H12A	0.3663	0.9165	0.8121	0.051*
H12B	0.3944	1.0087	0.9058	0.051*
C13	0.2917 (2)	0.9210 (2)	1.0154 (4)	0.0552 (8)
H13A	0.2303	0.9561	0.9799	0.066*
H13B	0.2748	0.8533	1.0124	0.066*
C14	0.4045 (2)	0.8996 (2)	1.2216 (4)	0.0616 (8)
H14A	0.3910	0.8312	1.2215	0.074*
H14B	0.4184	0.9190	1.3251	0.074*
C15	0.5006 (2)	0.9204 (2)	1.1257 (3)	0.0595 (9)
H15A	0.5177	0.9880	1.1310	0.071*
H15B	0.5608	0.8844	1.1631	0.071*
C16	0.3346 (3)	0.4603 (2)	0.1784 (5)	0.0888 (13)
H16A	0.2810	0.4639	0.2552	0.133*
H16B	0.3850	0.4116	0.2047	0.133*
H16C	0.3024	0.4448	0.0831	0.133*
C17	0.4705 (3)	0.5571 (3)	0.0525 (5)	0.0855 (13)
H17A	0.5021	0.6196	0.0533	0.128*
H17B	0.4402	0.5449	−0.0453	0.128*
H17C	0.5236	0.5098	0.0738	0.128*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0421 (11)	0.0899 (15)	0.0471 (12)	−0.0209 (10)	0.0090 (10)	−0.0154 (11)
O2	0.0366 (11)	0.1086 (17)	0.0593 (13)	0.0192 (11)	−0.0110 (11)	−0.0273 (12)
O3	0.0509 (12)	0.0789 (14)	0.0452 (11)	0.0120 (11)	0.0080 (9)	0.0015 (10)
N1	0.0498 (16)	0.0608 (15)	0.0693 (18)	0.0048 (12)	−0.0095 (14)	−0.0306 (13)
N2	0.0353 (12)	0.0696 (15)	0.0375 (12)	0.0122 (11)	−0.0063 (11)	−0.0107 (11)
C1	0.0382 (15)	0.0469 (14)	0.0443 (16)	0.0039 (12)	0.0031 (13)	−0.0048 (12)
C2	0.0342 (14)	0.0419 (13)	0.0400 (14)	0.0046 (11)	0.0011 (12)	−0.0038 (11)
C3	0.0314 (15)	0.0431 (14)	0.0446 (15)	−0.0028 (11)	−0.0034 (12)	−0.0046 (11)
C4	0.0312 (14)	0.0436 (13)	0.0419 (14)	−0.0025 (11)	0.0033 (12)	−0.0003 (12)
C5	0.0332 (13)	0.0360 (12)	0.0394 (14)	0.0048 (10)	−0.0043 (11)	0.0004 (11)
C6	0.0359 (15)	0.0431 (13)	0.0446 (14)	0.0041 (12)	0.0002 (12)	−0.0042 (11)
C7	0.0443 (17)	0.0410 (14)	0.0542 (17)	0.0081 (12)	−0.0123 (14)	−0.0087 (12)
C8	0.0376 (16)	0.0493 (15)	0.067 (2)	−0.0063 (12)	−0.0098 (15)	−0.0082 (14)
C9	0.0379 (16)	0.0511 (15)	0.0557 (17)	−0.0018 (13)	0.0043 (13)	−0.0048 (14)
C10	0.0350 (14)	0.0370 (12)	0.0428 (14)	−0.0022 (11)	−0.0006 (12)	−0.0015 (10)
C11	0.0350 (16)	0.0535 (15)	0.0460 (15)	0.0050 (12)	−0.0005 (13)	−0.0093 (13)
C12	0.0377 (15)	0.0492 (14)	0.0417 (14)	0.0086 (12)	0.0018 (12)	−0.0014 (12)
C13	0.0396 (17)	0.071 (2)	0.0551 (19)	0.0011 (14)	−0.0013 (14)	0.0017 (15)
C14	0.064 (2)	0.077 (2)	0.0447 (16)	0.0134 (17)	−0.0017 (16)	−0.0045 (16)
C15	0.0465 (18)	0.086 (2)	0.0455 (17)	0.0145 (17)	−0.0083 (14)	−0.0217 (17)
C16	0.099 (3)	0.0587 (18)	0.109 (3)	−0.0026 (19)	−0.028 (3)	−0.032 (2)
C17	0.077 (2)	0.106 (3)	0.073 (2)	0.011 (2)	−0.002 (2)	−0.053 (2)

Geometric parameters (Å, º) top

O1—C4	1.349 (3)	C6—H6A	0.9300
O1—H1	0.8200	C7—C8	1.409 (4)
O2—C11	1.235 (3)	C8—C9	1.360 (4)
O3—C14	1.413 (4)	C8—H8A	0.9300
O3—C13	1.426 (4)	C9—C10	1.411 (4)
N1—C7	1.395 (4)	C9—H9A	0.9300
N1—C17	1.448 (4)	C12—C13	1.487 (4)
N1—C16	1.458 (4)	C12—H12A	0.9700
N2—C11	1.359 (3)	C12—H12B	0.9700
N2—C15	1.461 (4)	C13—H13A	0.9700
N2—C12	1.463 (3)	C13—H13B	0.9700
C1—C2	1.370 (3)	C14—C15	1.508 (4)
C1—C10	1.413 (4)	C14—H14A	0.9700
C1—H1A	0.9300	C14—H14B	0.9700
C2—C3	1.414 (4)	C15—H15A	0.9700
C2—C11	1.487 (4)	C15—H15B	0.9700
C3—C4	1.368 (4)	C16—H16A	0.9600
C3—H3A	0.9300	C16—H16B	0.9600
C4—C5	1.426 (3)	C16—H16C	0.9600
C5—C6	1.407 (4)	C17—H17A	0.9600
C5—C10	1.412 (4)	C17—H17B	0.9600
C6—C7	1.387 (4)	C17—H17C	0.9600

C4—O1—H1	109.5	O2—C11—C2	120.9 (2)
C14—O3—C13	110.4 (2)	N2—C11—C2	120.3 (2)
C7—N1—C17	117.8 (2)	N2—C12—C13	110.5 (2)
C7—N1—C16	118.2 (3)	N2—C12—H12A	109.5
C17—N1—C16	115.0 (3)	C13—C12—H12A	109.5
C11—N2—C15	118.9 (2)	N2—C12—H12B	109.5
C11—N2—C12	127.2 (2)	C13—C12—H12B	109.5
C15—N2—C12	111.4 (2)	H12A—C12—H12B	108.1
C2—C1—C10	120.9 (3)	O3—C13—C12	112.2 (2)
C2—C1—H1A	119.5	O3—C13—H13A	109.2
C10—C1—H1A	119.5	C12—C13—H13A	109.2
C1—C2—C3	119.5 (2)	O3—C13—H13B	109.2
C1—C2—C11	121.6 (2)	C12—C13—H13B	109.2
C3—C2—C11	118.4 (2)	H13A—C13—H13B	107.9
C4—C3—C2	121.0 (2)	O3—C14—C15	111.7 (3)
C4—C3—H3A	119.5	O3—C14—H14A	109.3
C2—C3—H3A	119.5	C15—C14—H14A	109.3
O1—C4—C3	124.4 (2)	O3—C14—H14B	109.3
O1—C4—C5	115.3 (2)	C15—C14—H14B	109.3
C3—C4—C5	120.3 (2)	H14A—C14—H14B	107.9
C6—C5—C10	120.2 (2)	N2—C15—C14	109.2 (2)
C6—C5—C4	121.1 (2)	N2—C15—H15A	109.8
C10—C5—C4	118.7 (2)	C14—C15—H15A	109.8
C7—C6—C5	121.3 (2)	N2—C15—H15B	109.8
C7—C6—H6A	119.4	C14—C15—H15B	109.8
C5—C6—H6A	119.4	H15A—C15—H15B	108.3
C6—C7—N1	122.4 (3)	N1—C16—H16A	109.5
C6—C7—C8	117.7 (2)	N1—C16—H16B	109.5
N1—C7—C8	119.9 (2)	H16A—C16—H16B	109.5
C9—C8—C7	121.9 (3)	N1—C16—H16C	109.5
C9—C8—H8A	119.1	H16A—C16—H16C	109.5
C7—C8—H8A	119.1	H16B—C16—H16C	109.5
C8—C9—C10	121.3 (3)	N1—C17—H17A	109.5
C8—C9—H9A	119.4	N1—C17—H17B	109.5
C10—C9—H9A	119.4	H17A—C17—H17B	109.5
C9—C10—C5	117.6 (2)	N1—C17—H17C	109.5
C9—C10—C1	122.8 (3)	H17A—C17—H17C	109.5
C5—C10—C1	119.6 (2)	H17B—C17—H17C	109.5
O2—C11—N2	118.7 (3)

C10—C1—C2—C3	−0.7 (4)	C6—C5—C10—C9	−2.2 (3)
C10—C1—C2—C11	−172.5 (2)	C4—C5—C10—C9	−179.9 (2)
C1—C2—C3—C4	1.8 (4)	C6—C5—C10—C1	176.7 (2)
C11—C2—C3—C4	173.8 (2)	C4—C5—C10—C1	−1.0 (3)
C2—C3—C4—O1	179.2 (2)	C2—C1—C10—C9	179.2 (2)
C2—C3—C4—C5	−2.4 (4)	C2—C1—C10—C5	0.4 (4)
O1—C4—C5—C6	2.9 (4)	C15—N2—C11—O2	−6.4 (4)
C3—C4—C5—C6	−175.7 (2)	C12—N2—C11—O2	154.2 (3)
O1—C4—C5—C10	−179.5 (2)	C15—N2—C11—C2	170.5 (3)
C3—C4—C5—C10	2.0 (4)	C12—N2—C11—C2	−28.8 (4)
C10—C5—C6—C7	−0.8 (3)	C1—C2—C11—O2	138.2 (3)
C4—C5—C6—C7	176.9 (2)	C3—C2—C11—O2	−33.7 (4)
C5—C6—C7—N1	−179.1 (2)	C1—C2—C11—N2	−38.7 (4)
C5—C6—C7—C8	3.4 (4)	C3—C2—C11—N2	149.4 (3)
C17—N1—C7—C6	−1.3 (4)	C11—N2—C12—C13	144.1 (3)
C16—N1—C7—C6	144.3 (3)	C15—N2—C12—C13	−54.0 (3)
C17—N1—C7—C8	176.1 (3)	C14—O3—C13—C12	−57.6 (3)
C16—N1—C7—C8	−38.3 (4)	N2—C12—C13—O3	55.1 (3)
C6—C7—C8—C9	−3.1 (4)	C13—O3—C14—C15	58.8 (3)
N1—C7—C8—C9	179.3 (3)	C11—N2—C15—C14	−141.8 (3)
C7—C8—C9—C10	0.2 (4)	C12—N2—C15—C14	54.6 (3)
C8—C9—C10—C5	2.5 (4)	O3—C14—C15—N2	−57.5 (3)
C8—C9—C10—C1	−176.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.82	2.631 (3)	172
C17—H17C···Cgⁱⁱ	0.96	2.80	3.533 (2)	134

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

Experimental details

Crystal data
Chemical formula	C₁₇H₂₀N₂O₃
M_r	300.35
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	296
a, b, c (Å)	12.6250 (5), 13.9634 (6), 8.8369 (3)
V (Å³)	1557.84 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.41 × 0.18 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8069, 2044, 1475
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.115, 1.04
No. of reflections	2044
No. of parameters	200
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.15

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.82	2.631 (3)	171.9
C17—H17C···Cgⁱⁱ	0.96	2.80	3.533 (2)	134.2

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

References

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Crano, J. C. & Guglielmetti, R. J. (1999). Editors. Organic Photochromic and Thermochromic Compounds, Vol 1. New York: Plenum Press. Google Scholar
Gabbutt, C. D., Hepworth, J. D., Heron, B. M., Thomas, D. A., Kilner, C. & Partington, S. M. (2004). Heterocycles, 63, 567–582. CAS Google Scholar
Gabbutt, C. D., Heron, B. M., Instone, A. C., Thomas, D. A., Partington, S. M., Hursthouse, M. B. & Gelbrich, T. (2003). Eur. J. Org. Chem. pp. 1220–1230. Web of Science CSD CrossRef Google Scholar
Gemert, B. V. & Selvig, C. D. (2000). US Patent 6106744. Google Scholar
Kumar, A., Gemert, B. V. & Knowles, D. B. (1995). US Patent 5458814. Google Scholar
Nelson, C. M., Chopra, A., Knowles, D. B., Gemert, B. V. & Kumar, A. (2002). US Patent 6348604 B1. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 66| Part 1| January 2010| Page o66

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