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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808017108/lh2636sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536808017108/lh2636Isup2.hkl
Contains datablock I

CCDC reference: 696674

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in main residue
  • R factor = 0.051
  • wR factor = 0.130
  • Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.73 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14A PLAT301_ALERT_3_C Main Residue Disorder ......................... 5.00 Perc. PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.09 PLAT779_ALERT_4_C Suspect or Irrelevant (Bond) Angle in CIF ...... 42.50 Deg. C14A -N1 -C14 1.555 1.555 1.555
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 1.089 Tmax scaled 0.979 Tmin scaled 0.924 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 13
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

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)°.

Related literature top

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

Experimental top

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 top

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).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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. 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.
3',6'-Bis(diethylamino)-2-(2-hydroxyethylamino)spiro[isoindoline-1,9'- xanthen]-3-one top
Crystal data top
C30H36N4O3F(000) = 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 = 2.0–25.0°
b = 12.203 (4) ŵ = 0.08 mm1
c = 18.458 (6) ÅT = 298 K
β = 108.127 (5)°Block, white
V = 2626.4 (15) Å30.58 × 0.25 × 0.25 mm
Z = 4
Data collection top
Bruker SMART APEXII
diffractometer
4620 independent reflections
Radiation source: fine-focus sealed tube2841 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.064
ϕ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1414
Tmin = 0.849, Tmax = 0.900k = 1414
17363 measured reflectionsl = 2121
Refinement top
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)
Crystal data top
C30H36N4O3V = 2626.4 (15) Å3
Mr = 500.63Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.269 (4) ŵ = 0.08 mm1
b = 12.203 (4) ÅT = 298 K
c = 18.458 (6) Å0.58 × 0.25 × 0.25 mm
β = 108.127 (5)°
Data collection top
Bruker SMART APEXII
diffractometer
4620 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
2841 reflections with I > 2σ(I)
Tmin = 0.849, Tmax = 0.900Rint = 0.064
17363 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05013 restraints
wR(F2) = 0.129H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.21 e Å3
4620 reflectionsΔρmin = 0.20 e Å3
359 parameters
Special details top

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) top
xyzUiso*/UeqOcc. (<1)
O10.02779 (11)0.63551 (12)0.15665 (9)0.0590 (5)
O20.40178 (12)0.91274 (15)0.13067 (9)0.0670 (5)
O30.34132 (15)0.9162 (2)0.28884 (13)0.0941 (7)
H3O0.370 (3)0.915 (3)0.232 (2)0.141*
N10.31949 (16)0.86643 (19)0.30367 (13)0.0770 (7)
N20.19898 (16)0.38340 (17)0.02009 (11)0.0620 (5)
N30.22666 (13)0.83188 (15)0.15192 (9)0.0443 (4)
N40.23247 (17)0.76085 (17)0.20976 (11)0.0570 (5)
H1N0.313 (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)
H5A0.02920.98530.18630.056*
C60.02056 (15)0.82580 (18)0.16369 (11)0.0407 (5)
C70.14135 (15)0.81057 (17)0.11196 (11)0.0417 (5)
C80.15672 (16)0.69727 (18)0.07841 (11)0.0439 (5)
C90.25529 (17)0.6667 (2)0.02086 (13)0.0570 (6)
H9A0.31300.71860.00300.068*
C100.27173 (19)0.5653 (2)0.01066 (13)0.0593 (6)
H10A0.33980.54910.04870.071*
C110.18663 (17)0.48494 (19)0.01373 (12)0.0501 (6)
C120.08854 (17)0.51411 (19)0.07132 (12)0.0494 (6)
H12A0.03070.46260.08980.059*
C130.07482 (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*
C180.3044 (2)0.3522 (2)0.07672 (14)0.0690 (7)
H18A0.28900.29070.10540.083*
H18B0.33010.41270.11200.083*
C190.3997 (2)0.3211 (3)0.04619 (17)0.0877 (9)
H19A0.46650.30230.08770.132*
H19B0.41700.38170.01850.132*
H19C0.37660.25920.01270.132*
C200.1110 (2)0.2997 (2)0.00744 (14)0.0665 (7)
H20A0.03630.33390.01830.080*
H20B0.11830.24650.03280.080*
C210.1165 (2)0.2407 (2)0.07736 (15)0.0744 (8)
H21A0.05610.18740.09210.112*
H21B0.18930.20470.06680.112*
H21C0.10750.29240.11800.112*
C220.34216 (19)1.0120 (2)0.00789 (14)0.0593 (6)
H22A0.41181.04200.00780.071*
C230.2949 (2)1.0373 (2)0.06426 (14)0.0654 (7)
H23A0.33401.08320.10410.078*
C240.1899 (2)0.9951 (2)0.06186 (14)0.0692 (7)
H24A0.15741.01540.09910.083*
C250.13217 (19)0.9237 (2)0.00578 (13)0.0571 (6)
H25A0.06170.89490.00510.068*
C260.18049 (16)0.89571 (18)0.04935 (12)0.0455 (5)
C270.28307 (16)0.94066 (18)0.04841 (12)0.0482 (6)
C280.31390 (17)0.89661 (19)0.11342 (12)0.0499 (6)
C290.1807 (2)0.8051 (3)0.28589 (13)0.0694 (8)
H29A0.09860.81010.29530.083*
H29B0.19330.75340.32240.083*
C300.2233 (2)0.9153 (3)0.30112 (16)0.0804 (9)
H30A0.18420.93610.35350.097*
H30B0.20480.96930.26820.097*
Atomic displacement parameters (Å2) top
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, º) top
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—C2998.3 (2)N2—C11—C12—C13176.4 (2)
C7—N3—N4—C29103.7 (2)C10—C11—C12—C131.3 (3)
C13—O1—C1—C69.6 (3)C1—O1—C13—C88.6 (3)
C13—O1—C1—C2170.31 (18)C1—O1—C13—C12170.74 (18)
C6—C1—C2—C30.7 (4)C9—C8—C13—O1178.64 (18)
O1—C1—C2—C3179.3 (2)C7—C8—C13—O10.8 (3)
C16—N1—C3—C2175.4 (2)C9—C8—C13—C120.6 (3)
C14A—N1—C3—C227.0 (8)C7—C8—C13—C12179.92 (19)
C14—N1—C3—C221.6 (5)C11—C12—C13—O1178.19 (19)
C16—N1—C3—C44.9 (4)C11—C12—C13—C81.1 (3)
C14A—N1—C3—C4152.7 (8)C3—N1—C14—C1598.4 (4)
C14—N1—C3—C4158.7 (4)C16—N1—C14—C15106.1 (4)
C1—C2—C3—N1178.6 (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—C15A101.4 (9)
C2—C3—C4—C52.4 (3)C14—N1—C14A—C15A4.3 (8)
C3—C4—C5—C60.9 (3)C3—N1—C16—C1779.7 (3)
O1—C1—C6—C5177.82 (18)C14A—N1—C16—C17122.7 (8)
C2—C1—C6—C52.2 (3)C14—N1—C16—C1775.3 (4)
O1—C1—C6—C71.2 (3)C11—N2—C18—C1977.1 (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—C7179.54 (19)C18—N2—C20—C2192.5 (3)
C28—N3—C7—C8103.7 (2)C27—C22—C23—C242.3 (4)
N4—N3—C7—C856.2 (2)C22—C23—C24—C252.8 (4)
C28—N3—C7—C6132.94 (19)C23—C24—C25—C260.9 (4)
N4—N3—C7—C667.2 (2)C24—C25—C26—C271.4 (4)
C28—N3—C7—C2611.9 (2)C24—C25—C26—C7172.8 (2)
N4—N3—C7—C26171.83 (17)N3—C7—C26—C279.7 (2)
C1—C6—C7—N3116.1 (2)C8—C7—C26—C27106.1 (2)
C5—C6—C7—N362.9 (3)C6—C7—C26—C27128.69 (19)
C1—C6—C7—C87.3 (3)N3—C7—C26—C25175.7 (2)
C5—C6—C7—C8173.74 (18)C8—C7—C26—C2568.6 (3)
C1—C6—C7—C26132.5 (2)C6—C7—C26—C2556.6 (3)
C5—C6—C7—C2648.6 (3)C25—C26—C27—C221.8 (3)
N3—C7—C8—C13115.9 (2)C7—C26—C27—C22173.42 (19)
C6—C7—C8—C138.3 (3)C25—C26—C27—C28179.9 (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—C9171.09 (18)C23—C22—C27—C28177.8 (2)
C26—C7—C8—C943.6 (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—C27168.71 (18)
C8—C9—C10—C110.8 (4)C7—N3—C28—C279.8 (2)
C18—N2—C11—C12176.2 (2)C26—C27—C28—O2176.5 (2)
C20—N2—C11—C124.1 (3)C22—C27—C28—O21.7 (4)
C18—N2—C11—C106.1 (3)C26—C27—C28—N32.8 (2)
C20—N2—C11—C10178.3 (2)C22—C27—C28—N3179.1 (2)
C9—C10—C11—N2176.6 (2)N3—N4—C29—C3053.9 (3)
C9—C10—C11—C121.2 (4)N4—C29—C30—O357.8 (3)
Hydrogen-bond geometry (Å, º) top
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)

Experimental details

Crystal data
Chemical formulaC30H36N4O3
Mr500.63
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)12.269 (4), 12.203 (4), 18.458 (6)
β (°) 108.127 (5)
V3)2626.4 (15)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.58 × 0.25 × 0.25
Data collection
DiffractometerBruker SMART APEXII
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.849, 0.900
No. of measured, independent and
observed [I > 2σ(I)] reflections
17363, 4620, 2841
Rint0.064
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.129, 1.00
No. of reflections4620
No. of parameters359
No. of restraints13
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.21, 0.20

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), 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
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)
 

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