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ISSN: 2056-9890

Di­ethyl 3-amino-4-[(tri­phenyl­phosphor­anyl­­idene)amino]thieno[2,3-b]thio­phene-2,5-di­carboxyl­ate

aDepartment of Chemistry, Kaili College, Kaili 556000, People's Republic of China, bDepartment of Chemistry and Life Science, Xianning College, Xianning 437000, People's Republic of China, and cHubei Key Laboratory of Natural Products Research and Development, China Three Gorges University, Yichang 443002, People's Republic of China
*Correspondence e-mail: mgliu0427@yahoo.com.cn

(Received 12 May 2008; accepted 25 May 2008; online 7 June 2008)

The asymmetric unit of the title compound, C30H27N2O4PS2, consists of two crystallographically independent mol­ecules. The thieno[2,3-b]thio­phene ring systems are planar. One of the terminal ethyl groups is disordered over two positions; the site occupancy factors are ca 0.7 and 0.3. The crystal structure is stabilized by N—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds.

Related literature

Related preparation and biological activity are described by Walter (1999a[Walter, H. (1999a). PCT Int. Appl. No. 44; WO 9911631.],b[Walter, H. (1999b). PCT Int. Appl. No. 89; WO 9914202.]). For related literature, see: Ding et al. (2004[Ding, M. W., Xu, S. Z. & Zhao, J. F. (2004). J. Org. Chem. 69, 8366-8371.]). For the crystal structure of another fused pyrimidinone derivative, see: Liu & Hu (2006[Liu, M.-G. & Hu, Y.-G. (2006). Acta Cryst. E62, o3206-o3208.]). For related literature, see: Liao et al. (2007[Liao, Q.-B., Huang, J., Yang, Z.-Z. & Liu, M.-G. (2007). Acta Cryst. E63, o3824.]).

[Scheme 1]

Experimental

Crystal data
  • C30H27N2O4PS2

  • Mr = 574.63

  • Triclinic, [P \overline 1]

  • a = 13.1260 (9) Å

  • b = 15.3616 (10) Å

  • c = 16.6497 (11) Å

  • α = 68.140 (1)°

  • β = 71.043 (1)°

  • γ = 68.969 (1)°

  • V = 2836.5 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.28 mm−1

  • T = 298 (2) K

  • 0.20 × 0.10 × 0.06 mm

Data collection
  • Bruker SMART 4K CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.946, Tmax = 0.983

  • 20968 measured reflections

  • 10981 independent reflections

  • 6314 reflections with I > 2σ(I)

  • Rint = 0.053

Refinement
  • R[F2 > 2σ(F2)] = 0.068

  • wR(F2) = 0.159

  • S = 0.96

  • 10981 reflections

  • 727 parameters

  • 6 restraints

  • H-atom parameters constrained

  • Δρmax = 0.48 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C33—H33⋯O3 0.93 2.46 3.298 (5) 151
N4—H4B⋯O7 0.86 2.16 2.817 (4) 134
N4—H4A⋯N3 0.86 2.29 2.945 (4) 133
N2—H2B⋯O3 0.86 2.19 2.832 (4) 131
N2—H2A⋯N1 0.86 2.33 2.965 (4) 131

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Comment top

The derivatives of heterocycles containing the thienopyrimidine system, which are well known bioisosteres of quinazolines, are of great importance because of their remarkable biological properties (Walter, 1999a,b; Ding et al., 2004). As a part of our ongoing investigations on the preparation of derivatives of heterocyclic compounds (Liu & Hu, 2006; Liao et al., 2007), we have synthesized and structurally characterized characterized the title compound. In the crystal structure of the title compound two crystallographically independent molecules are found in the asymmetric unit. All ring atoms of the thieno[2,3-b]thiophene ring systems lie in a common plane, with maximum deviations of 0.01 (1) Å and 0.02 (1) Å. The crystal structure is stabilized by N—H···N, N—H···O and C—H···O hydrogen bonds (Table 1).

Related literature top

Related preparation and biological activity are described by Walter (1999a,b). For related literature, see: Ding et al., 2004. For crystal structures of other fused pyrimidinone derivatives, see: Liu & Hu (2006). For related literature, see: Liao et al. (2007).

Refinement top

One of the terminal ethyl groups is disordered over two sites with site occupation factors of 0.66 (2) and 0.34 (2). The following restraints have been applied for the disordered atoms: O—CH2 1.45 (1) Å, CH2—CH3 1.54 (1) Å and O···CH3 2.45 (1) Å. All H-atoms were positioned with idealized geometry and refined with fixed isotropic U values (Uiso(H) = 1.5Ueq(C) for methyl H atoms and Uiso(H) = 1.2Ueq(C) for all other H atoms) using a riding model with C—H = 0.93 Å, 0.97 Å = 0.96 Å and N—H = 0.86 Å.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound with labelling and displacement ellipsoids drawn at the 50% probability level.
Diethyl 3-amino-4-[(triphenylphosphoranylidene)amino]thieno[2,3-b]thiophene- 2,5-dicarboxylate top
Crystal data top
C30H27N2O4PS2Z = 4
Mr = 574.63F(000) = 1200
Triclinic, P1Dx = 1.346 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 13.1260 (9) ÅCell parameters from 2577 reflections
b = 15.3616 (10) Åθ = 2.3–19.7°
c = 16.6497 (11) ŵ = 0.28 mm1
α = 68.140 (1)°T = 298 K
β = 71.043 (1)°Block, yellow
γ = 68.969 (1)°0.20 × 0.10 × 0.06 mm
V = 2836.5 (3) Å3
Data collection top
Bruker SMART 4K CCD area-detector
diffractometer
10981 independent reflections
Radiation source: fine-focus sealed tube6314 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.053
ϕ and ω scansθmax = 26.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1516
Tmin = 0.946, Tmax = 0.983k = 1818
20968 measured reflectionsl = 1420
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)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159H-atom parameters constrained
S = 0.96 w = 1/[σ2(Fo2) + (0.0624P)2]
where P = (Fo2 + 2Fc2)/3
10981 reflections(Δ/σ)max = 0.001
727 parametersΔρmax = 0.48 e Å3
6 restraintsΔρmin = 0.28 e Å3
Crystal data top
C30H27N2O4PS2γ = 68.969 (1)°
Mr = 574.63V = 2836.5 (3) Å3
Triclinic, P1Z = 4
a = 13.1260 (9) ÅMo Kα radiation
b = 15.3616 (10) ŵ = 0.28 mm1
c = 16.6497 (11) ÅT = 298 K
α = 68.140 (1)°0.20 × 0.10 × 0.06 mm
β = 71.043 (1)°
Data collection top
Bruker SMART 4K CCD area-detector
diffractometer
10981 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
6314 reflections with I > 2σ(I)
Tmin = 0.946, Tmax = 0.983Rint = 0.053
20968 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0686 restraints
wR(F2) = 0.159H-atom parameters constrained
S = 0.96Δρmax = 0.48 e Å3
10981 reflectionsΔρmin = 0.28 e Å3
727 parameters
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 > 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)
C10.2610 (3)0.4257 (3)0.8472 (2)0.0461 (9)
C20.2866 (3)0.4036 (3)0.9289 (3)0.0608 (11)
H20.28960.45280.94710.073*
C30.3074 (4)0.3091 (3)0.9823 (3)0.0705 (13)
H30.32140.29511.03780.085*
C40.3078 (4)0.2357 (3)0.9548 (4)0.0772 (15)
H40.32380.17170.99090.093*
C50.2847 (4)0.2559 (3)0.8746 (3)0.0759 (14)
H50.28460.20570.85620.091*
C60.2617 (3)0.3504 (3)0.8208 (3)0.0609 (12)
H60.24650.36360.76600.073*
C70.1246 (3)0.6316 (3)0.8246 (2)0.0464 (9)
C80.0934 (3)0.7258 (3)0.7712 (3)0.0639 (12)
H80.12830.74220.71140.077*
C90.0103 (4)0.7958 (3)0.8068 (3)0.0803 (15)
H90.01040.85920.77050.096*
C100.0415 (4)0.7735 (3)0.8939 (4)0.0783 (14)
H100.09660.82140.91730.094*
C110.0122 (4)0.6801 (4)0.9473 (3)0.0740 (14)
H110.04750.66441.00710.089*
C120.0699 (3)0.6089 (3)0.9126 (3)0.0591 (11)
H120.08830.54520.94880.071*
C130.3626 (3)0.5803 (3)0.7625 (3)0.0474 (10)
C140.4623 (3)0.5437 (3)0.7082 (3)0.0580 (11)
H140.46290.50540.67590.070*
C150.5600 (4)0.5627 (3)0.7009 (4)0.0758 (14)
H150.62600.53720.66440.091*
C160.5595 (5)0.6190 (4)0.7476 (4)0.0951 (18)
H160.62520.63280.74230.114*
C170.4628 (5)0.6557 (4)0.8025 (4)0.0954 (17)
H170.46380.69310.83500.114*
C180.3640 (4)0.6374 (3)0.8099 (3)0.0712 (13)
H180.29850.66330.84650.085*
C190.1617 (3)0.5670 (2)0.6309 (2)0.0390 (9)
C200.0575 (3)0.5474 (3)0.6605 (2)0.0466 (9)
C210.0036 (3)0.5049 (3)0.7492 (3)0.0523 (10)
C220.1442 (4)0.4291 (4)0.8356 (3)0.106 (2)
H22A0.22060.43700.83490.127*
H22B0.14610.45260.88290.127*
C230.0812 (6)0.3255 (5)0.8516 (4)0.156 (3)
H23A0.07940.30290.80440.233*
H23B0.11710.28820.90700.233*
H23C0.00620.31810.85350.233*
C240.1894 (3)0.5986 (2)0.5359 (2)0.0375 (8)
C250.1080 (3)0.6043 (2)0.4975 (2)0.0460 (9)
C260.2835 (3)0.6265 (2)0.4709 (2)0.0402 (9)
C270.2694 (3)0.6522 (2)0.3857 (2)0.0429 (9)
N20.3742 (3)0.6258 (2)0.4942 (2)0.0568 (9)
H2A0.37590.60250.54940.068*
H2B0.42550.64580.45040.068*
C280.3516 (3)0.6807 (3)0.3064 (3)0.0508 (10)
C290.3981 (4)0.7238 (4)0.1496 (3)0.0856 (16)
H29A0.37800.79410.12410.103*
H29B0.47250.70340.16070.103*
C300.3979 (5)0.6781 (4)0.0880 (3)0.111 (2)
H30A0.41890.60860.11290.166*
H30B0.45030.69630.03330.166*
H30C0.32430.69890.07670.166*
C310.7449 (3)0.8334 (3)0.3607 (3)0.0460 (9)
C320.6524 (3)0.8387 (3)0.3338 (3)0.0507 (10)
H320.61510.89760.29950.061*
C330.6157 (3)0.7574 (3)0.3577 (3)0.0583 (11)
H330.55280.76200.34040.070*
C340.6709 (4)0.6700 (3)0.4066 (3)0.0672 (13)
H340.64620.61510.42160.081*
C350.7622 (4)0.6624 (3)0.4337 (3)0.0756 (14)
H350.79870.60270.46770.091*
C360.8008 (3)0.7439 (3)0.4105 (3)0.0639 (12)
H360.86350.73850.42830.077*
C370.8032 (3)0.9893 (3)0.2095 (3)0.0467 (9)
C380.7843 (4)1.0884 (3)0.1696 (3)0.0755 (14)
H380.75831.13010.20480.091*
C390.8030 (5)1.1264 (4)0.0797 (3)0.0946 (17)
H390.78961.19350.05460.114*
C400.8409 (4)1.0675 (5)0.0260 (3)0.0891 (16)
H400.85321.09390.03530.107*
C410.8603 (4)0.9702 (5)0.0631 (4)0.0893 (16)
H410.88710.92950.02680.107*
C420.8409 (4)0.9297 (4)0.1547 (3)0.0713 (13)
H420.85320.86260.17920.086*
C430.6981 (3)1.0324 (2)0.3743 (2)0.0402 (9)
C440.5824 (3)1.0483 (3)0.3927 (3)0.0601 (11)
H440.55301.00560.38550.072*
C450.5117 (4)1.1272 (3)0.4216 (3)0.0675 (13)
H450.43461.13770.43370.081*
C460.5541 (4)1.1899 (3)0.4326 (3)0.0674 (13)
H460.50581.24330.45170.081*
C470.6676 (4)1.1749 (3)0.4157 (3)0.0595 (11)
H470.69621.21750.42400.071*
C480.7390 (3)1.0968 (3)0.3864 (2)0.0509 (10)
H480.81601.08710.37460.061*
C490.9839 (3)0.9001 (2)0.3903 (2)0.0395 (9)
C500.9597 (3)0.8761 (2)0.4826 (3)0.0422 (9)
C510.8587 (3)0.8594 (3)0.5433 (3)0.0538 (11)
C520.7663 (10)0.8289 (6)0.7033 (9)0.081 (4)0.66 (2)
H52A0.69780.85650.68170.097*0.66 (2)
H52B0.76260.86260.74360.097*0.66 (2)
C530.7848 (11)0.7206 (7)0.7484 (9)0.106 (5)0.66 (2)
H53A0.78590.68910.70780.159*0.66 (2)
H53B0.72530.70960.79960.159*0.66 (2)
H53C0.85500.69430.76620.159*0.66 (2)
C52'0.774 (2)0.788 (3)0.6825 (9)0.081 (8)0.34 (2)
H52C0.78430.73110.66600.097*0.34 (2)
H52D0.70230.83320.67340.097*0.34 (2)
C53'0.781 (2)0.760 (2)0.7789 (8)0.112 (9)0.34 (2)
H53D0.84970.71070.78820.167*0.34 (2)
H53E0.71880.73530.81700.167*0.34 (2)
H53F0.77910.81620.79250.167*0.34 (2)
C541.0954 (3)0.9101 (2)0.3543 (2)0.0375 (8)
C551.1516 (3)0.8942 (2)0.4175 (2)0.0400 (9)
C561.1601 (3)0.9351 (2)0.2662 (2)0.0408 (9)
C571.2648 (3)0.9386 (2)0.2658 (2)0.0446 (9)
N41.1221 (3)0.9535 (2)0.1935 (2)0.0571 (9)
H4A1.05590.94730.20400.068*
H4B1.16620.97470.14460.068*
C581.3466 (3)0.9665 (3)0.1870 (3)0.0515 (10)
C591.5255 (3)1.0003 (4)0.1294 (3)0.0823 (16)
H59A1.51480.99790.07530.099*
H59B1.59970.95960.13710.099*
C601.5155 (5)1.1006 (4)0.1224 (5)0.142 (3)
H60A1.44141.14030.11600.214*
H60B1.56931.12520.07160.214*
H60C1.52921.10220.17500.214*
N10.2389 (2)0.5576 (2)0.67443 (19)0.0448 (8)
O10.0358 (2)0.4854 (2)0.81614 (18)0.0624 (8)
O20.0900 (2)0.4850 (2)0.75083 (18)0.0763 (9)
O30.4411 (2)0.6868 (2)0.30673 (18)0.0635 (8)
O40.3190 (2)0.6972 (2)0.23237 (18)0.0648 (8)
N30.9225 (2)0.9157 (2)0.3315 (2)0.0482 (8)
O50.7744 (2)0.8654 (2)0.52373 (19)0.0656 (8)
O60.8661 (2)0.8356 (2)0.6283 (2)0.0808 (10)
O71.3321 (2)0.9920 (2)0.1115 (2)0.0711 (9)
O81.4417 (2)0.9638 (2)0.20472 (18)0.0662 (8)
P10.23784 (8)0.54841 (7)0.77260 (7)0.0440 (3)
P20.79766 (8)0.93793 (7)0.32758 (7)0.0426 (3)
S10.00477 (8)0.56927 (8)0.57338 (7)0.0555 (3)
S20.14118 (8)0.64202 (8)0.38364 (7)0.0533 (3)
S31.07321 (8)0.86553 (7)0.52315 (6)0.0502 (3)
S41.28460 (8)0.90910 (8)0.37331 (7)0.0526 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.048 (2)0.048 (2)0.040 (2)0.0129 (18)0.0072 (18)0.0120 (18)
C20.067 (3)0.059 (3)0.054 (3)0.012 (2)0.018 (2)0.015 (2)
C30.075 (3)0.068 (3)0.050 (3)0.011 (3)0.016 (2)0.003 (2)
C40.064 (3)0.055 (3)0.084 (4)0.007 (2)0.016 (3)0.003 (3)
C50.089 (4)0.045 (3)0.091 (4)0.019 (2)0.017 (3)0.017 (3)
C60.068 (3)0.049 (3)0.063 (3)0.017 (2)0.009 (2)0.017 (2)
C70.050 (2)0.046 (2)0.046 (2)0.0141 (18)0.0124 (19)0.0133 (18)
C80.070 (3)0.053 (3)0.053 (3)0.008 (2)0.007 (2)0.012 (2)
C90.078 (3)0.050 (3)0.087 (4)0.003 (2)0.005 (3)0.017 (3)
C100.076 (3)0.063 (3)0.094 (4)0.014 (3)0.001 (3)0.042 (3)
C110.068 (3)0.087 (4)0.063 (3)0.020 (3)0.005 (2)0.036 (3)
C120.063 (3)0.057 (3)0.051 (3)0.009 (2)0.008 (2)0.019 (2)
C130.056 (2)0.044 (2)0.049 (2)0.0127 (19)0.023 (2)0.0117 (19)
C140.055 (3)0.049 (2)0.071 (3)0.011 (2)0.020 (2)0.017 (2)
C150.054 (3)0.070 (3)0.101 (4)0.020 (2)0.023 (3)0.014 (3)
C160.076 (4)0.102 (4)0.125 (5)0.045 (3)0.037 (4)0.019 (4)
C170.106 (5)0.111 (4)0.107 (5)0.052 (4)0.036 (4)0.041 (4)
C180.076 (3)0.075 (3)0.081 (3)0.022 (3)0.029 (3)0.032 (3)
C190.042 (2)0.0315 (18)0.048 (2)0.0106 (16)0.0103 (18)0.0157 (16)
C200.048 (2)0.050 (2)0.043 (2)0.0181 (18)0.0085 (18)0.0119 (18)
C210.046 (2)0.054 (2)0.056 (3)0.018 (2)0.008 (2)0.013 (2)
C220.088 (4)0.137 (5)0.084 (4)0.074 (4)0.026 (3)0.024 (4)
C230.197 (8)0.157 (7)0.116 (6)0.106 (6)0.051 (5)0.027 (5)
C240.039 (2)0.0314 (18)0.041 (2)0.0080 (16)0.0125 (17)0.0077 (16)
C250.041 (2)0.045 (2)0.048 (2)0.0110 (17)0.0105 (18)0.0098 (18)
C260.044 (2)0.0341 (19)0.047 (2)0.0090 (16)0.0127 (18)0.0153 (17)
C270.047 (2)0.044 (2)0.042 (2)0.0147 (17)0.0108 (18)0.0136 (17)
N20.056 (2)0.079 (2)0.044 (2)0.0329 (18)0.0101 (16)0.0139 (17)
C280.058 (3)0.055 (2)0.046 (3)0.021 (2)0.008 (2)0.019 (2)
C290.101 (4)0.119 (4)0.051 (3)0.069 (3)0.007 (3)0.022 (3)
C300.121 (5)0.157 (6)0.065 (4)0.082 (4)0.013 (3)0.031 (4)
C310.039 (2)0.047 (2)0.059 (3)0.0080 (17)0.0128 (19)0.0254 (19)
C320.047 (2)0.057 (2)0.059 (3)0.0169 (19)0.015 (2)0.022 (2)
C330.051 (2)0.072 (3)0.071 (3)0.024 (2)0.011 (2)0.036 (2)
C340.065 (3)0.054 (3)0.094 (4)0.023 (2)0.005 (3)0.038 (3)
C350.077 (3)0.043 (3)0.109 (4)0.005 (2)0.033 (3)0.025 (3)
C360.056 (3)0.048 (2)0.099 (4)0.006 (2)0.032 (2)0.028 (2)
C370.033 (2)0.064 (3)0.052 (3)0.0135 (18)0.0104 (18)0.025 (2)
C380.104 (4)0.073 (3)0.048 (3)0.022 (3)0.014 (3)0.020 (2)
C390.137 (5)0.089 (4)0.057 (4)0.035 (4)0.023 (3)0.015 (3)
C400.100 (4)0.116 (5)0.057 (3)0.047 (4)0.012 (3)0.019 (3)
C410.099 (4)0.121 (5)0.065 (4)0.042 (4)0.006 (3)0.054 (3)
C420.074 (3)0.084 (3)0.066 (3)0.026 (3)0.003 (3)0.039 (3)
C430.039 (2)0.047 (2)0.036 (2)0.0132 (17)0.0080 (16)0.0136 (17)
C440.049 (3)0.061 (3)0.069 (3)0.020 (2)0.006 (2)0.019 (2)
C450.045 (3)0.068 (3)0.074 (3)0.011 (2)0.002 (2)0.018 (3)
C460.078 (3)0.055 (3)0.055 (3)0.006 (2)0.005 (2)0.021 (2)
C470.074 (3)0.054 (3)0.062 (3)0.014 (2)0.019 (2)0.029 (2)
C480.053 (2)0.049 (2)0.057 (3)0.0088 (19)0.017 (2)0.024 (2)
C490.039 (2)0.0315 (18)0.052 (3)0.0061 (16)0.0138 (18)0.0168 (17)
C500.037 (2)0.039 (2)0.052 (3)0.0110 (16)0.0116 (18)0.0114 (17)
C510.047 (3)0.051 (2)0.058 (3)0.013 (2)0.012 (2)0.010 (2)
C520.079 (6)0.084 (7)0.064 (8)0.014 (5)0.003 (6)0.024 (5)
C530.116 (8)0.099 (8)0.114 (12)0.054 (7)0.004 (8)0.044 (7)
C52'0.076 (12)0.12 (2)0.038 (10)0.050 (16)0.017 (9)0.013 (12)
C53'0.139 (18)0.11 (2)0.087 (15)0.060 (18)0.008 (14)0.013 (14)
C540.039 (2)0.0356 (19)0.045 (2)0.0086 (16)0.0151 (18)0.0156 (16)
C550.0346 (19)0.041 (2)0.047 (2)0.0129 (16)0.0118 (17)0.0102 (17)
C560.041 (2)0.042 (2)0.044 (2)0.0057 (17)0.0170 (18)0.0161 (17)
C570.042 (2)0.048 (2)0.048 (2)0.0153 (18)0.0134 (18)0.0128 (18)
N40.0465 (19)0.082 (2)0.047 (2)0.0200 (17)0.0123 (16)0.0198 (18)
C580.051 (2)0.052 (2)0.048 (3)0.0124 (19)0.013 (2)0.011 (2)
C590.046 (3)0.122 (4)0.062 (3)0.034 (3)0.003 (2)0.005 (3)
C600.099 (5)0.097 (5)0.192 (7)0.051 (4)0.037 (5)0.030 (4)
N10.0485 (18)0.0506 (18)0.0420 (19)0.0201 (15)0.0104 (15)0.0138 (15)
O10.0661 (19)0.080 (2)0.0462 (18)0.0334 (15)0.0117 (15)0.0117 (15)
O20.0663 (19)0.108 (2)0.0554 (19)0.0536 (18)0.0124 (15)0.0029 (17)
O30.0550 (18)0.083 (2)0.065 (2)0.0353 (16)0.0010 (15)0.0294 (16)
O40.0712 (19)0.090 (2)0.0372 (17)0.0402 (16)0.0035 (14)0.0119 (15)
N30.0374 (17)0.063 (2)0.058 (2)0.0117 (15)0.0158 (15)0.0293 (17)
O50.0432 (17)0.077 (2)0.078 (2)0.0220 (15)0.0091 (15)0.0223 (16)
O60.0546 (18)0.111 (3)0.053 (2)0.0268 (17)0.0046 (15)0.0002 (18)
O70.0635 (19)0.094 (2)0.0507 (19)0.0274 (16)0.0103 (15)0.0122 (17)
O80.0489 (17)0.092 (2)0.0561 (19)0.0327 (15)0.0109 (14)0.0076 (15)
P10.0494 (6)0.0432 (5)0.0414 (6)0.0139 (5)0.0122 (5)0.0112 (4)
P20.0369 (5)0.0489 (6)0.0498 (6)0.0116 (4)0.0124 (5)0.0204 (5)
S10.0443 (6)0.0740 (7)0.0502 (7)0.0234 (5)0.0116 (5)0.0123 (5)
S20.0501 (6)0.0683 (7)0.0440 (6)0.0205 (5)0.0137 (5)0.0118 (5)
S30.0464 (6)0.0618 (6)0.0438 (6)0.0194 (5)0.0160 (5)0.0070 (5)
S40.0426 (6)0.0695 (7)0.0497 (6)0.0240 (5)0.0155 (5)0.0085 (5)
Geometric parameters (Å, º) top
C1—C61.379 (5)C33—C341.365 (5)
C1—C21.396 (5)C33—H330.9300
C1—P11.811 (4)C34—C351.366 (6)
C2—C31.372 (5)C34—H340.9300
C2—H20.9300C35—C361.393 (6)
C3—C41.365 (6)C35—H350.9300
C3—H30.9300C36—H360.9300
C4—C51.364 (6)C37—C381.380 (5)
C4—H40.9300C37—C421.385 (5)
C5—C61.376 (5)C37—P21.812 (4)
C5—H50.9300C38—C391.362 (6)
C6—H60.9300C38—H380.9300
C7—C121.378 (5)C39—C401.362 (7)
C7—C81.380 (5)C39—H390.9300
C7—P11.794 (4)C40—C411.350 (7)
C8—C91.382 (5)C40—H400.9300
C8—H80.9300C41—C421.390 (6)
C9—C101.356 (6)C41—H410.9300
C9—H90.9300C42—H420.9300
C10—C111.369 (6)C43—C481.381 (5)
C10—H100.9300C43—C441.395 (5)
C11—C121.383 (5)C43—P21.800 (4)
C11—H110.9300C44—C451.377 (5)
C12—H120.9300C44—H440.9300
C13—C141.388 (5)C45—C461.361 (6)
C13—C181.389 (5)C45—H450.9300
C13—P11.812 (4)C46—C471.372 (6)
C14—C151.374 (6)C46—H460.9300
C14—H140.9300C47—C481.373 (5)
C15—C161.359 (7)C47—H470.9300
C15—H150.9300C48—H480.9300
C16—C171.371 (7)C49—N31.365 (4)
C16—H160.9300C49—C501.393 (5)
C17—C181.381 (6)C49—C541.432 (5)
C17—H170.9300C50—C511.423 (5)
C18—H180.9300C50—S31.761 (4)
C19—N11.367 (4)C51—O51.216 (4)
C19—C201.396 (5)C51—O61.349 (5)
C19—C241.433 (5)C52—O61.492 (7)
C20—C211.429 (5)C52—C531.513 (8)
C20—S11.760 (4)C52—H52A0.9700
C21—O11.216 (4)C52—H52B0.9700
C21—O21.359 (5)C53—H53A0.9600
C22—O21.456 (5)C53—H53B0.9600
C22—C231.473 (8)C53—H53C0.9600
C22—H22A0.9700C52'—O61.491 (9)
C22—H22B0.9700C52'—C53'1.523 (10)
C23—H23A0.9600C52'—H52C0.9700
C23—H23B0.9600C52'—H52D0.9700
C23—H23C0.9600C53'—H53D0.9600
C24—C251.376 (5)C53'—H53E0.9600
C24—C261.431 (5)C53'—H53F0.9600
C25—S11.711 (4)C54—C551.376 (5)
C25—S21.716 (4)C54—C561.424 (5)
C26—N21.362 (4)C55—S31.709 (4)
C26—C271.380 (5)C55—S41.722 (3)
C27—C281.443 (5)C56—N41.352 (4)
C27—S21.757 (4)C56—C571.392 (5)
N2—H2A0.8581C57—C581.433 (5)
N2—H2B0.8612C57—S41.759 (4)
C28—O31.213 (4)N4—H4A0.8621
C28—O41.342 (4)N4—H4B0.8573
C29—C301.445 (6)C58—O71.225 (4)
C29—O41.449 (5)C58—O81.357 (5)
C29—H29A0.9700C59—O81.455 (5)
C29—H29B0.9700C59—C601.462 (7)
C30—H30A0.9600C59—H59A0.9700
C30—H30B0.9600C59—H59B0.9700
C30—H30C0.9600C60—H60A0.9600
C31—C321.392 (5)C60—H60B0.9600
C31—C361.393 (5)C60—H60C0.9600
C31—P21.804 (4)N1—P11.583 (3)
C32—C331.373 (5)N3—P21.568 (3)
C32—H320.9300
C6—C1—C2118.4 (4)C31—C36—H36120.1
C6—C1—P1119.7 (3)C35—C36—H36120.1
C2—C1—P1121.7 (3)C38—C37—C42117.4 (4)
C3—C2—C1120.0 (4)C38—C37—P2121.1 (3)
C3—C2—H2120.0C42—C37—P2120.9 (3)
C1—C2—H2120.0C39—C38—C37121.5 (4)
C4—C3—C2120.5 (5)C39—C38—H38119.3
C4—C3—H3119.7C37—C38—H38119.3
C2—C3—H3119.7C40—C39—C38120.9 (5)
C5—C4—C3120.1 (4)C40—C39—H39119.6
C5—C4—H4119.9C38—C39—H39119.6
C3—C4—H4119.9C41—C40—C39119.0 (5)
C4—C5—C6120.1 (5)C41—C40—H40120.5
C4—C5—H5120.0C39—C40—H40120.5
C6—C5—H5120.0C40—C41—C42121.2 (5)
C5—C6—C1120.8 (4)C40—C41—H41119.4
C5—C6—H6119.6C42—C41—H41119.4
C1—C6—H6119.6C37—C42—C41120.0 (4)
C12—C7—C8118.9 (4)C37—C42—H42120.0
C12—C7—P1125.1 (3)C41—C42—H42120.0
C8—C7—P1116.0 (3)C48—C43—C44118.5 (4)
C7—C8—C9119.9 (4)C48—C43—P2117.6 (3)
C7—C8—H8120.1C44—C43—P2123.8 (3)
C9—C8—H8120.1C45—C44—C43120.1 (4)
C10—C9—C8121.0 (4)C45—C44—H44120.0
C10—C9—H9119.5C43—C44—H44120.0
C8—C9—H9119.5C46—C45—C44120.3 (4)
C9—C10—C11119.7 (4)C46—C45—H45119.8
C9—C10—H10120.2C44—C45—H45119.8
C11—C10—H10120.2C45—C46—C47120.4 (4)
C10—C11—C12120.1 (4)C45—C46—H46119.8
C10—C11—H11120.0C47—C46—H46119.8
C12—C11—H11120.0C46—C47—C48119.9 (4)
C7—C12—C11120.5 (4)C46—C47—H47120.1
C7—C12—H12119.8C48—C47—H47120.1
C11—C12—H12119.8C47—C48—C43120.8 (4)
C14—C13—C18118.0 (4)C47—C48—H48119.6
C14—C13—P1119.4 (3)C43—C48—H48119.6
C18—C13—P1122.5 (3)N3—C49—C50132.5 (3)
C15—C14—C13121.6 (4)N3—C49—C54117.2 (3)
C15—C14—H14119.2C50—C49—C54110.3 (3)
C13—C14—H14119.2C49—C50—C51128.1 (4)
C16—C15—C14119.4 (5)C49—C50—S3112.4 (3)
C16—C15—H15120.3C51—C50—S3119.6 (3)
C14—C15—H15120.3O5—C51—O6122.4 (4)
C15—C16—C17120.5 (5)O5—C51—C50125.8 (4)
C15—C16—H16119.7O6—C51—C50111.7 (4)
C16—C17—C18120.5 (5)O6—C52—C53103.9 (6)
C16—C17—H17119.8O6—C52—H52A111.0
C18—C17—H17119.8C53—C52—H52A111.0
C17—C18—C13119.9 (5)O6—C52—H52B111.0
C17—C18—H18120.0C53—C52—H52B111.0
C13—C18—H18120.0H52A—C52—H52B109.0
N1—C19—C20132.6 (3)O6—C52'—C53'106.4 (9)
N1—C19—C24117.7 (3)O6—C52'—H52C110.4
C20—C19—C24109.7 (3)C53'—C52'—H52C110.4
C19—C20—C21128.2 (4)O6—C52'—H52D110.4
C19—C20—S1113.1 (3)C53'—C52'—H52D110.4
C21—C20—S1118.4 (3)H52C—C52'—H52D108.6
O1—C21—O2122.3 (4)C52'—C53'—H53D109.5
O1—C21—C20126.3 (4)C52'—C53'—H53E109.5
O2—C21—C20111.3 (4)H53D—C53'—H53E109.5
O2—C22—C23109.0 (5)C52'—C53'—H53F109.5
O2—C22—H22A109.9H53D—C53'—H53F109.5
C23—C22—H22A109.9H53E—C53'—H53F109.5
O2—C22—H22B109.9C55—C54—C56112.9 (3)
C23—C22—H22B109.9C55—C54—C49113.9 (3)
H22A—C22—H22B108.3C56—C54—C49133.3 (3)
C22—C23—H23A109.5C54—C55—S3112.7 (3)
C22—C23—H23B109.5C54—C55—S4113.4 (3)
H23A—C23—H23B109.5S3—C55—S4133.8 (2)
C22—C23—H23C109.5N4—C56—C57125.6 (3)
H23A—C23—H23C109.5N4—C56—C54123.2 (3)
H23B—C23—H23C109.5C57—C56—C54111.2 (3)
C25—C24—C26112.0 (3)C56—C57—C58124.3 (4)
C25—C24—C19113.9 (3)C56—C57—S4112.5 (3)
C26—C24—C19134.2 (3)C58—C57—S4123.1 (3)
C24—C25—S1113.1 (3)C56—N4—H4A115.3
C24—C25—S2113.9 (3)C56—N4—H4B113.5
S1—C25—S2133.0 (2)H4A—N4—H4B130.9
N2—C26—C27126.4 (3)O7—C58—O8123.2 (4)
N2—C26—C24121.9 (3)O7—C58—C57124.1 (4)
C27—C26—C24111.7 (3)O8—C58—C57112.7 (4)
C26—C27—C28124.4 (3)O8—C59—C60109.7 (4)
C26—C27—S2112.5 (3)O8—C59—H59A109.7
C28—C27—S2123.1 (3)C60—C59—H59A109.7
C26—N2—H2A117.3O8—C59—H59B109.7
C26—N2—H2B115.0C60—C59—H59B109.7
H2A—N2—H2B127.6H59A—C59—H59B108.2
O3—C28—O4123.9 (4)C59—C60—H60A109.5
O3—C28—C27123.9 (4)C59—C60—H60B109.5
O4—C28—C27112.2 (4)H60A—C60—H60B109.5
C30—C29—O4110.2 (4)C59—C60—H60C109.5
C30—C29—H29A109.6H60A—C60—H60C109.5
O4—C29—H29A109.6H60B—C60—H60C109.5
C30—C29—H29B109.6C19—N1—P1135.7 (3)
O4—C29—H29B109.6C21—O2—C22116.8 (3)
H29A—C29—H29B108.1C28—O4—C29115.9 (3)
C29—C30—H30A109.5C49—N3—P2139.8 (3)
C29—C30—H30B109.5C51—O6—C52'105.2 (7)
H30A—C30—H30B109.5C51—O6—C52121.7 (8)
C29—C30—H30C109.5C52'—O6—C5230.3 (9)
H30A—C30—H30C109.5C58—O8—C59116.8 (3)
H30B—C30—H30C109.5N1—P1—C7116.42 (16)
C32—C31—C36118.7 (4)N1—P1—C1115.43 (17)
C32—C31—P2121.5 (3)C7—P1—C1111.13 (17)
C36—C31—P2119.6 (3)N1—P1—C13104.62 (17)
C33—C32—C31120.5 (4)C7—P1—C13105.05 (18)
C33—C32—H32119.7C1—P1—C13102.30 (17)
C31—C32—H32119.7N3—P2—C43116.30 (17)
C34—C33—C32120.3 (4)N3—P2—C31116.02 (16)
C34—C33—H33119.8C43—P2—C31111.32 (16)
C32—C33—H33119.8N3—P2—C37102.20 (16)
C33—C34—C35120.5 (4)C43—P2—C37104.06 (16)
C33—C34—H34119.7C31—P2—C37104.99 (18)
C35—C34—H34119.7C25—S1—C2090.27 (18)
C34—C35—C36120.1 (4)C25—S2—C2789.98 (18)
C34—C35—H35119.9C55—S3—C5090.79 (17)
C36—C35—H35119.9C55—S4—C5789.99 (17)
C31—C36—C35119.7 (4)
C6—C1—C2—C32.6 (6)C55—C54—C56—N4179.7 (3)
P1—C1—C2—C3177.7 (3)C49—C54—C56—N41.8 (6)
C1—C2—C3—C42.7 (7)C55—C54—C56—C570.8 (4)
C2—C3—C4—C51.6 (7)C49—C54—C56—C57177.7 (3)
C3—C4—C5—C60.4 (7)N4—C56—C57—C582.7 (6)
C4—C5—C6—C10.4 (7)C54—C56—C57—C58176.7 (3)
C2—C1—C6—C51.5 (6)N4—C56—C57—S4179.5 (3)
P1—C1—C6—C5176.7 (3)C54—C56—C57—S41.1 (4)
C12—C7—C8—C91.4 (6)C56—C57—C58—O71.5 (6)
P1—C7—C8—C9177.1 (4)S4—C57—C58—O7176.1 (3)
C7—C8—C9—C100.1 (8)C56—C57—C58—O8180.0 (3)
C8—C9—C10—C110.8 (8)S4—C57—C58—O82.4 (5)
C9—C10—C11—C120.0 (8)C20—C19—N1—P119.4 (6)
C8—C7—C12—C112.2 (6)C24—C19—N1—P1163.9 (3)
P1—C7—C12—C11176.2 (3)O1—C21—O2—C226.6 (6)
C10—C11—C12—C71.5 (7)C20—C21—O2—C22171.7 (4)
C18—C13—C14—C150.1 (6)C23—C22—O2—C2178.1 (6)
P1—C13—C14—C15177.5 (3)O3—C28—O4—C290.1 (6)
C13—C14—C15—C160.3 (7)C27—C28—O4—C29178.5 (3)
C14—C15—C16—C170.9 (8)C30—C29—O4—C28141.1 (4)
C15—C16—C17—C181.2 (9)C50—C49—N3—P217.1 (7)
C16—C17—C18—C131.0 (8)C54—C49—N3—P2162.3 (3)
C14—C13—C18—C170.4 (6)O5—C51—O6—C52'19.1 (18)
P1—C13—C18—C17177.1 (4)C50—C51—O6—C52'161.2 (17)
N1—C19—C20—C214.0 (6)O5—C51—O6—C528.9 (7)
C24—C19—C20—C21172.9 (4)C50—C51—O6—C52170.9 (5)
N1—C19—C20—S1177.7 (3)C53'—C52'—O6—C51180 (3)
C24—C19—C20—S10.8 (4)C53'—C52'—O6—C5252.4 (19)
C19—C20—C21—O16.6 (7)C53—C52—O6—C51107.4 (14)
S1—C20—C21—O1180.0 (3)C53—C52—O6—C52'44 (2)
C19—C20—C21—O2171.6 (3)O7—C58—O8—C594.6 (6)
S1—C20—C21—O21.8 (4)C57—C58—O8—C59174.0 (3)
N1—C19—C24—C25178.8 (3)C60—C59—O8—C5898.3 (5)
C20—C19—C24—C251.4 (4)C19—N1—P1—C745.8 (4)
N1—C19—C24—C261.6 (5)C19—N1—P1—C187.2 (4)
C20—C19—C24—C26179.0 (3)C19—N1—P1—C13161.2 (3)
C26—C24—C25—S1178.9 (2)C12—C7—P1—N1141.8 (3)
C19—C24—C25—S11.4 (4)C8—C7—P1—N139.8 (4)
C26—C24—C25—S20.3 (4)C12—C7—P1—C16.9 (4)
C19—C24—C25—S2179.9 (2)C8—C7—P1—C1174.7 (3)
C25—C24—C26—N2179.6 (3)C12—C7—P1—C13103.0 (4)
C19—C24—C26—N20.8 (6)C8—C7—P1—C1375.4 (3)
C25—C24—C26—C270.0 (4)C6—C1—P1—N19.4 (4)
C19—C24—C26—C27179.6 (3)C2—C1—P1—N1165.7 (3)
N2—C26—C27—C281.5 (6)C6—C1—P1—C7126.0 (3)
C24—C26—C27—C28178.0 (3)C2—C1—P1—C758.9 (4)
N2—C26—C27—S2179.2 (3)C6—C1—P1—C13122.3 (3)
C24—C26—C27—S20.3 (4)C2—C1—P1—C1352.8 (3)
C26—C27—C28—O31.5 (6)C14—C13—P1—N143.2 (3)
S2—C27—C28—O3178.9 (3)C18—C13—P1—N1139.3 (3)
C26—C27—C28—O4176.9 (3)C14—C13—P1—C7166.4 (3)
S2—C27—C28—O40.6 (5)C18—C13—P1—C716.2 (4)
C36—C31—C32—C331.3 (6)C14—C13—P1—C177.5 (3)
P2—C31—C32—C33178.1 (3)C18—C13—P1—C1100.0 (4)
C31—C32—C33—C341.3 (6)C49—N3—P2—C4346.9 (4)
C32—C33—C34—C351.1 (7)C49—N3—P2—C3187.0 (4)
C33—C34—C35—C360.9 (7)C49—N3—P2—C37159.5 (4)
C32—C31—C36—C351.1 (6)C48—C43—P2—N318.3 (3)
P2—C31—C36—C35177.9 (3)C44—C43—P2—N3166.5 (3)
C34—C35—C36—C310.9 (7)C48—C43—P2—C31154.2 (3)
C42—C37—C38—C390.6 (7)C44—C43—P2—C3130.6 (4)
P2—C37—C38—C39171.0 (4)C48—C43—P2—C3793.2 (3)
C37—C38—C39—C400.1 (8)C44—C43—P2—C3782.0 (3)
C38—C39—C40—C410.2 (9)C32—C31—P2—N3158.5 (3)
C39—C40—C41—C420.9 (9)C36—C31—P2—N318.2 (4)
C38—C37—C42—C411.2 (6)C32—C31—P2—C4365.4 (4)
P2—C37—C42—C41170.5 (4)C36—C31—P2—C43117.8 (3)
C40—C41—C42—C371.4 (8)C32—C31—P2—C3746.6 (3)
C48—C43—C44—C450.5 (6)C36—C31—P2—C37130.2 (3)
P2—C43—C44—C45174.6 (3)C38—C37—P2—N391.4 (3)
C43—C44—C45—C460.2 (6)C42—C37—P2—N379.9 (3)
C44—C45—C46—C470.5 (7)C38—C37—P2—C4330.0 (4)
C45—C46—C47—C480.8 (6)C42—C37—P2—C43158.6 (3)
C46—C47—C48—C430.5 (6)C38—C37—P2—C31147.0 (3)
C44—C43—C48—C470.2 (6)C42—C37—P2—C3141.6 (4)
P2—C43—C48—C47175.3 (3)C24—C25—S1—C200.7 (3)
N3—C49—C50—C510.9 (6)S2—C25—S1—C20178.9 (3)
C54—C49—C50—C51179.7 (3)C19—C20—S1—C250.1 (3)
N3—C49—C50—S3179.8 (3)C21—C20—S1—C25174.3 (3)
C54—C49—C50—S30.4 (4)C24—C25—S2—C270.5 (3)
C49—C50—C51—O51.6 (6)S1—C25—S2—C27178.6 (3)
S3—C50—C51—O5179.1 (3)C26—C27—S2—C250.5 (3)
C49—C50—C51—O6178.7 (3)C28—C27—S2—C25178.2 (3)
S3—C50—C51—O60.6 (4)C54—C55—S3—C500.6 (3)
N3—C49—C54—C55179.4 (3)S4—C55—S3—C50178.3 (3)
C50—C49—C54—C550.1 (4)C49—C50—S3—C550.6 (3)
N3—C49—C54—C560.9 (5)C51—C50—S3—C55180.0 (3)
C50—C49—C54—C56178.5 (3)C54—C55—S4—C570.4 (3)
C56—C54—C55—S3179.3 (2)S3—C55—S4—C57178.6 (3)
C49—C54—C55—S30.5 (4)C56—C57—S4—C550.8 (3)
C56—C54—C55—S40.2 (4)C58—C57—S4—C55177.0 (3)
C49—C54—C55—S4178.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C33—H33···O30.932.463.298 (5)151
N4—H4B···O70.862.162.817 (4)134
N4—H4A···N30.862.292.945 (4)133
N2—H2B···O30.862.192.832 (4)131
N2—H2A···N10.862.332.965 (4)131

Experimental details

Crystal data
Chemical formulaC30H27N2O4PS2
Mr574.63
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)13.1260 (9), 15.3616 (10), 16.6497 (11)
α, β, γ (°)68.140 (1), 71.043 (1), 68.969 (1)
V3)2836.5 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.28
Crystal size (mm)0.20 × 0.10 × 0.06
Data collection
DiffractometerBruker SMART 4K CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.946, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections
20968, 10981, 6314
Rint0.053
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.068, 0.159, 0.96
No. of reflections10981
No. of parameters727
No. of restraints6
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.48, 0.28

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C33—H33···O30.932.463.298 (5)150.6
N4—H4B···O70.862.162.817 (4)133.7
N4—H4A···N30.862.292.945 (4)133.0
N2—H2B···O30.862.192.832 (4)130.8
N2—H2A···N10.862.332.965 (4)131.0
 

Acknowledgements

The authors gratefully acknowledge financial support of this work by the Opening Foundation of the Key Laboratory of Three Gorges University of China (grant No. 2006NP01).

References

First citationBruker (2001). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationDing, M. W., Xu, S. Z. & Zhao, J. F. (2004). J. Org. Chem. 69, 8366–8371.  Web of Science CrossRef PubMed CAS Google Scholar
First citationLiao, Q.-B., Huang, J., Yang, Z.-Z. & Liu, M.-G. (2007). Acta Cryst. E63, o3824.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationLiu, M.-G. & Hu, Y.-G. (2006). Acta Cryst. E62, o3206–o3208.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWalter, H. (1999a). PCT Int. Appl. No. 44; WO 9911631.  Google Scholar
First citationWalter, H. (1999b). PCT Int. Appl. No. 89; WO 9914202.  Google Scholar

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