Ethyl 4-(1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-2-yl)benzoate

Chan, Y.C.; Salhin, A.; Khairuddean, M.; Hemamalini, M.; Fun, H.-K.

doi:10.1107/S160053681005049X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Pages o98-o99

https://doi.org/10.1107/S160053681005049X

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Ethyl 4-(1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-2-yl)benzoate

Yi Chen Chan,^a Abdussalam Salhin,^a ‡ Melati Khairuddean,^a Madhukar Hemamalini ^b and Hoong-Kun Fun ^b ^*§

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 25 November 2010; accepted 2 December 2010; online 11 December 2010)

The title compound, C₂₁H₁₅NO₄, was synthesized by reducing the Schiff base obtained from acenaphthenequinone and ethyl-4-aminobenzoate. The dihedral angle between the essentially planar 1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinoline ring system [maximum deviation = 0.061 (2) Å] and the benzene ring is 75.08 (10)°. In the crystal, molecules are connected via weak intermolecular C—H⋯O hydrogen bonds, forming a two-dimensional network. The ethyl group is disordered over two sets of sites with a refined occupancy ratio of 0.502 (12):0.498 (12).

Related literature

For details and applications of acenaphthenquinone-based Schiff bases, see: Maldanis et al. (2002 ); Son et al. (2006 ); Mhaidat et al. (2009 ); Rodriguez-Argüelles et al. (1997 ); McDavid et al. (1951 ); Salhin et al. (2007 , 2008 , 2009 ); Tameem et al. (2006 , 2007 , 2008 ); Shalash et al. (2010 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₁H₁₅NO₄
M_r = 345.34
Monoclinic, C c
a = 5.2025 (7) Å
b = 18.066 (3) Å
c = 17.560 (2) Å
β = 98.365 (2)°
V = 1632.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.49 × 0.21 × 0.08 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.953, T_max = 0.992
15726 measured reflections
2393 independent reflections
2157 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.171
S = 1.07
2393 reflections
256 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O3ⁱ	0.93	2.60	3.249 (4)	127
C14—H14A⋯O1ⁱⁱ	0.93	2.41	3.312 (3)	165
Symmetry codes: (i) $[x, -y, z-{\script{1\over 2}}]$ ; (ii) x+1, y, z.

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: https://doi.org/10.1107/S160053681005049X/lh5180sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681005049X/lh5180Isup2.hkl

checkCIF report

Comment top

Acenaphthenequinone-based Schiff bases have been widely synthesized due to their significant applications in chemistry (Maldanis et al., 2002; Son et al., 2006), physics (Mhaidat et al., 2009) and pharmacology (Rodriguez-Argüelles et al., 1997; McDavid et al., 1951). As a continuation of the interest of our research group on the synthesis of Schiff base derivatives (Salhin et al., 2007, 2008, 2009; Tameem et al., 2006, 2007, 2008; Shalash et al., 2010), the title compound was prepared through the reduction of the Schiff base which was obtained from the condensation reaction of acenaphthenequinone and ethyl-4-aminobenzoate.

The molecular structure of the title compound is shown in Fig. 1. The 1,3-dioxo-1H-benzo[de]isoquinoline (O1–O2/N1/C1–C12) ring is approximately planar with maximum deviation of 0.061 (2) Å for atom N1. The ethyl group is disordered over two sites with a refined occupancy ratio of 0.502 (12):0.498 (12). The dihedral angle between the 1,3-dioxo-1H-benzo[de]isoquinoline (O1–O2/N1/C1–C12) ring and the benzene (C13–C18) ring is 75.08 (10)°.

In the crystal structure (Fig. 2), adjacent molecules are connected via intermolecular C7—H7A···O3ⁱ and C14—H14A···O1ⁱⁱ (Table 1) hydrogen bonds to form a two-dimensional network.

Related literature top

For details and applications of acenaphthenquinone Schiff bases, see: Maldanis et al. (2002); Son et al. (2006); Mhaidat et al. (2009); Rodriguez-Argüelles et al. (1997); McDavid et al. (1951); Salhin et al. (2007, 2008, 2009); Tameem et al. (2006, 2007, 2008); Shalash et al. (2010). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of acenaphthenequinone (0.182 g, 1 mmol), ethyl-4-aminobenzoate (0.165 g, 1 mmol) and methanol (30 mL) was allowed to reflux for overnight. The synthesized Schiff base was then reduced using NaBH₄ in ethanol with stirring at room temperature. Crystal of (I) suitable for X-ray crystallography was obtained by recrystallization from ethanol.

Structure description top

In the crystal structure (Fig. 2), adjacent molecules are connected via intermolecular C7—H7A···O3ⁱ and C14—H14A···O1ⁱⁱ (Table 1) hydrogen bonds to form a two-dimensional network.

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 and the atom-numbering scheme. Dotted lines represents the disorder component.
	Fig. 2. The crystal packing of the title compound with hydrogen bonds shown as dashed lines.

Ethyl 4-(1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-2-yl)benzoate top

Crystal data top

C₂₁H₁₅NO₄	F(000) = 720
M_r = 345.34	D_x = 1.405 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 5950 reflections
a = 5.2025 (7) Å	θ = 2.5–30.0°
b = 18.066 (3) Å	µ = 0.10 mm⁻¹
c = 17.560 (2) Å	T = 100 K
β = 98.365 (2)°	Needle, colourless
V = 1632.8 (4) Å³	0.49 × 0.21 × 0.08 mm
Z = 4

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	2393 independent reflections
Radiation source: fine-focus sealed tube	2157 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
φ and ω scans	θ_max = 30.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→7
T_min = 0.953, T_max = 0.992	k = −25→25
15726 measured reflections	l = −24→24

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.171	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0659P)² + 3.4903P] where P = (F_o² + 2F_c²)/3
2393 reflections	(Δ/σ)_max < 0.001
256 parameters	Δρ_max = 0.56 e Å⁻³
4 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₂₁H₁₅NO₄	V = 1632.8 (4) Å³
M_r = 345.34	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 5.2025 (7) Å	µ = 0.10 mm⁻¹
b = 18.066 (3) Å	T = 100 K
c = 17.560 (2) Å	0.49 × 0.21 × 0.08 mm
β = 98.365 (2)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	2393 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2157 reflections with I > 2σ(I)
T_min = 0.953, T_max = 0.992	R_int = 0.040
15726 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	4 restraints
wR(F²) = 0.171	H-atom parameters constrained
S = 1.07	Δρ_max = 0.56 e Å⁻³
2393 reflections	Δρ_min = −0.38 e Å⁻³
256 parameters

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 s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	Occ. (<1)
O1	0.6572 (6)	0.08698 (16)	0.20848 (18)	0.0348 (6)
O2	1.3670 (6)	−0.02019 (16)	0.3453 (2)	0.0378 (7)
O3	0.9558 (11)	0.3058 (3)	0.5083 (2)	0.0746 (15)
O4	1.2949 (12)	0.3339 (3)	0.4533 (4)	0.105 (2)
C1	0.7860 (7)	0.0310 (2)	0.2216 (2)	0.0259 (7)
C2	0.7297 (7)	−0.0388 (2)	0.1797 (2)	0.0271 (7)
C3	0.5174 (8)	−0.0424 (2)	0.1229 (2)	0.0336 (8)
H3A	0.4150	−0.0007	0.1106	0.040*
C4	0.4555 (9)	−0.1099 (3)	0.0835 (3)	0.0386 (9)
H4A	0.3117	−0.1125	0.0453	0.046*
C5	0.6070 (8)	−0.1716 (2)	0.1013 (2)	0.0334 (8)
H5A	0.5639	−0.2158	0.0753	0.040*
C6	0.8256 (7)	−0.1689 (2)	0.1583 (2)	0.0293 (8)
C7	0.9882 (8)	−0.2308 (2)	0.1776 (2)	0.0332 (8)
H7A	0.9477	−0.2756	0.1527	0.040*
C8	1.2041 (9)	−0.2262 (2)	0.2323 (3)	0.0338 (8)
H8A	1.3093	−0.2674	0.2440	0.041*
C9	1.2662 (8)	−0.1586 (2)	0.2707 (2)	0.0293 (7)
H9A	1.4141	−0.1554	0.3073	0.035*
C10	1.1111 (7)	−0.09719 (19)	0.2547 (2)	0.0254 (7)
C11	0.8898 (7)	−0.1011 (2)	0.1980 (2)	0.0245 (7)
C12	1.1773 (7)	−0.0277 (2)	0.2972 (2)	0.0267 (7)
N1	1.0028 (6)	0.03130 (17)	0.27965 (19)	0.0254 (6)
C13	1.0402 (7)	0.0969 (2)	0.3273 (2)	0.0262 (7)
C14	1.2342 (7)	0.1468 (2)	0.3184 (2)	0.0290 (7)
H14A	1.3454	0.1382	0.2824	0.035*
C15	1.2614 (8)	0.2100 (2)	0.3639 (3)	0.0345 (9)
H15A	1.3917	0.2440	0.3587	0.041*
C16	1.0928 (9)	0.2223 (2)	0.4175 (2)	0.0358 (9)
C17	0.9001 (8)	0.1711 (3)	0.4258 (2)	0.0363 (9)
H17A	0.7891	0.1793	0.4619	0.044*
C18	0.8716 (8)	0.1078 (2)	0.3807 (2)	0.0322 (8)
H18A	0.7424	0.0735	0.3861	0.039*
C19	1.1063 (12)	0.2905 (3)	0.4660 (3)	0.0525 (14)
C20	1.244 (3)	0.4000 (7)	0.5078 (9)	0.065 (4)	0.493 (17)
H20A	1.0810	0.4252	0.4906	0.078*	0.493 (17)
H20B	1.2509	0.3847	0.5610	0.078*	0.493 (17)
C21	1.483 (3)	0.4465 (6)	0.4943 (9)	0.066 (4)	0.493 (17)
H21A	1.4944	0.4896	0.5267	0.098*	0.493 (17)
H21B	1.4645	0.4615	0.4414	0.098*	0.493 (17)
H21C	1.6374	0.4173	0.5066	0.098*	0.493 (17)
C20A	1.343 (4)	0.4184 (10)	0.4745 (8)	0.074 (5)	0.507 (17)
H20C	1.4622	0.4431	0.4452	0.088*	0.507 (17)
H20D	1.1854	0.4470	0.4749	0.088*	0.507 (17)
C21A	1.470 (3)	0.3911 (11)	0.5553 (10)	0.103 (7)	0.507 (17)
H21D	1.4901	0.4322	0.5904	0.155*	0.507 (17)
H21E	1.6372	0.3701	0.5517	0.155*	0.507 (17)
H21F	1.3610	0.3543	0.5737	0.155*	0.507 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0360 (15)	0.0291 (14)	0.0376 (15)	0.0107 (12)	−0.0006 (12)	−0.0021 (11)
O2	0.0347 (15)	0.0267 (14)	0.0483 (17)	0.0047 (11)	−0.0064 (13)	−0.0026 (12)
O3	0.126 (4)	0.056 (2)	0.043 (2)	0.035 (3)	0.014 (2)	−0.0126 (18)
O4	0.102 (4)	0.056 (3)	0.152 (6)	−0.014 (3)	0.003 (4)	−0.071 (3)
C1	0.0237 (15)	0.0251 (17)	0.0286 (17)	0.0035 (12)	0.0027 (13)	−0.0016 (13)
C2	0.0257 (16)	0.0246 (17)	0.0311 (18)	−0.0002 (13)	0.0050 (14)	−0.0010 (13)
C3	0.0293 (19)	0.034 (2)	0.036 (2)	0.0037 (15)	−0.0017 (16)	−0.0033 (16)
C4	0.034 (2)	0.042 (2)	0.037 (2)	0.0004 (17)	−0.0010 (17)	−0.0098 (18)
C5	0.0343 (19)	0.0318 (19)	0.0340 (19)	−0.0042 (16)	0.0048 (16)	−0.0082 (15)
C6	0.0308 (18)	0.0262 (18)	0.0315 (18)	−0.0034 (14)	0.0069 (15)	−0.0025 (14)
C7	0.042 (2)	0.0202 (16)	0.039 (2)	−0.0004 (15)	0.0101 (17)	−0.0030 (14)
C8	0.041 (2)	0.0174 (16)	0.043 (2)	0.0069 (15)	0.0071 (17)	−0.0006 (15)
C9	0.0309 (18)	0.0197 (15)	0.0367 (19)	0.0027 (13)	0.0023 (15)	0.0004 (14)
C10	0.0268 (17)	0.0191 (15)	0.0306 (17)	0.0019 (12)	0.0053 (14)	0.0026 (13)
C11	0.0241 (16)	0.0217 (15)	0.0283 (16)	−0.0006 (12)	0.0054 (13)	−0.0006 (12)
C12	0.0269 (16)	0.0202 (15)	0.0324 (17)	0.0021 (13)	0.0024 (13)	0.0033 (13)
N1	0.0261 (14)	0.0195 (13)	0.0302 (15)	0.0014 (11)	0.0028 (12)	−0.0017 (11)
C13	0.0255 (16)	0.0226 (16)	0.0295 (17)	0.0059 (13)	0.0008 (13)	−0.0019 (13)
C14	0.0282 (17)	0.0219 (16)	0.0370 (19)	0.0033 (13)	0.0052 (14)	−0.0028 (14)
C15	0.0288 (18)	0.0224 (17)	0.051 (2)	0.0011 (14)	0.0009 (17)	−0.0081 (16)
C16	0.041 (2)	0.0303 (19)	0.0328 (19)	0.0131 (16)	−0.0068 (16)	−0.0080 (15)
C17	0.039 (2)	0.041 (2)	0.0277 (18)	0.0122 (17)	0.0023 (16)	−0.0033 (16)
C18	0.0335 (19)	0.033 (2)	0.0305 (18)	0.0038 (15)	0.0059 (15)	0.0003 (15)
C19	0.075 (4)	0.032 (2)	0.044 (2)	0.021 (2)	−0.013 (2)	−0.0114 (19)
C20	0.092 (11)	0.041 (6)	0.058 (8)	−0.012 (6)	0.003 (7)	−0.022 (6)
C21	0.079 (9)	0.033 (5)	0.085 (10)	−0.031 (6)	0.014 (8)	−0.014 (5)
C20A	0.082 (12)	0.074 (11)	0.068 (9)	0.014 (9)	0.023 (8)	−0.015 (8)
C21A	0.068 (11)	0.102 (14)	0.15 (2)	0.012 (9)	0.047 (12)	0.023 (13)

Geometric parameters (Å, º) top

O1—C1	1.217 (5)	C12—N1	1.405 (4)
O2—C12	1.210 (5)	N1—C13	1.448 (5)
O3—C19	1.188 (7)	C13—C14	1.379 (5)
O4—C19	1.300 (9)	C13—C18	1.387 (5)
O4—C20	1.576 (14)	C14—C15	1.389 (5)
O4—C20A	1.581 (19)	C14—H14A	0.9300
C1—N1	1.406 (5)	C15—C16	1.394 (6)
C1—C2	1.468 (5)	C15—H15A	0.9300
C2—C3	1.377 (5)	C16—C17	1.387 (7)
C2—C11	1.410 (5)	C16—C19	1.494 (6)
C3—C4	1.417 (6)	C17—C18	1.386 (6)
C3—H3A	0.9300	C17—H17A	0.9300
C4—C5	1.375 (6)	C18—H18A	0.9300
C4—H4A	0.9300	C20—C21	1.546 (10)
C5—C6	1.402 (6)	C20—H20A	0.9700
C5—H5A	0.9300	C20—H20B	0.9700
C6—C7	1.415 (6)	C21—H21A	0.9600
C6—C11	1.424 (5)	C21—H21B	0.9600
C7—C8	1.370 (6)	C21—H21C	0.9600
C7—H7A	0.9300	C20A—C21A	1.555 (10)
C8—C9	1.409 (5)	C20A—H20C	0.9700
C8—H8A	0.9300	C20A—H20D	0.9700
C9—C10	1.376 (5)	C21A—H21D	0.9600
C9—H9A	0.9300	C21A—H21E	0.9600
C10—C11	1.410 (5)	C21A—H21F	0.9600
C10—C12	1.476 (5)

C19—O4—C20	98.9 (7)	C1—N1—C13	116.7 (3)
C19—O4—C20A	129.7 (8)	C14—C13—C18	122.0 (4)
C20—O4—C20A	33.0 (6)	C14—C13—N1	120.5 (3)
O1—C1—N1	119.7 (3)	C18—C13—N1	117.5 (3)
O1—C1—C2	123.7 (3)	C13—C14—C15	119.1 (4)
N1—C1—C2	116.6 (3)	C13—C14—H14A	120.5
C3—C2—C11	120.8 (3)	C15—C14—H14A	120.5
C3—C2—C1	118.9 (3)	C14—C15—C16	119.9 (4)
C11—C2—C1	120.2 (3)	C14—C15—H15A	120.1
C2—C3—C4	119.7 (4)	C16—C15—H15A	120.1
C2—C3—H3A	120.1	C17—C16—C15	120.0 (4)
C4—C3—H3A	120.1	C17—C16—C19	117.7 (4)
C5—C4—C3	120.3 (4)	C15—C16—C19	122.3 (5)
C5—C4—H4A	119.8	C18—C17—C16	120.6 (4)
C3—C4—H4A	119.8	C18—C17—H17A	119.7
C4—C5—C6	120.8 (4)	C16—C17—H17A	119.7
C4—C5—H5A	119.6	C17—C18—C13	118.5 (4)
C6—C5—H5A	119.6	C17—C18—H18A	120.8
C5—C6—C7	122.5 (4)	C13—C18—H18A	120.8
C5—C6—C11	119.3 (3)	O3—C19—O4	123.3 (5)
C7—C6—C11	118.2 (3)	O3—C19—C16	124.6 (6)
C8—C7—C6	121.4 (4)	O4—C19—C16	112.0 (5)
C8—C7—H7A	119.3	C21—C20—O4	96.2 (9)
C6—C7—H7A	119.3	C21—C20—H20A	112.5
C7—C8—C9	119.7 (4)	O4—C20—H20A	112.5
C7—C8—H8A	120.1	C21—C20—H20B	112.5
C9—C8—H8A	120.1	O4—C20—H20B	112.5
C10—C9—C8	121.0 (4)	H20A—C20—H20B	110.0
C10—C9—H9A	119.5	C21A—C20A—O4	86.6 (13)
C8—C9—H9A	119.5	C21A—C20A—H20C	114.2
C9—C10—C11	119.8 (3)	O4—C20A—H20C	114.2
C9—C10—C12	119.7 (3)	C21A—C20A—H20D	114.2
C11—C10—C12	120.4 (3)	O4—C20A—H20D	114.2
C2—C11—C10	121.0 (3)	H20C—C20A—H20D	111.4
C2—C11—C6	119.1 (3)	C20A—C21A—H21D	109.5
C10—C11—C6	119.9 (3)	C20A—C21A—H21E	109.5
O2—C12—N1	120.3 (3)	H21D—C21A—H21E	109.5
O2—C12—C10	123.7 (3)	C20A—C21A—H21F	109.5
N1—C12—C10	116.0 (3)	H21D—C21A—H21F	109.5
C12—N1—C1	125.5 (3)	H21E—C21A—H21F	109.5
C12—N1—C13	117.8 (3)

O1—C1—C2—C3	−1.1 (6)	C10—C12—N1—C1	−5.3 (5)
N1—C1—C2—C3	179.1 (4)	O2—C12—N1—C13	−7.6 (5)
O1—C1—C2—C11	179.5 (4)	C10—C12—N1—C13	171.5 (3)
N1—C1—C2—C11	−0.3 (5)	O1—C1—N1—C12	−175.6 (4)
C11—C2—C3—C4	1.3 (6)	C2—C1—N1—C12	4.3 (5)
C1—C2—C3—C4	−178.1 (4)	O1—C1—N1—C13	7.6 (5)
C2—C3—C4—C5	−0.3 (7)	C2—C1—N1—C13	−172.6 (3)
C3—C4—C5—C6	−0.4 (7)	C12—N1—C13—C14	76.6 (4)
C4—C5—C6—C7	−179.1 (4)	C1—N1—C13—C14	−106.3 (4)
C4—C5—C6—C11	0.1 (6)	C12—N1—C13—C18	−104.4 (4)
C5—C6—C7—C8	178.5 (4)	C1—N1—C13—C18	72.7 (4)
C11—C6—C7—C8	−0.8 (6)	C18—C13—C14—C15	−0.3 (6)
C6—C7—C8—C9	0.4 (6)	N1—C13—C14—C15	178.6 (3)
C7—C8—C9—C10	0.8 (6)	C13—C14—C15—C16	−0.2 (6)
C8—C9—C10—C11	−1.4 (6)	C14—C15—C16—C17	0.7 (6)
C8—C9—C10—C12	178.5 (4)	C14—C15—C16—C19	−177.7 (4)
C3—C2—C11—C10	178.4 (4)	C15—C16—C17—C18	−0.6 (6)
C1—C2—C11—C10	−2.2 (5)	C19—C16—C17—C18	177.9 (4)
C3—C2—C11—C6	−1.6 (5)	C16—C17—C18—C13	0.1 (6)
C1—C2—C11—C6	177.8 (3)	C14—C13—C18—C17	0.3 (6)
C9—C10—C11—C2	−179.0 (4)	N1—C13—C18—C17	−178.6 (3)
C12—C10—C11—C2	1.1 (5)	C20—O4—C19—O3	0.3 (10)
C9—C10—C11—C6	1.0 (5)	C20A—O4—C19—O3	−13.0 (13)
C12—C10—C11—C6	−179.0 (3)	C20—O4—C19—C16	176.7 (7)
C5—C6—C11—C2	0.8 (5)	C20A—O4—C19—C16	163.4 (9)
C7—C6—C11—C2	−179.9 (4)	C17—C16—C19—O3	−4.0 (7)
C5—C6—C11—C10	−179.1 (4)	C15—C16—C19—O3	174.4 (5)
C7—C6—C11—C10	0.2 (5)	C17—C16—C19—O4	179.7 (5)
C9—C10—C12—O2	1.7 (6)	C15—C16—C19—O4	−1.9 (7)
C11—C10—C12—O2	−178.4 (4)	C19—O4—C20—C21	176.4 (10)
C9—C10—C12—N1	−177.4 (3)	C20A—O4—C20—C21	−22.5 (12)
C11—C10—C12—N1	2.5 (5)	C19—O4—C20A—C21A	84.2 (13)
O2—C12—N1—C1	175.5 (4)	C20—O4—C20A—C21A	59.5 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O3ⁱ	0.93	2.60	3.249 (4)	127
C14—H14A···O1ⁱⁱ	0.93	2.41	3.312 (3)	165

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₅NO₄
M_r	345.34
Crystal system, space group	Monoclinic, Cc
Temperature (K)	100
a, b, c (Å)	5.2025 (7), 18.066 (3), 17.560 (2)
β (°)	98.365 (2)
V (Å³)	1632.8 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.49 × 0.21 × 0.08

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.953, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	15726, 2393, 2157
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.171, 1.07
No. of reflections	2393
No. of parameters	256
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.38

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O3ⁱ	0.93	2.60	3.249 (4)	127
C14—H14A···O1ⁱⁱ	0.93	2.41	3.312 (3)	165

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

Footnotes

‡Additional correspondence author, e-mail: abdussalam@usm.my.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

YCC, AS and MK acknowledge financial support by the Universiti Sains Malaysia (USM) under the Science Fund Grant No. 1001/PKIMIA/823003. HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

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