1-[5-(2H-1,3-Benzodioxol-5-yl)-3-(4-methyl­phen­yl)-2-pyrazolin-1-yl]ethanone

Loh, W.-S.; Razak, I.A.; Abdul Rahiman, M.; Ravikumar, G.N.

doi:10.1107/S1600536813008817

organic compounds

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ISSN: 2056-9890

Volume 69| Part 5| May 2013| Page o726

https://doi.org/10.1107/S1600536813008817

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1-[5-(2H-1,3-Benzodioxol-5-yl)-3-(4-methylphenyl)-2-pyrazolin-1-yl]ethanone

Wan-Sin Loh,^a ‡ Ibrahim Abdul Razak,^a ^*§ M. Abdul Rahiman ^b and G. N. Ravikumar ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of PG studies in Chemistry, Government Science College, Hassan 573 201, India
^*Correspondence e-mail: arazaki@usm.my

(Received 13 March 2013; accepted 1 April 2013; online 13 April 2013)

In the title compound, C₁₉H₁₈N₂O₃, the pyrazoline ring is close to being planar (r.m.s. deviation = 0.035 Å) and subtends dihedral angles of 2.11 (8) and 82.63 (8)° with the p-tolyl and benzene rings, respectively. In the crystal, C—H⋯O and C—H⋯N hydrogen bonds link the molecules, forming a three-dimensional network. A weak C—H⋯π interaction involving the benzene ring is also observed.

Related literature

For background to pyrazoline derivatives, see: Mamolo et al. (2003 ); Bansal et al. (2001 ); Manna et al. (2005 ); Ahn et al. (2004 ); Rajendra Prasad et al. (2005 ). For a related structure, see: Du (2009 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₉H₁₈N₂O₃
M_r = 322.35
Monoclinic, P 2₁ /c
a = 7.9564 (1) Å
b = 24.1170 (4) Å
c = 8.4660 (1) Å
β = 105.380 (1)°
V = 1566.32 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.35 × 0.26 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.968, T_max = 0.984
18850 measured reflections
4828 independent reflections
3778 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.136
S = 1.09
4828 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C3/C5–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O3ⁱ	0.95	2.42	3.229 (2)	142
C4—H4A⋯O3ⁱⁱ	0.99	2.38	3.225 (2)	143
C9—H9B⋯O2ⁱⁱⁱ	0.99	2.59	3.371 (2)	136
C18—H18B⋯N2^iv	0.98	2.56	3.526 (2)	169
C19—H19A⋯O3^v	0.98	2.57	3.377 (2)	139
C19—H19A⋯Cg1^vi	0.98	2.93	3.6013 (18)	127
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x, y, z+1; (iii) x+1, y, z; (iv) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (v) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (vi) $[x+1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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: https://doi.org/10.1107/S1600536813008817/hb7056sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813008817/hb7056Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813008817/hb7056Isup3.cml

checkCIF report

Comment top

Considerable attention has been focused on pyrazoline derivatives due to their interesting biological activities. Some of the pyrazoline derivatives are reported to possess antifungal (Mamolo et al., 2003), anti-inflammatory (Bansal et al., 2001), anticancer (Manna et al., 2005), antidiabetic (Ahn et al., 2004) and antidepressant (Rajendra Prasad et al., 2005) properties.

In the title compound, Fig. 1, the benzodioxole ring system (C1–C7/O1/O2) and the pyrazole ring (C8–C10/N1/N2) are almost planar with maximum deviations of 0.081 (2) Å at atom C4 and 0.029 (2) Å at atom C8, respectively. They are almost perpendicular to each other with the dihedral angle of 82.08 (7)°. The pyrazole ring also forms dihedral angle of 2.11 (8)° with the benzene ring (C11–C16). Bond lengths and angles are almost comparable with the related structure (Du, 2009).

In the crystal, Fig. 2, C—H···O and C—H···N hydrogen bonds (Table 1) link the molecules to form three dimensional network and also feature C—H···π interactions (Table 1) involving the benzene ring (Cg1; C1–C3/C5–C7).

Related literature top

For background to pyrazoline derivatives, see: Mamolo et al. (2003); Bansal et al. (2001); Manna et al. (2005); Ahn et al. (2004); Rajendra Prasad et al. (2005). For a related structure, see: Du (2009). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

1-p-Tolyl-3(3',4'-methylene dioxyphenyl)-2-propen-1-one (0.005 mol) and hydrazine hydrate (0.005 mol) in acetic acid (15 ml) was refluxed for 6 h. The solid on cooling was collected and washed well with cold water and alcohol. It was dried and recrystallized from ethanol-dioxan. Colourless blocks were obtained by slow evaporation of a DMF/ethanol solution (1:2 v/v).

Structure description top

For background to pyrazoline derivatives, see: Mamolo et al. (2003); Bansal et al. (2001); Manna et al. (2005); Ahn et al. (2004); Rajendra Prasad et al. (2005). For a related structure, see: Du (2009). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

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 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound, viewed along the c axis. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

1-[5-(2H-1,3-Benzodioxol-5-yl)-3-(4-methylphenyl)-2-pyrazolin-1-yl]ethanone top

Crystal data top

C₁₉H₁₈N₂O₃	F(000) = 680
M_r = 322.35	D_x = 1.367 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6808 reflections
a = 7.9564 (1) Å	θ = 2.6–30.6°
b = 24.1170 (4) Å	µ = 0.09 mm⁻¹
c = 8.4660 (1) Å	T = 100 K
β = 105.380 (1)°	Block, colourless
V = 1566.32 (4) Å³	0.35 × 0.26 × 0.18 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	4828 independent reflections
Radiation source: fine-focus sealed tube	3778 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
φ and ω scans	θ_max = 30.7°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→7
T_min = 0.968, T_max = 0.984	k = −28→34
18850 measured reflections	l = −12→12

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0389P)² + 1.3146P] where P = (F_o² + 2F_c²)/3
4828 reflections	(Δ/σ)_max = 0.001
219 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₉H₁₈N₂O₃	V = 1566.32 (4) Å³
M_r = 322.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.9564 (1) Å	µ = 0.09 mm⁻¹
b = 24.1170 (4) Å	T = 100 K
c = 8.4660 (1) Å	0.35 × 0.26 × 0.18 mm
β = 105.380 (1)°

Data collection top

Bruker APEXII CCD diffractometer	4828 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3778 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.984	R_int = 0.032
18850 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	0 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 1.09	Δρ_max = 0.39 e Å⁻³
4828 reflections	Δρ_min = −0.29 e Å⁻³
219 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 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	0.20199 (17)	0.52198 (5)	0.40364 (15)	0.0242 (3)
O2	0.18293 (16)	0.61783 (5)	0.38140 (14)	0.0204 (3)
O3	0.40078 (16)	0.60685 (5)	−0.20460 (14)	0.0212 (3)
N1	0.54641 (18)	0.67124 (5)	−0.03118 (16)	0.0164 (3)
N2	0.59601 (18)	0.72596 (5)	0.00463 (16)	0.0154 (3)
C1	0.5458 (2)	0.54240 (7)	0.1907 (2)	0.0197 (3)
H1A	0.6263	0.5232	0.1455	0.024*
C2	0.4417 (2)	0.51184 (7)	0.2695 (2)	0.0212 (3)
H2A	0.4504	0.4726	0.2796	0.025*
C3	0.3269 (2)	0.54167 (7)	0.33134 (18)	0.0172 (3)
C4	0.1270 (2)	0.57023 (7)	0.4575 (2)	0.0223 (4)
H4A	0.1669	0.5735	0.5783	0.027*
H4B	−0.0018	0.5676	0.4250	0.027*
C5	0.3156 (2)	0.59905 (6)	0.31861 (18)	0.0157 (3)
C6	0.4180 (2)	0.62926 (6)	0.24358 (18)	0.0156 (3)
H6A	0.4103	0.6685	0.2371	0.019*
C7	0.5353 (2)	0.59965 (6)	0.17627 (18)	0.0163 (3)
C8	0.6489 (2)	0.63082 (7)	0.08798 (19)	0.0172 (3)
H8A	0.7085	0.6040	0.0306	0.021*
C9	0.7850 (2)	0.66945 (7)	0.19965 (19)	0.0178 (3)
H9A	0.7825	0.6660	0.3155	0.021*
H9B	0.9041	0.6611	0.1910	0.021*
C10	0.7271 (2)	0.72633 (7)	0.13314 (18)	0.0156 (3)
C11	0.8090 (2)	0.77833 (7)	0.20273 (18)	0.0157 (3)
C12	0.9503 (2)	0.77802 (7)	0.34314 (19)	0.0181 (3)
H12A	0.9944	0.7438	0.3928	0.022*
C13	1.0259 (2)	0.82764 (7)	0.40982 (19)	0.0197 (3)
H13A	1.1210	0.8268	0.5053	0.024*
C14	0.9654 (2)	0.87859 (7)	0.34000 (19)	0.0185 (3)
C15	0.8254 (2)	0.87857 (7)	0.19888 (19)	0.0184 (3)
H15A	0.7829	0.9128	0.1481	0.022*
C16	0.7481 (2)	0.82948 (7)	0.13228 (18)	0.0174 (3)
H16A	0.6523	0.8305	0.0373	0.021*
C17	0.4283 (2)	0.65621 (7)	−0.17337 (18)	0.0163 (3)
C18	0.3369 (2)	0.70214 (7)	−0.28355 (19)	0.0188 (3)
H18A	0.2313	0.6875	−0.3600	0.028*
H18B	0.4147	0.7172	−0.3453	0.028*
H18C	0.3051	0.7316	−0.2171	0.028*
C19	1.0460 (2)	0.93221 (7)	0.4153 (2)	0.0246 (4)
H19A	1.1729	0.9302	0.4352	0.037*
H19B	1.0166	0.9383	0.5193	0.037*
H19C	1.0008	0.9630	0.3404	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0277 (7)	0.0191 (6)	0.0290 (6)	−0.0026 (5)	0.0129 (5)	0.0007 (5)
O2	0.0195 (6)	0.0193 (6)	0.0251 (6)	0.0014 (5)	0.0105 (5)	−0.0008 (5)
O3	0.0242 (6)	0.0163 (6)	0.0221 (5)	−0.0015 (5)	0.0045 (5)	−0.0032 (4)
N1	0.0187 (7)	0.0131 (6)	0.0164 (6)	−0.0010 (5)	0.0030 (5)	0.0003 (5)
N2	0.0162 (7)	0.0136 (6)	0.0172 (6)	−0.0019 (5)	0.0061 (5)	−0.0016 (5)
C1	0.0212 (8)	0.0160 (7)	0.0217 (7)	0.0044 (6)	0.0055 (6)	−0.0013 (6)
C2	0.0261 (9)	0.0128 (7)	0.0242 (7)	0.0008 (6)	0.0059 (7)	0.0023 (6)
C3	0.0175 (8)	0.0174 (7)	0.0162 (7)	−0.0035 (6)	0.0031 (6)	0.0011 (6)
C4	0.0223 (9)	0.0236 (8)	0.0221 (7)	−0.0027 (7)	0.0078 (7)	−0.0021 (6)
C5	0.0140 (7)	0.0167 (7)	0.0148 (6)	0.0017 (6)	0.0010 (6)	−0.0023 (5)
C6	0.0164 (8)	0.0116 (7)	0.0173 (6)	0.0016 (6)	0.0017 (6)	−0.0012 (5)
C7	0.0170 (8)	0.0157 (7)	0.0146 (6)	−0.0005 (6)	0.0016 (6)	0.0006 (5)
C8	0.0172 (8)	0.0163 (7)	0.0177 (7)	0.0025 (6)	0.0042 (6)	0.0012 (6)
C9	0.0151 (8)	0.0182 (7)	0.0193 (7)	−0.0003 (6)	0.0032 (6)	0.0011 (6)
C10	0.0152 (8)	0.0179 (7)	0.0155 (6)	−0.0006 (6)	0.0072 (6)	0.0000 (6)
C11	0.0139 (7)	0.0191 (7)	0.0156 (6)	−0.0018 (6)	0.0067 (6)	−0.0009 (6)
C12	0.0156 (8)	0.0199 (8)	0.0192 (7)	0.0012 (6)	0.0053 (6)	0.0003 (6)
C13	0.0154 (8)	0.0241 (8)	0.0185 (7)	−0.0011 (6)	0.0023 (6)	−0.0031 (6)
C14	0.0170 (8)	0.0200 (8)	0.0197 (7)	−0.0015 (6)	0.0068 (6)	−0.0041 (6)
C15	0.0190 (8)	0.0178 (8)	0.0190 (7)	0.0019 (6)	0.0060 (6)	−0.0005 (6)
C16	0.0163 (8)	0.0208 (8)	0.0152 (6)	−0.0011 (6)	0.0042 (6)	−0.0005 (6)
C17	0.0169 (8)	0.0175 (7)	0.0165 (6)	−0.0001 (6)	0.0080 (6)	−0.0017 (6)
C18	0.0188 (8)	0.0189 (8)	0.0177 (7)	−0.0010 (6)	0.0028 (6)	0.0003 (6)
C19	0.0242 (9)	0.0218 (8)	0.0263 (8)	−0.0016 (7)	0.0041 (7)	−0.0060 (7)

Geometric parameters (Å, º) top

O1—C3	1.382 (2)	C9—C10	1.508 (2)
O1—C4	1.436 (2)	C9—H9A	0.9900
O2—C5	1.378 (2)	C9—H9B	0.9900
O2—C4	1.443 (2)	C10—C11	1.463 (2)
O3—C17	1.2265 (19)	C11—C16	1.399 (2)
N1—C17	1.3651 (19)	C11—C12	1.403 (2)
N1—N2	1.3877 (18)	C12—C13	1.390 (2)
N1—C8	1.482 (2)	C12—H12A	0.9500
N2—C10	1.292 (2)	C13—C14	1.393 (2)
C1—C7	1.387 (2)	C13—H13A	0.9500
C1—C2	1.403 (2)	C14—C15	1.401 (2)
C1—H1A	0.9500	C14—C19	1.508 (2)
C2—C3	1.371 (2)	C15—C16	1.383 (2)
C2—H2A	0.9500	C15—H15A	0.9500
C3—C5	1.389 (2)	C16—H16A	0.9500
C4—H4A	0.9900	C17—C18	1.506 (2)
C4—H4B	0.9900	C18—H18A	0.9800
C5—C6	1.369 (2)	C18—H18B	0.9800
C6—C7	1.410 (2)	C18—H18C	0.9800
C6—H6A	0.9500	C19—H19A	0.9800
C7—C8	1.516 (2)	C19—H19B	0.9800
C8—C9	1.546 (2)	C19—H19C	0.9800
C8—H8A	1.0000

C3—O1—C4	105.69 (13)	C10—C9—H9B	111.2
C5—O2—C4	105.61 (13)	C8—C9—H9B	111.2
C17—N1—N2	122.31 (13)	H9A—C9—H9B	109.1
C17—N1—C8	123.46 (13)	N2—C10—C11	121.24 (14)
N2—N1—C8	113.80 (12)	N2—C10—C9	113.99 (14)
C10—N2—N1	108.04 (13)	C11—C10—C9	124.76 (13)
C7—C1—C2	122.41 (16)	C16—C11—C12	118.35 (14)
C7—C1—H1A	118.8	C16—C11—C10	121.13 (14)
C2—C1—H1A	118.8	C12—C11—C10	120.52 (14)
C3—C2—C1	116.31 (15)	C13—C12—C11	120.18 (15)
C3—C2—H2A	121.8	C13—C12—H12A	119.9
C1—C2—H2A	121.8	C11—C12—H12A	119.9
C2—C3—O1	128.25 (15)	C12—C13—C14	121.57 (14)
C2—C3—C5	121.95 (16)	C12—C13—H13A	119.2
O1—C3—C5	109.69 (15)	C14—C13—H13A	119.2
O1—C4—O2	107.41 (13)	C13—C14—C15	117.95 (15)
O1—C4—H4A	110.2	C13—C14—C19	121.13 (14)
O2—C4—H4A	110.2	C15—C14—C19	120.92 (15)
O1—C4—H4B	110.2	C16—C15—C14	120.99 (15)
O2—C4—H4B	110.2	C16—C15—H15A	119.5
H4A—C4—H4B	108.5	C14—C15—H15A	119.5
C6—C5—O2	127.96 (14)	C15—C16—C11	120.96 (14)
C6—C5—C3	122.14 (15)	C15—C16—H16A	119.5
O2—C5—C3	109.77 (14)	C11—C16—H16A	119.5
C5—C6—C7	117.22 (14)	O3—C17—N1	119.32 (14)
C5—C6—H6A	121.4	O3—C17—C18	123.45 (14)
C7—C6—H6A	121.4	N1—C17—C18	117.23 (14)
C1—C7—C6	119.95 (15)	C17—C18—H18A	109.5
C1—C7—C8	120.50 (15)	C17—C18—H18B	109.5
C6—C7—C8	119.54 (14)	H18A—C18—H18B	109.5
N1—C8—C7	111.69 (13)	C17—C18—H18C	109.5
N1—C8—C9	100.92 (12)	H18A—C18—H18C	109.5
C7—C8—C9	114.17 (13)	H18B—C18—H18C	109.5
N1—C8—H8A	109.9	C14—C19—H19A	109.5
C7—C8—H8A	109.9	C14—C19—H19B	109.5
C9—C8—H8A	109.9	H19A—C19—H19B	109.5
C10—C9—C8	102.99 (12)	C14—C19—H19C	109.5
C10—C9—H9A	111.2	H19A—C19—H19C	109.5
C8—C9—H9A	111.2	H19B—C19—H19C	109.5

C17—N1—N2—C10	−170.21 (15)	C1—C7—C8—C9	−114.22 (16)
C8—N1—N2—C10	2.53 (18)	C6—C7—C8—C9	66.00 (18)
C7—C1—C2—C3	0.5 (2)	N1—C8—C9—C10	4.62 (16)
C1—C2—C3—O1	175.04 (15)	C7—C8—C9—C10	−115.32 (15)
C1—C2—C3—C5	−0.8 (2)	N1—N2—C10—C11	−179.57 (14)
C4—O1—C3—C2	175.73 (16)	N1—N2—C10—C9	1.01 (19)
C4—O1—C3—C5	−8.00 (17)	C8—C9—C10—N2	−3.82 (19)
C3—O1—C4—O2	13.04 (16)	C8—C9—C10—C11	176.78 (15)
C5—O2—C4—O1	−13.22 (16)	N2—C10—C11—C16	0.0 (2)
C4—O2—C5—C6	−175.69 (15)	C9—C10—C11—C16	179.32 (16)
C4—O2—C5—C3	8.42 (16)	N2—C10—C11—C12	179.46 (16)
C2—C3—C5—C6	0.1 (2)	C9—C10—C11—C12	−1.2 (2)
O1—C3—C5—C6	−176.47 (13)	C16—C11—C12—C13	0.4 (2)
C2—C3—C5—O2	176.25 (14)	C10—C11—C12—C13	−179.11 (15)
O1—C3—C5—O2	−0.30 (17)	C11—C12—C13—C14	−0.4 (3)
O2—C5—C6—C7	−174.44 (14)	C12—C13—C14—C15	−0.3 (3)
C3—C5—C6—C7	1.0 (2)	C12—C13—C14—C19	178.74 (16)
C2—C1—C7—C6	0.6 (2)	C13—C14—C15—C16	0.9 (3)
C2—C1—C7—C8	−179.21 (14)	C19—C14—C15—C16	−178.14 (16)
C5—C6—C7—C1	−1.3 (2)	C14—C15—C16—C11	−0.8 (3)
C5—C6—C7—C8	178.49 (13)	C12—C11—C16—C15	0.2 (2)
C17—N1—C8—C7	−70.29 (19)	C10—C11—C16—C15	179.70 (15)
N2—N1—C8—C7	117.07 (14)	N2—N1—C17—O3	173.77 (15)
C17—N1—C8—C9	168.00 (15)	C8—N1—C17—O3	1.7 (2)
N2—N1—C8—C9	−4.64 (17)	N2—N1—C17—C18	−6.8 (2)
C1—C7—C8—N1	132.07 (15)	C8—N1—C17—C18	−178.84 (15)
C6—C7—C8—N1	−47.70 (18)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C3/C5–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O3ⁱ	0.95	2.42	3.229 (2)	142
C4—H4A···O3ⁱⁱ	0.99	2.38	3.225 (2)	143
C9—H9B···O2ⁱⁱⁱ	0.99	2.59	3.371 (2)	136
C18—H18B···N2^iv	0.98	2.56	3.526 (2)	169
C19—H19A···O3^v	0.98	2.57	3.377 (2)	139
C19—H19A···Cg1^vi	0.98	2.93	3.6013 (18)	127

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x, y, z+1; (iii) x+1, y, z; (iv) x, −y+3/2, z−1/2; (v) x+1, −y+3/2, z+1/2; (vi) x+1, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈N₂O₃
M_r	322.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.9564 (1), 24.1170 (4), 8.4660 (1)
β (°)	105.380 (1)
V (Å³)	1566.32 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.35 × 0.26 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.968, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	18850, 4828, 3778
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.719

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.136, 1.09
No. of reflections	4828
No. of parameters	219
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.29

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C3/C5–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O3ⁱ	0.95	2.42	3.229 (2)	142
C4—H4A···O3ⁱⁱ	0.99	2.38	3.225 (2)	143
C9—H9B···O2ⁱⁱⁱ	0.99	2.59	3.371 (2)	136
C18—H18B···N2^iv	0.98	2.56	3.526 (2)	169
C19—H19A···O3^v	0.98	2.57	3.377 (2)	139
C19—H19A···Cg1^vi	0.98	2.93	3.6013 (18)	127

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x, y, z+1; (iii) x+1, y, z; (iv) x, −y+3/2, z−1/2; (v) x+1, −y+3/2, z+1/2; (vi) x+1, −y+1/2, z−1/2.

Footnotes

‡Thomson Reuters ResearcherID: C-7581-2009.

§Thomson Reuters ResearcherID: A-5599-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks Malaysian Government and USM for the award of the post of Research Officer under the Research University Grant (1001/PFIZIK/811160).

References

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