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In the title compound, C14H10BrN, the dihedral angle between the two aromatic rings is 48.34 (14)°. Weak C—H...Br and C—H...N interactions are the principal intermolecular forces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803025571/ob6317sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803025571/ob6317Isup2.hkl
Contains datablock I

CCDC reference: 227889

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.045
  • wR factor = 0.088
  • Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
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 2284 Count of symmetry unique reflns 1319 Completeness (_total/calc) 173.16% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 965 Fraction of Friedel pairs measured 0.732 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

4'-Bromomethylbiphenyl-2-carbonitrile top
Crystal data top
C14H10BrNF(000) = 2176
Mr = 272.14Dx = 1.538 Mg m3
Orthorhombic, Fdd2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2dCell parameters from 1496 reflections
a = 47.219 (12) Åθ = 2.4–20.6°
b = 24.229 (6) ŵ = 3.47 mm1
c = 4.1085 (10) ÅT = 293 K
V = 4700 (2) Å3Prism, colourless
Z = 160.3 × 0.2 × 0.2 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2284 independent reflections
Radiation source: fine-focus sealed tube1610 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.075
φ and ω scansθmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 5852
Tmin = 0.43, Tmax = 0.50k = 2924
6379 measured reflectionsl = 54
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.088 w = 1/[σ2(Fo2) + (0.02P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
2284 reflectionsΔρmax = 0.44 e Å3
145 parametersΔρmin = 0.34 e Å3
1 restraintAbsolute structure: Flack (1983), 965 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.014 (15)
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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

21.9209 (0.0998) x - 0.1847 (0.0528) y - 3.6388 (0.0046) z = 5.4707 (0.0434)

* 0.0016 (0.0037) C2 * -0.0013 (0.0040) C3 * 0.0003 (0.0040) C4 * 0.0003 (0.0036) C5 * -0.0001 (0.0040) C6 * -0.0009 (0.0040) C7

Rms deviation of fitted atoms = 0.0009

16.4269 (0.1123) x + 2.4815 (0.0646) y + 3.8288 (0.0040) z = 7.6557 (0.0414)

Angle to previous plane (with approximate e.s.d.) = 48.34 (0.14)

* 0.0051 (0.0039) C8 * 0.0028 (0.0049) C9 * -0.0088 (0.0057) C10 * 0.0066 (0.0054) C11 * 0.0015 (0.0046) C12 * -0.0072 (0.0040) C13

Rms deviation of fitted atoms = 0.0059

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br0.272011 (12)0.65748 (2)0.49307 (17)0.0614 (2)
C10.30571 (10)0.62629 (18)0.2846 (16)0.0509 (14)
H1A0.32360.64600.39750.061*
H1B0.30250.63770.07150.061*
C20.30797 (10)0.56493 (19)0.3227 (12)0.0406 (13)
C30.28709 (10)0.53046 (19)0.1995 (15)0.0462 (13)
H30.27050.54890.10140.055*
C40.29008 (10)0.47354 (18)0.2199 (15)0.0445 (12)
H40.27470.45220.14380.053*
C50.31403 (10)0.45058 (19)0.3654 (11)0.0382 (13)
C60.33463 (9)0.48542 (18)0.4878 (16)0.0431 (12)
H50.35290.47230.58310.052*
C70.33114 (10)0.54225 (18)0.4641 (15)0.0419 (12)
H60.34680.56460.55130.050*
C80.31705 (10)0.38964 (19)0.3880 (12)0.0396 (13)
C90.29460 (11)0.35779 (18)0.5044 (18)0.0547 (14)
H90.27600.37300.53050.066*
C100.29691 (13)0.3008 (2)0.5284 (19)0.0725 (19)
H100.28100.28160.60640.087*
C110.32143 (12)0.2747 (2)0.4442 (19)0.0704 (18)
H110.32220.23710.48920.084*
C120.34392 (12)0.3043 (2)0.3272 (14)0.0566 (17)
H120.36070.28810.28900.068*
C130.34199 (10)0.36196 (19)0.2958 (14)0.0437 (14)
C140.36506 (12)0.3904 (2)0.1625 (13)0.0463 (15)
N10.38449 (10)0.41217 (16)0.0496 (14)0.0642 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br0.0633 (4)0.0500 (3)0.0709 (4)0.0116 (3)0.0080 (4)0.0071 (4)
C10.056 (3)0.042 (3)0.055 (4)0.001 (2)0.007 (3)0.005 (3)
C20.040 (3)0.040 (3)0.042 (3)0.005 (2)0.005 (3)0.003 (2)
C30.037 (3)0.049 (3)0.052 (4)0.006 (2)0.006 (3)0.004 (3)
C40.039 (3)0.045 (3)0.049 (3)0.004 (2)0.006 (3)0.009 (3)
C50.035 (3)0.041 (3)0.039 (3)0.002 (2)0.008 (2)0.000 (2)
C60.039 (3)0.044 (3)0.046 (3)0.001 (2)0.005 (3)0.003 (3)
C70.038 (3)0.043 (3)0.044 (3)0.003 (2)0.006 (3)0.001 (3)
C80.035 (3)0.039 (3)0.045 (3)0.004 (2)0.001 (2)0.001 (2)
C90.047 (3)0.046 (3)0.071 (4)0.002 (2)0.008 (4)0.002 (4)
C100.076 (4)0.048 (3)0.094 (5)0.016 (3)0.021 (5)0.010 (4)
C110.071 (4)0.037 (3)0.103 (5)0.000 (3)0.010 (5)0.004 (4)
C120.064 (4)0.036 (3)0.070 (5)0.009 (3)0.000 (3)0.000 (3)
C130.044 (3)0.037 (3)0.051 (4)0.003 (2)0.004 (3)0.001 (3)
C140.042 (3)0.042 (3)0.055 (4)0.005 (2)0.007 (3)0.002 (3)
N10.052 (3)0.054 (3)0.086 (4)0.001 (2)0.009 (3)0.005 (3)
Geometric parameters (Å, º) top
Br—C11.959 (5)C7—H60.9830
C1—C21.499 (6)C8—C91.396 (6)
C1—H1A1.0754C8—C131.407 (6)
C1—H1B0.9305C9—C101.389 (7)
C2—C71.355 (6)C9—H90.9577
C2—C31.388 (6)C10—C111.364 (7)
C3—C41.389 (6)C10—H100.9396
C3—H30.9877C11—C121.369 (7)
C4—C51.395 (6)C11—H110.9303
C4—H40.9453C12—C131.407 (6)
C5—C61.383 (6)C12—H120.8997
C5—C81.486 (6)C13—C141.401 (7)
C6—C71.390 (6)C14—N11.155 (6)
C6—H51.0007
C2—C1—Br113.3 (4)C2—C7—H6122.6
C2—C1—H1A109.8C6—C7—H6115.5
Br—C1—H1A106.2C9—C8—C13117.7 (4)
C2—C1—H1B113.8C9—C8—C5119.8 (4)
Br—C1—H1B99.5C13—C8—C5122.5 (4)
H1A—C1—H1B113.7C10—C9—C8121.0 (5)
C7—C2—C3119.1 (4)C10—C9—H9116.5
C7—C2—C1120.3 (4)C8—C9—H9121.5
C3—C2—C1120.6 (5)C11—C10—C9120.7 (5)
C2—C3—C4120.2 (5)C11—C10—H10122.3
C2—C3—H3116.1C9—C10—H10117.0
C4—C3—H3123.7C10—C11—C12120.3 (5)
C3—C4—C5120.3 (4)C10—C11—H11116.0
C3—C4—H4116.5C12—C11—H11123.5
C5—C4—H4123.1C11—C12—C13120.2 (5)
C6—C5—C4118.9 (4)C11—C12—H12121.2
C6—C5—C8121.1 (4)C13—C12—H12118.3
C4—C5—C8120.1 (4)C14—C13—C12118.3 (5)
C5—C6—C7119.7 (5)C14—C13—C8121.4 (4)
C5—C6—H5123.8C12—C13—C8120.2 (4)
C7—C6—H5116.3N1—C14—C13177.7 (6)
C2—C7—C6121.8 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1B···Bri0.932.823.699 (6)158
C1—H1A···N1ii1.082.613.634 (8)159
C9—H9···Briii0.963.053.750 (6)131
Symmetry codes: (i) x, y, z1; (ii) x+3/4, y+1/4, z+3/4; (iii) x+1/2, y+1, z+1/2.
 

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