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The crystal structure of the title compound, C15H28ClN5, is stabilized by inter­molecular N—H...N hydrogen bonds, forming zigzag chains running along the c axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807031637/bt2407sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807031637/bt2407Isup2.hkl
Contains datablock I

CCDC reference: 658980

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.054
  • wR factor = 0.161
  • Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.42 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.55 Ratio PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C12
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C6 PLAT320_ALERT_2_C Check Hybridisation of C11 in Main Residue . ? PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5 PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C5 - C6 ... 1.43 Ang.
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 2 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

Comment top

The title compound is an intermediate in the synthesis of hindered light stabilizers (Borzatta & Carrozza, 1991). This kind of compounds is widely used (Deng et al., 2006).

The triazine ring is essentially planar. The r.m.s. deviation from the mean plane is 0.014 (3) Å.

Intermolecular N—H···N hydrogen bonds link the molecules into zigzag-like chains running along the c axis.

Related literature top

For general background, see: Borzatta & Carrozza (1991). For related structures, see: Deng et al. (2006). For related literature, see: Kaiser & Thurston (1951).

Experimental top

The title compound was prepared according to the method of Kaiser & Thurston (1951). 2,4,6-Trichloro-1,3,5-triazine (40.0 g, 0.217 mol) was dissolved in toluene (120 ml) and then cooled to 278 K. With stirring, a solution of 2,4,4-trimethylpentan-2-amine (27.5 g, 0.213 mol) in toluene (50 ml) was then added dropwise to the mixture over a period of 0.5 h. A solution of Na2CO3 (23.02 g, 0.217 mol) in water (50 ml) was then added dropwise for 0.5 h. The mixture was stirred at 273–278 K for a further 3 h, 1-butylamine(15.5 g, 0.213 mol) and solid Na2CO3 (23.02 g, 0.217 mol) were added to the mixture, maintaining the temperature at 338 k for 5 h. The organic layer was washed with water and then concentrated in vacuo. The title compound (57.8 g) was obtained as a powder form in a yield of 86.5%. Crystals were obtained by slow evaporation of a solution of methanol.

Refinement top

The coordinates of the H atoms bonded to N were refined with Uiso(H) = 1.2Ueq(N). All H atoms bonded to C were positioned geometrically (C—H = 0.96–0.97 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5eq(Cmethyl).

Structure description top

The title compound is an intermediate in the synthesis of hindered light stabilizers (Borzatta & Carrozza, 1991). This kind of compounds is widely used (Deng et al., 2006).

The triazine ring is essentially planar. The r.m.s. deviation from the mean plane is 0.014 (3) Å.

Intermolecular N—H···N hydrogen bonds link the molecules into zigzag-like chains running along the c axis.

For general background, see: Borzatta & Carrozza (1991). For related structures, see: Deng et al. (2006). For related literature, see: Kaiser & Thurston (1951).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; 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.

Figures top
[Figure 1] Fig. 1. A view of the molecule (I). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
2-Butylamino-6-chloro-4-(2,4,4-trimethylpentan-2-ylamino)-1,3,5-triazine top
Crystal data top
C15H28ClN5Dx = 1.146 Mg m3
Mr = 313.87Melting point = 156–158 K
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 19.411 (4) ÅCell parameters from 2586 reflections
b = 8.2182 (17) Åθ = 2.5–23.1°
c = 23.245 (5) ŵ = 0.21 mm1
β = 101.091 (4)°T = 294 K
V = 3638.9 (13) Å3Block, colourless
Z = 80.22 × 0.20 × 0.18 mm
F(000) = 1360
Data collection top
Bruker SMART CCD area-detector
diffractometer
3213 independent reflections
Radiation source: fine-focus sealed tube2283 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
φ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2222
Tmin = 0.955, Tmax = 0.963k = 99
8608 measured reflectionsl = 2711
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0795P)2 + 3.6231P]
where P = (Fo2 + 2Fc2)/3
3213 reflections(Δ/σ)max = 0.002
200 parametersΔρmax = 0.57 e Å3
0 restraintsΔρmin = 0.30 e Å3
Crystal data top
C15H28ClN5V = 3638.9 (13) Å3
Mr = 313.87Z = 8
Monoclinic, C2/cMo Kα radiation
a = 19.411 (4) ŵ = 0.21 mm1
b = 8.2182 (17) ÅT = 294 K
c = 23.245 (5) Å0.22 × 0.20 × 0.18 mm
β = 101.091 (4)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
3213 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2283 reflections with I > 2σ(I)
Tmin = 0.955, Tmax = 0.963Rint = 0.032
8608 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0540 restraints
wR(F2) = 0.161H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.57 e Å3
3213 reflectionsΔρmin = 0.30 e Å3
200 parameters
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
xyzUiso*/Ueq
Cl11.11711 (4)0.02496 (10)0.15825 (3)0.0586 (3)
N11.00664 (10)0.0414 (3)0.08007 (9)0.0376 (5)
N21.00846 (10)0.1316 (3)0.17761 (8)0.0375 (5)
N30.90867 (10)0.1911 (3)0.10248 (8)0.0367 (5)
N40.91215 (12)0.1087 (3)0.00839 (9)0.0441 (6)
H40.9338 (16)0.063 (4)0.0112 (14)0.053*
N50.91392 (11)0.2638 (3)0.19970 (9)0.0406 (6)
H50.9351 (15)0.245 (4)0.2334 (13)0.049*
C11.03346 (12)0.0595 (3)0.13587 (11)0.0358 (6)
C20.94263 (12)0.1942 (3)0.15820 (10)0.0338 (6)
C30.94272 (12)0.1153 (3)0.06501 (10)0.0344 (6)
C80.84288 (13)0.3361 (3)0.19418 (11)0.0420 (7)
C90.78787 (14)0.2044 (4)0.17388 (15)0.0580 (8)
H9A0.79020.17160.13470.087*
H9B0.74200.24660.17460.087*
H9C0.79690.11220.19960.087*
C100.83748 (17)0.3866 (4)0.25678 (13)0.0659 (9)
H10A0.87190.46880.27040.099*
H10B0.84580.29360.28220.099*
H10C0.79140.42900.25690.099*
C110.82914 (15)0.4783 (3)0.15022 (13)0.0478 (7)
H11A0.78110.51250.14940.057*
H11B0.82990.43160.11200.057*
C120.87304 (19)0.6361 (4)0.15384 (16)0.0684 (10)
C130.9485 (2)0.6015 (5)0.1488 (3)0.124 (2)
H13A0.94910.54040.11380.185*
H13B0.97100.53990.18230.185*
H13C0.97300.70240.14730.185*
C140.8716 (3)0.7385 (5)0.2077 (2)0.131 (2)
H14A0.89700.68390.24180.196*
H14B0.82380.75450.21200.196*
H14C0.89290.84210.20360.196*
C150.8392 (3)0.7383 (5)0.1007 (2)0.1218 (18)
H15A0.86440.83880.10070.183*
H15B0.79120.76070.10290.183*
H15C0.84090.67930.06540.183*
C40.84612 (15)0.1883 (4)0.01574 (12)0.0559 (8)
H4A0.81340.16880.01020.067*
H4B0.82670.13890.05330.067*
C50.8518 (2)0.3659 (5)0.02418 (16)0.0793 (11)
H5A0.80510.40890.03840.095*
H5B0.86940.41540.01370.095*
C60.8958 (2)0.4149 (5)0.0636 (2)0.0987 (14)
H6A0.87820.36710.10170.118*
H6B0.94270.37300.04960.118*
C70.8997 (3)0.6042 (6)0.0704 (2)0.149 (2)
H7A0.92260.62970.10230.223*
H7B0.92580.65030.03480.223*
H7C0.85310.64850.07810.223*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0456 (4)0.0801 (6)0.0485 (4)0.0282 (4)0.0048 (3)0.0040 (4)
N10.0381 (12)0.0436 (13)0.0323 (11)0.0069 (9)0.0096 (9)0.0024 (10)
N20.0337 (11)0.0484 (13)0.0314 (11)0.0066 (9)0.0089 (9)0.0011 (10)
N30.0357 (11)0.0443 (12)0.0312 (11)0.0055 (9)0.0089 (9)0.0029 (10)
N40.0415 (13)0.0603 (16)0.0312 (12)0.0123 (11)0.0087 (9)0.0062 (11)
N50.0383 (12)0.0559 (14)0.0287 (11)0.0112 (10)0.0092 (9)0.0030 (11)
C10.0332 (13)0.0395 (14)0.0359 (14)0.0056 (11)0.0097 (11)0.0013 (11)
C20.0349 (13)0.0365 (14)0.0314 (13)0.0008 (10)0.0103 (10)0.0003 (11)
C30.0372 (13)0.0365 (14)0.0307 (13)0.0010 (11)0.0098 (10)0.0005 (11)
C80.0371 (14)0.0516 (17)0.0409 (15)0.0100 (12)0.0163 (11)0.0002 (13)
C90.0413 (16)0.0580 (19)0.079 (2)0.0018 (14)0.0215 (15)0.0076 (17)
C100.072 (2)0.081 (2)0.0524 (18)0.0291 (18)0.0321 (16)0.0016 (17)
C110.0474 (16)0.0467 (16)0.0521 (17)0.0094 (13)0.0168 (13)0.0014 (14)
C120.083 (2)0.0458 (18)0.084 (2)0.0018 (17)0.036 (2)0.0050 (18)
C130.090 (3)0.069 (3)0.229 (6)0.028 (2)0.073 (4)0.005 (3)
C140.216 (6)0.061 (3)0.131 (4)0.027 (3)0.071 (4)0.039 (3)
C150.180 (5)0.061 (3)0.132 (4)0.001 (3)0.048 (4)0.034 (3)
C40.0498 (17)0.079 (2)0.0374 (15)0.0144 (16)0.0053 (13)0.0014 (15)
C50.083 (3)0.090 (3)0.062 (2)0.020 (2)0.0057 (19)0.010 (2)
C60.091 (3)0.095 (3)0.112 (3)0.015 (3)0.024 (3)0.002 (3)
C70.202 (7)0.114 (4)0.128 (5)0.052 (4)0.028 (4)0.032 (4)
Geometric parameters (Å, º) top
Cl1—C11.750 (2)C12—C141.514 (5)
N1—C11.310 (3)C12—C131.518 (5)
N1—C31.365 (3)C12—C151.532 (5)
N2—C11.307 (3)C13—H13A0.9600
N2—C21.371 (3)C13—H13B0.9600
N3—C21.336 (3)C13—H13C0.9600
N3—C31.344 (3)C14—H14A0.9600
N4—C31.337 (3)C14—H14B0.9600
N4—C41.452 (3)C14—H14C0.9600
N4—H40.77 (3)C15—H15A0.9600
N5—C21.333 (3)C15—H15B0.9600
N5—C81.484 (3)C15—H15C0.9600
N5—H50.83 (3)C4—C51.480 (5)
C8—C91.530 (4)C4—H4A0.9700
C8—C101.536 (4)C4—H4B0.9700
C8—C111.541 (4)C5—C61.425 (5)
C9—H9A0.9600C5—H5A0.9700
C9—H9B0.9600C5—H5B0.9700
C9—H9C0.9600C6—C71.567 (6)
C10—H10A0.9600C6—H6A0.9700
C10—H10B0.9600C6—H6B0.9700
C10—H10C0.9600C7—H7A0.9600
C11—C121.545 (4)C7—H7B0.9600
C11—H11A0.9700C7—H7C0.9600
C11—H11B0.9700
C1—N1—C3111.8 (2)C14—C12—C11114.4 (3)
C1—N2—C2112.4 (2)C13—C12—C11111.6 (3)
C2—N3—C3115.1 (2)C15—C12—C11105.6 (3)
C3—N4—C4123.6 (2)C12—C13—H13A109.5
C3—N4—H4114 (2)C12—C13—H13B109.5
C4—N4—H4122 (2)H13A—C13—H13B109.5
C2—N5—C8128.3 (2)C12—C13—H13C109.5
C2—N5—H5114 (2)H13A—C13—H13C109.5
C8—N5—H5116 (2)H13B—C13—H13C109.5
N2—C1—N1130.8 (2)C12—C14—H14A109.5
N2—C1—Cl1114.49 (18)C12—C14—H14B109.5
N1—C1—Cl1114.74 (18)H14A—C14—H14B109.5
N5—C2—N3120.8 (2)C12—C14—H14C109.5
N5—C2—N2114.6 (2)H14A—C14—H14C109.5
N3—C2—N2124.6 (2)H14B—C14—H14C109.5
N4—C3—N3118.5 (2)C12—C15—H15A109.5
N4—C3—N1116.3 (2)C12—C15—H15B109.5
N3—C3—N1125.2 (2)H15A—C15—H15B109.5
N5—C8—C9109.0 (2)C12—C15—H15C109.5
N5—C8—C10104.9 (2)H15A—C15—H15C109.5
C9—C8—C10108.2 (2)H15B—C15—H15C109.5
N5—C8—C11113.6 (2)N4—C4—C5114.4 (3)
C9—C8—C11108.1 (2)N4—C4—H4A108.7
C10—C8—C11112.9 (2)C5—C4—H4A108.7
C8—C9—H9A109.5N4—C4—H4B108.7
C8—C9—H9B109.5C5—C4—H4B108.7
H9A—C9—H9B109.5H4A—C4—H4B107.6
C8—C9—H9C109.5C6—C5—C4115.6 (3)
H9A—C9—H9C109.5C6—C5—H5A108.4
H9B—C9—H9C109.5C4—C5—H5A108.4
C8—C10—H10A109.5C6—C5—H5B108.4
C8—C10—H10B109.5C4—C5—H5B108.4
H10A—C10—H10B109.5H5A—C5—H5B107.4
C8—C10—H10C109.5C5—C6—C7113.1 (4)
H10A—C10—H10C109.5C5—C6—H6A109.0
H10B—C10—H10C109.5C7—C6—H6A109.0
C8—C11—C12125.2 (3)C5—C6—H6B109.0
C8—C11—H11A106.0C7—C6—H6B109.0
C12—C11—H11A106.0H6A—C6—H6B107.8
C8—C11—H11B106.0C6—C7—H7A109.5
C12—C11—H11B106.0C6—C7—H7B109.5
H11A—C11—H11B106.3H7A—C7—H7B109.5
C14—C12—C13109.9 (4)C6—C7—H7C109.5
C14—C12—C15106.8 (3)H7A—C7—H7C109.5
C13—C12—C15108.1 (4)H7B—C7—H7C109.5
C2—N2—C1—N11.4 (4)C1—N1—C3—N4177.6 (2)
C2—N2—C1—Cl1179.32 (17)C1—N1—C3—N33.2 (4)
C3—N1—C1—N21.7 (4)C2—N5—C8—C960.6 (3)
C3—N1—C1—Cl1177.58 (17)C2—N5—C8—C10176.3 (3)
C8—N5—C2—N34.2 (4)C2—N5—C8—C1160.0 (4)
C8—N5—C2—N2177.0 (2)N5—C8—C11—C1258.3 (3)
C3—N3—C2—N5179.1 (2)C9—C8—C11—C12179.4 (3)
C3—N3—C2—N22.3 (4)C10—C8—C11—C1261.0 (3)
C1—N2—C2—N5177.7 (2)C8—C11—C12—C1463.0 (4)
C1—N2—C2—N33.6 (4)C8—C11—C12—C1362.5 (4)
C4—N4—C3—N34.2 (4)C8—C11—C12—C15179.8 (3)
C4—N4—C3—N1176.5 (3)C3—N4—C4—C577.2 (4)
C2—N3—C3—N4179.5 (2)N4—C4—C5—C661.1 (4)
C2—N3—C3—N11.4 (4)C4—C5—C6—C7179.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···N1i0.77 (3)2.31 (3)3.079 (3)171 (3)
N5—H5···N2ii0.83 (3)2.34 (3)3.151 (3)167 (3)
Symmetry codes: (i) x+2, y, z; (ii) x+2, y, z+1/2.

Experimental details

Crystal data
Chemical formulaC15H28ClN5
Mr313.87
Crystal system, space groupMonoclinic, C2/c
Temperature (K)294
a, b, c (Å)19.411 (4), 8.2182 (17), 23.245 (5)
β (°) 101.091 (4)
V3)3638.9 (13)
Z8
Radiation typeMo Kα
µ (mm1)0.21
Crystal size (mm)0.22 × 0.20 × 0.18
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.955, 0.963
No. of measured, independent and
observed [I > 2σ(I)] reflections
8608, 3213, 2283
Rint0.032
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.161, 1.04
No. of reflections3213
No. of parameters200
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.57, 0.30

Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···N1i0.77 (3)2.31 (3)3.079 (3)171 (3)
N5—H5···N2ii0.83 (3)2.34 (3)3.151 (3)167 (3)
Symmetry codes: (i) x+2, y, z; (ii) x+2, y, z+1/2.
 

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