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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): o2243.
Published online 2010 August 11. doi:  10.1107/S1600536810030618
PMCID: PMC3008017

2-(2,3-Dioxoindolin-1-yl)ethyl 4-(4-nitro­phen­yl)piperazine-1-carbodithio­ate

Abstract

In the title compound, C21H20N4O4S2, the piperazine ring adopts a chair conformation. The 1-ethyl­indoline-2,3-dione system links to one N atom of the piperazine ring via a carbodithio­ate group. The indoline-2,3-dione ring and the nitro­benzene ring subtend adihedral angle of 37.27 (7)°. In the crystal structure, weak C—H(...)O and π–π stacking inter­actions [centroid–centroid distances = 3.534 (5) and 3.797 (5) Å] may help to establish the packing.

Related literature

For the fungicidal activity of dithio­carbamates, see: Farghaly et al. (1999 [triangle]); Xu et al. (2002 [triangle]); Ozkirimli et al. (2005 [triangle]) and for their anti­bacterial activity, see: Chourasia et al. (1999 [triangle]); Imamura et al. (2001 [triangle]). For the effective anti­tumor activity of dithio­carbamates, see: Cao et al. (2005 [triangle]); Gaspari et al. (2006 [triangle]). For a description of the Cambridge Structural Database, see: Allen (2002 [triangle]).

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Object name is e-66-o2243-scheme1.jpg

Experimental

Crystal data

  • C21H20N4O4S2
  • M r = 456.53
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2243-efi1.jpg
  • a = 34.4244 (8) Å
  • b = 6.8754 (2) Å
  • c = 17.9938 (4) Å
  • β = 103.185 (1)°
  • V = 4146.53 (18) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.29 mm−1
  • T = 296 K
  • 0.15 × 0.13 × 0.10 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • 25340 measured reflections
  • 5843 independent reflections
  • 4309 reflections with I > 2σ(I)
  • R int = 0.027

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.107
  • S = 1.03
  • 5843 reflections
  • 280 parameters
  • H-atom parameters constrained
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: APEX2 and SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (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: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810030618/zq2052sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030618/zq2052Isup2.hkl

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

Acknowledgments

This work was supported by the National Natural Science Foundation of China (project No. 20972099) and the Beijing Municipal Commission of Education (project No. KM200710028008).

supplementary crystallographic information

Comment

Dithiocarbamates represent a broad spectrum of biological activities such as fungicidal (Farghaly et al., 1999; Xu et al., 2002; Ozkirimli et al., 2005) and antibacterial effects (Chourasia et al., 1999; Imamura et al., 2001). Dithiocarbamates were also proved to have in vitro and in vivo effective antitumor activities (Cao et al., 2005; Gaspari et al., 2006). In an effort to obtain new and more potent antibacterial and antitumor compounds, we synthesized the title compound, a kind of novel dithiocarbamate derivative. Here, we report the crystal structure of the title compound.

The X-ray crystal analysis shown that the piperazine ring adopts a chair conformation. The indole-2,3-dione ring and the nitrobenzene ring exhibit a dihedral angle of 37.27 (7)° (Fig.1). Considering the molecule with a U shape conformation, two molecules arrange in a face-to-face mode interacting through intermolecular hydrogen bonding (C13—H13···O2i (nitro) = 2.52 Å, D···A 3.252 (2) Å, D—H···A 136.2°). The dimers are further stacked through π–π and C—H···O intermolecular interactions: C5—H5···O3ii (dione) = 2.33 Å (D···A 3.125 (1) Å, D—H···A 143.3°) and the centroid-centroid distance between the C1—C2—C3—C4—C5—C6 (benzene) and C11iii—C16iii—C17iii—C18iii—N4iii (pyrrole) rings is 3.534 (5) Å, and the distance between the C1—C2—C3—C4—C5—C6 (benzene) and C11iii—C12iii—C13iii—C14iii—C15iii—C16iii rings is 3.797 (5) Å. The packing structure is shown along the a axis in Fig.2 [symmetry codes: (i) –x+0.5, -y + 1/2, -z + 1; (ii) x, -y + 2, z + 1/2; (iii) x, -y + 1, z + 1/2].

Experimental

A suspension of 1-(4-nitrophenyl) piperazine (2.4 mmol), carbon disulfide (0.72 ml,12 mmol) and anhydrous potassium phosphate (0.51 g, 2.4 mmol) in N,N-dimethylformamide (15 ml) was stirred at room temperature for 30 min. Then, 1-(2-bromoethyl) indoline-2,3-dione (2 mmol) was added and the stirring was continued for 30 min. The reaction mixture was poured into water (100 ml) and the resulting precipitate was separated by filtration and purified by column chromatography (CC) on silica gel with dichloromethane/methanol = 95:5, v/v, as an eluent, to give the title compound (Rf = 0.79, dichloromethane/methanol = 95:5, v/v; m.p. 252–254°C; yield 90.6%). The orange crystals of the title compound were obtained by slow evaporation from a solution of dichloromethane/N,N-dimethylformamide 50:50 (v/v) at room temperature.

Refinement

All the H atoms were discernible in the difference electron density maps. Nevertheless, the hydrogen atoms were placed into idealized positions and allowed to ride on the carrier atoms, with C—H = 0.93 and 0.97 Å for aryl and methylene H atoms, respectively, and with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The title molecule with the atomic numbering scheme. The displacement ellipsoids are shown at the 50% probability level.
Fig. 2.
The packing structure of the title compound. The red dashed lines indicate the intermolecular C—H···O interactions, while the π–π stacking interactions are omitted for clarity.

Crystal data

C21H20N4O4S2F(000) = 1904
Mr = 456.53Dx = 1.463 Mg m3Dm = 1.463 Mg m3Dm measured by not measured
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 34.4244 (8) ÅCell parameters from 8247 reflections
b = 6.8754 (2) Åθ = 2.3–29.2°
c = 17.9938 (4) ŵ = 0.29 mm1
β = 103.185 (1)°T = 296 K
V = 4146.53 (18) Å3Block, orange
Z = 80.15 × 0.13 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer4309 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.027
graphiteθmax = 29.8°, θmin = 2.3°
phi and ω scansh = −45→48
25340 measured reflectionsk = −9→7
5843 independent reflectionsl = −24→22

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0528P)2 + 1.1993P] where P = (Fo2 + 2Fc2)/3
5843 reflections(Δ/σ)max < 0.001
280 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = −0.18 e Å3

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 > 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)

xyzUiso*/Ueq
C10.22169 (4)0.0960 (3)0.55107 (9)0.0525 (4)
C20.20345 (5)−0.0339 (3)0.49616 (10)0.0586 (4)
H20.2133−0.15970.49600.070*
C30.17055 (5)0.0221 (2)0.44143 (9)0.0522 (4)
H30.1585−0.06640.40420.063*
C40.15485 (4)0.2101 (2)0.44084 (8)0.0418 (3)
C50.17505 (5)0.3391 (3)0.49705 (9)0.0529 (4)
H50.16600.46640.49740.063*
C60.20780 (5)0.2823 (3)0.55145 (10)0.0561 (4)
H60.22050.37000.58840.067*
C70.10263 (5)0.1336 (2)0.32661 (9)0.0469 (3)
H7A0.10460.00090.34530.056*
H7B0.11750.14260.28700.056*
C80.05960 (5)0.1827 (2)0.29344 (9)0.0476 (3)
H8A0.04930.09910.25000.057*
H8B0.04410.15950.33130.057*
C90.07011 (5)0.5142 (2)0.33419 (8)0.0499 (4)
H9A0.05440.49550.37210.060*
H9B0.06730.64870.31750.060*
C100.11353 (5)0.4710 (2)0.36929 (9)0.0509 (4)
H10A0.12950.50700.33350.061*
H10B0.12220.54930.41490.061*
C110.12259 (4)0.8667 (2)0.12798 (7)0.0400 (3)
C120.13746 (5)0.7170 (3)0.17715 (9)0.0526 (4)
H120.12500.59620.17330.063*
C130.17187 (5)0.7545 (4)0.23274 (10)0.0698 (6)
H130.18260.65580.26660.084*
C140.19059 (5)0.9315 (4)0.23961 (11)0.0757 (6)
H140.21350.95090.27790.091*
C150.17588 (5)1.0806 (3)0.19041 (11)0.0672 (5)
H150.18851.20120.19480.081*
C160.14155 (4)1.0463 (2)0.13361 (9)0.0483 (4)
C170.12020 (5)1.1645 (2)0.07061 (10)0.0509 (4)
C180.08641 (4)1.0341 (2)0.02587 (8)0.0436 (3)
C190.06096 (4)0.7055 (2)0.04397 (8)0.0415 (3)
H19A0.07450.58330.05920.050*
H19B0.05170.7040−0.01110.050*
C200.02520 (4)0.7204 (2)0.07963 (8)0.0411 (3)
H20A0.00610.62120.05730.049*
H20B0.01260.84590.06650.049*
C220.04231 (4)0.4390 (2)0.19615 (7)0.0368 (3)
N10.12011 (4)0.26548 (18)0.38917 (7)0.0420 (3)
N20.05537 (4)0.38618 (19)0.26924 (7)0.0446 (3)
N30.25633 (5)0.0353 (3)0.60869 (9)0.0688 (4)
N40.08920 (3)0.86365 (18)0.06542 (6)0.0386 (3)
O10.27296 (4)0.1532 (3)0.65616 (9)0.0878 (5)
O20.26757 (6)−0.1329 (3)0.60752 (10)0.1117 (7)
O30.12620 (4)1.32892 (19)0.05188 (9)0.0767 (4)
O40.06274 (4)1.07378 (18)−0.03291 (6)0.0592 (3)
S10.031276 (12)0.28227 (6)0.12387 (2)0.04687 (11)
S20.036236 (11)0.69395 (5)0.18228 (2)0.04120 (10)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0424 (8)0.0715 (12)0.0423 (8)0.0063 (8)0.0071 (6)0.0042 (8)
C20.0598 (10)0.0559 (11)0.0567 (10)0.0124 (8)0.0061 (8)0.0048 (8)
C30.0558 (9)0.0501 (9)0.0463 (8)0.0047 (7)0.0025 (7)−0.0024 (7)
C40.0403 (7)0.0501 (9)0.0361 (7)0.0013 (6)0.0108 (6)0.0001 (6)
C50.0470 (8)0.0566 (10)0.0516 (9)0.0072 (7)0.0043 (7)−0.0127 (8)
C60.0455 (8)0.0718 (12)0.0479 (9)0.0012 (8)0.0047 (7)−0.0132 (8)
C70.0557 (8)0.0401 (8)0.0420 (8)0.0016 (7)0.0051 (6)−0.0050 (6)
C80.0551 (8)0.0400 (8)0.0429 (8)−0.0050 (7)0.0011 (6)0.0027 (6)
C90.0687 (10)0.0426 (9)0.0328 (7)0.0089 (7)−0.0002 (6)−0.0043 (6)
C100.0633 (9)0.0414 (8)0.0417 (8)−0.0043 (7)−0.0011 (7)−0.0021 (7)
C110.0381 (7)0.0504 (8)0.0315 (7)0.0028 (6)0.0078 (5)0.0015 (6)
C120.0474 (8)0.0650 (11)0.0425 (8)0.0055 (7)0.0040 (6)0.0119 (7)
C130.0485 (9)0.1117 (17)0.0451 (9)0.0125 (10)0.0025 (7)0.0187 (10)
C140.0451 (9)0.130 (2)0.0468 (10)−0.0066 (11)−0.0011 (7)−0.0083 (11)
C150.0524 (10)0.0881 (15)0.0624 (11)−0.0210 (10)0.0160 (8)−0.0200 (10)
C160.0455 (8)0.0548 (10)0.0470 (8)−0.0061 (7)0.0158 (6)−0.0067 (7)
C170.0543 (9)0.0430 (9)0.0628 (10)0.0008 (7)0.0289 (8)0.0016 (7)
C180.0490 (8)0.0447 (8)0.0405 (7)0.0114 (6)0.0177 (6)0.0067 (6)
C190.0469 (7)0.0418 (8)0.0329 (7)0.0010 (6)0.0029 (5)−0.0030 (6)
C200.0401 (7)0.0442 (8)0.0348 (7)0.0019 (6)−0.0005 (5)0.0030 (6)
C220.0335 (6)0.0390 (7)0.0363 (7)−0.0002 (5)0.0048 (5)−0.0025 (5)
N10.0470 (6)0.0385 (7)0.0374 (6)0.0021 (5)0.0032 (5)−0.0027 (5)
N20.0545 (7)0.0387 (7)0.0357 (6)0.0014 (5)0.0000 (5)−0.0014 (5)
N30.0573 (9)0.0930 (14)0.0513 (9)0.0138 (9)0.0020 (7)0.0054 (9)
N40.0404 (6)0.0400 (6)0.0333 (6)0.0021 (5)0.0042 (5)0.0037 (5)
O10.0680 (8)0.1118 (13)0.0681 (9)0.0036 (9)−0.0170 (7)−0.0075 (9)
O20.1188 (14)0.1077 (14)0.0826 (11)0.0530 (12)−0.0310 (10)−0.0040 (10)
O30.0829 (9)0.0482 (7)0.1107 (11)−0.0045 (7)0.0461 (9)0.0118 (7)
O40.0647 (7)0.0675 (8)0.0443 (6)0.0220 (6)0.0101 (5)0.0179 (5)
S10.0547 (2)0.0437 (2)0.0383 (2)−0.00326 (16)0.00241 (15)−0.00880 (15)
S20.0496 (2)0.0381 (2)0.03489 (18)0.00262 (14)0.00753 (14)−0.00231 (14)

Geometric parameters (Å, °)

C1—C61.368 (3)C11—C161.390 (2)
C1—C21.373 (2)C11—N41.4136 (18)
C1—N31.452 (2)C12—C131.389 (2)
C2—C31.375 (2)C12—H120.9300
C2—H20.9300C13—C141.369 (3)
C3—C41.400 (2)C13—H130.9300
C3—H30.9300C14—C151.374 (3)
C4—N11.3899 (19)C14—H140.9300
C4—C51.404 (2)C15—C161.395 (2)
C5—C61.371 (2)C15—H150.9300
C5—H50.9300C16—C171.451 (2)
C6—H60.9300C17—O31.211 (2)
C7—N11.4635 (19)C17—C181.542 (2)
C7—C81.504 (2)C18—O41.2097 (17)
C7—H7A0.9700C18—N41.3633 (19)
C7—H7B0.9700C19—N41.4511 (19)
C8—N21.462 (2)C19—C201.516 (2)
C8—H8A0.9700C19—H19A0.9700
C8—H8B0.9700C19—H19B0.9700
C9—N21.4585 (18)C20—S21.8080 (14)
C9—C101.513 (2)C20—H20A0.9700
C9—H9A0.9700C20—H20B0.9700
C9—H9B0.9700C22—N21.3394 (17)
C10—N11.4624 (19)C22—S11.6650 (14)
C10—H10A0.9700C22—S21.7760 (14)
C10—H10B0.9700N3—O21.221 (2)
C11—C121.377 (2)N3—O11.221 (2)
C6—C1—C2120.64 (15)C13—C12—H12121.5
C6—C1—N3119.78 (16)C14—C13—C12122.45 (19)
C2—C1—N3119.58 (17)C14—C13—H13118.8
C1—C2—C3120.01 (17)C12—C13—H13118.8
C1—C2—H2120.0C13—C14—C15120.56 (17)
C3—C2—H2120.0C13—C14—H14119.7
C2—C3—C4121.14 (16)C15—C14—H14119.7
C2—C3—H3119.4C14—C15—C16118.17 (19)
C4—C3—H3119.4C14—C15—H15120.9
N1—C4—C3121.97 (14)C16—C15—H15120.9
N1—C4—C5121.19 (14)C11—C16—C15120.60 (17)
C3—C4—C5116.79 (14)C11—C16—C17107.15 (14)
C6—C5—C4121.74 (16)C15—C16—C17132.16 (17)
C6—C5—H5119.1O3—C17—C16130.71 (17)
C4—C5—H5119.1O3—C17—C18123.61 (17)
C1—C6—C5119.65 (16)C16—C17—C18105.65 (13)
C1—C6—H6120.2O4—C18—N4127.11 (15)
C5—C6—H6120.2O4—C18—C17127.08 (15)
N1—C7—C8111.19 (13)N4—C18—C17105.80 (12)
N1—C7—H7A109.4N4—C19—C20113.34 (12)
C8—C7—H7A109.4N4—C19—H19A108.9
N1—C7—H7B109.4C20—C19—H19A108.9
C8—C7—H7B109.4N4—C19—H19B108.9
H7A—C7—H7B108.0C20—C19—H19B108.9
N2—C8—C7110.79 (13)H19A—C19—H19B107.7
N2—C8—H8A109.5C19—C20—S2115.08 (10)
C7—C8—H8A109.5C19—C20—H20A108.5
N2—C8—H8B109.5S2—C20—H20A108.5
C7—C8—H8B109.5C19—C20—H20B108.5
H8A—C8—H8B108.1S2—C20—H20B108.5
N2—C9—C10110.25 (13)H20A—C20—H20B107.5
N2—C9—H9A109.6N2—C22—S1123.85 (11)
C10—C9—H9A109.6N2—C22—S2114.09 (10)
N2—C9—H9B109.6S1—C22—S2122.04 (8)
C10—C9—H9B109.6C4—N1—C10119.33 (12)
H9A—C9—H9B108.1C4—N1—C7119.01 (12)
N1—C10—C9112.02 (13)C10—N1—C7113.37 (12)
N1—C10—H10A109.2C22—N2—C9126.91 (13)
C9—C10—H10A109.2C22—N2—C8122.69 (12)
N1—C10—H10B109.2C9—N2—C8110.23 (11)
C9—C10—H10B109.2O2—N3—O1122.74 (18)
H10A—C10—H10B107.9O2—N3—C1118.16 (18)
C12—C11—C16121.17 (14)O1—N3—C1119.10 (18)
C12—C11—N4128.02 (15)C18—N4—C11110.53 (12)
C16—C11—N4110.75 (13)C18—N4—C19122.84 (12)
C11—C12—C13117.04 (18)C11—N4—C19126.64 (12)
C11—C12—H12121.5C22—S2—C20103.51 (7)
C6—C1—C2—C3−0.9 (3)C5—C4—N1—C1027.1 (2)
N3—C1—C2—C3179.84 (16)C3—C4—N1—C7−9.1 (2)
C1—C2—C3—C4−0.6 (3)C5—C4—N1—C7173.37 (14)
C2—C3—C4—N1−175.64 (15)C9—C10—N1—C4−161.47 (12)
C2—C3—C4—C52.0 (2)C9—C10—N1—C750.45 (17)
N1—C4—C5—C6175.60 (15)C8—C7—N1—C4161.00 (13)
C3—C4—C5—C6−2.0 (2)C8—C7—N1—C10−50.81 (18)
C2—C1—C6—C50.8 (3)S1—C22—N2—C9172.05 (12)
N3—C1—C6—C5−179.89 (15)S2—C22—N2—C9−9.64 (19)
C4—C5—C6—C10.7 (3)S1—C22—N2—C8−2.8 (2)
N1—C7—C8—N255.31 (17)S2—C22—N2—C8175.50 (11)
N2—C9—C10—N1−54.06 (17)C10—C9—N2—C22−116.39 (16)
C16—C11—C12—C130.6 (2)C10—C9—N2—C858.99 (17)
N4—C11—C12—C13177.47 (15)C7—C8—N2—C22115.48 (15)
C11—C12—C13—C140.2 (3)C7—C8—N2—C9−60.14 (16)
C12—C13—C14—C15−0.5 (3)C6—C1—N3—O2178.82 (19)
C13—C14—C15—C160.0 (3)C2—C1—N3—O2−1.9 (3)
C12—C11—C16—C15−1.2 (2)C6—C1—N3—O1−1.1 (3)
N4—C11—C16—C15−178.54 (13)C2—C1—N3—O1178.16 (17)
C12—C11—C16—C17175.79 (13)O4—C18—N4—C11175.30 (14)
N4—C11—C16—C17−1.57 (16)C17—C18—N4—C11−3.55 (14)
C14—C15—C16—C110.9 (2)O4—C18—N4—C19−4.8 (2)
C14—C15—C16—C17−175.21 (16)C17—C18—N4—C19176.33 (12)
C11—C16—C17—O3−178.79 (16)C12—C11—N4—C18−173.73 (14)
C15—C16—C17—O3−2.3 (3)C16—C11—N4—C183.40 (16)
C11—C16—C17—C18−0.57 (15)C12—C11—N4—C196.4 (2)
C15—C16—C17—C18175.91 (16)C16—C11—N4—C19−176.48 (13)
O3—C17—C18—O42.1 (2)C20—C19—N4—C18−88.55 (15)
C16—C17—C18—O4−176.31 (14)C20—C19—N4—C1191.31 (16)
O3—C17—C18—N4−179.08 (15)N2—C22—S2—C20172.63 (10)
C16—C17—C18—N42.54 (14)S1—C22—S2—C20−9.02 (10)
N4—C19—C20—S2−66.16 (15)C19—C20—S2—C22−77.72 (12)
C3—C4—N1—C10−155.40 (14)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C13—H13···O2i0.932.523.252 (2)136.
C5—H5···O3ii0.932.333.125 (2)143.

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

Table 2 π–π interactions (Å)'

CgCgCg···Cg (Å)sym. code
Cg1Cg23.534 (5)x, -y+1, z+0.5
Cg1Cg33.797 (5)x, -y+1, z+0.5

* Cg1, Cg2 and Cg3 are the centroids of the C1-C2-C3-C4-C5-C6 (benzene), C11-C16-C17-C18-N4 (pyrrole) and C11-C12-C13-C14-C15-C16 rings, respectively.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZQ2052).

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