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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o156.
Published online 2007 December 6. doi:  10.1107/S1600536807062721
PMCID: PMC2915224

2-(4-Methoxy­phen­yl)phenanthro[9,10-d]imidazole methanol solvate

Abstract

The title compound, C22H16N2O·CH4O, is a product of the condensation reaction between phenanthrene­quinone and 4-methoxy­benzadehyde. There are two imidazole mol­ecules and two methanol molecules in the asymmetric unit. The phenanthryl and imidazole rings are almost parallel in both mol­ecules, with inter­planar angles of 6.65 (1) and 5.40 (3)°. The dihedral angles between the imidazole and the attached benzene rings are 5.40 (3) and 6.65 (1)° in the two molecules. Inter­molecular O—H(...)N and N—H(...)O hydrogen bonds stabilize the crystal packing.

Related literature

For an example of fluorescence properties, see: Krebs & Spanggaard (2002 [triangle]). For a related structure, see: Krebs et al. (2001 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o156-scheme1.jpg

Experimental

Crystal data

  • C22H16N2O·CH4O
  • M r = 356.41
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o156-efi1.jpg
  • a = 17.755 (3) Å
  • b = 17.681 (3) Å
  • c = 25.131 (4) Å
  • β = 107.890 (3)°
  • V = 7508 (2) Å3
  • Z = 16
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 298 (2) K
  • 0.47 × 0.34 × 0.16 mm

Data collection

  • Bruker SMART CCD area detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004 [triangle]) T min = 0.963, T max = 0.987
  • 19569 measured reflections
  • 6972 independent reflections
  • 3852 reflections with I > 2σ(I)
  • R int = 0.050

Refinement

  • R[F 2 > 2σ(F 2)] = 0.055
  • wR(F 2) = 0.131
  • S = 0.95
  • 6972 reflections
  • 493 parameters
  • H-atom parameters constrained
  • Δρmax = 0.13 e Å−3
  • Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2001 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807062721/sq2004sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062721/sq2004Isup2.hkl

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

Acknowledgments

The authors acknowledge Dr Jianping Ma of Shandong Normal University for his help in the crystallographic analysis.

supplementary crystallographic information

Comment

The 1H-phenanthro[9,10 - d]imidazole is a promising building block in the field of molecular materials. It has many desirable properties such as good heat stability, ease of introduction into molecules used as chromophores with high extinction coefficient, readily tunable absorption wavelength, and fluorescent properties. For these reasons, the molecule is used as a large planar synthetic building block in supramolecular chemistry (Krebs & Spanggaard, 2002). As part of our studies of phenanthro[9,10 - d]imidazole derivatives, we report here the structure of the title compound (I), a 1:1 solvate with MeOH.

The bond lengths and angles in (I) agree well with those reported for the related compounds (Krebs et al., 2001). There are two molecules in the asymmetric unit. The phenanthryl and imidazole rings in each molecule are almost parallel, with the interplanar angles being 6.65 (1)° and 5.40 (3)°.

There are intermolecular O4—H4A···N4, O3—H3A···N2, N3—H3···O3, and N1—H1···O4 close contacts (Table 2) in the crystal for (I). These contacts and the cross-linking interactions stabilize the crystal packing.

Experimental

A mixture of phenanthrenequinone (4.161 g, 20 mmol), 4-methoxybenzaldehyde (2.723 g, 20 mmol), and ammonium acetate (7.708 g, 100 mmol) in acetic acid (50 ml) was refluxed for 1 h. Upon cooling to room temperature, the precipitate obtained on addition of water was purified by flash column chromatography on silica gel. Single crystals suitable for X-ray diffraction were obtained by recrystallization from methanol solution.

Refinement

All non-hydrogen atoms were refined with anisotropic displacement parameters. Hydrogen atoms attached to anisotropically refined atoms were placed in geometrically idealized positions and included as riding atoms with aromatic C—H = 0.93 Å and Uiso(H) = 1.2*Ueq(C); methyl C—H = 0.97 Å and Uiso(H) = 1.5*Ueq(C); O—H = 0.82 Å and Uiso(H) = 1.2*Ueq(O); N—H = 0.86 Å and Uiso(H) = 1.2*Ueq(N).

Figures

Fig. 1.
The molecular structure of (I) with the atom-numbering scheme and ellipsoids drawn at the 30% probability level. Both independent imidazole and methanol solvate molecules are shown.
Fig. 2.
The packing diagram for (I) viewed along the c axis. Hydrogen bonds are shown as dashed lines.

Crystal data

C22H16N2O·CH4OF000 = 3008
Mr = 356.41Dx = 1.261 Mg m3
Monoclinic, C2/cMelting point: 527 K
Hall symbol: -C 2ycMo Kα radiation λ = 0.71073 Å
a = 17.755 (3) ÅCell parameters from 2357 reflections
b = 17.681 (3) Åθ = 2.3–20.6º
c = 25.131 (4) ŵ = 0.08 mm1
β = 107.890 (3)ºT = 298 (2) K
V = 7508 (2) Å3Plan, colourless
Z = 160.47 × 0.34 × 0.16 mm

Data collection

Bruker SMART CCD area detector diffractometer6972 independent reflections
Radiation source: fine-focus sealed tube3852 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.050
T = 298(2) Kθmax = 25.5º
[var phi] and ω scansθmin = 1.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 2004)h = −20→21
Tmin = 0.963, Tmax = 0.987k = −18→21
19569 measured reflectionsl = −30→30

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H-atom parameters constrained
wR(F2) = 0.131  w = 1/[σ2(Fo2) + (0.0426P)2] where P = (Fo2 + 2Fc2)/3
S = 0.95(Δ/σ)max < 0.001
6972 reflectionsΔρmax = 0.13 e Å3
493 parametersΔρmin = −0.13 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 F2against 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
C10.00685 (14)0.41421 (11)0.03594 (9)0.0457 (6)
C2−0.05442 (14)0.42635 (12)0.06132 (10)0.0488 (6)
C3−0.13452 (14)0.41336 (13)0.03316 (11)0.0612 (7)
H3B−0.14940.3949−0.00330.073*
C4−0.19126 (16)0.42739 (15)0.05849 (12)0.0730 (8)
H4−0.24430.41850.03940.088*
C5−0.16933 (17)0.45483 (15)0.11244 (13)0.0717 (8)
H5−0.20780.46410.12970.086*
C6−0.09215 (16)0.46835 (13)0.14050 (11)0.0637 (7)
H6−0.07890.48680.17690.076*
C7−0.03134 (15)0.45537 (12)0.11639 (10)0.0518 (6)
C80.05131 (15)0.47244 (12)0.14516 (10)0.0521 (6)
C90.07707 (17)0.50153 (15)0.19970 (11)0.0696 (8)
H90.03990.50950.21840.084*
C100.15405 (19)0.51847 (16)0.22634 (12)0.0838 (9)
H100.16870.53690.26280.101*
C110.21063 (18)0.50848 (17)0.19957 (12)0.0917 (10)
H110.26330.52030.21770.110*
C120.18846 (16)0.48101 (15)0.14599 (11)0.0729 (8)
H120.22650.47510.12780.087*
C130.11032 (15)0.46176 (12)0.11817 (10)0.0523 (6)
C140.08366 (13)0.43179 (11)0.06299 (9)0.0451 (6)
C150.07191 (14)0.38688 (12)−0.02125 (10)0.0475 (6)
C160.09225 (14)0.36201 (12)−0.07017 (10)0.0481 (6)
C170.03205 (15)0.34411 (13)−0.11865 (10)0.0591 (7)
H17−0.02030.3476−0.11890.071*
C180.04807 (16)0.32133 (13)−0.16623 (10)0.0641 (7)
H180.00670.3094−0.19810.077*
C190.12526 (17)0.31611 (13)−0.16687 (10)0.0589 (7)
C200.18619 (15)0.33390 (13)−0.11954 (10)0.0597 (7)
H200.23840.3305−0.11970.072*
C210.16935 (15)0.35687 (12)−0.07173 (10)0.0568 (7)
H210.21080.3691−0.04000.068*
C220.21299 (17)0.28221 (18)−0.21888 (12)0.1021 (11)
H22A0.24050.3297−0.21220.153*
H22B0.21100.2637−0.25520.153*
H22C0.24040.2464−0.19090.153*
C230.59455 (13)0.43889 (12)0.05693 (9)0.0468 (6)
C240.58717 (13)0.43623 (13)0.11163 (10)0.0525 (6)
C250.57882 (15)0.36890 (15)0.13888 (11)0.0660 (7)
H250.57610.32290.12040.079*
C260.57471 (17)0.37032 (18)0.19234 (12)0.0803 (9)
H260.56970.32550.21030.096*
C270.57810 (17)0.43864 (19)0.21961 (12)0.0822 (9)
H270.57630.43950.25620.099*
C280.58407 (16)0.50466 (17)0.19342 (11)0.0754 (8)
H280.58450.55010.21220.090*
C290.58955 (14)0.50622 (14)0.13907 (10)0.0554 (6)
C300.59432 (13)0.57775 (14)0.11076 (11)0.0563 (6)
C310.59150 (15)0.64903 (16)0.13541 (12)0.0706 (8)
H310.58850.65150.17170.085*
C320.59311 (17)0.71454 (16)0.10672 (15)0.0826 (9)
H320.59050.76080.12360.099*
C330.59845 (17)0.71294 (16)0.05339 (14)0.0807 (9)
H330.59980.75790.03450.097*
C340.60174 (15)0.64507 (14)0.02809 (12)0.0681 (7)
H340.60510.6442−0.00810.082*
C350.60016 (13)0.57697 (13)0.05601 (10)0.0531 (6)
C360.60142 (13)0.50504 (12)0.03021 (10)0.0470 (6)
C370.60503 (13)0.41509 (13)−0.02666 (9)0.0472 (6)
C380.60895 (13)0.37375 (13)−0.07583 (9)0.0504 (6)
C390.61133 (15)0.29564 (14)−0.07878 (10)0.0606 (7)
H390.61170.2673−0.04750.073*
C400.61311 (15)0.25848 (14)−0.12690 (11)0.0659 (7)
H400.61440.2059−0.12780.079*
C410.61303 (17)0.29935 (17)−0.17316 (11)0.0722 (8)
C420.61049 (19)0.37649 (17)−0.17058 (11)0.0900 (10)
H420.61030.4046−0.20190.108*
C430.60826 (17)0.41370 (15)−0.12323 (11)0.0749 (8)
H430.60630.4663−0.12300.090*
C440.6210 (3)0.1907 (2)−0.22710 (14)0.1336 (16)
H44A0.66850.1726−0.20010.200*
H44B0.62190.1779−0.26400.200*
H44C0.57590.1677−0.22030.200*
C450.3353 (2)0.36715 (17)0.10140 (14)0.1058 (12)
H45A0.38870.38450.11780.159*
H45B0.33580.31910.08370.159*
H45C0.31030.36180.13010.159*
C460.67782 (19)0.20684 (18)0.09661 (14)0.1066 (11)
H46A0.69140.24320.12640.160*
H46B0.72000.20350.08030.160*
H46C0.66980.15830.11110.160*
N10.59680 (11)0.38208 (10)0.02006 (7)0.0503 (5)
H10.59360.33440.02560.060*
N20.60849 (11)0.48982 (10)−0.02171 (8)0.0515 (5)
N30.12500 (11)0.41427 (10)0.02640 (7)0.0496 (5)
H30.17510.41960.03240.060*
N4−0.00083 (11)0.38598 (10)−0.01671 (7)0.0498 (5)
O10.61638 (14)0.26985 (12)−0.22247 (8)0.1066 (8)
O20.13454 (11)0.29238 (10)−0.21638 (7)0.0811 (6)
O30.29293 (9)0.42005 (10)0.06127 (7)0.0671 (5)
H3A0.32390.44440.04970.101*
O40.60764 (11)0.22969 (9)0.05543 (8)0.0670 (5)
H4A0.57730.19360.04670.100*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0442 (16)0.0433 (13)0.0494 (15)−0.0028 (11)0.0143 (13)0.0034 (11)
C20.0448 (16)0.0468 (14)0.0543 (16)−0.0003 (11)0.0144 (13)0.0054 (11)
C30.0467 (17)0.0692 (17)0.0664 (18)0.0000 (13)0.0154 (15)−0.0022 (13)
C40.0459 (18)0.087 (2)0.084 (2)−0.0004 (15)0.0162 (17)−0.0036 (16)
C50.051 (2)0.084 (2)0.087 (2)0.0026 (15)0.0304 (18)−0.0023 (16)
C60.063 (2)0.0697 (18)0.0632 (18)0.0026 (14)0.0262 (17)−0.0007 (13)
C70.0510 (17)0.0503 (14)0.0555 (16)−0.0016 (12)0.0183 (14)0.0050 (11)
C80.0555 (18)0.0530 (15)0.0488 (15)−0.0019 (12)0.0173 (14)0.0027 (11)
C90.063 (2)0.092 (2)0.0567 (18)−0.0030 (16)0.0230 (16)−0.0077 (14)
C100.069 (2)0.118 (3)0.0590 (19)−0.0111 (19)0.0118 (18)−0.0222 (16)
C110.060 (2)0.138 (3)0.073 (2)−0.0167 (18)0.0150 (18)−0.0346 (19)
C120.055 (2)0.102 (2)0.0629 (19)−0.0105 (16)0.0195 (16)−0.0223 (15)
C130.0489 (17)0.0533 (15)0.0523 (16)−0.0058 (12)0.0123 (14)−0.0017 (11)
C140.0455 (16)0.0445 (14)0.0473 (15)−0.0063 (11)0.0170 (13)0.0016 (10)
C150.0456 (16)0.0460 (14)0.0501 (15)−0.0043 (11)0.0138 (13)0.0033 (11)
C160.0473 (16)0.0485 (14)0.0473 (15)−0.0077 (11)0.0128 (13)0.0022 (11)
C170.0495 (17)0.0760 (18)0.0534 (16)−0.0096 (13)0.0184 (14)0.0026 (13)
C180.0570 (19)0.0855 (19)0.0462 (16)−0.0162 (15)0.0105 (14)−0.0049 (13)
C190.066 (2)0.0627 (16)0.0512 (17)−0.0064 (14)0.0231 (16)−0.0037 (12)
C200.0525 (18)0.0690 (17)0.0592 (17)−0.0027 (13)0.0197 (15)−0.0057 (13)
C210.0506 (17)0.0628 (16)0.0551 (16)−0.0064 (12)0.0131 (14)−0.0037 (12)
C220.081 (3)0.154 (3)0.082 (2)0.006 (2)0.041 (2)−0.020 (2)
C230.0355 (14)0.0550 (15)0.0495 (15)−0.0035 (11)0.0124 (12)0.0043 (12)
C240.0398 (15)0.0668 (17)0.0517 (15)−0.0008 (12)0.0153 (13)0.0077 (13)
C250.069 (2)0.0697 (18)0.0633 (18)−0.0016 (14)0.0257 (16)0.0096 (13)
C260.089 (2)0.093 (2)0.065 (2)−0.0011 (17)0.0319 (19)0.0168 (17)
C270.086 (2)0.109 (3)0.0541 (19)−0.0026 (19)0.0253 (18)0.0034 (18)
C280.071 (2)0.096 (2)0.0592 (19)−0.0017 (16)0.0200 (16)−0.0068 (16)
C290.0391 (15)0.0707 (18)0.0556 (16)−0.0012 (12)0.0134 (13)−0.0030 (13)
C300.0380 (15)0.0638 (17)0.0649 (18)−0.0021 (12)0.0126 (13)−0.0049 (13)
C310.0551 (19)0.076 (2)0.081 (2)0.0004 (15)0.0211 (17)−0.0118 (16)
C320.071 (2)0.063 (2)0.115 (3)0.0017 (16)0.029 (2)−0.0114 (18)
C330.075 (2)0.060 (2)0.110 (3)0.0066 (15)0.032 (2)0.0086 (17)
C340.0615 (19)0.0601 (18)0.082 (2)0.0070 (14)0.0211 (16)0.0093 (15)
C350.0343 (14)0.0578 (16)0.0646 (17)0.0017 (12)0.0114 (13)0.0033 (13)
C360.0315 (14)0.0555 (16)0.0537 (16)0.0005 (11)0.0124 (12)0.0065 (12)
C370.0374 (14)0.0547 (16)0.0485 (15)−0.0067 (11)0.0117 (12)0.0088 (12)
C380.0416 (15)0.0579 (16)0.0497 (16)−0.0085 (12)0.0108 (13)0.0066 (12)
C390.0669 (19)0.0655 (18)0.0549 (17)−0.0066 (14)0.0267 (15)0.0082 (13)
C400.075 (2)0.0658 (17)0.0630 (19)−0.0090 (14)0.0296 (16)−0.0002 (14)
C410.086 (2)0.082 (2)0.0515 (18)−0.0163 (17)0.0256 (17)−0.0037 (15)
C420.138 (3)0.083 (2)0.0513 (19)−0.022 (2)0.033 (2)0.0096 (15)
C430.102 (2)0.0657 (18)0.0552 (18)−0.0145 (16)0.0213 (17)0.0077 (14)
C440.224 (5)0.101 (3)0.099 (3)−0.033 (3)0.082 (3)−0.034 (2)
C450.126 (3)0.095 (2)0.109 (3)0.024 (2)0.054 (3)0.039 (2)
C460.070 (2)0.126 (3)0.103 (3)0.009 (2)−0.003 (2)−0.017 (2)
N10.0485 (13)0.0509 (12)0.0520 (13)−0.0066 (10)0.0159 (11)0.0070 (10)
N20.0432 (13)0.0544 (13)0.0557 (13)−0.0025 (9)0.0132 (11)0.0076 (9)
N30.0436 (12)0.0558 (12)0.0510 (12)−0.0090 (9)0.0169 (11)−0.0015 (9)
N40.0463 (13)0.0532 (12)0.0492 (13)−0.0027 (9)0.0135 (11)0.0031 (9)
O10.167 (2)0.1000 (17)0.0643 (14)−0.0238 (15)0.0526 (15)−0.0116 (11)
O20.0743 (15)0.1156 (16)0.0573 (12)−0.0037 (11)0.0261 (11)−0.0177 (10)
O30.0538 (12)0.0723 (12)0.0782 (13)−0.0097 (10)0.0250 (11)0.0134 (9)
O40.0602 (13)0.0616 (11)0.0740 (13)−0.0136 (9)0.0130 (11)0.0048 (9)

Geometric parameters (Å, °)

C1—C141.360 (3)C25—H250.9300
C1—N41.381 (3)C26—C271.381 (4)
C1—C21.436 (3)C26—H260.9300
C2—C31.399 (3)C27—C281.360 (3)
C2—C71.414 (3)C27—H270.9300
C3—C41.370 (3)C28—C291.399 (3)
C3—H3B0.9300C28—H280.9300
C4—C51.379 (3)C29—C301.466 (3)
C4—H40.9300C30—C351.411 (3)
C5—C61.356 (3)C30—C311.412 (3)
C5—H50.9300C31—C321.369 (3)
C6—C71.410 (3)C31—H310.9300
C6—H60.9300C32—C331.373 (4)
C7—C81.454 (3)C32—H320.9300
C8—C91.403 (3)C33—C341.368 (3)
C8—C131.425 (3)C33—H330.9300
C9—C101.358 (4)C34—C351.398 (3)
C9—H90.9300C34—H340.9300
C10—C111.382 (3)C35—C361.431 (3)
C10—H100.9300C36—N21.375 (3)
C11—C121.371 (3)C37—N21.327 (3)
C11—H110.9300C37—N11.358 (2)
C12—C131.391 (3)C37—C381.456 (3)
C12—H120.9300C38—C431.382 (3)
C13—C141.423 (3)C38—C391.384 (3)
C14—N31.377 (2)C39—C401.385 (3)
C15—N41.331 (3)C39—H390.9300
C15—N31.365 (3)C40—C411.368 (3)
C15—C161.452 (3)C40—H400.9300
C16—C211.384 (3)C41—O11.363 (3)
C16—C171.388 (3)C41—C421.367 (3)
C17—C181.372 (3)C42—C431.371 (3)
C17—H170.9300C42—H420.9300
C18—C191.379 (3)C43—H430.9300
C18—H180.9300C44—O11.408 (3)
C19—O21.370 (3)C44—H44A0.9600
C19—C201.376 (3)C44—H44B0.9600
C20—C211.385 (3)C44—H44C0.9600
C20—H200.9300C45—O31.411 (3)
C21—H210.9300C45—H45A0.9600
C22—O21.425 (3)C45—H45B0.9600
C22—H22A0.9600C45—H45C0.9600
C22—H22B0.9600C46—O41.412 (3)
C22—H22C0.9600C46—H46A0.9600
C23—C361.373 (3)C46—H46B0.9600
C23—N11.375 (3)C46—H46C0.9600
C23—C241.421 (3)N1—H10.8600
C24—C251.404 (3)N3—H30.8600
C24—C291.411 (3)O3—H3A0.8200
C25—C261.368 (3)O4—H4A0.8200
C14—C1—N4110.51 (19)C28—C27—C26120.6 (3)
C14—C1—C2121.6 (2)C28—C27—H27119.7
N4—C1—C2127.9 (2)C26—C27—H27119.7
C3—C2—C7119.9 (2)C27—C28—C29121.9 (3)
C3—C2—C1122.8 (2)C27—C28—H28119.0
C7—C2—C1117.2 (2)C29—C28—H28119.0
C4—C3—C2120.9 (2)C28—C29—C24117.3 (2)
C4—C3—H3B119.5C28—C29—C30121.5 (2)
C2—C3—H3B119.5C24—C29—C30121.1 (2)
C3—C4—C5119.7 (3)C35—C30—C31117.4 (2)
C3—C4—H4120.2C35—C30—C29119.8 (2)
C5—C4—H4120.2C31—C30—C29122.8 (2)
C6—C5—C4120.6 (3)C32—C31—C30121.0 (3)
C6—C5—H5119.7C32—C31—H31119.5
C4—C5—H5119.7C30—C31—H31119.5
C5—C6—C7122.2 (3)C31—C32—C33121.0 (3)
C5—C6—H6118.9C31—C32—H32119.5
C7—C6—H6118.9C33—C32—H32119.5
C6—C7—C2116.7 (2)C34—C33—C32119.8 (3)
C6—C7—C8122.8 (2)C34—C33—H33120.1
C2—C7—C8120.4 (2)C32—C33—H33120.1
C9—C8—C13116.6 (2)C33—C34—C35120.8 (3)
C9—C8—C7122.6 (2)C33—C34—H34119.6
C13—C8—C7120.9 (2)C35—C34—H34119.6
C10—C9—C8122.7 (2)C34—C35—C30120.0 (2)
C10—C9—H9118.7C34—C35—C36122.2 (2)
C8—C9—H9118.7C30—C35—C36117.8 (2)
C9—C10—C11120.3 (3)C23—C36—N2110.2 (2)
C9—C10—H10119.9C23—C36—C35121.3 (2)
C11—C10—H10119.9N2—C36—C35128.5 (2)
C12—C11—C10119.4 (3)N2—C37—N1111.16 (19)
C12—C11—H11120.3N2—C37—C38124.52 (19)
C10—C11—H11120.3N1—C37—C38124.3 (2)
C11—C12—C13121.5 (2)C43—C38—C39117.1 (2)
C11—C12—H12119.3C43—C38—C37119.0 (2)
C13—C12—H12119.3C39—C38—C37123.8 (2)
C12—C13—C14124.3 (2)C38—C39—C40121.9 (2)
C12—C13—C8119.6 (2)C38—C39—H39119.0
C14—C13—C8116.1 (2)C40—C39—H39119.0
C1—C14—N3105.9 (2)C41—C40—C39119.8 (2)
C1—C14—C13123.7 (2)C41—C40—H40120.1
N3—C14—C13130.5 (2)C39—C40—H40120.1
N4—C15—N3110.84 (19)O1—C41—C42115.9 (2)
N4—C15—C16124.7 (2)O1—C41—C40125.6 (3)
N3—C15—C16124.5 (2)C42—C41—C40118.6 (2)
C21—C16—C17117.5 (2)C41—C42—C43122.0 (2)
C21—C16—C15123.3 (2)C41—C42—H42119.0
C17—C16—C15119.2 (2)C43—C42—H42119.0
C18—C17—C16121.5 (2)C42—C43—C38120.5 (2)
C18—C17—H17119.3C42—C43—H43119.7
C16—C17—H17119.3C38—C43—H43119.7
C17—C18—C19120.2 (2)O1—C44—H44A109.5
C17—C18—H18119.9O1—C44—H44B109.5
C19—C18—H18119.9H44A—C44—H44B109.5
O2—C19—C20125.0 (2)O1—C44—H44C109.5
O2—C19—C18115.4 (2)H44A—C44—H44C109.5
C20—C19—C18119.7 (2)H44B—C44—H44C109.5
C19—C20—C21119.7 (2)O3—C45—H45A109.5
C19—C20—H20120.2O3—C45—H45B109.5
C21—C20—H20120.2H45A—C45—H45B109.5
C16—C21—C20121.5 (2)O3—C45—H45C109.5
C16—C21—H21119.2H45A—C45—H45C109.5
C20—C21—H21119.2H45B—C45—H45C109.5
O2—C22—H22A109.5O4—C46—H46A109.5
O2—C22—H22B109.5O4—C46—H46B109.5
H22A—C22—H22B109.5H46A—C46—H46B109.5
O2—C22—H22C109.5O4—C46—H46C109.5
H22A—C22—H22C109.5H46A—C46—H46C109.5
H22B—C22—H22C109.5H46B—C46—H46C109.5
C36—C23—N1105.50 (19)C37—N1—C23107.56 (18)
C36—C23—C24123.4 (2)C37—N1—H1126.2
N1—C23—C24131.1 (2)C23—N1—H1126.2
C25—C24—C29119.8 (2)C37—N2—C36105.59 (17)
C25—C24—C23123.7 (2)C15—N3—C14107.44 (18)
C29—C24—C23116.5 (2)C15—N3—H3126.3
C26—C25—C24120.6 (3)C14—N3—H3126.3
C26—C25—H25119.7C15—N4—C1105.36 (19)
C24—C25—H25119.7C41—O1—C44118.4 (2)
C25—C26—C27119.8 (3)C19—O2—C22118.1 (2)
C25—C26—H26120.1C45—O3—H3A109.5
C27—C26—H26120.1C46—O4—H4A109.5
C14—C1—C2—C3175.8 (2)C27—C28—C29—C30178.7 (2)
N4—C1—C2—C3−3.1 (3)C25—C24—C29—C280.6 (4)
C14—C1—C2—C7−1.8 (3)C23—C24—C29—C28−178.7 (2)
N4—C1—C2—C7179.4 (2)C25—C24—C29—C30−177.0 (2)
C7—C2—C3—C4−0.9 (3)C23—C24—C29—C303.8 (3)
C1—C2—C3—C4−178.4 (2)C28—C29—C30—C35179.7 (2)
C2—C3—C4—C50.1 (4)C24—C29—C30—C35−2.8 (3)
C3—C4—C5—C60.3 (4)C28—C29—C30—C31−1.8 (4)
C4—C5—C6—C70.1 (4)C24—C29—C30—C31175.7 (2)
C5—C6—C7—C2−0.8 (3)C35—C30—C31—C321.0 (4)
C5—C6—C7—C8177.5 (2)C29—C30—C31—C32−177.5 (2)
C3—C2—C7—C61.2 (3)C30—C31—C32—C33−0.8 (4)
C1—C2—C7—C6178.88 (19)C31—C32—C33—C340.4 (4)
C3—C2—C7—C8−177.1 (2)C32—C33—C34—C35−0.3 (4)
C1—C2—C7—C80.5 (3)C33—C34—C35—C300.6 (4)
C6—C7—C8—C91.5 (3)C33—C34—C35—C36178.3 (2)
C2—C7—C8—C9179.8 (2)C31—C30—C35—C34−0.9 (3)
C6—C7—C8—C13−177.0 (2)C29—C30—C35—C34177.6 (2)
C2—C7—C8—C131.3 (3)C31—C30—C35—C36−178.8 (2)
C13—C8—C9—C10−0.5 (4)C29—C30—C35—C36−0.2 (3)
C7—C8—C9—C10−179.1 (3)N1—C23—C36—N2−0.5 (2)
C8—C9—C10—C111.1 (5)C24—C23—C36—N2179.3 (2)
C9—C10—C11—C12−0.3 (5)N1—C23—C36—C35179.0 (2)
C10—C11—C12—C13−1.0 (5)C24—C23—C36—C35−1.1 (3)
C11—C12—C13—C14−178.9 (3)C34—C35—C36—C23−175.6 (2)
C11—C12—C13—C81.6 (4)C30—C35—C36—C232.1 (3)
C9—C8—C13—C12−0.8 (3)C34—C35—C36—N23.8 (4)
C7—C8—C13—C12177.8 (2)C30—C35—C36—N2−178.4 (2)
C9—C8—C13—C14179.6 (2)N2—C37—C38—C43−6.9 (3)
C7—C8—C13—C14−1.8 (3)N1—C37—C38—C43172.7 (2)
N4—C1—C14—N30.1 (2)N2—C37—C38—C39174.9 (2)
C2—C1—C14—N3−178.94 (18)N1—C37—C38—C39−5.6 (4)
N4—C1—C14—C13−179.68 (19)C43—C38—C39—C400.1 (4)
C2—C1—C14—C131.3 (3)C37—C38—C39—C40178.4 (2)
C12—C13—C14—C1−179.0 (2)C38—C39—C40—C410.4 (4)
C8—C13—C14—C10.5 (3)C39—C40—C41—O1178.5 (3)
C12—C13—C14—N31.3 (4)C39—C40—C41—C42−0.6 (4)
C8—C13—C14—N3−179.2 (2)O1—C41—C42—C43−179.0 (3)
N4—C15—C16—C21−173.7 (2)C40—C41—C42—C430.2 (5)
N3—C15—C16—C216.2 (3)C41—C42—C43—C380.4 (5)
N4—C15—C16—C178.1 (3)C39—C38—C43—C42−0.5 (4)
N3—C15—C16—C17−172.0 (2)C37—C38—C43—C42−178.9 (3)
C21—C16—C17—C180.7 (3)N2—C37—N1—C230.2 (2)
C15—C16—C17—C18179.1 (2)C38—C37—N1—C23−179.4 (2)
C16—C17—C18—C19−0.4 (4)C36—C23—N1—C370.2 (2)
C17—C18—C19—O2179.6 (2)C24—C23—N1—C37−179.7 (2)
C17—C18—C19—C200.0 (4)N1—C37—N2—C36−0.6 (2)
O2—C19—C20—C21−179.6 (2)C38—C37—N2—C36179.0 (2)
C18—C19—C20—C210.0 (4)C23—C36—N2—C370.7 (2)
C17—C16—C21—C20−0.8 (3)C35—C36—N2—C37−178.8 (2)
C15—C16—C21—C20−179.1 (2)N4—C15—N3—C14−0.1 (2)
C19—C20—C21—C160.4 (3)C16—C15—N3—C14179.96 (19)
C36—C23—C24—C25178.9 (2)C1—C14—N3—C150.0 (2)
N1—C23—C24—C25−1.3 (4)C13—C14—N3—C15179.8 (2)
C36—C23—C24—C29−1.9 (3)N3—C15—N4—C10.2 (2)
N1—C23—C24—C29178.0 (2)C16—C15—N4—C1−179.91 (19)
C29—C24—C25—C26−1.5 (4)C14—C1—N4—C15−0.2 (2)
C23—C24—C25—C26177.7 (2)C2—C1—N4—C15178.8 (2)
C24—C25—C26—C270.6 (4)C42—C41—O1—C44178.5 (3)
C25—C26—C27—C281.2 (5)C40—C41—O1—C44−0.6 (5)
C26—C27—C28—C29−2.1 (4)C20—C19—O2—C222.7 (4)
C27—C28—C29—C241.2 (4)C18—C19—O2—C22−176.9 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O4—H4A···N4i0.821.942.755 (2)173
O3—H3A···N2ii0.821.952.768 (2)175
N3—H3···O30.861.992.840 (3)168
N1—H1···O40.861.982.825 (2)166

Symmetry codes: (i) −x+1/2, −y+1/2, −z; (ii) −x+1, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SQ2004).

References

  • Bruker (2001). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Krebs, F. C., Lindvold, L. R. & Jorgensen, M. (2001). Tetrahedron Lett.62, 6753–6757.
  • Krebs, F. C. & Spanggaard, H. (2002). J. Org. Chem 67, 7185–7192. [PubMed]
  • Sheldrick, G. M. (1997). SHELXS97 and SHELXL97 University of Göttingen, Germany.
  • Sheldrick, G. M. (2001). SHELXTL Version 5.0. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2004). SADABS University of Göttingen, Germany.

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