5-Methyl-3,3-bis­(morpholin-4-yl)-1-[2-(morpholin-4-yl)eth­yl]-2,3-dihydro-1H-indol-2-one

Lin, H.-H.; Wu, W.-Y.; Zhang, J.-J.; Cao, S.-L.

doi:10.1107/S1600536812007155

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o821

doi:10.1107/S1600536812007155

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5-Methyl-3,3-bis(morpholin-4-yl)-1-[2-(morpholin-4-yl)ethyl]-2,3-dihydro-1H-indol-2-one

Hui-Hui Lin,^a Wei-Yao Wu,^a Jing-Jing Zhang ^a and Sheng-Li Cao ^a ^*

^aDepartment of Chemistry, Capital Normal University, Beijing 100048, People's Republic of China
^*Correspondence e-mail: slcao@cnu.edu.cn

(Received 8 February 2012; accepted 17 February 2012; online 24 February 2012)

In the title compound, C₂₃H₃₄N₄O₄, the morpholine rings adopt chair conformations. The N atom of the indol-2-one group is linked to the N atom of one morpholine ring through a flexible ethyl group with an almost cif conformation. In the crystal, molecules are linked by C—H⋯O interactions into infinite chains along the c direction. The almost parallel infinite chains are further interconnected via other sets of C—H⋯O interactions, forming a three-dimensional framework.

Related literature

For background to and activities of indoline-2,3-dione and its derivatives, see Chiyanzu et al. (2005 ); Karali (2002 ); Sirisoma et al. (2009 ); Solomon et al. (2009 ); Sriram et al. (2004 ). For structural analogues of indoline-2,3-dione (isatin), see: Wang et al. (2012 ).

Experimental

Crystal data

C₂₃H₃₄N₄O₄
M_r = 430.54
Monoclinic, P 2₁ /c
a = 10.1772 (10) Å
b = 14.2576 (14) Å
c = 15.8950 (16) Å
β = 97.332 (2)°
V = 2287.5 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.40 × 0.30 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.660, T_max = 0.746
12380 measured reflections
5355 independent reflections
2599 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.141
S = 1.01
5355 reflections
280 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20B⋯O3ⁱ	0.97	2.62	3.109 (3)	112
C15—H15A⋯O3ⁱⁱ	0.97	2.52	3.480 (2)	173
C17—H17A⋯O2ⁱⁱⁱ	0.97	2.66	3.395 (3)	132
C13—H13B⋯O4^iv	0.97	2.64	3.318 (3)	128
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z; (iii) x-1, y, z; (iv) -x+1, -y+1, -z.

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: 10.1107/S1600536812007155/zq2153sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812007155/zq2153Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812007155/zq2153Isup3.cml

checkCIF report

Comment top

Mannich base derivatives of indoline-2,3-dione (isatin) were reported having a wide range of biological activities such as antibacterial (Chiyanzu et al., 2005), anti-HIV (Sriram et al., 2004) and anticancer activity (Karali, 2002; Sirisoma et al., 2009; Solomon et al., 2009). To obtain isatin Mannich base analogues with a flexible ethylene linker between the N atom of the isatin and the amine group of the morpholine, we designed the reaction of 1-(2-bromoethyl)-5-methylindoline-2,3-dione with an excess of morpholine. Interestingly, an additional nucleophilic addition of morpholine to one carbonyl group on the isatin simultaneously occurred to give the title compound (Scheme 1), which might also exhibit potential antitumor properties. Herein, we report the crystal structure of this new compound.

In the title compound, C₂₃H₃₄N₄O₄, the morpholine rings adopt chair conformations. The N1 atom of the indol-2-one moiety is linked to the N2 atom of a morpholine ring through a flexible ethylene group with an almost cis conformation [the torsion angle N1—C10—C11—N2 is 59.7 (3)°, as shown in Fig. 1]. Such a fashion is different from the trans conformation [corresponding torsion angle of 175.74 (11)°] found in 2-(5-fluoro-2,3-dioxoindolin-1-yl)ethyl 4-methylpiperazine-1-carbodithioate reported by us recently (Wang et al., 2012). The two morpholine groups at C9 (sp³) exhibit a N4—C9—N3 bond angle of 107.45 (15)°. Along the c axis, the molecules are interconnected and arranged into arrays through intermolecular C20—H20B(methylene)···O3ⁱ(ether) interactions (see Table 1 and Fig. 2). The almost parallel arrays formed are further interconnected via other sets of C—H(methylene)···O(ether) interactions (Table 1), forming a three-dimensional framework (Fig. 3).

Related literature top

For background to and activities of indoline-2,3-dione and its derivatives, see Chiyanzu et al. (2005); Karali (2002); Sirisoma et al. (2009); Solomon et al. (2009); Sriram et al. (2004). For structural analogues of indoline-2,3-dione (isatin), see: Wang et al. (2012).

Experimental top

To a solution of 1-(2-bromoethyl)-5-methylindoline-2,3-dione (0.27 g, 1 mmol) in N,N-dimethylformamide (5 ml) was added morpholine dropwise (0.52 g, 6 mmol). The mixture was stirred at 80–90°C for 3 h. The colourless crystals of the title compound were deposited by evaporation of the resulting solution at room temperature for one day (m.p. 450.2–451.9 K; yield 53%).

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 title molecule with the atomic numbering scheme. The displacement ellipsoids of the non-H atoms are shown at the 30% probability level. All H atoms are omitted for clarity.
	Fig. 2. The array of the title compound along the c direction. The red-dashed lines indicate C—H···O interactions. H atoms are omitted for clarity, except those involved in bonding interactions.
	Fig. 3. View down the c direction of the stacking structure of the title compound.

5-Methyl-3,3-bis(morpholin-4-yl)-1-[2-(morpholin-4-yl)ethyl]- 2,3-dihydro-1H-indol-2-one top

Crystal data top

C₂₃H₃₄N₄O₄	Z = 4
M_r = 430.54	F(000) = 928
Monoclinic, P2₁/c	D_x = 1.250 Mg m⁻³
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.1772 (10) Å	µ = 0.09 mm⁻¹
b = 14.2576 (14) Å	T = 296 K
c = 15.8950 (16) Å	Block, colourless
β = 97.332 (2)°	0.40 × 0.30 × 0.20 mm
V = 2287.5 (4) Å³

Data collection top

Bruker APEXII CCD diffractometer	5355 independent reflections
Radiation source: fine-focus sealed tube	2599 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ω scans	θ_max = 28.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −13→10
T_min = 0.660, T_max = 0.746	k = −18→14
12380 measured reflections	l = −20→20

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0533P)² + 0.0135P] P = (F_o² + 2F_c²)/3
5355 reflections	(Δ/σ)_max < 0.001
280 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₃H₃₄N₄O₄	V = 2287.5 (4) Å³
M_r = 430.54	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.1772 (10) Å	µ = 0.09 mm⁻¹
b = 14.2576 (14) Å	T = 296 K
c = 15.8950 (16) Å	0.40 × 0.30 × 0.20 mm
β = 97.332 (2)°

Data collection top

Bruker APEXII CCD diffractometer	5355 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2599 reflections with I > 2σ(I)
T_min = 0.660, T_max = 0.746	R_int = 0.040
12380 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 1.01	Δρ_max = 0.18 e Å⁻³
5355 reflections	Δρ_min = −0.16 e Å⁻³
280 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.

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.

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

	x	y	z	U_iso*/U_eq
N1	0.58843 (17)	0.24574 (12)	0.17404 (11)	0.0495 (5)
N2	0.80352 (17)	0.17783 (11)	0.08141 (13)	0.0561 (5)
N3	0.36653 (15)	0.22400 (10)	−0.00090 (9)	0.0398 (4)
N4	0.29148 (16)	0.34238 (10)	0.08565 (9)	0.0404 (4)
O1	0.58871 (14)	0.35530 (10)	0.06837 (9)	0.0577 (4)
O2	0.90210 (18)	0.16969 (14)	−0.07774 (12)	0.0859 (6)
O3	0.31081 (16)	0.09322 (10)	−0.13528 (9)	0.0579 (4)
O4	0.17921 (17)	0.52235 (10)	0.10253 (10)	0.0706 (5)
C1	0.3731 (2)	0.19469 (12)	0.15619 (12)	0.0404 (5)
C2	0.2663 (2)	0.14541 (13)	0.17824 (12)	0.0460 (5)
H2A	0.1832	0.1533	0.1471	0.055*
C3	0.2818 (2)	0.08355 (13)	0.24716 (14)	0.0533 (6)
C4	0.4063 (3)	0.07408 (15)	0.29203 (14)	0.0619 (7)
H4A	0.4176	0.0328	0.3377	0.074*
C5	0.5156 (3)	0.12359 (16)	0.27181 (14)	0.0608 (6)
H5A	0.5987	0.1160	0.3029	0.073*
C6	0.4963 (2)	0.18449 (13)	0.20389 (13)	0.0460 (5)
C7	0.1639 (3)	0.03148 (16)	0.27269 (16)	0.0784 (8)
H7A	0.1921	−0.0078	0.3207	0.118*
H7B	0.1253	−0.0066	0.2262	0.118*
H7C	0.0995	0.0757	0.2874	0.118*
C8	0.5323 (2)	0.29554 (14)	0.10519 (13)	0.0440 (5)
C9	0.38464 (19)	0.26432 (12)	0.08495 (12)	0.0389 (5)
C10	0.7280 (2)	0.25298 (17)	0.20717 (15)	0.0660 (7)
H10A	0.7376	0.2489	0.2686	0.079*
H10B	0.7611	0.3137	0.1922	0.079*
C11	0.8101 (2)	0.17647 (17)	0.17284 (16)	0.0702 (7)
H11A	0.9018	0.1836	0.1975	0.084*
H11B	0.7795	0.1160	0.1903	0.084*
C12	0.8768 (2)	0.25529 (14)	0.05026 (17)	0.0640 (7)
H12A	0.9702	0.2493	0.0712	0.077*
H12B	0.8452	0.3142	0.0707	0.077*
C13	0.8582 (3)	0.25463 (18)	−0.04466 (18)	0.0795 (8)
H13A	0.7651	0.2636	−0.0651	0.095*
H13B	0.9070	0.3065	−0.0651	0.095*
C14	0.8346 (3)	0.09313 (19)	−0.0469 (2)	0.0904 (9)
H14A	0.8684	0.0352	−0.0678	0.108*
H14B	0.7411	0.0974	−0.0681	0.108*
C15	0.8511 (3)	0.09099 (15)	0.0481 (2)	0.0774 (8)
H15A	0.8019	0.0385	0.0672	0.093*
H15B	0.9439	0.0824	0.0695	0.093*
C16	0.2317 (2)	0.19163 (14)	−0.02867 (12)	0.0491 (5)
H16A	0.1688	0.2409	−0.0204	0.059*
H16B	0.2117	0.1376	0.0045	0.059*
C17	0.2202 (2)	0.16579 (16)	−0.12093 (13)	0.0588 (6)
H17A	0.1306	0.1451	−0.1400	0.071*
H17B	0.2379	0.2206	−0.1538	0.071*
C18	0.4419 (2)	0.12244 (16)	−0.10682 (13)	0.0577 (6)
H18A	0.4637	0.1760	−0.1401	0.069*
H18B	0.5028	0.0721	−0.1157	0.069*
C19	0.4594 (2)	0.14893 (13)	−0.01383 (13)	0.0511 (6)
H19A	0.4426	0.0949	0.0203	0.061*
H19B	0.5495	0.1699	0.0033	0.061*
C20	0.2886 (2)	0.38543 (13)	0.16874 (12)	0.0491 (6)
H20A	0.3701	0.4197	0.1852	0.059*
H20B	0.2805	0.3373	0.2109	0.059*
C21	0.1725 (2)	0.45096 (14)	0.16374 (15)	0.0614 (6)
H21A	0.0914	0.4155	0.1494	0.074*
H21B	0.1695	0.4795	0.2188	0.074*
C22	0.1873 (3)	0.48121 (16)	0.02166 (15)	0.0686 (7)
H22A	0.1942	0.5305	−0.0196	0.082*
H22B	0.1067	0.4463	0.0040	0.082*
C23	0.3039 (2)	0.41675 (13)	0.02300 (13)	0.0537 (6)
H23A	0.3060	0.3894	−0.0327	0.064*
H23B	0.3855	0.4514	0.0383	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0419 (10)	0.0561 (11)	0.0486 (11)	0.0033 (9)	−0.0009 (9)	0.0031 (9)
N2	0.0502 (12)	0.0428 (10)	0.0761 (14)	0.0041 (9)	0.0118 (10)	0.0083 (9)
N3	0.0421 (10)	0.0395 (9)	0.0387 (10)	0.0038 (8)	0.0082 (8)	−0.0013 (7)
N4	0.0493 (11)	0.0361 (9)	0.0369 (9)	0.0081 (8)	0.0094 (8)	0.0025 (7)
O1	0.0517 (10)	0.0513 (9)	0.0712 (11)	−0.0052 (7)	0.0115 (8)	0.0084 (8)
O2	0.0714 (13)	0.0905 (13)	0.1004 (15)	0.0057 (11)	0.0289 (11)	−0.0122 (11)
O3	0.0659 (11)	0.0584 (9)	0.0510 (9)	−0.0035 (8)	0.0136 (8)	−0.0120 (7)
O4	0.0982 (14)	0.0441 (9)	0.0708 (11)	0.0230 (9)	0.0155 (10)	0.0018 (8)
C1	0.0480 (13)	0.0383 (11)	0.0353 (11)	0.0058 (9)	0.0071 (10)	0.0006 (9)
C2	0.0505 (14)	0.0431 (12)	0.0454 (13)	0.0036 (10)	0.0093 (10)	0.0023 (10)
C3	0.0735 (17)	0.0400 (12)	0.0493 (13)	0.0079 (11)	0.0189 (13)	0.0099 (10)
C4	0.0773 (19)	0.0588 (14)	0.0523 (15)	0.0212 (14)	0.0189 (14)	0.0196 (12)
C5	0.0644 (17)	0.0677 (15)	0.0492 (14)	0.0214 (13)	0.0028 (12)	0.0088 (12)
C6	0.0518 (14)	0.0449 (12)	0.0413 (12)	0.0088 (10)	0.0061 (11)	0.0027 (10)
C7	0.092 (2)	0.0689 (16)	0.0790 (18)	−0.0034 (15)	0.0303 (16)	0.0272 (14)
C8	0.0450 (13)	0.0410 (12)	0.0468 (13)	0.0047 (10)	0.0085 (11)	−0.0034 (10)
C9	0.0424 (12)	0.0387 (11)	0.0357 (11)	0.0042 (9)	0.0054 (9)	0.0025 (9)
C10	0.0501 (15)	0.0861 (17)	0.0581 (15)	0.0003 (13)	−0.0069 (12)	−0.0005 (13)
C11	0.0475 (15)	0.0740 (16)	0.087 (2)	0.0135 (13)	0.0007 (14)	0.0196 (14)
C12	0.0577 (16)	0.0464 (13)	0.089 (2)	0.0013 (11)	0.0130 (14)	0.0057 (12)
C13	0.080 (2)	0.0721 (18)	0.089 (2)	0.0104 (15)	0.0226 (17)	0.0107 (15)
C14	0.081 (2)	0.073 (2)	0.121 (3)	0.0015 (16)	0.029 (2)	−0.0298 (18)
C15	0.0638 (17)	0.0423 (14)	0.130 (3)	0.0052 (12)	0.0270 (17)	0.0000 (15)
C16	0.0449 (13)	0.0583 (13)	0.0444 (13)	−0.0028 (11)	0.0062 (10)	−0.0068 (10)
C17	0.0561 (15)	0.0720 (15)	0.0475 (14)	0.0010 (13)	0.0037 (12)	−0.0057 (11)
C18	0.0589 (16)	0.0608 (14)	0.0560 (15)	0.0041 (12)	0.0174 (12)	−0.0102 (11)
C19	0.0514 (14)	0.0501 (13)	0.0522 (14)	0.0074 (11)	0.0076 (11)	−0.0048 (10)
C20	0.0627 (15)	0.0422 (11)	0.0428 (12)	0.0040 (11)	0.0088 (11)	−0.0023 (9)
C21	0.0774 (18)	0.0490 (13)	0.0602 (15)	0.0120 (12)	0.0177 (13)	−0.0042 (11)
C22	0.089 (2)	0.0560 (14)	0.0606 (16)	0.0260 (13)	0.0103 (14)	0.0119 (12)
C23	0.0662 (16)	0.0461 (12)	0.0502 (13)	0.0121 (11)	0.0127 (12)	0.0117 (10)

Geometric parameters (Å, º) top

N1—C8	1.367 (2)	C10—H10A	0.9700
N1—C6	1.407 (2)	C10—H10B	0.9700
N1—C10	1.454 (3)	C11—H11A	0.9700
N2—C11	1.446 (3)	C11—H11B	0.9700
N2—C15	1.453 (3)	C12—C13	1.496 (3)
N2—C12	1.454 (2)	C12—H12A	0.9700
N3—C19	1.460 (2)	C12—H12B	0.9700
N3—C16	1.462 (2)	C13—H13A	0.9700
N3—C9	1.471 (2)	C13—H13B	0.9700
N4—C20	1.460 (2)	C14—C15	1.498 (4)
N4—C9	1.463 (2)	C14—H14A	0.9700
N4—C23	1.471 (2)	C14—H14B	0.9700
O1—C8	1.218 (2)	C15—H15A	0.9700
O2—C14	1.411 (3)	C15—H15B	0.9700
O2—C13	1.415 (3)	C16—C17	1.502 (3)
O3—C18	1.415 (2)	C16—H16A	0.9700
O3—C17	1.423 (2)	C16—H16B	0.9700
O4—C21	1.416 (2)	C17—H17A	0.9700
O4—C22	1.425 (3)	C17—H17B	0.9700
C1—C2	1.377 (3)	C18—C19	1.514 (3)
C1—C6	1.387 (3)	C18—H18A	0.9700
C1—C9	1.522 (2)	C18—H18B	0.9700
C2—C3	1.400 (3)	C19—H19A	0.9700
C2—H2A	0.9300	C19—H19B	0.9700
C3—C4	1.379 (3)	C20—C21	1.500 (3)
C3—C7	1.510 (3)	C20—H20A	0.9700
C4—C5	1.389 (3)	C20—H20B	0.9700
C4—H4A	0.9300	C21—H21A	0.9700
C5—C6	1.380 (3)	C21—H21B	0.9700
C5—H5A	0.9300	C22—C23	1.499 (3)
C7—H7A	0.9600	C22—H22A	0.9700
C7—H7B	0.9600	C22—H22B	0.9700
C7—H7C	0.9600	C23—H23A	0.9700
C8—C9	1.561 (3)	C23—H23B	0.9700
C10—C11	1.518 (3)

C8—N1—C6	111.35 (17)	O2—C13—C12	112.0 (2)
C8—N1—C10	122.82 (18)	O2—C13—H13A	109.2
C6—N1—C10	125.73 (18)	C12—C13—H13A	109.2
C11—N2—C15	112.30 (19)	O2—C13—H13B	109.2
C11—N2—C12	113.09 (19)	C12—C13—H13B	109.2
C15—N2—C12	108.31 (18)	H13A—C13—H13B	107.9
C19—N3—C16	109.01 (15)	O2—C14—C15	111.7 (2)
C19—N3—C9	114.25 (15)	O2—C14—H14A	109.3
C16—N3—C9	113.90 (14)	C15—C14—H14A	109.3
C20—N4—C9	114.50 (15)	O2—C14—H14B	109.3
C20—N4—C23	108.83 (14)	C15—C14—H14B	109.3
C9—N4—C23	115.55 (14)	H14A—C14—H14B	107.9
C14—O2—C13	110.01 (18)	N2—C15—C14	110.5 (2)
C18—O3—C17	109.76 (15)	N2—C15—H15A	109.6
C21—O4—C22	109.72 (15)	C14—C15—H15A	109.6
C2—C1—C6	119.68 (18)	N2—C15—H15B	109.6
C2—C1—C9	131.34 (19)	C14—C15—H15B	109.6
C6—C1—C9	108.97 (17)	H15A—C15—H15B	108.1
C1—C2—C3	120.5 (2)	N3—C16—C17	108.96 (16)
C1—C2—H2A	119.8	N3—C16—H16A	109.9
C3—C2—H2A	119.8	C17—C16—H16A	109.9
C4—C3—C2	118.1 (2)	N3—C16—H16B	109.9
C4—C3—C7	121.5 (2)	C17—C16—H16B	109.9
C2—C3—C7	120.4 (2)	H16A—C16—H16B	108.3
C3—C4—C5	122.7 (2)	O3—C17—C16	111.33 (18)
C3—C4—H4A	118.6	O3—C17—H17A	109.4
C5—C4—H4A	118.6	C16—C17—H17A	109.4
C6—C5—C4	117.5 (2)	O3—C17—H17B	109.4
C6—C5—H5A	121.2	C16—C17—H17B	109.4
C4—C5—H5A	121.2	H17A—C17—H17B	108.0
C5—C6—C1	121.5 (2)	O3—C18—C19	111.97 (17)
C5—C6—N1	128.3 (2)	O3—C18—H18A	109.2
C1—C6—N1	110.19 (17)	C19—C18—H18A	109.2
C3—C7—H7A	109.5	O3—C18—H18B	109.2
C3—C7—H7B	109.5	C19—C18—H18B	109.2
H7A—C7—H7B	109.5	H18A—C18—H18B	107.9
C3—C7—H7C	109.5	N3—C19—C18	108.84 (17)
H7A—C7—H7C	109.5	N3—C19—H19A	109.9
H7B—C7—H7C	109.5	C18—C19—H19A	109.9
O1—C8—N1	125.00 (19)	N3—C19—H19B	109.9
O1—C8—C9	126.93 (18)	C18—C19—H19B	109.9
N1—C8—C9	108.04 (17)	H19A—C19—H19B	108.3
N4—C9—N3	107.45 (15)	N4—C20—C21	108.70 (17)
N4—C9—C1	112.29 (14)	N4—C20—H20A	109.9
N3—C9—C1	115.03 (15)	C21—C20—H20A	109.9
N4—C9—C8	112.91 (15)	N4—C20—H20B	109.9
N3—C9—C8	107.82 (14)	C21—C20—H20B	109.9
C1—C9—C8	101.32 (16)	H20A—C20—H20B	108.3
N1—C10—C11	112.09 (19)	O4—C21—C20	112.16 (18)
N1—C10—H10A	109.2	O4—C21—H21A	109.2
C11—C10—H10A	109.2	C20—C21—H21A	109.2
N1—C10—H10B	109.2	O4—C21—H21B	109.2
C11—C10—H10B	109.2	C20—C21—H21B	109.2
H10A—C10—H10B	107.9	H21A—C21—H21B	107.9
N2—C11—C10	113.24 (18)	O4—C22—C23	112.10 (19)
N2—C11—H11A	108.9	O4—C22—H22A	109.2
C10—C11—H11A	108.9	C23—C22—H22A	109.2
N2—C11—H11B	108.9	O4—C22—H22B	109.2
C10—C11—H11B	108.9	C23—C22—H22B	109.2
H11A—C11—H11B	107.7	H22A—C22—H22B	107.9
N2—C12—C13	109.5 (2)	N4—C23—C22	108.35 (17)
N2—C12—H12A	109.8	N4—C23—H23A	110.0
C13—C12—H12A	109.8	C22—C23—H23A	110.0
N2—C12—H12B	109.8	N4—C23—H23B	110.0
C13—C12—H12B	109.8	C22—C23—H23B	110.0
H12A—C12—H12B	108.2	H23A—C23—H23B	108.4

C6—C1—C2—C3	−1.5 (3)	C2—C1—C9—C8	175.79 (18)
C9—C1—C2—C3	179.17 (18)	C6—C1—C9—C8	−3.60 (19)
C1—C2—C3—C4	0.3 (3)	O1—C8—C9—N4	−55.5 (2)
C1—C2—C3—C7	178.40 (18)	N1—C8—C9—N4	122.73 (16)
C2—C3—C4—C5	0.4 (3)	O1—C8—C9—N3	63.0 (2)
C7—C3—C4—C5	−177.7 (2)	N1—C8—C9—N3	−118.73 (16)
C3—C4—C5—C6	0.1 (3)	O1—C8—C9—C1	−175.82 (18)
C4—C5—C6—C1	−1.4 (3)	N1—C8—C9—C1	2.43 (18)
C4—C5—C6—N1	176.15 (19)	C8—N1—C10—C11	−95.5 (2)
C2—C1—C6—C5	2.1 (3)	C6—N1—C10—C11	80.6 (2)
C9—C1—C6—C5	−178.48 (18)	C15—N2—C11—C10	−164.15 (18)
C2—C1—C6—N1	−175.87 (16)	C12—N2—C11—C10	72.9 (2)
C9—C1—C6—N1	3.6 (2)	N1—C10—C11—N2	59.7 (3)
C8—N1—C6—C5	−179.7 (2)	C11—N2—C12—C13	−176.73 (18)
C10—N1—C6—C5	3.8 (3)	C15—N2—C12—C13	58.1 (2)
C8—N1—C6—C1	−2.0 (2)	C14—O2—C13—C12	57.4 (3)
C10—N1—C6—C1	−178.44 (18)	N2—C12—C13—O2	−59.1 (3)
C6—N1—C8—O1	177.82 (17)	C13—O2—C14—C15	−56.3 (3)
C10—N1—C8—O1	−5.6 (3)	C11—N2—C15—C14	176.5 (2)
C6—N1—C8—C9	−0.5 (2)	C12—N2—C15—C14	−57.9 (3)
C10—N1—C8—C9	176.11 (17)	O2—C14—C15—N2	57.9 (3)
C20—N4—C9—N3	174.99 (14)	C19—N3—C16—C17	−59.6 (2)
C23—N4—C9—N3	−57.4 (2)	C9—N3—C16—C17	171.50 (16)
C20—N4—C9—C1	47.5 (2)	C18—O3—C17—C16	−58.4 (2)
C23—N4—C9—C1	175.20 (17)	N3—C16—C17—O3	59.8 (2)
C20—N4—C9—C8	−66.3 (2)	C17—O3—C18—C19	57.7 (2)
C23—N4—C9—C8	61.4 (2)	C16—N3—C19—C18	58.5 (2)
C19—N3—C9—N4	175.91 (14)	C9—N3—C19—C18	−172.81 (15)
C16—N3—C9—N4	−57.90 (19)	O3—C18—C19—N3	−58.3 (2)
C19—N3—C9—C1	−58.3 (2)	C9—N4—C20—C21	−169.33 (16)
C16—N3—C9—C1	67.9 (2)	C23—N4—C20—C21	59.7 (2)
C19—N3—C9—C8	53.93 (19)	C22—O4—C21—C20	57.3 (3)
C16—N3—C9—C8	−179.89 (15)	N4—C20—C21—O4	−59.2 (2)
C2—C1—C9—N4	55.1 (3)	C21—O4—C22—C23	−57.4 (3)
C6—C1—C9—N4	−124.33 (17)	C20—N4—C23—C22	−59.6 (2)
C2—C1—C9—N3	−68.2 (2)	C9—N4—C23—C22	169.92 (18)
C6—C1—C9—N3	112.37 (18)	O4—C22—C23—N4	59.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20B···O3ⁱ	0.97	2.62	3.109 (3)	112
C15—H15A···O3ⁱⁱ	0.97	2.52	3.480 (2)	173
C17—H17A···O2ⁱⁱⁱ	0.97	2.66	3.395 (3)	132
C13—H13B···O4^iv	0.97	2.64	3.318 (3)	128

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, −y, −z; (iii) x−1, y, z; (iv) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₃H₃₄N₄O₄
M_r	430.54
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.1772 (10), 14.2576 (14), 15.8950 (16)
β (°)	97.332 (2)
V (Å³)	2287.5 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.660, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	12380, 5355, 2599
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.141, 1.01
No. of reflections	5355
No. of parameters	280
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.16

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
C20—H20B···O3ⁱ	0.97	2.62	3.109 (3)	112
C15—H15A···O3ⁱⁱ	0.97	2.52	3.480 (2)	173
C17—H17A···O2ⁱⁱⁱ	0.97	2.66	3.395 (3)	132
C13—H13B···O4^iv	0.97	2.64	3.318 (3)	128

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, −y, −z; (iii) x−1, y, z; (iv) −x+1, −y+1, −z.

Acknowledgements

The authors are grateful to the National Natural Science Foundation of China (project No. 20972099) and the Beijing Municipal Commission of Education for financial support.

References

Bruker (2007). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chiyanzu, I., Clarkson, C., Smith, P. J., Lehman, J., Gut, J., Rosenthal, P. J. & Chibale, K. (2005). Bioorg. Med. Chem. 13, 3249–3261. Web of Science CrossRef PubMed CAS Google Scholar
Karali, N. (2002). Eur. J. Med. Chem. 37, 909–918. Web of Science PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sirisoma, N., Pervin, A., Drewe, J., Tseng, B. & Cai, S. X. (2009). Bioorg. Med. Chem. Lett. 19, 2710–2713. Web of Science CrossRef PubMed CAS Google Scholar
Solomon, V. R., Hu, C. & Lee, H. (2009). Bioorg. Med. Chem. 17, 7585–7592. Web of Science CrossRef PubMed CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sriram, D., Bal, T. R. & Yogeeswari, P. (2004). Bioorg. Med. Chem. 12, 5865–5873. Web of Science CrossRef PubMed CAS Google Scholar
Wang, Y., Lin, H.-H. & Cao, S.-L. (2012). Acta Cryst. E68, o94–o95. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 68| Part 3| March 2012| Page o821

doi:10.1107/S1600536812007155

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

5-Methyl-3,3-bis­­(morpholin-4-yl)-1-[2-(morpholin-4-yl)eth­yl]-2,3-di­hydro-1H-indol-2-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

5-Methyl-3,3-bis(morpholin-4-yl)-1-[2-(morpholin-4-yl)ethyl]-2,3-dihydro-1H-indol-2-one