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The title compound, C12H12N4, is a trans-azobenzene which crystallizes with an inversion center at the midpoint of the N=N bond.
Supporting information
CCDC reference: 636660
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.034
- wR factor = 0.098
- Data-to-parameter ratio = 12.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2B ... ?
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 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
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL.
2,2'-diaminoazobenzene
top
Crystal data top
C12H12N4 | F(000) = 448 |
Mr = 212.26 | Dx = 1.362 Mg m−3 Dm = 1.32 Mg m−3 Dm measured by flotation in ???? |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 157 reflections |
a = 22.278 (6) Å | θ = 2.3–28.1° |
b = 5.8647 (16) Å | µ = 0.09 mm−1 |
c = 8.254 (2) Å | T = 100 K |
β = 106.357 (3)° | Block, orange–red |
V = 1034.8 (5) Å3 | 0.20 × 0.10 × 0.07 mm |
Z = 4 | |
Data collection top
Siemens SMART CCD diffractometer | 1003 independent reflections |
Radiation source: fine-focus sealed tube | 929 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
ω scans | θmax = 25.9°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Siemens, 1996) | h = −27→27 |
Tmin = 0.983, Tmax = 0.990 | k = −7→7 |
3927 measured reflections | l = −9→10 |
Refinement top
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)] = 0.034 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.098 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0584P)2 + 0.6927P] where P = (Fo2 + 2Fc2)/3 |
1003 reflections | (Δ/σ)max < 0.001 |
81 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.01100 (4) | 0.09432 (15) | 0.48469 (11) | 0.0164 (3) | |
N2 | 0.06365 (5) | 0.48594 (16) | 0.41750 (12) | 0.0196 (3) | |
C1 | 0.07248 (5) | 0.14153 (18) | 0.58466 (12) | 0.0154 (3) | |
C2 | 0.09767 (5) | 0.34962 (18) | 0.54716 (12) | 0.0158 (3) | |
C3 | 0.15849 (5) | 0.40897 (19) | 0.64058 (14) | 0.0186 (3) | |
H3A | 0.1760 | 0.5444 | 0.6170 | 0.022* | |
C4 | 0.19264 (5) | 0.26818 (19) | 0.76747 (14) | 0.0206 (3) | |
H4A | 0.2329 | 0.3104 | 0.8287 | 0.025* | |
C5 | 0.16749 (5) | 0.0628 (2) | 0.80508 (13) | 0.0204 (3) | |
H5A | 0.1907 | −0.0307 | 0.8910 | 0.024* | |
C6 | 0.10796 (5) | 0.00022 (18) | 0.71356 (13) | 0.0178 (3) | |
H6A | 0.0912 | −0.1367 | 0.7374 | 0.021* | |
H2B | 0.0770 (7) | 0.627 (3) | 0.4141 (17) | 0.030 (4)* | |
H2A | 0.0230 (8) | 0.458 (3) | 0.3846 (18) | 0.033 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0181 (5) | 0.0164 (5) | 0.0159 (5) | −0.0006 (3) | 0.0066 (4) | −0.0012 (3) |
N2 | 0.0197 (5) | 0.0170 (5) | 0.0215 (5) | −0.0013 (4) | 0.0048 (4) | 0.0022 (4) |
C1 | 0.0162 (5) | 0.0174 (5) | 0.0140 (5) | 0.0002 (4) | 0.0064 (4) | −0.0031 (4) |
C2 | 0.0188 (5) | 0.0160 (5) | 0.0146 (5) | 0.0020 (4) | 0.0079 (4) | −0.0021 (4) |
C3 | 0.0191 (6) | 0.0170 (6) | 0.0217 (6) | −0.0031 (4) | 0.0089 (4) | −0.0022 (4) |
C4 | 0.0155 (5) | 0.0249 (6) | 0.0205 (6) | −0.0010 (4) | 0.0037 (4) | −0.0038 (4) |
C5 | 0.0200 (6) | 0.0227 (6) | 0.0172 (5) | 0.0031 (4) | 0.0033 (4) | 0.0015 (4) |
C6 | 0.0210 (6) | 0.0166 (5) | 0.0171 (5) | −0.0003 (4) | 0.0077 (4) | 0.0000 (4) |
Geometric parameters (Å, º) top
N1—N1i | 1.2641 (18) | C3—C4 | 1.3816 (16) |
N1—C1 | 1.4131 (14) | C3—H3A | 0.9300 |
N2—C2 | 1.3792 (14) | C4—C5 | 1.3999 (16) |
N2—H2B | 0.884 (16) | C4—H4A | 0.9300 |
N2—H2A | 0.884 (16) | C5—C6 | 1.3783 (16) |
C1—C6 | 1.4036 (15) | C5—H5A | 0.9300 |
C1—C2 | 1.4135 (15) | C6—H6A | 0.9300 |
C2—C3 | 1.4011 (15) | | |
| | | |
N1i—N1—C1 | 114.92 (11) | C4—C3—H3A | 119.7 |
C2—N2—H2B | 116.9 (9) | C2—C3—H3A | 119.7 |
C2—N2—H2A | 115.0 (10) | C3—C4—C5 | 120.86 (10) |
H2B—N2—H2A | 119.2 (13) | C3—C4—H4A | 119.6 |
C6—C1—N1 | 124.98 (10) | C5—C4—H4A | 119.6 |
C6—C1—C2 | 120.15 (10) | C6—C5—C4 | 119.41 (10) |
N1—C1—C2 | 114.87 (9) | C6—C5—H5A | 120.3 |
N2—C2—C3 | 121.20 (10) | C4—C5—H5A | 120.3 |
N2—C2—C1 | 120.34 (10) | C5—C6—C1 | 120.52 (10) |
C3—C2—C1 | 118.43 (10) | C5—C6—H6A | 119.7 |
C4—C3—C2 | 120.63 (10) | C1—C6—H6A | 119.7 |
| | | |
N1i—N1—C1—C6 | −2.03 (17) | C1—C2—C3—C4 | −0.68 (16) |
N1i—N1—C1—C2 | 178.34 (10) | C2—C3—C4—C5 | 0.33 (16) |
C6—C1—C2—N2 | 178.18 (9) | C3—C4—C5—C6 | 0.29 (16) |
N1—C1—C2—N2 | −2.17 (14) | C4—C5—C6—C1 | −0.55 (16) |
C6—C1—C2—C3 | 0.42 (15) | N1—C1—C6—C5 | −179.42 (9) |
N1—C1—C2—C3 | −179.93 (8) | C2—C1—C6—C5 | 0.19 (16) |
N2—C2—C3—C4 | −178.42 (9) | | |
Symmetry code: (i) −x, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···N1 | 0.884 (18) | 2.330 (17) | 2.7064 (15) | 105.7 (13) |
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