Propyl 4-(3,4-di­cyano­phenoxy)­benzoate

The title compound, C₁₈H₁₄N₂O₃, a phthalo­nitrile derivative, contains two aromatic rings, one of which carries two cyano groups. The crystal structure is stabilized by one intramol­ecular C—H...O and two intermolecular C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.061
• wR factor = 0.153
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT026_ALERT_3_A Ratio Observed / Unique Reflections too Low ....         29 Perc.

Alert level B
PLAT411_ALERT_2_B Short Inter H...H Contact  H11    ..  H11     ..       2.06 Ang.

Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.80 mm
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O3
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C10
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C11
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C13
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C12
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C15
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C17A
PLAT301_ALERT_3_C Main Residue  Disorder .........................      12.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C1     -   C3     ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C2     -   C4     ...       1.43 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      19.70 Deg.
              C16A -O3   -C16B    1.555   1.555   1.555

   1 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  14 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
  12 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   0 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-RED32 (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, 1997).

Propyl 4-(3,4-dicyanophenoxy)benzoate

Crystal data

C18H14N2O3	F(000) = 640
Mr = 306.31	Dx = 1.257 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3195 reflections
a = 5.0843 (9) Å	θ = 1.4–21.3°
b = 29.440 (5) Å	µ = 0.09 mm^−1
c = 10.823 (2) Å	T = 293 K
β = 92.419 (16)°	Needle, colourless
V = 1618.5 (5) Å^3	0.80 × 0.35 × 0.09 mm
Z = 4

Data collection

Stoe IPDS-2 diffractometer	868 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.096
Graphite monochromator	θmax = 25.5°, θmin = 1.4°
Detector resolution: 6.67 pixels mm^-1	h = −5→6
ω scans	k = −35→35
10034 measured reflections	l = −13→13
3009 independent reflections

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)] = 0.061	H-atom parameters constrained
wR(F^2) = 0.153	w = 1/[σ^2(Fo^2) + (0.0483P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.81	(Δ/σ)max < 0.001
3009 reflections	Δρmax = 0.23 e Å^−3
231 parameters	Δρmin = −0.16 e Å^−3
262 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: 0.0129 (17)

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	Occ. (<1)
O1	0.3641 (5)	0.36397 (8)	0.8101 (3)	0.1392 (10)
O2	0.0825 (6)	0.57261 (9)	0.8801 (3)	0.1521 (12)
O3	−0.2105 (7)	0.55220 (8)	0.7352 (3)	0.1500 (11)
N1	−0.1601 (8)	0.18313 (11)	1.0819 (4)	0.1644 (16)
N2	−0.3756 (8)	0.30476 (11)	1.1820 (4)	0.1445 (14)
C1	−0.0704 (9)	0.21427 (14)	1.0356 (4)	0.1240 (14)
C2	−0.2271 (10)	0.30158 (12)	1.1057 (4)	0.1112 (13)
C3	0.0398 (8)	0.25337 (10)	0.9768 (4)	0.1019 (11)
C4	−0.0413 (7)	0.29661 (11)	1.0113 (3)	0.0980 (10)
C5	0.0597 (7)	0.33489 (11)	0.9562 (3)	0.1007 (10)
H5	0.0060	0.3638	0.9788	0.121*
C6	0.2412 (8)	0.32896 (12)	0.8674 (4)	0.1054 (11)
C7	0.3279 (7)	0.28609 (13)	0.8325 (3)	0.1148 (12)
H7	0.4541	0.2830	0.7733	0.138*
C8	0.2228 (8)	0.24825 (12)	0.8873 (4)	0.1153 (12)
H8	0.2753	0.2193	0.8640	0.138*
C9	0.2581 (11)	0.40800 (18)	0.8185 (5)	0.13923 (8)
C10	0.3781 (11)	0.43966 (17)	0.8860 (5)	0.171 (2)
H10	0.5261	0.4327	0.9358	0.205*
C11	0.2785 (10)	0.48421 (13)	0.8813 (5)	0.1601 (17)
H11	0.3617	0.5064	0.9301	0.192*
C12	0.0713 (9)	0.49588 (13)	0.8103 (4)	0.11635 (7)
C13	−0.0495 (9)	0.46318 (14)	0.7412 (4)	0.1510 (16)
H13	−0.1977	0.4699	0.6912	0.181*
C14	0.0552 (11)	0.41801 (12)	0.7466 (5)	0.1524 (17)
H14	−0.0236	0.3954	0.6977	0.183*
C15	−0.0178 (10)	0.54405 (13)	0.8138 (4)	0.1116 (12)
C16A	−0.357 (4)	0.5952 (8)	0.7297 (17)	0.142 (5)	0.526 (17)
H16A	−0.4716	0.5972	0.7988	0.170*	0.526 (17)
H16B	−0.2348	0.6206	0.7348	0.170*	0.526 (17)
C17A	−0.509 (4)	0.5971 (5)	0.6154 (15)	0.151 (5)	0.526 (17)
H17A	−0.6761	0.6091	0.6412	0.182*	0.526 (17)
H17B	−0.4281	0.6221	0.5727	0.182*	0.526 (17)
C18A	−0.572 (4)	0.5738 (5)	0.5368 (18)	0.202 (6)	0.526 (17)
H18A	−0.6672	0.5908	0.4740	0.302*	0.526 (17)
H18B	−0.6832	0.5502	0.5671	0.302*	0.526 (17)
H18C	−0.4192	0.5604	0.5026	0.302*	0.526 (17)
C16B	−0.267 (5)	0.6021 (8)	0.7224 (19)	0.143 (5)	0.474 (17)
H16C	−0.4042	0.6107	0.7773	0.172*	0.474 (17)
H16D	−0.1097	0.6194	0.7453	0.172*	0.474 (17)
C17B	−0.349 (4)	0.6120 (5)	0.5969 (18)	0.160 (5)	0.474 (17)
H17C	−0.5115	0.6286	0.6055	0.191*	0.474 (17)
H17D	−0.2217	0.6344	0.5724	0.191*	0.474 (17)
C18B	−0.388 (5)	0.5916 (6)	0.5092 (14)	0.176 (7)	0.474 (17)
H18D	−0.4372	0.6118	0.4425	0.265*	0.474 (17)
H18E	−0.5284	0.5705	0.5214	0.265*	0.474 (17)
H18F	−0.2319	0.5753	0.4894	0.265*	0.474 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.152 (2)	0.0873 (16)	0.184 (3)	0.0217 (16)	0.0719 (19)	0.0083 (16)
O2	0.192 (3)	0.0918 (16)	0.171 (3)	0.0132 (18)	−0.016 (2)	−0.0311 (18)
O3	0.179 (3)	0.0914 (18)	0.177 (3)	0.0252 (17)	−0.032 (2)	−0.0117 (17)
N1	0.202 (4)	0.089 (2)	0.203 (4)	−0.011 (2)	0.024 (3)	0.012 (2)
N2	0.172 (4)	0.105 (2)	0.161 (3)	0.003 (2)	0.056 (3)	0.009 (2)
C1	0.144 (4)	0.080 (2)	0.148 (4)	0.010 (3)	0.005 (3)	−0.006 (3)
C2	0.128 (4)	0.084 (2)	0.123 (4)	0.004 (2)	0.021 (3)	0.000 (2)
C3	0.118 (3)	0.068 (2)	0.121 (3)	0.008 (2)	0.011 (2)	0.005 (2)
C4	0.106 (3)	0.080 (2)	0.109 (3)	0.006 (2)	0.017 (2)	0.002 (2)
C5	0.109 (3)	0.078 (2)	0.117 (3)	0.007 (2)	0.030 (2)	−0.002 (2)
C6	0.112 (3)	0.078 (2)	0.128 (3)	0.007 (2)	0.027 (2)	0.008 (2)
C7	0.127 (3)	0.087 (2)	0.132 (3)	0.022 (2)	0.032 (2)	−0.010 (2)
C8	0.133 (3)	0.082 (2)	0.133 (3)	0.013 (2)	0.015 (3)	−0.009 (2)
C9	0.150	0.150	0.120	0.016 (4)	0.033 (3)	0.012 (3)
C10	0.202 (5)	0.124 (3)	0.182 (4)	0.031 (3)	−0.044 (4)	−0.021 (3)
C11	0.195 (4)	0.090 (3)	0.192 (4)	0.023 (3)	−0.031 (4)	−0.030 (3)
C12	0.120	0.100	0.130	0.008 (3)	0.017 (2)	0.009 (2)
C13	0.164 (4)	0.099 (3)	0.187 (4)	0.001 (3)	−0.038 (3)	−0.034 (3)
C14	0.196 (5)	0.076 (3)	0.185 (4)	−0.010 (3)	0.009 (3)	−0.036 (3)
C15	0.128 (4)	0.087 (3)	0.121 (4)	0.009 (2)	0.015 (3)	0.004 (2)
C16A	0.168 (11)	0.086 (8)	0.170 (7)	0.020 (7)	−0.001 (7)	−0.008 (6)
C17A	0.174 (11)	0.092 (7)	0.186 (9)	0.025 (7)	−0.013 (8)	0.007 (7)
C18A	0.228 (14)	0.121 (9)	0.249 (14)	−0.027 (8)	−0.076 (11)	−0.027 (9)
C16B	0.164 (11)	0.070 (7)	0.190 (8)	0.021 (8)	−0.040 (8)	−0.020 (6)
C17B	0.180 (12)	0.096 (8)	0.200 (9)	−0.012 (7)	−0.034 (9)	0.000 (8)
C18B	0.254 (18)	0.127 (11)	0.150 (9)	0.042 (11)	0.027 (11)	−0.018 (8)

Geometric parameters (Å, º)

O1—C6	1.367 (4)	C11—H11	0.9300
O1—C9	1.408 (5)	C12—C13	1.351 (5)
O2—C15	1.204 (4)	C12—C15	1.490 (5)
O3—C15	1.293 (4)	C13—C14	1.433 (5)
O3—C16A	1.47 (2)	C13—H13	0.9300
O3—C16B	1.50 (3)	C14—H14	0.9300
N1—C1	1.148 (4)	C16A—C17A	1.433 (11)
N2—C2	1.146 (5)	C16A—H16A	0.9700
C1—C3	1.440 (5)	C16A—H16B	0.9700
C2—C4	1.428 (5)	C17A—C18A	1.129 (11)
C3—C8	1.379 (5)	C17A—H17A	0.9700
C3—C4	1.394 (4)	C17A—H17B	0.9700
C4—C5	1.384 (4)	C18A—H18A	0.9600
C5—C6	1.371 (4)	C18A—H18B	0.9600
C5—H5	0.9300	C18A—H18C	0.9600
C6—C7	1.394 (4)	C16B—C17B	1.433 (13)
C7—C8	1.380 (5)	C16B—H16C	0.9700
C7—H7	0.9300	C16B—H16D	0.9700
C8—H8	0.9300	C17B—C18B	1.133 (11)
C9—C14	1.300 (5)	C17B—H17C	0.9700
C9—C10	1.317 (6)	C17B—H17D	0.9700
C10—C11	1.406 (5)	C18B—H18D	0.9600
C10—H10	0.9300	C18B—H18E	0.9600
C11—C12	1.323 (5)	C18B—H18F	0.9600
C6—O1—C9	118.8 (3)	C13—C14—H14	119.4
C15—O3—C16A	123.7 (8)	O2—C15—O3	123.5 (4)
C15—O3—C16B	112.2 (8)	O2—C15—C12	123.9 (5)
C16A—O3—C16B	19.7 (15)	O3—C15—C12	112.5 (4)
N1—C1—C3	179.5 (5)	C17A—C16A—O3	108.9 (13)
N2—C2—C4	178.8 (4)	C17A—C16A—H16A	109.9
C8—C3—C4	120.2 (4)	O3—C16A—H16A	109.9
C8—C3—C1	120.6 (3)	C17A—C16A—H16B	109.9
C4—C3—C1	119.1 (4)	O3—C16A—H16B	109.9
C5—C4—C3	120.6 (4)	H16A—C16A—H16B	108.3
C5—C4—C2	119.6 (3)	C18A—C17A—C16A	138.8 (14)
C3—C4—C2	119.8 (4)	C18A—C17A—H17A	102.4
C6—C5—C4	118.1 (3)	C16A—C17A—H17A	102.4
C6—C5—H5	121.0	C18A—C17A—H17B	102.4
C4—C5—H5	121.0	C16A—C17A—H17B	102.4
O1—C6—C5	123.8 (3)	H17A—C17A—H17B	104.9
O1—C6—C7	113.8 (4)	C17A—C18A—H18A	109.5
C5—C6—C7	122.3 (3)	C17A—C18A—H18B	109.5
C8—C7—C6	118.8 (4)	H18A—C18A—H18B	109.5
C8—C7—H7	120.6	C17A—C18A—H18C	109.5
C6—C7—H7	120.6	H18A—C18A—H18C	109.5
C3—C8—C7	119.9 (4)	H18B—C18A—H18C	109.5
C3—C8—H8	120.0	C17B—C16B—O3	109.4 (14)
C7—C8—H8	120.0	C17B—C16B—H16C	109.8
C14—C9—C10	120.6 (5)	O3—C16B—H16C	109.8
C14—C9—O1	117.8 (5)	C17B—C16B—H16D	109.8
C10—C9—O1	121.2 (5)	O3—C16B—H16D	109.8
C9—C10—C11	118.9 (5)	H16C—C16B—H16D	108.2
C9—C10—H10	120.6	C18B—C17B—C16B	136.1 (15)
C11—C10—H10	120.6	C18B—C17B—H17C	103.1
C12—C11—C10	122.7 (4)	C16B—C17B—H17C	103.1
C12—C11—H11	118.7	C18B—C17B—H17D	103.1
C10—C11—H11	118.7	C16B—C17B—H17D	103.1
C11—C12—C13	118.0 (4)	H17C—C17B—H17D	105.1
C11—C12—C15	117.9 (4)	C17B—C18B—H18D	109.5
C13—C12—C15	124.1 (5)	C17B—C18B—H18E	109.5
C12—C13—C14	118.7 (4)	H18D—C18B—H18E	109.5
C12—C13—H13	120.7	C17B—C18B—H18F	109.5
C14—C13—H13	120.7	H18D—C18B—H18F	109.5
C9—C14—C13	121.3 (5)	H18E—C18B—H18F	109.5
C9—C14—H14	119.4
C8—C3—C4—C5	0.2 (5)	C10—C11—C12—C15	179.5 (4)
C1—C3—C4—C5	−179.7 (3)	C11—C12—C13—C14	−1.1 (7)
C8—C3—C4—C2	−178.8 (4)	C15—C12—C13—C14	−179.7 (4)
C1—C3—C4—C2	1.3 (5)	C10—C9—C14—C13	−2.0 (8)
C3—C4—C5—C6	−0.1 (5)	O1—C9—C14—C13	−174.2 (4)
C2—C4—C5—C6	178.9 (3)	C12—C13—C14—C9	1.7 (7)
C9—O1—C6—C5	−16.0 (6)	C16A—O3—C15—O2	−9.5 (12)
C9—O1—C6—C7	167.4 (4)	C16B—O3—C15—O2	8.7 (11)
C4—C5—C6—O1	−177.0 (3)	C16A—O3—C15—C12	172.3 (10)
C4—C5—C6—C7	−0.7 (5)	C16B—O3—C15—C12	−169.5 (10)
O1—C6—C7—C8	178.1 (3)	C11—C12—C15—O2	−2.3 (6)
C5—C6—C7—C8	1.5 (6)	C13—C12—C15—O2	176.2 (4)
C4—C3—C8—C7	0.6 (6)	C11—C12—C15—O3	175.8 (4)
C1—C3—C8—C7	−179.6 (3)	C13—C12—C15—O3	−5.7 (6)
C6—C7—C8—C3	−1.4 (6)	C15—O3—C16A—C17A	166.0 (10)
C6—O1—C9—C14	−79.0 (5)	C16B—O3—C16A—C17A	107 (5)
C6—O1—C9—C10	108.9 (5)	O3—C16A—C17A—C18A	12 (4)
C14—C9—C10—C11	1.7 (8)	C15—O3—C16B—C17B	145.3 (12)
O1—C9—C10—C11	173.6 (4)	C16A—O3—C16B—C17B	−85 (4)
C9—C10—C11—C12	−1.2 (8)	O3—C16B—C17B—C18B	3 (4)
C10—C11—C12—C13	0.9 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O2	0.93	2.46	2.786 (5)	101
C5—H5···O2^i	0.93	2.47	3.345 (4)	157
C16A—H16A···O2^ii	0.97	2.57	3.41 (2)	145

Symmetry codes: (i) −x, −y+1, −z+2; (ii) x−1, y, z.