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In the title compound, C18H26ClN5, there are four mol­ecules in the asymmetric unit, two of which show disorder of their tert-butyl groups in 0.58 (2):0.42 (2) and 0.753 (4):0.247 (4) ratios. A complex network of N—H...N hydrogen bonds helps to establish the packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807042559/hb2528sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807042559/hb2528Isup2.hkl
Contains datablock I

CCDC reference: 664195

Key indicators

  • Single-crystal X-ray study
  • T = 113 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in main residue
  • R factor = 0.056
  • wR factor = 0.134
  • Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.00 Ratio PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.99 Ratio PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.32 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.04 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.30 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.09 Ratio
Alert level C CELLV02_ALERT_1_C The supplied cell volume s.u. differs from that calculated from the cell parameter s.u.'s by > 2 Calculated cell volume su = 15.18 Cell volume su given = 13.00 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg. PLAT213_ALERT_2_C Atom C9' has ADP max/min Ratio ............. 3.10 prola PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C35 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C6 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C24 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C31 PLAT301_ALERT_3_C Main Residue Disorder ......................... 6.00 Perc. PLAT411_ALERT_2_C Short Inter H...H Contact H32 .. H48B .. 2.14 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 18.80 Deg. C11' -C6 -C11 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 22.40 Deg. C9 -C6 -C9' 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 22.80 Deg. C10' -C6 -C10 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 30.00 Deg. C64' -C60 -C64 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 43.30 Deg. C65 -C60 -C65' 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 30.60 Deg. C63 -C60 -C63' 1.555 1.555 1.555
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 96
0 ALERT level A = In general: serious problem 6 ALERT level B = Potentially serious problem 18 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 15 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 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 in the preparation of hindered light stabilizers (Borzatta & Carrozza, 1991; Deng et al., 2006).

There are four molecules of (I) in the asymmetic unit, with simplar conformations, although two of the molecules show disorder of their tert-butyl groupings. In each case, the triazine ring is essentially planar (Fig. 1). The molecules are linked by strong, near-linear, intermolecular N—H···N hydrogen bonds (Table 1).

Related literature top

For related literature, see: Borzatta & Carrozza (1991); Deng et al. (2006). For synthesis, 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 (20.0 g, 0.109 mol) was dissolved in toluene (65 ml) and then cooled to 278 K. With stirring, a solution of 2,4,4-trimethylpentan-2-amine (13.75 g, 0.107 mol) in toluene (35 ml) was then added dropwise to the mixture over a period of 30 min. Then, a solution of Na2CO3 (11.51 g, 0.109 mol) in water (30 ml) was then added dropwise for 30 min. The mixture was stirred at 273–278 K for a further 3 h and phenylmethanamine (11.61 g, 0.109 mol) and solid Na2CO3 (11.51 g, 0.109 mol) were added to the mixture, maintaining the temperature at 358 K for 4.5 h. The organic layer was washed with water and then concentrated in vacuo. The title compound (28.47 g) was obtained in powder form in a yield of 75.4%. Colourles blocks (I) were obtained by slow evaporation of a solution of methanol (m.p. 421–423 K).

Refinement top

The N-bound H atoms were located in a difference map and their positions and Uiso values were freely refined.

The C-bound H atoms were positioned geometrically (C—H = 0.98–0.99 Å), and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Structure description top

The title compound, (I), is an important intermediate in the preparation of hindered light stabilizers (Borzatta & Carrozza, 1991; Deng et al., 2006).

There are four molecules of (I) in the asymmetic unit, with simplar conformations, although two of the molecules show disorder of their tert-butyl groupings. In each case, the triazine ring is essentially planar (Fig. 1). The molecules are linked by strong, near-linear, intermolecular N—H···N hydrogen bonds (Table 1).

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

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1996); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).

Figures top
[Figure 1] Fig. 1. A view of the structure of the Cl2 molecule in (I). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
N2-Benzyl-6-chloro-N4-(2,4,4-trimethylpentan-2-yl)-1,3,5-triazine- 2,4-diamine top
Crystal data top
C18H26ClN5Z = 8
Mr = 347.89F(000) = 1488
Triclinic, P1Dx = 1.206 Mg m3
Hall symbol: -P 1Melting point = 421–423 K
a = 8.0987 (16) ÅMo Kα radiation, λ = 0.71073 Å
b = 20.811 (4) ÅCell parameters from 8593 reflections
c = 23.984 (5) Åθ = 1.8–27.9°
α = 105.36 (3)°µ = 0.21 mm1
β = 96.33 (3)°T = 113 K
γ = 96.46 (3)°Block, colorless
V = 3831.6 (13) Å30.34 × 0.32 × 0.18 mm
Data collection top
Rigaku Saturn
diffractometer
17590 independent reflections
Radiation source: rotating anode14508 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.035
Detector resolution: 7.31 pixels mm-1θmax = 27.8°, θmin = 1.5°
ω scansh = 1010
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
k = 2727
Tmin = 0.932, Tmax = 0.963l = 3131
35937 measured reflections
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0532P)2 + 1.4707P]
where P = (Fo2 + 2Fc2)/3
17590 reflections(Δ/σ)max = 0.001
979 parametersΔρmax = 0.55 e Å3
96 restraintsΔρmin = 0.53 e Å3
Crystal data top
C18H26ClN5γ = 96.46 (3)°
Mr = 347.89V = 3831.6 (13) Å3
Triclinic, P1Z = 8
a = 8.0987 (16) ÅMo Kα radiation
b = 20.811 (4) ŵ = 0.21 mm1
c = 23.984 (5) ÅT = 113 K
α = 105.36 (3)°0.34 × 0.32 × 0.18 mm
β = 96.33 (3)°
Data collection top
Rigaku Saturn
diffractometer
17590 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
14508 reflections with I > 2σ(I)
Tmin = 0.932, Tmax = 0.963Rint = 0.035
35937 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05696 restraints
wR(F2) = 0.134H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.55 e Å3
17590 reflectionsΔρmin = 0.53 e Å3
979 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*/UeqOcc. (<1)
Cl10.25176 (6)0.22828 (2)0.156778 (19)0.02256 (11)
N10.51718 (18)0.39243 (7)0.10231 (6)0.0168 (3)
N20.45024 (19)0.34162 (7)0.17781 (6)0.0177 (3)
N30.33144 (18)0.28719 (7)0.07868 (6)0.0165 (3)
N40.61749 (19)0.44332 (7)0.20073 (7)0.0180 (3)
N50.3981 (2)0.33659 (8)0.00755 (7)0.0188 (3)
C10.5267 (2)0.39225 (9)0.15850 (7)0.0161 (4)
C20.3578 (2)0.29361 (9)0.13527 (7)0.0165 (4)
C30.4182 (2)0.33940 (9)0.06421 (7)0.0160 (3)
C40.7199 (2)0.50406 (9)0.19479 (8)0.0189 (4)
C50.8540 (2)0.48759 (9)0.15411 (8)0.0206 (4)
H5A0.91100.53140.15200.025*
H5B0.79190.46460.11460.025*
C60.9950 (2)0.44549 (10)0.16437 (8)0.0239 (4)
C70.7949 (3)0.54427 (10)0.25749 (8)0.0265 (4)
H7A0.70450.55940.27940.040*
H7B0.87290.58350.25680.040*
H7C0.85520.51560.27640.040*
C80.6039 (3)0.54624 (10)0.16903 (9)0.0266 (4)
H8A0.55230.52060.12930.040*
H8B0.66990.58820.16790.040*
H8C0.51580.55670.19350.040*
C91.111 (2)0.4693 (7)0.2234 (4)0.056 (4)0.42 (2)
H9A1.04920.45960.25390.084*0.42 (2)
H9B1.14790.51790.23280.084*0.42 (2)
H9C1.20860.44550.22100.084*0.42 (2)
C100.9190 (13)0.3714 (4)0.1544 (9)0.043 (3)0.42 (2)
H10A1.00950.34390.15420.065*0.42 (2)
H10B0.84500.35550.11680.065*0.42 (2)
H10C0.85410.36790.18590.065*0.42 (2)
C111.108 (2)0.4471 (9)0.1174 (6)0.043 (3)0.42 (2)
H11A1.19430.41820.12020.064*0.42 (2)
H11B1.16210.49350.12330.064*0.42 (2)
H11C1.04010.43080.07860.064*0.42 (2)
C9'1.1350 (11)0.4899 (6)0.2119 (5)0.065 (3)0.58 (2)
H9'11.09310.50090.24950.097*0.58 (2)
H9'21.17030.53150.20180.097*0.58 (2)
H9'31.23100.46550.21450.097*0.58 (2)
C10'0.9370 (13)0.3817 (5)0.1808 (5)0.049 (2)0.58 (2)
H10D0.84280.35470.15170.073*0.58 (2)
H10E0.90080.39380.21940.073*0.58 (2)
H10F1.02990.35540.18170.073*0.58 (2)
C11'1.0693 (14)0.4258 (6)0.1073 (3)0.0358 (18)0.58 (2)
H11D1.16530.40220.11290.054*0.58 (2)
H11E1.10640.46650.09610.054*0.58 (2)
H11F0.98360.39610.07640.054*0.58 (2)
C120.4864 (2)0.38653 (9)0.01533 (8)0.0198 (4)
H12A0.49940.43110.01390.024*
H12B0.41660.38920.05100.024*
C130.6584 (2)0.37214 (9)0.03011 (8)0.0199 (4)
C140.7036 (3)0.30838 (11)0.03965 (10)0.0302 (5)
H14A0.62660.27230.03590.036*
C150.8611 (3)0.29648 (12)0.05476 (10)0.0365 (5)
H15A0.89090.25250.06100.044*
C160.9740 (3)0.34835 (12)0.06067 (9)0.0327 (5)
H161.08150.34030.07080.039*
C170.9296 (3)0.41180 (12)0.05183 (10)0.0348 (5)
H171.00660.44750.05610.042*
C180.7725 (3)0.42401 (11)0.03661 (9)0.0299 (5)
H180.74310.46800.03060.036*
Cl20.41948 (6)0.53961 (2)0.346225 (19)0.02303 (11)
N60.60553 (19)0.36615 (7)0.39037 (6)0.0179 (3)
N70.54407 (19)0.42739 (7)0.32025 (6)0.0184 (3)
N80.49763 (19)0.47124 (7)0.41881 (6)0.0178 (3)
N90.6442 (2)0.32725 (8)0.29300 (7)0.0194 (3)
N100.5585 (2)0.41230 (8)0.48486 (7)0.0196 (3)
C190.5968 (2)0.37354 (9)0.33635 (7)0.0167 (4)
C200.4964 (2)0.47114 (9)0.36373 (8)0.0172 (4)
C210.5555 (2)0.41615 (9)0.43003 (7)0.0166 (4)
C220.6925 (2)0.26095 (9)0.29462 (8)0.0198 (4)
C230.8450 (2)0.26562 (10)0.34155 (8)0.0218 (4)
H23A0.80660.28220.37990.026*
H23B0.86450.21870.33810.026*
C241.0196 (2)0.30679 (11)0.34632 (9)0.0275 (4)
C250.7218 (3)0.22687 (10)0.23221 (8)0.0276 (4)
H25A0.61540.21730.20570.041*
H25B0.76560.18460.23120.041*
H25C0.80310.25690.21980.041*
C260.5431 (2)0.21836 (10)0.30844 (9)0.0262 (4)
H26A0.51900.24010.34760.039*
H26B0.57070.17330.30690.039*
H26C0.44420.21450.27960.039*
C271.1306 (3)0.29118 (16)0.39577 (12)0.0548 (8)
H27A1.13600.24270.38580.082*
H27B1.08280.30480.43220.082*
H27C1.24410.31600.40090.082*
C281.0154 (3)0.38242 (12)0.36303 (14)0.0533 (7)
H28A1.13030.40650.37030.080*
H28B0.96290.39550.39850.080*
H28C0.95030.39400.33110.080*
C291.1032 (3)0.28702 (15)0.29119 (11)0.0500 (7)
H29A1.04510.30260.26030.075*
H29B1.09680.23790.27810.075*
H29C1.22120.30790.29990.075*
C300.6211 (2)0.35846 (9)0.50476 (8)0.0195 (4)
H30A0.59380.31630.47240.023*
H30B0.56150.35180.53710.023*
C310.8088 (2)0.37065 (9)0.52564 (8)0.0204 (4)
C320.8865 (3)0.31716 (11)0.53284 (11)0.0358 (5)
H320.82200.27370.52350.043*
C331.0568 (3)0.32539 (13)0.55349 (11)0.0403 (6)
H331.10730.28780.55850.048*
C341.1519 (3)0.38748 (13)0.56667 (11)0.0426 (6)
H341.26880.39350.58020.051*
C351.0751 (3)0.44103 (14)0.55990 (16)0.0713 (11)
H351.13990.48450.56920.086*
C360.9044 (3)0.43288 (12)0.53970 (14)0.0537 (8)
H360.85370.47070.53560.064*
Cl31.14070 (7)0.03951 (2)0.64751 (2)0.02864 (12)
N110.90224 (19)0.12914 (7)0.61493 (6)0.0176 (3)
N121.01421 (19)0.07117 (8)0.68179 (6)0.0197 (3)
N131.01909 (19)0.02732 (8)0.57954 (6)0.0189 (3)
N140.9165 (2)0.17138 (8)0.71538 (7)0.0210 (3)
N150.9065 (2)0.08231 (8)0.51668 (6)0.0187 (3)
C370.9436 (2)0.12389 (9)0.66904 (7)0.0176 (4)
C381.0467 (2)0.02792 (9)0.63493 (8)0.0191 (4)
C390.9421 (2)0.08014 (9)0.57184 (7)0.0168 (4)
C400.8286 (2)0.23066 (9)0.71594 (8)0.0210 (4)
C410.6431 (2)0.20115 (9)0.68843 (8)0.0206 (4)
H41A0.64790.16470.65270.025*
H41B0.59470.17920.71610.025*
C420.5123 (2)0.24412 (9)0.67094 (8)0.0227 (4)
C430.9193 (2)0.27622 (10)0.68524 (9)0.0250 (4)
H43A1.03870.28680.70170.038*
H43B0.87020.31800.69080.038*
H43C0.90760.25320.64340.038*
C440.8433 (3)0.26835 (10)0.78098 (8)0.0303 (5)
H44A0.78580.23930.80130.045*
H44B0.79130.30940.78520.045*
H44C0.96210.28040.79800.045*
C450.5010 (3)0.30788 (10)0.71917 (9)0.0318 (5)
H45A0.60400.34000.72520.048*
H45B0.48770.29620.75560.048*
H45C0.40420.32830.70760.048*
C460.3414 (3)0.19809 (11)0.65819 (11)0.0350 (5)
H46A0.31520.18790.69410.052*
H46B0.34690.15610.62840.052*
H46C0.25370.22110.64390.052*
C470.5413 (3)0.26333 (11)0.61505 (9)0.0291 (5)
H47A0.44630.28400.60240.044*
H47B0.55120.22280.58430.044*
H47C0.64490.29550.62270.044*
C480.8381 (2)0.13786 (9)0.50105 (8)0.0192 (4)
H48A0.89270.14730.46850.023*
H48B0.86740.17850.53490.023*
C490.6487 (2)0.12544 (9)0.48282 (8)0.0198 (4)
C500.5413 (3)0.08988 (10)0.50896 (9)0.0246 (4)
H500.58640.07010.53760.029*
C510.3679 (3)0.08275 (10)0.49370 (10)0.0297 (5)
H510.29540.05820.51180.036*
C520.3012 (3)0.11149 (12)0.45208 (11)0.0360 (5)
H520.18290.10720.44200.043*
C530.4066 (3)0.14630 (13)0.42534 (11)0.0400 (6)
H530.36100.16560.39650.048*
C540.5797 (3)0.15324 (11)0.44046 (9)0.0298 (5)
H540.65170.17720.42170.036*
Cl40.31144 (6)0.73479 (2)0.15285 (2)0.02536 (11)
N160.04068 (19)0.89942 (7)0.10058 (6)0.0178 (3)
N170.11611 (19)0.84876 (8)0.17520 (6)0.0189 (3)
N180.22056 (19)0.79254 (7)0.07524 (6)0.0175 (3)
N190.0458 (2)0.95158 (8)0.19963 (7)0.0206 (3)
N200.1436 (2)0.84117 (8)0.00481 (6)0.0186 (3)
C550.0378 (2)0.89986 (9)0.15664 (8)0.0174 (4)
C560.2033 (2)0.80012 (9)0.13198 (8)0.0178 (4)
C570.1327 (2)0.84514 (9)0.06163 (7)0.0166 (4)
C580.1483 (3)1.01300 (9)0.19478 (8)0.0248 (4)
C590.2904 (2)0.99697 (10)0.15752 (9)0.0272 (4)
H59A0.34691.04080.15540.033*
H59B0.23460.97260.11740.033*
C600.4322 (3)0.95702 (12)0.17192 (10)0.0369 (5)
C610.2131 (3)1.05436 (12)0.25774 (10)0.0443 (6)
H61A0.11861.06970.27720.067*
H61B0.29281.09350.25780.067*
H61C0.26961.02640.27860.067*
C620.0340 (3)1.05308 (10)0.16575 (10)0.0329 (5)
H62A0.00971.02660.12550.049*
H62B0.09901.09570.16560.049*
H62C0.05981.06240.18770.049*
C630.3762 (5)0.8940 (2)0.1873 (2)0.0516 (10)0.753 (4)
H63A0.29090.86490.15590.077*0.753 (4)
H63B0.32830.90530.22380.077*0.753 (4)
H63C0.47250.87040.19220.077*0.753 (4)
C640.5174 (5)0.9369 (2)0.11552 (16)0.0456 (9)0.753 (4)
H64A0.61420.91460.12340.068*0.753 (4)
H64B0.55500.97740.10420.068*0.753 (4)
H64C0.43630.90600.08370.068*0.753 (4)
C650.5730 (5)1.0033 (2)0.21834 (18)0.0660 (12)0.753 (4)
H65A0.53551.01260.25680.099*0.753 (4)
H65B0.59991.04570.20860.099*0.753 (4)
H65C0.67330.98100.21920.099*0.753 (4)
C63'0.3532 (14)0.8805 (4)0.1520 (6)0.0510 (15)0.247 (4)
H63D0.43950.85300.15920.076*0.247 (4)
H63E0.30950.86720.11010.076*0.247 (4)
H63F0.26140.87340.17410.076*0.247 (4)
C64'0.5729 (13)0.9674 (6)0.1397 (5)0.0512 (14)0.247 (4)
H64D0.65330.93680.14460.077*0.247 (4)
H64E0.62911.01410.15500.077*0.247 (4)
H64F0.53010.95830.09810.077*0.247 (4)
C65'0.4932 (16)0.9692 (7)0.2389 (3)0.0663 (16)0.247 (4)
H65D0.40080.95310.25720.099*0.247 (4)
H65E0.52941.01740.25740.099*0.247 (4)
H65F0.58760.94460.24380.099*0.247 (4)
C660.0526 (2)0.89078 (9)0.01753 (8)0.0189 (4)
H66A0.03790.93520.01200.023*
H66B0.12130.89420.05310.023*
C670.1189 (2)0.87506 (9)0.03230 (8)0.0195 (4)
C680.1535 (3)0.80974 (10)0.04905 (10)0.0302 (5)
H680.06970.77340.05040.036*
C690.3099 (3)0.79679 (11)0.06397 (11)0.0372 (5)
H690.33220.75170.07530.045*
C700.4326 (3)0.84886 (11)0.06239 (9)0.0323 (5)
H700.53990.83990.07210.039*
C710.3991 (3)0.91358 (12)0.04675 (11)0.0394 (6)
H710.48260.94970.04640.047*
C720.2429 (3)0.92689 (11)0.03128 (11)0.0337 (5)
H720.22140.97210.01990.040*
H40.605 (3)0.4400 (10)0.2346 (10)0.024 (6)*
H50.339 (3)0.3010 (12)0.0155 (10)0.035 (7)*
H90.611 (3)0.3310 (10)0.2585 (9)0.021 (5)*
H100.534 (3)0.4500 (12)0.5119 (10)0.037 (6)*
H140.963 (3)0.1670 (10)0.7469 (9)0.022 (6)*
H150.931 (3)0.0484 (12)0.4890 (11)0.039 (7)*
H190.033 (3)0.9481 (12)0.2344 (11)0.034 (7)*
H200.198 (3)0.8040 (12)0.0189 (10)0.030 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0266 (2)0.0209 (2)0.0187 (2)0.00383 (18)0.00524 (17)0.00532 (17)
N10.0178 (7)0.0168 (7)0.0149 (7)0.0020 (6)0.0026 (6)0.0031 (6)
N20.0189 (8)0.0175 (7)0.0151 (7)0.0007 (6)0.0026 (6)0.0031 (6)
N30.0168 (7)0.0171 (7)0.0147 (7)0.0007 (6)0.0035 (6)0.0030 (6)
N40.0217 (8)0.0162 (7)0.0142 (7)0.0009 (6)0.0035 (6)0.0023 (6)
N50.0199 (8)0.0183 (8)0.0157 (7)0.0026 (6)0.0006 (6)0.0038 (6)
C10.0158 (8)0.0160 (8)0.0157 (8)0.0026 (7)0.0020 (7)0.0029 (7)
C20.0157 (8)0.0170 (8)0.0173 (8)0.0033 (7)0.0057 (7)0.0038 (7)
C30.0141 (8)0.0166 (8)0.0167 (8)0.0023 (7)0.0023 (7)0.0036 (7)
C40.0206 (9)0.0130 (8)0.0205 (9)0.0016 (7)0.0028 (7)0.0018 (7)
C50.0203 (9)0.0194 (9)0.0217 (9)0.0012 (7)0.0035 (7)0.0057 (7)
C60.0182 (9)0.0296 (10)0.0231 (10)0.0044 (8)0.0020 (7)0.0063 (8)
C70.0290 (11)0.0214 (10)0.0228 (10)0.0039 (8)0.0045 (8)0.0019 (8)
C80.0290 (11)0.0205 (10)0.0312 (11)0.0065 (8)0.0068 (8)0.0069 (8)
C90.068 (8)0.051 (6)0.038 (5)0.035 (5)0.021 (5)0.004 (4)
C100.024 (3)0.033 (4)0.085 (8)0.015 (3)0.014 (5)0.029 (5)
C110.035 (6)0.052 (8)0.048 (5)0.022 (5)0.018 (5)0.014 (5)
C9'0.020 (3)0.093 (7)0.060 (5)0.020 (4)0.012 (3)0.011 (4)
C10'0.044 (4)0.061 (4)0.064 (5)0.032 (3)0.021 (4)0.041 (4)
C11'0.031 (4)0.048 (5)0.039 (3)0.020 (3)0.017 (3)0.019 (3)
C120.0228 (9)0.0192 (9)0.0168 (8)0.0002 (7)0.0016 (7)0.0058 (7)
C130.0226 (9)0.0224 (9)0.0144 (8)0.0018 (7)0.0020 (7)0.0053 (7)
C140.0273 (11)0.0243 (10)0.0393 (12)0.0045 (8)0.0091 (9)0.0075 (9)
C150.0358 (13)0.0325 (12)0.0438 (13)0.0132 (10)0.0122 (10)0.0091 (10)
C160.0247 (11)0.0465 (13)0.0271 (11)0.0078 (10)0.0068 (8)0.0086 (10)
C170.0268 (11)0.0407 (13)0.0398 (13)0.0001 (10)0.0099 (9)0.0162 (10)
C180.0295 (11)0.0264 (11)0.0370 (12)0.0028 (9)0.0081 (9)0.0137 (9)
Cl20.0296 (2)0.0206 (2)0.0194 (2)0.00947 (18)0.00033 (18)0.00568 (17)
N60.0208 (8)0.0187 (8)0.0141 (7)0.0046 (6)0.0032 (6)0.0033 (6)
N70.0218 (8)0.0183 (8)0.0146 (7)0.0033 (6)0.0019 (6)0.0037 (6)
N80.0196 (8)0.0182 (7)0.0151 (7)0.0050 (6)0.0014 (6)0.0033 (6)
N90.0264 (8)0.0175 (8)0.0145 (7)0.0064 (6)0.0025 (6)0.0040 (6)
N100.0252 (8)0.0208 (8)0.0149 (7)0.0081 (7)0.0047 (6)0.0058 (6)
C190.0170 (8)0.0168 (8)0.0149 (8)0.0013 (7)0.0012 (7)0.0029 (7)
C200.0165 (8)0.0156 (8)0.0183 (8)0.0020 (7)0.0003 (7)0.0040 (7)
C210.0163 (8)0.0170 (8)0.0149 (8)0.0004 (7)0.0004 (7)0.0037 (7)
C220.0235 (9)0.0169 (9)0.0183 (9)0.0051 (7)0.0024 (7)0.0033 (7)
C230.0235 (10)0.0241 (10)0.0191 (9)0.0071 (8)0.0042 (7)0.0065 (8)
C240.0192 (10)0.0355 (11)0.0263 (10)0.0056 (8)0.0042 (8)0.0051 (9)
C250.0372 (12)0.0232 (10)0.0199 (9)0.0111 (9)0.0027 (8)0.0002 (8)
C260.0255 (10)0.0202 (10)0.0308 (11)0.0007 (8)0.0018 (8)0.0059 (8)
C270.0255 (12)0.090 (2)0.0485 (16)0.0002 (13)0.0087 (11)0.0279 (15)
C280.0269 (12)0.0358 (14)0.086 (2)0.0069 (10)0.0103 (13)0.0010 (13)
C290.0297 (13)0.0741 (19)0.0410 (14)0.0010 (12)0.0176 (11)0.0059 (13)
C300.0246 (10)0.0178 (9)0.0163 (8)0.0038 (7)0.0031 (7)0.0048 (7)
C310.0230 (10)0.0217 (9)0.0164 (8)0.0053 (7)0.0026 (7)0.0043 (7)
C320.0278 (11)0.0295 (11)0.0550 (15)0.0055 (9)0.0019 (10)0.0213 (11)
C330.0304 (12)0.0454 (14)0.0543 (15)0.0130 (11)0.0030 (11)0.0278 (12)
C340.0259 (12)0.0445 (14)0.0484 (15)0.0061 (10)0.0071 (10)0.0026 (11)
C350.0333 (15)0.0303 (14)0.128 (3)0.0046 (11)0.0209 (17)0.0017 (16)
C360.0322 (13)0.0213 (11)0.096 (2)0.0017 (10)0.0116 (13)0.0069 (13)
Cl30.0402 (3)0.0260 (2)0.0201 (2)0.0180 (2)0.0017 (2)0.00425 (18)
N110.0196 (8)0.0164 (7)0.0154 (7)0.0038 (6)0.0024 (6)0.0015 (6)
N120.0221 (8)0.0192 (8)0.0164 (7)0.0048 (6)0.0007 (6)0.0028 (6)
N130.0211 (8)0.0186 (8)0.0160 (7)0.0055 (6)0.0007 (6)0.0028 (6)
N140.0267 (9)0.0209 (8)0.0145 (8)0.0077 (7)0.0003 (6)0.0028 (6)
N150.0250 (8)0.0177 (8)0.0139 (7)0.0077 (6)0.0019 (6)0.0037 (6)
C370.0166 (8)0.0185 (9)0.0158 (8)0.0019 (7)0.0005 (7)0.0028 (7)
C380.0202 (9)0.0181 (9)0.0176 (9)0.0035 (7)0.0004 (7)0.0034 (7)
C390.0165 (8)0.0172 (9)0.0152 (8)0.0011 (7)0.0016 (7)0.0029 (7)
C400.0268 (10)0.0176 (9)0.0172 (9)0.0066 (8)0.0034 (7)0.0010 (7)
C410.0227 (9)0.0184 (9)0.0223 (9)0.0045 (7)0.0078 (7)0.0060 (7)
C420.0226 (10)0.0205 (9)0.0268 (10)0.0056 (8)0.0089 (8)0.0066 (8)
C430.0238 (10)0.0200 (9)0.0299 (10)0.0022 (8)0.0041 (8)0.0048 (8)
C440.0431 (13)0.0254 (11)0.0196 (10)0.0114 (9)0.0026 (9)0.0003 (8)
C450.0362 (12)0.0264 (11)0.0367 (12)0.0141 (9)0.0147 (10)0.0077 (9)
C460.0236 (11)0.0337 (12)0.0494 (14)0.0061 (9)0.0093 (10)0.0121 (10)
C470.0295 (11)0.0308 (11)0.0298 (11)0.0086 (9)0.0038 (9)0.0116 (9)
C480.0232 (9)0.0180 (9)0.0179 (9)0.0061 (7)0.0022 (7)0.0067 (7)
C490.0229 (9)0.0165 (9)0.0194 (9)0.0058 (7)0.0032 (7)0.0025 (7)
C500.0270 (10)0.0220 (10)0.0254 (10)0.0038 (8)0.0037 (8)0.0079 (8)
C510.0251 (10)0.0256 (11)0.0399 (12)0.0004 (8)0.0076 (9)0.0118 (9)
C520.0215 (11)0.0406 (13)0.0487 (14)0.0049 (9)0.0002 (10)0.0189 (11)
C530.0264 (12)0.0508 (15)0.0516 (15)0.0071 (10)0.0016 (10)0.0319 (12)
C540.0254 (11)0.0365 (12)0.0333 (11)0.0069 (9)0.0040 (9)0.0193 (9)
Cl40.0315 (3)0.0222 (2)0.0201 (2)0.00605 (19)0.00489 (19)0.00582 (18)
N160.0177 (7)0.0193 (8)0.0150 (7)0.0001 (6)0.0011 (6)0.0041 (6)
N170.0204 (8)0.0188 (8)0.0152 (7)0.0013 (6)0.0006 (6)0.0035 (6)
N180.0185 (8)0.0182 (7)0.0143 (7)0.0005 (6)0.0025 (6)0.0036 (6)
N190.0239 (8)0.0191 (8)0.0154 (8)0.0040 (6)0.0014 (6)0.0022 (6)
N200.0215 (8)0.0185 (8)0.0129 (7)0.0019 (6)0.0012 (6)0.0023 (6)
C550.0157 (8)0.0188 (9)0.0163 (8)0.0020 (7)0.0016 (7)0.0031 (7)
C560.0194 (9)0.0163 (8)0.0178 (8)0.0011 (7)0.0039 (7)0.0050 (7)
C570.0144 (8)0.0180 (9)0.0172 (8)0.0036 (7)0.0029 (7)0.0040 (7)
C580.0279 (10)0.0185 (9)0.0228 (10)0.0068 (8)0.0027 (8)0.0017 (8)
C590.0216 (10)0.0275 (10)0.0321 (11)0.0030 (8)0.0028 (8)0.0109 (9)
C600.0231 (11)0.0446 (14)0.0434 (13)0.0027 (10)0.0001 (9)0.0160 (11)
C610.0544 (16)0.0348 (13)0.0290 (12)0.0208 (11)0.0066 (11)0.0054 (10)
C620.0352 (12)0.0207 (10)0.0449 (13)0.0040 (9)0.0109 (10)0.0110 (9)
C630.0415 (17)0.059 (2)0.072 (2)0.0204 (15)0.0201 (19)0.039 (2)
C640.0376 (18)0.056 (2)0.0485 (19)0.0175 (15)0.0118 (15)0.0174 (16)
C650.0374 (19)0.084 (3)0.063 (2)0.0076 (17)0.0108 (16)0.0044 (19)
C63'0.041 (2)0.057 (2)0.070 (3)0.019 (2)0.019 (3)0.034 (3)
C64'0.043 (2)0.058 (3)0.056 (3)0.015 (2)0.011 (2)0.016 (2)
C65'0.044 (2)0.080 (3)0.063 (3)0.009 (2)0.013 (2)0.009 (2)
C660.0221 (9)0.0189 (9)0.0171 (8)0.0026 (7)0.0037 (7)0.0073 (7)
C670.0202 (9)0.0220 (9)0.0162 (8)0.0039 (7)0.0020 (7)0.0054 (7)
C680.0258 (11)0.0222 (10)0.0408 (12)0.0018 (8)0.0078 (9)0.0052 (9)
C690.0312 (12)0.0275 (11)0.0503 (14)0.0106 (9)0.0112 (10)0.0016 (10)
C700.0243 (11)0.0393 (12)0.0343 (12)0.0103 (9)0.0079 (9)0.0082 (10)
C710.0256 (11)0.0326 (12)0.0641 (16)0.0034 (9)0.0151 (11)0.0175 (11)
C720.0263 (11)0.0217 (10)0.0554 (14)0.0052 (8)0.0117 (10)0.0120 (10)
Geometric parameters (Å, º) top
Cl1—C21.7489 (19)Cl3—C381.7472 (19)
N1—C31.342 (2)N11—C371.340 (2)
N1—C11.342 (2)N11—C391.342 (2)
N2—C21.313 (2)N12—C381.314 (2)
N2—C11.372 (2)N12—C371.380 (2)
N3—C21.319 (2)N13—C381.319 (2)
N3—C31.370 (2)N13—C391.367 (2)
N4—C11.336 (2)N14—C371.334 (2)
N4—C41.480 (2)N14—C401.490 (2)
N4—H40.85 (2)N14—H140.84 (2)
N5—C31.336 (2)N15—C391.336 (2)
N5—C121.454 (2)N15—C481.453 (2)
N5—H50.85 (2)N15—H150.89 (2)
C4—C71.532 (3)C40—C431.521 (3)
C4—C81.542 (3)C40—C441.534 (3)
C4—C51.546 (3)C40—C411.558 (3)
C5—C61.552 (3)C41—C421.553 (3)
C5—H5A0.9900C41—H41A0.9900
C5—H5B0.9900C41—H41B0.9900
C6—C10'1.522 (6)C42—C451.531 (3)
C6—C11'1.530 (6)C42—C471.531 (3)
C6—C111.533 (8)C42—C461.542 (3)
C6—C91.535 (7)C43—H43A0.9800
C6—C9'1.536 (6)C43—H43B0.9800
C6—C101.540 (7)C43—H43C0.9800
C7—H7A0.9800C44—H44A0.9800
C7—H7B0.9800C44—H44B0.9800
C7—H7C0.9800C44—H44C0.9800
C8—H8A0.9800C45—H45A0.9800
C8—H8B0.9800C45—H45B0.9800
C8—H8C0.9800C45—H45C0.9800
C9—H9A0.9800C46—H46A0.9800
C9—H9B0.9800C46—H46B0.9800
C9—H9C0.9800C46—H46C0.9800
C10—H10A0.9800C47—H47A0.9800
C10—H10B0.9800C47—H47B0.9800
C10—H10C0.9800C47—H47C0.9800
C11—H11A0.9800C48—C491.522 (3)
C11—H11B0.9800C48—H48A0.9900
C11—H11C0.9800C48—H48B0.9900
C9'—H9'10.9800C49—C501.385 (3)
C9'—H9'20.9800C49—C541.392 (3)
C9'—H9'30.9800C50—C511.392 (3)
C10'—H10D0.9800C50—H500.9500
C10'—H10E0.9800C51—C521.384 (3)
C10'—H10F0.9800C51—H510.9500
C11'—H11D0.9800C52—C531.376 (3)
C11'—H11E0.9800C52—H520.9500
C11'—H11F0.9800C53—C541.390 (3)
C12—C131.517 (3)C53—H530.9500
C12—H12A0.9900C54—H540.9500
C12—H12B0.9900Cl4—C561.7480 (19)
C13—C141.384 (3)N16—C551.340 (2)
C13—C181.393 (3)N16—C571.342 (2)
C14—C151.395 (3)N17—C561.311 (2)
C14—H14A0.9500N17—C551.376 (2)
C15—C161.381 (3)N18—C561.317 (2)
C15—H15A0.9500N18—C571.370 (2)
C16—C171.376 (3)N19—C551.332 (2)
C16—H160.9500N19—C581.483 (2)
C17—C181.394 (3)N19—H190.87 (2)
C17—H170.9500N20—C571.336 (2)
C18—H180.9500N20—C661.451 (2)
Cl2—C201.7475 (18)N20—H200.87 (2)
N6—C191.340 (2)C58—C611.527 (3)
N6—C211.344 (2)C58—C621.541 (3)
N7—C201.315 (2)C58—C591.546 (3)
N7—C191.374 (2)C59—C601.552 (3)
N8—C201.319 (2)C59—H59A0.9900
N8—C211.365 (2)C59—H59B0.9900
N9—C191.340 (2)C60—C64'1.473 (7)
N9—C221.485 (2)C60—C631.490 (4)
N9—H90.87 (2)C60—C651.540 (4)
N10—C211.336 (2)C60—C641.566 (4)
N10—C301.448 (2)C60—C65'1.572 (7)
N10—H100.93 (2)C60—C63'1.574 (8)
C22—C251.534 (3)C61—H61A0.9800
C22—C261.537 (3)C61—H61B0.9800
C22—C231.553 (3)C61—H61C0.9800
C23—C241.545 (3)C62—H62A0.9800
C23—H23A0.9900C62—H62B0.9800
C23—H23B0.9900C62—H62C0.9800
C24—C281.523 (3)C63—H63A0.9800
C24—C291.532 (3)C63—H63B0.9800
C24—C271.535 (3)C63—H63C0.9800
C25—H25A0.9800C64—H64A0.9800
C25—H25B0.9800C64—H64B0.9800
C25—H25C0.9800C64—H64C0.9800
C26—H26A0.9800C65—H65A0.9800
C26—H26B0.9800C65—H65B0.9800
C26—H26C0.9800C65—H65C0.9800
C27—H27A0.9800C63'—H63D0.9800
C27—H27B0.9800C63'—H63E0.9800
C27—H27C0.9800C63'—H63F0.9800
C28—H28A0.9800C64'—H64D0.9800
C28—H28B0.9800C64'—H64E0.9800
C28—H28C0.9800C64'—H64F0.9800
C29—H29A0.9800C65'—H65D0.9800
C29—H29B0.9800C65'—H65E0.9800
C29—H29C0.9800C65'—H65F0.9800
C30—C311.518 (3)C66—C671.520 (3)
C30—H30A0.9900C66—H66A0.9900
C30—H30B0.9900C66—H66B0.9900
C31—C361.370 (3)C67—C681.382 (3)
C31—C321.378 (3)C67—C721.382 (3)
C32—C331.389 (3)C68—C691.389 (3)
C32—H320.9500C68—H680.9500
C33—C341.367 (3)C69—C701.375 (3)
C33—H330.9500C69—H690.9500
C34—C351.373 (4)C70—C711.366 (3)
C34—H340.9500C70—H700.9500
C35—C361.390 (3)C71—C721.394 (3)
C35—H350.9500C71—H710.9500
C36—H360.9500C72—H720.9500
C3—N1—C1114.95 (15)C37—N11—C39115.23 (15)
C2—N2—C1112.59 (15)C38—N12—C37112.49 (15)
C2—N3—C3112.39 (15)C38—N13—C39112.45 (15)
C1—N4—C4128.27 (16)C37—N14—C40127.89 (16)
C1—N4—H4112.2 (15)C37—N14—H14112.3 (14)
C4—N4—H4119.4 (14)C40—N14—H14119.7 (14)
C3—N5—C12122.93 (15)C39—N15—C48123.26 (15)
C3—N5—H5115.9 (16)C39—N15—H15116.7 (15)
C12—N5—H5120.8 (16)C48—N15—H15120.0 (15)
N4—C1—N1120.58 (17)N14—C37—N11120.34 (16)
N4—C1—N2114.53 (16)N14—C37—N12115.08 (16)
N1—C1—N2124.89 (16)N11—C37—N12124.58 (16)
N2—C2—N3129.94 (17)N12—C38—N13129.98 (17)
N2—C2—Cl1115.24 (14)N12—C38—Cl3115.36 (14)
N3—C2—Cl1114.81 (13)N13—C38—Cl3114.66 (13)
N5—C3—N1118.79 (16)N15—C39—N11118.75 (16)
N5—C3—N3116.04 (15)N15—C39—N13116.09 (15)
N1—C3—N3125.16 (16)N11—C39—N13125.16 (16)
N4—C4—C7104.89 (15)N14—C40—C43110.35 (16)
N4—C4—C8109.24 (15)N14—C40—C44104.19 (15)
C7—C4—C8108.56 (15)C43—C40—C44108.77 (16)
N4—C4—C5113.26 (14)N14—C40—C41105.76 (15)
C7—C4—C5113.24 (16)C43—C40—C41115.28 (16)
C8—C4—C5107.53 (15)C44—C40—C41111.89 (16)
C4—C5—C6123.98 (16)C42—C41—C40123.57 (16)
C4—C5—H5A106.3C42—C41—H41A106.4
C6—C5—H5A106.3C40—C41—H41A106.4
C4—C5—H5B106.3C42—C41—H41B106.4
C6—C5—H5B106.3C40—C41—H41B106.4
H5A—C5—H5B106.4H41A—C41—H41B106.5
C10'—C6—C11'108.6 (4)C45—C42—C47109.11 (17)
C10'—C6—C11123.2 (7)C45—C42—C46107.95 (17)
C11'—C6—C1118.8 (5)C47—C42—C46107.61 (17)
C10'—C6—C987.4 (5)C45—C42—C41114.06 (17)
C11'—C6—C9120.3 (8)C47—C42—C41112.53 (16)
C11—C6—C9106.5 (7)C46—C42—C41105.22 (16)
C10'—C6—C9'109.5 (4)C40—C43—H43A109.5
C11'—C6—C9'107.6 (5)C40—C43—H43B109.5
C11—C6—C9'90.5 (7)H43A—C43—H43B109.5
C9—C6—C9'22.4 (6)C40—C43—H43C109.5
C10'—C6—C1022.8 (4)H43A—C43—H43C109.5
C11'—C6—C1089.9 (6)H43B—C43—H43C109.5
C11—C6—C10107.2 (5)C40—C44—H44A109.5
C9—C6—C10108.5 (5)C40—C44—H44B109.5
C9'—C6—C10129.4 (5)H44A—C44—H44B109.5
C10'—C6—C5114.8 (4)C40—C44—H44C109.5
C11'—C6—C5106.8 (5)H44A—C44—H44C109.5
C11—C6—C5106.5 (7)H44B—C44—H44C109.5
C9—C6—C5117.6 (6)C42—C45—H45A109.5
C9'—C6—C5109.3 (5)C42—C45—H45B109.5
C10—C6—C5110.0 (4)H45A—C45—H45B109.5
C4—C7—H7A109.5C42—C45—H45C109.5
C4—C7—H7B109.5H45A—C45—H45C109.5
H7A—C7—H7B109.5H45B—C45—H45C109.5
C4—C7—H7C109.5C42—C46—H46A109.5
H7A—C7—H7C109.5C42—C46—H46B109.5
H7B—C7—H7C109.5H46A—C46—H46B109.5
C4—C8—H8A109.5C42—C46—H46C109.5
C4—C8—H8B109.5H46A—C46—H46C109.5
H8A—C8—H8B109.5H46B—C46—H46C109.5
C4—C8—H8C109.5C42—C47—H47A109.5
H8A—C8—H8C109.5C42—C47—H47B109.5
H8B—C8—H8C109.5H47A—C47—H47B109.5
C6—C9—H9A109.5C42—C47—H47C109.5
C6—C9—H9B109.5H47A—C47—H47C109.5
C6—C9—H9C109.5H47B—C47—H47C109.5
C6—C10—H10A109.5N15—C48—C49114.48 (16)
C6—C10—H10B109.5N15—C48—H48A108.6
C6—C10—H10C109.5C49—C48—H48A108.6
C6—C11—H11A109.5N15—C48—H48B108.6
C6—C11—H11B109.5C49—C48—H48B108.6
C6—C11—H11C109.5H48A—C48—H48B107.6
C6—C9'—H9'1109.5C50—C49—C54118.62 (18)
C6—C9'—H9'2109.5C50—C49—C48122.09 (17)
H9'1—C9'—H9'2109.5C54—C49—C48119.22 (18)
C6—C9'—H9'3109.5C49—C50—C51120.71 (19)
H9'1—C9'—H9'3109.5C49—C50—H50119.6
H9'2—C9'—H9'3109.5C51—C50—H50119.6
C6—C10'—H10D109.5C52—C51—C50120.0 (2)
C6—C10'—H10E109.5C52—C51—H51120.0
H10D—C10'—H10E109.5C50—C51—H51120.0
C6—C10'—H10F109.5C53—C52—C51119.8 (2)
H10D—C10'—H10F109.5C53—C52—H52120.1
H10E—C10'—H10F109.5C51—C52—H52120.1
C6—C11'—H11D109.5C52—C53—C54120.2 (2)
C6—C11'—H11E109.5C52—C53—H53119.9
H11D—C11'—H11E109.5C54—C53—H53119.9
C6—C11'—H11F109.5C53—C54—C49120.7 (2)
H11D—C11'—H11F109.5C53—C54—H54119.7
H11E—C11'—H11F109.5C49—C54—H54119.7
N5—C12—C13114.27 (15)C55—N16—C57115.08 (16)
N5—C12—H12A108.7C56—N17—C55112.68 (15)
C13—C12—H12A108.7C56—N18—C57112.29 (15)
N5—C12—H12B108.7C55—N19—C58128.10 (17)
C13—C12—H12B108.7C55—N19—H19113.4 (16)
H12A—C12—H12B107.6C58—N19—H19118.4 (16)
C14—C13—C18118.67 (18)C57—N20—C66123.28 (16)
C14—C13—C12122.10 (18)C57—N20—H20115.8 (15)
C18—C13—C12119.18 (17)C66—N20—H20120.4 (15)
C13—C14—C15120.6 (2)N19—C55—N16121.02 (17)
C13—C14—H14A119.7N19—C55—N17114.32 (16)
C15—C14—H14A119.7N16—C55—N17124.66 (16)
C16—C15—C14120.3 (2)N17—C56—N18130.00 (17)
C16—C15—H15A119.9N17—C56—Cl4114.97 (14)
C14—C15—H15A119.9N18—C56—Cl4115.02 (14)
C17—C16—C15119.5 (2)N20—C57—N16118.83 (17)
C17—C16—H16120.2N20—C57—N18115.96 (16)
C15—C16—H16120.2N16—C57—N18125.21 (16)
C16—C17—C18120.4 (2)N19—C58—C61105.07 (17)
C16—C17—H17119.8N19—C58—C62109.08 (16)
C18—C17—H17119.8C61—C58—C62108.82 (18)
C13—C18—C17120.4 (2)N19—C58—C59112.79 (16)
C13—C18—H18119.8C61—C58—C59113.11 (18)
C17—C18—H18119.8C62—C58—C59107.85 (17)
C19—N6—C21115.00 (15)C58—C59—C60124.08 (18)
C20—N7—C19112.49 (15)C58—C59—H59A106.3
C20—N8—C21112.58 (15)C60—C59—H59A106.3
C19—N9—C22127.59 (16)C58—C59—H59B106.3
C19—N9—H9113.5 (14)C60—C59—H59B106.3
C22—N9—H9115.6 (14)H59A—C59—H59B106.4
C21—N10—C30123.30 (15)C64'—C60—C63125.7 (5)
C21—N10—H10116.1 (14)C64'—C60—C6575.0 (5)
C30—N10—H10119.9 (14)C63—C60—C65111.7 (3)
N6—C19—N9120.68 (16)C64'—C60—C59110.6 (5)
N6—C19—N7124.97 (15)C63—C60—C59115.5 (2)
N9—C19—N7114.34 (16)C65—C60—C59110.8 (2)
N7—C20—N8129.78 (17)C64'—C60—C6430.0 (5)
N7—C20—Cl2115.44 (14)C63—C60—C64107.6 (3)
N8—C20—Cl2114.78 (13)C65—C60—C64104.2 (3)
N10—C21—N6118.81 (16)C59—C60—C64106.2 (2)
N10—C21—N8116.04 (15)C64'—C60—C65'112.0 (6)
N6—C21—N8125.14 (16)C63—C60—C65'72.2 (5)
N9—C22—C25105.41 (15)C65—C60—C65'43.3 (5)
N9—C22—C26108.75 (15)C59—C60—C65'115.1 (5)
C25—C22—C26107.91 (16)C64—C60—C65'134.1 (5)
N9—C22—C23113.99 (15)C64'—C60—C63'109.6 (6)
C25—C22—C23113.25 (16)C63—C60—C63'30.6 (4)
C26—C22—C23107.34 (16)C65—C60—C63'137.7 (5)
C24—C23—C22124.97 (17)C59—C60—C63'106.5 (5)
C24—C23—H23A106.1C64—C60—C63'83.4 (5)
C22—C23—H23A106.1C65'—C60—C63'102.4 (6)
C24—C23—H23B106.1C58—C61—H61A109.5
C22—C23—H23B106.1C58—C61—H61B109.5
H23A—C23—H23B106.3H61A—C61—H61B109.5
C28—C24—C29109.1 (2)C58—C61—H61C109.5
C28—C24—C27108.0 (2)H61A—C61—H61C109.5
C29—C24—C27107.4 (2)H61B—C61—H61C109.5
C28—C24—C23112.44 (17)C58—C62—H62A109.5
C29—C24—C23114.03 (18)C58—C62—H62B109.5
C27—C24—C23105.61 (18)H62A—C62—H62B109.5
C22—C25—H25A109.5C58—C62—H62C109.5
C22—C25—H25B109.5H62A—C62—H62C109.5
H25A—C25—H25B109.5H62B—C62—H62C109.5
C22—C25—H25C109.5C60—C63—H63A109.5
H25A—C25—H25C109.5C60—C63—H63B109.5
H25B—C25—H25C109.5C60—C63—H63C109.5
C22—C26—H26A109.5C60—C64—H64A109.5
C22—C26—H26B109.5C60—C64—H64B109.5
H26A—C26—H26B109.5C60—C64—H64C109.5
C22—C26—H26C109.5C60—C65—H65A109.5
H26A—C26—H26C109.5C60—C65—H65B109.5
H26B—C26—H26C109.5C60—C65—H65C109.5
C24—C27—H27A109.5C60—C63'—H63D109.5
C24—C27—H27B109.5C60—C63'—H63E109.5
H27A—C27—H27B109.5H63D—C63'—H63E109.5
C24—C27—H27C109.5C60—C63'—H63F109.5
H27A—C27—H27C109.5H63D—C63'—H63F109.5
H27B—C27—H27C109.5H63E—C63'—H63F109.5
C24—C28—H28A109.5C60—C64'—H64D109.5
C24—C28—H28B109.5C60—C64'—H64E109.5
H28A—C28—H28B109.5H64D—C64'—H64E109.5
C24—C28—H28C109.5C60—C64'—H64F109.5
H28A—C28—H28C109.5H64D—C64'—H64F109.5
H28B—C28—H28C109.5H64E—C64'—H64F109.5
C24—C29—H29A109.5C60—C65'—H65D109.5
C24—C29—H29B109.5C60—C65'—H65E109.5
H29A—C29—H29B109.5H65D—C65'—H65E109.5
C24—C29—H29C109.5C60—C65'—H65F109.5
H29A—C29—H29C109.5H65D—C65'—H65F109.5
H29B—C29—H29C109.5H65E—C65'—H65F109.5
N10—C30—C31114.48 (16)N20—C66—C67114.16 (15)
N10—C30—H30A108.6N20—C66—H66A108.7
C31—C30—H30A108.6C67—C66—H66A108.7
N10—C30—H30B108.6N20—C66—H66B108.7
C31—C30—H30B108.6C67—C66—H66B108.7
H30A—C30—H30B107.6H66A—C66—H66B107.6
C36—C31—C32118.1 (2)C68—C67—C72118.38 (18)
C36—C31—C30123.17 (18)C68—C67—C66121.88 (18)
C32—C31—C30118.71 (18)C72—C67—C66119.70 (17)
C31—C32—C33121.5 (2)C67—C68—C69120.6 (2)
C31—C32—H32119.2C67—C68—H68119.7
C33—C32—H32119.2C69—C68—H68119.7
C34—C33—C32120.0 (2)C70—C69—C68120.4 (2)
C34—C33—H33120.0C70—C69—H69119.8
C32—C33—H33120.0C68—C69—H69119.8
C33—C34—C35118.7 (2)C71—C70—C69119.5 (2)
C33—C34—H34120.6C71—C70—H70120.2
C35—C34—H34120.6C69—C70—H70120.2
C34—C35—C36121.2 (2)C70—C71—C72120.2 (2)
C34—C35—H35119.4C70—C71—H71119.9
C36—C35—H35119.4C72—C71—H71119.9
C31—C36—C35120.4 (2)C67—C72—C71120.8 (2)
C31—C36—H36119.8C67—C72—H72119.6
C35—C36—H36119.8C71—C72—H72119.6
C4—N4—C1—N11.5 (3)C40—N14—C37—N115.8 (3)
C4—N4—C1—N2177.59 (16)C40—N14—C37—N12173.85 (17)
C3—N1—C1—N4178.05 (16)C39—N11—C37—N14177.08 (17)
C3—N1—C1—N23.0 (2)C39—N11—C37—N123.3 (3)
C2—N2—C1—N4177.79 (15)C38—N12—C37—N14176.42 (17)
C2—N2—C1—N13.2 (2)C38—N12—C37—N113.9 (3)
C1—N2—C2—N31.1 (3)C37—N12—C38—N131.5 (3)
C1—N2—C2—Cl1178.40 (12)C37—N12—C38—Cl3178.67 (13)
C3—N3—C2—N20.9 (3)C39—N13—C38—N121.2 (3)
C3—N3—C2—Cl1179.60 (12)C39—N13—C38—Cl3178.60 (13)
C12—N5—C3—N13.7 (3)C48—N15—C39—N114.8 (3)
C12—N5—C3—N3177.45 (15)C48—N15—C39—N13174.53 (16)
C1—N1—C3—N5178.20 (15)C37—N11—C39—N15179.27 (16)
C1—N1—C3—N30.6 (2)C37—N11—C39—N130.1 (3)
C2—N3—C3—N5180.00 (15)C38—N13—C39—N15178.64 (16)
C2—N3—C3—N11.2 (2)C38—N13—C39—N112.0 (3)
C1—N4—C4—C7179.82 (17)C37—N14—C40—C4361.0 (2)
C1—N4—C4—C864.0 (2)C37—N14—C40—C44177.59 (19)
C1—N4—C4—C555.9 (2)C37—N14—C40—C4164.3 (2)
N4—C4—C5—C658.9 (2)N14—C40—C41—C42169.69 (16)
C7—C4—C5—C660.4 (2)C43—C40—C41—C4247.5 (2)
C8—C4—C5—C6179.71 (16)C44—C40—C41—C4277.5 (2)
C4—C5—C6—C10'45.1 (6)C40—C41—C42—C4550.4 (2)
C4—C5—C6—C11'165.5 (5)C40—C41—C42—C4774.6 (2)
C4—C5—C6—C11174.9 (7)C40—C41—C42—C46168.54 (17)
C4—C5—C6—C955.6 (9)C39—N15—C48—C4998.3 (2)
C4—C5—C6—C9'78.3 (6)N15—C48—C49—C5036.4 (2)
C4—C5—C6—C1069.3 (8)N15—C48—C49—C54146.64 (18)
C3—N5—C12—C1386.8 (2)C54—C49—C50—C510.8 (3)
N5—C12—C13—C1420.3 (2)C48—C49—C50—C51176.20 (17)
N5—C12—C13—C18162.29 (17)C49—C50—C51—C520.1 (3)
C18—C13—C14—C150.8 (3)C50—C51—C52—C530.9 (3)
C12—C13—C14—C15178.20 (19)C51—C52—C53—C540.7 (4)
C13—C14—C15—C160.3 (3)C52—C53—C54—C490.2 (4)
C14—C15—C16—C170.3 (3)C50—C49—C54—C530.9 (3)
C15—C16—C17—C180.4 (3)C48—C49—C54—C53176.1 (2)
C14—C13—C18—C170.7 (3)C58—N19—C55—N161.9 (3)
C12—C13—C18—C17178.15 (19)C58—N19—C55—N17177.43 (17)
C16—C17—C18—C130.0 (3)C57—N16—C55—N19178.45 (16)
C21—N6—C19—N9179.58 (16)C57—N16—C55—N172.2 (2)
C21—N6—C19—N70.8 (3)C56—N17—C55—N19177.13 (16)
C22—N9—C19—N67.0 (3)C56—N17—C55—N163.5 (2)
C22—N9—C19—N7174.08 (16)C55—N17—C56—N182.7 (3)
C20—N7—C19—N62.1 (3)C55—N17—C56—Cl4178.07 (12)
C20—N7—C19—N9179.06 (16)C57—N18—C56—N170.6 (3)
C19—N7—C20—N82.3 (3)C57—N18—C56—Cl4179.83 (12)
C19—N7—C20—Cl2177.57 (12)C66—N20—C57—N163.8 (3)
C21—N8—C20—N71.1 (3)C66—N20—C57—N18177.05 (15)
C21—N8—C20—Cl2178.76 (12)C55—N16—C57—N20179.26 (16)
C30—N10—C21—N63.2 (3)C55—N16—C57—N180.2 (2)
C30—N10—C21—N8177.96 (16)C56—N18—C57—N20179.90 (15)
C19—N6—C21—N10179.27 (16)C56—N18—C57—N161.0 (2)
C19—N6—C21—N80.6 (3)C55—N19—C58—C61179.9 (2)
C20—N8—C21—N10179.21 (16)C55—N19—C58—C6263.4 (2)
C20—N8—C21—N60.5 (3)C55—N19—C58—C5956.4 (3)
C19—N9—C22—C25175.88 (18)N19—C58—C59—C6059.4 (3)
C19—N9—C22—C2660.4 (2)C61—C58—C59—C6059.7 (3)
C19—N9—C22—C2359.3 (2)C62—C58—C59—C60179.89 (18)
N9—C22—C23—C2456.2 (2)C58—C59—C60—C64'163.0 (6)
C25—C22—C23—C2464.3 (2)C58—C59—C60—C6346.5 (3)
C26—C22—C23—C24176.73 (17)C58—C59—C60—C6581.8 (3)
C22—C23—C24—C2866.9 (3)C58—C59—C60—C64165.7 (2)
C22—C23—C24—C2958.0 (3)C58—C59—C60—C65'34.8 (6)
C22—C23—C24—C27175.60 (19)C58—C59—C60—C63'77.9 (5)
C21—N10—C30—C3187.3 (2)C57—N20—C66—C6790.7 (2)
N10—C30—C31—C3616.8 (3)N20—C66—C67—C6828.2 (2)
N10—C30—C31—C32165.53 (18)N20—C66—C67—C72154.30 (18)
C36—C31—C32—C330.3 (4)C72—C67—C68—C690.6 (3)
C30—C31—C32—C33178.0 (2)C66—C67—C68—C69178.1 (2)
C31—C32—C33—C340.6 (4)C67—C68—C69—C700.1 (4)
C32—C33—C34—C351.0 (4)C68—C69—C70—C710.8 (4)
C33—C34—C35—C360.4 (5)C69—C70—C71—C721.4 (4)
C32—C31—C36—C350.8 (4)C68—C67—C72—C710.0 (3)
C30—C31—C36—C35178.5 (3)C66—C67—C72—C71177.6 (2)
C34—C35—C36—C310.5 (5)C70—C71—C72—C670.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N20—H20···N3i0.87 (2)2.14 (2)3.007 (2)179 (2)
N19—H19···N12ii0.87 (2)2.22 (2)3.085 (2)174 (2)
N15—H15···N13iii0.89 (2)2.06 (3)2.953 (2)176 (2)
N14—H14···N17ii0.84 (2)2.24 (2)3.078 (2)172 (2)
N10—H10···N8ii0.93 (2)2.06 (2)2.989 (2)171 (2)
N9—H9···N20.87 (2)2.29 (2)3.127 (2)163.3 (19)
N5—H5···N18i0.85 (2)2.14 (2)2.984 (2)172 (2)
N4—H4···N70.85 (2)2.24 (2)3.085 (2)174 (2)
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z+1; (iii) x+2, y, z+1.

Experimental details

Crystal data
Chemical formulaC18H26ClN5
Mr347.89
Crystal system, space groupTriclinic, P1
Temperature (K)113
a, b, c (Å)8.0987 (16), 20.811 (4), 23.984 (5)
α, β, γ (°)105.36 (3), 96.33 (3), 96.46 (3)
V3)3831.6 (13)
Z8
Radiation typeMo Kα
µ (mm1)0.21
Crystal size (mm)0.34 × 0.32 × 0.18
Data collection
DiffractometerRigaku Saturn
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2005)
Tmin, Tmax0.932, 0.963
No. of measured, independent and
observed [I > 2σ(I)] reflections
35937, 17590, 14508
Rint0.035
(sin θ/λ)max1)0.656
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.134, 1.08
No. of reflections17590
No. of parameters979
No. of restraints96
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.55, 0.53

Computer programs: CrystalClear (Rigaku/MSC, 2005), CrystalClear, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1996), CrystalStructure (Rigaku/MSC, 2005).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N20—H20···N3i0.87 (2)2.14 (2)3.007 (2)179 (2)
N19—H19···N12ii0.87 (2)2.22 (2)3.085 (2)174 (2)
N15—H15···N13iii0.89 (2)2.06 (3)2.953 (2)176 (2)
N14—H14···N17ii0.84 (2)2.24 (2)3.078 (2)172 (2)
N10—H10···N8ii0.93 (2)2.06 (2)2.989 (2)171 (2)
N9—H9···N20.87 (2)2.29 (2)3.127 (2)163.3 (19)
N5—H5···N18i0.85 (2)2.14 (2)2.984 (2)172 (2)
N4—H4···N70.85 (2)2.24 (2)3.085 (2)174 (2)
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z+1; (iii) x+2, y, z+1.
 

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