1-(2,6-Diisopropyl-phen-oxy)-4-phenyl-phthalazine.

In the title mol-ecule, C(26)H(26)N(2)O, the phenyl and phen-oxy rings form dihedral angles of 54.66 (7) and 84.83 (6)°, respectively, with the phthalazine mean plane. The crystal packing exhibits weak C-H⋯π inter-actions.

Related literature

For details of the synthesis, see: Tong et al. (2008 ▶, 2012 ▶). For related structures, see: Dilek et al. (2004 ▶); Rajnikant et al. (2006 ▶); Sakthivel et al. (2011 ▶).

Experimental

Crystal data

C26H26N2O

M = 382.49

Monoclinic,

a = 14.079 (10) Å

b = 8.369 (6) Å

c = 19.244 (13) Å

β = 109.104 (9)°

V = 2143 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 273 K

0.31 × 0.29 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.978, T max = 0.990

9404 measured reflections

3596 independent reflections

2028 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.165

S = 0.90

3596 reflections

267 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812033296/cv5322sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033296/cv5322Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812033296/cv5322Isup3.cml

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

C26H26N2O	F(000) = 816
Mr = 382.49	Dx = 1.186 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1750 reflections
a = 14.079 (10) Å	θ = 2.7–22.8°
b = 8.369 (6) Å	µ = 0.07 mm−1
c = 19.244 (13) Å	T = 273 K
β = 109.104 (9)°	Block, colourless
V = 2143 (3) Å3	0.31 × 0.29 × 0.14 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3596 independent reflections
Radiation source: fine-focus sealed tube	2028 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
ω scans	θmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −16→12
Tmin = 0.978, Tmax = 0.990	k = −9→9
9404 measured reflections	l = −22→22

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)] = 0.046	H-atom parameters constrained
wR(F2) = 0.165	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
S = 0.90	(Δ/σ)max < 0.001
3596 reflections	Δρmax = 0.16 e Å−3
267 parameters	Δρmin = −0.15 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0064 (16)

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	0.34098 (10)	0.39831 (14)	0.11904 (7)	0.0538 (4)
N1	0.21896 (13)	0.28031 (18)	0.02336 (10)	0.0589 (5)
N2	0.13859 (13)	0.29298 (18)	−0.04103 (10)	0.0586 (5)
C1	−0.05395 (18)	0.5056 (3)	−0.26486 (13)	0.0669 (7)
H1	−0.0493	0.5583	−0.3061	0.080*
C2	0.02474 (16)	0.5119 (2)	−0.19941 (12)	0.0585 (6)
H2	0.0821	0.5702	−0.1967	0.070*
C3	0.01925 (14)	0.4318 (2)	−0.13752 (12)	0.0476 (5)
C4	−0.06648 (16)	0.3467 (3)	−0.14229 (13)	0.0598 (6)
H4	−0.0711	0.2920	−0.1015	0.072*
C5	−0.14592 (17)	0.3428 (3)	−0.20810 (15)	0.0703 (7)
H5	−0.2041	0.2866	−0.2110	0.084*
C6	−0.13891 (19)	0.4214 (3)	−0.26883 (15)	0.0707 (8)
H6	−0.1921	0.4175	−0.3129	0.085*
C7	0.11235 (17)	0.7351 (2)	−0.05706 (12)	0.0573 (6)
H7	0.0554	0.7465	−0.0982	0.069*
C8	0.16031 (18)	0.8674 (2)	−0.02080 (13)	0.0628 (7)
H8	0.1361	0.9684	−0.0379	0.075*
C9	0.24466 (17)	0.8534 (2)	0.04120 (12)	0.0605 (6)
H9	0.2776	0.9448	0.0645	0.073*
C10	0.27973 (15)	0.7063 (2)	0.06820 (12)	0.0519 (6)
H10	0.3353	0.6973	0.1106	0.062*
C11	0.23150 (14)	0.5686 (2)	0.03174 (11)	0.0443 (5)
C12	0.14875 (14)	0.5808 (2)	−0.03242 (11)	0.0452 (5)
C13	0.10543 (15)	0.4343 (2)	−0.06729 (11)	0.0480 (5)
C14	0.26126 (14)	0.4091 (2)	0.05578 (11)	0.0471 (5)
C15	0.38186 (15)	0.2456 (2)	0.14320 (11)	0.0474 (5)
C16	0.46379 (16)	0.1981 (2)	0.12297 (12)	0.0560 (6)
C17	0.50782 (17)	0.0537 (3)	0.15145 (14)	0.0668 (7)
H17	0.5622	0.0166	0.1387	0.080*
C18	0.47331 (18)	−0.0360 (3)	0.19788 (13)	0.0666 (7)
H18	0.5039	−0.1328	0.2160	0.080*
C19	0.39335 (17)	0.0175 (2)	0.21759 (12)	0.0612 (6)
H19	0.3707	−0.0437	0.2494	0.073*
C20	0.34555 (15)	0.1613 (2)	0.19098 (11)	0.0517 (6)
C21	0.5026 (2)	0.2971 (3)	0.07181 (16)	0.0760 (8)
H21	0.4835	0.4084	0.0759	0.091*
C22	0.4544 (2)	0.2473 (4)	−0.00709 (16)	0.1097 (11)
H22A	0.4731	0.1392	−0.0132	0.165*
H22B	0.4767	0.3166	−0.0384	0.165*
H22C	0.3826	0.2543	−0.0200	0.165*
C23	0.6165 (2)	0.2921 (4)	0.09240 (17)	0.1019 (10)
H23A	0.6368	0.1891	0.0804	0.153*
H23B	0.6465	0.3109	0.1442	0.153*
H23C	0.6382	0.3731	0.0656	0.153*
C24	0.25826 (17)	0.2197 (3)	0.21399 (14)	0.0654 (7)
H24	0.2486	0.3334	0.2016	0.079*
C25	0.16130 (18)	0.1335 (4)	0.17186 (16)	0.0937 (9)
H25A	0.1694	0.0209	0.1815	0.141*
H25B	0.1459	0.1524	0.1201	0.141*
H25C	0.1075	0.1729	0.1874	0.141*
C26	0.2778 (2)	0.2039 (3)	0.29605 (15)	0.0852 (8)
H26A	0.2816	0.0929	0.3092	0.128*
H26B	0.2240	0.2535	0.3085	0.128*
H26C	0.3401	0.2555	0.3224	0.128*

	U11	U22	U33	U12	U13	U23
O1	0.0598 (9)	0.0348 (7)	0.0532 (9)	0.0037 (6)	0.0002 (7)	0.0011 (6)
N1	0.0646 (11)	0.0363 (9)	0.0595 (12)	−0.0007 (8)	−0.0018 (9)	0.0003 (8)
N2	0.0653 (11)	0.0372 (9)	0.0587 (12)	−0.0017 (8)	0.0003 (9)	0.0007 (8)
C1	0.0774 (16)	0.0641 (14)	0.0521 (15)	0.0064 (13)	0.0114 (12)	−0.0010 (11)
C2	0.0643 (13)	0.0506 (12)	0.0563 (15)	−0.0018 (10)	0.0138 (11)	−0.0013 (11)
C3	0.0519 (12)	0.0370 (10)	0.0505 (14)	0.0041 (9)	0.0121 (10)	−0.0036 (9)
C4	0.0614 (14)	0.0543 (13)	0.0605 (15)	−0.0038 (11)	0.0155 (12)	−0.0015 (11)
C5	0.0563 (14)	0.0654 (15)	0.0784 (19)	−0.0089 (12)	0.0072 (13)	−0.0137 (13)
C6	0.0710 (16)	0.0656 (15)	0.0588 (17)	0.0075 (13)	−0.0016 (13)	−0.0094 (12)
C7	0.0664 (13)	0.0404 (11)	0.0563 (14)	0.0078 (10)	0.0081 (11)	0.0039 (10)
C8	0.0878 (16)	0.0348 (10)	0.0587 (15)	0.0072 (11)	0.0145 (13)	0.0019 (10)
C9	0.0790 (16)	0.0352 (11)	0.0620 (15)	−0.0052 (10)	0.0157 (13)	−0.0046 (10)
C10	0.0599 (13)	0.0419 (11)	0.0499 (13)	−0.0044 (9)	0.0127 (10)	−0.0039 (9)
C11	0.0489 (11)	0.0346 (10)	0.0489 (13)	−0.0002 (8)	0.0150 (10)	0.0007 (8)
C12	0.0499 (11)	0.0380 (10)	0.0471 (13)	0.0017 (9)	0.0151 (10)	0.0000 (8)
C13	0.0511 (11)	0.0382 (10)	0.0516 (14)	0.0016 (9)	0.0124 (10)	0.0012 (9)
C14	0.0503 (12)	0.0363 (10)	0.0499 (13)	0.0009 (9)	0.0100 (10)	0.0011 (9)
C15	0.0531 (12)	0.0356 (10)	0.0431 (12)	0.0004 (9)	0.0015 (10)	−0.0001 (8)
C16	0.0579 (13)	0.0504 (12)	0.0547 (14)	0.0041 (11)	0.0115 (11)	−0.0023 (10)
C17	0.0661 (14)	0.0667 (14)	0.0645 (16)	0.0174 (12)	0.0169 (12)	0.0064 (12)
C18	0.0709 (15)	0.0567 (13)	0.0616 (16)	0.0210 (12)	0.0072 (13)	0.0125 (11)
C19	0.0735 (15)	0.0501 (12)	0.0541 (15)	0.0063 (11)	0.0128 (12)	0.0103 (10)
C20	0.0558 (12)	0.0428 (11)	0.0486 (13)	0.0022 (9)	0.0062 (10)	−0.0012 (9)
C21	0.0927 (19)	0.0602 (14)	0.086 (2)	0.0058 (13)	0.0440 (16)	0.0081 (13)
C22	0.117 (2)	0.139 (3)	0.069 (2)	0.004 (2)	0.0252 (18)	0.0288 (19)
C23	0.095 (2)	0.127 (3)	0.095 (2)	−0.0228 (19)	0.0463 (18)	−0.0186 (19)
C24	0.0721 (15)	0.0506 (12)	0.0747 (18)	0.0056 (11)	0.0255 (13)	0.0055 (11)
C25	0.0593 (16)	0.127 (2)	0.092 (2)	0.0058 (16)	0.0200 (15)	0.0062 (18)
C26	0.0941 (19)	0.0898 (19)	0.074 (2)	−0.0024 (15)	0.0309 (16)	−0.0057 (15)

O1—C14	1.362 (2)	C15—C20	1.383 (3)
O1—C15	1.416 (2)	C15—C16	1.391 (3)
N1—C14	1.289 (2)	C16—C17	1.386 (3)
N1—N2	1.382 (2)	C16—C21	1.519 (3)
N2—C13	1.311 (2)	C17—C18	1.372 (3)
C1—C6	1.369 (3)	C17—H17	0.9300
C1—C2	1.380 (3)	C18—C19	1.375 (3)
C1—H1	0.9300	C18—H18	0.9300
C2—C3	1.390 (3)	C19—C20	1.392 (3)
C2—H2	0.9300	C19—H19	0.9300
C3—C4	1.379 (3)	C20—C24	1.517 (3)
C3—C13	1.492 (3)	C21—C22	1.505 (4)
C4—C5	1.389 (3)	C21—C23	1.522 (4)
C4—H4	0.9300	C21—H21	0.9800
C5—C6	1.373 (4)	C22—H22A	0.9600
C5—H5	0.9300	C22—H22B	0.9600
C6—H6	0.9300	C22—H22C	0.9600
C7—C8	1.364 (3)	C23—H23A	0.9600
C7—C12	1.412 (3)	C23—H23B	0.9600
C7—H7	0.9300	C23—H23C	0.9600
C8—C9	1.386 (3)	C24—C26	1.518 (4)
C8—H8	0.9300	C24—C25	1.522 (3)
C9—C10	1.364 (3)	C24—H24	0.9800
C9—H9	0.9300	C25—H25A	0.9600
C10—C11	1.403 (3)	C25—H25B	0.9600
C10—H10	0.9300	C25—H25C	0.9600
C11—C12	1.397 (3)	C26—H26A	0.9600
C11—C14	1.430 (3)	C26—H26B	0.9600
C12—C13	1.435 (3)	C26—H26C	0.9600
C14—O1—C15	118.74 (13)	C15—C16—C21	122.17 (19)
C14—N1—N2	118.87 (15)	C18—C17—C16	121.8 (2)
C13—N2—N1	119.92 (15)	C18—C17—H17	119.1
C6—C1—C2	119.8 (2)	C16—C17—H17	119.1
C6—C1—H1	120.1	C17—C18—C19	119.9 (2)
C2—C1—H1	120.1	C17—C18—H18	120.1
C1—C2—C3	120.7 (2)	C19—C18—H18	120.1
C1—C2—H2	119.6	C18—C19—C20	121.4 (2)
C3—C2—H2	119.6	C18—C19—H19	119.3
C4—C3—C2	119.00 (19)	C20—C19—H19	119.3
C4—C3—C13	120.14 (19)	C15—C20—C19	116.5 (2)
C2—C3—C13	120.84 (19)	C15—C20—C24	122.73 (18)
C3—C4—C5	119.9 (2)	C19—C20—C24	120.8 (2)
C3—C4—H4	120.0	C22—C21—C16	111.3 (2)
C5—C4—H4	120.0	C22—C21—C23	110.1 (2)
C6—C5—C4	120.3 (2)	C16—C21—C23	112.9 (2)
C6—C5—H5	119.9	C22—C21—H21	107.4
C4—C5—H5	119.9	C16—C21—H21	107.4
C1—C6—C5	120.3 (2)	C23—C21—H21	107.4
C1—C6—H6	119.9	C21—C22—H22A	109.5
C5—C6—H6	119.9	C21—C22—H22B	109.5
C8—C7—C12	120.4 (2)	H22A—C22—H22B	109.5
C8—C7—H7	119.8	C21—C22—H22C	109.5
C12—C7—H7	119.8	H22A—C22—H22C	109.5
C7—C8—C9	120.84 (19)	H22B—C22—H22C	109.5
C7—C8—H8	119.6	C21—C23—H23A	109.5
C9—C8—H8	119.6	C21—C23—H23B	109.5
C10—C9—C8	120.39 (18)	H23A—C23—H23B	109.5
C10—C9—H9	119.8	C21—C23—H23C	109.5
C8—C9—H9	119.8	H23A—C23—H23C	109.5
C9—C10—C11	119.66 (19)	H23B—C23—H23C	109.5
C9—C10—H10	120.2	C20—C24—C26	112.8 (2)
C11—C10—H10	120.2	C20—C24—C25	111.3 (2)
C12—C11—C10	120.60 (16)	C26—C24—C25	109.8 (2)
C12—C11—C14	115.19 (16)	C20—C24—H24	107.6
C10—C11—C14	124.21 (18)	C26—C24—H24	107.6
C11—C12—C7	118.01 (16)	C25—C24—H24	107.6
C11—C12—C13	117.06 (16)	C24—C25—H25A	109.5
C7—C12—C13	124.90 (18)	C24—C25—H25B	109.5
N2—C13—C12	123.21 (18)	H25A—C25—H25B	109.5
N2—C13—C3	114.73 (16)	C24—C25—H25C	109.5
C12—C13—C3	122.06 (16)	H25A—C25—H25C	109.5
N1—C14—O1	119.47 (16)	H25B—C25—H25C	109.5
N1—C14—C11	125.72 (18)	C24—C26—H26A	109.5
O1—C14—C11	114.81 (16)	C24—C26—H26B	109.5
C20—C15—C16	124.11 (18)	H26A—C26—H26B	109.5
C20—C15—O1	118.68 (18)	C24—C26—H26C	109.5
C16—C15—O1	116.85 (18)	H26A—C26—H26C	109.5
C17—C16—C15	116.3 (2)	H26B—C26—H26C	109.5
C17—C16—C21	121.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···Cg	0.93	2.77	3.624 (2)	154

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C15–C20 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯Cg	0.93	2.77	3.624 (2)	154