4-(2,3-Dimethyl­phen­oxy)phthalonitrile

Ağar, A.

doi:10.1107/S1600536807002255

4-(2,3-Dimethylphenoxy)phthalonitrile

In the title compound, C₁₆H₁₂N₂O, the planes of the 2,3-dimethylphenoxy group and phthalonitrile unit make a dihedral angle of 89.32 (4)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807002255/at2203sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807002255/at2203Isup2.hkl Contains datablock I

CCDC reference: 636120

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Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R factor = 0.035
wR factor = 0.111
Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C1     -   C8      ..       7.24 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C12    -   C13     ..      11.12 su

Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.63 mm
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.57 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C2     -   C3      ..       6.56 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C1     -   C8     ...       1.43 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C2     -   C3     ...       1.43 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          1
            N2  -C2  -C3  -C4     -8.00 11.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          2
            N2  -C2  -C3  -C8     17.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         16
            N1  -C1  -C8  -C7      1.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         17
            N1  -C1  -C8  -C3     17.00  0.00   1.555   1.555   1.555   1.555

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  12 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1999).

4-(2,3-dimethylphenoxy)phthalonitrile top

Crystal data top

C₁₆H₁₂N₂O	F(000) = 1040
M_r = 248.28	D_x = 1.225 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 18432 reflections
a = 13.7432 (9) Å	θ = 1.9–27.2°
b = 9.3259 (5) Å	µ = 0.08 mm⁻¹
c = 21.0744 (15) Å	T = 293 K
β = 94.476 (6)°	Prism, colourless
V = 2692.8 (3) Å³	0.63 × 0.54 × 0.38 mm
Z = 8

Data collection top

Stoe IPDS 2 diffractometer	2645 independent reflections
Radiation source: fine-focus sealed tube	1989 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.0°, θ_min = 1.9°
ω scans	h = −16→16
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −11→11
T_min = 0.901, T_max = 0.984	l = −25→25
18971 measured reflections

Refinement top

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)] = 0.035	H-atom parameters constrained
wR(F²) = 0.111	w = 1/[σ²(F_o²) + (0.0613P)² + 0.229P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
2645 reflections	Δρ_max = 0.12 e Å⁻³
175 parameters	Δρ_min = −0.09 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0056 (8)

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
C1	0.27302 (10)	0.11680 (14)	0.56493 (7)	0.0690 (3)
C2	0.42565 (9)	0.05577 (14)	0.66005 (6)	0.0678 (3)
C3	0.35394 (8)	0.16213 (11)	0.67122 (5)	0.0550 (3)
C4	0.35966 (8)	0.23459 (12)	0.72852 (5)	0.0590 (3)
H4	0.4101	0.2153	0.7593	0.071*
C5	0.28971 (9)	0.33602 (13)	0.73963 (6)	0.0637 (3)
C6	0.21331 (9)	0.36176 (15)	0.69428 (6)	0.0731 (4)
H6	0.1652	0.4277	0.7026	0.088*
C7	0.20810 (9)	0.29126 (14)	0.63756 (6)	0.0695 (3)
H7	0.1570	0.3107	0.6072	0.083*
C8	0.27831 (8)	0.19065 (12)	0.62456 (5)	0.0579 (3)
C9	0.37329 (9)	0.40969 (14)	0.83754 (6)	0.0691 (3)
C10	0.44570 (13)	0.50703 (18)	0.82820 (8)	0.0915 (5)
H10	0.4412	0.5690	0.7935	0.110*
C11	0.52538 (13)	0.5093 (2)	0.87219 (12)	0.1118 (7)
H11	0.5763	0.5731	0.8673	0.134*
C12	0.52938 (13)	0.4179 (3)	0.92290 (10)	0.1073 (7)
H12	0.5835	0.4209	0.9522	0.129*
C13	0.45623 (12)	0.32150 (18)	0.93212 (7)	0.0861 (5)
C14	0.37491 (10)	0.31702 (14)	0.88809 (6)	0.0704 (4)
C15	0.29126 (14)	0.21853 (19)	0.89607 (9)	0.1040 (5)
H15A	0.2437	0.2289	0.8605	0.156*
H15B	0.2620	0.2420	0.9346	0.156*
H15C	0.3142	0.1213	0.8982	0.156*
C16	0.46482 (19)	0.2234 (3)	0.98860 (8)	0.1414 (9)
H16A	0.5272	0.2371	1.0117	0.212*
H16B	0.4589	0.1257	0.9745	0.212*
H16C	0.4139	0.2446	1.0158	0.212*
N1	0.26834 (11)	0.05860 (15)	0.51731 (6)	0.0951 (4)
N2	0.48340 (10)	−0.02824 (16)	0.65194 (7)	0.1012 (5)
O1	0.28954 (7)	0.41345 (12)	0.79451 (5)	0.0876 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0691 (8)	0.0699 (7)	0.0658 (8)	0.0038 (6)	−0.0085 (6)	0.0046 (6)
C2	0.0569 (7)	0.0773 (8)	0.0674 (7)	0.0106 (6)	−0.0069 (5)	−0.0071 (6)
C3	0.0474 (6)	0.0570 (6)	0.0603 (6)	0.0024 (4)	0.0022 (5)	0.0051 (5)
C4	0.0492 (6)	0.0674 (7)	0.0590 (6)	0.0073 (5)	−0.0038 (5)	0.0018 (5)
C5	0.0597 (7)	0.0678 (7)	0.0628 (7)	0.0117 (5)	−0.0008 (5)	−0.0012 (6)
C6	0.0645 (8)	0.0773 (8)	0.0761 (8)	0.0238 (6)	−0.0050 (6)	−0.0002 (7)
C7	0.0605 (7)	0.0747 (8)	0.0705 (8)	0.0128 (6)	−0.0125 (5)	0.0085 (6)
C8	0.0556 (6)	0.0597 (6)	0.0572 (6)	−0.0012 (5)	−0.0025 (5)	0.0068 (5)
C9	0.0660 (7)	0.0754 (8)	0.0655 (7)	0.0143 (6)	0.0027 (6)	−0.0168 (6)
C10	0.0959 (11)	0.0875 (10)	0.0942 (10)	−0.0017 (9)	0.0278 (9)	−0.0121 (8)
C11	0.0801 (11)	0.1244 (15)	0.1335 (17)	−0.0248 (10)	0.0253 (11)	−0.0539 (14)
C12	0.0751 (10)	0.1436 (17)	0.0998 (13)	0.0186 (11)	−0.0146 (9)	−0.0598 (13)
C13	0.0877 (10)	0.0988 (10)	0.0695 (8)	0.0247 (9)	−0.0083 (7)	−0.0273 (8)
C14	0.0738 (8)	0.0704 (7)	0.0670 (7)	0.0094 (6)	0.0044 (6)	−0.0170 (6)
C15	0.1136 (13)	0.0920 (11)	0.1084 (12)	−0.0150 (10)	0.0218 (10)	−0.0133 (10)
C16	0.183 (2)	0.1590 (19)	0.0775 (11)	0.0615 (18)	−0.0182 (12)	−0.0026 (12)
N1	0.1074 (10)	0.1006 (9)	0.0742 (8)	0.0121 (8)	−0.0129 (7)	−0.0117 (7)
N2	0.0834 (8)	0.1136 (10)	0.1038 (10)	0.0408 (8)	−0.0105 (7)	−0.0216 (8)
O1	0.0780 (6)	0.1074 (7)	0.0753 (6)	0.0367 (5)	−0.0081 (5)	−0.0221 (5)

Geometric parameters (Å, º) top

C1—N1	1.1384 (17)	C9—O1	1.4090 (15)
N2—C2	1.1376 (17)	C10—C11	1.379 (3)
C1—C8	1.4298 (18)	C10—H10	0.9300
C2—C3	1.4307 (16)	C11—C12	1.365 (3)
C3—C4	1.3806 (16)	C11—H11	0.9300
C3—C8	1.3994 (14)	C12—C13	1.374 (3)
C4—C5	1.3817 (16)	C12—H12	0.9300
C4—H4	0.9300	C13—C14	1.3964 (19)
C5—O1	1.3636 (15)	C13—C16	1.499 (2)
C5—C6	1.3844 (16)	C14—C15	1.491 (2)
C6—C7	1.3613 (18)	C15—H15A	0.9600
C6—H6	0.9300	C15—H15B	0.9600
C7—C8	1.3884 (17)	C15—H15C	0.9600
C7—H7	0.9300	C16—H16A	0.9600
C9—C14	1.3706 (19)	C16—H16B	0.9600
C9—C10	1.372 (2)	C16—H16C	0.9600

N1—C1—C8	179.55 (15)	C12—C11—C10	119.87 (18)
N2—C2—C3	179.03 (14)	C12—C11—H11	120.1
C4—C3—C8	120.67 (10)	C10—C11—H11	120.1
C4—C3—C2	119.36 (10)	C11—C12—C13	122.30 (15)
C8—C3—C2	119.97 (10)	C11—C12—H12	118.9
C3—C4—C5	119.37 (10)	C13—C12—H12	118.9
C3—C4—H4	120.3	C12—C13—C14	118.83 (16)
C5—C4—H4	120.3	C12—C13—C16	119.91 (18)
O1—C5—C4	123.61 (10)	C14—C13—C16	121.26 (18)
O1—C5—C6	116.25 (10)	C9—C14—C13	117.47 (14)
C4—C5—C6	120.13 (11)	C9—C14—C15	120.68 (13)
C7—C6—C5	120.50 (11)	C13—C14—C15	121.84 (15)
C7—C6—H6	119.8	C14—C15—H15A	109.5
C5—C6—H6	119.8	C14—C15—H15B	109.5
C6—C7—C8	120.66 (11)	H15A—C15—H15B	109.5
C6—C7—H7	119.7	C14—C15—H15C	109.5
C8—C7—H7	119.7	H15A—C15—H15C	109.5
C7—C8—C3	118.64 (11)	H15B—C15—H15C	109.5
C7—C8—C1	120.69 (10)	C13—C16—H16A	109.5
C3—C8—C1	120.67 (11)	C13—C16—H16B	109.5
C14—C9—C10	124.09 (14)	H16A—C16—H16B	109.5
C14—C9—O1	118.61 (13)	C13—C16—H16C	109.5
C10—C9—O1	117.15 (14)	H16A—C16—H16C	109.5
C9—C10—C11	117.43 (18)	H16B—C16—H16C	109.5
C9—C10—H10	121.3	C5—O1—C9	118.51 (9)
C11—C10—H10	121.3

N2—C2—C3—C4	−8 (11)	O1—C9—C10—C11	176.43 (13)
N2—C2—C3—C8	172 (100)	C9—C10—C11—C12	−0.6 (2)
C8—C3—C4—C5	0.08 (18)	C10—C11—C12—C13	0.2 (3)
C2—C3—C4—C5	−179.18 (11)	C11—C12—C13—C14	0.0 (2)
C3—C4—C5—O1	−179.64 (12)	C11—C12—C13—C16	179.81 (16)
C3—C4—C5—C6	1.67 (19)	C10—C9—C14—C13	−0.87 (19)
O1—C5—C6—C7	178.95 (13)	O1—C9—C14—C13	−176.22 (11)
C4—C5—C6—C7	−2.3 (2)	C10—C9—C14—C15	177.52 (13)
C5—C6—C7—C8	1.1 (2)	O1—C9—C14—C15	2.17 (18)
C6—C7—C8—C3	0.67 (19)	C12—C13—C14—C9	0.35 (19)
C6—C7—C8—C1	−179.85 (13)	C16—C13—C14—C9	−179.49 (14)
C4—C3—C8—C7	−1.25 (17)	C12—C13—C14—C15	−178.02 (13)
C2—C3—C8—C7	178.01 (11)	C16—C13—C14—C15	2.1 (2)
C4—C3—C8—C1	179.27 (11)	C4—C5—O1—C9	11.8 (2)
C2—C3—C8—C1	−1.47 (17)	C6—C5—O1—C9	−169.48 (13)
N1—C1—C8—C7	11 (27)	C14—C9—O1—C5	−97.13 (15)
N1—C1—C8—C3	−170 (100)	C10—C9—O1—C5	87.19 (15)
C14—C9—C10—C11	1.0 (2)

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4-(2,3-Dimethyl­phen­oxy)phthalonitrile

Supporting information

Key indicators

checkCIF/PLATON results

4-(2,3-Dimethylphenoxy)phthalonitrile