Literature DB >> 21202873

2-[4-(Dimethyl-amino)phen-yl]imidazo[4,5-f][1,10]phenanthroline sesquihydrate.

Gang-Qiang Yin1.   

Abstract

There are two formula units in the asymmetric unit of the title compound, C(21)H(17)N(5)·1.5H(2)O. The imidazo[4,5-f][1,10]phen-an-throline unit is almost coplanar with the benzene ring, the dihedral angles between them being 8.91 (5) and 4.93 (6)° in the two mol-ecules. The crystal structure is stabilized by a series of hydrogen bonds between the water mol-ecules and the N atoms of the imidazophenanthroline groups.

Entities:  

Year:  2008        PMID： 21202873      PMCID： PMC2961644          DOI： 10.1107/S1600536808016930

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

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

Experimental

Crystal data

C21H17N5·1.5H2O M = 386.42 Triclinic, 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. 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
C21H17N5·1.5(H2O)Z = 4
Mr = 386.42F000 = 772
Triclinic, P1Dx = 1.324 Mg m−3
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 mm−1
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
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
φ 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 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 Å−3
520 parametersΔρmin = −0.21 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
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.
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)*
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)
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)
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)
Table 1

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) ; (ii) ; (iii) ; (iv) .

  1 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290
  1 in total
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1.  2-Phenyl-1H-1,3,7,8-tetra-azacyclo-penta-[l]phenanthrene.

Authors:  Hong-Min Xi
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-09-20

2.  2-(1H-Imidazo[4,5-f][1,10]phenanthrolin-2-yl)phenol monohydrate.

Authors:  Wen-Zhi Zhang; Li Li; Ying-Hui Xiao
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-06-25

3.  3-(1H-Imidazo[4,5-f][1,10]phenanthrolin-2-yl)benzonitrile methanol solvate.

Authors:  Wen-Lan Wang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-12-04
  3 in total

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