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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): o1676.
Published online 2009 June 24. doi:  10.1107/S1600536809023629
PMCID: PMC2969425

4-(1-Adamantylmeth­yl)-N-(2-chloro-9-isopropyl-9H-purin-6-yl)aniline

Abstract

The asymmetric unit of the title compound, C25H30ClN5, consists of two mol­ecules with slightly different geometrical parameters. The dihedral angles between the purine and benzene rings are 39.54 (5) and 23.69 (5)° in the two mol­ecules. The adamantane cages consist of three fused cyclo­hexane rings in classical chair conformations, with C—C—C angles in the range 108 (2)–111 (2)°. In the crystal, mol­ecules are linked into dimers via two N—H(...)N hydrogen bonds.

Related literature

The title compound was prepared according to a modification of the procedure of Fiorini & Abel (1998 [triangle]). For the synthesis and/or biological activity of related compounds, see: Hardcastle et al. (2002 [triangle]); Villhauer et al., (2003 [triangle]). For related structures, see: Trávníček & Zatloukal (2004 [triangle]); Trávníček & Popa (2007a [triangle],b [triangle]); Rouchal et al. (2009a [triangle],b [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1676-scheme1.jpg

Experimental

Crystal data

  • C25H30ClN5
  • M r = 435.99
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1676-efi1.jpg
  • a = 11.731 (1) Å
  • b = 13.421 (1) Å
  • c = 15.531 (1) Å
  • α = 72.002 (7)°
  • β = 81.912 (7)°
  • γ = 79.688 (7)°
  • V = 2278.4 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.19 mm−1
  • T = 120 K
  • 0.20 × 0.20 × 0.10 mm

Data collection

  • Kuma KM-4-CCD diffractometer
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 [triangle]) T min = 0.962, T max = 0.981
  • 17173 measured reflections
  • 7983 independent reflections
  • 4502 reflections with I > 2σ(I)
  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.033
  • wR(F 2) = 0.081
  • S = 0.85
  • 7983 reflections
  • 563 parameters
  • H-atom parameters constrained
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.28 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 [triangle]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809023629/im2124sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809023629/im2124Isup2.hkl

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

Acknowledgments

The financial support of this work by the Science Foundation of Czech Republic (grant No. 203/06/P362) and by the Czech Ministry of Education (project No. MSM 7088352101) is gratefully acknowledged.

supplementary crystallographic information

Comment

The published structure represents a typical member of a new trisubstituted purine series currently synthesized in our laboratory. These molecules belong to the family of purine derivatives that exhibit a wide range of biological activities. Purine based molecules with suitable substituents at the most active centers can present low-molecular-weight inhibitors of cyclin-dependent kinases playing a crucial role in the regulation of the cell division cycle (Hardcastle et al., 2002). A unique adamantane moiety is frequently linked into known medicaments or drug candidates with the aim to improve the biological properties of these structures, e.g. a novel potent hypoglycemic agent reported by Villhauer et al. (2003).

The title compound (Fig. 1) crystallizes with two geometrically slightly different molecules in the asymmetric unit that are linked into dimers by two N–H···N hydrogen bonds (Table 1). The dihedral angles between purine and benzene rings are 39.54 (5)° and 23.69 (5)°. The torsion angles describing the orientation of isopropyl, purine, benzene and adamantane moiety C22–N5–C23–H23A, C21–C18–N1–C15 and C17–C12–C11–C1 are -177.4 (2), 174.9 (2) and -94.6 (3)° respectively. The corresponding values of torsion angles for the second conformer are 144.0 (2), 173.9 (2) and -98.4 (2)° respectively.

Experimental

The title compound was prepared according to a slightly modified literature procedure (Fiorini & Abel, 1998). 2,6-Dichloro-9-(propan-2-yl)-9H-purine (0.85 mmol, 196 mg) and 4-[(1-adamantyl)methyl]aniline hydrochloride (0.90 mmol, 250 mg) were dissolved in a mixture of DMF (2.5 ml) and triethylamine (1.70 mmol, 0.24 ml). The resulting solution was stirred at 363 K for required time (according to TLC). After the reaction was complete, the mixture was diluted with water and extracted with diethyl ether (5 times 15 ml). The connected organic layers were washed twice with brine and dried over sodium sulfate. The desired product was obtained by evaporation of the solvent in vacuum followed by purification of the crude product using column chromatography (silica gel; light petroleum/ethyl acetate (1:1 v/v) as a colorless crystalline powder (152 mg, 41%, mp 453–457 K). The single crystals suitable for X-ray analysis were grown by liquid diffusion (acetone/hexane, 1:3 v/v) at room temperature within 24 h.

Refinement

Hydrogen atoms were positioned geometrically and refined as riding using standard SHELXTL facilities, with their Uiso set to either 1.2Ueq or 1.5Ueq (methyl) of their parent atoms.

Figures

Fig. 1.
ORTEP plot of the asymmetric unit with atoms represented as 50% probability ellipsoids (H-bonds are denoted as dashed lines).

Crystal data

C25H30ClN5Z = 4
Mr = 435.99F(000) = 928
Triclinic, P1Dx = 1.271 Mg m3
Hall symbol: -P 1Melting point: 455 K
a = 11.731 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.421 (1) ÅCell parameters from 7983 reflections
c = 15.531 (1) Åθ = 2.8–25.0°
α = 72.002 (7)°µ = 0.19 mm1
β = 81.912 (7)°T = 120 K
γ = 79.688 (7)°Plate, colourless
V = 2278.4 (3) Å30.20 × 0.20 × 0.10 mm

Data collection

Kuma KM-4-CCD diffractometer7983 independent reflections
Radiation source: fine-focus sealed tube4502 reflections with I > 2σ(I)
graphiteRint = 0.030
Detector resolution: 0.06 pixels mm-1θmax = 25.0°, θmin = 2.8°
ω scansh = −13→13
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)k = −15→10
Tmin = 0.962, Tmax = 0.981l = −18→18
17173 measured 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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081H-atom parameters constrained
S = 0.85w = 1/[σ2(Fo2) + (0.0366P)2] where P = (Fo2 + 2Fc2)/3
7983 reflections(Δ/σ)max = 0.002
563 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = −0.28 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 > 2σ(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
Cl10.66480 (5)0.02196 (4)1.09703 (4)0.02989 (16)
N10.47703 (14)0.31228 (13)0.84935 (11)0.0212 (4)
H1A0.46620.33520.79110.025*
N20.56519 (14)0.16913 (14)0.96467 (11)0.0213 (4)
N30.64870 (14)0.00011 (13)0.93892 (11)0.0203 (4)
N40.54147 (15)0.16914 (14)0.72689 (11)0.0253 (5)
N50.62661 (14)−0.00033 (14)0.78420 (11)0.0233 (4)
C10.15565 (17)0.67309 (16)1.02665 (14)0.0192 (5)
C20.07127 (18)0.59104 (16)1.05850 (14)0.0228 (5)
H2B0.07990.55101.12300.027*
H2C0.09050.54031.02220.027*
C3−0.05581 (18)0.64537 (17)1.04799 (14)0.0230 (5)
H3B−0.10930.59061.06890.028*
C4−0.06925 (18)0.70646 (17)0.94756 (14)0.0252 (6)
H4B−0.05090.65670.91030.030*
H4C−0.15070.74110.94040.030*
C50.01297 (18)0.79041 (17)0.91466 (14)0.0258 (6)
H5A0.00420.82960.84920.031*
C6−0.01802 (19)0.86830 (16)0.97223 (14)0.0261 (6)
H6A0.03400.92330.95140.031*
H6B−0.09920.90370.96520.031*
C7−0.00410 (18)0.80685 (17)1.07278 (14)0.0256 (6)
H7A−0.02340.85711.11040.031*
C80.12254 (18)0.75150 (17)1.08348 (14)0.0237 (5)
H8A0.17590.80541.06370.028*
H8B0.13140.71311.14830.028*
C90.13970 (17)0.73551 (17)0.92593 (13)0.0221 (5)
H9A0.19300.78940.90470.027*
H9B0.15990.68650.88810.027*
C10−0.08652 (18)0.72313 (16)1.10517 (14)0.0239 (5)
H10A−0.16800.75791.09870.029*
H10B−0.07890.68451.17010.029*
C110.28362 (18)0.62051 (17)1.03993 (14)0.0247 (5)
H11A0.33340.67731.02020.030*
H11B0.28980.58661.10580.030*
C120.33367 (17)0.53798 (18)0.99061 (14)0.0216 (5)
C130.38638 (17)0.56703 (17)0.90161 (14)0.0222 (5)
H13A0.38880.64000.87130.027*
C140.43523 (17)0.49333 (17)0.85604 (14)0.0221 (5)
H14A0.47030.51590.79560.027*
C150.43260 (17)0.38575 (17)0.89960 (14)0.0186 (5)
C160.38099 (18)0.35447 (17)0.98847 (14)0.0237 (5)
H16A0.37880.28151.01880.028*
C170.33275 (18)0.42993 (17)1.03266 (14)0.0251 (6)
H17A0.29810.40731.09320.030*
C180.53343 (17)0.21243 (17)0.87816 (14)0.0183 (5)
C190.62045 (18)0.06941 (18)0.98556 (14)0.0210 (5)
C200.61511 (18)0.04658 (17)0.85336 (14)0.0205 (5)
C210.56177 (17)0.15023 (17)0.81755 (14)0.0198 (5)
C220.58096 (18)0.07720 (17)0.71132 (14)0.0250 (6)
H22A0.57810.06550.65440.030*
C230.67589 (19)−0.11099 (17)0.78976 (15)0.0260 (6)
H23A0.6980−0.14730.85300.031*
C240.7855 (2)−0.11393 (19)0.72457 (17)0.0487 (8)
H24A0.8410−0.07570.73830.073*
H24B0.7653−0.08030.66200.073*
H24C0.8205−0.18760.73150.073*
C250.5850 (2)−0.16786 (18)0.77139 (17)0.0418 (7)
H25A0.5161−0.16380.81460.063*
H25B0.6172−0.24230.77850.063*
H25C0.5631−0.13420.70920.063*
Cl510.28331 (5)0.58057 (5)0.30212 (4)0.02837 (15)
N510.52129 (14)0.32715 (13)0.54043 (11)0.0190 (4)
H51A0.53630.30690.59770.023*
N520.40140 (14)0.44895 (13)0.43181 (11)0.0181 (4)
N530.22379 (14)0.55319 (13)0.47526 (11)0.0181 (4)
N540.35856 (14)0.41024 (13)0.68229 (11)0.0186 (4)
N550.19479 (14)0.52510 (13)0.63989 (11)0.0175 (4)
C510.84156 (17)−0.02070 (16)0.35781 (13)0.0178 (5)
C520.72001 (17)−0.04891 (16)0.35767 (14)0.0221 (5)
H52B0.6931−0.01790.29610.027*
H52C0.6640−0.01880.40030.027*
C530.72440 (19)−0.17002 (17)0.38639 (15)0.0266 (6)
H53B0.6452−0.18730.38550.032*
C540.76341 (19)−0.21829 (17)0.48350 (14)0.0288 (6)
H54B0.7077−0.18890.52670.035*
H54C0.7648−0.29600.50250.035*
C550.88519 (19)−0.19224 (16)0.48462 (14)0.0242 (5)
H55A0.9108−0.22270.54740.029*
C560.97131 (19)−0.23935 (17)0.41818 (14)0.0261 (6)
H56A1.0503−0.22360.41920.031*
H56B0.9741−0.31720.43680.031*
C570.93224 (18)−0.19142 (16)0.32160 (14)0.0241 (5)
H57A0.9883−0.22180.27830.029*
C580.92764 (18)−0.06962 (16)0.29220 (14)0.0255 (6)
H58A1.0062−0.05190.29170.031*
H58B0.9031−0.03940.22980.031*
C590.88055 (18)−0.07101 (16)0.45488 (14)0.0227 (5)
H59A0.9585−0.05340.45660.027*
H59B0.8255−0.04100.49800.027*
C600.81062 (19)−0.21660 (17)0.31982 (15)0.0291 (6)
H60A0.8121−0.29420.33730.035*
H60B0.7856−0.18600.25760.035*
C610.84161 (18)0.10059 (15)0.32633 (14)0.0228 (5)
H61A0.92120.11430.32830.027*
H61B0.82340.12790.26210.027*
C620.75770 (17)0.16313 (15)0.38065 (14)0.0183 (5)
C630.78513 (18)0.17167 (15)0.46234 (14)0.0206 (5)
H63A0.85860.13880.48390.025*
C640.70683 (17)0.22741 (15)0.51275 (14)0.0195 (5)
H64A0.72730.23230.56820.023*
C650.59856 (17)0.27620 (15)0.48277 (14)0.0174 (5)
C660.56996 (18)0.27038 (16)0.40016 (14)0.0233 (5)
H66A0.49690.30390.37820.028*
C670.65035 (19)0.21459 (16)0.35056 (14)0.0234 (5)
H67A0.63110.21160.29410.028*
C680.42732 (17)0.40287 (16)0.51939 (14)0.0179 (5)
C690.30520 (18)0.52051 (16)0.41747 (14)0.0185 (5)
C700.25453 (17)0.50790 (15)0.56185 (13)0.0160 (5)
C710.35421 (17)0.43674 (15)0.58869 (13)0.0157 (5)
C720.26190 (18)0.46506 (16)0.70871 (14)0.0199 (5)
H72A0.24060.46310.77050.024*
C730.08037 (17)0.59161 (16)0.64500 (14)0.0192 (5)
H73A0.07890.65540.59050.023*
C740.06466 (19)0.62912 (17)0.72953 (14)0.0261 (6)
H74A0.13070.66440.73010.039*
H74B0.06070.56820.78390.039*
H74C−0.00750.67900.72900.039*
C75−0.01608 (18)0.53080 (18)0.64186 (15)0.0304 (6)
H75A−0.00310.50970.58580.046*
H75B−0.09140.57610.64320.046*
H75C−0.01590.46760.69450.046*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0341 (4)0.0329 (4)0.0208 (3)−0.0003 (3)−0.0101 (3)−0.0043 (3)
N10.0266 (11)0.0203 (11)0.0170 (10)0.0020 (9)−0.0042 (8)−0.0079 (9)
N20.0215 (10)0.0241 (12)0.0188 (10)−0.0026 (9)−0.0046 (8)−0.0064 (9)
N30.0234 (11)0.0186 (11)0.0179 (10)0.0003 (8)−0.0045 (8)−0.0044 (9)
N40.0317 (11)0.0236 (12)0.0217 (11)0.0007 (9)−0.0068 (9)−0.0088 (9)
N50.0262 (11)0.0203 (11)0.0227 (11)0.0001 (9)−0.0042 (8)−0.0061 (9)
C10.0206 (12)0.0184 (13)0.0202 (12)0.0007 (10)−0.0006 (9)−0.0105 (10)
C20.0313 (14)0.0195 (13)0.0170 (12)−0.0022 (11)−0.0026 (10)−0.0049 (10)
C30.0229 (13)0.0242 (14)0.0213 (13)−0.0050 (11)−0.0002 (10)−0.0056 (11)
C40.0210 (13)0.0306 (15)0.0244 (13)−0.0016 (11)−0.0030 (10)−0.0096 (11)
C50.0269 (13)0.0289 (14)0.0168 (12)−0.0010 (11)−0.0040 (10)−0.0005 (11)
C60.0266 (14)0.0204 (14)0.0263 (13)0.0013 (11)−0.0001 (10)−0.0036 (11)
C70.0308 (14)0.0257 (14)0.0221 (13)−0.0022 (11)0.0027 (10)−0.0128 (11)
C80.0282 (14)0.0253 (14)0.0195 (13)−0.0032 (11)−0.0015 (10)−0.0096 (11)
C90.0222 (13)0.0255 (14)0.0184 (12)−0.0059 (11)0.0003 (10)−0.0056 (10)
C100.0227 (13)0.0244 (14)0.0202 (13)0.0045 (11)−0.0006 (10)−0.0052 (11)
C110.0244 (13)0.0293 (14)0.0239 (13)−0.0016 (11)−0.0056 (10)−0.0127 (11)
C120.0149 (12)0.0286 (15)0.0235 (13)−0.0011 (10)−0.0070 (10)−0.0096 (11)
C130.0220 (13)0.0167 (13)0.0253 (14)0.0000 (10)−0.0032 (10)−0.0033 (11)
C140.0217 (13)0.0233 (14)0.0174 (12)−0.0013 (11)−0.0016 (10)−0.0012 (11)
C150.0156 (12)0.0224 (14)0.0175 (12)−0.0003 (10)−0.0057 (9)−0.0051 (11)
C160.0250 (13)0.0174 (13)0.0253 (14)0.0007 (11)−0.0049 (10)−0.0020 (11)
C170.0271 (14)0.0274 (15)0.0173 (12)0.0004 (11)−0.0022 (10)−0.0040 (11)
C180.0158 (12)0.0171 (13)0.0227 (13)−0.0029 (10)−0.0023 (10)−0.0063 (11)
C190.0184 (12)0.0255 (15)0.0177 (12)−0.0045 (11)−0.0048 (10)−0.0020 (11)
C200.0192 (12)0.0255 (14)0.0182 (13)−0.0058 (10)0.0002 (10)−0.0077 (11)
C210.0197 (12)0.0188 (13)0.0215 (13)−0.0012 (10)−0.0058 (10)−0.0061 (11)
C220.0356 (14)0.0191 (14)0.0184 (13)0.0027 (11)−0.0086 (11)−0.0038 (11)
C230.0312 (14)0.0193 (14)0.0252 (13)0.0056 (11)−0.0042 (11)−0.0074 (11)
C240.0436 (17)0.0399 (18)0.0519 (18)0.0125 (14)0.0044 (14)−0.0121 (14)
C250.0486 (17)0.0218 (15)0.0589 (18)−0.0019 (13)−0.0133 (14)−0.0153 (13)
Cl510.0277 (3)0.0355 (4)0.0161 (3)0.0008 (3)−0.0039 (2)−0.0012 (3)
N510.0185 (10)0.0229 (11)0.0162 (10)0.0018 (9)−0.0042 (8)−0.0082 (8)
N520.0168 (10)0.0177 (11)0.0201 (10)−0.0023 (8)−0.0016 (8)−0.0060 (8)
N530.0177 (10)0.0173 (10)0.0193 (10)−0.0014 (8)−0.0012 (8)−0.0062 (8)
N540.0199 (10)0.0188 (11)0.0164 (10)0.0014 (8)−0.0025 (8)−0.0063 (8)
N550.0177 (10)0.0186 (11)0.0142 (10)0.0006 (8)−0.0036 (8)−0.0027 (8)
C510.0188 (12)0.0155 (13)0.0193 (12)−0.0001 (10)0.0017 (9)−0.0082 (10)
C520.0225 (13)0.0222 (14)0.0210 (12)0.0010 (10)−0.0059 (10)−0.0061 (10)
C530.0234 (13)0.0270 (15)0.0327 (14)−0.0081 (11)−0.0049 (11)−0.0098 (12)
C540.0354 (15)0.0186 (14)0.0304 (14)−0.0040 (11)0.0003 (11)−0.0059 (11)
C550.0352 (14)0.0189 (14)0.0171 (12)0.0014 (11)−0.0118 (10)−0.0020 (10)
C560.0284 (14)0.0183 (13)0.0331 (14)0.0020 (11)−0.0105 (11)−0.0094 (11)
C570.0270 (13)0.0208 (14)0.0273 (13)0.0018 (11)0.0005 (10)−0.0153 (11)
C580.0256 (13)0.0259 (14)0.0268 (13)−0.0050 (11)0.0024 (10)−0.0116 (11)
C590.0251 (13)0.0212 (14)0.0247 (13)−0.0019 (10)−0.0037 (10)−0.0110 (11)
C600.0370 (15)0.0225 (14)0.0325 (14)−0.0040 (12)−0.0104 (11)−0.0118 (12)
C610.0233 (13)0.0183 (13)0.0250 (13)−0.0029 (10)0.0023 (10)−0.0058 (11)
C620.0217 (12)0.0105 (12)0.0200 (12)−0.0032 (10)0.0038 (10)−0.0025 (10)
C630.0194 (12)0.0147 (13)0.0272 (13)−0.0001 (10)−0.0017 (10)−0.0069 (11)
C640.0183 (12)0.0199 (13)0.0218 (12)−0.0027 (10)−0.0042 (10)−0.0074 (11)
C650.0178 (12)0.0110 (12)0.0224 (13)−0.0033 (10)0.0014 (10)−0.0043 (10)
C660.0224 (13)0.0227 (14)0.0229 (13)0.0030 (11)−0.0083 (10)−0.0047 (11)
C670.0334 (14)0.0195 (13)0.0160 (12)0.0000 (11)−0.0045 (10)−0.0044 (10)
C680.0156 (12)0.0160 (13)0.0238 (13)−0.0080 (10)−0.0025 (10)−0.0046 (10)
C690.0188 (12)0.0191 (13)0.0180 (12)−0.0032 (10)−0.0044 (10)−0.0045 (10)
C700.0173 (12)0.0150 (12)0.0159 (12)−0.0058 (10)−0.0012 (9)−0.0029 (10)
C710.0176 (12)0.0138 (12)0.0144 (12)−0.0008 (10)−0.0022 (9)−0.0028 (10)
C720.0218 (13)0.0247 (14)0.0161 (12)−0.0043 (11)0.0001 (10)−0.0103 (11)
C730.0169 (12)0.0177 (13)0.0204 (12)0.0027 (10)−0.0006 (9)−0.0051 (10)
C740.0273 (13)0.0223 (14)0.0258 (13)0.0020 (11)0.0008 (10)−0.0073 (11)
C750.0236 (13)0.0323 (15)0.0367 (15)−0.0048 (11)−0.0045 (11)−0.0110 (12)

Geometric parameters (Å, °)

Cl1—C191.768 (2)Cl51—C691.757 (2)
N1—C181.352 (2)N51—C681.360 (2)
N1—C151.425 (2)N51—C651.421 (2)
N1—H1A0.8800N51—H51A0.8800
N2—C191.340 (2)N52—C691.340 (2)
N2—C181.365 (2)N52—C681.362 (2)
N3—C191.318 (2)N53—C691.327 (2)
N3—C201.363 (2)N53—C701.364 (2)
N4—C221.321 (2)N54—C721.324 (2)
N4—C211.398 (2)N54—C711.392 (2)
N5—C221.376 (2)N55—C721.374 (2)
N5—C201.384 (2)N55—C701.375 (2)
N5—C231.475 (2)N55—C731.480 (2)
C1—C21.534 (3)C51—C521.540 (3)
C1—C81.539 (3)C51—C581.541 (3)
C1—C91.549 (3)C51—C591.547 (3)
C1—C111.553 (3)C51—C611.548 (3)
C2—C31.545 (3)C52—C531.540 (3)
C2—H2B0.9900C52—H52B0.9900
C2—H2C0.9900C52—H52C0.9900
C3—C101.535 (3)C53—C601.537 (3)
C3—C41.537 (3)C53—C541.545 (3)
C3—H3B1.0000C53—H53B1.0000
C4—C51.535 (3)C54—C551.534 (3)
C4—H4B0.9900C54—H54B0.9900
C4—H4C0.9900C54—H54C0.9900
C5—C61.541 (3)C55—C561.538 (3)
C5—C91.544 (3)C55—C591.541 (3)
C5—H5A1.0000C55—H55A1.0000
C6—C71.541 (3)C56—C571.538 (3)
C6—H6A0.9900C56—H56A0.9900
C6—H6B0.9900C56—H56B0.9900
C7—C101.534 (3)C57—C601.530 (3)
C7—C81.544 (3)C57—C581.548 (3)
C7—H7A1.0000C57—H57A1.0000
C8—H8A0.9900C58—H58A0.9900
C8—H8B0.9900C58—H58B0.9900
C9—H9A0.9900C59—H59A0.9900
C9—H9B0.9900C59—H59B0.9900
C10—H10A0.9900C60—H60A0.9900
C10—H10B0.9900C60—H60B0.9900
C11—C121.524 (3)C61—C621.514 (3)
C11—H11A0.9900C61—H61A0.9900
C11—H11B0.9900C61—H61B0.9900
C12—C171.396 (3)C62—C671.391 (3)
C12—C131.399 (3)C62—C631.394 (3)
C13—C141.387 (3)C63—C641.389 (3)
C13—H13A0.9500C63—H63A0.9500
C14—C151.396 (3)C64—C651.392 (3)
C14—H14A0.9500C64—H64A0.9500
C15—C161.395 (3)C65—C661.399 (3)
C16—C171.390 (3)C66—C671.394 (3)
C16—H16A0.9500C66—H66A0.9500
C17—H17A0.9500C67—H67A0.9500
C18—C211.411 (3)C68—C711.415 (3)
C20—C211.394 (3)C70—C711.394 (3)
C22—H22A0.9500C72—H72A0.9500
C23—C251.521 (3)C73—C741.523 (3)
C23—C241.523 (3)C73—C751.523 (3)
C23—H23A1.0000C73—H73A1.0000
C24—H24A0.9800C74—H74A0.9800
C24—H24B0.9800C74—H74B0.9800
C24—H24C0.9800C74—H74C0.9800
C25—H25A0.9800C75—H75A0.9800
C25—H25B0.9800C75—H75B0.9800
C25—H25C0.9800C75—H75C0.9800
C18—N1—C15129.36 (18)C68—N51—C65129.02 (17)
C18—N1—H1A115.3C68—N51—H51A115.5
C15—N1—H1A115.3C65—N51—H51A115.5
C19—N2—C18116.78 (18)C69—N52—C68117.47 (17)
C19—N3—C20108.67 (17)C69—N53—C70109.58 (16)
C22—N4—C21103.30 (17)C72—N54—C71102.93 (16)
C22—N5—C20105.48 (17)C72—N55—C70105.18 (16)
C22—N5—C23128.16 (17)C72—N55—C73129.36 (17)
C20—N5—C23126.35 (17)C70—N55—C73125.42 (16)
C2—C1—C8108.20 (17)C52—C51—C58108.83 (16)
C2—C1—C9108.59 (16)C52—C51—C59108.02 (16)
C8—C1—C9108.03 (17)C58—C51—C59108.37 (16)
C2—C1—C11111.68 (17)C52—C51—C61111.60 (16)
C8—C1—C11108.59 (16)C58—C51—C61108.54 (16)
C9—C1—C11111.63 (17)C59—C51—C61111.40 (16)
C1—C2—C3110.83 (17)C51—C52—C53110.02 (16)
C1—C2—H2B109.5C51—C52—H52B109.7
C3—C2—H2B109.5C53—C52—H52B109.7
C1—C2—H2C109.5C51—C52—H52C109.7
C3—C2—H2C109.5C53—C52—H52C109.7
H2B—C2—H2C108.1H52B—C52—H52C108.2
C10—C3—C4109.15 (17)C60—C53—C52109.65 (18)
C10—C3—C2109.64 (16)C60—C53—C54109.59 (17)
C4—C3—C2109.33 (17)C52—C53—C54109.72 (17)
C10—C3—H3B109.6C60—C53—H53B109.3
C4—C3—H3B109.6C52—C53—H53B109.3
C2—C3—H3B109.6C54—C53—H53B109.3
C5—C4—C3109.98 (17)C55—C54—C53109.22 (17)
C5—C4—H4B109.7C55—C54—H54B109.8
C3—C4—H4B109.7C53—C54—H54B109.8
C5—C4—H4C109.7C55—C54—H54C109.8
C3—C4—H4C109.7C53—C54—H54C109.8
H4B—C4—H4C108.2H54B—C54—H54C108.3
C4—C5—C6109.03 (18)C54—C55—C56109.45 (17)
C4—C5—C9109.24 (17)C54—C55—C59108.79 (17)
C6—C5—C9109.56 (17)C56—C55—C59109.54 (17)
C4—C5—H5A109.7C54—C55—H55A109.7
C6—C5—H5A109.7C56—C55—H55A109.7
C9—C5—H5A109.7C59—C55—H55A109.7
C7—C6—C5109.09 (17)C57—C56—C55109.45 (17)
C7—C6—H6A109.9C57—C56—H56A109.8
C5—C6—H6A109.9C55—C56—H56A109.8
C7—C6—H6B109.9C57—C56—H56B109.8
C5—C6—H6B109.9C55—C56—H56B109.8
H6A—C6—H6B108.3H56A—C56—H56B108.2
C10—C7—C6109.60 (17)C60—C57—C56109.76 (18)
C10—C7—C8109.20 (17)C60—C57—C58108.50 (17)
C6—C7—C8109.73 (17)C56—C57—C58109.97 (17)
C10—C7—H7A109.4C60—C57—H57A109.5
C6—C7—H7A109.4C56—C57—H57A109.5
C8—C7—H7A109.4C58—C57—H57A109.5
C1—C8—C7111.05 (16)C51—C58—C57110.60 (17)
C1—C8—H8A109.4C51—C58—H58A109.5
C7—C8—H8A109.4C57—C58—H58A109.5
C1—C8—H8B109.4C51—C58—H58B109.5
C7—C8—H8B109.4C57—C58—H58B109.5
H8A—C8—H8B108.0H58A—C58—H58B108.1
C5—C9—C1110.86 (17)C55—C59—C51111.33 (16)
C5—C9—H9A109.5C55—C59—H59A109.4
C1—C9—H9A109.5C51—C59—H59A109.4
C5—C9—H9B109.5C55—C59—H59B109.4
C1—C9—H9B109.5C51—C59—H59B109.4
H9A—C9—H9B108.1H59A—C59—H59B108.0
C7—C10—C3109.30 (17)C57—C60—C53109.58 (17)
C7—C10—H10A109.8C57—C60—H60A109.8
C3—C10—H10A109.8C53—C60—H60A109.8
C7—C10—H10B109.8C57—C60—H60B109.8
C3—C10—H10B109.8C53—C60—H60B109.8
H10A—C10—H10B108.3H60A—C60—H60B108.2
C12—C11—C1117.28 (16)C62—C61—C51116.11 (17)
C12—C11—H11A108.0C62—C61—H61A108.3
C1—C11—H11A108.0C51—C61—H61A108.3
C12—C11—H11B108.0C62—C61—H61B108.3
C1—C11—H11B108.0C51—C61—H61B108.3
H11A—C11—H11B107.2H61A—C61—H61B107.4
C17—C12—C13116.8 (2)C67—C62—C63117.53 (18)
C17—C12—C11121.9 (2)C67—C62—C61121.10 (19)
C13—C12—C11121.3 (2)C63—C62—C61121.38 (18)
C14—C13—C12122.5 (2)C64—C63—C62121.09 (19)
C14—C13—H13A118.8C64—C63—H63A119.5
C12—C13—H13A118.8C62—C63—H63A119.5
C13—C14—C15119.6 (2)C63—C64—C65120.62 (19)
C13—C14—H14A120.2C63—C64—H64A119.7
C15—C14—H14A120.2C65—C64—H64A119.7
C16—C15—C14119.2 (2)C64—C65—C66119.31 (19)
C16—C15—N1122.3 (2)C64—C65—N51117.14 (18)
C14—C15—N1118.37 (19)C66—C65—N51123.53 (18)
C17—C16—C15120.1 (2)C67—C66—C65118.95 (19)
C17—C16—H16A120.0C67—C66—H66A120.5
C15—C16—H16A120.0C65—C66—H66A120.5
C16—C17—C12121.9 (2)C62—C67—C66122.47 (19)
C16—C17—H17A119.0C62—C67—H67A118.8
C12—C17—H17A119.0C66—C67—H67A118.8
N1—C18—N2122.07 (19)N51—C68—N52121.44 (19)
N1—C18—C21119.73 (19)N51—C68—C71120.41 (18)
N2—C18—C21118.20 (19)N52—C68—C71118.15 (18)
N3—C19—N2132.44 (19)N53—C69—N52131.12 (18)
N3—C19—Cl1113.81 (16)N53—C69—Cl51114.79 (15)
N2—C19—Cl1113.75 (16)N52—C69—Cl51114.09 (15)
N3—C20—N5126.69 (19)N53—C70—N55126.88 (18)
N3—C20—C21127.4 (2)N53—C70—C71126.86 (19)
N5—C20—C21105.88 (18)N55—C70—C71106.25 (17)
C20—C21—N4110.77 (18)N54—C71—C70110.81 (17)
C20—C21—C18116.36 (19)N54—C71—C68132.71 (18)
N4—C21—C18132.77 (19)C70—C71—C68116.44 (18)
N4—C22—N5114.56 (18)N54—C72—N55114.83 (18)
N4—C22—H22A122.7N54—C72—H72A122.6
N5—C22—H22A122.7N55—C72—H72A122.6
N5—C23—C25110.12 (17)N55—C73—C74110.12 (16)
N5—C23—C24109.93 (18)N55—C73—C75109.84 (16)
C25—C23—C24112.2 (2)C74—C73—C75112.51 (18)
N5—C23—H23A108.1N55—C73—H73A108.1
C25—C23—H23A108.1C74—C73—H73A108.1
C24—C23—H23A108.1C75—C73—H73A108.1
C23—C24—H24A109.5C73—C74—H74A109.5
C23—C24—H24B109.5C73—C74—H74B109.5
H24A—C24—H24B109.5H74A—C74—H74B109.5
C23—C24—H24C109.5C73—C74—H74C109.5
H24A—C24—H24C109.5H74A—C74—H74C109.5
H24B—C24—H24C109.5H74B—C74—H74C109.5
C23—C25—H25A109.5C73—C75—H75A109.5
C23—C25—H25B109.5C73—C75—H75B109.5
H25A—C25—H25B109.5H75A—C75—H75B109.5
C23—C25—H25C109.5C73—C75—H75C109.5
H25A—C25—H25C109.5H75A—C75—H75C109.5
H25B—C25—H25C109.5H75B—C75—H75C109.5
C8—C1—C2—C358.5 (2)C58—C51—C52—C5358.5 (2)
C9—C1—C2—C3−58.6 (2)C59—C51—C52—C53−59.0 (2)
C11—C1—C2—C3177.92 (16)C61—C51—C52—C53178.21 (16)
C1—C2—C3—C10−59.9 (2)C51—C52—C53—C60−59.7 (2)
C1—C2—C3—C459.7 (2)C51—C52—C53—C5460.7 (2)
C10—C3—C4—C560.3 (2)C60—C53—C54—C5559.9 (2)
C2—C3—C4—C5−59.6 (2)C52—C53—C54—C55−60.6 (2)
C3—C4—C5—C6−60.2 (2)C53—C54—C55—C56−60.1 (2)
C3—C4—C5—C959.5 (2)C53—C54—C55—C5959.5 (2)
C4—C5—C6—C760.0 (2)C54—C55—C56—C5760.2 (2)
C9—C5—C6—C7−59.5 (2)C59—C55—C56—C57−59.0 (2)
C5—C6—C7—C10−60.5 (2)C55—C56—C57—C60−59.9 (2)
C5—C6—C7—C859.4 (2)C55—C56—C57—C5859.4 (2)
C2—C1—C8—C7−58.8 (2)C52—C51—C58—C57−59.2 (2)
C9—C1—C8—C758.6 (2)C59—C51—C58—C5758.0 (2)
C11—C1—C8—C7179.78 (17)C61—C51—C58—C57179.16 (17)
C10—C7—C8—C160.1 (2)C60—C57—C58—C5160.4 (2)
C6—C7—C8—C1−60.0 (2)C56—C57—C58—C51−59.7 (2)
C4—C5—C9—C1−59.2 (2)C54—C55—C59—C51−60.2 (2)
C6—C5—C9—C160.1 (2)C56—C55—C59—C5159.4 (2)
C2—C1—C9—C558.4 (2)C52—C51—C59—C5559.4 (2)
C8—C1—C9—C5−58.7 (2)C58—C51—C59—C55−58.4 (2)
C11—C1—C9—C5−178.01 (17)C61—C51—C59—C55−177.72 (17)
C6—C7—C10—C360.6 (2)C56—C57—C60—C5359.7 (2)
C8—C7—C10—C3−59.6 (2)C58—C57—C60—C53−60.5 (2)
C4—C3—C10—C7−60.1 (2)C52—C53—C60—C5760.8 (2)
C2—C3—C10—C759.7 (2)C54—C53—C60—C57−59.7 (2)
C2—C1—C11—C1259.7 (2)C52—C51—C61—C6257.5 (2)
C8—C1—C11—C12178.91 (18)C58—C51—C61—C62177.43 (17)
C9—C1—C11—C12−62.1 (2)C59—C51—C61—C62−63.3 (2)
C1—C11—C12—C17−94.6 (2)C51—C61—C62—C67−98.4 (2)
C1—C11—C12—C1387.5 (2)C51—C61—C62—C6381.8 (2)
C17—C12—C13—C140.4 (3)C67—C62—C63—C641.5 (3)
C11—C12—C13—C14178.31 (18)C61—C62—C63—C64−178.71 (18)
C12—C13—C14—C15−0.1 (3)C62—C63—C64—C650.1 (3)
C13—C14—C15—C16−0.2 (3)C63—C64—C65—C66−1.2 (3)
C13—C14—C15—N1176.24 (17)C63—C64—C65—N51176.95 (18)
C18—N1—C15—C16−37.7 (3)C68—N51—C65—C64160.18 (19)
C18—N1—C15—C14146.1 (2)C68—N51—C65—C66−21.7 (3)
C14—C15—C16—C170.1 (3)C64—C65—C66—C670.8 (3)
N1—C15—C16—C17−176.15 (17)N51—C65—C66—C67−177.28 (18)
C15—C16—C17—C120.2 (3)C63—C62—C67—C66−2.0 (3)
C13—C12—C17—C16−0.4 (3)C61—C62—C67—C66178.24 (19)
C11—C12—C17—C16−178.37 (18)C65—C66—C67—C620.9 (3)
C15—N1—C18—N2−5.6 (3)C65—N51—C68—N52−6.8 (3)
C15—N1—C18—C21174.88 (19)C65—N51—C68—C71173.91 (19)
C19—N2—C18—N1179.85 (18)C69—N52—C68—N51178.00 (18)
C19—N2—C18—C21−0.6 (3)C69—N52—C68—C71−2.7 (3)
C20—N3—C19—N22.2 (3)C70—N53—C69—N525.2 (3)
C20—N3—C19—Cl1−177.30 (14)C70—N53—C69—Cl51−175.13 (14)
C18—N2—C19—N3−2.6 (3)C68—N52—C69—N53−3.6 (3)
C18—N2—C19—Cl1177.00 (14)C68—N52—C69—Cl51176.80 (14)
C19—N3—C20—N5−178.37 (19)C69—N53—C70—N55177.51 (19)
C19—N3—C20—C211.2 (3)C69—N53—C70—C71−0.9 (3)
C22—N5—C20—N3−179.8 (2)C72—N55—C70—N53−177.88 (19)
C23—N5—C20—N31.1 (3)C73—N55—C70—N534.3 (3)
C22—N5—C20—C210.5 (2)C72—N55—C70—C710.8 (2)
C23—N5—C20—C21−178.52 (18)C73—N55—C70—C71−176.98 (17)
N3—C20—C21—N4179.46 (19)C72—N54—C71—C700.5 (2)
N5—C20—C21—N4−0.9 (2)C72—N54—C71—C68−176.9 (2)
N3—C20—C21—C18−3.8 (3)N53—C70—C71—N54177.86 (18)
N5—C20—C21—C18175.82 (17)N55—C70—C71—N54−0.8 (2)
C22—N4—C21—C200.9 (2)N53—C70—C71—C68−4.3 (3)
C22—N4—C21—C18−175.1 (2)N55—C70—C71—C68176.99 (17)
N1—C18—C21—C20−177.17 (19)N51—C68—C71—N542.5 (3)
N2—C18—C21—C203.3 (3)N52—C68—C71—N54−176.80 (19)
N1—C18—C21—N4−1.4 (3)N51—C68—C71—C70−174.68 (17)
N2—C18—C21—N4179.1 (2)N52—C68—C71—C706.0 (3)
C21—N4—C22—N5−0.6 (2)C71—N54—C72—N550.1 (2)
C20—N5—C22—N40.1 (2)C70—N55—C72—N54−0.6 (2)
C23—N5—C22—N4179.07 (19)C73—N55—C72—N54177.10 (18)
C22—N5—C23—C25−59.4 (3)C72—N55—C73—C7426.2 (3)
C20—N5—C23—C25119.4 (2)C70—N55—C73—C74−156.61 (18)
C22—N5—C23—C2464.7 (3)C72—N55—C73—C75−98.3 (2)
C20—N5—C23—C24−116.5 (2)C70—N55—C73—C7578.9 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···N540.882.142.940 (2)152
N51—H51A···N40.882.273.026 (2)144

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2124).

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