

Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808017108/lh2636sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536808017108/lh2636Isup2.hkl |
CCDC reference: 696674
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
(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
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.
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).
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).
C30H36N4O3 | F(000) = 1072 |
Mr = 500.63 | Dx = 1.266 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3630 reflections |
a = 12.269 (4) Å | θ = 2.0–25.0° |
b = 12.203 (4) Å | µ = 0.08 mm−1 |
c = 18.458 (6) Å | T = 298 K |
β = 108.127 (5)° | Block, white |
V = 2626.4 (15) Å3 | 0.58 × 0.25 × 0.25 mm |
Z = 4 |
Bruker SMART APEXII diffractometer | 4620 independent reflections |
Radiation source: fine-focus sealed tube | 2841 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.064 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −14→14 |
Tmin = 0.849, Tmax = 0.900 | k = −14→14 |
17363 measured reflections | l = −21→21 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.050 | H 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 reflections | Δρmax = 0.21 e Å−3 |
359 parameters | Δρmin = −0.20 e Å−3 |
13 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.026 (4) |
C30H36N4O3 | V = 2626.4 (15) Å3 |
Mr = 500.63 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.269 (4) Å | µ = 0.08 mm−1 |
b = 12.203 (4) Å | T = 298 K |
c = 18.458 (6) Å | 0.58 × 0.25 × 0.25 mm |
β = 108.127 (5)° |
Bruker SMART APEXII diffractometer | 4620 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 2841 reflections with I > 2σ(I) |
Tmin = 0.849, Tmax = 0.900 | Rint = 0.064 |
17363 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 13 restraints |
wR(F2) = 0.129 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.21 e Å−3 |
4620 reflections | Δρmin = −0.20 e Å−3 |
359 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.02779 (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* | |
N1 | 0.31949 (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* | |
C1 | 0.05554 (16) | 0.74041 (19) | 0.18219 (11) | 0.0459 (5) | |
C2 | 0.16682 (17) | 0.7528 (2) | 0.22812 (12) | 0.0551 (6) | |
H2A | 0.2155 | 0.6925 | 0.2386 | 0.066* | |
C3 | 0.20776 (17) | 0.8541 (2) | 0.25922 (13) | 0.0525 (6) | |
C4 | 0.13007 (17) | 0.94070 (19) | 0.24316 (12) | 0.0488 (6) | |
H4A | 0.1530 | 1.0093 | 0.2643 | 0.059* | |
C5 | 0.02040 (17) | 0.92561 (18) | 0.19652 (12) | 0.0468 (5) | |
H5A | −0.0292 | 0.9853 | 0.1863 | 0.056* | |
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 | −0.3130 | 0.7186 | 0.0030 | 0.068* | |
C10 | −0.27173 (19) | 0.5653 (2) | −0.01066 (13) | 0.0593 (6) | |
H10A | −0.3398 | 0.5491 | −0.0487 | 0.071* | |
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 | −0.0307 | 0.4626 | 0.0898 | 0.059* | |
C13 | −0.07482 (16) | 0.61794 (18) | 0.10178 (11) | 0.0436 (5) | |
C14 | 0.4083 (4) | 0.7842 (6) | 0.2970 (4) | 0.062 (2) | 0.720 (17) |
H14A | 0.3815 | 0.7481 | 0.2478 | 0.074* | 0.720 (17) |
H14B | 0.4792 | 0.8221 | 0.3002 | 0.074* | 0.720 (17) |
C15 | 0.4301 (7) | 0.7010 (7) | 0.3586 (4) | 0.099 (2) | 0.720 (17) |
H15A | 0.4863 | 0.6496 | 0.3533 | 0.149* | 0.720 (17) |
H15B | 0.3601 | 0.6631 | 0.3550 | 0.149* | 0.720 (17) |
H15C | 0.4580 | 0.7367 | 0.4072 | 0.149* | 0.720 (17) |
C14A | 0.3796 (13) | 0.7676 (16) | 0.3463 (9) | 0.074 (7) | 0.280 (17) |
H14C | 0.4289 | 0.7869 | 0.3969 | 0.088* | 0.280 (17) |
H14D | 0.3254 | 0.7120 | 0.3505 | 0.088* | 0.280 (17) |
C15A | 0.4469 (17) | 0.731 (2) | 0.2969 (13) | 0.111 (7) | 0.280 (17) |
H15D | 0.4904 | 0.6668 | 0.3187 | 0.166* | 0.280 (17) |
H15E | 0.4983 | 0.7881 | 0.2928 | 0.166* | 0.280 (17) |
H15F | 0.3959 | 0.7135 | 0.2472 | 0.166* | 0.280 (17) |
C16 | 0.3656 (2) | 0.9732 (2) | 0.33183 (16) | 0.0739 (8) | |
H16A | 0.4332 | 0.9633 | 0.3757 | 0.089* | |
H16B | 0.3092 | 1.0128 | 0.3485 | 0.089* | |
C17 | 0.3969 (2) | 1.0400 (3) | 0.27363 (18) | 0.0852 (9) | |
H17A | 0.4269 | 1.1094 | 0.2953 | 0.128* | |
H17B | 0.3299 | 1.0517 | 0.2305 | 0.128* | |
H17C | 0.4539 | 1.0020 | 0.2576 | 0.128* | |
C18 | −0.3044 (2) | 0.3522 (2) | −0.07672 (14) | 0.0690 (7) | |
H18A | −0.2890 | 0.2907 | −0.1054 | 0.083* | |
H18B | −0.3301 | 0.4127 | −0.1120 | 0.083* | |
C19 | −0.3997 (2) | 0.3211 (3) | −0.04619 (17) | 0.0877 (9) | |
H19A | −0.4665 | 0.3023 | −0.0877 | 0.132* | |
H19B | −0.4170 | 0.3817 | −0.0185 | 0.132* | |
H19C | −0.3766 | 0.2592 | −0.0127 | 0.132* | |
C20 | −0.1110 (2) | 0.2997 (2) | 0.00744 (14) | 0.0665 (7) | |
H20A | −0.0363 | 0.3339 | 0.0183 | 0.080* | |
H20B | −0.1183 | 0.2465 | −0.0328 | 0.080* | |
C21 | −0.1165 (2) | 0.2407 (2) | 0.07736 (15) | 0.0744 (8) | |
H21A | −0.0561 | 0.1874 | 0.0921 | 0.112* | |
H21B | −0.1893 | 0.2047 | 0.0668 | 0.112* | |
H21C | −0.1075 | 0.2924 | 0.1180 | 0.112* | |
C22 | −0.34216 (19) | 1.0120 (2) | −0.00789 (14) | 0.0593 (6) | |
H22A | −0.4118 | 1.0420 | −0.0078 | 0.071* | |
C23 | −0.2949 (2) | 1.0373 (2) | −0.06426 (14) | 0.0654 (7) | |
H23A | −0.3340 | 1.0832 | −0.1041 | 0.078* | |
C24 | −0.1899 (2) | 0.9951 (2) | −0.06186 (14) | 0.0692 (7) | |
H24A | −0.1574 | 1.0154 | −0.0991 | 0.083* | |
C25 | −0.13217 (19) | 0.9237 (2) | −0.00578 (13) | 0.0571 (6) | |
H25A | −0.0617 | 0.8949 | −0.0051 | 0.068* | |
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 | −0.0986 | 0.8101 | 0.2953 | 0.083* | |
H29B | −0.1933 | 0.7534 | 0.3224 | 0.083* | |
C30 | −0.2233 (2) | 0.9153 (3) | 0.30112 (16) | 0.0804 (9) | |
H30A | −0.1842 | 0.9361 | 0.3535 | 0.097* | |
H30B | −0.2048 | 0.9693 | 0.2682 | 0.097* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0457 (8) | 0.0423 (10) | 0.0714 (10) | 0.0041 (7) | −0.0072 (7) | −0.0086 (8) |
O2 | 0.0416 (8) | 0.0841 (14) | 0.0751 (11) | 0.0098 (8) | 0.0178 (8) | 0.0037 (9) |
O3 | 0.0625 (11) | 0.143 (2) | 0.0822 (13) | 0.0030 (11) | 0.0306 (10) | −0.0282 (13) |
N1 | 0.0511 (11) | 0.0595 (16) | 0.0937 (16) | 0.0007 (10) | −0.0163 (11) | −0.0167 (13) |
N2 | 0.0701 (12) | 0.0476 (13) | 0.0588 (13) | −0.0039 (10) | 0.0065 (10) | −0.0138 (10) |
N3 | 0.0412 (9) | 0.0439 (11) | 0.0479 (10) | 0.0031 (8) | 0.0141 (7) | 0.0043 (9) |
N4 | 0.0620 (11) | 0.0576 (14) | 0.0535 (12) | 0.0019 (10) | 0.0211 (10) | 0.0056 (10) |
C1 | 0.0424 (11) | 0.0430 (15) | 0.0490 (13) | −0.0023 (10) | 0.0093 (9) | −0.0057 (10) |
C2 | 0.0467 (12) | 0.0491 (16) | 0.0587 (14) | 0.0057 (11) | 0.0009 (10) | −0.0040 (12) |
C3 | 0.0426 (11) | 0.0570 (17) | 0.0505 (13) | −0.0034 (11) | 0.0039 (9) | −0.0047 (11) |
C4 | 0.0479 (12) | 0.0478 (15) | 0.0502 (13) | −0.0037 (10) | 0.0146 (10) | −0.0092 (11) |
C5 | 0.0431 (11) | 0.0436 (15) | 0.0547 (13) | 0.0025 (10) | 0.0167 (10) | −0.0038 (11) |
C6 | 0.0376 (10) | 0.0411 (14) | 0.0427 (11) | 0.0011 (9) | 0.0115 (8) | 0.0000 (10) |
C7 | 0.0368 (10) | 0.0389 (14) | 0.0484 (12) | −0.0003 (9) | 0.0117 (9) | −0.0015 (10) |
C8 | 0.0395 (10) | 0.0429 (14) | 0.0467 (12) | 0.0005 (10) | 0.0097 (9) | −0.0005 (10) |
C9 | 0.0465 (12) | 0.0463 (16) | 0.0650 (15) | 0.0033 (11) | −0.0019 (10) | −0.0006 (12) |
C10 | 0.0540 (13) | 0.0500 (16) | 0.0581 (15) | −0.0037 (12) | −0.0055 (11) | −0.0046 (12) |
C11 | 0.0545 (13) | 0.0475 (15) | 0.0454 (13) | −0.0040 (11) | 0.0115 (10) | −0.0019 (11) |
C12 | 0.0487 (12) | 0.0407 (15) | 0.0538 (14) | 0.0038 (10) | 0.0086 (10) | −0.0014 (11) |
C13 | 0.0382 (10) | 0.0451 (14) | 0.0430 (12) | −0.0011 (10) | 0.0061 (9) | −0.0005 (10) |
C14 | 0.039 (2) | 0.073 (4) | 0.067 (3) | −0.001 (2) | 0.007 (2) | −0.008 (3) |
C15 | 0.116 (4) | 0.091 (5) | 0.083 (4) | 0.042 (4) | 0.021 (3) | 0.013 (3) |
C14A | 0.058 (8) | 0.085 (14) | 0.068 (9) | −0.009 (8) | 0.006 (6) | −0.020 (7) |
C15A | 0.089 (11) | 0.114 (16) | 0.137 (16) | 0.022 (9) | 0.046 (10) | −0.030 (12) |
C16 | 0.0539 (13) | 0.074 (2) | 0.0739 (18) | −0.0028 (13) | −0.0099 (13) | −0.0210 (16) |
C17 | 0.0611 (16) | 0.084 (2) | 0.109 (2) | −0.0023 (15) | 0.0243 (16) | −0.0150 (19) |
C18 | 0.0865 (17) | 0.0548 (18) | 0.0527 (15) | −0.0111 (14) | 0.0029 (13) | −0.0077 (12) |
C19 | 0.0829 (18) | 0.075 (2) | 0.092 (2) | −0.0107 (16) | 0.0089 (16) | 0.0116 (17) |
C20 | 0.0777 (16) | 0.0508 (17) | 0.0700 (17) | −0.0048 (13) | 0.0216 (13) | −0.0173 (13) |
C21 | 0.0750 (17) | 0.071 (2) | 0.0689 (17) | −0.0050 (14) | 0.0101 (13) | −0.0033 (15) |
C22 | 0.0542 (13) | 0.0487 (16) | 0.0643 (16) | 0.0053 (11) | 0.0026 (12) | 0.0008 (13) |
C23 | 0.0765 (17) | 0.0556 (17) | 0.0541 (15) | −0.0006 (13) | 0.0058 (13) | 0.0085 (13) |
C24 | 0.0820 (17) | 0.071 (2) | 0.0526 (15) | −0.0097 (15) | 0.0179 (13) | 0.0046 (14) |
C25 | 0.0563 (13) | 0.0583 (17) | 0.0585 (15) | 0.0003 (12) | 0.0206 (11) | 0.0047 (13) |
C26 | 0.0426 (11) | 0.0405 (14) | 0.0485 (13) | −0.0011 (9) | 0.0069 (9) | −0.0037 (10) |
C27 | 0.0421 (11) | 0.0428 (14) | 0.0529 (14) | −0.0006 (10) | 0.0048 (9) | 0.0013 (11) |
C28 | 0.0363 (11) | 0.0513 (15) | 0.0580 (14) | 0.0023 (10) | 0.0086 (10) | −0.0027 (11) |
C29 | 0.0540 (13) | 0.103 (2) | 0.0488 (15) | 0.0018 (14) | 0.0126 (11) | 0.0089 (15) |
C30 | 0.0612 (15) | 0.114 (3) | 0.0668 (17) | −0.0129 (16) | 0.0209 (13) | −0.0303 (17) |
O1—C13 | 1.365 (2) | C15—H15B | 0.9600 |
O1—C1 | 1.370 (3) | C15—H15C | 0.9600 |
O2—C28 | 1.231 (2) | C14A—C15A | 1.48 (4) |
O3—C30 | 1.394 (3) | C14A—H14C | 0.9700 |
O3—H3O | 0.99 (4) | C14A—H14D | 0.9700 |
N1—C3 | 1.369 (3) | C15A—H15D | 0.9600 |
N1—C16 | 1.450 (3) | C15A—H15E | 0.9600 |
N1—C14A | 1.50 (2) | C15A—H15F | 0.9600 |
N1—C14 | 1.514 (8) | C16—C17 | 1.491 (4) |
N2—C11 | 1.374 (3) | C16—H16A | 0.9700 |
N2—C18 | 1.438 (3) | C16—H16B | 0.9700 |
N2—C20 | 1.457 (3) | C17—H17A | 0.9600 |
N3—C28 | 1.342 (3) | C17—H17B | 0.9600 |
N3—N4 | 1.394 (2) | C17—H17C | 0.9600 |
N3—C7 | 1.479 (2) | C18—C19 | 1.496 (4) |
N4—C29 | 1.454 (3) | C18—H18A | 0.9700 |
N4—H1N | 0.96 (3) | C18—H18B | 0.9700 |
C1—C6 | 1.370 (3) | C19—H19A | 0.9600 |
C1—C2 | 1.373 (3) | C19—H19B | 0.9600 |
C2—C3 | 1.389 (3) | C19—H19C | 0.9600 |
C2—H2A | 0.9300 | C20—C21 | 1.497 (4) |
C3—C4 | 1.392 (3) | C20—H20A | 0.9700 |
C4—C5 | 1.365 (3) | C20—H20B | 0.9700 |
C4—H4A | 0.9300 | C21—H21A | 0.9600 |
C5—C6 | 1.383 (3) | C21—H21B | 0.9600 |
C5—H5A | 0.9300 | C21—H21C | 0.9600 |
C6—C7 | 1.504 (3) | C22—C23 | 1.375 (3) |
C7—C8 | 1.503 (3) | C22—C27 | 1.376 (3) |
C7—C26 | 1.517 (3) | C22—H22A | 0.9300 |
C8—C13 | 1.365 (3) | C23—C24 | 1.375 (3) |
C8—C9 | 1.389 (3) | C23—H23A | 0.9300 |
C9—C10 | 1.355 (3) | C24—C25 | 1.370 (3) |
C9—H9A | 0.9300 | C24—H24A | 0.9300 |
C10—C11 | 1.401 (3) | C25—C26 | 1.371 (3) |
C10—H10A | 0.9300 | C25—H25A | 0.9300 |
C11—C12 | 1.382 (3) | C26—C27 | 1.368 (3) |
C12—C13 | 1.375 (3) | C27—C28 | 1.468 (3) |
C12—H12A | 0.9300 | C29—C30 | 1.501 (4) |
C14—C15 | 1.485 (13) | C29—H29A | 0.9700 |
C14—H14A | 0.9700 | C29—H29B | 0.9700 |
C14—H14B | 0.9700 | C30—H30A | 0.9700 |
C15—H15A | 0.9600 | C30—H30B | 0.9700 |
C13—O1—C1 | 118.37 (16) | H14C—C14A—H14D | 109.3 |
C30—O3—H3O | 101 (2) | C14A—C15A—H15D | 109.5 |
C3—N1—C16 | 121.3 (2) | C14A—C15A—H15E | 109.5 |
C3—N1—C14A | 117.6 (5) | H15D—C15A—H15E | 109.5 |
C16—N1—C14A | 117.4 (4) | C14A—C15A—H15F | 109.5 |
C3—N1—C14 | 119.3 (2) | H15D—C15A—H15F | 109.5 |
C16—N1—C14 | 114.5 (2) | H15E—C15A—H15F | 109.5 |
C14A—N1—C14 | 42.5 (6) | N1—C16—C17 | 113.1 (2) |
C11—N2—C18 | 121.1 (2) | N1—C16—H16A | 109.0 |
C11—N2—C20 | 120.56 (19) | C17—C16—H16A | 109.0 |
C18—N2—C20 | 117.9 (2) | N1—C16—H16B | 109.0 |
C28—N3—N4 | 123.30 (17) | C17—C16—H16B | 109.0 |
C28—N3—C7 | 114.26 (17) | H16A—C16—H16B | 107.8 |
N4—N3—C7 | 119.03 (16) | C16—C17—H17A | 109.5 |
N3—N4—C29 | 113.5 (2) | C16—C17—H17B | 109.5 |
N3—N4—H1N | 105.4 (16) | H17A—C17—H17B | 109.5 |
C29—N4—H1N | 109.4 (15) | C16—C17—H17C | 109.5 |
C6—C1—O1 | 123.23 (17) | H17A—C17—H17C | 109.5 |
C6—C1—C2 | 122.7 (2) | H17B—C17—H17C | 109.5 |
O1—C1—C2 | 114.11 (19) | N2—C18—C19 | 115.1 (2) |
C1—C2—C3 | 121.0 (2) | N2—C18—H18A | 108.5 |
C1—C2—H2A | 119.5 | C19—C18—H18A | 108.5 |
C3—C2—H2A | 119.5 | N2—C18—H18B | 108.5 |
N1—C3—C2 | 120.7 (2) | C19—C18—H18B | 108.5 |
N1—C3—C4 | 122.4 (2) | H18A—C18—H18B | 107.5 |
C2—C3—C4 | 116.86 (19) | C18—C19—H19A | 109.5 |
C5—C4—C3 | 120.5 (2) | C18—C19—H19B | 109.5 |
C5—C4—H4A | 119.8 | H19A—C19—H19B | 109.5 |
C3—C4—H4A | 119.8 | C18—C19—H19C | 109.5 |
C4—C5—C6 | 123.2 (2) | H19A—C19—H19C | 109.5 |
C4—C5—H5A | 118.4 | H19B—C19—H19C | 109.5 |
C6—C5—H5A | 118.4 | N2—C20—C21 | 114.2 (2) |
C1—C6—C5 | 115.73 (18) | N2—C20—H20A | 108.7 |
C1—C6—C7 | 121.66 (19) | C21—C20—H20A | 108.7 |
C5—C6—C7 | 122.61 (18) | N2—C20—H20B | 108.7 |
N3—C7—C8 | 110.47 (16) | C21—C20—H20B | 108.7 |
N3—C7—C6 | 111.84 (16) | H20A—C20—H20B | 107.6 |
C8—C7—C6 | 110.36 (16) | C20—C21—H21A | 109.5 |
N3—C7—C26 | 98.86 (15) | C20—C21—H21B | 109.5 |
C8—C7—C26 | 110.30 (17) | H21A—C21—H21B | 109.5 |
C6—C7—C26 | 114.52 (17) | C20—C21—H21C | 109.5 |
C13—C8—C9 | 115.6 (2) | H21A—C21—H21C | 109.5 |
C13—C8—C7 | 122.46 (18) | H21B—C21—H21C | 109.5 |
C9—C8—C7 | 121.98 (19) | C23—C22—C27 | 117.8 (2) |
C10—C9—C8 | 123.4 (2) | C23—C22—H22A | 121.1 |
C10—C9—H9A | 118.3 | C27—C22—H22A | 121.1 |
C8—C9—H9A | 118.3 | C24—C23—C22 | 120.2 (2) |
C9—C10—C11 | 120.3 (2) | C24—C23—H23A | 119.9 |
C9—C10—H10A | 119.8 | C22—C23—H23A | 119.9 |
C11—C10—H10A | 119.8 | C25—C24—C23 | 121.5 (2) |
N2—C11—C12 | 121.9 (2) | C25—C24—H24A | 119.3 |
N2—C11—C10 | 121.3 (2) | C23—C24—H24A | 119.3 |
C12—C11—C10 | 116.8 (2) | C24—C25—C26 | 118.6 (2) |
C13—C12—C11 | 121.2 (2) | C24—C25—H25A | 120.7 |
C13—C12—H12A | 119.4 | C26—C25—H25A | 120.7 |
C11—C12—H12A | 119.4 | C27—C26—C25 | 119.9 (2) |
O1—C13—C8 | 122.78 (19) | C27—C26—C7 | 110.87 (18) |
O1—C13—C12 | 114.55 (18) | C25—C26—C7 | 128.97 (19) |
C8—C13—C12 | 122.67 (19) | C26—C27—C22 | 122.0 (2) |
C15—C14—N1 | 110.7 (7) | C26—C27—C28 | 108.24 (18) |
C15—C14—H14A | 109.5 | C22—C27—C28 | 129.8 (2) |
N1—C14—H14A | 109.5 | O2—C28—N3 | 125.1 (2) |
C15—C14—H14B | 109.5 | O2—C28—C27 | 128.5 (2) |
N1—C14—H14B | 109.5 | N3—C28—C27 | 106.41 (17) |
H14A—C14—H14B | 108.1 | N4—C29—C30 | 116.2 (2) |
C14—C15—H15A | 109.5 | N4—C29—H29A | 108.2 |
C14—C15—H15B | 109.5 | C30—C29—H29A | 108.2 |
H15A—C15—H15B | 109.5 | N4—C29—H29B | 108.2 |
C14—C15—H15C | 109.5 | C30—C29—H29B | 108.2 |
H15A—C15—H15C | 109.5 | H29A—C29—H29B | 107.4 |
H15B—C15—H15C | 109.5 | O3—C30—C29 | 112.4 (2) |
C15A—C14A—N1 | 101.4 (18) | O3—C30—H30A | 109.1 |
C15A—C14A—H14C | 111.5 | C29—C30—H30A | 109.1 |
N1—C14A—H14C | 111.5 | O3—C30—H30B | 109.1 |
C15A—C14A—H14D | 111.5 | C29—C30—H30B | 109.1 |
N1—C14A—H14D | 111.5 | H30A—C30—H30B | 107.9 |
C28—N3—N4—C29 | −98.3 (2) | N2—C11—C12—C13 | 176.4 (2) |
C7—N3—N4—C29 | 103.7 (2) | C10—C11—C12—C13 | −1.3 (3) |
C13—O1—C1—C6 | 9.6 (3) | C1—O1—C13—C8 | −8.6 (3) |
C13—O1—C1—C2 | −170.31 (18) | C1—O1—C13—C12 | 170.74 (18) |
C6—C1—C2—C3 | 0.7 (4) | C9—C8—C13—O1 | 178.64 (18) |
O1—C1—C2—C3 | −179.3 (2) | C7—C8—C13—O1 | −0.8 (3) |
C16—N1—C3—C2 | 175.4 (2) | C9—C8—C13—C12 | −0.6 (3) |
C14A—N1—C3—C2 | −27.0 (8) | C7—C8—C13—C12 | 179.92 (19) |
C14—N1—C3—C2 | 21.6 (5) | C11—C12—C13—O1 | −178.19 (19) |
C16—N1—C3—C4 | −4.9 (4) | C11—C12—C13—C8 | 1.1 (3) |
C14A—N1—C3—C4 | 152.7 (8) | C3—N1—C14—C15 | −98.4 (4) |
C14—N1—C3—C4 | −158.7 (4) | C16—N1—C14—C15 | 106.1 (4) |
C1—C2—C3—N1 | −178.6 (2) | C14A—N1—C14—C15 | 1.5 (7) |
C1—C2—C3—C4 | 1.6 (3) | C3—N1—C14A—C15A | 100.1 (9) |
N1—C3—C4—C5 | 177.9 (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—C6 | 0.9 (3) | C3—N1—C16—C17 | −79.7 (3) |
O1—C1—C6—C5 | 177.82 (18) | C14A—N1—C16—C17 | 122.7 (8) |
C2—C1—C6—C5 | −2.2 (3) | C14—N1—C16—C17 | 75.3 (4) |
O1—C1—C6—C7 | −1.2 (3) | C11—N2—C18—C19 | −77.1 (3) |
C2—C1—C6—C7 | 178.74 (19) | C20—N2—C18—C19 | 95.2 (3) |
C4—C5—C6—C1 | 1.5 (3) | C11—N2—C20—C21 | 79.8 (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—C8 | 56.2 (2) | C22—C23—C24—C25 | 2.8 (4) |
C28—N3—C7—C6 | 132.94 (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—C26 | 11.9 (2) | C24—C25—C26—C7 | 172.8 (2) |
N4—N3—C7—C26 | 171.83 (17) | N3—C7—C26—C27 | −9.7 (2) |
C1—C6—C7—N3 | 116.1 (2) | C8—C7—C26—C27 | 106.1 (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—C25 | 175.7 (2) |
C5—C6—C7—C8 | 173.74 (18) | C8—C7—C26—C25 | −68.6 (3) |
C1—C6—C7—C26 | −132.5 (2) | C6—C7—C26—C25 | 56.6 (3) |
C5—C6—C7—C26 | 48.6 (3) | C25—C26—C27—C22 | 1.8 (3) |
N3—C7—C8—C13 | −115.9 (2) | C7—C26—C27—C22 | −173.42 (19) |
C6—C7—C8—C13 | 8.3 (3) | C25—C26—C27—C28 | −179.9 (2) |
C26—C7—C8—C13 | 135.9 (2) | C7—C26—C27—C28 | 4.9 (2) |
N3—C7—C8—C9 | 64.7 (3) | C23—C22—C27—C26 | 0.1 (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—O2 | 10.5 (3) |
C13—C8—C9—C10 | 0.5 (3) | C7—N3—C28—O2 | 169.5 (2) |
C7—C8—C9—C10 | 179.9 (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—C12 | 176.2 (2) | C26—C27—C28—O2 | −176.5 (2) |
C20—N2—C11—C12 | 4.1 (3) | C22—C27—C28—O2 | 1.7 (4) |
C18—N2—C11—C10 | −6.1 (3) | C26—C27—C28—N3 | 2.8 (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—C30 | 53.9 (3) |
C9—C10—C11—C12 | 1.2 (4) | N4—C29—C30—O3 | 57.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3O···O2 | 1.00 (4) | 1.79 (4) | 2.780 (3) | 172 (4) |
N4—H1N···O2 | 0.96 (3) | 2.45 (2) | 2.828 (3) | 103 (2) |
Experimental details
Crystal data | |
Chemical formula | C30H36N4O3 |
Mr | 500.63 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 12.269 (4), 12.203 (4), 18.458 (6) |
β (°) | 108.127 (5) |
V (Å3) | 2626.4 (15) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.58 × 0.25 × 0.25 |
Data collection | |
Diffractometer | Bruker SMART APEXII diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.849, 0.900 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17363, 4620, 2841 |
Rint | 0.064 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.129, 1.00 |
No. of reflections | 4620 |
No. of parameters | 359 |
No. of restraints | 13 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.21, −0.20 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3O···O2 | 1.00 (4) | 1.79 (4) | 2.780 (3) | 172 (4) |
N4—H1N···O2 | 0.96 (3) | 2.45 (2) | 2.828 (3) | 103 (2) |
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)°.