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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805028990/bt6737sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805028990/bt6737Isup2.hkl
Contains datablock I

CCDC reference: 287476

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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 C9O1 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 [ΔS(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.

Refinement top

H atoms were positioned geometrically and were treated as riding on their parent atoms, with C—H distances of 0.93–0.98 Å, an N—H distance of 0.86 Å and Uiso(H) = 1.2Ueq(N,C). Please check changes to text.

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
[Figure 1] Fig. 1. The molecular structure of title compound, showing 30% probability displacement ellipsoids.
[Figure 2] 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
C20H18ClN3O3Z = 2
Mr = 383.82F(000) = 400
Triclinic, P1Dx = 1.405 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.4698 (5) ÅCell parameters from 5235 reflections
b = 9.3359 (6) Åθ = 2.2–27.2°
c = 12.6058 (8) ŵ = 0.24 mm1
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 tubeRint = 0.016
Graphite monochromatorθmax = 28.0°, θmin = 1.7°
ω scansh = 1111
7852 measured reflectionsk = 1211
4067 independent reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0795P)2 + 0.1853P]
where P = (Fo2 + 2Fc2)/3
4067 reflections(Δ/σ)max < 0.001
244 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
C20H18ClN3O3γ = 79.334 (1)°
Mr = 383.82V = 907.49 (10) Å3
Triclinic, P1Z = 2
a = 8.4698 (5) ÅMo Kα radiation
b = 9.3359 (6) ŵ = 0.24 mm1
c = 12.6058 (8) ÅT = 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 reflectionsRint = 0.016
4067 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.128H-atom parameters constrained
S = 1.02Δρmax = 0.31 e Å3
4067 reflectionsΔρmin = 0.23 e Å3
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
xyzUiso*/Ueq
Cl10.05788 (5)0.23832 (5)0.49497 (3)0.05686 (15)
O10.34666 (14)0.36659 (12)0.01487 (8)0.0473 (3)
O20.1362 (3)0.0653 (3)0.1201 (2)0.1259 (8)
O30.1325 (2)0.0243 (2)0.29225 (15)0.0917 (5)
N10.36516 (15)0.06695 (13)0.16276 (10)0.0418 (3)
N100.46895 (15)0.40243 (13)0.14350 (10)0.0441 (3)
H100.52280.47640.10080.053*
N230.0761 (2)0.07547 (19)0.19242 (16)0.0648 (4)
C20.30473 (16)0.20214 (13)0.20889 (10)0.0347 (3)
C30.11091 (16)0.20958 (14)0.24386 (10)0.0352 (3)
H30.07840.13490.31580.042*
C40.08125 (19)0.15147 (16)0.15075 (12)0.0442 (3)
H40.07300.23530.08570.053*
C50.2389 (2)0.04150 (17)0.11284 (13)0.0484 (3)
H50.28070.06670.02910.058*
C60.2247 (3)0.1275 (2)0.1541 (2)0.0742 (6)
H6A0.12750.14790.21890.089*
H6B0.21700.16870.09320.089*
C70.3826 (3)0.1915 (2)0.18785 (18)0.0668 (5)
H7A0.47480.20540.12170.080*
H7B0.36910.28640.24320.080*
C80.4092 (3)0.07268 (17)0.24016 (17)0.0596 (4)
H8A0.33690.07920.31740.072*
H8B0.52450.08130.24160.072*
C90.37309 (17)0.33404 (15)0.10935 (11)0.0381 (3)
C110.47039 (16)0.33828 (15)0.25740 (12)0.0385 (3)
C120.37553 (15)0.21774 (14)0.30077 (11)0.0346 (3)
C130.35386 (17)0.14260 (15)0.41373 (12)0.0390 (3)
H130.28910.06320.44460.047*
C140.43042 (18)0.18739 (17)0.48078 (13)0.0445 (3)
H140.41760.13680.55680.053*
C150.52490 (19)0.30589 (19)0.43563 (14)0.0502 (4)
H150.57530.33380.48180.060*
C160.54646 (19)0.38455 (18)0.32274 (14)0.0487 (3)
H160.60960.46510.29240.058*
C170.01671 (16)0.35786 (15)0.26425 (11)0.0378 (3)
C180.05603 (17)0.38292 (17)0.37443 (12)0.0421 (3)
C190.1332 (2)0.5225 (2)0.39248 (16)0.0545 (4)
H190.17880.53660.46670.065*
C200.1420 (2)0.63970 (19)0.30064 (18)0.0608 (4)
H200.19260.73350.31250.073*
C210.0760 (2)0.61806 (18)0.19109 (17)0.0584 (4)
H210.08430.69680.12890.070*
C220.0027 (2)0.47949 (17)0.17329 (14)0.0481 (3)
H220.04760.46690.09870.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0541 (2)0.0758 (3)0.0341 (2)0.00738 (19)0.00593 (16)0.00883 (17)
O10.0621 (6)0.0484 (6)0.0300 (5)0.0245 (5)0.0068 (4)0.0010 (4)
O20.1121 (15)0.186 (2)0.1263 (17)0.0626 (15)0.0561 (13)0.0535 (16)
O30.0855 (10)0.1058 (12)0.0854 (11)0.0629 (10)0.0084 (9)0.0262 (9)
N10.0485 (6)0.0362 (6)0.0387 (6)0.0116 (5)0.0023 (5)0.0115 (5)
N100.0515 (7)0.0419 (6)0.0376 (6)0.0247 (5)0.0072 (5)0.0005 (5)
N230.0569 (8)0.0706 (10)0.0828 (11)0.0212 (7)0.0197 (8)0.0333 (9)
C20.0420 (6)0.0310 (6)0.0292 (6)0.0131 (5)0.0044 (5)0.0037 (5)
C30.0412 (6)0.0346 (6)0.0303 (6)0.0142 (5)0.0067 (5)0.0046 (5)
C40.0544 (8)0.0439 (7)0.0391 (7)0.0185 (6)0.0129 (6)0.0084 (6)
C50.0603 (9)0.0485 (8)0.0392 (7)0.0180 (7)0.0052 (6)0.0163 (6)
C60.0850 (14)0.0489 (9)0.0995 (16)0.0191 (9)0.0214 (12)0.0309 (10)
C70.0799 (12)0.0416 (8)0.0730 (12)0.0080 (8)0.0031 (10)0.0228 (8)
C80.0760 (11)0.0370 (8)0.0640 (10)0.0019 (7)0.0183 (9)0.0125 (7)
C90.0436 (7)0.0353 (6)0.0320 (6)0.0136 (5)0.0025 (5)0.0050 (5)
C110.0370 (6)0.0381 (6)0.0392 (7)0.0091 (5)0.0080 (5)0.0064 (5)
C120.0347 (6)0.0332 (6)0.0343 (6)0.0060 (5)0.0070 (5)0.0063 (5)
C130.0404 (6)0.0357 (6)0.0368 (6)0.0037 (5)0.0087 (5)0.0039 (5)
C140.0437 (7)0.0491 (8)0.0398 (7)0.0038 (6)0.0156 (6)0.0097 (6)
C150.0454 (8)0.0595 (9)0.0545 (9)0.0032 (6)0.0232 (7)0.0184 (7)
C160.0451 (7)0.0501 (8)0.0559 (9)0.0160 (6)0.0157 (7)0.0112 (7)
C170.0372 (6)0.0394 (7)0.0386 (7)0.0118 (5)0.0087 (5)0.0089 (5)
C180.0365 (6)0.0518 (8)0.0413 (7)0.0116 (6)0.0090 (5)0.0137 (6)
C190.0457 (8)0.0633 (10)0.0620 (10)0.0085 (7)0.0085 (7)0.0319 (8)
C200.0555 (9)0.0453 (8)0.0837 (13)0.0066 (7)0.0129 (9)0.0247 (8)
C210.0609 (10)0.0400 (8)0.0695 (11)0.0082 (7)0.0171 (8)0.0039 (7)
C220.0538 (8)0.0431 (7)0.0450 (8)0.0100 (6)0.0110 (6)0.0057 (6)
Geometric parameters (Å, º) top
Cl1—C181.738 (2)C7—H7A0.9700
O1—C91.227 (2)C7—H7B0.9700
O2—N231.204 (2)C8—H8A0.9700
O3—N231.196 (2)C8—H8B0.9700
N1—C81.467 (2)C11—C161.379 (2)
N1—C21.471 (2)C11—C121.3941 (17)
N1—C51.478 (2)C12—C131.3792 (18)
N10—C91.345 (2)C13—C141.392 (2)
N10—C111.402 (2)C13—H130.9300
N10—H100.8600C14—C151.377 (2)
N23—C41.508 (2)C14—H140.9300
C2—C121.5080 (18)C15—C161.387 (2)
C2—C91.5525 (16)C15—H150.9300
C2—C31.5562 (18)C16—H160.9300
C3—C171.5083 (18)C17—C221.397 (2)
C3—C41.5199 (18)C17—C181.3989 (19)
C3—H30.9800C18—C191.389 (2)
C4—C51.558 (2)C19—C201.373 (3)
C4—H40.9800C19—H190.9300
C5—C61.538 (2)C20—C211.376 (3)
C5—H50.9800C20—H200.9300
C6—C71.498 (3)C21—C221.383 (2)
C6—H6A0.9700C21—H210.9300
C6—H6B0.9700C22—H220.9300
C7—C81.514 (3)
C8—N1—C2118.2 (1)N1—C8—C7102.80 (15)
C8—N1—C5108.8 (1)N1—C8—H8A111.2
C2—N1—C5108.5 (1)C7—C8—H8A111.2
C9—N10—C11111.65 (11)N1—C8—H8B111.2
C9—N10—H10124.2C7—C8—H8B111.2
C11—N10—H10124.2H8A—C8—H8B109.1
O3—N23—O2123.01 (18)O1—C9—N10126.39 (12)
O3—N23—C4120.45 (15)O1—C9—C2125.17 (12)
O2—N23—C4116.49 (19)N10—C9—C2108.41 (11)
N1—C2—C12117.29 (11)C16—C11—C12122.51 (13)
N1—C2—C9105.63 (10)C16—C11—N10127.76 (12)
C12—C2—C9101.46 (10)C12—C11—N10109.71 (11)
N1—C2—C3104.95 (10)C13—C12—C11119.25 (12)
C12—C2—C3114.32 (10)C13—C12—C2131.92 (12)
C9—C2—C3113.09 (11)C11—C12—C2108.71 (11)
C17—C3—C4117.04 (11)C12—C13—C14118.99 (13)
C17—C3—C2115.72 (10)C12—C13—H13120.5
C4—C3—C2102.03 (10)C14—C13—H13120.5
C17—C3—H3107.1C15—C14—C13120.66 (13)
C4—C3—H3107.1C15—C14—H14119.7
C2—C3—H3107.1C13—C14—H14119.7
N23—C4—C3112.03 (12)C14—C15—C16121.40 (14)
N23—C4—C5111.62 (12)C14—C15—H15119.3
C3—C4—C5105.76 (12)C16—C15—H15119.3
N23—C4—H4109.1C11—C16—C15117.19 (14)
C3—C4—H4109.1C11—C16—H16121.4
C5—C4—H4109.1C15—C16—H16121.4
N1—C5—C6104.77 (14)C22—C17—C18116.41 (13)
N1—C5—C4106.03 (11)C22—C17—C3121.41 (12)
C6—C5—C4118.27 (14)C18—C17—C3122.14 (12)
N1—C5—H5109.1C19—C18—C17121.82 (14)
C6—C5—H5109.1C19—C18—Cl1117.13 (12)
C4—C5—H5109.1C17—C18—Cl1121.03 (11)
C7—C6—C5104.07 (15)C20—C19—C18119.88 (15)
C7—C6—H6A110.9C20—C19—H19120.1
C5—C6—H6A110.9C18—C19—H19120.1
C7—C6—H6B110.9C19—C20—C21119.87 (16)
C5—C6—H6B110.9C19—C20—H20120.1
H6A—C6—H6B109.0C21—C20—H20120.1
C6—C7—C8102.55 (15)C20—C21—C22120.14 (16)
C6—C7—H7A111.3C20—C21—H21119.9
C8—C7—H7A111.3C22—C21—H21119.9
C6—C7—H7B111.3C21—C22—C17121.84 (15)
C8—C7—H7B111.3C21—C22—H22119.1
H7A—C7—H7B109.2C17—C22—H22119.1
C8—N1—C2—C1232.98 (18)C3—C2—C9—O156.78 (17)
C5—N1—C2—C12157.28 (11)N1—C2—C9—N10120.78 (12)
C8—N1—C2—C9145.09 (14)C12—C2—C9—N102.07 (14)
C5—N1—C2—C990.60 (12)C3—C2—C9—N10124.98 (12)
C8—N1—C2—C395.15 (15)C9—N10—C11—C16175.86 (14)
C5—N1—C2—C329.2 (1)C9—N10—C11—C122.09 (17)
N1—C2—C3—C17164.23 (10)C16—C11—C12—C131.1 (2)
C12—C2—C3—C1765.87 (14)N10—C11—C12—C13177.00 (12)
C9—C2—C3—C1749.59 (14)C16—C11—C12—C2177.48 (13)
N1—C2—C3—C436.0 (1)N10—C11—C12—C20.61 (15)
C12—C2—C3—C4165.92 (11)N1—C2—C12—C1370.61 (18)
C9—C2—C3—C478.63 (12)C9—C2—C12—C13174.93 (14)
O3—N23—C4—C323.6 (2)C3—C2—C12—C1352.87 (19)
O2—N23—C4—C3158.91 (19)N1—C2—C12—C11113.61 (12)
O3—N23—C4—C594.8 (2)C9—C2—C12—C110.84 (13)
O2—N23—C4—C582.7 (2)C3—C2—C12—C11122.91 (12)
C17—C3—C4—N2381.46 (15)C11—C12—C13—C141.33 (19)
C2—C3—C4—N23151.17 (12)C2—C12—C13—C14176.75 (13)
C17—C3—C4—C5156.73 (11)C12—C13—C14—C150.7 (2)
C2—C3—C4—C529.4 (1)C13—C14—C15—C160.2 (2)
C8—N1—C5—C66.5 (2)C12—C11—C16—C150.1 (2)
C2—N1—C5—C6136.19 (13)N10—C11—C16—C15177.57 (14)
C8—N1—C5—C4119.35 (13)C14—C15—C16—C110.5 (2)
C2—N1—C5—C410.4 (1)C4—C3—C17—C2243.94 (17)
N23—C4—C5—N1134.97 (13)C2—C3—C17—C2276.44 (16)
C3—C4—C5—N112.9 (1)C4—C3—C17—C18138.35 (13)
N23—C4—C5—C617.9 (2)C2—C3—C17—C18101.27 (14)
C3—C4—C5—C6104.22 (16)C22—C17—C18—C192.1 (2)
N1—C5—C6—C719.4 (2)C3—C17—C18—C19175.75 (12)
C4—C5—C6—C7137.15 (16)C22—C17—C18—Cl1176.32 (10)
C5—C6—C7—C837.0 (2)C3—C17—C18—Cl15.87 (18)
C2—N1—C8—C7153.58 (13)C17—C18—C19—C201.2 (2)
C5—N1—C8—C729.4 (2)Cl1—C18—C19—C20177.28 (13)
C6—C7—C8—N140.9 (2)C18—C19—C20—C210.7 (3)
C11—N10—C9—O1179.18 (14)C19—C20—C21—C221.5 (3)
C11—N10—C9—C22.61 (16)C20—C21—C22—C170.6 (3)
N1—C2—C9—O157.46 (17)C18—C17—C22—C211.2 (2)
C12—C2—C9—O1179.69 (14)C3—C17—C22—C21176.62 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···Cl10.982.553.108 (1)116
N10—H10···O1i0.861.992.843 (1)172
Symmetry code: (i) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC20H18ClN3O3
Mr383.82
Crystal system, space groupTriclinic, 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)
V3)907.49 (10)
Z2
Radiation typeMo Kα
µ (mm1)0.24
Crystal size (mm)0.22 × 0.21 × 0.19
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
7852, 4067, 3661
Rint0.016
(sin θ/λ)max1)0.661
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.128, 1.02
No. of reflections4067
No. of parameters244
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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—C181.738 (2)N1—C21.471 (2)
O1—C91.227 (2)N1—C51.478 (2)
O2—N231.204 (2)N10—C91.345 (2)
O3—N231.196 (2)N10—C111.402 (2)
N1—C81.467 (2)N23—C41.508 (2)
C8—N1—C2118.2 (1)C2—N1—C5108.5 (1)
C8—N1—C5108.8 (1)
C5—N1—C2—C329.2 (1)C3—C4—C5—N112.9 (1)
N1—C2—C3—C436.0 (1)N1—C5—C6—C719.4 (2)
C2—C3—C4—C529.4 (1)C5—C6—C7—C837.0 (2)
C8—N1—C5—C66.5 (2)C5—N1—C8—C729.4 (2)
C2—N1—C5—C410.4 (1)C6—C7—C8—N140.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···Cl10.982.553.108 (1)116
N10—H10···O1i0.861.992.843 (1)172
Symmetry code: (i) x+1, y+1, z.
 

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