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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2010 May 29;66(Pt 6):o1504. doi: 10.1107/S1600536810015126

2-[(2,4-Dihydroxy­benzyl­idene)amino]-3′,6′-bis­(ethyl­amino)spiro­[isoindoline-1,9′-xanthen]-3-one

Zhi-Hong Xu a, Yan-Ling Zhang a, Yan-Ru Zhao a, Feng-Ling Yang a,*
PMCID: PMC2979423  PMID: 21579564

Abstract

The title compound, C35H36N4O4, was prepared as a spiro­lactam ring formation of rhodamine B dye for comparison with a ring-opened form. The xanthene ring system is approximately planar. The r.m.s. deviation from planarity is 0.064 (6) Å for the xanthene ring. The dihedral angles formed by the spiro­lactam and 2,4-dihydroxy­benzene rings with the xanthene ring system are 86.6 (9) and 88.0 (9)°, respectively.

Related literature

For the structures of rhodamine derivatives bearing a lactam moiety, see: Deng et al. (2009 ▶); Kwon et al. (2005 ▶); Tian & Peng (2008 ▶); Wu et al. (2007 ▶); Xu et al. (2009 ▶); Zhang et al. (2008 ▶).graphic file with name e-66-o1504-scheme1.jpg

Experimental

Crystal data

  • C35H36N4O4

  • M r = 576.68

  • Monoclinic, Inline graphic

  • a = 9.4461 (4) Å

  • b = 26.6905 (12) Å

  • c = 12.2453 (5) Å

  • β = 104.423 (2)°

  • V = 2990.0 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 296 K

  • 0.25 × 0.23 × 0.21 mm

Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.979, T max = 0.982

  • 15630 measured reflections

  • 5310 independent reflections

  • 2162 reflections with I > 2σ(I)

  • R int = 0.087

Refinement

  • R[F 2 > 2σ(F 2)] = 0.070

  • wR(F 2) = 0.215

  • S = 1.02

  • 5310 reflections

  • 393 parameters

  • H-atom parameters constrained

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; 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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810015126/jh2147sup1.cif

e-66-o1504-sup1.cif (27.5KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015126/jh2147Isup2.hkl

e-66-o1504-Isup2.hkl (265.3KB, hkl)

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

Acknowledgments

The authors thank the Natural Science Foundation of the Education Department of Henan Province (2010B150029) and Science and Technique Foundation of Henan Province (0624290013, 082300420110) for support.

supplementary crystallographic information

Comment

Among many fluorescent compounds, rhodamine dyes are known to have excellent photophysical properties, and they are one of the most widely used fluorophores for labeling and sensing biomolecules. There are a few single-crystal reports about rhodamine derivatives bearing a lactam moiety (Xu et al., 2009; Kwon et al., 2005; Wu et al., 2007; Zhang et al., 2008; Tian et al., 2008; Deng et al., 2009). Detailed information on their molecular and crystal structures is necessary to understand their photophysical and photochemical properties.

In agreement with other reported models , (Xu et al., 2009; Wu et al., 2007; Zhang et al., 2008; Tian et al., 2008;) the main skeleton of the molecule is formed by the xanthene ring and the spirolactam-ring. As shown in Figure 1, The atoms of the xanthene ring or the spirolactam-ring are both nearly planar and are almost perpendicular to each other. The dihedral angle between the xanthene mean planes and the spirolactam ring fragment is 86.6 (9)°. The dihedral angle between the xanthene mean planes and the 2,4-dihydroxybenzene ring is 88.0 (9)°.

Experimental

A portion of rhodamine B hydrazide (0.46 g, 1 mmol) and 2,4-dihydroxybenzaldehyde (0.16 g, 1.2 mmol) were mixed in 20 ml e thanol and three drops HAc was added. The reaction solution was refluxed for 3 hours under N2 atmosphere, the reslulting solution was evaporated to 10 ml and allowed to stand at room temperature overnight. The reddish crystals which appeared next day were filtered and washed by ethanol to give 0.46 g of the title compound in 80% yield. Single crystals suitable for X-ray measurements were obtained from mother liquid by slow evaporation at room temperature.

Refinement

The H atoms attached to C, N and O atoms were placed in geometrically calculated positions (C—H = 0.93–0.97 Å and O—H = 0.82 Å) and refined as riding, with Uiso(H) = 1.2Ueq(C, N) or 1.5Ueq(methyl C, O).

Figures

Fig. 1.

Fig. 1.

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The molecular structure of the title compound, with displacement ellipsoids drawn at 30% probability level.

Crystal data

C35H36N4O4 F(000) = 1224
Mr = 576.68 Dx = 1.281 Mg m−3Dm = 1.281 Mg m−3Dm measured by not measured
Monoclinic, P21/c Mo Kα radiation, λ = 0.71073 Å
a = 9.4461 (4) Å Cell parameters from 922 reflections
b = 26.6905 (12) Å θ = 2.3–17.5°
c = 12.2453 (5) Å µ = 0.09 mm−1
β = 104.423 (2)° T = 296 K
V = 2990.0 (2) Å3 Block, colorless
Z = 4 0.25 × 0.23 × 0.21 mm
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Data collection

Bruker APEXII CCD diffractometer 5310 independent reflections
Radiation source: fine-focus sealed tube 2162 reflections with I > 2σ(I)
graphite Rint = 0.087
φ and ω scans θmax = 25.1°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) h = −11→7
Tmin = 0.979, Tmax = 0.982 k = −31→30
15630 measured reflections l = −14→14
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Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.070 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.215 H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0857P)2] where P = (Fo2 + 2Fc2)/3
5310 reflections (Δ/σ)max < 0.001
393 parameters Δρmax = 0.25 e Å−3
0 restraints Δρmin = −0.22 e Å−3
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Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
C1 0.3223 (7) 0.6153 (3) 0.9041 (5) 0.133 (2)
H1A 0.3370 0.6138 0.8294 0.199*
H1B 0.3921 0.5940 0.9532 0.199*
H1C 0.3348 0.6491 0.9313 0.199*
C2 0.1753 (7) 0.5984 (2) 0.9018 (4) 0.103 (2)
H2A 0.1604 0.5990 0.9774 0.124*
H2B 0.1613 0.5644 0.8736 0.124*
C3 0.0711 (7) 0.6969 (3) 0.9716 (6) 0.157 (3)
H3A 0.0060 0.7223 0.9861 0.236*
H3B 0.1598 0.7123 0.9635 0.236*
H3C 0.0932 0.6737 1.0335 0.236*
C4 0.0080 (7) 0.6728 (3) 0.8778 (5) 0.142 (3)
H4A −0.0179 0.6983 0.8199 0.170*
H4B −0.0835 0.6601 0.8892 0.170*
C5 0.0391 (5) 0.62734 (19) 0.7115 (4) 0.0658 (13)
C6 −0.0518 (5) 0.66052 (17) 0.6381 (4) 0.0682 (14)
H6 −0.0908 0.6879 0.6675 0.082*
C7 −0.0847 (4) 0.65369 (17) 0.5250 (4) 0.0619 (12)
H7 −0.1472 0.6764 0.4792 0.074*
C8 −0.0288 (4) 0.61409 (15) 0.4742 (3) 0.0472 (10)
C9 0.0635 (4) 0.58217 (15) 0.5468 (3) 0.0501 (11)
C10 0.0969 (5) 0.58814 (18) 0.6619 (4) 0.0651 (13)
H10 0.1595 0.5654 0.7076 0.078*
C11 0.1123 (4) 0.53531 (15) 0.3966 (3) 0.0490 (11)
C12 0.1954 (5) 0.49728 (16) 0.3683 (4) 0.0580 (12)
H12 0.2569 0.4789 0.4253 0.070*
C13 0.1896 (4) 0.48581 (17) 0.2564 (4) 0.0562 (11)
C14 0.3593 (6) 0.41531 (19) 0.3137 (4) 0.0833 (16)
H14A 0.3737 0.3835 0.2797 0.100*
H14B 0.3058 0.4088 0.3703 0.100*
C15 0.5050 (6) 0.4366 (2) 0.3703 (5) 0.110 (2)
H15A 0.5603 0.4420 0.3154 0.165*
H15B 0.5563 0.4135 0.4265 0.165*
H15C 0.4920 0.4678 0.4053 0.165*
C16 0.3493 (8) 0.4691 (3) 0.0552 (6) 0.142 (3)
H16A 0.3051 0.5018 0.0458 0.213*
H16B 0.3526 0.4560 −0.0172 0.213*
H16C 0.4468 0.4716 0.1023 0.213*
C17 0.2632 (7) 0.4358 (2) 0.1076 (5) 0.1038 (19)
H17A 0.2971 0.4017 0.1033 0.125*
H17B 0.1619 0.4373 0.0650 0.125*
C18 0.0957 (5) 0.51575 (18) 0.1741 (4) 0.0656 (13)
H18 0.0884 0.5099 0.0980 0.079*
C19 0.0150 (5) 0.55344 (17) 0.2056 (4) 0.0637 (13)
H19 −0.0455 0.5726 0.1496 0.076*
C20 0.0197 (4) 0.56410 (15) 0.3172 (3) 0.0471 (10)
C21 −0.0665 (4) 0.60681 (15) 0.3484 (3) 0.0477 (10)
C22 −0.2316 (4) 0.60356 (16) 0.2994 (3) 0.0493 (10)
C23 −0.3254 (5) 0.56787 (17) 0.3198 (3) 0.0613 (12)
H23 −0.2916 0.5398 0.3635 0.074*
C24 −0.4729 (5) 0.57535 (19) 0.2726 (4) 0.0709 (14)
H24 −0.5396 0.5519 0.2859 0.085*
C25 −0.5239 (5) 0.6164 (2) 0.2065 (4) 0.0705 (14)
H25 −0.6240 0.6206 0.1777 0.085*
C26 −0.4286 (5) 0.65122 (17) 0.1826 (4) 0.0640 (13)
H26 −0.4621 0.6785 0.1359 0.077*
C27 −0.2806 (4) 0.64420 (15) 0.2306 (3) 0.0489 (11)
C28 −0.1560 (4) 0.67624 (17) 0.2241 (4) 0.0535 (11)
C29 0.1563 (5) 0.70297 (18) 0.2756 (4) 0.0663 (13)
H29 0.0997 0.7142 0.2066 0.080*
C30 0.3057 (5) 0.72331 (17) 0.3196 (4) 0.0587 (12)
C31 0.3612 (6) 0.75637 (19) 0.2560 (4) 0.0783 (15)
H31 0.3067 0.7650 0.1842 0.094*
C32 0.4987 (6) 0.7771 (2) 0.2981 (5) 0.0872 (17)
H32 0.5375 0.7990 0.2541 0.105*
C33 0.5776 (5) 0.7650 (2) 0.4060 (5) 0.0733 (14)
C34 0.5267 (5) 0.73148 (19) 0.4713 (4) 0.0706 (14)
H34 0.5822 0.7228 0.5427 0.085*
C35 0.3870 (5) 0.71047 (17) 0.4268 (4) 0.0649 (13)
N1 0.0690 (5) 0.63236 (18) 0.8272 (4) 0.0940 (15)
N2 0.2709 (4) 0.44784 (15) 0.2266 (3) 0.0749 (12)
N3 −0.0361 (3) 0.65359 (12) 0.2909 (3) 0.0519 (9)
N4 0.1058 (4) 0.67119 (13) 0.3293 (3) 0.0587 (10)
O1 −0.1568 (3) 0.71531 (11) 0.1705 (3) 0.0705 (9)
O2 0.7101 (4) 0.78780 (16) 0.4427 (3) 0.1002 (13)
H2 0.7411 0.7832 0.5106 0.150*
O3 0.3414 (4) 0.67909 (15) 0.4958 (3) 0.0928 (12)
H3 0.2595 0.6687 0.4647 0.139*
O4 0.1295 (3) 0.54163 (11) 0.5103 (2) 0.0666 (9)
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
C1 0.120 (6) 0.175 (7) 0.096 (5) 0.019 (5) 0.013 (4) −0.032 (5)
C2 0.098 (5) 0.142 (6) 0.069 (4) −0.001 (4) 0.022 (4) −0.030 (4)
C3 0.114 (6) 0.197 (8) 0.153 (7) 0.006 (5) 0.019 (5) −0.095 (6)
C4 0.121 (5) 0.196 (8) 0.091 (5) 0.065 (5) −0.009 (4) −0.077 (5)
C5 0.049 (3) 0.086 (4) 0.056 (3) 0.009 (3) 0.000 (2) −0.021 (3)
C6 0.054 (3) 0.072 (4) 0.074 (3) 0.012 (2) 0.006 (3) −0.022 (3)
C7 0.055 (3) 0.058 (3) 0.064 (3) 0.013 (2) −0.003 (2) 0.001 (2)
C8 0.038 (2) 0.048 (3) 0.050 (3) −0.0026 (19) 0.001 (2) 0.000 (2)
C9 0.044 (3) 0.050 (3) 0.051 (3) 0.010 (2) 0.002 (2) −0.004 (2)
C10 0.060 (3) 0.079 (4) 0.048 (3) 0.016 (2) −0.002 (2) −0.006 (3)
C11 0.055 (3) 0.050 (3) 0.038 (3) 0.001 (2) 0.003 (2) 0.002 (2)
C12 0.059 (3) 0.060 (3) 0.049 (3) 0.008 (2) 0.002 (2) 0.004 (2)
C13 0.051 (3) 0.058 (3) 0.057 (3) 0.001 (2) 0.009 (2) −0.002 (2)
C14 0.096 (4) 0.068 (4) 0.090 (4) 0.023 (3) 0.032 (3) −0.011 (3)
C15 0.078 (4) 0.108 (5) 0.139 (5) 0.017 (4) 0.018 (4) 0.001 (4)
C16 0.118 (6) 0.199 (8) 0.121 (6) 0.016 (5) 0.053 (5) 0.015 (5)
C17 0.114 (5) 0.110 (5) 0.093 (5) 0.028 (4) 0.037 (4) −0.003 (4)
C18 0.068 (3) 0.080 (4) 0.045 (3) 0.013 (3) 0.008 (2) 0.000 (2)
C19 0.063 (3) 0.070 (3) 0.051 (3) 0.015 (2) 0.001 (2) 0.010 (2)
C20 0.045 (3) 0.051 (3) 0.043 (2) 0.000 (2) 0.006 (2) 0.006 (2)
C21 0.037 (2) 0.049 (3) 0.051 (3) −0.0030 (19) 0.0008 (19) 0.004 (2)
C22 0.043 (3) 0.051 (3) 0.048 (2) −0.006 (2) 0.000 (2) −0.003 (2)
C23 0.047 (3) 0.068 (3) 0.062 (3) −0.007 (2) 0.000 (2) 0.009 (2)
C24 0.054 (3) 0.078 (4) 0.075 (3) −0.017 (2) 0.003 (3) 0.005 (3)
C25 0.040 (3) 0.087 (4) 0.076 (3) −0.007 (3) −0.003 (2) 0.006 (3)
C26 0.048 (3) 0.066 (3) 0.071 (3) 0.006 (2) 0.002 (2) 0.010 (3)
C27 0.039 (3) 0.049 (3) 0.052 (3) −0.001 (2) 0.000 (2) 0.006 (2)
C28 0.051 (3) 0.051 (3) 0.055 (3) 0.003 (2) 0.006 (2) 0.004 (2)
C29 0.061 (3) 0.068 (4) 0.063 (3) 0.003 (3) 0.002 (3) −0.003 (3)
C30 0.058 (3) 0.062 (3) 0.053 (3) −0.003 (2) 0.007 (2) −0.001 (2)
C31 0.087 (4) 0.085 (4) 0.066 (3) −0.012 (3) 0.026 (3) 0.009 (3)
C32 0.079 (4) 0.102 (5) 0.081 (4) −0.039 (3) 0.021 (3) −0.010 (3)
C33 0.052 (3) 0.092 (4) 0.077 (4) −0.024 (3) 0.018 (3) −0.018 (3)
C34 0.054 (3) 0.084 (4) 0.071 (3) −0.018 (3) 0.012 (3) −0.009 (3)
C35 0.069 (3) 0.055 (3) 0.078 (4) −0.009 (2) 0.032 (3) 0.005 (3)
N1 0.084 (3) 0.123 (4) 0.063 (3) 0.032 (3) −0.004 (2) −0.031 (3)
N2 0.083 (3) 0.080 (3) 0.061 (3) 0.027 (2) 0.016 (2) −0.002 (2)
N3 0.037 (2) 0.051 (2) 0.062 (2) −0.0056 (17) 0.0025 (17) 0.0110 (18)
N4 0.053 (2) 0.050 (2) 0.072 (3) −0.0094 (18) 0.015 (2) 0.010 (2)
O1 0.058 (2) 0.061 (2) 0.084 (2) 0.0002 (15) 0.0007 (16) 0.0266 (18)
O2 0.070 (2) 0.137 (3) 0.092 (3) −0.056 (2) 0.016 (2) −0.017 (3)
O3 0.075 (3) 0.109 (3) 0.081 (2) −0.028 (2) −0.0046 (19) 0.027 (2)
O4 0.078 (2) 0.069 (2) 0.0468 (19) 0.0292 (17) 0.0047 (16) 0.0023 (16)
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Geometric parameters (Å, °)

C1—C2 1.453 (7) C16—H16B 0.9600
C1—H1A 0.9600 C16—H16C 0.9600
C1—H1B 0.9600 C17—N2 1.476 (6)
C1—H1C 0.9600 C17—H17A 0.9700
C2—N1 1.486 (7) C17—H17B 0.9700
C2—H2A 0.9700 C18—C19 1.374 (6)
C2—H2B 0.9700 C18—H18 0.9300
C3—C4 1.323 (7) C19—C20 1.386 (5)
C3—H3A 0.9600 C19—H19 0.9300
C3—H3B 0.9600 C20—C21 1.504 (5)
C3—H3C 0.9600 C21—N3 1.496 (5)
C4—N1 1.434 (6) C21—C22 1.527 (5)
C4—H4A 0.9700 C22—C23 1.366 (5)
C4—H4B 0.9700 C22—C27 1.381 (5)
C5—N1 1.380 (5) C23—C24 1.384 (6)
C5—C10 1.388 (6) C23—H23 0.9300
C5—C6 1.395 (6) C24—C25 1.376 (6)
C6—C7 1.354 (5) C24—H24 0.9300
C6—H6 0.9300 C25—C26 1.376 (6)
C7—C8 1.396 (5) C25—H25 0.9300
C7—H7 0.9300 C26—C27 1.388 (5)
C8—C9 1.375 (5) C26—H26 0.9300
C8—C21 1.504 (5) C27—C28 1.473 (5)
C9—C10 1.375 (5) C28—O1 1.231 (5)
C9—O4 1.377 (4) C28—N3 1.362 (5)
C10—H10 0.9300 C29—N4 1.240 (5)
C11—C20 1.370 (5) C29—C30 1.482 (6)
C11—O4 1.371 (4) C29—H29 0.9300
C11—C12 1.380 (5) C30—C31 1.365 (6)
C12—C13 1.391 (5) C30—C35 1.389 (6)
C12—H12 0.9300 C31—C32 1.388 (6)
C13—N2 1.374 (5) C31—H31 0.9300
C13—C18 1.413 (6) C32—C33 1.385 (7)
C14—N2 1.465 (6) C32—H32 0.9300
C14—C15 1.490 (7) C33—O2 1.363 (5)
C14—H14A 0.9700 C33—C34 1.364 (6)
C14—H14B 0.9700 C34—C35 1.413 (6)
C15—H15A 0.9600 C34—H34 0.9300
C15—H15B 0.9600 C35—O3 1.335 (5)
C15—H15C 0.9600 N3—N4 1.388 (4)
C16—C17 1.458 (7) O2—H2 0.8200
C16—H16A 0.9600 O3—H3 0.8200
C2—C1—H1A 109.5 N2—C17—H17B 108.8
C2—C1—H1B 109.5 H17A—C17—H17B 107.7
H1A—C1—H1B 109.5 C19—C18—C13 120.5 (4)
C2—C1—H1C 109.5 C19—C18—H18 119.8
H1A—C1—H1C 109.5 C13—C18—H18 119.8
H1B—C1—H1C 109.5 C18—C19—C20 122.9 (4)
C1—C2—N1 108.6 (5) C18—C19—H19 118.5
C1—C2—H2A 110.0 C20—C19—H19 118.5
N1—C2—H2A 110.0 C11—C20—C19 116.3 (4)
C1—C2—H2B 110.0 C11—C20—C21 122.3 (4)
N1—C2—H2B 110.0 C19—C20—C21 121.3 (4)
H2A—C2—H2B 108.3 N3—C21—C8 110.5 (3)
C4—C3—H3A 109.5 N3—C21—C20 109.5 (3)
C4—C3—H3B 109.5 C8—C21—C20 110.6 (3)
H3A—C3—H3B 109.5 N3—C21—C22 99.2 (3)
C4—C3—H3C 109.5 C8—C21—C22 111.6 (3)
H3A—C3—H3C 109.5 C20—C21—C22 114.9 (3)
H3B—C3—H3C 109.5 C23—C22—C27 121.7 (4)
C3—C4—N1 126.8 (6) C23—C22—C21 127.8 (4)
C3—C4—H4A 105.6 C27—C22—C21 110.5 (3)
N1—C4—H4A 105.6 C22—C23—C24 117.1 (4)
C3—C4—H4B 105.6 C22—C23—H23 121.5
N1—C4—H4B 105.6 C24—C23—H23 121.5
H4A—C4—H4B 106.1 C25—C24—C23 121.9 (4)
N1—C5—C10 121.3 (4) C25—C24—H24 119.0
N1—C5—C6 122.4 (4) C23—C24—H24 119.0
C10—C5—C6 116.3 (4) C26—C25—C24 120.8 (4)
C7—C6—C5 121.4 (4) C26—C25—H25 119.6
C7—C6—H6 119.3 C24—C25—H25 119.6
C5—C6—H6 119.3 C25—C26—C27 117.5 (4)
C6—C7—C8 122.9 (4) C25—C26—H26 121.2
C6—C7—H7 118.6 C27—C26—H26 121.2
C8—C7—H7 118.6 C22—C27—C26 120.9 (4)
C9—C8—C7 115.5 (4) C22—C27—C28 109.7 (4)
C9—C8—C21 122.2 (4) C26—C27—C28 129.3 (4)
C7—C8—C21 122.4 (4) O1—C28—N3 126.1 (4)
C8—C9—C10 122.5 (4) O1—C28—C27 128.4 (4)
C8—C9—O4 122.8 (4) N3—C28—C27 105.4 (4)
C10—C9—O4 114.6 (4) N4—C29—C30 121.0 (4)
C9—C10—C5 121.4 (4) N4—C29—H29 119.5
C9—C10—H10 119.3 C30—C29—H29 119.5
C5—C10—H10 119.3 C31—C30—C35 119.9 (4)
C20—C11—O4 123.0 (4) C31—C30—C29 119.7 (4)
C20—C11—C12 122.4 (4) C35—C30—C29 120.4 (4)
O4—C11—C12 114.5 (4) C30—C31—C32 120.2 (5)
C11—C12—C13 121.6 (4) C30—C31—H31 119.9
C11—C12—H12 119.2 C32—C31—H31 119.9
C13—C12—H12 119.2 C33—C32—C31 119.6 (5)
N2—C13—C12 122.4 (4) C33—C32—H32 120.2
N2—C13—C18 121.4 (4) C31—C32—H32 120.2
C12—C13—C18 116.2 (4) O2—C33—C34 121.9 (5)
N2—C14—C15 114.0 (5) O2—C33—C32 116.2 (5)
N2—C14—H14A 108.8 C34—C33—C32 121.9 (4)
C15—C14—H14A 108.8 C33—C34—C35 117.8 (4)
N2—C14—H14B 108.8 C33—C34—H34 121.1
C15—C14—H14B 108.8 C35—C34—H34 121.1
H14A—C14—H14B 107.7 O3—C35—C30 124.3 (4)
C14—C15—H15A 109.5 O3—C35—C34 115.0 (4)
C14—C15—H15B 109.5 C30—C35—C34 120.7 (4)
H15A—C15—H15B 109.5 C5—N1—C4 121.0 (5)
C14—C15—H15C 109.5 C5—N1—C2 120.4 (4)
H15A—C15—H15C 109.5 C4—N1—C2 118.4 (4)
H15B—C15—H15C 109.5 C13—N2—C14 119.9 (4)
C17—C16—H16A 109.5 C13—N2—C17 121.9 (4)
C17—C16—H16B 109.5 C14—N2—C17 117.9 (4)
H16A—C16—H16B 109.5 C28—N3—N4 129.9 (3)
C17—C16—H16C 109.5 C28—N3—C21 115.1 (3)
H16A—C16—H16C 109.5 N4—N3—C21 113.9 (3)
H16B—C16—H16C 109.5 C29—N4—N3 121.3 (4)
C16—C17—N2 114.0 (5) C33—O2—H2 109.5
C16—C17—H17A 108.8 C35—O3—H3 109.5
N2—C17—H17A 108.8 C11—O4—C9 118.5 (3)
C16—C17—H17B 108.8
N1—C5—C6—C7 −177.1 (4) C25—C26—C27—C28 −176.9 (4)
C10—C5—C6—C7 1.8 (7) C22—C27—C28—O1 179.4 (4)
C5—C6—C7—C8 −1.2 (7) C26—C27—C28—O1 −3.2 (8)
C6—C7—C8—C9 −0.3 (6) C22—C27—C28—N3 −0.6 (5)
C6—C7—C8—C21 179.8 (4) C26—C27—C28—N3 176.8 (4)
C7—C8—C9—C10 1.1 (6) N4—C29—C30—C31 176.7 (4)
C21—C8—C9—C10 −179.0 (4) N4—C29—C30—C35 −5.8 (7)
C7—C8—C9—O4 −179.2 (4) C35—C30—C31—C32 0.1 (7)
C21—C8—C9—O4 0.7 (6) C29—C30—C31—C32 177.6 (5)
C8—C9—C10—C5 −0.4 (7) C30—C31—C32—C33 −1.6 (8)
O4—C9—C10—C5 179.8 (4) C31—C32—C33—O2 −178.3 (5)
N1—C5—C10—C9 177.9 (4) C31—C32—C33—C34 2.7 (8)
C6—C5—C10—C9 −1.1 (7) O2—C33—C34—C35 178.8 (4)
C20—C11—C12—C13 −0.2 (7) C32—C33—C34—C35 −2.2 (8)
O4—C11—C12—C13 179.5 (4) C31—C30—C35—O3 179.1 (5)
C11—C12—C13—N2 −179.5 (4) C29—C30—C35—O3 1.6 (7)
C11—C12—C13—C18 0.9 (6) C31—C30—C35—C34 0.3 (7)
N2—C13—C18—C19 179.8 (4) C29—C30—C35—C34 −177.1 (4)
C12—C13—C18—C19 −0.7 (7) C33—C34—C35—O3 −178.1 (4)
C13—C18—C19—C20 −0.3 (7) C33—C34—C35—C30 0.7 (7)
O4—C11—C20—C19 179.6 (4) C10—C5—N1—C4 −179.5 (5)
C12—C11—C20—C19 −0.8 (6) C6—C5—N1—C4 −0.6 (8)
O4—C11—C20—C21 2.7 (6) C10—C5—N1—C2 5.7 (7)
C12—C11—C20—C21 −177.6 (4) C6—C5—N1—C2 −175.4 (5)
C18—C19—C20—C11 1.0 (6) C3—C4—N1—C5 −145.1 (8)
C18—C19—C20—C21 177.9 (4) C3—C4—N1—C2 29.7 (12)
C9—C8—C21—N3 −126.4 (4) C1—C2—N1—C5 78.6 (6)
C7—C8—C21—N3 53.5 (5) C1—C2—N1—C4 −96.3 (7)
C9—C8—C21—C20 −5.0 (5) C12—C13—N2—C14 4.7 (7)
C7—C8—C21—C20 174.9 (4) C18—C13—N2—C14 −175.8 (4)
C9—C8—C21—C22 124.3 (4) C12—C13—N2—C17 179.7 (5)
C7—C8—C21—C22 −55.8 (5) C18—C13—N2—C17 −0.8 (7)
C11—C20—C21—N3 125.3 (4) C15—C14—N2—C13 −83.1 (6)
C19—C20—C21—N3 −51.4 (5) C15—C14—N2—C17 101.7 (6)
C11—C20—C21—C8 3.4 (5) C16—C17—N2—C13 79.7 (7)
C19—C20—C21—C8 −173.3 (4) C16—C17—N2—C14 −105.3 (6)
C11—C20—C21—C22 −124.1 (4) O1—C28—N3—N4 11.1 (7)
C19—C20—C21—C22 59.2 (5) C27—C28—N3—N4 −168.9 (4)
N3—C21—C22—C23 179.7 (4) O1—C28—N3—C21 178.8 (4)
C8—C21—C22—C23 −63.9 (6) C27—C28—N3—C21 −1.2 (5)
C20—C21—C22—C23 63.1 (6) C8—C21—N3—C28 −115.0 (4)
N3—C21—C22—C27 −2.5 (4) C20—C21—N3—C28 122.9 (4)
C8—C21—C22—C27 113.9 (4) C22—C21—N3—C28 2.2 (4)
C20—C21—C22—C27 −119.1 (4) C8—C21—N3—N4 54.7 (4)
C27—C22—C23—C24 −2.9 (7) C20—C21—N3—N4 −67.4 (4)
C21—C22—C23—C24 174.6 (4) C22—C21—N3—N4 171.9 (3)
C22—C23—C24—C25 1.0 (7) C30—C29—N4—N3 177.2 (4)
C23—C24—C25—C26 1.6 (8) C28—N3—N4—C29 −27.2 (7)
C24—C25—C26—C27 −2.2 (7) C21—N3—N4—C29 165.0 (4)
C23—C22—C27—C26 2.3 (7) C20—C11—O4—C9 −7.5 (6)
C21—C22—C27—C26 −175.6 (4) C12—C11—O4—C9 172.8 (4)
C23—C22—C27—C28 180.0 (4) C8—C9—O4—C11 5.7 (6)
C21—C22—C27—C28 2.1 (5) C10—C9—O4—C11 −174.5 (4)
C25—C26—C27—C22 0.3 (6)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2147).

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810015126/jh2147sup1.cif

e-66-o1504-sup1.cif (27.5KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015126/jh2147Isup2.hkl

e-66-o1504-Isup2.hkl (265.3KB, hkl)

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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