(Z)-3′,6′-Bis(diethyl­amino)-2-(4-oxopent-2-en-2-yl­amino)­spiro­[isoindoline-1,9′-xanthen]-3-one

Guo, C.-B.; He, R.-C.; Li, A.-M.

doi:10.1107/S1600536812027602

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2205

https://doi.org/10.1107/S1600536812027602

Open

access

(Z)-3′,6′-Bis(diethylamino)-2-(4-oxopent-2-en-2-ylamino)spiro[isoindoline-1,9′-xanthen]-3-one

Chang-Bin Guo,^a ^* Ri-Cai He ^a and Ai-Min Li ^a

^aDepartment of Chemistry, Capital Normal University, Beijing 100048, People's Republic of China
^*Correspondence e-mail: changbin.guo@gmail.com

(Received 11 June 2012; accepted 18 June 2012; online 27 June 2012)

In the title compound, C₃₃H₃₈N₄O₃, the mean planes of the 9H-xanthene unit and spirolactam (nine-atom) core are almost mutually perpendicular at 87.26 (6)°. Intramolecular N—H⋯O and C—H⋯N interactions influence the 4-oxopent-2-en-2-ylamino conformation. In the crystal, weak C—H⋯O hydrogen bonds link the molecules into chains along [001].

Related literature

For the use of Rhodamine B derivatives as fluorescent chemosensors, see: Zhang et al. (2007 ); Soh et al. (2007 ). For a related structure, see: Xiang et al. (2006 ).

Experimental

Crystal data

C₃₃H₃₈N₄O₃
M_r = 538.67
Monoclinic, P 2₁ /c
a = 17.4255 (3) Å
b = 15.0965 (3) Å
c = 11.5354 (2) Å
β = 103.008 (1)°
V = 2956.68 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.26 × 0.26 × 0.24 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.666, T_max = 0.746
24441 measured reflections
7000 independent reflections
4223 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.165
S = 1.04
7000 reflections
365 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1⋯O3	0.88 (2)	1.92 (2)	2.641 (2)	139 (2)
C33—H33A⋯N2	0.96	2.30	2.785 (3)	110
C7—H7B⋯O3ⁱ	0.97	2.60	3.334 (3)	133
Symmetry code: (i) x, y, z-1.

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 and SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812027602/gg2084sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812027602/gg2084Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812027602/gg2084Isup3.cml

checkCIF report

Comment top

Rhodamine B derivatives are known to have excellent photophysical properties, such as the long absorption and emission wavelengths elongated to the visible region. Therefore, they have been extensively used as fluorescent chemosensors for heavy and transition metal ions, such as Cu(II) (Zhang et al., 2007) and Hg(II) chemical sensor (Soh et al., 2007). Herein, we report the synthesis and crystal structure of a new Rhodamine B derivative, namely (Z)-3',6'-bis(diethylamino)-2-(4-oxopent-2-en-2-ylamino)spiroisoindoline- [1,9'-xanthen]-3-one.

In the title compound C₃₃H₃₈N₄O₃, the mean plane of the 9H-xanthene moiety and that of the spirolactam moiety are almost perpendicular to each other (Fig. 1). Two N,N-diethylamino groups bond to the 9H-xanthene moiety at C5 and C15, respectivly, while a 4-oxopent-2-en-2-ylamino links to the spirolactam moiety at N2 position (Fig. 1). The 9H-xanthene fragment exhibits a butterfly-like conformation with two benzene rings (C12-C13-C14-C15-C16-C17 and C1-C2-C3-C4-C5-C6, respectively) exhibiting a dihedral angle of 160.06 (4)°. For the 4-oxopent-2-en-2-ylamino group, the double bond between C29 and C30 shows a Z-configuration. The structure of the title compound is similar to that of other reported Rhodamine B derivatives (Xiang et al. 2006). The molecular packing is stabilized by an intermolecular interaction (C7—H7B···O3ⁱ, C7O3ⁱ = 3.334 (3) Å, C7—H7B···O3ⁱ = 133 °).

Related literature top

For the use of Rhodamine B derivatives as fluorescent chemosensors, see: Zhang et al. (2007); Soh et al. (2007). For a related structure, see: Xiang et al. (2006).

Experimental top

To a solution of 2-amino-3',6'-bis(diethylamino)spiro [isoindoline-1,9'-xanthen]-3-one (0.50 g, 1.09 mmol) in 3 mL absolute anhydrous ethanol was added 0.5 mL pentane-2,4-dione and CAN (5% mol), then the resulting mixture was stirred at room temperature for 6 h. The reaction mixture was dissolved in 20 mL CH₂Cl₂, washed twice with water and dried over Na₂SO₄, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (EA:PE=1:1, v/v) to yield the title compound as a white powder (0.47 g, 80.1%). Crystals suitable for X-ray analysis were obtained by slow evaporation of a solution of the title compound in ethanol at room temperature in four days.

Structure description top

For the use of Rhodamine B derivatives as fluorescent chemosensors, see: Zhang et al. (2007); Soh et al. (2007). For a related structure, see: Xiang et al. (2006).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 and SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The structure of (I) with 35% probability displacement ellipsoids and the atom numbering scheme.
	Fig. 2. The crystal structure packing structure of (I).

(Z)-3',6'-Bis(diethylamino)-2-(4-oxopent-2-en-2- ylamino)spiro[isoindoline-1,9'-xanthen]-3-one top

Crystal data top

C₃₃H₃₈N₄O₃	F(000) = 1152
M_r = 538.67	D_x = 1.210 Mg m⁻³ D_m = 1.210 Mg m⁻³ D_m measured by not measured
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7869 reflections
a = 17.4255 (3) Å	θ = 2.5–28.8°
b = 15.0965 (3) Å	µ = 0.08 mm⁻¹
c = 11.5354 (2) Å	T = 296 K
β = 103.008 (1)°	Block, colorless
V = 2956.68 (9) Å³	0.26 × 0.26 × 0.24 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	7000 independent reflections
Radiation source: fine-focus sealed tube	4223 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ω scans	θ_max = 28.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −22→22
T_min = 0.666, T_max = 0.746	k = −19→19
24441 measured reflections	l = −15→15

Refinement top

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.165	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0751P)² + 0.4182P] where P = (F_o² + 2F_c²)/3
7000 reflections	(Δ/σ)_max < 0.001
365 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₃₃H₃₈N₄O₃	V = 2956.68 (9) Å³
M_r = 538.67	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.4255 (3) Å	µ = 0.08 mm⁻¹
b = 15.0965 (3) Å	T = 296 K
c = 11.5354 (2) Å	0.26 × 0.26 × 0.24 mm
β = 103.008 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	7000 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	4223 reflections with I > 2σ(I)
T_min = 0.666, T_max = 0.746	R_int = 0.038
24441 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.165	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.31 e Å⁻³
7000 reflections	Δρ_min = −0.23 e Å⁻³
365 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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

	x	y	z	U_iso*/U_eq
C1	0.72483 (9)	0.55285 (12)	0.35969 (17)	0.0411 (4)
C2	0.79924 (9)	0.58683 (11)	0.40887 (16)	0.0391 (4)
C3	0.85265 (10)	0.58468 (13)	0.33574 (18)	0.0480 (5)
H3A	0.9032	0.6065	0.3652	0.058*
C4	0.83408 (11)	0.55181 (14)	0.22229 (18)	0.0516 (5)
H4A	0.8721	0.5512	0.1773	0.062*
C5	0.75792 (10)	0.51884 (13)	0.17260 (17)	0.0464 (4)
C6	0.70398 (10)	0.51974 (12)	0.24555 (17)	0.0461 (4)
H6A	0.6534	0.4978	0.2168	0.055*
C7	0.79176 (13)	0.50105 (16)	−0.0224 (2)	0.0622 (6)
H7A	0.8178	0.5578	−0.0046	0.075*
H7B	0.7609	0.5034	−0.1036	0.075*
C8	0.85292 (16)	0.43034 (19)	−0.0135 (3)	0.0839 (8)
H8A	0.8857	0.4430	−0.0681	0.126*
H8B	0.8276	0.3741	−0.0330	0.126*
H8C	0.8846	0.4286	0.0661	0.126*
C9	0.65814 (12)	0.46323 (16)	0.0011 (2)	0.0661 (6)
H9A	0.6348	0.4319	0.0580	0.079*
H9B	0.6592	0.4230	−0.0641	0.079*
C10	0.60719 (17)	0.5411 (2)	−0.0460 (3)	0.1075 (11)
H10A	0.5551	0.5209	−0.0825	0.161*
H10B	0.6291	0.5717	−0.1040	0.161*
H10C	0.6047	0.5807	0.0182	0.161*
C11	0.81924 (9)	0.61870 (11)	0.53530 (16)	0.0393 (4)
C12	0.74476 (9)	0.64566 (12)	0.57294 (17)	0.0417 (4)
C13	0.74226 (11)	0.70387 (13)	0.66550 (18)	0.0523 (5)
H13A	0.7879	0.7342	0.7011	0.063*
C14	0.67532 (11)	0.71844 (14)	0.70650 (19)	0.0555 (5)
H14A	0.6761	0.7598	0.7665	0.067*
C15	0.60520 (10)	0.67139 (13)	0.65862 (17)	0.0479 (5)
C16	0.60620 (10)	0.61550 (12)	0.56295 (18)	0.0473 (5)
H16A	0.5607	0.5851	0.5268	0.057*
C17	0.67389 (10)	0.60457 (12)	0.52103 (17)	0.0423 (4)
C18	0.46914 (11)	0.62613 (16)	0.6584 (2)	0.0612 (6)
H18A	0.4395	0.6212	0.7199	0.073*
H18B	0.4863	0.5670	0.6431	0.073*
C19	0.41471 (14)	0.6596 (2)	0.5467 (3)	0.0848 (8)
H19A	0.3709	0.6198	0.5239	0.127*
H19B	0.4427	0.6630	0.4841	0.127*
H19C	0.3958	0.7174	0.5610	0.127*
C20	0.53268 (13)	0.74897 (16)	0.7899 (2)	0.0663 (6)
H20A	0.5831	0.7544	0.8459	0.080*
H20B	0.4942	0.7309	0.8342	0.080*
C21	0.50958 (18)	0.83815 (19)	0.7354 (3)	0.0957 (9)
H21A	0.5069	0.8800	0.7970	0.144*
H21B	0.4590	0.8340	0.6814	0.144*
H21C	0.5481	0.8575	0.6930	0.144*
C28	0.92523 (10)	0.57242 (13)	0.69867 (18)	0.0491 (5)
C27	0.94264 (10)	0.66190 (12)	0.65927 (17)	0.0464 (5)
C26	1.00665 (11)	0.71638 (15)	0.7041 (2)	0.0592 (6)
H26A	1.0454	0.6993	0.7697	0.071*
C25	1.01124 (11)	0.79624 (15)	0.6490 (2)	0.0605 (6)
H25A	1.0532	0.8341	0.6783	0.073*
C24	0.95405 (11)	0.82103 (14)	0.5504 (2)	0.0569 (5)
H24A	0.9591	0.8745	0.5127	0.068*
C23	0.88946 (10)	0.76746 (13)	0.50691 (19)	0.0506 (5)
H23A	0.8507	0.7848	0.4414	0.061*
C22	0.88396 (9)	0.68792 (12)	0.56306 (17)	0.0417 (4)
C29	0.83791 (10)	0.39074 (12)	0.59552 (18)	0.0469 (5)
C33	0.90031 (14)	0.38742 (16)	0.5252 (3)	0.0764 (7)
H33A	0.9179	0.4464	0.5140	0.115*
H33B	0.8791	0.3609	0.4490	0.115*
H33C	0.9440	0.3528	0.5673	0.115*
C30	0.80224 (11)	0.31622 (13)	0.6247 (2)	0.0559 (5)
H30A	0.8153	0.2625	0.5946	0.067*
C31	0.74681 (12)	0.31462 (15)	0.6976 (2)	0.0601 (6)
C32	0.72173 (19)	0.22546 (19)	0.7353 (3)	0.1099 (11)
H32A	0.6843	0.2336	0.7840	0.165*
H32B	0.7669	0.1944	0.7798	0.165*
H32C	0.6980	0.1916	0.6660	0.165*
N1	0.73857 (9)	0.48717 (13)	0.05820 (15)	0.0580 (5)
N2	0.85909 (8)	0.54639 (10)	0.61756 (14)	0.0445 (4)
N3	0.81807 (9)	0.47045 (10)	0.63140 (15)	0.0463 (4)
N4	0.53859 (9)	0.67999 (12)	0.70403 (16)	0.0569 (5)
O1	0.66609 (7)	0.55024 (9)	0.42302 (12)	0.0517 (4)
O2	0.96133 (9)	0.52827 (11)	0.78133 (15)	0.0744 (5)
O3	0.71972 (9)	0.38277 (11)	0.73323 (15)	0.0710 (5)
H1	0.7807 (13)	0.4688 (15)	0.671 (2)	0.070 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0388 (8)	0.0427 (9)	0.0429 (11)	−0.0010 (7)	0.0111 (8)	−0.0032 (9)
C2	0.0391 (8)	0.0402 (9)	0.0368 (10)	−0.0009 (7)	0.0060 (7)	−0.0023 (8)
C3	0.0387 (8)	0.0578 (11)	0.0466 (12)	−0.0077 (8)	0.0078 (8)	−0.0049 (10)
C4	0.0479 (10)	0.0644 (12)	0.0455 (12)	−0.0067 (9)	0.0172 (9)	−0.0065 (10)
C5	0.0504 (10)	0.0489 (10)	0.0399 (11)	−0.0005 (8)	0.0100 (9)	−0.0055 (9)
C6	0.0417 (9)	0.0512 (11)	0.0442 (12)	−0.0061 (8)	0.0072 (8)	−0.0094 (9)
C7	0.0704 (13)	0.0709 (14)	0.0463 (13)	−0.0035 (11)	0.0156 (10)	−0.0087 (11)
C8	0.0891 (17)	0.0923 (19)	0.0758 (19)	0.0133 (14)	0.0305 (15)	−0.0065 (15)
C9	0.0631 (12)	0.0859 (17)	0.0471 (13)	−0.0102 (11)	0.0073 (11)	−0.0177 (12)
C10	0.0870 (18)	0.146 (3)	0.081 (2)	0.0269 (19)	0.0007 (16)	0.011 (2)
C11	0.0376 (8)	0.0405 (9)	0.0380 (10)	−0.0016 (7)	0.0047 (7)	−0.0005 (8)
C12	0.0394 (8)	0.0442 (10)	0.0407 (11)	−0.0020 (7)	0.0073 (8)	−0.0033 (9)
C13	0.0481 (10)	0.0574 (12)	0.0509 (13)	−0.0086 (8)	0.0101 (9)	−0.0171 (10)
C14	0.0564 (11)	0.0600 (12)	0.0521 (13)	−0.0046 (9)	0.0167 (10)	−0.0203 (11)
C15	0.0461 (9)	0.0549 (11)	0.0430 (12)	0.0032 (8)	0.0108 (8)	−0.0039 (10)
C16	0.0407 (8)	0.0547 (11)	0.0461 (12)	−0.0053 (8)	0.0090 (8)	−0.0097 (10)
C17	0.0444 (9)	0.0441 (10)	0.0384 (11)	−0.0029 (7)	0.0092 (8)	−0.0081 (9)
C18	0.0515 (10)	0.0751 (15)	0.0618 (15)	−0.0025 (10)	0.0229 (11)	−0.0047 (12)
C19	0.0626 (13)	0.108 (2)	0.0784 (19)	−0.0008 (13)	0.0049 (13)	−0.0022 (17)
C20	0.0628 (12)	0.0779 (15)	0.0641 (15)	0.0054 (11)	0.0270 (11)	−0.0147 (13)
C21	0.106 (2)	0.0736 (18)	0.105 (2)	0.0087 (15)	0.0189 (18)	−0.0119 (17)
C28	0.0422 (9)	0.0573 (12)	0.0446 (12)	−0.0013 (8)	0.0029 (9)	0.0054 (10)
C27	0.0408 (8)	0.0536 (11)	0.0434 (11)	−0.0055 (8)	0.0066 (8)	−0.0021 (9)
C26	0.0455 (10)	0.0753 (15)	0.0516 (13)	−0.0125 (9)	−0.0001 (9)	−0.0002 (12)
C25	0.0480 (10)	0.0632 (13)	0.0693 (16)	−0.0180 (9)	0.0113 (11)	−0.0093 (12)
C24	0.0572 (11)	0.0474 (11)	0.0680 (15)	−0.0082 (9)	0.0182 (11)	−0.0020 (11)
C23	0.0487 (10)	0.0474 (11)	0.0532 (13)	−0.0014 (8)	0.0062 (9)	0.0025 (10)
C22	0.0384 (8)	0.0458 (10)	0.0397 (11)	−0.0030 (7)	0.0064 (8)	−0.0049 (9)
C29	0.0438 (9)	0.0476 (11)	0.0469 (12)	0.0064 (8)	0.0049 (8)	−0.0012 (9)
C33	0.0751 (14)	0.0654 (14)	0.099 (2)	0.0142 (11)	0.0411 (14)	−0.0054 (14)
C30	0.0557 (11)	0.0431 (11)	0.0652 (15)	0.0015 (8)	0.0058 (10)	−0.0049 (10)
C31	0.0600 (11)	0.0571 (13)	0.0596 (15)	−0.0134 (10)	0.0058 (11)	−0.0025 (12)
C32	0.126 (2)	0.0762 (18)	0.134 (3)	−0.0367 (17)	0.043 (2)	0.007 (2)
N1	0.0552 (9)	0.0793 (12)	0.0401 (10)	−0.0082 (8)	0.0122 (8)	−0.0151 (9)
N2	0.0445 (7)	0.0429 (8)	0.0433 (9)	−0.0051 (6)	0.0039 (7)	0.0028 (7)
N3	0.0479 (8)	0.0430 (9)	0.0508 (10)	−0.0037 (7)	0.0166 (8)	−0.0003 (8)
N4	0.0488 (8)	0.0699 (11)	0.0556 (11)	0.0002 (8)	0.0190 (8)	−0.0136 (9)
O1	0.0432 (6)	0.0642 (8)	0.0505 (8)	−0.0143 (6)	0.0164 (6)	−0.0221 (7)
O2	0.0680 (9)	0.0804 (11)	0.0629 (11)	−0.0071 (8)	−0.0106 (8)	0.0246 (9)
O3	0.0750 (9)	0.0730 (11)	0.0710 (12)	−0.0168 (8)	0.0293 (9)	−0.0126 (9)

Geometric parameters (Å, º) top

C1—C6	1.378 (3)	C18—C19	1.505 (3)
C1—O1	1.386 (2)	C18—H18A	0.9700
C1—C2	1.391 (2)	C18—H18B	0.9700
C2—C3	1.390 (2)	C19—H19A	0.9600
C2—C11	1.500 (3)	C19—H19B	0.9600
C3—C4	1.369 (3)	C19—H19C	0.9600
C3—H3A	0.9300	C20—N4	1.456 (3)
C4—C5	1.412 (3)	C20—C21	1.502 (4)
C4—H4A	0.9300	C20—H20A	0.9700
C5—N1	1.372 (2)	C20—H20B	0.9700
C5—C6	1.396 (2)	C21—H21A	0.9600
C6—H6A	0.9300	C21—H21B	0.9600
C7—N1	1.468 (3)	C21—H21C	0.9600
C7—C8	1.496 (3)	C28—O2	1.216 (2)
C7—H7A	0.9700	C28—N2	1.368 (2)
C7—H7B	0.9700	C28—C27	1.478 (3)
C8—H8A	0.9600	C27—C22	1.386 (3)
C8—H8B	0.9600	C27—C26	1.389 (3)
C8—H8C	0.9600	C26—C25	1.374 (3)
C9—N1	1.454 (3)	C26—H26A	0.9300
C9—C10	1.500 (4)	C25—C24	1.385 (3)
C9—H9A	0.9700	C25—H25A	0.9300
C9—H9B	0.9700	C24—C23	1.385 (3)
C10—H10A	0.9600	C24—H24A	0.9300
C10—H10B	0.9600	C23—C22	1.378 (3)
C10—H10C	0.9600	C23—H23A	0.9300
C11—N2	1.509 (2)	C29—N3	1.343 (2)
C11—C12	1.514 (2)	C29—C30	1.364 (3)
C11—C22	1.518 (2)	C29—C33	1.497 (3)
C12—C13	1.391 (3)	C33—H33A	0.9600
C12—C17	1.391 (2)	C33—H33B	0.9600
C13—C14	1.371 (3)	C33—H33C	0.9600
C13—H13A	0.9300	C30—C31	1.416 (3)
C14—C15	1.414 (3)	C30—H30A	0.9300
C14—H14A	0.9300	C31—O3	1.240 (3)
C15—N4	1.383 (2)	C31—C32	1.509 (3)
C15—C16	1.392 (3)	C32—H32A	0.9600
C16—C17	1.382 (2)	C32—H32B	0.9600
C16—H16A	0.9300	C32—H32C	0.9600
C17—O1	1.379 (2)	N2—N3	1.379 (2)
C18—N4	1.455 (3)	N3—H1	0.88 (2)

C6—C1—O1	115.22 (14)	C18—C19—H19B	109.5
C6—C1—C2	122.99 (16)	H19A—C19—H19B	109.5
O1—C1—C2	121.79 (16)	C18—C19—H19C	109.5
C3—C2—C1	115.71 (16)	H19A—C19—H19C	109.5
C3—C2—C11	123.82 (14)	H19B—C19—H19C	109.5
C1—C2—C11	120.39 (15)	N4—C20—C21	114.2 (2)
C4—C3—C2	122.84 (16)	N4—C20—H20A	108.7
C4—C3—H3A	118.6	C21—C20—H20A	108.7
C2—C3—H3A	118.6	N4—C20—H20B	108.7
C3—C4—C5	120.94 (17)	C21—C20—H20B	108.7
C3—C4—H4A	119.5	H20A—C20—H20B	107.6
C5—C4—H4A	119.5	C20—C21—H21A	109.5
N1—C5—C6	122.01 (16)	C20—C21—H21B	109.5
N1—C5—C4	121.20 (16)	H21A—C21—H21B	109.5
C6—C5—C4	116.79 (17)	C20—C21—H21C	109.5
C1—C6—C5	120.72 (16)	H21A—C21—H21C	109.5
C1—C6—H6A	119.6	H21B—C21—H21C	109.5
C5—C6—H6A	119.6	O2—C28—N2	125.88 (18)
N1—C7—C8	113.3 (2)	O2—C28—C27	129.50 (18)
N1—C7—H7A	108.9	N2—C28—C27	104.58 (16)
C8—C7—H7A	108.9	C22—C27—C26	121.10 (18)
N1—C7—H7B	108.9	C22—C27—C28	109.86 (15)
C8—C7—H7B	108.9	C26—C27—C28	129.03 (18)
H7A—C7—H7B	107.7	C25—C26—C27	118.22 (19)
C7—C8—H8A	109.5	C25—C26—H26A	120.9
C7—C8—H8B	109.5	C27—C26—H26A	120.9
H8A—C8—H8B	109.5	C26—C25—C24	120.76 (18)
C7—C8—H8C	109.5	C26—C25—H25A	119.6
H8A—C8—H8C	109.5	C24—C25—H25A	119.6
H8B—C8—H8C	109.5	C23—C24—C25	121.02 (19)
N1—C9—C10	113.6 (2)	C23—C24—H24A	119.5
N1—C9—H9A	108.8	C25—C24—H24A	119.5
C10—C9—H9A	108.8	C22—C23—C24	118.40 (18)
N1—C9—H9B	108.8	C22—C23—H23A	120.8
C10—C9—H9B	108.8	C24—C23—H23A	120.8
H9A—C9—H9B	107.7	C23—C22—C27	120.44 (16)
C9—C10—H10A	109.5	C23—C22—C11	128.89 (16)
C9—C10—H10B	109.5	C27—C22—C11	110.67 (15)
H10A—C10—H10B	109.5	N3—C29—C30	119.99 (17)
C9—C10—H10C	109.5	N3—C29—C33	117.77 (17)
H10A—C10—H10C	109.5	C30—C29—C33	122.24 (18)
H10B—C10—H10C	109.5	C29—C33—H33A	109.5
C2—C11—N2	110.65 (14)	C29—C33—H33B	109.5
C2—C11—C12	109.78 (13)	H33A—C33—H33B	109.5
N2—C11—C12	108.48 (14)	C29—C33—H33C	109.5
C2—C11—C22	115.13 (15)	H33A—C33—H33C	109.5
N2—C11—C22	98.65 (13)	H33B—C33—H33C	109.5
C12—C11—C22	113.49 (14)	C29—C30—C31	124.77 (19)
C13—C12—C17	115.72 (16)	C29—C30—H30A	117.6
C13—C12—C11	124.54 (15)	C31—C30—H30A	117.6
C17—C12—C11	119.46 (16)	O3—C31—C30	122.95 (19)
C14—C13—C12	122.82 (17)	O3—C31—C32	119.2 (2)
C14—C13—H13A	118.6	C30—C31—C32	117.8 (2)
C12—C13—H13A	118.6	C31—C32—H32A	109.5
C13—C14—C15	120.80 (18)	C31—C32—H32B	109.5
C13—C14—H14A	119.6	H32A—C32—H32B	109.5
C15—C14—H14A	119.6	C31—C32—H32C	109.5
N4—C15—C16	121.23 (16)	H32A—C32—H32C	109.5
N4—C15—C14	122.02 (17)	H32B—C32—H32C	109.5
C16—C15—C14	116.75 (16)	C5—N1—C9	121.71 (16)
C17—C16—C15	120.92 (16)	C5—N1—C7	120.39 (16)
C17—C16—H16A	119.5	C9—N1—C7	115.47 (17)
C15—C16—H16A	119.5	C28—N2—N3	122.57 (16)
O1—C17—C16	115.08 (15)	C28—N2—C11	114.82 (14)
O1—C17—C12	122.17 (15)	N3—N2—C11	119.79 (13)
C16—C17—C12	122.76 (17)	C29—N3—N2	122.22 (16)
N4—C18—C19	115.8 (2)	C29—N3—H1	114.1 (15)
N4—C18—H18A	108.3	N2—N3—H1	123.3 (15)
C19—C18—H18A	108.3	C15—N4—C18	120.76 (16)
N4—C18—H18B	108.3	C15—N4—C20	121.22 (17)
C19—C18—H18B	108.3	C18—N4—C20	117.73 (16)
H18A—C18—H18B	107.4	C17—O1—C1	117.87 (13)
C18—C19—H19A	109.5

C6—C1—C2—C3	−0.7 (3)	C26—C27—C22—C23	2.4 (3)
O1—C1—C2—C3	179.48 (16)	C28—C27—C22—C23	−176.69 (17)
C6—C1—C2—C11	−177.65 (17)	C26—C27—C22—C11	−177.41 (17)
O1—C1—C2—C11	2.5 (3)	C28—C27—C22—C11	3.5 (2)
C1—C2—C3—C4	0.3 (3)	C2—C11—C22—C23	53.6 (2)
C11—C2—C3—C4	177.12 (18)	N2—C11—C22—C23	171.29 (18)
C2—C3—C4—C5	0.8 (3)	C12—C11—C22—C23	−74.1 (2)
C3—C4—C5—N1	178.90 (19)	C2—C11—C22—C27	−126.66 (17)
C3—C4—C5—C6	−1.4 (3)	N2—C11—C22—C27	−8.93 (18)
O1—C1—C6—C5	179.87 (17)	C12—C11—C22—C27	105.64 (18)
C2—C1—C6—C5	0.0 (3)	N3—C29—C30—C31	−3.6 (3)
N1—C5—C6—C1	−179.30 (19)	C33—C29—C30—C31	175.6 (2)
C4—C5—C6—C1	1.0 (3)	C29—C30—C31—O3	7.0 (4)
C3—C2—C11—N2	−82.0 (2)	C29—C30—C31—C32	−171.5 (2)
C1—C2—C11—N2	94.69 (18)	C6—C5—N1—C9	8.0 (3)
C3—C2—C11—C12	158.27 (17)	C4—C5—N1—C9	−172.3 (2)
C1—C2—C11—C12	−25.0 (2)	C6—C5—N1—C7	169.48 (19)
C3—C2—C11—C22	28.7 (2)	C4—C5—N1—C7	−10.9 (3)
C1—C2—C11—C22	−154.56 (16)	C10—C9—N1—C5	79.8 (3)
C2—C11—C12—C13	−157.51 (18)	C10—C9—N1—C7	−82.5 (3)
N2—C11—C12—C13	81.5 (2)	C8—C7—N1—C5	87.5 (3)
C22—C11—C12—C13	−27.1 (3)	C8—C7—N1—C9	−109.9 (2)
C2—C11—C12—C17	28.9 (2)	O2—C28—N2—N3	10.4 (3)
N2—C11—C12—C17	−92.1 (2)	C27—C28—N2—N3	−171.76 (15)
C22—C11—C12—C17	159.33 (17)	O2—C28—N2—C11	171.30 (19)
C17—C12—C13—C14	2.0 (3)	C27—C28—N2—C11	−10.9 (2)
C11—C12—C13—C14	−171.81 (19)	C2—C11—N2—C28	133.47 (16)
C12—C13—C14—C15	2.5 (3)	C12—C11—N2—C28	−106.05 (17)
C13—C14—C15—N4	175.21 (19)	C22—C11—N2—C28	12.38 (19)
C13—C14—C15—C16	−4.7 (3)	C2—C11—N2—N3	−65.08 (19)
N4—C15—C16—C17	−177.43 (18)	C12—C11—N2—N3	55.4 (2)
C14—C15—C16—C17	2.5 (3)	C22—C11—N2—N3	173.83 (15)
C15—C16—C17—O1	−177.51 (18)	C30—C29—N3—N2	171.54 (17)
C15—C16—C17—C12	2.0 (3)	C33—C29—N3—N2	−7.6 (3)
C13—C12—C17—O1	175.24 (18)	C28—N2—N3—C29	−85.6 (2)
C11—C12—C17—O1	−10.6 (3)	C11—N2—N3—C29	114.41 (19)
C13—C12—C17—C16	−4.3 (3)	C16—C15—N4—C18	4.3 (3)
C11—C12—C17—C16	169.85 (17)	C14—C15—N4—C18	−175.7 (2)
O2—C28—C27—C22	−178.0 (2)	C16—C15—N4—C20	−169.4 (2)
N2—C28—C27—C22	4.3 (2)	C14—C15—N4—C20	10.7 (3)
O2—C28—C27—C26	3.0 (4)	C19—C18—N4—C15	−83.0 (3)
N2—C28—C27—C26	−174.7 (2)	C19—C18—N4—C20	90.9 (2)
C22—C27—C26—C25	−1.3 (3)	C21—C20—N4—C15	81.3 (3)
C28—C27—C26—C25	177.6 (2)	C21—C20—N4—C18	−92.6 (3)
C27—C26—C25—C24	−0.9 (3)	C16—C17—O1—C1	164.94 (16)
C26—C25—C24—C23	2.1 (3)	C12—C17—O1—C1	−14.6 (3)
C25—C24—C23—C22	−1.1 (3)	C6—C1—O1—C17	−160.98 (17)
C24—C23—C22—C27	−1.2 (3)	C2—C1—O1—C17	18.9 (2)
C24—C23—C22—C11	178.60 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1···O3	0.88 (2)	1.92 (2)	2.641 (2)	139 (2)
C33—H33A···N2	0.96	2.30	2.785 (3)	110
C7—H7B···O3ⁱ	0.97	2.60	3.334 (3)	133

Symmetry code: (i) x, y, z−1.

Experimental details

Crystal data
Chemical formula	C₃₃H₃₈N₄O₃
M_r	538.67
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	17.4255 (3), 15.0965 (3), 11.5354 (2)
β (°)	103.008 (1)
V (Å³)	2956.68 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.26 × 0.26 × 0.24

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.666, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	24441, 7000, 4223
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.659

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.165, 1.04
No. of reflections	7000
No. of parameters	365
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.23

Computer programs: APEX2 (Bruker, 2007), APEX2 and SAINT (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1···O3	0.88 (2)	1.92 (2)	2.641 (2)	139 (2)
C33—H33A···N2	0.96	2.30	2.785 (3)	110
C7—H7B···O3ⁱ	0.97	2.60	3.334 (3)	133

Symmetry code: (i) x, y, z−1.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (project No. 30873140), the Program for Excellent Talents of Beijing City (project No. 20071D0501600227) and the Beijing Municipal Commission of Education (project No. KM201010028011).

References

Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Soh, J. H., Swamy, K. M. K., Kim, S. K., Kim, S., Lee, S. H. & Yoon, J. (2007). Tetrahedron Lett. 48, 5966–5969. Web of Science CrossRef CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xiang, Y., Tong, A. J., Jin, P. Y. & Ju, Y. (2006). Org. Lett. 8, 2863–2866. Web of Science CrossRef PubMed CAS Google Scholar
Zhang, X., Shiraishi, Y. & Hirai, T. (2007). Org. Lett. 9, 5039–5042. Web of Science CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2205

https://doi.org/10.1107/S1600536812027602

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

(Z)-3′,6′-Bis(di­ethyl­amino)-2-(4-oxopent-2-en-2-yl­amino)­spiro­[isoindoline-1,9′-xanthen]-3-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(Z)-3′,6′-Bis(diethylamino)-2-(4-oxopent-2-en-2-ylamino)spiro[isoindoline-1,9′-xanthen]-3-one