6-Chloro-N2-propyl-N4-(2,4,4-trimethyl­pentan-2-yl)-1,3,5-triazine-2,4-diamine

Jiang, Y.-P.; Qiu, T.; Wang, L.-E.; Wang, J.-N.

doi:10.1107/S1600536807025950

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6-Chloro-N²-propyl-N⁴-(2,4,4-trimethylpentan-2-yl)-1,3,5-triazine-2,4-diamine

Y.-P. Jiang, T. Qiu, L.-E. Wang and J.-N. Wang

In the title compound, C₁₄H₂₆ClN₅, the triazine ring is almost planar and both pendant alkyl chains are disordered; the site occupancy ratios are 0.5:0.5 for the tert-butyl chain and approximately 0.6:0.4 for the n-propyl chain. The crystal packing is consolidated by N—H

N hydrogen bonds, resulting in infinite chains propagating along [001].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807025950/hb2437sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807025950/hb2437Isup2.hkl Contains datablock I

CCDC reference: 655594

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R factor = 0.061
wR factor = 0.199
Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.63 Ratio
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for       C10'

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.76
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.77 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C9'
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C11
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C13'
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C8
PLAT301_ALERT_3_C Main Residue  Disorder .........................      23.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H6A    ..  H11E    ..       1.84 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          3
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      26.00 Deg.
              C11  -C8   -C11'    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      22.30 Deg.
              C10' -C8   -C10     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      29.60 Deg.
              C9   -C8   -C9'     1.555   1.555   1.555

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......        124

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  14 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  11 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 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, (I), is an important intermediate of hindered light stabilizers (Borzatta & Carrozza, 1991). The triazine ring in (I) is essentially planar with an r.m.s. deviation from the mean plane of 0.0173 Å. Both alkyl side chains are disordered. The crystal packing is consolidated by N—H···N hydrogen bonds (Table 1).

Related literature top

For a related structure, see: Deng et al. (2006). For background, see: Kaiser & Thurston (1951); Borzatta & Carrozza, (1991).

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. Then 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. Propan-1-amine (12.80 g, 0.217 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 title compound (52.18 g) was obtained in powder form in a yield of 80.2%. Crystals of (I) were obtained by slow evaporation of a solution of methanol.

Structure description top

For a related structure, see: Deng et al. (2006). For background, see: Kaiser & Thurston (1951); Borzatta & Carrozza, (1991).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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

Fig. 1. A view of (I) with displacement ellopsoids drawn at the 30% probability level and H atoms are shown as spheres of arbitrary radius.

6-Chloro-N²-propyl-N⁴-(2,4,4-trimethylpentan-2-yl)-1,3,5-triazine- 2,4-diamine top

Crystal data top

C₁₄H₂₆ClN₅	F(000) = 1296
M_r = 299.85	D_x = 1.147 Mg m⁻³
Monoclinic, C2/c	Melting point = 427–429 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 19.354 (4) Å	Cell parameters from 2001 reflections
b = 8.1265 (16) Å	θ = 2.7–21.9°
c = 22.312 (4) Å	µ = 0.22 mm⁻¹
β = 98.211 (4)°	T = 294 K
V = 3473.3 (11) Å³	Prism, colorless
Z = 8	0.24 × 0.20 × 0.14 mm

Data collection top

Bruker SMART 1000 CCD diffractometer	3070 independent reflections
Radiation source: fine-focus sealed tube	1927 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −22→22
T_min = 0.949, T_max = 0.970	k = −9→9
8715 measured reflections	l = −26→21

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.200	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.1008P)² + 4.0532P] where P = (F_o² + 2F_c²)/3
3070 reflections	(Δ/σ)_max = 0.001
227 parameters	Δρ_max = 0.82 e Å⁻³
124 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₄H₂₆ClN₅	V = 3473.3 (11) Å³
M_r = 299.85	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 19.354 (4) Å	µ = 0.22 mm⁻¹
b = 8.1265 (16) Å	T = 294 K
c = 22.312 (4) Å	0.24 × 0.20 × 0.14 mm
β = 98.211 (4)°

Data collection top

Bruker SMART 1000 CCD diffractometer	3070 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	1927 reflections with I > 2σ(I)
T_min = 0.949, T_max = 0.970	R_int = 0.043
8715 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	124 restraints
wR(F²) = 0.200	H-atom parameters constrained
S = 1.04	Δρ_max = 0.82 e Å⁻³
3070 reflections	Δρ_min = −0.30 e Å⁻³
227 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	1.12154 (5)	0.54065 (15)	0.15428 (4)	0.0679 (4)
N1	1.01263 (14)	0.5960 (3)	0.07597 (11)	0.0428 (7)
N2	1.01295 (13)	0.7029 (3)	0.17513 (11)	0.0410 (7)
N3	0.91505 (13)	0.7532 (3)	0.09899 (11)	0.0409 (7)
N4	0.91928 (15)	0.6518 (4)	0.00350 (12)	0.0561 (9)
H4	0.9410	0.5949	−0.0204	0.067*
N5	0.91712 (13)	0.8346 (4)	0.19857 (12)	0.0438 (7)
H5	0.9419	0.8406	0.2337	0.053*
C1	1.03866 (16)	0.6232 (4)	0.13245 (15)	0.0409 (8)
C2	0.94741 (16)	0.7621 (4)	0.15558 (14)	0.0366 (8)
C3	0.94923 (17)	0.6693 (4)	0.06058 (14)	0.0407 (8)
C4	0.84639 (17)	0.9060 (4)	0.19365 (16)	0.0441 (8)
C5	0.79276 (19)	0.7711 (5)	0.1755 (2)	0.0646 (11)
H5A	0.7965	0.7341	0.1353	0.097*
H5B	0.7467	0.8136	0.1767	0.097*
H5C	0.8013	0.6805	0.2032	0.097*
C6	0.8389 (2)	0.9614 (6)	0.25784 (18)	0.0707 (12)
H6A	0.8720	1.0470	0.2702	0.106*
H6B	0.8474	0.8697	0.2850	0.106*
H6C	0.7925	1.0021	0.2586	0.106*
C7	0.83308 (19)	1.0435 (4)	0.14660 (17)	0.0529 (9)
H7A	0.7848	1.0766	0.1461	0.063*
H7B	0.8357	0.9926	0.1077	0.063*
C8	0.8755 (2)	1.2031 (5)	0.1477 (2)	0.0786 (14)
C9	0.9459 (5)	1.1708 (16)	0.1267 (5)	0.081 (3)	0.50
H9A	0.9720	1.2715	0.1280	0.122*	0.50
H9B	0.9386	1.1292	0.0861	0.122*	0.50
H9C	0.9714	1.0913	0.1530	0.122*	0.50
C10	0.8316 (8)	1.301 (2)	0.0956 (7)	0.111 (5)	0.50
H10A	0.8526	1.4068	0.0916	0.166*	0.50
H10B	0.7850	1.3154	0.1047	0.166*	0.50
H10C	0.8302	1.2413	0.0583	0.166*	0.50
C11	0.8522 (8)	1.3241 (19)	0.1929 (6)	0.110 (5)	0.50
H11A	0.8794	1.4230	0.1933	0.165*	0.50
H11B	0.8587	1.2757	0.2325	0.165*	0.50
H11C	0.8037	1.3500	0.1812	0.165*	0.50
C9'	0.9560 (5)	1.1719 (18)	0.1623 (6)	0.100 (4)	0.50
H9'A	0.9804	1.2749	0.1629	0.150*	0.50
H9'B	0.9706	1.1020	0.1317	0.150*	0.50
H9'C	0.9664	1.1196	0.2011	0.150*	0.50
C10'	0.8601 (9)	1.299 (3)	0.0881 (7)	0.133 (6)	0.50
H10D	0.8874	1.3978	0.0908	0.200*	0.50
H10E	0.8114	1.3264	0.0807	0.200*	0.50
H10F	0.8718	1.2321	0.0555	0.200*	0.50
C11'	0.8846 (7)	1.3011 (17)	0.2076 (5)	0.090 (4)	0.50
H11D	0.9120	1.3978	0.2033	0.135*	0.50
H11E	0.9078	1.2337	0.2396	0.135*	0.50
H11F	0.8396	1.3328	0.2170	0.135*	0.50
C12	0.8530 (2)	0.7219 (6)	−0.02092 (18)	0.0785 (15)	0.592 (8)
H12A	0.8196	0.6870	0.0051	0.094*	0.592 (8)
H12B	0.8389	0.6708	−0.0601	0.094*	0.592 (8)
C13	0.8442 (6)	0.8996 (11)	−0.0295 (5)	0.119 (3)	0.592 (8)
H13A	0.8581	0.9583	0.0081	0.143*	0.592 (8)
H13B	0.7961	0.9269	−0.0448	0.143*	0.592 (8)
C14	0.8909 (6)	0.9395 (18)	−0.0745 (5)	0.129 (3)	0.592 (8)
H14A	0.8929	1.0567	−0.0794	0.193*	0.592 (8)
H14B	0.8732	0.8896	−0.1126	0.193*	0.592 (8)
H14C	0.9368	0.8980	−0.0607	0.193*	0.592 (8)
C12'	0.8530 (2)	0.7219 (6)	−0.02092 (18)	0.0785 (15)	0.408 (8)
H12C	0.8317	0.7718	0.0115	0.094*	0.408 (8)
H12D	0.8222	0.6356	−0.0390	0.094*	0.408 (8)
C13'	0.8621 (9)	0.8539 (16)	−0.0695 (6)	0.122 (3)	0.408 (8)
H13C	0.8866	0.8072	−0.1005	0.146*	0.408 (8)
H13D	0.8167	0.8919	−0.0887	0.146*	0.408 (8)
C14'	0.9031 (9)	0.995 (2)	−0.0388 (9)	0.127 (4)	0.408 (8)
H14D	0.8821	1.0974	−0.0534	0.190*	0.408 (8)
H14E	0.9502	0.9909	−0.0475	0.190*	0.408 (8)
H14F	0.9032	0.9881	0.0042	0.190*	0.408 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0464 (6)	0.0923 (8)	0.0621 (7)	0.0296 (5)	−0.0018 (5)	−0.0159 (5)
N1	0.0408 (15)	0.0505 (18)	0.0374 (16)	0.0101 (13)	0.0058 (12)	−0.0052 (13)
N2	0.0356 (14)	0.0494 (17)	0.0384 (15)	0.0072 (13)	0.0063 (12)	−0.0056 (13)
N3	0.0414 (15)	0.0463 (17)	0.0348 (15)	0.0116 (13)	0.0042 (12)	−0.0024 (12)
N4	0.0573 (19)	0.073 (2)	0.0359 (16)	0.0262 (17)	−0.0011 (14)	−0.0091 (15)
N5	0.0354 (14)	0.0586 (19)	0.0375 (15)	0.0113 (13)	0.0054 (12)	−0.0083 (13)
C1	0.0343 (17)	0.043 (2)	0.045 (2)	0.0076 (15)	0.0056 (15)	−0.0022 (15)
C2	0.0341 (16)	0.0370 (19)	0.0390 (18)	0.0026 (14)	0.0061 (14)	−0.0030 (14)
C3	0.0436 (18)	0.042 (2)	0.0363 (18)	0.0059 (15)	0.0046 (15)	−0.0012 (14)
C4	0.0374 (18)	0.043 (2)	0.054 (2)	0.0100 (15)	0.0130 (16)	0.0000 (16)
C5	0.045 (2)	0.055 (3)	0.098 (3)	0.0007 (18)	0.020 (2)	0.007 (2)
C6	0.072 (3)	0.083 (3)	0.063 (3)	0.029 (2)	0.030 (2)	−0.001 (2)
C7	0.051 (2)	0.044 (2)	0.065 (2)	0.0107 (18)	0.0143 (18)	0.0011 (18)
C8	0.091 (3)	0.045 (3)	0.106 (4)	0.000 (2)	0.039 (3)	0.001 (2)
C9	0.085 (6)	0.064 (5)	0.102 (7)	−0.015 (5)	0.042 (5)	0.004 (6)
C10	0.122 (9)	0.081 (6)	0.135 (8)	0.001 (7)	0.039 (7)	0.051 (6)
C11	0.126 (9)	0.071 (7)	0.131 (8)	0.006 (7)	0.014 (7)	−0.027 (6)
C9'	0.102 (7)	0.079 (6)	0.125 (8)	−0.026 (5)	0.035 (6)	−0.001 (7)
C10'	0.150 (10)	0.111 (8)	0.146 (9)	−0.011 (8)	0.047 (7)	0.046 (7)
C11'	0.097 (8)	0.060 (6)	0.113 (7)	−0.012 (6)	0.016 (6)	−0.018 (5)
C12	0.075 (3)	0.107 (4)	0.048 (2)	0.038 (3)	−0.012 (2)	−0.015 (2)
C13	0.121 (4)	0.122 (4)	0.112 (4)	0.010 (3)	0.013 (3)	−0.005 (3)
C14	0.131 (5)	0.129 (5)	0.126 (5)	0.002 (4)	0.016 (4)	0.002 (4)
C12'	0.075 (3)	0.107 (4)	0.048 (2)	0.038 (3)	−0.012 (2)	−0.015 (2)
C13'	0.121 (4)	0.122 (4)	0.121 (4)	0.007 (4)	0.014 (4)	−0.001 (4)
C14'	0.129 (5)	0.128 (5)	0.122 (5)	0.003 (4)	0.016 (4)	−0.003 (4)

Geometric parameters (Å, º) top

Cl1—C1	1.743 (3)	C9—H9B	0.9600
N1—C1	1.307 (4)	C9—H9C	0.9600
N1—C3	1.363 (4)	C10—H10A	0.9600
N2—C1	1.307 (4)	C10—H10B	0.9600
N2—C2	1.369 (4)	C10—H10C	0.9600
N3—C2	1.329 (4)	C11—H11A	0.9600
N3—C3	1.342 (4)	C11—H11B	0.9600
N4—C3	1.329 (4)	C11—H11C	0.9600
N4—C12	1.438 (5)	C9'—H9'A	0.9600
N4—H4	0.8600	C9'—H9'B	0.9600
N5—C2	1.331 (4)	C9'—H9'C	0.9600
N5—C4	1.476 (4)	C10'—H10D	0.9600
N5—H5	0.8600	C10'—H10E	0.9600
C4—C5	1.524 (5)	C10'—H10F	0.9600
C4—C6	1.528 (5)	C11'—H11D	0.9600
C4—C7	1.529 (5)	C11'—H11E	0.9600
C5—H5A	0.9600	C11'—H11F	0.9600
C5—H5B	0.9600	C12—C13	1.464 (8)
C5—H5C	0.9600	C12—H12A	0.9700
C6—H6A	0.9600	C12—H12B	0.9700
C6—H6B	0.9600	C13—C14	1.478 (9)
C6—H6C	0.9600	C13—H13A	0.9700
C7—C8	1.534 (6)	C13—H13B	0.9700
C7—H7A	0.9700	C14—H14A	0.9600
C7—H7B	0.9700	C14—H14B	0.9600
C8—C11	1.522 (9)	C14—H14C	0.9600
C8—C9	1.524 (8)	C13'—C14'	1.506 (10)
C8—C10'	1.533 (9)	C13'—H13C	0.9700
C8—C11'	1.543 (8)	C13'—H13D	0.9700
C8—C10	1.557 (9)	C14'—H14D	0.9600
C8—C9'	1.566 (9)	C14'—H14E	0.9600
C9—H9A	0.9600	C14'—H14F	0.9600

C1—N1—C3	112.2 (3)	C8—C9—H9A	109.5
C1—N2—C2	112.0 (3)	C8—C9—H9B	109.5
C2—N3—C3	115.2 (3)	H9A—C9—H9B	109.5
C3—N4—C12	124.4 (3)	C8—C9—H9C	109.5
C3—N4—H4	117.8	H9A—C9—H9C	109.5
C12—N4—H4	117.8	H9B—C9—H9C	109.5
C2—N5—C4	128.3 (3)	C8—C10—H10A	109.5
C2—N5—H5	115.9	C8—C10—H10B	109.5
C4—N5—H5	115.9	H10A—C10—H10B	109.5
N2—C1—N1	130.6 (3)	C8—C10—H10C	109.5
N2—C1—Cl1	114.7 (2)	H10A—C10—H10C	109.5
N1—C1—Cl1	114.6 (2)	H10B—C10—H10C	109.5
N3—C2—N5	120.8 (3)	C8—C11—H11A	109.5
N3—C2—N2	125.0 (3)	C8—C11—H11B	109.5
N5—C2—N2	114.2 (3)	H11A—C11—H11B	109.5
N4—C3—N3	118.6 (3)	C8—C11—H11C	109.5
N4—C3—N1	116.6 (3)	H11A—C11—H11C	109.5
N3—C3—N1	124.7 (3)	H11B—C11—H11C	109.5
N5—C4—C5	109.0 (3)	C8—C9'—H9'A	109.5
N5—C4—C6	104.9 (3)	C8—C9'—H9'B	109.5
C5—C4—C6	107.9 (3)	H9'A—C9'—H9'B	109.5
N5—C4—C7	113.7 (3)	C8—C9'—H9'C	109.5
C5—C4—C7	107.6 (3)	H9'A—C9'—H9'C	109.5
C6—C4—C7	113.5 (3)	H9'B—C9'—H9'C	109.5
C4—C5—H5A	109.5	C8—C10'—H10D	109.5
C4—C5—H5B	109.5	C8—C10'—H10E	109.5
H5A—C5—H5B	109.5	H10D—C10'—H10E	109.5
C4—C5—H5C	109.5	C8—C10'—H10F	109.5
H5A—C5—H5C	109.5	H10D—C10'—H10F	109.5
H5B—C5—H5C	109.5	H10E—C10'—H10F	109.5
C4—C6—H6A	109.5	C8—C11'—H11D	109.5
C4—C6—H6B	109.5	C8—C11'—H11E	109.5
H6A—C6—H6B	109.5	H11D—C11'—H11E	109.5
C4—C6—H6C	109.5	C8—C11'—H11F	109.5
H6A—C6—H6C	109.5	H11D—C11'—H11F	109.5
H6B—C6—H6C	109.5	H11E—C11'—H11F	109.5
C4—C7—C8	124.7 (3)	N4—C12—C13	121.4 (6)
C4—C7—H7A	106.1	N4—C12—H12A	107.0
C8—C7—H7A	106.1	C13—C12—H12A	107.0
C4—C7—H7B	106.1	N4—C12—H12B	107.0
C8—C7—H7B	106.1	C13—C12—H12B	107.0
H7A—C7—H7B	106.3	H12A—C12—H12B	106.7
C11—C8—C9	132.6 (9)	C12—C13—C14	103.6 (9)
C11—C8—C10'	102.0 (12)	C12—C13—H13A	111.0
C9—C8—C10'	83.9 (8)	C14—C13—H13A	111.0
C11—C8—C7	110.4 (8)	C12—C13—H13B	111.0
C9—C8—C7	110.4 (6)	C14—C13—H13B	111.0
C10'—C8—C7	112.2 (10)	H13A—C13—H13B	109.0
C11—C8—C11'	26.0 (7)	C13—C14—H14A	109.5
C9—C8—C11'	111.0 (8)	C13—C14—H14B	109.5
C10'—C8—C11'	118.2 (12)	H14A—C14—H14B	109.5
C7—C8—C11'	116.4 (6)	C13—C14—H14C	109.5
C11—C8—C10	89.0 (10)	H14A—C14—H14C	109.5
C9—C8—C10	106.0 (8)	H14B—C14—H14C	109.5
C10'—C8—C10	22.3 (10)	C14'—C13'—H13C	110.0
C7—C8—C10	100.7 (8)	C14'—C13'—H13D	110.0
C11'—C8—C10	111.4 (10)	H13C—C13'—H13D	108.4
C11—C8—C9'	110.3 (9)	C13'—C14'—H14D	109.5
C9—C8—C9'	29.6 (6)	C13'—C14'—H14E	109.5
C10'—C8—C9'	109.1 (8)	H14D—C14'—H14E	109.5
C7—C8—C9'	112.4 (6)	C13'—C14'—H14F	109.5
C11'—C8—C9'	85.3 (8)	H14D—C14'—H14F	109.5
C10—C8—C9'	131.2 (8)	H14E—C14'—H14F	109.5

C2—N2—C1—N1	1.6 (5)	C1—N1—C3—N3	−3.1 (5)
C2—N2—C1—Cl1	−178.9 (2)	C2—N5—C4—C5	61.2 (4)
C3—N1—C1—N2	2.2 (6)	C2—N5—C4—C6	176.6 (3)
C3—N1—C1—Cl1	−177.3 (2)	C2—N5—C4—C7	−58.9 (5)
C3—N3—C2—N5	−176.4 (3)	N5—C4—C7—C8	−59.1 (4)
C3—N3—C2—N2	4.6 (5)	C5—C4—C7—C8	−179.9 (3)
C4—N5—C2—N3	3.2 (5)	C6—C4—C7—C8	60.7 (4)
C4—N5—C2—N2	−177.7 (3)	C4—C7—C8—C11	−79.3 (8)
C1—N2—C2—N3	−5.3 (5)	C4—C7—C8—C9	76.1 (7)
C1—N2—C2—N5	175.7 (3)	C4—C7—C8—C10'	167.8 (9)
C12—N4—C3—N3	2.1 (6)	C4—C7—C8—C11'	−51.6 (8)
C12—N4—C3—N1	−179.3 (4)	C4—C7—C8—C10	−172.2 (8)
C2—N3—C3—N4	178.4 (3)	C4—C7—C8—C9'	44.4 (7)
C2—N3—C3—N1	−0.1 (5)	C3—N4—C12—C13	69.5 (7)
C1—N1—C3—N4	178.5 (3)	N4—C12—C13—C14	63.0 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N1ⁱ	0.86	2.25	3.099 (4)	169
N5—H5···N2ⁱⁱ	0.86	2.38	3.135 (4)	147

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+2, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₂₆ClN₅
M_r	299.85
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	294
a, b, c (Å)	19.354 (4), 8.1265 (16), 22.312 (4)
β (°)	98.211 (4)
V (Å³)	3473.3 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.24 × 0.20 × 0.14

Data collection
Diffractometer	Bruker SMART 1000 CCD
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.949, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	8715, 3070, 1927
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.200, 1.04
No. of reflections	3070
No. of parameters	227
No. of restraints	124
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.82, −0.30

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N1ⁱ	0.86	2.25	3.099 (4)	169
N5—H5···N2ⁱⁱ	0.86	2.38	3.135 (4)	147

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+2, y, −z+1/2.

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