organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

2-[(E)-2-(Benzyl­­idene­amino)­eth­yl]-3′,6′-bis­­(di­ethyl­amino)­spiro­[isoindoline-1,9′-xanthen]-3-one

aDepartment of Basic Science, Tianjin Agriculturial College, Tianjin Jinjing Road No. 22, Tianjin 300384, People's Republic of China
*Correspondence e-mail: wei-zhen@126.com

(Received 8 April 2011; accepted 27 May 2011; online 18 June 2011)

In the title compound, C37H40N4O2, the xanthene and spiro­lactam rings are almost planar, with r.m.s. deviations from the mean planes of 0.223 (2) and 0.057 (2) Å, respectively, and form a dihedral angle of 85.76 (3)°. The dihedral angle between the xanthene mean plane and the benzene ring is 87.16 (5)°. One of the two ethyl groups of one of the diethyl­amino groups is disordered over two sets of sites [0.76 (1):0.24 (1)].

Related literature

For related structures and background to rhodamine dyes, see: Xu et al. (2010a[Xu, Z., Guo, W., Su, B., Shen, X.-K. & Yang, F. (2010a). Acta Cryst. E66, o1500.],b[Xu, Z.-H., Zhang, Y.-L., Zhao, Y.-R. & Yang, F.-L. (2010b). Acta Cryst. E66, o1504.]); Zhang et al. (2008[Zhang, L.-Z., Peng, X.-J., Gao, S. & Fan, J.-L. (2008). Acta Cryst. E64, o403.]); Tian et al. (2008[Tian, M.-Z. & Peng, X.-J. (2008). Acta Cryst. E64, o1645.]); Kwon et al. (2005[Kwon, J. Y., Jang, Y. J., Kim, K. M., Nam, W. & Yoon, I. (2005). J. Am. Chem. Soc. 127, 10107-10111.]); Wu et al. (2007[Wu, D., Huang, W., Duan, C. Y., Lin, Z. H. & Meng, Q. J. (2007). Inorg. Chem. 46, 1538-1540.]).

[Scheme 1]

Experimental

Crystal data
  • C37H40N4O2

  • Mr = 572.73

  • Triclinic, [P \overline 1]

  • a = 9.842 (2) Å

  • b = 13.151 (3) Å

  • c = 13.552 (3) Å

  • α = 74.43 (3)°

  • β = 81.92 (3)°

  • γ = 69.12 (3)°

  • V = 1576.7 (7) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 293 K

  • 0.26 × 0.22 × 0.20 mm

Data collection
  • Rigaku Saturn diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.981, Tmax = 0.985

  • 17336 measured reflections

  • 6168 independent reflections

  • 4273 reflections with I > 2σ(I)

  • Rint = 0.033

Refinement
  • R[F2 > 2σ(F2)] = 0.057

  • wR(F2) = 0.174

  • S = 1.06

  • 6168 reflections

  • 399 parameters

  • 2 restraints

  • H-atom parameters constrained

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.24 e Å−3

Data collection: CrystalClear (Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

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 on rhodamine derivatives bearing a lactam moiety (Xu et al., 2010a;2010b Kwon et al., 2005; Wu et al., 2007; Zhang et al., 2008; Tian et al., 2008). Detailed information on their molecular and crystal structures is necessary to understand their photophysical and photochemical properties.

In the title compound, C37H20N4O2, the xanthene and spirolactam-rings are almost planar, with r.m.s. deviations from the mean planes of 0.223 (2)Å and 0.057 (2)Å, respectively, and form a dihedral angle of 85.76 (3)°. The dihedral angle between the xanthene mean plane and the benzene ring is 87.16 (5)°. During refinement, one of the two ethyl groups bonded to N4 appeared disordered. The corresponding occupancies refined to final values of 0.76/0.24 (1).

Related literature top

For related structures and background to rhodamine dyes, see: Xu et al. (2010a,b); Zhang et al. (2008); Tian et al. (2008); Kwon et al. (2005); Wu et al. (2007).

Experimental top

N-(rhodamine-6 G)lactam-ethylenediamine (10m mol) was dissolved in 20 ml of ethanol, followed by addition of benzaldehyde(15m mol). The solution was stirred and refluxed for 4 h when white precipitate appeared,the resulting crude product was obtained by filteration. then the product was disolved in ethanol,Single crystals suitable for X-ray measurements were obtained from ethanol by slow evaporation at room temperature.

Refinement top

During refinement, one of the two ethyl groups bonded to N4 appeared disordered. The corresponding occupancies refined to final values of 0.76/0.24 (1), and were kept fixed afterwards. The disordered model was refined using the tools availablein SHELXL97 (Sheldrick, 2008): SADI for restraining distances, EADP to correlate anisotropic thermal parameters for related disordered atoms.

All H atoms were geometrically positioned and treated as riding on their parent atoms, with C—H = 0.93 Å for the aromatic, 0.96 Å for the methyl H atoms and C—H= 0.97 Å for methylene, with Uiso(H)= 1.2 Ueq(C aromatic) or,1.5Ueq(C methyl).

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Only the major part of the ethyl group attached to N4 has been drawn, for clarity.
2-[(E)-2-(Benzylideneamino)ethyl]-3',6'- bis(diethylamino)spiro[isoindoline-1,9'-xanthen]-3-one top
Crystal data top
C37H40N4O2Z = 2
Mr = 572.73F(000) = 612
Triclinic, P1Dx = 1.206 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.842 (2) ÅCell parameters from 3876 reflections
b = 13.151 (3) Åθ = 1.6–29.0°
c = 13.552 (3) ŵ = 0.08 mm1
α = 74.43 (3)°T = 293 K
β = 81.92 (3)°Prism, colourless
γ = 69.12 (3)°0.26 × 0.22 × 0.20 mm
V = 1576.7 (7) Å3
Data collection top
Rigaku Saturn
diffractometer
6168 independent reflections
Radiation source: fine-focus sealed tube4273 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
Detector resolution: 7.31 pixels mm-1θmax = 26.0°, θmin = 1.6°
ω scansh = 1212
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2008)
k = 1616
Tmin = 0.981, Tmax = 0.985l = 1616
17336 measured reflections
Refinement top
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) = 0.174H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.1016P)2]
where P = (Fo2 + 2Fc2)/3
6168 reflections(Δ/σ)max < 0.001
399 parametersΔρmax = 0.29 e Å3
2 restraintsΔρmin = 0.24 e Å3
Crystal data top
C37H40N4O2γ = 69.12 (3)°
Mr = 572.73V = 1576.7 (7) Å3
Triclinic, P1Z = 2
a = 9.842 (2) ÅMo Kα radiation
b = 13.151 (3) ŵ = 0.08 mm1
c = 13.552 (3) ÅT = 293 K
α = 74.43 (3)°0.26 × 0.22 × 0.20 mm
β = 81.92 (3)°
Data collection top
Rigaku Saturn
diffractometer
6168 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2008)
4273 reflections with I > 2σ(I)
Tmin = 0.981, Tmax = 0.985Rint = 0.033
17336 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0572 restraints
wR(F2) = 0.174H-atom parameters constrained
S = 1.06Δρmax = 0.29 e Å3
6168 reflectionsΔρmin = 0.24 e Å3
399 parameters
Special details top

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 andgoodness 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) top
xyzUiso*/UeqOcc. (<1)
O10.33256 (15)0.41003 (11)0.03815 (10)0.0723 (4)
O20.36695 (14)0.00487 (9)0.43694 (9)0.0579 (4)
N10.31962 (15)0.25956 (11)0.16827 (10)0.0456 (4)
N20.00271 (18)0.22023 (14)0.08727 (13)0.0650 (5)
N30.04621 (17)0.22186 (14)0.60535 (13)0.0665 (5)
N40.72011 (19)0.26509 (12)0.27732 (12)0.0652 (5)
C10.37105 (19)0.34525 (14)0.12145 (13)0.0506 (4)
C20.47929 (18)0.34194 (13)0.18879 (13)0.0487 (4)
C30.5722 (2)0.40412 (15)0.17296 (16)0.0628 (5)
H30.56700.46260.11530.075*
C40.6718 (2)0.37619 (17)0.24543 (18)0.0741 (6)
H40.73550.41630.23630.089*
C50.6800 (2)0.28913 (18)0.33248 (17)0.0697 (6)
H50.74860.27190.38040.084*
C60.5866 (2)0.22835 (16)0.34780 (13)0.0569 (5)
H60.59040.17080.40610.068*
C70.48760 (18)0.25501 (13)0.27459 (12)0.0451 (4)
C80.38313 (18)0.19473 (13)0.26923 (11)0.0423 (4)
C90.26660 (18)0.20220 (13)0.35566 (11)0.0418 (4)
C100.26648 (18)0.10992 (13)0.43410 (12)0.0451 (4)
C110.16418 (19)0.11548 (15)0.51642 (13)0.0529 (4)
H110.16960.05120.56790.063*
C120.05450 (19)0.21522 (15)0.52287 (13)0.0515 (4)
C130.0518 (2)0.30963 (15)0.44214 (13)0.0551 (5)
H130.02140.37790.44240.066*
C140.1558 (2)0.30175 (14)0.36355 (13)0.0526 (4)
H140.15230.36610.31280.063*
C150.46646 (17)0.07377 (13)0.26878 (11)0.0423 (4)
C160.45792 (18)0.01265 (13)0.35126 (12)0.0446 (4)
C170.54006 (19)0.12331 (14)0.35451 (13)0.0512 (4)
H170.52990.17860.41160.061*
C180.63747 (19)0.15355 (14)0.27427 (13)0.0500 (4)
C190.6473 (2)0.06638 (15)0.18986 (13)0.0585 (5)
H190.71040.08290.13410.070*
C200.5653 (2)0.04237 (15)0.18886 (13)0.0553 (5)
H200.57580.09810.13230.066*
C210.2309 (2)0.22241 (15)0.11800 (14)0.0547 (5)
H21A0.25800.14160.14120.066*
H21B0.25390.23970.04470.066*
C220.0696 (2)0.27255 (18)0.13600 (17)0.0683 (6)
H22A0.04430.25970.20900.082*
H22B0.03830.35270.10700.082*
C230.1125 (2)0.28245 (17)0.03626 (15)0.0606 (5)
H230.14290.35930.03030.073*
C240.1941 (2)0.23795 (17)0.01401 (14)0.0579 (5)
C250.1574 (2)0.12469 (18)0.00607 (15)0.0657 (5)
H250.07940.07490.03280.079*
C260.2341 (3)0.0835 (2)0.05482 (16)0.0771 (6)
H260.20640.00700.05010.093*
C270.3511 (3)0.1566 (3)0.10997 (18)0.0909 (8)
H270.40450.12980.14200.109*
C280.3891 (3)0.2687 (3)0.1178 (2)0.1100 (10)
H280.46880.31800.15520.132*
C290.3110 (3)0.3104 (2)0.07097 (19)0.0887 (7)
H290.33730.38720.07800.106*
C300.1847 (2)0.31369 (18)0.59963 (17)0.0753 (6)
H30A0.26000.28400.63560.090*
H30B0.20900.34410.52830.090*
C310.1861 (3)0.4074 (2)0.6441 (2)0.1015 (8)
H31A0.27970.46510.63600.152*
H31B0.11220.43780.60890.152*
H31C0.16710.37910.71570.152*
C320.0309 (2)0.12577 (18)0.69285 (16)0.0714 (6)
H32A0.07780.15260.75330.086*
H32B0.07180.08780.70520.086*
C330.0946 (3)0.0433 (2)0.6787 (2)0.1069 (9)
H33A0.07360.02040.73620.160*
H33B0.05290.01940.61690.160*
H33C0.19810.07780.67400.160*
C340.8377 (3)0.2893 (2)0.1969 (2)0.0724 (8)0.76
H34A0.92110.27070.20640.087*0.76
H34B0.80120.24560.12940.087*0.76
C350.8722 (4)0.4042 (3)0.1772 (3)0.0838 (11)0.76
H35A0.89850.46030.23990.101*0.76
H35B0.95190.41700.12710.101*0.76
H35C0.78830.40830.15210.101*0.76
C34'0.7532 (10)0.3164 (7)0.1892 (6)0.0724 (8)0.24
H34C0.72300.25660.12840.087*0.24
H34D0.69660.36550.19670.087*0.24
C35'0.9113 (12)0.3765 (11)0.1716 (13)0.0838 (11)0.24
H35D0.96230.32350.15120.101*0.24
H35E0.92410.41540.11850.101*0.24
H35F0.94930.42940.23380.101*0.24
C360.7264 (2)0.34727 (17)0.37557 (17)0.0726 (6)
H36A0.72330.31190.43050.087*
H36B0.81850.40800.37720.087*
C370.6059 (3)0.3945 (2)0.3947 (2)0.0971 (8)
H37A0.51410.33460.38950.146*
H37B0.61160.44300.46220.146*
H37C0.61410.43640.34470.146*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0802 (10)0.0692 (9)0.0529 (8)0.0277 (8)0.0096 (7)0.0163 (7)
O20.0672 (8)0.0433 (7)0.0453 (7)0.0118 (6)0.0151 (6)0.0002 (5)
N10.0533 (8)0.0474 (8)0.0364 (7)0.0224 (7)0.0069 (6)0.0005 (6)
N20.0600 (10)0.0694 (10)0.0723 (11)0.0221 (8)0.0126 (9)0.0222 (8)
N30.0568 (10)0.0709 (10)0.0628 (10)0.0188 (8)0.0170 (8)0.0147 (8)
N40.0704 (11)0.0488 (9)0.0634 (10)0.0074 (8)0.0043 (8)0.0128 (7)
C10.0550 (10)0.0468 (9)0.0428 (9)0.0187 (8)0.0009 (8)0.0016 (7)
C20.0527 (10)0.0439 (9)0.0494 (10)0.0218 (8)0.0033 (8)0.0060 (7)
C30.0675 (12)0.0515 (11)0.0722 (13)0.0327 (10)0.0081 (10)0.0077 (9)
C40.0715 (14)0.0742 (14)0.0979 (17)0.0446 (12)0.0074 (12)0.0334 (13)
C50.0708 (13)0.0849 (15)0.0701 (13)0.0379 (12)0.0069 (10)0.0277 (11)
C60.0650 (12)0.0646 (11)0.0467 (10)0.0285 (10)0.0059 (9)0.0114 (8)
C70.0509 (9)0.0464 (9)0.0412 (9)0.0225 (8)0.0015 (7)0.0091 (7)
C80.0510 (9)0.0420 (9)0.0347 (8)0.0213 (7)0.0037 (7)0.0017 (6)
C90.0488 (9)0.0409 (9)0.0370 (8)0.0185 (8)0.0020 (7)0.0066 (7)
C100.0479 (9)0.0425 (9)0.0430 (9)0.0172 (8)0.0007 (7)0.0059 (7)
C110.0591 (11)0.0514 (10)0.0461 (10)0.0249 (9)0.0088 (8)0.0054 (8)
C120.0502 (10)0.0578 (11)0.0507 (10)0.0227 (9)0.0050 (8)0.0171 (8)
C130.0559 (11)0.0497 (10)0.0541 (10)0.0115 (8)0.0003 (8)0.0126 (8)
C140.0643 (11)0.0449 (10)0.0444 (9)0.0184 (9)0.0008 (8)0.0044 (7)
C150.0466 (9)0.0437 (9)0.0367 (8)0.0194 (7)0.0008 (7)0.0042 (7)
C160.0475 (9)0.0474 (10)0.0396 (8)0.0205 (8)0.0034 (7)0.0077 (7)
C170.0565 (10)0.0426 (10)0.0482 (10)0.0155 (8)0.0019 (8)0.0041 (7)
C180.0472 (9)0.0503 (10)0.0510 (10)0.0134 (8)0.0032 (8)0.0131 (8)
C190.0634 (12)0.0615 (12)0.0445 (10)0.0178 (10)0.0106 (8)0.0137 (8)
C200.0623 (11)0.0529 (11)0.0434 (9)0.0189 (9)0.0073 (8)0.0051 (8)
C210.0599 (11)0.0590 (11)0.0493 (10)0.0219 (9)0.0108 (8)0.0125 (8)
C220.0575 (12)0.0759 (13)0.0827 (14)0.0222 (10)0.0096 (10)0.0340 (11)
C230.0518 (11)0.0662 (12)0.0636 (12)0.0170 (10)0.0020 (9)0.0192 (10)
C240.0488 (10)0.0715 (13)0.0538 (11)0.0186 (9)0.0001 (8)0.0188 (9)
C250.0618 (12)0.0814 (15)0.0604 (12)0.0309 (11)0.0017 (9)0.0183 (10)
C260.0852 (16)0.1079 (17)0.0617 (13)0.0579 (14)0.0115 (12)0.0309 (12)
C270.0702 (15)0.161 (3)0.0698 (15)0.0571 (17)0.0031 (12)0.0519 (16)
C280.0725 (17)0.159 (3)0.098 (2)0.0152 (18)0.0340 (15)0.047 (2)
C290.0691 (14)0.1021 (18)0.0879 (17)0.0075 (13)0.0237 (13)0.0300 (14)
C300.0560 (12)0.0891 (15)0.0778 (14)0.0188 (11)0.0111 (10)0.0295 (12)
C310.103 (2)0.0996 (19)0.0962 (18)0.0119 (15)0.0012 (15)0.0454 (15)
C320.0767 (14)0.0844 (14)0.0616 (12)0.0423 (12)0.0242 (10)0.0242 (10)
C330.115 (2)0.114 (2)0.116 (2)0.0718 (18)0.0348 (17)0.0437 (17)
C340.0742 (19)0.0536 (15)0.0874 (18)0.0204 (13)0.0190 (16)0.0261 (13)
C350.098 (3)0.072 (2)0.0880 (19)0.0393 (16)0.0252 (19)0.0309 (19)
C34'0.0742 (19)0.0536 (15)0.0874 (18)0.0204 (13)0.0190 (16)0.0261 (13)
C35'0.098 (3)0.072 (2)0.0880 (19)0.0393 (16)0.0252 (19)0.0309 (19)
C360.0678 (13)0.0586 (12)0.0777 (14)0.0027 (11)0.0078 (11)0.0169 (11)
C370.122 (2)0.0702 (15)0.0990 (19)0.0350 (15)0.0047 (17)0.0172 (13)
Geometric parameters (Å, º) top
O1—C11.2319 (19)C21—H21A0.9700
O2—C101.377 (2)C21—H21B0.9700
O2—C161.3810 (19)C22—H22A0.9700
N1—C11.364 (2)C22—H22B0.9700
N1—C211.455 (2)C23—C241.468 (3)
N1—C81.491 (2)C23—H230.9300
N2—C231.261 (2)C24—C291.378 (3)
N2—C221.463 (2)C24—C251.379 (3)
N3—C121.385 (2)C25—C261.387 (3)
N3—C301.459 (3)C25—H250.9300
N3—C321.461 (3)C26—C271.370 (3)
N4—C181.393 (2)C26—H260.9300
N4—C361.466 (3)C27—C281.364 (4)
N4—C341.482 (3)C27—H270.9300
N4—C34'1.467 (7)C28—C291.386 (3)
C1—C21.479 (2)C28—H280.9300
C2—C71.383 (2)C29—H290.9300
C2—C31.391 (2)C30—C311.506 (3)
C3—C41.371 (3)C30—H30A0.9700
C3—H30.9300C30—H30B0.9700
C4—C51.395 (3)C31—H31A0.9600
C4—H40.9300C31—H31B0.9600
C5—C61.381 (3)C31—H31C0.9600
C5—H50.9300C32—C331.496 (3)
C6—C71.378 (2)C32—H32A0.9700
C6—H60.9300C32—H32B0.9700
C7—C81.524 (2)C33—H33A0.9600
C8—C151.509 (2)C33—H33B0.9600
C8—C91.517 (2)C33—H33C0.9600
C9—C101.382 (2)C34—C351.515 (4)
C9—C141.393 (2)C34—H34A0.9700
C10—C111.393 (2)C34—H34B0.9801
C11—C121.385 (3)C35—H35A0.9600
C11—H110.9300C35—H35B0.9600
C12—C131.412 (2)C35—H35C0.9600
C13—C141.367 (2)C34'—C35'1.492 (9)
C13—H130.9300C34'—H34C0.9696
C14—H140.9300C34'—H34D0.9710
C15—C161.381 (2)C35'—H35D0.9600
C15—C201.395 (2)C35'—H35E0.9600
C16—C171.382 (2)C35'—H35F0.9600
C17—C181.388 (2)C36—C371.488 (3)
C17—H170.9300C36—H36A0.9700
C18—C191.406 (2)C36—H36B0.9700
C19—C201.366 (2)C37—H37A0.9600
C19—H190.9300C37—H37B0.9600
C20—H200.9300C37—H37C0.9600
C21—C221.498 (3)
C10—O2—C16118.54 (12)N2—C22—C21108.56 (16)
C1—N1—C21123.41 (14)N2—C22—H22A110.0
C1—N1—C8113.61 (13)C21—C22—H22A110.0
C21—N1—C8122.21 (13)N2—C22—H22B110.0
C23—N2—C22118.20 (18)C21—C22—H22B110.0
C12—N3—C30121.57 (16)H22A—C22—H22B108.4
C12—N3—C32120.37 (16)N2—C23—C24122.38 (19)
C30—N3—C32116.85 (16)N2—C23—H23118.8
C18—N4—C36118.08 (16)C24—C23—H23118.8
C18—N4—C34118.14 (17)C29—C24—C25118.5 (2)
C36—N4—C34119.76 (17)C29—C24—C23119.7 (2)
C18—N4—C34'124.8 (4)C25—C24—C23121.83 (18)
C36—N4—C34'112.6 (4)C24—C25—C26121.4 (2)
O1—C1—N1124.55 (17)C24—C25—H25119.3
O1—C1—C2128.61 (16)C26—C25—H25119.3
N1—C1—C2106.83 (13)C27—C26—C25119.3 (2)
C7—C2—C3120.98 (17)C27—C26—H26120.3
C7—C2—C1108.63 (14)C25—C26—H26120.3
C3—C2—C1130.17 (16)C28—C27—C26119.8 (2)
C4—C3—C2117.64 (17)C28—C27—H27120.1
C4—C3—H3121.2C26—C27—H27120.1
C2—C3—H3121.2C27—C28—C29121.0 (2)
C3—C4—C5121.62 (18)C27—C28—H28119.5
C3—C4—H4119.2C29—C28—H28119.5
C5—C4—H4119.2C24—C29—C28119.9 (3)
C6—C5—C4120.29 (19)C24—C29—H29120.0
C6—C5—H5119.9C28—C29—H29120.0
C4—C5—H5119.9N3—C30—C31114.5 (2)
C7—C6—C5118.37 (17)N3—C30—H30A108.6
C7—C6—H6120.8C31—C30—H30A108.6
C5—C6—H6120.8N3—C30—H30B108.6
C6—C7—C2121.08 (16)C31—C30—H30B108.6
C6—C7—C8128.26 (14)H30A—C30—H30B107.6
C2—C7—C8110.54 (14)C30—C31—H31A109.5
N1—C8—C15111.68 (13)C30—C31—H31B109.5
N1—C8—C9111.33 (13)H31A—C31—H31B109.5
C15—C8—C9110.18 (12)C30—C31—H31C109.5
N1—C8—C7100.36 (12)H31A—C31—H31C109.5
C15—C8—C7110.20 (13)H31B—C31—H31C109.5
C9—C8—C7112.79 (13)N3—C32—C33113.9 (2)
C10—C9—C14115.44 (15)N3—C32—H32A108.8
C10—C9—C8121.58 (14)C33—C32—H32A108.8
C14—C9—C8122.95 (13)N3—C32—H32B108.8
O2—C10—C9122.77 (15)C33—C32—H32B108.8
O2—C10—C11114.51 (14)H32A—C32—H32B107.7
C9—C10—C11122.72 (16)C32—C33—H33A109.5
C12—C11—C10121.02 (16)C32—C33—H33B109.5
C12—C11—H11119.5H33A—C33—H33B109.5
C10—C11—H11119.5C32—C33—H33C109.5
N3—C12—C11121.37 (16)H33A—C33—H33C109.5
N3—C12—C13121.87 (16)H33B—C33—H33C109.5
C11—C12—C13116.76 (16)N4—C34—C35112.9 (2)
C14—C13—C12120.69 (16)N4—C34—H34A112.6
C14—C13—H13119.7C35—C34—H34A115.5
C12—C13—H13119.7N4—C34—H34B109.8
C13—C14—C9123.34 (15)C35—C34—H34B97.1
C13—C14—H14118.3H34A—C34—H34B107.5
C9—C14—H14118.3N4—C34'—C35'113.8 (9)
C16—C15—C20115.59 (15)N4—C34'—H34C107.5
C16—C15—C8121.89 (14)C35'—C34'—H34C106.6
C20—C15—C8122.34 (14)N4—C34'—H34D109.6
O2—C16—C15122.60 (15)C35'—C34'—H34D111.1
O2—C16—C17114.83 (14)H34B—C34'—H34D146.2
C15—C16—C17122.57 (16)H34C—C34'—H34D107.9
C16—C17—C18121.29 (15)C34'—C35'—H35D109.5
C16—C17—H17119.4C34'—C35'—H35E109.5
C18—C17—H17119.4H35D—C35'—H35E109.5
C17—C18—N4121.37 (16)C34'—C35'—H35F109.5
C17—C18—C19116.72 (16)H35D—C35'—H35F109.5
N4—C18—C19121.91 (16)H35E—C35'—H35F109.5
C20—C19—C18120.76 (16)N4—C36—C37113.50 (19)
C20—C19—H19119.6N4—C36—H36A108.9
C18—C19—H19119.6C37—C36—H36A108.9
C19—C20—C15123.05 (16)N4—C36—H36B108.9
C19—C20—H20118.5C37—C36—H36B108.9
C15—C20—H20118.5H36A—C36—H36B107.7
N1—C21—C22115.50 (15)C36—C37—H37A109.5
N1—C21—H21A108.4C36—C37—H37B109.5
C22—C21—H21A108.4H37A—C37—H37B109.5
N1—C21—H21B108.4C36—C37—H37C109.5
C22—C21—H21B108.4H37A—C37—H37C109.5
H21A—C21—H21B107.5H37B—C37—H37C109.5
C21—N1—C1—O110.6 (3)N1—C8—C15—C16138.91 (15)
C8—N1—C1—O1179.33 (17)C9—C8—C15—C1614.6 (2)
C21—N1—C1—C2168.62 (15)C7—C8—C15—C16110.44 (17)
C8—N1—C1—C21.50 (19)N1—C8—C15—C2046.1 (2)
O1—C1—C2—C7179.92 (18)C9—C8—C15—C20170.38 (15)
N1—C1—C2—C70.79 (19)C7—C8—C15—C2064.54 (19)
O1—C1—C2—C35.3 (3)C10—O2—C16—C159.4 (2)
N1—C1—C2—C3173.79 (18)C10—O2—C16—C17170.81 (14)
C7—C2—C3—C40.1 (3)C20—C15—C16—O2179.04 (15)
C1—C2—C3—C4174.11 (18)C8—C15—C16—O23.7 (2)
C2—C3—C4—C50.4 (3)C20—C15—C16—C170.8 (2)
C3—C4—C5—C60.0 (3)C8—C15—C16—C17176.08 (15)
C4—C5—C6—C70.9 (3)O2—C16—C17—C18179.34 (15)
C5—C6—C7—C21.4 (3)C15—C16—C17—C180.5 (3)
C5—C6—C7—C8174.27 (18)C16—C17—C18—N4179.84 (16)
C3—C2—C7—C61.0 (3)C16—C17—C18—C190.4 (3)
C1—C2—C7—C6176.16 (16)C36—N4—C18—C1713.2 (3)
C3—C2—C7—C8175.35 (16)C34—N4—C18—C17170.6 (2)
C1—C2—C7—C80.18 (19)C34'—N4—C18—C17141.0 (5)
C1—N1—C8—C15118.30 (15)C36—N4—C18—C19167.39 (18)
C21—N1—C8—C1552.0 (2)C34—N4—C18—C1910.0 (3)
C1—N1—C8—C9118.08 (15)C34'—N4—C18—C1938.4 (5)
C21—N1—C8—C971.67 (19)C17—C18—C19—C200.7 (3)
C1—N1—C8—C71.53 (17)N4—C18—C19—C20179.88 (18)
C21—N1—C8—C7168.72 (15)C18—C19—C20—C151.1 (3)
C6—C7—C8—N1175.03 (17)C16—C15—C20—C191.1 (3)
C2—C7—C8—N10.97 (17)C8—C15—C20—C19176.36 (16)
C6—C7—C8—C1557.2 (2)C1—N1—C21—C2294.8 (2)
C2—C7—C8—C15118.84 (15)C8—N1—C21—C2295.9 (2)
C6—C7—C8—C966.4 (2)C23—N2—C22—C21135.87 (19)
C2—C7—C8—C9117.58 (15)N1—C21—C22—N2175.59 (14)
N1—C8—C9—C10138.75 (15)C22—N2—C23—C24178.91 (17)
C15—C8—C9—C1014.3 (2)N2—C23—C24—C29178.3 (2)
C7—C8—C9—C10109.32 (17)N2—C23—C24—C251.7 (3)
N1—C8—C9—C1443.2 (2)C29—C24—C25—C260.7 (3)
C15—C8—C9—C14167.67 (14)C23—C24—C25—C26179.25 (17)
C7—C8—C9—C1468.73 (19)C24—C25—C26—C271.6 (3)
C16—O2—C10—C99.7 (2)C25—C26—C27—C281.1 (4)
C16—O2—C10—C11169.93 (14)C26—C27—C28—C290.2 (4)
C14—C9—C10—O2178.82 (15)C25—C24—C29—C280.6 (3)
C8—C9—C10—O23.0 (2)C23—C24—C29—C28179.4 (2)
C14—C9—C10—C110.8 (2)C27—C28—C29—C241.0 (4)
C8—C9—C10—C11177.40 (15)C12—N3—C30—C3197.3 (2)
O2—C10—C11—C12178.66 (15)C32—N3—C30—C3195.2 (2)
C9—C10—C11—C121.0 (3)C12—N3—C32—C3384.8 (2)
C30—N3—C12—C11161.22 (18)C30—N3—C32—C3382.9 (2)
C32—N3—C12—C115.9 (3)C18—N4—C34—C35153.8 (3)
C30—N3—C12—C1319.7 (3)C36—N4—C34—C3549.1 (4)
C32—N3—C12—C13173.26 (17)C34'—N4—C34—C3542.0 (6)
C10—C11—C12—N3178.91 (17)C18—N4—C34'—C35'128.0 (7)
C10—C11—C12—C130.3 (3)C36—N4—C34'—C35'76.5 (9)
N3—C12—C13—C14177.52 (17)C34—N4—C34'—C35'33.5 (7)
C11—C12—C13—C141.6 (3)C18—N4—C36—C3787.3 (2)
C12—C13—C14—C91.9 (3)C34—N4—C36—C37115.6 (2)
C10—C9—C14—C130.7 (3)C34'—N4—C36—C3769.9 (5)
C8—C9—C14—C13178.82 (16)

Experimental details

Crystal data
Chemical formulaC37H40N4O2
Mr572.73
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)9.842 (2), 13.151 (3), 13.552 (3)
α, β, γ (°)74.43 (3), 81.92 (3), 69.12 (3)
V3)1576.7 (7)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.26 × 0.22 × 0.20
Data collection
DiffractometerRigaku Saturn
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2008)
Tmin, Tmax0.981, 0.985
No. of measured, independent and
observed [I > 2σ(I)] reflections
17336, 6168, 4273
Rint0.033
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.174, 1.06
No. of reflections6168
No. of parameters399
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.29, 0.24

Computer programs: CrystalClear (Rigaku, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

The authors thank the Science Development Committee of Tianjin Agricultural college (research grant No. 2009 N02).

References

First citationKwon, J. Y., Jang, Y. J., Kim, K. M., Nam, W. & Yoon, I. (2005). J. Am. Chem. Soc. 127, 10107–10111.  Web of Science CrossRef PubMed CAS
First citationRigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationTian, M.-Z. & Peng, X.-J. (2008). Acta Cryst. E64, o1645.  Web of Science CSD CrossRef IUCr Journals
First citationWu, D., Huang, W., Duan, C. Y., Lin, Z. H. & Meng, Q. J. (2007). Inorg. Chem. 46, 1538–1540.  Web of Science CSD CrossRef PubMed CAS
First citationXu, Z., Guo, W., Su, B., Shen, X.-K. & Yang, F. (2010a). Acta Cryst. E66, o1500.  Web of Science CSD CrossRef IUCr Journals
First citationXu, Z.-H., Zhang, Y.-L., Zhao, Y.-R. & Yang, F.-L. (2010b). Acta Cryst. E66, o1504.  Web of Science CSD CrossRef IUCr Journals
First citationZhang, L.-Z., Peng, X.-J., Gao, S. & Fan, J.-L. (2008). Acta Cryst. E64, o403.  Web of Science CSD CrossRef IUCr Journals

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