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Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): o1162.
Published online 2008 May 30. doi:  10.1107/S1600536808015626
PMCID: PMC2961414

2-Amino-4′-bromo-2′,5-dioxo-4H,5H-pyrano[3,2-c]chromene-4-spiro-3′(2′H)-1′H-indole-3-carbonitrile N,N-dimethyl­formamide solvate

Abstract

In the mol­ecule of the title compound, C20H10BrN3O4·C3H7NO, the spiro pyran ring adopts a twist conformation. The indole and coumarin ring systems are each nearly planar, and are oriented at a dihedral angle of 79.29 (3)°. In the crystal structure, inter­molecular N—H(...)O, N—H(...)N, C—H(...)O and C—H(...)N hydrogen bonds link the mol­ecules.

Related literature

For general background, see: da Silva et al. (2001 [triangle]); Joshi & Chand (1982 [triangle]); Abdel-Rahman et al. (2004 [triangle]); Zhu et al. (2007 [triangle]). For ring-puckering parameters, see: Cremer & Pople (1975 [triangle]).

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Object name is e-64-o1162-scheme1.jpg

Experimental

Crystal data

  • C20H10BrN3O4·C3H7NO
  • M r = 509.32
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1162-efi1.jpg
  • a = 17.004 (3) Å
  • b = 9.0452 (15) Å
  • c = 14.415 (3) Å
  • β = 108.340 (3)°
  • V = 2104.5 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.00 mm−1
  • T = 153 (2) K
  • 0.45 × 0.30 × 0.20 mm

Data collection

  • Rigaku Mercury diffractometer
  • Absorption correction: multi-scan (Jacobson, 1998 [triangle]) T min = 0.434, T max = 0.670
  • 19919 measured reflections
  • 3847 independent reflections
  • 3597 reflections with I > 2σ(I)
  • R int = 0.031

Refinement

  • R[F 2 > 2σ(F 2)] = 0.031
  • wR(F 2) = 0.067
  • S = 1.09
  • 3847 reflections
  • 309 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.56 e Å−3
  • Δρmin = −0.38 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2001 [triangle]); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEPII (Johnson, 1976 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808015626/hk2467sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015626/hk2467Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was partially supported by the Natural Science Foundation of Jiangsu Province (grant No. BK2006048), the National Natural Science Foundation of China (grant No. 20672079) and a research grant from the Innovation Project for Graduate Students of Jiangsu Province.

supplementary crystallographic information

Comment

The indole nucleus is the well known heterocycle (da-Silva et al., 2001). Compounds carrying the indole moiety exhibit antibacterial and fungicidal activities (Joshi & Chand, 1982). Spirooxindole ring systems are found in a number of alkaloids like horsifiline, spirotryprostatin and elacomine (Abdel-Rahman et al., 2004). As a part of our programme devoted to the preparation of heterocyclic compounds involving indole derivatives (Zhu et al., 2007), we have synthesized a series of spirooxindoles via reactions of substituted isatins together with malononitrile and 4-hydroxycoumarin in water. We report herein the crystal structure of the title compound, (I).

In the molecule of (I), (Fig. 1), rings B (N3/C3/C7/C8/C13), C (C8-C13), D (O3/C4/C5/C14/C15/C20) and E (C15-C20) are, of course, planar. The dihedral angles between them are B/C = 1.51 (3)° and D/E = 4.24 (3)°. So, rings B, C and D,E are nearly coplanar. The coplanar ring systems are oriented at a dihedral angle of 79.29 (3)°. Ring A (O1/C1-C5) adopts twisted conformation, having total puckering amplitude, QT, of 0.122 (3) Å (Cremer & Pople, 1975).

In the crystal structure, intermolecular N-H···O, N-H···N, C-H···O and C-H···N hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure.

Experimental

Compound (I) was prepared by the reaction of 4-bromoisatin (1 mmol), malononitrile (1 mmol) and 4-hydroxycoumarin (1 mmol) in water (5 ml). The reaction was catalyzed by TEBAC (triethylbenzylammonium chloride, 1 mmol). After stirring at 333 K for 5 h, the reaction mixture was cooled and washed with small amount of ethanol. The crude product was filtered and single crystals of the title compound were obtained from DMF solution by slow evaporation at room temperature (yield; 80%, m.p. > 573 K). Spectroscopic analysis: IR (KBr, n, cm-1): 3372, 3310, 3179, 2192, 1728, 1674, 1605, 1450, 1358, 1234, 1111, 1080, 972, 910, 872, 764, 578. 1H NMR (400 MHz, DMSO-d6): 10.99 (s, 1H, NH), 7.96 (d, 1H, J = 7.6 Hz, ArH), 7.84 (br s, 2H, NH2), 7.79 (t, 1H, J = 8.4 Hz, ArH), 7.53–7.59 (m, 2H, ArH), 7.21 (t, 1H, J = 8.0 Hz, ArH), 7.12 (d, 1H, J = 8.0 Hz, ArH), 6.91 (d, 1H, J = 7.6 Hz, ArH).

Refinement

H atoms (for NH2) were located in a difference syntheses and refined [N-H = 0.89 (3) and 0.84 (3) Å; Uiso(H) = 0.022 (7) and 0.018 (6) Å2]. The remaining H atoms were positioned geometrically, with N-H = 0.88 Å (for NH) and C-H = 0.95 and 0.98 Å for aromatic and methyl H and constrained to ride on their parent atoms with Uiso(H) = xUeq(C,N), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level.
Fig. 2.
A packing diagram of (I). Hydrogen bonds are shown as dashed lines.

Crystal data

C20H10BrN3O4·C3H7NOF000 = 1032
Mr = 509.32Dx = 1.607 Mg m3
Monoclinic, P21/cMelting point > 573 K
Hall symbol: -P 2 y b cMo Kα radiation λ = 0.71070 Å
a = 17.004 (3) ÅCell parameters from 7931 reflections
b = 9.0452 (15) Åθ = 3.2–25.3º
c = 14.415 (3) ŵ = 2.00 mm1
β = 108.340 (3)ºT = 153 (2) K
V = 2104.5 (7) Å3Block, colorless
Z = 40.45 × 0.30 × 0.20 mm

Data collection

Rigaku Mercury diffractometer3847 independent reflections
Radiation source: fine-focus sealed tube3597 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.031
Detector resolution: 7.31 pixels mm-1θmax = 25.3º
T = 153(2) Kθmin = 3.2º
ω scansh = −17→20
Absorption correction: multi-scan(Jacobson, 1998)k = −10→9
Tmin = 0.434, Tmax = 0.670l = −17→17
19919 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.067  w = 1/[σ2(Fo2) + (0.0219P)2 + 2.2795P] where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.002
3847 reflectionsΔρmax = 0.56 e Å3
309 parametersΔρmin = −0.38 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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 > 2sigma(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)

xyzUiso*/Ueq
Br10.674546 (15)−0.23487 (3)0.370899 (16)0.02528 (8)
O10.72297 (9)0.17427 (16)0.38347 (10)0.0165 (3)
O20.80028 (9)0.17370 (16)0.69972 (11)0.0195 (3)
O30.54289 (9)0.16195 (17)0.51984 (11)0.0205 (3)
O40.61528 (9)0.00093 (17)0.62894 (11)0.0218 (3)
O50.86929 (11)0.5130 (2)0.42641 (12)0.0350 (4)
N10.84875 (12)0.1416 (2)0.37211 (14)0.0165 (4)
H1A0.8332 (15)0.211 (3)0.3263 (19)0.022 (7)*
H1B0.8976 (16)0.110 (3)0.3921 (17)0.018 (6)*
N20.97044 (12)−0.0393 (2)0.58997 (14)0.0245 (4)
N30.80382 (11)−0.07714 (19)0.72793 (13)0.0170 (4)
H30.8267−0.07670.79180.020*
N40.94175 (11)0.5142 (2)0.58794 (13)0.0216 (4)
C10.79982 (12)0.1140 (2)0.42627 (15)0.0135 (4)
C20.81869 (12)0.0379 (2)0.51188 (15)0.0135 (4)
C30.75548 (12)−0.0029 (2)0.56233 (15)0.0132 (4)
C40.67684 (12)0.0815 (2)0.51288 (15)0.0135 (4)
C50.66610 (13)0.1649 (2)0.43275 (15)0.0143 (4)
C60.90223 (13)−0.0065 (2)0.55498 (15)0.0159 (4)
C70.78839 (12)0.0454 (2)0.67200 (15)0.0154 (4)
C80.74743 (12)−0.1686 (2)0.57294 (15)0.0140 (4)
C90.71969 (13)−0.2801 (2)0.50567 (15)0.0166 (4)
C100.72305 (14)−0.4273 (2)0.53575 (17)0.0206 (5)
H100.7035−0.50390.48910.025*
C110.75512 (14)−0.4604 (2)0.63403 (18)0.0229 (5)
H110.7577−0.56070.65430.027*
C120.78381 (13)−0.3505 (2)0.70414 (17)0.0199 (5)
H120.8059−0.37390.77160.024*
C130.77895 (13)−0.2058 (2)0.67179 (15)0.0153 (4)
C140.61196 (13)0.0753 (2)0.55878 (15)0.0168 (5)
C150.53467 (13)0.2528 (2)0.44043 (16)0.0178 (5)
C160.46555 (14)0.3429 (3)0.41187 (18)0.0247 (5)
H160.42520.33890.44480.030*
C170.45632 (14)0.4387 (3)0.33474 (18)0.0264 (5)
H170.40970.50260.31530.032*
C180.51418 (14)0.4430 (3)0.28502 (17)0.0240 (5)
H180.50660.50870.23150.029*
C190.58252 (13)0.3522 (2)0.31330 (16)0.0195 (5)
H190.62200.35500.27910.023*
C200.59384 (13)0.2557 (2)0.39248 (15)0.0156 (4)
C210.90376 (15)0.5775 (3)0.50259 (18)0.0290 (6)
H210.90340.68250.50070.035*
C220.98163 (16)0.6027 (3)0.67431 (19)0.0330 (6)
H22A0.97250.70790.65810.050*
H22B1.04120.58210.69680.050*
H22C0.95800.57770.72620.050*
C230.94561 (18)0.3560 (3)0.6002 (2)0.0376 (7)
H23A0.90970.32570.63820.056*
H23B1.00280.32640.63470.056*
H23C0.92700.30820.53590.056*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.03215 (15)0.02519 (14)0.01580 (13)−0.00378 (10)0.00365 (10)−0.00394 (9)
O10.0129 (7)0.0220 (8)0.0152 (8)0.0032 (6)0.0053 (6)0.0050 (6)
O20.0243 (8)0.0164 (8)0.0170 (8)−0.0025 (6)0.0051 (7)−0.0043 (6)
O30.0157 (8)0.0256 (9)0.0225 (8)0.0047 (6)0.0095 (7)0.0063 (7)
O40.0234 (8)0.0243 (9)0.0204 (8)0.0027 (7)0.0110 (7)0.0059 (7)
O50.0318 (10)0.0512 (12)0.0194 (9)0.0038 (9)0.0042 (8)−0.0030 (8)
N10.0130 (10)0.0197 (10)0.0172 (10)0.0038 (8)0.0051 (8)0.0054 (8)
N20.0193 (11)0.0316 (12)0.0235 (10)0.0053 (9)0.0079 (9)0.0070 (9)
N30.0199 (10)0.0187 (10)0.0105 (9)0.0003 (8)0.0022 (7)0.0023 (7)
N40.0205 (10)0.0256 (11)0.0180 (10)−0.0003 (8)0.0051 (8)0.0019 (8)
C10.0119 (10)0.0122 (10)0.0160 (10)−0.0005 (8)0.0037 (8)−0.0037 (8)
C20.0129 (10)0.0137 (11)0.0139 (10)0.0000 (8)0.0043 (8)−0.0003 (8)
C30.0137 (10)0.0142 (11)0.0119 (10)−0.0009 (8)0.0045 (8)−0.0006 (8)
C40.0131 (10)0.0135 (10)0.0133 (10)−0.0008 (8)0.0034 (8)−0.0025 (8)
C50.0141 (10)0.0153 (11)0.0143 (10)−0.0015 (8)0.0055 (8)−0.0040 (8)
C60.0216 (12)0.0145 (11)0.0140 (11)−0.0012 (9)0.0089 (9)0.0020 (8)
C70.0122 (10)0.0194 (12)0.0151 (11)0.0003 (8)0.0051 (9)0.0014 (9)
C80.0121 (10)0.0137 (11)0.0179 (11)0.0012 (8)0.0070 (9)0.0016 (8)
C90.0137 (10)0.0213 (11)0.0158 (11)0.0000 (9)0.0063 (9)−0.0006 (9)
C100.0195 (11)0.0158 (11)0.0290 (13)−0.0023 (9)0.0112 (10)−0.0042 (9)
C110.0224 (12)0.0145 (11)0.0356 (14)0.0031 (9)0.0146 (11)0.0060 (10)
C120.0191 (11)0.0201 (12)0.0222 (12)0.0030 (9)0.0090 (10)0.0061 (9)
C130.0133 (10)0.0172 (11)0.0167 (11)0.0013 (8)0.0064 (9)0.0009 (9)
C140.0161 (11)0.0160 (11)0.0172 (11)0.0000 (9)0.0036 (9)−0.0026 (9)
C150.0163 (11)0.0187 (11)0.0175 (11)−0.0012 (9)0.0042 (9)0.0002 (9)
C160.0181 (12)0.0276 (13)0.0312 (13)0.0031 (10)0.0117 (10)0.0008 (10)
C170.0180 (12)0.0272 (13)0.0313 (13)0.0085 (10)0.0041 (10)0.0050 (10)
C180.0186 (12)0.0263 (13)0.0237 (12)0.0025 (10)0.0016 (10)0.0071 (10)
C190.0179 (11)0.0212 (12)0.0182 (11)0.0009 (9)0.0040 (9)0.0015 (9)
C200.0131 (10)0.0158 (11)0.0159 (11)−0.0019 (8)0.0018 (9)−0.0014 (8)
C210.0244 (13)0.0374 (15)0.0263 (14)0.0049 (11)0.0097 (11)0.0008 (11)
C220.0299 (14)0.0340 (15)0.0299 (14)0.0011 (11)0.0017 (11)−0.0052 (11)
C230.0446 (17)0.0293 (15)0.0357 (15)−0.0074 (12)0.0078 (13)0.0020 (12)

Geometric parameters (Å, °)

Br1—C91.895 (2)C8—C91.376 (3)
O1—C11.370 (2)C8—C131.396 (3)
O1—C51.371 (2)C9—C101.395 (3)
O2—C71.223 (3)C10—C111.381 (3)
O3—C141.376 (3)C10—H100.9500
O3—C151.380 (3)C11—C121.392 (3)
O4—C141.201 (3)C11—H110.9500
O5—C211.219 (3)C12—C131.383 (3)
N1—C11.331 (3)C12—H120.9500
N1—H1A0.89 (3)C15—C161.382 (3)
N1—H1B0.84 (3)C15—C201.389 (3)
N2—C61.149 (3)C16—C171.379 (3)
N3—C71.347 (3)C16—H160.9500
N3—C131.404 (3)C17—C181.388 (3)
N3—H30.8800C17—H170.9500
N4—C211.326 (3)C18—C191.376 (3)
N4—C231.441 (3)C18—H180.9500
N4—C221.456 (3)C19—C201.401 (3)
C1—C21.360 (3)C19—H190.9500
C2—C61.418 (3)C21—H210.9500
C2—C31.521 (3)C22—H22A0.9800
C3—C41.509 (3)C22—H22B0.9800
C3—C81.517 (3)C22—H22C0.9800
C3—C71.564 (3)C23—H23A0.9800
C4—C51.343 (3)C23—H23B0.9800
C4—C141.455 (3)C23—H23C0.9800
C5—C201.440 (3)
C1—O1—C5118.06 (16)C12—C11—H11119.2
C14—O3—C15121.88 (16)C13—C12—C11117.5 (2)
C1—N1—H1A118.2 (16)C13—C12—H12121.3
C1—N1—H1B118.0 (16)C11—C12—H12121.3
H1A—N1—H1B122 (2)C12—C13—C8122.3 (2)
C7—N3—C13111.74 (17)C12—C13—N3127.9 (2)
C7—N3—H3124.1C8—C13—N3109.74 (18)
C13—N3—H3124.1O4—C14—O3118.06 (19)
C21—N4—C23122.2 (2)O4—C14—C4124.3 (2)
C21—N4—C22121.1 (2)O3—C14—C4117.68 (18)
C23—N4—C22116.8 (2)O3—C15—C16116.93 (19)
N1—C1—C2127.9 (2)O3—C15—C20121.61 (19)
N1—C1—O1110.17 (18)C16—C15—C20121.4 (2)
C2—C1—O1121.94 (18)C17—C16—C15118.8 (2)
C1—C2—C6117.31 (18)C17—C16—H16120.6
C1—C2—C3123.80 (18)C15—C16—H16120.6
C6—C2—C3118.89 (18)C16—C17—C18121.0 (2)
C4—C3—C8116.89 (17)C16—C17—H17119.5
C4—C3—C2107.82 (17)C18—C17—H17119.5
C8—C3—C2112.82 (17)C19—C18—C17120.0 (2)
C4—C3—C7108.55 (16)C19—C18—H18120.0
C8—C3—C7100.89 (16)C17—C18—H18120.0
C2—C3—C7109.49 (16)C18—C19—C20120.0 (2)
C5—C4—C14119.68 (19)C18—C19—H19120.0
C5—C4—C3123.41 (18)C20—C19—H19120.0
C14—C4—C3116.85 (18)C15—C20—C19118.8 (2)
C4—C5—O1123.57 (19)C15—C20—C5116.64 (19)
C4—C5—C20122.36 (19)C19—C20—C5124.40 (19)
O1—C5—C20114.06 (18)O5—C21—N4125.8 (3)
N2—C6—C2178.5 (2)O5—C21—H21117.1
O2—C7—N3127.16 (19)N4—C21—H21117.1
O2—C7—C3124.40 (19)N4—C22—H22A109.5
N3—C7—C3108.38 (17)N4—C22—H22B109.5
C9—C8—C13118.63 (19)H22A—C22—H22B109.5
C9—C8—C3132.46 (19)N4—C22—H22C109.5
C13—C8—C3108.84 (18)H22A—C22—H22C109.5
C8—C9—C10120.6 (2)H22B—C22—H22C109.5
C8—C9—Br1120.17 (16)N4—C23—H23A109.5
C10—C9—Br1119.23 (16)N4—C23—H23B109.5
C11—C10—C9119.3 (2)H23A—C23—H23B109.5
C11—C10—H10120.3N4—C23—H23C109.5
C9—C10—H10120.3H23A—C23—H23C109.5
C10—C11—C12121.7 (2)H23B—C23—H23C109.5
C10—C11—H11119.2
C5—O1—C1—N1−175.77 (17)C13—C8—C9—Br1178.87 (15)
C5—O1—C1—C24.4 (3)C3—C8—C9—Br1−4.6 (3)
N1—C1—C2—C66.6 (3)C8—C9—C10—C11−0.4 (3)
O1—C1—C2—C6−173.60 (18)Br1—C9—C10—C11−179.33 (16)
N1—C1—C2—C3−172.6 (2)C9—C10—C11—C120.4 (3)
O1—C1—C2—C37.1 (3)C10—C11—C12—C130.1 (3)
C1—C2—C3—C4−11.5 (3)C11—C12—C13—C8−0.6 (3)
C6—C2—C3—C4169.26 (18)C11—C12—C13—N3−179.9 (2)
C1—C2—C3—C8119.1 (2)C9—C8—C13—C120.5 (3)
C6—C2—C3—C8−60.1 (2)C3—C8—C13—C12−176.78 (19)
C1—C2—C3—C7−129.4 (2)C9—C8—C13—N3179.94 (18)
C6—C2—C3—C751.3 (2)C3—C8—C13—N32.6 (2)
C8—C3—C4—C5−122.6 (2)C7—N3—C13—C12−178.8 (2)
C2—C3—C4—C55.7 (3)C7—N3—C13—C81.8 (2)
C7—C3—C4—C5124.3 (2)C15—O3—C14—O4178.80 (19)
C8—C3—C4—C1460.4 (2)C15—O3—C14—C4−0.4 (3)
C2—C3—C4—C14−171.33 (17)C5—C4—C14—O4178.0 (2)
C7—C3—C4—C14−52.8 (2)C3—C4—C14—O4−4.8 (3)
C14—C4—C5—O1−178.31 (18)C5—C4—C14—O3−2.9 (3)
C3—C4—C5—O14.7 (3)C3—C4—C14—O3174.33 (17)
C14—C4—C5—C203.2 (3)C14—O3—C15—C16−175.4 (2)
C3—C4—C5—C20−173.79 (19)C14—O3—C15—C203.4 (3)
C1—O1—C5—C4−10.4 (3)O3—C15—C16—C17178.0 (2)
C1—O1—C5—C20168.17 (17)C20—C15—C16—C17−0.8 (3)
C13—N3—C7—O2177.2 (2)C15—C16—C17—C181.3 (4)
C13—N3—C7—C3−5.3 (2)C16—C17—C18—C19−0.8 (4)
C4—C3—C7—O2−52.7 (3)C17—C18—C19—C20−0.2 (3)
C8—C3—C7—O2−176.1 (2)O3—C15—C20—C19−178.96 (19)
C2—C3—C7—O264.8 (3)C16—C15—C20—C19−0.2 (3)
C4—C3—C7—N3129.72 (18)O3—C15—C20—C5−3.0 (3)
C8—C3—C7—N36.3 (2)C16—C15—C20—C5175.7 (2)
C2—C3—C7—N3−112.82 (19)C18—C19—C20—C150.7 (3)
C4—C3—C8—C960.5 (3)C18—C19—C20—C5−174.9 (2)
C2—C3—C8—C9−65.3 (3)C4—C5—C20—C15−0.3 (3)
C7—C3—C8—C9177.9 (2)O1—C5—C20—C15−178.91 (18)
C4—C3—C8—C13−122.70 (19)C4—C5—C20—C19175.4 (2)
C2—C3—C8—C13111.45 (19)O1—C5—C20—C19−3.2 (3)
C7—C3—C8—C13−5.3 (2)C23—N4—C21—O5−0.7 (4)
C13—C8—C9—C100.0 (3)C22—N4—C21—O5179.4 (2)
C3—C8—C9—C10176.5 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.89 (3)2.02 (3)2.891 (2)165 (2)
N1—H1B···N2ii0.84 (3)2.27 (3)3.090 (3)166 (2)
N3—H3···O5iii0.881.932.785 (2)163
C11—H11···O2iv0.952.543.462 (3)165
C19—H19···O4i0.952.503.173 (3)128
C22—H22A···N2v0.982.483.443 (3)166

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2467).

References

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