2′-(2-Chloro­phen­yl)-1′-nitro-2′,3′,4′,5′,6′,7′-hexa­hydro-1H-indole-3-spiro-3′-1′H-pyrrolizin-2(3H)-one

Usha, G.; Selvanayagam, S.; Velmurugan, D.; Ravikumar, K.; Raghunathan, R.

doi:10.1107/S1600536805028990

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2′-(2-Chlorophenyl)-1′-nitro-2′,3′,4′,5′,6′,7′-hexahydro-1H-indole-3-spiro-3′-1′H-pyrrolizin-2(3H)-one

G. Usha, S. Selvanayagam, D. Velmurugan, K. Ravikumar and R. Raghunathan

The structure of the title cycloadduct, C₂₀H₁₈N₃O₃Cl, has been determined. The inversion-related molecules are held together by N—H

O hydrogen bonds, forming R²₂(8) rings. 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/S1600536805028990/bt6737sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805028990/bt6737Isup2.hkl Contains datablock I

CCDC reference: 287476

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R factor = 0.042
wR factor = 0.127
Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



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    O     Ueq(max)/Ueq(min) ...       2.66 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O3     -   N23     ..       5.87 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C6
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N23

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 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
   4 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

Nitro compounds are excellent precursors for aromatic amines and medicinally important compounds; they are also well known for their uses as explosives, dye intermediates and battery cathodes (Sivasamy et al., 1988). Some of the indole alkaloids extracted from plants have been found to exhibit cytotoxic, antitumour and antiparasitic properties (Quetin-Leclercq, 1994). Pyrido[1,2-a]indole derivatives have been identified as potent inhibitors of human immunodeficiency virus type 1 (Taylor et al., 1999). In view of the wide range of biological activities and industrial applications associated with the title adduct, (I), we have undertaken the X-ray analysis of the pyrrolizidine alkaloid.

Bond lengths and bond angles of the pyrrolizidine group and the oxindole unit present no unexpected features and are in the same range as observed in reported stuctures (Govind et al., 2004; Usha et al., 2005). The C9═O1 double bond is slightly elongated [1.227 (2) Å] as a result of the hydrogen bonding. This is similar to what was found for the analogus bond in 1-naphthaleneacetic acid (Rajan, 1984), which forms hydrogen-bonded dimers.

In the title adduct, each molecule forms a centrosymmetric dimer by N—H···O hydrogen bonds generating R²₂(8) rings. Although atom Cl1 plays no role in hydrogen bonding, it participates in a fairly weak intra-molecular contact (Table 2).

The pyrrolizidine nucleus is composed of two five-membered rings. The N1/C2–C5 ring adopts a twist conformation, with a smallest asymmetry parameter (Nardelli, 1983) of ΔC₂(C5) = 0.009 (1)°. The asymmetry parameters [Δ_S(C7) = 0.044 (1)° and ΔC₂(C5) = 0.040 (1)°] show the envelope conformation of the N1/C5–C8 ring. The overall conformation of the pyrrolizidine nucleus is folded about the bridgehead bond, N1—C5. The extent of twist about the N1—C5 bond is given by the dihedral angle between the mean planes through the two five-membered rings, which is 51.3 (1)°. This observation is consistent with the structure reported by Usha et al. (2005).

Experimental top

A mixture of 2-chloronitrostyrene (1 mmol), isatin (1 mmol) and proline (1 mmol) in methanol (20 ml) was refluxed until the disappearance of the starting materials. After the completion of the reaction, the reaction mixture was concentrated in vacuo and the residue was subjected to column chromatography with hexane–ethylacetate (8:2), to give the pure cycloadduct. Crystals suitable for a single-crystal X-ray structure determination 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 compound, showing 30% probability displacement ellipsoids.
	Fig. 2. The crystal structure showing the formation of hydrogen-bonded R²₂(8) rings. View direction is along the a axis. Hydrogen bonds are shown as dashed lines.

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

Crystal data top

C₂₀H₁₈ClN₃O₃	Z = 2
M_r = 383.82	F(000) = 400
Triclinic, P1	D_x = 1.405 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4698 (5) Å	Cell parameters from 5235 reflections
b = 9.3359 (6) Å	θ = 2.2–27.2°
c = 12.6058 (8) Å	µ = 0.24 mm⁻¹
α = 74.394 (1)°	T = 293 K
β = 72.025 (1)°	Block, colourless
γ = 79.334 (1)°	0.22 × 0.21 × 0.19 mm
V = 907.49 (10) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3661 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.016
Graphite monochromator	θ_max = 28.0°, θ_min = 1.7°
ω scans	h = −11→11
7852 measured reflections	k = −12→11
4067 independent reflections	l = −16→16

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0795P)² + 0.1853P] where P = (F_o² + 2F_c²)/3
4067 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₀H₁₈ClN₃O₃	γ = 79.334 (1)°
M_r = 383.82	V = 907.49 (10) Å³
Triclinic, P1	Z = 2
a = 8.4698 (5) Å	Mo Kα radiation
b = 9.3359 (6) Å	µ = 0.24 mm⁻¹
c = 12.6058 (8) Å	T = 293 K
α = 74.394 (1)°	0.22 × 0.21 × 0.19 mm
β = 72.025 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3661 reflections with I > 2σ(I)
7852 measured reflections	R_int = 0.016
4067 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.128	H-atom parameters constrained
S = 1.02	Δρ_max = 0.31 e Å⁻³
4067 reflections	Δρ_min = −0.23 e Å⁻³
244 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
Cl1	−0.05788 (5)	0.23832 (5)	0.49497 (3)	0.05686 (15)
O1	0.34666 (14)	0.36659 (12)	0.01487 (8)	0.0473 (3)
O2	−0.1362 (3)	0.0653 (3)	0.1201 (2)	0.1259 (8)
O3	−0.1325 (2)	0.0243 (2)	0.29225 (15)	0.0917 (5)
N1	0.36516 (15)	0.06695 (13)	0.16276 (10)	0.0418 (3)
N10	0.46895 (15)	0.40243 (13)	0.14350 (10)	0.0441 (3)
H10	0.5228	0.4764	0.1008	0.053*
N23	−0.0761 (2)	0.07547 (19)	0.19242 (16)	0.0648 (4)
C2	0.30473 (16)	0.20214 (13)	0.20889 (10)	0.0347 (3)
C3	0.11091 (16)	0.20958 (14)	0.24386 (10)	0.0352 (3)
H3	0.0784	0.1349	0.3158	0.042*
C4	0.08125 (19)	0.15147 (16)	0.15075 (12)	0.0442 (3)
H4	0.0730	0.2353	0.0857	0.053*
C5	0.2389 (2)	0.04150 (17)	0.11284 (13)	0.0484 (3)
H5	0.2807	0.0667	0.0291	0.058*
C6	0.2247 (3)	−0.1275 (2)	0.1541 (2)	0.0742 (6)
H6A	0.1275	−0.1479	0.2189	0.089*
H6B	0.2170	−0.1687	0.0932	0.089*
C7	0.3826 (3)	−0.1915 (2)	0.18785 (18)	0.0668 (5)
H7A	0.4748	−0.2054	0.1217	0.080*
H7B	0.3691	−0.2864	0.2432	0.080*
C8	0.4092 (3)	−0.07268 (17)	0.24016 (17)	0.0596 (4)
H8A	0.3369	−0.0792	0.3174	0.072*
H8B	0.5245	−0.0813	0.2416	0.072*
C9	0.37309 (17)	0.33404 (15)	0.10935 (11)	0.0381 (3)
C11	0.47039 (16)	0.33828 (15)	0.25740 (12)	0.0385 (3)
C12	0.37553 (15)	0.21774 (14)	0.30077 (11)	0.0346 (3)
C13	0.35386 (17)	0.14260 (15)	0.41373 (12)	0.0390 (3)
H13	0.2891	0.0632	0.4446	0.047*
C14	0.43042 (18)	0.18739 (17)	0.48078 (13)	0.0445 (3)
H14	0.4176	0.1368	0.5568	0.053*
C15	0.52490 (19)	0.30589 (19)	0.43563 (14)	0.0502 (4)
H15	0.5753	0.3338	0.4818	0.060*
C16	0.54646 (19)	0.38455 (18)	0.32274 (14)	0.0487 (3)
H16	0.6096	0.4651	0.2924	0.058*
C17	0.01671 (16)	0.35786 (15)	0.26425 (11)	0.0378 (3)
C18	−0.05603 (17)	0.38292 (17)	0.37443 (12)	0.0421 (3)
C19	−0.1332 (2)	0.5225 (2)	0.39248 (16)	0.0545 (4)
H19	−0.1788	0.5366	0.4667	0.065*
C20	−0.1420 (2)	0.63970 (19)	0.30064 (18)	0.0608 (4)
H20	−0.1926	0.7335	0.3125	0.073*
C21	−0.0760 (2)	0.61806 (18)	0.19109 (17)	0.0584 (4)
H21	−0.0843	0.6968	0.1289	0.070*
C22	0.0027 (2)	0.47949 (17)	0.17329 (14)	0.0481 (3)
H22	0.0476	0.4669	0.0987	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0541 (2)	0.0758 (3)	0.0341 (2)	−0.00738 (19)	−0.00593 (16)	−0.00883 (17)
O1	0.0621 (6)	0.0484 (6)	0.0300 (5)	−0.0245 (5)	−0.0068 (4)	−0.0010 (4)
O2	0.1121 (15)	0.186 (2)	0.1263 (17)	−0.0626 (15)	−0.0561 (13)	−0.0535 (16)
O3	0.0855 (10)	0.1058 (12)	0.0854 (11)	−0.0629 (10)	0.0084 (9)	−0.0262 (9)
N1	0.0485 (6)	0.0362 (6)	0.0387 (6)	−0.0116 (5)	−0.0023 (5)	−0.0115 (5)
N10	0.0515 (7)	0.0419 (6)	0.0376 (6)	−0.0247 (5)	−0.0072 (5)	0.0005 (5)
N23	0.0569 (8)	0.0706 (10)	0.0828 (11)	−0.0212 (7)	−0.0197 (8)	−0.0333 (9)
C2	0.0420 (6)	0.0310 (6)	0.0292 (6)	−0.0131 (5)	−0.0044 (5)	−0.0037 (5)
C3	0.0412 (6)	0.0346 (6)	0.0303 (6)	−0.0142 (5)	−0.0067 (5)	−0.0046 (5)
C4	0.0544 (8)	0.0439 (7)	0.0391 (7)	−0.0185 (6)	−0.0129 (6)	−0.0084 (6)
C5	0.0603 (9)	0.0485 (8)	0.0392 (7)	−0.0180 (7)	−0.0052 (6)	−0.0163 (6)
C6	0.0850 (14)	0.0489 (9)	0.0995 (16)	−0.0191 (9)	−0.0214 (12)	−0.0309 (10)
C7	0.0799 (12)	0.0416 (8)	0.0730 (12)	−0.0080 (8)	−0.0031 (10)	−0.0228 (8)
C8	0.0760 (11)	0.0370 (8)	0.0640 (10)	−0.0019 (7)	−0.0183 (9)	−0.0125 (7)
C9	0.0436 (7)	0.0353 (6)	0.0320 (6)	−0.0136 (5)	−0.0025 (5)	−0.0050 (5)
C11	0.0370 (6)	0.0381 (6)	0.0392 (7)	−0.0091 (5)	−0.0080 (5)	−0.0064 (5)
C12	0.0347 (6)	0.0332 (6)	0.0343 (6)	−0.0060 (5)	−0.0070 (5)	−0.0063 (5)
C13	0.0404 (6)	0.0357 (6)	0.0368 (6)	−0.0037 (5)	−0.0087 (5)	−0.0039 (5)
C14	0.0437 (7)	0.0491 (8)	0.0398 (7)	0.0038 (6)	−0.0156 (6)	−0.0097 (6)
C15	0.0454 (8)	0.0595 (9)	0.0545 (9)	−0.0032 (6)	−0.0232 (7)	−0.0184 (7)
C16	0.0451 (7)	0.0501 (8)	0.0559 (9)	−0.0160 (6)	−0.0157 (7)	−0.0112 (7)
C17	0.0372 (6)	0.0394 (7)	0.0386 (7)	−0.0118 (5)	−0.0087 (5)	−0.0089 (5)
C18	0.0365 (6)	0.0518 (8)	0.0413 (7)	−0.0116 (6)	−0.0090 (5)	−0.0137 (6)
C19	0.0457 (8)	0.0633 (10)	0.0620 (10)	−0.0085 (7)	−0.0085 (7)	−0.0319 (8)
C20	0.0555 (9)	0.0453 (8)	0.0837 (13)	−0.0066 (7)	−0.0129 (9)	−0.0247 (8)
C21	0.0609 (10)	0.0400 (8)	0.0695 (11)	−0.0082 (7)	−0.0171 (8)	−0.0039 (7)
C22	0.0538 (8)	0.0431 (7)	0.0450 (8)	−0.0100 (6)	−0.0110 (6)	−0.0057 (6)

Geometric parameters (Å, º) top

Cl1—C18	1.738 (2)	C7—H7A	0.9700
O1—C9	1.227 (2)	C7—H7B	0.9700
O2—N23	1.204 (2)	C8—H8A	0.9700
O3—N23	1.196 (2)	C8—H8B	0.9700
N1—C8	1.467 (2)	C11—C16	1.379 (2)
N1—C2	1.471 (2)	C11—C12	1.3941 (17)
N1—C5	1.478 (2)	C12—C13	1.3792 (18)
N10—C9	1.345 (2)	C13—C14	1.392 (2)
N10—C11	1.402 (2)	C13—H13	0.9300
N10—H10	0.8600	C14—C15	1.377 (2)
N23—C4	1.508 (2)	C14—H14	0.9300
C2—C12	1.5080 (18)	C15—C16	1.387 (2)
C2—C9	1.5525 (16)	C15—H15	0.9300
C2—C3	1.5562 (18)	C16—H16	0.9300
C3—C17	1.5083 (18)	C17—C22	1.397 (2)
C3—C4	1.5199 (18)	C17—C18	1.3989 (19)
C3—H3	0.9800	C18—C19	1.389 (2)
C4—C5	1.558 (2)	C19—C20	1.373 (3)
C4—H4	0.9800	C19—H19	0.9300
C5—C6	1.538 (2)	C20—C21	1.376 (3)
C5—H5	0.9800	C20—H20	0.9300
C6—C7	1.498 (3)	C21—C22	1.383 (2)
C6—H6A	0.9700	C21—H21	0.9300
C6—H6B	0.9700	C22—H22	0.9300
C7—C8	1.514 (3)

C8—N1—C2	118.2 (1)	N1—C8—C7	102.80 (15)
C8—N1—C5	108.8 (1)	N1—C8—H8A	111.2
C2—N1—C5	108.5 (1)	C7—C8—H8A	111.2
C9—N10—C11	111.65 (11)	N1—C8—H8B	111.2
C9—N10—H10	124.2	C7—C8—H8B	111.2
C11—N10—H10	124.2	H8A—C8—H8B	109.1
O3—N23—O2	123.01 (18)	O1—C9—N10	126.39 (12)
O3—N23—C4	120.45 (15)	O1—C9—C2	125.17 (12)
O2—N23—C4	116.49 (19)	N10—C9—C2	108.41 (11)
N1—C2—C12	117.29 (11)	C16—C11—C12	122.51 (13)
N1—C2—C9	105.63 (10)	C16—C11—N10	127.76 (12)
C12—C2—C9	101.46 (10)	C12—C11—N10	109.71 (11)
N1—C2—C3	104.95 (10)	C13—C12—C11	119.25 (12)
C12—C2—C3	114.32 (10)	C13—C12—C2	131.92 (12)
C9—C2—C3	113.09 (11)	C11—C12—C2	108.71 (11)
C17—C3—C4	117.04 (11)	C12—C13—C14	118.99 (13)
C17—C3—C2	115.72 (10)	C12—C13—H13	120.5
C4—C3—C2	102.03 (10)	C14—C13—H13	120.5
C17—C3—H3	107.1	C15—C14—C13	120.66 (13)
C4—C3—H3	107.1	C15—C14—H14	119.7
C2—C3—H3	107.1	C13—C14—H14	119.7
N23—C4—C3	112.03 (12)	C14—C15—C16	121.40 (14)
N23—C4—C5	111.62 (12)	C14—C15—H15	119.3
C3—C4—C5	105.76 (12)	C16—C15—H15	119.3
N23—C4—H4	109.1	C11—C16—C15	117.19 (14)
C3—C4—H4	109.1	C11—C16—H16	121.4
C5—C4—H4	109.1	C15—C16—H16	121.4
N1—C5—C6	104.77 (14)	C22—C17—C18	116.41 (13)
N1—C5—C4	106.03 (11)	C22—C17—C3	121.41 (12)
C6—C5—C4	118.27 (14)	C18—C17—C3	122.14 (12)
N1—C5—H5	109.1	C19—C18—C17	121.82 (14)
C6—C5—H5	109.1	C19—C18—Cl1	117.13 (12)
C4—C5—H5	109.1	C17—C18—Cl1	121.03 (11)
C7—C6—C5	104.07 (15)	C20—C19—C18	119.88 (15)
C7—C6—H6A	110.9	C20—C19—H19	120.1
C5—C6—H6A	110.9	C18—C19—H19	120.1
C7—C6—H6B	110.9	C19—C20—C21	119.87 (16)
C5—C6—H6B	110.9	C19—C20—H20	120.1
H6A—C6—H6B	109.0	C21—C20—H20	120.1
C6—C7—C8	102.55 (15)	C20—C21—C22	120.14 (16)
C6—C7—H7A	111.3	C20—C21—H21	119.9
C8—C7—H7A	111.3	C22—C21—H21	119.9
C6—C7—H7B	111.3	C21—C22—C17	121.84 (15)
C8—C7—H7B	111.3	C21—C22—H22	119.1
H7A—C7—H7B	109.2	C17—C22—H22	119.1

C8—N1—C2—C12	32.98 (18)	C3—C2—C9—O1	−56.78 (17)
C5—N1—C2—C12	157.28 (11)	N1—C2—C9—N10	−120.78 (12)
C8—N1—C2—C9	145.09 (14)	C12—C2—C9—N10	2.07 (14)
C5—N1—C2—C9	−90.60 (12)	C3—C2—C9—N10	124.98 (12)
C8—N1—C2—C3	−95.15 (15)	C9—N10—C11—C16	−175.86 (14)
C5—N1—C2—C3	29.2 (1)	C9—N10—C11—C12	2.09 (17)
N1—C2—C3—C17	−164.23 (10)	C16—C11—C12—C13	1.1 (2)
C12—C2—C3—C17	65.87 (14)	N10—C11—C12—C13	−177.00 (12)
C9—C2—C3—C17	−49.59 (14)	C16—C11—C12—C2	177.48 (13)
N1—C2—C3—C4	−36.0 (1)	N10—C11—C12—C2	−0.61 (15)
C12—C2—C3—C4	−165.92 (11)	N1—C2—C12—C13	−70.61 (18)
C9—C2—C3—C4	78.63 (12)	C9—C2—C12—C13	174.93 (14)
O3—N23—C4—C3	−23.6 (2)	C3—C2—C12—C13	52.87 (19)
O2—N23—C4—C3	158.91 (19)	N1—C2—C12—C11	113.61 (12)
O3—N23—C4—C5	94.8 (2)	C9—C2—C12—C11	−0.84 (13)
O2—N23—C4—C5	−82.7 (2)	C3—C2—C12—C11	−122.91 (12)
C17—C3—C4—N23	−81.46 (15)	C11—C12—C13—C14	−1.33 (19)
C2—C3—C4—N23	151.17 (12)	C2—C12—C13—C14	−176.75 (13)
C17—C3—C4—C5	156.73 (11)	C12—C13—C14—C15	0.7 (2)
C2—C3—C4—C5	29.4 (1)	C13—C14—C15—C16	0.2 (2)
C8—N1—C5—C6	−6.5 (2)	C12—C11—C16—C15	−0.1 (2)
C2—N1—C5—C6	−136.19 (13)	N10—C11—C16—C15	177.57 (14)
C8—N1—C5—C4	119.35 (13)	C14—C15—C16—C11	−0.5 (2)
C2—N1—C5—C4	−10.4 (1)	C4—C3—C17—C22	−43.94 (17)
N23—C4—C5—N1	−134.97 (13)	C2—C3—C17—C22	76.44 (16)
C3—C4—C5—N1	−12.9 (1)	C4—C3—C17—C18	138.35 (13)
N23—C4—C5—C6	−17.9 (2)	C2—C3—C17—C18	−101.27 (14)
C3—C4—C5—C6	104.22 (16)	C22—C17—C18—C19	−2.1 (2)
N1—C5—C6—C7	−19.4 (2)	C3—C17—C18—C19	175.75 (12)
C4—C5—C6—C7	−137.15 (16)	C22—C17—C18—Cl1	176.32 (10)
C5—C6—C7—C8	37.0 (2)	C3—C17—C18—Cl1	−5.87 (18)
C2—N1—C8—C7	153.58 (13)	C17—C18—C19—C20	1.2 (2)
C5—N1—C8—C7	29.4 (2)	Cl1—C18—C19—C20	−177.28 (13)
C6—C7—C8—N1	−40.9 (2)	C18—C19—C20—C21	0.7 (3)
C11—N10—C9—O1	179.18 (14)	C19—C20—C21—C22	−1.5 (3)
C11—N10—C9—C2	−2.61 (16)	C20—C21—C22—C17	0.6 (3)
N1—C2—C9—O1	57.46 (17)	C18—C17—C22—C21	1.2 (2)
C12—C2—C9—O1	−179.69 (14)	C3—C17—C22—C21	−176.62 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cl1	0.98	2.55	3.108 (1)	116
N10—H10···O1ⁱ	0.86	1.99	2.843 (1)	172

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈ClN₃O₃
M_r	383.82
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.4698 (5), 9.3359 (6), 12.6058 (8)
α, β, γ (°)	74.394 (1), 72.025 (1), 79.334 (1)
V (Å³)	907.49 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.22 × 0.21 × 0.19

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7852, 4067, 3661
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.128, 1.02
No. of reflections	4067
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.23

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

Cl1—C18	1.738 (2)	N1—C2	1.471 (2)
O1—C9	1.227 (2)	N1—C5	1.478 (2)
O2—N23	1.204 (2)	N10—C9	1.345 (2)
O3—N23	1.196 (2)	N10—C11	1.402 (2)
N1—C8	1.467 (2)	N23—C4	1.508 (2)

C8—N1—C2	118.2 (1)	C2—N1—C5	108.5 (1)
C8—N1—C5	108.8 (1)

C5—N1—C2—C3	29.2 (1)	C3—C4—C5—N1	−12.9 (1)
N1—C2—C3—C4	−36.0 (1)	N1—C5—C6—C7	−19.4 (2)
C2—C3—C4—C5	29.4 (1)	C5—C6—C7—C8	37.0 (2)
C8—N1—C5—C6	−6.5 (2)	C5—N1—C8—C7	29.4 (2)
C2—N1—C5—C4	−10.4 (1)	C6—C7—C8—N1	−40.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cl1	0.98	2.55	3.108 (1)	116
N10—H10···O1ⁱ	0.86	1.99	2.843 (1)	172

Symmetry code: (i) −x+1, −y+1, −z.

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