Crystal structure of 7-bromo-4-oxo-4H-chromene-3-carbaldehyde

Ishikawa, Y.

doi:10.1107/S1600536814018108

organic compounds

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Volume 70| Part 9| September 2014| Page o996

doi:10.1107/S1600536814018108

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Crystal structure of 7-bromo-4-oxo-4H-chromene-3-carbaldehyde

Yoshinobu Ishikawa ^a ^*

^aSchool of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan
^*Correspondence e-mail: ishi206@u-shizuoka-ken.ac.jp

Edited by E. R. T. Tiekink, University of Malaya, Malaysia (Received 6 August 2014; accepted 7 August 2014; online 13 August 2014)

In the title compound, C₁₀H₅BrO₃, a brominated 3-formylchromone derivative, all atoms are essentially coplanar (r.m.s. = 0.0631 Å for the non-H atoms), with the largest deviation from the least-squares plane [0.215 (3) Å] being for the formyl O atom. In the crystal, molecules are linked into tapes through C—H⋯O hydrogen bonds and these tapes are assembled by stacking interactions [centroid–centroid distance between the pyran rings = 3.858 (3) Å] to form supramolecular layers that stack along the c axis.

Keywords: crystal structure; chromone; C—H⋯O hydrogen bonding; stacking interaction.

CCDC reference: 1018275

1. Related literature

For related structures, see: Ishikawa (2014a ,b ). For halogen bonding, see: Auffinger et al. (2004 ); Metrangolo et al. (2005 ); Wilcken et al. (2013 ); Sirimulla et al. (2013 ). For halogen–halogen interactions, see: Metrangolo & Resnati (2014 ); Mukherjee & Desiraju (2014 ).

2. Experimental

2.1. Crystal data

C₁₀H₅BrO₃
M_r = 253.05
Monoclinic, P 2₁ /c
a = 3.8580 (18) Å
b = 6.054 (4) Å
c = 37.268 (13) Å
β = 90.39 (4)°
V = 870.4 (8) Å³
Z = 4
Mo Kα radiation
μ = 4.71 mm⁻¹
T = 100 K
0.45 × 0.20 × 0.10 mm

2.1.2. Data collection

Rigaku AFC-7R diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.339, T_max = 0.624
4817 measured reflections
1980 independent reflections
1710 reflections with F² > 2σ(F²)
R_int = 0.024
3 standard reflections every 150 reflections intensity decay: 4.8%

2.1.3. Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.109
S = 1.07
1980 reflections
127 parameters
H-atom parameters constrained
Δρ_max = 1.26 e Å⁻³
Δρ_min = −1.73 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7ⁱ—H4ⁱ⋯O2	0.95	2.30	3.149 (4)	149 (1)
C1ⁱⁱ—H1ⁱⁱ⋯O3	0.95	2.37	3.228 (5)	149 (1)
Symmetry codes: (i) x+1, y+1, z; (ii) -x, -y+1, -z+1.

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999 $[Rigaku (1999). WinAFC Diffractometer Control Software. Rigaku Corporation, Tokyo, Japan.]$ ); cell refinement: WinAFC Diffractometer Control Software; data reduction: WinAFC Diffractometer Control Software; program(s) used to solve structure: SIR2008 (Burla et al., 2007 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: CrystalStructure (Rigaku, 2010 ); software used to prepare material for publication: CrystalStructure.

Supporting information

CCDC reference: 1018275

Crystal structure: contains datablocks General, I. DOI: 10.1107/S1600536814018108/tk5337sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814018108/tk5337Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814018108/tk5337Isup3.cml

checkCIF report

Structural commentary top

Halogen bonding and halogen···halogen interaction have recently attracted much attention in medicinal chemistry, chemical biology, supramolecular chemistry and crystal engineering (Auffinger et al., 2004, Metrangolo et al., 2005, Wilcken et al., 2013, Sirimulla et al., 2013, Mukherjee & Desiraju, 2014, Metrangolo & Resnati, 2014). We have recently reported the crystal structures of a dibrominated 3-formylchromone derivative 6,8-dibromo-4-oxo-4H-chromene-3-carbaldehyde (Ishikawa, 2014a) and a monobrominated 3-formylchromone derivative 6-bromo-4-oxo-4H-chromene-3-carbaldehyde (Ishikawa, 2014b). Halogen bonding between the formyl oxygen atom and the bromine atom at 8-position and type II halogen···halogen interaction between the bromine atoms at 6-position are observed in 6,8-dibromo-4-oxo-4H-chromene-3-carbaldehyde (Fig.3, top). On the other hand, halogen bonding between the formyl oxygen atom and the bromine atom at 6-position is found in 6-bromo-4-oxo-4H-chromene-3-carbaldehyde (Fig.3, middle). As part of our interest in these types of chemical bonding, we herein report the crystal structure of a monobrominated 3-formylchromone derivative 7-bromo-4-oxo-4H-chromene-3-carbaldehyde.

The objective of this study is to reveal whether a short contact is found for the bromine atom at 7-position. The mean deviation of the least-square planes for the non-hydrogen atoms is 0.0631 Å, and the largest deviation is 0.215 (3) Å for the formyl O3 atom (Fig. 1). In the crystal, the molecules are linked through C–H···O hydrogen bonds between the translation-symmetryⁱ and inversion-symmetry equivalents^ii,iii to form tapes [i: x + 1, y + 1, z, ii: –x, –y + 1, –z + 1, iii: –x + 1, –y + 2, –z + 1], which are further assembled by stacking interactions [centroid–centroid distance between the pyran rings of the 4H-chromene units = 3.858 (3) Å], as shown in Fig. 2. A short contact for the bromine atom at 7-position is not observed (Fig. 3, bottom).

Synthesis and crystallization top

To a solution of 4-bromo-2-hydroxyacetophenone (4.7 mmol) in N,N-dimethylformamide (15 ml) was added drop-wise POCl₃ (11.6 mmol) at 0 °C. After the mixture was stirred for 14 h at room temperature, water (50 ml) was added. The precipitates were collected, washed with water, and dried in vacuo (yield: 84%). ¹H NMR (400 MHz, CDCl₃): δ = 7.48 (d, 1H, J = 8.8 Hz), 7.57 (s, 1H), 8.24 (d, 1H, J = 8.8 Hz), 8.52 (s, 1H), 10.37 (s, 1H). DART-MS calcd for [C₁₀H₅BrO₃ + H⁺]: 252.950, found 252.981. Single crystals suitable for X-ray diffraction were obtained from a 1,2-dichloroethane/cyclohexane solution of the title compound at room temperature.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. The C(sp²)-bound hydrogen atoms were placed in geometrical positions [C–H 0.95 Å, U_iso(H) = 1.2U_eq(C)], and refined using a riding model.

Related literature top

For related structures, see: Ishikawa (2014a,b). For halogen bonding, see: Auffinger et al. (2004); Metrangolo et al. (2005); Wilcken et al. (2013); Sirimulla et al. (2013). For halogen–halogen interactions, see: Metrangolo & Resnati (2014); Mukherjee & Desiraju (2014).

Computing details top

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell refinement: WinAFC Diffractometer Control Software (Rigaku, 1999); data reduction: WinAFC Diffractometer Control Software (Rigaku, 1999); program(s) used to solve structure: SIR2008 (Burla et al., 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are shown as small spheres of arbitrary radius.
	Fig. 2. A packing view of the title compound. C—H···O hydrogen bonds are represented by dashed lines.
	Fig. 3. Sphere models of the crystal structures of 6,8-dibromo-4-oxo-4H-chromene-3-carbaldehyde (top, Ishikawa, 2014a), 6-bromo-4-oxo-4H-chromene-3-carbaldehyde (middle, Ishikawa, 2014b), and the title compound (bottom, this work).

7-Bromo-4-oxo-4H-chromene-3-carbaldehyde top

Crystal data top

C₁₀H₅BrO₃	F(000) = 496.00
M_r = 253.05	D_x = 1.931 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 3.8580 (18) Å	θ = 15.3–17.5°
b = 6.054 (4) Å	µ = 4.71 mm⁻¹
c = 37.268 (13) Å	T = 100 K
β = 90.39 (4)°	Plate, colourless
V = 870.4 (8) Å³	0.45 × 0.20 × 0.10 mm
Z = 4

Data collection top

Rigaku AFC-7R diffractometer	R_int = 0.024
ω scans	θ_max = 27.5°
Absorption correction: ψ scan (North et al., 1968)	h = −5→2
T_min = 0.339, T_max = 0.624	k = −7→7
4817 measured reflections	l = −48→48
1980 independent reflections	3 standard reflections every 150 reflections
1710 reflections with F² > 2σ(F²)	intensity decay: 4.8%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0756P)² + 0.989P] where P = (F_o² + 2F_c²)/3
1980 reflections	(Δ/σ)_max = 0.002
127 parameters	Δρ_max = 1.26 e Å⁻³
0 restraints	Δρ_min = −1.73 e Å⁻³
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₀H₅BrO₃	V = 870.4 (8) Å³
M_r = 253.05	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 3.8580 (18) Å	µ = 4.71 mm⁻¹
b = 6.054 (4) Å	T = 100 K
c = 37.268 (13) Å	0.45 × 0.20 × 0.10 mm
β = 90.39 (4)°

Data collection top

Rigaku AFC-7R diffractometer	1710 reflections with F² > 2σ(F²)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.024
T_min = 0.339, T_max = 0.624	3 standard reflections every 150 reflections
4817 measured reflections	intensity decay: 4.8%
1980 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.07	Δρ_max = 1.26 e Å⁻³
1980 reflections	Δρ_min = −1.73 e Å⁻³
127 parameters

Special details top

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	U_iso*/U_eq
Br1	0.08234 (8)	0.06978 (6)	0.719199 (7)	0.01987 (15)
O1	0.1286 (6)	0.3047 (4)	0.58604 (6)	0.0198 (5)
O2	0.6540 (7)	0.8813 (4)	0.60418 (6)	0.0253 (6)
O3	0.2989 (8)	0.7487 (5)	0.50270 (6)	0.0321 (6)
C1	0.1969 (9)	0.4490 (6)	0.55957 (8)	0.0199 (7)
C2	0.3614 (9)	0.6437 (6)	0.56382 (8)	0.0190 (7)
C3	0.4862 (8)	0.7122 (6)	0.59908 (8)	0.0181 (6)
C4	0.4730 (9)	0.6080 (6)	0.66421 (8)	0.0173 (6)
C5	0.3830 (9)	0.4628 (6)	0.69123 (8)	0.0187 (7)
C6	0.2140 (8)	0.2670 (6)	0.68222 (8)	0.0167 (6)
C7	0.1322 (8)	0.2111 (6)	0.64716 (8)	0.0170 (6)
C8	0.3930 (9)	0.5598 (5)	0.62828 (8)	0.0169 (7)
C9	0.2221 (8)	0.3622 (6)	0.62059 (8)	0.0164 (6)
C10	0.4165 (9)	0.7874 (7)	0.53244 (9)	0.0256 (8)
H1	0.1233	0.4106	0.5360	0.0238*
H2	0.5900	0.7415	0.6700	0.0207*
H3	0.4357	0.4961	0.7156	0.0224*
H4	0.0197	0.0759	0.6415	0.0203*
H5	0.5512	0.9174	0.5356	0.0307*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0190 (3)	0.0305 (3)	0.01010 (19)	−0.00138 (11)	0.00019 (12)	0.00367 (11)
O1	0.0260 (12)	0.0252 (12)	0.0083 (10)	−0.0074 (10)	−0.0036 (9)	−0.0010 (9)
O2	0.0336 (14)	0.0259 (12)	0.0162 (11)	−0.0107 (11)	−0.0033 (10)	−0.0010 (10)
O3	0.0437 (16)	0.0392 (15)	0.0133 (12)	−0.0131 (12)	−0.0067 (11)	0.0046 (11)
C1	0.0209 (16)	0.0291 (18)	0.0095 (14)	−0.0034 (13)	−0.0018 (12)	−0.0010 (12)
C2	0.0214 (16)	0.0261 (16)	0.0096 (13)	−0.0028 (13)	−0.0008 (12)	0.0006 (12)
C3	0.0197 (15)	0.0240 (15)	0.0107 (14)	−0.0011 (12)	0.0011 (11)	−0.0015 (12)
C4	0.0175 (15)	0.0245 (16)	0.0098 (14)	−0.0003 (12)	−0.0021 (11)	−0.0049 (12)
C5	0.0192 (16)	0.0268 (17)	0.0099 (14)	−0.0008 (12)	−0.0015 (12)	−0.0030 (12)
C6	0.0149 (14)	0.0260 (16)	0.0091 (13)	0.0001 (12)	−0.0003 (10)	0.0001 (12)
C7	0.0154 (14)	0.0226 (15)	0.0128 (14)	−0.0035 (12)	−0.0017 (11)	−0.0022 (12)
C8	0.0179 (15)	0.0231 (16)	0.0095 (14)	−0.0023 (12)	−0.0013 (12)	−0.0014 (11)
C9	0.0175 (15)	0.0247 (15)	0.0070 (13)	−0.0010 (12)	−0.0022 (11)	−0.0043 (12)
C10	0.0299 (19)	0.0299 (17)	0.0171 (16)	−0.0078 (15)	−0.0006 (14)	0.0021 (14)

Geometric parameters (Å, º) top

Br1—C6	1.895 (4)	C4—C8	1.403 (5)
O1—C1	1.345 (4)	C5—C6	1.393 (5)
O1—C9	1.379 (4)	C6—C7	1.384 (5)
O2—C3	1.226 (4)	C7—C9	1.394 (5)
O3—C10	1.217 (5)	C8—C9	1.395 (5)
C1—C2	1.348 (5)	C1—H1	0.950
C2—C3	1.457 (5)	C4—H2	0.950
C2—C10	1.474 (5)	C5—H3	0.950
C3—C8	1.473 (5)	C7—H4	0.950
C4—C5	1.382 (5)	C10—H5	0.950

O1···C3	2.866 (5)	C10···H1	2.5501
O2···C1	3.561 (5)	H1···H5	3.4843
O2···C4	2.873 (4)	H2···H3	2.3357
O2···C10	2.877 (5)	Br1···H2ⁱ	3.2968
O3···C1	2.820 (4)	Br1···H2ⁱⁱ	3.3454
C1···C7	3.578 (5)	Br1···H3ⁱⁱⁱ	3.5917
C1···C8	2.748 (5)	Br1···H3^x	3.1886
C2···C9	2.772 (5)	Br1···H3^xi	3.0827
C4···C7	2.810 (5)	O1···H5ⁱⁱ	3.4250
C5···C9	2.769 (5)	O2···H4^iv	3.0581
C6···C8	2.771 (5)	O2···H4^v	2.2984
O1···O2ⁱ	3.224 (4)	O3···H1^ix	2.3733
O1···O2ⁱⁱ	3.334 (4)	O3···H1^vii	2.8324
O1···C3ⁱⁱⁱ	3.533 (5)	O3···H5ⁱⁱⁱ	3.3041
O2···O1^iv	3.334 (4)	O3···H5^viii	2.5428
O2···O1^v	3.224 (4)	C2···H1^vi	3.4277
O2···C2^vi	3.440 (5)	C3···H4^iv	3.2588
O2···C3^vi	3.376 (5)	C3···H4^v	3.3965
O2···C7^iv	3.263 (4)	C4···H2ⁱⁱⁱ	3.5093
O2···C7^v	3.149 (4)	C4···H4^iv	3.4320
O2···C8^vi	3.562 (5)	C5···H2ⁱⁱⁱ	3.5776
O2···C9^iv	3.412 (5)	C6···H2ⁱⁱ	3.5270
O3···O3^vii	3.394 (5)	C6···H3ⁱⁱⁱ	3.5409
O3···O3^viii	3.422 (5)	C7···H2ⁱⁱ	3.4509
O3···C1^ix	3.228 (5)	C7···H4^vi	3.5285
O3···C1^vii	3.265 (5)	C8···H4^iv	3.4764
O3···C10ⁱⁱⁱ	3.595 (5)	C10···H1^vi	3.5572
O3···C10^viii	3.290 (5)	C10···H1^ix	3.4940
C1···O3^ix	3.228 (5)	C10···H1^vii	3.3402
C1···O3^vii	3.265 (5)	C10···H5ⁱⁱⁱ	3.4327
C1···C2ⁱⁱⁱ	3.437 (5)	C10···H5^viii	3.1048
C1···C3ⁱⁱⁱ	3.504 (5)	H1···O3^ix	2.3733
C2···O2ⁱⁱⁱ	3.440 (5)	H1···O3^vii	2.8324
C2···C1^vi	3.437 (5)	H1···C2ⁱⁱⁱ	3.4277
C3···O1^vi	3.533 (5)	H1···C10ⁱⁱⁱ	3.5572
C3···O2ⁱⁱⁱ	3.376 (5)	H1···C10^ix	3.4940
C3···C1^vi	3.504 (5)	H1···C10^vii	3.3402
C4···C6^vi	3.586 (5)	H1···H1^ix	3.0401
C4···C7^vi	3.559 (5)	H1···H5ⁱⁱ	3.4115
C5···C6^vi	3.437 (5)	H1···H5^vii	3.5617
C6···C4ⁱⁱⁱ	3.586 (5)	H2···Br1^iv	3.3454
C6···C5ⁱⁱⁱ	3.437 (5)	H2···Br1^v	3.2968
C7···O2ⁱ	3.149 (4)	H2···C4^vi	3.5093
C7···O2ⁱⁱ	3.263 (4)	H2···C5^vi	3.5776
C7···C4ⁱⁱⁱ	3.559 (5)	H2···C6^iv	3.5270
C8···O2ⁱⁱⁱ	3.562 (5)	H2···C7^iv	3.4509
C8···C9^vi	3.429 (5)	H2···H4^iv	3.1684
C9···O2ⁱⁱ	3.412 (5)	H2···H4^v	2.8291
C9···C8ⁱⁱⁱ	3.429 (5)	H3···Br1^vi	3.5917
C10···O3^vi	3.595 (5)	H3···Br1^xii	3.1886
C10···O3^viii	3.290 (5)	H3···Br1^xiii	3.0827
C10···C10^viii	3.593 (6)	H3···C6^vi	3.5409
Br1···H3	2.9226	H4···O2ⁱ	2.2984
Br1···H4	2.9055	H4···O2ⁱⁱ	3.0581
O1···H4	2.5249	H4···C3ⁱ	3.3965
O2···H2	2.6093	H4···C3ⁱⁱ	3.2588
O2···H5	2.5934	H4···C4ⁱⁱ	3.4320
O3···H1	2.4901	H4···C7ⁱⁱⁱ	3.5285
C1···H5	3.2749	H4···C8ⁱⁱ	3.4764
C3···H1	3.2825	H4···H2ⁱ	2.8291
C3···H2	2.6775	H4···H2ⁱⁱ	3.1684
C3···H5	2.6858	H5···O1^iv	3.4250
C5···H4	3.2949	H5···O3^vi	3.3041
C6···H2	3.2513	H5···O3^viii	2.5428
C7···H3	3.2879	H5···C10^vi	3.4327
C8···H3	3.2793	H5···C10^viii	3.1048
C8···H4	3.3027	H5···H1^iv	3.4115
C9···H1	3.1864	H5···H1^vii	3.5617
C9···H2	3.2628	H5···H5^viii	2.8597

C1—O1—C9	118.0 (3)	C4—C8—C9	118.4 (3)
O1—C1—C2	125.2 (3)	O1—C9—C7	115.7 (3)
C1—C2—C3	120.5 (3)	O1—C9—C8	121.9 (3)
C1—C2—C10	119.6 (3)	C7—C9—C8	122.4 (3)
C3—C2—C10	120.0 (3)	O3—C10—C2	123.6 (4)
O2—C3—C2	123.3 (3)	O1—C1—H1	117.410
O2—C3—C8	122.7 (3)	C2—C1—H1	117.401
C2—C3—C8	114.0 (3)	C5—C4—H2	119.709
C5—C4—C8	120.6 (3)	C8—C4—H2	119.732
C4—C5—C6	119.0 (3)	C4—C5—H3	120.507
Br1—C6—C5	119.2 (3)	C6—C5—H3	120.495
Br1—C6—C7	118.2 (3)	C6—C7—H4	121.481
C5—C6—C7	122.6 (3)	C9—C7—H4	121.508
C6—C7—C9	117.0 (3)	O3—C10—H5	118.165
C3—C8—C4	121.4 (3)	C2—C10—H5	118.205
C3—C8—C9	120.2 (3)

C1—O1—C9—C7	177.4 (3)	C8—C4—C5—C6	0.5 (5)
C1—O1—C9—C8	−2.2 (4)	C8—C4—C5—H3	−179.5
C9—O1—C1—C2	2.5 (5)	H2—C4—C5—C6	−179.5
C9—O1—C1—H1	−177.5	H2—C4—C5—H3	0.5
O1—C1—C2—C3	0.9 (5)	H2—C4—C8—C3	−0.0
O1—C1—C2—C10	−179.4 (3)	H2—C4—C8—C9	179.8
H1—C1—C2—C3	−179.1	C4—C5—C6—Br1	−178.8 (3)
H1—C1—C2—C10	0.6	C4—C5—C6—C7	0.1 (5)
C1—C2—C3—O2	175.8 (3)	H3—C5—C6—Br1	1.1
C1—C2—C3—C8	−4.2 (5)	H3—C5—C6—C7	−179.9
C1—C2—C10—O3	5.6 (5)	Br1—C6—C7—C9	178.02 (18)
C1—C2—C10—H5	−174.4	Br1—C6—C7—H4	−2.0
C3—C2—C10—O3	−174.7 (3)	C5—C6—C7—C9	−0.9 (5)
C3—C2—C10—H5	5.3	C5—C6—C7—H4	179.1
C10—C2—C3—O2	−3.9 (5)	C6—C7—C9—O1	−178.3 (3)
C10—C2—C3—C8	176.1 (3)	C6—C7—C9—C8	1.2 (5)
O2—C3—C8—C4	4.2 (5)	H4—C7—C9—O1	1.7
O2—C3—C8—C9	−175.6 (3)	H4—C7—C9—C8	−178.8
C2—C3—C8—C4	−175.8 (3)	C3—C8—C9—O1	−1.4 (5)
C2—C3—C8—C9	4.4 (4)	C3—C8—C9—C7	179.2 (3)
C5—C4—C8—C3	180.0 (3)	C4—C8—C9—O1	178.8 (3)
C5—C4—C8—C9	−0.2 (5)	C4—C8—C9—C7	−0.7 (5)

Symmetry codes: (i) x−1, y−1, z; (ii) x, y−1, z; (iii) x−1, y, z; (iv) x, y+1, z; (v) x+1, y+1, z; (vi) x+1, y, z; (vii) −x+1, −y+1, −z+1; (viii) −x+1, −y+2, −z+1; (ix) −x, −y+1, −z+1; (x) −x, y−1/2, −z+3/2; (xi) −x+1, y−1/2, −z+3/2; (xii) −x, y+1/2, −z+3/2; (xiii) −x+1, y+1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7^v—H4^v···O2	0.95	2.30	3.149 (4)	149 (1)
C1^ix—H1^ix···O3	0.95	2.37	3.228 (5)	149 (1)

Symmetry codes: (v) x+1, y+1, z; (ix) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7ⁱ—H4ⁱ···O2	0.95	2.30	3.149 (4)	148.7 (2)
C1ⁱⁱ—H1ⁱⁱ···O3	0.95	2.37	3.228 (5)	149.4 (2)

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

Acknowledgements

The University of Shizuoka is acknowledged for instrument support.

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