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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o349.
Published online 2010 January 13. doi:  10.1107/S1600536810000899
PMCID: PMC2979750

N-(5-Amino-2-methyl­phen­yl)-4-(3-pyri­dyl)­pyrimidin-2-amine

Abstract

The title compound, C16H15N5, crystallizes with two independent mol­ecules (A and B) in the asymmetric unit. The dihedral angles of the pyrimidine ring with the benzene and pyridyl rings are 22.3 (1) and 53.2 (9)°, respectively, in mol­ecule A, and 6.8 (1) and 11.6 (9)° in mol­ecule B. The crystal packing is influenced by the collective action of weak inter­molecular N—H(...)N hydrogen bonds, a π–π stacking inter­action between neighbouring pyridyl rings of mol­ecule A [centroid–centroid distance = 3.8395 (10) Å] and C—H(...)π inter­actions.

Related literature

For imatinib mesylate, see: Druker et al. (1996 [triangle], 2001 [triangle]); Kalaycio (2004 [triangle]); Peggs & Mackinnon (2003 [triangle]). For related structures, see: Hu et al. (2006 [triangle]); Lynch & McClenaghan (2001 [triangle]); Santoni et al. (2008 [triangle]); Wolska et al. (2003 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For MOPAC Parameterized Model 3 calculation, see: Schmidt & Polik (2007 [triangle]).

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Object name is e-66-0o349-scheme1.jpg

Experimental

Crystal data

  • C16H15N5
  • M r = 277.33
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o349-efi1.jpg
  • a = 9.2242 (3) Å
  • b = 12.5399 (4) Å
  • c = 12.8594 (4) Å
  • α = 72.719 (3)°
  • β = 89.724 (3)°
  • γ = 77.712 (3)°
  • V = 1385.05 (8) Å3
  • Z = 4
  • Cu Kα radiation
  • μ = 0.67 mm−1
  • T = 200 K
  • 0.55 × 0.48 × 0.37 mm

Data collection

  • Oxford Diffraction Gemini R diffractometer
  • 11476 measured reflections
  • 5337 independent reflections
  • 4629 reflections with I > 2σ(I)
  • R int = 0.041

Refinement

  • R[F 2 > 2σ(F 2)] = 0.066
  • wR(F 2) = 0.198
  • S = 1.08
  • 5337 reflections
  • 381 parameters
  • H-atom parameters constrained
  • Δρmax = 0.32 e Å−3
  • Δρmin = −0.36 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 [triangle]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810000899/is2512sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000899/is2512Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

QNMHA thanks the University of Mysore for the use of their research facilities. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

supplementary crystallographic information

Comment

The title compound, (I), C16H15N5, is an intermediate in the synthesis of imatinib mesylate, a specific inhibitor of Bcr-Abl kinase, produces clinical remission in CML patients with minimal toxicity (Druker et al., 1996, 2001). This selective inhibition of Bcr-Abl kinase by STI-571 has been a successful therapeutic strategy for CML because of the high efficacy and mild side effects of this compound (Peggs & Mackinnon, 2003; Kalaycio, 2004). Imatinib, a 2-phenylaminopyrimidine derivative that functions as a specific inhibitor of a number of tyrosine kinase enzymes, is a drug used to treat certain types of cancer and is used in treating chronic myelogenous leukemia (CML), gastrointestinal stromal tumors (GISTs) and a number of other malignancies. It is the first member of a new class of agents that act by inhibiting particular tyrosine kinase enzymes, instead of non-specifically inhibiting rapidly dividing cells. The crystal structures of related compounds, viz, 2-amino-4-(4-pyridyl)pyrimidine and the 1:1 adduct with 4-aminobenzoic acid (Lynch & McClenaghan, 2001), 4-(2-pyridyl)-1H,2H-pyrido[1,2-c]pyrimidine-1,3-dione (Wolska et al., 2003), 3-(4-methylphenyl)-2-(1-pyridyl)-3H-benzo[4,5]furo[3,2-d]pyrimidin-4-one (Hu et al., 2006), and 5-phenyl-2-(4-pyridyl)pyrimidine (Santoni et al., 2008) have been reported. In view of the importance of the title compound, its crystal structure is reported.

The title compound crystallizes with two molecules (A & B) in the asymmetric unit (Fig. 1 & 2). The molecular structure consists of an amine nitrogen atom bonded to 5-amino-2-methylphenyl and 3-pyridyl-2-pyrimidine groups, respectively. Bond lengths and bond angles are all within expected ranges (Allen et al., 1987). The dihedral angles between the mean planes of the 2-pyrimidine ring and the phenyl and pyridyl rings are 22.3 (1) and 53.2 (9)° in A, and 6.8 (1) and 11.6 (9)° in B, respectively, presenting a much different structural arrangement in each of these molecules. Crystal packing is influenced by the collective action of weak intermolecular N—H···N hydrogen bond interactions (Table 1 and Fig. 3), π-π stacking interactions between nearby pyridyl A rings, [Cg1···Cg1iv = 3.8395 Å; slippage = 1.520 Å; Cg1 is the centroid of C12A–C15A/N5A/C16A ring; symmetry code: (iv) -x, -y, 2 - z] and C—H···π interactions between the pyridyl A and phenyl A rings and between the phenyl A and B rings (Table 1).

A geometry optimized MOPAC PM3 (Parameterized Model 3) computational calculation (Schmidt & Polik, 2007), in vacuo, on each molecule separately supports these observations. The dihedral angle between the mean planes of the 2-pyrimidine ring and the phenyl and pyridyl rings change to 36.86, 40.06° in A and 0.00, 9.95° in B, respectively, providing support to these effects and contribute to the packing of these molecules into chains propagating along the [011].

Experimental

The title compound was obtained as a gift sample from INTERMED LABS PRIVATE LTD., Bangalore, India. X-ray quality crystals were grown from methanol: ethyl acetate (9:1) by slow evaporation of solvent mixture. The melting range was found to be 398–401 K.

Refinement

All of the H atoms were placed in their calculated positions and then refined using the riding model, with C—N = 0.88 Å and C—H = 0.95–0.98 Å, and with Uiso(H) = 1.19–1.50Ueq(C, N).

Figures

Fig. 1.
Molecular structure of (I), C16H15N5, molecule A, showing the atom labeling scheme and 50% probability displacement ellipsoids.
Fig. 2.
Molecular structure of (I), C16H15N5, molecule B, showing the atom labeling scheme and 50% probability displacement ellipsoids.
Fig. 3.
The molecular packing for (I) viewed down the a axis. Dashed lines indicate weak N—H···N intermolecular hydrogen bond interactions which link the molecule into chains propagating along the [011].

Crystal data

C16H15N5Z = 4
Mr = 277.33F(000) = 584
Triclinic, P1Dx = 1.330 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54184 Å
a = 9.2242 (3) ÅCell parameters from 8631 reflections
b = 12.5399 (4) Åθ = 4.4–73.5°
c = 12.8594 (4) ŵ = 0.67 mm1
α = 72.719 (3)°T = 200 K
β = 89.724 (3)°Prism, yellow-orange
γ = 77.712 (3)°0.55 × 0.48 × 0.37 mm
V = 1385.05 (8) Å3

Data collection

Oxford Diffraction Gemini R diffractometer4629 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.041
graphiteθmax = 73.7°, θmin = 4.4°
Detector resolution: 10.5081 pixels mm-1h = −11→10
[var phi] and ω scansk = −15→15
11476 measured reflectionsl = −15→15
5337 independent reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.198H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.1456P)2 + 0.1456P] where P = (Fo2 + 2Fc2)/3
5337 reflections(Δ/σ)max = 0.008
381 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = −0.36 e Å3

Special details

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)

xyzUiso*/Ueq
N1A0.45135 (18)1.19152 (15)0.78047 (14)0.0532 (4)
H1AA0.48131.24720.79650.064*
H1AB0.49891.12000.81040.064*
N2A0.09164 (16)1.06549 (11)0.59640 (10)0.0367 (3)
H2AB0.07311.07180.52750.044*
N3A0.00963 (15)0.89841 (12)0.63377 (10)0.0351 (3)
N4A0.09680 (14)0.95804 (11)0.77803 (10)0.0315 (3)
N5A0.22563 (16)0.91112 (13)1.09733 (11)0.0402 (3)
C1A0.14467 (17)1.15507 (13)0.61884 (11)0.0325 (3)
C2A0.27421 (17)1.12989 (14)0.68428 (12)0.0354 (3)
H2AA0.32671.05250.71360.043*
C3A0.32847 (18)1.21663 (15)0.70762 (13)0.0384 (4)
C4A0.2529 (2)1.33008 (14)0.66004 (13)0.0402 (4)
H4AA0.29001.39080.67200.048*
C5A0.1243 (2)1.35351 (14)0.59555 (13)0.0405 (4)
H5AA0.07401.43120.56440.049*
C6A0.06427 (18)1.26855 (14)0.57380 (11)0.0349 (3)
C7A−0.0847 (2)1.29936 (16)0.51227 (14)0.0449 (4)
H7AA−0.10311.23220.49490.067*
H7AB−0.08521.36140.44450.067*
H7AC−0.16271.32450.55730.067*
C8A0.06709 (16)0.97057 (13)0.67282 (11)0.0307 (3)
C9A−0.02004 (18)0.80801 (14)0.70933 (13)0.0364 (4)
H9AA−0.06060.75500.68560.044*
C10A0.00484 (18)0.78733 (14)0.81973 (12)0.0352 (3)
H10A−0.01750.72220.87170.042*
C11A0.06433 (15)0.86674 (13)0.85112 (12)0.0305 (3)
C12A0.09418 (16)0.85691 (13)0.96677 (11)0.0309 (3)
C13A0.02152 (18)0.79443 (15)1.05046 (13)0.0379 (4)
H13A−0.04850.75481.03470.045*
C14A0.05232 (19)0.79062 (15)1.15671 (13)0.0410 (4)
H14A0.00430.74841.21520.049*
C15A0.15462 (19)0.84969 (15)1.17594 (13)0.0396 (4)
H15A0.17580.84651.24920.048*
C16A0.19464 (18)0.91374 (14)0.99509 (12)0.0352 (3)
H16A0.24410.95700.93830.042*
N1B0.6390 (2)0.87330 (16)0.93581 (14)0.0577 (5)
H1BA0.70290.91690.93340.069*
H1BB0.60780.83800.99880.069*
N2B0.35671 (16)0.69036 (13)0.74824 (11)0.0410 (3)
H2BB0.32410.69490.68250.049*
N3B0.23997 (18)0.54289 (14)0.79199 (12)0.0442 (4)
N4B0.33110 (14)0.60433 (12)0.93401 (11)0.0351 (3)
N5B0.40511 (18)0.59479 (14)1.25219 (12)0.0479 (4)
C1B0.44747 (17)0.76724 (14)0.74862 (13)0.0365 (4)
C2B0.49205 (18)0.78610 (14)0.84372 (13)0.0386 (4)
H2BA0.45740.74840.91150.046*
C3B0.58759 (18)0.86016 (15)0.84028 (15)0.0409 (4)
C4B0.63588 (18)0.91542 (15)0.73977 (15)0.0436 (4)
H4BA0.70050.96610.73570.052*
C5B0.58953 (19)0.89634 (15)0.64595 (15)0.0439 (4)
H5BA0.62380.93470.57830.053*
C6B0.49516 (18)0.82354 (15)0.64661 (13)0.0402 (4)
C7B0.4463 (2)0.80618 (19)0.54245 (15)0.0525 (5)
H7BA0.50100.84440.48240.079*
H7BB0.33950.83880.52660.079*
H7BC0.46650.72410.55060.079*
C8B0.30922 (17)0.61004 (14)0.82990 (13)0.0351 (3)
C9B0.1970 (3)0.46071 (19)0.86902 (16)0.0539 (5)
H9BA0.14910.41030.84690.065*
C10B0.2180 (3)0.44439 (18)0.97932 (16)0.0528 (5)
H10B0.18920.38291.03230.063*
C11B0.28304 (18)0.52179 (14)1.00929 (14)0.0373 (4)
C12B0.30358 (18)0.51873 (14)1.12446 (13)0.0374 (4)
C13B0.2455 (2)0.44605 (18)1.20945 (15)0.0509 (5)
H13B0.19050.39521.19540.061*
C14B0.2686 (3)0.44835 (19)1.31517 (16)0.0563 (5)
H14B0.23030.39901.37470.068*
C15B0.3480 (2)0.52349 (18)1.33216 (15)0.0494 (4)
H15B0.36310.52481.40480.059*
C16B0.3822 (2)0.59124 (16)1.15134 (14)0.0420 (4)
H16B0.42220.64161.09370.050*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N1A0.0455 (8)0.0539 (9)0.0633 (10)−0.0141 (7)−0.0140 (7)−0.0198 (8)
N2A0.0504 (8)0.0383 (7)0.0242 (6)−0.0166 (6)−0.0026 (5)−0.0088 (5)
N3A0.0419 (7)0.0404 (7)0.0270 (6)−0.0152 (6)−0.0007 (5)−0.0119 (5)
N4A0.0344 (6)0.0360 (7)0.0262 (6)−0.0104 (5)0.0003 (5)−0.0107 (5)
N5A0.0437 (7)0.0474 (8)0.0311 (7)−0.0121 (6)−0.0043 (5)−0.0129 (6)
C1A0.0392 (8)0.0361 (8)0.0248 (6)−0.0131 (6)0.0039 (5)−0.0100 (5)
C2A0.0367 (8)0.0372 (8)0.0336 (7)−0.0106 (6)0.0018 (6)−0.0109 (6)
C3A0.0381 (8)0.0463 (9)0.0345 (8)−0.0159 (7)0.0019 (6)−0.0132 (6)
C4A0.0502 (9)0.0402 (8)0.0358 (8)−0.0195 (7)0.0028 (6)−0.0130 (6)
C5A0.0546 (10)0.0343 (8)0.0319 (7)−0.0109 (7)−0.0007 (6)−0.0082 (6)
C6A0.0413 (8)0.0394 (8)0.0238 (6)−0.0101 (6)0.0001 (6)−0.0084 (6)
C7A0.0495 (9)0.0448 (9)0.0381 (8)−0.0037 (7)−0.0097 (7)−0.0135 (7)
C8A0.0321 (7)0.0344 (7)0.0271 (7)−0.0087 (6)0.0005 (5)−0.0107 (5)
C9A0.0409 (8)0.0419 (8)0.0332 (8)−0.0184 (6)0.0025 (6)−0.0153 (6)
C10A0.0389 (8)0.0396 (8)0.0299 (7)−0.0158 (6)0.0035 (6)−0.0097 (6)
C11A0.0285 (7)0.0364 (7)0.0274 (7)−0.0076 (6)0.0016 (5)−0.0106 (6)
C12A0.0304 (7)0.0350 (7)0.0271 (7)−0.0056 (6)0.0003 (5)−0.0100 (6)
C13A0.0391 (8)0.0466 (9)0.0306 (8)−0.0144 (7)0.0032 (6)−0.0121 (6)
C14A0.0451 (9)0.0497 (9)0.0278 (8)−0.0125 (7)0.0073 (6)−0.0099 (6)
C15A0.0460 (9)0.0457 (9)0.0262 (7)−0.0050 (7)−0.0026 (6)−0.0132 (6)
C16A0.0379 (8)0.0411 (8)0.0281 (7)−0.0123 (6)0.0003 (6)−0.0103 (6)
N1B0.0666 (11)0.0661 (11)0.0539 (9)−0.0375 (9)0.0047 (8)−0.0222 (8)
N2B0.0444 (7)0.0495 (8)0.0332 (7)−0.0205 (6)0.0025 (5)−0.0117 (6)
N3B0.0504 (8)0.0514 (8)0.0397 (7)−0.0241 (7)0.0054 (6)−0.0182 (6)
N4B0.0319 (6)0.0393 (7)0.0362 (7)−0.0123 (5)0.0042 (5)−0.0118 (5)
N5B0.0513 (9)0.0535 (9)0.0423 (8)−0.0134 (7)−0.0011 (6)−0.0183 (7)
C1B0.0322 (7)0.0371 (8)0.0401 (8)−0.0099 (6)0.0039 (6)−0.0101 (6)
C2B0.0376 (8)0.0407 (8)0.0397 (8)−0.0139 (7)0.0062 (6)−0.0117 (7)
C3B0.0355 (8)0.0400 (8)0.0490 (9)−0.0108 (6)0.0017 (7)−0.0145 (7)
C4B0.0354 (8)0.0401 (8)0.0570 (10)−0.0152 (7)0.0061 (7)−0.0123 (7)
C5B0.0384 (8)0.0433 (9)0.0461 (9)−0.0110 (7)0.0081 (7)−0.0067 (7)
C6B0.0362 (8)0.0424 (9)0.0392 (8)−0.0084 (7)0.0032 (6)−0.0084 (7)
C7B0.0612 (11)0.0611 (11)0.0365 (9)−0.0258 (9)0.0064 (8)−0.0079 (8)
C8B0.0314 (7)0.0384 (8)0.0374 (8)−0.0103 (6)0.0033 (6)−0.0127 (6)
C9B0.0702 (12)0.0605 (11)0.0472 (10)−0.0402 (10)0.0110 (9)−0.0229 (9)
C10B0.0721 (13)0.0568 (11)0.0424 (9)−0.0398 (10)0.0124 (8)−0.0164 (8)
C11B0.0350 (8)0.0407 (8)0.0383 (8)−0.0121 (6)0.0061 (6)−0.0124 (6)
C12B0.0357 (8)0.0403 (8)0.0376 (8)−0.0093 (6)0.0047 (6)−0.0132 (7)
C13B0.0584 (11)0.0587 (11)0.0436 (10)−0.0277 (9)0.0129 (8)−0.0176 (8)
C14B0.0692 (13)0.0637 (12)0.0393 (9)−0.0244 (10)0.0153 (8)−0.0140 (8)
C15B0.0547 (10)0.0569 (11)0.0365 (9)−0.0077 (8)0.0032 (7)−0.0174 (8)
C16B0.0441 (9)0.0460 (9)0.0379 (8)−0.0145 (7)0.0023 (7)−0.0125 (7)

Geometric parameters (Å, °)

N1A—C3A1.394 (2)N1B—C3B1.386 (2)
N1A—H1AA0.8800N1B—H1BA0.8800
N1A—H1AB0.8800N1B—H1BB0.8800
N2A—C8A1.3606 (19)N2B—C8B1.365 (2)
N2A—C1A1.4186 (19)N2B—C1B1.406 (2)
N2A—H2AB0.8800N2B—H2BB0.8800
N3A—C9A1.334 (2)N3B—C9B1.328 (2)
N3A—C8A1.3522 (19)N3B—C8B1.353 (2)
N4A—C11A1.3371 (19)N4B—C8B1.333 (2)
N4A—C8A1.3377 (18)N4B—C11B1.342 (2)
N5A—C16A1.336 (2)N5B—C16B1.330 (2)
N5A—C15A1.338 (2)N5B—C15B1.336 (3)
C1A—C2A1.388 (2)C1B—C2B1.392 (2)
C1A—C6A1.406 (2)C1B—C6B1.410 (2)
C2A—C3A1.397 (2)C2B—C3B1.402 (2)
C2A—H2AA0.9500C2B—H2BA0.9500
C3A—C4A1.396 (2)C3B—C4B1.394 (2)
C4A—C5A1.378 (2)C4B—C5B1.384 (3)
C4A—H4AA0.9500C4B—H4BA0.9500
C5A—C6A1.396 (2)C5B—C6B1.387 (2)
C5A—H5AA0.9500C5B—H5BA0.9500
C6A—C7A1.505 (2)C6B—C7B1.505 (2)
C7A—H7AA0.9800C7B—H7BA0.9800
C7A—H7AB0.9800C7B—H7BB0.9800
C7A—H7AC0.9800C7B—H7BC0.9800
C9A—C10A1.376 (2)C9B—C10B1.380 (3)
C9A—H9AA0.9500C9B—H9BA0.9500
C10A—C11A1.389 (2)C10B—C11B1.387 (2)
C10A—H10A0.9500C10B—H10B0.9500
C11A—C12A1.4776 (19)C11B—C12B1.482 (2)
C12A—C13A1.392 (2)C12B—C13B1.387 (2)
C12A—C16A1.392 (2)C12B—C16B1.394 (2)
C13A—C14A1.382 (2)C13B—C14B1.387 (3)
C13A—H13A0.9500C13B—H13B0.9500
C14A—C15A1.382 (2)C14B—C15B1.375 (3)
C14A—H14A0.9500C14B—H14B0.9500
C15A—H15A0.9500C15B—H15B0.9500
C16A—H16A0.9500C16B—H16B0.9500
C3A—N1A—H1AA120.0C3B—N1B—H1BA120.0
C3A—N1A—H1AB120.0C3B—N1B—H1BB120.0
H1AA—N1A—H1AB120.0H1BA—N1B—H1BB120.0
C8A—N2A—C1A125.27 (12)C8B—N2B—C1B132.56 (13)
C8A—N2A—H2AB117.4C8B—N2B—H2BB113.7
C1A—N2A—H2AB117.4C1B—N2B—H2BB113.7
C9A—N3A—C8A115.26 (12)C9B—N3B—C8B114.62 (14)
C11A—N4A—C8A116.85 (13)C8B—N4B—C11B116.88 (14)
C16A—N5A—C15A117.00 (14)C16B—N5B—C15B116.92 (16)
C2A—C1A—C6A121.09 (14)C2B—C1B—N2B122.80 (14)
C2A—C1A—N2A119.94 (14)C2B—C1B—C6B120.89 (15)
C6A—C1A—N2A118.97 (14)N2B—C1B—C6B116.30 (14)
C1A—C2A—C3A120.97 (15)C1B—C2B—C3B120.59 (15)
C1A—C2A—H2AA119.5C1B—C2B—H2BA119.7
C3A—C2A—H2AA119.5C3B—C2B—H2BA119.7
N1A—C3A—C4A120.05 (15)N1B—C3B—C4B120.74 (16)
N1A—C3A—C2A121.35 (16)N1B—C3B—C2B120.41 (16)
C4A—C3A—C2A118.55 (14)C4B—C3B—C2B118.76 (16)
C5A—C4A—C3A119.66 (15)C5B—C4B—C3B119.87 (15)
C5A—C4A—H4AA120.2C5B—C4B—H4BA120.1
C3A—C4A—H4AA120.2C3B—C4B—H4BA120.1
C4A—C5A—C6A123.15 (15)C4B—C5B—C6B122.78 (16)
C4A—C5A—H5AA118.4C4B—C5B—H5BA118.6
C6A—C5A—H5AA118.4C6B—C5B—H5BA118.6
C5A—C6A—C1A116.50 (14)C5B—C6B—C1B117.11 (16)
C5A—C6A—C7A120.24 (15)C5B—C6B—C7B121.02 (15)
C1A—C6A—C7A123.11 (14)C1B—C6B—C7B121.86 (15)
C6A—C7A—H7AA109.5C6B—C7B—H7BA109.5
C6A—C7A—H7AB109.5C6B—C7B—H7BB109.5
H7AA—C7A—H7AB109.5H7BA—C7B—H7BB109.5
C6A—C7A—H7AC109.5C6B—C7B—H7BC109.5
H7AA—C7A—H7AC109.5H7BA—C7B—H7BC109.5
H7AB—C7A—H7AC109.5H7BB—C7B—H7BC109.5
N4A—C8A—N3A125.95 (14)N4B—C8B—N3B126.65 (15)
N4A—C8A—N2A118.49 (13)N4B—C8B—N2B120.66 (14)
N3A—C8A—N2A115.53 (12)N3B—C8B—N2B112.68 (14)
N3A—C9A—C10A123.62 (14)N3B—C9B—C10B123.72 (16)
N3A—C9A—H9AA118.2N3B—C9B—H9BA118.1
C10A—C9A—H9AA118.2C10B—C9B—H9BA118.1
C9A—C10A—C11A116.47 (14)C9B—C10B—C11B116.98 (16)
C9A—C10A—H10A121.8C9B—C10B—H10B121.5
C11A—C10A—H10A121.8C11B—C10B—H10B121.5
N4A—C11A—C10A121.83 (13)N4B—C11B—C10B121.01 (15)
N4A—C11A—C12A115.68 (13)N4B—C11B—C12B116.35 (14)
C10A—C11A—C12A122.49 (14)C10B—C11B—C12B122.65 (15)
C13A—C12A—C16A117.58 (14)C13B—C12B—C16B117.07 (15)
C13A—C12A—C11A122.18 (14)C13B—C12B—C11B122.48 (15)
C16A—C12A—C11A120.21 (13)C16B—C12B—C11B120.45 (15)
C14A—C13A—C12A119.29 (15)C12B—C13B—C14B119.26 (18)
C14A—C13A—H13A120.4C12B—C13B—H13B120.4
C12A—C13A—H13A120.4C14B—C13B—H13B120.4
C13A—C14A—C15A118.45 (15)C15B—C14B—C13B118.68 (18)
C13A—C14A—H14A120.8C15B—C14B—H14B120.7
C15A—C14A—H14A120.8C13B—C14B—H14B120.7
N5A—C15A—C14A123.75 (14)N5B—C15B—C14B123.59 (16)
N5A—C15A—H15A118.1N5B—C15B—H15B118.2
C14A—C15A—H15A118.1C14B—C15B—H15B118.2
N5A—C16A—C12A123.93 (14)N5B—C16B—C12B124.47 (16)
N5A—C16A—H16A118.0N5B—C16B—H16B117.8
C12A—C16A—H16A118.0C12B—C16B—H16B117.8
C8A—N2A—C1A—C2A53.0 (2)C8B—N2B—C1B—C2B−9.9 (3)
C8A—N2A—C1A—C6A−127.07 (16)C8B—N2B—C1B—C6B168.66 (17)
C6A—C1A—C2A—C3A0.2 (2)N2B—C1B—C2B—C3B177.37 (15)
N2A—C1A—C2A—C3A−179.91 (14)C6B—C1B—C2B—C3B−1.1 (3)
C1A—C2A—C3A—N1A174.58 (15)C1B—C2B—C3B—N1B−176.01 (16)
C1A—C2A—C3A—C4A−2.6 (2)C1B—C2B—C3B—C4B0.6 (3)
N1A—C3A—C4A—C5A−174.45 (16)N1B—C3B—C4B—C5B176.50 (17)
C2A—C3A—C4A—C5A2.8 (2)C2B—C3B—C4B—C5B−0.1 (3)
C3A—C4A—C5A—C6A−0.5 (3)C3B—C4B—C5B—C6B0.1 (3)
C4A—C5A—C6A—C1A−1.9 (2)C4B—C5B—C6B—C1B−0.5 (3)
C4A—C5A—C6A—C7A173.70 (16)C4B—C5B—C6B—C7B179.38 (17)
C2A—C1A—C6A—C5A2.0 (2)C2B—C1B—C6B—C5B1.0 (2)
N2A—C1A—C6A—C5A−177.91 (13)N2B—C1B—C6B—C5B−177.55 (14)
C2A—C1A—C6A—C7A−173.39 (14)C2B—C1B—C6B—C7B−178.88 (16)
N2A—C1A—C6A—C7A6.7 (2)N2B—C1B—C6B—C7B2.6 (2)
C11A—N4A—C8A—N3A−1.2 (2)C11B—N4B—C8B—N3B1.8 (2)
C11A—N4A—C8A—N2A176.72 (13)C11B—N4B—C8B—N2B−179.01 (14)
C9A—N3A—C8A—N4A0.7 (2)C9B—N3B—C8B—N4B−3.2 (3)
C9A—N3A—C8A—N2A−177.29 (13)C9B—N3B—C8B—N2B177.55 (17)
C1A—N2A—C8A—N4A−1.1 (2)C1B—N2B—C8B—N4B9.8 (3)
C1A—N2A—C8A—N3A176.99 (14)C1B—N2B—C8B—N3B−170.97 (17)
C8A—N3A—C9A—C10A0.0 (2)C8B—N3B—C9B—C10B0.9 (3)
N3A—C9A—C10A—C11A−0.1 (2)N3B—C9B—C10B—C11B2.4 (3)
C8A—N4A—C11A—C10A1.0 (2)C8B—N4B—C11B—C10B1.9 (2)
C8A—N4A—C11A—C12A−178.27 (12)C8B—N4B—C11B—C12B−178.07 (13)
C9A—C10A—C11A—N4A−0.5 (2)C9B—C10B—C11B—N4B−3.9 (3)
C9A—C10A—C11A—C12A178.78 (14)C9B—C10B—C11B—C12B176.12 (18)
N4A—C11A—C12A—C13A156.70 (14)N4B—C11B—C12B—C13B173.11 (16)
C10A—C11A—C12A—C13A−22.6 (2)C10B—C11B—C12B—C13B−6.9 (3)
N4A—C11A—C12A—C16A−21.4 (2)N4B—C11B—C12B—C16B−6.2 (2)
C10A—C11A—C12A—C16A159.27 (15)C10B—C11B—C12B—C16B173.81 (18)
C16A—C12A—C13A—C14A−0.5 (2)C16B—C12B—C13B—C14B−0.3 (3)
C11A—C12A—C13A—C14A−178.66 (14)C11B—C12B—C13B—C14B−179.66 (17)
C12A—C13A—C14A—C15A0.2 (3)C12B—C13B—C14B—C15B0.4 (3)
C16A—N5A—C15A—C14A−0.4 (3)C16B—N5B—C15B—C14B0.0 (3)
C13A—C14A—C15A—N5A0.3 (3)C13B—C14B—C15B—N5B−0.2 (3)
C15A—N5A—C16A—C12A0.0 (2)C15B—N5B—C16B—C12B0.0 (3)
C13A—C12A—C16A—N5A0.4 (2)C13B—C12B—C16B—N5B0.2 (3)
C11A—C12A—C16A—N5A178.63 (14)C11B—C12B—C16B—N5B179.52 (16)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1A—H1AA···N5Bi0.882.363.154 (2)151
N2A—H2AB···N3Aii0.882.112.9815 (17)170
N1B—H1BA···N5Ai0.882.313.130 (2)155
C2A—H2AA···Cg30.952.873.7834 (19)162
C14A—H14A···Cg2iii0.952.643.4709 (18)146

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2512).

References

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