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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): o136.
Published online 2008 December 17. doi:  10.1107/S1600536808042098
PMCID: PMC2968054

6-Bromo-1-butylindoline-2,3-dione

Abstract

There are two independent mol­ecules in the asymmetric unit of the title compound, C12H12BrNO2. The C—C bond lengths of the two carbonyl C atoms of the five-membered rings are distinctly longer than a normal Csp 2—Csp 2 single bond. One of the mol­ecules makes parallel self-coupled (inversion) dimers by π–π inter­actions with phen­yl–phenyl inter­planar distances of 3.403 (2) Å. The other mol­ecule also forms self-dimers at longer phen­yl–phenyl plane distances [3.649 (2) Å]. In the crystal, a C—H(...)O interaction is seen.

Related literature

For synthesis and applications, see: Kopka et al. (2006 [triangle]); Pirrung et al. (2005 [triangle]); Zhou et al. (2006 [triangle]). For related crystal structures, see: Goldschmidt & Llewellyn (1950 [triangle]); Palenik et al. (1990 [triangle]).

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Object name is e-65-0o136-scheme1.jpg

Experimental

Crystal data

  • C12H12BrNO2
  • M r = 282.14
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o136-efi1.jpg
  • a = 13.3097 (2) Å
  • b = 11.8793 (2) Å
  • c = 16.2238 (2) Å
  • β = 112.340 (1)°
  • V = 2372.62 (6) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 3.45 mm−1
  • T = 296 (2) K
  • 0.37 × 0.13 × 0.11 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.526, T max = 0.744 (expected range = 0.487–0.689)
  • 16713 measured reflections
  • 5170 independent reflections
  • 2424 reflections with I > 2σ(I)
  • R int = 0.076

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.070
  • S = 0.93
  • 5170 reflections
  • 364 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.39 e Å−3
  • Δρmin = −0.49 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXL97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808042098/cs2100sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042098/cs2100Isup2.hkl

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

Acknowledgments

This work are supported by the PhD Foundation of the Ministry of Education of China and by the National Natural Science Foundation of China (grant No. 50673054).

supplementary crystallographic information

Comment

Isatin, 2,3-indolinedione is traditionally obtained from oxidation of oxindole and indigo blue. Its derivates have long been used as precursors of medicines and reductive dyes (Zhou et al., 2006; Pirrung et al., 2005; Kopka et al., 2006). The first crystal structure report on isatin was by Goldschmidt and Llewellyn, 1950. Here we report the crystal structure of N-butyl-6-bromoisatin. There are two independent molecules in the asymmetric unit with very similar bond parameters. Except for the fused aromatic bond of C3[equals, single dot above]C8 in one molecule and C23[equals, single dot above]C28 bond in the other molecule, four other bonds in the five-membered heterocyclic rings can be classified as single C—C bonds and π-conjugated C[equals, single dot above]N bonds. The C1—C2 (1.545 (4) Å) and C21—C22 (1.558 (4) Å) bond lengths are longer than expected for a C(sp2)-C(sp2) single bond. This may be the result of the repulsion of the lone pair electrons of the two oxygen atoms in cis-diones (Palenik et al., 1990). Nitrogen atoms and their three bonded carbons are perfectly co-planar, showing that the sp2 N atoms allocate two pz electrons for π-bonding. The bond lengths of the π-conjugated N[equals, single dot above]C bonds (c.f. Table 1) are much shorter than a single C—N bond length. Molecules are packed in dimers (Figure 2). One kind of the independent molecules are linked through a symmetry center to form dimer stack A while two other molecules form another dimer stack B. Mean planes of A and B dimers have a dihedral angle of 85.8 (1)°. The phenyl-phenyl spacing (3.40 (1) Å) in A dimers is considerably shorter than the spacing (3.65 (1) Å) in teh B dimers, indicating relatively stronger intermolecular π-π interactions between these A molecules. The intermolecular interactions in dimer A are further strengthened by C–Br short contacts. The C1···Br1[-x+1, -y+1, -z] and C2···Br1[-x+1, -y+1, -z] in dimer A are 3.476 (3) Å and 3.538 (3) Å, respectively. By comparison, the corresponding C···Br contacts in dimer B are much longer with the shortest distance being 3.672 (4) Å for C22···Br2[-x+1, -y+1, -z]. It may be the result of these different C···Br contacts that the C1—C2 bond length in dimer A is marginally shorter than the C21—C22 bond in dimer B. Amongst intermolecular C—H···O hydrogen bonds the strongest is the C7—H7···O3 one between dimers A and B (see Table 2).

Experimental

6-Bromoisatin (10.5 g) was dissolved in 100 ml DMSO in a three-necked flask. Then KI (3.50 g), cetyltrimethyl ammonium bromide (1.00 g), and KOH (30.0 g) in 20.0 g water were added. Then 40.0 ml of n-bromobutane was added drop-wise into the above mixture with stirring. The mixture was stirred at 343 K for 2 days under nitrogen protection. The reaction mixture was washed by water, extracted with CHCl3, then the chloroform layer was dried by Na2SO4. After vaporizing the solvent, the crude product was purified by column chromatography, resulting in 9.5 g (yield 71%) N-butyl-6-bromoisatin product. The compound was dissolved in chloroform again. On most of the solvent evaporating at room temperature orange lump title crystals were formed.

Refinement

All H atoms except those on the methyl groups were initially found in difference electron density syntheses and were used in the least-squares refinement. Six H atoms on two terminal methyls could also be located in the difference maps but some H—C bond parameters in the methyl groups became unreasonable. So HFIX 137 instructions were used to restrain the methyl H-positions.

Figures

Fig. 1.
Two N-butyl-6-bromoisatin molecules in the asymmetric unit with 30% probability displacement ellipsoids
Fig. 2.
The molecular packing of the crystal showing the dimer structure [symmetry code: (i)-x+1, -y+1, -z]

Crystal data

C12H12BrNO2F(000) = 1136
Mr = 282.14Dx = 1.580 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3677 reflections
a = 13.3097 (2) Åθ = 2.2–23.8°
b = 11.8793 (2) ŵ = 3.45 mm1
c = 16.2238 (2) ÅT = 296 K
β = 112.340 (1)°Plank, orange
V = 2372.62 (6) Å30.37 × 0.13 × 0.11 mm
Z = 8

Data collection

Bruker APEXII CCD diffractometer5170 independent reflections
Radiation source: fine-focus sealed tube2424 reflections with I > 2σ(I)
graphiteRint = 0.076
Detector resolution: 10.0 pixels mm-1θmax = 27.0°, θmin = 1.7°
phi and ω scansh = −16→17
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −15→10
Tmin = 0.526, Tmax = 0.744l = −20→20
16713 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.070w = 1/[σ2(Fo2) + (0.0158P)2] where P = (Fo2 + 2Fc2)/3
S = 0.93(Δ/σ)max = 0.001
5170 reflectionsΔρmax = 0.39 e Å3
364 parametersΔρmin = −0.49 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00147 (12)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Br10.25474 (2)0.52247 (4)0.03130 (3)0.07546 (17)
O10.82928 (15)0.3064 (2)0.18511 (13)0.0649 (7)
O20.82426 (16)0.5497 (2)0.22161 (15)0.0682 (7)
N10.64300 (18)0.3303 (3)0.12570 (15)0.0448 (7)
C10.7490 (2)0.3648 (3)0.1675 (2)0.0477 (9)
C20.7445 (2)0.4919 (3)0.18633 (19)0.0475 (9)
C30.6286 (2)0.5203 (3)0.15321 (19)0.0431 (9)
C40.5754 (3)0.6195 (4)0.1517 (2)0.0519 (10)
H40.616 (2)0.688 (3)0.1810 (18)0.058 (10)*
C50.4628 (3)0.6193 (4)0.1150 (2)0.0535 (10)
H50.4240 (19)0.690 (3)0.1167 (16)0.047 (9)*
C60.4095 (2)0.5211 (4)0.0815 (2)0.0476 (9)
C70.4595 (2)0.4196 (4)0.0807 (2)0.0435 (9)
H70.4227 (18)0.351 (2)0.0576 (16)0.036 (9)*
C80.5720 (2)0.4213 (3)0.11826 (18)0.0382 (8)
C90.6102 (3)0.2182 (3)0.0965 (3)0.0504 (10)
H9A0.538 (2)0.218 (3)0.040 (2)0.073 (10)*
H9B0.659 (2)0.185 (3)0.081 (2)0.078 (13)*
C100.5921 (3)0.1458 (4)0.1651 (3)0.0640 (11)
H10B0.537 (2)0.185 (2)0.1859 (17)0.052 (9)*
H10A0.658 (2)0.147 (3)0.221 (2)0.070 (11)*
C110.5557 (4)0.0275 (4)0.1272 (3)0.0831 (14)
H11A0.613 (3)−0.012 (3)0.121 (2)0.100*
H11B0.477 (3)0.032 (3)0.085 (2)0.100*
C120.5496 (3)−0.0541 (4)0.1927 (3)0.1061 (15)
H12A0.6201−0.06280.23920.138 (10)*
H12B0.5253−0.12530.16410.138 (10)*
H12C0.4993−0.02760.21790.138 (10)*
Br20.25658 (2)−0.10901 (4)0.09621 (3)0.07726 (17)
O3−0.32733 (16)−0.1957 (2)0.03877 (14)0.0728 (8)
O4−0.30063 (18)−0.2190 (2)−0.13304 (15)0.0795 (8)
N2−0.14314 (18)−0.1581 (2)0.08915 (16)0.0493 (7)
C21−0.2438 (3)−0.1837 (3)0.0266 (2)0.0550 (10)
C22−0.2278 (3)−0.1969 (3)−0.0632 (2)0.0538 (9)
C23−0.1117 (2)−0.1769 (3)−0.0404 (2)0.0446 (8)
C24−0.0483 (3)−0.1808 (3)−0.0900 (3)0.0552 (10)
H24−0.084 (2)−0.193 (3)−0.1480 (19)0.060 (11)*
C250.0612 (3)−0.1618 (3)−0.0495 (3)0.0599 (10)
H250.1067 (18)−0.164 (2)−0.0805 (16)0.035 (8)*
C260.1047 (2)−0.1379 (3)0.0399 (2)0.0513 (9)
C270.0439 (2)−0.1332 (3)0.0925 (2)0.0501 (10)
H270.0727 (17)−0.120 (2)0.1503 (16)0.034 (9)*
C28−0.0653 (2)−0.1544 (3)0.0505 (2)0.0443 (8)
C29−0.1191 (3)−0.1497 (4)0.1850 (2)0.0545 (11)
H29A−0.1731 (19)−0.188 (2)0.1991 (16)0.045 (9)*
H29B−0.056 (2)−0.198 (3)0.2144 (19)0.068 (11)*
C30−0.1031 (3)−0.0315 (4)0.2208 (3)0.0592 (11)
H30B−0.049 (2)0.010 (3)0.200 (2)0.077 (11)*
H30A−0.162 (2)0.016 (3)0.195 (2)0.067 (12)*
C31−0.0728 (4)−0.0318 (4)0.3219 (3)0.0771 (13)
H31B−0.002 (3)−0.071 (3)0.355 (2)0.112 (17)*
H31A−0.133 (3)−0.073 (3)0.333 (2)0.103 (14)*
C32−0.0463 (3)0.0819 (4)0.3617 (2)0.0941 (14)
H32A0.01220.11320.34830.129 (9)*
H32B−0.02490.07660.42520.129 (9)*
H32C−0.10900.12950.33760.129 (9)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.03753 (19)0.1118 (4)0.0741 (3)0.0122 (2)0.01790 (17)0.0168 (3)
O10.0405 (12)0.082 (2)0.0631 (16)0.0147 (13)0.0090 (11)−0.0007 (14)
O20.0450 (13)0.081 (2)0.0662 (16)−0.0181 (13)0.0076 (12)−0.0127 (15)
N10.0369 (14)0.046 (2)0.0473 (17)−0.0027 (15)0.0110 (12)−0.0079 (17)
C10.0397 (19)0.060 (3)0.039 (2)−0.0006 (19)0.0107 (16)0.001 (2)
C20.0372 (17)0.062 (3)0.038 (2)−0.0066 (19)0.0086 (15)0.003 (2)
C30.0376 (17)0.049 (3)0.038 (2)−0.0040 (19)0.0091 (15)−0.005 (2)
C40.056 (2)0.045 (3)0.051 (2)−0.007 (2)0.0165 (18)−0.006 (2)
C50.053 (2)0.051 (3)0.056 (2)0.010 (2)0.0202 (19)0.002 (2)
C60.0317 (16)0.069 (3)0.039 (2)0.006 (2)0.0095 (15)0.005 (2)
C70.0361 (18)0.049 (3)0.042 (2)−0.008 (2)0.0114 (16)−0.003 (2)
C80.0375 (17)0.044 (2)0.0305 (18)0.0009 (18)0.0100 (14)0.0031 (18)
C90.052 (2)0.043 (3)0.053 (3)0.005 (2)0.016 (2)−0.007 (2)
C100.072 (3)0.050 (3)0.064 (3)−0.009 (2)0.019 (2)−0.004 (3)
C110.087 (3)0.075 (4)0.077 (3)−0.005 (3)0.020 (3)0.003 (3)
C120.121 (4)0.080 (4)0.107 (4)−0.018 (3)0.032 (3)−0.006 (4)
Br20.0453 (2)0.0909 (4)0.0969 (3)0.0008 (2)0.0285 (2)−0.0097 (3)
O30.0427 (12)0.090 (2)0.0790 (17)−0.0143 (13)0.0160 (12)−0.0119 (15)
O40.0672 (15)0.094 (2)0.0514 (16)−0.0202 (15)−0.0066 (13)−0.0106 (16)
N20.0385 (14)0.070 (2)0.0342 (16)−0.0056 (14)0.0078 (12)−0.0067 (16)
C210.048 (2)0.059 (3)0.049 (2)−0.008 (2)0.0089 (18)−0.010 (2)
C220.055 (2)0.042 (3)0.052 (2)−0.0093 (19)0.0065 (18)−0.004 (2)
C230.0489 (19)0.043 (2)0.036 (2)−0.0037 (17)0.0100 (17)−0.0023 (19)
C240.072 (3)0.050 (3)0.036 (2)−0.003 (2)0.012 (2)−0.003 (2)
C250.069 (3)0.063 (3)0.059 (3)0.007 (2)0.036 (2)0.003 (2)
C260.0444 (18)0.050 (3)0.057 (2)0.0006 (17)0.0175 (18)−0.001 (2)
C270.0423 (19)0.064 (3)0.038 (2)0.0006 (18)0.0095 (18)−0.006 (2)
C280.0395 (17)0.050 (2)0.038 (2)−0.0023 (16)0.0089 (16)−0.0028 (19)
C290.048 (2)0.070 (3)0.048 (2)−0.007 (2)0.0202 (19)−0.004 (2)
C300.057 (2)0.064 (3)0.058 (3)−0.006 (2)0.023 (2)−0.008 (3)
C310.103 (4)0.076 (4)0.065 (3)−0.021 (3)0.046 (3)−0.020 (3)
C320.116 (3)0.101 (4)0.076 (3)−0.027 (3)0.048 (2)−0.029 (3)

Geometric parameters (Å, °)

Br1—C61.906 (3)Br2—C261.907 (3)
O1—C11.214 (3)O3—C211.209 (3)
O2—C21.210 (3)O4—C221.208 (3)
N1—C11.375 (3)N2—C211.373 (3)
N1—C81.411 (4)N2—C281.401 (3)
N1—C91.425 (4)N2—C291.467 (4)
C1—C21.545 (4)C21—C221.558 (4)
C2—C31.468 (4)C22—C231.465 (4)
C3—C41.370 (4)C23—C241.370 (4)
C3—C81.395 (4)C23—C281.391 (4)
C4—C51.387 (4)C24—C251.371 (4)
C4—H40.99 (3)C24—H240.89 (3)
C5—C61.366 (4)C25—C261.372 (4)
C5—H51.00 (3)C25—H250.92 (2)
C6—C71.379 (4)C26—C271.382 (4)
C7—C81.386 (4)C27—C281.374 (4)
C7—H70.95 (3)C27—H270.88 (2)
C9—C101.496 (5)C29—C301.503 (5)
C9—H9A1.05 (3)C29—H29A0.95 (3)
C9—H9B0.87 (3)C29—H29B0.98 (3)
C10—C111.536 (6)C30—C311.532 (5)
C10—H10B1.03 (3)C30—H30B1.04 (3)
C10—H10A0.99 (3)C30—H30A0.93 (3)
C11—C121.464 (6)C31—C321.481 (5)
C11—H11A0.94 (4)C31—H31B1.00 (4)
C11—H11B1.01 (3)C31—H31A1.01 (4)
C12—H12A0.9600C32—H32A0.9600
C12—H12B0.9600C32—H32B0.9600
C12—H12C0.9600C32—H32C0.9600
C1—N1—C8110.0 (3)C21—N2—C28110.9 (2)
C1—N1—C9124.8 (3)C21—N2—C29123.9 (3)
C8—N1—C9125.3 (3)C28—N2—C29124.9 (2)
O1—C1—N1126.3 (3)O3—C21—N2127.2 (3)
O1—C1—C2127.4 (3)O3—C21—C22127.0 (3)
N1—C1—C2106.3 (3)N2—C21—C22105.7 (3)
O2—C2—C3130.8 (4)O4—C22—C23131.7 (3)
O2—C2—C1123.8 (3)O4—C22—C21123.5 (3)
C3—C2—C1105.5 (3)C23—C22—C21104.7 (3)
C4—C3—C8121.5 (3)C24—C23—C28120.3 (3)
C4—C3—C2132.0 (3)C24—C23—C22132.2 (3)
C8—C3—C2106.5 (3)C28—C23—C22107.4 (3)
C3—C4—C5118.2 (4)C23—C24—C25119.6 (3)
C3—C4—H4120.7 (16)C23—C24—H24115.6 (18)
C5—C4—H4120.8 (16)C25—C24—H24124.7 (19)
C6—C5—C4119.1 (4)C24—C25—C26119.0 (3)
C6—C5—H5122.6 (15)C24—C25—H25122.3 (15)
C4—C5—H5118.3 (15)C26—C25—H25118.7 (15)
C5—C6—C7124.8 (3)C25—C26—C27123.4 (3)
C5—C6—Br1118.4 (3)C25—C26—Br2119.2 (3)
C7—C6—Br1116.8 (3)C27—C26—Br2117.4 (3)
C6—C7—C8115.3 (3)C28—C27—C26116.3 (3)
C6—C7—H7125.2 (15)C28—C27—H27120.7 (16)
C8—C7—H7119.5 (15)C26—C27—H27123.0 (16)
C7—C8—C3121.1 (3)C27—C28—C23121.4 (3)
C7—C8—N1127.1 (3)C27—C28—N2127.3 (3)
C3—C8—N1111.8 (3)C23—C28—N2111.3 (2)
N1—C9—C10113.9 (3)N2—C29—C30114.5 (3)
N1—C9—H9A110.8 (17)N2—C29—H29A110.0 (15)
C10—C9—H9A107.0 (17)C30—C29—H29A111.5 (17)
N1—C9—H9B111 (2)N2—C29—H29B106.1 (17)
C10—C9—H9B108 (2)C30—C29—H29B112.8 (18)
H9A—C9—H9B106 (3)H29A—C29—H29B101 (2)
C9—C10—C11110.1 (4)C29—C30—C31110.6 (4)
C9—C10—H10B108.8 (16)C29—C30—H30B109.3 (18)
C11—C10—H10B112.8 (16)C31—C30—H30B115.0 (17)
C9—C10—H10A109.7 (18)C29—C30—H30A115 (2)
C11—C10—H10A114.1 (19)C31—C30—H30A109 (2)
H10B—C10—H10A101 (2)H30B—C30—H30A98 (3)
C12—C11—C10114.3 (4)C32—C31—C30112.8 (4)
C12—C11—H11A91 (3)C32—C31—H31B100 (2)
C10—C11—H11A111 (2)C30—C31—H31B113 (2)
C12—C11—H11B101 (2)C32—C31—H31A116 (2)
C10—C11—H11B108 (2)C30—C31—H31A107 (2)
H11A—C11—H11B129 (3)H31B—C31—H31A109 (3)
C11—C12—H12A109.5C31—C32—H32A109.5
C11—C12—H12B109.5C31—C32—H32B109.5
H12A—C12—H12B109.5H32A—C32—H32B109.5
C11—C12—H12C109.5C31—C32—H32C109.5
H12A—C12—H12C109.5H32A—C32—H32C109.5
H12B—C12—H12C109.5H32B—C32—H32C109.5
C8—N1—C1—O1179.0 (3)C28—N2—C21—O3178.2 (4)
C9—N1—C1—O10.6 (5)C29—N2—C21—O35.0 (6)
C8—N1—C1—C2−1.6 (3)C28—N2—C21—C22−0.5 (4)
C9—N1—C1—C2180.0 (3)C29—N2—C21—C22−173.6 (3)
O1—C1—C2—O20.6 (5)O3—C21—C22—O41.8 (6)
N1—C1—C2—O2−178.8 (3)N2—C21—C22—O4−179.6 (3)
O1—C1—C2—C3−179.3 (3)O3—C21—C22—C23−178.2 (3)
N1—C1—C2—C31.3 (3)N2—C21—C22—C230.4 (3)
O2—C2—C3—C40.2 (6)O4—C22—C23—C24−2.7 (7)
C1—C2—C3—C4−180.0 (3)C21—C22—C23—C24177.3 (4)
O2—C2—C3—C8179.6 (3)O4—C22—C23—C28179.8 (4)
C1—C2—C3—C8−0.5 (3)C21—C22—C23—C28−0.2 (4)
C8—C3—C4—C50.7 (5)C28—C23—C24—C25−0.3 (5)
C2—C3—C4—C5180.0 (3)C22—C23—C24—C25−177.6 (4)
C3—C4—C5—C6−0.5 (5)C23—C24—C25—C26−0.8 (5)
C4—C5—C6—C7−0.2 (5)C24—C25—C26—C270.8 (6)
C4—C5—C6—Br1−179.9 (2)C24—C25—C26—Br2−179.0 (3)
C5—C6—C7—C80.8 (5)C25—C26—C27—C280.2 (5)
Br1—C6—C7—C8−179.6 (2)Br2—C26—C27—C28−180.0 (2)
C6—C7—C8—C3−0.6 (4)C26—C27—C28—C23−1.3 (5)
C6—C7—C8—N1−179.6 (3)C26—C27—C28—N2177.9 (3)
C4—C3—C8—C7−0.1 (5)C24—C23—C28—C271.4 (5)
C2—C3—C8—C7−179.6 (3)C22—C23—C28—C27179.3 (3)
C4—C3—C8—N1179.1 (3)C24—C23—C28—N2−177.9 (3)
C2—C3—C8—N1−0.4 (3)C22—C23—C28—N20.0 (4)
C1—N1—C8—C7−179.6 (3)C21—N2—C28—C27−179.0 (3)
C9—N1—C8—C7−1.2 (5)C29—N2—C28—C27−5.9 (5)
C1—N1—C8—C31.3 (3)C21—N2—C28—C230.3 (4)
C9—N1—C8—C3179.7 (3)C29—N2—C28—C23173.4 (3)
C1—N1—C9—C1089.8 (4)C21—N2—C29—C30−106.6 (4)
C8—N1—C9—C10−88.3 (4)C28—N2—C29—C3081.2 (4)
N1—C9—C10—C11179.3 (3)N2—C29—C30—C31−177.1 (3)
C9—C10—C11—C12172.4 (4)C29—C30—C31—C32174.8 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C7—H7···O3i0.95 (3)2.44 (3)3.367 (5)165 (2)

Symmetry codes: (i) −x, −y, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CS2100).

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