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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3011.
Published online 2009 November 7. doi:  10.1107/S160053680904608X
PMCID: PMC2972140

3-Hydr­oxy-3-phenyl­isoindolin-1-one 0.33-hydrate

Abstract

The asymmetric unit of the title compound, C14H11NO2·0.33H2O, contains three 3-hydr­oxy-3-phenyl­isoindolin-1-one (HPIO) mol­ecules and one water mol­ecule. The three independent HPIO mol­ecules differ in the orientations of hydr­oxy and phenyl groups substituted at the 3-position with respect to the planar [r.m.s. deviations of 0.0173, 0.0170 and 0.0102 Å] dihydro­isoindolin-1-one ring system. In the crystal structure, mol­ecules are linked into a three-dimensional network by O—H(...)O, N—H(...)O and C—H(...)O hydrogen bonds.

Related literature

For general background, see: Antoniadis et al. (1994 [triangle]); Tonzola et al. (2003 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For the preparation, see: Imai et al. (1975 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o3011-scheme1.jpg

Experimental

Crystal data

  • C14H11NO2·0.33H2O
  • M r = 231.24
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3011-efi1.jpg
  • a = 11.709 (2) Å
  • b = 12.621 (3) Å
  • c = 14.572 (3) Å
  • α = 67.84 (3)°
  • β = 74.65 (3)°
  • γ = 64.54 (3)°
  • V = 1787.1 (8) Å3
  • Z = 6
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 298 K
  • 0.30 × 0.20 × 0.20 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.944, T max = 0.963
  • 6996 measured reflections
  • 6996 independent reflections
  • 4605 reflections with I > 2σ(I)
  • 3 standard reflections every 200 reflections intensity decay: none

Refinement

  • R[F 2 > 2σ(F 2)] = 0.057
  • wR(F 2) = 0.181
  • S = 1.12
  • 6996 reflections
  • 478 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.25 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1985 [triangle]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 [triangle]); 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/S160053680904608X/ci2953sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904608X/ci2953Isup2.hkl

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

Acknowledgments

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

supplementary crystallographic information

Comment

HPIO is an important intermediate used to synthesize the monomer 2-benzoylbenzenamine, which can be utilized to synthesize organic semiconductors and conjugated polymers (Tonzola et al., 2003), which are of wide current interest for applications in electronic and optoelectronic devices including light-emitting diodes, thin film transistors, and photovoltaic cells (Antoniadis et al., 1994). We report here the crystal structure of the title compound which is of interest to us in the field.

The asymmetric unit of the title compound contains three HPIO molecules and one water molecule (Fig. 1). Bond lengths (Allen et al., 1987) and angles are within normal ranges. In all independent molecules, dihydroisoindolin-1-one ring systems are planar. The five membered ring forms dihedral angles of 2.3 (2) and 81.2 (2) °, respectively, with the fused and substituted benzene rings in molecule A (with N1) [0.6 (2) and 68.1 (2)° in molecule B (with N2) and 1.2 (2) and 75.5 (2)°, respectively, in molecule C (with N3)].

In the crystal structure, molecules are linked via intermolecular O—H···O, N—H···O and C—H···O hydrogen bonds (Table 1 and Fig. 2) forming a three-dimensional network.

Experimental

3-Hydroxy-3-phenylisoindolin-1-one (HPIO) was prepared by the method reported in the literature (Imai et al., 1975). Single crystals of the title compound were obtained by dissolving HPIO (0.5 g, 2.22 mmol) in methanol (50 ml) and evaporating the solvent slowly at room temperature for about 10 d.

Refinement

Water H atoms were located in a difference map and their positional parameters were refined, with Uiso(H) = 1.5Ueq(O). The remaining H atoms were positioned geometrically [O-H = 0.82 Å, N-H = 0.86 Å and C-H = 0.93 Å] and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,O), where x = 1.2 for aromatic H and x = 1.5 for other H.

Figures

Fig. 1.
The asymmetric unit of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level. Hydrogen bonds are shown as dashed lines.
Fig. 2.
A packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

Crystal data

C14H11NO2·0.33H2OZ = 6
Mr = 231.24F(000) = 728
Triclinic, P1Dx = 1.289 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.709 (2) ÅCell parameters from 25 reflections
b = 12.621 (3) Åθ = 10–13°
c = 14.572 (3) ŵ = 0.09 mm1
α = 67.84 (3)°T = 298 K
β = 74.65 (3)°Block, colourless
γ = 64.54 (3)°0.30 × 0.20 × 0.20 mm
V = 1787.1 (8) Å3

Data collection

Enraf–Nonius CAD-4 diffractometer4605 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.0000
graphiteθmax = 26.0°, θmin = 1.5°
ω/2θ scansh = −13→14
Absorption correction: ψ scan (North et al., 1968)k = −14→15
Tmin = 0.944, Tmax = 0.963l = 0→17
6996 measured reflections3 standard reflections every 200 reflections
6996 independent reflections intensity decay: none

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.181H atoms treated by a mixture of independent and constrained refinement
S = 1.12w = 1/[σ2(Fo2) + (0.0652P)2 + 1.1495P] where P = (Fo2 + 2Fc2)/3
6996 reflections(Δ/σ)max = 0.001
478 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = −0.25 e Å3

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
O10.1027 (2)0.2239 (2)0.95488 (15)0.0503 (5)
H1A0.07240.21670.91390.075*
O20.0699 (2)0.61190 (19)0.79620 (16)0.0542 (5)
N10.1280 (2)0.4033 (2)0.83025 (17)0.0439 (6)
H1B0.10480.40630.77780.053*
C10.5483 (4)0.0646 (4)0.7840 (4)0.0899 (13)
H10.62730.01520.75990.108*
C20.5120 (4)0.1896 (4)0.7529 (3)0.0794 (12)
H20.56610.22660.70650.095*
C30.3948 (3)0.2610 (3)0.7906 (3)0.0639 (9)
H30.37080.34620.76890.077*
C40.3124 (3)0.2090 (3)0.8598 (2)0.0434 (7)
C50.3507 (4)0.0836 (3)0.8886 (4)0.0882 (14)
H50.29750.04530.93460.106*
C60.4669 (5)0.0142 (4)0.8503 (5)0.119 (2)
H60.4907−0.07080.87090.143*
C70.1856 (3)0.2888 (2)0.9045 (2)0.0386 (6)
C80.1136 (2)0.5052 (3)0.8493 (2)0.0399 (6)
C90.1633 (3)0.4612 (3)0.9459 (2)0.0407 (6)
C100.1674 (3)0.5279 (3)1.0002 (2)0.0539 (8)
H100.13930.61340.97660.065*
C110.2148 (3)0.4633 (4)1.0911 (2)0.0603 (9)
H110.22050.50531.12910.072*
C120.2535 (3)0.3369 (4)1.1254 (2)0.0591 (9)
H120.28280.29521.18760.071*
C130.2502 (3)0.2704 (3)1.0709 (2)0.0510 (7)
H130.27790.18491.09450.061*
C140.2041 (3)0.3352 (3)0.9794 (2)0.0390 (6)
O30.0019 (2)0.8023 (2)0.18177 (15)0.0557 (6)
H3B−0.04070.77520.23250.083*
O40.1616 (2)0.64274 (19)0.46174 (15)0.0526 (5)
N20.1539 (2)0.6800 (2)0.29605 (17)0.0446 (6)
H2B0.17550.60500.29800.053*
C150.2730 (5)0.8050 (4)−0.0626 (3)0.0816 (12)
H150.24860.8449−0.12650.098*
C160.1838 (3)0.8231 (3)0.0205 (2)0.0622 (9)
H160.09960.87480.01190.075*
C170.2194 (3)0.7649 (3)0.1155 (2)0.0473 (7)
C180.3464 (3)0.6891 (4)0.1264 (3)0.0667 (9)
H180.37210.64990.18980.080*
C190.4351 (4)0.6715 (4)0.0433 (4)0.0873 (13)
H190.51990.62150.05150.105*
C200.3984 (5)0.7271 (5)−0.0495 (3)0.0897 (14)
H200.45760.7130−0.10460.108*
C210.1212 (3)0.7829 (3)0.2061 (2)0.0416 (6)
C220.1074 (3)0.8883 (3)0.2399 (2)0.0423 (6)
C230.0788 (3)1.0112 (3)0.1874 (3)0.0568 (8)
H230.06961.04060.11980.068*
C240.0643 (3)1.0898 (3)0.2394 (3)0.0678 (10)
H240.04301.17360.20620.081*
C250.0807 (4)1.0460 (3)0.3391 (3)0.0719 (11)
H250.07241.10030.37150.086*
C260.1091 (3)0.9229 (3)0.3913 (2)0.0554 (8)
H260.11990.89290.45860.066*
C270.1211 (3)0.8455 (2)0.3396 (2)0.0419 (6)
C280.1476 (3)0.7119 (3)0.3762 (2)0.0402 (6)
O50.2249 (2)0.40894 (18)0.33786 (14)0.0473 (5)
H5B0.16740.38540.34360.071*
O60.1264 (2)0.3143 (2)0.66810 (15)0.0557 (6)
N30.2147 (2)0.3849 (2)0.50830 (16)0.0412 (5)
H3C0.19080.45970.50790.049*
C290.5960 (3)0.3590 (4)0.4472 (3)0.0738 (11)
H290.63420.35530.49730.089*
C300.4778 (3)0.3506 (3)0.4691 (3)0.0600 (9)
H300.43730.34080.53420.072*
C310.4188 (3)0.3566 (3)0.3968 (2)0.0419 (6)
C320.4800 (3)0.3715 (3)0.3006 (2)0.0602 (9)
H320.44110.37710.25010.072*
C330.6010 (4)0.3783 (4)0.2792 (3)0.0781 (12)
H330.64310.38670.21450.094*
C340.6572 (4)0.3728 (4)0.3520 (3)0.0773 (11)
H340.73710.37840.33720.093*
C350.2898 (3)0.3428 (2)0.42214 (19)0.0391 (6)
C360.1860 (3)0.2991 (3)0.5875 (2)0.0432 (7)
C370.2412 (3)0.1844 (3)0.5597 (2)0.0424 (6)
C380.2368 (3)0.0686 (3)0.6142 (3)0.0623 (9)
H380.19580.05320.67910.075*
C390.2958 (4)−0.0228 (3)0.5678 (3)0.0717 (10)
H390.2949−0.10140.60200.086*
C400.3562 (4)0.0020 (3)0.4710 (3)0.0656 (10)
H400.3943−0.06060.44110.079*
C410.3615 (3)0.1166 (3)0.4173 (3)0.0541 (8)
H410.40350.13160.35270.065*
C420.3023 (3)0.2079 (2)0.4630 (2)0.0410 (6)
O1W0.0303 (3)0.3376 (3)0.3690 (2)0.0759 (8)
H1WA−0.008 (5)0.354 (4)0.315 (4)0.114*
H1WB−0.026 (5)0.345 (4)0.420 (4)0.114*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0551 (13)0.0628 (13)0.0497 (12)−0.0363 (11)−0.0012 (10)−0.0211 (10)
O20.0586 (13)0.0456 (12)0.0562 (13)−0.0191 (10)−0.0069 (10)−0.0134 (10)
N10.0532 (14)0.0459 (14)0.0395 (13)−0.0187 (11)−0.0084 (11)−0.0179 (11)
C10.065 (3)0.082 (3)0.106 (3)−0.001 (2)0.003 (2)−0.050 (3)
C20.053 (2)0.099 (3)0.073 (3)−0.027 (2)0.0112 (18)−0.027 (2)
C30.059 (2)0.060 (2)0.067 (2)−0.0218 (17)0.0077 (17)−0.0238 (18)
C40.0428 (16)0.0470 (17)0.0462 (16)−0.0164 (13)−0.0070 (13)−0.0194 (13)
C50.064 (2)0.050 (2)0.126 (4)−0.0151 (18)0.013 (2)−0.024 (2)
C60.082 (3)0.059 (3)0.181 (6)−0.012 (2)0.023 (3)−0.042 (3)
C70.0422 (15)0.0399 (15)0.0364 (14)−0.0182 (12)−0.0042 (12)−0.0113 (12)
C80.0348 (14)0.0382 (16)0.0471 (16)−0.0134 (12)0.0005 (12)−0.0170 (13)
C90.0355 (14)0.0526 (17)0.0434 (15)−0.0222 (13)0.0031 (12)−0.0230 (13)
C100.0531 (18)0.064 (2)0.061 (2)−0.0305 (16)0.0060 (15)−0.0358 (17)
C110.063 (2)0.089 (3)0.054 (2)−0.038 (2)0.0010 (16)−0.0424 (19)
C120.0525 (19)0.092 (3)0.0448 (18)−0.0316 (18)−0.0058 (14)−0.0272 (18)
C130.0563 (18)0.0587 (19)0.0407 (16)−0.0253 (15)−0.0066 (14)−0.0128 (14)
C140.0380 (14)0.0475 (16)0.0380 (15)−0.0189 (12)−0.0006 (11)−0.0189 (13)
O30.0577 (13)0.0825 (16)0.0399 (11)−0.0455 (12)−0.0054 (10)−0.0098 (11)
O40.0713 (14)0.0485 (12)0.0430 (12)−0.0271 (11)−0.0111 (10)−0.0107 (10)
N20.0631 (16)0.0383 (13)0.0404 (13)−0.0248 (12)−0.0098 (11)−0.0110 (10)
C150.106 (3)0.115 (3)0.045 (2)−0.065 (3)0.009 (2)−0.029 (2)
C160.063 (2)0.085 (3)0.0456 (18)−0.0389 (19)−0.0002 (16)−0.0178 (17)
C170.0559 (18)0.0552 (18)0.0485 (17)−0.0347 (15)0.0027 (14)−0.0239 (15)
C180.061 (2)0.082 (3)0.061 (2)−0.0303 (19)0.0005 (17)−0.0250 (19)
C190.064 (2)0.105 (3)0.090 (3)−0.029 (2)0.014 (2)−0.045 (3)
C200.095 (3)0.123 (4)0.074 (3)−0.061 (3)0.032 (3)−0.059 (3)
C210.0470 (16)0.0453 (16)0.0397 (15)−0.0251 (13)−0.0078 (12)−0.0094 (12)
C220.0405 (15)0.0444 (16)0.0471 (16)−0.0227 (13)0.0009 (12)−0.0151 (13)
C230.060 (2)0.0446 (18)0.062 (2)−0.0211 (15)−0.0017 (16)−0.0128 (15)
C240.067 (2)0.0382 (18)0.087 (3)−0.0183 (16)0.0015 (19)−0.0162 (18)
C250.097 (3)0.053 (2)0.079 (3)−0.036 (2)0.011 (2)−0.038 (2)
C260.069 (2)0.0528 (19)0.0528 (19)−0.0250 (16)−0.0026 (16)−0.0245 (15)
C270.0459 (16)0.0388 (15)0.0446 (16)−0.0195 (13)0.0010 (12)−0.0162 (13)
C280.0463 (16)0.0435 (16)0.0375 (15)−0.0232 (13)−0.0058 (12)−0.0113 (13)
O50.0585 (13)0.0504 (12)0.0399 (11)−0.0260 (10)−0.0110 (9)−0.0107 (9)
O60.0637 (14)0.0718 (15)0.0409 (12)−0.0392 (12)0.0130 (10)−0.0234 (11)
N30.0503 (14)0.0398 (13)0.0381 (12)−0.0220 (11)0.0020 (10)−0.0156 (10)
C290.057 (2)0.092 (3)0.089 (3)−0.041 (2)−0.014 (2)−0.027 (2)
C300.058 (2)0.083 (2)0.0530 (19)−0.0395 (18)−0.0024 (15)−0.0216 (18)
C310.0401 (15)0.0452 (16)0.0445 (16)−0.0196 (13)−0.0003 (12)−0.0166 (13)
C320.057 (2)0.074 (2)0.0505 (19)−0.0325 (18)0.0054 (15)−0.0175 (17)
C330.062 (2)0.087 (3)0.074 (3)−0.039 (2)0.022 (2)−0.018 (2)
C340.054 (2)0.077 (3)0.105 (3)−0.039 (2)0.000 (2)−0.020 (2)
C350.0430 (15)0.0429 (15)0.0358 (14)−0.0189 (12)0.0002 (12)−0.0165 (12)
C360.0468 (16)0.0550 (18)0.0392 (16)−0.0299 (14)−0.0009 (13)−0.0161 (14)
C370.0446 (16)0.0419 (15)0.0419 (16)−0.0193 (13)−0.0077 (12)−0.0085 (13)
C380.074 (2)0.052 (2)0.061 (2)−0.0341 (18)−0.0042 (17)−0.0071 (16)
C390.087 (3)0.0427 (19)0.089 (3)−0.0301 (19)−0.016 (2)−0.0133 (19)
C400.073 (2)0.0432 (19)0.087 (3)−0.0134 (17)−0.024 (2)−0.0270 (18)
C410.0511 (18)0.0538 (19)0.063 (2)−0.0159 (15)−0.0050 (15)−0.0287 (16)
C420.0461 (16)0.0389 (15)0.0450 (16)−0.0199 (13)−0.0083 (13)−0.0133 (13)
O1W0.0722 (18)0.119 (2)0.0572 (16)−0.0538 (17)−0.0077 (12)−0.0265 (16)

Geometric parameters (Å, °)

O1—C71.415 (3)C19—H190.93
O1—H1A0.82C20—H200.93
O2—C81.227 (3)C21—C221.518 (4)
N1—C81.348 (3)C22—C271.374 (4)
N1—C71.443 (3)C22—C231.377 (4)
N1—H1B0.86C23—C241.393 (5)
C1—C61.347 (6)C23—H230.93
C1—C21.364 (6)C24—C251.379 (5)
C1—H10.93C24—H240.93
C2—C31.382 (5)C25—C261.379 (5)
C2—H20.93C25—H250.93
C3—C41.381 (4)C26—C271.386 (4)
C3—H30.93C26—H260.93
C4—C51.368 (5)C27—C281.479 (4)
C4—C71.531 (4)O5—C351.399 (3)
C5—C61.368 (6)O5—H5B0.82
C5—H50.93O6—C361.235 (3)
C6—H60.93N3—C361.335 (3)
C7—C141.516 (4)N3—C351.466 (3)
C8—C91.481 (4)N3—H3C0.86
C9—C141.370 (4)C29—C341.367 (6)
C9—C101.377 (4)C29—C301.376 (5)
C10—C111.383 (5)C29—H290.93
C10—H100.93C30—C311.369 (4)
C11—C121.378 (5)C30—H300.93
C11—H110.93C31—C321.379 (4)
C12—C131.373 (4)C31—C351.527 (4)
C12—H120.93C32—C331.401 (5)
C13—C141.384 (4)C32—H320.93
C13—H130.93C33—C341.356 (6)
O3—C211.429 (3)C33—H330.93
O3—H3B0.82C34—H340.93
O4—C281.227 (3)C35—C421.530 (4)
N2—C281.347 (3)C36—C371.476 (4)
N2—C211.451 (4)C37—C421.385 (4)
N2—H2B0.86C37—C381.391 (4)
C15—C201.387 (6)C38—C391.385 (5)
C15—C161.395 (5)C38—H380.93
C15—H150.93C39—C401.385 (5)
C16—C171.380 (4)C39—H390.93
C16—H160.93C40—C411.381 (5)
C17—C181.392 (5)C40—H400.93
C17—C211.521 (4)C41—C421.379 (4)
C18—C191.390 (5)C41—H410.93
C18—H180.93O1W—H1WA0.92 (5)
C19—C201.357 (6)O1W—H1WB0.86 (5)
C7—O1—H1A109.5O3—C21—C17107.3 (2)
C8—N1—C7114.9 (2)N2—C21—C17113.4 (2)
C8—N1—H1B122.6C22—C21—C17114.7 (2)
C7—N1—H1B122.6C27—C22—C23121.0 (3)
C6—C1—C2118.5 (4)C27—C22—C21109.3 (2)
C6—C1—H1120.8C23—C22—C21129.7 (3)
C2—C1—H1120.8C22—C23—C24117.4 (3)
C1—C2—C3119.8 (4)C22—C23—H23121.3
C1—C2—H2120.1C24—C23—H23121.3
C3—C2—H2120.1C25—C24—C23121.4 (3)
C4—C3—C2121.6 (3)C25—C24—H24119.3
C4—C3—H3119.2C23—C24—H24119.3
C2—C3—H3119.2C26—C25—C24120.9 (3)
C5—C4—C3117.3 (3)C26—C25—H25119.5
C5—C4—C7121.7 (3)C24—C25—H25119.5
C3—C4—C7121.0 (3)C25—C26—C27117.4 (3)
C4—C5—C6120.4 (4)C25—C26—H26121.3
C4—C5—H5119.8C27—C26—H26121.3
C6—C5—H5119.8C22—C27—C26121.8 (3)
C1—C6—C5122.5 (4)C22—C27—C28108.8 (2)
C1—C6—H6118.8C26—C27—C28129.3 (3)
C5—C6—H6118.8O4—C28—N2126.4 (3)
O1—C7—N1113.3 (2)O4—C28—C27127.7 (3)
O1—C7—C14106.9 (2)N2—C28—C27106.0 (2)
N1—C7—C14101.0 (2)C35—O5—H5B109.5
O1—C7—C4112.2 (2)C36—N3—C35115.4 (2)
N1—C7—C4110.9 (2)C36—N3—H3C122.3
C14—C7—C4111.9 (2)C35—N3—H3C122.3
O2—C8—N1126.5 (3)C34—C29—C30120.1 (4)
O2—C8—C9127.7 (3)C34—C29—H29120.0
N1—C8—C9105.8 (2)C30—C29—H29120.0
C14—C9—C10122.1 (3)C31—C30—C29121.3 (3)
C14—C9—C8108.5 (2)C31—C30—H30119.4
C10—C9—C8129.4 (3)C29—C30—H30119.4
C9—C10—C11117.6 (3)C30—C31—C32118.7 (3)
C9—C10—H10121.2C30—C31—C35121.1 (3)
C11—C10—H10121.2C32—C31—C35120.2 (3)
C12—C11—C10120.2 (3)C31—C32—C33119.7 (3)
C12—C11—H11119.9C31—C32—H32120.1
C10—C11—H11119.9C33—C32—H32120.1
C13—C12—C11122.1 (3)C34—C33—C32120.5 (4)
C13—C12—H12118.9C34—C33—H33119.8
C11—C12—H12118.9C32—C33—H33119.8
C12—C13—C14117.5 (3)C33—C34—C29119.8 (3)
C12—C13—H13121.2C33—C34—H34120.1
C14—C13—H13121.2C29—C34—H34120.1
C9—C14—C13120.5 (3)O5—C35—N3111.1 (2)
C9—C14—C7109.8 (2)O5—C35—C31108.5 (2)
C13—C14—C7129.8 (3)N3—C35—C31111.6 (2)
C21—O3—H3B109.5O5—C35—C42113.3 (2)
C28—N2—C21114.4 (2)N3—C35—C4299.9 (2)
C28—N2—H2B122.8C31—C35—C42112.3 (2)
C21—N2—H2B122.8O6—C36—N3125.8 (3)
C20—C15—C16119.6 (4)O6—C36—C37127.7 (3)
C20—C15—H15120.2N3—C36—C37106.5 (2)
C16—C15—H15120.2C42—C37—C38121.7 (3)
C17—C16—C15120.6 (4)C42—C37—C36108.4 (2)
C17—C16—H16119.7C38—C37—C36129.9 (3)
C15—C16—H16119.7C39—C38—C37117.4 (3)
C16—C17—C18118.6 (3)C39—C38—H38121.3
C16—C17—C21120.4 (3)C37—C38—H38121.3
C18—C17—C21121.0 (3)C38—C39—C40120.5 (3)
C19—C18—C17120.7 (4)C38—C39—H39119.8
C19—C18—H18119.6C40—C39—H39119.8
C17—C18—H18119.6C41—C40—C39122.1 (3)
C20—C19—C18120.1 (4)C41—C40—H40118.9
C20—C19—H19119.9C39—C40—H40118.9
C18—C19—H19119.9C42—C41—C40117.6 (3)
C19—C20—C15120.4 (4)C42—C41—H41121.2
C19—C20—H20119.8C40—C41—H41121.2
C15—C20—H20119.8C41—C42—C37120.8 (3)
O3—C21—N2110.4 (2)C41—C42—C35129.5 (3)
O3—C21—C22109.9 (2)C37—C42—C35109.7 (2)
N2—C21—C22101.1 (2)H1WA—O1W—H1WB110 (4)
C6—C1—C2—C30.8 (7)O3—C21—C22—C23−64.4 (4)
C1—C2—C3—C40.1 (6)N2—C21—C22—C23178.9 (3)
C2—C3—C4—C5−0.8 (5)C17—C21—C22—C2356.5 (4)
C2—C3—C4—C7177.1 (3)C27—C22—C23—C24−0.1 (5)
C3—C4—C5—C60.6 (7)C21—C22—C23—C24176.1 (3)
C7—C4—C5—C6−177.3 (4)C22—C23—C24—C251.5 (5)
C2—C1—C6—C5−1.1 (9)C23—C24—C25—C26−1.6 (6)
C4—C5—C6—C10.3 (9)C24—C25—C26—C270.3 (5)
C8—N1—C7—O1115.3 (3)C23—C22—C27—C26−1.1 (5)
C8—N1—C7—C141.3 (3)C21—C22—C27—C26−178.1 (3)
C8—N1—C7—C4−117.5 (3)C23—C22—C27—C28178.4 (3)
C5—C4—C7—O1−15.9 (4)C21—C22—C27—C281.5 (3)
C3—C4—C7—O1166.2 (3)C25—C26—C27—C221.0 (5)
C5—C4—C7—N1−143.8 (3)C25—C26—C27—C28−178.4 (3)
C3—C4—C7—N138.4 (4)C21—N2—C28—O4174.3 (3)
C5—C4—C7—C14104.3 (4)C21—N2—C28—C27−5.9 (3)
C3—C4—C7—C14−73.6 (4)C22—C27—C28—O4−177.6 (3)
C7—N1—C8—O2178.3 (3)C26—C27—C28—O41.9 (5)
C7—N1—C8—C9−0.7 (3)C22—C27—C28—N22.5 (3)
O2—C8—C9—C14−179.3 (3)C26—C27—C28—N2−178.0 (3)
N1—C8—C9—C14−0.3 (3)C34—C29—C30—C31−0.4 (6)
O2—C8—C9—C103.1 (5)C29—C30—C31—C32−0.2 (5)
N1—C8—C9—C10−178.0 (3)C29—C30—C31—C35177.9 (3)
C14—C9—C10—C110.1 (4)C30—C31—C32—C331.0 (5)
C8—C9—C10—C11177.4 (3)C35—C31—C32—C33−177.0 (3)
C9—C10—C11—C12−1.3 (5)C31—C32—C33—C34−1.4 (6)
C10—C11—C12—C131.8 (5)C32—C33—C34—C290.8 (6)
C11—C12—C13—C14−1.0 (5)C30—C29—C34—C330.1 (6)
C10—C9—C14—C130.7 (4)C36—N3—C35—O5120.6 (3)
C8—C9—C14—C13−177.1 (3)C36—N3—C35—C31−118.1 (3)
C10—C9—C14—C7179.0 (3)C36—N3—C35—C420.8 (3)
C8—C9—C14—C71.2 (3)C30—C31—C35—O5151.3 (3)
C12—C13—C14—C9−0.2 (4)C32—C31—C35—O5−30.6 (4)
C12—C13—C14—C7−178.1 (3)C30—C31—C35—N328.6 (4)
O1—C7—C14—C9−120.2 (2)C32—C31—C35—N3−153.3 (3)
N1—C7—C14—C9−1.4 (3)C30—C31—C35—C42−82.6 (3)
C4—C7—C14—C9116.6 (3)C32—C31—C35—C4295.4 (3)
O1—C7—C14—C1357.9 (4)C35—N3—C36—O6178.2 (3)
N1—C7—C14—C13176.7 (3)C35—N3—C36—C37−0.8 (3)
C4—C7—C14—C13−65.3 (4)O6—C36—C37—C42−178.6 (3)
C20—C15—C16—C170.4 (6)N3—C36—C37—C420.4 (3)
C15—C16—C17—C180.8 (5)O6—C36—C37—C382.3 (5)
C15—C16—C17—C21−178.8 (3)N3—C36—C37—C38−178.7 (3)
C16—C17—C18—C19−0.6 (5)C42—C37—C38—C39−0.2 (5)
C21—C17—C18—C19178.9 (3)C36—C37—C38—C39178.7 (3)
C17—C18—C19—C20−0.8 (6)C37—C38—C39—C40−0.1 (5)
C18—C19—C20—C152.0 (7)C38—C39—C40—C410.7 (6)
C16—C15—C20—C19−1.9 (7)C39—C40—C41—C42−1.0 (5)
C28—N2—C21—O3−109.8 (3)C40—C41—C42—C370.7 (4)
C28—N2—C21—C226.5 (3)C40—C41—C42—C35−178.5 (3)
C28—N2—C21—C17129.8 (3)C38—C37—C42—C41−0.1 (4)
C16—C17—C21—O331.1 (4)C36—C37—C42—C41−179.2 (3)
C18—C17—C21—O3−148.5 (3)C38—C37—C42—C35179.2 (3)
C16—C17—C21—N2153.3 (3)C36—C37—C42—C350.1 (3)
C18—C17—C21—N2−26.3 (4)O5—C35—C42—C4160.6 (4)
C16—C17—C21—C22−91.3 (3)N3—C35—C42—C41178.8 (3)
C18—C17—C21—C2289.2 (3)C31—C35—C42—C41−62.8 (4)
O3—C21—C22—C27112.1 (3)O5—C35—C42—C37−118.7 (3)
N2—C21—C22—C27−4.5 (3)N3—C35—C42—C37−0.5 (3)
C17—C21—C22—C27−126.9 (3)C31—C35—C42—C37117.9 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1W—H1WA···O2i0.92 (6)1.78 (6)2.697 (4)175 (6)
O1W—H1WB···O4i0.86 (6)2.01 (6)2.871 (4)177 (7)
O1—H1A···O3i0.821.962.777 (3)179
O3—H3B···O6i0.821.832.634 (3)166
O5—H5B···O1W0.821.852.668 (5)174
N1—H1B···O60.862.212.981 (3)149
N2—H2B···O50.862.163.003 (3)167
N3—H3C···O40.862.042.873 (3)162
C24—H24···O2ii0.932.443.284 (4)151
C34—H34···O2iii0.932.583.387 (6)146

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2953).

References

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  • Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
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