7-Chloro-4-oxo-4H-chromene-3-carbaldehyde

Ishikawa, Y.

doi:10.1107/S1600536814014925

organic compounds

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Volume 70| Part 8| August 2014| Page o831

doi:10.1107/S1600536814014925

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7-Chloro-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

(Received 24 June 2014; accepted 24 June 2014; online 2 July 2014)

In the title compound, C₁₀H₅ClO₃, a chlorinated 3-formylchromone derivative, all atoms are essentially coplanar (r.m.s. deviation = 0.0592 Å for all non-H atoms), with the largest deviation from the least-squares plane [0.1792 (19) Å] being for the chromone-ring carbonyl O atom. In the crystal, molecules are linked through C—H⋯O hydrogen bonds to form tetrads, which are assembled by stacking interactions [centroid–centroid distance between the pyran rings = 3.823 (3) Å] and van der Waals contacts between the Cl atoms [Cl⋯Cl = 3.4483 (16) Å and C—Cl⋯Cl = 171.73 (7)°] into a three-dimensional architecture.

Keywords: crystal structure.

CCDC reference: 1010095

Related literature

For related structures, see: Ishikawa & Motohashi (2013 ); 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 ).

Experimental

Crystal data

C₁₀H₅ClO₃
M_r = 208.60
Triclinic, $[P \overline 1]$
a = 3.823 (2) Å
b = 5.973 (3) Å
c = 18.386 (8) Å
α = 85.99 (4)°
β = 87.74 (4)°
γ = 86.58 (4)°
V = 417.8 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.43 mm⁻¹
T = 100 K
0.42 × 0.25 × 0.08 mm

Data collection

Rigaku AFC-7R diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.865, T_max = 0.966
2429 measured reflections
1899 independent reflections
1690 reflections with F² > 2σ(F²)
R_int = 0.050
3 standard reflections every 150 reflections intensity decay: −1.1%

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.104
S = 1.10
1899 reflections
127 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H4⋯O2ⁱ	0.95	2.34	3.204 (3)	151 (1)
C1—H1⋯O3ⁱⁱ	0.95	2.37	3.209 (3)	148 (1)
Symmetry codes: (i) x+1, y+1, z; (ii) -x+1, -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: 1010095

Crystal structure: contains datablocks General, I. DOI: 10.1107/S1600536814014925/tk5323sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814014925/tk5323Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814014925/tk5323Isup3.cml

checkCIF report

Structural commentary top

Halogen bonding and halogen···halogen interactions 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 dichlorinated 3-formylchromone derivative 6,8-dichloro-4-oxochromene-3-carbaldehyde (Ishikawa & Motohashi, 2013), and monochlorinated 3-formylchromone derivatives 6-chloro-4-oxo-4H-chromene-3-carbaldehyde (Ishikawa, 2014a) and 8-chloro-4-oxo-4H-chromene-3-carbaldehyde (Ishikawa, 2014b). Halogen bonding between the formyl oxygen atom and the chlorine atom at 8-position and type I halogen···halogen interaction between the chlorine atoms at 6-position are observed in 6,8-dichloro-4-oxochromene-3-carbaldehyde (Fig·2 A). On the other hand, van der Waals contacts between the formyl oxygen atom and the chlorine atom at 6-position in 6-chloro-4-oxo-4H-chromene-3-carbaldehyde (Fig·2 B) and between the formyl oxygen atom and the chlorine atom at 8-position in 8-chloro-4-oxo-4H-chromene-3-carbaldehyde (Fig·2 C) are found. As part of our interest in these types of chemical bonding, we herein report the crystal structure of a monochlorinated 3-formylchromone derivative 7-chloro-4-oxo-4H-chromene-3-carbaldehyde. The objective of this study is to reveal whether a short contact is found for the chlorine atom at 7-position.

The mean deviation of the least-square planes for the non-hydrogen atoms is 0.0592 Å, and the largest deviation is 0.1792 (19) Å for O3.

In the crystal, the molecules are linked through C–H···O hydrogen bonds among the translation-symmetryⁱ and inversion-symmetry equivalents^ii,iii to form tetrads [i: x – 1, y – 1, z, ii: –x, –y, –z + 1, iii: –x + 1, –y + 1, –z + 1], which are assembled by stacking interactions [centroid–centroid distance between the pyran rings = 3.823 (3) Å], as shown in Fig. 1.

Van der Waals contacts between the chlorine atoms of inversion-symmetry equivalents are found [Cl1···Cl1^iv = 3.4483 (16) Å, C6–Cl1···Cl1^iv = 171.73 (7)°, iv: –x + 1, –y + 2, –z + 2], as shown in Fig. 2D. Thus, significant short contact for the chlorine atom at 7-position is not observed. Whereas the characteristic short Cl···O contact is observed in the dichlorinated 3-formylchromone (Fig. 2A), such a short contact is not found in the monochlorinated ones (Fig. 2B, C and D). These findings should be helpful to understand interactions of halogenated ligands with proteins, and thus invaluable for rational drug design.

Synthesis and crystallization top

To a solution of 4-chloro-2-hydroxyacetophenone (5.9 mmol) in N,N-dimethylformamide (15 ml) was added dropwise POCl₃ (14.7 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: 85%). 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 [C₁₀H₅Cl₁O₃ + H⁺]: 209.001, found 209.029. 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 & Motohashi (2013); 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. A packing view of the title compound, with displacement ellipsoids drawn at the 50% probability level. C—H···O hydrogen bonds are represented by dashed lines.
	Fig. 2. Sphere models of the crystal structures of 6,8-dichloro-4-oxochromene-3-carbaldehyde (A, Ishikawa & Motohashi, 2013), 6-chloro-4-oxo-4H-chromene-3-carbaldehyde (B, Ishikawa, 2014a), 8-chloro-4-oxo-4H-chromene-3-carbaldehyde (C, Ishikawa, 2014b), and the title compound (D).

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

Crystal data top

C₁₀H₅ClO₃	Z = 2
M_r = 208.60	F(000) = 212.00
Triclinic, P1	D_x = 1.658 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 3.823 (2) Å	Cell parameters from 25 reflections
b = 5.973 (3) Å	θ = 15.2–17.0°
c = 18.386 (8) Å	µ = 0.43 mm⁻¹
α = 85.99 (4)°	T = 100 K
β = 87.74 (4)°	Plate, yellow
γ = 86.58 (4)°	0.42 × 0.25 × 0.08 mm
V = 417.8 (4) Å³

Data collection top

Rigaku AFC-7R diffractometer	R_int = 0.050
ω–2θ scans	θ_max = 27.5°
Absorption correction: ψ scan (North et al., 1968)	h = −4→2
T_min = 0.865, T_max = 0.966	k = −7→7
2429 measured reflections	l = −23→23
1899 independent reflections	3 standard reflections every 150 reflections
1690 reflections with F² > 2σ(F²)	intensity decay: −1.1%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0425P)² + 0.5019P] where P = (F_o² + 2F_c²)/3
1899 reflections	(Δ/σ)_max = 0.001
127 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.50 e Å⁻³
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₀H₅ClO₃	γ = 86.58 (4)°
M_r = 208.60	V = 417.8 (4) Å³
Triclinic, P1	Z = 2
a = 3.823 (2) Å	Mo Kα radiation
b = 5.973 (3) Å	µ = 0.43 mm⁻¹
c = 18.386 (8) Å	T = 100 K
α = 85.99 (4)°	0.42 × 0.25 × 0.08 mm
β = 87.74 (4)°

Data collection top

Rigaku AFC-7R diffractometer	1690 reflections with F² > 2σ(F²)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.050
T_min = 0.865, T_max = 0.966	3 standard reflections every 150 reflections
2429 measured reflections	intensity decay: −1.1%
1899 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.10	Δρ_max = 0.41 e Å⁻³
1899 reflections	Δρ_min = −0.50 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
Cl1	0.40101 (12)	0.80466 (8)	0.94032 (2)	0.01990 (15)
O1	0.3743 (4)	0.6471 (3)	0.67507 (7)	0.0171 (3)
O2	−0.1431 (4)	0.0675 (3)	0.71337 (8)	0.0199 (3)
O3	0.2057 (5)	0.2458 (3)	0.50473 (8)	0.0265 (4)
C1	0.3077 (5)	0.5184 (4)	0.62091 (10)	0.0162 (4)
C2	0.1464 (5)	0.3212 (4)	0.62998 (10)	0.0160 (4)
C3	0.0256 (5)	0.2365 (3)	0.70234 (10)	0.0152 (4)
C4	0.0441 (5)	0.3071 (4)	0.83526 (10)	0.0159 (4)
C5	0.1313 (5)	0.4379 (4)	0.88996 (10)	0.0164 (4)
C6	0.2909 (5)	0.6400 (3)	0.87083 (10)	0.0150 (4)
C7	0.3697 (5)	0.7116 (3)	0.79955 (10)	0.0153 (4)
C8	0.1182 (5)	0.3730 (3)	0.76188 (10)	0.0138 (4)
C9	0.2831 (5)	0.5741 (3)	0.74571 (10)	0.0140 (4)
C10	0.0936 (6)	0.1938 (4)	0.56551 (11)	0.0201 (4)
H1	0.3784	0.5687	0.5727	0.0194*
H2	−0.0674	0.1709	0.8474	0.0191*
H3	0.0840	0.3919	0.9397	0.0197*
H4	0.4785	0.8490	0.7877	0.0183*
H5	−0.0367	0.0629	0.5723	0.0241*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0221 (3)	0.0227 (3)	0.0159 (3)	−0.00304 (17)	−0.00206 (16)	−0.00573 (17)
O1	0.0201 (7)	0.0185 (7)	0.0129 (7)	−0.0055 (5)	0.0019 (5)	−0.0007 (5)
O2	0.0204 (7)	0.0195 (7)	0.0207 (8)	−0.0079 (6)	0.0003 (6)	−0.0018 (6)
O3	0.0359 (9)	0.0303 (9)	0.0146 (8)	−0.0111 (7)	0.0031 (6)	−0.0054 (6)
C1	0.0151 (9)	0.0198 (9)	0.0139 (9)	−0.0017 (7)	−0.0004 (7)	−0.0019 (7)
C2	0.0145 (9)	0.0181 (9)	0.0154 (9)	−0.0010 (7)	−0.0012 (7)	−0.0018 (7)
C3	0.0108 (8)	0.0168 (9)	0.0181 (9)	−0.0001 (7)	−0.0010 (7)	−0.0015 (7)
C4	0.0122 (9)	0.0182 (9)	0.0171 (9)	−0.0010 (7)	0.0001 (7)	0.0011 (7)
C5	0.0158 (9)	0.0179 (9)	0.0151 (9)	0.0001 (7)	0.0010 (7)	0.0007 (7)
C6	0.0134 (9)	0.0181 (9)	0.0138 (9)	0.0002 (7)	−0.0021 (7)	−0.0042 (7)
C7	0.0126 (9)	0.0167 (9)	0.0167 (9)	−0.0017 (7)	−0.0004 (7)	−0.0016 (7)
C8	0.0109 (8)	0.0152 (9)	0.0151 (9)	−0.0000 (6)	0.0005 (7)	−0.0010 (7)
C9	0.0121 (8)	0.0173 (9)	0.0122 (9)	−0.0005 (7)	0.0004 (6)	0.0007 (7)
C10	0.0225 (10)	0.0232 (10)	0.0154 (10)	−0.0048 (8)	−0.0013 (7)	−0.0036 (8)

Geometric parameters (Å, º) top

Cl1—C6	1.745 (2)	C4—C8	1.402 (3)
O1—C1	1.341 (3)	C5—C6	1.402 (3)
O1—C9	1.379 (3)	C6—C7	1.377 (3)
O2—C3	1.231 (3)	C7—C9	1.392 (3)
O3—C10	1.208 (3)	C8—C9	1.398 (3)
C1—C2	1.359 (3)	C1—H1	0.950
C2—C3	1.458 (3)	C4—H2	0.950
C2—C10	1.480 (3)	C5—H3	0.950
C3—C8	1.476 (3)	C7—H4	0.950
C4—C5	1.378 (3)	C10—H5	0.950

O1···C3	2.865 (3)	C10···H1	2.5619
O1···C6	3.598 (3)	H1···H5	3.4961
O2···C1	3.577 (3)	H2···H3	2.3320
O2···C4	2.877 (3)	Cl1···H2ⁱⁱⁱ	3.1871
O2···C10	2.895 (3)	Cl1···H2^iv	3.4009
O3···C1	2.827 (3)	Cl1···H3ⁱⁱ	3.4824
C1···C7	3.578 (3)	Cl1···H3^xi	3.0426
C1···C8	2.759 (3)	Cl1···H3^xii	3.1343
C2···C9	2.777 (3)	O1···H5ⁱⁱⁱ	3.3638
C4···C7	2.809 (3)	O2···H4^v	2.3412
C5···C9	2.769 (3)	O2···H4^vi	2.9752
C6···C8	2.769 (3)	O3···H1^ix	2.8238
Cl1···Cl1ⁱ	3.4483 (16)	O3···H1^x	2.3652
Cl1···C5ⁱⁱ	3.578 (3)	O3···H5ⁱⁱ	3.2929
O1···O2ⁱⁱⁱ	3.202 (3)	O3···H5^viii	2.5304
O1···O2^iv	3.333 (3)	C1···H5ⁱⁱⁱ	3.5044
O1···C2ⁱⁱ	3.540 (3)	C2···H1^vii	3.3800
O1···C3ⁱⁱ	3.415 (3)	C2···H5ⁱⁱ	3.5566
O1···C8ⁱⁱ	3.571 (3)	C3···H4^v	3.4647
O2···O1^v	3.333 (3)	C3···H4^vi	3.1692
O2···O1^vi	3.202 (3)	C4···H2ⁱⁱ	3.4575
O2···C2^vii	3.397 (3)	C4···H4^vi	3.2692
O2···C3^vii	3.286 (3)	C5···H2ⁱⁱ	3.4558
O2···C7^v	3.204 (3)	C5···H3^xi	3.4146
O2···C7^vi	3.185 (3)	C6···H2ⁱⁱⁱ	3.3840
O2···C8^vii	3.393 (3)	C6···H3ⁱⁱ	3.5349
O2···C9^vi	3.309 (3)	C7···H2ⁱⁱⁱ	3.2808
O3···O3^viii	3.430 (3)	C7···H4^vii	3.4681
O3···O3^ix	3.332 (3)	C8···H4^vi	3.3537
O3···C1^ix	3.278 (3)	C9···H4^vii	3.4840
O3···C1^x	3.209 (3)	C10···H1^vii	3.4338
O3···C10^viii	3.289 (3)	C10···H1^ix	3.3580
C1···O3^ix	3.278 (3)	C10···H1^x	3.4611
C1···O3^x	3.209 (3)	C10···H5ⁱⁱ	3.3751
C1···C2ⁱⁱ	3.356 (3)	C10···H5^viii	3.0735
C1···C3ⁱⁱ	3.468 (3)	H1···O3^ix	2.8238
C2···O1^vii	3.540 (3)	H1···O3^x	2.3652
C2···O2ⁱⁱ	3.397 (3)	H1···C2ⁱⁱ	3.3800
C2···C1^vii	3.356 (3)	H1···C10ⁱⁱ	3.4338
C3···O1^vii	3.415 (3)	H1···C10^ix	3.3580
C3···O2ⁱⁱ	3.286 (3)	H1···C10^x	3.4611
C3···C1^vii	3.468 (3)	H1···H1^x	2.9506
C3···C9^vii	3.481 (3)	H1···H5ⁱⁱⁱ	3.2659
C4···C6^vii	3.467 (3)	H1···H5^ix	3.5735
C4···C7^vii	3.476 (3)	H2···Cl1^v	3.4009
C5···Cl1^vii	3.578 (3)	H2···Cl1^vi	3.1871
C5···C6^vii	3.386 (4)	H2···C4^vii	3.4575
C6···C4ⁱⁱ	3.467 (3)	H2···C5^vii	3.4558
C6···C5ⁱⁱ	3.386 (4)	H2···C6^vi	3.3840
C7···O2ⁱⁱⁱ	3.185 (3)	H2···C7^vi	3.2808
C7···O2^iv	3.204 (3)	H2···H4^v	2.9597
C7···C4ⁱⁱ	3.476 (3)	H2···H4^vi	2.9822
C7···C8ⁱⁱ	3.479 (3)	H3···Cl1^vii	3.4824
C8···O1^vii	3.571 (3)	H3···Cl1^xi	3.0426
C8···O2ⁱⁱ	3.393 (3)	H3···Cl1^xii	3.1343
C8···C7^vii	3.479 (3)	H3···C5^xi	3.4146
C8···C9^vii	3.360 (3)	H3···C6^vii	3.5349
C9···O2ⁱⁱⁱ	3.309 (3)	H3···H3^xi	2.6802
C9···C3ⁱⁱ	3.481 (3)	H4···O2ⁱⁱⁱ	2.9752
C9···C8ⁱⁱ	3.360 (3)	H4···O2^iv	2.3412
C10···O3^viii	3.289 (3)	H4···C3ⁱⁱⁱ	3.1692
C10···C10^viii	3.575 (4)	H4···C3^iv	3.4647
Cl1···H3	2.8121	H4···C4ⁱⁱⁱ	3.2692
Cl1···H4	2.8064	H4···C7ⁱⁱ	3.4681
O1···H4	2.5238	H4···C8ⁱⁱⁱ	3.3537
O2···H2	2.6135	H4···C9ⁱⁱ	3.4840
O2···H5	2.6106	H4···H2ⁱⁱⁱ	2.9822
O3···H1	2.5045	H4···H2^iv	2.9597
C1···H5	3.2854	H5···O1^vi	3.3638
C3···H1	3.2928	H5···O3^vii	3.2929
C3···H2	2.6818	H5···O3^viii	2.5304
C3···H5	2.6956	H5···C1^vi	3.5044
C5···H4	3.2981	H5···C2^vii	3.5566
C6···H2	3.2536	H5···C10^vii	3.3751
C7···H3	3.2895	H5···C10^viii	3.0735
C8···H3	3.2766	H5···H1^vi	3.2659
C8···H4	3.3034	H5···H1^ix	3.5735
C9···H1	3.1896	H5···H5^viii	2.8132
C9···H2	3.2637

C1—O1—C9	118.62 (16)	C4—C8—C9	118.32 (18)
O1—C1—C2	124.73 (17)	O1—C9—C7	115.76 (17)
C1—C2—C3	120.42 (18)	O1—C9—C8	121.83 (18)
C1—C2—C10	119.24 (17)	C7—C9—C8	122.41 (17)
C3—C2—C10	120.34 (18)	O3—C10—C2	124.1 (2)
O2—C3—C2	123.38 (18)	O1—C1—H1	117.638
O2—C3—C8	122.38 (17)	C2—C1—H1	117.633
C2—C3—C8	114.24 (17)	C5—C4—H2	119.644
C5—C4—C8	120.70 (18)	C8—C4—H2	119.653
C4—C5—C6	118.78 (17)	C4—C5—H3	120.611
Cl1—C6—C5	118.56 (15)	C6—C5—H3	120.611
Cl1—C6—C7	118.76 (15)	C6—C7—H4	121.444
C5—C6—C7	122.66 (18)	C9—C7—H4	121.444
C6—C7—C9	117.11 (18)	O3—C10—H5	117.967
C3—C8—C4	121.70 (17)	C2—C10—H5	117.976
C3—C8—C9	119.98 (17)

C1—O1—C9—C7	177.96 (14)	C8—C4—C5—C6	0.9 (3)
C1—O1—C9—C8	−1.3 (3)	C8—C4—C5—H3	−179.1
C9—O1—C1—C2	1.8 (3)	H2—C4—C5—C6	−179.1
C9—O1—C1—H1	−178.2	H2—C4—C5—H3	0.9
O1—C1—C2—C3	1.1 (3)	H2—C4—C8—C3	0.4
O1—C1—C2—C10	−179.09 (14)	H2—C4—C8—C9	−179.8
H1—C1—C2—C3	−178.9	C4—C5—C6—Cl1	−179.93 (14)
H1—C1—C2—C10	0.9	C4—C5—C6—C7	−1.1 (3)
C1—C2—C3—O2	174.85 (16)	H3—C5—C6—Cl1	0.1
C1—C2—C3—C8	−4.3 (3)	H3—C5—C6—C7	178.9
C1—C2—C10—O3	5.1 (3)	Cl1—C6—C7—C9	178.98 (11)
C1—C2—C10—H5	−174.9	Cl1—C6—C7—H4	−1.0
C3—C2—C10—O3	−175.13 (16)	C5—C6—C7—C9	0.2 (3)
C3—C2—C10—H5	4.9	C5—C6—C7—H4	−179.8
C10—C2—C3—O2	−4.9 (3)	C6—C7—C9—O1	−178.22 (14)
C10—C2—C3—C8	175.94 (14)	C6—C7—C9—C8	1.0 (3)
O2—C3—C8—C4	5.4 (3)	H4—C7—C9—O1	1.8
O2—C3—C8—C9	−174.38 (15)	H4—C7—C9—C8	−179.0
C2—C3—C8—C4	−175.44 (14)	C3—C8—C9—O1	−2.2 (3)
C2—C3—C8—C9	4.8 (3)	C3—C8—C9—C7	178.65 (14)
C5—C4—C8—C3	−179.64 (15)	C4—C8—C9—O1	178.01 (14)
C5—C4—C8—C9	0.1 (3)	C4—C8—C9—C7	−1.1 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H4···O2^iv	0.95	2.34	3.204 (3)	151 (1)
C1—H1···O3^x	0.95	2.37	3.209 (3)	148 (1)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H4···O2ⁱ	0.95	2.341	3.204 (3)	150.78 (12)
C1—H1···O3ⁱⁱ	0.95	2.365	3.209 (3)	147.81 (13)

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

Acknowledgements

The University of Shizuoka is acknowledged for instrumental support.

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