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Acta Cryst. (2007). E63, o3909
https://doi.org/10.1107/S1600536807041591
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rac-12a,11b-Diphenyl-1,2,3,4,5,11-hexa­hydro-2,3,4a,5a,10a,11a-hexa­azabenz[f]indeno[2,1,8-ija]naphth[2,3-f]azulene-1,4,10-trione chloro­form solvate

S.-L. Hu, J.-M. Zhang, G. Yan and S. Wang
The title compound, C25H20N6O3·CHCl3, a rigid glycoluril derivative, is an inter­mediate for the synthesis of mol­ecular tweezers. The crystal structure is stabilized by inter­molecular C—H...O and N—H...O hydrogen bonds. The chloro­form solvent mol­ecule is disordered over two positions; the site occupancy factors are ca 0.89 and 0.11.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807041591/kp2109sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807041591/kp2109Isup2.hkl
Contains datablock I

CCDC reference: 660367

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in solvent or counterion
  • R factor = 0.056
  • wR factor = 0.171
  • Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found




Alert level C
ABSTY03_ALERT_1_C  The _exptl_absorpt_correction_type has been given as none.
            However values have been given for Tmin and Tmax. Remove
            these if an absorption correction has not been applied.
  From the CIF: _exptl_absorpt_correction_T_min   0.858
  From the CIF: _exptl_absorpt_correction_T_max   0.891
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.106
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.11
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged ....       H26A
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.94 Ratio
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C26
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      43.00 Perc.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      26.90 Deg.
              CL2  -C26  -CL2'    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      31.20 Deg.
              CL1' -C26  -CL1     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      25.50 Deg.
              CL3  -C26  -CL3'    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      12.00 Deg.
              H26A -C26  -H26B    1.555   1.555   1.555


Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C12    = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C19    = ...          S
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         18


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

   4 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
   3 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check
Comment top

The glycoluryl skeleton has served as an important building blocks for preparations of supramolecular systems including molecular clips (Rowan et al., 1999; Yin et al., 2006; Li et al., 2006; Hu et al., 2007), molecular capsules (Hof et al., 2002; Rebek 2005) and the cucurbit[n]uryl family (Lagona et al., 2003). Many methylene-bridged glycoluryl dimers have been synthesized by dimerization reaction of glycoluryl derivatives (Wu et al., 2002). In this paper we report the crystal structure of the title compound (I).

The chirality of the molecule is induced by the inverted nitrogen atoms generating two chiral carbon atoms of the same absolute configuration (C12 and C19). The space group is centrosymmetric and the crystalline compound is a racemate. In the crystal structure of (I) (Fig. 1) the interplanar angle between the two five-membered rings C11/N4/C12/C19/N5 and C10/N3/C12/C19/N5 is 69.5 (1)° whereas the angle between the planes of the two benzene rings C13/C14/C15/C16/C17/C18 and C20/C21/C22/C23/C24/C25 is 66.4 (2) °. The aromatic ring (C1/C2/C3/C4/C5/C6) is coplanar with the five-membered (C1/C6/C7/N1/N2) ring. The molecules are connected by intermolecular C—H···O and N—H···O hydrogen bonds (Table 1and Fig. 2).

Related literature top

For related literature, see: Hof et al. (2002); Hu et al. (2007); Lagona et al. (2003); Li et al. (2006); Rebek (2005); Rowan et al. (1999); Wu et al. (2002); Yin et al. (2006); Sheldrick (2003).

Experimental top

The title compound was synthesized in analogy to the literature procedure of Lagona et al. (2003), Crystals appropriate for data collection were obtained by slow evaporation from a methanol-chloroform solution (1:20 V/V) of (I).

Refinement top

The H atoms were constrained to an ideal geometry and constrained to ride on their parent atoms as follows: methylene H with d(C—H)=0.97 Å and Uiso(H) = 1.2Ueq(C); methine H with d(C—H)=0.98 Å and Uiso(H) = 1.2Ueq(C); aromatic H with d(C—H)=0.93 Å and Uiso(H) = 1.2Ueq(C). The solvent molecule chloroform is disorder over two sites; the site-occupancy factors for the two orientations were refined by DFIX, giving 0.891 (4) and 0.109 (4) for the major and minor components, respectively.

Structure description top

The glycoluryl skeleton has served as an important building blocks for preparations of supramolecular systems including molecular clips (Rowan et al., 1999; Yin et al., 2006; Li et al., 2006; Hu et al., 2007), molecular capsules (Hof et al., 2002; Rebek 2005) and the cucurbit[n]uryl family (Lagona et al., 2003). Many methylene-bridged glycoluryl dimers have been synthesized by dimerization reaction of glycoluryl derivatives (Wu et al., 2002). In this paper we report the crystal structure of the title compound (I).

The chirality of the molecule is induced by the inverted nitrogen atoms generating two chiral carbon atoms of the same absolute configuration (C12 and C19). The space group is centrosymmetric and the crystalline compound is a racemate. In the crystal structure of (I) (Fig. 1) the interplanar angle between the two five-membered rings C11/N4/C12/C19/N5 and C10/N3/C12/C19/N5 is 69.5 (1)° whereas the angle between the planes of the two benzene rings C13/C14/C15/C16/C17/C18 and C20/C21/C22/C23/C24/C25 is 66.4 (2) °. The aromatic ring (C1/C2/C3/C4/C5/C6) is coplanar with the five-membered (C1/C6/C7/N1/N2) ring. The molecules are connected by intermolecular C—H···O and N—H···O hydrogen bonds (Table 1and Fig. 2).

For related literature, see: Hof et al. (2002); Hu et al. (2007); Lagona et al. (2003); Li et al. (2006); Rebek (2005); Rowan et al. (1999); Wu et al. (2002); Yin et al. (2006); Sheldrick (2003).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; 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: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. View of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms atoms shown as circles of arbitrary radii. Higher populated orientation of disordered solvate molecule is shown.
[Figure 2] Fig. 2. The molecular packing of (I) viewed along the b axis.
rac-12a,11b-Diphenyl-1,2,3,4,5,11-hexahydro-2,3,4a,5a,10a,11a-hexaazabenz[f]indeno[2,1,8-ija]naphth[2,3-f]azulene-1,4,10-trione chloroform solvate top
Crystal data top
C25H20N6O3.CHCl3F(000) = 1176
Mr = 571.84Dx = 1.463 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9009 reflections
a = 17.3315 (12) Åθ = 2.3–26.2°
b = 8.4507 (6) ŵ = 0.40 mm−1
c = 17.7874 (12) ÅT = 292 K
β = 94.652 (1)°Block, colourless
V = 2596.6 (3) Å30.40 × 0.30 × 0.30 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		3995 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.106
Graphite monochromatorθmax = 26.0°, θmin = 2.3°
φ and ω scansh = −21→21
26236 measured reflectionsk = −10→10
5081 independent reflectionsl = −21→21
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) = 0.171H atoms treated by a mixture of independent and constrained refinement
S = 1.12 w = 1/[σ2(Fo2) + (0.1P)2 + 0.1644P]
where P = (Fo2 + 2Fc2)/3
5081 reflections(Δ/σ)max < 0.001
368 parametersΔρmax = 0.55 e Å−3
18 restraintsΔρmin = −0.45 e Å−3
Crystal data top
C25H20N6O3.CHCl3V = 2596.6 (3) Å3
Mr = 571.84Z = 4
Monoclinic, P21/nMo Kα radiation
a = 17.3315 (12) ŵ = 0.40 mm−1
b = 8.4507 (6) ÅT = 292 K
c = 17.7874 (12) Å0.40 × 0.30 × 0.30 mm
β = 94.652 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		3995 reflections with I > 2σ(I)
26236 measured reflectionsRint = 0.106
5081 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05618 restraints
wR(F2) = 0.171H atoms treated by a mixture of independent and constrained refinement
S = 1.12Δρmax = 0.55 e Å−3
5081 reflectionsΔρmin = −0.45 e Å−3
368 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)
C1−0.01228 (12)0.6113 (2)0.09136 (11)0.0406 (5)
C2−0.08340 (13)0.6849 (3)0.07437 (13)0.0512 (6)
H2−0.08970.76490.03850.061*
C3−0.14406 (14)0.6327 (3)0.11352 (14)0.0579 (6)
H3−0.19250.67900.10370.070*
C4−0.13512 (15)0.5126 (3)0.16741 (14)0.0614 (7)
H4−0.17770.47960.19190.074*
C5−0.06507 (15)0.4427 (3)0.18466 (13)0.0548 (6)
H5−0.05920.36370.22110.066*
C6−0.00201 (13)0.4933 (2)0.14600 (11)0.0416 (5)
C70.07793 (12)0.4425 (2)0.15020 (11)0.0401 (5)
C80.19109 (11)0.5352 (2)0.08132 (11)0.0364 (4)
H8A0.21800.45130.10990.044*
H8B0.19490.51340.02820.044*
C90.07849 (11)0.7535 (2)0.00801 (11)0.0366 (4)
H9A0.09970.7030−0.03480.044*
H9B0.03270.8116−0.01080.044*
C100.24996 (12)0.7221 (2)0.17428 (11)0.0383 (4)
C110.11468 (11)0.9955 (2)0.08124 (10)0.0358 (4)
C120.21600 (10)0.8227 (2)0.05273 (10)0.0313 (4)
C130.25256 (11)0.8065 (2)−0.02170 (10)0.0365 (4)
C140.31630 (13)0.7111 (3)−0.02762 (13)0.0485 (5)
H140.33670.65390.01400.058*
C150.35027 (16)0.7001 (3)−0.09556 (16)0.0656 (7)
H150.39320.6354−0.09900.079*
C160.32150 (18)0.7826 (4)−0.15692 (15)0.0730 (8)
H160.34430.7735−0.20230.088*
C170.25842 (18)0.8798 (4)−0.15183 (15)0.0716 (8)
H170.23900.9378−0.19360.086*
C180.22375 (14)0.8913 (3)−0.08427 (12)0.0513 (6)
H180.18090.9565−0.08110.062*
C190.24895 (11)0.9617 (2)0.10817 (10)0.0337 (4)
C200.31752 (12)1.0523 (2)0.08231 (12)0.0405 (5)
C210.39225 (14)1.0119 (3)0.10742 (17)0.0604 (6)
H210.40100.93280.14350.073*
C220.45422 (17)1.0884 (4)0.0792 (2)0.0852 (10)
H220.50451.05940.09580.102*
C230.4419 (2)1.2067 (5)0.0271 (2)0.0919 (11)
H230.48381.25830.00850.110*
C240.3686 (2)1.2488 (4)0.00243 (19)0.0841 (10)
H240.36051.3292−0.03300.101*
C250.30584 (16)1.1725 (3)0.02971 (15)0.0579 (6)
H250.25581.20220.01270.069*
C260.46631 (16)0.5204 (3)0.23715 (15)0.0657 (7)
H26A0.443 (2)0.596 (4)0.270 (2)0.079*0.89
H26B0.4541 (8)0.5929 (15)0.2749 (7)0.079*0.11
Cl10.41377 (9)0.34312 (14)0.23910 (8)0.1022 (6)0.891 (4)
Cl20.56162 (7)0.4907 (3)0.27090 (7)0.1030 (6)0.891 (4)
Cl30.46003 (13)0.59902 (19)0.14665 (6)0.1049 (6)0.891 (4)
Cl1'0.3909 (5)0.4067 (16)0.2006 (8)0.128 (5)*0.109 (4)
Cl2'0.5452 (5)0.4011 (15)0.2668 (6)0.099 (4)*0.109 (4)
Cl3'0.5003 (8)0.6358 (12)0.1606 (6)0.106 (4)*0.109 (4)
N10.11038 (9)0.53202 (19)0.09645 (9)0.0394 (4)
N20.05607 (9)0.6324 (2)0.05924 (11)0.0449 (4)
N30.22939 (9)0.68300 (17)0.09983 (8)0.0336 (4)
N40.13463 (9)0.86380 (18)0.04135 (9)0.0346 (4)
N50.26771 (11)0.8756 (2)0.17713 (9)0.0426 (4)
N60.18148 (10)1.0629 (2)0.11157 (10)0.0401 (4)
O10.11387 (9)0.34349 (17)0.19079 (9)0.0515 (4)
O20.25289 (11)0.62845 (19)0.22639 (8)0.0567 (5)
O30.04941 (8)1.04336 (18)0.08530 (8)0.0476 (4)
H60.1812 (15)1.133 (2)0.1474 (11)0.057*
H5A0.2804 (14)0.920 (3)0.2196 (9)0.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0391 (11)0.0430 (11)0.0388 (11)−0.0064 (8)−0.0024 (8)−0.0056 (8)
C20.0422 (12)0.0570 (14)0.0530 (13)−0.0005 (10)−0.0038 (10)0.0019 (10)
C30.0409 (12)0.0740 (16)0.0588 (15)0.0014 (11)0.0031 (11)−0.0066 (12)
C40.0514 (14)0.0790 (18)0.0560 (15)−0.0111 (13)0.0173 (11)−0.0100 (13)
C50.0602 (15)0.0600 (14)0.0449 (13)−0.0103 (11)0.0082 (10)0.0001 (10)
C60.0469 (12)0.0424 (11)0.0348 (10)−0.0067 (9)−0.0001 (8)−0.0049 (8)
C70.0466 (11)0.0359 (10)0.0364 (10)−0.0057 (8)−0.0051 (8)−0.0004 (8)
C80.0376 (10)0.0318 (10)0.0388 (10)0.0017 (8)−0.0033 (8)−0.0017 (8)
C90.0349 (10)0.0434 (11)0.0305 (9)0.0003 (8)−0.0046 (7)0.0028 (8)
C100.0414 (11)0.0392 (10)0.0331 (10)−0.0020 (8)−0.0045 (8)0.0019 (8)
C110.0399 (11)0.0390 (10)0.0285 (9)0.0033 (8)0.0025 (7)0.0036 (7)
C120.0323 (9)0.0320 (9)0.0290 (9)0.0006 (7)−0.0016 (7)−0.0005 (7)
C130.0375 (10)0.0398 (10)0.0323 (10)−0.0046 (8)0.0024 (8)−0.0029 (8)
C140.0437 (12)0.0572 (13)0.0449 (12)0.0042 (10)0.0066 (9)−0.0007 (10)
C150.0526 (15)0.0804 (18)0.0671 (17)0.0074 (13)0.0247 (12)−0.0071 (14)
C160.0769 (19)0.098 (2)0.0480 (15)0.0016 (17)0.0300 (13)0.0021 (14)
C170.0815 (19)0.095 (2)0.0406 (13)0.0067 (16)0.0161 (13)0.0168 (13)
C180.0557 (13)0.0604 (14)0.0383 (12)0.0059 (11)0.0074 (10)0.0079 (10)
C190.0362 (10)0.0333 (9)0.0307 (9)0.0010 (7)−0.0020 (7)−0.0008 (7)
C200.0407 (11)0.0360 (10)0.0449 (11)−0.0052 (8)0.0047 (9)−0.0064 (8)
C210.0445 (13)0.0547 (14)0.0811 (18)−0.0027 (10)−0.0009 (12)−0.0069 (12)
C220.0457 (15)0.092 (2)0.120 (3)−0.0150 (15)0.0184 (16)−0.028 (2)
C230.077 (2)0.098 (2)0.106 (3)−0.040 (2)0.039 (2)−0.019 (2)
C240.108 (3)0.0687 (19)0.079 (2)−0.0324 (18)0.0289 (18)0.0080 (15)
C250.0628 (15)0.0493 (13)0.0619 (15)−0.0099 (11)0.0066 (12)0.0081 (11)
C260.0740 (17)0.0701 (17)0.0544 (15)0.0191 (14)0.0131 (12)−0.0052 (13)
Cl10.1324 (10)0.0798 (7)0.0974 (9)−0.0179 (6)0.0280 (7)−0.0191 (6)
Cl20.0727 (7)0.1422 (15)0.0931 (8)0.0284 (7)0.0004 (5)−0.0072 (7)
Cl30.1443 (14)0.1069 (9)0.0636 (6)0.0391 (9)0.0090 (7)0.0229 (5)
N10.0385 (9)0.0366 (9)0.0418 (9)−0.0007 (7)−0.0050 (7)0.0047 (7)
N20.0320 (9)0.0491 (10)0.0530 (11)−0.0022 (7)−0.0008 (7)0.0133 (8)
N30.0391 (9)0.0307 (8)0.0300 (8)0.0003 (6)−0.0040 (6)0.0006 (6)
N40.0322 (8)0.0381 (8)0.0328 (8)0.0025 (6)−0.0025 (6)−0.0021 (6)
N50.0582 (11)0.0375 (9)0.0298 (9)−0.0048 (8)−0.0097 (8)−0.0003 (7)
N60.0420 (9)0.0373 (9)0.0410 (9)0.0036 (7)0.0022 (7)−0.0093 (7)
O10.0560 (10)0.0462 (8)0.0508 (9)−0.0017 (7)−0.0054 (7)0.0123 (7)
O20.0823 (12)0.0475 (9)0.0372 (8)−0.0149 (8)−0.0140 (8)0.0126 (7)
O30.0375 (8)0.0588 (9)0.0463 (8)0.0139 (7)0.0022 (6)−0.0015 (7)
Geometric parameters (Å, º) top
C1—N21.368 (3)C14—C151.390 (3)
C1—C21.392 (3)C14—H140.9300
C1—C61.394 (3)C15—C161.355 (4)
C2—C31.380 (3)C15—H150.9300
C2—H20.9300C16—C171.376 (4)
C3—C41.396 (4)C16—H160.9300
C3—H30.9300C17—C181.390 (3)
C4—C51.362 (4)C17—H170.9300
C4—H40.9300C18—H180.9300
C5—C61.404 (3)C19—N51.440 (2)
C5—H50.9300C19—N61.454 (2)
C6—C71.446 (3)C19—C201.516 (3)
C7—O11.240 (2)C20—C211.378 (3)
C7—N11.375 (3)C20—C251.385 (3)
C8—N31.440 (2)C21—C221.382 (4)
C8—N11.446 (3)C21—H210.9300
C8—H8A0.9700C22—C231.369 (5)
C8—H8B0.9700C22—H220.9300
C9—N41.440 (2)C23—C241.357 (5)
C9—N21.444 (2)C23—H230.9300
C9—H9A0.9700C24—C251.386 (4)
C9—H9B0.9700C24—H240.9300
C10—O21.217 (2)C25—H250.9300
C10—N51.333 (3)C26—Cl1'1.707 (7)
C10—N31.383 (2)C26—Cl21.730 (3)
C11—O31.209 (2)C26—Cl31.737 (3)
C11—N61.362 (3)C26—Cl2'1.746 (6)
C11—N41.379 (2)C26—Cl11.755 (3)
C12—N41.450 (2)C26—Cl3'1.811 (7)
C12—N31.456 (2)C26—H26A0.98 (4)
C12—C131.520 (3)C26—H26B0.945 (8)
C12—C191.608 (2)N1—N21.394 (2)
C13—C141.378 (3)N5—H5A0.857 (10)
C13—C181.382 (3)N6—H60.868 (10)
N2—C1—C2129.3 (2)N6—C19—C12102.02 (14)
N2—C1—C6108.56 (18)C20—C19—C12115.52 (15)
C2—C1—C6122.1 (2)C21—C20—C25118.9 (2)
C3—C2—C1116.5 (2)C21—C20—C19121.0 (2)
C3—C2—H2121.8C25—C20—C19120.0 (2)
C1—C2—H2121.8C20—C21—C22120.2 (3)
C2—C3—C4122.2 (2)C20—C21—H21119.9
C2—C3—H3118.9C22—C21—H21119.9
C4—C3—H3118.9C23—C22—C21120.3 (3)
C5—C4—C3121.1 (2)C23—C22—H22119.8
C5—C4—H4119.4C21—C22—H22119.8
C3—C4—H4119.4C24—C23—C22120.0 (3)
C4—C5—C6118.2 (2)C24—C23—H23120.0
C4—C5—H5120.9C22—C23—H23120.0
C6—C5—H5120.9C23—C24—C25120.4 (3)
C1—C6—C5119.9 (2)C23—C24—H24119.8
C1—C6—C7108.41 (18)C25—C24—H24119.8
C5—C6—C7131.7 (2)C20—C25—C24120.1 (3)
O1—C7—N1124.20 (19)C20—C25—H25120.0
O1—C7—C6131.6 (2)C24—C25—H25120.0
N1—C7—C6104.19 (16)Cl1'—C26—Cl2136.9 (5)
N3—C8—N1114.13 (16)Cl1'—C26—Cl382.8 (5)
N3—C8—H8A108.7Cl2—C26—Cl3111.31 (17)
N1—C8—H8A108.7Cl1'—C26—Cl2'110.3 (5)
N3—C8—H8B108.7Cl2—C26—Cl2'26.9 (4)
N1—C8—H8B108.7Cl3—C26—Cl2'119.3 (4)
H8A—C8—H8B107.6Cl1'—C26—Cl131.2 (5)
N4—C9—N2113.96 (15)Cl2—C26—Cl1110.59 (16)
N4—C9—H9A108.8Cl3—C26—Cl1110.56 (17)
N2—C9—H9A108.8Cl2'—C26—Cl184.0 (4)
N4—C9—H9B108.8Cl1'—C26—Cl3'107.6 (5)
N2—C9—H9B108.8Cl2—C26—Cl3'88.8 (4)
H9A—C9—H9B107.7Cl3—C26—Cl3'25.5 (4)
O2—C10—N5127.50 (18)Cl2'—C26—Cl3'104.1 (4)
O2—C10—N3124.42 (19)Cl1—C26—Cl3'132.5 (5)
N5—C10—N3108.05 (16)Cl1'—C26—H26A105 (2)
O3—C11—N6127.32 (18)Cl2—C26—H26A108 (2)
O3—C11—N4125.12 (18)Cl3—C26—H26A108 (2)
N6—C11—N4107.51 (17)Cl2'—C26—H26A123 (2)
N4—C12—N3112.47 (15)Cl1—C26—H26A108 (2)
N4—C12—C13111.68 (14)Cl3'—C26—H26A106 (2)
N3—C12—C13111.72 (15)Cl1'—C26—H26B115.3 (8)
N4—C12—C19101.76 (13)Cl2—C26—H26B96.3 (9)
N3—C12—C19101.96 (13)Cl3—C26—H26B114.2 (9)
C13—C12—C19116.60 (15)Cl2'—C26—H26B112.0 (8)
C14—C13—C18118.75 (19)Cl1—C26—H26B113.1 (9)
C14—C13—C12120.85 (18)Cl3'—C26—H26B106.9 (8)
C18—C13—C12120.38 (18)H26A—C26—H26B12 (2)
C13—C14—C15120.3 (2)C7—N1—N2111.51 (16)
C13—C14—H14119.9C7—N1—C8126.60 (16)
C15—C14—H14119.9N2—N1—C8121.76 (16)
C16—C15—C14120.8 (2)C1—N2—N1107.27 (16)
C16—C15—H15119.6C1—N2—C9129.95 (17)
C14—C15—H15119.6N1—N2—C9121.67 (15)
C15—C16—C17119.8 (2)C10—N3—C8120.30 (16)
C15—C16—H16120.1C10—N3—C12111.95 (15)
C17—C16—H16120.1C8—N3—C12121.53 (14)
C16—C17—C18120.0 (2)C11—N4—C9123.04 (16)
C16—C17—H17120.0C11—N4—C12113.75 (15)
C18—C17—H17120.0C9—N4—C12121.30 (15)
C13—C18—C17120.4 (2)C10—N5—C19115.06 (16)
C13—C18—H18119.8C10—N5—H5A120.2 (18)
C17—C18—H18119.8C19—N5—H5A123.6 (18)
N5—C19—N6112.86 (16)C11—N6—C19113.47 (16)
N5—C19—C20112.66 (16)C11—N6—H6121.3 (17)
N6—C19—C20111.60 (16)C19—N6—H6118.8 (18)
N5—C19—C12101.41 (14)
N2—C1—C2—C3176.2 (2)C23—C24—C25—C20−0.2 (5)
C6—C1—C2—C3−1.2 (3)O1—C7—N1—N2179.60 (18)
C1—C2—C3—C40.0 (4)C6—C7—N1—N2−0.6 (2)
C2—C3—C4—C51.1 (4)O1—C7—N1—C8−4.5 (3)
C3—C4—C5—C6−0.9 (4)C6—C7—N1—C8175.28 (17)
N2—C1—C6—C5−176.52 (19)N3—C8—N1—C7−112.6 (2)
C2—C1—C6—C51.4 (3)N3—C8—N1—N262.9 (2)
N2—C1—C6—C72.4 (2)C2—C1—N2—N1179.6 (2)
C2—C1—C6—C7−179.69 (19)C6—C1—N2—N1−2.7 (2)
C4—C5—C6—C1−0.3 (3)C2—C1—N2—C911.7 (4)
C4—C5—C6—C7−178.9 (2)C6—C1—N2—C9−170.53 (19)
C1—C6—C7—O1178.7 (2)C7—N1—N2—C12.1 (2)
C5—C6—C7—O1−2.6 (4)C8—N1—N2—C1−174.03 (17)
C1—C6—C7—N1−1.1 (2)C7—N1—N2—C9171.13 (17)
C5—C6—C7—N1177.6 (2)C8—N1—N2—C9−5.0 (3)
N4—C12—C13—C14−153.83 (18)N4—C9—N2—C1109.2 (2)
N3—C12—C13—C14−26.9 (2)N4—C9—N2—N1−57.1 (2)
C19—C12—C13—C1489.8 (2)O2—C10—N3—C815.8 (3)
N4—C12—C13—C1828.2 (3)N5—C10—N3—C8−166.13 (17)
N3—C12—C13—C18155.12 (19)O2—C10—N3—C12168.5 (2)
C19—C12—C13—C18−88.2 (2)N5—C10—N3—C12−13.4 (2)
C18—C13—C14—C15−0.5 (3)N1—C8—N3—C1075.2 (2)
C12—C13—C14—C15−178.5 (2)N1—C8—N3—C12−74.9 (2)
C13—C14—C15—C160.0 (4)N4—C12—N3—C10−97.09 (18)
C14—C15—C16—C170.7 (5)C13—C12—N3—C10136.40 (17)
C15—C16—C17—C18−1.0 (5)C19—C12—N3—C1011.15 (19)
C14—C13—C18—C170.2 (4)N4—C12—N3—C855.2 (2)
C12—C13—C18—C17178.3 (2)C13—C12—N3—C8−71.3 (2)
C16—C17—C18—C130.5 (4)C19—C12—N3—C8163.46 (16)
N4—C12—C19—N5111.33 (15)O3—C11—N4—C9−9.1 (3)
N3—C12—C19—N5−4.98 (18)N6—C11—N4—C9173.40 (16)
C13—C12—C19—N5−126.92 (17)O3—C11—N4—C12−173.50 (18)
N4—C12—C19—N6−5.30 (17)N6—C11—N4—C129.0 (2)
N3—C12—C19—N6−121.60 (15)N2—C9—N4—C11−85.1 (2)
C13—C12—C19—N6116.45 (17)N2—C9—N4—C1278.2 (2)
N4—C12—C19—C20−126.54 (16)N3—C12—N4—C11106.46 (17)
N3—C12—C19—C20117.15 (17)C13—C12—N4—C11−127.01 (16)
C13—C12—C19—C20−4.8 (2)C19—C12—N4—C11−1.91 (19)
N5—C19—C20—C2120.5 (3)N3—C12—N4—C9−58.2 (2)
N6—C19—C20—C21148.6 (2)C13—C12—N4—C968.3 (2)
C12—C19—C20—C21−95.4 (2)C19—C12—N4—C9−166.61 (15)
N5—C19—C20—C25−162.89 (19)O2—C10—N5—C19−172.2 (2)
N6—C19—C20—C25−34.7 (3)N3—C10—N5—C199.9 (2)
C12—C19—C20—C2581.2 (2)N6—C19—N5—C10105.7 (2)
C25—C20—C21—C22−1.2 (4)C20—C19—N5—C10−126.81 (19)
C19—C20—C21—C22175.4 (2)C12—C19—N5—C10−2.7 (2)
C20—C21—C22—C231.0 (5)O3—C11—N6—C19169.48 (19)
C21—C22—C23—C24−0.4 (5)N4—C11—N6—C19−13.1 (2)
C22—C23—C24—C250.0 (5)N5—C19—N6—C11−96.61 (19)
C21—C20—C25—C240.8 (4)C20—C19—N6—C11135.33 (17)
C19—C20—C25—C24−175.9 (2)C12—C19—N6—C1111.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5A···O1i0.86 (1)2.42 (2)3.004 (2)126 (2)
N5—H5A···O2i0.86 (1)2.11 (2)2.782 (2)135 (2)
N6—H6···O2i0.87 (1)2.44 (2)3.062 (2)130 (2)
N6—H6···O1ii0.87 (1)2.30 (2)3.041 (2)144 (2)
C8—H8A···O10.972.572.938 (3)103
C14—H14···N30.932.512.832 (3)101
C18—H18···N40.932.512.827 (3)100
C21—H21···N50.932.482.821 (3)102
C26—H26A···O1i0.98 (4)2.43 (4)3.364 (3)158 (3)
C9—H9B···O3iii0.972.233.165 (2)161
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) x, y+1, z; (iii) −x, −y+2, −z.

Experimental details

Crystal data
Chemical formulaC25H20N6O3.CHCl3
Mr571.84
Crystal system, space groupMonoclinic, P21/n
Temperature (K)292
a, b, c (Å)17.3315 (12), 8.4507 (6), 17.7874 (12)
β (°) 94.652 (1)
V (Å3)2596.6 (3)
Z4
Radiation typeMo Kα
µ (mm−1)0.40
Crystal size (mm)0.40 × 0.30 × 0.30
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		26236, 5081, 3995
Rint0.106
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.171, 1.12
No. of reflections5081
No. of parameters368
No. of restraints18
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.55, −0.45

Computer programs: SMART (Bruker, 2001), SMART, SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 2000), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5A···O1i0.857 (10)2.42 (2)3.004 (2)126 (2)
N5—H5A···O2i0.857 (10)2.11 (2)2.782 (2)135 (2)
N6—H6···O2i0.868 (10)2.44 (2)3.062 (2)130 (2)
N6—H6···O1ii0.868 (10)2.298 (17)3.041 (2)144 (2)
C8—H8A···O10.972.572.938 (3)102.8
C14—H14···N30.932.512.832 (3)100.5
C18—H18···N40.932.512.827 (3)100.4
C21—H21···N50.932.482.821 (3)101.7
C26—H26A···O1i0.98 (4)2.43 (4)3.364 (3)158 (3)
C9—H9B···O3iii0.972.233.165 (2)161.4
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) x, y+1, z; (iii) −x, −y+2, −z.
 

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