3',6'-Bis(diethyl-amino)-2-phenyl-spiro[isoindoline-1,9'-xanthen]-3-one.

The title compound, C(34)H(35)O(2)N(3), was synthesized by the reaction of 2-[3,6-bis-(diethyl-amino)-9H-xanthen-9-yl]benzoyl chloride with aniline. In the mol-ecular structure, the dihedral angles between the isoindoline and xanthene planes and between the isoindoline and benzene planes are 86.9 (3) and 47.0 (2)°, respectively. The mol-ecular packing in the crystal structure is stabilized by weak C-H⋯O hydrogen bonding.

Related literature

For applications of rhodamine-based dyes as probes and sensors, see: Zheng et al. (2008 ▶); Wu et al. (2007 ▶). For a related structure, see: Kwon et al. (2005 ▶).

Experimental

Crystal data

C34H35N3O2

M = 517.65

Monoclinic,

a = 12.0213 (5) Å

b = 12.6315 (4) Å

c = 18.9700 (7) Å

β = 107.456 (4)°

V = 2747.88 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 173 K

0.30 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire3 (Gemini Ultra Mo) detector

Absorption correction: none

29794 measured reflections

5403 independent reflections

4396 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.103

S = 1.06

5403 reflections

352 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809020248/xu2519sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020248/xu2519Isup2.hkl

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

C34H35N3O2	F(000) = 1104
Mr = 517.65	Dx = 1.251 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 16600 reflections
a = 12.0213 (5) Å	θ = 2.4–32.7°
b = 12.6315 (4) Å	µ = 0.08 mm−1
c = 18.9700 (7) Å	T = 173 K
β = 107.456 (4)°	Block, colourless
V = 2747.88 (18) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire3 (Gemini ultra Mo) detector	4396 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
graphite	θmax = 26.0°, θmin = 2.4°
Detector resolution: 16.1903 pixels mm-1	h = −14→14
φ and ω scans	k = −15→15
29794 measured reflections	l = −21→23
5403 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0572P)2 + 0.4462P] where P = (Fo2 + 2Fc2)/3
5403 reflections	(Δ/σ)max = 0.006
352 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

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
C1	0.71114 (11)	0.71818 (10)	0.15020 (7)	0.0228 (3)
C2	0.82352 (12)	0.71273 (11)	0.14514 (8)	0.0267 (3)
H2A	0.8558	0.7722	0.1277	0.032*
C3	0.88993 (11)	0.62080 (11)	0.16541 (7)	0.0247 (3)
C4	0.83537 (12)	0.53371 (10)	0.18815 (7)	0.0240 (3)
H4A	0.8767	0.4690	0.2011	0.029*
C5	0.72318 (11)	0.54138 (10)	0.19186 (7)	0.0219 (3)
H5A	0.6893	0.4815	0.2077	0.026*
C6	0.65727 (11)	0.63372 (10)	0.17327 (7)	0.0192 (3)
C7	0.53398 (11)	0.64059 (10)	0.17788 (7)	0.0192 (3)
C8	0.48969 (11)	0.75350 (9)	0.16449 (7)	0.0192 (3)
C9	0.38198 (11)	0.78341 (10)	0.17203 (7)	0.0212 (3)
H9A	0.3381	0.7321	0.1890	0.025*
C10	0.33646 (11)	0.88340 (10)	0.15613 (7)	0.0225 (3)
H10A	0.2624	0.8995	0.1617	0.027*
C11	0.39947 (11)	0.96252 (10)	0.13143 (7)	0.0219 (3)
C12	0.50750 (12)	0.93349 (10)	0.12374 (7)	0.0235 (3)
H12A	0.5524	0.9844	0.1073	0.028*
C13	0.54985 (11)	0.83143 (10)	0.13973 (7)	0.0214 (3)
C14	0.44953 (11)	0.56635 (10)	0.12430 (7)	0.0214 (3)
C15	0.41783 (12)	0.56501 (11)	0.04796 (8)	0.0275 (3)
H15A	0.4507	0.6137	0.0216	0.033*
C16	0.33642 (13)	0.49019 (12)	0.01089 (8)	0.0340 (4)
H16A	0.3143	0.4871	−0.0415	0.041*
C17	0.28681 (13)	0.41981 (12)	0.04928 (9)	0.0349 (4)
H17A	0.2307	0.3698	0.0228	0.042*
C18	0.31836 (12)	0.42201 (11)	0.12532 (9)	0.0308 (3)
H18A	0.2847	0.3743	0.1519	0.037*
C19	0.40063 (11)	0.49595 (10)	0.16190 (8)	0.0235 (3)
C20	0.45099 (12)	0.51313 (10)	0.24234 (8)	0.0237 (3)
C21	0.60912 (11)	0.62493 (10)	0.31955 (7)	0.0219 (3)
C22	0.66767 (14)	0.54632 (12)	0.36746 (8)	0.0341 (3)
H22A	0.6536	0.4739	0.3542	0.041*
C23	0.74656 (14)	0.57334 (13)	0.43449 (8)	0.0393 (4)
H23A	0.7852	0.5192	0.4676	0.047*
C24	0.76971 (14)	0.67813 (13)	0.45384 (8)	0.0385 (4)
H24A	0.8240	0.6965	0.4999	0.046*
C25	0.71330 (15)	0.75539 (13)	0.40563 (9)	0.0439 (4)
H25A	0.7297	0.8277	0.4182	0.053*
C26	0.63245 (14)	0.72939 (11)	0.33859 (8)	0.0360 (4)
H26A	0.5933	0.7838	0.3059	0.043*
C27	0.41811 (13)	1.14312 (11)	0.08587 (8)	0.0327 (3)
H27A	0.3609	1.1947	0.0563	0.039*
H27B	0.4559	1.1081	0.0523	0.039*
C28	0.51015 (15)	1.20246 (12)	0.14500 (10)	0.0418 (4)
H28A	0.5487	1.2541	0.1216	0.063*
H28B	0.5681	1.1522	0.1740	0.063*
H28C	0.4732	1.2394	0.1776	0.063*
C29	0.25151 (14)	1.09900 (12)	0.13220 (9)	0.0372 (4)
H29A	0.2611	1.1744	0.1470	0.045*
H29B	0.2431	1.0579	0.1747	0.045*
C30	0.14156 (16)	1.08697 (19)	0.06812 (11)	0.0630 (6)
H30A	0.0747	1.1124	0.0827	0.094*
H30B	0.1302	1.0122	0.0540	0.094*
H30C	0.1485	1.1285	0.0260	0.094*
C31	1.06594 (13)	0.70793 (12)	0.15060 (10)	0.0379 (4)
H31A	1.1479	0.7048	0.1825	0.045*
H31B	1.0301	0.7720	0.1646	0.045*
C32	1.06523 (17)	0.71910 (15)	0.07113 (10)	0.0540 (5)
H32A	1.1085	0.7829	0.0659	0.081*
H32B	0.9846	0.7248	0.0391	0.081*
H32C	1.1022	0.6569	0.0569	0.081*
C33	1.06374 (13)	0.51390 (12)	0.17186 (8)	0.0319 (3)
H33A	1.0513	0.4745	0.2140	0.038*
H33B	1.1485	0.5266	0.1831	0.038*
C34	1.02314 (13)	0.44583 (12)	0.10308 (9)	0.0364 (4)
H34A	1.0664	0.3789	0.1113	0.055*
H34B	1.0372	0.4833	0.0613	0.055*
H34C	0.9396	0.4313	0.0922	0.055*
N1	0.35614 (10)	1.06343 (9)	0.11526 (7)	0.0306 (3)
N2	1.00455 (10)	0.61526 (10)	0.16542 (7)	0.0332 (3)
N3	0.52732 (9)	0.59642 (8)	0.25021 (6)	0.0205 (2)
O1	0.65733 (8)	0.81453 (7)	0.12950 (6)	0.0307 (2)
O2	0.42961 (9)	0.46357 (8)	0.29198 (6)	0.0345 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0214 (7)	0.0196 (6)	0.0281 (7)	0.0008 (5)	0.0084 (6)	−0.0007 (5)
C2	0.0222 (7)	0.0232 (7)	0.0372 (8)	−0.0038 (5)	0.0128 (6)	−0.0019 (6)
C3	0.0176 (7)	0.0295 (7)	0.0257 (7)	0.0001 (5)	0.0045 (5)	−0.0075 (6)
C4	0.0218 (7)	0.0243 (7)	0.0244 (7)	0.0057 (5)	0.0048 (5)	−0.0009 (5)
C5	0.0229 (7)	0.0223 (7)	0.0203 (6)	−0.0001 (5)	0.0064 (5)	0.0006 (5)
C6	0.0169 (6)	0.0216 (6)	0.0188 (6)	−0.0003 (5)	0.0048 (5)	−0.0016 (5)
C7	0.0177 (6)	0.0211 (6)	0.0187 (6)	−0.0007 (5)	0.0053 (5)	0.0013 (5)
C8	0.0180 (6)	0.0198 (6)	0.0188 (6)	−0.0001 (5)	0.0040 (5)	−0.0001 (5)
C9	0.0185 (7)	0.0229 (7)	0.0221 (6)	−0.0016 (5)	0.0060 (5)	0.0013 (5)
C10	0.0169 (6)	0.0252 (7)	0.0241 (6)	0.0025 (5)	0.0041 (5)	−0.0009 (5)
C11	0.0217 (7)	0.0204 (6)	0.0207 (6)	0.0029 (5)	0.0019 (5)	0.0002 (5)
C12	0.0231 (7)	0.0206 (7)	0.0275 (7)	−0.0015 (5)	0.0085 (6)	0.0036 (5)
C13	0.0180 (7)	0.0229 (7)	0.0232 (6)	0.0007 (5)	0.0062 (5)	0.0001 (5)
C14	0.0153 (6)	0.0205 (6)	0.0273 (7)	0.0032 (5)	0.0049 (5)	−0.0040 (5)
C15	0.0227 (7)	0.0306 (7)	0.0285 (7)	0.0033 (6)	0.0068 (6)	−0.0008 (6)
C16	0.0259 (8)	0.0414 (9)	0.0286 (7)	0.0081 (6)	−0.0012 (6)	−0.0116 (6)
C17	0.0207 (7)	0.0287 (8)	0.0492 (9)	−0.0006 (6)	0.0015 (7)	−0.0164 (7)
C18	0.0219 (7)	0.0220 (7)	0.0483 (9)	0.0001 (6)	0.0100 (6)	−0.0046 (6)
C19	0.0181 (7)	0.0194 (6)	0.0334 (7)	0.0035 (5)	0.0083 (6)	−0.0026 (5)
C20	0.0217 (7)	0.0186 (6)	0.0341 (7)	0.0024 (5)	0.0132 (6)	0.0022 (5)
C21	0.0197 (7)	0.0269 (7)	0.0197 (6)	0.0037 (5)	0.0071 (5)	−0.0011 (5)
C22	0.0398 (9)	0.0287 (8)	0.0311 (8)	0.0039 (7)	0.0065 (7)	0.0052 (6)
C23	0.0395 (9)	0.0459 (10)	0.0277 (8)	0.0082 (7)	0.0029 (7)	0.0120 (7)
C24	0.0360 (9)	0.0513 (10)	0.0233 (7)	0.0056 (7)	0.0014 (6)	−0.0050 (7)
C25	0.0471 (10)	0.0341 (9)	0.0377 (9)	0.0041 (7)	−0.0069 (8)	−0.0114 (7)
C26	0.0410 (9)	0.0259 (7)	0.0318 (8)	0.0069 (6)	−0.0033 (7)	0.0000 (6)
C27	0.0348 (8)	0.0229 (7)	0.0407 (8)	0.0070 (6)	0.0118 (7)	0.0098 (6)
C28	0.0411 (10)	0.0309 (8)	0.0529 (10)	0.0000 (7)	0.0131 (8)	0.0054 (7)
C29	0.0386 (9)	0.0259 (7)	0.0519 (10)	0.0125 (7)	0.0209 (8)	0.0079 (7)
C30	0.0363 (10)	0.0903 (16)	0.0623 (12)	0.0247 (10)	0.0148 (9)	0.0299 (11)
C31	0.0181 (7)	0.0366 (9)	0.0593 (11)	−0.0060 (6)	0.0123 (7)	−0.0130 (7)
C32	0.0554 (12)	0.0458 (10)	0.0569 (11)	−0.0162 (9)	0.0110 (9)	0.0081 (9)
C33	0.0193 (7)	0.0420 (9)	0.0339 (8)	0.0091 (6)	0.0075 (6)	0.0021 (6)
C34	0.0303 (8)	0.0384 (8)	0.0430 (9)	0.0028 (7)	0.0149 (7)	−0.0043 (7)
N1	0.0279 (7)	0.0227 (6)	0.0424 (7)	0.0074 (5)	0.0123 (6)	0.0073 (5)
N2	0.0184 (6)	0.0320 (7)	0.0504 (8)	0.0006 (5)	0.0123 (6)	−0.0056 (6)
N3	0.0212 (6)	0.0196 (5)	0.0215 (5)	−0.0002 (4)	0.0075 (4)	0.0022 (4)
O1	0.0242 (5)	0.0210 (5)	0.0540 (7)	0.0036 (4)	0.0225 (5)	0.0089 (4)
O2	0.0385 (6)	0.0315 (6)	0.0391 (6)	−0.0055 (5)	0.0202 (5)	0.0072 (4)

C1—O1	1.3789 (15)	C21—C22	1.3870 (19)
C1—C2	1.3846 (19)	C21—N3	1.4320 (16)
C1—C6	1.3854 (18)	C22—C23	1.382 (2)
C2—C3	1.3961 (19)	C22—H22A	0.9500
C2—H2A	0.9500	C23—C24	1.380 (2)
C3—N2	1.3796 (18)	C23—H23A	0.9500
C3—C4	1.413 (2)	C24—C25	1.370 (2)
C4—C5	1.3749 (19)	C24—H24A	0.9500
C4—H4A	0.9500	C25—C26	1.389 (2)
C5—C6	1.3945 (18)	C25—H25A	0.9500
C5—H5A	0.9500	C26—H26A	0.9500
C6—C7	1.5131 (18)	C27—N1	1.4588 (19)
C7—N3	1.5054 (16)	C27—C28	1.516 (2)
C7—C8	1.5170 (17)	C27—H27A	0.9900
C7—C14	1.5245 (17)	C27—H27B	0.9900
C8—C13	1.3842 (18)	C28—H28A	0.9800
C8—C9	1.3967 (18)	C28—H28B	0.9800
C9—C10	1.3735 (18)	C28—H28C	0.9800
C9—H9A	0.9500	C29—N1	1.4593 (19)
C10—C11	1.4161 (19)	C29—C30	1.511 (3)
C10—H10A	0.9500	C29—H29A	0.9900
C11—N1	1.3763 (17)	C29—H29B	0.9900
C11—C12	1.3985 (19)	C30—H30A	0.9800
C12—C13	1.3858 (18)	C30—H30B	0.9800
C12—H12A	0.9500	C30—H30C	0.9800
C13—O1	1.3795 (16)	C31—N2	1.4555 (19)
C14—C19	1.3773 (19)	C31—C32	1.512 (3)
C14—C15	1.3826 (19)	C31—H31A	0.9900
C15—C16	1.390 (2)	C31—H31B	0.9900
C15—H15A	0.9500	C32—H32A	0.9800
C16—C17	1.392 (2)	C32—H32B	0.9800
C16—H16A	0.9500	C32—H32C	0.9800
C17—C18	1.377 (2)	C33—N2	1.4520 (18)
C17—H17A	0.9500	C33—C34	1.516 (2)
C18—C19	1.3858 (19)	C33—H33A	0.9900
C18—H18A	0.9500	C33—H33B	0.9900
C19—C20	1.4790 (19)	C34—H34A	0.9800
C20—O2	1.2207 (16)	C34—H34B	0.9800
C20—N3	1.3744 (17)	C34—H34C	0.9800
C21—C26	1.3744 (19)
O1—C1—C2	114.10 (11)	C24—C23—H23A	119.7
O1—C1—C6	123.08 (12)	C22—C23—H23A	119.7
C2—C1—C6	122.81 (12)	C25—C24—C23	119.08 (14)
C1—C2—C3	120.76 (12)	C25—C24—H24A	120.5
C1—C2—H2A	119.6	C23—C24—H24A	120.5
C3—C2—H2A	119.6	C24—C25—C26	120.88 (15)
N2—C3—C2	122.06 (13)	C24—C25—H25A	119.6
N2—C3—C4	121.03 (12)	C26—C25—H25A	119.6
C2—C3—C4	116.88 (12)	C21—C26—C25	119.95 (13)
C5—C4—C3	120.87 (12)	C21—C26—H26A	120.0
C5—C4—H4A	119.6	C25—C26—H26A	120.0
C3—C4—H4A	119.6	N1—C27—C28	113.66 (13)
C4—C5—C6	122.52 (12)	N1—C27—H27A	108.8
C4—C5—H5A	118.7	C28—C27—H27A	108.8
C6—C5—H5A	118.7	N1—C27—H27B	108.8
C1—C6—C5	116.11 (12)	C28—C27—H27B	108.8
C1—C6—C7	122.20 (11)	H27A—C27—H27B	107.7
C5—C6—C7	121.69 (11)	C27—C28—H28A	109.5
N3—C7—C6	110.63 (10)	C27—C28—H28B	109.5
N3—C7—C8	112.90 (10)	H28A—C28—H28B	109.5
C6—C7—C8	110.18 (10)	C27—C28—H28C	109.5
N3—C7—C14	99.96 (10)	H28A—C28—H28C	109.5
C6—C7—C14	113.21 (10)	H28B—C28—H28C	109.5
C8—C7—C14	109.67 (10)	N1—C29—C30	113.30 (15)
C13—C8—C9	115.92 (11)	N1—C29—H29A	108.9
C13—C8—C7	122.18 (12)	C30—C29—H29A	108.9
C9—C8—C7	121.79 (11)	N1—C29—H29B	108.9
C10—C9—C8	123.15 (12)	C30—C29—H29B	108.9
C10—C9—H9A	118.4	H29A—C29—H29B	107.7
C8—C9—H9A	118.4	C29—C30—H30A	109.5
C9—C10—C11	120.28 (12)	C29—C30—H30B	109.5
C9—C10—H10A	119.9	H30A—C30—H30B	109.5
C11—C10—H10A	119.9	C29—C30—H30C	109.5
N1—C11—C12	121.39 (12)	H30A—C30—H30C	109.5
N1—C11—C10	121.54 (12)	H30B—C30—H30C	109.5
C12—C11—C10	117.07 (11)	N2—C31—C32	114.59 (13)
C13—C12—C11	120.85 (12)	N2—C31—H31A	108.6
C13—C12—H12A	119.6	C32—C31—H31A	108.6
C11—C12—H12A	119.6	N2—C31—H31B	108.6
O1—C13—C8	122.99 (11)	C32—C31—H31B	108.6
O1—C13—C12	114.28 (11)	H31A—C31—H31B	107.6
C8—C13—C12	122.73 (12)	C31—C32—H32A	109.5
C19—C14—C15	120.55 (12)	C31—C32—H32B	109.5
C19—C14—C7	110.74 (11)	H32A—C32—H32B	109.5
C15—C14—C7	128.69 (12)	C31—C32—H32C	109.5
C14—C15—C16	117.98 (14)	H32A—C32—H32C	109.5
C14—C15—H15A	121.0	H32B—C32—H32C	109.5
C16—C15—H15A	121.0	N2—C33—C34	113.87 (12)
C15—C16—C17	121.11 (14)	N2—C33—H33A	108.8
C15—C16—H16A	119.4	C34—C33—H33A	108.8
C17—C16—H16A	119.4	N2—C33—H33B	108.8
C18—C17—C16	120.57 (13)	C34—C33—H33B	108.8
C18—C17—H17A	119.7	H33A—C33—H33B	107.7
C16—C17—H17A	119.7	C33—C34—H34A	109.5
C17—C18—C19	117.97 (14)	C33—C34—H34B	109.5
C17—C18—H18A	121.0	H34A—C34—H34B	109.5
C19—C18—H18A	121.0	C33—C34—H34C	109.5
C14—C19—C18	121.81 (13)	H34A—C34—H34C	109.5
C14—C19—C20	109.47 (11)	H34B—C34—H34C	109.5
C18—C19—C20	128.71 (13)	C11—N1—C27	121.45 (12)
O2—C20—N3	126.65 (13)	C11—N1—C29	121.98 (12)
O2—C20—C19	127.22 (13)	C27—N1—C29	116.38 (11)
N3—C20—C19	106.13 (11)	C3—N2—C33	120.59 (12)
C26—C21—C22	119.45 (13)	C3—N2—C31	121.56 (12)
C26—C21—N3	120.83 (12)	C33—N2—C31	117.48 (12)
C22—C21—N3	119.70 (12)	C20—N3—C21	122.99 (11)
C23—C22—C21	119.97 (14)	C20—N3—C7	113.63 (10)
C23—C22—H22A	120.0	C21—N3—C7	122.30 (10)
C21—C22—H22A	120.0	C1—O1—C13	118.40 (10)
C24—C23—C22	120.65 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C31—H31B···O2i	0.99	2.56	3.4032 (19)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C31—H31B⋯O2i	0.99	2.56	3.4032 (19)	144

Symmetry code: (i) .