4-(4-Methyl-phen-yl)-2-(prop-2-yn-1-yl)phthalazin-1(2H)-one.

In the title compound, C18H14N2O, the dihedral angle between the methyl-phenyl ring and the phthalazone ring system (r.m.s. deviation = 0.034 Å) is 53.93 (9)°. In the crystal, mol-ecules are connected by C-H⋯O hydrogen bonds, forming chains along [101]. The chains are linked by π-π inter-actions [centroid-centroid distance 3.6990 (12) Å], forming layers parallel to (10-1).

Related literature

For general background and the biological and pharmacological properties of phthalazine derivatives, see: Abd alla et al. (2010 ▶); Awadallah et al. (2012 ▶); Khalil et al. (2009 ▶); Kim et al. (2008 ▶); Ryu et al. (2007 ▶). For a related structure, see: Bausch et al. (1997 ▶).

Experimental

Crystal data

C18H14N2O

M = 274.31

Monoclinic,

a = 11.9917 (19) Å

b = 9.7116 (16) Å

c = 12.602 (2) Å

β = 101.285 (7)°

V = 1439.2 (4) Å3

Z = 4

Cu Kα radiation

μ = 0.63 mm−1

T = 296 K

0.23 × 0.20 × 0.19 mm

Data collection

Bruker X8 Proteum diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.864, T max = 0.886

8733 measured reflections

2337 independent reflections

2093 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.132

S = 1.10

2337 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813034880/is5329sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813034880/is5329Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813034880/is5329Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C18H14N2O	F(000) = 576
Mr = 274.31	Dx = 1.266 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 2337 reflections
a = 11.9917 (19) Å	θ = 4.7–64.6°
b = 9.7116 (16) Å	µ = 0.63 mm−1
c = 12.602 (2) Å	T = 296 K
β = 101.285 (7)°	Block, yellow
V = 1439.2 (4) Å3	0.23 × 0.20 × 0.19 mm
Z = 4

Bruker X8 Proteum diffractometer	2337 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	2093 reflections with I > 2σ(I)
Helios multilayer optics monochromator	Rint = 0.036
Detector resolution: 10.7 pixels mm-1	θmax = 64.6°, θmin = 4.7°
φ and ω scans	h = −13→12
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −10→11
Tmin = 0.864, Tmax = 0.886	l = −8→14
8733 measured reflections

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)] = 0.044	H-atom parameters constrained
wR(F2) = 0.132	w = 1/[σ2(Fo2) + (0.0698P)2 + 0.2752P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.003
2337 reflections	Δρmax = 0.15 e Å−3
192 parameters	Δρmin = −0.15 e Å−3
0 restraints	Extinction correction: SHELXL, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0090 (9)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.19809 (12)	−0.11059 (16)	1.21105 (8)	0.0755 (5)
N1	0.22126 (12)	0.03101 (14)	0.95663 (10)	0.0524 (4)
N2	0.23069 (12)	0.00807 (15)	1.06549 (10)	0.0548 (5)
C1	0.07580 (12)	−0.14488 (16)	0.92636 (11)	0.0464 (5)
C2	0.09215 (13)	−0.17108 (17)	1.03779 (11)	0.0486 (5)
C3	0.17640 (14)	−0.09248 (18)	1.11276 (12)	0.0536 (5)
C4	0.14781 (13)	−0.04216 (16)	0.88990 (11)	0.0468 (5)
C5	−0.01049 (14)	−0.21765 (18)	0.85760 (13)	0.0562 (5)
C6	−0.07462 (15)	−0.3140 (2)	0.89874 (15)	0.0645 (6)
C7	−0.05524 (16)	−0.3416 (2)	1.00855 (15)	0.0647 (6)
C8	0.02715 (15)	−0.27061 (19)	1.07770 (14)	0.0588 (6)
C9	0.31525 (16)	0.0952 (2)	1.13355 (14)	0.0646 (6)
C10	0.43037 (18)	0.0402 (2)	1.14605 (14)	0.0653 (7)
C11	0.5226 (2)	−0.0013 (3)	1.1548 (2)	0.0997 (10)
C12	0.14520 (13)	−0.01379 (17)	0.77355 (12)	0.0473 (5)
C13	0.13700 (15)	0.11933 (18)	0.73343 (13)	0.0554 (6)
C14	0.13974 (16)	0.1456 (2)	0.62603 (13)	0.0604 (6)
C15	0.15141 (14)	0.0409 (2)	0.55518 (12)	0.0567 (6)
C16	0.15944 (16)	−0.0918 (2)	0.59542 (13)	0.0638 (6)
C17	0.15584 (16)	−0.11952 (19)	0.70219 (13)	0.0583 (6)
C18	0.15649 (17)	0.0690 (2)	0.43701 (13)	0.0708 (7)
H5	−0.02440	−0.20060	0.78360	0.0670*
H6	−0.13170	−0.36110	0.85220	0.0770*
H7	−0.09810	−0.40830	1.03530	0.0780*
H8	0.03990	−0.28870	1.15150	0.0710*
H9A	0.31310	0.18630	1.10180	0.0770*
H9B	0.29570	0.10410	1.20440	0.0770*
H11	0.59650	−0.03440	1.16180	0.1200*
H13	0.12950	0.19220	0.77940	0.0660*
H14	0.13360	0.23590	0.60110	0.0720*
H16	0.16750	−0.16440	0.54940	0.0760*
H17	0.16060	−0.21010	0.72650	0.0700*
H18A	0.12210	0.15650	0.41580	0.1060*
H18B	0.11620	−0.00210	0.39220	0.1060*
H18C	0.23440	0.07020	0.42870	0.1060*

	U11	U22	U33	U12	U13	U23
O1	0.0829 (9)	0.1064 (11)	0.0305 (6)	−0.0022 (8)	−0.0054 (6)	0.0047 (6)
N1	0.0592 (8)	0.0597 (8)	0.0341 (7)	0.0033 (6)	−0.0011 (6)	−0.0022 (6)
N2	0.0602 (8)	0.0656 (9)	0.0324 (7)	0.0008 (7)	−0.0062 (6)	−0.0062 (6)
C1	0.0452 (8)	0.0546 (9)	0.0356 (8)	0.0106 (7)	−0.0011 (6)	−0.0001 (6)
C2	0.0463 (8)	0.0616 (10)	0.0347 (8)	0.0120 (7)	0.0004 (6)	0.0012 (7)
C3	0.0546 (9)	0.0684 (11)	0.0338 (8)	0.0099 (8)	−0.0010 (7)	−0.0002 (7)
C4	0.0485 (8)	0.0534 (9)	0.0340 (8)	0.0077 (7)	−0.0029 (6)	−0.0022 (6)
C5	0.0558 (9)	0.0676 (11)	0.0398 (8)	0.0020 (8)	−0.0041 (7)	−0.0023 (7)
C6	0.0544 (10)	0.0732 (12)	0.0611 (11)	−0.0037 (9)	−0.0001 (8)	−0.0053 (9)
C7	0.0560 (10)	0.0724 (12)	0.0646 (11)	−0.0008 (9)	0.0089 (8)	0.0059 (9)
C8	0.0555 (9)	0.0757 (12)	0.0446 (9)	0.0087 (8)	0.0084 (7)	0.0102 (8)
C9	0.0735 (12)	0.0688 (12)	0.0429 (9)	−0.0040 (9)	−0.0094 (8)	−0.0117 (8)
C10	0.0669 (12)	0.0716 (12)	0.0519 (10)	−0.0129 (9)	−0.0015 (8)	−0.0003 (8)
C11	0.0672 (15)	0.0930 (17)	0.135 (2)	−0.0067 (13)	0.0102 (14)	0.0109 (15)
C12	0.0463 (8)	0.0578 (9)	0.0338 (8)	0.0043 (7)	−0.0016 (6)	−0.0019 (6)
C13	0.0683 (10)	0.0552 (10)	0.0416 (9)	−0.0007 (8)	0.0081 (7)	−0.0051 (7)
C14	0.0725 (11)	0.0613 (10)	0.0462 (9)	−0.0006 (8)	0.0089 (8)	0.0060 (8)
C15	0.0498 (9)	0.0820 (12)	0.0360 (8)	−0.0015 (8)	0.0027 (7)	−0.0015 (8)
C16	0.0757 (12)	0.0726 (12)	0.0424 (9)	0.0067 (9)	0.0102 (8)	−0.0125 (8)
C17	0.0726 (11)	0.0572 (10)	0.0434 (9)	0.0116 (8)	0.0075 (8)	−0.0021 (7)
C18	0.0664 (11)	0.1084 (16)	0.0362 (9)	−0.0050 (11)	0.0064 (8)	0.0095 (9)

O1—C3	1.2275 (18)	C14—C15	1.378 (3)
N1—N2	1.3725 (18)	C15—C16	1.381 (3)
N1—C4	1.303 (2)	C15—C18	1.527 (2)
N2—C3	1.373 (2)	C16—C17	1.381 (2)
N2—C9	1.463 (2)	C5—H5	0.9300
C1—C2	1.4026 (19)	C6—H6	0.9300
C1—C4	1.452 (2)	C7—H7	0.9300
C1—C5	1.404 (2)	C8—H8	0.9300
C2—C3	1.457 (2)	C9—H9A	0.9700
C2—C8	1.396 (2)	C9—H9B	0.9700
C4—C12	1.486 (2)	C11—H11	0.9300
C5—C6	1.375 (3)	C13—H13	0.9300
C6—C7	1.384 (3)	C14—H14	0.9300
C7—C8	1.369 (3)	C16—H16	0.9300
C9—C10	1.460 (3)	C17—H17	0.9300
C10—C11	1.162 (3)	C18—H18A	0.9600
C12—C13	1.385 (2)	C18—H18B	0.9600
C12—C17	1.387 (2)	C18—H18C	0.9600
C13—C14	1.384 (2)
N2—N1—C4	118.01 (13)	C15—C16—C17	121.75 (17)
N1—N2—C3	126.58 (13)	C12—C17—C16	120.78 (17)
N1—N2—C9	113.85 (13)	C1—C5—H5	120.00
C3—N2—C9	119.36 (13)	C6—C5—H5	120.00
C2—C1—C4	117.79 (13)	C5—C6—H6	120.00
C2—C1—C5	117.93 (14)	C7—C6—H6	120.00
C4—C1—C5	124.26 (13)	C6—C7—H7	120.00
C1—C2—C3	119.84 (14)	C8—C7—H7	120.00
C1—C2—C8	120.52 (14)	C2—C8—H8	120.00
C3—C2—C8	119.64 (13)	C7—C8—H8	120.00
O1—C3—N2	121.00 (16)	N2—C9—H9A	109.00
O1—C3—C2	124.23 (16)	N2—C9—H9B	109.00
N2—C3—C2	114.77 (13)	C10—C9—H9A	109.00
N1—C4—C1	122.64 (13)	C10—C9—H9B	109.00
N1—C4—C12	114.62 (14)	H9A—C9—H9B	108.00
C1—C4—C12	122.73 (13)	C10—C11—H11	180.00
C1—C5—C6	120.59 (15)	C12—C13—H13	119.00
C5—C6—C7	120.79 (17)	C14—C13—H13	120.00
C6—C7—C8	119.87 (18)	C13—C14—H14	119.00
C2—C8—C7	120.25 (16)	C15—C14—H14	119.00
N2—C9—C10	112.59 (16)	C15—C16—H16	119.00
C9—C10—C11	178.6 (2)	C17—C16—H16	119.00
C4—C12—C13	121.31 (14)	C12—C17—H17	120.00
C4—C12—C17	121.03 (15)	C16—C17—H17	120.00
C13—C12—C17	117.61 (14)	C15—C18—H18A	109.00
C12—C13—C14	121.04 (16)	C15—C18—H18B	109.00
C13—C14—C15	121.49 (17)	C15—C18—H18C	110.00
C14—C15—C16	117.33 (15)	H18A—C18—H18B	109.00
C14—C15—C18	121.90 (17)	H18A—C18—H18C	109.00
C16—C15—C18	120.77 (16)	H18B—C18—H18C	109.00
C4—N1—N2—C3	5.4 (2)	C8—C2—C3—O1	2.6 (3)
C4—N1—N2—C9	−179.97 (16)	C8—C2—C3—N2	−176.34 (16)
N2—N1—C4—C1	0.6 (2)	C1—C2—C8—C7	−1.5 (3)
N2—N1—C4—C12	−178.36 (14)	C3—C2—C8—C7	177.55 (17)
N1—N2—C3—O1	174.12 (16)	N1—C4—C12—C13	−50.0 (2)
N1—N2—C3—C2	−6.9 (2)	N1—C4—C12—C17	127.20 (17)
C9—N2—C3—O1	−0.3 (3)	C1—C4—C12—C13	131.06 (17)
C9—N2—C3—C2	178.71 (15)	C1—C4—C12—C17	−51.7 (2)
N1—N2—C9—C10	−83.42 (18)	C1—C5—C6—C7	−0.2 (3)
C3—N2—C9—C10	91.67 (19)	C5—C6—C7—C8	1.3 (3)
C4—C1—C2—C3	2.2 (2)	C6—C7—C8—C2	−0.4 (3)
C4—C1—C2—C8	−178.72 (15)	C4—C12—C13—C14	177.07 (16)
C5—C1—C2—C3	−176.58 (15)	C17—C12—C13—C14	−0.2 (3)
C5—C1—C2—C8	2.5 (2)	C4—C12—C17—C16	−176.53 (17)
C2—C1—C4—N1	−4.1 (2)	C13—C12—C17—C16	0.8 (3)
C2—C1—C4—C12	174.76 (15)	C12—C13—C14—C15	−0.4 (3)
C5—C1—C4—N1	174.61 (16)	C13—C14—C15—C16	0.5 (3)
C5—C1—C4—C12	−6.5 (2)	C13—C14—C15—C18	−178.98 (17)
C2—C1—C5—C6	−1.6 (2)	C14—C15—C16—C17	0.1 (3)
C4—C1—C5—C6	179.67 (16)	C18—C15—C16—C17	179.55 (18)
C1—C2—C3—O1	−178.30 (17)	C15—C16—C17—C12	−0.7 (3)
C1—C2—C3—N2	2.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1i	0.93	2.45	3.322 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.93	2.45	3.322 (2)	157

Symmetry code: (i) .