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Acta Crystallogr Sect E Struct Rep Online. 2008 July 1; 64(Pt 7): o1236.
Published online 2008 June 7. doi:  10.1107/S1600536808016930
PMCID: PMC2961644

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

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 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1236-scheme1.jpg

Experimental

Crystal data

  • C21H17N5·1.5H2O
  • M r = 386.42
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1236-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

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

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.
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 = 386.42F000 = 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 = 1.5–28.3º
c = 14.0297 (11) ŵ = 0.09 mm1
α = 73.685 (9)ºT = 293 (2) K
β = 81.909 (10)ºPrism, yellow
γ = 79.163 (9)º0.45 × 0.35 × 0.30 mm
V = 1838.9 (3) Å3

Data collection

Bruker SMART CCD area-detector diffractometer8974 independent reflections
Radiation source: fine-focus sealed tube5671 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.042
T = 293(2) Kθmax = 28.3º
[var phi] and ω scansθmin = 1.9º
Absorption correction: multi-scan(CrystalClear; Rigaku/MSC, 2000)h = −14→14
Tmin = 0.961, Tmax = 0.974k = −16→13
15313 measured reflectionsl = −18→17

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H 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 reflectionsΔρmax = 0.35 e Å3
520 parametersΔρmin = −0.21 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
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)
H6A−0.00780.42810.77290.052*
C7−0.07076 (16)0.55909 (14)0.66489 (12)0.0392 (4)
H7A−0.14760.57610.69850.047*
C8−0.03942 (15)0.62191 (14)0.57195 (12)0.0347 (4)
H8A−0.09400.68360.54130.042*
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)
H15A0.24411.0036−0.01540.047*
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)
H18A−0.03100.94530.26480.048*
C190.00444 (16)1.05446 (14)0.13433 (13)0.0409 (4)
H19A−0.06541.10670.14150.049*
C200.15919 (19)1.19547 (17)−0.11149 (14)0.0590 (6)
H20A0.23751.1995−0.09160.089*
H20B0.12971.2649−0.15710.089*
H20C0.16891.1361−0.14350.089*
C21−0.03024 (19)1.26246 (16)−0.01427 (16)0.0599 (6)
H21A−0.03261.27690.04970.090*
H21B−0.10681.2402−0.01980.090*
H21C−0.01851.3289−0.06600.090*
C220.54717 (18)−0.06149 (16)0.22080 (14)0.0497 (5)
H22A0.5276−0.13310.24680.060*
C230.50237 (17)0.00110 (16)0.13110 (14)0.0462 (5)
H23A0.4529−0.02780.09930.055*
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)
H36A0.57230.4959−0.14180.047*
C370.62105 (16)0.64571 (14)−0.21179 (12)0.0380 (4)
H37A0.57590.6583−0.26610.046*
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)
H40A0.80360.7539−0.11820.060*
C410.6379 (2)0.83872 (18)−0.37374 (14)0.0590 (6)
H41A0.65660.9068−0.42020.089*
H41B0.54980.8424−0.36040.089*
H41C0.67150.7769−0.40160.089*
C420.7699 (2)0.90254 (18)−0.28036 (16)0.0651 (6)
H42A0.75830.9659−0.33690.098*
H42B0.85500.8677−0.28300.098*
H42C0.74860.9265−0.22010.098*
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)
H3B−0.00490.78410.37230.037*
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)
H7B0.59170.3326−0.02970.042*
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)

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, °)

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—C3−1.8 (3)N6—C26—C31—C30−178.01 (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—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—N1177.18 (14)C31—C30—C32—N8−177.90 (15)
C3—C4—C5—C10178.31 (14)N8—C32—C33—N91.17 (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—C91.2 (3)C30—C32—C33—C253.8 (2)
C7—C8—C9—C100.6 (2)C24—C25—C33—N9−5.0 (3)
C7—C8—C9—C12−177.95 (16)C26—C25—C33—N9176.56 (15)
C8—C9—C10—N2−2.3 (2)C24—C25—C33—C32174.52 (15)
C12—C9—C10—N2176.43 (15)C26—C25—C33—C32−3.9 (2)
C8—C9—C10—C5178.43 (14)N8—C34—C35—C396.5 (3)
C12—C9—C10—C5−2.9 (2)N9—C34—C35—C39−171.90 (15)
N1—C5—C10—N25.9 (2)N8—C34—C35—C36−172.97 (16)
C4—C5—C10—N2−174.34 (15)N9—C34—C35—C368.6 (2)
N1—C5—C10—C9−174.76 (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—C12−1.8 (2)C36—C37—C38—N10−179.81 (16)
C3—C4—C11—N4−1.1 (3)C36—C37—C38—C400.0 (3)
C5—C4—C11—N4179.86 (16)C36—C35—C39—C40−0.4 (3)
N4—C11—C12—N30.25 (18)C34—C35—C39—C40−179.87 (17)
C4—C11—C12—N3−178.41 (14)C35—C39—C40—C380.5 (3)
N4—C11—C12—C9−177.31 (15)N10—C38—C40—C39179.53 (18)
C4—C11—C12—C94.0 (2)C37—C38—C40—C39−0.3 (3)
C8—C9—C12—C11176.98 (15)C2—C1—N1—C51.2 (3)
C10—C9—C12—C11−1.6 (2)C4—C5—N1—C10.7 (2)
C8—C9—C12—N30.0 (3)C10—C5—N1—C1−179.54 (14)
C10—C9—C12—N3−178.55 (15)C7—C6—N2—C100.0 (3)
N5—C14—C15—C16177.78 (18)C9—C10—N2—C61.9 (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—C120.15 (18)
C15—C16—C17—C182.6 (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—C1611.0 (3)C9—C12—N3—C13177.13 (16)
N3—C13—C17—C16−171.95 (15)N3—C13—N4—C110.00 (18)
N4—C13—C17—C18−167.74 (17)C17—C13—N4—C11177.27 (16)
N3—C13—C17—C189.3 (3)C12—C11—N4—C13−0.15 (18)
C16—C17—C18—C19−2.0 (3)C4—C11—N4—C13178.34 (16)
C13—C17—C18—C19176.88 (18)C15—C14—N5—C21−176.70 (19)
C17—C18—C19—C14−0.2 (3)C19—C14—N5—C212.0 (3)
N5—C14—C19—C18−177.12 (18)C15—C14—N5—C20−0.2 (3)
C15—C14—C19—C181.7 (3)C19—C14—N5—C20178.50 (18)
N6—C22—C23—C241.4 (3)C23—C22—N6—C26−0.8 (3)
C22—C23—C24—C250.0 (3)C25—C26—N6—C22−1.1 (2)
C23—C24—C25—C26−1.8 (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—N6−179.01 (14)C26—C31—N7—C28178.98 (16)
C24—C25—C26—C31−177.51 (14)N9—C34—N8—C320.32 (18)
C33—C25—C26—C311.0 (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—C300.2 (3)C30—C32—N8—C34176.63 (16)
C27—C29—C30—C310.1 (3)N8—C34—N9—C330.40 (18)
C27—C29—C30—C32−176.62 (17)C35—C34—N9—C33179.00 (14)
C29—C30—C31—N7−0.2 (2)C32—C33—N9—C34−0.94 (16)
C32—C30—C31—N7176.68 (15)C25—C33—N9—C34178.63 (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—C424.6 (3)
N6—C26—C31—N73.1 (2)C37—C38—N10—C41−9.3 (3)
C25—C26—C31—N7−176.97 (15)C40—C38—N10—C41170.87 (18)

Hydrogen-bond geometry (Å, °)

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, 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

  • 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.
  • Rigaku/MSC (2000). CrystalClear Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Sun, M., Chen, G., Ling, B.-P. & Liu, Y.-X. (2007). Acta Cryst. E63, o1210–o1211.

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