[(2-{[3′,6′-Bis(ethyl­amino)-2′,7′-dimethyl-3-oxospiro­[1H-isoindole-1,9′-9H-xanthen]-2-yl}eth­yl)amino­meth­yl]phenol

Zhang, L.-Z.; Peng, X.-J.; Gao, S.; Fan, J.-L.

doi:10.1107/S1600536807068742

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o403

doi:10.1107/S1600536807068742

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ADDENDA AND ERRATA

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[(2-{[3′,6′-Bis(ethylamino)-2′,7′-dimethyl-3-oxospiro[1H-isoindole-1,9′-9H-xanthen]-2-yl}ethyl)aminomethyl]phenol

Li-Zhu Zhang,^a Xiao-Jun Peng,^a ^* Shang Gao ^a and Jiang-Li Fan ^a

^aState Key Laboratory of Fine Chemicals, Dalian University of Technology, 158 Zhongshan Road, Dalian 116012, People's Republic of China
^*Correspondence e-mail: pengxj@dlut.edu.cn

(Received 19 November 2007; accepted 29 December 2007; online 9 January 2008)

The title compound, C₃₅H₃₈N₄O₃, was prepared as a spirolactam ring formation of rhodamine dye for comparison with a ring-opened form. The xanthene ring system is approximately planar. The dihedral angles formed by the spirolactam and phenol rings with the xanthene ring system are 85.7 and 109.4°, respectively. Each of the molecules in the crystal structure contains one intramolecular O—H⋯N hydrogen bond, and they form intermolecular N—H⋯O hydrogen-bonded chains along the [100] direction. Weak intermolecular C—H⋯O hydrogen-bonding contacts connect the infinite chains via crystallographic inversion centres to form a two-dimensional network.

Related literature

For related literature, see: Kwon et al. (2005 ); Wu et al. (2007 ); De Silva et al. (1997 ).

Experimental

Crystal data

C₃₅H₃₆N₄O₃
M_r = 560.68
Triclinic, $[P \overline 1]$
a = 11.6453 (5) Å
b = 11.8588 (3) Å
c = 12.9822 (3) Å
α = 116.3210 (10)°
β = 103.173 (2)°
γ = 98.337 (2)°
V = 1501.21 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 273 (2) K
0.30 × 0.30 × 0.25 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.976, T_max = 0.980
9518 measured reflections
5018 independent reflections
3667 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.169
S = 1.01
5018 reflections
383 parameters
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯N2	0.82	2.01	2.685 (3)	139
N3—H3B⋯O3ⁱ	0.86	2.32	3.144 (1)	160
C9—H9A⋯O2ⁱⁱ	0.93	2.59	3.468 (3)	157
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+3, -z+1.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2001 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807068742/si2058sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807068742/si2058Isup2.hkl

checkCIF report

Comment top

Rhodamine dyes are widely used in fluorescent labels and other present biological techniques (De Silva et al., 1997). There are a few single-crystal reports about the rhodamine derivatives bearing the lactam moiety (Kwon et al., 2005; Wu et al.,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 dyes, the title compound (Fig. 1) was prepared by the reaction of N-(rhodamine-6 G) lactam-ethylenediamine with 2-hydroxybenzaldehyde.

In agreement with other reported models, the main skeleton of the molecule is formed from the xanthene ring and the spirolactam-ring (Kwon et al., 2005; Wu et al., 2007). The atoms of the xanthene ring or the spirolactam-ring are almost coplanar. The planes formed have r.m.s. deviations from the mean plane of only 0.0248 Å for the xanthene ring and 0.0231 Å for the spirolactam-ring, respectively. The dihedral angle between the planes of the xanthene ring and the spirolactam-ring fragment is 85.7°. The phenol part of the molecule (C30 benzene ring plus O3) is close to being planar, with an r.m.s. deviation for the fitted atoms of 0.0065 Å. The dihedral angle with the planes of the xanthene ring and the spirolactam-ring fragment is 109.4° and 107.8° respectively. Each of the molecules in the crystal structure contains one O—H···N intramolecular hydrogen bond, and they form infinite intermolecular N—H···O hydrogen bonded chains along [1 0 0]. Weak intermolecular C—H···O hydrogen bonding contacts connect the infinite chains via crystallographic inversion centres to form a two-dimensional network (Table 1).

Related literature top

For related literature, see: Kwon et al. (2005); Wu et al. (2007); De Silva et al. (1997).

Experimental top

N-(rhodamine-6 G) lactam-ethylenediamine (500 mg, 1.2 mmol) was dissolved in 20 ml of methanol, followed by addition of 2-hydroxybenzaldehyde (146 mg, 1.2 mmol). The yellow solution was mixed for 1 h at room temperature, and then added NaBH₄ until the reactant disappeared on TLC. The solvent was removed by rotatory evaporation. The resulting crude product was purified by column chromatography to give 317 mg of the title compound (white solid) in 47.1% yield. Single crystals suitable for X-ray measurements were obtained from hexane/dichloromethane (1:1, v/v) solution by slow evaporation at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (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 (Bruker, 1997).

Figures top

Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at 30% probability level.

[(2-{[3',6'-Bis(ethylamino)-2',7'-dimethyl-3-oxospiro[1H-isoindole-1,9'-\ 9H-xanthen]-2-yl}ethyl)aminomethyl]phenol top

Crystal data top

C₃₅H₃₆N₄O₃	Z = 2
M_r = 560.68	F(000) = 596
Triclinic, P1	D_x = 1.240 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.6453 (5) Å	Cell parameters from 2891 reflections
b = 11.8588 (3) Å	θ = 2.7–27.2°
c = 12.9822 (3) Å	µ = 0.08 mm⁻¹
α = 116.321 (1)°	T = 273 K
β = 103.173 (2)°	Block, white
γ = 98.337 (2)°	0.30 × 0.30 × 0.25 mm
V = 1501.21 (8) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	5018 independent reflections
Radiation source: fine-focus sealed tube	3667 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −13→12
T_min = 0.976, T_max = 0.980	k = −14→13
9518 measured reflections	l = −15→15

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.056	w = 1/[σ²(F_o²) + (0.0943P)² + 0.4133P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.169	(Δ/σ)_max < 0.001
S = 1.01	Δρ_max = 0.55 e Å⁻³
5018 reflections	Δρ_min = −0.34 e Å⁻³
383 parameters

Crystal data top

C₃₅H₃₆N₄O₃	γ = 98.337 (2)°
M_r = 560.68	V = 1501.21 (8) Å³
Triclinic, P1	Z = 2
a = 11.6453 (5) Å	Mo Kα radiation
b = 11.8588 (3) Å	µ = 0.08 mm⁻¹
c = 12.9822 (3) Å	T = 273 K
α = 116.321 (1)°	0.30 × 0.30 × 0.25 mm
β = 103.173 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	5018 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	3667 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.980	R_int = 0.020
9518 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.169	H-atom parameters constrained
S = 1.01	Δρ_max = 0.55 e Å⁻³
5018 reflections	Δρ_min = −0.34 e Å⁻³
383 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
O1	0.61529 (16)	0.99784 (14)	0.12430 (14)	0.0552 (4)
O2	0.52746 (17)	1.55773 (17)	0.38418 (16)	0.0697 (5)
O3	0.10319 (17)	1.2888 (2)	−0.06993 (17)	0.0752 (6)
H3A	0.1732	1.3180	−0.0213	0.113*
N1	0.55473 (16)	1.35526 (16)	0.27576 (15)	0.0430 (4)
N2	0.34153 (17)	1.29474 (18)	−0.01746 (17)	0.0496 (5)
N3	0.88189 (19)	1.10924 (19)	−0.06256 (18)	0.0571 (5)
H3B	0.9285	1.1680	−0.0682	0.068*
N4	0.35515 (18)	0.83845 (18)	0.29282 (19)	0.0539 (5)
H4A	0.3082	0.8541	0.3369	0.065*
C1	0.6847 (2)	1.0985 (2)	0.11824 (19)	0.0440 (5)
C2	0.7442 (2)	1.0584 (2)	0.0336 (2)	0.0477 (6)
H2B	0.7345	0.9694	−0.0143	0.057*
C3	0.8187 (2)	1.1487 (2)	0.0184 (2)	0.0443 (5)
C4	0.82894 (19)	1.2838 (2)	0.0902 (2)	0.0439 (5)
C5	0.7681 (2)	1.3186 (2)	0.1733 (2)	0.0442 (5)
H5A	0.7758	1.4072	0.2205	0.053*
C6	0.69504 (19)	1.2290 (2)	0.19164 (19)	0.0413 (5)
C7	0.63690 (19)	1.2743 (2)	0.29058 (19)	0.0407 (5)
C8	0.56535 (19)	1.1577 (2)	0.29171 (19)	0.0413 (5)
C9	0.5015 (2)	1.1743 (2)	0.37370 (19)	0.0448 (5)
H9A	0.5057	1.2593	0.4294	0.054*
C10	0.4326 (2)	1.0719 (2)	0.3771 (2)	0.0448 (5)
C11	0.4261 (2)	0.9423 (2)	0.2921 (2)	0.0441 (5)
C12	0.4884 (2)	0.9238 (2)	0.2102 (2)	0.0477 (6)
H12A	0.4847	0.8392	0.1540	0.057*
C13	0.5566 (2)	1.0302 (2)	0.21049 (19)	0.0432 (5)
C14	0.9068 (2)	1.3854 (2)	0.0759 (2)	0.0593 (7)
H14A	0.8967	1.4698	0.1244	0.089*
H14B	0.8818	1.3633	−0.0080	0.089*
H14C	0.9916	1.3879	0.1023	0.089*
C15	0.8734 (3)	0.9726 (2)	−0.1390 (2)	0.0617 (7)
H15A	0.7899	0.9267	−0.1946	0.074*
H15B	0.8922	0.9328	−0.0884	0.074*
C16	0.9601 (3)	0.9574 (3)	−0.2109 (3)	0.0731 (8)
H16A	0.9549	0.8663	−0.2572	0.110*
H16B	1.0426	1.0050	−0.1563	0.110*
H16C	0.9382	0.9914	−0.2651	0.110*
C17	0.3645 (2)	1.0961 (2)	0.4661 (2)	0.0599 (7)
H17A	0.3775	1.1887	0.5149	0.090*
H17B	0.3941	1.0612	0.5177	0.090*
H17C	0.2783	1.0540	0.4229	0.090*
C18	0.3572 (2)	0.7054 (2)	0.2223 (2)	0.0558 (6)
H18A	0.4406	0.6995	0.2449	0.067*
H18B	0.3307	0.6794	0.1366	0.067*
C19	0.2740 (3)	0.6137 (3)	0.2434 (3)	0.0710 (8)
H19A	0.2798	0.5262	0.1987	0.106*
H19B	0.1907	0.6153	0.2162	0.106*
H19C	0.2986	0.6411	0.3286	0.106*
C20	0.7308 (2)	1.3743 (2)	0.41426 (19)	0.0440 (5)
C21	0.8369 (2)	1.3621 (2)	0.4758 (2)	0.0566 (6)
H21A	0.8599	1.2852	0.4427	0.068*
C22	0.9085 (3)	1.4675 (3)	0.5882 (3)	0.0679 (8)
H22A	0.9807	1.4613	0.6312	0.081*
C23	0.8745 (3)	1.5813 (3)	0.6375 (2)	0.0728 (8)
H23A	0.9235	1.6504	0.7138	0.087*
C24	0.7691 (3)	1.5944 (2)	0.5756 (2)	0.0646 (7)
H24A	0.7464	1.6715	0.6087	0.077*
C25	0.6977 (2)	1.4891 (2)	0.4624 (2)	0.0492 (6)
C26	0.5851 (2)	1.4766 (2)	0.3749 (2)	0.0497 (6)
C27	0.4445 (2)	1.3027 (2)	0.1728 (2)	0.0482 (6)
H27A	0.3760	1.3217	0.2018	0.058*
H27B	0.4277	1.2082	0.1272	0.058*
C28	0.4528 (2)	1.3576 (2)	0.0890 (2)	0.0518 (6)
H28A	0.4637	1.4514	0.1323	0.062*
H28B	0.5237	1.3433	0.0629	0.062*
C29	0.3371 (2)	1.3596 (2)	−0.0916 (2)	0.0552 (6)
H29A	0.3996	1.4300	−0.0749	0.066*
C30	0.2200 (2)	1.2987 (2)	−0.1972 (2)	0.0526 (6)
C31	0.2189 (3)	1.2780 (3)	−0.3105 (3)	0.0811 (9)
H31A	0.2927	1.2992	−0.3230	0.097*
C32	0.1091 (5)	1.2257 (4)	−0.4065 (3)	0.1077 (13)
H32A	0.1095	1.2120	−0.4827	0.129*
C33	0.0009 (4)	1.1948 (4)	−0.3886 (4)	0.1007 (12)
H33A	−0.0724	1.1579	−0.4533	0.121*
C34	−0.0008 (3)	1.2176 (3)	−0.2758 (3)	0.0790 (9)
H34A	−0.0752	1.1992	−0.2633	0.095*
C35	0.1079 (2)	1.2677 (2)	−0.1814 (2)	0.0554 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0714 (11)	0.0304 (8)	0.0645 (10)	0.0073 (7)	0.0418 (9)	0.0170 (7)
O2	0.0791 (13)	0.0448 (11)	0.0760 (12)	0.0301 (9)	0.0223 (10)	0.0201 (9)
O3	0.0627 (12)	0.0906 (14)	0.0746 (12)	0.0092 (10)	0.0367 (10)	0.0397 (11)
N1	0.0433 (10)	0.0308 (9)	0.0472 (10)	0.0084 (7)	0.0125 (8)	0.0147 (8)
N2	0.0487 (11)	0.0499 (11)	0.0488 (10)	0.0077 (8)	0.0154 (9)	0.0255 (9)
N3	0.0664 (14)	0.0418 (11)	0.0643 (12)	0.0082 (9)	0.0374 (11)	0.0220 (9)
N4	0.0567 (12)	0.0400 (11)	0.0742 (13)	0.0135 (9)	0.0381 (11)	0.0281 (10)
C1	0.0464 (13)	0.0336 (12)	0.0499 (12)	0.0046 (9)	0.0183 (10)	0.0197 (10)
C2	0.0537 (14)	0.0333 (12)	0.0498 (12)	0.0064 (10)	0.0215 (11)	0.0150 (10)
C3	0.0421 (12)	0.0404 (12)	0.0481 (12)	0.0070 (9)	0.0154 (10)	0.0212 (10)
C4	0.0391 (12)	0.0396 (12)	0.0514 (12)	0.0053 (9)	0.0126 (10)	0.0240 (10)
C5	0.0444 (12)	0.0312 (11)	0.0534 (13)	0.0080 (9)	0.0160 (10)	0.0189 (10)
C6	0.0406 (12)	0.0339 (12)	0.0462 (12)	0.0068 (9)	0.0131 (10)	0.0188 (9)
C7	0.0417 (12)	0.0310 (11)	0.0478 (12)	0.0101 (9)	0.0164 (10)	0.0174 (9)
C8	0.0416 (12)	0.0332 (12)	0.0476 (12)	0.0088 (9)	0.0153 (10)	0.0189 (9)
C9	0.0490 (13)	0.0335 (12)	0.0476 (12)	0.0126 (9)	0.0182 (10)	0.0151 (9)
C10	0.0450 (13)	0.0414 (13)	0.0514 (12)	0.0144 (9)	0.0212 (10)	0.0226 (10)
C11	0.0429 (12)	0.0383 (12)	0.0551 (13)	0.0113 (9)	0.0207 (10)	0.0242 (10)
C12	0.0543 (14)	0.0306 (12)	0.0574 (13)	0.0099 (9)	0.0264 (11)	0.0180 (10)
C13	0.0467 (13)	0.0343 (12)	0.0500 (12)	0.0108 (9)	0.0225 (10)	0.0190 (9)
C14	0.0681 (17)	0.0454 (14)	0.0726 (16)	0.0115 (12)	0.0338 (14)	0.0323 (12)
C15	0.0718 (17)	0.0482 (15)	0.0566 (14)	0.0065 (12)	0.0287 (13)	0.0185 (11)
C16	0.090 (2)	0.0556 (17)	0.0761 (18)	0.0213 (14)	0.0462 (16)	0.0256 (14)
C17	0.0671 (17)	0.0506 (15)	0.0685 (16)	0.0173 (12)	0.0378 (14)	0.0272 (12)
C18	0.0567 (15)	0.0409 (14)	0.0734 (16)	0.0100 (11)	0.0284 (13)	0.0289 (12)
C19	0.0705 (18)	0.0525 (16)	0.103 (2)	0.0137 (13)	0.0413 (17)	0.0444 (15)
C20	0.0461 (13)	0.0355 (12)	0.0484 (12)	0.0045 (9)	0.0173 (10)	0.0203 (10)
C21	0.0550 (15)	0.0514 (15)	0.0626 (15)	0.0112 (11)	0.0156 (12)	0.0305 (12)
C22	0.0561 (16)	0.0651 (19)	0.0697 (17)	0.0000 (13)	0.0007 (13)	0.0373 (15)
C23	0.082 (2)	0.0507 (17)	0.0541 (15)	−0.0072 (14)	−0.0010 (15)	0.0191 (13)
C24	0.0790 (19)	0.0370 (14)	0.0550 (14)	0.0029 (12)	0.0096 (14)	0.0141 (11)
C25	0.0537 (14)	0.0350 (12)	0.0501 (13)	0.0052 (10)	0.0144 (11)	0.0173 (10)
C26	0.0579 (15)	0.0345 (13)	0.0537 (13)	0.0133 (10)	0.0216 (12)	0.0179 (10)
C27	0.0440 (13)	0.0391 (12)	0.0564 (13)	0.0067 (9)	0.0149 (11)	0.0218 (10)
C28	0.0499 (14)	0.0466 (13)	0.0555 (13)	0.0077 (10)	0.0193 (11)	0.0234 (11)
C29	0.0521 (14)	0.0588 (15)	0.0633 (15)	0.0076 (11)	0.0234 (12)	0.0377 (12)
C30	0.0605 (15)	0.0501 (14)	0.0597 (14)	0.0229 (11)	0.0288 (12)	0.0310 (12)
C31	0.096 (2)	0.105 (3)	0.0682 (19)	0.0437 (19)	0.0405 (18)	0.0533 (18)
C32	0.139 (4)	0.131 (3)	0.065 (2)	0.055 (3)	0.026 (2)	0.057 (2)
C33	0.099 (3)	0.100 (3)	0.095 (3)	0.023 (2)	−0.004 (2)	0.060 (2)
C34	0.0605 (18)	0.074 (2)	0.105 (2)	0.0163 (14)	0.0102 (17)	0.0549 (18)
C35	0.0571 (16)	0.0462 (14)	0.0669 (16)	0.0177 (11)	0.0229 (13)	0.0291 (12)

Geometric parameters (Å, º) top

O1—C13	1.382 (3)	C15—H15B	0.97
O1—C1	1.384 (2)	C16—H16A	0.96
O2—C26	1.229 (3)	C16—H16B	0.96
O3—C35	1.371 (3)	C16—H16C	0.96
O3—H3A	0.82	C17—H17A	0.96
N1—C26	1.362 (3)	C17—H17B	0.96
N1—C27	1.439 (3)	C17—H17C	0.96
N1—C7	1.491 (3)	C18—C19	1.509 (3)
N2—C28	1.461 (3)	C18—H18A	0.97
N2—C29	1.472 (3)	C18—H18B	0.97
N3—C3	1.372 (3)	C19—H19A	0.96
N3—C15	1.450 (3)	C19—H19B	0.96
N3—H3B	0.86	C19—H19C	0.96
N4—C11	1.385 (3)	C20—C21	1.375 (3)
N4—C18	1.438 (3)	C20—C25	1.379 (3)
N4—H4A	0.86	C21—C22	1.383 (4)
C1—C2	1.375 (3)	C21—H21A	0.93
C1—C6	1.380 (3)	C22—C23	1.376 (4)
C2—C3	1.390 (3)	C22—H22A	0.93
C2—H2B	0.93	C23—C24	1.376 (4)
C3—C4	1.421 (3)	C23—H23A	0.93
C4—C5	1.369 (3)	C24—C25	1.387 (3)
C4—C14	1.506 (3)	C24—H24A	0.93
C5—C6	1.401 (3)	C25—C26	1.466 (3)
C5—H5A	0.93	C27—C28	1.509 (3)
C6—C7	1.512 (3)	C27—H27A	0.97
C7—C8	1.514 (3)	C27—H27B	0.97
C7—C20	1.522 (3)	C28—H28A	0.97
C8—C13	1.379 (3)	C28—H28B	0.97
C8—C9	1.393 (3)	C29—C30	1.498 (3)
C9—C10	1.378 (3)	C29—H29A	0.93
C9—H9A	0.93	C30—C31	1.376 (4)
C10—C11	1.417 (3)	C30—C35	1.390 (3)
C10—C17	1.496 (3)	C31—C32	1.390 (5)
C11—C12	1.377 (3)	C31—H31A	0.93
C12—C13	1.387 (3)	C32—C33	1.360 (5)
C12—H12A	0.93	C32—H32A	0.93
C14—H14A	0.96	C33—C34	1.372 (5)
C14—H14B	0.96	C33—H33A	0.93
C14—H14C	0.96	C34—C35	1.374 (4)
C15—C16	1.501 (4)	C34—H34A	0.93
C15—H15A	0.97

C13—O1—C1	118.30 (16)	C10—C17—H17A	109.5
C35—O3—H3A	109.5	C10—C17—H17B	109.5
C26—N1—C27	123.37 (19)	H17A—C17—H17B	109.5
C26—N1—C7	113.76 (17)	C10—C17—H17C	109.5
C27—N1—C7	122.35 (16)	H17A—C17—H17C	109.5
C28—N2—C29	112.26 (18)	H17B—C17—H17C	109.5
C3—N3—C15	122.76 (19)	N4—C18—C19	110.8 (2)
C3—N3—H3B	118.6	N4—C18—H18A	109.5
C15—N3—H3B	118.6	C19—C18—H18A	109.5
C11—N4—C18	122.31 (19)	N4—C18—H18B	109.5
C11—N4—H4A	118.8	C19—C18—H18B	109.5
C18—N4—H4A	118.8	H18A—C18—H18B	108.1
C2—C1—C6	122.20 (19)	C18—C19—H19A	109.5
C2—C1—O1	114.70 (18)	C18—C19—H19B	109.5
C6—C1—O1	123.09 (19)	H19A—C19—H19B	109.5
C1—C2—C3	121.2 (2)	C18—C19—H19C	109.5
C1—C2—H2B	119.4	H19A—C19—H19C	109.5
C3—C2—H2B	119.4	H19B—C19—H19C	109.5
N3—C3—C2	121.2 (2)	C21—C20—C25	120.9 (2)
N3—C3—C4	120.58 (19)	C21—C20—C7	128.6 (2)
C2—C3—C4	118.2 (2)	C25—C20—C7	110.5 (2)
C5—C4—C3	118.36 (19)	C20—C21—C22	118.2 (3)
C5—C4—C14	121.3 (2)	C20—C21—H21A	120.9
C3—C4—C14	120.3 (2)	C22—C21—H21A	120.9
C4—C5—C6	124.1 (2)	C23—C22—C21	121.1 (3)
C4—C5—H5A	118.0	C23—C22—H22A	119.5
C6—C5—H5A	118.0	C21—C22—H22A	119.5
C1—C6—C5	116.0 (2)	C22—C23—C24	120.9 (2)
C1—C6—C7	122.45 (18)	C22—C23—H23A	119.5
C5—C6—C7	121.51 (18)	C24—C23—H23A	119.5
N1—C7—C6	111.72 (17)	C23—C24—C25	118.1 (3)
N1—C7—C8	109.84 (17)	C23—C24—H24A	121.0
C6—C7—C8	110.45 (17)	C25—C24—H24A	121.0
N1—C7—C20	99.86 (16)	C20—C25—C24	120.8 (2)
C6—C7—C20	111.95 (17)	C20—C25—C26	109.02 (19)
C8—C7—C20	112.63 (17)	C24—C25—C26	130.1 (2)
C13—C8—C9	116.30 (19)	O2—C26—N1	124.8 (2)
C13—C8—C7	122.44 (19)	O2—C26—C25	128.6 (2)
C9—C8—C7	121.24 (18)	N1—C26—C25	106.6 (2)
C10—C9—C8	123.8 (2)	N1—C27—C28	113.04 (18)
C10—C9—H9A	118.1	N1—C27—H27A	109.0
C8—C9—H9A	118.1	C28—C27—H27A	109.0
C9—C10—C11	118.1 (2)	N1—C27—H27B	109.0
C9—C10—C17	121.2 (2)	C28—C27—H27B	109.0
C11—C10—C17	120.7 (2)	H27A—C27—H27B	107.8
C12—C11—N4	122.2 (2)	N2—C28—C27	110.51 (18)
C12—C11—C10	119.00 (19)	N2—C28—H28A	109.5
N4—C11—C10	118.74 (19)	C27—C28—H28A	109.5
C11—C12—C13	120.7 (2)	N2—C28—H28B	109.5
C11—C12—H12A	119.7	C27—C28—H28B	109.5
C13—C12—H12A	119.7	H28A—C28—H28B	108.1
C8—C13—O1	123.17 (18)	N2—C29—C30	111.97 (19)
C8—C13—C12	122.1 (2)	N2—C29—H29A	124.0
O1—C13—C12	114.72 (18)	C30—C29—H29A	124.0
C4—C14—H14A	109.5	C31—C30—C35	117.9 (3)
C4—C14—H14B	109.5	C31—C30—C29	121.6 (2)
H14A—C14—H14B	109.5	C35—C30—C29	120.4 (2)
C4—C14—H14C	109.5	C30—C31—C32	120.9 (3)
H14A—C14—H14C	109.5	C30—C31—H31A	119.5
H14B—C14—H14C	109.5	C32—C31—H31A	119.5
N3—C15—C16	111.8 (2)	C33—C32—C31	119.8 (3)
N3—C15—H15A	109.2	C33—C32—H32A	120.1
C16—C15—H15A	109.2	C31—C32—H32A	120.1
N3—C15—H15B	109.2	C32—C33—C34	120.5 (3)
C16—C15—H15B	109.2	C32—C33—H33A	119.8
H15A—C15—H15B	107.9	C34—C33—H33A	119.8
C15—C16—H16A	109.5	C33—C34—C35	119.6 (3)
C15—C16—H16B	109.5	C33—C34—H34A	120.2
H16A—C16—H16B	109.5	C35—C34—H34A	120.2
C15—C16—H16C	109.5	O3—C35—C34	118.3 (3)
H16A—C16—H16C	109.5	O3—C35—C30	120.5 (2)
H16B—C16—H16C	109.5	C34—C35—C30	121.2 (3)

C13—O1—C1—C2	177.43 (19)	C9—C8—C13—C12	−0.1 (3)
C13—O1—C1—C6	−2.0 (3)	C7—C8—C13—C12	−178.4 (2)
C6—C1—C2—C3	0.3 (4)	C1—O1—C13—C8	−1.0 (3)
O1—C1—C2—C3	−179.1 (2)	C1—O1—C13—C12	179.64 (19)
C15—N3—C3—C2	1.6 (4)	C11—C12—C13—C8	0.0 (4)
C15—N3—C3—C4	−179.2 (2)	C11—C12—C13—O1	179.4 (2)
C1—C2—C3—N3	177.4 (2)	C3—N3—C15—C16	−175.0 (2)
C1—C2—C3—C4	−1.9 (3)	C11—N4—C18—C19	178.4 (2)
N3—C3—C4—C5	−177.3 (2)	N1—C7—C20—C21	−175.0 (2)
C2—C3—C4—C5	1.9 (3)	C6—C7—C20—C21	−56.6 (3)
N3—C3—C4—C14	1.7 (3)	C8—C7—C20—C21	68.6 (3)
C2—C3—C4—C14	−179.1 (2)	N1—C7—C20—C25	4.0 (2)
C3—C4—C5—C6	−0.5 (3)	C6—C7—C20—C25	122.4 (2)
C14—C4—C5—C6	−179.5 (2)	C8—C7—C20—C25	−112.4 (2)
C2—C1—C6—C5	1.1 (3)	C25—C20—C21—C22	1.1 (3)
O1—C1—C6—C5	−179.5 (2)	C7—C20—C21—C22	180.0 (2)
C2—C1—C6—C7	−175.8 (2)	C20—C21—C22—C23	0.2 (4)
O1—C1—C6—C7	3.6 (3)	C21—C22—C23—C24	−1.0 (4)
C4—C5—C6—C1	−1.0 (3)	C22—C23—C24—C25	0.4 (4)
C4—C5—C6—C7	175.9 (2)	C21—C20—C25—C24	−1.6 (3)
C26—N1—C7—C6	−123.32 (19)	C7—C20—C25—C24	179.3 (2)
C27—N1—C7—C6	64.6 (2)	C21—C20—C25—C26	176.9 (2)
C26—N1—C7—C8	113.8 (2)	C7—C20—C25—C26	−2.2 (3)
C27—N1—C7—C8	−58.3 (2)	C23—C24—C25—C20	0.8 (4)
C26—N1—C7—C20	−4.8 (2)	C23—C24—C25—C26	−177.4 (2)
C27—N1—C7—C20	−176.83 (18)	C27—N1—C26—O2	−5.4 (4)
C1—C6—C7—N1	−124.7 (2)	C7—N1—C26—O2	−177.4 (2)
C5—C6—C7—N1	58.6 (3)	C27—N1—C26—C25	175.75 (19)
C1—C6—C7—C8	−2.1 (3)	C7—N1—C26—C25	3.8 (2)
C5—C6—C7—C8	−178.85 (18)	C20—C25—C26—O2	−179.7 (2)
C1—C6—C7—C20	124.3 (2)	C24—C25—C26—O2	−1.4 (4)
C5—C6—C7—C20	−52.5 (3)	C20—C25—C26—N1	−0.9 (3)
N1—C7—C8—C13	123.0 (2)	C24—C25—C26—N1	177.4 (2)
C6—C7—C8—C13	−0.7 (3)	C26—N1—C27—C28	77.5 (3)
C20—C7—C8—C13	−126.7 (2)	C7—N1—C27—C28	−111.2 (2)
N1—C7—C8—C9	−55.2 (3)	C29—N2—C28—C27	170.9 (2)
C6—C7—C8—C9	−178.86 (19)	N1—C27—C28—N2	176.43 (18)
C20—C7—C8—C9	55.1 (3)	C28—N2—C29—C30	−177.25 (19)
C13—C8—C9—C10	0.1 (3)	N2—C29—C30—C31	−139.0 (3)
C7—C8—C9—C10	178.4 (2)	N2—C29—C30—C35	44.5 (3)
C8—C9—C10—C11	−0.1 (3)	C35—C30—C31—C32	−1.0 (4)
C8—C9—C10—C17	−179.0 (2)	C29—C30—C31—C32	−177.6 (3)
C18—N4—C11—C12	10.5 (4)	C30—C31—C32—C33	0.2 (6)
C18—N4—C11—C10	−170.9 (2)	C31—C32—C33—C34	1.5 (6)
C9—C10—C11—C12	0.0 (3)	C32—C33—C34—C35	−2.3 (5)
C17—C10—C11—C12	178.9 (2)	C33—C34—C35—O3	−179.7 (3)
C9—C10—C11—N4	−178.7 (2)	C33—C34—C35—C30	1.4 (4)
C17—C10—C11—N4	0.2 (3)	C31—C30—C35—O3	−178.7 (2)
N4—C11—C12—C13	178.7 (2)	C29—C30—C35—O3	−2.0 (4)
C10—C11—C12—C13	0.1 (3)	C31—C30—C35—C34	0.2 (4)
C9—C8—C13—O1	−179.5 (2)	C29—C30—C35—C34	176.9 (2)
C7—C8—C13—O1	2.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···N2	0.82	2.01	2.685 (3)	139
N3—H3B···O3ⁱ	0.86	2.32	3.144 (1)	160
C9—H9A···O2ⁱⁱ	0.93	2.59	3.468 (3)	157

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+3, −z+1.

Experimental details

Crystal data
Chemical formula	C₃₅H₃₆N₄O₃
M_r	560.68
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	11.6453 (5), 11.8588 (3), 12.9822 (3)
α, β, γ (°)	116.321 (1), 103.173 (2), 98.337 (2)
V (Å³)	1501.21 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.30 × 0.25

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.976, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	9518, 5018, 3667
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.169, 1.01
No. of reflections	5018
No. of parameters	383
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.34

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···N2	0.82	2.01	2.685 (3)	139
N3—H3B···O3ⁱ	0.86	2.32	3.144 (1)	160
C9—H9A···O2ⁱⁱ	0.93	2.59	3.468 (3)	157

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+3, −z+1.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant Nos. 20376010 and 20472012) and the Natural Science Foundation of Liaoning Provence (grant No. 20062186).

References

Bruker (1997). SADABS (Version 2.03) and SHELXTL (Version 5.10). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
De Silva, A. P., Gunaratne, H. Q. N., Gunnlaugsson, T., Huxley, A. J. M., McCoy, C. P., Rademacher, J. T. & Rice, T. E. (1997). Chem. Rev. 97, 1515–1566. CrossRef PubMed CAS Web of Science Google Scholar
Kwon, J. Y., Jang, Y. J., Lee, Y. J., Kim, K. M., Seo, M. S., Nam, W. & Yoon, J. (2005). J. Am. Chem. Soc. 127, 10107–10111. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wu, J. S., Hwang, I. C., Kwang, S. K. & Jong, S. K. (2007). Org. Lett. 9, 907–910. Web of Science CSD CrossRef PubMed Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

[(2-{[3′,6′-Bis(ethyl­amino)-2′,7′-di­methyl-3-oxo­spiro­[1H-iso­indole-1,9′-9H-xanthen]-2-yl}eth­yl)amino­meth­yl]phenol

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

[(2-{[3′,6′-Bis(ethylamino)-2′,7′-dimethyl-3-oxospiro[1H-isoindole-1,9′-9H-xanthen]-2-yl}ethyl)aminomethyl]phenol