Download citation
Download citation
link to html
The title compound, C24H28N6O2, is a derivative of glycoluril with two phenyl substituents on the convex face of the glycouril system. Each N atom of the separate rings of the flexible U-shaped glycoluril clip carries an ethyl substituent. Inter­molecular non-classical C—H...O hydrogen bonds contribute to the stability of the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807058400/lw2043sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807058400/lw2043Isup2.hkl
Contains datablock I

CCDC reference: 672991

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.060
  • wR factor = 0.164
  • Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.105 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.10 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.22 Ratio
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 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 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Molecular clips and tweezers are interesting because of their supramolecular properties, like self-assembling and molecular recognition of small electron-deficient guest molecules (Degen et al., 2007; Klarner et al., 2003). Glycoluril and its derivatives have during the past two decades established an impressive career as a building block during supramolecular chemistry (Freeman et al., 1981; Rowan et al., 1999; Rebek, 2005; Wu, Fettinger et al., 2002). Based on glycouril, molecular clips, molecular tweezers, cucurbituril cotaxanes, molecular mapsules and molecular basket have been designed and synthesized(Rowan et al., 1999; Elemans et al.,2000). As a part of our ongoing investigation of glycoluril derivatives (Li et al., 2006), we report here the structure of the title compound (I) (Fig. 1).

The molecular structure of (I) is shown in Fig. 1. It is a flexible glycouril clip, each N atom from separate rings of which carries an ethyl substituent. Intermolecular non-classical C—H···O hydrogen bonds contribute to the stability of the structure (Table 1).

Related literature top

For the preparation of the title compound, see: Li et al. (2006). For related literature, see: Degen et al., (2007); Elemans et al. (2000); Freeman et al. (1981); Klarner & Kahlert (2003); Rebek (2005); Rowan et al. (1999); Wu et al. (2002).

Experimental top

The title compound was synthesized according to the procedure of Li, et al. (2006) in 12% isolated yield. Crystals of (I) suitable for X-ray data collection were obtained by slow evaporation of a chloroform and methanol solution in ratio of 15:1 at 293 K.

Refinement top

All H atoms were positioned geometrically (C—H = 0.96–0.97 Å) and refined using a riding model, with Uiso(H) = 1.2Ueq(C) (1.5Ueq(C) for methyl of the parent atoms.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Spek, 2003.

Figures top
[Figure 1] Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 10% probability level. H atoms are represented by spheres of arbitrary radius.
2,6-Diethyl-8 b,8c-diphenylperhydro-2,3a,4a,6,7a,8a- hexaazacyclopenta[def]fluorene-4,8-dione top
Crystal data top
C24H28N6O2Z = 2
Mr = 432.52F(000) = 460
Triclinic, P1Dx = 1.312 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.6963 (9) ÅCell parameters from 1908 reflections
b = 10.3704 (10) Åθ = 2.3–23.7°
c = 13.0294 (13) ŵ = 0.09 mm1
α = 76.885 (2)°T = 295 K
β = 73.233 (1)°Block, blue
γ = 84.576 (1)°0.20 × 0.20 × 0.10 mm
V = 1095.21 (19) Å3
Data collection top
Bruker SMART 4K CCD area-detector
diffractometer
2885 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.105
Graphite monochromatorθmax = 26.0°, θmin = 1.7°
ϕ and ω scansh = 1010
7080 measured reflectionsk = 1211
4255 independent reflectionsl = 1616
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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.068P)2]
where P = (Fo2 + 2Fc2)/3
4255 reflections(Δ/σ)max < 0.001
291 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
C24H28N6O2γ = 84.576 (1)°
Mr = 432.52V = 1095.21 (19) Å3
Triclinic, P1Z = 2
a = 8.6963 (9) ÅMo Kα radiation
b = 10.3704 (10) ŵ = 0.09 mm1
c = 13.0294 (13) ÅT = 295 K
α = 76.885 (2)°0.20 × 0.20 × 0.10 mm
β = 73.233 (1)°
Data collection top
Bruker SMART 4K CCD area-detector
diffractometer
2885 reflections with I > 2σ(I)
7080 measured reflectionsRint = 0.105
4255 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0610 restraints
wR(F2) = 0.164H-atom parameters constrained
S = 0.99Δρmax = 0.25 e Å3
4255 reflectionsΔρmin = 0.23 e Å3
291 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
C10.0890 (4)0.2902 (3)0.9644 (2)0.0645 (8)
H1A0.13910.27091.01570.097*
H1B0.09870.38350.96610.097*
H1C0.02260.26350.98390.097*
C20.1698 (3)0.2160 (2)0.8515 (2)0.0457 (6)
H2A0.28500.23130.83770.055*
H2B0.13620.25110.79860.055*
C30.1908 (3)0.0040 (2)0.90159 (19)0.0391 (6)
H3A0.16460.05510.97630.047*
H3B0.13370.08090.90230.047*
C40.1900 (3)0.0064 (2)0.71965 (19)0.0393 (6)
H4A0.13250.07830.70910.047*
H4B0.16380.05920.67480.047*
C50.4739 (3)0.0717 (2)0.89922 (18)0.0328 (5)
C60.4730 (3)0.0729 (2)0.63566 (17)0.0305 (5)
C70.4254 (2)0.0817 (2)0.74911 (16)0.0283 (5)
C80.3877 (2)0.2307 (2)0.72892 (17)0.0299 (5)
C90.3722 (3)0.2996 (2)0.8109 (2)0.0437 (6)
H90.38050.25500.87970.052*
C100.3441 (4)0.4357 (3)0.7899 (2)0.0599 (8)
H100.33450.48220.84470.072*
C110.3304 (3)0.5026 (3)0.6891 (3)0.0574 (8)
H110.31050.59370.67600.069*
C120.3462 (3)0.4342 (3)0.6077 (2)0.0492 (7)
H120.33730.47940.53920.059*
C130.3753 (3)0.2983 (2)0.62682 (19)0.0385 (6)
H130.38660.25260.57120.046*
C140.6075 (2)0.0377 (2)0.72159 (16)0.0279 (5)
C150.7302 (2)0.1463 (2)0.67807 (18)0.0314 (5)
C160.7865 (3)0.1967 (2)0.7500 (2)0.0418 (6)
H160.74840.16490.82520.050*
C170.8994 (3)0.2942 (3)0.7098 (2)0.0519 (7)
H170.93730.32770.75800.062*
C180.9557 (3)0.3416 (3)0.5991 (2)0.0536 (7)
H181.03260.40640.57240.064*
C190.8986 (3)0.2936 (3)0.5272 (2)0.0495 (7)
H190.93600.32670.45210.059*
C200.7859 (3)0.1962 (2)0.56666 (19)0.0404 (6)
H200.74720.16410.51810.048*
C210.7575 (3)0.1426 (3)0.8167 (2)0.0436 (6)
H21A0.85660.09560.79690.052*
H21B0.74710.20010.88820.052*
C220.7572 (3)0.1410 (2)0.6332 (2)0.0455 (6)
H22A0.74850.19760.58530.055*
H22B0.85590.09310.59890.055*
C230.6583 (4)0.3353 (3)0.7767 (2)0.0571 (7)
H23A0.66300.37730.71650.068*
H23B0.54920.30160.80230.068*
C240.6991 (5)0.4366 (3)0.8681 (3)0.0896 (12)
H24A0.81150.46020.84710.134*
H24B0.63720.51390.88280.134*
H24C0.67450.40030.93270.134*
N10.1345 (2)0.07304 (19)0.83424 (16)0.0393 (5)
N20.3631 (2)0.01826 (17)0.86419 (14)0.0304 (4)
N30.3625 (2)0.01628 (17)0.68186 (14)0.0303 (4)
N40.6222 (2)0.04582 (18)0.82483 (14)0.0316 (4)
N50.6212 (2)0.04532 (18)0.64235 (14)0.0323 (4)
N60.7685 (2)0.2239 (2)0.73700 (17)0.0449 (5)
O10.4475 (2)0.15622 (16)0.98420 (12)0.0451 (5)
O20.4458 (2)0.15742 (16)0.59266 (12)0.0425 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.061 (2)0.0429 (16)0.078 (2)0.0049 (14)0.0077 (16)0.0041 (15)
C20.0360 (14)0.0336 (14)0.0638 (17)0.0038 (11)0.0060 (12)0.0119 (12)
C30.0284 (13)0.0375 (13)0.0457 (14)0.0013 (10)0.0016 (10)0.0125 (11)
C40.0277 (13)0.0391 (14)0.0544 (15)0.0013 (11)0.0134 (11)0.0134 (12)
C50.0341 (13)0.0350 (13)0.0306 (12)0.0086 (10)0.0067 (10)0.0092 (10)
C60.0332 (13)0.0301 (12)0.0289 (12)0.0025 (10)0.0069 (10)0.0090 (10)
C70.0263 (11)0.0292 (12)0.0288 (11)0.0020 (9)0.0036 (9)0.0097 (9)
C80.0221 (11)0.0277 (12)0.0385 (13)0.0017 (9)0.0044 (9)0.0087 (10)
C90.0537 (16)0.0340 (13)0.0438 (14)0.0018 (12)0.0093 (12)0.0142 (11)
C100.082 (2)0.0369 (15)0.0650 (19)0.0007 (15)0.0156 (17)0.0256 (14)
C110.0582 (19)0.0290 (14)0.082 (2)0.0036 (13)0.0156 (16)0.0132 (15)
C120.0477 (16)0.0362 (14)0.0576 (17)0.0016 (12)0.0143 (13)0.0022 (12)
C130.0370 (14)0.0333 (13)0.0438 (14)0.0005 (11)0.0081 (11)0.0093 (11)
C140.0219 (11)0.0313 (12)0.0301 (11)0.0021 (9)0.0039 (9)0.0093 (9)
C150.0218 (11)0.0306 (12)0.0393 (13)0.0002 (9)0.0041 (9)0.0081 (10)
C160.0388 (14)0.0419 (14)0.0444 (14)0.0075 (11)0.0085 (11)0.0095 (11)
C170.0467 (16)0.0436 (16)0.0706 (19)0.0145 (13)0.0218 (14)0.0098 (14)
C180.0341 (15)0.0373 (14)0.082 (2)0.0126 (12)0.0143 (14)0.0053 (14)
C190.0358 (14)0.0463 (15)0.0527 (16)0.0070 (12)0.0007 (12)0.0046 (13)
C200.0354 (14)0.0414 (14)0.0401 (14)0.0058 (11)0.0043 (11)0.0059 (11)
C210.0295 (13)0.0438 (15)0.0566 (16)0.0015 (11)0.0146 (12)0.0058 (12)
C220.0357 (14)0.0437 (15)0.0538 (16)0.0073 (12)0.0015 (12)0.0214 (13)
C230.0547 (18)0.0364 (15)0.080 (2)0.0035 (13)0.0194 (15)0.0142 (14)
C240.112 (3)0.0472 (19)0.108 (3)0.005 (2)0.039 (2)0.0013 (19)
N10.0267 (10)0.0334 (11)0.0545 (13)0.0037 (9)0.0057 (9)0.0086 (9)
N20.0253 (10)0.0320 (10)0.0300 (10)0.0041 (8)0.0005 (8)0.0078 (8)
N30.0256 (10)0.0302 (10)0.0369 (10)0.0012 (8)0.0074 (8)0.0118 (8)
N40.0255 (10)0.0324 (10)0.0352 (10)0.0023 (8)0.0066 (8)0.0051 (8)
N50.0282 (10)0.0330 (10)0.0342 (10)0.0028 (8)0.0027 (8)0.0136 (8)
N60.0329 (12)0.0394 (12)0.0598 (14)0.0054 (9)0.0105 (10)0.0110 (10)
O10.0485 (11)0.0458 (10)0.0347 (9)0.0089 (8)0.0067 (8)0.0011 (8)
O20.0494 (11)0.0406 (9)0.0439 (10)0.0024 (8)0.0132 (8)0.0206 (8)
Geometric parameters (Å, º) top
C1—C21.497 (3)C12—C131.387 (3)
C1—H1A0.9600C12—H120.9300
C1—H1B0.9600C13—H130.9300
C1—H1C0.9600C14—N41.458 (3)
C2—N11.465 (3)C14—N51.461 (3)
C2—H2A0.9700C14—C151.522 (3)
C2—H2B0.9700C15—C201.382 (3)
C3—N11.457 (3)C15—C161.388 (3)
C3—N21.459 (3)C16—C171.382 (3)
C3—H3A0.9700C16—H160.9300
C3—H3B0.9700C17—C181.370 (4)
C4—N11.456 (3)C17—H170.9300
C4—N31.461 (3)C18—C191.378 (4)
C4—H4A0.9700C18—H180.9300
C4—H4B0.9700C19—C201.380 (3)
C5—O11.224 (2)C19—H190.9300
C5—N21.377 (3)C20—H200.9300
C5—N41.379 (3)C21—N61.458 (3)
C6—O21.216 (2)C21—N41.468 (3)
C6—N31.375 (3)C21—H21A0.9700
C6—N51.377 (3)C21—H21B0.9700
C7—N21.458 (3)C22—N61.453 (3)
C7—N31.464 (2)C22—N51.466 (3)
C7—C81.528 (3)C22—H22A0.9700
C7—C141.566 (3)C22—H22B0.9700
C8—C91.384 (3)C23—N61.474 (3)
C8—C131.385 (3)C23—C241.500 (4)
C9—C101.387 (4)C23—H23A0.9700
C9—H90.9300C23—H23B0.9700
C10—C111.371 (4)C24—H24A0.9600
C10—H100.9300C24—H24B0.9600
C11—C121.373 (4)C24—H24C0.9600
C11—H110.9300
C2—C1—H1A109.5C20—C15—C16119.4 (2)
C2—C1—H1B109.5C20—C15—C14120.36 (19)
H1A—C1—H1B109.5C16—C15—C14120.3 (2)
C2—C1—H1C109.5C17—C16—C15119.9 (2)
H1A—C1—H1C109.5C17—C16—H16120.0
H1B—C1—H1C109.5C15—C16—H16120.0
N1—C2—C1113.7 (2)C18—C17—C16120.3 (2)
N1—C2—H2A108.8C18—C17—H17119.9
C1—C2—H2A108.8C16—C17—H17119.9
N1—C2—H2B108.8C17—C18—C19120.2 (2)
C1—C2—H2B108.8C17—C18—H18119.9
H2A—C2—H2B107.7C19—C18—H18119.9
N1—C3—N2113.90 (18)C18—C19—C20119.9 (2)
N1—C3—H3A108.8C18—C19—H19120.0
N2—C3—H3A108.8C20—C19—H19120.0
N1—C3—H3B108.8C19—C20—C15120.3 (2)
N2—C3—H3B108.8C19—C20—H20119.8
H3A—C3—H3B107.7C15—C20—H20119.8
N1—C4—N3113.84 (18)N6—C21—N4113.91 (18)
N1—C4—H4A108.8N6—C21—H21A108.8
N3—C4—H4A108.8N4—C21—H21A108.8
N1—C4—H4B108.8N6—C21—H21B108.8
N3—C4—H4B108.8N4—C21—H21B108.8
H4A—C4—H4B107.7H21A—C21—H21B107.7
O1—C5—N2126.2 (2)N6—C22—N5114.39 (19)
O1—C5—N4125.5 (2)N6—C22—H22A108.7
N2—C5—N4108.24 (18)N5—C22—H22A108.7
O2—C6—N3126.1 (2)N6—C22—H22B108.7
O2—C6—N5126.1 (2)N5—C22—H22B108.7
N3—C6—N5107.80 (17)H22A—C22—H22B107.6
N2—C7—N3109.20 (15)N6—C23—C24112.2 (2)
N2—C7—C8111.82 (17)N6—C23—H23A109.2
N3—C7—C8112.05 (17)C24—C23—H23A109.2
N2—C7—C14103.45 (16)N6—C23—H23B109.2
N3—C7—C14103.08 (16)C24—C23—H23B109.2
C8—C7—C14116.52 (16)H23A—C23—H23B107.9
C9—C8—C13119.7 (2)C23—C24—H24A109.5
C9—C8—C7120.3 (2)C23—C24—H24B109.5
C13—C8—C7119.94 (19)H24A—C24—H24B109.5
C8—C9—C10119.5 (2)C23—C24—H24C109.5
C8—C9—H9120.2H24A—C24—H24C109.5
C10—C9—H9120.2H24B—C24—H24C109.5
C11—C10—C9120.8 (2)C4—N1—C3109.47 (17)
C11—C10—H10119.6C4—N1—C2112.71 (19)
C9—C10—H10119.6C3—N1—C2115.28 (19)
C10—C11—C12119.6 (2)C5—N2—C7111.13 (17)
C10—C11—H11120.2C5—N2—C3122.64 (18)
C12—C11—H11120.2C7—N2—C3115.74 (17)
C11—C12—C13120.5 (2)C6—N3—C4122.70 (18)
C11—C12—H12119.8C6—N3—C7111.66 (17)
C13—C12—H12119.8C4—N3—C7115.74 (17)
C8—C13—C12119.8 (2)C5—N4—C14111.48 (18)
C8—C13—H13120.1C5—N4—C21123.05 (19)
C12—C13—H13120.1C14—N4—C21115.96 (18)
N4—C14—N5109.15 (17)C6—N5—C14111.84 (17)
N4—C14—C15111.90 (16)C6—N5—C22123.01 (19)
N5—C14—C15111.68 (17)C14—N5—C22115.18 (17)
N4—C14—C7102.98 (15)C22—N6—C21110.28 (18)
N5—C14—C7102.89 (15)C22—N6—C23113.4 (2)
C15—C14—C7117.46 (18)C21—N6—C23114.3 (2)
N2—C7—C8—C929.1 (3)C14—C7—N2—C510.5 (2)
N3—C7—C8—C9152.1 (2)N3—C7—N2—C347.2 (2)
C14—C7—C8—C989.6 (2)C8—C7—N2—C377.4 (2)
N2—C7—C8—C13153.51 (19)C14—C7—N2—C3156.44 (17)
N3—C7—C8—C1330.5 (3)N1—C3—N2—C589.5 (2)
C14—C7—C8—C1387.8 (2)N1—C3—N2—C752.2 (3)
C13—C8—C9—C100.1 (4)O2—C6—N3—C422.0 (3)
C7—C8—C9—C10177.5 (2)N5—C6—N3—C4160.69 (18)
C8—C9—C10—C110.5 (4)O2—C6—N3—C7166.1 (2)
C9—C10—C11—C120.6 (4)N5—C6—N3—C716.6 (2)
C10—C11—C12—C130.2 (4)N1—C4—N3—C691.0 (2)
C9—C8—C13—C120.5 (3)N1—C4—N3—C751.7 (3)
C7—C8—C13—C12177.9 (2)N2—C7—N3—C699.8 (2)
C11—C12—C13—C80.4 (4)C8—C7—N3—C6135.78 (19)
N2—C7—C14—N40.65 (18)C14—C7—N3—C69.7 (2)
N3—C7—C14—N4113.10 (16)N2—C7—N3—C447.0 (2)
C8—C7—C14—N4123.77 (18)C8—C7—N3—C477.4 (2)
N2—C7—C14—N5114.10 (16)C14—C7—N3—C4156.51 (17)
N3—C7—C14—N50.36 (19)O1—C5—N4—C14166.56 (19)
C8—C7—C14—N5122.78 (18)N2—C5—N4—C1416.5 (2)
N2—C7—C14—C15122.80 (18)O1—C5—N4—C2121.7 (3)
N3—C7—C14—C15123.45 (18)N2—C5—N4—C21161.32 (18)
C8—C7—C14—C150.3 (3)N5—C14—N4—C599.4 (2)
N4—C14—C15—C20151.3 (2)C15—C14—N4—C5136.47 (19)
N5—C14—C15—C2028.6 (3)C7—C14—N4—C59.4 (2)
C7—C14—C15—C2089.9 (3)N5—C14—N4—C2148.1 (2)
N4—C14—C15—C1629.1 (3)C15—C14—N4—C2176.0 (2)
N5—C14—C15—C16151.8 (2)C7—C14—N4—C21156.92 (17)
C7—C14—C15—C1689.7 (2)N6—C21—N4—C592.6 (3)
C20—C15—C16—C171.1 (4)N6—C21—N4—C1450.8 (3)
C14—C15—C16—C17179.2 (2)O2—C6—N5—C14165.8 (2)
C15—C16—C17—C180.1 (4)N3—C6—N5—C1416.9 (2)
C16—C17—C18—C190.8 (4)O2—C6—N5—C2222.0 (3)
C17—C18—C19—C200.8 (4)N3—C6—N5—C22160.70 (19)
C18—C19—C20—C150.2 (4)N4—C14—N5—C698.52 (19)
C16—C15—C20—C191.1 (4)C15—C14—N5—C6137.22 (19)
C14—C15—C20—C19179.2 (2)C7—C14—N5—C610.3 (2)
N3—C4—N1—C351.3 (2)N4—C14—N5—C2248.3 (2)
N3—C4—N1—C278.4 (2)C15—C14—N5—C2276.0 (2)
N2—C3—N1—C451.5 (2)C7—C14—N5—C22157.17 (17)
N2—C3—N1—C276.7 (3)N6—C22—N5—C690.8 (2)
C1—C2—N1—C4169.8 (2)N6—C22—N5—C1451.9 (3)
C1—C2—N1—C363.6 (3)N5—C22—N6—C2149.9 (3)
O1—C5—N2—C7166.2 (2)N5—C22—N6—C2379.8 (3)
N4—C5—N2—C716.9 (2)N4—C21—N6—C2249.0 (3)
O1—C5—N2—C323.0 (3)N4—C21—N6—C2380.2 (3)
N4—C5—N2—C3160.07 (18)C24—C23—N6—C22166.3 (3)
N3—C7—N2—C598.73 (19)C24—C23—N6—C2166.1 (3)
C8—C7—N2—C5136.70 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16···O1i0.932.563.427 (3)155
C13—H13···O2ii0.932.563.410 (3)152
C20—H20···O2ii0.932.523.387 (3)155
Symmetry codes: (i) x+1, y, z+2; (ii) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC24H28N6O2
Mr432.52
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)8.6963 (9), 10.3704 (10), 13.0294 (13)
α, β, γ (°)76.885 (2), 73.233 (1), 84.576 (1)
V3)1095.21 (19)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.20 × 0.20 × 0.10
Data collection
DiffractometerBruker SMART 4K CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
7080, 4255, 2885
Rint0.105
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.061, 0.164, 0.99
No. of reflections4255
No. of parameters291
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.25, 0.23

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), PLATON (Spek, 2003.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16···O1i0.932.563.427 (3)154.9
C13—H13···O2ii0.932.563.410 (3)152.4
C20—H20···O2ii0.932.523.387 (3)154.7
Symmetry codes: (i) x+1, y, z+2; (ii) x+1, y, z+1.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds