Crystal structure of diethyl 2,2′-[((1E,1′E)-{[(1R,4R)-cyclo­hexane-1,4-di­yl]bis­(aza­nylyl­idene)}bis­(methanylyl­idene))bis­(1H-pyrrole-2,1-di­yl)]di­acetate

Alshawi, J.; Yousif, M.; Zangana, K.H.; Vitorica Yrezabal, I.J.; Winpenny, R.; Al-Jeboori, M.J.

doi:10.1107/S2056989015002674

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 71| Part 3| March 2015| Pages o165-o166

doi:10.1107/S2056989015002674

Open

access

Crystal structure of diethyl 2,2′-[((1E,1′E)-{[(1R,4R)-cyclohexane-1,4-diyl]bis(azanylylidene)}bis(methanylylidene))bis(1H-pyrrole-2,1-diyl)]diacetate

Jasim Alshawi,^a Muoayed Yousif,^a Karzan H. Zangana,^b Inigo J. Vitorica Yrezabal,^b Richard Winpenny ^b and Mohamad J. Al-Jeboori ^c ^*

^aDepartment of Chemistry, College of Education for Pure Science, University of Basrah, Iraq, ^bSchool of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, England, 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 H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 6 February 2015; accepted 8 February 2015; online 13 February 2015)

The whole molecule of the title compound, C₂₄H₃₂N₄O₄, is generated by inversion symmetry. The cyclohexane ring adopts a chair conformation and the conformation about the C=N bonds is E. The pyrrole rings have an anti confirmation with respect to the cyclohexane moiety and the ethyl acetate groups have extended conformations. In the crystal, molecules are linked by pairs of C—H⋯O hydrogen bonds forming chains, enclosing R₂²(10) ring motifs with inversion symmetry, propagating parallel to the (101) plane.

Keywords: crystal structure; Schiff base; bispyrrole; C—H⋯O hydrogen bonding.

CCDC reference: 1048163

1. Related literature

For general background on the applications of Schiff bases and the use of pyrrole compounds, see: Köse et al. (2015 ); Trofimov et al. (2015 ). For the synthesis of dipyrrole Schiff bases 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 Schiff bases, see: Yang et al. (2004 ); Ourari et al. (2013 ).

2. Experimental

2.1. Crystal data

C₂₄H₃₂N₄O₄
M_r = 440.54
Triclinic, $[P \overline 1]$
a = 8.5531 (6) Å
b = 8.8379 (7) Å
c = 9.6492 (9) Å
α = 115.166 (9)°
β = 92.105 (7)°
γ = 113.288 (8)°
V = 587.68 (10) Å³
Z = 1
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 ) T_min = 0.933, T_max = 1.000
4657 measured reflections
2734 independent reflections
1827 reflections with I > 2σ(I)
R_int = 0.028

2.3. Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.124
S = 1.07
2734 reflections
146 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯O16ⁱ	0.97	2.50	3.317 (3)	142
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL2014 and PLATON.

Supporting information

CCDC reference: 1048163

Crystal structure: contains datablocks Gobal, I. DOI: 10.1107/S2056989015002674/su5080sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015002674/su5080Isup2.hkl

checkCIF report

Synthesis top

The title compound was prepared in a two step procedure:

Synthesis of ethyl (2-formyl-1H-pyrrole-1-yl)-acetate (L): prepared by reported procedures (Koriatopoulou et al., 2008; Singh & Pal, 2010) as follows: To a mixture of 1H-pyrrole-2-carbaldehyde (1.00 g, 10.51 mmol), K₂CO₃ (2.90g, 21.02 mmol) and (2.64 g, 10.51 mmol) of 18-crown-6 in dry 1,4-dioxane (20ml), was added drop wise a solution of ethyl bromoacetate (2.00 g, 12 mmol) in dry 1,4-dioxane (20 ml), over a period of 30 min. The reaction mixture was allowed to reflux under a nitrogen atmosphere for 6 h, 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 (15 ml), 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), giving compound (L) as a yellow oil product (yield: 0.75 g, 75%). NMR data (p.p.m), δH: (500 MHz, CDCl₃): 1.20 (3H, t, C12—H), 4.15 (2H, q, C11—H), 4.97 (2H, s, C8—H), 6.21 (1H, t, C3—H), 6.84 (1H, d, C4—H), 6.90 (1H, d, C2—H) and 9.45 (1H, s, C6—H); δC (125.75 MHz, CDCl3), 14.13 C12, 50.25 C8, 61.63 C11, 110.20 C3, 124.61 C4, 131.71 C5 and 132.10 C2. C=O for the carboxylate moiety at 168.37 (C12) and at 179.74 for C6. The positive ES mass spectrum at m/z = 182.4 (M+H)⁺ (62%) for C₉H₁₁NO₃, requires = 181.1. The other peaks detected at m/z =153.4 (100%), 109.3 (6%), 95 (9%) and 67 (4%) correspond to [M—CH₂CH₃]⁺, [M-(CH₂CH₃+CO₂)]⁺, [M-(CH₂CH₃+CO₂+CH₂)]⁺ and [M-(CH₂CH₃+CO₂+CH₂+CO)]+, respectively. IR (ATR cm^-1): 1650 ν(C=O) aldehyde moiety. 1710 ν(C=O) ester group.

Synthesis of the title Schiff-base: performed using conventional procedures (Yang et al., 2004; Ourari et al., 2013). To a mixture of L (1.81 g, 10 mmol) in ethanol (20 ml) with 3 drops of glacial acetic acid, a solution of 1,4-diaminocyclohexan (0.57 g, 5 mmol) in ethanol (20ml) was added drop wise 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: 1.09g, 60%). Crystals were obtained by slow evaporation of a solution in methanol/acetone. NMR data (p.p.m), δH (500 MHz, CDCl₃): 1.19 (6H, t,C15, 15–H), 1.47 (C10, 10- ,4H, q), δH = 1.67 (C9, 9-, 4H, q), 2.94 (2H, p, C8, 8–H), 4.10 (4H, q,C14, 14–H), 5.03 (C11, 11–H, 4H, s), 6.11 (2H, t, C3, 3–H), 6.38 (2H, d, C4, 4–H), 6.61 (2H, d, C2, 2–H) and 8.07 (2H, s, C6, 6–H); δC (125.75 MHz, CDCl3), 14.28 (C15, 15-). 32.61 (C10, 10- and C19, 9- ), 51.13 (C11, 11-), 61.07 (C14, 14- ), 68.8 (C8, 8-), 108.53 (C2, 2-), 116.58 (C5, 5-), 127.69 (C3, 3-), 129.93 (C4, 4-), 150.04 (C6, 6-), C=O 169.37 (C12, 12-). The positive ES mass spectrum at m/z = 441.52 (M+H)⁺ (100%) for C₂₄H₃₂N₄O₄, requires = 440.24. The other peaks detected at m/z = 412.42 (5%), 383 (3%), 295.19 (9%) and 267.1 (4%) correspond to [M—CH₂CH₃]⁺, [M-(2CH₂CH₃)]⁺, [M-(2CH₂CH₃+2CO₂)]⁺ and [M(2CH₂CH₃+2CO₂+2CH₂)]⁺, respectively. IR (ATR, cm^-1): 1580 (C=N), 1630 (C=O).

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. All H atoms were placed in calculated positions and treated as riding atoms: C—H = 0.95 - 0.99 Å with U_iso(H) = 1.5U_eq(C) for methyl H atoms and = 1.2U_eq(C) for other H atoms.

Comment top

The whole molecule of the title compound, Fig.1, is generated by inversion symmetry. The cyclohexane ring adopts a chair conformation and the conformation about the C═N bonds is E. The pyrrole rings crystallize in the anti-confirmation with respect to the cyclohexane moiety and the ethyl acetate moieties have extended conformations.

In the crystal, molecules are linked by pairs of C—H···O hydrogen bonds forming chains, enclosing R²₂(10) ring motifs with inversion symmetry, propagating parallel to plane (101); see Table 1 and Fig. 2.

Infrared spectrum indicated typical absorbance bands of the functional –C═ N and carbonyl –C═O at 1580 and 1630 cm^-1, respectively. The positive ES mass spectrum of the bis Schiff-base showed a parent ion peak at m/z = 441.52 (M+H)⁺, corresponding to C₂₆H₃₂N₄O₄, for which the required value is 440.24. The N7═C6 bond distance [1.270 (2) Å] is shorter than the N2—C8 bond distance [1.458 (2) Å], indicating a double bond order. However, the N1—C5 bond distance [1.384 (2) Å] indicates resonance has occurred in the pyrrole system between the lone pair electron of the nitrogen atom and the pyrrole ring.

Related literature top

For general background on the applications of Schiff bases and the use of pyrrole compounds, see: Kösea et al. (2015); Trofimov et al. (2015). For the synthesis of dipyrrole Schiff bases 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 Schiff bases, 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: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

Figures top

	Fig. 1. A view of the molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view along the b axis of the crystal packing of the title compound. The C—H···O hydrogen bonds are drawn as dashed lines (see Table 1 for details; H atom not involved in hydrogen bonding have been omitted for clarity).

Diethyl 2,2'-[((1E,1'E)-{[(1R,4R)-cyclohexane-1,4-diyl]bis(azanylylidene)}bis(methanylylidene))bis(1H-pyrrole-2,1-diyl)]diacetate top

Crystal data top

C₂₄H₃₂N₄O₄	Z = 1
M_r = 440.54	F(000) = 236
Triclinic, P1	D_x = 1.245 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5531 (6) Å	Cell parameters from 1515 reflections
b = 8.8379 (7) Å	θ = 3.3–26.7°
c = 9.6492 (9) Å	µ = 0.09 mm⁻¹
α = 115.166 (9)°	T = 150 K
β = 92.105 (7)°	Block, colourless
γ = 113.288 (8)°	0.4 × 0.3 × 0.3 mm
V = 587.68 (10) Å³

Data collection top

Agilent SuperNova (single source at offset, Atlas) diffractometer	2734 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1827 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.028
Detector resolution: 10.37 pixels mm^-1	θ_max = 29.4°, θ_min = 2.9°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −10→12
T_min = 0.933, T_max = 1.000	l = −13→8
4657 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.055	H-atom parameters constrained
wR(F²) = 0.124	w = 1/[σ²(F_o²) + (0.0363P)² + 0.1039P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
2734 reflections	Δρ_max = 0.18 e Å⁻³
146 parameters	Δρ_min = −0.25 e Å⁻³
0 restraints

Crystal data top

C₂₄H₃₂N₄O₄	γ = 113.288 (8)°
M_r = 440.54	V = 587.68 (10) Å³
Triclinic, P1	Z = 1
a = 8.5531 (6) Å	Mo Kα radiation
b = 8.8379 (7) Å	µ = 0.09 mm⁻¹
c = 9.6492 (9) Å	T = 150 K
α = 115.166 (9)°	0.4 × 0.3 × 0.3 mm
β = 92.105 (7)°

Data collection top

Agilent SuperNova (single source at offset, Atlas) diffractometer	2734 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	1827 reflections with I > 2σ(I)
T_min = 0.933, T_max = 1.000	R_int = 0.028
4657 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.07	Δρ_max = 0.18 e Å⁻³
2734 reflections	Δρ_min = −0.25 e Å⁻³
146 parameters

Special details top

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

	x	y	z	U_iso*/U_eq
O13	0.46898 (16)	0.46998 (17)	0.19574 (15)	0.0317 (3)
O16	0.63475 (17)	0.71083 (17)	0.43494 (15)	0.0338 (4)
N1	0.67517 (19)	0.9650 (2)	0.32094 (18)	0.0274 (4)
N7	0.87176 (19)	0.7539 (2)	0.17968 (18)	0.0313 (4)
C12	0.5599 (2)	0.6517 (3)	0.3013 (2)	0.0270 (4)
C6	0.9477 (2)	0.9265 (3)	0.2821 (2)	0.0297 (5)
H6	1.0695	0.9854	0.3163	0.036*
C5	0.8559 (2)	1.0361 (2)	0.3483 (2)	0.0275 (4)
C10	0.9066 (2)	0.4733 (2)	0.1181 (2)	0.0311 (5)
H10A	0.7851	0.3992	0.0575	0.037*
H10B	0.9087	0.4935	0.2252	0.037*
C11	0.5474 (2)	0.7689 (2)	0.2290 (2)	0.0279 (4)
H11A	0.5653	0.7192	0.1233	0.033*
H11B	0.4302	0.7597	0.2201	0.033*
C2	0.6355 (3)	1.1083 (3)	0.4039 (2)	0.0317 (5)
H2	0.5229	1.0970	0.4061	0.038*
C9	1.0097 (2)	0.3654 (3)	0.0461 (2)	0.0307 (5)
H9A	0.9545	0.2438	0.0420	0.037*
H9B	1.1280	0.4334	0.1127	0.037*
C8	0.9819 (2)	0.6620 (2)	0.1201 (2)	0.0304 (5)
H8	1.1007	0.7412	0.1897	0.036*
C4	0.9269 (3)	1.2260 (3)	0.4484 (2)	0.0340 (5)
H4	1.0459	1.3098	0.4864	0.041*
C3	0.7880 (3)	1.2712 (3)	0.4833 (2)	0.0377 (5)
H3	0.7980	1.3898	0.5483	0.045*
C14	0.4577 (3)	0.3383 (3)	0.2513 (2)	0.0400 (5)
H14A	0.4025	0.3576	0.3392	0.048*
H14B	0.5743	0.3562	0.2869	0.048*
C15	0.3512 (3)	0.1451 (3)	0.1175 (3)	0.0544 (7)
H15A	0.4111	0.1242	0.0342	0.082*
H15B	0.2388	0.1314	0.0787	0.082*
H15C	0.3349	0.0551	0.1534	0.082*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O13	0.0352 (8)	0.0259 (7)	0.0293 (8)	0.0091 (6)	0.0017 (6)	0.0141 (6)
O16	0.0378 (8)	0.0349 (7)	0.0245 (8)	0.0133 (6)	0.0036 (6)	0.0140 (6)
N1	0.0295 (8)	0.0254 (8)	0.0269 (9)	0.0133 (7)	0.0060 (6)	0.0114 (7)
N7	0.0275 (8)	0.0302 (8)	0.0281 (9)	0.0150 (7)	0.0050 (7)	0.0054 (7)
C12	0.0238 (10)	0.0303 (10)	0.0253 (10)	0.0116 (8)	0.0079 (8)	0.0124 (8)
C6	0.0255 (10)	0.0337 (10)	0.0262 (10)	0.0119 (9)	0.0061 (8)	0.0126 (9)
C5	0.0291 (10)	0.0282 (10)	0.0231 (10)	0.0120 (8)	0.0062 (8)	0.0115 (8)
C10	0.0250 (10)	0.0340 (10)	0.0249 (10)	0.0115 (9)	0.0054 (8)	0.0083 (8)
C11	0.0250 (10)	0.0305 (10)	0.0265 (10)	0.0120 (8)	0.0052 (8)	0.0129 (8)
C2	0.0412 (11)	0.0355 (10)	0.0299 (11)	0.0252 (10)	0.0127 (9)	0.0178 (9)
C9	0.0259 (10)	0.0280 (10)	0.0300 (11)	0.0104 (8)	0.0039 (8)	0.0089 (8)
C8	0.0204 (9)	0.0302 (10)	0.0293 (11)	0.0116 (8)	0.0034 (7)	0.0050 (8)
C4	0.0361 (11)	0.0269 (10)	0.0308 (11)	0.0105 (9)	0.0062 (9)	0.0106 (9)
C3	0.0519 (13)	0.0269 (10)	0.0341 (12)	0.0207 (10)	0.0109 (10)	0.0118 (9)
C14	0.0480 (13)	0.0336 (11)	0.0396 (13)	0.0130 (10)	0.0065 (10)	0.0240 (10)
C15	0.0690 (16)	0.0316 (11)	0.0498 (15)	0.0101 (12)	−0.0021 (12)	0.0217 (11)

Geometric parameters (Å, º) top

O13—C12	1.336 (2)	C6—C5	1.441 (2)
O13—C14	1.448 (2)	C5—C4	1.375 (2)
O16—C12	1.203 (2)	C10—C9	1.522 (2)
N1—C5	1.384 (2)	C10—C8	1.522 (3)
N1—C11	1.452 (2)	C2—C3	1.365 (3)
N1—C2	1.363 (2)	C9—C8ⁱ	1.526 (3)
N7—C6	1.270 (2)	C8—C9ⁱ	1.526 (3)
N7—C8	1.458 (2)	C4—C3	1.405 (3)
C12—C11	1.506 (3)	C14—C15	1.490 (3)

C12—O13—C14	116.15 (15)	C4—C5—C6	127.83 (17)
C5—N1—C11	126.32 (15)	C8—C10—C9	111.74 (14)
C2—N1—C5	108.70 (15)	N1—C11—C12	112.58 (15)
C2—N1—C11	124.84 (15)	N1—C2—C3	108.91 (17)
C6—N7—C8	117.71 (15)	C10—C9—C8ⁱ	111.47 (17)
O13—C12—C11	109.47 (16)	N7—C8—C10	109.64 (14)
O16—C12—O13	124.75 (19)	N7—C8—C9ⁱ	109.49 (17)
O16—C12—C11	125.74 (17)	C10—C8—C9ⁱ	110.20 (15)
N7—C6—C5	123.74 (17)	C5—C4—C3	107.99 (18)
N1—C5—C6	124.91 (15)	C2—C3—C4	107.14 (17)
C4—C5—N1	107.27 (16)	O13—C14—C15	107.88 (18)

O13—C12—C11—N1	−166.07 (14)	C11—N1—C5—C6	3.5 (3)
O16—C12—C11—N1	16.3 (3)	C11—N1—C5—C4	−176.36 (17)
N1—C5—C4—C3	0.4 (2)	C11—N1—C2—C3	176.43 (17)
N1—C2—C3—C4	−0.3 (2)	C2—N1—C5—C6	179.33 (19)
N7—C6—C5—N1	6.4 (3)	C2—N1—C5—C4	−0.6 (2)
N7—C6—C5—C4	−173.7 (2)	C2—N1—C11—C12	−110.7 (2)
C12—O13—C14—C15	179.68 (16)	C9—C10—C8—N7	176.06 (15)
C6—N7—C8—C10	134.27 (18)	C9—C10—C8—C9ⁱ	55.5 (2)
C6—N7—C8—C9ⁱ	−104.71 (19)	C8—N7—C6—C5	178.46 (18)
C6—C5—C4—C3	−179.5 (2)	C8—C10—C9—C8ⁱ	−56.2 (2)
C5—N1—C11—C12	64.5 (2)	C14—O13—C12—O16	2.0 (3)
C5—N1—C2—C3	0.6 (2)	C14—O13—C12—C11	−175.70 (15)
C5—C4—C3—C2	0.0 (2)

Symmetry code: (i) −x+2, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O16ⁱⁱ	0.97	2.50	3.317 (3)	142

Symmetry code: (ii) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O16ⁱ	0.97	2.50	3.317 (3)	142

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

The authors are grateful to the Iraqi Ministry for Higher Education for providing six months funding for JA's PhD scholarship.

References

Agilent (2013). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Koriatopoulou, K., Karousis, N. & Varvounis, G. (2008). Tetrahedron, 64, 10009–10013. Web of Science CrossRef CAS Google Scholar
Köse, M., Ceyhan, G., Tümer, M., Demirtaş, İ., Gönül, İ. & McKee, V. (2015). Spectrochim. Acta Part A, 137, 477–485. Google Scholar
Meghdadi, S., Amirnasr, M., Mereiter, K. & Karimi Abdolmaleki, M. (2010). Acta Cryst. E66, m332–m333. Web of Science CSD CrossRef IUCr Journals Google Scholar
Munro, O., Strydom, S. & Grimmer, C. (2004). New J. Chem. 28, 34–42. Web of Science CSD CrossRef CAS Google Scholar
Ourari, A., Aggoun, D. & Ouahab, L. (2013). Inorg. Chem. Commun. 33, 118–124. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Singh, K. & Pal, D. (2010). J. Serb. Chem. Soc. 75, 917–927. Web of Science CrossRef CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Trofimov, B. A., Mikhaleva, A., Schmidt, E. Y. & Sobenina, L. N. (2015). In Chemistry of Pyrroles. Boca Raton: CRC Press. Google Scholar
Yang, L., Shan, X., Chen, Q., Wang, Z. & Ma, J. S. (2004). Eur. J. Inorg. Chem. 2004, 1474–1477. Web of Science CSD CrossRef Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 71| Part 3| March 2015| Pages o165-o166

doi:10.1107/S2056989015002674

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

Crystal structure of di­ethyl 2,2′-[((1E,1′E)-{[(1R,4R)-cyclo­hexane-1,4-di­yl]bis­­(aza­nylyl­­idene)}bis­­(methanylyl­­idene))bis­­(1H-pyrrole-2,1-di­yl)]di­acetate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of diethyl 2,2′-[((1E,1′E)-{[(1R,4R)-cyclohexane-1,4-diyl]bis(azanylylidene)}bis(methanylylidene))bis(1H-pyrrole-2,1-diyl)]diacetate