supplementary materials


nc2321 scheme

Acta Cryst. (2013). E69, o1831-o1832    [ doi:10.1107/S160053681303170X ]

N-(4-Meth­oxy­phen­yl)-6-methyl-2-phenyl-5-{[4-(tri­fluoro­meth­yl)anilino]meth­yl}pyrimidin-4-amine

J. Cieplik, J. Pluta, I. Bryndal and T. Lis

Abstract top

The title compound, C26H23F3N4O, crystallizes with two symmetry-independent mol­ecules in the asymmetric unit, denoted A and B, which differ mainly in the rotation of the meth­oxy­phenyl ring. The -CF3 group of mol­ecule B is disordered by rotation, with the F atoms split over two sets of sites; the occupancy factor for the major component is 0.853 (4). The dihedral angles between the pyrimidine ring and the attached phenyl, meth­oxy­phenyl and tri­fluoro­methyl­phenyl rings are 8.1 (2), 37.5 (2) and 70.7 (2)°, respectively, in mol­ecule A, and 9.3 (2), 5.3 (2) and 79.7 (2)° in mol­ecule B. An intra­molecular N-H...N hydrogen bond occurs in each mol­ecule. In the crystal, two crystallographically independent mol­ecules associate into a dimer via a pair of N-H...N hydrogen bonds, with a resulting R22(12) ring motif and [pi]-[pi] stacking inter­actions [centroid-centroid distance = 3.517 (4) Å] between the pyrimidine rings. For the A mol­ecules, there are inter­molecular C-H...O hydrogen bonds between an aryl C atom of meth­oxy­phenyl ring and a meth­oxy O atom of an adjacent mol­ecule. A similar inter­action is lacking in the B mol­ecules.

Comment top

The present paper is a continuation of our earlier works about the synthesis and biological activity of 6-methyl-2-phenyl-5-substitued pyrimidine derivatives (Cieplik et al., 1995, 2008) as well as their structural data (Cieplik, Pluta et al., 2006, 2012;Cieplik, Stolarczyk et al., 2012).

The title compound, namely N-(4-methoxyphenyl)-6-methyl-2-phenyl-5-[(4-trifluoromethylanilino)methyl]pyrimidin-4-amine, crystallizes with two symmetry-independent molecules in the asymmetric unit, hereafter referred to as A and B (Fig. 1). The molecules differ in the orientation of the methoxyphenyl group with respect to the pyrimidine ring; the angle between the least-squares planes through the pyrimidine and aryl rings is 37.5 (2)° in molecule A and 5.3 (2)° in molecule B. For both molecules, the phenyl ring attached to the atom C2 is nearly co-planar with the pyrimidine ring [dihedral angle = 8.1 (2) and 9.3 (2)° in molecule A and B, respectively], whereas the trifluoromethylphenyl ring attached to the atom C5 is almost perpendicular to pyrimidine ring plane [dihedral angle = 70.7 (2) and 79.7 (2)° in molecule A and B, respectively].

In the crystal structure, the N5 amide atom of molecule A acts as hydrogen-bond donor to the pyrimidine atom N1 of molecule B at (-x + 1, -y + 1, -z + 1). Simultaneously, the amide atom N5 of molecule B acts as hydrogen-bond donor to the pyrimidine atom N3 of molecule A at (-x + 1, -y + 1, -z + 1). The result is the formation of a centrosymmetric hydrogen-bonded dimer with the R22(12) ring motif. Furthemore, between pyrimidine rings of adjacent molecules within a dimer there is also an aromatic π-π stacking interaction (Fig. 2). The angle between the planes of these rings is 1.24 (9)°. The distance between the ring centroids of molecules at (x, y, z) and (-x + 1, -y + 1, -z + 1) is 3.517 (2) Å with an interplanar spacing of 3.488 (4) Å and a centroid offset of 0.45 Å. For molecules A, there are intermolecular C—H···O hydrogen bonds formed between the aryl atom C43A of the methoxyphenyl ring as a donor and the methoxy atom O4A at (-x + 2, -y + 1, -z + 2) as an acceptor (Fig. 2). A similar interaction is lacking in the B molecule. On the whole, a three-dimensional arrangment in the crystal structure consists of neighboring dimers, held together by C—H···O, C—F···π and C—H···π interactions as well as ππ interactions [the shortest centroid-centroid distance is 3.574 (4) Å].

Related literature top

For the antibacterial activity of 6-methyl-2-phenyl-5-substituted pyrimidine derivatives, see: Cieplik et al. (1995, 2008). For related structures, see: Cieplik, Pluta et al. (2006, 2012); Cieplik, Stolarczyk et al. (2012).

Experimental top

The title compound was obtained by adopting the procedure described previously by Cieplik et al. (1995). 4 g of 5-(chloromethyl)-N-(4-methoxyphenyl)-6-methyl-2-phenylpyrimidin-4-amine was dissolved in 30 ml of chloroform, and 3 g of 4-(trifluoromethyl)aniline. The reaction mixture was refluxed for 5 h with vigorous stirring, then was cooled and poured into 200 ml of water. The aqueous solution was extracted three times with chloroform (50 ml). The combined chloroform phases were dried over MgSO4, filtered and concentrated under vacuum. The oily residue was purified by column chromatography on silica gel (200–300 mesh) using CHCl3 as the eluent and by crystallization from methanol to give single crystals (yield: 4.3 g, 78.7%, m.p. 469–471 K).

Refinement top

The C—H H atoms were positioned with idealized geometry (methyl H atoms allowed to rotate but not to tip) and were refined with Uiso(H) = 1.2 Ueq(C) (1.5 for methyl H atoms) using a riding model with C—H distances between 0.95–0.99 Å. The –CF3 group in molecule B is disordered with the F atoms split over two sets of sites and were refined with the occupancy factors of 0.853 (4) and 0.147 (4). The F atoms of higher occupancy were refined anisotropic, whereas those of lower occupancy were refined isotropic.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. View of two symmetry independent molecules of the title compound with labelling scheme and displacement ellipsoids drawn at the 50% probability level. F atoms with the occupancy fator of 0.147 (4) and H atoms are shown as small spheres of arbitrary radii. The dotted lines indicate intramolecular N—H···O hydrogen bonds. Thick dashed lines represent fragment of a minor component of the disordered CF3 group.
[Figure 2] Fig. 2. The arrangement of molecules A (light orange line) and B (black line), showing the intermolecular N—H···N and C—H···O hydrogen bonds (thick dashed lines). Thin dashed lines indicate intramolecular N—H···O interactions. The atoms of disordered CF3 group (with the smaller occupancy factor) and H atoms not involved in hydrogen bonding have been omitted for clarity.
N-(4-Methoxyphenyl)-6-methyl-2-phenyl-5-{[4-(trifluoromethyl)anilino]methyl}pyrimidin-4-amine top
Crystal data top
C26H23F3N4OZ = 4
Mr = 464.48F(000) = 968
Triclinic, P1Dx = 1.370 Mg m3
Hall symbol: -P 1Melting point: 470 K
a = 8.724 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 15.141 (6) ÅCell parameters from 6466 reflections
c = 17.844 (7) Åθ = 2.8–29.8°
α = 93.89 (3)°µ = 0.10 mm1
β = 99.19 (3)°T = 100 K
γ = 103.26 (3)°Plate, light yellow
V = 2251.3 (15) Å30.43 × 0.08 × 0.04 mm
Data collection top
Oxford Diffraction Xcalibur PX
diffractometer with Ruby CCD
8352 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
Graphite monochromatorθmax = 29.8°, θmin = 2.8°
ω scansh = 1212
19792 measured reflectionsk = 2020
11372 independent reflectionsl = 2316
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0405P)2 + 1.2149P]
where P = (Fo2 + 2Fc2)/3
11372 reflections(Δ/σ)max = 0.001
642 parametersΔρmax = 0.44 e Å3
0 restraintsΔρmin = 0.43 e Å3
Crystal data top
C26H23F3N4Oγ = 103.26 (3)°
Mr = 464.48V = 2251.3 (15) Å3
Triclinic, P1Z = 4
a = 8.724 (3) ÅMo Kα radiation
b = 15.141 (6) ŵ = 0.10 mm1
c = 17.844 (7) ÅT = 100 K
α = 93.89 (3)°0.43 × 0.08 × 0.04 mm
β = 99.19 (3)°
Data collection top
Oxford Diffraction Xcalibur PX
diffractometer with Ruby CCD
8352 reflections with I > 2σ(I)
19792 measured reflectionsRint = 0.022
11372 independent reflectionsθmax = 29.8°
Refinement top
R[F2 > 2σ(F2)] = 0.054H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.125Δρmax = 0.44 e Å3
S = 1.03Δρmin = 0.43 e Å3
11372 reflectionsAbsolute structure: ?
642 parametersAbsolute structure parameter: ?
0 restraintsRogers parameter: ?
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)
N1A0.76237 (16)0.96728 (9)0.70258 (8)0.0196 (3)
C2A0.77090 (18)0.93972 (10)0.77236 (9)0.0173 (3)
C21A0.72164 (19)0.99489 (11)0.83225 (9)0.0185 (3)
C22A0.6485 (2)1.06514 (11)0.81371 (10)0.0225 (3)
H22A0.63201.07920.76240.027*
C23A0.5994 (2)1.11491 (12)0.86999 (11)0.0275 (4)
H23A0.54981.16280.85690.033*
C24A0.6225 (2)1.09485 (12)0.94470 (11)0.0301 (4)
H24A0.58751.12830.98280.036*
C25A0.6969 (2)1.02575 (12)0.96409 (10)0.0296 (4)
H25A0.71381.01221.01550.036*
C26A0.7467 (2)0.97631 (11)0.90814 (10)0.0242 (4)
H26A0.79840.92940.92170.029*
N3A0.81915 (16)0.86598 (9)0.79446 (8)0.0186 (3)
C4A0.87545 (19)0.81943 (10)0.74295 (9)0.0183 (3)
N4A0.93179 (18)0.74611 (10)0.76491 (8)0.0217 (3)
H4A0.939 (2)0.7078 (13)0.7290 (11)0.026*
C41A0.95084 (19)0.71744 (11)0.83927 (9)0.0198 (3)
C42A0.9273 (2)0.62391 (11)0.84616 (10)0.0228 (3)
H42A0.89680.58140.80150.027*
C43A0.9480 (2)0.59278 (12)0.91726 (10)0.0264 (4)
H43A0.93300.52920.92110.032*
C44A0.9908 (2)0.65398 (12)0.98311 (10)0.0239 (4)
C45A1.0181 (2)0.74671 (11)0.97710 (10)0.0226 (3)
H45A1.05000.78891.02190.027*
C46A0.9988 (2)0.77814 (11)0.90561 (9)0.0214 (3)
H46A1.01860.84190.90200.026*
O4A1.00329 (17)0.61577 (9)1.05081 (7)0.0336 (3)
C47A1.0558 (3)0.67576 (14)1.11979 (11)0.0378 (5)
H4A10.97990.71371.12430.057*
H4A21.16180.71501.11920.057*
H4A31.06200.63991.16340.057*
C5A0.87760 (19)0.84423 (10)0.66810 (9)0.0180 (3)
C57A0.9519 (2)0.79518 (11)0.61278 (9)0.0195 (3)
H5A10.95970.82870.56730.023*
H5A21.06170.79440.63720.023*
N5A0.85839 (17)0.70154 (9)0.58888 (8)0.0178 (3)
H5A0.758 (2)0.6910 (12)0.5904 (10)0.021*
C51A0.89123 (19)0.65284 (11)0.52727 (9)0.0172 (3)
C52A1.02539 (19)0.68484 (11)0.49402 (9)0.0197 (3)
H52A1.09870.74120.51450.024*
C53A1.0522 (2)0.63490 (11)0.43130 (9)0.0214 (3)
H53A1.14260.65770.40860.026*
C54A0.9476 (2)0.55191 (11)0.40175 (9)0.0209 (3)
C55A0.8172 (2)0.51759 (11)0.43617 (9)0.0212 (3)
H55A0.74760.45970.41710.025*
C56A0.78866 (19)0.56739 (11)0.49788 (9)0.0204 (3)
H56A0.69880.54370.52070.024*
C58A0.9720 (2)0.50213 (12)0.33149 (10)0.0260 (4)
F1A0.91413 (14)0.41104 (7)0.32686 (6)0.0357 (3)
F2A1.12666 (14)0.51503 (9)0.32574 (7)0.0447 (3)
F3A0.89861 (17)0.52706 (9)0.26695 (6)0.0454 (3)
C6A0.81483 (19)0.91782 (11)0.65045 (9)0.0193 (3)
C61A0.8028 (2)0.94979 (12)0.57186 (10)0.0277 (4)
H6A10.90810.98510.56540.042*
H6A20.72620.98830.56610.042*
H6A30.76610.89680.53310.042*
N1B0.48661 (16)0.31970 (9)0.39572 (8)0.0185 (3)
C2B0.54512 (18)0.24961 (11)0.41791 (9)0.0171 (3)
C21B0.55299 (19)0.23597 (11)0.50022 (9)0.0186 (3)
C22B0.5151 (2)0.30014 (12)0.54944 (9)0.0227 (3)
H22B0.47930.35000.52950.027*
C23B0.5289 (2)0.29203 (13)0.62693 (10)0.0280 (4)
H23B0.50320.33630.65980.034*
C24B0.5802 (2)0.21937 (13)0.65650 (10)0.0315 (4)
H24B0.59030.21400.70970.038*
C25B0.6169 (2)0.15432 (13)0.60817 (10)0.0297 (4)
H25B0.65140.10430.62830.036*
C26B0.6031 (2)0.16238 (11)0.53047 (10)0.0229 (4)
H26B0.62780.11760.49770.028*
N3B0.59856 (16)0.19190 (9)0.37388 (7)0.0184 (3)
C4B0.59796 (19)0.20995 (11)0.30120 (9)0.0186 (3)
N4B0.64158 (17)0.15329 (10)0.25047 (8)0.0220 (3)
H4B0.626 (2)0.1677 (13)0.2041 (12)0.026*
C41B0.70212 (19)0.07495 (11)0.25837 (9)0.0206 (3)
C42B0.7607 (2)0.04472 (12)0.19507 (10)0.0261 (4)
H42B0.75780.07720.15140.031*
C43B0.8222 (2)0.03115 (12)0.19513 (11)0.0292 (4)
H43B0.86140.05050.15170.035*
C44B0.8273 (2)0.07956 (12)0.25850 (11)0.0277 (4)
C45B0.7691 (2)0.05076 (12)0.32163 (11)0.0268 (4)
H45B0.77200.08370.36510.032*
C46B0.7062 (2)0.02651 (12)0.32151 (10)0.0236 (4)
H46B0.66640.04570.36480.028*
O4B0.88977 (17)0.15441 (9)0.25234 (8)0.0371 (3)
C47B0.9141 (3)0.20049 (15)0.31864 (13)0.0446 (6)
H4B10.81110.22380.33450.067*
H4B20.98650.15790.36000.067*
H4B30.96130.25150.30700.067*
C5B0.5562 (2)0.28906 (11)0.27414 (9)0.0203 (3)
C57B0.5920 (2)0.31925 (12)0.19865 (9)0.0247 (4)
H5B10.57590.38150.19480.030*
H5B20.70560.32180.19660.030*
N5B0.49060 (18)0.25812 (10)0.13371 (8)0.0234 (3)
H5B0.393 (2)0.2313 (13)0.1434 (11)0.028*
C51B0.4906 (2)0.28915 (11)0.06128 (9)0.0218 (3)
C52B0.6123 (2)0.36088 (13)0.04864 (10)0.0296 (4)
H52B0.69780.38910.08920.035*
C53B0.6088 (2)0.39129 (13)0.02353 (10)0.0310 (4)
H53B0.69100.44100.03180.037*
C54B0.4866 (2)0.34952 (12)0.08293 (9)0.0235 (4)
C55B0.3669 (2)0.27637 (12)0.07117 (10)0.0259 (4)
H55B0.28350.24690.11230.031*
C56B0.3694 (2)0.24656 (12)0.00045 (10)0.0255 (4)
H56B0.28750.19650.00820.031*
C58B0.4802 (2)0.38445 (14)0.15878 (10)0.0305 (4)
F1B0.4052 (4)0.31867 (17)0.21585 (9)0.0929 (11)0.853 (4)
F2B0.3985 (4)0.4458 (2)0.16732 (12)0.1126 (15)0.853 (4)
F3B0.6199 (2)0.4160 (2)0.17813 (11)0.0692 (8)0.853 (4)
F1C0.3625 (10)0.3680 (7)0.2021 (5)0.032 (2)*0.147 (4)
F2C0.5351 (12)0.4789 (6)0.1502 (5)0.038 (3)*0.147 (4)
F3C0.5767 (19)0.3600 (10)0.1951 (8)0.071 (4)*0.147 (4)
C6B0.49560 (19)0.34027 (11)0.32344 (9)0.0194 (3)
C61B0.4404 (2)0.42421 (12)0.30291 (10)0.0259 (4)
H6B10.53370.47580.30680.039*
H6B20.37160.43820.33810.039*
H6B30.38010.41320.25050.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0220 (7)0.0186 (7)0.0189 (7)0.0071 (6)0.0037 (6)0.0009 (5)
C2A0.0169 (7)0.0165 (7)0.0177 (8)0.0026 (6)0.0036 (6)0.0005 (6)
C21A0.0185 (8)0.0171 (7)0.0194 (8)0.0022 (6)0.0058 (6)0.0005 (6)
C22A0.0243 (8)0.0207 (8)0.0229 (8)0.0065 (7)0.0051 (7)0.0003 (7)
C23A0.0265 (9)0.0232 (9)0.0341 (10)0.0096 (7)0.0067 (8)0.0027 (8)
C24A0.0318 (10)0.0282 (9)0.0310 (10)0.0067 (8)0.0135 (8)0.0080 (8)
C25A0.0390 (11)0.0292 (9)0.0215 (9)0.0074 (8)0.0110 (8)0.0017 (7)
C26A0.0316 (9)0.0207 (8)0.0219 (8)0.0077 (7)0.0073 (7)0.0019 (7)
N3A0.0223 (7)0.0170 (6)0.0172 (7)0.0057 (5)0.0046 (5)0.0010 (5)
C4A0.0197 (8)0.0160 (7)0.0189 (8)0.0042 (6)0.0034 (6)0.0001 (6)
N4A0.0300 (8)0.0194 (7)0.0188 (7)0.0112 (6)0.0070 (6)0.0009 (6)
C41A0.0196 (8)0.0203 (8)0.0216 (8)0.0073 (6)0.0050 (6)0.0040 (6)
C42A0.0251 (9)0.0186 (8)0.0248 (9)0.0075 (7)0.0027 (7)0.0003 (7)
C43A0.0307 (9)0.0168 (8)0.0314 (10)0.0070 (7)0.0013 (8)0.0059 (7)
C44A0.0246 (9)0.0243 (8)0.0250 (9)0.0080 (7)0.0047 (7)0.0104 (7)
C45A0.0265 (9)0.0220 (8)0.0197 (8)0.0070 (7)0.0039 (7)0.0017 (7)
C46A0.0257 (9)0.0176 (8)0.0222 (8)0.0066 (7)0.0053 (7)0.0033 (6)
O4A0.0495 (9)0.0272 (7)0.0250 (7)0.0104 (6)0.0042 (6)0.0112 (5)
C47A0.0551 (13)0.0376 (11)0.0242 (10)0.0178 (10)0.0052 (9)0.0098 (8)
C5A0.0190 (8)0.0174 (7)0.0165 (7)0.0026 (6)0.0041 (6)0.0017 (6)
C57A0.0217 (8)0.0182 (8)0.0188 (8)0.0042 (6)0.0062 (6)0.0002 (6)
N5A0.0159 (6)0.0177 (6)0.0198 (7)0.0037 (5)0.0051 (6)0.0013 (5)
C51A0.0184 (7)0.0186 (7)0.0162 (7)0.0088 (6)0.0013 (6)0.0012 (6)
C52A0.0174 (8)0.0197 (8)0.0214 (8)0.0053 (6)0.0022 (6)0.0007 (6)
C53A0.0205 (8)0.0248 (8)0.0200 (8)0.0074 (7)0.0046 (7)0.0000 (7)
C54A0.0222 (8)0.0233 (8)0.0179 (8)0.0114 (7)0.0012 (7)0.0012 (6)
C55A0.0221 (8)0.0174 (8)0.0217 (8)0.0055 (6)0.0022 (7)0.0021 (6)
C56A0.0189 (8)0.0202 (8)0.0223 (8)0.0057 (6)0.0035 (7)0.0016 (7)
C58A0.0263 (9)0.0298 (9)0.0229 (9)0.0123 (7)0.0013 (7)0.0027 (7)
F1A0.0466 (7)0.0272 (6)0.0321 (6)0.0128 (5)0.0037 (5)0.0099 (5)
F2A0.0304 (6)0.0562 (8)0.0449 (7)0.0093 (6)0.0127 (5)0.0229 (6)
F3A0.0727 (9)0.0526 (8)0.0187 (5)0.0369 (7)0.0015 (6)0.0002 (5)
C6A0.0204 (8)0.0186 (8)0.0173 (8)0.0028 (6)0.0031 (6)0.0005 (6)
C61A0.0406 (11)0.0285 (9)0.0176 (8)0.0148 (8)0.0063 (8)0.0037 (7)
N1B0.0168 (6)0.0215 (7)0.0181 (7)0.0056 (5)0.0039 (5)0.0050 (5)
C2B0.0132 (7)0.0204 (8)0.0172 (8)0.0023 (6)0.0032 (6)0.0035 (6)
C21B0.0169 (7)0.0219 (8)0.0183 (8)0.0050 (6)0.0056 (6)0.0042 (6)
C22B0.0273 (9)0.0238 (8)0.0216 (8)0.0121 (7)0.0079 (7)0.0066 (7)
C23B0.0396 (11)0.0301 (9)0.0211 (9)0.0166 (8)0.0125 (8)0.0045 (7)
C24B0.0480 (12)0.0355 (10)0.0198 (9)0.0195 (9)0.0151 (8)0.0116 (8)
C25B0.0437 (11)0.0287 (9)0.0255 (9)0.0189 (8)0.0137 (8)0.0123 (8)
C26B0.0291 (9)0.0227 (8)0.0221 (8)0.0118 (7)0.0105 (7)0.0055 (7)
N3B0.0180 (7)0.0206 (7)0.0169 (7)0.0048 (5)0.0036 (5)0.0029 (5)
C4B0.0162 (7)0.0216 (8)0.0169 (8)0.0028 (6)0.0029 (6)0.0013 (6)
N4B0.0259 (8)0.0247 (7)0.0163 (7)0.0070 (6)0.0051 (6)0.0033 (6)
C41B0.0178 (8)0.0213 (8)0.0210 (8)0.0025 (6)0.0035 (6)0.0014 (7)
C42B0.0265 (9)0.0265 (9)0.0242 (9)0.0017 (7)0.0094 (7)0.0003 (7)
C43B0.0271 (9)0.0271 (9)0.0326 (10)0.0031 (7)0.0124 (8)0.0060 (8)
C44B0.0222 (9)0.0213 (8)0.0376 (10)0.0049 (7)0.0035 (8)0.0043 (8)
C45B0.0269 (9)0.0248 (9)0.0277 (9)0.0057 (7)0.0029 (8)0.0031 (7)
C46B0.0236 (9)0.0247 (8)0.0216 (8)0.0042 (7)0.0049 (7)0.0000 (7)
O4B0.0387 (8)0.0280 (7)0.0479 (9)0.0147 (6)0.0100 (7)0.0011 (6)
C47B0.0470 (13)0.0369 (11)0.0510 (14)0.0230 (10)0.0045 (11)0.0005 (10)
C5B0.0209 (8)0.0231 (8)0.0155 (8)0.0032 (7)0.0020 (6)0.0034 (6)
C57B0.0261 (9)0.0265 (9)0.0205 (8)0.0037 (7)0.0046 (7)0.0049 (7)
N5B0.0235 (7)0.0269 (8)0.0184 (7)0.0026 (6)0.0035 (6)0.0049 (6)
C51B0.0253 (9)0.0248 (8)0.0193 (8)0.0109 (7)0.0075 (7)0.0060 (7)
C52B0.0289 (10)0.0368 (10)0.0192 (9)0.0025 (8)0.0015 (7)0.0024 (8)
C53B0.0347 (10)0.0356 (10)0.0217 (9)0.0030 (8)0.0090 (8)0.0069 (8)
C54B0.0305 (9)0.0276 (9)0.0171 (8)0.0126 (7)0.0082 (7)0.0066 (7)
C55B0.0277 (9)0.0305 (9)0.0211 (8)0.0114 (8)0.0031 (7)0.0029 (7)
C56B0.0258 (9)0.0258 (9)0.0249 (9)0.0053 (7)0.0046 (7)0.0055 (7)
C58B0.0378 (11)0.0373 (11)0.0196 (9)0.0136 (9)0.0066 (8)0.0066 (8)
F1B0.153 (2)0.0736 (16)0.0148 (8)0.0459 (16)0.0155 (10)0.0035 (8)
F2B0.191 (3)0.169 (3)0.0605 (13)0.157 (3)0.0730 (17)0.0816 (16)
F3B0.0387 (9)0.116 (2)0.0414 (10)0.0134 (11)0.0035 (8)0.0516 (12)
C6B0.0171 (8)0.0214 (8)0.0182 (8)0.0023 (6)0.0012 (6)0.0045 (6)
C61B0.0295 (9)0.0292 (9)0.0228 (9)0.0128 (8)0.0051 (7)0.0101 (7)
Geometric parameters (Å, º) top
N1A—C2A1.336 (2)C2B—N3B1.345 (2)
N1A—C6A1.354 (2)C2B—C21B1.490 (2)
C2A—N3A1.342 (2)C21B—C22B1.396 (2)
C2A—C21A1.488 (2)C21B—C26B1.398 (2)
C21A—C22A1.393 (2)C22B—C23B1.385 (2)
C21A—C26A1.395 (2)C22B—H22B0.9500
C22A—C23A1.394 (2)C23B—C24B1.385 (2)
C22A—H22A0.9500C23B—H23B0.9500
C23A—C24A1.381 (3)C24B—C25B1.391 (3)
C23A—H23A0.9500C24B—H24B0.9500
C24A—C25A1.387 (3)C25B—C26B1.388 (2)
C24A—H24A0.9500C25B—H25B0.9500
C25A—C26A1.390 (2)C26B—H26B0.9500
C25A—H25A0.9500N3B—C4B1.343 (2)
C26A—H26A0.9500C4B—N4B1.362 (2)
N3A—C4A1.341 (2)C4B—C5B1.422 (2)
C4A—N4A1.370 (2)N4B—C41B1.411 (2)
C4A—C5A1.414 (2)N4B—H4B0.87 (2)
N4A—C41A1.420 (2)C41B—C46B1.385 (2)
N4A—H4A0.86 (2)C41B—C42B1.403 (2)
C41A—C46A1.392 (2)C42B—C43B1.375 (3)
C41A—C42A1.400 (2)C42B—H42B0.9500
C42A—C43A1.383 (2)C43B—C44B1.389 (3)
C42A—H42A0.9500C43B—H43B0.9500
C43A—C44A1.390 (3)C44B—O4B1.371 (2)
C43A—H43A0.9500C44B—C45B1.391 (3)
C44A—O4A1.374 (2)C45B—C46B1.402 (2)
C44A—C45A1.384 (2)C45B—H45B0.9500
C45A—C46A1.390 (2)C46B—H46B0.9500
C45A—H45A0.9500O4B—C47B1.425 (3)
C46A—H46A0.9500C47B—H4B10.9800
O4A—C47A1.424 (2)C47B—H4B20.9800
C47A—H4A10.9800C47B—H4B30.9800
C47A—H4A20.9800C5B—C6B1.378 (2)
C47A—H4A30.9800C5B—C57B1.508 (2)
C5A—C6A1.383 (2)C57B—N5B1.461 (2)
C5A—C57A1.507 (2)C57B—H5B10.9900
C57A—N5A1.461 (2)C57B—H5B20.9900
C57A—H5A10.9900N5B—C51B1.405 (2)
C57A—H5A20.9900N5B—H5B0.91 (2)
N5A—C51A1.386 (2)C51B—C56B1.392 (3)
N5A—H5A0.860 (19)C51B—C52B1.392 (3)
C51A—C52A1.399 (2)C52B—C53B1.395 (3)
C51A—C56A1.406 (2)C52B—H52B0.9500
C52A—C53A1.389 (2)C53B—C54B1.378 (3)
C52A—H52A0.9500C53B—H53B0.9500
C53A—C54A1.386 (2)C54B—C55B1.390 (3)
C53A—H53A0.9500C54B—C58B1.484 (2)
C54A—C55A1.392 (2)C55B—C56B1.382 (2)
C54A—C58A1.489 (2)C55B—H55B0.9500
C55A—C56A1.380 (2)C56B—H56B0.9500
C55A—H55A0.9500C58B—F1C1.147 (9)
C56A—H56A0.9500C58B—F3C1.245 (13)
C58A—F2A1.340 (2)C58B—F2B1.297 (3)
C58A—F3A1.347 (2)C58B—F3B1.312 (3)
C58A—F1A1.348 (2)C58B—F1B1.345 (3)
C6A—C61A1.510 (2)C58B—F2C1.390 (8)
C61A—H6A10.9800C6B—C61B1.506 (2)
C61A—H6A20.9800C61B—H6B10.9800
C61A—H6A30.9800C61B—H6B20.9800
N1B—C2B1.336 (2)C61B—H6B30.9800
N1B—C6B1.357 (2)
C2A—N1A—C6A116.17 (14)N3B—C2B—C21B117.67 (14)
N1A—C2A—N3A126.42 (14)C22B—C21B—C26B118.70 (15)
N1A—C2A—C21A117.79 (14)C22B—C21B—C2B119.33 (14)
N3A—C2A—C21A115.80 (14)C26B—C21B—C2B121.93 (14)
C22A—C21A—C26A118.80 (15)C23B—C22B—C21B120.84 (15)
C22A—C21A—C2A120.90 (15)C23B—C22B—H22B119.6
C26A—C21A—C2A120.30 (15)C21B—C22B—H22B119.6
C21A—C22A—C23A120.38 (16)C22B—C23B—C24B120.04 (16)
C21A—C22A—H22A119.8C22B—C23B—H23B120.0
C23A—C22A—H22A119.8C24B—C23B—H23B120.0
C24A—C23A—C22A120.27 (17)C23B—C24B—C25B119.87 (16)
C24A—C23A—H23A119.9C23B—C24B—H24B120.1
C22A—C23A—H23A119.9C25B—C24B—H24B120.1
C23A—C24A—C25A119.93 (16)C26B—C25B—C24B120.14 (16)
C23A—C24A—H24A120.0C26B—C25B—H25B119.9
C25A—C24A—H24A120.0C24B—C25B—H25B119.9
C24A—C25A—C26A119.92 (17)C25B—C26B—C21B120.41 (15)
C24A—C25A—H25A120.0C25B—C26B—H26B119.8
C26A—C25A—H25A120.0C21B—C26B—H26B119.8
C25A—C26A—C21A120.70 (16)C4B—N3B—C2B115.63 (14)
C25A—C26A—H26A119.7N3B—C4B—N4B120.65 (15)
C21A—C26A—H26A119.7N3B—C4B—C5B122.21 (14)
C4A—N3A—C2A116.58 (14)N4B—C4B—C5B117.12 (15)
N3A—C4A—N4A117.90 (15)C4B—N4B—C41B132.62 (15)
N3A—C4A—C5A121.85 (14)C4B—N4B—H4B112.9 (13)
N4A—C4A—C5A120.26 (14)C41B—N4B—H4B114.5 (13)
C4A—N4A—C41A127.03 (14)C46B—C41B—C42B118.77 (16)
C4A—N4A—H4A116.4 (13)C46B—C41B—N4B125.95 (15)
C41A—N4A—H4A115.5 (13)C42B—C41B—N4B115.27 (15)
C46A—C41A—C42A118.36 (15)C43B—C42B—C41B121.18 (17)
C46A—C41A—N4A123.10 (15)C43B—C42B—H42B119.4
C42A—C41A—N4A118.48 (15)C41B—C42B—H42B119.4
C43A—C42A—C41A120.64 (16)C42B—C43B—C44B120.17 (17)
C43A—C42A—H42A119.7C42B—C43B—H43B119.9
C41A—C42A—H42A119.7C44B—C43B—H43B119.9
C42A—C43A—C44A120.37 (16)O4B—C44B—C43B115.42 (16)
C42A—C43A—H43A119.8O4B—C44B—C45B125.17 (18)
C44A—C43A—H43A119.8C43B—C44B—C45B119.41 (16)
O4A—C44A—C45A124.72 (16)C44B—C45B—C46B120.39 (17)
O4A—C44A—C43A115.69 (15)C44B—C45B—H45B119.8
C45A—C44A—C43A119.58 (16)C46B—C45B—H45B119.8
C44A—C45A—C46A120.07 (16)C41B—C46B—C45B120.07 (16)
C44A—C45A—H45A120.0C41B—C46B—H46B120.0
C46A—C45A—H45A120.0C45B—C46B—H46B120.0
C45A—C46A—C41A120.93 (15)C44B—O4B—C47B117.60 (16)
C45A—C46A—H46A119.5O4B—C47B—H4B1109.5
C41A—C46A—H46A119.5O4B—C47B—H4B2109.5
C44A—O4A—C47A117.84 (14)H4B1—C47B—H4B2109.5
O4A—C47A—H4A1109.5O4B—C47B—H4B3109.5
O4A—C47A—H4A2109.5H4B1—C47B—H4B3109.5
H4A1—C47A—H4A2109.5H4B2—C47B—H4B3109.5
O4A—C47A—H4A3109.5C6B—C5B—C4B116.38 (15)
H4A1—C47A—H4A3109.5C6B—C5B—C57B122.28 (15)
H4A2—C47A—H4A3109.5C4B—C5B—C57B121.08 (15)
C6A—C5A—C4A116.23 (14)N5B—C57B—C5B112.42 (14)
C6A—C5A—C57A122.67 (15)N5B—C57B—H5B1109.1
C4A—C5A—C57A121.03 (14)C5B—C57B—H5B1109.1
N5A—C57A—C5A111.76 (14)N5B—C57B—H5B2109.1
N5A—C57A—H5A1109.3C5B—C57B—H5B2109.1
C5A—C57A—H5A1109.3H5B1—C57B—H5B2107.9
N5A—C57A—H5A2109.3C51B—N5B—C57B117.00 (14)
C5A—C57A—H5A2109.3C51B—N5B—H5B115.1 (13)
H5A1—C57A—H5A2107.9C57B—N5B—H5B112.8 (12)
C51A—N5A—C57A119.11 (14)C56B—C51B—C52B119.07 (16)
C51A—N5A—H5A113.0 (12)C56B—C51B—N5B119.87 (16)
C57A—N5A—H5A116.4 (12)C52B—C51B—N5B121.05 (16)
N5A—C51A—C52A122.27 (15)C51B—C52B—C53B120.07 (17)
N5A—C51A—C56A119.24 (15)C51B—C52B—H52B120.0
C52A—C51A—C56A118.47 (14)C53B—C52B—H52B120.0
C53A—C52A—C51A120.50 (15)C54B—C53B—C52B120.23 (18)
C53A—C52A—H52A119.7C54B—C53B—H53B119.9
C51A—C52A—H52A119.7C52B—C53B—H53B119.9
C54A—C53A—C52A120.26 (16)C53B—C54B—C55B119.99 (16)
C54A—C53A—H53A119.9C53B—C54B—C58B119.97 (17)
C52A—C53A—H53A119.9C55B—C54B—C58B120.02 (17)
C53A—C54A—C55A119.80 (15)C56B—C55B—C54B119.89 (17)
C53A—C54A—C58A119.59 (16)C56B—C55B—H55B120.1
C55A—C54A—C58A120.56 (16)C54B—C55B—H55B120.1
C56A—C55A—C54A120.23 (16)C55B—C56B—C51B120.72 (17)
C56A—C55A—H55A119.9C55B—C56B—H56B119.6
C54A—C55A—H55A119.9C51B—C56B—H56B119.6
C55A—C56A—C51A120.66 (16)F1C—C58B—F3C103.9 (8)
C55A—C56A—H56A119.7F2B—C58B—F3B108.4 (2)
C51A—C56A—H56A119.7F2B—C58B—F1B103.4 (2)
F2A—C58A—F3A106.24 (15)F3B—C58B—F1B103.09 (19)
F2A—C58A—F1A105.81 (14)F1C—C58B—F2C106.0 (6)
F3A—C58A—F1A104.94 (14)F3C—C58B—F2C102.1 (8)
F2A—C58A—C54A112.95 (15)F1C—C58B—C54B120.7 (4)
F3A—C58A—C54A112.84 (14)F3C—C58B—C54B112.0 (6)
F1A—C58A—C54A113.37 (16)F2B—C58B—C54B113.64 (16)
N1A—C6A—C5A122.52 (15)F3B—C58B—C54B115.09 (17)
N1A—C6A—C61A115.20 (14)F1B—C58B—C54B112.06 (18)
C5A—C6A—C61A122.27 (14)F2C—C58B—C54B110.3 (4)
C6A—C61A—H6A1109.5N1B—C6B—C5B121.65 (15)
C6A—C61A—H6A2109.5N1B—C6B—C61B115.08 (14)
H6A1—C61A—H6A2109.5C5B—C6B—C61B123.23 (15)
C6A—C61A—H6A3109.5C6B—C61B—H6B1109.5
H6A1—C61A—H6A3109.5C6B—C61B—H6B2109.5
H6A2—C61A—H6A3109.5H6B1—C61B—H6B2109.5
C2B—N1B—C6B116.87 (14)C6B—C61B—H6B3109.5
N1B—C2B—N3B126.61 (15)H6B1—C61B—H6B3109.5
N1B—C2B—C21B115.72 (14)H6B2—C61B—H6B3109.5
C6A—N1A—C2A—N3A3.3 (2)N3B—C2B—C21B—C22B173.11 (15)
C6A—N1A—C2A—C21A177.16 (14)N1B—C2B—C21B—C26B176.34 (15)
N1A—C2A—C21A—C22A8.7 (2)N3B—C2B—C21B—C26B4.5 (2)
N3A—C2A—C21A—C22A170.91 (15)C26B—C21B—C22B—C23B0.9 (3)
N1A—C2A—C21A—C26A171.94 (15)C2B—C21B—C22B—C23B176.72 (16)
N3A—C2A—C21A—C26A8.4 (2)C21B—C22B—C23B—C24B0.3 (3)
C26A—C21A—C22A—C23A0.9 (3)C22B—C23B—C24B—C25B0.4 (3)
C2A—C21A—C22A—C23A178.45 (16)C23B—C24B—C25B—C26B0.4 (3)
C21A—C22A—C23A—C24A0.2 (3)C24B—C25B—C26B—C21B0.3 (3)
C22A—C23A—C24A—C25A0.9 (3)C22B—C21B—C26B—C25B0.9 (3)
C23A—C24A—C25A—C26A0.6 (3)C2B—C21B—C26B—C25B176.66 (16)
C24A—C25A—C26A—C21A0.5 (3)N1B—C2B—N3B—C4B2.8 (2)
C22A—C21A—C26A—C25A1.2 (3)C21B—C2B—N3B—C4B176.25 (14)
C2A—C21A—C26A—C25A178.12 (16)C2B—N3B—C4B—N4B176.55 (14)
N1A—C2A—N3A—C4A5.3 (2)C2B—N3B—C4B—C5B5.0 (2)
C21A—C2A—N3A—C4A175.08 (14)N3B—C4B—N4B—C41B4.7 (3)
C2A—N3A—C4A—N4A177.33 (14)C5B—C4B—N4B—C41B173.80 (16)
C2A—N3A—C4A—C5A2.7 (2)C4B—N4B—C41B—C46B12.1 (3)
N3A—C4A—N4A—C41A5.9 (3)C4B—N4B—C41B—C42B168.68 (17)
C5A—C4A—N4A—C41A174.03 (16)C46B—C41B—C42B—C43B0.4 (3)
C4A—N4A—C41A—C46A36.2 (3)N4B—C41B—C42B—C43B179.65 (16)
C4A—N4A—C41A—C42A146.82 (17)C41B—C42B—C43B—C44B0.1 (3)
C46A—C41A—C42A—C43A1.3 (2)C42B—C43B—C44B—O4B179.52 (16)
N4A—C41A—C42A—C43A178.51 (16)C42B—C43B—C44B—C45B0.2 (3)
C41A—C42A—C43A—C44A0.8 (3)O4B—C44B—C45B—C46B179.38 (16)
C42A—C43A—C44A—O4A178.00 (16)C43B—C44B—C45B—C46B0.1 (3)
C42A—C43A—C44A—C45A2.3 (3)C42B—C41B—C46B—C45B0.5 (2)
O4A—C44A—C45A—C46A178.66 (16)N4B—C41B—C46B—C45B179.63 (16)
C43A—C44A—C45A—C46A1.6 (3)C44B—C45B—C46B—C41B0.2 (3)
C44A—C45A—C46A—C41A0.5 (3)C43B—C44B—O4B—C47B173.20 (17)
C42A—C41A—C46A—C45A2.0 (2)C45B—C44B—O4B—C47B7.5 (3)
N4A—C41A—C46A—C45A179.01 (16)N3B—C4B—C5B—C6B8.4 (2)
C45A—C44A—O4A—C47A3.3 (3)N4B—C4B—C5B—C6B173.10 (15)
C43A—C44A—O4A—C47A176.40 (17)N3B—C4B—C5B—C57B165.89 (15)
N3A—C4A—C5A—C6A1.5 (2)N4B—C4B—C5B—C57B12.6 (2)
N4A—C4A—C5A—C6A178.51 (15)C6B—C5B—C57B—N5B115.30 (18)
N3A—C4A—C5A—C57A175.67 (15)C4B—C5B—C57B—N5B70.8 (2)
N4A—C4A—C5A—C57A4.3 (2)C5B—C57B—N5B—C51B167.43 (14)
C6A—C5A—C57A—N5A113.92 (17)C57B—N5B—C51B—C56B163.61 (15)
C4A—C5A—C57A—N5A69.1 (2)C57B—N5B—C51B—C52B17.9 (2)
C5A—C57A—N5A—C51A167.33 (13)C56B—C51B—C52B—C53B2.2 (3)
C57A—N5A—C51A—C52A9.6 (2)N5B—C51B—C52B—C53B179.23 (17)
C57A—N5A—C51A—C56A171.81 (14)C51B—C52B—C53B—C54B1.1 (3)
N5A—C51A—C52A—C53A178.62 (15)C52B—C53B—C54B—C55B0.5 (3)
C56A—C51A—C52A—C53A2.8 (2)C52B—C53B—C54B—C58B177.63 (17)
C51A—C52A—C53A—C54A1.1 (2)C53B—C54B—C55B—C56B1.0 (3)
C52A—C53A—C54A—C55A1.5 (2)C58B—C54B—C55B—C56B177.13 (16)
C52A—C53A—C54A—C58A176.02 (15)C54B—C55B—C56B—C51B0.2 (3)
C53A—C54A—C55A—C56A2.3 (2)C52B—C51B—C56B—C55B1.8 (3)
C58A—C54A—C55A—C56A175.15 (15)N5B—C51B—C56B—C55B179.70 (15)
C54A—C55A—C56A—C51A0.6 (2)C53B—C54B—C58B—F1C159.3 (6)
N5A—C51A—C56A—C55A179.41 (14)C55B—C54B—C58B—F1C18.8 (7)
C52A—C51A—C56A—C55A1.9 (2)C53B—C54B—C58B—F3C77.9 (8)
C53A—C54A—C58A—F2A32.5 (2)C55B—C54B—C58B—F3C104.0 (8)
C55A—C54A—C58A—F2A150.03 (16)C53B—C54B—C58B—F2B90.5 (3)
C53A—C54A—C58A—F3A88.0 (2)C55B—C54B—C58B—F2B87.6 (3)
C55A—C54A—C58A—F3A89.5 (2)C53B—C54B—C58B—F3B35.3 (3)
C53A—C54A—C58A—F1A152.88 (15)C55B—C54B—C58B—F3B146.6 (2)
C55A—C54A—C58A—F1A29.7 (2)C53B—C54B—C58B—F1B152.7 (2)
C2A—N1A—C6A—C5A1.6 (2)C55B—C54B—C58B—F1B29.2 (3)
C2A—N1A—C6A—C61A179.52 (15)C53B—C54B—C58B—F2C35.1 (5)
C4A—C5A—C6A—N1A3.7 (2)C55B—C54B—C58B—F2C143.0 (5)
C57A—C5A—C6A—N1A173.41 (15)C2B—N1B—C6B—C5B2.6 (2)
C4A—C5A—C6A—C61A177.44 (16)C2B—N1B—C6B—C61B175.34 (14)
C57A—C5A—C6A—C61A5.4 (3)C4B—C5B—C6B—N1B4.3 (2)
C6B—N1B—C2B—N3B6.7 (2)C57B—C5B—C6B—N1B169.86 (15)
C6B—N1B—C2B—C21B172.44 (14)C4B—C5B—C6B—C61B177.91 (15)
N1B—C2B—C21B—C22B6.1 (2)C57B—C5B—C6B—C61B7.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5A—H5A···N1Bi0.860 (19)2.16 (2)3.012 (2)172.6 (17)
N5B—H5B···N3Ai0.91 (2)2.54 (2)3.403 (2)159.7 (17)
C43A—H43A···O4Aii0.952.453.355 (2)159
N4A—H4A···N5A0.86 (2)2.48 (2)3.099 (2)130.2 (16)
N4B—H4B···N5B0.87 (2)2.31 (2)3.021 (2)139.0 (17)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+2, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5A—H5A···N1Bi0.860 (19)2.16 (2)3.012 (2)172.6 (17)
N5B—H5B···N3Ai0.91 (2)2.54 (2)3.403 (2)159.7 (17)
C43A—H43A···O4Aii0.952.453.355 (2)159.4
N4A—H4A···N5A0.86 (2)2.48 (2)3.099 (2)130.2 (16)
N4B—H4B···N5B0.87 (2)2.31 (2)3.021 (2)139.0 (17)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+2, y+1, z+2.
references
References top

Brandenburg, K. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.

Cieplik, J., Machoń, Z., Zimecki, M. & Wieczorek, Z. (1995). Il Farmaco, 50, 131–136.

Cieplik, J., Pluta, J., Bryndal, I. & Lis, T. (2006). Acta Cryst. C62, o259–o261.

Cieplik, J., Pluta, J., Bryndal, I. & Lis, T. (2012). Acta Cryst. E68, o3412.

Cieplik, J., Raginia, M., Pluta, J., Gubrynowicz, O., Bryndal, I. & Lis, T. (2008). Acta Pol. Pharm. 65, 427–434.

Cieplik, J., Stolarczyk, M., Bryndal, I. & Lis, T. (2012). Acta Cryst. E68, o1729–o1730.

Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.