Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055523/hb2630sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055523/hb2630Isup2.hkl |
CCDC reference: 672877
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.002 Å
- R factor = 0.031
- wR factor = 0.086
- Data-to-parameter ratio = 15.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT420_ALERT_2_C D-H Without Acceptor N4 - H4 ... ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H4 .. N3 .. 2.65 Ang.
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 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 1 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 related literature, see: Manasek & Hrdlovik (1990); Mathias & Simanek (1994).
2,4,6-Trichloro-1,3,5-triazine (9.22 g, 0.05 mol), and 4-methoxylaniline (6.15 g, 0.05 mol) were added to 60 ml diethyl ether with stirring at 268 K for 2 h. A solution of Na2CO3 (2.76 g, 0.026 mol) in water (20 ml) was then added dropwise over 1 h. The reaction mixture was stirred at 273–278 K for a further 3 h. The precipitate was filtered off, and the acetone was evaporated under reduced pressure. The title compound (12.13 g) was obtained in a yield of 89.5%. Colourless blocks of (I) (m.p. 442–443 K) were obtained by slow evaporation of a mixture of ethyl acetate and ethanol.
The N-bound H atom was located in a difference map and freely refined. All other H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 Å or 0.96 Å and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).
C10H8Cl2N4O | F(000) = 552 |
Mr = 271.10 | Dx = 1.535 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3751 reflections |
a = 7.6090 (16) Å | θ = 3.0–26.4° |
b = 20.635 (4) Å | µ = 0.54 mm−1 |
c = 8.3081 (17) Å | T = 294 K |
β = 115.908 (3)° | Block, colourless |
V = 1173.3 (4) Å3 | 0.24 × 0.22 × 0.18 mm |
Z = 4 |
Bruker SMART CCD diffractometer | 2400 independent reflections |
Radiation source: fine-focus sealed tube | 2016 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
ω scans | θmax = 26.4°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.881, Tmax = 0.909 | k = −25→25 |
6560 measured reflections | l = −10→8 |
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)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.087 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0425P)2 + 0.3097P] where P = (Fo2 + 2Fc2)/3 |
2400 reflections | (Δ/σ)max = 0.001 |
159 parameters | Δρmax = 0.18 e Å−3 |
1 restraint | Δρmin = −0.36 e Å−3 |
C10H8Cl2N4O | V = 1173.3 (4) Å3 |
Mr = 271.10 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.6090 (16) Å | µ = 0.54 mm−1 |
b = 20.635 (4) Å | T = 294 K |
c = 8.3081 (17) Å | 0.24 × 0.22 × 0.18 mm |
β = 115.908 (3)° |
Bruker SMART CCD diffractometer | 2400 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2016 reflections with I > 2σ(I) |
Tmin = 0.881, Tmax = 0.909 | Rint = 0.019 |
6560 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | 1 restraint |
wR(F2) = 0.087 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.18 e Å−3 |
2400 reflections | Δρmin = −0.36 e Å−3 |
159 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 | ||
Cl1 | 0.48399 (7) | 0.55535 (2) | 0.67070 (6) | 0.05566 (16) | |
Cl2 | 0.92722 (8) | 0.62654 (2) | 1.33265 (6) | 0.06189 (18) | |
O1 | −0.0465 (2) | 0.89691 (6) | 0.24801 (16) | 0.0534 (3) | |
N1 | 0.6998 (2) | 0.59535 (6) | 0.99908 (18) | 0.0410 (3) | |
N2 | 0.69411 (19) | 0.70612 (6) | 1.09037 (17) | 0.0385 (3) | |
N3 | 0.49723 (19) | 0.67436 (6) | 0.78247 (17) | 0.0382 (3) | |
N4 | 0.4870 (2) | 0.77990 (7) | 0.88813 (18) | 0.0419 (3) | |
C1 | 0.5709 (2) | 0.61570 (8) | 0.8365 (2) | 0.0377 (4) | |
C2 | 0.7551 (2) | 0.64553 (8) | 1.1163 (2) | 0.0390 (4) | |
C3 | 0.5590 (2) | 0.71897 (7) | 0.9180 (2) | 0.0349 (3) | |
C4 | 0.3479 (2) | 0.80867 (8) | 0.7242 (2) | 0.0364 (3) | |
C5 | 0.1925 (2) | 0.77394 (8) | 0.5928 (2) | 0.0404 (4) | |
H5 | 0.1749 | 0.7304 | 0.6103 | 0.048* | |
C6 | 0.0648 (2) | 0.80499 (8) | 0.4360 (2) | 0.0416 (4) | |
H6 | −0.0367 | 0.7817 | 0.3485 | 0.050* | |
C7 | 0.0880 (2) | 0.87127 (8) | 0.4087 (2) | 0.0396 (4) | |
C8 | 0.2396 (3) | 0.90674 (8) | 0.5418 (2) | 0.0420 (4) | |
H8 | 0.2544 | 0.9507 | 0.5263 | 0.050* | |
C9 | 0.3686 (2) | 0.87490 (8) | 0.6984 (2) | 0.0407 (4) | |
H9 | 0.4696 | 0.8981 | 0.7866 | 0.049* | |
C10 | −0.0269 (3) | 0.96487 (9) | 0.2171 (3) | 0.0571 (5) | |
H10A | −0.0403 | 0.9902 | 0.3081 | 0.086* | |
H10B | −0.1267 | 0.9770 | 0.1018 | 0.086* | |
H10C | 0.0993 | 0.9725 | 0.2209 | 0.086* | |
H4 | 0.534 (3) | 0.8050 (9) | 0.9843 (19) | 0.057 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0621 (3) | 0.0410 (2) | 0.0471 (3) | −0.00029 (19) | 0.0083 (2) | −0.01340 (18) |
Cl2 | 0.0728 (3) | 0.0490 (3) | 0.0365 (2) | 0.0036 (2) | −0.0015 (2) | 0.00528 (18) |
O1 | 0.0634 (8) | 0.0446 (7) | 0.0401 (7) | 0.0091 (6) | 0.0115 (6) | 0.0059 (5) |
N1 | 0.0439 (8) | 0.0353 (7) | 0.0363 (7) | 0.0004 (6) | 0.0106 (6) | 0.0015 (5) |
N2 | 0.0415 (7) | 0.0371 (7) | 0.0310 (6) | −0.0014 (6) | 0.0103 (6) | −0.0010 (5) |
N3 | 0.0434 (7) | 0.0338 (7) | 0.0320 (7) | 0.0009 (6) | 0.0116 (6) | −0.0009 (5) |
N4 | 0.0507 (8) | 0.0343 (7) | 0.0323 (7) | 0.0039 (6) | 0.0103 (6) | −0.0047 (6) |
C1 | 0.0384 (8) | 0.0353 (8) | 0.0360 (8) | −0.0034 (6) | 0.0130 (7) | −0.0039 (6) |
C2 | 0.0395 (8) | 0.0395 (8) | 0.0325 (8) | −0.0011 (7) | 0.0108 (7) | 0.0038 (6) |
C3 | 0.0358 (8) | 0.0351 (8) | 0.0319 (7) | −0.0013 (6) | 0.0132 (6) | 0.0005 (6) |
C4 | 0.0397 (8) | 0.0341 (8) | 0.0337 (8) | 0.0052 (6) | 0.0145 (7) | −0.0019 (6) |
C5 | 0.0436 (9) | 0.0315 (8) | 0.0424 (9) | 0.0003 (7) | 0.0155 (7) | −0.0009 (6) |
C6 | 0.0404 (9) | 0.0375 (8) | 0.0397 (8) | 0.0019 (7) | 0.0110 (7) | −0.0048 (7) |
C7 | 0.0442 (9) | 0.0389 (9) | 0.0354 (8) | 0.0089 (7) | 0.0173 (7) | 0.0012 (6) |
C8 | 0.0518 (10) | 0.0307 (8) | 0.0437 (9) | 0.0029 (7) | 0.0211 (8) | −0.0004 (7) |
C9 | 0.0443 (9) | 0.0335 (8) | 0.0406 (9) | −0.0008 (7) | 0.0152 (7) | −0.0073 (7) |
C10 | 0.0694 (13) | 0.0470 (11) | 0.0521 (11) | 0.0145 (9) | 0.0238 (10) | 0.0148 (9) |
Cl1—C1 | 1.7576 (16) | C4—C9 | 1.403 (2) |
Cl2—C2 | 1.7443 (16) | C4—C5 | 1.406 (2) |
O1—C7 | 1.384 (2) | C5—C6 | 1.395 (2) |
O1—C10 | 1.445 (2) | C5—H5 | 0.9300 |
N1—C1 | 1.343 (2) | C6—C7 | 1.410 (2) |
N1—C2 | 1.356 (2) | C6—H6 | 0.9300 |
N2—C2 | 1.318 (2) | C7—C8 | 1.405 (2) |
N2—C3 | 1.3755 (19) | C8—C9 | 1.404 (2) |
N3—C1 | 1.327 (2) | C8—H8 | 0.9300 |
N3—C3 | 1.369 (2) | C9—H9 | 0.9300 |
N4—C3 | 1.350 (2) | C10—H10A | 0.9600 |
N4—C4 | 1.438 (2) | C10—H10B | 0.9600 |
N4—H4 | 0.886 (9) | C10—H10C | 0.9600 |
C7—O1—C10 | 116.87 (14) | C6—C5—H5 | 120.1 |
C1—N1—C2 | 110.15 (13) | C4—C5—H5 | 120.1 |
C2—N2—C3 | 113.75 (13) | C5—C6—C7 | 120.69 (15) |
C1—N3—C3 | 113.13 (13) | C5—C6—H6 | 119.7 |
C3—N4—C4 | 129.06 (13) | C7—C6—H6 | 119.7 |
C3—N4—H4 | 114.0 (13) | O1—C7—C8 | 124.52 (15) |
C4—N4—H4 | 117.0 (13) | O1—C7—C6 | 115.71 (14) |
N3—C1—N1 | 129.79 (14) | C8—C7—C6 | 119.77 (15) |
N3—C1—Cl1 | 114.99 (12) | C9—C8—C7 | 119.12 (15) |
N1—C1—Cl1 | 115.21 (12) | C9—C8—H8 | 120.4 |
N2—C2—N1 | 129.06 (14) | C7—C8—H8 | 120.4 |
N2—C2—Cl2 | 115.70 (12) | C4—C9—C8 | 121.16 (15) |
N1—C2—Cl2 | 115.23 (12) | C4—C9—H9 | 119.4 |
N4—C3—N3 | 120.61 (14) | C8—C9—H9 | 119.4 |
N4—C3—N2 | 115.44 (14) | O1—C10—H10A | 109.5 |
N3—C3—N2 | 123.95 (14) | O1—C10—H10B | 109.5 |
C9—C4—C5 | 119.36 (14) | H10A—C10—H10B | 109.5 |
C9—C4—N4 | 117.49 (14) | O1—C10—H10C | 109.5 |
C5—C4—N4 | 123.13 (14) | H10A—C10—H10C | 109.5 |
C6—C5—C4 | 119.86 (15) | H10B—C10—H10C | 109.5 |
C3—N3—C1—N1 | −3.0 (3) | C3—N4—C4—C9 | −147.41 (18) |
C3—N3—C1—Cl1 | 176.03 (11) | C3—N4—C4—C5 | 33.8 (3) |
C2—N1—C1—N3 | −0.3 (3) | C9—C4—C5—C6 | 2.1 (2) |
C2—N1—C1—Cl1 | −179.33 (12) | N4—C4—C5—C6 | −179.15 (15) |
C3—N2—C2—N1 | −1.7 (3) | C4—C5—C6—C7 | −0.9 (3) |
C3—N2—C2—Cl2 | 179.86 (11) | C10—O1—C7—C8 | 0.2 (2) |
C1—N1—C2—N2 | 2.9 (3) | C10—O1—C7—C6 | 179.60 (16) |
C1—N1—C2—Cl2 | −178.59 (12) | C5—C6—C7—O1 | 179.70 (15) |
C4—N4—C3—N3 | −1.4 (3) | C5—C6—C7—C8 | −0.9 (3) |
C4—N4—C3—N2 | 178.88 (15) | O1—C7—C8—C9 | −179.16 (16) |
C1—N3—C3—N4 | −175.35 (15) | C6—C7—C8—C9 | 1.5 (2) |
C1—N3—C3—N2 | 4.4 (2) | C5—C4—C9—C8 | −1.5 (2) |
C2—N2—C3—N4 | 177.34 (15) | N4—C4—C9—C8 | 179.69 (15) |
C2—N2—C3—N3 | −2.4 (2) | C7—C8—C9—C4 | −0.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···N3i | 0.89 (1) | 2.65 (2) | 3.377 (2) | 141 (2) |
Symmetry code: (i) x, −y+3/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C10H8Cl2N4O |
Mr | 271.10 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 294 |
a, b, c (Å) | 7.6090 (16), 20.635 (4), 8.3081 (17) |
β (°) | 115.908 (3) |
V (Å3) | 1173.3 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.54 |
Crystal size (mm) | 0.24 × 0.22 × 0.18 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.881, 0.909 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6560, 2400, 2016 |
Rint | 0.019 |
(sin θ/λ)max (Å−1) | 0.626 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.087, 1.05 |
No. of reflections | 2400 |
No. of parameters | 159 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.18, −0.36 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···N3i | 0.886 (9) | 2.646 (15) | 3.377 (2) | 140.6 (17) |
Symmetry code: (i) x, −y+3/2, z+1/2. |
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2,4,6-Trichloro-1,3,5-triazine and its derivatives have been widely investigated, in fields such as drugs and light stabilizers (Mathias & Simanek, 1994; Manasek & Hrdlovik, 1990).
In the present paper, we describe the title compound, (I), (Fig. 1) which has been synthesied from 4-methoxylaniline and 2,4,6-trichloro-1,3,5-triazine. The bond lengths and angles in (I) are within normal ranges. The dihedral angle between the triazine ring and the benzene ring is 29.57 (8)°. The crystal packing is stabilized by weak N—H···N interactions (Table 1, Fig. 2).