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ISSN: 2056-9890

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

aDepartment of Chemistry, Guangdong Medical College, Zhanjiang, Guangdong 524023, People's Republic of China
*Correspondence e-mail: yingq666@sohu.com

(Received 10 May 2008; accepted 4 June 2008; online 7 June 2008)

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[Sun, M., Chen, G., Ling, B.-P. & Liu, Y.-X. (2007). Acta Cryst. E63, o1210-o1211.]). For bond-length data, see: Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data
  • C21H17N5·1.5H2O

  • Mr = 386.42

  • Triclinic, [P \overline 1]

  • 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[Rigaku/MSC (2000). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.]) Tmin = 0.961, Tmax = 0.974

  • 15313 measured reflections

  • 8974 independent reflections

  • 5671 reflections with I > 2σ(I)

  • Rint = 0.042

Refinement
  • R[F2 > 2σ(F2)] = 0.051

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y, z-1; (iii) x, y+1, z; (iv) x-1, y, z.

Data collection: CrystalClear (Rigaku/MSC, 2000[Rigaku/MSC (2000). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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.

Related literature top

For related literature, see: Sun et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental top

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 top

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.

Computing details top

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

Figures top
[Figure 1] Fig. 1. A view of the compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level.
2-[4-(Dimethylamino)phenyl]imidazo[4,5-f][1,10]phenanthroline sesquihydrate top
Crystal data top
C21H17N5·1.5(H2O)Z = 4
Mr = 386.42F(000) = 772
Triclinic, P1Dx = 1.324 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.0503 (9) ÅCell parameters from 4754 reflections
b = 12.6386 (8) Åθ = 1.5–28.3°
c = 14.0297 (11) ŵ = 0.09 mm1
α = 73.685 (9)°T = 293 K
β = 81.909 (10)°Prism, yellow
γ = 79.163 (9)°0.45 × 0.35 × 0.30 mm
V = 1838.9 (3) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
8974 independent reflections
Radiation source: fine-focus sealed tube5671 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
ϕ and ω scansθmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2000)
h = 1414
Tmin = 0.961, Tmax = 0.974k = 1613
15313 measured reflectionsl = 1817
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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H atoms treated by a mixture of independent and constrained refinement
S = 0.96 w = 1/[σ2(Fo2) + (0.0641P)2]
where P = (Fo2 + 2Fc2)/3
8974 reflections(Δ/σ)max < 0.001
520 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C21H17N5·1.5(H2O)γ = 79.163 (9)°
Mr = 386.42V = 1838.9 (3) Å3
Triclinic, P1Z = 4
a = 11.0503 (9) ÅMo Kα radiation
b = 12.6386 (8) ŵ = 0.09 mm1
c = 14.0297 (11) ÅT = 293 K
α = 73.685 (9)°0.45 × 0.35 × 0.30 mm
β = 81.909 (10)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
8974 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2000)
5671 reflections with I > 2σ(I)
Tmin = 0.961, Tmax = 0.974Rint = 0.042
15313 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.138H atoms treated by a mixture of independent and constrained refinement
S = 0.96Δρmax = 0.35 e Å3
8974 reflectionsΔρmin = 0.22 e Å3
520 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.45171 (15)0.33283 (14)0.52723 (13)0.0392 (4)
H1A0.49720.26570.55940.047*
C20.50296 (15)0.39220 (14)0.43682 (13)0.0387 (4)
H2A0.58140.36650.41040.046*
C30.43558 (15)0.48961 (14)0.38724 (12)0.0348 (4)
H3A0.46760.53080.32610.042*
C40.31834 (14)0.52678 (12)0.42896 (11)0.0289 (3)
C50.27578 (14)0.46184 (13)0.52285 (12)0.0301 (3)
C60.01425 (16)0.46905 (15)0.70863 (13)0.0431 (4)
H6A0.00780.42810.77290.052*
C70.07076 (16)0.55909 (14)0.66489 (12)0.0392 (4)
H7A0.14760.57610.69850.047*
C80.03942 (15)0.62191 (14)0.57195 (12)0.0347 (4)
H8A0.09400.68360.54130.042*
C90.07598 (14)0.59251 (12)0.52306 (11)0.0291 (3)
C100.15556 (14)0.49771 (13)0.57175 (11)0.0296 (3)
C110.23794 (14)0.62512 (13)0.38244 (11)0.0293 (3)
C120.12222 (14)0.65243 (12)0.42739 (11)0.0297 (3)
C130.15243 (15)0.77516 (13)0.28321 (12)0.0322 (4)
C140.08692 (15)1.07618 (13)0.04811 (12)0.0356 (4)
C150.18800 (15)0.99284 (14)0.04114 (12)0.0395 (4)
H15A0.24411.00360.01540.047*
C160.20693 (16)0.89581 (14)0.11507 (13)0.0386 (4)
H16A0.27460.84200.10680.046*
C170.12777 (14)0.87548 (13)0.20225 (11)0.0323 (4)
C180.02535 (16)0.95707 (14)0.20844 (13)0.0404 (4)
H18A0.03100.94530.26480.048*
C190.00444 (16)1.05446 (14)0.13433 (13)0.0409 (4)
H19A0.06541.10670.14150.049*
C200.15919 (19)1.19547 (17)0.11149 (14)0.0590 (6)
H20A0.23751.19950.09160.089*
H20B0.12971.26490.15710.089*
H20C0.16891.13610.14350.089*
C210.03024 (19)1.26246 (16)0.01427 (16)0.0599 (6)
H21A0.03261.27690.04970.090*
H21B0.10681.24020.01980.090*
H21C0.01851.32890.06600.090*
C220.54717 (18)0.06149 (16)0.22080 (14)0.0497 (5)
H22A0.52760.13310.24680.060*
C230.50237 (17)0.00110 (16)0.13110 (14)0.0462 (5)
H23A0.45290.02780.09930.055*
C240.53193 (15)0.10615 (15)0.08978 (13)0.0384 (4)
H24A0.50300.14970.02970.046*
C250.60662 (14)0.14625 (13)0.14012 (12)0.0329 (4)
C260.64498 (15)0.07783 (14)0.23243 (12)0.0350 (4)
C270.8597 (2)0.18442 (16)0.39974 (15)0.0555 (5)
H27A0.90770.20440.43930.067*
C280.8253 (2)0.07935 (16)0.42726 (15)0.0534 (5)
H28A0.85200.02990.48590.064*
C290.82222 (18)0.25814 (15)0.31362 (14)0.0467 (5)
H29A0.84450.32900.29360.056*
C300.74997 (15)0.22578 (13)0.25602 (12)0.0353 (4)
C310.71856 (15)0.11709 (13)0.28993 (12)0.0349 (4)
C320.71051 (15)0.29322 (13)0.16206 (12)0.0340 (4)
C330.64546 (14)0.25301 (13)0.10671 (12)0.0323 (4)
C340.68171 (15)0.42218 (13)0.02556 (12)0.0356 (4)
C350.68460 (15)0.52469 (14)0.05363 (12)0.0365 (4)
C360.61896 (16)0.54779 (14)0.13666 (12)0.0389 (4)
H36A0.57230.49590.14180.047*
C370.62105 (16)0.64571 (14)0.21179 (12)0.0380 (4)
H37A0.57590.65830.26610.046*
C380.68999 (16)0.72604 (14)0.20729 (13)0.0396 (4)
C390.75241 (18)0.60484 (16)0.04965 (14)0.0478 (5)
H39A0.79690.59210.00510.057*
C400.75633 (19)0.70268 (15)0.12370 (14)0.0501 (5)
H40A0.80360.75390.11820.060*
C410.6379 (2)0.83872 (18)0.37374 (14)0.0590 (6)
H41A0.65660.90680.42020.089*
H41B0.54980.84240.36040.089*
H41C0.67150.77690.40160.089*
C420.7699 (2)0.90254 (18)0.28036 (16)0.0651 (6)
H42A0.75830.96590.33690.098*
H42B0.85500.86770.28300.098*
H42C0.74860.92650.22010.098*
N10.34306 (12)0.36491 (11)0.57079 (10)0.0360 (3)
N20.12422 (13)0.43701 (12)0.66596 (10)0.0379 (3)
N30.06820 (12)0.74814 (11)0.36341 (9)0.0311 (3)
H3B0.00490.78410.37230.037*
N40.25682 (12)0.70252 (11)0.29184 (10)0.0328 (3)
N50.07091 (14)1.17421 (13)0.02435 (11)0.0501 (4)
N60.61562 (14)0.02608 (12)0.27155 (11)0.0437 (4)
N70.75716 (14)0.04518 (12)0.37563 (11)0.0433 (4)
N80.73203 (13)0.39979 (11)0.11132 (10)0.0375 (3)
N90.62862 (12)0.33528 (11)0.01943 (10)0.0349 (3)
H7B0.59170.33260.02970.042*
N100.69184 (17)0.82371 (13)0.28192 (11)0.0537 (4)
O10.53530 (14)0.29356 (11)0.85874 (10)0.0434 (3)
O20.81559 (12)0.80854 (12)0.38807 (11)0.0495 (4)
O30.67079 (13)0.57209 (13)0.21453 (11)0.0546 (4)
H30.769 (2)0.873 (2)0.3756 (17)0.075 (7)*
H10.474 (2)0.3296 (19)0.8380 (16)0.064 (7)*
H50.723 (2)0.5821 (19)0.2531 (17)0.078 (8)*
H20.597 (2)0.297 (2)0.8037 (19)0.092 (9)*
H40.774 (2)0.757 (2)0.3773 (19)0.098 (9)*
H60.709 (2)0.522 (2)0.181 (2)0.097 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0366 (9)0.0371 (9)0.0415 (10)0.0016 (8)0.0144 (8)0.0061 (8)
C20.0330 (8)0.0421 (10)0.0435 (10)0.0035 (7)0.0054 (7)0.0160 (8)
C30.0350 (8)0.0402 (9)0.0314 (9)0.0090 (7)0.0053 (7)0.0096 (7)
C40.0298 (8)0.0300 (8)0.0291 (8)0.0070 (6)0.0076 (6)0.0074 (7)
C50.0310 (8)0.0299 (8)0.0312 (8)0.0075 (7)0.0092 (7)0.0063 (7)
C60.0430 (10)0.0497 (11)0.0294 (9)0.0084 (9)0.0006 (8)0.0005 (8)
C70.0365 (9)0.0438 (10)0.0349 (9)0.0081 (8)0.0010 (7)0.0072 (8)
C80.0342 (8)0.0344 (9)0.0361 (9)0.0067 (7)0.0053 (7)0.0086 (7)
C90.0311 (8)0.0281 (8)0.0304 (8)0.0086 (6)0.0062 (6)0.0070 (7)
C100.0324 (8)0.0300 (8)0.0272 (8)0.0098 (7)0.0073 (6)0.0036 (7)
C110.0312 (8)0.0315 (8)0.0265 (8)0.0083 (7)0.0072 (6)0.0051 (7)
C120.0328 (8)0.0281 (8)0.0288 (8)0.0074 (6)0.0083 (6)0.0042 (7)
C130.0340 (8)0.0325 (8)0.0309 (9)0.0095 (7)0.0017 (7)0.0074 (7)
C140.0340 (8)0.0333 (9)0.0347 (9)0.0049 (7)0.0046 (7)0.0010 (7)
C150.0372 (9)0.0408 (10)0.0330 (9)0.0038 (8)0.0039 (7)0.0027 (8)
C160.0374 (9)0.0346 (9)0.0385 (10)0.0019 (7)0.0021 (8)0.0041 (8)
C170.0342 (8)0.0330 (8)0.0284 (8)0.0085 (7)0.0051 (7)0.0028 (7)
C180.0373 (9)0.0385 (9)0.0370 (10)0.0047 (8)0.0057 (7)0.0018 (8)
C190.0352 (9)0.0370 (9)0.0398 (10)0.0030 (7)0.0028 (8)0.0018 (8)
C200.0584 (12)0.0519 (12)0.0471 (12)0.0040 (10)0.0041 (10)0.0115 (10)
C210.0555 (12)0.0444 (11)0.0599 (13)0.0072 (10)0.0013 (10)0.0054 (10)
C220.0594 (12)0.0454 (11)0.0507 (12)0.0228 (9)0.0038 (10)0.0139 (9)
C230.0457 (10)0.0566 (12)0.0457 (11)0.0211 (9)0.0022 (9)0.0208 (9)
C240.0355 (9)0.0452 (10)0.0369 (10)0.0088 (8)0.0025 (7)0.0133 (8)
C250.0293 (8)0.0360 (9)0.0346 (9)0.0040 (7)0.0001 (7)0.0135 (7)
C260.0350 (8)0.0365 (9)0.0358 (9)0.0049 (7)0.0016 (7)0.0143 (7)
C270.0761 (14)0.0497 (11)0.0509 (12)0.0159 (11)0.0289 (10)0.0144 (10)
C280.0730 (14)0.0482 (11)0.0426 (11)0.0135 (10)0.0199 (10)0.0081 (9)
C290.0603 (12)0.0384 (10)0.0469 (11)0.0114 (9)0.0159 (9)0.0122 (9)
C300.0392 (9)0.0337 (8)0.0351 (9)0.0038 (7)0.0046 (7)0.0130 (7)
C310.0374 (9)0.0345 (9)0.0329 (9)0.0017 (7)0.0060 (7)0.0102 (7)
C320.0355 (8)0.0327 (8)0.0351 (9)0.0025 (7)0.0047 (7)0.0122 (7)
C330.0313 (8)0.0347 (8)0.0310 (9)0.0009 (7)0.0057 (7)0.0102 (7)
C340.0354 (8)0.0353 (9)0.0378 (10)0.0042 (7)0.0029 (7)0.0134 (8)
C350.0384 (9)0.0355 (9)0.0363 (9)0.0048 (7)0.0042 (7)0.0108 (7)
C360.0402 (9)0.0369 (9)0.0414 (10)0.0084 (8)0.0047 (8)0.0111 (8)
C370.0419 (9)0.0406 (9)0.0328 (9)0.0046 (8)0.0089 (7)0.0104 (8)
C380.0464 (10)0.0386 (9)0.0334 (9)0.0074 (8)0.0007 (8)0.0103 (8)
C390.0606 (12)0.0489 (11)0.0398 (10)0.0169 (10)0.0183 (9)0.0087 (9)
C400.0635 (12)0.0439 (11)0.0488 (11)0.0208 (10)0.0141 (10)0.0092 (9)
C410.0721 (14)0.0602 (13)0.0424 (12)0.0160 (11)0.0035 (10)0.0069 (10)
C420.0895 (16)0.0610 (14)0.0502 (13)0.0392 (13)0.0047 (12)0.0061 (10)
N10.0347 (7)0.0348 (7)0.0368 (8)0.0045 (6)0.0093 (6)0.0045 (6)
N20.0388 (8)0.0419 (8)0.0292 (8)0.0089 (7)0.0055 (6)0.0004 (6)
N30.0296 (7)0.0305 (7)0.0305 (7)0.0038 (6)0.0040 (6)0.0036 (6)
N40.0337 (7)0.0328 (7)0.0299 (7)0.0062 (6)0.0047 (6)0.0036 (6)
N50.0471 (9)0.0417 (9)0.0400 (9)0.0060 (7)0.0071 (7)0.0103 (7)
N60.0519 (9)0.0367 (8)0.0449 (9)0.0121 (7)0.0070 (7)0.0097 (7)
N70.0544 (9)0.0396 (8)0.0372 (8)0.0072 (7)0.0163 (7)0.0064 (7)
N80.0425 (8)0.0322 (7)0.0391 (8)0.0052 (6)0.0077 (6)0.0102 (6)
N90.0351 (7)0.0374 (8)0.0334 (8)0.0042 (6)0.0076 (6)0.0099 (6)
N100.0777 (12)0.0483 (9)0.0387 (9)0.0280 (9)0.0114 (8)0.0024 (7)
O10.0402 (7)0.0500 (8)0.0377 (7)0.0026 (6)0.0087 (6)0.0085 (6)
O20.0374 (7)0.0348 (7)0.0691 (10)0.0051 (6)0.0072 (6)0.0013 (7)
O30.0456 (8)0.0702 (10)0.0561 (9)0.0041 (7)0.0200 (7)0.0309 (8)
Geometric parameters (Å, º) top
C1—N11.315 (2)C23—H23A0.9300
C1—C21.384 (2)C24—C251.400 (2)
C1—H1A0.9300C24—H24A0.9300
C2—C31.369 (2)C25—C261.411 (2)
C2—H2A0.9300C25—C331.425 (2)
C3—C41.398 (2)C26—N61.355 (2)
C3—H3A0.9300C26—C311.456 (2)
C4—C51.412 (2)C27—C291.365 (3)
C4—C111.433 (2)C27—C281.385 (3)
C5—N11.3570 (19)C27—H27A0.9300
C5—C101.460 (2)C28—N71.315 (2)
C6—N21.321 (2)C28—H28A0.9300
C6—C71.386 (2)C29—C301.396 (2)
C6—H6A0.9300C29—H29A0.9300
C7—C81.358 (2)C30—C311.414 (2)
C7—H7A0.9300C30—C321.430 (2)
C8—C91.398 (2)C31—N71.356 (2)
C8—H8A0.9300C32—C331.376 (2)
C9—C101.410 (2)C32—N81.383 (2)
C9—C121.420 (2)C33—N91.375 (2)
C10—N21.363 (2)C34—N81.332 (2)
C11—C121.372 (2)C34—N91.366 (2)
C11—N41.3855 (19)C34—C351.453 (2)
C12—N31.3763 (19)C35—C391.386 (2)
C13—N41.329 (2)C35—C361.391 (2)
C13—N31.3630 (19)C36—C371.384 (2)
C13—C171.456 (2)C36—H36A0.9300
C14—N51.364 (2)C37—C381.398 (2)
C14—C151.397 (2)C37—H37A0.9300
C14—C191.402 (2)C38—N101.378 (2)
C15—C161.369 (2)C38—C401.402 (3)
C15—H15A0.9300C39—C401.377 (3)
C16—C171.391 (2)C39—H39A0.9300
C16—H16A0.9300C40—H40A0.9300
C17—C181.391 (2)C41—N101.445 (2)
C18—C191.375 (2)C41—H41A0.9600
C18—H18A0.9300C41—H41B0.9600
C19—H19A0.9300C41—H41C0.9600
C20—N51.448 (2)C42—N101.442 (3)
C20—H20A0.9600C42—H42A0.9600
C20—H20B0.9600C42—H42B0.9600
C20—H20C0.9600C42—H42C0.9600
C21—N51.445 (2)N3—H3B0.8600
C21—H21A0.9600N9—H7B0.8600
C21—H21B0.9600O1—H10.78 (2)
C21—H21C0.9600O1—H20.95 (3)
C22—N61.318 (2)O2—H30.86 (2)
C22—C231.387 (3)O2—H40.92 (3)
C22—H22A0.9300O3—H50.89 (3)
C23—C241.372 (2)O3—H60.90 (3)
N1—C1—C2124.46 (15)C26—C25—C33116.55 (15)
N1—C1—H1A117.8N6—C26—C25122.21 (16)
C2—C1—H1A117.8N6—C26—C31117.10 (15)
C3—C2—C1118.45 (16)C25—C26—C31120.69 (15)
C3—C2—H2A120.8C29—C27—C28118.96 (19)
C1—C2—H2A120.8C29—C27—H27A120.5
C2—C3—C4119.64 (15)C28—C27—H27A120.5
C2—C3—H3A120.2N7—C28—C27124.08 (18)
C4—C3—H3A120.2N7—C28—H28A118.0
C3—C4—C5117.56 (14)C27—C28—H28A118.0
C3—C4—C11124.56 (14)C27—C29—C30119.16 (17)
C5—C4—C11117.88 (14)C27—C29—H29A120.4
N1—C5—C4122.17 (14)C30—C29—H29A120.4
N1—C5—C10117.56 (14)C29—C30—C31118.13 (16)
C4—C5—C10120.27 (14)C29—C30—C32124.34 (16)
N2—C6—C7125.02 (15)C31—C30—C32117.44 (15)
N2—C6—H6A117.5N7—C31—C30121.65 (16)
C7—C6—H6A117.5N7—C31—C26117.60 (15)
C8—C7—C6118.58 (16)C30—C31—C26120.74 (15)
C8—C7—H7A120.7C33—C32—N8110.09 (14)
C6—C7—H7A120.7C33—C32—C30121.00 (15)
C7—C8—C9119.08 (15)N8—C32—C30128.87 (16)
C7—C8—H8A120.5N9—C33—C32106.12 (14)
C9—C8—H8A120.5N9—C33—C25130.44 (15)
C8—C9—C10118.70 (14)C32—C33—C25123.44 (15)
C8—C9—C12125.07 (14)N8—C34—N9111.70 (14)
C10—C9—C12116.21 (14)N8—C34—C35124.89 (16)
N2—C10—C9121.60 (14)N9—C34—C35123.40 (15)
N2—C10—C5117.57 (14)C39—C35—C36116.67 (16)
C9—C10—C5120.82 (14)C39—C35—C34121.45 (16)
C12—C11—N4110.16 (13)C36—C35—C34121.88 (16)
C12—C11—C4120.34 (14)C37—C36—C35121.91 (17)
N4—C11—C4129.48 (14)C37—C36—H36A119.0
C11—C12—N3106.02 (13)C35—C36—H36A119.0
C11—C12—C9124.25 (14)C36—C37—C38121.05 (16)
N3—C12—C9129.68 (14)C36—C37—H37A119.5
N4—C13—N3111.78 (13)C38—C37—H37A119.5
N4—C13—C17126.34 (14)N10—C38—C37121.09 (17)
N3—C13—C17121.82 (14)N10—C38—C40121.86 (17)
N5—C14—C15121.61 (15)C37—C38—C40117.05 (16)
N5—C14—C19121.95 (15)C40—C39—C35122.46 (18)
C15—C14—C19116.43 (14)C40—C39—H39A118.8
C16—C15—C14121.96 (15)C35—C39—H39A118.8
C16—C15—H15A119.0C39—C40—C38120.86 (18)
C14—C15—H15A119.0C39—C40—H40A119.6
C15—C16—C17121.85 (16)C38—C40—H40A119.6
C15—C16—H16A119.1N10—C41—H41A109.5
C17—C16—H16A119.1N10—C41—H41B109.5
C16—C17—C18116.35 (14)H41A—C41—H41B109.5
C16—C17—C13121.61 (14)N10—C41—H41C109.5
C18—C17—C13122.02 (14)H41A—C41—H41C109.5
C19—C18—C17122.41 (15)H41B—C41—H41C109.5
C19—C18—H18A118.8N10—C42—H42A109.5
C17—C18—H18A118.8N10—C42—H42B109.5
C18—C19—C14120.94 (15)H42A—C42—H42B109.5
C18—C19—H19A119.5N10—C42—H42C109.5
C14—C19—H19A119.5H42A—C42—H42C109.5
N5—C20—H20A109.5H42B—C42—H42C109.5
N5—C20—H20B109.5C1—N1—C5117.67 (14)
H20A—C20—H20B109.5C6—N2—C10116.97 (14)
N5—C20—H20C109.5C13—N3—C12107.03 (13)
H20A—C20—H20C109.5C13—N3—H3B126.5
H20B—C20—H20C109.5C12—N3—H3B126.5
N5—C21—H21A109.5C13—N4—C11105.00 (13)
N5—C21—H21B109.5C14—N5—C21121.34 (14)
H21A—C21—H21B109.5C14—N5—C20120.76 (14)
N5—C21—H21C109.5C21—N5—C20117.81 (14)
H21A—C21—H21C109.5C22—N6—C26117.48 (16)
H21B—C21—H21C109.5C28—N7—C31118.01 (16)
N6—C22—C23124.27 (17)C34—N8—C32105.13 (14)
N6—C22—H22A117.9C34—N9—C33106.95 (14)
C23—C22—H22A117.9C34—N9—H7B126.5
C24—C23—C22119.17 (18)C33—N9—H7B126.5
C24—C23—H23A120.4C38—N10—C42120.77 (17)
C22—C23—H23A120.4C38—N10—C41120.65 (16)
C23—C24—C25118.49 (17)C42—N10—C41117.20 (16)
C23—C24—H24A120.8H1—O1—H2107 (2)
C25—C24—H24A120.8H3—O2—H4108 (2)
C24—C25—C26118.34 (15)H5—O3—H6109 (2)
C24—C25—C33125.09 (15)
N1—C1—C2—C31.8 (3)N6—C26—C31—C30178.01 (14)
C1—C2—C3—C40.5 (3)C25—C26—C31—C301.9 (2)
C2—C3—C4—C51.3 (2)C29—C30—C32—C33176.12 (16)
C2—C3—C4—C11177.76 (15)C31—C30—C32—C330.6 (2)
C3—C4—C5—N11.9 (2)C29—C30—C32—N81.2 (3)
C11—C4—C5—N1177.18 (14)C31—C30—C32—N8177.90 (15)
C3—C4—C5—C10178.31 (14)N8—C32—C33—N91.17 (17)
C11—C4—C5—C102.6 (2)C30—C32—C33—N9176.61 (14)
N2—C6—C7—C81.6 (3)N8—C32—C33—C25178.44 (14)
C6—C7—C8—C91.2 (3)C30—C32—C33—C253.8 (2)
C7—C8—C9—C100.6 (2)C24—C25—C33—N95.0 (3)
C7—C8—C9—C12177.95 (16)C26—C25—C33—N9176.56 (15)
C8—C9—C10—N22.3 (2)C24—C25—C33—C32174.52 (15)
C12—C9—C10—N2176.43 (15)C26—C25—C33—C323.9 (2)
C8—C9—C10—C5178.43 (14)N8—C34—C35—C396.5 (3)
C12—C9—C10—C52.9 (2)N9—C34—C35—C39171.90 (15)
N1—C5—C10—N25.9 (2)N8—C34—C35—C36172.97 (16)
C4—C5—C10—N2174.34 (15)N9—C34—C35—C368.6 (2)
N1—C5—C10—C9174.76 (14)C39—C35—C36—C370.1 (3)
C4—C5—C10—C95.0 (2)C34—C35—C36—C37179.58 (15)
C3—C4—C11—C12177.28 (15)C35—C36—C37—C380.1 (3)
C5—C4—C11—C121.8 (2)C36—C37—C38—N10179.81 (16)
C3—C4—C11—N41.1 (3)C36—C37—C38—C400.0 (3)
C5—C4—C11—N4179.86 (16)C36—C35—C39—C400.4 (3)
N4—C11—C12—N30.25 (18)C34—C35—C39—C40179.87 (17)
C4—C11—C12—N3178.41 (14)C35—C39—C40—C380.5 (3)
N4—C11—C12—C9177.31 (15)N10—C38—C40—C39179.53 (18)
C4—C11—C12—C94.0 (2)C37—C38—C40—C390.3 (3)
C8—C9—C12—C11176.98 (15)C2—C1—N1—C51.2 (3)
C10—C9—C12—C111.6 (2)C4—C5—N1—C10.7 (2)
C8—C9—C12—N30.0 (3)C10—C5—N1—C1179.54 (14)
C10—C9—C12—N3178.55 (15)C7—C6—N2—C100.0 (3)
N5—C14—C15—C16177.78 (18)C9—C10—N2—C61.9 (2)
C19—C14—C15—C161.0 (3)C5—C10—N2—C6178.74 (15)
C14—C15—C16—C171.2 (3)N4—C13—N3—C120.15 (18)
C15—C16—C17—C182.6 (3)C17—C13—N3—C12177.26 (14)
C15—C16—C17—C13176.22 (17)C11—C12—N3—C130.24 (17)
N4—C13—C17—C1611.0 (3)C9—C12—N3—C13177.13 (16)
N3—C13—C17—C16171.95 (15)N3—C13—N4—C110.00 (18)
N4—C13—C17—C18167.74 (17)C17—C13—N4—C11177.27 (16)
N3—C13—C17—C189.3 (3)C12—C11—N4—C130.15 (18)
C16—C17—C18—C192.0 (3)C4—C11—N4—C13178.34 (16)
C13—C17—C18—C19176.88 (18)C15—C14—N5—C21176.70 (19)
C17—C18—C19—C140.2 (3)C19—C14—N5—C212.0 (3)
N5—C14—C19—C18177.12 (18)C15—C14—N5—C200.2 (3)
C15—C14—C19—C181.7 (3)C19—C14—N5—C20178.50 (18)
N6—C22—C23—C241.4 (3)C23—C22—N6—C260.8 (3)
C22—C23—C24—C250.0 (3)C25—C26—N6—C221.1 (2)
C23—C24—C25—C261.8 (2)C31—C26—N6—C22178.83 (15)
C23—C24—C25—C33179.79 (15)C27—C28—N7—C310.2 (3)
C24—C25—C26—N62.4 (2)C30—C31—N7—C280.1 (3)
C33—C25—C26—N6179.01 (14)C26—C31—N7—C28178.98 (16)
C24—C25—C26—C31177.51 (14)N9—C34—N8—C320.32 (18)
C33—C25—C26—C311.0 (2)C35—C34—N8—C32178.26 (15)
C29—C27—C28—N70.4 (3)C33—C32—N8—C340.93 (17)
C28—C27—C29—C300.2 (3)C30—C32—N8—C34176.63 (16)
C27—C29—C30—C310.1 (3)N8—C34—N9—C330.40 (18)
C27—C29—C30—C32176.62 (17)C35—C34—N9—C33179.00 (14)
C29—C30—C31—N70.2 (2)C32—C33—N9—C340.94 (16)
C32—C30—C31—N7176.68 (15)C25—C33—N9—C34178.63 (16)
C29—C30—C31—C26179.08 (15)C37—C38—N10—C42175.56 (18)
C32—C30—C31—C262.2 (2)C40—C38—N10—C424.6 (3)
N6—C26—C31—N73.1 (2)C37—C38—N10—C419.3 (3)
C25—C26—C31—N7176.97 (15)C40—C38—N10—C41170.87 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H6···N80.90 (3)2.01 (3)2.870 (2)159 (2)
C18—H18A···N30.932.612.919 (2)100
O1—H1···O3i0.78 (2)1.93 (2)2.711 (2)176 (2)
O1—H2···N4i0.95 (3)1.95 (3)2.891 (2)170 (2)
N9—H7B···O1ii0.861.982.820 (2)166
O2—H3···N6iii0.86 (2)2.34 (2)3.047 (2)139 (2)
O2—H3···N7iii0.86 (2)2.15 (2)2.899 (2)144 (2)
O2—H4···N1i0.92 (3)2.11 (3)2.943 (2)151 (2)
N3—H3B···O2iv0.861.942.751 (2)157
O3—H5···N2i0.89 (3)2.10 (3)2.969 (2)163 (2)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y, z1; (iii) x, y+1, z; (iv) x1, y, z.

Experimental details

Crystal data
Chemical formulaC21H17N5·1.5(H2O)
Mr386.42
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)11.0503 (9), 12.6386 (8), 14.0297 (11)
α, β, γ (°)73.685 (9), 81.909 (10), 79.163 (9)
V3)1838.9 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.45 × 0.35 × 0.30
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2000)
Tmin, Tmax0.961, 0.974
No. of measured, independent and
observed [I > 2σ(I)] reflections
15313, 8974, 5671
Rint0.042
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.138, 0.96
No. of reflections8974
No. of parameters520
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.35, 0.22

Computer programs: CrystalClear (Rigaku/MSC, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick,/MSC 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H6···N80.90 (3)2.01 (3)2.870 (2)159 (2)
C18—H18A···N30.932.612.919 (2)100.3
O1—H1···O3i0.78 (2)1.93 (2)2.711 (2)176 (2)
O1—H2···N4i0.95 (3)1.95 (3)2.891 (2)170 (2)
N9—H7B···O1ii0.861.982.820 (2)166.4
O2—H3···N6iii0.86 (2)2.34 (2)3.047 (2)139 (2)
O2—H3···N7iii0.86 (2)2.15 (2)2.899 (2)144 (2)
O2—H4···N1i0.92 (3)2.11 (3)2.943 (2)151 (2)
N3—H3B···O2iv0.861.942.751 (2)156.7
O3—H5···N2i0.89 (3)2.10 (3)2.969 (2)163 (2)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y, z1; (iii) x, y+1, z; (iv) x1, y, z.
 

Acknowledgements

I acknowledge financial support from the NSF of Guangdong Province

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationRigaku/MSC (2000). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSun, M., Chen, G., Ling, B.-P. & Liu, Y.-X. (2007). Acta Cryst. E63, o1210–o1211.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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