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Acta Cryst. (2007). E63, o3677    [ doi:10.1107/S1600536807037221 ]

3',6'-Bis(diethylamino)-2-propylspiro[isoindoline-1,9'-xanthen]-3-one

L.-Z. Zhang, X.-J. Peng, S. Gao and X.-Q. Chen

Abstract top

In the crystal structure of the title compound, C31H37N3O2, the dihedral angle between the planes of the xanthene ring system and the spirolactam ring is 90.3°.

Comment top

Rhodamine dyes are widely used as fluorescent labels (De Silva et al., 1997) but only a few of such compounds were characterized by single-crystal X-ray diffraction (Kwon et al., 2005). However, for the understanding of their photophysical and photochemical properties, information on their molecular and crystal structures are needed. As part of our ongoing work on rhodamine dyes, we report here the synthesis and crystal structure of the title compound 3',6'-Bis(diethylamino)-2-propyl-spiro[isoindoline-1,9'-[xanthen]-3-one (I).

As similar compounds the main skeleton of the molecule is built up of an xanthene ring which is connected to an spirolactam-ring (Kwon et al., 2005). The lactam moiety is oriented nearly orthogonal to the xanthene moiety. The dihedral angle between the planes of the xanthene ring and the spirolactam-ring amount to 90.3°.

Related literature top

For related literature, see: De Silva et al. (1997); Kwon et al. (2005).

Experimental top

Rhodamine B(1 g, 2.26 mmol) and 1-aminopropane (0.186 ml, 2.26 mmol) were refluxed in 20 ml of methanol for about 3 h until the color changes into light yellow. The crude product were purified by column chromatography (eluation with MeOH/CH2Cl2 = 100:1, v/v). After removal of the solvent in vacuum the solid were dried in vacuum to afford the title compound in 53% yield. Single crystals suitable for X-ray measurements were obtained from a hexane/dichloromethane (1:1, v/v) solution by slow evaporation of the solvent at room temperature.

Refinement top

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

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SMART (Bruker, 1997); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. Crystal structure of compound I, with labelling and displacement ellipsoids drawn at the 30% probability level.
3',6'-Bis(diethylamino)-2-propylspiro[isoindoline-1,9'-xanthen]-3-one top
Crystal data top
C31H37N3O2Z = 2
Mr = 483.64F000 = 520
Triclinic, P1Dx = 1.186 Mg m−3
Hall symbol: -P 1Melting point: 482 K
a = 11.1697 (4) ÅMo Kα radiation
λ = 0.71073 Å
b = 11.8605 (4) ÅCell parameters from 2231 reflections
c = 12.4512 (4) Åθ = 3.5–22.9º
α = 82.838 (3)ºµ = 0.07 mm−1
β = 64.605 (2)ºT = 273 (2) K
γ = 65.588 (2)ºBlock, white
V = 1354.13 (8) Å30.55 × 0.40 × 0.20 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer		4699 independent reflections
Radiation source: fine-focus sealed tube2963 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.027
T = 273(2) Kθmax = 25.0º
φ and ω scansθmin = 2.7º
Absorption correction: multi-scan
(SADABS; Bruker, 1997)		h = −13→13
Tmin = 0.960, Tmax = 0.985k = −13→14
9526 measured reflectionsl = −14→14
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full  w = 1/[σ2(Fo2) + (0.1086P)2 + 0.0965P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.061(Δ/σ)max < 0.001
wR(F2) = 0.201Δρmax = 0.32 e Å−3
S = 1.07Δρmin = −0.24 e Å−3
4699 reflectionsExtinction correction: none
330 parameters
Crystal data top
C31H37N3O2γ = 65.588 (2)º
Mr = 483.64V = 1354.13 (8) Å3
Triclinic, P1Z = 2
a = 11.1697 (4) ÅMo Kα
b = 11.8605 (4) ŵ = 0.07 mm−1
c = 12.4512 (4) ÅT = 273 (2) K
α = 82.838 (3)º0.55 × 0.40 × 0.20 mm
β = 64.605 (2)º
Data collection top
Bruker APEXII CCD area-detector
diffractometer		4699 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)		2963 reflections with I > 2σ(I)
Tmin = 0.960, Tmax = 0.985Rint = 0.027
9526 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.061330 parameters
wR(F2) = 0.201H-atom parameters constrained
S = 1.07Δρmax = 0.32 e Å−3
4699 reflectionsΔρmin = −0.24 e Å−3
Special details top

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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O20.6833 (2)0.94710 (14)0.39573 (15)0.0663 (5)
C230.6694 (2)1.1572 (2)0.3635 (2)0.0504 (6)
C120.6414 (2)1.0462 (2)0.2257 (2)0.0510 (6)
C170.6604 (2)0.9467 (2)0.2956 (2)0.0519 (6)
N10.5045 (2)1.27294 (17)0.26636 (17)0.0539 (5)
C160.6599 (3)0.8367 (2)0.2691 (2)0.0578 (6)
H16A0.67420.77130.31820.069*
O10.4211 (2)1.44106 (16)0.16568 (17)0.0752 (6)
C150.6385 (2)0.8222 (2)0.1706 (2)0.0572 (6)
C180.6879 (3)1.0524 (2)0.4273 (2)0.0534 (6)
C140.6199 (3)0.9239 (2)0.0986 (3)0.0647 (7)
H14A0.60690.91810.03090.078*
C110.6423 (2)1.16741 (19)0.2536 (2)0.0507 (6)
C190.7147 (3)1.0421 (2)0.5268 (2)0.0620 (7)
H19A0.72860.96850.56540.074*
C10.7490 (3)1.2028 (2)0.1450 (2)0.0527 (6)
C70.5201 (3)1.3512 (2)0.1766 (2)0.0556 (6)
C130.6208 (3)1.0308 (2)0.1271 (2)0.0619 (7)
H13A0.60691.09650.07820.074*
C220.6769 (3)1.2555 (2)0.4076 (2)0.0638 (7)
H22A0.66431.32840.36780.077*
N30.6333 (2)0.71471 (19)0.1450 (2)0.0701 (6)
C60.6758 (3)1.3061 (2)0.0986 (2)0.0533 (6)
C50.7487 (3)1.3516 (2)−0.0066 (2)0.0653 (7)
H5A0.69871.4194−0.03910.078*
C210.7022 (3)1.2489 (2)0.5072 (3)0.0680 (7)
H21A0.70661.31680.53290.082*
C200.7214 (3)1.1418 (3)0.5705 (2)0.0647 (7)
C20.8976 (3)1.1444 (2)0.0910 (2)0.0655 (7)
H2A0.94731.07550.12280.079*
N20.7448 (3)1.1347 (2)0.6709 (2)0.0883 (8)
C240.6286 (4)0.6961 (3)0.0341 (3)0.0823 (9)
H24A0.55620.77060.02180.099*
H24B0.59780.62900.04170.099*
C260.6551 (3)0.6089 (3)0.2187 (3)0.0798 (9)
H26A0.60900.55930.20960.096*
H26B0.60730.63940.30150.096*
C30.9713 (3)1.1913 (3)−0.0121 (3)0.0756 (8)
H3A1.07181.1540−0.04930.091*
C40.8970 (3)1.2929 (3)−0.0605 (3)0.0726 (8)
H4A0.94841.3218−0.13050.087*
C80.3672 (3)1.2806 (2)0.3566 (3)0.0710 (7)
H8A0.38011.20220.39390.085*
H8B0.30241.29370.31920.085*
C300.7497 (4)1.2395 (3)0.7168 (3)0.0939 (10)
H30A0.72811.23070.80090.113*
H30B0.67411.31510.71010.113*
C270.8098 (4)0.5279 (3)0.1898 (3)0.0949 (10)
H27A0.81560.46600.24700.142*
H27B0.85850.57730.19230.142*
H27C0.85510.48830.11160.142*
C280.7645 (4)1.0192 (4)0.7386 (3)0.1097 (12)
H28A0.74291.03940.81980.132*
H28B0.69830.98480.74120.132*
C310.8902 (4)1.2535 (4)0.6561 (4)0.1210 (14)
H31A0.88221.32620.68990.182*
H31B0.91351.26170.57260.182*
H31C0.96511.18170.66680.182*
C250.7684 (4)0.6666 (3)−0.0731 (3)0.1066 (12)
H25A0.75360.6651−0.14330.160*
H25B0.83740.5869−0.06720.160*
H25C0.80440.7287−0.07790.160*
C290.9134 (5)0.9280 (5)0.6809 (4)0.1498 (18)
H29A0.92640.85580.72620.225*
H29B0.97870.96320.67650.225*
H29C0.93290.90510.60190.225*
C90.2953 (4)1.3869 (4)0.4548 (3)0.1138 (13)
H9A0.35511.37050.49770.137*
H9B0.28871.46490.41770.137*
C100.1492 (5)1.3971 (5)0.5393 (4)0.1599 (19)
H10A0.10251.46930.59260.240*
H10B0.15691.32450.58420.240*
H10C0.09341.40410.49590.240*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.1059 (14)0.0485 (10)0.0647 (11)−0.0381 (9)−0.0486 (10)0.0116 (8)
C230.0564 (13)0.0408 (13)0.0578 (14)−0.0173 (10)−0.0287 (11)0.0015 (10)
C120.0576 (14)0.0424 (13)0.0595 (14)−0.0185 (11)−0.0316 (12)0.0030 (11)
C170.0585 (14)0.0433 (13)0.0580 (14)−0.0183 (11)−0.0296 (12)0.0018 (11)
N10.0569 (12)0.0427 (11)0.0613 (12)−0.0165 (9)−0.0274 (10)0.0039 (9)
C160.0707 (16)0.0426 (13)0.0670 (16)−0.0241 (12)−0.0337 (13)0.0046 (11)
O10.0851 (13)0.0534 (11)0.0837 (13)−0.0134 (10)−0.0481 (11)0.0118 (9)
C150.0602 (15)0.0449 (14)0.0747 (17)−0.0192 (11)−0.0350 (13)−0.0037 (12)
C180.0625 (14)0.0473 (14)0.0555 (14)−0.0226 (11)−0.0279 (12)0.0016 (11)
C140.0780 (17)0.0527 (15)0.0790 (18)−0.0223 (13)−0.0495 (15)0.0024 (13)
C110.0590 (14)0.0370 (12)0.0604 (14)−0.0165 (10)−0.0315 (12)0.0043 (10)
C190.0761 (17)0.0582 (15)0.0586 (15)−0.0263 (13)−0.0357 (13)0.0066 (12)
C10.0636 (15)0.0440 (13)0.0592 (14)−0.0231 (11)−0.0310 (12)0.0007 (11)
C70.0735 (17)0.0379 (13)0.0632 (15)−0.0183 (12)−0.0387 (13)0.0011 (11)
C130.0783 (17)0.0465 (14)0.0753 (17)−0.0221 (12)−0.0493 (15)0.0105 (12)
C220.0762 (17)0.0500 (15)0.0777 (18)−0.0268 (13)−0.0416 (15)0.0045 (12)
N30.0911 (16)0.0474 (12)0.0889 (16)−0.0300 (11)−0.0488 (13)−0.0014 (11)
C60.0732 (16)0.0413 (13)0.0548 (14)−0.0243 (12)−0.0333 (13)0.0019 (11)
C50.094 (2)0.0524 (15)0.0645 (17)−0.0372 (15)−0.0399 (16)0.0065 (12)
C210.0804 (18)0.0606 (17)0.0773 (18)−0.0289 (14)−0.0416 (15)−0.0074 (14)
C200.0667 (16)0.0704 (18)0.0612 (16)−0.0243 (13)−0.0314 (13)−0.0037 (13)
C20.0672 (17)0.0530 (15)0.0758 (18)−0.0201 (13)−0.0316 (14)−0.0020 (13)
N20.124 (2)0.0885 (18)0.0758 (16)−0.0421 (16)−0.0630 (16)0.0043 (14)
C240.101 (2)0.0649 (18)0.106 (2)−0.0342 (16)−0.059 (2)−0.0102 (16)
C260.093 (2)0.0589 (18)0.101 (2)−0.0389 (16)−0.0416 (18)−0.0053 (15)
C30.0724 (18)0.083 (2)0.0725 (19)−0.0376 (16)−0.0210 (16)−0.0096 (16)
C40.090 (2)0.0753 (19)0.0616 (17)−0.0474 (17)−0.0253 (16)0.0025 (14)
C80.0680 (17)0.0606 (16)0.0827 (19)−0.0221 (13)−0.0356 (15)0.0125 (14)
C300.107 (2)0.114 (3)0.078 (2)−0.047 (2)−0.0444 (19)−0.0174 (18)
C270.104 (3)0.071 (2)0.118 (3)−0.0303 (18)−0.056 (2)−0.0036 (18)
C280.107 (3)0.160 (4)0.075 (2)−0.064 (3)−0.035 (2)−0.013 (2)
C310.121 (3)0.152 (4)0.121 (3)−0.061 (3)−0.065 (3)−0.015 (3)
C250.144 (3)0.107 (3)0.091 (3)−0.065 (2)−0.050 (3)−0.003 (2)
C290.104 (3)0.213 (5)0.132 (4)−0.052 (3)−0.060 (3)0.005 (3)
C90.078 (2)0.163 (4)0.070 (2)−0.037 (2)−0.0146 (18)0.003 (2)
C100.111 (3)0.195 (5)0.124 (4)−0.031 (3)−0.033 (3)0.000 (3)
Geometric parameters (Å, °) top
O2—C171.377 (3)N2—C301.462 (4)
O2—C181.382 (3)N2—C281.503 (5)
C23—C181.379 (3)C24—C251.490 (4)
C23—C221.396 (3)C24—H24A0.9700
C23—C111.504 (3)C24—H24B0.9700
C12—C171.375 (3)C26—C271.490 (4)
C12—C131.389 (3)C26—H26A0.9700
C12—C111.525 (3)C26—H26B0.9700
C17—C161.388 (3)C3—C41.387 (4)
N1—C71.360 (3)C3—H3A0.9300
N1—C81.434 (3)C4—H4A0.9300
N1—C111.486 (3)C8—C91.561 (5)
C16—C151.388 (3)C8—H8A0.9700
C16—H16A0.9300C8—H8B0.9700
O1—C71.223 (3)C30—C311.492 (5)
C15—N31.382 (3)C30—H30A0.9700
C15—C141.409 (3)C30—H30B0.9700
C18—C191.374 (3)C27—H27A0.9600
C14—C131.364 (3)C27—H27B0.9600
C14—H14A0.9300C27—H27C0.9600
C11—C11.522 (3)C28—C291.461 (5)
C19—C201.402 (3)C28—H28A0.9700
C19—H19A0.9300C28—H28B0.9700
C1—C21.377 (3)C31—H31A0.9600
C1—C61.380 (3)C31—H31B0.9600
C7—C61.472 (3)C31—H31C0.9600
C13—H13A0.9300C25—H25A0.9600
C22—C211.372 (3)C25—H25B0.9600
C22—H22A0.9300C25—H25C0.9600
N3—C241.451 (4)C29—H29A0.9600
N3—C261.459 (4)C29—H29B0.9600
C6—C51.393 (3)C29—H29C0.9600
C5—C41.374 (4)C9—C101.476 (5)
C5—H5A0.9300C9—H9A0.9700
C21—C201.398 (4)C9—H9B0.9700
C21—H21A0.9300C10—H10A0.9600
C20—N21.368 (3)C10—H10B0.9600
C2—C31.389 (4)C10—H10C0.9600
C2—H2A0.9300
C17—O2—C18118.45 (18)N3—C24—H24B108.6
C18—C23—C22115.6 (2)C25—C24—H24B108.6
C18—C23—C11123.18 (19)H24A—C24—H24B107.5
C22—C23—C11121.2 (2)N3—C26—C27114.2 (3)
C17—C12—C13116.2 (2)N3—C26—H26A108.7
C17—C12—C11122.7 (2)C27—C26—H26A108.7
C13—C12—C11121.2 (2)N3—C26—H26B108.7
C12—C17—O2123.11 (19)C27—C26—H26B108.7
C12—C17—C16122.1 (2)H26A—C26—H26B107.6
O2—C17—C16114.7 (2)C2—C3—C4120.9 (3)
C7—N1—C8123.7 (2)C2—C3—H3A119.5
C7—N1—C11113.66 (19)C4—C3—H3A119.5
C8—N1—C11122.12 (19)C5—C4—C3121.0 (3)
C17—C16—C15121.4 (2)C5—C4—H4A119.5
C17—C16—H16A119.3C3—C4—H4A119.5
C15—C16—H16A119.3N1—C8—C9113.4 (2)
N3—C15—C16122.1 (2)N1—C8—H8A108.9
N3—C15—C14121.4 (2)C9—C8—H8A108.9
C16—C15—C14116.5 (2)N1—C8—H8B108.9
C19—C18—C23123.3 (2)C9—C8—H8B108.9
C19—C18—O2113.8 (2)H8A—C8—H8B107.7
C23—C18—O2122.9 (2)N2—C30—C31115.3 (3)
C13—C14—C15120.7 (2)N2—C30—H30A108.5
C13—C14—H14A119.6C31—C30—H30A108.5
C15—C14—H14A119.6N2—C30—H30B108.5
N1—C11—C23112.03 (17)C31—C30—H30B108.5
N1—C11—C1100.24 (17)H30A—C30—H30B107.5
C23—C11—C1114.03 (18)C26—C27—H27A109.5
N1—C11—C12110.26 (17)C26—C27—H27B109.5
C23—C11—C12109.73 (18)H27A—C27—H27B109.5
C1—C11—C12110.24 (18)C26—C27—H27C109.5
C18—C19—C20120.5 (2)H27A—C27—H27C109.5
C18—C19—H19A119.7H27B—C27—H27C109.5
C20—C19—H19A119.7C29—C28—N2109.8 (3)
C2—C1—C6120.7 (2)C29—C28—H28A109.7
C2—C1—C11129.0 (2)N2—C28—H28A109.7
C6—C1—C11110.2 (2)C29—C28—H28B109.7
O1—C7—N1125.2 (2)N2—C28—H28B109.7
O1—C7—C6128.1 (2)H28A—C28—H28B108.2
N1—C7—C6106.7 (2)C30—C31—H31A109.5
C14—C13—C12123.1 (2)C30—C31—H31B109.5
C14—C13—H13A118.5H31A—C31—H31B109.5
C12—C13—H13A118.5C30—C31—H31C109.5
C21—C22—C23122.6 (2)H31A—C31—H31C109.5
C21—C22—H22A118.7H31B—C31—H31C109.5
C23—C22—H22A118.7C24—C25—H25A109.5
C15—N3—C24120.9 (2)C24—C25—H25B109.5
C15—N3—C26121.1 (2)H25A—C25—H25B109.5
C24—N3—C26117.3 (2)C24—C25—H25C109.5
C1—C6—C5121.4 (2)H25A—C25—H25C109.5
C1—C6—C7108.8 (2)H25B—C25—H25C109.5
C5—C6—C7129.8 (2)C28—C29—H29A109.5
C4—C5—C6117.8 (3)C28—C29—H29B109.5
C4—C5—H5A121.1H29A—C29—H29B109.5
C6—C5—H5A121.1C28—C29—H29C109.5
C22—C21—C20121.0 (2)H29A—C29—H29C109.5
C22—C21—H21A119.5H29B—C29—H29C109.5
C20—C21—H21A119.5C10—C9—C8110.9 (3)
N2—C20—C21121.6 (2)C10—C9—H9A109.5
N2—C20—C19121.6 (3)C8—C9—H9A109.5
C21—C20—C19116.9 (2)C10—C9—H9B109.5
C1—C2—C3118.2 (3)C8—C9—H9B109.5
C1—C2—H2A120.9H9A—C9—H9B108.0
C3—C2—H2A120.9C9—C10—H10A109.5
C20—N2—C30121.3 (3)C9—C10—H10B109.5
C20—N2—C28121.1 (2)H10A—C10—H10B109.5
C30—N2—C28117.6 (3)C9—C10—H10C109.5
N3—C24—C25114.8 (2)H10A—C10—H10C109.5
N3—C24—H24A108.6H10B—C10—H10C109.5
C25—C24—H24A108.6
C13—C12—C17—O2179.4 (2)C8—N1—C7—C6−175.5 (2)
C11—C12—C17—O2−0.8 (4)C11—N1—C7—C6−3.4 (2)
C13—C12—C17—C160.4 (3)C15—C14—C13—C120.9 (4)
C11—C12—C17—C16−179.8 (2)C17—C12—C13—C14−0.5 (4)
C18—O2—C17—C12−0.2 (3)C11—C12—C13—C14179.7 (2)
C18—O2—C17—C16178.9 (2)C18—C23—C22—C210.5 (4)
C12—C17—C16—C15−0.7 (4)C11—C23—C22—C21−179.7 (2)
O2—C17—C16—C15−179.8 (2)C16—C15—N3—C24−172.4 (2)
C17—C16—C15—N3−178.0 (2)C14—C15—N3—C248.6 (4)
C17—C16—C15—C141.1 (4)C16—C15—N3—C26−2.0 (4)
C22—C23—C18—C19−1.1 (4)C14—C15—N3—C26178.9 (2)
C11—C23—C18—C19179.1 (2)C2—C1—C6—C52.7 (3)
C22—C23—C18—O2179.9 (2)C11—C1—C6—C5−175.1 (2)
C11—C23—C18—O20.0 (4)C2—C1—C6—C7−177.88 (19)
C17—O2—C18—C19−178.6 (2)C11—C1—C6—C74.3 (2)
C17—O2—C18—C230.5 (3)O1—C7—C6—C1179.2 (2)
N3—C15—C14—C13178.0 (2)N1—C7—C6—C1−0.6 (2)
C16—C15—C14—C13−1.1 (4)O1—C7—C6—C5−1.5 (4)
C7—N1—C11—C23126.9 (2)N1—C7—C6—C5178.7 (2)
C8—N1—C11—C23−60.9 (3)C1—C6—C5—C4−2.4 (3)
C7—N1—C11—C15.6 (2)C7—C6—C5—C4178.3 (2)
C8—N1—C11—C1177.8 (2)C23—C22—C21—C20−0.2 (4)
C7—N1—C11—C12−110.6 (2)C22—C21—C20—N2−179.2 (2)
C8—N1—C11—C1261.6 (3)C22—C21—C20—C190.5 (4)
C18—C23—C11—N1122.0 (2)C18—C19—C20—N2178.6 (2)
C22—C23—C11—N1−57.9 (3)C18—C19—C20—C21−1.1 (4)
C18—C23—C11—C1−125.1 (2)C6—C1—C2—C3−1.0 (3)
C22—C23—C11—C155.1 (3)C11—C1—C2—C3176.5 (2)
C18—C23—C11—C12−0.8 (3)C21—C20—N2—C300.5 (4)
C22—C23—C11—C12179.3 (2)C19—C20—N2—C30−179.2 (3)
C17—C12—C11—N1−122.7 (2)C21—C20—N2—C28179.7 (3)
C13—C12—C11—N157.2 (3)C19—C20—N2—C280.0 (4)
C17—C12—C11—C231.2 (3)C15—N3—C24—C2574.5 (3)
C13—C12—C11—C23−179.0 (2)C26—N3—C24—C25−96.2 (3)
C17—C12—C11—C1127.6 (2)C15—N3—C26—C27−82.3 (3)
C13—C12—C11—C1−52.6 (3)C24—N3—C26—C2788.4 (3)
C23—C18—C19—C201.5 (4)C1—C2—C3—C4−1.0 (4)
O2—C18—C19—C20−179.4 (2)C6—C5—C4—C30.4 (4)
N1—C11—C1—C2176.6 (2)C2—C3—C4—C51.3 (4)
C23—C11—C1—C256.7 (3)C7—N1—C8—C9−77.3 (3)
C12—C11—C1—C2−67.2 (3)C11—N1—C8—C9111.3 (3)
N1—C11—C1—C6−5.8 (2)C20—N2—C30—C31−81.0 (4)
C23—C11—C1—C6−125.7 (2)C28—N2—C30—C3199.8 (4)
C12—C11—C1—C6110.4 (2)C20—N2—C28—C2981.2 (4)
C8—N1—C7—O14.7 (4)C30—N2—C28—C29−99.6 (3)
C11—N1—C7—O1176.7 (2)N1—C8—C9—C10175.2 (3)
Selected geometric parameters (Å, °) top
O2—C171.377 (3)O1—C71.223 (3)
O2—C181.382 (3)C15—N31.382 (3)
C23—C111.504 (3)C11—C11.522 (3)
C12—C111.525 (3)C20—N21.368 (3)
N1—C111.486 (3)
N1—C11—C23112.03 (17)N1—C11—C12110.26 (17)
N1—C11—C1100.24 (17)C23—C11—C12109.73 (18)
C23—C11—C1114.03 (18)C1—C11—C12110.24 (18)
Acknowledgements top

This work was supported by the National Natural Science Foundation of China (20376010 and 20472012) and the Natural Science Foundation of Liaoning Provence (20062186).

references
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