The geometric parameters of the title compound, C
9H
10N
2O
2, which crystallizes with two molecules in the asymmetric unit, are in the usual ranges. The molecules are essentially planar (r.m.s. deviations for all non-H atoms are 0.084 and 0.110 Å for the two molecules in the asymmetric unit). The crystal packing is stabilized by N—H
O hydrogen bonds.
Supporting information
CCDC reference: 674077
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.002 Å
- R factor = 0.036
- wR factor = 0.097
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for C2 - C7 .. 7.14 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for C2A - C7A .. 7.58 su
Alert level C
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2 - C7 ... 1.44 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2A - C7A ... 1.44 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor N1A - H1C ... ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1C .. N2A .. 2.74 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 6
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
5 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
5 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
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
2-Amino-4,5-dimethoxybenzonitrile was obtained as a gift sample from SeQuent
Scientific Limited, Mangalore and was recrystallized from methanol by slow
evaporation technique [m.p: 369–374 K]).
All H atoms were found in a difference map, but those bonded to C were
geometrically positioned and refined with fixed individual displacement
parameters [Uiso(H) = 1.2 or 1.5Ueq(C)] using a riding model
with C—H = 0.95 or 0.98 Å. The H atoms of the amino group was freely
refined.
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
2-Amino-4,5-dimethoxybenzonitrile
top
Crystal data top
C9H10N2O2 | F(000) = 752 |
Mr = 178.19 | Dx = 1.322 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 21499 reflections |
a = 13.2649 (9) Å | θ = 3.6–26.8° |
b = 17.0653 (9) Å | µ = 0.10 mm−1 |
c = 7.9635 (5) Å | T = 173 K |
β = 96.769 (5)° | Block, colourless |
V = 1790.13 (19) Å3 | 0.33 × 0.29 × 0.24 mm |
Z = 8 | |
Data collection top
STOE IPDS II two-circle- diffractometer | 3163 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.038 |
Graphite monochromator | θmax = 26.7°, θmin = 3.5° |
ω scans | h = −16→16 |
23314 measured reflections | k = −21→21 |
3722 independent reflections | l = −10→9 |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.097 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.060P)2 + 0.2526P] where P = (Fo2 + 2Fc2)/3 |
3722 reflections | (Δ/σ)max < 0.001 |
255 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
Crystal data top
C9H10N2O2 | V = 1790.13 (19) Å3 |
Mr = 178.19 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.2649 (9) Å | µ = 0.10 mm−1 |
b = 17.0653 (9) Å | T = 173 K |
c = 7.9635 (5) Å | 0.33 × 0.29 × 0.24 mm |
β = 96.769 (5)° | |
Data collection top
STOE IPDS II two-circle- diffractometer | 3163 reflections with I > 2σ(I) |
23314 measured reflections | Rint = 0.038 |
3722 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.097 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.15 e Å−3 |
3722 reflections | Δρmin = −0.21 e Å−3 |
255 parameters | |
Special details top
Experimental. ; |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.07571 (6) | 0.74641 (5) | 0.29441 (12) | 0.0305 (2) | |
O2 | 0.06985 (6) | 0.59747 (5) | 0.23025 (10) | 0.02477 (19) | |
N1 | 0.38490 (8) | 0.54952 (7) | 0.58981 (14) | 0.0286 (2) | |
H1A | 0.3905 (12) | 0.5060 (10) | 0.526 (2) | 0.038 (4)* | |
H1B | 0.4457 (12) | 0.5714 (9) | 0.632 (2) | 0.034 (4)* | |
N2 | 0.46025 (9) | 0.73153 (8) | 0.77100 (17) | 0.0435 (3) | |
C1 | 0.31110 (8) | 0.60122 (7) | 0.51816 (14) | 0.0211 (2) | |
C2 | 0.31248 (8) | 0.68144 (7) | 0.55662 (15) | 0.0233 (2) | |
C3 | 0.23499 (8) | 0.73219 (7) | 0.48324 (15) | 0.0251 (2) | |
H3 | 0.2378 | 0.7865 | 0.5099 | 0.030* | |
C4 | 0.15563 (8) | 0.70339 (6) | 0.37346 (14) | 0.0225 (2) | |
C5 | 0.15205 (8) | 0.62171 (7) | 0.33777 (14) | 0.0204 (2) | |
C6 | 0.22811 (8) | 0.57221 (6) | 0.40866 (14) | 0.0214 (2) | |
H6 | 0.2244 | 0.5178 | 0.3832 | 0.026* | |
C7 | 0.39404 (9) | 0.71128 (7) | 0.67434 (16) | 0.0286 (3) | |
C8 | 0.08316 (10) | 0.83018 (7) | 0.30592 (17) | 0.0319 (3) | |
H8A | 0.0823 | 0.8464 | 0.4238 | 0.048* | |
H8B | 0.0256 | 0.8540 | 0.2358 | 0.048* | |
H8C | 0.1467 | 0.8474 | 0.2660 | 0.048* | |
C9 | 0.05401 (9) | 0.51431 (7) | 0.21645 (17) | 0.0286 (3) | |
H9A | 0.1075 | 0.4908 | 0.1579 | 0.043* | |
H9B | −0.0123 | 0.5039 | 0.1523 | 0.043* | |
H9C | 0.0560 | 0.4915 | 0.3298 | 0.043* | |
O1A | 0.58742 (6) | 0.49611 (5) | 0.81914 (11) | 0.0304 (2) | |
O2A | 0.63026 (6) | 0.61035 (5) | 0.62874 (10) | 0.0270 (2) | |
N1A | 0.88591 (8) | 0.71281 (6) | 1.06092 (15) | 0.0286 (2) | |
H1C | 0.9030 (12) | 0.7465 (10) | 0.986 (2) | 0.038 (4)* | |
H1D | 0.9361 (12) | 0.6981 (10) | 1.139 (2) | 0.038 (4)* | |
N2A | 0.87001 (9) | 0.59744 (7) | 1.42142 (14) | 0.0371 (3) | |
C1A | 0.81333 (8) | 0.65744 (6) | 1.00388 (14) | 0.0220 (2) | |
C2A | 0.78575 (8) | 0.59755 (7) | 1.11092 (14) | 0.0226 (2) | |
C3A | 0.71054 (8) | 0.54145 (7) | 1.05269 (15) | 0.0246 (2) | |
H3A | 0.6942 | 0.5004 | 1.1254 | 0.030* | |
C4A | 0.66133 (8) | 0.54648 (6) | 0.89099 (15) | 0.0229 (2) | |
C5A | 0.68523 (8) | 0.60922 (6) | 0.78508 (14) | 0.0217 (2) | |
C6A | 0.76065 (8) | 0.66260 (6) | 0.83953 (14) | 0.0224 (2) | |
H6A | 0.7771 | 0.7031 | 0.7656 | 0.027* | |
C7A | 0.83205 (9) | 0.59568 (7) | 1.28329 (15) | 0.0266 (3) | |
C8A | 0.57605 (10) | 0.42399 (8) | 0.9070 (2) | 0.0380 (3) | |
H8A1 | 0.6417 | 0.3971 | 0.9254 | 0.057* | |
H8A2 | 0.5267 | 0.3906 | 0.8393 | 0.057* | |
H8A3 | 0.5520 | 0.4350 | 1.0163 | 0.057* | |
C9A | 0.64180 (10) | 0.67832 (8) | 0.52425 (16) | 0.0313 (3) | |
H9A1 | 0.6245 | 0.7257 | 0.5844 | 0.047* | |
H9A2 | 0.5964 | 0.6736 | 0.4183 | 0.047* | |
H9A3 | 0.7122 | 0.6818 | 0.4992 | 0.047* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0276 (4) | 0.0193 (4) | 0.0418 (5) | 0.0027 (3) | −0.0070 (4) | 0.0019 (3) |
O2 | 0.0227 (4) | 0.0215 (4) | 0.0277 (4) | 0.0003 (3) | −0.0073 (3) | 0.0001 (3) |
N1 | 0.0231 (5) | 0.0303 (5) | 0.0301 (6) | 0.0035 (4) | −0.0061 (4) | −0.0019 (4) |
N2 | 0.0316 (6) | 0.0483 (7) | 0.0477 (7) | −0.0039 (5) | −0.0069 (5) | −0.0177 (6) |
C1 | 0.0193 (5) | 0.0258 (5) | 0.0183 (5) | 0.0003 (4) | 0.0018 (4) | 0.0006 (4) |
C2 | 0.0196 (5) | 0.0272 (6) | 0.0228 (6) | −0.0038 (4) | 0.0013 (4) | −0.0024 (4) |
C3 | 0.0250 (5) | 0.0204 (5) | 0.0299 (6) | −0.0035 (4) | 0.0037 (5) | −0.0021 (4) |
C4 | 0.0214 (5) | 0.0212 (5) | 0.0246 (6) | 0.0011 (4) | 0.0012 (4) | 0.0026 (4) |
C5 | 0.0192 (5) | 0.0232 (5) | 0.0182 (5) | −0.0015 (4) | 0.0000 (4) | −0.0001 (4) |
C6 | 0.0222 (5) | 0.0200 (5) | 0.0214 (5) | 0.0007 (4) | 0.0004 (4) | −0.0014 (4) |
C7 | 0.0244 (5) | 0.0293 (6) | 0.0318 (7) | −0.0009 (5) | 0.0019 (5) | −0.0062 (5) |
C8 | 0.0365 (6) | 0.0188 (6) | 0.0400 (7) | 0.0044 (5) | 0.0036 (5) | −0.0002 (5) |
C9 | 0.0282 (6) | 0.0218 (6) | 0.0328 (6) | 0.0001 (4) | −0.0094 (5) | −0.0058 (5) |
O1A | 0.0284 (4) | 0.0273 (4) | 0.0339 (5) | −0.0062 (3) | −0.0030 (4) | 0.0005 (4) |
O2A | 0.0282 (4) | 0.0269 (4) | 0.0238 (4) | 0.0015 (3) | −0.0061 (3) | 0.0025 (3) |
N1A | 0.0261 (5) | 0.0265 (5) | 0.0313 (6) | −0.0031 (4) | −0.0052 (4) | 0.0020 (4) |
N2A | 0.0396 (6) | 0.0458 (7) | 0.0245 (6) | 0.0030 (5) | −0.0018 (5) | 0.0021 (5) |
C1A | 0.0192 (5) | 0.0210 (5) | 0.0254 (6) | 0.0041 (4) | 0.0009 (4) | −0.0014 (4) |
C2A | 0.0213 (5) | 0.0257 (6) | 0.0203 (5) | 0.0047 (4) | 0.0003 (4) | −0.0002 (4) |
C3A | 0.0252 (5) | 0.0241 (5) | 0.0248 (6) | 0.0015 (4) | 0.0041 (4) | 0.0037 (4) |
C4A | 0.0198 (5) | 0.0217 (5) | 0.0269 (6) | 0.0004 (4) | 0.0014 (4) | −0.0019 (4) |
C5A | 0.0208 (5) | 0.0230 (5) | 0.0207 (5) | 0.0061 (4) | −0.0001 (4) | −0.0010 (4) |
C6A | 0.0226 (5) | 0.0208 (5) | 0.0235 (6) | 0.0029 (4) | 0.0015 (4) | 0.0028 (4) |
C7A | 0.0258 (5) | 0.0293 (6) | 0.0249 (6) | 0.0037 (4) | 0.0035 (5) | 0.0016 (5) |
C8A | 0.0356 (7) | 0.0248 (6) | 0.0523 (9) | −0.0058 (5) | −0.0001 (6) | 0.0031 (6) |
C9A | 0.0339 (6) | 0.0328 (6) | 0.0254 (6) | 0.0046 (5) | −0.0041 (5) | 0.0079 (5) |
Geometric parameters (Å, º) top
O1—C4 | 1.3790 (13) | O1A—C4A | 1.3767 (14) |
O1—C8 | 1.4353 (14) | O1A—C8A | 1.4323 (16) |
O2—C5 | 1.3686 (13) | O2A—C5A | 1.3668 (13) |
O2—C9 | 1.4369 (14) | O2A—C9A | 1.4461 (15) |
N1—C1 | 1.3895 (15) | N1A—C1A | 1.3867 (15) |
N1—H1A | 0.907 (17) | N1A—H1C | 0.876 (18) |
N1—H1B | 0.916 (16) | N1A—H1D | 0.894 (17) |
N2—C7 | 1.1506 (17) | N2A—C7A | 1.1549 (16) |
C1—C2 | 1.4023 (16) | C1A—C2A | 1.4067 (16) |
C1—C6 | 1.4110 (15) | C1A—C6A | 1.4118 (15) |
C2—C3 | 1.4165 (16) | C2A—C3A | 1.4205 (16) |
C2—C7 | 1.4387 (16) | C2A—C7A | 1.4365 (16) |
C3—C4 | 1.3774 (16) | C3A—C4A | 1.3761 (16) |
C3—H3 | 0.9500 | C3A—H3A | 0.9500 |
C4—C5 | 1.4222 (16) | C4A—C5A | 1.4217 (16) |
C5—C6 | 1.3841 (15) | C5A—C6A | 1.3844 (16) |
C6—H6 | 0.9500 | C6A—H6A | 0.9500 |
C8—H8A | 0.9800 | C8A—H8A1 | 0.9800 |
C8—H8B | 0.9800 | C8A—H8A2 | 0.9800 |
C8—H8C | 0.9800 | C8A—H8A3 | 0.9800 |
C9—H9A | 0.9800 | C9A—H9A1 | 0.9800 |
C9—H9B | 0.9800 | C9A—H9A2 | 0.9800 |
C9—H9C | 0.9800 | C9A—H9A3 | 0.9800 |
| | | |
C4—O1—C8 | 117.24 (9) | C4A—O1A—C8A | 116.39 (10) |
C5—O2—C9 | 116.42 (8) | C5A—O2A—C9A | 117.02 (9) |
C1—N1—H1A | 113.0 (10) | C1A—N1A—H1C | 116.8 (10) |
C1—N1—H1B | 116.0 (10) | C1A—N1A—H1D | 118.0 (11) |
H1A—N1—H1B | 114.4 (14) | H1C—N1A—H1D | 115.3 (14) |
N1—C1—C2 | 122.66 (10) | N1A—C1A—C2A | 121.11 (10) |
N1—C1—C6 | 119.44 (10) | N1A—C1A—C6A | 120.65 (10) |
C2—C1—C6 | 117.82 (10) | C2A—C1A—C6A | 118.13 (10) |
C1—C2—C3 | 121.10 (10) | C1A—C2A—C3A | 120.98 (10) |
C1—C2—C7 | 118.51 (10) | C1A—C2A—C7A | 118.86 (10) |
C3—C2—C7 | 120.38 (10) | C3A—C2A—C7A | 120.11 (10) |
C4—C3—C2 | 120.45 (10) | C4A—C3A—C2A | 120.06 (10) |
C4—C3—H3 | 119.8 | C4A—C3A—H3A | 120.0 |
C2—C3—H3 | 119.8 | C2A—C3A—H3A | 120.0 |
C3—C4—O1 | 126.07 (10) | C3A—C4A—O1A | 125.87 (10) |
C3—C4—C5 | 118.79 (10) | C3A—C4A—C5A | 119.20 (10) |
O1—C4—C5 | 115.14 (9) | O1A—C4A—C5A | 114.92 (10) |
O2—C5—C6 | 124.01 (10) | O2A—C5A—C6A | 124.35 (10) |
O2—C5—C4 | 115.25 (9) | O2A—C5A—C4A | 114.76 (10) |
C6—C5—C4 | 120.74 (10) | C6A—C5A—C4A | 120.87 (10) |
C5—C6—C1 | 121.06 (10) | C5A—C6A—C1A | 120.65 (10) |
C5—C6—H6 | 119.5 | C5A—C6A—H6A | 119.7 |
C1—C6—H6 | 119.5 | C1A—C6A—H6A | 119.7 |
N2—C7—C2 | 176.72 (14) | N2A—C7A—C2A | 177.18 (13) |
O1—C8—H8A | 109.5 | O1A—C8A—H8A1 | 109.5 |
O1—C8—H8B | 109.5 | O1A—C8A—H8A2 | 109.5 |
H8A—C8—H8B | 109.5 | H8A1—C8A—H8A2 | 109.5 |
O1—C8—H8C | 109.5 | O1A—C8A—H8A3 | 109.5 |
H8A—C8—H8C | 109.5 | H8A1—C8A—H8A3 | 109.5 |
H8B—C8—H8C | 109.5 | H8A2—C8A—H8A3 | 109.5 |
O2—C9—H9A | 109.5 | O2A—C9A—H9A1 | 109.5 |
O2—C9—H9B | 109.5 | O2A—C9A—H9A2 | 109.5 |
H9A—C9—H9B | 109.5 | H9A1—C9A—H9A2 | 109.5 |
O2—C9—H9C | 109.5 | O2A—C9A—H9A3 | 109.5 |
H9A—C9—H9C | 109.5 | H9A1—C9A—H9A3 | 109.5 |
H9B—C9—H9C | 109.5 | H9A2—C9A—H9A3 | 109.5 |
| | | |
N1—C1—C2—C3 | −178.93 (11) | N1A—C1A—C2A—C3A | 179.28 (10) |
C6—C1—C2—C3 | −2.21 (16) | C6A—C1A—C2A—C3A | 3.07 (16) |
N1—C1—C2—C7 | 0.37 (17) | N1A—C1A—C2A—C7A | 1.77 (16) |
C6—C1—C2—C7 | 177.09 (10) | C6A—C1A—C2A—C7A | −174.44 (10) |
C1—C2—C3—C4 | 0.76 (17) | C1A—C2A—C3A—C4A | −1.89 (16) |
C7—C2—C3—C4 | −178.52 (11) | C7A—C2A—C3A—C4A | 175.59 (10) |
C2—C3—C4—O1 | 179.78 (11) | C2A—C3A—C4A—O1A | 179.91 (10) |
C2—C3—C4—C5 | 1.13 (17) | C2A—C3A—C4A—C5A | −1.31 (16) |
C8—O1—C4—C3 | 10.31 (17) | C8A—O1A—C4A—C3A | −13.65 (17) |
C8—O1—C4—C5 | −171.00 (10) | C8A—O1A—C4A—C5A | 167.52 (10) |
C9—O2—C5—C6 | 11.52 (16) | C9A—O2A—C5A—C6A | −9.50 (15) |
C9—O2—C5—C4 | −168.80 (10) | C9A—O2A—C5A—C4A | 172.09 (10) |
C3—C4—C5—O2 | 178.75 (10) | C3A—C4A—C5A—O2A | −178.21 (10) |
O1—C4—C5—O2 | −0.04 (14) | O1A—C4A—C5A—O2A | 0.71 (14) |
C3—C4—C5—C6 | −1.55 (16) | C3A—C4A—C5A—C6A | 3.32 (16) |
O1—C4—C5—C6 | 179.66 (10) | O1A—C4A—C5A—C6A | −177.76 (10) |
O2—C5—C6—C1 | 179.73 (10) | O2A—C5A—C6A—C1A | 179.57 (10) |
C4—C5—C6—C1 | 0.06 (17) | C4A—C5A—C6A—C1A | −2.12 (16) |
N1—C1—C6—C5 | 178.63 (10) | N1A—C1A—C6A—C5A | −177.29 (10) |
C2—C1—C6—C5 | 1.79 (16) | C2A—C1A—C6A—C5A | −1.06 (16) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2Ai | 0.907 (17) | 2.336 (17) | 3.2296 (14) | 168.1 (14) |
N1—H1B···O2A | 0.916 (16) | 2.540 (16) | 3.3954 (13) | 155.7 (13) |
N1—H1B···O1A | 0.916 (16) | 2.597 (15) | 3.1979 (13) | 123.7 (12) |
N1A—H1C···N2Aii | 0.876 (18) | 2.738 (18) | 3.4217 (17) | 135.9 (14) |
N1A—H1D···O1iii | 0.894 (17) | 2.257 (17) | 3.0036 (13) | 140.9 (14) |
N1A—H1D···O2iii | 0.894 (17) | 2.514 (17) | 3.2971 (13) | 146.7 (14) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+3/2, z−1/2; (iii) x+1, y, z+1. |
Experimental details
Crystal data |
Chemical formula | C9H10N2O2 |
Mr | 178.19 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 173 |
a, b, c (Å) | 13.2649 (9), 17.0653 (9), 7.9635 (5) |
β (°) | 96.769 (5) |
V (Å3) | 1790.13 (19) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.33 × 0.29 × 0.24 |
|
Data collection |
Diffractometer | STOE IPDS II two-circle- diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 23314, 3722, 3163 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.632 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.097, 1.02 |
No. of reflections | 3722 |
No. of parameters | 255 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.15, −0.21 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2Ai | 0.907 (17) | 2.336 (17) | 3.2296 (14) | 168.1 (14) |
N1—H1B···O2A | 0.916 (16) | 2.540 (16) | 3.3954 (13) | 155.7 (13) |
N1—H1B···O1A | 0.916 (16) | 2.597 (15) | 3.1979 (13) | 123.7 (12) |
N1A—H1C···N2Aii | 0.876 (18) | 2.738 (18) | 3.4217 (17) | 135.9 (14) |
N1A—H1D···O1iii | 0.894 (17) | 2.257 (17) | 3.0036 (13) | 140.9 (14) |
N1A—H1D···O2iii | 0.894 (17) | 2.514 (17) | 3.2971 (13) | 146.7 (14) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+3/2, z−1/2; (iii) x+1, y, z+1. |
Nitriles are close relatives of azoles and hydrazones and are parent compounds for the preparation of various functional organic materials having triazole, imidazole or thidiazole moieties (İkizler & Sancak, 1992; 1995; 1998). The synthesis of new azoles has been a very active area of research and an important aspect is the incorporation of functional units such as, cyanomethyl group in ravuconazol (Urbina et al., 2001). Nitrile derivatives have many industrial applications. For example, phthalonitriles have been used as starting materials for phthalocyanines (Jin et al., 1994), which are important components for dyes, pigments, gas sensors, optical limiters and liquid crystals. They are also used in medicine as singlet oxygen photosensitizers for photodynamic therapy (Brewis et al., 2003). Some related crystal structures, viz., (2-cyanomethoxy-6-methoxyphenoxy)acetonitrile (Sancak, 2005), p-decylphenyl isocyanide and p-decylbenzonitrile: isomorphous isonitrile/nitrile isomers (Britton et al., 2004) and 2-[2-(cyanomethoxy)phenoxy]acetonitrile (Ustabaş et al., 2004) have been reported. A new nitrile derivative was obtained from the industry as a gift sample and its structure is reported.
Geometric parameters of the title compound, which crystallizes with two molecules in the asymmetric unit, are in the usual ranges. The molecules are essentially planar (r.m.s. deviation for all non-H atoms 0.084 Å and 0.110 Å for the two molecules in the asymmetric unit). The crystal packing is stabilized by N—H···O hydrogen bonds.