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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805029107/bt6738sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805029107/bt6738Isup2.hkl
Contains datablock I

CCDC reference: 287477

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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 CO double bond is slightly elongated [C9O1 = 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.

Refinement top

H atoms were positioned geometrically and treated as riding on their parent atoms with aromatic C—H distances in the range 0.93–0.97 Å and an N—H distance of 0.86 Å, and with Uiso(H) = 1.5Ueq(C) for methyl H and 1.2Ueq(N,C) for other H atoms.

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 adduct, showing 30% probability displacement ellipsoids.
[Figure 2] 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
C20H19N3O3F(000) = 1472
Mr = 349.38Dx = 1.372 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 7483 reflections
a = 23.8981 (15) Åθ = 2.5–26.5°
b = 7.5886 (4) ŵ = 0.09 mm1
c = 19.137 (1) ÅT = 293 K
β = 102.941 (2)°Block, colourless
V = 3382.4 (3) Å30.23 × 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 tubeRint = 0.018
Graphite monochromatorθmax = 28.0°, θmin = 2.2°
ω scansh = 3031
13982 measured reflectionsk = 99
3921 independent reflectionsl = 2525
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0985P)2 + 1.7117P]
where P = (Fo2 + 2Fc2)/3
3921 reflections(Δ/σ)max < 0.001
235 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
C20H19N3O3V = 3382.4 (3) Å3
Mr = 349.38Z = 8
Monoclinic, C2/cMo Kα radiation
a = 23.8981 (15) ŵ = 0.09 mm1
b = 7.5886 (4) ÅT = 293 K
c = 19.137 (1) Å0.23 × 0.21 × 0.20 mm
β = 102.941 (2)°
Data collection top
CCD Area Detector
diffractometer
3373 reflections with I > 2σ(I)
13982 measured reflectionsRint = 0.018
3921 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.164H-atom parameters constrained
S = 1.03Δρmax = 0.29 e Å3
3921 reflectionsΔρmin = 0.29 e Å3
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
xyzUiso*/Ueq
O10.07159 (5)0.02311 (14)0.06395 (6)0.0512 (3)
O20.27239 (8)0.0114 (4)0.18077 (14)0.1251 (9)
O30.25603 (8)0.2023 (3)0.25370 (12)0.1132 (7)
N10.08805 (5)0.10616 (17)0.21380 (6)0.0436 (3)
N100.00611 (5)0.20074 (17)0.05533 (7)0.0445 (3)
H100.01980.16010.02040.053*
N230.23993 (6)0.0986 (2)0.20513 (10)0.0650 (5)
C20.08624 (6)0.22227 (18)0.15167 (7)0.0371 (3)
C30.15020 (5)0.26078 (18)0.15331 (7)0.0367 (3)
H30.16400.33850.19450.044*
C40.17707 (6)0.0804 (2)0.17411 (8)0.0440 (3)
H40.17180.00780.13080.053*
C50.14116 (7)0.0006 (2)0.22439 (10)0.0518 (4)
H50.13070.12150.20870.062*
C60.16539 (11)0.0018 (5)0.30496 (12)0.1010 (10)
H6A0.17730.11960.32160.121*
H6B0.19810.07670.31770.121*
C70.11687 (10)0.0609 (3)0.33690 (11)0.0705 (5)
H7A0.09120.03520.34190.085*
H7B0.13110.11520.38340.085*
C80.08778 (11)0.1922 (3)0.28300 (9)0.0728 (6)
H8A0.04890.21470.28780.087*
H8B0.10880.30250.28780.087*
C90.05515 (6)0.11579 (18)0.08476 (7)0.0397 (3)
C110.00235 (6)0.3636 (2)0.08866 (8)0.0408 (3)
C120.04882 (6)0.38338 (18)0.14655 (7)0.0380 (3)
C130.05582 (7)0.5407 (2)0.18389 (8)0.0467 (4)
H130.08710.55710.22220.056*
C140.01571 (8)0.6740 (2)0.16365 (9)0.0538 (4)
H140.02010.78030.18840.065*
C150.03060 (8)0.6494 (2)0.10691 (10)0.0584 (4)
H150.05740.73930.09440.070*
C160.03812 (7)0.4937 (2)0.06811 (9)0.0535 (4)
H160.06930.47770.02970.064*
C170.16435 (6)0.3511 (2)0.08923 (7)0.0395 (3)
C180.16935 (7)0.2624 (2)0.02743 (8)0.0492 (4)
H180.16310.14140.02400.059*
C190.18361 (8)0.3528 (3)0.02910 (10)0.0614 (5)
H190.18730.29160.06990.074*
C200.19233 (9)0.5317 (3)0.02532 (11)0.0670 (5)
H200.20190.59140.06350.080*
C210.18695 (9)0.6217 (3)0.03473 (11)0.0682 (5)
H210.19250.74300.03730.082*
C220.17320 (8)0.5322 (2)0.09184 (10)0.0532 (4)
H220.16980.59440.13260.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0497 (6)0.0439 (6)0.0534 (6)0.0012 (4)0.0023 (5)0.0150 (5)
O20.0705 (11)0.176 (2)0.1421 (18)0.0555 (13)0.0530 (12)0.0464 (17)
O30.0751 (11)0.1170 (15)0.1170 (15)0.0209 (10)0.0428 (10)0.0099 (13)
N10.0408 (6)0.0482 (7)0.0400 (6)0.0025 (5)0.0052 (5)0.0009 (5)
N100.0353 (6)0.0497 (7)0.0422 (6)0.0014 (5)0.0046 (5)0.0104 (5)
N230.0434 (8)0.0808 (11)0.0687 (10)0.0111 (7)0.0081 (7)0.0333 (9)
C20.0340 (6)0.0399 (7)0.0346 (6)0.0027 (5)0.0018 (5)0.0052 (5)
C30.0328 (6)0.0391 (7)0.0346 (6)0.0006 (5)0.0000 (5)0.0033 (5)
C40.0415 (7)0.0453 (8)0.0422 (7)0.0049 (6)0.0029 (6)0.0008 (6)
C50.0523 (9)0.0420 (8)0.0613 (10)0.0029 (6)0.0134 (7)0.0091 (7)
C60.0788 (15)0.164 (3)0.0608 (13)0.0419 (17)0.0180 (11)0.0545 (16)
C70.0788 (13)0.0821 (14)0.0485 (10)0.0018 (11)0.0099 (9)0.0132 (9)
C80.0909 (14)0.0873 (14)0.0391 (9)0.0276 (12)0.0122 (9)0.0023 (9)
C90.0370 (7)0.0412 (7)0.0379 (7)0.0053 (5)0.0019 (5)0.0049 (5)
C110.0344 (6)0.0476 (8)0.0392 (7)0.0008 (5)0.0057 (5)0.0041 (6)
C120.0335 (6)0.0420 (7)0.0377 (7)0.0013 (5)0.0061 (5)0.0035 (5)
C130.0455 (8)0.0468 (8)0.0455 (8)0.0013 (6)0.0055 (6)0.0093 (6)
C140.0574 (9)0.0470 (8)0.0583 (9)0.0045 (7)0.0157 (7)0.0102 (7)
C150.0537 (9)0.0587 (10)0.0619 (10)0.0180 (8)0.0112 (8)0.0017 (8)
C160.0401 (8)0.0639 (10)0.0520 (9)0.0101 (7)0.0007 (6)0.0043 (7)
C170.0300 (6)0.0465 (7)0.0389 (7)0.0005 (5)0.0011 (5)0.0002 (6)
C180.0482 (8)0.0521 (9)0.0473 (8)0.0047 (7)0.0107 (6)0.0016 (7)
C190.0563 (10)0.0834 (13)0.0472 (9)0.0093 (9)0.0174 (7)0.0014 (9)
C200.0586 (11)0.0824 (14)0.0624 (11)0.0048 (9)0.0188 (9)0.0193 (10)
C210.0742 (13)0.0576 (10)0.0720 (13)0.0165 (9)0.0145 (10)0.0091 (9)
C220.0552 (9)0.0507 (9)0.0514 (9)0.0113 (7)0.0069 (7)0.0031 (7)
Geometric parameters (Å, º) top
O1—C91.222 (2)C7—H7B0.9700
O2—N231.191 (3)C8—H8A0.9700
O3—N231.213 (3)C8—H8B0.9700
N1—C21.473 (2)C11—C161.376 (2)
N1—C51.481 (2)C11—C121.3901 (19)
N1—C81.478 (2)C12—C131.382 (2)
N10—C91.346 (2)C13—C141.388 (2)
N10—C111.403 (2)C13—H130.9300
N10—H100.8600C14—C151.379 (3)
N23—C41.493 (2)C14—H140.9300
C2—C121.5048 (19)C15—C161.386 (3)
C2—C31.5495 (18)C15—H150.9300
C2—C91.5552 (18)C16—H160.9300
C3—C171.5081 (19)C17—C221.389 (2)
C3—C41.526 (2)C17—C181.389 (2)
C3—H30.9800C18—C191.386 (2)
C4—C51.553 (2)C18—H180.9300
C4—H40.9800C19—C201.373 (3)
C5—C61.521 (3)C19—H190.9300
C5—H50.9800C20—C211.367 (3)
C6—C71.504 (3)C20—H200.9300
C6—H6A0.9700C21—C221.387 (3)
C6—H6B0.9700C21—H210.9300
C7—C81.490 (3)C22—H220.9300
C7—H7A0.9700
C2—N1—C5107.9 (1)N1—C8—C7103.28 (17)
C2—N1—C8117.0 (1)N1—C8—H8A111.1
C5—N1—C8107.2 (1)C7—C8—H8A111.1
C9—N10—C11111.73 (11)N1—C8—H8B111.1
C9—N10—H10124.1C7—C8—H8B111.1
C11—N10—H10124.1H8A—C8—H8B109.1
O2—N23—O3122.5 (2)O1—C9—N10126.18 (13)
O2—N23—C4118.6 (2)O1—C9—C2125.95 (13)
O3—N23—C4118.86 (18)N10—C9—C2107.84 (12)
N1—C2—C12116.64 (11)C16—C11—C12122.37 (14)
N1—C2—C3104.23 (10)C16—C11—N10127.91 (14)
C12—C2—C3114.65 (11)C12—C11—N10109.65 (12)
N1—C2—C9106.03 (11)C13—C12—C11119.19 (13)
C12—C2—C9101.61 (11)C13—C12—C2131.82 (13)
C3—C2—C9113.70 (11)C11—C12—C2108.74 (12)
C17—C3—C4117.51 (12)C12—C13—C14119.28 (14)
C17—C3—C2117.97 (11)C12—C13—H13120.4
C4—C3—C2101.06 (11)C14—C13—H13120.4
C17—C3—H3106.5C15—C14—C13120.26 (15)
C4—C3—H3106.5C15—C14—H14119.9
C2—C3—H3106.5C13—C14—H14119.9
N23—C4—C3110.38 (13)C14—C15—C16121.49 (16)
N23—C4—C5115.90 (13)C14—C15—H15119.3
C3—C4—C5104.96 (12)C16—C15—H15119.3
N23—C4—H4108.5C11—C16—C15117.39 (15)
C3—C4—H4108.5C11—C16—H16121.3
C5—C4—H4108.5C15—C16—H16121.3
N1—C5—C6105.19 (15)C22—C17—C18117.94 (15)
N1—C5—C4105.90 (12)C22—C17—C3118.72 (14)
C6—C5—C4119.52 (17)C18—C17—C3123.34 (13)
N1—C5—H5108.6C19—C18—C17120.51 (16)
C6—C5—H5108.6C19—C18—H18119.7
C4—C5—H5108.6C17—C18—H18119.7
C7—C6—C5104.89 (18)C20—C19—C18120.60 (18)
C7—C6—H6A110.8C20—C19—H19119.7
C5—C6—H6A110.8C18—C19—H19119.7
C7—C6—H6B110.8C21—C20—C19119.76 (18)
C5—C6—H6B110.8C21—C20—H20120.1
H6A—C6—H6B108.8C19—C20—H20120.1
C8—C7—C6102.29 (17)C20—C21—C22120.06 (18)
C8—C7—H7A111.3C20—C21—H21120.0
C6—C7—H7A111.3C22—C21—H21120.0
C8—C7—H7B111.3C21—C22—C17121.12 (17)
C6—C7—H7B111.3C21—C22—H22119.4
H7A—C7—H7B109.2C17—C22—H22119.4
C5—N1—C2—C12159.01 (12)C12—C2—C9—O1175.92 (14)
C8—N1—C2—C1238.21 (18)C3—C2—C9—O152.2 (2)
C5—N1—C2—C331.5 (1)N1—C2—C9—N10116.29 (13)
C8—N1—C2—C389.28 (16)C12—C2—C9—N106.06 (15)
C5—N1—C2—C988.76 (13)C3—C2—C9—N10129.79 (13)
C8—N1—C2—C9150.43 (14)C9—N10—C11—C16172.24 (16)
N1—C2—C3—C17169.54 (11)C9—N10—C11—C124.67 (18)
C12—C2—C3—C1761.76 (16)C16—C11—C12—C131.8 (2)
C9—C2—C3—C1754.55 (16)N10—C11—C12—C13175.29 (13)
N1—C2—C3—C440.0 (1)C16—C11—C12—C2176.78 (14)
C12—C2—C3—C4168.70 (11)N10—C11—C12—C20.33 (16)
C9—C2—C3—C474.99 (13)N1—C2—C12—C1374.5 (2)
O2—N23—C4—C3127.59 (18)C3—C2—C12—C1347.7 (2)
O3—N23—C4—C351.8 (2)C9—C2—C12—C13170.75 (16)
O2—N23—C4—C5113.3 (2)N1—C2—C12—C11111.39 (13)
O3—N23—C4—C567.3 (2)C3—C2—C12—C11126.42 (13)
C17—C3—C4—N2371.17 (16)C9—C2—C12—C113.35 (15)
C2—C3—C4—N23158.99 (13)C11—C12—C13—C141.3 (2)
C17—C3—C4—C5163.27 (12)C2—C12—C13—C14174.85 (15)
C2—C3—C4—C533.4 (1)C12—C13—C14—C150.0 (3)
C2—N1—C5—C6137.50 (17)C13—C14—C15—C160.9 (3)
C8—N1—C5—C610.7 (2)C12—C11—C16—C151.0 (3)
C2—N1—C5—C410.1 (2)N10—C11—C16—C15175.55 (16)
C8—N1—C5—C4116.73 (16)C14—C15—C16—C110.4 (3)
N23—C4—C5—N1137.66 (15)C4—C3—C17—C22140.90 (14)
C3—C4—C5—N115.6 (2)C2—C3—C17—C2297.67 (16)
N23—C4—C5—C619.3 (2)C4—C3—C17—C1838.75 (18)
C3—C4—C5—C6102.70 (19)C2—C3—C17—C1882.68 (17)
N1—C5—C6—C715.2 (3)C22—C17—C18—C191.0 (2)
C4—C5—C6—C7133.9 (2)C3—C17—C18—C19178.69 (14)
C5—C6—C7—C835.0 (3)C17—C18—C19—C200.8 (3)
C2—N1—C8—C7154.05 (16)C18—C19—C20—C210.0 (3)
C5—N1—C8—C732.8 (2)C19—C20—C21—C220.5 (3)
C6—C7—C8—N141.6 (3)C20—C21—C22—C170.4 (3)
C11—N10—C9—O1175.23 (14)C18—C17—C22—C210.4 (2)
C11—N10—C9—C26.76 (16)C3—C17—C22—C21179.29 (16)
N1—C2—C9—O161.72 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6B···O30.972.263.001 (4)133
N10—H10···O1i0.862.082.929 (2)169
C20—H20···O2ii0.932.583.285 (3)133
Symmetry codes: (i) x, y, z; (ii) x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC20H19N3O3
Mr349.38
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)23.8981 (15), 7.5886 (4), 19.137 (1)
β (°) 102.941 (2)
V3)3382.4 (3)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.23 × 0.21 × 0.20
Data collection
DiffractometerCCD Area Detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
13982, 3921, 3373
Rint0.018
(sin θ/λ)max1)0.660
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.164, 1.03
No. of reflections3921
No. of parameters235
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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—C91.222 (2)N1—C81.478 (2)
O2—N231.191 (3)N10—C91.346 (2)
O3—N231.213 (3)N10—C111.403 (2)
N1—C21.473 (2)N23—C41.493 (2)
N1—C51.481 (2)
C2—N1—C5107.9 (1)C5—N1—C8107.2 (1)
C2—N1—C8117.0 (1)
C5—N1—C2—C331.5 (1)C3—C4—C5—N115.6 (2)
N1—C2—C3—C440.0 (1)N1—C5—C6—C715.2 (3)
C2—C3—C4—C533.4 (1)C5—C6—C7—C835.0 (3)
C8—N1—C5—C610.7 (2)C5—N1—C8—C732.8 (2)
C2—N1—C5—C410.1 (2)C6—C7—C8—N141.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6B···O30.972.263.001 (4)133
N10—H10···O1i0.862.082.929 (2)169
C20—H20···O2ii0.932.583.285 (3)133
Symmetry codes: (i) x, y, z; (ii) x+1/2, y+1/2, z.
 

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