Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807037221/nc2050sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807037221/nc2050Isup2.hkl |
CCDC reference: 660188
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.004 Å
- R factor = 0.061
- wR factor = 0.201
- Data-to-parameter ratio = 14.2
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for N2 - C28 .. 20.08 su PLAT230_ALERT_2_B Hirshfeld Test Diff for N3 - C26 .. 7.78 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C8 - C9 .. 13.72 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C9 - C10 .. 10.20 su
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 40 Ang. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.17 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.48 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C8 .. 6.19 su
0 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Rhodamine B(1 g, 2.26 mmol) and 1-aminopropane (0.186 ml, 2.26 mmol) were refluxed in 20 ml of methanol for about 3 h until the color changes into light yellow. The crude product were purified by column chromatography (eluation with MeOH/CH2Cl2 = 100:1, v/v). After removal of the solvent in vacuum the solid were dried in vacuum to afford the title compound in 53% yield. Single crystals suitable for X-ray measurements were obtained from a hexane/dichloromethane (1:1, v/v) solution by slow evaporation of the solvent at room temperature.
The C—H H were placed in geometrically calculated positions (C—H = 0.93–0.97 Å) and refined as riding, with Uiso(H) = 1.2Ueq(C) (1.5Ueq for methyl H atoms).
Rhodamine dyes are widely used as fluorescent labels (De Silva et al., 1997) but only a few of such compounds were characterized by single-crystal X-ray diffraction (Kwon et al., 2005). However, for the understanding of their photophysical and photochemical properties, information on their molecular and crystal structures are needed. As part of our ongoing work on rhodamine dyes, we report here the synthesis and crystal structure of the title compound 3',6'-Bis(diethylamino)-2-propyl-spiro[isoindoline-1,9'-[xanthen]-3-one (I).
As similar compounds the main skeleton of the molecule is built up of an xanthene ring which is connected to an spirolactam-ring (Kwon et al., 2005). The lactam moiety is oriented nearly orthogonal to the xanthene moiety. The dihedral angle between the planes of the xanthene ring and the spirolactam-ring amount to 90.3°.
For related literature, see: De Silva et al. (1997); Kwon et al. (2005).
Data collection: APEX2 (Bruker, 2005); cell refinement: SMART (Bruker, 1997); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
Fig. 1. Crystal structure of compound I, with labelling and displacement ellipsoids drawn at the 30% probability level. |
C31H37N3O2 | Z = 2 |
Mr = 483.64 | F(000) = 520 |
Triclinic, P1 | Dx = 1.186 Mg m−3 |
Hall symbol: -P 1 | Melting point: 482 K |
a = 11.1697 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.8605 (4) Å | Cell parameters from 2231 reflections |
c = 12.4512 (4) Å | θ = 3.5–22.9° |
α = 82.838 (3)° | µ = 0.07 mm−1 |
β = 64.605 (2)° | T = 273 K |
γ = 65.588 (2)° | Block, white |
V = 1354.13 (8) Å3 | 0.55 × 0.40 × 0.20 mm |
Bruker APEXII CCD area-detector diffractometer | 4699 independent reflections |
Radiation source: fine-focus sealed tube | 2963 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
φ and ω scans | θmax = 25.0°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −13→13 |
Tmin = 0.960, Tmax = 0.985 | k = −13→14 |
9526 measured reflections | l = −14→14 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.061 | w = 1/[σ2(Fo2) + (0.1086P)2 + 0.0965P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.201 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 0.32 e Å−3 |
4699 reflections | Δρmin = −0.24 e Å−3 |
330 parameters |
C31H37N3O2 | γ = 65.588 (2)° |
Mr = 483.64 | V = 1354.13 (8) Å3 |
Triclinic, P1 | Z = 2 |
a = 11.1697 (4) Å | Mo Kα radiation |
b = 11.8605 (4) Å | µ = 0.07 mm−1 |
c = 12.4512 (4) Å | T = 273 K |
α = 82.838 (3)° | 0.55 × 0.40 × 0.20 mm |
β = 64.605 (2)° |
Bruker APEXII CCD area-detector diffractometer | 4699 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | 2963 reflections with I > 2σ(I) |
Tmin = 0.960, Tmax = 0.985 | Rint = 0.027 |
9526 measured reflections |
R[F2 > 2σ(F2)] = 0.061 | 0 restraints |
wR(F2) = 0.201 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.32 e Å−3 |
4699 reflections | Δρmin = −0.24 e Å−3 |
330 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O2 | 0.6833 (2) | 0.94710 (14) | 0.39573 (15) | 0.0663 (5) | |
C23 | 0.6694 (2) | 1.1572 (2) | 0.3635 (2) | 0.0504 (6) | |
C12 | 0.6414 (2) | 1.0462 (2) | 0.2257 (2) | 0.0510 (6) | |
C17 | 0.6604 (2) | 0.9467 (2) | 0.2956 (2) | 0.0519 (6) | |
N1 | 0.5045 (2) | 1.27294 (17) | 0.26636 (17) | 0.0539 (5) | |
C16 | 0.6599 (3) | 0.8367 (2) | 0.2691 (2) | 0.0578 (6) | |
H16A | 0.6742 | 0.7713 | 0.3182 | 0.069* | |
O1 | 0.4211 (2) | 1.44106 (16) | 0.16568 (17) | 0.0752 (6) | |
C15 | 0.6385 (2) | 0.8222 (2) | 0.1706 (2) | 0.0572 (6) | |
C18 | 0.6879 (3) | 1.0524 (2) | 0.4273 (2) | 0.0534 (6) | |
C14 | 0.6199 (3) | 0.9239 (2) | 0.0986 (3) | 0.0647 (7) | |
H14A | 0.6069 | 0.9181 | 0.0309 | 0.078* | |
C11 | 0.6423 (2) | 1.16741 (19) | 0.2536 (2) | 0.0507 (6) | |
C19 | 0.7147 (3) | 1.0421 (2) | 0.5268 (2) | 0.0620 (7) | |
H19A | 0.7286 | 0.9685 | 0.5654 | 0.074* | |
C1 | 0.7490 (3) | 1.2028 (2) | 0.1450 (2) | 0.0527 (6) | |
C7 | 0.5201 (3) | 1.3512 (2) | 0.1766 (2) | 0.0556 (6) | |
C13 | 0.6208 (3) | 1.0308 (2) | 0.1271 (2) | 0.0619 (7) | |
H13A | 0.6069 | 1.0965 | 0.0782 | 0.074* | |
C22 | 0.6769 (3) | 1.2555 (2) | 0.4076 (2) | 0.0638 (7) | |
H22A | 0.6643 | 1.3284 | 0.3678 | 0.077* | |
N3 | 0.6333 (2) | 0.71471 (19) | 0.1450 (2) | 0.0701 (6) | |
C6 | 0.6758 (3) | 1.3061 (2) | 0.0986 (2) | 0.0533 (6) | |
C5 | 0.7487 (3) | 1.3516 (2) | −0.0066 (2) | 0.0653 (7) | |
H5A | 0.6987 | 1.4194 | −0.0391 | 0.078* | |
C21 | 0.7022 (3) | 1.2489 (2) | 0.5072 (3) | 0.0680 (7) | |
H21A | 0.7066 | 1.3168 | 0.5329 | 0.082* | |
C20 | 0.7214 (3) | 1.1418 (3) | 0.5705 (2) | 0.0647 (7) | |
C2 | 0.8976 (3) | 1.1444 (2) | 0.0910 (2) | 0.0655 (7) | |
H2A | 0.9473 | 1.0755 | 0.1228 | 0.079* | |
N2 | 0.7448 (3) | 1.1347 (2) | 0.6709 (2) | 0.0883 (8) | |
C24 | 0.6286 (4) | 0.6961 (3) | 0.0341 (3) | 0.0823 (9) | |
H24A | 0.5562 | 0.7706 | 0.0218 | 0.099* | |
H24B | 0.5978 | 0.6290 | 0.0417 | 0.099* | |
C26 | 0.6551 (3) | 0.6089 (3) | 0.2187 (3) | 0.0798 (9) | |
H26A | 0.6090 | 0.5593 | 0.2096 | 0.096* | |
H26B | 0.6073 | 0.6394 | 0.3015 | 0.096* | |
C3 | 0.9713 (3) | 1.1913 (3) | −0.0121 (3) | 0.0756 (8) | |
H3A | 1.0718 | 1.1540 | −0.0493 | 0.091* | |
C4 | 0.8970 (3) | 1.2929 (3) | −0.0605 (3) | 0.0726 (8) | |
H4A | 0.9484 | 1.3218 | −0.1305 | 0.087* | |
C8 | 0.3672 (3) | 1.2806 (2) | 0.3566 (3) | 0.0710 (7) | |
H8A | 0.3801 | 1.2022 | 0.3939 | 0.085* | |
H8B | 0.3024 | 1.2937 | 0.3192 | 0.085* | |
C30 | 0.7497 (4) | 1.2395 (3) | 0.7168 (3) | 0.0939 (10) | |
H30A | 0.7281 | 1.2307 | 0.8009 | 0.113* | |
H30B | 0.6741 | 1.3151 | 0.7101 | 0.113* | |
C27 | 0.8098 (4) | 0.5279 (3) | 0.1898 (3) | 0.0949 (10) | |
H27A | 0.8156 | 0.4660 | 0.2470 | 0.142* | |
H27B | 0.8585 | 0.5773 | 0.1923 | 0.142* | |
H27C | 0.8551 | 0.4883 | 0.1116 | 0.142* | |
C28 | 0.7645 (4) | 1.0192 (4) | 0.7386 (3) | 0.1097 (12) | |
H28A | 0.7429 | 1.0394 | 0.8198 | 0.132* | |
H28B | 0.6983 | 0.9848 | 0.7412 | 0.132* | |
C31 | 0.8902 (4) | 1.2535 (4) | 0.6561 (4) | 0.1210 (14) | |
H31A | 0.8822 | 1.3262 | 0.6899 | 0.182* | |
H31B | 0.9135 | 1.2617 | 0.5726 | 0.182* | |
H31C | 0.9651 | 1.1817 | 0.6668 | 0.182* | |
C25 | 0.7684 (4) | 0.6666 (3) | −0.0731 (3) | 0.1066 (12) | |
H25A | 0.7536 | 0.6651 | −0.1433 | 0.160* | |
H25B | 0.8374 | 0.5869 | −0.0672 | 0.160* | |
H25C | 0.8044 | 0.7287 | −0.0779 | 0.160* | |
C29 | 0.9134 (5) | 0.9280 (5) | 0.6809 (4) | 0.1498 (18) | |
H29A | 0.9264 | 0.8558 | 0.7262 | 0.225* | |
H29B | 0.9787 | 0.9632 | 0.6765 | 0.225* | |
H29C | 0.9329 | 0.9051 | 0.6019 | 0.225* | |
C9 | 0.2953 (4) | 1.3869 (4) | 0.4548 (3) | 0.1138 (13) | |
H9A | 0.3551 | 1.3705 | 0.4977 | 0.137* | |
H9B | 0.2887 | 1.4649 | 0.4177 | 0.137* | |
C10 | 0.1492 (5) | 1.3971 (5) | 0.5393 (4) | 0.1599 (19) | |
H10A | 0.1025 | 1.4693 | 0.5926 | 0.240* | |
H10B | 0.1569 | 1.3245 | 0.5842 | 0.240* | |
H10C | 0.0934 | 1.4041 | 0.4959 | 0.240* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.1059 (14) | 0.0485 (10) | 0.0647 (11) | −0.0381 (9) | −0.0486 (10) | 0.0116 (8) |
C23 | 0.0564 (13) | 0.0408 (13) | 0.0578 (14) | −0.0173 (10) | −0.0287 (11) | 0.0015 (10) |
C12 | 0.0576 (14) | 0.0424 (13) | 0.0595 (14) | −0.0185 (11) | −0.0316 (12) | 0.0030 (11) |
C17 | 0.0585 (14) | 0.0433 (13) | 0.0580 (14) | −0.0183 (11) | −0.0296 (12) | 0.0018 (11) |
N1 | 0.0569 (12) | 0.0427 (11) | 0.0613 (12) | −0.0165 (9) | −0.0274 (10) | 0.0039 (9) |
C16 | 0.0707 (16) | 0.0426 (13) | 0.0670 (16) | −0.0241 (12) | −0.0337 (13) | 0.0046 (11) |
O1 | 0.0851 (13) | 0.0534 (11) | 0.0837 (13) | −0.0134 (10) | −0.0481 (11) | 0.0118 (9) |
C15 | 0.0602 (15) | 0.0449 (14) | 0.0747 (17) | −0.0192 (11) | −0.0350 (13) | −0.0037 (12) |
C18 | 0.0625 (14) | 0.0473 (14) | 0.0555 (14) | −0.0226 (11) | −0.0279 (12) | 0.0016 (11) |
C14 | 0.0780 (17) | 0.0527 (15) | 0.0790 (18) | −0.0223 (13) | −0.0495 (15) | 0.0024 (13) |
C11 | 0.0590 (14) | 0.0370 (12) | 0.0604 (14) | −0.0165 (10) | −0.0315 (12) | 0.0043 (10) |
C19 | 0.0761 (17) | 0.0582 (15) | 0.0586 (15) | −0.0263 (13) | −0.0357 (13) | 0.0066 (12) |
C1 | 0.0636 (15) | 0.0440 (13) | 0.0592 (14) | −0.0231 (11) | −0.0310 (12) | 0.0007 (11) |
C7 | 0.0735 (17) | 0.0379 (13) | 0.0632 (15) | −0.0183 (12) | −0.0387 (13) | 0.0011 (11) |
C13 | 0.0783 (17) | 0.0465 (14) | 0.0753 (17) | −0.0221 (12) | −0.0493 (15) | 0.0105 (12) |
C22 | 0.0762 (17) | 0.0500 (15) | 0.0777 (18) | −0.0268 (13) | −0.0416 (15) | 0.0045 (12) |
N3 | 0.0911 (16) | 0.0474 (12) | 0.0889 (16) | −0.0300 (11) | −0.0488 (13) | −0.0014 (11) |
C6 | 0.0732 (16) | 0.0413 (13) | 0.0548 (14) | −0.0243 (12) | −0.0333 (13) | 0.0019 (11) |
C5 | 0.094 (2) | 0.0524 (15) | 0.0645 (17) | −0.0372 (15) | −0.0399 (16) | 0.0065 (12) |
C21 | 0.0804 (18) | 0.0606 (17) | 0.0773 (18) | −0.0289 (14) | −0.0416 (15) | −0.0074 (14) |
C20 | 0.0667 (16) | 0.0704 (18) | 0.0612 (16) | −0.0243 (13) | −0.0314 (13) | −0.0037 (13) |
C2 | 0.0672 (17) | 0.0530 (15) | 0.0758 (18) | −0.0201 (13) | −0.0316 (14) | −0.0020 (13) |
N2 | 0.124 (2) | 0.0885 (18) | 0.0758 (16) | −0.0421 (16) | −0.0630 (16) | 0.0043 (14) |
C24 | 0.101 (2) | 0.0649 (18) | 0.106 (2) | −0.0342 (16) | −0.059 (2) | −0.0102 (16) |
C26 | 0.093 (2) | 0.0589 (18) | 0.101 (2) | −0.0389 (16) | −0.0416 (18) | −0.0053 (15) |
C3 | 0.0724 (18) | 0.083 (2) | 0.0725 (19) | −0.0376 (16) | −0.0210 (16) | −0.0096 (16) |
C4 | 0.090 (2) | 0.0753 (19) | 0.0616 (17) | −0.0474 (17) | −0.0253 (16) | 0.0025 (14) |
C8 | 0.0680 (17) | 0.0606 (16) | 0.0827 (19) | −0.0221 (13) | −0.0356 (15) | 0.0125 (14) |
C30 | 0.107 (2) | 0.114 (3) | 0.078 (2) | −0.047 (2) | −0.0444 (19) | −0.0174 (18) |
C27 | 0.104 (3) | 0.071 (2) | 0.118 (3) | −0.0303 (18) | −0.056 (2) | −0.0036 (18) |
C28 | 0.107 (3) | 0.160 (4) | 0.075 (2) | −0.064 (3) | −0.035 (2) | −0.013 (2) |
C31 | 0.121 (3) | 0.152 (4) | 0.121 (3) | −0.061 (3) | −0.065 (3) | −0.015 (3) |
C25 | 0.144 (3) | 0.107 (3) | 0.091 (3) | −0.065 (2) | −0.050 (3) | −0.003 (2) |
C29 | 0.104 (3) | 0.213 (5) | 0.132 (4) | −0.052 (3) | −0.060 (3) | 0.005 (3) |
C9 | 0.078 (2) | 0.163 (4) | 0.070 (2) | −0.037 (2) | −0.0146 (18) | 0.003 (2) |
C10 | 0.111 (3) | 0.195 (5) | 0.124 (4) | −0.031 (3) | −0.033 (3) | 0.000 (3) |
O2—C17 | 1.377 (3) | N2—C30 | 1.462 (4) |
O2—C18 | 1.382 (3) | N2—C28 | 1.503 (5) |
C23—C18 | 1.379 (3) | C24—C25 | 1.490 (4) |
C23—C22 | 1.396 (3) | C24—H24A | 0.9700 |
C23—C11 | 1.504 (3) | C24—H24B | 0.9700 |
C12—C17 | 1.375 (3) | C26—C27 | 1.490 (4) |
C12—C13 | 1.389 (3) | C26—H26A | 0.9700 |
C12—C11 | 1.525 (3) | C26—H26B | 0.9700 |
C17—C16 | 1.388 (3) | C3—C4 | 1.387 (4) |
N1—C7 | 1.360 (3) | C3—H3A | 0.9300 |
N1—C8 | 1.434 (3) | C4—H4A | 0.9300 |
N1—C11 | 1.486 (3) | C8—C9 | 1.561 (5) |
C16—C15 | 1.388 (3) | C8—H8A | 0.9700 |
C16—H16A | 0.9300 | C8—H8B | 0.9700 |
O1—C7 | 1.223 (3) | C30—C31 | 1.492 (5) |
C15—N3 | 1.382 (3) | C30—H30A | 0.9700 |
C15—C14 | 1.409 (3) | C30—H30B | 0.9700 |
C18—C19 | 1.374 (3) | C27—H27A | 0.9600 |
C14—C13 | 1.364 (3) | C27—H27B | 0.9600 |
C14—H14A | 0.9300 | C27—H27C | 0.9600 |
C11—C1 | 1.522 (3) | C28—C29 | 1.461 (5) |
C19—C20 | 1.402 (3) | C28—H28A | 0.9700 |
C19—H19A | 0.9300 | C28—H28B | 0.9700 |
C1—C2 | 1.377 (3) | C31—H31A | 0.9600 |
C1—C6 | 1.380 (3) | C31—H31B | 0.9600 |
C7—C6 | 1.472 (3) | C31—H31C | 0.9600 |
C13—H13A | 0.9300 | C25—H25A | 0.9600 |
C22—C21 | 1.372 (3) | C25—H25B | 0.9600 |
C22—H22A | 0.9300 | C25—H25C | 0.9600 |
N3—C24 | 1.451 (4) | C29—H29A | 0.9600 |
N3—C26 | 1.459 (4) | C29—H29B | 0.9600 |
C6—C5 | 1.393 (3) | C29—H29C | 0.9600 |
C5—C4 | 1.374 (4) | C9—C10 | 1.476 (5) |
C5—H5A | 0.9300 | C9—H9A | 0.9700 |
C21—C20 | 1.398 (4) | C9—H9B | 0.9700 |
C21—H21A | 0.9300 | C10—H10A | 0.9600 |
C20—N2 | 1.368 (3) | C10—H10B | 0.9600 |
C2—C3 | 1.389 (4) | C10—H10C | 0.9600 |
C2—H2A | 0.9300 | ||
C17—O2—C18 | 118.45 (18) | N3—C24—H24B | 108.6 |
C18—C23—C22 | 115.6 (2) | C25—C24—H24B | 108.6 |
C18—C23—C11 | 123.18 (19) | H24A—C24—H24B | 107.5 |
C22—C23—C11 | 121.2 (2) | N3—C26—C27 | 114.2 (3) |
C17—C12—C13 | 116.2 (2) | N3—C26—H26A | 108.7 |
C17—C12—C11 | 122.7 (2) | C27—C26—H26A | 108.7 |
C13—C12—C11 | 121.2 (2) | N3—C26—H26B | 108.7 |
C12—C17—O2 | 123.11 (19) | C27—C26—H26B | 108.7 |
C12—C17—C16 | 122.1 (2) | H26A—C26—H26B | 107.6 |
O2—C17—C16 | 114.7 (2) | C2—C3—C4 | 120.9 (3) |
C7—N1—C8 | 123.7 (2) | C2—C3—H3A | 119.5 |
C7—N1—C11 | 113.66 (19) | C4—C3—H3A | 119.5 |
C8—N1—C11 | 122.12 (19) | C5—C4—C3 | 121.0 (3) |
C17—C16—C15 | 121.4 (2) | C5—C4—H4A | 119.5 |
C17—C16—H16A | 119.3 | C3—C4—H4A | 119.5 |
C15—C16—H16A | 119.3 | N1—C8—C9 | 113.4 (2) |
N3—C15—C16 | 122.1 (2) | N1—C8—H8A | 108.9 |
N3—C15—C14 | 121.4 (2) | C9—C8—H8A | 108.9 |
C16—C15—C14 | 116.5 (2) | N1—C8—H8B | 108.9 |
C19—C18—C23 | 123.3 (2) | C9—C8—H8B | 108.9 |
C19—C18—O2 | 113.8 (2) | H8A—C8—H8B | 107.7 |
C23—C18—O2 | 122.9 (2) | N2—C30—C31 | 115.3 (3) |
C13—C14—C15 | 120.7 (2) | N2—C30—H30A | 108.5 |
C13—C14—H14A | 119.6 | C31—C30—H30A | 108.5 |
C15—C14—H14A | 119.6 | N2—C30—H30B | 108.5 |
N1—C11—C23 | 112.03 (17) | C31—C30—H30B | 108.5 |
N1—C11—C1 | 100.24 (17) | H30A—C30—H30B | 107.5 |
C23—C11—C1 | 114.03 (18) | C26—C27—H27A | 109.5 |
N1—C11—C12 | 110.26 (17) | C26—C27—H27B | 109.5 |
C23—C11—C12 | 109.73 (18) | H27A—C27—H27B | 109.5 |
C1—C11—C12 | 110.24 (18) | C26—C27—H27C | 109.5 |
C18—C19—C20 | 120.5 (2) | H27A—C27—H27C | 109.5 |
C18—C19—H19A | 119.7 | H27B—C27—H27C | 109.5 |
C20—C19—H19A | 119.7 | C29—C28—N2 | 109.8 (3) |
C2—C1—C6 | 120.7 (2) | C29—C28—H28A | 109.7 |
C2—C1—C11 | 129.0 (2) | N2—C28—H28A | 109.7 |
C6—C1—C11 | 110.2 (2) | C29—C28—H28B | 109.7 |
O1—C7—N1 | 125.2 (2) | N2—C28—H28B | 109.7 |
O1—C7—C6 | 128.1 (2) | H28A—C28—H28B | 108.2 |
N1—C7—C6 | 106.7 (2) | C30—C31—H31A | 109.5 |
C14—C13—C12 | 123.1 (2) | C30—C31—H31B | 109.5 |
C14—C13—H13A | 118.5 | H31A—C31—H31B | 109.5 |
C12—C13—H13A | 118.5 | C30—C31—H31C | 109.5 |
C21—C22—C23 | 122.6 (2) | H31A—C31—H31C | 109.5 |
C21—C22—H22A | 118.7 | H31B—C31—H31C | 109.5 |
C23—C22—H22A | 118.7 | C24—C25—H25A | 109.5 |
C15—N3—C24 | 120.9 (2) | C24—C25—H25B | 109.5 |
C15—N3—C26 | 121.1 (2) | H25A—C25—H25B | 109.5 |
C24—N3—C26 | 117.3 (2) | C24—C25—H25C | 109.5 |
C1—C6—C5 | 121.4 (2) | H25A—C25—H25C | 109.5 |
C1—C6—C7 | 108.8 (2) | H25B—C25—H25C | 109.5 |
C5—C6—C7 | 129.8 (2) | C28—C29—H29A | 109.5 |
C4—C5—C6 | 117.8 (3) | C28—C29—H29B | 109.5 |
C4—C5—H5A | 121.1 | H29A—C29—H29B | 109.5 |
C6—C5—H5A | 121.1 | C28—C29—H29C | 109.5 |
C22—C21—C20 | 121.0 (2) | H29A—C29—H29C | 109.5 |
C22—C21—H21A | 119.5 | H29B—C29—H29C | 109.5 |
C20—C21—H21A | 119.5 | C10—C9—C8 | 110.9 (3) |
N2—C20—C21 | 121.6 (2) | C10—C9—H9A | 109.5 |
N2—C20—C19 | 121.6 (3) | C8—C9—H9A | 109.5 |
C21—C20—C19 | 116.9 (2) | C10—C9—H9B | 109.5 |
C1—C2—C3 | 118.2 (3) | C8—C9—H9B | 109.5 |
C1—C2—H2A | 120.9 | H9A—C9—H9B | 108.0 |
C3—C2—H2A | 120.9 | C9—C10—H10A | 109.5 |
C20—N2—C30 | 121.3 (3) | C9—C10—H10B | 109.5 |
C20—N2—C28 | 121.1 (2) | H10A—C10—H10B | 109.5 |
C30—N2—C28 | 117.6 (3) | C9—C10—H10C | 109.5 |
N3—C24—C25 | 114.8 (2) | H10A—C10—H10C | 109.5 |
N3—C24—H24A | 108.6 | H10B—C10—H10C | 109.5 |
C25—C24—H24A | 108.6 | ||
C13—C12—C17—O2 | 179.4 (2) | C8—N1—C7—C6 | −175.5 (2) |
C11—C12—C17—O2 | −0.8 (4) | C11—N1—C7—C6 | −3.4 (2) |
C13—C12—C17—C16 | 0.4 (3) | C15—C14—C13—C12 | 0.9 (4) |
C11—C12—C17—C16 | −179.8 (2) | C17—C12—C13—C14 | −0.5 (4) |
C18—O2—C17—C12 | −0.2 (3) | C11—C12—C13—C14 | 179.7 (2) |
C18—O2—C17—C16 | 178.9 (2) | C18—C23—C22—C21 | 0.5 (4) |
C12—C17—C16—C15 | −0.7 (4) | C11—C23—C22—C21 | −179.7 (2) |
O2—C17—C16—C15 | −179.8 (2) | C16—C15—N3—C24 | −172.4 (2) |
C17—C16—C15—N3 | −178.0 (2) | C14—C15—N3—C24 | 8.6 (4) |
C17—C16—C15—C14 | 1.1 (4) | C16—C15—N3—C26 | −2.0 (4) |
C22—C23—C18—C19 | −1.1 (4) | C14—C15—N3—C26 | 178.9 (2) |
C11—C23—C18—C19 | 179.1 (2) | C2—C1—C6—C5 | 2.7 (3) |
C22—C23—C18—O2 | 179.9 (2) | C11—C1—C6—C5 | −175.1 (2) |
C11—C23—C18—O2 | 0.0 (4) | C2—C1—C6—C7 | −177.88 (19) |
C17—O2—C18—C19 | −178.6 (2) | C11—C1—C6—C7 | 4.3 (2) |
C17—O2—C18—C23 | 0.5 (3) | O1—C7—C6—C1 | 179.2 (2) |
N3—C15—C14—C13 | 178.0 (2) | N1—C7—C6—C1 | −0.6 (2) |
C16—C15—C14—C13 | −1.1 (4) | O1—C7—C6—C5 | −1.5 (4) |
C7—N1—C11—C23 | 126.9 (2) | N1—C7—C6—C5 | 178.7 (2) |
C8—N1—C11—C23 | −60.9 (3) | C1—C6—C5—C4 | −2.4 (3) |
C7—N1—C11—C1 | 5.6 (2) | C7—C6—C5—C4 | 178.3 (2) |
C8—N1—C11—C1 | 177.8 (2) | C23—C22—C21—C20 | −0.2 (4) |
C7—N1—C11—C12 | −110.6 (2) | C22—C21—C20—N2 | −179.2 (2) |
C8—N1—C11—C12 | 61.6 (3) | C22—C21—C20—C19 | 0.5 (4) |
C18—C23—C11—N1 | 122.0 (2) | C18—C19—C20—N2 | 178.6 (2) |
C22—C23—C11—N1 | −57.9 (3) | C18—C19—C20—C21 | −1.1 (4) |
C18—C23—C11—C1 | −125.1 (2) | C6—C1—C2—C3 | −1.0 (3) |
C22—C23—C11—C1 | 55.1 (3) | C11—C1—C2—C3 | 176.5 (2) |
C18—C23—C11—C12 | −0.8 (3) | C21—C20—N2—C30 | 0.5 (4) |
C22—C23—C11—C12 | 179.3 (2) | C19—C20—N2—C30 | −179.2 (3) |
C17—C12—C11—N1 | −122.7 (2) | C21—C20—N2—C28 | 179.7 (3) |
C13—C12—C11—N1 | 57.2 (3) | C19—C20—N2—C28 | 0.0 (4) |
C17—C12—C11—C23 | 1.2 (3) | C15—N3—C24—C25 | 74.5 (3) |
C13—C12—C11—C23 | −179.0 (2) | C26—N3—C24—C25 | −96.2 (3) |
C17—C12—C11—C1 | 127.6 (2) | C15—N3—C26—C27 | −82.3 (3) |
C13—C12—C11—C1 | −52.6 (3) | C24—N3—C26—C27 | 88.4 (3) |
C23—C18—C19—C20 | 1.5 (4) | C1—C2—C3—C4 | −1.0 (4) |
O2—C18—C19—C20 | −179.4 (2) | C6—C5—C4—C3 | 0.4 (4) |
N1—C11—C1—C2 | 176.6 (2) | C2—C3—C4—C5 | 1.3 (4) |
C23—C11—C1—C2 | 56.7 (3) | C7—N1—C8—C9 | −77.3 (3) |
C12—C11—C1—C2 | −67.2 (3) | C11—N1—C8—C9 | 111.3 (3) |
N1—C11—C1—C6 | −5.8 (2) | C20—N2—C30—C31 | −81.0 (4) |
C23—C11—C1—C6 | −125.7 (2) | C28—N2—C30—C31 | 99.8 (4) |
C12—C11—C1—C6 | 110.4 (2) | C20—N2—C28—C29 | 81.2 (4) |
C8—N1—C7—O1 | 4.7 (4) | C30—N2—C28—C29 | −99.6 (3) |
C11—N1—C7—O1 | 176.7 (2) | N1—C8—C9—C10 | 175.2 (3) |
Experimental details
Crystal data | |
Chemical formula | C31H37N3O2 |
Mr | 483.64 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 273 |
a, b, c (Å) | 11.1697 (4), 11.8605 (4), 12.4512 (4) |
α, β, γ (°) | 82.838 (3), 64.605 (2), 65.588 (2) |
V (Å3) | 1354.13 (8) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.55 × 0.40 × 0.20 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 1997) |
Tmin, Tmax | 0.960, 0.985 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9526, 4699, 2963 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.061, 0.201, 1.07 |
No. of reflections | 4699 |
No. of parameters | 330 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.32, −0.24 |
Computer programs: APEX2 (Bruker, 2005), SMART (Bruker, 1997), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
O2—C17 | 1.377 (3) | O1—C7 | 1.223 (3) |
O2—C18 | 1.382 (3) | C15—N3 | 1.382 (3) |
C23—C11 | 1.504 (3) | C11—C1 | 1.522 (3) |
C12—C11 | 1.525 (3) | C20—N2 | 1.368 (3) |
N1—C11 | 1.486 (3) | ||
N1—C11—C23 | 112.03 (17) | N1—C11—C12 | 110.26 (17) |
N1—C11—C1 | 100.24 (17) | C23—C11—C12 | 109.73 (18) |
C23—C11—C1 | 114.03 (18) | C1—C11—C12 | 110.24 (18) |
Rhodamine dyes are widely used as fluorescent labels (De Silva et al., 1997) but only a few of such compounds were characterized by single-crystal X-ray diffraction (Kwon et al., 2005). However, for the understanding of their photophysical and photochemical properties, information on their molecular and crystal structures are needed. As part of our ongoing work on rhodamine dyes, we report here the synthesis and crystal structure of the title compound 3',6'-Bis(diethylamino)-2-propyl-spiro[isoindoline-1,9'-[xanthen]-3-one (I).
As similar compounds the main skeleton of the molecule is built up of an xanthene ring which is connected to an spirolactam-ring (Kwon et al., 2005). The lactam moiety is oriented nearly orthogonal to the xanthene moiety. The dihedral angle between the planes of the xanthene ring and the spirolactam-ring amount to 90.3°.