10-(4-Methyl­benzyl­idene)anthracen-9(10H)-one

Almansour, A.I.; Arumugam, N.; Karama, U.; Razak, I.A.; Arshad, S.

doi:10.1107/S1600536812000827

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 2| February 2012| Pages o478-o479

doi:10.1107/S1600536812000827

Open

access

10-(4-Methylbenzylidene)anthracen-9(10H)-one

Abdulrahman I. Almansour,^a Natarajan Arumugam,^a ‡ Usama Karama,^a Ibrahim Abdul Razak ^b ^*§ and Suhana Arshad ^b

^aDepartment of Chemistry, College of Sciences, King Saud University, PO Box 2455, Riyadh 11451, Saudi Arabia, and ^bSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: arazaki@usm.my

(Received 4 January 2012; accepted 9 January 2012; online 21 January 2012)

In the title compound, C₂₂H₁₆O, the six-membered ring within the anthrone moiety adopts a shallow boat conformation, with puckering parameters Q = 0.2860 (17) Å, Θ = 99.1 (3)° and Φ = 114.8 (3)°. The dihedral angle between the outer benzene rings is 26.53 (8)°. The mean plane through the anthrone ring system makes a dihedral angle of 38.73 (6)° with the pendant benzene ring. In the crystal, molecules are linked by C—H⋯O hydrogen bonds into zigzag chains propagating along the c-axis direction and weak C—H⋯π interactions further consolidate the structure.

Related literature

For a related structure and background to anthrone derivatives, see: Arumugam et al. (2011 ). For related structures, see: Wen & Li (2008 ); Zhou et al. (2004 ). For the synthesis, see: Prinz et al. (2003 ). For ring conformations, see: Cremer & Pople (1975 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₂H₁₆O
M_r = 296.35
Orthorhombic, P n a 2₁
a = 7.2959 (1) Å
b = 16.3853 (2) Å
c = 13.0028 (2) Å
V = 1554.43 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.33 × 0.27 × 0.21 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.975, T_max = 0.985
20184 measured reflections
2757 independent reflections
2575 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.122
S = 1.09
2757 reflections
209 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.19 e Å⁻³
Absolute structure: Flack (1983 ), 2319 Friedel pairs
Flack parameter: 0 (10)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C16–C21 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O1ⁱ	0.95	2.35	3.275 (2)	164
C22—H22C⋯Cg1ⁱⁱ	0.98	2.94	3.726 (2)	138
C17—H17A⋯Cg2ⁱⁱⁱ	0.95	2.76	3.5073 (16)	136
Symmetry codes: (i) $[-x+1, -y, z+{\script{1\over 2}}]$ ; (ii) $[-x, -y, z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812000827/hb6592sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812000827/hb6592Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812000827/hb6592Isup3.cml

checkCIF report

Comment top

As part of our ongoing studies of anthrone derivatives (Arumugam et al., 2011), we have undertaken the X-ray crystal structure determination of the title compound, (I).

In the molecular structure (Fig 1), the six-membered ring (C1/C6–C8/C13/C14) within the anthracene moiety adopts a boat conformation with puckering parameters Q= 0.2860 (17) Å, Θ= 99.1 (3)° and Φ= 114.8 (3)° (Cremer & Pople, 1975). This differs from the planar anthracene ring reported in related structure (Arumugam et al., 2011). The mean plane through the anthracene ring (C1–C14) makes a dihedral angle of 38.73 (6)° with the phenyl ring (C16–C21). The bond lengths and angles are comparable those in the related structure (Wen & Li, 2008; Zhou et al., 2004).

The crystal packing is shown in Fig. 2. The molecules are linked by the intermolecular C3—H3A···O1 hydrogen bonds (Table 1) into infinite one dimensional zigzag chain along the c-axis. In addition, the crystal structure are further stabilized by the intermolecular C22—H22C···Cg1 and C17—H17A···Cg2 (Table 1) interactions (Cg1 and Cg2 are the centroids of C1–C6 and C16–C21 rings, respectively).

Related literature top

For a related structure and background to anthrone derivatives, see: Arumugam et al. (2011). For related structures, see: Wen & Li (2008); Zhou et al. (2004). For the synthesis, see: Prinz et al. (2003). For ring conformations, see: Cremer & Pople (1975). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

The title compound was synthesized as reported (Prinz et al., 2003) and crystallized EtOAc by slow evaporation technique.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound. The H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

10-(4-Methylbenzylidene)anthracen-9(10H)-one top

Crystal data top

C₂₂H₁₆O	F(000) = 624
M_r = 296.35	D_x = 1.266 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 8371 reflections
a = 7.2959 (1) Å	θ = 3.1–31.7°
b = 16.3853 (2) Å	µ = 0.08 mm⁻¹
c = 13.0028 (2) Å	T = 100 K
V = 1554.43 (4) Å³	Block, yellow
Z = 4	0.33 × 0.27 × 0.21 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	2757 independent reflections
Radiation source: fine-focus sealed tube	2575 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ϕ and ω scans	θ_max = 31.8°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
T_min = 0.975, T_max = 0.985	k = −24→21
20184 measured reflections	l = −19→17

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.122	w = 1/[σ²(F_o²) + (0.0831P)² + 0.1277P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.002
2757 reflections	Δρ_max = 0.40 e Å⁻³
209 parameters	Δρ_min = −0.19 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 2319 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0 (10)

Crystal data top

C₂₂H₁₆O	V = 1554.43 (4) Å³
M_r = 296.35	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 7.2959 (1) Å	µ = 0.08 mm⁻¹
b = 16.3853 (2) Å	T = 100 K
c = 13.0028 (2) Å	0.33 × 0.27 × 0.21 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	2757 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2575 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.985	R_int = 0.030
20184 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.122	Δρ_max = 0.40 e Å⁻³
S = 1.09	Δρ_min = −0.19 e Å⁻³
2757 reflections	Absolute structure: Flack (1983), 2319 Friedel pairs
209 parameters	Absolute structure parameter: 0 (10)
1 restraint

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
O1	0.22961 (18)	0.09172 (9)	0.36336 (11)	0.0332 (3)
C1	0.34392 (19)	0.11506 (9)	0.63231 (12)	0.0204 (3)
C2	0.4267 (2)	0.07120 (10)	0.71248 (13)	0.0249 (3)
H2A	0.4357	0.0949	0.7789	0.030*
C3	0.4956 (2)	−0.00689 (11)	0.69531 (15)	0.0297 (4)
H3A	0.5527	−0.0357	0.7500	0.036*
C4	0.4818 (2)	−0.04321 (11)	0.59886 (16)	0.0311 (4)
H4A	0.5270	−0.0969	0.5880	0.037*
C5	0.4016 (2)	−0.00049 (10)	0.51897 (15)	0.0274 (3)
H5A	0.3917	−0.0250	0.4530	0.033*
C6	0.3352 (2)	0.07847 (10)	0.53448 (12)	0.0223 (3)
C7	0.2696 (2)	0.12531 (10)	0.44437 (12)	0.0234 (3)
C8	0.2672 (2)	0.21516 (11)	0.45515 (12)	0.0239 (3)
C9	0.2547 (3)	0.26344 (13)	0.36613 (16)	0.0328 (4)
H9A	0.2415	0.2381	0.3008	0.039*
C10	0.2613 (3)	0.34737 (13)	0.37306 (18)	0.0384 (5)
H10A	0.2514	0.3799	0.3129	0.046*
C11	0.2828 (2)	0.38405 (12)	0.46872 (18)	0.0351 (4)
H11A	0.2905	0.4418	0.4733	0.042*
C12	0.2931 (2)	0.33765 (10)	0.55740 (16)	0.0281 (3)
H12A	0.3071	0.3638	0.6221	0.034*
C13	0.2829 (2)	0.25202 (10)	0.55238 (13)	0.0227 (3)
C14	0.2792 (2)	0.20019 (9)	0.64518 (12)	0.0203 (3)
C15	0.2111 (2)	0.23176 (9)	0.73396 (12)	0.0223 (3)
H15A	0.1904	0.2890	0.7325	0.027*
C16	0.1643 (2)	0.19219 (9)	0.83166 (12)	0.0220 (3)
C17	0.2006 (2)	0.23303 (10)	0.92404 (14)	0.0274 (3)
H17A	0.2577	0.2851	0.9224	0.033*
C18	0.1542 (2)	0.19832 (12)	1.01808 (13)	0.0293 (3)
H18A	0.1828	0.2265	1.0799	0.035*
C19	0.0662 (2)	0.12249 (11)	1.02327 (13)	0.0269 (3)
C20	0.0247 (2)	0.08341 (10)	0.93057 (13)	0.0240 (3)
H20A	−0.0385	0.0327	0.9321	0.029*
C21	0.0736 (2)	0.11680 (9)	0.83647 (12)	0.0223 (3)
H21A	0.0454	0.0884	0.7748	0.027*
C22	0.0189 (3)	0.08462 (15)	1.12512 (15)	0.0386 (4)
H22A	0.0738	0.1168	1.1807	0.058*
H22B	0.0665	0.0287	1.1276	0.058*
H22C	−0.1146	0.0836	1.1335	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0306 (6)	0.0475 (7)	0.0215 (5)	0.0048 (5)	−0.0009 (5)	−0.0047 (5)
C1	0.0160 (6)	0.0216 (6)	0.0235 (6)	0.0018 (4)	0.0013 (5)	0.0038 (5)
C2	0.0206 (6)	0.0296 (7)	0.0245 (6)	0.0027 (6)	−0.0003 (6)	0.0064 (6)
C3	0.0224 (6)	0.0301 (7)	0.0364 (9)	0.0063 (6)	0.0030 (6)	0.0117 (7)
C4	0.0247 (7)	0.0260 (7)	0.0425 (9)	0.0062 (6)	0.0062 (7)	0.0039 (7)
C5	0.0226 (7)	0.0275 (7)	0.0321 (8)	0.0018 (6)	0.0051 (6)	−0.0029 (6)
C6	0.0172 (6)	0.0272 (7)	0.0225 (6)	0.0009 (5)	0.0019 (5)	0.0028 (5)
C7	0.0178 (6)	0.0317 (7)	0.0207 (7)	0.0026 (5)	0.0025 (5)	0.0010 (6)
C8	0.0181 (6)	0.0317 (7)	0.0219 (7)	0.0035 (5)	0.0034 (5)	0.0074 (6)
C9	0.0257 (7)	0.0466 (10)	0.0261 (7)	0.0071 (7)	0.0057 (6)	0.0138 (8)
C10	0.0300 (8)	0.0449 (10)	0.0403 (10)	0.0085 (7)	0.0091 (7)	0.0259 (9)
C11	0.0244 (8)	0.0312 (8)	0.0495 (11)	0.0028 (6)	0.0096 (7)	0.0173 (8)
C12	0.0205 (7)	0.0250 (7)	0.0387 (9)	−0.0004 (5)	0.0062 (6)	0.0080 (7)
C13	0.0164 (6)	0.0252 (7)	0.0264 (7)	0.0012 (5)	0.0019 (5)	0.0071 (6)
C14	0.0168 (6)	0.0221 (6)	0.0221 (6)	−0.0005 (4)	−0.0005 (5)	0.0030 (5)
C15	0.0225 (7)	0.0215 (6)	0.0227 (7)	−0.0007 (5)	0.0008 (5)	0.0006 (5)
C16	0.0219 (7)	0.0242 (6)	0.0198 (6)	0.0007 (5)	0.0010 (6)	−0.0011 (5)
C17	0.0260 (7)	0.0315 (8)	0.0249 (7)	−0.0038 (6)	0.0009 (6)	−0.0060 (6)
C18	0.0264 (8)	0.0416 (9)	0.0198 (7)	−0.0010 (6)	−0.0008 (6)	−0.0062 (6)
C19	0.0205 (7)	0.0394 (8)	0.0208 (6)	0.0018 (6)	0.0013 (6)	0.0031 (6)
C20	0.0208 (6)	0.0272 (7)	0.0239 (7)	0.0019 (5)	0.0011 (6)	0.0025 (6)
C21	0.0224 (6)	0.0235 (6)	0.0210 (6)	0.0001 (5)	0.0020 (5)	−0.0002 (5)
C22	0.0322 (9)	0.0613 (12)	0.0224 (8)	−0.0067 (8)	0.0017 (7)	0.0081 (8)

Geometric parameters (Å, º) top

O1—C7	1.224 (2)	C11—H11A	0.9500
C1—C2	1.403 (2)	C12—C13	1.407 (2)
C1—C6	1.408 (2)	C12—H12A	0.9500
C1—C14	1.482 (2)	C13—C14	1.476 (2)
C2—C3	1.393 (2)	C14—C15	1.359 (2)
C2—H2A	0.9500	C15—C16	1.467 (2)
C3—C4	1.392 (3)	C15—H15A	0.9500
C3—H3A	0.9500	C16—C17	1.400 (2)
C4—C5	1.382 (3)	C16—C21	1.403 (2)
C4—H4A	0.9500	C17—C18	1.390 (2)
C5—C6	1.396 (2)	C17—H17A	0.9500
C5—H5A	0.9500	C18—C19	1.400 (3)
C6—C7	1.480 (2)	C18—H18A	0.9500
C7—C8	1.479 (2)	C19—C20	1.398 (2)
C8—C13	1.406 (2)	C19—C22	1.503 (3)
C8—C9	1.405 (2)	C20—C21	1.387 (2)
C9—C10	1.379 (3)	C20—H20A	0.9500
C9—H9A	0.9500	C21—H21A	0.9500
C10—C11	1.390 (4)	C22—H22A	0.9800
C10—H10A	0.9500	C22—H22B	0.9800
C11—C12	1.383 (3)	C22—H22C	0.9800

C2—C1—C6	118.21 (14)	C13—C12—H12A	119.8
C2—C1—C14	122.37 (15)	C8—C13—C12	118.33 (15)
C6—C1—C14	119.25 (14)	C8—C13—C14	119.12 (14)
C3—C2—C1	120.46 (16)	C12—C13—C14	122.48 (15)
C3—C2—H2A	119.8	C15—C14—C13	118.82 (13)
C1—C2—H2A	119.8	C15—C14—C1	124.79 (14)
C4—C3—C2	120.73 (15)	C13—C14—C1	116.33 (14)
C4—C3—H3A	119.6	C14—C15—C16	130.74 (13)
C2—C3—H3A	119.6	C14—C15—H15A	114.6
C5—C4—C3	119.43 (15)	C16—C15—H15A	114.6
C5—C4—H4A	120.3	C17—C16—C21	118.16 (14)
C3—C4—H4A	120.3	C17—C16—C15	119.18 (13)
C4—C5—C6	120.50 (17)	C21—C16—C15	122.54 (14)
C4—C5—H5A	119.8	C18—C17—C16	120.85 (15)
C6—C5—H5A	119.8	C18—C17—H17A	119.6
C5—C6—C1	120.63 (15)	C16—C17—H17A	119.6
C5—C6—C7	118.58 (15)	C17—C18—C19	121.12 (15)
C1—C6—C7	120.60 (14)	C17—C18—H18A	119.4
O1—C7—C8	121.76 (15)	C19—C18—H18A	119.4
O1—C7—C6	121.69 (15)	C20—C19—C18	117.66 (15)
C8—C7—C6	116.42 (14)	C20—C19—C22	121.40 (16)
C13—C8—C9	120.29 (16)	C18—C19—C22	120.94 (16)
C13—C8—C7	120.79 (13)	C21—C20—C19	121.62 (14)
C9—C8—C7	118.89 (16)	C21—C20—H20A	119.2
C10—C9—C8	120.4 (2)	C19—C20—H20A	119.2
C10—C9—H9A	119.8	C20—C21—C16	120.53 (15)
C8—C9—H9A	119.8	C20—C21—H21A	119.7
C9—C10—C11	119.57 (17)	C16—C21—H21A	119.7
C9—C10—H10A	120.2	C19—C22—H22A	109.5
C11—C10—H10A	120.2	C19—C22—H22B	109.5
C12—C11—C10	120.96 (17)	H22A—C22—H22B	109.5
C12—C11—H11A	119.5	C19—C22—H22C	109.5
C10—C11—H11A	119.5	H22A—C22—H22C	109.5
C11—C12—C13	120.45 (18)	H22B—C22—H22C	109.5
C11—C12—H12A	119.8

C6—C1—C2—C3	−0.9 (2)	C9—C8—C13—C14	174.59 (15)
C14—C1—C2—C3	−176.04 (15)	C7—C8—C13—C14	−7.4 (2)
C1—C2—C3—C4	−0.8 (3)	C11—C12—C13—C8	1.7 (2)
C2—C3—C4—C5	1.2 (3)	C11—C12—C13—C14	−175.30 (15)
C3—C4—C5—C6	0.1 (3)	C8—C13—C14—C15	−150.02 (15)
C4—C5—C6—C1	−1.8 (2)	C12—C13—C14—C15	27.0 (2)
C4—C5—C6—C7	173.23 (15)	C8—C13—C14—C1	27.30 (19)
C2—C1—C6—C5	2.2 (2)	C12—C13—C14—C1	−155.71 (14)
C14—C1—C6—C5	177.49 (14)	C2—C1—C14—C15	−32.6 (2)
C2—C1—C6—C7	−172.75 (14)	C6—C1—C14—C15	152.29 (16)
C14—C1—C6—C7	2.6 (2)	C2—C1—C14—C13	150.25 (14)
C5—C6—C7—O1	18.3 (2)	C6—C1—C14—C13	−24.9 (2)
C1—C6—C7—O1	−166.66 (15)	C13—C14—C15—C16	169.27 (16)
C5—C6—C7—C8	−157.66 (14)	C1—C14—C15—C16	−7.8 (3)
C1—C6—C7—C8	17.4 (2)	C14—C15—C16—C17	142.24 (19)
O1—C7—C8—C13	169.11 (15)	C14—C15—C16—C21	−41.8 (3)
C6—C7—C8—C13	−14.9 (2)	C21—C16—C17—C18	2.4 (2)
O1—C7—C8—C9	−12.8 (2)	C15—C16—C17—C18	178.48 (17)
C6—C7—C8—C9	163.10 (15)	C16—C17—C18—C19	−1.5 (3)
C13—C8—C9—C10	1.3 (3)	C17—C18—C19—C20	−0.7 (3)
C7—C8—C9—C10	−176.73 (16)	C17—C18—C19—C22	179.07 (18)
C8—C9—C10—C11	0.8 (3)	C18—C19—C20—C21	2.0 (2)
C9—C10—C11—C12	−1.6 (3)	C22—C19—C20—C21	−177.81 (17)
C10—C11—C12—C13	0.3 (3)	C19—C20—C21—C16	−1.1 (2)
C9—C8—C13—C12	−2.5 (2)	C17—C16—C21—C20	−1.1 (2)
C7—C8—C13—C12	175.48 (14)	C15—C16—C21—C20	−177.09 (14)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C16–C21 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O1ⁱ	0.95	2.35	3.275 (2)	164
C22—H22C···Cg1ⁱⁱ	0.98	2.94	3.726 (2)	138
C17—H17A···Cg2ⁱⁱⁱ	0.95	2.76	3.5073 (16)	136

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

Experimental details

Crystal data
Chemical formula	C₂₂H₁₆O
M_r	296.35
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	100
a, b, c (Å)	7.2959 (1), 16.3853 (2), 13.0028 (2)
V (Å³)	1554.43 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.33 × 0.27 × 0.21

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.975, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	20184, 2757, 2575
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.741

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.122, 1.09
No. of reflections	2757
No. of parameters	209
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.19
Absolute structure	Flack (1983), 2319 Friedel pairs
Absolute structure parameter	0 (10)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C16–C21 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O1ⁱ	0.95	2.35	3.275 (2)	164
C22—H22C···Cg1ⁱⁱ	0.98	2.94	3.726 (2)	138
C17—H17A···Cg2ⁱⁱⁱ	0.95	2.76	3.5073 (16)	136

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

Footnotes

‡Additional correspondence author, e-mail: anatarajan@ksu.edu.sa.

§Thomson Reuters ResearcherID: A-5599-2009.

Acknowledgements

This project was supported by King Saud University, Deanship of Scientific Research, College of Science Research Center. SA and IAR thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811151.

References

Arumugam, N., Almansour, A. I., Karama, U., Rosli, M. M. & Razak, I. A. (2011). Acta Cryst. E67, o2251. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Prinz, H., Ishii, Y., Hirano, T., Stoiber, T., Camacho Gomez, J. A., Schmidt, P., Dussmann, H., Burger, A. M., Prehn, J. H., Gunther, E. G., Unger, E. & Umezawa, K. (2003). J. Med. Chem. 46, 3382–3394. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wen, Z.-G. & Li, J.-M. (2008). Acta Cryst. E64, o1931. Web of Science CrossRef IUCr Journals Google Scholar
Zhou, W., Hu, W.-X. & Rao, G.-W. (2004). Acta Cryst. E60, o1234–o1235. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 2| February 2012| Pages o478-o479

doi:10.1107/S1600536812000827

Open

access