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The title phthalonitrile derivative, C22H13ClN2O3, contains three aromatic rings, which are not coplanar. The crystal structure is stabilized by inter­molecular C—H...N contacts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805016648/jh6007sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805016648/jh6007Isup2.hkl
Contains datablock I

CCDC reference: 274453

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.037
  • wR factor = 0.105
  • Data-to-parameter ratio = 10.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT230_ALERT_2_C Hirshfeld Test Diff for C7 - C8 .. 5.07 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17 PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C17 -C22 1.37 Ang. 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 - C8 ... 1.45 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2 - C3 ... 1.44 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 26.00 From the CIF: _reflns_number_total 3213 Count of symmetry unique reflns 2013 Completeness (_total/calc) 159.61% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1200 Fraction of Friedel pairs measured 0.596 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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, 1999).

Benzyl 2-(2-chloro-4,5-dicyanophenoxy)benzoate top
Crystal data top
C22H13ClN2O3F(000) = 400
Mr = 388.79Dx = 1.360 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 5493 reflections
a = 8.124 (1) Åθ = 2.5–27.9°
b = 7.2832 (5) ŵ = 0.23 mm1
c = 16.3599 (19) ÅT = 293 K
β = 101.298 (9)°Prism, colourless
V = 949.24 (17) Å30.36 × 0.31 × 0.26 mm
Z = 2
Data collection top
Stoe IPDS-II
diffractometer
3213 independent reflections
Radiation source: fine-focus sealed tube2127 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.055
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 2.5°
ω scansh = 1010
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 87
Tmin = 0.936, Tmax = 0.964l = 2019
5547 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.037 w = 1/[σ2(Fo2) + (0.0587P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.105(Δ/σ)max < 0.001
S = 0.92Δρmax = 0.13 e Å3
3213 reflectionsΔρmin = 0.14 e Å3
298 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.017 (3)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 1200 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.01 (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
xyzUiso*/Ueq
C10.0345 (5)0.1200 (7)0.6007 (2)0.0871 (11)
C20.0524 (4)0.2170 (6)0.7706 (2)0.0673 (9)
C30.1205 (3)0.0452 (5)0.74903 (18)0.0572 (8)
C40.1930 (3)0.0726 (5)0.81221 (18)0.0533 (7)
C50.2533 (3)0.2415 (5)0.79352 (16)0.0510 (7)
C60.2455 (4)0.2878 (5)0.71039 (18)0.0613 (8)
C70.1747 (4)0.1695 (7)0.6470 (2)0.0729 (10)
C80.1113 (4)0.0036 (6)0.66625 (18)0.0655 (8)
C90.3427 (4)0.3157 (4)0.93561 (18)0.0524 (7)
C100.2066 (4)0.3226 (5)0.9735 (2)0.0651 (9)
C110.2279 (6)0.2767 (5)1.0570 (2)0.0772 (10)
C120.3804 (6)0.2334 (5)1.1007 (2)0.0766 (10)
C130.5186 (5)0.2359 (5)1.0638 (2)0.0645 (9)
C140.5021 (4)0.2753 (4)0.97953 (18)0.0525 (7)
C150.6564 (4)0.2731 (4)0.9433 (2)0.0604 (8)
C160.7717 (5)0.2304 (7)0.8228 (3)0.0799 (11)
C170.7136 (4)0.1848 (5)0.7331 (2)0.0710 (10)
C180.7504 (6)0.2994 (8)0.6728 (3)0.0958 (13)
C190.7047 (8)0.2544 (12)0.5889 (3)0.121 (2)
C200.6215 (7)0.0979 (12)0.5655 (3)0.127 (2)
H200.59030.06750.50930.153*
C210.5830 (8)0.0166 (11)0.6257 (4)0.1204 (17)
C220.6288 (6)0.0257 (7)0.7070 (3)0.0981 (12)
H220.60230.05490.74650.118*
Cl10.32739 (12)0.49633 (15)0.68676 (6)0.0856 (3)
N10.0250 (6)0.2214 (7)0.5508 (2)0.1213 (15)
N20.0018 (5)0.3505 (6)0.7900 (2)0.0931 (10)
O10.3210 (2)0.3670 (3)0.85151 (12)0.0560 (5)
O20.7947 (3)0.3007 (4)0.98418 (16)0.0825 (7)
O30.6261 (2)0.2332 (3)0.86204 (13)0.0653 (6)
H40.205 (3)0.026 (4)0.8735 (18)0.052 (7)*
H70.167 (4)0.212 (5)0.593 (2)0.072 (10)*
H100.103 (5)0.348 (5)0.943 (2)0.076 (11)*
H110.125 (4)0.287 (5)1.076 (2)0.064 (9)*
H120.414 (5)0.186 (6)1.164 (3)0.107 (13)*
H130.624 (4)0.214 (5)1.090 (2)0.072 (11)*
H16A0.849 (7)0.159 (8)0.859 (3)0.135 (19)*
H16B0.832 (5)0.358 (6)0.832 (2)0.090 (12)*
H180.796 (5)0.403 (6)0.686 (3)0.091 (15)*
H190.745 (6)0.350 (8)0.557 (4)0.137 (18)*
H210.525 (7)0.124 (9)0.613 (4)0.13 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.098 (3)0.106 (3)0.051 (2)0.016 (2)0.0006 (19)0.019 (2)
C20.0674 (18)0.083 (3)0.0531 (18)0.0046 (19)0.0147 (15)0.0214 (19)
C30.0513 (15)0.072 (2)0.0469 (16)0.0081 (15)0.0065 (12)0.0087 (16)
C40.0530 (16)0.065 (2)0.0400 (16)0.0047 (14)0.0045 (13)0.0009 (16)
C50.0462 (14)0.066 (2)0.0391 (15)0.0108 (14)0.0035 (11)0.0002 (15)
C60.0616 (16)0.074 (2)0.0487 (18)0.0124 (16)0.0108 (14)0.0120 (17)
C70.078 (2)0.100 (3)0.0405 (19)0.023 (2)0.0097 (16)0.004 (2)
C80.0694 (18)0.083 (2)0.0405 (16)0.009 (2)0.0032 (13)0.0123 (18)
C90.0635 (17)0.0475 (17)0.0448 (16)0.0054 (13)0.0075 (13)0.0024 (14)
C100.069 (2)0.068 (2)0.059 (2)0.0034 (17)0.0142 (16)0.0139 (17)
C110.099 (3)0.076 (3)0.064 (2)0.009 (2)0.035 (2)0.015 (2)
C120.123 (3)0.061 (2)0.0483 (19)0.007 (2)0.022 (2)0.0070 (19)
C130.091 (2)0.0438 (19)0.0513 (18)0.0005 (17)0.0030 (17)0.0033 (16)
C140.0629 (16)0.0409 (17)0.0498 (16)0.0038 (13)0.0015 (13)0.0023 (14)
C150.0645 (18)0.0494 (19)0.063 (2)0.0003 (16)0.0028 (15)0.0026 (17)
C160.0596 (19)0.105 (3)0.077 (2)0.003 (2)0.0191 (17)0.004 (3)
C170.0604 (18)0.082 (3)0.075 (2)0.0103 (17)0.0226 (17)0.009 (2)
C180.091 (3)0.101 (4)0.101 (4)0.009 (3)0.032 (2)0.008 (3)
C190.119 (4)0.169 (6)0.083 (4)0.005 (4)0.039 (3)0.027 (4)
C200.123 (4)0.181 (7)0.079 (3)0.018 (4)0.025 (3)0.014 (4)
C210.145 (5)0.122 (5)0.092 (4)0.010 (4)0.019 (3)0.016 (4)
C220.123 (3)0.094 (3)0.077 (3)0.011 (3)0.019 (2)0.000 (3)
Cl10.1015 (7)0.0872 (7)0.0726 (6)0.0110 (6)0.0280 (5)0.0267 (5)
N10.155 (3)0.133 (4)0.064 (2)0.015 (3)0.010 (2)0.034 (3)
N20.105 (2)0.095 (3)0.086 (2)0.023 (2)0.0343 (19)0.024 (2)
O10.0606 (11)0.0594 (14)0.0449 (11)0.0024 (9)0.0023 (9)0.0026 (10)
O20.0595 (13)0.0963 (19)0.0815 (16)0.0055 (12)0.0113 (11)0.0041 (14)
O30.0553 (11)0.0771 (16)0.0637 (13)0.0021 (11)0.0121 (10)0.0080 (12)
Geometric parameters (Å, º) top
C1—N11.136 (5)C12—H121.07 (4)
C1—C81.445 (6)C13—C141.390 (5)
C2—N21.137 (5)C13—H130.89 (3)
C2—C31.440 (6)C14—C151.488 (4)
C3—C41.383 (4)C15—O21.206 (4)
C3—C81.388 (4)C15—O31.336 (4)
C4—C51.380 (4)C16—O31.452 (4)
C4—H41.04 (3)C16—C171.488 (5)
C5—O11.354 (4)C16—H16A0.93 (6)
C5—C61.391 (4)C16—H16B1.05 (4)
C6—C71.384 (5)C17—C181.370 (6)
C6—Cl11.732 (4)C17—C221.373 (6)
C7—C81.374 (6)C18—C191.389 (8)
C7—H70.93 (4)C18—H180.85 (4)
C9—C101.371 (4)C19—C201.343 (9)
C9—C141.384 (4)C19—H190.97 (6)
C9—O11.403 (3)C20—C211.373 (9)
C10—C111.383 (5)C20—H200.9300
C10—H100.91 (4)C21—C221.344 (7)
C11—C121.342 (6)C21—H210.92 (6)
C11—H110.95 (3)C22—H220.9300
C12—C131.375 (6)
N1—C1—C8177.9 (5)C14—C13—H13114 (2)
N2—C2—C3177.9 (4)C9—C14—C13117.3 (3)
C4—C3—C8120.3 (3)C9—C14—C15124.8 (3)
C4—C3—C2118.9 (3)C13—C14—C15117.9 (3)
C8—C3—C2120.8 (3)O2—C15—O3123.9 (3)
C5—C4—C3120.3 (3)O2—C15—C14122.9 (3)
C5—C4—H4122.0 (17)O3—C15—C14113.2 (2)
C3—C4—H4117.6 (17)O3—C16—C17108.1 (3)
O1—C5—C4124.0 (2)O3—C16—H16A103 (3)
O1—C5—C6117.1 (3)C17—C16—H16A124 (3)
C4—C5—C6118.9 (3)O3—C16—H16B109 (2)
C7—C6—C5121.0 (3)C17—C16—H16B113 (2)
C7—C6—Cl1120.0 (3)H16A—C16—H16B99 (4)
C5—C6—Cl1119.0 (3)C18—C17—C22117.2 (4)
C8—C7—C6119.6 (3)C18—C17—C16120.2 (4)
C8—C7—H7123 (2)C22—C17—C16122.6 (4)
C6—C7—H7117 (2)C17—C18—C19121.0 (6)
C7—C8—C3119.9 (3)C17—C18—H18120 (3)
C7—C8—C1120.2 (3)C19—C18—H18119 (3)
C3—C8—C1119.9 (4)C20—C19—C18120.3 (6)
C10—C9—C14121.9 (3)C20—C19—H19131 (3)
C10—C9—O1118.4 (3)C18—C19—H19108 (3)
C14—C9—O1119.4 (2)C19—C20—C21118.9 (6)
C9—C10—C11118.8 (4)C19—C20—H20120.5
C9—C10—H10120 (2)C21—C20—H20120.5
C11—C10—H10121 (2)C22—C21—C20120.9 (7)
C12—C11—C10120.5 (4)C22—C21—H21117 (4)
C12—C11—H11129 (2)C20—C21—H21122 (4)
C10—C11—H11111 (2)C21—C22—C17121.8 (5)
C11—C12—C13120.7 (4)C21—C22—H22119.1
C11—C12—H12129 (2)C17—C22—H22119.1
C13—C12—H12110 (2)C5—O1—C9117.6 (2)
C12—C13—C14120.7 (4)C15—O3—C16115.9 (2)
C12—C13—H13125 (2)
C8—C3—C4—C51.5 (4)O1—C9—C14—C153.0 (5)
C2—C3—C4—C5177.4 (3)C12—C13—C14—C91.5 (4)
C3—C4—C5—O1177.8 (3)C12—C13—C14—C15179.2 (3)
C3—C4—C5—C62.4 (4)C9—C14—C15—O2153.6 (3)
O1—C5—C6—C7178.5 (3)C13—C14—C15—O225.7 (5)
C4—C5—C6—C71.7 (4)C9—C14—C15—O328.0 (4)
O1—C5—C6—Cl12.0 (3)C13—C14—C15—O3152.7 (3)
C4—C5—C6—Cl1177.9 (2)O3—C16—C17—C18124.5 (4)
C5—C6—C7—C80.1 (5)O3—C16—C17—C2258.4 (5)
Cl1—C6—C7—C8179.4 (3)C22—C17—C18—C190.6 (6)
C6—C7—C8—C30.8 (5)C16—C17—C18—C19176.7 (4)
C6—C7—C8—C1179.0 (3)C17—C18—C19—C200.8 (8)
C4—C3—C8—C70.1 (4)C18—C19—C20—C210.2 (9)
C2—C3—C8—C7178.9 (3)C19—C20—C21—C220.5 (9)
C4—C3—C8—C1179.6 (3)C20—C21—C22—C170.7 (9)
C2—C3—C8—C10.8 (5)C18—C17—C22—C210.1 (6)
C14—C9—C10—C114.0 (5)C16—C17—C22—C21177.4 (5)
O1—C9—C10—C11178.4 (3)C4—C5—O1—C95.2 (4)
C9—C10—C11—C122.6 (6)C6—C5—O1—C9174.6 (2)
C10—C11—C12—C130.8 (6)C10—C9—O1—C580.3 (3)
C11—C12—C13—C142.9 (5)C14—C9—O1—C5105.2 (3)
C10—C9—C14—C132.0 (4)O2—C15—O3—C162.1 (5)
O1—C9—C14—C13176.2 (3)C14—C15—O3—C16179.5 (3)
C10—C9—C14—C15177.3 (3)C17—C16—O3—C15179.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···N1i0.93 (4)2.45 (4)3.322 (5)155 (3)
Symmetry code: (i) x, y+1/2, z+1.
 

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