



Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680802730X/at2616sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S160053680802730X/at2616Isup2.hkl |
CCDC reference: 702577
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.004 Å
- R factor = 0.067
- wR factor = 0.158
- Data-to-parameter ratio = 18.1
checkCIF/PLATON results
No syntax errors found
Alert level G 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 0 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 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 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
3-(Benzyloxy)pyridin-2-amine (0.020 g, 0.1 mmol) was added to a solution containing ethanol (8 ml) and ether (4 ml). The mixture was stirred at room temperature for 10 min and then filtered off. After a few days, colourless single crystals were obtained.
All H atoms attached to C and N atom were fixed geometrically and treated as riding with C—H = 0.93 Å (aromatic) or 0.97 Å (methylene) and N—H = 0.86 Å, and with Uiso(H) =1.2Ueq(C or N).
Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
C12H12N2O | F(000) = 848 |
Mr = 200.24 | Dx = 1.239 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 21430 reflections |
a = 12.852 (3) Å | θ = 3.1–27.5° |
b = 7.4068 (15) Å | µ = 0.08 mm−1 |
c = 22.561 (4) Å | T = 293 K |
V = 2147.6 (8) Å3 | Block, colourless |
Z = 8 | 0.15 × 0.10 × 0.07 mm |
Bruker SMART 1K CCD area-detector diffractometer | 2458 independent reflections |
Radiation source: fine-focus sealed tube | 1375 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.084 |
Detector resolution: 8.192 pixels mm-1 | θmax = 27.5°, θmin = 3.2° |
Thin–slice ω scans | h = −16→16 |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | k = −9→9 |
Tmin = 0.982, Tmax = 0.991 | l = −29→29 |
19827 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)] = 0.067 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.157 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0492P)2 + 0.5758P] where P = (Fo2 + 2Fc2)/3 |
2458 reflections | (Δ/σ)max < 0.001 |
136 parameters | Δρmax = 0.13 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
C12H12N2O | V = 2147.6 (8) Å3 |
Mr = 200.24 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 12.852 (3) Å | µ = 0.08 mm−1 |
b = 7.4068 (15) Å | T = 293 K |
c = 22.561 (4) Å | 0.15 × 0.10 × 0.07 mm |
Bruker SMART 1K CCD area-detector diffractometer | 2458 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | 1375 reflections with I > 2σ(I) |
Tmin = 0.982, Tmax = 0.991 | Rint = 0.084 |
19827 measured reflections |
R[F2 > 2σ(F2)] = 0.067 | 0 restraints |
wR(F2) = 0.157 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.13 e Å−3 |
2458 reflections | Δρmin = −0.15 e Å−3 |
136 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 | ||
C1 | 0.66421 (18) | 0.4734 (3) | −0.00746 (11) | 0.0624 (7) | |
H1A | 0.6925 | 0.3609 | 0.0012 | 0.075* | |
C2 | 0.65962 (19) | 0.5359 (4) | −0.06581 (11) | 0.0689 (7) | |
H2A | 0.6860 | 0.4667 | −0.0967 | 0.083* | |
C3 | 0.61591 (19) | 0.6997 (4) | −0.07666 (11) | 0.0648 (7) | |
H3A | 0.6124 | 0.7391 | −0.1157 | 0.078* | |
C4 | 0.58293 (17) | 0.7505 (3) | 0.02173 (10) | 0.0501 (6) | |
C5 | 0.62616 (17) | 0.5814 (3) | 0.03648 (10) | 0.0502 (6) | |
C6 | 0.65634 (19) | 0.3704 (3) | 0.11541 (11) | 0.0630 (7) | |
H6A | 0.7283 | 0.3488 | 0.1046 | 0.076* | |
H6B | 0.6135 | 0.2785 | 0.0969 | 0.076* | |
C7 | 0.64405 (17) | 0.3635 (3) | 0.18162 (11) | 0.0546 (6) | |
C8 | 0.5582 (2) | 0.4375 (3) | 0.20964 (11) | 0.0659 (7) | |
H8A | 0.5056 | 0.4899 | 0.1871 | 0.079* | |
C9 | 0.5499 (2) | 0.4343 (4) | 0.27071 (12) | 0.0763 (8) | |
H9A | 0.4922 | 0.4855 | 0.2891 | 0.092* | |
C10 | 0.6265 (3) | 0.3558 (4) | 0.30437 (13) | 0.0833 (9) | |
H10A | 0.6213 | 0.3540 | 0.3455 | 0.100* | |
C11 | 0.7103 (3) | 0.2807 (4) | 0.27693 (13) | 0.0899 (9) | |
H11A | 0.7617 | 0.2256 | 0.2996 | 0.108* | |
C12 | 0.7201 (2) | 0.2850 (3) | 0.21579 (12) | 0.0726 (8) | |
H12A | 0.7784 | 0.2346 | 0.1978 | 0.087* | |
N1 | 0.54785 (16) | 0.8603 (3) | 0.06572 (8) | 0.0714 (7) | |
H1B | 0.5227 | 0.9648 | 0.0572 | 0.086* | |
H1C | 0.5508 | 0.8253 | 0.1020 | 0.086* | |
N2 | 0.57740 (15) | 0.8083 (3) | −0.03408 (8) | 0.0577 (5) | |
O1 | 0.62485 (13) | 0.5449 (2) | 0.09615 (7) | 0.0628 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0613 (16) | 0.0619 (15) | 0.0641 (17) | 0.0114 (13) | −0.0064 (12) | −0.0070 (13) |
C2 | 0.0723 (17) | 0.0770 (18) | 0.0575 (17) | 0.0122 (14) | 0.0023 (13) | −0.0152 (14) |
C3 | 0.0654 (16) | 0.0796 (18) | 0.0494 (14) | 0.0048 (14) | 0.0042 (12) | −0.0011 (13) |
C4 | 0.0492 (13) | 0.0506 (13) | 0.0506 (13) | 0.0023 (11) | 0.0016 (10) | 0.0002 (11) |
C5 | 0.0462 (13) | 0.0560 (14) | 0.0484 (13) | 0.0015 (10) | −0.0037 (10) | −0.0016 (11) |
C6 | 0.0676 (17) | 0.0540 (15) | 0.0673 (17) | 0.0115 (12) | −0.0057 (13) | 0.0004 (12) |
C7 | 0.0581 (15) | 0.0411 (12) | 0.0645 (15) | 0.0025 (11) | −0.0048 (12) | 0.0068 (11) |
C8 | 0.0588 (15) | 0.0680 (16) | 0.0709 (17) | 0.0074 (13) | −0.0004 (13) | 0.0095 (13) |
C9 | 0.0757 (19) | 0.0759 (19) | 0.077 (2) | 0.0016 (15) | 0.0155 (15) | 0.0037 (15) |
C10 | 0.105 (2) | 0.079 (2) | 0.0653 (18) | 0.0010 (18) | 0.0042 (17) | 0.0146 (16) |
C11 | 0.105 (3) | 0.091 (2) | 0.074 (2) | 0.0223 (19) | −0.0172 (18) | 0.0197 (17) |
C12 | 0.0774 (19) | 0.0659 (17) | 0.0747 (18) | 0.0221 (14) | −0.0066 (14) | 0.0062 (14) |
N1 | 0.1049 (18) | 0.0599 (12) | 0.0493 (11) | 0.0246 (12) | 0.0085 (11) | 0.0024 (10) |
N2 | 0.0612 (13) | 0.0633 (12) | 0.0486 (11) | 0.0010 (10) | 0.0049 (9) | 0.0027 (10) |
O1 | 0.0838 (12) | 0.0531 (10) | 0.0517 (10) | 0.0124 (8) | −0.0015 (8) | 0.0041 (8) |
C1—C5 | 1.365 (3) | C6—H6B | 0.9700 |
C1—C2 | 1.397 (3) | C7—C12 | 1.374 (3) |
C1—H1A | 0.9300 | C7—C8 | 1.384 (3) |
C2—C3 | 1.359 (3) | C8—C9 | 1.382 (3) |
C2—H2A | 0.9300 | C8—H8A | 0.9300 |
C3—N2 | 1.347 (3) | C9—C10 | 1.373 (4) |
C3—H3A | 0.9300 | C9—H9A | 0.9300 |
C4—N2 | 1.332 (3) | C10—C11 | 1.361 (4) |
C4—N1 | 1.360 (3) | C10—H10A | 0.9300 |
C4—C5 | 1.410 (3) | C11—C12 | 1.386 (4) |
C5—O1 | 1.373 (3) | C11—H11A | 0.9300 |
C6—O1 | 1.422 (3) | C12—H12A | 0.9300 |
C6—C7 | 1.503 (3) | N1—H1B | 0.8600 |
C6—H6A | 0.9700 | N1—H1C | 0.8600 |
C5—C1—C2 | 118.4 (2) | C12—C7—C6 | 119.8 (2) |
C5—C1—H1A | 120.8 | C8—C7—C6 | 121.6 (2) |
C2—C1—H1A | 120.8 | C9—C8—C7 | 120.7 (2) |
C3—C2—C1 | 118.9 (2) | C9—C8—H8A | 119.7 |
C3—C2—H2A | 120.5 | C7—C8—H8A | 119.7 |
C1—C2—H2A | 120.5 | C10—C9—C8 | 120.2 (3) |
N2—C3—C2 | 123.8 (2) | C10—C9—H9A | 119.9 |
N2—C3—H3A | 118.1 | C8—C9—H9A | 119.9 |
C2—C3—H3A | 118.1 | C11—C10—C9 | 119.3 (3) |
N2—C4—N1 | 118.7 (2) | C11—C10—H10A | 120.4 |
N2—C4—C5 | 122.0 (2) | C9—C10—H10A | 120.4 |
N1—C4—C5 | 119.3 (2) | C10—C11—C12 | 121.1 (3) |
C1—C5—O1 | 127.0 (2) | C10—C11—H11A | 119.5 |
C1—C5—C4 | 119.4 (2) | C12—C11—H11A | 119.5 |
O1—C5—C4 | 113.67 (19) | C7—C12—C11 | 120.2 (3) |
O1—C6—C7 | 107.75 (18) | C7—C12—H12A | 119.9 |
O1—C6—H6A | 110.2 | C11—C12—H12A | 119.9 |
C7—C6—H6A | 110.2 | C4—N1—H1B | 120.0 |
O1—C6—H6B | 110.2 | C4—N1—H1C | 120.0 |
C7—C6—H6B | 110.2 | H1B—N1—H1C | 120.0 |
H6A—C6—H6B | 108.5 | C4—N2—C3 | 117.5 (2) |
C12—C7—C8 | 118.6 (2) | C5—O1—C6 | 118.36 (18) |
C5—C1—C2—C3 | −1.2 (4) | C7—C8—C9—C10 | −0.6 (4) |
C1—C2—C3—N2 | 0.9 (4) | C8—C9—C10—C11 | −0.3 (4) |
C2—C1—C5—O1 | −179.2 (2) | C9—C10—C11—C12 | 1.1 (5) |
C2—C1—C5—C4 | 0.6 (3) | C8—C7—C12—C11 | 0.0 (4) |
N2—C4—C5—C1 | 0.4 (3) | C6—C7—C12—C11 | 178.9 (2) |
N1—C4—C5—C1 | −178.1 (2) | C10—C11—C12—C7 | −1.0 (5) |
N2—C4—C5—O1 | −179.8 (2) | N1—C4—N2—C3 | 177.8 (2) |
N1—C4—C5—O1 | 1.7 (3) | C5—C4—N2—C3 | −0.7 (3) |
O1—C6—C7—C12 | −137.2 (2) | C2—C3—N2—C4 | 0.0 (4) |
O1—C6—C7—C8 | 41.6 (3) | C1—C5—O1—C6 | −6.8 (3) |
C12—C7—C8—C9 | 0.7 (4) | C4—C5—O1—C6 | 173.45 (19) |
C6—C7—C8—C9 | −178.1 (2) | C7—C6—O1—C5 | −177.93 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···N2i | 0.86 | 2.18 | 3.021 (3) | 166 |
N1—H1C···O1 | 0.86 | 2.29 | 2.628 (3) | 104 |
Symmetry code: (i) −x+1, −y+2, −z. |
Experimental details
Crystal data | |
Chemical formula | C12H12N2O |
Mr | 200.24 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 293 |
a, b, c (Å) | 12.852 (3), 7.4068 (15), 22.561 (4) |
V (Å3) | 2147.6 (8) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.15 × 0.10 × 0.07 |
Data collection | |
Diffractometer | Bruker SMART 1K CCD area-detector diffractometer |
Absorption correction | Multi-scan (CrystalClear; Rigaku, 2005) |
Tmin, Tmax | 0.982, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19827, 2458, 1375 |
Rint | 0.084 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.067, 0.157, 1.07 |
No. of reflections | 2458 |
No. of parameters | 136 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.13, −0.15 |
Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···N2i | 0.86 | 2.18 | 3.021 (3) | 166 |
N1—H1C···O1 | 0.86 | 2.29 | 2.628 (3) | 104 |
Symmetry code: (i) −x+1, −y+2, −z. |
Benzyl ethers and their derivatives are used as protecting group (Sharma et al., 2004) for alcohols and phenols in the synthesis of natural products (Evans et al., 2002). Here we report the synthesis and structure of the title compound, namely 3-(benzyloxy)pyridin-2-amine (I).
In the title compound (I) (Fig.1), the dihedral angle between the pyridine ring plane and benzene ring plane is 35.94 (12)°. In the crystal structure, centrosymmetrically related molecules are linked by a pair of N—H···N hydrogen bonds to form a dimer with an R22(8) ring motif (Fig. 2). In addition, there is an intramolecular N—H···O interaction (Table 1).