Hydrogen bonding in 1′-nitro-2′-phenyl-2′,3′,4′,5′,6′,7′-hexa­hydro-1H-indole-3-spiro-3′-1′H-pyrrolizidin-2(3H)-one: mol­ecular chains built from alternating R_{2}^{2}(18) and R_{2}^{2}(8) rings

Usha, G.; Selvanayagam, S.; Velmurugan, D.; Ravikumar, K.; Poornachandran, M.

doi:10.1107/S1600536805029107

Hydrogen bonding in 1′-nitro-2′-phenyl-2′,3′,4′,5′,6′,7′-hexahydro-1H-indole-3-spiro-3′-1′H-pyrrolizidin-2(3H)-one: molecular chains built from alternating $R_{2}^{2}$ (18) and $R_{2}^{2}$ (8) rings

G. Usha, S. Selvanayagam, D. Velmurugan, K. Ravikumar and M. Poornachandran

In the title cycloadduct, C₂₀H₁₉N₃O₃, the molecules form centrosymmetric dimers linked by N—H

O hydrogen bonds, forming an R₂²(8) ring. The overall conformation of the pyrrolizidine nucleus is folded about the bridging bond.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805029107/bt6738sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805029107/bt6738Isup2.hkl Contains datablock I

CCDC reference: 287477

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R factor = 0.053
wR factor = 0.164
Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         C6
PLAT430_ALERT_2_B Short Inter D...A Contact  O2     ..  O3      ..       2.81 Ang.

Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.75 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N23    -   C4      ..       5.57 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C8
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N23
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C7

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

The chemistry of indole compounds has been extensively studied partly due to their use as pharmaceutical and industrial products. Some of the indole derivatives are used as neuroprotectants (Stolc, 1999). Spiro-indoles have been reported to show fungicidal activity (Ali et al., 1989). 5-Chloro-3-(phenylsulfonyl)indole-2-carboxamide is reported to be a highly potent non-nucleoside inhibitor of HIV-1 reverse transcriptase (Williams et al., 1993). The pyrrolizidine alkaloids are well documented for their mutagenic, antineoplastic, carcinogenic, hepatotoxic and many pharmacological activities. In view of the wide spectrum of biological activity of indole and pyrrolizidine derivatives, the X-ray analysis of a pyrrolizidine alkaloid, (I), has been undertaken and the structural details are presented in this communication.

The bond lengths and angles of the indole and benzene ring systems are normal. The pyrrolizidine ring-fusion distance [N1–C5 = 1.481 (2) Å] is in the same range as the other two N—C distances and compares quite well with those observed in related structures (Hay et al., 1982; Sussman & Wodak, 1973; Usha et al., 2005). Bond distances and angles around atom C2 are somewhat distorted, which is due to the spiro-atom character.

The C═O double bond is slightly elongated [C9═O1 = 1.222 (2) Å] due to the hydrogen bonding. This is similar to what was observed for the analogus bond in 1-naphthaleneacetic acid (Rajan, 1984), which forms hydrogen-bonded dimers.

In the title adduct, each molecule is linked to a centrosymmetrically related molecule by N—H···O hydrogen bonds forming R₂²(8) rings. The nitro group does not play any role in hydrogen bonding, but participates in fairly weak intramolecular contacts (Table 2).

In the pyrrolizidine nucleus, both five-membered rings adopt twist conformations. The smallest displacement asymmetry parameters (Nardelli, 1983) are ΔC₂(C5) = 0.018 (1) and ΔC₂(C5) = 0.015 (1)°. The overall conformation of the pyrrolizidine nucleus is folded about the bridging bond, viz. N1—C5. The angle between the best planes of the two rings is 54.2 (1)°. This observation is consistent with the structure reported by Usha et al. (2005).

Experimental top

A mixture of nitrostyrene (1 mmol), isatin (1 mmol) and proline (1 mmol) in methanol (20 ml) was refluxed until the disappearance of starting materials. After completion of the reaction, the reaction mixture was concentrated in vacuo and the residue was subjected to column chromatography with a hexane–ethyl acetate mixture (8:2) in order to get the pure cycloadduct. Crystals suitable for sigle-crystal X-ray diffraction were grown by slow evaporation of a methanol solution.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Figures top

	Fig. 1. The molecular structure of title adduct, showing 30% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound, viewed on to the ac plane. Hydrogen bonds are shown as dashed lines.

1'-nitro-2'-phenyl-2',3',4',5',6',7'-hexahydro-1H-indole- 3-spiro-3'-1'H-pyrrolizin-2(3H)-one top

Crystal data top

C₂₀H₁₉N₃O₃	F(000) = 1472
M_r = 349.38	D_x = 1.372 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7483 reflections
a = 23.8981 (15) Å	θ = 2.5–26.5°
b = 7.5886 (4) Å	µ = 0.09 mm⁻¹
c = 19.137 (1) Å	T = 293 K
β = 102.941 (2)°	Block, colourless
V = 3382.4 (3) Å³	0.23 × 0.21 × 0.20 mm
Z = 8

Data collection top

CCD Area Detector diffractometer	3373 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.018
Graphite monochromator	θ_max = 28.0°, θ_min = 2.2°
ω scans	h = −30→31
13982 measured reflections	k = −9→9
3921 independent reflections	l = −25→25

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.164	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0985P)² + 1.7117P] where P = (F_o² + 2F_c²)/3
3921 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₂₀H₁₉N₃O₃	V = 3382.4 (3) Å³
M_r = 349.38	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 23.8981 (15) Å	µ = 0.09 mm⁻¹
b = 7.5886 (4) Å	T = 293 K
c = 19.137 (1) Å	0.23 × 0.21 × 0.20 mm
β = 102.941 (2)°

Data collection top

CCD Area Detector diffractometer	3373 reflections with I > 2σ(I)
13982 measured reflections	R_int = 0.018
3921 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.164	H-atom parameters constrained
S = 1.03	Δρ_max = 0.29 e Å⁻³
3921 reflections	Δρ_min = −0.29 e Å⁻³
235 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
O1	0.07159 (5)	−0.02311 (14)	0.06395 (6)	0.0512 (3)
O2	0.27239 (8)	0.0114 (4)	0.18077 (14)	0.1251 (9)
O3	0.25603 (8)	0.2023 (3)	0.25370 (12)	0.1132 (7)
N1	0.08805 (5)	0.10616 (17)	0.21380 (6)	0.0436 (3)
N10	0.00611 (5)	0.20074 (17)	0.05533 (7)	0.0445 (3)
H10	−0.0198	0.1601	0.0204	0.053*
N23	0.23993 (6)	0.0986 (2)	0.20513 (10)	0.0650 (5)
C2	0.08624 (6)	0.22227 (18)	0.15167 (7)	0.0371 (3)
C3	0.15020 (5)	0.26078 (18)	0.15331 (7)	0.0367 (3)
H3	0.1640	0.3385	0.1945	0.044*
C4	0.17707 (6)	0.0804 (2)	0.17411 (8)	0.0440 (3)
H4	0.1718	0.0078	0.1308	0.053*
C5	0.14116 (7)	−0.0006 (2)	0.22439 (10)	0.0518 (4)
H5	0.1307	−0.1215	0.2087	0.062*
C6	0.16539 (11)	−0.0018 (5)	0.30496 (12)	0.1010 (10)
H6A	0.1773	−0.1196	0.3216	0.121*
H6B	0.1981	0.0767	0.3177	0.121*
C7	0.11687 (10)	0.0609 (3)	0.33690 (11)	0.0705 (5)
H7A	0.0912	−0.0352	0.3419	0.085*
H7B	0.1311	0.1152	0.3834	0.085*
C8	0.08778 (11)	0.1922 (3)	0.28300 (9)	0.0728 (6)
H8A	0.0489	0.2147	0.2878	0.087*
H8B	0.1088	0.3025	0.2878	0.087*
C9	0.05515 (6)	0.11579 (18)	0.08476 (7)	0.0397 (3)
C11	0.00235 (6)	0.3636 (2)	0.08866 (8)	0.0408 (3)
C12	0.04882 (6)	0.38338 (18)	0.14655 (7)	0.0380 (3)
C13	0.05582 (7)	0.5407 (2)	0.18389 (8)	0.0467 (4)
H13	0.0871	0.5571	0.2222	0.056*
C14	0.01571 (8)	0.6740 (2)	0.16365 (9)	0.0538 (4)
H14	0.0201	0.7803	0.1884	0.065*
C15	−0.03060 (8)	0.6494 (2)	0.10691 (10)	0.0584 (4)
H15	−0.0574	0.7393	0.0944	0.070*
C16	−0.03812 (7)	0.4937 (2)	0.06811 (9)	0.0535 (4)
H16	−0.0693	0.4777	0.0297	0.064*
C17	0.16435 (6)	0.3511 (2)	0.08923 (7)	0.0395 (3)
C18	0.16935 (7)	0.2624 (2)	0.02743 (8)	0.0492 (4)
H18	0.1631	0.1414	0.0240	0.059*
C19	0.18361 (8)	0.3528 (3)	−0.02910 (10)	0.0614 (5)
H19	0.1873	0.2916	−0.0699	0.074*
C20	0.19233 (9)	0.5317 (3)	−0.02532 (11)	0.0670 (5)
H20	0.2019	0.5914	−0.0635	0.080*
C21	0.18695 (9)	0.6217 (3)	0.03473 (11)	0.0682 (5)
H21	0.1925	0.7430	0.0373	0.082*
C22	0.17320 (8)	0.5322 (2)	0.09184 (10)	0.0532 (4)
H22	0.1698	0.5944	0.1326	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0497 (6)	0.0439 (6)	0.0534 (6)	0.0012 (4)	−0.0023 (5)	−0.0150 (5)
O2	0.0705 (11)	0.176 (2)	0.1421 (18)	0.0555 (13)	0.0530 (12)	0.0464 (17)
O3	0.0751 (11)	0.1170 (15)	0.1170 (15)	−0.0209 (10)	−0.0428 (10)	0.0099 (13)
N1	0.0408 (6)	0.0482 (7)	0.0400 (6)	−0.0025 (5)	0.0052 (5)	0.0009 (5)
N10	0.0353 (6)	0.0497 (7)	0.0422 (6)	−0.0014 (5)	−0.0046 (5)	−0.0104 (5)
N23	0.0434 (8)	0.0808 (11)	0.0687 (10)	0.0111 (7)	0.0081 (7)	0.0333 (9)
C2	0.0340 (6)	0.0399 (7)	0.0346 (6)	−0.0027 (5)	0.0018 (5)	−0.0052 (5)
C3	0.0328 (6)	0.0391 (7)	0.0346 (6)	−0.0006 (5)	0.0000 (5)	−0.0033 (5)
C4	0.0415 (7)	0.0453 (8)	0.0422 (7)	0.0049 (6)	0.0029 (6)	0.0008 (6)
C5	0.0523 (9)	0.0420 (8)	0.0613 (10)	0.0029 (6)	0.0134 (7)	0.0091 (7)
C6	0.0788 (15)	0.164 (3)	0.0608 (13)	0.0419 (17)	0.0180 (11)	0.0545 (16)
C7	0.0788 (13)	0.0821 (14)	0.0485 (10)	−0.0018 (11)	0.0099 (9)	0.0132 (9)
C8	0.0909 (14)	0.0873 (14)	0.0391 (9)	0.0276 (12)	0.0122 (9)	0.0023 (9)
C9	0.0370 (7)	0.0412 (7)	0.0379 (7)	−0.0053 (5)	0.0019 (5)	−0.0049 (5)
C11	0.0344 (6)	0.0476 (8)	0.0392 (7)	−0.0008 (5)	0.0057 (5)	−0.0041 (6)
C12	0.0335 (6)	0.0420 (7)	0.0377 (7)	−0.0013 (5)	0.0061 (5)	−0.0035 (5)
C13	0.0455 (8)	0.0468 (8)	0.0455 (8)	−0.0013 (6)	0.0055 (6)	−0.0093 (6)
C14	0.0574 (9)	0.0470 (8)	0.0583 (9)	0.0045 (7)	0.0157 (7)	−0.0102 (7)
C15	0.0537 (9)	0.0587 (10)	0.0619 (10)	0.0180 (8)	0.0112 (8)	−0.0017 (8)
C16	0.0401 (8)	0.0639 (10)	0.0520 (9)	0.0101 (7)	0.0007 (6)	−0.0043 (7)
C17	0.0300 (6)	0.0465 (7)	0.0389 (7)	−0.0005 (5)	0.0011 (5)	0.0002 (6)
C18	0.0482 (8)	0.0521 (9)	0.0473 (8)	0.0047 (7)	0.0107 (6)	−0.0016 (7)
C19	0.0563 (10)	0.0834 (13)	0.0472 (9)	0.0093 (9)	0.0174 (7)	0.0014 (9)
C20	0.0586 (11)	0.0824 (14)	0.0624 (11)	−0.0048 (9)	0.0188 (9)	0.0193 (10)
C21	0.0742 (13)	0.0576 (10)	0.0720 (13)	−0.0165 (9)	0.0145 (10)	0.0091 (9)
C22	0.0552 (9)	0.0507 (9)	0.0514 (9)	−0.0113 (7)	0.0069 (7)	−0.0031 (7)

Geometric parameters (Å, º) top

O1—C9	1.222 (2)	C7—H7B	0.9700
O2—N23	1.191 (3)	C8—H8A	0.9700
O3—N23	1.213 (3)	C8—H8B	0.9700
N1—C2	1.473 (2)	C11—C16	1.376 (2)
N1—C5	1.481 (2)	C11—C12	1.3901 (19)
N1—C8	1.478 (2)	C12—C13	1.382 (2)
N10—C9	1.346 (2)	C13—C14	1.388 (2)
N10—C11	1.403 (2)	C13—H13	0.9300
N10—H10	0.8600	C14—C15	1.379 (3)
N23—C4	1.493 (2)	C14—H14	0.9300
C2—C12	1.5048 (19)	C15—C16	1.386 (3)
C2—C3	1.5495 (18)	C15—H15	0.9300
C2—C9	1.5552 (18)	C16—H16	0.9300
C3—C17	1.5081 (19)	C17—C22	1.389 (2)
C3—C4	1.526 (2)	C17—C18	1.389 (2)
C3—H3	0.9800	C18—C19	1.386 (2)
C4—C5	1.553 (2)	C18—H18	0.9300
C4—H4	0.9800	C19—C20	1.373 (3)
C5—C6	1.521 (3)	C19—H19	0.9300
C5—H5	0.9800	C20—C21	1.367 (3)
C6—C7	1.504 (3)	C20—H20	0.9300
C6—H6A	0.9700	C21—C22	1.387 (3)
C6—H6B	0.9700	C21—H21	0.9300
C7—C8	1.490 (3)	C22—H22	0.9300
C7—H7A	0.9700

C2—N1—C5	107.9 (1)	N1—C8—C7	103.28 (17)
C2—N1—C8	117.0 (1)	N1—C8—H8A	111.1
C5—N1—C8	107.2 (1)	C7—C8—H8A	111.1
C9—N10—C11	111.73 (11)	N1—C8—H8B	111.1
C9—N10—H10	124.1	C7—C8—H8B	111.1
C11—N10—H10	124.1	H8A—C8—H8B	109.1
O2—N23—O3	122.5 (2)	O1—C9—N10	126.18 (13)
O2—N23—C4	118.6 (2)	O1—C9—C2	125.95 (13)
O3—N23—C4	118.86 (18)	N10—C9—C2	107.84 (12)
N1—C2—C12	116.64 (11)	C16—C11—C12	122.37 (14)
N1—C2—C3	104.23 (10)	C16—C11—N10	127.91 (14)
C12—C2—C3	114.65 (11)	C12—C11—N10	109.65 (12)
N1—C2—C9	106.03 (11)	C13—C12—C11	119.19 (13)
C12—C2—C9	101.61 (11)	C13—C12—C2	131.82 (13)
C3—C2—C9	113.70 (11)	C11—C12—C2	108.74 (12)
C17—C3—C4	117.51 (12)	C12—C13—C14	119.28 (14)
C17—C3—C2	117.97 (11)	C12—C13—H13	120.4
C4—C3—C2	101.06 (11)	C14—C13—H13	120.4
C17—C3—H3	106.5	C15—C14—C13	120.26 (15)
C4—C3—H3	106.5	C15—C14—H14	119.9
C2—C3—H3	106.5	C13—C14—H14	119.9
N23—C4—C3	110.38 (13)	C14—C15—C16	121.49 (16)
N23—C4—C5	115.90 (13)	C14—C15—H15	119.3
C3—C4—C5	104.96 (12)	C16—C15—H15	119.3
N23—C4—H4	108.5	C11—C16—C15	117.39 (15)
C3—C4—H4	108.5	C11—C16—H16	121.3
C5—C4—H4	108.5	C15—C16—H16	121.3
N1—C5—C6	105.19 (15)	C22—C17—C18	117.94 (15)
N1—C5—C4	105.90 (12)	C22—C17—C3	118.72 (14)
C6—C5—C4	119.52 (17)	C18—C17—C3	123.34 (13)
N1—C5—H5	108.6	C19—C18—C17	120.51 (16)
C6—C5—H5	108.6	C19—C18—H18	119.7
C4—C5—H5	108.6	C17—C18—H18	119.7
C7—C6—C5	104.89 (18)	C20—C19—C18	120.60 (18)
C7—C6—H6A	110.8	C20—C19—H19	119.7
C5—C6—H6A	110.8	C18—C19—H19	119.7
C7—C6—H6B	110.8	C21—C20—C19	119.76 (18)
C5—C6—H6B	110.8	C21—C20—H20	120.1
H6A—C6—H6B	108.8	C19—C20—H20	120.1
C8—C7—C6	102.29 (17)	C20—C21—C22	120.06 (18)
C8—C7—H7A	111.3	C20—C21—H21	120.0
C6—C7—H7A	111.3	C22—C21—H21	120.0
C8—C7—H7B	111.3	C21—C22—C17	121.12 (17)
C6—C7—H7B	111.3	C21—C22—H22	119.4
H7A—C7—H7B	109.2	C17—C22—H22	119.4

C5—N1—C2—C12	−159.01 (12)	C12—C2—C9—O1	175.92 (14)
C8—N1—C2—C12	−38.21 (18)	C3—C2—C9—O1	52.2 (2)
C5—N1—C2—C3	−31.5 (1)	N1—C2—C9—N10	116.29 (13)
C8—N1—C2—C3	89.28 (16)	C12—C2—C9—N10	−6.06 (15)
C5—N1—C2—C9	88.76 (13)	C3—C2—C9—N10	−129.79 (13)
C8—N1—C2—C9	−150.43 (14)	C9—N10—C11—C16	172.24 (16)
N1—C2—C3—C17	169.54 (11)	C9—N10—C11—C12	−4.67 (18)
C12—C2—C3—C17	−61.76 (16)	C16—C11—C12—C13	−1.8 (2)
C9—C2—C3—C17	54.55 (16)	N10—C11—C12—C13	175.29 (13)
N1—C2—C3—C4	40.0 (1)	C16—C11—C12—C2	−176.78 (14)
C12—C2—C3—C4	168.70 (11)	N10—C11—C12—C2	0.33 (16)
C9—C2—C3—C4	−74.99 (13)	N1—C2—C12—C13	74.5 (2)
O2—N23—C4—C3	−127.59 (18)	C3—C2—C12—C13	−47.7 (2)
O3—N23—C4—C3	51.8 (2)	C9—C2—C12—C13	−170.75 (16)
O2—N23—C4—C5	113.3 (2)	N1—C2—C12—C11	−111.39 (13)
O3—N23—C4—C5	−67.3 (2)	C3—C2—C12—C11	126.42 (13)
C17—C3—C4—N23	71.17 (16)	C9—C2—C12—C11	3.35 (15)
C2—C3—C4—N23	−158.99 (13)	C11—C12—C13—C14	1.3 (2)
C17—C3—C4—C5	−163.27 (12)	C2—C12—C13—C14	174.85 (15)
C2—C3—C4—C5	−33.4 (1)	C12—C13—C14—C15	0.0 (3)
C2—N1—C5—C6	137.50 (17)	C13—C14—C15—C16	−0.9 (3)
C8—N1—C5—C6	10.7 (2)	C12—C11—C16—C15	1.0 (3)
C2—N1—C5—C4	10.1 (2)	N10—C11—C16—C15	−175.55 (16)
C8—N1—C5—C4	−116.73 (16)	C14—C15—C16—C11	0.4 (3)
N23—C4—C5—N1	137.66 (15)	C4—C3—C17—C22	−140.90 (14)
C3—C4—C5—N1	15.6 (2)	C2—C3—C17—C22	97.67 (16)
N23—C4—C5—C6	19.3 (2)	C4—C3—C17—C18	38.75 (18)
C3—C4—C5—C6	−102.70 (19)	C2—C3—C17—C18	−82.68 (17)
N1—C5—C6—C7	15.2 (3)	C22—C17—C18—C19	1.0 (2)
C4—C5—C6—C7	133.9 (2)	C3—C17—C18—C19	−178.69 (14)
C5—C6—C7—C8	−35.0 (3)	C17—C18—C19—C20	−0.8 (3)
C2—N1—C8—C7	−154.05 (16)	C18—C19—C20—C21	0.0 (3)
C5—N1—C8—C7	−32.8 (2)	C19—C20—C21—C22	0.5 (3)
C6—C7—C8—N1	41.6 (3)	C20—C21—C22—C17	−0.4 (3)
C11—N10—C9—O1	−175.23 (14)	C18—C17—C22—C21	−0.4 (2)
C11—N10—C9—C2	6.76 (16)	C3—C17—C22—C21	179.29 (16)
N1—C2—C9—O1	−61.72 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6B···O3	0.97	2.26	3.001 (4)	133
N10—H10···O1ⁱ	0.86	2.08	2.929 (2)	169
C20—H20···O2ⁱⁱ	0.93	2.58	3.285 (3)	133

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₉N₃O₃
M_r	349.38
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	23.8981 (15), 7.5886 (4), 19.137 (1)
β (°)	102.941 (2)
V (Å³)	3382.4 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.23 × 0.21 × 0.20

Data collection
Diffractometer	CCD Area Detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13982, 3921, 3373
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.164, 1.03
No. of reflections	3921
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.29

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003), SHELXL97 and PARST (Nardelli, 1995).

Selected geometric parameters (Å, º) top

O1—C9	1.222 (2)	N1—C8	1.478 (2)
O2—N23	1.191 (3)	N10—C9	1.346 (2)
O3—N23	1.213 (3)	N10—C11	1.403 (2)
N1—C2	1.473 (2)	N23—C4	1.493 (2)
N1—C5	1.481 (2)

C2—N1—C5	107.9 (1)	C5—N1—C8	107.2 (1)
C2—N1—C8	117.0 (1)

C5—N1—C2—C3	−31.5 (1)	C3—C4—C5—N1	15.6 (2)
N1—C2—C3—C4	40.0 (1)	N1—C5—C6—C7	15.2 (3)
C2—C3—C4—C5	−33.4 (1)	C5—C6—C7—C8	−35.0 (3)
C8—N1—C5—C6	10.7 (2)	C5—N1—C8—C7	−32.8 (2)
C2—N1—C5—C4	10.1 (2)	C6—C7—C8—N1	41.6 (3)