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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 4| April 2015| Pages o259-o260
doi:10.1107/S2056989015005113

Crystal structure of di­ethyl 3,3′-{2,2′-(1E)-[1,4-phenyl­enebis(azan-1-yl-1-yl­­idene)]bis­­(methan-1-yl-1-yl­­idene)bis­­(1H-pyrrole-2,1-di­yl)}di­propano­ate

CROSSMARK_Color_square_no_text.svg
Jasim Alshawi,a Muoayed Yousif,a Gregore Timco,b Inigo J. Vitorica Yrezabal,b Richard Winpennyb and Mohamad J. Al-Jebooric*

aDepartment of Chemistry, College of Education for Pure Science, University of Basrah, Iraq, bSchool of chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, UK, and cDepartment of Chemistry, College of Education (Ibn Al-Haitham) for Pure Science, University of Baghdad, Iraq
*Correspondence e-mail: mohamadaljeboori@yahoo.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 11 February 2015; accepted 12 March 2015; online 25 March 2015)

The complete mol­ecule of the title compound, C26H30N4O4, is generated by crystallographic inversion symmetry. The dihedral angle between the planes of the benzene and pyrrole rings is 45.20 (11)°; the N atom bonded to the the benzene ring and the pyrrole N atom are in a syn conformation. The side chain adopts an extended conformation [N—C—C—C = 169.07 (17)° and C—O—C—C = −176.54 (17)°]. No directional inter­actions could be identified in the crystal packing.

CCDC reference: 1053761

Similar articles

1. Related literature

For the synthesis of di­pyrrole Schiff base ligands, see: Meghdadi et al.(2010[Meghdadi, S., Amirnasr, M., Mereiter, K. & Karimi Abdolmaleki, M. (2010). Acta Cryst. E66, m332-m333.]); Munro et al. (2004[Munro, O., Strydom, S. & Grimmer, C. (2004). New. J. Chem. 28, 34-42.]). For the synthesis of pyrrole ester precursors, see: Koriatopoulou et al. (2008[Koriatopoulou, K., Karousis, N. & Varvounis, G. (2008). Tetrahedron, 64, 10009-10013.]); Singh & Pal (2010[Singh, K. & Pal, D. (2010). J. Serb. Chem. Soc. 75, 917-927.]). For the preparation of the title compound, see: Yang et al. (2004[Yang, L., Shan, X., Chen, Q., Wang, Z. & Ma, J. S. (2004). Eur. J. Inorg. Chem. pp. 1474-1477.]); Ourari et al. (2013[Ourari, A., Aggoun, D. & Ouahab, L. (2013). Inorg. Chem. Commun. 33, 118-124.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C26H30N4O4

  • Mr = 462.54

  • Monoclinic, C 2/c

  • a = 21.6153 (10) Å

  • b = 8.1227 (4) Å

  • c = 13.9404 (8) Å

  • β = 94.395 (5)°

  • V = 2440.4 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 150 K

  • 0.4 × 0.3 × 0.3 mm

2.2. Data collection

  • Agilent SuperNova (Single source at offset, Atlas) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]) Tmin = 0.613, Tmax = 1.000

  • 6592 measured reflections

  • 2900 independent reflections

  • 1697 reflections with I > 2σ(I)

  • Rint = 0.063

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 0.138

  • S = 1.10

  • 2900 reflections

  • 155 parameters

  • H-atom parameters constrained

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.26 e Å−3

Data collection: CrysAlis PRO (Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.

Supporting information

CCDC reference: 1053761

Crystal structure: contains datablock I. DOI: 10.1107/S2056989015005113/hb7371sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015005113/hb7371Isup2.hkl

checkCIF report


Comment top

The Schiff base diethyl 3,3'-(2,2'-(1E)-(1,4-phenylenebis(azan-1-yl-1-ylidene))bis (methan-1-yl-1-ylidene)bis(1H-pyrrole-2,1-diyl))dipropanoate was prepared in two steps. The reaction of 1H-pyrrole-2-carbaldehyde with ethyl bromopropanoate resulted in the formation of (2-formyl-1H-pyrrole-1-yl)-propanoate (Koriatopoulou et al. (2008) and Singh & Pal (2010)). The reaction of two moles of the pyrrole ester with p-phenylenediamine gave the title of Schiff-base compound (Yang et al., 2004; Ourari et al., 2013). The compound with molar mass 462.54 g mol-1, crystallizes in monoclinic crystal structure with a space group c12 /c1 and had a calculated density 1.259 g cm-3. The asymetric unit consists of half the molecule, the molecule is completed by inversion symmetry. Infrared spectra indidicates typical absorbance bands of the

functional -C=N and carbonyl -C=O at 1595 and 1680 cm-1, respectively. The positive ES mass spectrum of the bis Schiff base showed a parent ion peak at m/z = 463.7 (M+H)+, corresponding to C26H30N4O4, for which the required value=462.3. The values distance (1.270Å) observed for (N7-C6) is shorter than (N7-C8) (1.458Å), indicating a double bond order. The distance observed at (1.384Å) for (N1-C5), revealed a resonance is occurred in the pyrrole system between lon pair electron of the nitrogen atom and the pyrrole ring. Other bond lengths and bond angles are within reported values.

Related literature top

For the synthesis of dipyrrole Schiff base ligands, see: Meghdadi et al.(2010); Munro et al. (2004). For the synthesis of pyrrole ester precursors, see: Koriatopoulou et al. (2008); Singh & Pal (2010). For the preparation of the title compound, see: Yang et al. (2004); Ourari et al. (2013).

Experimental top

FT-IR data were recorded on Agilent 8400s FT-IR while NMR data were collected on Bruker 500 MHz spectrometer in CDCl3 solutions. The assignment of the chemical shifts for the NMR data were made following numbering shown in structure. The title compound was prepared in two steps and as follows: Preparation of ethyl(2-formyl-1H-pyrrole-1-yl)-propanoate(L): It was prepared by literature procedures (Koriatopoulou et al., (2008); Singh & Pal (2010), as follows: To a mixture of 1H-pyrrole-2-carbaldehyde(1.00g,10.51mmol), K2CO3 (2.90g, 21.02mmol) and (2.64g, 10.51mmol) of 18-crown-6 in dry 1,4-dioxane (20ml), was added a solution of ethyl bromopropanoate (2.17g, 12mmol) in dry 1,4-dioxane (20ml)dropwise over a period of 30 min.The reaction mixture was allowed to reflux under nitrogen atmosphere for 6h, and then the solvent was removed under reduced pressure. Water (50ml) was added to the residue, and the mixture was extracted with ethyl acetate (3 × 15ml). The combined organic layers were washed with brine (15ml), and then dried over Na2SO4.The solvent was removed under reduced pressure, and the oily residue was purified by flash chromatography with an eluent mixture (33% ethyl acetate / hexane), yield 0.70 g (70%) of the title compound as a yellow oil product.IR (ATR cm-1): 1660 ν(C=O) aldehyde moiety. 172 0 ν (C=O) ester group. NMR data (p.p.m),δH (500 MHz, CDCl3): 1.10 (3H, t, C13-H), 2.70 (2H, t, C9-H), 4.01 (2H, Q, C12-H), 4.47 (2H, t, C8-H), 6.09 (1H, t, C3-H),6.83 (1H, d, C4-H), 6.94 (1H, d, C2-H) and 9.43 (1H, s, C6-H); δC (125.75 MHz, CDCl3):14.06 C13, 35.68 C9, 44.71 C8, 60.62 C12,109.53 C3, 125.17 C 4, 131.02 C5 and 132.23 C2, and C=O of the carboxylate moiety at 171.17 (C10) and 179.15 for C6. The positive ES mass spectrum at m/z =196.4 (M+H)+ (80 %) for C10H13NO3, requires =195.1. The other peaks which detected at m/z =167.4 (100 %), 123.3 (50 %), 95.2 (5 %) and 67 (6 %) correspond to [M-CH2CH3]+, [M-(CH2CH3+CO2)]+, [M-(CH2CH3+CO2+CH2+CH2)]+ and [M-(CH2CH3+CO2+CH2CH2+CO)]+, respectively.Synthesis of the title Schiff-base:achieved using standard method as follows: To a mixture of L (1.95g, 10mmol) in ethanol (20ml)with 3 drops of glacial acetic acid, a solution of p-phenylendiamine (0.5g, 5mmol) in ethanol (20ml) was added dropwise over a period of 20 min. The reaction mixture was allowed to reflux for 3h, and then cooled to room temperature. A white precipitate was collected by filtration and recrystallised from ethanol, yield 1.07g (55%). Crystals were obtained from evaporation of a mixture of methanol/acetone at room temperature. IR (ATR,cm-1): at line % / 1595 (C=N),1680 (C=O). 1H NMR dH (500 MHz, CDCl3, p.p.m) δH: 1.16 (6H, t, C16, 16–H), 2.85 (4H, t, C12, 12–H), 4.05 (4H, q, C15, 15–H), 4.67 (4H, t, C11,11–H), 6.11 (2H, t, C3, 3–H), 6.58 (2H, d, C4,4–H), 6.83 (2H, d, C2, 2–H), 7.11 (4H, s, C9, 9, C10, 10–H) and 8.25 (2H, s, C6, 6–H): 13C NMR (125.75 MHz, CDCl3, p.p.m) δC: 14.29 (C16, 16-), 36.14 (C12, 12-), 44.98 (C11, 11-), 60.62 (C15,15-), 108.85 (C 3, 3-), 119.88 (C2, 2-), 121.57 (C9,8-) and C10,10-), 129.16 and 129.17 to (C4, 4- and C5, 5-), 149.38 (C6, 6-) and 150.02 (C 8, 8-). C=O at 171.12 (C13,13-). ). The positive ES mass spectrum at m/z = 463.7 (M+H)+ (42%) for C26H30N4O4, requires =462.3. The other peaks detected at m/z =405.2 (3%), 361.6 (12%), 317.2 (3%) and 261.4 (3%) correspond to [M-2(CH2CH3)]+, [M-(2(CH2CH3)+CO2)]+, [M-(2CH2CH3+2CO2)]+ and [M-(2CH2CH3+2CO2+2CH2CH2)]+, espectively.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1.

The refinement was H atom attached to N1 was located in the difference Fourier map and refined isotropically. All other H atoms were placed in calculated positions with d(C—H) = 0.95 Å for aromatic, 0.99 for CH2 and 0.98 Å for CH3 atoms. The Uiso values were constrained to be 1.5Ueq of the carrier atom for methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups.

Structure description top

The Schiff base diethyl 3,3'-(2,2'-(1E)-(1,4-phenylenebis(azan-1-yl-1-ylidene))bis (methan-1-yl-1-ylidene)bis(1H-pyrrole-2,1-diyl))dipropanoate was prepared in two steps. The reaction of 1H-pyrrole-2-carbaldehyde with ethyl bromopropanoate resulted in the formation of (2-formyl-1H-pyrrole-1-yl)-propanoate (Koriatopoulou et al. (2008) and Singh & Pal (2010)). The reaction of two moles of the pyrrole ester with p-phenylenediamine gave the title of Schiff-base compound (Yang et al., 2004; Ourari et al., 2013). The compound with molar mass 462.54 g mol-1, crystallizes in monoclinic crystal structure with a space group c12 /c1 and had a calculated density 1.259 g cm-3. The asymetric unit consists of half the molecule, the molecule is completed by inversion symmetry. Infrared spectra indidicates typical absorbance bands of the

functional -C=N and carbonyl -C=O at 1595 and 1680 cm-1, respectively. The positive ES mass spectrum of the bis Schiff base showed a parent ion peak at m/z = 463.7 (M+H)+, corresponding to C26H30N4O4, for which the required value=462.3. The values distance (1.270Å) observed for (N7-C6) is shorter than (N7-C8) (1.458Å), indicating a double bond order. The distance observed at (1.384Å) for (N1-C5), revealed a resonance is occurred in the pyrrole system between lon pair electron of the nitrogen atom and the pyrrole ring. Other bond lengths and bond angles are within reported values.

For the synthesis of dipyrrole Schiff base ligands, see: Meghdadi et al.(2010); Munro et al. (2004). For the synthesis of pyrrole ester precursors, see: Koriatopoulou et al. (2008); Singh & Pal (2010). For the preparation of the title compound, see: Yang et al. (2004); Ourari et al. (2013).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
Diethyl 3,3'-{2,2'-(1E)-[1,4-phenylenebis(azan-1-yl-1-ylidene)]bis(methan-1-yl-1-ylidene)bis(1H-pyrrole-2,1-diyl)}dipropanoate top
Crystal data top
C26H30N4O4F(000) = 984
Mr = 462.54Dx = 1.259 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 21.6153 (10) ÅCell parameters from 1750 reflections
b = 8.1227 (4) Åθ = 3.8–27.5°
c = 13.9404 (8) ŵ = 0.09 mm−1
β = 94.395 (5)°T = 150 K
V = 2440.4 (2) Å3Block, clear light colourless
Z = 40.4 × 0.3 × 0.3 mm
Data collection top
Agilent SuperNova (Single source at offset, Atlas)
diffractometer		2900 independent reflections
Radiation source: SuperNova (Mo) X-ray Source1697 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.063
Detector resolution: 10.3705 pixels mm-1θmax = 29.5°, θmin = 2.9°
ω scansh = −18→29
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)		k = −10→7
Tmin = 0.613, Tmax = 1.000l = −19→18
6592 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H-atom parameters constrained
wR(F2) = 0.138 w = 1/[σ2(Fo2) + (0.0338P)2 + 0.0686P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
2900 reflectionsΔρmax = 0.22 e Å−3
155 parametersΔρmin = −0.26 e Å−3
0 restraints
Crystal data top
C26H30N4O4V = 2440.4 (2) Å3
Mr = 462.54Z = 4
Monoclinic, C2/cMo Kα radiation
a = 21.6153 (10) ŵ = 0.09 mm−1
b = 8.1227 (4) ÅT = 150 K
c = 13.9404 (8) Å0.4 × 0.3 × 0.3 mm
β = 94.395 (5)°
Data collection top
Agilent SuperNova (Single source at offset, Atlas)
diffractometer		2900 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)		1697 reflections with I > 2σ(I)
Tmin = 0.613, Tmax = 1.000Rint = 0.063
6592 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0550 restraints
wR(F2) = 0.138H-atom parameters constrained
S = 1.10Δρmax = 0.22 e Å−3
2900 reflectionsΔρmin = −0.26 e Å−3
155 parameters
Special details top

Experimental. CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O140.34059 (6)0.02364 (17)0.24674 (10)0.0286 (4)
N10.45878 (7)0.29578 (19)0.01458 (12)0.0225 (4)
O170.41066 (7)0.2126 (2)0.29870 (11)0.0385 (4)
N70.34834 (7)0.5212 (2)0.01854 (13)0.0231 (4)
C130.38269 (9)0.1407 (2)0.23355 (16)0.0240 (5)
C60.37626 (9)0.4878 (2)−0.05699 (16)0.0233 (5)
H60.36150.5387−0.11400.028*
C50.42829 (9)0.3787 (2)−0.06151 (16)0.0227 (5)
C80.29823 (9)0.6351 (2)0.00733 (15)0.0213 (5)
C90.29548 (9)0.7593 (2)0.07499 (16)0.0242 (5)
H90.32580.76540.12600.029*
C20.50726 (9)0.2115 (3)−0.01898 (17)0.0285 (5)
H20.53530.14660.01810.034*
C110.44300 (9)0.2904 (3)0.11490 (15)0.0248 (5)
H11A0.43080.39960.13450.030*
H11B0.47940.25810.15560.030*
C120.39047 (9)0.1701 (3)0.12900 (15)0.0247 (5)
H12A0.35210.21350.09830.030*
H12B0.39910.06630.09830.030*
C150.33162 (10)−0.0179 (3)0.34693 (16)0.0307 (6)
H15A0.32050.07960.38200.037*
H15B0.3694−0.06360.37820.037*
C100.25193 (9)0.6253 (2)−0.06747 (16)0.0244 (5)
H100.25280.5411−0.11260.029*
C40.45880 (9)0.3440 (3)−0.14264 (17)0.0283 (5)
H40.44840.3843−0.20420.034*
C30.50810 (10)0.2377 (3)−0.11602 (17)0.0318 (6)
H30.53610.1933−0.15640.038*
C160.28000 (11)−0.1429 (3)0.34458 (18)0.0412 (6)
H16A0.2913−0.23750.30850.062*
H16B0.2427−0.09530.31470.062*
H16C0.2731−0.17560.40910.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O140.0361 (8)0.0298 (9)0.0205 (9)−0.0087 (7)0.0052 (7)−0.0004 (7)
N10.0217 (9)0.0226 (10)0.0236 (10)0.0014 (7)0.0051 (8)0.0034 (8)
O170.0397 (9)0.0498 (11)0.0266 (10)−0.0165 (8)0.0054 (8)−0.0087 (8)
N70.0234 (9)0.0209 (9)0.0255 (10)0.0023 (7)0.0057 (8)−0.0010 (8)
C130.0213 (11)0.0228 (11)0.0283 (13)−0.0002 (9)0.0032 (10)−0.0042 (10)
C60.0258 (11)0.0184 (11)0.0260 (12)−0.0029 (8)0.0042 (10)0.0040 (10)
C50.0241 (10)0.0189 (11)0.0257 (12)0.0002 (8)0.0064 (9)0.0021 (10)
C80.0212 (10)0.0192 (11)0.0242 (12)0.0008 (8)0.0071 (9)0.0028 (10)
C90.0209 (10)0.0260 (12)0.0255 (12)−0.0006 (9)0.0005 (9)−0.0031 (10)
C20.0236 (11)0.0255 (12)0.0375 (14)0.0074 (9)0.0106 (10)0.0027 (11)
C110.0236 (10)0.0270 (12)0.0239 (12)0.0000 (9)0.0019 (9)0.0010 (10)
C120.0262 (11)0.0254 (12)0.0226 (12)0.0010 (9)0.0023 (9)−0.0028 (10)
C150.0414 (13)0.0290 (13)0.0230 (13)−0.0002 (10)0.0102 (11)0.0002 (11)
C100.0260 (11)0.0219 (11)0.0257 (13)0.0001 (9)0.0040 (10)−0.0070 (10)
C40.0323 (12)0.0261 (12)0.0275 (13)0.0012 (9)0.0099 (10)0.0063 (11)
C30.0330 (12)0.0293 (13)0.0351 (15)0.0075 (10)0.0153 (11)0.0018 (11)
C160.0551 (16)0.0357 (14)0.0347 (15)−0.0100 (11)0.0152 (13)0.0024 (12)
Geometric parameters (Å, º) top
O14—C131.338 (2)C2—C31.371 (3)
O14—C151.464 (2)C11—H11A0.9700
N1—C51.381 (3)C11—H11B0.9700
N1—C21.364 (2)C11—C121.522 (3)
N1—C111.465 (3)C12—H12A0.9700
O17—C131.203 (2)C12—H12B0.9700
N7—C61.282 (2)C15—H15A0.9700
N7—C81.424 (2)C15—H15B0.9700
C13—C121.499 (3)C15—C161.507 (3)
C6—H60.9300C10—C9i1.387 (3)
C6—C51.437 (3)C10—H100.9300
C5—C41.381 (3)C4—H40.9300
C8—C91.386 (3)C4—C31.399 (3)
C8—C101.391 (3)C3—H30.9300
C9—H90.9300C16—H16A0.9600
C9—C10i1.387 (3)C16—H16B0.9600
C2—H20.9300C16—H16C0.9600
C13—O14—C15115.83 (16)C12—C11—H11B109.2
C5—N1—C11127.98 (16)C13—C12—C11111.61 (17)
C2—N1—C5108.38 (18)C13—C12—H12A109.3
C2—N1—C11123.62 (18)C13—C12—H12B109.3
C6—N7—C8116.70 (18)C11—C12—H12A109.3
O14—C13—C12112.02 (18)C11—C12—H12B109.3
O17—C13—O14123.3 (2)H12A—C12—H12B108.0
O17—C13—C12124.69 (18)O14—C15—H15A110.4
N7—C6—H6117.1O14—C15—H15B110.4
N7—C6—C5125.9 (2)O14—C15—C16106.64 (18)
C5—C6—H6117.1H15A—C15—H15B108.6
N1—C5—C6126.61 (19)C16—C15—H15A110.4
N1—C5—C4107.45 (17)C16—C15—H15B110.4
C4—C5—C6125.9 (2)C8—C10—H10119.9
C9—C8—N7118.06 (19)C9i—C10—C8120.20 (18)
C9—C8—C10119.07 (18)C9i—C10—H10119.9
C10—C8—N7122.86 (18)C5—C4—H4126.0
C8—C9—H9119.6C5—C4—C3108.1 (2)
C8—C9—C10i120.71 (19)C3—C4—H4126.0
C10i—C9—H9119.6C2—C3—C4106.86 (18)
N1—C2—H2125.4C2—C3—H3126.6
N1—C2—C3109.23 (19)C4—C3—H3126.6
C3—C2—H2125.4C15—C16—H16A109.5
N1—C11—H11A109.2C15—C16—H16B109.5
N1—C11—H11B109.2C15—C16—H16C109.5
N1—C11—C12111.88 (17)H16A—C16—H16B109.5
H11A—C11—H11B107.9H16A—C16—H16C109.5
C12—C11—H11A109.2H16B—C16—H16C109.5
O14—C13—C12—C11−174.17 (16)C5—N1—C11—C1279.5 (2)
N1—C5—C4—C30.5 (2)C5—C4—C3—C2−0.8 (2)
N1—C2—C3—C40.9 (2)C8—N7—C6—C5179.01 (17)
N1—C11—C12—C13169.07 (17)C9—C8—C10—C9i1.3 (3)
O17—C13—C12—C115.8 (3)C2—N1—C5—C6−177.15 (19)
N7—C6—C5—N1−2.6 (3)C2—N1—C5—C40.0 (2)
N7—C6—C5—C4−179.3 (2)C2—N1—C11—C12−98.6 (2)
N7—C8—C9—C10i179.47 (17)C11—N1—C5—C64.5 (3)
N7—C8—C10—C9i−179.52 (18)C11—N1—C5—C4−178.28 (18)
C13—O14—C15—C16176.56 (17)C11—N1—C2—C3177.83 (18)
C6—N7—C8—C9−134.2 (2)C15—O14—C13—O17−2.2 (3)
C6—N7—C8—C1046.7 (3)C15—O14—C13—C12177.75 (16)
C6—C5—C4—C3177.72 (19)C10—C8—C9—C10i−1.4 (3)
C5—N1—C2—C3−0.6 (2)
Symmetry code: (i) −x+1/2, −y+3/2, −z.

Experimental details

Crystal data
Chemical formulaC26H30N4O4
Mr462.54
Crystal system, space groupMonoclinic, C2/c
Temperature (K)150
a, b, c (Å)21.6153 (10), 8.1227 (4), 13.9404 (8)
β (°) 94.395 (5)
V (Å3)2440.4 (2)
Z4
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.4 × 0.3 × 0.3
Data collection
DiffractometerAgilent SuperNova (Single source at offset, Atlas)
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2013)
Tmin, Tmax0.613, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		6592, 2900, 1697
Rint0.063
(sin θ/λ)max (Å−1)0.693
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.138, 1.10
No. of reflections2900
No. of parameters155
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.22, −0.26

Computer programs: CrysAlis PRO (Agilent, 2013), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), OLEX2 (Dolomanov et al., 2009).

 

Acknowledgements

The authors would like to thank the `Iraqi Ministry for Higher Education' for providing six months funding for JA's PhD scholarship.

References

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ISSN: 2056-9890
Volume 71| Part 4| April 2015| Pages o259-o260
doi:10.1107/S2056989015005113
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