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Acta Crystallogr Sect E Struct Rep Online. 2008 July 1; 64(Pt 7): o1252.
Published online 2008 June 13. doi:  10.1107/S1600536808017108
PMCID: PMC2961713

3′,6′-Bis(diethyl­amino)-2-(2-hydroxy­ethyl­amino)spiro­[isoindoline-1,9′-xanthen]-3-one

Abstract

In the title mol­ecule, C30H36N4O3, the dihedral angle between the planes of the xanthene and spiro­lactam rings systems is 88.69 (4)°. Both C atoms of one of the ethyl groups are disordered over two sites with occupancies 0.72 (2)/0.28 (2). The conformation of the mol­ecule may be influenced by two intra­molecular hydrogen bonds.

Related literature

For related literature, see: Zhang et al. (2007 [triangle]); Wu et al. (2007 [triangle]); Bae & Tae 2007 [triangle]).

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Object name is e-64-o1252-scheme1.jpg

Experimental

Crystal data

  • C30H36N4O3
  • M r = 500.63
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1252-efi1.jpg
  • a = 12.269 (4) Å
  • b = 12.203 (4) Å
  • c = 18.458 (6) Å
  • β = 108.127 (5)°
  • V = 2626.4 (15) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 298 (2) K
  • 0.58 × 0.25 × 0.25 mm

Data collection

  • Bruker SMART APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.849, T max = 0.900 (expected range = 0.924–0.979)
  • 17363 measured reflections
  • 4620 independent reflections
  • 2841 reflections with I > 2σ(I)
  • R int = 0.064

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.129
  • S = 1.00
  • 4620 reflections
  • 359 parameters
  • 13 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808017108/lh2636sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017108/lh2636Isup2.hkl

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

Acknowledgments

Financial support in part by the Natural Science Foundation of China (20376010 and 20472012) and Shanxi Scholarship Council of China (200310) is gratefully acknowledged.

supplementary crystallographic information

Comment

Rhodamine dyes are molecules used extensively as fluorescent labeling reagents and dye laser sources because of their excellent photophysical properties, such as long absorption and emission wavelengths elongated to visible region, high fluorescence quantum yield, and large absorption coefficient. (Zhang et al., 2007; Wu et al., 2007; Bae & Tae, 2007). Detailed information on their molecular and crystal structures is necessary to understand their photophysical and photochemical properties. As part of our own work on rhodamine derivatives, we report here the synthesis and crystal structure of the title compound (I).

As shown in Fig.1, the xanthene ring is close to planar with an r.m.s. deviation of 0.089 (9) Å. The lactam moiety of the molecule is oriented nearly orthogonal to the xanthene moiety i.e. the dihedral angle between the planes of the xanthene and the spirolactam rings systems is 88.69 (4)°.

Experimental

Sodium borohydride (15.2 mg, 0.4 mmol) was slowly added to a solution of compound 3',6'-Bis(diethylamino)-2-(2-oxoethylideneamino)spiro [isoindoline-1,9'-xanthen]-3-one (150 mg, 0.3 mmol) in ethanol (20 ml). The reaction mixture was stirred for 2 h at room temperature and solvent was totally removed under reduced pressure. The crude product was dissolved in CH2Cl2 (20 ml) and 3 ml of an aqueous solution of K2CO3 was added. The organic layer was dried over MgSO4. After filtration, the solvent was removed under reduced pressure. The residue was placed on a silica gel column (200–300 mesh). The column was eluted with a mixture (2:1, v/v) of petroleum spirit/ethyl acetate, to give 136 mg of the title compound (90%). Crystals were grown by dissolving the compound in CH2Cl2 and slowly diffusing n-hexane into the solution.

Refinement

H atoms bonded to Catoms were positioned geometrically (C—H = 0.93–0.97 Å) and refined as riding, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). The positional parameters of the H atoms bonded to N and O were refined independently with Uiso(H) = 1.5Ueq(N,O).

Figures

Fig. 1.
The molecular structure of (I), showing the atom-numbering scheme and displacement ellipsoids at the 30% probability level. H atoms bonded to C atoms have been omitted and the disorder is not shown.

Crystal data

C30H36N4O3F000 = 1072
Mr = 500.63Dx = 1.266 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3630 reflections
a = 12.269 (4) Åθ = 2.0–25.0º
b = 12.203 (4) ŵ = 0.08 mm1
c = 18.458 (6) ÅT = 298 (2) K
β = 108.127 (5)ºBlock, white
V = 2626.4 (15) Å30.58 × 0.25 × 0.25 mm
Z = 4

Data collection

Bruker SMART APEXII diffractometer4620 independent reflections
Radiation source: fine-focus sealed tube2841 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.064
T = 298(2) Kθmax = 25.0º
[var phi] and ω scansθmin = 2.0º
Absorption correction: multi-scan(SADABS; Bruker, 2005)h = −14→14
Tmin = 0.849, Tmax = 0.900k = −14→14
17363 measured reflectionsl = −21→21

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.129  w = 1/[σ2(Fo2) + (0.0755P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.002
4620 reflectionsΔρmax = 0.21 e Å3
359 parametersΔρmin = −0.20 e Å3
13 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.026 (4)

Special details

Experimental. 1H NMR (CDCl3, 400MHz, Me4Si): δ 7.91 (d, 1H, J=6.4 Hz, C6H4), 7.52-7.47 (m, 2H, C6H4), 7.15 (d, 1H, J= 6.4 Hz), 6.41 (m, 4H, Xanthene-H), 6.26 (dd, 2H, J= 8.8 Hz, J= 2.4 Hz, Xanthene-H), 4.65 (t, 1H, J= 7.2 Hz, NH), 4.45 (t, 1H, J= 6.0 Hz, OH), 3.36-3.31 (m, 10H, CH2O, CH2), 2.46-2.45 (m, 2H, CH2N), 1.16 (t, 12H, J=6.8 Hz, CH3); 13C NMR (CDCl3, 100MHz, Me4Si): δ 168.31, 164.31, 153.97, 151.59, 149.05, 133.17, 129.99, 128.51, 123.08, 124.20, 107.97, 105.29, 97.98, 66.39, 58.76, 52.83, 44.51, 12.75. HRMS(ESI): calcd for C30H36N4O3 [M+Na]+ 523.2685; found 523.2671.
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 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
O10.02779 (11)0.63551 (12)0.15665 (9)0.0590 (5)
O2−0.40178 (12)0.91274 (15)0.13067 (9)0.0670 (5)
O3−0.34132 (15)0.9162 (2)0.28884 (13)0.0941 (7)
H3O−0.370 (3)0.915 (3)0.232 (2)0.141*
N10.31949 (16)0.86643 (19)0.30367 (13)0.0770 (7)
N2−0.19898 (16)0.38340 (17)−0.02009 (11)0.0620 (5)
N3−0.22666 (13)0.83188 (15)0.15192 (9)0.0443 (4)
N4−0.23247 (17)0.76085 (17)0.20976 (11)0.0570 (5)
H1N−0.313 (2)0.749 (2)0.2013 (14)0.085*
C10.05554 (16)0.74041 (19)0.18219 (11)0.0459 (5)
C20.16682 (17)0.7528 (2)0.22812 (12)0.0551 (6)
H2A0.21550.69250.23860.066*
C30.20776 (17)0.8541 (2)0.25922 (13)0.0525 (6)
C40.13007 (17)0.94070 (19)0.24316 (12)0.0488 (6)
H4A0.15301.00930.26430.059*
C50.02040 (17)0.92561 (18)0.19652 (12)0.0468 (5)
H5A−0.02920.98530.18630.056*
C6−0.02056 (15)0.82580 (18)0.16369 (11)0.0407 (5)
C7−0.14135 (15)0.81057 (17)0.11196 (11)0.0417 (5)
C8−0.15672 (16)0.69727 (18)0.07841 (11)0.0439 (5)
C9−0.25529 (17)0.6667 (2)0.02086 (13)0.0570 (6)
H9A−0.31300.71860.00300.068*
C10−0.27173 (19)0.5653 (2)−0.01066 (13)0.0593 (6)
H10A−0.33980.5491−0.04870.071*
C11−0.18663 (17)0.48494 (19)0.01373 (12)0.0501 (6)
C12−0.08854 (17)0.51411 (19)0.07132 (12)0.0494 (6)
H12A−0.03070.46260.08980.059*
C13−0.07482 (16)0.61794 (18)0.10178 (11)0.0436 (5)
C140.4083 (4)0.7842 (6)0.2970 (4)0.062 (2)0.720 (17)
H14A0.38150.74810.24780.074*0.720 (17)
H14B0.47920.82210.30020.074*0.720 (17)
C150.4301 (7)0.7010 (7)0.3586 (4)0.099 (2)0.720 (17)
H15A0.48630.64960.35330.149*0.720 (17)
H15B0.36010.66310.35500.149*0.720 (17)
H15C0.45800.73670.40720.149*0.720 (17)
C14A0.3796 (13)0.7676 (16)0.3463 (9)0.074 (7)0.280 (17)
H14C0.42890.78690.39690.088*0.280 (17)
H14D0.32540.71200.35050.088*0.280 (17)
C15A0.4469 (17)0.731 (2)0.2969 (13)0.111 (7)0.280 (17)
H15D0.49040.66680.31870.166*0.280 (17)
H15E0.49830.78810.29280.166*0.280 (17)
H15F0.39590.71350.24720.166*0.280 (17)
C160.3656 (2)0.9732 (2)0.33183 (16)0.0739 (8)
H16A0.43320.96330.37570.089*
H16B0.30921.01280.34850.089*
C170.3969 (2)1.0400 (3)0.27363 (18)0.0852 (9)
H17A0.42691.10940.29530.128*
H17B0.32991.05170.23050.128*
H17C0.45391.00200.25760.128*
C18−0.3044 (2)0.3522 (2)−0.07672 (14)0.0690 (7)
H18A−0.28900.2907−0.10540.083*
H18B−0.33010.4127−0.11200.083*
C19−0.3997 (2)0.3211 (3)−0.04619 (17)0.0877 (9)
H19A−0.46650.3023−0.08770.132*
H19B−0.41700.3817−0.01850.132*
H19C−0.37660.2592−0.01270.132*
C20−0.1110 (2)0.2997 (2)0.00744 (14)0.0665 (7)
H20A−0.03630.33390.01830.080*
H20B−0.11830.2465−0.03280.080*
C21−0.1165 (2)0.2407 (2)0.07736 (15)0.0744 (8)
H21A−0.05610.18740.09210.112*
H21B−0.18930.20470.06680.112*
H21C−0.10750.29240.11800.112*
C22−0.34216 (19)1.0120 (2)−0.00789 (14)0.0593 (6)
H22A−0.41181.0420−0.00780.071*
C23−0.2949 (2)1.0373 (2)−0.06426 (14)0.0654 (7)
H23A−0.33401.0832−0.10410.078*
C24−0.1899 (2)0.9951 (2)−0.06186 (14)0.0692 (7)
H24A−0.15741.0154−0.09910.083*
C25−0.13217 (19)0.9237 (2)−0.00578 (13)0.0571 (6)
H25A−0.06170.8949−0.00510.068*
C26−0.18049 (16)0.89571 (18)0.04935 (12)0.0455 (5)
C27−0.28307 (16)0.94066 (18)0.04841 (12)0.0482 (6)
C28−0.31390 (17)0.89661 (19)0.11342 (12)0.0499 (6)
C29−0.1807 (2)0.8051 (3)0.28589 (13)0.0694 (8)
H29A−0.09860.81010.29530.083*
H29B−0.19330.75340.32240.083*
C30−0.2233 (2)0.9153 (3)0.30112 (16)0.0804 (9)
H30A−0.18420.93610.35350.097*
H30B−0.20480.96930.26820.097*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0457 (8)0.0423 (10)0.0714 (10)0.0041 (7)−0.0072 (7)−0.0086 (8)
O20.0416 (8)0.0841 (14)0.0751 (11)0.0098 (8)0.0178 (8)0.0037 (9)
O30.0625 (11)0.143 (2)0.0822 (13)0.0030 (11)0.0306 (10)−0.0282 (13)
N10.0511 (11)0.0595 (16)0.0937 (16)0.0007 (10)−0.0163 (11)−0.0167 (13)
N20.0701 (12)0.0476 (13)0.0588 (13)−0.0039 (10)0.0065 (10)−0.0138 (10)
N30.0412 (9)0.0439 (11)0.0479 (10)0.0031 (8)0.0141 (7)0.0043 (9)
N40.0620 (11)0.0576 (14)0.0535 (12)0.0019 (10)0.0211 (10)0.0056 (10)
C10.0424 (11)0.0430 (15)0.0490 (13)−0.0023 (10)0.0093 (9)−0.0057 (10)
C20.0467 (12)0.0491 (16)0.0587 (14)0.0057 (11)0.0009 (10)−0.0040 (12)
C30.0426 (11)0.0570 (17)0.0505 (13)−0.0034 (11)0.0039 (9)−0.0047 (11)
C40.0479 (12)0.0478 (15)0.0502 (13)−0.0037 (10)0.0146 (10)−0.0092 (11)
C50.0431 (11)0.0436 (15)0.0547 (13)0.0025 (10)0.0167 (10)−0.0038 (11)
C60.0376 (10)0.0411 (14)0.0427 (11)0.0011 (9)0.0115 (8)0.0000 (10)
C70.0368 (10)0.0389 (14)0.0484 (12)−0.0003 (9)0.0117 (9)−0.0015 (10)
C80.0395 (10)0.0429 (14)0.0467 (12)0.0005 (10)0.0097 (9)−0.0005 (10)
C90.0465 (12)0.0463 (16)0.0650 (15)0.0033 (11)−0.0019 (10)−0.0006 (12)
C100.0540 (13)0.0500 (16)0.0581 (15)−0.0037 (12)−0.0055 (11)−0.0046 (12)
C110.0545 (13)0.0475 (15)0.0454 (13)−0.0040 (11)0.0115 (10)−0.0019 (11)
C120.0487 (12)0.0407 (15)0.0538 (14)0.0038 (10)0.0086 (10)−0.0014 (11)
C130.0382 (10)0.0451 (14)0.0430 (12)−0.0011 (10)0.0061 (9)−0.0005 (10)
C140.039 (2)0.073 (4)0.067 (3)−0.001 (2)0.007 (2)−0.008 (3)
C150.116 (4)0.091 (5)0.083 (4)0.042 (4)0.021 (3)0.013 (3)
C14A0.058 (8)0.085 (14)0.068 (9)−0.009 (8)0.006 (6)−0.020 (7)
C15A0.089 (11)0.114 (16)0.137 (16)0.022 (9)0.046 (10)−0.030 (12)
C160.0539 (13)0.074 (2)0.0739 (18)−0.0028 (13)−0.0099 (13)−0.0210 (16)
C170.0611 (16)0.084 (2)0.109 (2)−0.0023 (15)0.0243 (16)−0.0150 (19)
C180.0865 (17)0.0548 (18)0.0527 (15)−0.0111 (14)0.0029 (13)−0.0077 (12)
C190.0829 (18)0.075 (2)0.092 (2)−0.0107 (16)0.0089 (16)0.0116 (17)
C200.0777 (16)0.0508 (17)0.0700 (17)−0.0048 (13)0.0216 (13)−0.0173 (13)
C210.0750 (17)0.071 (2)0.0689 (17)−0.0050 (14)0.0101 (13)−0.0033 (15)
C220.0542 (13)0.0487 (16)0.0643 (16)0.0053 (11)0.0026 (12)0.0008 (13)
C230.0765 (17)0.0556 (17)0.0541 (15)−0.0006 (13)0.0058 (13)0.0085 (13)
C240.0820 (17)0.071 (2)0.0526 (15)−0.0097 (15)0.0179 (13)0.0046 (14)
C250.0563 (13)0.0583 (17)0.0585 (15)0.0003 (12)0.0206 (11)0.0047 (13)
C260.0426 (11)0.0405 (14)0.0485 (13)−0.0011 (9)0.0069 (9)−0.0037 (10)
C270.0421 (11)0.0428 (14)0.0529 (14)−0.0006 (10)0.0048 (9)0.0013 (11)
C280.0363 (11)0.0513 (15)0.0580 (14)0.0023 (10)0.0086 (10)−0.0027 (11)
C290.0540 (13)0.103 (2)0.0488 (15)0.0018 (14)0.0126 (11)0.0089 (15)
C300.0612 (15)0.114 (3)0.0668 (17)−0.0129 (16)0.0209 (13)−0.0303 (17)

Geometric parameters (Å, °)

O1—C131.365 (2)C15—H15B0.9600
O1—C11.370 (3)C15—H15C0.9600
O2—C281.231 (2)C14A—C15A1.48 (4)
O3—C301.394 (3)C14A—H14C0.9700
O3—H3O0.99 (4)C14A—H14D0.9700
N1—C31.369 (3)C15A—H15D0.9600
N1—C161.450 (3)C15A—H15E0.9600
N1—C14A1.50 (2)C15A—H15F0.9600
N1—C141.514 (8)C16—C171.491 (4)
N2—C111.374 (3)C16—H16A0.9700
N2—C181.438 (3)C16—H16B0.9700
N2—C201.457 (3)C17—H17A0.9600
N3—C281.342 (3)C17—H17B0.9600
N3—N41.394 (2)C17—H17C0.9600
N3—C71.479 (2)C18—C191.496 (4)
N4—C291.454 (3)C18—H18A0.9700
N4—H1N0.96 (3)C18—H18B0.9700
C1—C61.370 (3)C19—H19A0.9600
C1—C21.373 (3)C19—H19B0.9600
C2—C31.389 (3)C19—H19C0.9600
C2—H2A0.9300C20—C211.497 (4)
C3—C41.392 (3)C20—H20A0.9700
C4—C51.365 (3)C20—H20B0.9700
C4—H4A0.9300C21—H21A0.9600
C5—C61.383 (3)C21—H21B0.9600
C5—H5A0.9300C21—H21C0.9600
C6—C71.504 (3)C22—C231.375 (3)
C7—C81.503 (3)C22—C271.376 (3)
C7—C261.517 (3)C22—H22A0.9300
C8—C131.365 (3)C23—C241.375 (3)
C8—C91.389 (3)C23—H23A0.9300
C9—C101.355 (3)C24—C251.370 (3)
C9—H9A0.9300C24—H24A0.9300
C10—C111.401 (3)C25—C261.371 (3)
C10—H10A0.9300C25—H25A0.9300
C11—C121.382 (3)C26—C271.368 (3)
C12—C131.375 (3)C27—C281.468 (3)
C12—H12A0.9300C29—C301.501 (4)
C14—C151.485 (13)C29—H29A0.9700
C14—H14A0.9700C29—H29B0.9700
C14—H14B0.9700C30—H30A0.9700
C15—H15A0.9600C30—H30B0.9700
C13—O1—C1118.37 (16)H14C—C14A—H14D109.3
C30—O3—H3O101 (2)C14A—C15A—H15D109.5
C3—N1—C16121.3 (2)C14A—C15A—H15E109.5
C3—N1—C14A117.6 (5)H15D—C15A—H15E109.5
C16—N1—C14A117.4 (4)C14A—C15A—H15F109.5
C3—N1—C14119.3 (2)H15D—C15A—H15F109.5
C16—N1—C14114.5 (2)H15E—C15A—H15F109.5
C14A—N1—C1442.5 (6)N1—C16—C17113.1 (2)
C11—N2—C18121.1 (2)N1—C16—H16A109.0
C11—N2—C20120.56 (19)C17—C16—H16A109.0
C18—N2—C20117.9 (2)N1—C16—H16B109.0
C28—N3—N4123.30 (17)C17—C16—H16B109.0
C28—N3—C7114.26 (17)H16A—C16—H16B107.8
N4—N3—C7119.03 (16)C16—C17—H17A109.5
N3—N4—C29113.5 (2)C16—C17—H17B109.5
N3—N4—H1N105.4 (16)H17A—C17—H17B109.5
C29—N4—H1N109.4 (15)C16—C17—H17C109.5
C6—C1—O1123.23 (17)H17A—C17—H17C109.5
C6—C1—C2122.7 (2)H17B—C17—H17C109.5
O1—C1—C2114.11 (19)N2—C18—C19115.1 (2)
C1—C2—C3121.0 (2)N2—C18—H18A108.5
C1—C2—H2A119.5C19—C18—H18A108.5
C3—C2—H2A119.5N2—C18—H18B108.5
N1—C3—C2120.7 (2)C19—C18—H18B108.5
N1—C3—C4122.4 (2)H18A—C18—H18B107.5
C2—C3—C4116.86 (19)C18—C19—H19A109.5
C5—C4—C3120.5 (2)C18—C19—H19B109.5
C5—C4—H4A119.8H19A—C19—H19B109.5
C3—C4—H4A119.8C18—C19—H19C109.5
C4—C5—C6123.2 (2)H19A—C19—H19C109.5
C4—C5—H5A118.4H19B—C19—H19C109.5
C6—C5—H5A118.4N2—C20—C21114.2 (2)
C1—C6—C5115.73 (18)N2—C20—H20A108.7
C1—C6—C7121.66 (19)C21—C20—H20A108.7
C5—C6—C7122.61 (18)N2—C20—H20B108.7
N3—C7—C8110.47 (16)C21—C20—H20B108.7
N3—C7—C6111.84 (16)H20A—C20—H20B107.6
C8—C7—C6110.36 (16)C20—C21—H21A109.5
N3—C7—C2698.86 (15)C20—C21—H21B109.5
C8—C7—C26110.30 (17)H21A—C21—H21B109.5
C6—C7—C26114.52 (17)C20—C21—H21C109.5
C13—C8—C9115.6 (2)H21A—C21—H21C109.5
C13—C8—C7122.46 (18)H21B—C21—H21C109.5
C9—C8—C7121.98 (19)C23—C22—C27117.8 (2)
C10—C9—C8123.4 (2)C23—C22—H22A121.1
C10—C9—H9A118.3C27—C22—H22A121.1
C8—C9—H9A118.3C24—C23—C22120.2 (2)
C9—C10—C11120.3 (2)C24—C23—H23A119.9
C9—C10—H10A119.8C22—C23—H23A119.9
C11—C10—H10A119.8C25—C24—C23121.5 (2)
N2—C11—C12121.9 (2)C25—C24—H24A119.3
N2—C11—C10121.3 (2)C23—C24—H24A119.3
C12—C11—C10116.8 (2)C24—C25—C26118.6 (2)
C13—C12—C11121.2 (2)C24—C25—H25A120.7
C13—C12—H12A119.4C26—C25—H25A120.7
C11—C12—H12A119.4C27—C26—C25119.9 (2)
O1—C13—C8122.78 (19)C27—C26—C7110.87 (18)
O1—C13—C12114.55 (18)C25—C26—C7128.97 (19)
C8—C13—C12122.67 (19)C26—C27—C22122.0 (2)
C15—C14—N1110.7 (7)C26—C27—C28108.24 (18)
C15—C14—H14A109.5C22—C27—C28129.8 (2)
N1—C14—H14A109.5O2—C28—N3125.1 (2)
C15—C14—H14B109.5O2—C28—C27128.5 (2)
N1—C14—H14B109.5N3—C28—C27106.41 (17)
H14A—C14—H14B108.1N4—C29—C30116.2 (2)
C14—C15—H15A109.5N4—C29—H29A108.2
C14—C15—H15B109.5C30—C29—H29A108.2
H15A—C15—H15B109.5N4—C29—H29B108.2
C14—C15—H15C109.5C30—C29—H29B108.2
H15A—C15—H15C109.5H29A—C29—H29B107.4
H15B—C15—H15C109.5O3—C30—C29112.4 (2)
C15A—C14A—N1101.4 (18)O3—C30—H30A109.1
C15A—C14A—H14C111.5C29—C30—H30A109.1
N1—C14A—H14C111.5O3—C30—H30B109.1
C15A—C14A—H14D111.5C29—C30—H30B109.1
N1—C14A—H14D111.5H30A—C30—H30B107.9
C28—N3—N4—C29−98.3 (2)N2—C11—C12—C13176.4 (2)
C7—N3—N4—C29103.7 (2)C10—C11—C12—C13−1.3 (3)
C13—O1—C1—C69.6 (3)C1—O1—C13—C8−8.6 (3)
C13—O1—C1—C2−170.31 (18)C1—O1—C13—C12170.74 (18)
C6—C1—C2—C30.7 (4)C9—C8—C13—O1178.64 (18)
O1—C1—C2—C3−179.3 (2)C7—C8—C13—O1−0.8 (3)
C16—N1—C3—C2175.4 (2)C9—C8—C13—C12−0.6 (3)
C14A—N1—C3—C2−27.0 (8)C7—C8—C13—C12179.92 (19)
C14—N1—C3—C221.6 (5)C11—C12—C13—O1−178.19 (19)
C16—N1—C3—C4−4.9 (4)C11—C12—C13—C81.1 (3)
C14A—N1—C3—C4152.7 (8)C3—N1—C14—C15−98.4 (4)
C14—N1—C3—C4−158.7 (4)C16—N1—C14—C15106.1 (4)
C1—C2—C3—N1−178.6 (2)C14A—N1—C14—C151.5 (7)
C1—C2—C3—C41.6 (3)C3—N1—C14A—C15A100.1 (9)
N1—C3—C4—C5177.9 (2)C16—N1—C14A—C15A−101.4 (9)
C2—C3—C4—C5−2.4 (3)C14—N1—C14A—C15A−4.3 (8)
C3—C4—C5—C60.9 (3)C3—N1—C16—C17−79.7 (3)
O1—C1—C6—C5177.82 (18)C14A—N1—C16—C17122.7 (8)
C2—C1—C6—C5−2.2 (3)C14—N1—C16—C1775.3 (4)
O1—C1—C6—C7−1.2 (3)C11—N2—C18—C19−77.1 (3)
C2—C1—C6—C7178.74 (19)C20—N2—C18—C1995.2 (3)
C4—C5—C6—C11.5 (3)C11—N2—C20—C2179.8 (3)
C4—C5—C6—C7−179.54 (19)C18—N2—C20—C21−92.5 (3)
C28—N3—C7—C8−103.7 (2)C27—C22—C23—C24−2.3 (4)
N4—N3—C7—C856.2 (2)C22—C23—C24—C252.8 (4)
C28—N3—C7—C6132.94 (19)C23—C24—C25—C26−0.9 (4)
N4—N3—C7—C6−67.2 (2)C24—C25—C26—C27−1.4 (4)
C28—N3—C7—C2611.9 (2)C24—C25—C26—C7172.8 (2)
N4—N3—C7—C26171.83 (17)N3—C7—C26—C27−9.7 (2)
C1—C6—C7—N3116.1 (2)C8—C7—C26—C27106.1 (2)
C5—C6—C7—N3−62.9 (3)C6—C7—C26—C27−128.69 (19)
C1—C6—C7—C8−7.3 (3)N3—C7—C26—C25175.7 (2)
C5—C6—C7—C8173.74 (18)C8—C7—C26—C25−68.6 (3)
C1—C6—C7—C26−132.5 (2)C6—C7—C26—C2556.6 (3)
C5—C6—C7—C2648.6 (3)C25—C26—C27—C221.8 (3)
N3—C7—C8—C13−115.9 (2)C7—C26—C27—C22−173.42 (19)
C6—C7—C8—C138.3 (3)C25—C26—C27—C28−179.9 (2)
C26—C7—C8—C13135.9 (2)C7—C26—C27—C284.9 (2)
N3—C7—C8—C964.7 (3)C23—C22—C27—C260.1 (3)
C6—C7—C8—C9−171.09 (18)C23—C22—C27—C28−177.8 (2)
C26—C7—C8—C9−43.6 (3)N4—N3—C28—O210.5 (3)
C13—C8—C9—C100.5 (3)C7—N3—C28—O2169.5 (2)
C7—C8—C9—C10179.9 (2)N4—N3—C28—C27−168.71 (18)
C8—C9—C10—C11−0.8 (4)C7—N3—C28—C27−9.8 (2)
C18—N2—C11—C12176.2 (2)C26—C27—C28—O2−176.5 (2)
C20—N2—C11—C124.1 (3)C22—C27—C28—O21.7 (4)
C18—N2—C11—C10−6.1 (3)C26—C27—C28—N32.8 (2)
C20—N2—C11—C10−178.3 (2)C22—C27—C28—N3−179.1 (2)
C9—C10—C11—N2−176.6 (2)N3—N4—C29—C3053.9 (3)
C9—C10—C11—C121.2 (4)N4—C29—C30—O357.8 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3O···O21.00 (4)1.79 (4)2.780 (3)172 (4)
N4—H1N···O20.96 (3)2.45 (2)2.828 (3)103 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2636).

References

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  • Bruker (2005). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Wu, D., Huang, W., Duan, C.-Y., Lin, Z.-H. & Meng, Q.-J. (2007). Inorg. Chem.46, 1538–1540. [PubMed]
  • Zhang, X., Shiraishi, Y. & Hirai, T. (2007). Org. Lett.9, 5039–5042. [PubMed]

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