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The title phthalonitrile derivative, C14H6BrClN2O, contains two aromatic rings, which are almost perpendicular.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805021057/at6020sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805021057/at6020Isup2.hkl
Contains datablock I

CCDC reference: 282227

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.057
  • wR factor = 0.144
  • Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.102 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.10 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.64 mm PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.03 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C1 - C3 ... 1.46 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2 - C8 ... 1.43 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32; 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-Bromo-4-chlorophenoxy)phthalonitrile top
Crystal data top
C14H6BrClN2OF(000) = 1312
Mr = 333.57Dx = 1.657 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 21214 reflections
a = 14.2841 (14) Åθ = 1.8–27.2°
b = 8.3753 (5) ŵ = 3.27 mm1
c = 22.353 (2) ÅT = 293 K
V = 2674.2 (4) Å3Prism, colourless
Z = 80.64 × 0.34 × 0.19 mm
Data collection top
Stoe IPDS-2
diffractometer
2634 independent reflections
Radiation source: fine-focus sealed tube1468 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.102
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 1.8°
ω scansh = 1717
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 1010
Tmin = 0.192, Tmax = 0.523l = 2727
22144 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0548P)2 + 2.1953P]
where P = (Fo2 + 2Fc2)/3
2634 reflections(Δ/σ)max < 0.001
172 parametersΔρmax = 0.79 e Å3
0 restraintsΔρmin = 0.49 e Å3
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
Br10.13757 (6)0.22601 (7)0.33038 (3)0.0849 (3)
Cl10.33324 (18)0.0948 (2)0.15419 (7)0.1051 (7)
N10.3715 (5)0.2415 (5)0.5198 (2)0.0925 (19)
C10.3711 (5)0.1101 (6)0.5088 (2)0.0639 (15)
C50.3538 (5)0.2658 (6)0.4208 (3)0.0698 (16)
C30.3705 (4)0.0595 (5)0.4934 (2)0.0557 (14)
O10.3347 (4)0.3231 (4)0.36488 (18)0.0957 (17)
C40.3526 (5)0.1050 (5)0.4352 (2)0.0646 (17)
H40.33990.02880.40600.078*
C90.3334 (6)0.2175 (7)0.3166 (3)0.075 (2)
C60.3722 (5)0.3797 (6)0.4640 (3)0.0735 (18)
H60.37200.48750.45390.088*
C140.2499 (5)0.1643 (6)0.2937 (2)0.0660 (17)
C80.3912 (4)0.1732 (6)0.5371 (2)0.0605 (15)
C130.2491 (5)0.0692 (6)0.2431 (2)0.0680 (16)
H130.19290.03440.22670.082*
C120.3319 (6)0.0277 (7)0.2178 (2)0.0757 (19)
C110.4164 (6)0.0773 (8)0.2403 (3)0.090 (2)
H110.47220.04590.22240.108*
C70.3905 (5)0.3345 (6)0.5210 (3)0.0750 (19)
H70.40270.41180.54980.090*
C20.4116 (6)0.1255 (7)0.5970 (3)0.0764 (18)
N20.4290 (6)0.0853 (7)0.6445 (3)0.109 (2)
C100.4170 (7)0.1754 (8)0.2903 (3)0.092 (2)
H100.47330.21240.30590.110*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.1177 (6)0.0570 (3)0.0801 (4)0.0039 (4)0.0035 (4)0.0038 (3)
Cl10.157 (2)0.0952 (12)0.0630 (9)0.0024 (12)0.0175 (10)0.0053 (8)
N10.143 (6)0.050 (3)0.085 (3)0.008 (3)0.007 (3)0.009 (2)
C10.080 (5)0.053 (3)0.058 (3)0.001 (3)0.003 (3)0.004 (2)
C50.096 (5)0.040 (3)0.073 (3)0.005 (3)0.016 (4)0.003 (2)
C30.066 (4)0.041 (2)0.060 (3)0.001 (2)0.006 (3)0.005 (2)
O10.170 (5)0.0375 (19)0.080 (3)0.000 (2)0.043 (3)0.0024 (18)
C40.097 (5)0.034 (2)0.063 (3)0.004 (3)0.016 (3)0.006 (2)
C90.117 (7)0.041 (3)0.068 (4)0.003 (4)0.021 (4)0.013 (3)
C60.103 (6)0.037 (3)0.081 (4)0.001 (3)0.014 (4)0.010 (2)
C140.104 (5)0.043 (3)0.052 (3)0.007 (3)0.004 (3)0.009 (2)
C80.068 (5)0.052 (3)0.062 (3)0.006 (3)0.001 (3)0.006 (2)
C130.101 (5)0.051 (3)0.052 (3)0.002 (3)0.005 (3)0.010 (2)
C120.114 (7)0.061 (3)0.052 (3)0.005 (4)0.007 (4)0.015 (3)
C110.105 (7)0.074 (4)0.090 (5)0.006 (4)0.015 (5)0.020 (4)
C70.099 (6)0.047 (3)0.080 (4)0.004 (3)0.009 (3)0.021 (3)
C20.091 (5)0.069 (4)0.069 (4)0.006 (4)0.011 (4)0.014 (3)
N20.147 (7)0.103 (4)0.076 (4)0.009 (4)0.025 (4)0.005 (3)
C100.115 (7)0.061 (4)0.100 (5)0.020 (4)0.029 (5)0.022 (4)
Geometric parameters (Å, º) top
Br1—C141.874 (7)C6—C71.355 (8)
Cl1—C121.752 (6)C6—H60.9300
N1—C11.128 (6)C14—C131.384 (7)
C1—C31.461 (7)C8—C71.398 (7)
C5—O11.367 (6)C8—C21.428 (9)
C5—C61.382 (7)C13—C121.357 (9)
C5—C41.385 (7)C13—H130.9300
C3—C41.380 (7)C12—C111.372 (10)
C3—C81.396 (7)C11—C101.387 (9)
O1—C91.395 (7)C11—H110.9300
C4—H40.9300C7—H70.9300
C9—C141.372 (9)C2—N21.140 (7)
C9—C101.378 (10)C10—H100.9300
N1—C1—C3179.0 (6)C3—C8—C7118.5 (5)
O1—C5—C6115.7 (4)C3—C8—C2120.6 (5)
O1—C5—C4123.4 (5)C7—C8—C2120.9 (5)
C6—C5—C4120.8 (5)C12—C13—C14118.8 (7)
C4—C3—C8120.7 (4)C12—C13—H13120.6
C4—C3—C1119.4 (4)C14—C13—H13120.6
C8—C3—C1119.8 (4)C13—C12—C11122.4 (6)
C5—O1—C9119.2 (4)C13—C12—Cl1119.9 (6)
C3—C4—C5119.0 (4)C11—C12—Cl1117.7 (6)
C3—C4—H4120.5C12—C11—C10118.7 (8)
C5—C4—H4120.5C12—C11—H11120.6
C14—C9—C10120.8 (6)C10—C11—H11120.6
C14—C9—O1120.4 (7)C6—C7—C8121.0 (5)
C10—C9—O1118.8 (7)C6—C7—H7119.5
C7—C6—C5120.0 (5)C8—C7—H7119.5
C7—C6—H6120.0N2—C2—C8178.7 (8)
C5—C6—H6120.0C9—C10—C11119.4 (8)
C9—C14—C13119.9 (7)C9—C10—H10120.3
C9—C14—Br1119.5 (5)C11—C10—H10120.3
C13—C14—Br1120.6 (6)
C6—C5—O1—C9167.6 (7)C1—C3—C8—C7179.7 (6)
C4—C5—O1—C914.3 (10)C4—C3—C8—C2178.7 (6)
C8—C3—C4—C51.2 (10)C1—C3—C8—C21.1 (9)
C1—C3—C4—C5178.8 (6)C9—C14—C13—C121.4 (7)
O1—C5—C4—C3178.3 (6)Br1—C14—C13—C12179.7 (4)
C6—C5—C4—C30.3 (11)C14—C13—C12—C110.4 (8)
C5—O1—C9—C14101.8 (7)C14—C13—C12—Cl1179.2 (4)
C5—O1—C9—C1082.0 (7)C13—C12—C11—C100.9 (9)
O1—C5—C6—C7179.0 (6)Cl1—C12—C11—C10179.5 (4)
C4—C5—C6—C70.8 (11)C5—C6—C7—C80.1 (11)
C10—C9—C14—C131.0 (8)C3—C8—C7—C61.5 (10)
O1—C9—C14—C13175.2 (4)C2—C8—C7—C6179.3 (7)
C10—C9—C14—Br1179.4 (4)C14—C9—C10—C110.4 (9)
O1—C9—C14—Br13.2 (7)O1—C9—C10—C11176.6 (5)
C4—C3—C8—C72.1 (9)C12—C11—C10—C91.3 (9)
 

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