4-(2-Methoxy­phen­oxy)phthalonitrile

In the title compound, C₁₆H₁₂N₂O₂, the 2-methoxy­phen­oxy and phthalonitrile planes make a dihedral angle of 83.42 (7)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.028
• wR factor = 0.070
• Data-to-parameter ratio = 8.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C11    -   C12     ..       6.09 su
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.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.99
           From the CIF: _reflns_number_total               1463
           Count of symmetry unique reflns         1463
           Completeness (_total/calc)            100.00%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
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
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

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

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Computing details

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) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

4-(2-methoxyphenoxy)phthalonitrile

Crystal data

C15H10N2O2	F(000) = 520
Mr = 250.25	Dx = 1.309 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 16474 reflections
a = 7.790 (6) Å	θ = 3.3–25.1°
b = 8.329 (4) Å	µ = 0.09 mm^−1
c = 19.575 (12) Å	T = 293 K
V = 1270.0 (14) Å^3	Prism, colourless
Z = 4	0.55 × 0.41 × 0.29 mm

Data collection

Stoe IPDS-2 diffractometer	1463 independent reflections
Radiation source: fine-focus sealed tube	1223 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 2.1°
ω scans	h = −9→9
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −10→10
Tmin = 0.971, Tmax = 0.982	l = −24→24
14897 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.070	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0478P)^2] where P = (Fo^2 + 2Fc^2)/3
1463 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.10 e Å^−3
0 restraints	Δρmin = −0.11 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	1.0296 (3)	0.7711 (2)	0.01675 (9)	0.0712 (5)
C2	1.1300 (2)	0.5612 (2)	−0.08818 (9)	0.0614 (4)
C3	1.0497 (2)	0.4982 (2)	−0.02821 (8)	0.0546 (4)
C4	1.0198 (2)	0.33501 (19)	−0.02028 (9)	0.0601 (4)
H4	1.0508	0.2642	−0.0549	0.072*
C5	0.9449 (2)	0.27752 (19)	0.03812 (9)	0.0598 (4)
H5	0.9259	0.1679	0.0430	0.072*
C6	0.8971 (2)	0.38159 (18)	0.09009 (8)	0.0533 (4)
C7	0.9256 (2)	0.54417 (18)	0.08372 (8)	0.0552 (4)
H7	0.8942	0.6140	0.1186	0.066*
C8	1.0013 (2)	0.60235 (18)	0.02491 (8)	0.0539 (4)
C9	0.7957 (2)	0.40616 (19)	0.20357 (8)	0.0583 (4)
C10	0.9197 (3)	0.4083 (2)	0.25368 (9)	0.0703 (5)
H10	1.0208	0.3505	0.2481	0.084*
C11	0.8929 (3)	0.4961 (3)	0.31171 (11)	0.0830 (6)
H11	0.9754	0.4975	0.3460	0.100*
C12	0.7454 (3)	0.5810 (3)	0.31906 (10)	0.0863 (7)
H12	0.7287	0.6417	0.3584	0.104*
C13	0.6191 (3)	0.5792 (3)	0.26916 (11)	0.0784 (6)
H13	0.5189	0.6382	0.2751	0.094*
C14	0.6432 (2)	0.4890 (2)	0.21047 (9)	0.0629 (4)
C15	0.3717 (3)	0.5580 (4)	0.16376 (17)	0.1196 (10)
H15A	0.3124	0.5221	0.2039	0.179*
H15B	0.3026	0.5367	0.1242	0.179*
H15C	0.3930	0.6713	0.1671	0.179*
N2	1.1959 (2)	0.6133 (2)	−0.13535 (9)	0.0802 (5)
O1	0.82276 (17)	0.31185 (14)	0.14566 (6)	0.0674 (3)
O2	0.53138 (18)	0.4745 (2)	0.15787 (7)	0.0867 (4)
N1	1.0539 (4)	0.9050 (2)	0.00946 (10)	0.1101 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0958 (14)	0.0530 (10)	0.0649 (10)	0.0048 (9)	0.0216 (10)	−0.0055 (8)
C2	0.0627 (9)	0.0591 (10)	0.0624 (10)	0.0018 (8)	0.0031 (9)	−0.0086 (9)
C3	0.0516 (8)	0.0543 (8)	0.0578 (9)	0.0031 (7)	−0.0002 (7)	−0.0077 (7)
C4	0.0591 (9)	0.0525 (9)	0.0688 (10)	0.0049 (8)	0.0014 (8)	−0.0135 (8)
C5	0.0618 (9)	0.0437 (8)	0.0738 (10)	0.0022 (7)	0.0002 (8)	−0.0078 (7)
C6	0.0508 (8)	0.0493 (9)	0.0598 (8)	0.0016 (7)	−0.0027 (7)	0.0003 (7)
C7	0.0615 (9)	0.0478 (8)	0.0565 (8)	0.0050 (7)	0.0026 (7)	−0.0058 (7)
C8	0.0575 (9)	0.0468 (8)	0.0572 (8)	0.0051 (7)	0.0013 (8)	−0.0031 (7)
C9	0.0661 (9)	0.0534 (9)	0.0555 (9)	−0.0068 (8)	0.0024 (8)	0.0047 (7)
C10	0.0651 (10)	0.0720 (11)	0.0736 (11)	−0.0038 (9)	−0.0027 (9)	0.0076 (9)
C11	0.0855 (14)	0.0960 (15)	0.0673 (11)	−0.0145 (13)	−0.0071 (11)	0.0013 (11)
C12	0.1053 (18)	0.0939 (15)	0.0596 (11)	−0.0192 (15)	0.0165 (11)	−0.0103 (10)
C13	0.0731 (12)	0.0808 (12)	0.0812 (12)	0.0035 (11)	0.0237 (11)	0.0027 (11)
C14	0.0597 (9)	0.0657 (10)	0.0633 (10)	−0.0011 (9)	0.0019 (8)	0.0088 (8)
C15	0.0652 (13)	0.144 (2)	0.150 (2)	0.0208 (15)	−0.0129 (16)	0.019 (2)
N2	0.0851 (10)	0.0823 (11)	0.0732 (10)	−0.0044 (10)	0.0120 (9)	−0.0043 (8)
O1	0.0842 (8)	0.0513 (6)	0.0667 (7)	−0.0048 (6)	0.0091 (6)	0.0000 (5)
O2	0.0702 (8)	0.1016 (10)	0.0882 (9)	0.0069 (8)	−0.0142 (7)	0.0062 (8)
N1	0.180 (2)	0.0504 (9)	0.0994 (12)	−0.0005 (12)	0.0579 (15)	−0.0047 (9)

Geometric parameters (Å, º)

C1—N1	1.140 (2)	C9—C14	1.380 (3)
C1—C8	1.432 (3)	C9—O1	1.395 (2)
C2—N2	1.142 (2)	C10—C11	1.367 (3)
C2—C3	1.430 (3)	C10—H10	0.9300
C3—C4	1.388 (3)	C11—C12	1.357 (3)
C3—C8	1.406 (2)	C11—H11	0.9300
C4—C5	1.370 (3)	C12—C13	1.386 (3)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.387 (2)	C13—C14	1.386 (3)
C5—H5	0.9300	C13—H13	0.9300
C6—O1	1.363 (2)	C14—O2	1.354 (2)
C6—C7	1.378 (2)	C15—O2	1.430 (3)
C7—C8	1.381 (2)	C15—H15A	0.9600
C7—H7	0.9300	C15—H15B	0.9600
C9—C10	1.377 (3)	C15—H15C	0.9600
N1—C1—C8	178.9 (2)	C11—C10—C9	119.47 (19)
N2—C2—C3	178.75 (19)	C11—C10—H10	120.3
C4—C3—C8	118.47 (15)	C9—C10—H10	120.3
C4—C3—C2	121.64 (15)	C12—C11—C10	119.8 (2)
C8—C3—C2	119.89 (15)	C12—C11—H11	120.1
C5—C4—C3	120.48 (15)	C10—C11—H11	120.1
C5—C4—H4	119.8	C11—C12—C13	121.36 (19)
C3—C4—H4	119.8	C11—C12—H12	119.3
C4—C5—C6	120.51 (15)	C13—C12—H12	119.3
C4—C5—H5	119.7	C14—C13—C12	119.6 (2)
C6—C5—H5	119.7	C14—C13—H13	120.2
O1—C6—C7	124.03 (15)	C12—C13—H13	120.2
O1—C6—C5	115.66 (14)	O2—C14—C9	115.75 (16)
C7—C6—C5	120.31 (16)	O2—C14—C13	126.32 (18)
C6—C7—C8	119.26 (15)	C9—C14—C13	117.93 (17)
C6—C7—H7	120.4	O2—C15—H15A	109.5
C8—C7—H7	120.4	O2—C15—H15B	109.5
C7—C8—C3	120.97 (15)	H15A—C15—H15B	109.5
C7—C8—C1	120.21 (14)	O2—C15—H15C	109.5
C3—C8—C1	118.82 (15)	H15A—C15—H15C	109.5
C10—C9—C14	121.84 (17)	H15B—C15—H15C	109.5
C10—C9—O1	118.68 (16)	C6—O1—C9	118.23 (12)
C14—C9—O1	119.42 (15)	C14—O2—C15	117.04 (19)