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Acta Crystallographica Section E: Crystallographic Communications logoLink to Acta Crystallographica Section E: Crystallographic Communications
. 2021 Jan 8;77(Pt 2):83–85. doi: 10.1107/S2056989020016771

Crystal structure of 2,2′-{[(2-nitro­benz­yl)aza­nedi­yl]bis­(propane-3,1-di­yl)}bis­[1H-iso­indole-1,3(2H)-dione]

Ryne Holmberg a, Vanessa Franz a, Kristen M Moser a, Ricardo Solano a, Curtis Moore b, Arnold L Rheingold c, Gary L N Smith d,*
PMCID: PMC7869556  PMID: 33614130

The structure of the title compound exhibits a folded conformation with the three arms all on the same side of the tertiary N atom. The crystal packing features π–π inter­actions.

Keywords: crystal structure, phthalimides, π–π inter­actions, tripodal ligand

Abstract

The structure of the title compound, C29H26N4O6, exhibits a folded conformation with the three arms all on the same side of the tertiary N atom. The two phthalimide units make a dihedral angle of 12.18 (12)° and the dihedral angles between the benzyl plane and the phthalimide units are 68.08 (7) and 67.71 (7)°. The crystal packing features π–π inter­actions.

Chemical context  

The coordination chemistry of tripodal tetra­mine ligands has been reviewed and includes structures with pendant arms that are symmetric or asymmetric with respect to the presence of aliphatic and aromatic donor atoms (Blackman, 2005 ▸). The ligands coordinate transition metals or lanthanide ions using all four nitro­gen donor atoms. Tripodal amines have also been shown to coordinate to anions (Bose et al., 2011 ▸; Bazzicalupi et al., 2009 ▸; Kuswandi et al., 2006 ▸). The title compound is an inter­mediate for the synthesis of an asymmetrical tripodal tetra­mine. After removal of the phthalimide protecting groups and reduction of the nitro group, the title compound will become a tripodal ligand with two arms that contain aliphatic nitro­gens and one with an aromatic nitro­gen (Keypour et al., 2008a ▸,b ▸). Phthalimide compounds are of inter­est themselves because they have the tendency to exhibit a variety of supra­molecular inter­actions in the solid state. These include n–π, π–π, dipole–dipole, hydrogen bonding, and other supra­molecular inter­actions (Howell et al., 2003 ▸; Barrett et al., 1995 ▸).graphic file with name e-77-00083-scheme1.jpg

Structural commentary  

In the title compound (Fig. 1 ▸), the planes of the two phthalimide units (N1/C1–C8 and N3/C15–C22) make a dihedral angle of 12.18 (12)°. The dihedral angles between the benzyl plane and the phthalimide units are 68.08 (7) and 67.71 (7)°. This orientation creates a cavity around which the three arms are arranged. The bridgehead nitro­gen (N2) is located 2.104 (2) Å away from the plane created by the other three nitro­gen atoms.

Figure 1.

Figure 1

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The mol­ecular structure of the title compound, showing 50% probability ellipsoids.

Supra­molecular features  

The crystal structure consists of centrosymmetrical dimers with off-set π–π stacking between phthalimide groups (N3/C15–C22) running along the c-axis direction (Fig. 2 ▸). The centroid–centroid separation is 3.631 (4) Å. A second π–π stacking inter­action is found with one of the arms. The Cg(N1/C1–C8)⋯Cg(N3/C15–C22) centroid–centroid distance is 3.576 (4) Å. There is also a longer centrosymmetric interaction of the nitro benzyl groups (N4/C24–C29) with a distance of 4.694 (5) Å.

Figure 2.

Figure 2

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Mol­ecular packing of the title compound showing the π–π inter­actions (dashed lines).

Database survey  

A search of the Cambridge Structural Database (version 5.41, update of October 2020; Groom et al., 2016 ▸) for related compounds with a phthalimide unit gave 2623 hits. A search for the skeletal structure of N(CH2CH2CH2N)3 resulted in 149 entries. Similar off-set π–π stacking was seen in another compound with two phthalimide groups (REVYUM; Barrett et al., 1995 ▸). However, it was shown that an intra­molecular hydrogen bond between phthalimide groups resulted in no π–π stacking (VEHRUW; Brycki et al., 2006 ▸). More recently, a urea compound with two phthalimides showed π–π stacking and intra­molecular hydrogen bonding (PONZEZ; Medrano et al., 2014 ▸). Three structures with only one phthalimide group have also shown π–π inter­actions (VIDTUA; Brovarets et al., 2018 ▸; PAVHUR; Yang et al., 2012 ▸; SAGTIF; Shao et al., 2012 ▸). Another compound has been reported that has two phthalimide-protected nitro­gens with two carbon spacers versus three for the title compound, a benzyl group, and a trityl sulfide (WOJSIZ; Flörke et al., 2014 ▸). The dihedral angle between the planes of the phthalimide units is significantly different from the title compound at 77.86 (3)°. The crystal packing of this structure shows hydrogen bonding but not π–π stacking.

Synthesis and crystallization  

The title compound was prepared by using a previously reported method (Keypour et al., 2008 ▸ a). 3,3′-Diphthal­imido­di­propyl­amine (5.0 g, 13 mmol), 2-nitro­benzyl­chloride (2.6 g, 15 mmol), and potassium carbonate (1.8 g, 13 mmol) were heated at 433 K for one h to give the title compound. Crystals suitable for X-ray analysis were slowly grown from chloro­form.

Refinement  

Crystal data, data collection and structure refinement details are summarized in Table 1 ▸. H atoms were positioned geom­etrically (C—H = 0.95–0.99 Å) and refined using a riding model with U iso(H) = 1.2U eq(C).

Table 1. Experimental details.

Crystal data
Chemical formula C29H26N4O6
M r 526.54
Crystal system, space group Triclinic, P Inline graphic
Temperature (K) 120
a, b, c (Å) 7.8576 (10), 12.3468 (15), 14.1147 (17)
α, β, γ (°) 94.295 (1), 104.603 (1), 101.042 (1)
V (Å3) 1289.6 (3)
Z 2
Radiation type Mo Kα
μ (mm−1) 0.10
Crystal size (mm) 0.15 × 0.05 × 0.01
 
Data collection
Diffractometer Bruker APEX CCD
Absorption correction Multi-scan (SADABS; Krause et al., 2015 ▸)
T min, T max 0.986, 0.999
No. of measured, independent and observed [I > 2σ(I)] reflections 11940, 4518, 3422
R int 0.037
(sin θ/λ)max (Å−1) 0.604
 
Refinement
R[F 2 > 2σ(F 2)], wR(F 2), S 0.060, 0.124, 1.05
No. of reflections 4518
No. of parameters 352
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.22, −0.24
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Computer programs: APEX2 and SAINT (Bruker, 2014 ▸), and SHELXS97, SHELXL97, and SHELXTL (Sheldrick, 2008 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989020016771/zn2003sup1.cif

e-77-00083-sup1.cif (21.5KB, cif)
Click here for additional data file. (5.2KB, cdx)

Supporting information file. DOI: 10.1107/S2056989020016771/zn2003Isup4.cdx

Click here for additional data file. (10KB, cml)

Supporting information file. DOI: 10.1107/S2056989020016771/zn2003Isup3.cml

CCDC reference: 2052908

Additional supporting information: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by Research Associates, the Point Loma Nazarene University alumni support group.

supplementary crystallographic information

Crystal data

C29H26N4O6 Z = 2
Mr = 526.54 F(000) = 552
Triclinic, P1 Dx = 1.356 Mg m−3
a = 7.8576 (10) Å Mo Kα radiation, λ = 0.71073 Å
b = 12.3468 (15) Å Cell parameters from 4970 reflections
c = 14.1147 (17) Å θ = 2.4–25.4°
α = 94.295 (1)° µ = 0.10 mm−1
β = 104.603 (1)° T = 120 K
γ = 101.042 (1)° Plate, colorless
V = 1289.6 (3) Å3 0.15 × 0.05 × 0.01 mm
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Data collection

Bruker APEX CCD diffractometer 4518 independent reflections
Radiation source: fine-focus sealed tube 3422 reflections with I > 2σ(I)
Graphite monochromator Rint = 0.037
φ and ω scans θmax = 25.4°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Krause et al., 2015) h = −9→9
Tmin = 0.986, Tmax = 0.999 k = −14→14
11940 measured reflections l = −16→16
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Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124 H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0222P)2 + 1.5P] where P = (Fo2 + 2Fc2)/3
4518 reflections (Δ/σ)max < 0.001
352 parameters Δρmax = 0.22 e Å−3
0 restraints Δρmin = −0.24 e Å−3
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Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
C1 0.4890 (4) 0.8275 (2) 0.3635 (2) 0.0271 (7)
C2 0.6627 (4) 0.9044 (2) 0.3687 (2) 0.0243 (6)
C3 0.7287 (4) 1.0141 (2) 0.4092 (2) 0.0311 (7)
H3 0.6606 1.0541 0.4398 0.037*
C4 0.9008 (4) 1.0641 (3) 0.4031 (2) 0.0351 (8)
H4 0.9497 1.1401 0.4292 0.042*
C5 1.0010 (4) 1.0052 (3) 0.3599 (2) 0.0337 (8)
H5 1.1175 1.0414 0.3572 0.040*
C6 0.9345 (4) 0.8945 (3) 0.3206 (2) 0.0301 (7)
H6 1.0036 0.8536 0.2916 0.036*
C7 0.7637 (4) 0.8458 (2) 0.3253 (2) 0.0241 (6)
C8 0.6567 (4) 0.7305 (2) 0.2896 (2) 0.0245 (6)
C9 0.3523 (4) 0.6256 (2) 0.2976 (2) 0.0294 (7)
H9A 0.3190 0.6152 0.3600 0.035*
H9B 0.3999 0.5606 0.2796 0.035*
C10 0.1841 (4) 0.6293 (2) 0.2168 (2) 0.0256 (6)
H10A 0.1377 0.6952 0.2335 0.031*
H10B 0.2155 0.6367 0.1535 0.031*
C11 0.0385 (4) 0.5247 (2) 0.2048 (2) 0.0261 (6)
H11A −0.0070 0.5243 0.2641 0.031*
H11B −0.0633 0.5259 0.1472 0.031*
C12 0.1262 (3) 0.4048 (2) 0.0910 (2) 0.0237 (6)
H12A 0.1831 0.4769 0.0743 0.028*
H12B 0.0056 0.3794 0.0434 0.028*
C13 0.2396 (4) 0.3205 (2) 0.0790 (2) 0.0264 (7)
H13A 0.3572 0.3417 0.1297 0.032*
H13B 0.1775 0.2461 0.0883 0.032*
C14 0.2694 (4) 0.3165 (2) −0.0232 (2) 0.0264 (6)
H14A 0.1517 0.3070 −0.0728 0.032*
H14B 0.3454 0.3884 −0.0285 0.032*
C15 0.5367 (3) 0.2414 (2) −0.0430 (2) 0.0221 (6)
C16 0.5587 (3) 0.1320 (2) −0.08339 (19) 0.0206 (6)
C17 0.7090 (3) 0.0994 (2) −0.0999 (2) 0.0252 (6)
H17 0.8233 0.1495 −0.0828 0.030*
C18 0.6859 (4) −0.0095 (3) −0.1424 (2) 0.0286 (7)
H18 0.7866 −0.0343 −0.1547 0.034*
C19 0.5197 (4) −0.0827 (2) −0.1672 (2) 0.0268 (7)
H19 0.5079 −0.1564 −0.1969 0.032*
C20 0.3687 (4) −0.0497 (2) −0.1492 (2) 0.0256 (6)
H20 0.2545 −0.0997 −0.1652 0.031*
C21 0.3928 (3) 0.0578 (2) −0.10763 (19) 0.0203 (6)
C22 0.2602 (3) 0.1187 (2) −0.0827 (2) 0.0238 (6)
C23 −0.0218 (3) 0.3273 (2) 0.2100 (2) 0.0238 (6)
H23A 0.0068 0.2568 0.1872 0.029*
H23B −0.1465 0.3279 0.1729 0.029*
C24 −0.0079 (3) 0.3337 (2) 0.3192 (2) 0.0229 (6)
C25 −0.1560 (4) 0.3386 (2) 0.3552 (2) 0.0284 (7)
H25 −0.2697 0.3350 0.3098 0.034*
C26 −0.1421 (4) 0.3485 (3) 0.4551 (2) 0.0325 (7)
H26 −0.2470 0.3475 0.4771 0.039*
C27 0.0227 (4) 0.3597 (3) 0.5233 (2) 0.0337 (7)
H27 0.0318 0.3680 0.5920 0.040*
C28 0.1741 (4) 0.3589 (2) 0.4909 (2) 0.0282 (7)
H28 0.2892 0.3687 0.5368 0.034*
C29 0.1551 (4) 0.3436 (2) 0.3907 (2) 0.0247 (6)
N1 0.4939 (3) 0.72652 (19) 0.31379 (17) 0.0256 (6)
N2 0.1039 (3) 0.42205 (19) 0.19079 (16) 0.0217 (5)
N3 0.3550 (3) 0.22716 (19) −0.04578 (17) 0.0227 (5)
N4 0.3188 (3) 0.3337 (2) 0.36090 (19) 0.0298 (6)
O1 0.3652 (3) 0.84351 (18) 0.39538 (16) 0.0375 (5)
O2 0.6965 (3) 0.65364 (18) 0.24824 (15) 0.0328 (5)
O3 0.6476 (2) 0.32780 (17) −0.01314 (15) 0.0300 (5)
O4 0.1007 (2) 0.08489 (17) −0.09265 (15) 0.0315 (5)
O5 0.4580 (3) 0.4043 (2) 0.40052 (17) 0.0434 (6)
O6 0.3096 (3) 0.25346 (19) 0.30131 (17) 0.0373 (5)
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
C1 0.0285 (15) 0.0301 (18) 0.0236 (16) 0.0078 (13) 0.0073 (12) 0.0052 (13)
C2 0.0283 (14) 0.0226 (16) 0.0236 (16) 0.0086 (12) 0.0065 (11) 0.0071 (12)
C3 0.0363 (16) 0.0261 (18) 0.0316 (18) 0.0104 (14) 0.0071 (13) 0.0060 (14)
C4 0.0416 (18) 0.0235 (17) 0.0344 (19) 0.0016 (14) 0.0021 (14) 0.0095 (14)
C5 0.0295 (16) 0.0357 (19) 0.0338 (18) 0.0034 (14) 0.0059 (13) 0.0110 (15)
C6 0.0314 (15) 0.0358 (19) 0.0242 (16) 0.0113 (14) 0.0054 (12) 0.0076 (14)
C7 0.0290 (14) 0.0267 (17) 0.0179 (15) 0.0086 (12) 0.0055 (11) 0.0069 (12)
C8 0.0311 (15) 0.0264 (17) 0.0195 (15) 0.0127 (13) 0.0072 (11) 0.0069 (13)
C9 0.0335 (16) 0.0239 (17) 0.0293 (17) 0.0019 (13) 0.0086 (12) 0.0060 (13)
C10 0.0308 (15) 0.0202 (16) 0.0281 (16) 0.0076 (12) 0.0106 (12) 0.0035 (13)
C11 0.0295 (15) 0.0248 (17) 0.0275 (16) 0.0095 (12) 0.0113 (12) 0.0047 (13)
C12 0.0248 (14) 0.0283 (17) 0.0215 (15) 0.0091 (12) 0.0092 (11) 0.0066 (13)
C13 0.0275 (15) 0.0277 (17) 0.0277 (16) 0.0106 (12) 0.0100 (12) 0.0056 (13)
C14 0.0299 (15) 0.0269 (17) 0.0273 (16) 0.0114 (12) 0.0119 (12) 0.0057 (13)
C15 0.0218 (13) 0.0268 (17) 0.0203 (15) 0.0072 (13) 0.0081 (11) 0.0053 (12)
C16 0.0189 (13) 0.0275 (16) 0.0172 (14) 0.0078 (11) 0.0058 (10) 0.0040 (12)
C17 0.0193 (13) 0.0297 (17) 0.0288 (16) 0.0068 (12) 0.0090 (11) 0.0056 (13)
C18 0.0252 (14) 0.0369 (19) 0.0306 (17) 0.0145 (13) 0.0129 (12) 0.0084 (14)
C19 0.0307 (15) 0.0247 (17) 0.0269 (16) 0.0096 (12) 0.0091 (12) 0.0021 (13)
C20 0.0212 (13) 0.0286 (17) 0.0255 (16) 0.0023 (12) 0.0061 (11) 0.0028 (13)
C21 0.0190 (13) 0.0275 (17) 0.0177 (14) 0.0091 (11) 0.0073 (10) 0.0042 (12)
C22 0.0197 (14) 0.0337 (18) 0.0209 (15) 0.0094 (12) 0.0072 (11) 0.0072 (13)
C23 0.0223 (13) 0.0259 (16) 0.0232 (15) 0.0042 (12) 0.0073 (11) 0.0032 (12)
C24 0.0267 (14) 0.0184 (15) 0.0243 (15) 0.0044 (11) 0.0084 (11) 0.0033 (12)
C25 0.0251 (14) 0.0288 (17) 0.0321 (17) 0.0066 (12) 0.0078 (12) 0.0070 (14)
C26 0.0367 (16) 0.0370 (19) 0.0336 (18) 0.0152 (14) 0.0204 (13) 0.0100 (15)
C27 0.0499 (19) 0.0323 (19) 0.0247 (17) 0.0175 (15) 0.0135 (14) 0.0067 (14)
C28 0.0316 (15) 0.0228 (17) 0.0290 (17) 0.0078 (13) 0.0042 (12) 0.0045 (13)
C29 0.0267 (14) 0.0196 (15) 0.0307 (17) 0.0067 (12) 0.0108 (12) 0.0062 (13)
N1 0.0305 (13) 0.0226 (14) 0.0246 (13) 0.0056 (10) 0.0090 (10) 0.0026 (11)
N2 0.0239 (11) 0.0214 (13) 0.0234 (13) 0.0076 (10) 0.0107 (9) 0.0039 (10)
N3 0.0236 (12) 0.0243 (14) 0.0245 (13) 0.0104 (10) 0.0098 (9) 0.0045 (10)
N4 0.0275 (13) 0.0311 (16) 0.0341 (15) 0.0100 (12) 0.0096 (11) 0.0109 (13)
O1 0.0348 (12) 0.0385 (14) 0.0422 (14) 0.0066 (10) 0.0193 (10) −0.0035 (11)
O2 0.0415 (12) 0.0304 (13) 0.0296 (12) 0.0160 (10) 0.0103 (9) 0.0012 (10)
O3 0.0278 (10) 0.0280 (12) 0.0334 (12) 0.0031 (9) 0.0098 (9) 0.0008 (9)
O4 0.0189 (10) 0.0399 (13) 0.0379 (13) 0.0071 (9) 0.0114 (8) 0.0042 (10)
O5 0.0249 (11) 0.0481 (15) 0.0528 (15) 0.0032 (10) 0.0049 (10) 0.0100 (12)
O6 0.0431 (13) 0.0379 (14) 0.0391 (14) 0.0202 (11) 0.0168 (10) 0.0063 (11)
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Geometric parameters (Å, º)

C1—O1 1.212 (3) C14—H14B 0.9900
C1—N1 1.396 (4) C15—O3 1.211 (3)
C1—C2 1.487 (4) C15—N3 1.394 (3)
C2—C3 1.377 (4) C15—C16 1.485 (4)
C2—C7 1.388 (4) C16—C17 1.385 (4)
C3—C4 1.401 (4) C16—C21 1.388 (4)
C3—H3 0.9500 C17—C18 1.390 (4)
C4—C5 1.384 (4) C17—H17 0.9500
C4—H4 0.9500 C18—C19 1.384 (4)
C5—C6 1.384 (4) C18—H18 0.9500
C5—H5 0.9500 C19—C20 1.400 (4)
C6—C7 1.382 (4) C19—H19 0.9500
C6—H6 0.9500 C20—C21 1.369 (4)
C7—C8 1.486 (4) C20—H20 0.9500
C8—O2 1.209 (3) C21—C22 1.490 (4)
C8—N1 1.398 (4) C22—O4 1.211 (3)
C9—N1 1.464 (3) C22—N3 1.392 (4)
C9—C10 1.524 (4) C23—N2 1.469 (3)
C9—H9A 0.9900 C23—C24 1.512 (4)
C9—H9B 0.9900 C23—H23A 0.9900
C10—C11 1.520 (4) C23—H23B 0.9900
C10—H10A 0.9900 C24—C25 1.391 (4)
C10—H10B 0.9900 C24—C29 1.394 (4)
C11—N2 1.474 (3) C25—C26 1.381 (4)
C11—H11A 0.9900 C25—H25 0.9500
C11—H11B 0.9900 C26—C27 1.380 (4)
C12—N2 1.467 (3) C26—H26 0.9500
C12—C13 1.520 (4) C27—C28 1.379 (4)
C12—H12A 0.9900 C27—H27 0.9500
C12—H12B 0.9900 C28—C29 1.379 (4)
C13—C14 1.517 (4) C28—H28 0.9500
C13—H13A 0.9900 C29—N4 1.474 (4)
C13—H13B 0.9900 N4—O6 1.229 (3)
C14—N3 1.452 (3) N4—O5 1.234 (3)
C14—H14A 0.9900
O1—C1—N1 124.5 (3) O3—C15—N3 124.6 (3)
O1—C1—C2 129.7 (3) O3—C15—C16 129.6 (2)
N1—C1—C2 105.8 (2) N3—C15—C16 105.9 (2)
C3—C2—C7 121.3 (3) C17—C16—C21 120.9 (3)
C3—C2—C1 130.6 (3) C17—C16—C15 130.6 (2)
C7—C2—C1 108.1 (2) C21—C16—C15 108.5 (2)
C2—C3—C4 117.0 (3) C16—C17—C18 117.3 (3)
C2—C3—H3 121.5 C16—C17—H17 121.3
C4—C3—H3 121.5 C18—C17—H17 121.3
C5—C4—C3 121.5 (3) C19—C18—C17 121.5 (3)
C5—C4—H4 119.3 C19—C18—H18 119.2
C3—C4—H4 119.3 C17—C18—H18 119.2
C6—C5—C4 121.2 (3) C18—C19—C20 120.9 (3)
C6—C5—H5 119.4 C18—C19—H19 119.5
C4—C5—H5 119.4 C20—C19—H19 119.5
C7—C6—C5 117.3 (3) C21—C20—C19 117.1 (2)
C7—C6—H6 121.3 C21—C20—H20 121.5
C5—C6—H6 121.3 C19—C20—H20 121.5
C6—C7—C2 121.8 (3) C20—C21—C16 122.3 (2)
C6—C7—C8 129.9 (3) C20—C21—C22 130.1 (2)
C2—C7—C8 108.4 (2) C16—C21—C22 107.5 (2)
O2—C8—N1 125.2 (3) O4—C22—N3 124.9 (3)
O2—C8—C7 129.1 (3) O4—C22—C21 128.9 (3)
N1—C8—C7 105.7 (2) N3—C22—C21 106.3 (2)
N1—C9—C10 112.9 (2) N2—C23—C24 110.2 (2)
N1—C9—H9A 109.0 N2—C23—H23A 109.6
C10—C9—H9A 109.0 C24—C23—H23A 109.6
N1—C9—H9B 109.0 N2—C23—H23B 109.6
C10—C9—H9B 109.0 C24—C23—H23B 109.6
H9A—C9—H9B 107.8 H23A—C23—H23B 108.1
C11—C10—C9 111.1 (2) C25—C24—C29 115.5 (3)
C11—C10—H10A 109.4 C25—C24—C23 121.7 (2)
C9—C10—H10A 109.4 C29—C24—C23 122.6 (2)
C11—C10—H10B 109.4 C26—C25—C24 121.7 (3)
C9—C10—H10B 109.4 C26—C25—H25 119.1
H10A—C10—H10B 108.0 C24—C25—H25 119.1
N2—C11—C10 112.6 (2) C27—C26—C25 120.7 (3)
N2—C11—H11A 109.1 C27—C26—H26 119.7
C10—C11—H11A 109.1 C25—C26—H26 119.7
N2—C11—H11B 109.1 C28—C27—C26 119.4 (3)
C10—C11—H11B 109.1 C28—C27—H27 120.3
H11A—C11—H11B 107.8 C26—C27—H27 120.3
N2—C12—C13 113.8 (2) C27—C28—C29 118.7 (3)
N2—C12—H12A 108.8 C27—C28—H28 120.6
C13—C12—H12A 108.8 C29—C28—H28 120.6
N2—C12—H12B 108.8 C28—C29—C24 123.8 (3)
C13—C12—H12B 108.8 C28—C29—N4 116.1 (2)
H12A—C12—H12B 107.7 C24—C29—N4 120.1 (3)
C14—C13—C12 109.8 (2) C1—N1—C8 112.1 (2)
C14—C13—H13A 109.7 C1—N1—C9 123.7 (2)
C12—C13—H13A 109.7 C8—N1—C9 124.0 (2)
C14—C13—H13B 109.7 C12—N2—C23 111.5 (2)
C12—C13—H13B 109.7 C12—N2—C11 110.5 (2)
H13A—C13—H13B 108.2 C23—N2—C11 109.4 (2)
N3—C14—C13 113.3 (2) C22—N3—C15 111.8 (2)
N3—C14—H14A 108.9 C22—N3—C14 123.3 (2)
C13—C14—H14A 108.9 C15—N3—C14 124.5 (2)
N3—C14—H14B 108.9 O6—N4—O5 124.3 (3)
C13—C14—H14B 108.9 O6—N4—C29 118.0 (2)
H14A—C14—H14B 107.7 O5—N4—C29 117.7 (3)
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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989020016771/zn2003sup1.cif

e-77-00083-sup1.cif (21.5KB, cif)
Click here for additional data file. (5.2KB, cdx)

Supporting information file. DOI: 10.1107/S2056989020016771/zn2003Isup4.cdx

Click here for additional data file. (10KB, cml)

Supporting information file. DOI: 10.1107/S2056989020016771/zn2003Isup3.cml

CCDC reference: 2052908

Additional supporting information: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Crystallographic Communications are provided here courtesy of International Union of Crystallography

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