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Geometric parameters of the title compound, C
6H
7ClN
2, are in the usual ranges. The molecular structure shows one intramolecular N—H
Cl contact and the crystal packing is stabilized by an intermolecular N—H
N hydrogen bond.
Supporting information
CCDC reference: 636800
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C)= 0.002 Å
- R factor = 0.034
- wR factor = 0.093
- Data-to-parameter ratio = 13.3
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON and SHELXL97.
2-Chloro-4-methylpyridin-3-amine
top
Crystal data top
C6H7ClN2 | F(000) = 296 |
Mr = 142.59 | Dx = 1.440 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3355 reflections |
a = 3.9877 (8) Å | θ = 3.6–25.8° |
b = 12.8468 (15) Å | µ = 0.48 mm−1 |
c = 12.8408 (19) Å | T = 173 K |
β = 90.872 (14)° | Rod, colourless |
V = 657.75 (18) Å3 | 0.48 × 0.21 × 0.20 mm |
Z = 4 | |
Data collection top
Stoe IPDS-II two-circle diffractometer | 1226 independent reflections |
Radiation source: fine-focus sealed tube | 1109 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
ω scans | θmax = 25.6°, θmin = 3.6° |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −4→4 |
Tmin = 0.802, Tmax = 0.910 | k = −13→15 |
3879 measured reflections | l = −15→15 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.093 | w = 1/[σ2(Fo2) + (0.0536P)2 + 0.1927P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
1226 reflections | Δρmax = 0.33 e Å−3 |
92 parameters | Δρmin = −0.24 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.034 (8) |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.3824 (4) | 0.30002 (12) | 0.06150 (11) | 0.0250 (4) | |
C1 | 0.4225 (4) | 0.23558 (13) | 0.14121 (12) | 0.0208 (4) | |
Cl1 | 0.61995 (11) | 0.11678 (3) | 0.11410 (3) | 0.0269 (2) | |
C2 | 0.3202 (4) | 0.25351 (12) | 0.24415 (12) | 0.0201 (4) | |
N2 | 0.3645 (4) | 0.17923 (12) | 0.32181 (12) | 0.0267 (4) | |
H2A | 0.507 (6) | 0.1313 (19) | 0.3086 (19) | 0.038 (6)* | |
H2B | 0.372 (5) | 0.1991 (19) | 0.3838 (19) | 0.035 (6)* | |
C3 | 0.1565 (4) | 0.34844 (13) | 0.26263 (13) | 0.0213 (4) | |
C4 | 0.1151 (5) | 0.41751 (15) | 0.17928 (14) | 0.0266 (4) | |
H4 | 0.0073 | 0.4825 | 0.1897 | 0.032* | |
C5 | 0.2307 (5) | 0.39147 (14) | 0.08153 (14) | 0.0289 (5) | |
H5 | 0.2020 | 0.4400 | 0.0263 | 0.035* | |
C6 | 0.0272 (5) | 0.37306 (14) | 0.36974 (14) | 0.0265 (4) | |
H6A | −0.1131 | 0.4356 | 0.3663 | 0.040* | |
H6B | 0.2170 | 0.3851 | 0.4176 | 0.040* | |
H6C | −0.1062 | 0.3144 | 0.3949 | 0.040* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0295 (8) | 0.0283 (8) | 0.0174 (7) | −0.0006 (6) | 0.0000 (6) | 0.0019 (6) |
C1 | 0.0217 (9) | 0.0220 (8) | 0.0188 (8) | −0.0015 (7) | 0.0003 (6) | −0.0017 (6) |
Cl1 | 0.0331 (3) | 0.0257 (3) | 0.0220 (3) | 0.00514 (16) | 0.00271 (19) | −0.00252 (14) |
C2 | 0.0206 (9) | 0.0226 (9) | 0.0169 (8) | −0.0054 (6) | −0.0013 (6) | −0.0006 (6) |
N2 | 0.0393 (10) | 0.0251 (8) | 0.0157 (7) | 0.0015 (7) | 0.0025 (6) | 0.0006 (6) |
C3 | 0.0184 (8) | 0.0242 (8) | 0.0214 (8) | −0.0042 (7) | −0.0005 (6) | −0.0039 (7) |
C4 | 0.0282 (10) | 0.0249 (9) | 0.0266 (9) | 0.0032 (7) | −0.0037 (7) | −0.0017 (7) |
C5 | 0.0359 (11) | 0.0266 (10) | 0.0242 (9) | 0.0025 (7) | −0.0034 (8) | 0.0047 (7) |
C6 | 0.0276 (10) | 0.0289 (9) | 0.0231 (9) | −0.0017 (7) | 0.0023 (7) | −0.0055 (7) |
Geometric parameters (Å, º) top
N1—C1 | 1.324 (2) | C3—C4 | 1.398 (3) |
N1—C5 | 1.348 (2) | C3—C6 | 1.510 (2) |
C1—C2 | 1.408 (2) | C4—C5 | 1.385 (3) |
C1—Cl1 | 1.7546 (17) | C4—H4 | 0.9500 |
C2—N2 | 1.390 (2) | C5—H5 | 0.9500 |
C2—C3 | 1.405 (2) | C6—H6A | 0.9800 |
N2—H2A | 0.86 (3) | C6—H6B | 0.9800 |
N2—H2B | 0.84 (2) | C6—H6C | 0.9800 |
| | | |
C1—N1—C5 | 116.53 (15) | C5—C4—C3 | 120.23 (17) |
N1—C1—C2 | 126.15 (16) | C5—C4—H4 | 119.9 |
N1—C1—Cl1 | 116.09 (12) | C3—C4—H4 | 119.9 |
C2—C1—Cl1 | 117.76 (12) | N1—C5—C4 | 122.69 (16) |
N2—C2—C3 | 121.94 (15) | N1—C5—H5 | 118.7 |
N2—C2—C1 | 121.73 (15) | C4—C5—H5 | 118.7 |
C3—C2—C1 | 116.26 (14) | C3—C6—H6A | 109.5 |
C2—N2—H2A | 115.4 (16) | C3—C6—H6B | 109.5 |
C2—N2—H2B | 118.4 (16) | H6A—C6—H6B | 109.5 |
H2A—N2—H2B | 113 (2) | C3—C6—H6C | 109.5 |
C4—C3—C2 | 118.12 (15) | H6A—C6—H6C | 109.5 |
C4—C3—C6 | 121.77 (16) | H6B—C6—H6C | 109.5 |
C2—C3—C6 | 120.11 (15) | | |
| | | |
C5—N1—C1—C2 | 0.4 (3) | C1—C2—C3—C4 | −1.3 (2) |
C5—N1—C1—Cl1 | 179.95 (13) | N2—C2—C3—C6 | 0.9 (2) |
N1—C1—C2—N2 | 177.89 (16) | C1—C2—C3—C6 | 177.95 (15) |
Cl1—C1—C2—N2 | −1.7 (2) | C2—C3—C4—C5 | 0.6 (3) |
N1—C1—C2—C3 | 0.9 (2) | C6—C3—C4—C5 | −178.65 (17) |
Cl1—C1—C2—C3 | −178.67 (12) | C1—N1—C5—C4 | −1.2 (3) |
N2—C2—C3—C4 | −178.33 (16) | C3—C4—C5—N1 | 0.7 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···Cl1 | 0.86 (3) | 2.55 (3) | 2.9796 (17) | 111.9 (19) |
N2—H2B···N1i | 0.84 (2) | 2.28 (2) | 3.089 (2) | 162 (2) |
Symmetry code: (i) x, −y+1/2, z+1/2. |
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