Crystal structure of diethyl 2,2'-[((1E,1'E)-{[(1R,4R)-cyclo-hexane-1,4-di-yl]bis-(aza-nylyl-idene)}bis-(methanylyl-idene))bis-(1H-pyrrole-2,1-di-yl)]di-acetate.

The whole mol-ecule of the title compound, C24H32N4O4, is generated by inversion symmetry. The cyclo-hexane 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 cyclo-hexane moiety and the ethyl acetate groups have extended conformations. In the crystal, mol-ecules are linked by pairs of C-H⋯O hydrogen bonds forming chains, enclosing R 2 (2)(10) ring motifs with inversion symmetry, propagating parallel to the (101) plane.

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 ▸).

Experimental

Crystal data

C24H32N4O4

M = 440.54

Triclinic,

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

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

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.124

S = 1.07

2734 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.25 e Å−3

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.

Crystal structure: contains datablock(s) Gobal, I. DOI: 10.1107/S2056989015002674/su5080sup1.cif

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

Click here for additional data file.

. DOI: 10.1107/S2056989015002674/su5080fig1.tif

A view of the mol­ecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.

b . DOI: 10.1107/S2056989015002674/su5080fig2.tif

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).

CCDC reference: 1048163

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

C24H32N4O4	Z = 1
Mr = 440.54	F(000) = 236
Triclinic, P1	Dx = 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

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	Rint = 0.028
Detector resolution: 10.37 pixels mm-1	θmax = 29.4°, θmin = 2.9°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −10→12
Tmin = 0.933, Tmax = 1.000	l = −13→8
4657 measured reflections

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(Fo2) + (0.0363P)2 + 0.1039P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2734 reflections	Δρmax = 0.18 e Å−3
146 parameters	Δρmin = −0.25 e Å−3
0 restraints

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C14H14AO16i	0.97	2.50	3.317(3)	142

Symmetry code: (i) .