1-Benzoyl-4-(4-methyl-phen-yl)phthal-azine.

In the title mol-ecule, C(22)H(16)N(2)O, 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 inter-molecular C-H⋯O and C-H⋯N hydrogen bonds, as well as weak C-H⋯π inter-actions.

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 = 324.37

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.130

S = 1.07

3519 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.22 e Å−3

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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811050641/pv2486sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050641/pv2486Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811050641/pv2486Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C22H16N2O	F(000) = 680
Mr = 324.37	Dx = 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

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

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(Fo2) + (0.0546P)2 + 0.4182P] where P = (Fo2 + 2Fc2)/3
3519 reflections	(Δ/σ)max = 0.003
226 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···Cg1iv	0.93	2.76	3.549 (2)	143

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⋯Cg1iv	0.93	2.76	3.549 (2)	143

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .