1-Benzoyl-4-(4-methyl­phen­yl)phthal­azine

Sakthivel, K.; Srinivasan, K.; Natarajan, S.

doi:10.1107/S1600536811050641

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3497

https://doi.org/10.1107/S1600536811050641

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1-Benzoyl-4-(4-methylphenyl)phthalazine

Karuppusamy Sakthivel,^a Kannupal Srinivasan ^a and Sampath Natarajan ^b ^*

^aSchool of Chemistry, Bharathidasan University, Thiruchirapalli, Tamil Nadu 620 024, India, and ^bDepartment of Advanced Technology Fusion, Konkuk University, 1 Hwayang-dong, Gwangjin-gu, Seoul 143 701, Republic of Korea
^*Correspondence e-mail: sams76@gmail.com

(Received 12 November 2011; accepted 25 November 2011; online 30 November 2011)

In the title molecule, C₂₂H₁₆N₂O, the tolyl and benzoyl rings make dihedral angles 50.2 (5) and 56.4 (5)°, respectively, with the phthalazine ring system while the dihedral angle between the tolyl and benzoyl rings is 0.70 (4)°. The crystal structure is stabilized by intermolecular C—H⋯O and C—H⋯N hydrogen bonds, as well as weak C—H⋯π interactions.

Related literature

For the biological activity of phthalazine derivatives, see: Grasso et al. (2000 ). For related structures, see: Dilek et al. (2004 ); Rajnikant et al. (2006 ).

Experimental

Crystal data

C₂₂H₁₆N₂O
M_r = 324.37
Monoclinic, P 2₁ /c
a = 12.4873 (2) Å
b = 8.8011 (1) Å
c = 15.4425 (2) Å
β = 92.458 (1)°
V = 1695.60 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.10 × 0.06 × 0.04 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
30411 measured reflections
3519 independent reflections
2606 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.130
S = 1.07
3519 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1ⁱ	0.93	2.71	3.400 (3)	132
C13—H13⋯N2ⁱⁱ	0.93	2.73	3.654 (3)	170
C20—H20⋯N2ⁱⁱⁱ	0.93	2.61	3.522 (2)	166
C6—H6⋯Cg1^iv	0.93	2.76	3.549 (2)	143
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]$ ; (ii) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) x, y+1, z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811050641/pv2486sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811050641/pv2486Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811050641/pv2486Isup3.cml

checkCIF report

Comment top

Phthalazine (2,3 benzodiazine) is a well known heterocyclic system which is widely used in synthetic organic chemistry as an intermediate. Its derivatives possess remarkable biological activity, such as anticonvulsant antimicrobial, anti-inflammatory, antifungal, antibacterial, vasorelaxant and cardiotonic activity (Grasso et al., 2000).

In the title molecule (Fig. 1), the phthalazine moiety consists of a benzene and a pyridazine rings fused together and shows a planar conformation; the dihedral angle between these rings is 0.70 (4)°. A tolyl and a benzoyl rings are substituted on the pyridazine ring and dihedral angle of these rings with the pyridazine ring are 50.2 (5) and 56.4 (5)°, respectively. Though the molecules do not show any classical hydrogen bonds, these molecules are connected by C–H···O and C—H···N types of intermolecular hydrogen bonds. In addition to these, a C—H···π weak interaction also helps to consolidate the molecules in the unit cell crystal packing (Fig. 2 and Tab. 1). The molecular dimensions in the title compound are in excellent agreement with the corresponding molecular dimensions reported in closely related compounds (Dilek et al., 2004; Rajnikant et al., 2006).

Related literature top

For the biological activity of phthalazine derivatives, see: Grasso et al. (2000). For related structures, see: Dilek et al. (2004); Rajnikant et al. (2006).

Experimental top

The title compound was synthesized in 70% yield by heating the compounds 1-[2-(4-methylbenzoyl)phenyl]-2-phenylethane-1,2-dione (50 mg, 0.15 mmol) with hydrazine hydrate (11 mg, 0.23 mmol) under reflux in acetonitrile (5 ml) for 6 hr. The crystals suitable for crystallographic study were grown from dichloromethane by slow evaporation at room temperature.

Structure description top

For the biological activity of phthalazine derivatives, see: Grasso et al. (2000). For related structures, see: Dilek et al. (2004); Rajnikant et al. (2006).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. ORTEP diagram of the title molecule with the atom numbering scheme. Displacement ellipsoid are drawn at 30% probability level. H-atoms were removed for clarity.
	Fig. 2. Packing diagram of the title compound viewed down the c axis. Dashed lines indicate the hydrogen bonds between the molecules.

1-benzoyl-4-(4-methylphenyl)phthalazine top

Crystal data top

C₂₂H₁₆N₂O	F(000) = 680
M_r = 324.37	D_x = 1.271 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3519 reflections
a = 12.4873 (2) Å	θ = 1.6–26.6°
b = 8.8011 (1) Å	µ = 0.08 mm⁻¹
c = 15.4425 (2) Å	T = 296 K
β = 92.458 (1)°	Needle, orange
V = 1695.60 (4) Å³	0.10 × 0.06 × 0.04 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2606 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.036
Graphite monochromator	θ_max = 26.6°, θ_min = 1.6°
ω scans	h = −15→15
30411 measured reflections	k = −11→11
3519 independent reflections	l = −19→19

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0546P)² + 0.4182P] where P = (F_o² + 2F_c²)/3
3519 reflections	(Δ/σ)_max = 0.003
226 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₂H₁₆N₂O	V = 1695.60 (4) Å³
M_r = 324.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.4873 (2) Å	µ = 0.08 mm⁻¹
b = 8.8011 (1) Å	T = 296 K
c = 15.4425 (2) Å	0.10 × 0.06 × 0.04 mm
β = 92.458 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2606 reflections with I > 2σ(I)
30411 measured reflections	R_int = 0.036
3519 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.07	Δρ_max = 0.20 e Å⁻³
3519 reflections	Δρ_min = −0.22 e Å⁻³
226 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
O1	0.00887 (10)	0.14263 (15)	−0.07710 (9)	0.0706 (4)
N1	0.21706 (11)	0.03719 (15)	0.05410 (9)	0.0506 (3)
N2	0.27574 (11)	0.07622 (15)	0.12807 (9)	0.0503 (3)
C8	0.17846 (12)	0.30203 (17)	0.02488 (10)	0.0429 (3)
C1	0.17027 (12)	0.14321 (17)	0.00642 (10)	0.0447 (4)
C2	0.28673 (12)	0.22046 (18)	0.15030 (10)	0.0449 (4)
C3	0.23980 (12)	0.34210 (17)	0.10025 (10)	0.0450 (4)
C4	0.24861 (16)	0.49746 (19)	0.12311 (12)	0.0611 (5)
H4	0.2868	0.5256	0.1736	0.073*
C5	0.20122 (17)	0.6061 (2)	0.07141 (13)	0.0660 (5)
H5	0.2077	0.7079	0.0868	0.079*
C6	0.14337 (15)	0.56618 (19)	−0.00404 (12)	0.0607 (5)
H6	0.1127	0.6418	−0.0391	0.073*
C7	0.13101 (13)	0.41727 (19)	−0.02740 (11)	0.0521 (4)
H7	0.0914	0.3919	−0.0777	0.063*
C9	0.09674 (14)	0.08398 (18)	−0.06611 (10)	0.0503 (4)
C10	0.12936 (15)	−0.04512 (18)	−0.12021 (10)	0.0540 (4)
C11	0.04861 (19)	−0.1217 (2)	−0.16781 (12)	0.0716 (6)
H11	−0.0224	−0.0922	−0.1631	0.086*
C12	0.0726 (3)	−0.2391 (3)	−0.22112 (14)	0.0957 (8)
H12	0.0183	−0.2896	−0.2525	0.115*
C13	0.1773 (3)	−0.2824 (3)	−0.22833 (14)	0.1016 (10)
H13	0.1936	−0.3623	−0.2649	0.122*
C14	0.2591 (2)	−0.2087 (3)	−0.18174 (14)	0.0890 (8)
H14	0.3298	−0.2393	−0.1870	0.107*
C15	0.23530 (17)	−0.0885 (2)	−0.12707 (11)	0.0643 (5)
H15	0.2897	−0.0382	−0.0957	0.077*
C16	0.35062 (12)	0.24271 (18)	0.23300 (10)	0.0478 (4)
C17	0.32650 (14)	0.1561 (2)	0.30488 (11)	0.0541 (4)
H17	0.2690	0.0890	0.3010	0.065*
C18	0.38613 (14)	0.1678 (2)	0.38175 (11)	0.0596 (5)
H18	0.3686	0.1079	0.4287	0.071*
C19	0.47198 (14)	0.2676 (2)	0.39033 (12)	0.0605 (5)
C20	0.49709 (15)	0.3524 (2)	0.31882 (13)	0.0658 (5)
H20	0.5553	0.4183	0.3227	0.079*
C21	0.43727 (14)	0.3414 (2)	0.24106 (12)	0.0606 (5)
H21	0.4554	0.4007	0.1940	0.073*
C22	0.53529 (18)	0.2818 (3)	0.47533 (14)	0.0875 (7)
H22A	0.5060	0.2145	0.5171	0.131*
H22B	0.5314	0.3846	0.4958	0.131*
H22C	0.6088	0.2555	0.4671	0.131*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0648 (8)	0.0652 (8)	0.0797 (9)	0.0137 (7)	−0.0217 (7)	−0.0093 (7)
N1	0.0605 (8)	0.0396 (7)	0.0507 (8)	0.0036 (6)	−0.0103 (6)	−0.0013 (6)
N2	0.0585 (8)	0.0414 (7)	0.0500 (8)	0.0032 (6)	−0.0097 (6)	0.0009 (6)
C8	0.0470 (8)	0.0402 (8)	0.0417 (8)	0.0035 (6)	0.0054 (6)	0.0015 (6)
C1	0.0503 (9)	0.0402 (8)	0.0433 (8)	0.0041 (7)	−0.0009 (7)	−0.0005 (6)
C2	0.0481 (8)	0.0434 (8)	0.0433 (8)	−0.0008 (7)	0.0023 (6)	−0.0004 (6)
C3	0.0521 (9)	0.0400 (8)	0.0431 (8)	0.0014 (7)	0.0043 (7)	−0.0006 (6)
C4	0.0808 (12)	0.0418 (9)	0.0604 (11)	0.0007 (8)	−0.0029 (9)	−0.0081 (8)
C5	0.0881 (13)	0.0362 (9)	0.0740 (12)	0.0027 (9)	0.0056 (10)	−0.0027 (8)
C6	0.0724 (11)	0.0434 (9)	0.0666 (11)	0.0116 (8)	0.0078 (9)	0.0124 (8)
C7	0.0581 (9)	0.0485 (9)	0.0497 (9)	0.0075 (8)	0.0015 (7)	0.0061 (7)
C9	0.0608 (10)	0.0430 (8)	0.0463 (9)	0.0040 (7)	−0.0073 (7)	0.0026 (7)
C10	0.0795 (12)	0.0403 (8)	0.0413 (8)	0.0036 (8)	−0.0072 (8)	0.0037 (7)
C11	0.1067 (16)	0.0528 (10)	0.0531 (10)	−0.0058 (10)	−0.0220 (10)	−0.0002 (8)
C12	0.169 (3)	0.0557 (13)	0.0598 (13)	0.0008 (15)	−0.0239 (15)	−0.0070 (10)
C13	0.211 (3)	0.0494 (12)	0.0442 (11)	0.0230 (17)	0.0024 (16)	−0.0069 (9)
C14	0.141 (2)	0.0679 (13)	0.0594 (12)	0.0400 (14)	0.0193 (13)	0.0068 (11)
C15	0.0881 (13)	0.0544 (10)	0.0504 (10)	0.0150 (10)	0.0040 (9)	0.0048 (8)
C16	0.0494 (9)	0.0478 (9)	0.0460 (9)	0.0001 (7)	−0.0004 (7)	−0.0040 (7)
C17	0.0560 (10)	0.0568 (10)	0.0495 (9)	−0.0071 (8)	−0.0001 (7)	0.0006 (8)
C18	0.0622 (11)	0.0684 (12)	0.0479 (9)	−0.0002 (9)	−0.0001 (8)	0.0006 (8)
C19	0.0551 (10)	0.0716 (12)	0.0541 (10)	0.0070 (9)	−0.0069 (8)	−0.0126 (9)
C20	0.0542 (10)	0.0733 (13)	0.0690 (12)	−0.0138 (9)	−0.0054 (9)	−0.0104 (10)
C21	0.0603 (10)	0.0619 (11)	0.0596 (11)	−0.0127 (8)	0.0030 (8)	0.0014 (9)
C22	0.0823 (15)	0.1086 (18)	0.0694 (14)	0.0066 (13)	−0.0233 (11)	−0.0172 (13)

Geometric parameters (Å, º) top

O1—C9	1.2180 (19)	C11—H11	0.9300
N1—C1	1.3105 (19)	C12—C13	1.371 (4)
N1—N2	1.3740 (17)	C12—H12	0.9300
N2—C2	1.321 (2)	C13—C14	1.385 (4)
C8—C3	1.410 (2)	C13—H13	0.9300
C8—C7	1.411 (2)	C14—C15	1.393 (3)
C8—C1	1.429 (2)	C14—H14	0.9300
C1—C9	1.510 (2)	C15—H15	0.9300
C2—C3	1.431 (2)	C16—C21	1.389 (2)
C2—C16	1.489 (2)	C16—C17	1.390 (2)
C3—C4	1.415 (2)	C17—C18	1.378 (2)
C4—C5	1.364 (3)	C17—H17	0.9300
C4—H4	0.9300	C18—C19	1.388 (3)
C5—C6	1.389 (3)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.380 (3)
C6—C7	1.366 (2)	C19—C22	1.508 (2)
C6—H6	0.9300	C20—C21	1.390 (2)
C7—H7	0.9300	C20—H20	0.9300
C9—C10	1.478 (2)	C21—H21	0.9300
C10—C15	1.385 (3)	C22—H22A	0.9600
C10—C11	1.396 (3)	C22—H22B	0.9600
C11—C12	1.363 (3)	C22—H22C	0.9600

C1—N1—N2	119.87 (13)	C11—C12—H12	120.1
C2—N2—N1	120.15 (13)	C13—C12—H12	120.1
C3—C8—C7	119.50 (14)	C12—C13—C14	120.8 (2)
C3—C8—C1	116.16 (13)	C12—C13—H13	119.6
C7—C8—C1	124.34 (15)	C14—C13—H13	119.6
N1—C1—C8	123.91 (14)	C13—C14—C15	119.9 (2)
N1—C1—C9	114.40 (13)	C13—C14—H14	120.0
C8—C1—C9	121.43 (13)	C15—C14—H14	120.0
N2—C2—C3	122.89 (14)	C10—C15—C14	119.0 (2)
N2—C2—C16	113.28 (13)	C10—C15—H15	120.5
C3—C2—C16	123.82 (14)	C14—C15—H15	120.5
C8—C3—C4	118.76 (15)	C21—C16—C17	117.78 (15)
C8—C3—C2	117.00 (14)	C21—C16—C2	123.07 (15)
C4—C3—C2	124.21 (15)	C17—C16—C2	119.08 (14)
C5—C4—C3	120.25 (17)	C18—C17—C16	121.29 (16)
C5—C4—H4	119.9	C18—C17—H17	119.4
C3—C4—H4	119.9	C16—C17—H17	119.4
C4—C5—C6	120.71 (16)	C17—C18—C19	121.09 (17)
C4—C5—H5	119.6	C17—C18—H18	119.5
C6—C5—H5	119.6	C19—C18—H18	119.5
C7—C6—C5	120.83 (16)	C20—C19—C18	117.83 (16)
C7—C6—H6	119.6	C20—C19—C22	121.52 (19)
C5—C6—H6	119.6	C18—C19—C22	120.65 (19)
C6—C7—C8	119.90 (16)	C19—C20—C21	121.44 (17)
C6—C7—H7	120.0	C19—C20—H20	119.3
C8—C7—H7	120.0	C21—C20—H20	119.3
O1—C9—C10	121.04 (15)	C16—C21—C20	120.56 (17)
O1—C9—C1	118.19 (15)	C16—C21—H21	119.7
C10—C9—C1	120.74 (14)	C20—C21—H21	119.7
C15—C10—C11	119.84 (18)	C19—C22—H22A	109.5
C15—C10—C9	122.84 (16)	C19—C22—H22B	109.5
C11—C10—C9	117.29 (17)	H22A—C22—H22B	109.5
C12—C11—C10	120.8 (2)	C19—C22—H22C	109.5
C12—C11—H11	119.6	H22A—C22—H22C	109.5
C10—C11—H11	119.6	H22B—C22—H22C	109.5
C11—C12—C13	119.7 (2)

C1—N1—N2—C2	−1.3 (2)	C8—C1—C9—C10	142.14 (16)
N2—N1—C1—C8	1.9 (2)	O1—C9—C10—C15	161.87 (17)
N2—N1—C1—C9	−172.33 (14)	C1—C9—C10—C15	−20.2 (2)
C3—C8—C1—N1	−1.1 (2)	O1—C9—C10—C11	−16.1 (2)
C7—C8—C1—N1	178.05 (15)	C1—C9—C10—C11	161.76 (15)
C3—C8—C1—C9	172.76 (14)	C15—C10—C11—C12	0.0 (3)
C7—C8—C1—C9	−8.1 (2)	C9—C10—C11—C12	178.10 (17)
N1—N2—C2—C3	−0.1 (2)	C10—C11—C12—C13	−0.2 (3)
N1—N2—C2—C16	178.77 (13)	C11—C12—C13—C14	0.3 (4)
C7—C8—C3—C4	2.4 (2)	C12—C13—C14—C15	−0.3 (3)
C1—C8—C3—C4	−178.43 (15)	C11—C10—C15—C14	0.0 (3)
C7—C8—C3—C2	−179.47 (14)	C9—C10—C15—C14	−177.99 (16)
C1—C8—C3—C2	−0.3 (2)	C13—C14—C15—C10	0.2 (3)
N2—C2—C3—C8	0.9 (2)	N2—C2—C16—C21	128.64 (18)
C16—C2—C3—C8	−177.89 (14)	C3—C2—C16—C21	−52.5 (2)
N2—C2—C3—C4	178.88 (16)	N2—C2—C16—C17	−48.2 (2)
C16—C2—C3—C4	0.1 (3)	C3—C2—C16—C17	130.66 (17)
C8—C3—C4—C5	−2.0 (3)	C21—C16—C17—C18	0.2 (3)
C2—C3—C4—C5	179.96 (17)	C2—C16—C17—C18	177.20 (16)
C3—C4—C5—C6	0.3 (3)	C16—C17—C18—C19	0.5 (3)
C4—C5—C6—C7	1.2 (3)	C17—C18—C19—C20	−1.3 (3)
C5—C6—C7—C8	−0.8 (3)	C17—C18—C19—C22	178.72 (18)
C3—C8—C7—C6	−1.0 (2)	C18—C19—C20—C21	1.4 (3)
C1—C8—C7—C6	179.88 (16)	C22—C19—C20—C21	−178.63 (19)
N1—C1—C9—O1	134.47 (17)	C17—C16—C21—C20	−0.1 (3)
C8—C1—C9—O1	−39.9 (2)	C2—C16—C21—C20	−176.99 (16)
N1—C1—C9—C10	−43.5 (2)	C19—C20—C21—C16	−0.7 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1ⁱ	0.93	2.71	3.400 (3)	132
C13—H13···N2ⁱⁱ	0.93	2.73	3.654 (3)	170
C20—H20···N2ⁱⁱⁱ	0.93	2.61	3.522 (2)	166
C6—H6···Cg1^iv	0.93	2.76	3.549 (2)	143

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

Experimental details

Crystal data
Chemical formula	C₂₂H₁₆N₂O
M_r	324.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	12.4873 (2), 8.8011 (1), 15.4425 (2)
β (°)	92.458 (1)
V (Å³)	1695.60 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.10 × 0.06 × 0.04

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	30411, 3519, 2606
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.629

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.130, 1.07
No. of reflections	3519
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.22

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1ⁱ	0.93	2.71	3.400 (3)	132
C13—H13···N2ⁱⁱ	0.93	2.73	3.654 (3)	170
C20—H20···N2ⁱⁱⁱ	0.93	2.61	3.522 (2)	166
C6—H6···Cg1^iv	0.93	2.76	3.549 (2)	143

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

Acknowledgements

KS thanks the Department of Science and Technology (DST) and the Council of Scientific and Industrial Research (CSIR), India, for financial support.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dilek, N., Gunes, B., Ide, S., Ozcan, Y. & Tezcan, H. (2004). Anal. Sci. 20, x157–x158. CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Grasso, S., De Sarro, G., De Sarro, A., Micale, N., Zappalà, M., Puja, G., Baraldi, M. & De Micheli, C. (2000). J. Med. Chem. 43, 2851–2859. Web of Science CrossRef PubMed CAS Google Scholar
Rajnikant, Dinesh, Kamni, & Deshmukh, M. B. (2006). Crystallogr. Rep. 51, 615–618. 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

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