1-(4-Chloro­benzo­yl)-2,7-dimethoxy­naphthalene

Mitsui, R.; Nakaema, K.; Noguchi, K.; Okamoto, A.; Yonezawa, N.

doi:10.1107/S1600536808017297

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1278

doi:10.1107/S1600536808017297

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1-(4-Chlorobenzoyl)-2,7-dimethoxynaphthalene

Ryosuke Mitsui,^a Kosuke Nakaema,^a Keiichi Noguchi,^b Akiko Okamoto ^a and Noriyuki Yonezawa ^a ^*

^aDepartment of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology, 2-24-16 Naka-machi, Koganei, Tokyo 184-8588, Japan, and ^bInstrumentation Analysis Center, Tokyo University of Agriculture & Technology, 2-24-16 Naka-machi, Koganei, Tokyo 184-8588, Japan
^*Correspondence e-mail: yonezawa@cc.tuat.ac.jp

(Received 28 May 2008; accepted 9 June 2008; online 19 June 2008)

In the title compound, C₁₉H₁₅ClO₃, the dihedral angle between the naphthalene ring system and the benzene ring is 72.06 (7)°. The 4-chlorophenyl group and the carbonyl group are almost coplanar. An intermolecular C—H⋯O hydrogen bond is formed between an H atom of the 4-chlorophenyl group and the O atom of one methoxy group, forming a zigzag chain along the a axis.

Related literature

For the structures of closely related compounds, see: Nakaema et al. (2007 ); Nakaema, Okamoto et al. (2008 ); Nakaema, Watanabe et al. (2008 ).

Experimental

Crystal data

C₁₉H₁₅ClO₃
M_r = 326.76
Orthorhombic, P b c a
a = 6.6033 (3) Å
b = 16.0751 (7) Å
c = 30.2216 (12) Å
V = 3208.0 (2) Å³
Z = 8
Cu Kα radiation
μ = 2.21 mm⁻¹
T = 296 K
0.40 × 0.15 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.617, T_max = 0.801
54984 measured reflections
2919 independent reflections
2453 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.118
S = 1.11
2919 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O3ⁱ	0.93	2.58	3.401 (2)	148
Symmetry code: (i) x+1, y, z.

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ); program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808017297/is2299sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808017297/is2299Isup2.hkl

checkCIF report

Comment top

Recently we have reported the structure of 1,8-bis(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (Nakaema et al., 2007), 2-(4-chlorobenzoyl)-3,6-dimethoxynaphthalene (Nakaema, Okamoto et al., 2008) and 1,8-dibenzoyl-2,7-dimethoxynaphthalene (Nakaema, Watanabe et al., 2008). As part of our ongoing studies on the formation reaction and structure of the aroylated naphthalene derivatives synthesis and crystal structure analysis of the title compound, (I), were performed. The title compound was prepared by electrophilic aromatic aroylation reaction of 2,7-dimethoxynaphthalene with 4-chlorobenzoyl chloride.

An ORTEPIII (Burnett & Johnson, 1996) plot of (I) is displayed in Fig. 1. In the molecule of (I), the interplanar angle between the benzene ring (C12—C17) and the naphthalene ring (C1—C10) is 72.06 (7)°. The carbonyl group and the 4-chlorophenyl group are almost coplanar [O1—C11—C12—C17 torsion angle = -4.4 (2)°].

In the crystal structure, the molecular packing of (I) is mainly stabilized by van der Waals interaction. The molecules of (I) are aligned consecutively in stacks along the a axis (Fig. 2). Adjacent 4-chlorophenyl groups are exactly parallel, and the perpendicular distance between these planes is 3.660 (1) Å (Fig. 3). Figure 4 shows the herring-bone packing of the naphthalene ring in the crystal. The crystal packing is additionally stabilized by intermolecular C—H···O hydrogen bonding between the methoxy oxygen and a hydrogen atom of the nearby 4-chlorophenyl group of the adjacent molecule (C13—H13···O3ⁱ; Fig. 2 and Table 1).

Related literature top

For the structures of closely related compounds, see: Nakaema et al. (2007); Nakaema, Okamoto et al. (2008); Nakaema, Watanabe et al. (2008).

Experimental top

To a solution of 4-chlorobenzoyl chloride (77 mg, 0.44 mmol) and AlCl₃ (64 mg, 0.48 mmol) in nitrobenzene (1.0 ml) was added a solution of 2,7-dimethoxynaphthalene (0.40 M in nitrobenzene, 1.0 ml, 0.40 mmol) drop-wise at 0 °C. The reaction mixture was stirred for 6 h at 0 °C and immediately poured into H₂O (10 ml) and CHCl₃ (5 ml). The aqueous layer was extracted with CHCl₃ (3 × 5 ml). The combined organic layers were washed with aqueous 2 M NaOH (3 × 20 ml), brine (3 × 20 ml), and dried over MgSO₄ for overnight. The solvent was removed in vacuo and the crude material was purified by recrystallization from hexanes to give the title compound as a colorless platelets (m.p. 394.5–394.8 K, yield 102 mg, 78%).

Spectroscopic Data: ¹H NMR (300 MHz, CDCl₃) δ 7.87 (d, 1H), 7.78 (d, 2H), 7.72 (d, 1H), 7.39 (d, 2H), 7.15 (d, 1H), 7.02 (dd, 1H), 6.78 (d, 1H), 3.79 (s, 3H), 3.73 (s, 3H); ¹³C NMR (75 MHz, CDCl₃) δ 196.7, 159.0, 155.0, 139.7, 136.5, 133.0, 131.3, 130.8, 129.7, 128.8, 124.4, 121.1, 117.1, 110.1, 102.0, 56.2, 55.2; IR (KBr): 1667, 1628, 1587, 1575, 1513, 1278, 1241, 1047.

Anal. Calcd for C₁₉H₁₅ClO₃: C 69.84, H 4.63. Found: C 69.61, H 4.74.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), showing the atom-labeling scheme and 50% probability displacement ellipsoids.
	Fig. 2. The alignment of the molecules in the crystal structure, viewed along the a axis. H atoms are omitted.
	Fig. 3. The alignment of the molecules in the crystal structure, viewed in an oblique direction. H atoms are omitted.
	Fig. 4. The alignment of the molecules in the crystal structure, showing the herring-bone packing. H atoms are omitted.

1-(4-Chlorobenzoyl)-2,7-dimethoxynaphthalene top

Crystal data top

C₁₉H₁₅ClO₃	D_x = 1.353 Mg m⁻³
M_r = 326.76	Melting point = 394.5–394.8 K
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 46869 reflections
a = 6.6033 (3) Å	θ = 3.1–68.1°
b = 16.0751 (7) Å	µ = 2.21 mm⁻¹
c = 30.2216 (12) Å	T = 296 K
V = 3208.0 (2) Å³	Platelet, colorless
Z = 8	0.40 × 0.15 × 0.10 mm
F(000) = 1360

Data collection top

Rigaku R-AXIS RAPID diffractometer	2919 independent reflections
Radiation source: rotating anode	2453 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
Detector resolution: 10.00 pixels mm^-1	θ_max = 68.1°, θ_min = 5.5°
ω scans	h = −7→7
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −19→19
T_min = 0.617, T_max = 0.801	l = −36→36
54984 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: difference Fourier map
wR(F²) = 0.118	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.057P)² + 0.6411P] where P = (F_o² + 2F_c²)/3
2919 reflections	(Δ/σ)_max < 0.001
210 parameters	Δρ_max = 0.13 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₉H₁₅ClO₃	V = 3208.0 (2) Å³
M_r = 326.76	Z = 8
Orthorhombic, Pbca	Cu Kα radiation
a = 6.6033 (3) Å	µ = 2.21 mm⁻¹
b = 16.0751 (7) Å	T = 296 K
c = 30.2216 (12) Å	0.40 × 0.15 × 0.10 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2919 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2453 reflections with I > 2σ(I)
T_min = 0.617, T_max = 0.801	R_int = 0.032
54984 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 1.11	Δρ_max = 0.13 e Å⁻³
2919 reflections	Δρ_min = −0.33 e Å⁻³
210 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	1.30817 (12)	−0.12548 (4)	−0.02595 (2)	0.1046 (3)
O1	0.6267 (2)	−0.08777 (8)	0.13581 (5)	0.0831 (4)
O2	1.0971 (2)	−0.05318 (8)	0.18610 (5)	0.0795 (4)
O3	0.2593 (2)	0.17844 (8)	0.10247 (5)	0.0867 (4)
C1	0.8299 (2)	0.02580 (10)	0.15836 (5)	0.0558 (4)
C2	0.9962 (3)	0.02106 (11)	0.18585 (6)	0.0631 (4)
C3	1.0529 (3)	0.08948 (13)	0.21247 (6)	0.0725 (5)
H3	1.1655	0.0861	0.2308	0.087*
C4	0.9409 (3)	0.16017 (12)	0.21089 (6)	0.0730 (5)
H4	0.9805	0.2053	0.2281	0.088*
C5	0.7672 (3)	0.16779 (10)	0.18420 (5)	0.0616 (4)
C6	0.6488 (3)	0.24079 (11)	0.18207 (6)	0.0725 (5)
H6	0.6863	0.2864	0.1991	0.087*
C7	0.4820 (3)	0.24673 (11)	0.15594 (6)	0.0723 (5)
H7	0.4072	0.2957	0.1552	0.087*
C8	0.4234 (3)	0.17821 (10)	0.13003 (6)	0.0644 (4)
C9	0.5338 (3)	0.10614 (10)	0.13091 (5)	0.0588 (4)
H9	0.4928	0.0612	0.1137	0.071*
C10	0.7086 (2)	0.09875 (10)	0.15751 (5)	0.0546 (4)
C11	0.7780 (2)	−0.04641 (10)	0.12873 (6)	0.0572 (4)
C12	0.9101 (2)	−0.06394 (9)	0.09012 (5)	0.0542 (4)
C13	1.0749 (3)	−0.01439 (10)	0.07974 (6)	0.0632 (4)
H13	1.1037	0.0319	0.0971	0.076*
C14	1.1968 (3)	−0.03274 (12)	0.04398 (6)	0.0718 (5)
H14	1.3074	0.0007	0.0372	0.086*
C15	1.1529 (3)	−0.10086 (11)	0.01855 (6)	0.0700 (5)
C16	0.9900 (4)	−0.15030 (13)	0.02771 (7)	0.0839 (6)
H16	0.9615	−0.1961	0.0100	0.101*
C17	0.8687 (3)	−0.13182 (11)	0.06334 (7)	0.0736 (5)
H17	0.7573	−0.1653	0.0695	0.088*
C18	1.2729 (3)	−0.06178 (17)	0.21273 (7)	0.0894 (6)
H18A	1.3333	−0.1152	0.2075	0.107*
H18B	1.2363	−0.0571	0.2434	0.107*
H18C	1.3681	−0.0188	0.2053	0.107*
C19	0.1263 (3)	0.24781 (13)	0.10308 (9)	0.0925 (7)
H19A	0.0139	0.2374	0.0837	0.111*
H19B	0.1976	0.2965	0.0933	0.111*
H19C	0.0775	0.2564	0.1326	0.111*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1391 (6)	0.0859 (4)	0.0887 (4)	0.0050 (3)	0.0444 (4)	−0.0088 (3)
O1	0.0689 (8)	0.0647 (8)	0.1156 (11)	−0.0185 (6)	0.0228 (7)	−0.0237 (7)
O2	0.0751 (8)	0.0765 (9)	0.0869 (9)	0.0094 (7)	−0.0210 (7)	−0.0126 (7)
O3	0.0830 (9)	0.0638 (8)	0.1132 (11)	0.0160 (7)	−0.0117 (8)	−0.0033 (7)
C1	0.0563 (9)	0.0530 (8)	0.0580 (9)	−0.0081 (7)	0.0046 (7)	−0.0055 (7)
C2	0.0620 (10)	0.0644 (10)	0.0630 (10)	−0.0064 (8)	0.0019 (8)	−0.0055 (7)
C3	0.0746 (12)	0.0808 (13)	0.0622 (10)	−0.0154 (10)	−0.0051 (9)	−0.0111 (9)
C4	0.0908 (14)	0.0668 (11)	0.0613 (10)	−0.0239 (10)	0.0043 (9)	−0.0148 (8)
C5	0.0772 (11)	0.0532 (9)	0.0544 (8)	−0.0148 (8)	0.0137 (8)	−0.0073 (7)
C6	0.1007 (14)	0.0491 (9)	0.0677 (11)	−0.0127 (9)	0.0175 (10)	−0.0101 (7)
C7	0.0923 (13)	0.0464 (8)	0.0781 (12)	0.0022 (9)	0.0210 (11)	−0.0005 (8)
C8	0.0694 (11)	0.0526 (9)	0.0711 (10)	−0.0012 (8)	0.0096 (9)	0.0029 (7)
C9	0.0645 (10)	0.0483 (8)	0.0636 (9)	−0.0046 (7)	0.0062 (8)	−0.0052 (7)
C10	0.0628 (9)	0.0472 (8)	0.0539 (8)	−0.0094 (7)	0.0117 (7)	−0.0028 (6)
C11	0.0539 (9)	0.0465 (8)	0.0711 (10)	−0.0030 (7)	−0.0005 (7)	−0.0041 (7)
C12	0.0574 (9)	0.0442 (7)	0.0611 (9)	−0.0014 (7)	−0.0045 (7)	−0.0021 (6)
C13	0.0671 (10)	0.0543 (9)	0.0681 (10)	−0.0097 (8)	0.0017 (8)	−0.0088 (7)
C14	0.0748 (12)	0.0653 (11)	0.0752 (11)	−0.0092 (9)	0.0109 (9)	−0.0003 (9)
C15	0.0908 (13)	0.0565 (9)	0.0628 (10)	0.0047 (9)	0.0110 (9)	0.0016 (8)
C16	0.1138 (16)	0.0636 (11)	0.0742 (12)	−0.0172 (12)	0.0141 (11)	−0.0208 (9)
C17	0.0850 (12)	0.0592 (10)	0.0766 (12)	−0.0206 (9)	0.0066 (10)	−0.0143 (8)
C18	0.0724 (13)	0.1075 (17)	0.0884 (14)	0.0130 (12)	−0.0139 (11)	−0.0099 (12)
C19	0.0852 (14)	0.0726 (13)	0.1198 (18)	0.0214 (11)	0.0122 (13)	0.0190 (12)

Geometric parameters (Å, º) top

Cl1—C15	1.7366 (19)	C8—C9	1.369 (2)
O1—C11	1.219 (2)	C9—C10	1.412 (2)
O2—C2	1.367 (2)	C9—H9	0.9300
O2—C18	1.419 (2)	C11—C12	1.484 (2)
O3—C8	1.367 (2)	C12—C13	1.384 (2)
O3—C19	1.420 (2)	C12—C17	1.386 (2)
C1—C2	1.379 (2)	C13—C14	1.380 (2)
C1—C10	1.420 (2)	C13—H13	0.9300
C1—C11	1.506 (2)	C14—C15	1.369 (3)
C2—C3	1.413 (2)	C14—H14	0.9300
C3—C4	1.356 (3)	C15—C16	1.366 (3)
C3—H3	0.9300	C16—C17	1.375 (3)
C4—C5	1.408 (3)	C16—H16	0.9300
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.411 (3)	C18—H18A	0.9600
C5—C10	1.426 (2)	C18—H18B	0.9600
C6—C7	1.359 (3)	C18—H18C	0.9600
C6—H6	0.9300	C19—H19A	0.9600
C7—C8	1.406 (3)	C19—H19B	0.9600
C7—H7	0.9300	C19—H19C	0.9600

C2—O2—C18	119.13 (16)	O1—C11—C1	120.20 (15)
C8—O3—C19	119.00 (17)	C12—C11—C1	118.69 (13)
C2—C1—C10	120.37 (15)	C13—C12—C17	118.41 (16)
C2—C1—C11	119.81 (15)	C13—C12—C11	122.07 (14)
C10—C1—C11	119.82 (14)	C17—C12—C11	119.52 (15)
O2—C2—C1	116.08 (14)	C14—C13—C12	120.88 (16)
O2—C2—C3	123.20 (17)	C14—C13—H13	119.6
C1—C2—C3	120.71 (17)	C12—C13—H13	119.6
C4—C3—C2	119.21 (18)	C15—C14—C13	119.16 (17)
C4—C3—H3	120.4	C15—C14—H14	120.4
C2—C3—H3	120.4	C13—C14—H14	120.4
C3—C4—C5	122.49 (16)	C16—C15—C14	121.23 (18)
C3—C4—H4	118.8	C16—C15—Cl1	119.29 (15)
C5—C4—H4	118.8	C14—C15—Cl1	119.48 (15)
C4—C5—C6	123.35 (16)	C15—C16—C17	119.48 (17)
C4—C5—C10	118.52 (17)	C15—C16—H16	120.3
C6—C5—C10	118.12 (17)	C17—C16—H16	120.3
C7—C6—C5	122.26 (16)	C16—C17—C12	120.83 (18)
C7—C6—H6	118.9	C16—C17—H17	119.6
C5—C6—H6	118.9	C12—C17—H17	119.6
C6—C7—C8	119.47 (17)	O2—C18—H18A	109.5
C6—C7—H7	120.3	O2—C18—H18B	109.5
C8—C7—H7	120.3	H18A—C18—H18B	109.5
O3—C8—C9	115.86 (15)	O2—C18—H18C	109.5
O3—C8—C7	123.76 (16)	H18A—C18—H18C	109.5
C9—C8—C7	120.37 (18)	H18B—C18—H18C	109.5
C8—C9—C10	121.17 (15)	O3—C19—H19A	109.5
C8—C9—H9	119.4	O3—C19—H19B	109.5
C10—C9—H9	119.4	H19A—C19—H19B	109.5
C9—C10—C1	122.75 (14)	O3—C19—H19C	109.5
C9—C10—C5	118.59 (15)	H19A—C19—H19C	109.5
C1—C10—C5	118.66 (15)	H19B—C19—H19C	109.5
O1—C11—C12	121.07 (15)

C18—O2—C2—C1	178.33 (18)	C2—C1—C10—C5	2.5 (2)
C18—O2—C2—C3	−2.9 (3)	C11—C1—C10—C5	−176.81 (14)
C10—C1—C2—O2	176.63 (15)	C4—C5—C10—C9	179.66 (15)
C11—C1—C2—O2	−4.0 (2)	C6—C5—C10—C9	−1.1 (2)
C10—C1—C2—C3	−2.2 (2)	C4—C5—C10—C1	−1.1 (2)
C11—C1—C2—C3	177.18 (16)	C6—C5—C10—C1	178.16 (14)
O2—C2—C3—C4	−178.39 (17)	C2—C1—C11—O1	110.8 (2)
C1—C2—C3—C4	0.3 (3)	C10—C1—C11—O1	−69.8 (2)
C2—C3—C4—C5	1.1 (3)	C2—C1—C11—C12	−71.3 (2)
C3—C4—C5—C6	−179.95 (17)	C10—C1—C11—C12	108.01 (17)
C3—C4—C5—C10	−0.7 (3)	O1—C11—C12—C13	175.57 (17)
C4—C5—C6—C7	179.79 (17)	C1—C11—C12—C13	−2.2 (2)
C10—C5—C6—C7	0.6 (3)	O1—C11—C12—C17	−4.4 (3)
C5—C6—C7—C8	0.1 (3)	C1—C11—C12—C17	177.83 (16)
C19—O3—C8—C9	173.79 (17)	C17—C12—C13—C14	−0.9 (3)
C19—O3—C8—C7	−7.0 (3)	C11—C12—C13—C14	179.13 (17)
C6—C7—C8—O3	−179.41 (17)	C12—C13—C14—C15	0.2 (3)
C6—C7—C8—C9	−0.3 (3)	C13—C14—C15—C16	0.6 (3)
O3—C8—C9—C10	178.92 (15)	C13—C14—C15—Cl1	−178.88 (15)
C7—C8—C9—C10	−0.3 (3)	C14—C15—C16—C17	−0.5 (3)
C8—C9—C10—C1	−178.25 (15)	Cl1—C15—C16—C17	178.95 (18)
C8—C9—C10—C5	1.0 (2)	C15—C16—C17—C12	−0.3 (3)
C2—C1—C10—C9	−178.27 (15)	C13—C12—C17—C16	1.0 (3)
C11—C1—C10—C9	2.4 (2)	C11—C12—C17—C16	−179.07 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O3ⁱ	0.93	2.58	3.401 (2)	148

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₅ClO₃
M_r	326.76
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	6.6033 (3), 16.0751 (7), 30.2216 (12)
V (Å³)	3208.0 (2)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	2.21
Crystal size (mm)	0.40 × 0.15 × 0.10

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.617, 0.801
No. of measured, independent and observed [I > 2σ(I)] reflections	54984, 2919, 2453
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.118, 1.11
No. of reflections	2919
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.33

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O3ⁱ	0.93	2.58	3.401 (2)	148

Symmetry code: (i) x+1, y, z.

Acknowledgements

This work was partially supported by the Shorai Foundation for the Promotion of Science & Engineering, Tokyo, Japan.

References

Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory. Tennessee, USA. Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Nakaema, K., Okamoto, A., Imaizumi, M., Noguchi, K. & Yonezawa, N. (2008). Acta Cryst. E64, o612. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nakaema, K., Okamoto, A., Noguchi, K. & Yonezawa, N. (2007). Acta Cryst. E63, o4120. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nakaema, K., Watanabe, S., Okamoto, A., Noguchi, K. & Yonezawa, N. (2008). Acta Cryst. E64, o807. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar