4-(4-Benzyl­oxy­phenoxy)­phthalo­nitrile

The title compound, C₂₁H₁₄O₂N₂, consists of two substituted benzene rings and one phthalo­nitrile moiety. The dihedral angle between the first two benzene rings is 62.91 (1)°, and that between the phthalo­nitrile and the central benzene ring is 70.82 (1)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.056
• wR factor = 0.179
• Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         48 Perc.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT157_ALERT_4_C Non-standard Monoclinic Beta Angle less 90 Deg        81.89 Deg.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C1     -   C21      =       1.43 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C6     -   C20      =       1.44 Ang.

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

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

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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 PLUTON (Spek, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

4-(4-Benzyloxyphenoxy)phthalonitrile

Crystal data

C21H14N2O2	F(000) = 680
Mr = 326.36	Dx = 1.309 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4810 reflections
a = 20.149 (3) Å	θ = 1.9–25.0°
b = 10.8606 (8) Å	µ = 0.09 mm^−1
c = 7.6424 (10) Å	T = 293 K
β = 81.892 (11)°	Prismatic, colourless
V = 1655.7 (4) Å^3	0.42 × 0.31 × 0.10 mm
Z = 4

Data collection

Stoe IPDS-2 diffractometer	1505 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.071
Plane graphite monochromator	θmax = 26.0°, θmin = 2.0°
ω scans	h = −24→24
11417 measured reflections	k = −13→12
3163 independent reflections	l = −9→9

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.057	H-atom parameters constrained
wR(F^2) = 0.179	w = 1/[σ^2(Fo^2) + (0.0862P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max = 0.004
3163 reflections	Δρmax = 0.17 e Å^−3
227 parameters	Δρmin = −0.15 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.019 (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
N1	0.78552 (18)	0.7370 (3)	−0.1958 (4)	0.0875 (11)
C20	0.8161 (2)	0.6607 (4)	−0.1425 (5)	0.0679 (10)
C21	0.93288 (19)	0.5808 (4)	−0.3510 (6)	0.0808 (12)
N2	0.9481 (2)	0.6322 (4)	−0.4828 (5)	0.1086 (13)
O2	0.59573 (11)	0.35819 (19)	0.6401 (3)	0.0589 (6)
O1	0.85714 (12)	0.3648 (2)	0.3082 (3)	0.0721 (7)
C12	0.76766 (17)	0.4684 (3)	0.4963 (4)	0.0604 (9)
H12	0.7957	0.5352	0.5074	0.072*
C10	0.66123 (16)	0.3688 (3)	0.5659 (4)	0.0509 (8)
C9	0.68610 (17)	0.2689 (3)	0.4650 (4)	0.0589 (9)
H9	0.6587	0.2009	0.4561	0.071*
C14	0.49343 (16)	0.4253 (3)	0.8001 (4)	0.0510 (8)
C11	0.70231 (16)	0.4691 (3)	0.5829 (4)	0.0569 (8)
H11	0.6862	0.5362	0.6517	0.068*
C6	0.85448 (16)	0.5631 (3)	−0.0784 (4)	0.0585 (9)
C8	0.75032 (17)	0.2686 (3)	0.3780 (4)	0.0611 (9)
H8	0.7665	0.2017	0.3088	0.073*
C15	0.47869 (17)	0.3238 (3)	0.9097 (4)	0.0590 (9)
H15	0.5132	0.2772	0.9452	0.071*
C7	0.79091 (16)	0.3698 (3)	0.3948 (4)	0.0572 (8)
C5	0.83371 (16)	0.5107 (3)	0.0841 (4)	0.0571 (9)
H5	0.7948	0.5380	0.1532	0.069*
C19	0.44165 (17)	0.4937 (3)	0.7532 (4)	0.0608 (9)
H19	0.4509	0.5626	0.6816	0.073*
C17	0.36162 (18)	0.3601 (4)	0.9146 (5)	0.0677 (10)
H17	0.3173	0.3371	0.9504	0.081*
C16	0.41283 (19)	0.2922 (3)	0.9656 (5)	0.0663 (10)
H16	0.4031	0.2242	1.0387	0.080*
C13	0.56478 (16)	0.4594 (3)	0.7404 (4)	0.0573 (8)
H13A	0.5671	0.5331	0.6680	0.069*
H13B	0.5876	0.4754	0.8416	0.069*
C4	0.87118 (16)	0.4172 (3)	0.1437 (4)	0.0560 (8)
C1	0.91191 (17)	0.5206 (3)	−0.1865 (4)	0.0622 (9)
C18	0.37571 (19)	0.4615 (4)	0.8112 (5)	0.0687 (10)
H18	0.3410	0.5093	0.7795	0.082*
C2	0.94789 (18)	0.4243 (4)	−0.1249 (5)	0.0714 (10)
H2	0.9860	0.3944	−0.1950	0.086*
C3	0.92778 (17)	0.3727 (3)	0.0387 (5)	0.0688 (10)
H3	0.9521	0.3082	0.0785	0.083*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.098 (3)	0.078 (2)	0.081 (2)	0.009 (2)	0.0069 (19)	0.0184 (19)
C20	0.074 (2)	0.065 (2)	0.059 (2)	−0.001 (2)	0.0130 (18)	0.004 (2)
C21	0.068 (2)	0.092 (3)	0.075 (3)	−0.004 (2)	0.016 (2)	0.007 (2)
N2	0.107 (3)	0.126 (3)	0.080 (2)	0.001 (2)	0.029 (2)	0.019 (2)
O2	0.0583 (14)	0.0567 (14)	0.0584 (13)	−0.0062 (10)	0.0027 (11)	−0.0121 (11)
O1	0.0570 (14)	0.0856 (17)	0.0707 (16)	0.0069 (12)	0.0014 (12)	0.0168 (14)
C12	0.067 (2)	0.057 (2)	0.056 (2)	−0.0100 (17)	−0.0067 (17)	0.0067 (17)
C10	0.0563 (19)	0.0547 (19)	0.0413 (16)	−0.0038 (15)	−0.0059 (14)	0.0023 (15)
C9	0.067 (2)	0.0553 (19)	0.0518 (19)	−0.0071 (16)	0.0000 (16)	−0.0062 (16)
C14	0.060 (2)	0.0482 (17)	0.0443 (16)	0.0017 (15)	−0.0045 (14)	−0.0056 (15)
C11	0.061 (2)	0.0523 (19)	0.057 (2)	−0.0070 (16)	−0.0072 (16)	0.0015 (16)
C6	0.0549 (19)	0.056 (2)	0.062 (2)	−0.0034 (16)	0.0000 (16)	−0.0012 (17)
C8	0.068 (2)	0.060 (2)	0.055 (2)	0.0034 (18)	−0.0074 (17)	−0.0055 (17)
C15	0.073 (2)	0.0471 (18)	0.055 (2)	0.0025 (16)	−0.0025 (17)	0.0023 (16)
C7	0.0537 (19)	0.067 (2)	0.0499 (18)	0.0016 (17)	−0.0031 (15)	0.0083 (17)
C5	0.0553 (18)	0.060 (2)	0.053 (2)	−0.0018 (16)	0.0056 (16)	−0.0006 (16)
C19	0.073 (2)	0.060 (2)	0.049 (2)	0.0016 (18)	−0.0097 (17)	0.0047 (16)
C17	0.061 (2)	0.082 (3)	0.058 (2)	−0.006 (2)	0.0009 (18)	−0.010 (2)
C16	0.075 (2)	0.056 (2)	0.063 (2)	−0.0073 (19)	0.0058 (19)	−0.0005 (17)
C13	0.066 (2)	0.0502 (19)	0.055 (2)	−0.0019 (15)	−0.0049 (16)	−0.0076 (16)
C4	0.0533 (18)	0.061 (2)	0.0513 (19)	−0.0055 (16)	0.0011 (15)	0.0004 (17)
C1	0.060 (2)	0.071 (2)	0.051 (2)	−0.0102 (18)	0.0059 (17)	−0.0057 (17)
C18	0.064 (2)	0.083 (3)	0.061 (2)	0.0106 (19)	−0.0135 (18)	−0.004 (2)
C2	0.057 (2)	0.086 (3)	0.066 (2)	0.0042 (19)	0.0099 (18)	−0.003 (2)
C3	0.055 (2)	0.068 (2)	0.081 (3)	0.0037 (17)	−0.0007 (19)	0.000 (2)

Geometric parameters (Å, º)

N1—C20	1.142 (5)	C8—C7	1.387 (5)
C20—C6	1.438 (5)	C8—H8	0.9300
C21—N2	1.154 (5)	C15—C16	1.379 (5)
C21—C1	1.427 (5)	C15—H15	0.9300
O2—C10	1.366 (4)	C5—C4	1.380 (4)
O2—C13	1.432 (4)	C5—H5	0.9300
O1—C4	1.373 (4)	C19—C18	1.385 (5)
O1—C7	1.405 (4)	C19—H19	0.9300
C12—C7	1.365 (5)	C17—C18	1.362 (5)
C12—C11	1.388 (5)	C17—C16	1.369 (5)
C12—H12	0.9300	C17—H17	0.9300
C10—C9	1.383 (4)	C16—H16	0.9300
C10—C11	1.385 (4)	C13—H13A	0.9700
C9—C8	1.369 (5)	C13—H13B	0.9700
C9—H9	0.9300	C4—C3	1.386 (4)
C14—C19	1.369 (4)	C1—C2	1.392 (5)
C14—C15	1.391 (4)	C18—H18	0.9300
C14—C13	1.492 (4)	C2—C3	1.378 (5)
C11—H11	0.9300	C2—H2	0.9300
C6—C5	1.377 (4)	C3—H3	0.9300
C6—C1	1.402 (4)
N1—C20—C6	178.9 (4)	C6—C5—H5	120.3
N2—C21—C1	177.8 (5)	C4—C5—H5	120.3
C10—O2—C13	118.7 (2)	C14—C19—C18	120.7 (3)
C4—O1—C7	118.3 (3)	C14—C19—H19	119.6
C7—C12—C11	120.1 (3)	C18—C19—H19	119.6
C7—C12—H12	119.9	C18—C17—C16	119.8 (3)
C11—C12—H12	119.9	C18—C17—H17	120.1
O2—C10—C9	114.7 (3)	C16—C17—H17	120.1
O2—C10—C11	125.6 (3)	C17—C16—C15	120.6 (3)
C9—C10—C11	119.7 (3)	C17—C16—H16	119.7
C8—C9—C10	121.1 (3)	C15—C16—H16	119.7
C8—C9—H9	119.5	O2—C13—C14	107.5 (2)
C10—C9—H9	119.5	O2—C13—H13A	110.2
C19—C14—C15	118.8 (3)	C14—C13—H13A	110.2
C19—C14—C13	121.5 (3)	O2—C13—H13B	110.2
C15—C14—C13	119.7 (3)	C14—C13—H13B	110.2
C10—C11—C12	119.3 (3)	H13A—C13—H13B	108.5
C10—C11—H11	120.3	O1—C4—C5	123.7 (3)
C12—C11—H11	120.3	O1—C4—C3	115.6 (3)
C5—C6—C1	121.1 (3)	C5—C4—C3	120.6 (3)
C5—C6—C20	120.1 (3)	C2—C1—C6	118.3 (3)
C1—C6—C20	118.8 (3)	C2—C1—C21	122.6 (3)
C9—C8—C7	118.8 (3)	C6—C1—C21	119.0 (3)
C9—C8—H8	120.6	C17—C18—C19	120.1 (3)
C7—C8—H8	120.6	C17—C18—H18	119.9
C16—C15—C14	119.9 (3)	C19—C18—H18	119.9
C16—C15—H15	120.1	C3—C2—C1	120.8 (3)
C14—C15—H15	120.1	C3—C2—H2	119.6
C12—C7—C8	121.0 (3)	C1—C2—H2	119.6
C12—C7—O1	121.7 (3)	C2—C3—C4	119.7 (3)
C8—C7—O1	117.3 (3)	C2—C3—H3	120.1
C6—C5—C4	119.4 (3)	C4—C3—H3	120.1
C13—O2—C10—C9	−177.3 (3)	C18—C17—C16—C15	−1.6 (5)
C13—O2—C10—C11	2.0 (5)	C14—C15—C16—C17	−0.1 (5)
O2—C10—C9—C8	177.8 (3)	C10—O2—C13—C14	178.1 (3)
C11—C10—C9—C8	−1.5 (5)	C19—C14—C13—O2	−120.2 (3)
O2—C10—C11—C12	−178.4 (3)	C15—C14—C13—O2	61.5 (4)
C9—C10—C11—C12	0.8 (5)	C7—O1—C4—C5	24.8 (5)
C7—C12—C11—C10	0.3 (5)	C7—O1—C4—C3	−157.1 (3)
C10—C9—C8—C7	1.1 (5)	C6—C5—C4—O1	175.5 (3)
C19—C14—C15—C16	1.4 (5)	C6—C5—C4—C3	−2.6 (5)
C13—C14—C15—C16	179.8 (3)	C5—C6—C1—C2	−0.5 (5)
C11—C12—C7—C8	−0.8 (5)	C20—C6—C1—C2	−178.6 (3)
C11—C12—C7—O1	−178.6 (3)	C5—C6—C1—C21	−177.7 (3)
C9—C8—C7—C12	0.1 (5)	C20—C6—C1—C21	4.2 (5)
C9—C8—C7—O1	178.1 (3)	C16—C17—C18—C19	2.0 (5)
C4—O1—C7—C12	−86.6 (4)	C14—C19—C18—C17	−0.7 (5)
C4—O1—C7—C8	95.4 (4)	C6—C1—C2—C3	−0.4 (5)
C1—C6—C5—C4	2.0 (5)	C21—C1—C2—C3	176.7 (4)
C20—C6—C5—C4	−180.0 (3)	C1—C2—C3—C4	−0.2 (6)
C15—C14—C19—C18	−1.0 (5)	O1—C4—C3—C2	−176.5 (3)
C13—C14—C19—C18	−179.4 (3)	C5—C4—C3—C2	1.7 (5)