Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807057984/sj2419sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807057984/sj2419Isup2.hkl |
CCDC reference: 672969
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.058
- wR factor = 0.170
- Data-to-parameter ratio = 10.2
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.812 1.000 Tmin(prime) and Tmax expected: 0.985 0.994 RR(prime) = 0.820 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.82 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 C5 - C8 ... 1.43 Ang.
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.994 Tmax scaled 0.994 Tmin scaled 0.807 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 27.48 From the CIF: _reflns_number_total 1565 Count of symmetry unique reflns 1568 Completeness (_total/calc) 99.81% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For the preparation of tetrazole derivatives from nitrile compounds, see: Drew et al. (1984); Dunica et al. (1991); Szczesna & Urbanczyk-Lipkowska (2002); Wittenberger & Donner (1993). For the general chemistry of tetrazole compounds, see: Xiong et al. (2002).
To a solution of 4-formylbenzonitrile (6.55 g, 0.05 mol) in methanol (40 ml) was added phenylhydrazine (5.40 g, 0.05 mol) with stirring at room temperature. After 20 minutes, a mass of yellow precipitate appeared and was filtered. The crude product was recrystallized by slowly evaporating an ethanol solution to yield pale yellow block-like crystals, suitable for X-ray analysis.
Positional parameters of all the H atoms were calculated geometrically and were allowed to ride on the C atoms to which they are bonded, with d(C—H) = 0.93 and d(N—H) = 0.90 Å and Uiso(H) = 1.2Ueq(C or N). In the absence of significant anomalous scattering effects, Friedel pairs were merged.
Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 1999).
C14H11N3 | F(000) = 464 |
Mr = 221.26 | Dx = 1.253 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 9243 reflections |
a = 7.1442 (14) Å | θ = 3.2–27.5° |
b = 11.147 (2) Å | µ = 0.08 mm−1 |
c = 14.726 (3) Å | T = 293 K |
V = 1172.7 (4) Å3 | Block, yellow |
Z = 4 | 0.2 × 0.08 × 0.08 mm |
Mercury2 diffractometer | 1565 independent reflections |
Radiation source: fine-focus sealed tube | 984 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.074 |
Detector resolution: 13.6612 pixels mm-1 | θmax = 27.5°, θmin = 3.2° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | k = −14→14 |
Tmin = 0.812, Tmax = 1.0 | l = −19→19 |
11983 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.170 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0863P)2] where P = (Fo2 + 2Fc2)/3 |
1565 reflections | (Δ/σ)max < 0.001 |
154 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−3 |
C14H11N3 | V = 1172.7 (4) Å3 |
Mr = 221.26 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 7.1442 (14) Å | µ = 0.08 mm−1 |
b = 11.147 (2) Å | T = 293 K |
c = 14.726 (3) Å | 0.2 × 0.08 × 0.08 mm |
Mercury2 diffractometer | 1565 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | 984 reflections with I > 2σ(I) |
Tmin = 0.812, Tmax = 1.0 | Rint = 0.074 |
11983 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | 0 restraints |
wR(F2) = 0.170 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.14 e Å−3 |
1565 reflections | Δρmin = −0.14 e Å−3 |
154 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.4559 (4) | 0.4066 (3) | 0.51082 (19) | 0.0665 (8) | |
N2 | 0.4212 (5) | 0.2870 (3) | 0.5177 (2) | 0.0756 (9) | |
H2B | 0.4864 | 0.2514 | 0.4729 | 0.091* | |
N3 | 0.4871 (6) | 1.0614 (3) | 0.3748 (2) | 0.1010 (13) | |
C1 | 0.4160 (5) | 0.4567 (3) | 0.4354 (2) | 0.0671 (9) | |
H1 | 0.3704 | 0.4100 | 0.3880 | 0.081* | |
C2 | 0.4400 (4) | 0.5844 (3) | 0.4218 (2) | 0.0606 (9) | |
C3 | 0.5107 (5) | 0.6589 (3) | 0.4901 (2) | 0.0639 (9) | |
H3 | 0.5493 | 0.6256 | 0.5449 | 0.077* | |
C4 | 0.5241 (5) | 0.7814 (3) | 0.4772 (2) | 0.0674 (10) | |
H4 | 0.5704 | 0.8301 | 0.5233 | 0.081* | |
C5 | 0.4680 (5) | 0.8315 (3) | 0.3950 (2) | 0.0642 (9) | |
C6 | 0.4008 (5) | 0.7585 (3) | 0.3266 (2) | 0.0704 (10) | |
H6 | 0.3649 | 0.7915 | 0.2713 | 0.084* | |
C7 | 0.3871 (5) | 0.6374 (4) | 0.3406 (2) | 0.0675 (10) | |
H7 | 0.3410 | 0.5892 | 0.2941 | 0.081* | |
C8 | 0.4797 (6) | 0.9587 (4) | 0.3826 (2) | 0.0759 (11) | |
C9 | 0.4638 (5) | 0.2253 (3) | 0.5963 (2) | 0.0606 (8) | |
C10 | 0.5663 (5) | 0.2755 (3) | 0.6664 (2) | 0.0657 (9) | |
H10 | 0.6101 | 0.3538 | 0.6618 | 0.079* | |
C11 | 0.6031 (5) | 0.2089 (3) | 0.7430 (2) | 0.0732 (10) | |
H11 | 0.6708 | 0.2436 | 0.7902 | 0.088* | |
C12 | 0.5428 (6) | 0.0933 (3) | 0.7515 (3) | 0.0745 (11) | |
H12 | 0.5711 | 0.0490 | 0.8032 | 0.089* | |
C13 | 0.4383 (6) | 0.0427 (3) | 0.6814 (3) | 0.0752 (11) | |
H13 | 0.3935 | −0.0353 | 0.6866 | 0.090* | |
C14 | 0.4019 (5) | 0.1080 (3) | 0.6053 (2) | 0.0703 (10) | |
H14 | 0.3340 | 0.0732 | 0.5583 | 0.084* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0649 (17) | 0.0672 (19) | 0.0674 (19) | 0.0050 (15) | −0.0015 (15) | 0.0044 (14) |
N2 | 0.090 (2) | 0.069 (2) | 0.0686 (19) | 0.0038 (19) | −0.0102 (17) | −0.0012 (15) |
N3 | 0.131 (3) | 0.089 (2) | 0.083 (2) | 0.003 (3) | 0.007 (2) | 0.0146 (19) |
C1 | 0.067 (2) | 0.075 (2) | 0.060 (2) | −0.0034 (19) | −0.0108 (18) | −0.0002 (18) |
C2 | 0.0475 (17) | 0.084 (2) | 0.0508 (19) | 0.0019 (18) | −0.0020 (15) | 0.0015 (16) |
C3 | 0.0601 (19) | 0.077 (3) | 0.054 (2) | −0.0017 (18) | −0.0092 (17) | 0.0133 (17) |
C4 | 0.061 (2) | 0.082 (3) | 0.059 (2) | −0.007 (2) | −0.0104 (17) | 0.0004 (17) |
C5 | 0.057 (2) | 0.077 (2) | 0.058 (2) | 0.0018 (19) | 0.0046 (17) | 0.0081 (17) |
C6 | 0.068 (2) | 0.096 (3) | 0.0477 (19) | 0.007 (2) | −0.0026 (18) | 0.0090 (19) |
C7 | 0.068 (2) | 0.088 (3) | 0.0472 (18) | −0.003 (2) | −0.0016 (18) | 0.0006 (17) |
C8 | 0.078 (3) | 0.079 (3) | 0.070 (2) | 0.005 (2) | 0.009 (2) | 0.013 (2) |
C9 | 0.0610 (18) | 0.059 (2) | 0.062 (2) | 0.0036 (17) | −0.0030 (16) | −0.0030 (15) |
C10 | 0.073 (2) | 0.0580 (19) | 0.066 (2) | 0.0036 (19) | −0.005 (2) | −0.0059 (17) |
C11 | 0.088 (3) | 0.072 (2) | 0.060 (2) | 0.019 (2) | −0.0115 (19) | −0.0099 (18) |
C12 | 0.090 (3) | 0.065 (2) | 0.068 (2) | 0.017 (2) | 0.007 (2) | 0.0052 (17) |
C13 | 0.090 (3) | 0.061 (2) | 0.075 (2) | −0.004 (2) | 0.009 (2) | 0.0017 (18) |
C14 | 0.072 (2) | 0.069 (2) | 0.070 (2) | −0.002 (2) | 0.0021 (19) | −0.0084 (18) |
N1—C1 | 1.275 (4) | C6—C7 | 1.370 (4) |
N1—N2 | 1.359 (4) | C6—H6 | 0.9300 |
N2—C9 | 1.381 (4) | C7—H7 | 0.9300 |
N2—H2B | 0.9000 | C9—C10 | 1.384 (4) |
N3—C8 | 1.151 (4) | C9—C14 | 1.387 (4) |
C1—C2 | 1.448 (4) | C10—C11 | 1.375 (4) |
C1—H1 | 0.9300 | C10—H10 | 0.9300 |
C2—C7 | 1.387 (4) | C11—C12 | 1.365 (5) |
C2—C3 | 1.399 (4) | C11—H11 | 0.9300 |
C3—C4 | 1.382 (4) | C12—C13 | 1.393 (5) |
C3—H3 | 0.9300 | C12—H12 | 0.9300 |
C4—C5 | 1.393 (5) | C13—C14 | 1.361 (5) |
C4—H4 | 0.9300 | C13—H13 | 0.9300 |
C5—C6 | 1.381 (4) | C14—H14 | 0.9300 |
C5—C8 | 1.433 (5) | ||
C1—N1—N2 | 117.0 (3) | C6—C7—C2 | 122.0 (3) |
N1—N2—C9 | 120.7 (3) | C6—C7—H7 | 119.0 |
N1—N2—H2B | 106.5 | C2—C7—H7 | 119.0 |
C9—N2—H2B | 106.3 | N3—C8—C5 | 178.3 (4) |
N1—C1—C2 | 121.7 (3) | N2—C9—C10 | 122.8 (3) |
N1—C1—H1 | 119.2 | N2—C9—C14 | 118.6 (3) |
C2—C1—H1 | 119.2 | C10—C9—C14 | 118.6 (3) |
C7—C2—C3 | 117.8 (3) | C11—C10—C9 | 119.7 (3) |
C7—C2—C1 | 120.4 (3) | C11—C10—H10 | 120.2 |
C3—C2—C1 | 121.8 (3) | C9—C10—H10 | 120.2 |
C4—C3—C2 | 120.8 (3) | C12—C11—C10 | 121.6 (3) |
C4—C3—H3 | 119.6 | C12—C11—H11 | 119.2 |
C2—C3—H3 | 119.6 | C10—C11—H11 | 119.2 |
C3—C4—C5 | 119.7 (3) | C11—C12—C13 | 118.9 (3) |
C3—C4—H4 | 120.1 | C11—C12—H12 | 120.5 |
C5—C4—H4 | 120.1 | C13—C12—H12 | 120.5 |
C6—C5—C4 | 119.9 (3) | C14—C13—C12 | 119.8 (4) |
C6—C5—C8 | 120.7 (3) | C14—C13—H13 | 120.1 |
C4—C5—C8 | 119.4 (3) | C12—C13—H13 | 120.1 |
C7—C6—C5 | 119.7 (3) | C13—C14—C9 | 121.4 (4) |
C7—C6—H6 | 120.1 | C13—C14—H14 | 119.3 |
C5—C6—H6 | 120.1 | C9—C14—H14 | 119.3 |
C9—N2—N1—C1 | 178.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2B···N3i | 0.90 | 2.56 | 3.313 (5) | 141 |
Symmetry code: (i) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C14H11N3 |
Mr | 221.26 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 293 |
a, b, c (Å) | 7.1442 (14), 11.147 (2), 14.726 (3) |
V (Å3) | 1172.7 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.2 × 0.08 × 0.08 |
Data collection | |
Diffractometer | Mercury2 diffractometer |
Absorption correction | Multi-scan (CrystalClear; Rigaku, 2005) |
Tmin, Tmax | 0.812, 1.0 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11983, 1565, 984 |
Rint | 0.074 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.170, 1.09 |
No. of reflections | 1565 |
No. of parameters | 154 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.14, −0.14 |
Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2B···N3i | 0.90 | 2.56 | 3.313 (5) | 141.1 |
Symmetry code: (i) x, y−1, z. |
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Nitrile compounds are the precursor of tetrazole derivatives (Dunica, et al., 1991; Wittenberger, et al., 1993), which we have focused on for the design of noncentrosymmetric bulk materials (Xiong, et al.(2002)). We report here the crystal structure of the title compound, 4-(phenyl-hydrazonomethyl)benzonitrile, (I), Fig. 1.
In I, the C=N double bond (1.359 (4) Å) is in the range 1.34–1.38 Å found in other similar hydrazone complexes with a trans configuration (Szczesna & Urbanczyk-Lipkowska (2002); Drew, et al.(1984). The torsion angles of C9 - N2 - N1 - C1 is -178.7 (3)°. Dihedral angle between the two benzene rings is 13.56 (0.15) °. In the crystal structure molecules related by translation along b axis are connected by N2—H2B···N3 hydrogen bonds resulting in the formation of one dimensional chains along the b axis.