Crystal structure and Hirshfeld surface analysis of dibutyl 5,5′-(pentane-3,3-diyl)bis(1H-pyrrole-5-carboxylate)

Wang, H.; Yin, Z.

doi:10.1107/S205698901900567X

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ISSN: 2056-9890

Volume 75| Part 6| June 2019| Pages 711-713

https://doi.org/10.1107/S205698901900567X

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Crystal structure and Hirshfeld surface analysis of dibutyl 5,5′-(pentane-3,3-diyl)bis(1H-pyrrole-5-carboxylate)

Haijing Wang ^a,^b and Zhenming Yin ^a,^b ^*

^aCollege of Chemistry, Tianjin Key Laboratory of Structure and Performance for Functional Molecules, Tianjin Normal University, Tianjin 300387, People's Republic of China, and ^bKey Laboratory of Inorganic–Organic Hybrid Functional Materials Chemistry (Tianjin Normal University), Ministry of Education, Tianjin 300387, People's Republic of China
^*Correspondence e-mail: tjyinzm@aliyun.com

Edited by K. Fejfarova, Institute of Biotechnology CAS, Czech Republic (Received 22 March 2019; accepted 25 April 2019; online 3 May 2019)

The molecular structure of the title compound, C₂₃H₃₄N₂O₄, has C2 symmetry. In the crystal, interlocked dimers are formed through quadruple N—H⋯O hydrogen bonds between pyrrole N—H groups and carbonyl O atoms.

Keywords: dipyrromethane-dicarboxylate; crystal structure; hydrogen bonding.

CCDC reference: 1912079

1. Chemical context

Hydrogen-bonding interactions play an important role in the design of functional assemblies that exhibit a variety of properties and functions (Prins et al., 2001 ; Steiner, 2002 ). Pyrrole-2-carboxylate possesses one hydrogen-bond donor (N—H_pyrrole) and one acceptor (C=O), which favour the formation of centrosymmetric dimers with pairs of N—H⋯O hydrogen bonds (Figueira et al., 2015 ). The dimer motif is structurally similar to classic Watson–Crick nucleotide base-pairs. Calculations have revealed the dimer motif to be a robust supramolecular synthon in crystal engineering (Dubis et al., 2002 ). In previous work, we have shown a way to use the 2-carbonyl pyrrole dimer as a supramolecular connector to construct hexagonal and grid architectures (Yin et al., 2006 ). Here, we report the self-assembly of the title compound, via quadruple N—H⋯N hydrogen bonds.

2. Structural commentary

The structure of the title compound is shown in Fig. 1. The asymmetric unit contains one half-molecule as it possesses C2 symmetry. In the molecule, the two pyrrole-2-carboxylate groups are both in a syn conformation, with the carbonyl group arranged syn to its adjacent pyrrole NH group. The O1—C8—C7—N1 torsion angle is −8.2 (5)°. The dihedral angle between the pyrrole rings is 72.8 (2)°.

Figure 1
ORTEP diagram for the title compound, with displacement ellipsoids drawn at the 30% probability level. [Symmetry code: (A) x, $[1 \over 4]$ − y, $[1 \over 4]$ − z.]

3. Supramolecular features

Pairs of molecules of the title compound form interlocked dimers through four N1—H1⋯O1 hydrogen bonds between the pyrrole carbonyl oxygen atoms and pyrrole NH protons (Table 1, Fig. 2). This type of dimer has also been observed in our previous work (Yin et al., 2007 ). The dimers are connected into a three-dimensional supramolecular structure through C—H⋯π contacts (Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C4–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	2.12	2.962 (3)	165
C12—H12C⋯Cg1ⁱⁱ	0.96	3.21	3.944 (3)	135
Symmetry codes: (i) $[-x+{\script{5\over 4}}, -y+{\script{1\over 4}}, z]$ ; (ii) $[x+{\script{1\over 4}}, y+{\script{1\over 4}}, -z]$ .

Figure 2
Part of the crystal packing showing molecules linked by N—H⋯O hydrogen bonds (red dashed lines) and C—H⋯π contacts (green dashed lines). [Symmetry codes: (i) −x + $[{5\over 4}]$ , −y + $[{1\over 4}]$ , z; (ii) x + $[{1\over 4}]$ , y + $[{1\over 4}]$ − z.]

4. Hirshfeld surface

A Hirshfeld surface analysis with CrystalExplorer (Turner et al., 2017 ) was performed to give insights into the important intermolecular interactions. These are normalized by van der Waals radii through a red–white–blue color scheme, where the red spots denote close contacts of molecules. The three-dimensional d_norm surface of the title compound is shown in Fig. 3. The red points represent closer contacts and negative d_norm values on the surface corresponding to the N—H⋯O and C—H⋯π interactions mentioned above. The two-dimensional fingerprint plots in Fig. 4 shown the intermolecular contacts and their percentage distributions on the Hirshfeld surface. H⋯H interactions (74.8%) are present as a major contributor while H⋯O/O⋯H (14.5%), H⋯C/C⋯H (5.4%), C⋯C (2.7%) and H⋯N/N⋯H (0.9%) contacts also give significant contributions to the Hirshfeld surface.

Figure 3
The Hirshfeld surface of the title compound mapped over d_norm in the range −0.486 to 1.895 a.u. The intermolecular contacts can be seen in the red regions.

Figure 4
The two-dimensional fingerprint plots of title compound: (a) all contacts; (b) H⋯H, (c) H⋯O/O⋯H, (d) H⋯C/C⋯H, (e) H⋯N/N⋯H and (f) C⋯C.

5. Database survey

A search in the Cambridge Structural Database (Groom et al., 2016 ) returned over 60 entries for dipyrromethane-1,9-dicarbonyl derivatives, including seven entries whose supramolecular structures feature interlocked dimers (ILITAY, Love et al., 2003 ; ODUMOQ,Yin et al., 2007; PIRJAB, Xie et al., 1994 ; NIQBAR01, Mahanta et al., 2012 ; VACRID, Deliomeroglu et al., 2016 ; PUJMAJ, Kim, 2010 and SAVDUQ, Uppal et al., 2012 ). In the crystal of PUJMAJ (Kim, 2010), only one of the carbonyl groups is involved in hydrogen bonds with two pyrrole N—H groups.

6. Synthesis and crystallization

n-Butyl alcohol (370 mg, 5 mmol), 2,2′-ditrichlordipyrrolemethane (980 mg, 2 mmol) and triethylamine (0.5 mL) were added to acetonitrile (20 mL), and then the mixture was refluxed for 2h. The solution was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel (ethyl acetate/petroleum ether = 1:2), affording the title compound (white powder, 672 mg, 71%), m.p. = 388 K. ¹H NMR (400 MHz, DMSO-d₆); δ 0.64 (t, 6H, J = 7.2 Hz, –CH₃), 0.90 (t, 6H, J = 7.2 Hz, –CH₃), 1.31–1.41 (m, 4H, –CH₂–), 1.58–1.65 (m, 4H, –CH₂–), 2.15 (q, 4H, J = 7.2 Hz, Å –CH₂–), 4.15 (q, 4H, J = 6.8 Hz, –CH₂–), 5.97 (s, 2H, PyCH), 6.66 (s, 2H, PyCH), 11.22 (s, 2H, NH); HRMS (ESI) m/z calculated for C₂₃H₃₄N₂O₄, (M + H)⁺ 403.25186; found 403.25224. Crystals suitable for X-ray diffraction analysis were obtained by the slow evaporation of a CH₃OH solution of the title compound.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. N—H hydrogen atoms were located from a difference-Fourier map and freely refined. Other H atoms were placed in difference calculated positions (C—H = 0.96 or 0.97 Å) and included in the final cycles of refinement using a riding model, with U_iso(H) = 1.2U_eq(C).

Table 2
Experimental details

Crystal data
Chemical formula	C₂₃H₃₄N₂O₄
M_r	402.52
Crystal system, space group	Orthorhombic, Fddd
Temperature (K)	296
a, b, c (Å)	14.358 (6), 17.333 (7), 38.902 (19)
V (Å³)	9681 (7)
Z	16
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.32 × 0.28 × 0.26

Data collection
Diffractometer	Bruker SMART CCD area detector
Absorption correction	Multi-scan (SADABS; Bruker, 2001 )
T_min, T_max	0.822, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	11878, 2156, 1501
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.081, 0.278, 1.05
No. of reflections	2156
No. of parameters	134
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.34
Computer programs: SMART and SAINT (Bruker, 2001), SHELXS (Sheldrick, 2008 ), SHELXL (Sheldrick, 2015 ) and OLEX2 (Dolomanov et al., 2009 ).

Supporting information

CCDC reference: 1912079

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S205698901900567X/ff2158sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698901900567X/ff2158Isup2.hkl

checkCIF report

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Dibutyl 5,5'-(pentane-3,3-diyl)bis(1H-pyrrole-5-carboxylate) top

Crystal data top

C₂₃H₃₄N₂O₄	D_x = 1.105 Mg m⁻³
M_r = 402.52	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Fddd	Cell parameters from 3608 reflections
a = 14.358 (6) Å	θ = 2.4–23.4°
b = 17.333 (7) Å	µ = 0.08 mm⁻¹
c = 38.902 (19) Å	T = 296 K
V = 9681 (7) Å³	Block, colourless
Z = 16	0.32 × 0.28 × 0.26 mm
F(000) = 3488

Data collection top

Bruker SMART CCD area detector diffractometer	1501 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
phi and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −17→16
T_min = 0.822, T_max = 1.000	k = −20→18
11878 measured reflections	l = −46→44
2156 independent 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)] = 0.081	H-atom parameters constrained
wR(F²) = 0.278	w = 1/[σ²(F_o²) + (0.1517P)² + 16.1858P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.002
2156 reflections	Δρ_max = 0.38 e Å⁻³
134 parameters	Δρ_min = −0.34 e Å⁻³
2 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.68341 (16)	0.20703 (14)	0.05576 (7)	0.0943 (8)
O2	0.65735 (17)	0.33467 (14)	0.05760 (8)	0.1078 (10)
N1	0.51592 (15)	0.18458 (13)	0.09406 (6)	0.0673 (7)
H1	0.5364	0.1412	0.0865	0.081*
C1	0.2522 (3)	0.1657 (3)	0.08110 (13)	0.1320 (17)
H1A	0.2131	0.1822	0.0997	0.198*
H1B	0.2142	0.1459	0.0628	0.198*
H1C	0.2880	0.2087	0.0729	0.198*
C2	0.3186 (2)	0.1018 (2)	0.09382 (9)	0.0941 (11)
H2A	0.3591	0.0869	0.0750	0.113*
H2B	0.2819	0.0570	0.1001	0.113*
C3	0.3798 (3)	0.1250	0.1250	0.0756 (11)
C4	0.44025 (19)	0.19324 (17)	0.11502 (7)	0.0704 (8)
C5	0.4317 (2)	0.27091 (19)	0.12144 (10)	0.0906 (10)
H5	0.3864	0.2937	0.1352	0.109*
C6	0.5026 (3)	0.31011 (19)	0.10378 (10)	0.0919 (10)
H6	0.5126	0.3631	0.1036	0.110*
C7	0.5546 (2)	0.25550 (17)	0.08689 (8)	0.0749 (8)
C8	0.6375 (2)	0.26101 (19)	0.06550 (9)	0.0810 (9)
C9	0.7383 (3)	0.3480 (3)	0.03496 (16)	0.141 (2)
H9A	0.7953	0.3356	0.0471	0.169*
H9B	0.7342	0.3149	0.0149	0.169*
C10	0.7401 (4)	0.4274 (4)	0.02437 (19)	0.164 (2)
H10A	0.7967	0.4359	0.0113	0.197*
H10B	0.7440	0.4592	0.0448	0.197*
C11	0.6604 (5)	0.4549 (4)	0.0035 (2)	0.193 (3)
H11A	0.6551	0.4210	−0.0162	0.232*
H11B	0.6045	0.4478	0.0172	0.232*
C12	0.6597 (7)	0.5314 (4)	−0.0088 (2)	0.211 (4)
H12A	0.6611	0.5666	0.0102	0.316*
H12B	0.6042	0.5399	−0.0221	0.316*
H12C	0.7133	0.5398	−0.0231	0.316*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0756 (14)	0.0847 (16)	0.1227 (19)	0.0097 (12)	0.0142 (12)	0.0162 (13)
O2	0.0842 (17)	0.0826 (16)	0.157 (2)	0.0004 (12)	0.0174 (15)	0.0302 (14)
N1	0.0571 (13)	0.0653 (13)	0.0796 (15)	0.0047 (10)	−0.0016 (10)	0.0003 (11)
C1	0.089 (3)	0.169 (4)	0.138 (4)	−0.001 (3)	−0.041 (3)	0.027 (3)
C2	0.072 (2)	0.116 (3)	0.095 (2)	−0.0173 (18)	−0.0137 (16)	0.0109 (19)
C3	0.053 (2)	0.090 (3)	0.083 (2)	0.000	0.000	0.006 (2)
C4	0.0570 (15)	0.0767 (18)	0.0775 (17)	0.0077 (13)	−0.0020 (12)	0.0027 (14)
C5	0.084 (2)	0.083 (2)	0.104 (2)	0.0180 (17)	0.0106 (18)	−0.0065 (18)
C6	0.088 (2)	0.0640 (18)	0.124 (3)	0.0049 (15)	0.005 (2)	0.0003 (18)
C7	0.0648 (17)	0.0672 (17)	0.093 (2)	0.0018 (13)	−0.0053 (15)	0.0099 (14)
C8	0.0659 (18)	0.0748 (19)	0.102 (2)	0.0011 (15)	−0.0014 (16)	0.0153 (16)
C9	0.075 (2)	0.129 (3)	0.219 (6)	−0.003 (2)	0.039 (3)	0.043 (4)
C10	0.136 (4)	0.149 (4)	0.206 (6)	−0.016 (4)	0.033 (4)	0.071 (4)
C11	0.156 (6)	0.205 (6)	0.219 (7)	0.028 (5)	0.033 (5)	0.085 (6)
C12	0.276 (11)	0.175 (5)	0.182 (6)	0.040 (7)	0.051 (6)	0.036 (5)

Geometric parameters (Å, º) top

O1—C8	1.205 (4)	C5—H5	0.9300
O2—C8	1.344 (4)	C5—C6	1.404 (5)
O2—C9	1.477 (5)	C6—H6	0.9300
N1—H1	0.8600	C6—C7	1.372 (5)
N1—C4	1.367 (4)	C7—C8	1.456 (5)
N1—C7	1.377 (4)	C9—H9A	0.9700
C1—H1A	0.9600	C9—H9B	0.9700
C1—H1B	0.9600	C9—C10	1.436 (7)
C1—H1C	0.9600	C10—H10A	0.9700
C1—C2	1.542 (6)	C10—H10B	0.9700
C2—H2A	0.9700	C10—C11	1.481 (9)
C2—H2B	0.9700	C11—H11A	0.9700
C2—C3	1.551 (4)	C11—H11B	0.9700
C3—C2ⁱ	1.551 (4)	C11—C12	1.412 (8)
C3—C4	1.518 (4)	C12—H12A	0.9600
C3—C4ⁱ	1.518 (4)	C12—H12B	0.9600
C4—C5	1.375 (4)	C12—H12C	0.9600

C8—O2—C9	116.9 (3)	N1—C7—C8	120.3 (3)
C4—N1—H1	125.0	C6—C7—N1	107.4 (3)
C4—N1—C7	110.1 (2)	C6—C7—C8	132.3 (3)
C7—N1—H1	125.0	O1—C8—O2	123.4 (3)
H1A—C1—H1B	109.5	O1—C8—C7	125.1 (3)
H1A—C1—H1C	109.5	O2—C8—C7	111.5 (3)
H1B—C1—H1C	109.5	O2—C9—H9A	109.8
C2—C1—H1A	109.5	O2—C9—H9B	109.8
C2—C1—H1B	109.5	H9A—C9—H9B	108.2
C2—C1—H1C	109.5	C10—C9—O2	109.6 (4)
C1—C2—H2A	108.6	C10—C9—H9A	109.8
C1—C2—H2B	108.6	C10—C9—H9B	109.8
C1—C2—C3	114.5 (3)	C9—C10—H10A	108.1
H2A—C2—H2B	107.6	C9—C10—H10B	108.1
C3—C2—H2A	108.6	C9—C10—C11	116.8 (6)
C3—C2—H2B	108.6	H10A—C10—H10B	107.3
C2—C3—C2ⁱ	111.0 (4)	C11—C10—H10A	108.1
C4ⁱ—C3—C2ⁱ	109.02 (17)	C11—C10—H10B	108.1
C4ⁱ—C3—C2	108.81 (18)	C10—C11—H11A	107.4
C4—C3—C2ⁱ	108.81 (18)	C10—C11—H11B	107.4
C4—C3—C2	109.02 (17)	H11A—C11—H11B	106.9
C4ⁱ—C3—C4	110.2 (3)	C12—C11—C10	119.7 (8)
N1—C4—C3	121.5 (2)	C12—C11—H11A	107.4
N1—C4—C5	106.7 (3)	C12—C11—H11B	107.4
C5—C4—C3	131.7 (3)	C11—C12—H12A	109.5
C4—C5—H5	125.7	C11—C12—H12B	109.5
C4—C5—C6	108.7 (3)	C11—C12—H12C	109.5
C6—C5—H5	125.7	H12A—C12—H12B	109.5
C5—C6—H6	126.4	H12A—C12—H12C	109.5
C7—C6—C5	107.1 (3)	H12B—C12—H12C	109.5
C7—C6—H6	126.4

O2—C9—C10—C11	−62.9 (8)	C4ⁱ—C3—C4—N1	44.80 (19)
N1—C4—C5—C6	0.7 (4)	C4ⁱ—C3—C4—C5	−140.2 (4)
N1—C7—C8—O1	−8.2 (5)	C4—C5—C6—C7	−0.5 (4)
N1—C7—C8—O2	171.6 (3)	C5—C6—C7—N1	0.1 (4)
C1—C2—C3—C2ⁱ	59.3 (3)	C5—C6—C7—C8	−178.0 (3)
C1—C2—C3—C4	−60.5 (4)	C6—C7—C8—O1	169.8 (4)
C1—C2—C3—C4ⁱ	179.2 (3)	C6—C7—C8—O2	−10.4 (5)
C2—C3—C4—N1	−74.5 (3)	C7—N1—C4—C3	175.5 (2)
C2ⁱ—C3—C4—N1	164.3 (3)	C7—N1—C4—C5	−0.6 (3)
C2—C3—C4—C5	100.5 (4)	C8—O2—C9—C10	170.1 (5)
C2ⁱ—C3—C4—C5	−20.7 (4)	C9—O2—C8—O1	1.8 (6)
C3—C4—C5—C6	−174.9 (3)	C9—O2—C8—C7	−178.0 (4)
C4—N1—C7—C6	0.3 (3)	C9—C10—C11—C12	−177.5 (6)
C4—N1—C7—C8	178.7 (3)

Symmetry code: (i) x, −y+1/4, −z+1/4.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1/C4–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱⁱ	0.86	2.12	2.962 (3)	165
C12—H12C···Cg1ⁱⁱⁱ	0.96	3.21	3.944 (3)	135

Symmetry codes: (ii) −x+5/4, −y+1/4, z; (iii) x+1/4, y+1/4, −z.

Funding information

Funding for this research was provided by: National Natural Science Foundation of China (award No. 21172174).

References

Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Deliomeroglu, M. K., Lynch, V. M. & Sessler, J. L. (2016). Chem. Sci. 7, 3843–3850. Web of Science CSD CrossRef CAS PubMed Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Dubis, A. T. & Grabowski, S. J. (2002). New J. Chem. 26, 165–169. Web of Science CrossRef CAS Google Scholar
Figueira, C. A., Lopes, P. S., Gomes, C. S. B., Veiros, L. F. & Gomes, P. T. (2015). CrystEngComm, 17, 6406–6419. Web of Science CSD CrossRef CAS Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Kim, H.-J. (2010). Acta Cryst. E66, o566. Web of Science CSD CrossRef IUCr Journals Google Scholar
Love, J. B., Blake, A. J., Wilson, C., Reid, S. D., Novak, A. & Hitchcock, P. B. (2003). Chem. Commun. pp. 1682–1683. Web of Science CSD CrossRef Google Scholar
Mahanta, S. P., Kumar, B. S., Baskaran, S., Sivasankar, C. & Panda, P. K. (2012). Org. Lett. 14, 548–551. Web of Science CSD CrossRef CAS PubMed Google Scholar
Prins, L. J., Reinhoudt, D. N. & Timmerman, P. (2001). Angew. Chem. Int. Ed. 40, 2382–2426. 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
Steiner, T. (2002). Angew. Chem. Int. Ed. 41, 48–76. Web of Science CrossRef CAS Google Scholar
Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D. & Spackman, M. A. (2017). CrystalExplorer17. University of Western Australia. Google Scholar
Uppal, T., Hu, X., Fronczek, F. R., Maschek, S., Bobadova-Parvanova, P. & Vicente, M. G. H. (2012). Chem. Eur. J. 18, 3893–3905. Web of Science CSD CrossRef CAS PubMed Google Scholar
Xie, H., Lee, D. A., Senge, M. O. & Smith, K. M. (1994). J. Chem. Soc. Chem. Commun. pp. 791–792. CrossRef Web of Science Google Scholar
Yin, Z. & Li, Z. (2006). Tetrahedron Lett. 47, 7875–7879. Web of Science CSD CrossRef CAS Google Scholar
Yin, Z., Zhang, Y., He, J. & Cheng, J.-P. (2007). Chem. Commun. pp. 2599–2601. Web of Science CSD CrossRef Google Scholar

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CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 75| Part 6| June 2019| Pages 711-713

https://doi.org/10.1107/S205698901900567X

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research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure and Hirshfeld surface analysis of di­butyl 5,5′-(pentane-3,3-diyl)bis­(1H-pyrrole-5-carboxylate)

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Hirshfeld surface

5. Database survey

6. Synthesis and crystallization

7. Refinement

Supporting information

Funding information

References

research communications

Crystal structure and Hirshfeld surface analysis of dibutyl 5,5′-(pentane-3,3-diyl)bis(1H-pyrrole-5-carboxylate)

3. Supramolecular features