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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2008 Jun 7;64(Pt 7):o1236. doi: 10.1107/S1600536808016930

2-[4-(Dimethyl­amino)phen­yl]imidazo[4,5-f][1,10]phenanthroline sesquihydrate

Gang-Qiang Yin a,*
PMCID: PMC2961644  PMID: 21202873

Abstract

There are two formula units in the asymmetric unit of the title compound, C21H17N5·1.5H2O. The imidazo[4,5-f][1,10]phen­an­throline unit is almost coplanar with the benzene ring, the dihedral angles between them being 8.91 (5) and 4.93 (6)° in the two mol­ecules. The crystal structure is stabilized by a series of hydrogen bonds between the water mol­ecules and the N atoms of the imidazophenanthroline groups.

Related literature

For related literature, see: Sun et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).graphic file with name e-64-o1236-scheme1.jpg

Experimental

Crystal data

  • C21H17N5·1.5H2O

  • M r = 386.42

  • Triclinic, Inline graphic

  • a = 11.0503 (9) Å

  • b = 12.6386 (8) Å

  • c = 14.0297 (11) Å

  • α = 73.685 (9)°

  • β = 81.909 (10)°

  • γ = 79.163 (9)°

  • V = 1838.9 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 293 (2) K

  • 0.45 × 0.35 × 0.30 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2000 ▶) T min = 0.961, T max = 0.974

  • 15313 measured reflections

  • 8974 independent reflections

  • 5671 reflections with I > 2σ(I)

  • R int = 0.042

Refinement

  • R[F 2 > 2σ(F 2)] = 0.051

  • wR(F 2) = 0.138

  • S = 0.96

  • 8974 reflections

  • 520 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.21 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2000 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808016930/pk2098sup1.cif

e-64-o1236-sup1.cif (32.4KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016930/pk2098Isup2.hkl

e-64-o1236-Isup2.hkl (438.9KB, hkl)

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O3—H6⋯N8 0.90 (3) 2.01 (3) 2.870 (2) 159 (2)
C18—H18A⋯N3 0.93 2.61 2.919 (2) 100
O1—H1⋯O3i 0.78 (2) 1.93 (2) 2.711 (2) 176 (2)
O1—H2⋯N4i 0.95 (3) 1.95 (3) 2.891 (2) 170 (2)
N9—H7B⋯O1ii 0.86 1.98 2.820 (2) 166
O2—H3⋯N6iii 0.86 (2) 2.34 (2) 3.047 (2) 139 (2)
O2—H3⋯N7iii 0.86 (2) 2.15 (2) 2.899 (2) 144 (2)
O2—H4⋯N1i 0.92 (3) 2.11 (3) 2.943 (2) 151 (2)
N3—H3B⋯O2iv 0.86 1.94 2.751 (2) 157
O3—H5⋯N2i 0.89 (3) 2.10 (3) 2.969 (2) 163 (2)
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Symmetry codes: (i) Inline graphic; (ii) Inline graphic; (iii) Inline graphic; (iv) Inline graphic.

Acknowledgments

I acknowledge financial support from the NSF of Guangdong Province

supplementary crystallographic information

Comment

1,10-Phenanthroline and its derivatives are commonly used as ligands in metal complexes (e.g. Sun et al., 2007). We report here the structure of the title compound, which was synthesized from [4,5-f]1,10-phenanthroline. In this compound, all the bond lengths are within normal ranges (Allen et al., 1987). The asymmetric unit consists of two independent C21H17N5 molecules and three H2O molecules (Fig. 1). Each C21H17N5 molecule consists of imidazo- phenanthroline and phenyl rings. The imidazo[4,5-f]1,10-phenanthroline moiety is almost coplanar with the phenyl ring, with dihedral angles between them in each molecule of 8.91 (5)° and 4.93 (6)°. The three H2O molecules link the 2-(4'-Dimethylaminophenyl)imidazo[4,5-f]1,10-phenanthroline molecules by hydrogen bonds to the nitrogen atoms of the imidazo-phenantholine ring systems.

Experimental

1,10-phenanthroline-5,6-dione (1.5 mmol) and dimethylaminobenzaldehyde (1.5 mmol) were dissolved in CH3COOH-CH3COONH4 (1:1) solution(30 ml). The mixture was refluxed for 1.5 h under argon, after cooling, this mixture was diluted with water and neutralized with concentrated aqueous ammonia, immediately resulting a yellow precipitate, which was washed with water, acetone and diethyl ether respectively. Crystals of the title compound were obtained by recrystallization from dichloromethane.

Refinement

Coordinates of hydrogen atoms bonded to carbon atoms were calculated following the stereochemical rules with C—H distances of 0.93 Å for phenyl and 0.96 Å for methyl groups. The hydrogen atoms were included in the refinement using the riding-model approximation. Uiso(H) were defined as 1.2Ueq of the parent carbon atoms for phenyl and 1.5Ueq of the parent carbon atoms for the methyl groups. All H atoms on N atoms were positioned geometrically and refined as riding atoms, with N—H = 0.86 Å and Uiso(H) = 1.2Ueq(N). The H atoms of the waters were located in a Fourier map following isotropic refinement.

Figures

Fig. 1.

Fig. 1.

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A view of the compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level.

Crystal data

C21H17N5·1.5(H2O) Z = 4
Mr = 386.42 F000 = 772
Triclinic, P1 Dx = 1.324 Mg m−3
Hall symbol: -P 1 Mo Kα radiation λ = 0.71073 Å
a = 11.0503 (9) Å Cell parameters from 4754 reflections
b = 12.6386 (8) Å θ = 1.5–28.3º
c = 14.0297 (11) Å µ = 0.09 mm−1
α = 73.685 (9)º T = 293 (2) K
β = 81.909 (10)º Prism, yellow
γ = 79.163 (9)º 0.45 × 0.35 × 0.30 mm
V = 1838.9 (3) Å3
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Data collection

Bruker SMART CCD area-detector diffractometer 8974 independent reflections
Radiation source: fine-focus sealed tube 5671 reflections with I > 2σ(I)
Monochromator: graphite Rint = 0.042
T = 293(2) K θmax = 28.3º
φ and ω scans θmin = 1.9º
Absorption correction: multi-scan(CrystalClear; Rigaku/MSC, 2000) h = −14→14
Tmin = 0.961, Tmax = 0.974 k = −16→13
15313 measured reflections l = −18→17
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Refinement

Refinement on F2 Secondary atom site location: difference Fourier map
Least-squares matrix: full Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051 H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.138   w = 1/[σ2(Fo2) + (0.0641P)2] where P = (Fo2 + 2Fc2)/3
S = 0.96 (Δ/σ)max < 0.001
8974 reflections Δρmax = 0.35 e Å−3
520 parameters Δρmin = −0.21 e Å−3
Primary atom site location: structure-invariant direct methods Extinction correction: none
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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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
C1 0.45171 (15) 0.33283 (14) 0.52723 (13) 0.0392 (4)
H1A 0.4972 0.2657 0.5594 0.047*
C2 0.50296 (15) 0.39220 (14) 0.43682 (13) 0.0387 (4)
H2A 0.5814 0.3665 0.4104 0.046*
C3 0.43558 (15) 0.48961 (14) 0.38724 (12) 0.0348 (4)
H3A 0.4676 0.5308 0.3261 0.042*
C4 0.31834 (14) 0.52678 (12) 0.42896 (11) 0.0289 (3)
C5 0.27578 (14) 0.46184 (13) 0.52285 (12) 0.0301 (3)
C6 0.01425 (16) 0.46905 (15) 0.70863 (13) 0.0431 (4)
H6A −0.0078 0.4281 0.7729 0.052*
C7 −0.07076 (16) 0.55909 (14) 0.66489 (12) 0.0392 (4)
H7A −0.1476 0.5761 0.6985 0.047*
C8 −0.03942 (15) 0.62191 (14) 0.57195 (12) 0.0347 (4)
H8A −0.0940 0.6836 0.5413 0.042*
C9 0.07598 (14) 0.59251 (12) 0.52306 (11) 0.0291 (3)
C10 0.15556 (14) 0.49771 (13) 0.57175 (11) 0.0296 (3)
C11 0.23794 (14) 0.62512 (13) 0.38244 (11) 0.0293 (3)
C12 0.12222 (14) 0.65243 (12) 0.42739 (11) 0.0297 (3)
C13 0.15243 (15) 0.77516 (13) 0.28321 (12) 0.0322 (4)
C14 0.08692 (15) 1.07618 (13) 0.04811 (12) 0.0356 (4)
C15 0.18800 (15) 0.99284 (14) 0.04114 (12) 0.0395 (4)
H15A 0.2441 1.0036 −0.0154 0.047*
C16 0.20693 (16) 0.89581 (14) 0.11507 (13) 0.0386 (4)
H16A 0.2746 0.8420 0.1068 0.046*
C17 0.12777 (14) 0.87548 (13) 0.20225 (11) 0.0323 (4)
C18 0.02535 (16) 0.95707 (14) 0.20844 (13) 0.0404 (4)
H18A −0.0310 0.9453 0.2648 0.048*
C19 0.00444 (16) 1.05446 (14) 0.13433 (13) 0.0409 (4)
H19A −0.0654 1.1067 0.1415 0.049*
C20 0.15919 (19) 1.19547 (17) −0.11149 (14) 0.0590 (6)
H20A 0.2375 1.1995 −0.0916 0.089*
H20B 0.1297 1.2649 −0.1571 0.089*
H20C 0.1689 1.1361 −0.1435 0.089*
C21 −0.03024 (19) 1.26246 (16) −0.01427 (16) 0.0599 (6)
H21A −0.0326 1.2769 0.0497 0.090*
H21B −0.1068 1.2402 −0.0198 0.090*
H21C −0.0185 1.3289 −0.0660 0.090*
C22 0.54717 (18) −0.06149 (16) 0.22080 (14) 0.0497 (5)
H22A 0.5276 −0.1331 0.2468 0.060*
C23 0.50237 (17) 0.00110 (16) 0.13110 (14) 0.0462 (5)
H23A 0.4529 −0.0278 0.0993 0.055*
C24 0.53193 (15) 0.10615 (15) 0.08978 (13) 0.0384 (4)
H24A 0.5030 0.1497 0.0297 0.046*
C25 0.60662 (14) 0.14625 (13) 0.14012 (12) 0.0329 (4)
C26 0.64498 (15) 0.07783 (14) 0.23243 (12) 0.0350 (4)
C27 0.8597 (2) 0.18442 (16) 0.39974 (15) 0.0555 (5)
H27A 0.9077 0.2044 0.4393 0.067*
C28 0.8253 (2) 0.07935 (16) 0.42726 (15) 0.0534 (5)
H28A 0.8520 0.0299 0.4859 0.064*
C29 0.82222 (18) 0.25814 (15) 0.31362 (14) 0.0467 (5)
H29A 0.8445 0.3290 0.2936 0.056*
C30 0.74997 (15) 0.22578 (13) 0.25602 (12) 0.0353 (4)
C31 0.71856 (15) 0.11709 (13) 0.28993 (12) 0.0349 (4)
C32 0.71051 (15) 0.29322 (13) 0.16206 (12) 0.0340 (4)
C33 0.64546 (14) 0.25301 (13) 0.10671 (12) 0.0323 (4)
C34 0.68171 (15) 0.42218 (13) 0.02556 (12) 0.0356 (4)
C35 0.68460 (15) 0.52469 (14) −0.05363 (12) 0.0365 (4)
C36 0.61896 (16) 0.54779 (14) −0.13666 (12) 0.0389 (4)
H36A 0.5723 0.4959 −0.1418 0.047*
C37 0.62105 (16) 0.64571 (14) −0.21179 (12) 0.0380 (4)
H37A 0.5759 0.6583 −0.2661 0.046*
C38 0.68999 (16) 0.72604 (14) −0.20729 (13) 0.0396 (4)
C39 0.75241 (18) 0.60484 (16) −0.04965 (14) 0.0478 (5)
H39A 0.7969 0.5921 0.0051 0.057*
C40 0.75633 (19) 0.70268 (15) −0.12370 (14) 0.0501 (5)
H40A 0.8036 0.7539 −0.1182 0.060*
C41 0.6379 (2) 0.83872 (18) −0.37374 (14) 0.0590 (6)
H41A 0.6566 0.9068 −0.4202 0.089*
H41B 0.5498 0.8424 −0.3604 0.089*
H41C 0.6715 0.7769 −0.4016 0.089*
C42 0.7699 (2) 0.90254 (18) −0.28036 (16) 0.0651 (6)
H42A 0.7583 0.9659 −0.3369 0.098*
H42B 0.8550 0.8677 −0.2830 0.098*
H42C 0.7486 0.9265 −0.2201 0.098*
N1 0.34306 (12) 0.36491 (11) 0.57079 (10) 0.0360 (3)
N2 0.12422 (13) 0.43701 (12) 0.66596 (10) 0.0379 (3)
N3 0.06820 (12) 0.74814 (11) 0.36341 (9) 0.0311 (3)
H3B −0.0049 0.7841 0.3723 0.037*
N4 0.25682 (12) 0.70252 (11) 0.29184 (10) 0.0328 (3)
N5 0.07091 (14) 1.17421 (13) −0.02435 (11) 0.0501 (4)
N6 0.61562 (14) −0.02608 (12) 0.27155 (11) 0.0437 (4)
N7 0.75716 (14) 0.04518 (12) 0.37563 (11) 0.0433 (4)
N8 0.73203 (13) 0.39979 (11) 0.11132 (10) 0.0375 (3)
N9 0.62862 (12) 0.33528 (11) 0.01943 (10) 0.0349 (3)
H7B 0.5917 0.3326 −0.0297 0.042*
N10 0.69184 (17) 0.82371 (13) −0.28192 (11) 0.0537 (4)
O1 0.53530 (14) 0.29356 (11) 0.85874 (10) 0.0434 (3)
O2 0.81559 (12) 0.80854 (12) 0.38807 (11) 0.0495 (4)
O3 0.67079 (13) 0.57209 (13) 0.21453 (11) 0.0546 (4)
H3 0.769 (2) 0.873 (2) 0.3756 (17) 0.075 (7)*
H1 0.474 (2) 0.3296 (19) 0.8380 (16) 0.064 (7)*
H5 0.723 (2) 0.5821 (19) 0.2531 (17) 0.078 (8)*
H2 0.597 (2) 0.297 (2) 0.8037 (19) 0.092 (9)*
H4 0.774 (2) 0.757 (2) 0.3773 (19) 0.098 (9)*
H6 0.709 (2) 0.522 (2) 0.181 (2) 0.097 (10)*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
C1 0.0366 (9) 0.0371 (9) 0.0415 (10) 0.0016 (8) −0.0144 (8) −0.0061 (8)
C2 0.0330 (8) 0.0421 (10) 0.0435 (10) −0.0035 (7) −0.0054 (7) −0.0160 (8)
C3 0.0350 (8) 0.0402 (9) 0.0314 (9) −0.0090 (7) −0.0053 (7) −0.0096 (7)
C4 0.0298 (8) 0.0300 (8) 0.0291 (8) −0.0070 (6) −0.0076 (6) −0.0074 (7)
C5 0.0310 (8) 0.0299 (8) 0.0312 (8) −0.0075 (7) −0.0092 (7) −0.0063 (7)
C6 0.0430 (10) 0.0497 (11) 0.0294 (9) −0.0084 (9) −0.0006 (8) 0.0005 (8)
C7 0.0365 (9) 0.0438 (10) 0.0349 (9) −0.0081 (8) 0.0010 (7) −0.0072 (8)
C8 0.0342 (8) 0.0344 (9) 0.0361 (9) −0.0067 (7) −0.0053 (7) −0.0086 (7)
C9 0.0311 (8) 0.0281 (8) 0.0304 (8) −0.0086 (6) −0.0062 (6) −0.0070 (7)
C10 0.0324 (8) 0.0300 (8) 0.0272 (8) −0.0098 (7) −0.0073 (6) −0.0036 (7)
C11 0.0312 (8) 0.0315 (8) 0.0265 (8) −0.0083 (7) −0.0072 (6) −0.0051 (7)
C12 0.0328 (8) 0.0281 (8) 0.0288 (8) −0.0074 (6) −0.0083 (6) −0.0042 (7)
C13 0.0340 (8) 0.0325 (8) 0.0309 (9) −0.0095 (7) −0.0017 (7) −0.0074 (7)
C14 0.0340 (8) 0.0333 (9) 0.0347 (9) −0.0049 (7) −0.0046 (7) −0.0010 (7)
C15 0.0372 (9) 0.0408 (10) 0.0330 (9) −0.0038 (8) 0.0039 (7) −0.0027 (8)
C16 0.0374 (9) 0.0346 (9) 0.0385 (10) −0.0019 (7) −0.0021 (8) −0.0041 (8)
C17 0.0342 (8) 0.0330 (8) 0.0284 (8) −0.0085 (7) −0.0051 (7) −0.0028 (7)
C18 0.0373 (9) 0.0385 (9) 0.0370 (10) −0.0047 (8) 0.0057 (7) −0.0018 (8)
C19 0.0352 (9) 0.0370 (9) 0.0398 (10) 0.0030 (7) 0.0028 (8) −0.0018 (8)
C20 0.0584 (12) 0.0519 (12) 0.0471 (12) −0.0040 (10) 0.0041 (10) 0.0115 (10)
C21 0.0555 (12) 0.0444 (11) 0.0599 (13) 0.0072 (10) 0.0013 (10) 0.0054 (10)
C22 0.0594 (12) 0.0454 (11) 0.0507 (12) −0.0228 (9) −0.0038 (10) −0.0139 (9)
C23 0.0457 (10) 0.0566 (12) 0.0457 (11) −0.0211 (9) −0.0022 (9) −0.0208 (9)
C24 0.0355 (9) 0.0452 (10) 0.0369 (10) −0.0088 (8) −0.0025 (7) −0.0133 (8)
C25 0.0293 (8) 0.0360 (9) 0.0346 (9) −0.0040 (7) 0.0001 (7) −0.0135 (7)
C26 0.0350 (8) 0.0365 (9) 0.0358 (9) −0.0049 (7) −0.0016 (7) −0.0143 (7)
C27 0.0761 (14) 0.0497 (11) 0.0509 (12) −0.0159 (11) −0.0289 (10) −0.0144 (10)
C28 0.0730 (14) 0.0482 (11) 0.0426 (11) −0.0135 (10) −0.0199 (10) −0.0081 (9)
C29 0.0603 (12) 0.0384 (10) 0.0469 (11) −0.0114 (9) −0.0159 (9) −0.0122 (9)
C30 0.0392 (9) 0.0337 (8) 0.0351 (9) −0.0038 (7) −0.0046 (7) −0.0130 (7)
C31 0.0374 (9) 0.0345 (9) 0.0329 (9) −0.0017 (7) −0.0060 (7) −0.0102 (7)
C32 0.0355 (8) 0.0327 (8) 0.0351 (9) −0.0025 (7) −0.0047 (7) −0.0122 (7)
C33 0.0313 (8) 0.0347 (8) 0.0310 (9) −0.0009 (7) −0.0057 (7) −0.0102 (7)
C34 0.0354 (8) 0.0353 (9) 0.0378 (10) −0.0042 (7) −0.0029 (7) −0.0134 (8)
C35 0.0384 (9) 0.0355 (9) 0.0363 (9) −0.0048 (7) −0.0042 (7) −0.0108 (7)
C36 0.0402 (9) 0.0369 (9) 0.0414 (10) −0.0084 (8) −0.0047 (8) −0.0111 (8)
C37 0.0419 (9) 0.0406 (9) 0.0328 (9) −0.0046 (8) −0.0089 (7) −0.0104 (8)
C38 0.0464 (10) 0.0386 (9) 0.0334 (9) −0.0074 (8) 0.0007 (8) −0.0103 (8)
C39 0.0606 (12) 0.0489 (11) 0.0398 (10) −0.0169 (10) −0.0183 (9) −0.0087 (9)
C40 0.0635 (12) 0.0439 (11) 0.0488 (11) −0.0208 (10) −0.0141 (10) −0.0092 (9)
C41 0.0721 (14) 0.0602 (13) 0.0424 (12) −0.0160 (11) −0.0035 (10) −0.0069 (10)
C42 0.0895 (16) 0.0610 (14) 0.0502 (13) −0.0392 (13) −0.0047 (12) −0.0061 (10)
N1 0.0347 (7) 0.0348 (7) 0.0368 (8) −0.0045 (6) −0.0093 (6) −0.0045 (6)
N2 0.0388 (8) 0.0419 (8) 0.0292 (8) −0.0089 (7) −0.0055 (6) −0.0004 (6)
N3 0.0296 (7) 0.0305 (7) 0.0305 (7) −0.0038 (6) −0.0040 (6) −0.0036 (6)
N4 0.0337 (7) 0.0328 (7) 0.0299 (7) −0.0062 (6) −0.0047 (6) −0.0036 (6)
N5 0.0471 (9) 0.0417 (9) 0.0400 (9) 0.0060 (7) 0.0071 (7) 0.0103 (7)
N6 0.0519 (9) 0.0367 (8) 0.0449 (9) −0.0121 (7) −0.0070 (7) −0.0097 (7)
N7 0.0544 (9) 0.0396 (8) 0.0372 (8) −0.0072 (7) −0.0163 (7) −0.0064 (7)
N8 0.0425 (8) 0.0322 (7) 0.0391 (8) −0.0052 (6) −0.0077 (6) −0.0102 (6)
N9 0.0351 (7) 0.0374 (8) 0.0334 (8) −0.0042 (6) −0.0076 (6) −0.0099 (6)
N10 0.0777 (12) 0.0483 (9) 0.0387 (9) −0.0280 (9) −0.0114 (8) −0.0024 (7)
O1 0.0402 (7) 0.0500 (8) 0.0377 (7) −0.0026 (6) −0.0087 (6) −0.0085 (6)
O2 0.0374 (7) 0.0348 (7) 0.0691 (10) −0.0051 (6) −0.0072 (6) −0.0013 (7)
O3 0.0456 (8) 0.0702 (10) 0.0561 (9) 0.0041 (7) −0.0200 (7) −0.0309 (8)
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Geometric parameters (Å, °)

C1—N1 1.315 (2) C23—H23A 0.9300
C1—C2 1.384 (2) C24—C25 1.400 (2)
C1—H1A 0.9300 C24—H24A 0.9300
C2—C3 1.369 (2) C25—C26 1.411 (2)
C2—H2A 0.9300 C25—C33 1.425 (2)
C3—C4 1.398 (2) C26—N6 1.355 (2)
C3—H3A 0.9300 C26—C31 1.456 (2)
C4—C5 1.412 (2) C27—C29 1.365 (3)
C4—C11 1.433 (2) C27—C28 1.385 (3)
C5—N1 1.3570 (19) C27—H27A 0.9300
C5—C10 1.460 (2) C28—N7 1.315 (2)
C6—N2 1.321 (2) C28—H28A 0.9300
C6—C7 1.386 (2) C29—C30 1.396 (2)
C6—H6A 0.9300 C29—H29A 0.9300
C7—C8 1.358 (2) C30—C31 1.414 (2)
C7—H7A 0.9300 C30—C32 1.430 (2)
C8—C9 1.398 (2) C31—N7 1.356 (2)
C8—H8A 0.9300 C32—C33 1.376 (2)
C9—C10 1.410 (2) C32—N8 1.383 (2)
C9—C12 1.420 (2) C33—N9 1.375 (2)
C10—N2 1.363 (2) C34—N8 1.332 (2)
C11—C12 1.372 (2) C34—N9 1.366 (2)
C11—N4 1.3855 (19) C34—C35 1.453 (2)
C12—N3 1.3763 (19) C35—C39 1.386 (2)
C13—N4 1.329 (2) C35—C36 1.391 (2)
C13—N3 1.3630 (19) C36—C37 1.384 (2)
C13—C17 1.456 (2) C36—H36A 0.9300
C14—N5 1.364 (2) C37—C38 1.398 (2)
C14—C15 1.397 (2) C37—H37A 0.9300
C14—C19 1.402 (2) C38—N10 1.378 (2)
C15—C16 1.369 (2) C38—C40 1.402 (3)
C15—H15A 0.9300 C39—C40 1.377 (3)
C16—C17 1.391 (2) C39—H39A 0.9300
C16—H16A 0.9300 C40—H40A 0.9300
C17—C18 1.391 (2) C41—N10 1.445 (2)
C18—C19 1.375 (2) C41—H41A 0.9600
C18—H18A 0.9300 C41—H41B 0.9600
C19—H19A 0.9300 C41—H41C 0.9600
C20—N5 1.448 (2) C42—N10 1.442 (3)
C20—H20A 0.9600 C42—H42A 0.9600
C20—H20B 0.9600 C42—H42B 0.9600
C20—H20C 0.9600 C42—H42C 0.9600
C21—N5 1.445 (2) N3—H3B 0.8600
C21—H21A 0.9600 N9—H7B 0.8600
C21—H21B 0.9600 O1—H1 0.78 (2)
C21—H21C 0.9600 O1—H2 0.95 (3)
C22—N6 1.318 (2) O2—H3 0.86 (2)
C22—C23 1.387 (3) O2—H4 0.92 (3)
C22—H22A 0.9300 O3—H5 0.89 (3)
C23—C24 1.372 (2) O3—H6 0.90 (3)
N1—C1—C2 124.46 (15) C26—C25—C33 116.55 (15)
N1—C1—H1A 117.8 N6—C26—C25 122.21 (16)
C2—C1—H1A 117.8 N6—C26—C31 117.10 (15)
C3—C2—C1 118.45 (16) C25—C26—C31 120.69 (15)
C3—C2—H2A 120.8 C29—C27—C28 118.96 (19)
C1—C2—H2A 120.8 C29—C27—H27A 120.5
C2—C3—C4 119.64 (15) C28—C27—H27A 120.5
C2—C3—H3A 120.2 N7—C28—C27 124.08 (18)
C4—C3—H3A 120.2 N7—C28—H28A 118.0
C3—C4—C5 117.56 (14) C27—C28—H28A 118.0
C3—C4—C11 124.56 (14) C27—C29—C30 119.16 (17)
C5—C4—C11 117.88 (14) C27—C29—H29A 120.4
N1—C5—C4 122.17 (14) C30—C29—H29A 120.4
N1—C5—C10 117.56 (14) C29—C30—C31 118.13 (16)
C4—C5—C10 120.27 (14) C29—C30—C32 124.34 (16)
N2—C6—C7 125.02 (15) C31—C30—C32 117.44 (15)
N2—C6—H6A 117.5 N7—C31—C30 121.65 (16)
C7—C6—H6A 117.5 N7—C31—C26 117.60 (15)
C8—C7—C6 118.58 (16) C30—C31—C26 120.74 (15)
C8—C7—H7A 120.7 C33—C32—N8 110.09 (14)
C6—C7—H7A 120.7 C33—C32—C30 121.00 (15)
C7—C8—C9 119.08 (15) N8—C32—C30 128.87 (16)
C7—C8—H8A 120.5 N9—C33—C32 106.12 (14)
C9—C8—H8A 120.5 N9—C33—C25 130.44 (15)
C8—C9—C10 118.70 (14) C32—C33—C25 123.44 (15)
C8—C9—C12 125.07 (14) N8—C34—N9 111.70 (14)
C10—C9—C12 116.21 (14) N8—C34—C35 124.89 (16)
N2—C10—C9 121.60 (14) N9—C34—C35 123.40 (15)
N2—C10—C5 117.57 (14) C39—C35—C36 116.67 (16)
C9—C10—C5 120.82 (14) C39—C35—C34 121.45 (16)
C12—C11—N4 110.16 (13) C36—C35—C34 121.88 (16)
C12—C11—C4 120.34 (14) C37—C36—C35 121.91 (17)
N4—C11—C4 129.48 (14) C37—C36—H36A 119.0
C11—C12—N3 106.02 (13) C35—C36—H36A 119.0
C11—C12—C9 124.25 (14) C36—C37—C38 121.05 (16)
N3—C12—C9 129.68 (14) C36—C37—H37A 119.5
N4—C13—N3 111.78 (13) C38—C37—H37A 119.5
N4—C13—C17 126.34 (14) N10—C38—C37 121.09 (17)
N3—C13—C17 121.82 (14) N10—C38—C40 121.86 (17)
N5—C14—C15 121.61 (15) C37—C38—C40 117.05 (16)
N5—C14—C19 121.95 (15) C40—C39—C35 122.46 (18)
C15—C14—C19 116.43 (14) C40—C39—H39A 118.8
C16—C15—C14 121.96 (15) C35—C39—H39A 118.8
C16—C15—H15A 119.0 C39—C40—C38 120.86 (18)
C14—C15—H15A 119.0 C39—C40—H40A 119.6
C15—C16—C17 121.85 (16) C38—C40—H40A 119.6
C15—C16—H16A 119.1 N10—C41—H41A 109.5
C17—C16—H16A 119.1 N10—C41—H41B 109.5
C16—C17—C18 116.35 (14) H41A—C41—H41B 109.5
C16—C17—C13 121.61 (14) N10—C41—H41C 109.5
C18—C17—C13 122.02 (14) H41A—C41—H41C 109.5
C19—C18—C17 122.41 (15) H41B—C41—H41C 109.5
C19—C18—H18A 118.8 N10—C42—H42A 109.5
C17—C18—H18A 118.8 N10—C42—H42B 109.5
C18—C19—C14 120.94 (15) H42A—C42—H42B 109.5
C18—C19—H19A 119.5 N10—C42—H42C 109.5
C14—C19—H19A 119.5 H42A—C42—H42C 109.5
N5—C20—H20A 109.5 H42B—C42—H42C 109.5
N5—C20—H20B 109.5 C1—N1—C5 117.67 (14)
H20A—C20—H20B 109.5 C6—N2—C10 116.97 (14)
N5—C20—H20C 109.5 C13—N3—C12 107.03 (13)
H20A—C20—H20C 109.5 C13—N3—H3B 126.5
H20B—C20—H20C 109.5 C12—N3—H3B 126.5
N5—C21—H21A 109.5 C13—N4—C11 105.00 (13)
N5—C21—H21B 109.5 C14—N5—C21 121.34 (14)
H21A—C21—H21B 109.5 C14—N5—C20 120.76 (14)
N5—C21—H21C 109.5 C21—N5—C20 117.81 (14)
H21A—C21—H21C 109.5 C22—N6—C26 117.48 (16)
H21B—C21—H21C 109.5 C28—N7—C31 118.01 (16)
N6—C22—C23 124.27 (17) C34—N8—C32 105.13 (14)
N6—C22—H22A 117.9 C34—N9—C33 106.95 (14)
C23—C22—H22A 117.9 C34—N9—H7B 126.5
C24—C23—C22 119.17 (18) C33—N9—H7B 126.5
C24—C23—H23A 120.4 C38—N10—C42 120.77 (17)
C22—C23—H23A 120.4 C38—N10—C41 120.65 (16)
C23—C24—C25 118.49 (17) C42—N10—C41 117.20 (16)
C23—C24—H24A 120.8 H1—O1—H2 107 (2)
C25—C24—H24A 120.8 H3—O2—H4 108 (2)
C24—C25—C26 118.34 (15) H5—O3—H6 109 (2)
C24—C25—C33 125.09 (15)
N1—C1—C2—C3 −1.8 (3) N6—C26—C31—C30 −178.01 (14)
C1—C2—C3—C4 0.5 (3) C25—C26—C31—C30 1.9 (2)
C2—C3—C4—C5 1.3 (2) C29—C30—C32—C33 176.12 (16)
C2—C3—C4—C11 −177.76 (15) C31—C30—C32—C33 −0.6 (2)
C3—C4—C5—N1 −1.9 (2) C29—C30—C32—N8 −1.2 (3)
C11—C4—C5—N1 177.18 (14) C31—C30—C32—N8 −177.90 (15)
C3—C4—C5—C10 178.31 (14) N8—C32—C33—N9 1.17 (17)
C11—C4—C5—C10 −2.6 (2) C30—C32—C33—N9 −176.61 (14)
N2—C6—C7—C8 −1.6 (3) N8—C32—C33—C25 −178.44 (14)
C6—C7—C8—C9 1.2 (3) C30—C32—C33—C25 3.8 (2)
C7—C8—C9—C10 0.6 (2) C24—C25—C33—N9 −5.0 (3)
C7—C8—C9—C12 −177.95 (16) C26—C25—C33—N9 176.56 (15)
C8—C9—C10—N2 −2.3 (2) C24—C25—C33—C32 174.52 (15)
C12—C9—C10—N2 176.43 (15) C26—C25—C33—C32 −3.9 (2)
C8—C9—C10—C5 178.43 (14) N8—C34—C35—C39 6.5 (3)
C12—C9—C10—C5 −2.9 (2) N9—C34—C35—C39 −171.90 (15)
N1—C5—C10—N2 5.9 (2) N8—C34—C35—C36 −172.97 (16)
C4—C5—C10—N2 −174.34 (15) N9—C34—C35—C36 8.6 (2)
N1—C5—C10—C9 −174.76 (14) C39—C35—C36—C37 0.1 (3)
C4—C5—C10—C9 5.0 (2) C34—C35—C36—C37 179.58 (15)
C3—C4—C11—C12 177.28 (15) C35—C36—C37—C38 0.1 (3)
C5—C4—C11—C12 −1.8 (2) C36—C37—C38—N10 −179.81 (16)
C3—C4—C11—N4 −1.1 (3) C36—C37—C38—C40 0.0 (3)
C5—C4—C11—N4 179.86 (16) C36—C35—C39—C40 −0.4 (3)
N4—C11—C12—N3 0.25 (18) C34—C35—C39—C40 −179.87 (17)
C4—C11—C12—N3 −178.41 (14) C35—C39—C40—C38 0.5 (3)
N4—C11—C12—C9 −177.31 (15) N10—C38—C40—C39 179.53 (18)
C4—C11—C12—C9 4.0 (2) C37—C38—C40—C39 −0.3 (3)
C8—C9—C12—C11 176.98 (15) C2—C1—N1—C5 1.2 (3)
C10—C9—C12—C11 −1.6 (2) C4—C5—N1—C1 0.7 (2)
C8—C9—C12—N3 0.0 (3) C10—C5—N1—C1 −179.54 (14)
C10—C9—C12—N3 −178.55 (15) C7—C6—N2—C10 0.0 (3)
N5—C14—C15—C16 177.78 (18) C9—C10—N2—C6 1.9 (2)
C19—C14—C15—C16 −1.0 (3) C5—C10—N2—C6 −178.74 (15)
C14—C15—C16—C17 −1.2 (3) N4—C13—N3—C12 0.15 (18)
C15—C16—C17—C18 2.6 (3) C17—C13—N3—C12 −177.26 (14)
C15—C16—C17—C13 −176.22 (17) C11—C12—N3—C13 −0.24 (17)
N4—C13—C17—C16 11.0 (3) C9—C12—N3—C13 177.13 (16)
N3—C13—C17—C16 −171.95 (15) N3—C13—N4—C11 0.00 (18)
N4—C13—C17—C18 −167.74 (17) C17—C13—N4—C11 177.27 (16)
N3—C13—C17—C18 9.3 (3) C12—C11—N4—C13 −0.15 (18)
C16—C17—C18—C19 −2.0 (3) C4—C11—N4—C13 178.34 (16)
C13—C17—C18—C19 176.88 (18) C15—C14—N5—C21 −176.70 (19)
C17—C18—C19—C14 −0.2 (3) C19—C14—N5—C21 2.0 (3)
N5—C14—C19—C18 −177.12 (18) C15—C14—N5—C20 −0.2 (3)
C15—C14—C19—C18 1.7 (3) C19—C14—N5—C20 178.50 (18)
N6—C22—C23—C24 1.4 (3) C23—C22—N6—C26 −0.8 (3)
C22—C23—C24—C25 0.0 (3) C25—C26—N6—C22 −1.1 (2)
C23—C24—C25—C26 −1.8 (2) C31—C26—N6—C22 178.83 (15)
C23—C24—C25—C33 179.79 (15) C27—C28—N7—C31 0.2 (3)
C24—C25—C26—N6 2.4 (2) C30—C31—N7—C28 0.1 (3)
C33—C25—C26—N6 −179.01 (14) C26—C31—N7—C28 178.98 (16)
C24—C25—C26—C31 −177.51 (14) N9—C34—N8—C32 0.32 (18)
C33—C25—C26—C31 1.0 (2) C35—C34—N8—C32 −178.26 (15)
C29—C27—C28—N7 −0.4 (3) C33—C32—N8—C34 −0.93 (17)
C28—C27—C29—C30 0.2 (3) C30—C32—N8—C34 176.63 (16)
C27—C29—C30—C31 0.1 (3) N8—C34—N9—C33 0.40 (18)
C27—C29—C30—C32 −176.62 (17) C35—C34—N9—C33 179.00 (14)
C29—C30—C31—N7 −0.2 (2) C32—C33—N9—C34 −0.94 (16)
C32—C30—C31—N7 176.68 (15) C25—C33—N9—C34 178.63 (16)
C29—C30—C31—C26 −179.08 (15) C37—C38—N10—C42 −175.56 (18)
C32—C30—C31—C26 −2.2 (2) C40—C38—N10—C42 4.6 (3)
N6—C26—C31—N7 3.1 (2) C37—C38—N10—C41 −9.3 (3)
C25—C26—C31—N7 −176.97 (15) C40—C38—N10—C41 170.87 (18)
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Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A
O3—H6···N8 0.90 (3) 2.01 (3) 2.870 (2) 159 (2)
C18—H18A···N3 0.93 2.61 2.919 (2) 100
O1—H1···O3i 0.78 (2) 1.93 (2) 2.711 (2) 176 (2)
O1—H2···N4i 0.95 (3) 1.95 (3) 2.891 (2) 170 (2)
N9—H7B···O1ii 0.86 1.98 2.820 (2) 166
O2—H3···N6iii 0.86 (2) 2.34 (2) 3.047 (2) 139 (2)
O2—H3···N7iii 0.86 (2) 2.15 (2) 2.899 (2) 144 (2)
O2—H4···N1i 0.92 (3) 2.11 (3) 2.943 (2) 151 (2)
N3—H3B···O2iv 0.86 1.94 2.751 (2) 157
O3—H5···N2i 0.89 (3) 2.10 (3) 2.969 (2) 163 (2)
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Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y, z−1; (iii) x, y+1, z; (iv) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2098).

References

  1. Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  2. Rigaku/MSC (2000). CrystalClear Rigaku/MSC, The Woodlands, Texas, USA.
  3. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  4. Sun, M., Chen, G., Ling, B.-P. & Liu, Y.-X. (2007). Acta Cryst. E63, o1210–o1211.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808016930/pk2098sup1.cif

e-64-o1236-sup1.cif (32.4KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016930/pk2098Isup2.hkl

e-64-o1236-Isup2.hkl (438.9KB, hkl)

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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