Crystal structures of 2,5-di­azido-1,4-phenyl­ene di­acetate and 2,5-di­azido-1,4-phenyl­ene dibutyrate

Glöcklhofer, F.; Fröhlich, J.; Stöger, B.; Weil, M.

doi:10.1107/S1600536814013762

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ISSN: 2056-9890

Volume 70| Part 7| July 2014| Pages 39-42

https://doi.org/10.1107/S1600536814013762

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Crystal structures of 2,5-diazido-1,4-phenylene diacetate and 2,5-diazido-1,4-phenylene dibutyrate

Florian Glöcklhofer,^a Johannes Fröhlich,^a Berthold Stöger ^b and Matthias Weil ^b ^*

^aInstitute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163, A-1060 Vienna, Austria, and ^bInstitute for Chemical Technologies and Analytics, Division of Structural Chemistry, Vienna University of Technology, Getreidemarkt 9/164-SC, A-1060 Vienna, Austria
^*Correspondence e-mail: mweil@mail.zserv.tuwien.ac.at

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 11 June 2014; accepted 12 June 2014; online 23 June 2014)

The asymmetric units of the title compounds, C₁₀H₈N₆O₄, (I), and C₁₄H₁₆N₆O₄, (II), each contain half of the respective molecule which is completed by inversion symmetry. The two molecules differ in the ester moiety (acetate versus butyrate) and the crystal symmetry is different, i.e. triclinic for (I) and monoclinic for (II). The diazidophenylene moieties are essentially planar [maximum deviation of 0.0216 (7) Å for (I) and 0.0330 (14) Å for (II)], and the ester functionalities are almost perpendicular to these planes, making dihedral angles of 79.93 (3)° for (I) and 79.42 (6)° for (II). In the crystals of both (I) and (II), there are no significant intermolecular interactions present.

Keywords: crystal structure; click chemistry; azides.

CCDC references: 1008063; 1008064

1. Chemical context

In recent years, copper(I)-catalysed cycloaddition of organic azides and alkynes towards 1,4-disubstituted triazoles attained immense interest in various fields of organic chemistry and became famous as the `cream of the crop' of click chemistry (Moses & Moorhouse, 2007 ). In materials chemistry, this kind of reaction is often applied for the synthesis of functional polymers (Qin et al., 2010 ).

The title compounds, (I) and (II), were synthesized to investigate their applicability in such polymerizations, viz. AA–BB polymerizations with dialkynes. The synthetic accessibility of the two compounds from inexpensive starting materials is remarkable, making them suitable for large scale preparation. However, their electron-deficient character represents a challenge to the polymerization parameters. The crystal structures of (I) and (II) are reported herein.

2. Structural commentary

The molecular structures of (I) and (II) are displayed in Figs. 1 and 2, respectively. Both molecules possess inversion symmetry. Although the two molecules differ only in the ester moiety (acetate versus butyrate), the crystal symmetry is different, i.e. triclinic for (I), with Z = 1, and monoclinic for (II), with Z = 2. The diazidophenylene moieties do not differ significantly from planarity, with a maximum deviation of 0.0216 (7) Å in (I) and 0.0330 (14) Å in (II), for the unsubstituted atom C3 in both cases. The azide groups, both in trans positions to each other, deviate slightly from a linear arrangement, with an N—N—N angle of 173.01 (9)° for (I) and 172.59 (16)° for (II). The mean planes of the acetate [C—C(=O)—O)] and butyrate [C—C—C—C(=O)—O] groups are almost normal to the mean planes of the diazidophenylene moieties, with a dihedral angle of 79.93 (3)° for (I) and 79.42 (6)° for (II).

Figure 1
The molecular structure of compound (I)

, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 80% probability level. Unlabelled atoms are generated by the symmetry code (−x + 1, −y, −z).

Figure 2
The molecular structure of compound (II)

, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 80% probability level. Unlabelled atoms are generated by the symmetry code (−x + 1, −y, −z).

3. Supramolecular features

There are no notable features in terms of π–π stacking interactions or hydrogen bonding in either structure. The crystal packing of (I) and (II) seems to be dominated mainly by van der Waals forces (Figs. 3 and 4, respectively).

Figure 3
A view along [100] of the crystal packing of compound (I)

. Colour code: O red, C grey, N light-blue and H white.

Figure 4
A view along [010] of the crystal packing of compound (II)

. Colour code: O red, C grey, N light-blue and H white.

4. Database survey

In the Cambridge Structural Database (Version 5.35, last update February 2014; Allen, 2002 ) no structures of compounds containing a trans-diazidophenylene entity are listed, making the two examples presented herein the only ones reported so far.

5. Synthesis and crystallization

Both target compounds were synthesized following a two-step protocol (Fig. 5), previously published for 2,5-diazido-1,4-phenylene diacetate by Moore et al. (1969 ). In view of the light sensitivity of the intermediate compound 2,5-diazidobenzene-1,4-diol, all reactions were carried out under light protection.

Figure 5
Reaction scheme for the synthesis of the title compounds.

Preparation of 2,5-diazidobenzene-1,4-diol: 1,4-benzoquinone (10.81 g, 100.0 mmol, 1.0 equivalent) was dissolved in glacial acetic acid (100 ml, 1.0 M) and cooled to 288 K using an ice-water bath. NaN₃ (14.3 g, 220 mol, 2.2 equivalents) was dissolved in water (44 ml, 5.0 M) and added to the cooled and stirred solution of 1,4-benzoquinone in one portion. Stirring was stopped after 15 min and the flask was sealed and stored at 278 K overnight for crystallization. Vacuum filtration afforded a light-yellow solid, which was washed three times with water and dried in vacuo overnight to afford 2,5-diazidobenzene-1,4-diol (yield: 6.60 g, 34.4 mmol, 69%). 1,4-Benzoquinone serves as starting material and as oxidation reagent in this reaction, resulting in a theoretical molar yield of only half of the applied starting material (50 mmol).

Preparation of 2,5-diazido-1,4-phenylene diacetate, (I): 2,5-diazidobenzene-1,4-diol (1.92 g, 10.0 mmol) was added to preheated (313 K) acetic anhydride (100 ml, 0.1 M) in one portion and the reaction stirred until complete dissolution of the starting material. The reaction mixture was then allowed to cool to room temperature and stored overnight to allow 2,5-diazido-1,4-phenylene diacetate to crystallize. Vacuum filtration afforded light-orange crystals of compound (I), which were washed with water three time (yield: 1.73 g, 6.26 mmol, 63%). ¹H NMR (CDCl₃, 200 MHz): δ 6.89 (s, 2H), 2.33 (s, 6H); ¹³C NMR (CDCl₃, 50 MHz): δ 168.3 (s), 140.0 (s), 129.3 (s), 115.3 (d), 20.4 (q).

Preparation of 2,5-diazido-1,4-phenylene dibutyrate, (II): 2,5-diazidobenzene-1,4-diol (1.34 g, 7.0 mmol) was added to preheated (333 K) butyric anhydride (20 ml, 0.35 M) in one portion and the resulting suspension stirred for 45 min at this temperature. The reaction mixture was then allowed to cool to room temperature and stored for 5 days to allow 2,5-diazido-1,4-phenylene dibutyrate to crystallize. Vacuum filtration afforded yellow crystals of compound (II), which were washed with water three times and with ethanol twice (yield: 814 mg, 2.45 mmol, 35%). ¹H NMR (CDCl₃, 200 MHz): δ 6.88 (s, 2H), 2.57 (t, J = 7.4 Hz, 4H), 1.80 (sext, J = 7.4 Hz, 4H), 1.05 (t, J = 7.4 Hz, 6H); ¹³C NMR (CDCl₃, 50 MHz): δ 171.1 (s), 140.0 (s), 129.3 (s), 115.3 (d), 35.6 (t), 18.3 (t), 13.6 (q).

6. Refinement

For both structures, (I) and (II), the H atoms were included in calculated positions and treated as riding atoms, with C—H = 0.96 Å and U_iso(H) = 1.2U_eq(C).

Table 1
Experimental details

	(I)	(II)
Crystal data
Chemical formula	C₁₀H₈N₆O₄	C₁₄H₁₆N₆O₄
M_r	276.2	332.3
Crystal system, space group	Triclinic, P $[\overline{1}]$	Monoclinic, P2₁/n
Temperature (K)	100	100
a, b, c (Å)	5.4293 (6), 5.5678 (6), 10.4945 (12)	11.5875 (19), 5.1485 (8), 14.327 (2)
α, β, γ (°)	101.508 (3), 104.544 (3), 97.057 (3)	90, 108.496 (5), 90
V (Å³)	295.86 (6)	810.6 (2)
Z	1	2
Radiation type	Mo Kα	Mo Kα
μ (mm⁻¹)	0.12	0.10
Crystal size (mm)	0.65 × 0.55 × 0.25	0.65 × 0.25 × 0.08

Data collection
Diffractometer	Bruker Kappa APEXII CCD	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2013 )	Multi-scan (SADABS; Bruker, 2013)
T_min, T_max	0.92, 0.97	0.97, 0.99
No. of measured, independent and observed [I > 3σ(I)] reflections	15989, 2182, 1983	17268, 1781, 1211
R_int	0.037	0.043
(sin θ/λ)_max (Å⁻¹)	0.764	0.662

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.056, 3.22	0.042, 0.048, 2.15
No. of reflections	2182	1781
No. of parameters	91	109
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.23	0.26, −0.23
Computer programs: APEX2 and SAINT-Plus (Bruker, 2013), SUPERFLIP (Palatinus & Chapuis, 2007 ), JANA2006 (Petříček, et al., 2014 ), Mercury (Macrae et al., 2008 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC references: 1008063; 1008064

Crystal structure: contains datablocks general, I, II. DOI: https://doi.org/10.1107/S1600536814013762/su0008sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536814013762/su0008Isup2.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S1600536814013762/su0008IIsup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536814013762/su0008Isup4.cml

Supporting information file. DOI: https://doi.org/10.1107/S1600536814013762/su0008IIsup5.cml

checkCIF report

Computing details top

For both compounds, data collection: APEX2 (Bruker, 2013); cell refinement: SAINT-Plus (Bruker, 2013); data reduction: SAINT-Plus (Bruker, 2013); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: JANA2006 (Petříček, et al., 2014); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

(I) 2,5-Diazido-1,4-phenylene diacetate top

Crystal data top

C₁₀H₈N₆O₄	V = 295.86 (6) Å³
M_r = 276.2	Z = 1
Triclinic, P1	F(000) = 142
Hall symbol: -P 1	D_x = 1.550 Mg m⁻³
a = 5.4293 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 5.5678 (6) Å	θ = 3.8–32.8°
c = 10.4945 (12) Å	µ = 0.12 mm⁻¹
α = 101.508 (3)°	T = 100 K
β = 104.544 (3)°	Irregular, light-orange
γ = 97.057 (3)°	0.65 × 0.55 × 0.25 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2182 independent reflections
Radiation source: X-ray tube	1983 reflections with I > 3σ(I)
Graphite monochromator	R_int = 0.037
ω and φ scans	θ_max = 32.9°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2013)	h = −8→8
T_min = 0.92, T_max = 0.97	k = −8→8
15989 measured reflections	l = −15→16

Refinement top

Refinement on F	16 constraints
R[F > 3σ(F)] = 0.034	H-atom parameters constrained
wR(F) = 0.056	Weighting scheme based on measured s.u.'s w = 1/(σ²(F) + 0.0001F²)
S = 3.22	(Δ/σ)_max = 0.011
2182 reflections	Δρ_max = 0.46 e Å⁻³
91 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints

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

	x	y	z	U_iso*/U_eq
O1	0.25671 (10)	0.01146 (10)	0.20279 (5)	0.01189 (16)
O2	0.59540 (11)	0.28134 (10)	0.35546 (6)	0.01772 (18)
N1	0.36886 (13)	0.27117 (12)	−0.19926 (6)	0.0141 (2)
N2	0.19623 (12)	0.39755 (11)	−0.19328 (6)	0.01377 (19)
N3	0.04446 (14)	0.51922 (13)	−0.19896 (8)	0.0208 (2)
C1	0.42743 (13)	0.13837 (12)	−0.09681 (7)	0.0106 (2)
C2	0.38596 (13)	0.01109 (13)	0.10373 (7)	0.01038 (19)
C3	0.31388 (13)	0.14839 (12)	0.00901 (7)	0.0108 (2)
C4	0.38466 (14)	0.15794 (13)	0.33011 (7)	0.0119 (2)
C5	0.22479 (16)	0.13357 (15)	0.42495 (7)	0.0174 (2)
H1c3	0.185611	0.250721	0.016023	0.013*
H1c5	0.054271	0.162226	0.38606	0.0208*
H2c5	0.213484	−0.031171	0.440361	0.0208*
H3c5	0.303627	0.253962	0.509525	0.0208*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0113 (3)	0.0152 (2)	0.0096 (2)	0.00109 (19)	0.00522 (18)	0.00195 (18)
O2	0.0164 (3)	0.0197 (3)	0.0148 (3)	−0.0021 (2)	0.0057 (2)	0.0004 (2)
N1	0.0169 (3)	0.0155 (3)	0.0139 (3)	0.0069 (2)	0.0072 (2)	0.0064 (2)
N2	0.0161 (3)	0.0132 (3)	0.0137 (3)	0.0024 (2)	0.0056 (2)	0.0056 (2)
N3	0.0214 (4)	0.0201 (3)	0.0276 (4)	0.0089 (3)	0.0118 (3)	0.0119 (3)
C1	0.0113 (3)	0.0107 (3)	0.0096 (3)	0.0016 (2)	0.0032 (2)	0.0021 (2)
C2	0.0105 (3)	0.0116 (3)	0.0091 (3)	0.0012 (2)	0.0042 (2)	0.0011 (2)
C3	0.0106 (3)	0.0115 (3)	0.0107 (3)	0.0027 (2)	0.0040 (2)	0.0018 (2)
C4	0.0144 (3)	0.0124 (3)	0.0102 (3)	0.0039 (2)	0.0049 (2)	0.0028 (2)
C5	0.0186 (4)	0.0228 (4)	0.0129 (3)	0.0030 (3)	0.0091 (3)	0.0037 (3)

Geometric parameters (Å, º) top

O1—C2	1.3924 (10)	C1—C3	1.3943 (11)
O1—C4	1.3758 (8)	C2—C3	1.3810 (11)
O2—C4	1.1971 (9)	C3—H1c3	0.96
N1—N2	1.2456 (10)	C4—C5	1.4904 (12)
N1—C1	1.4167 (10)	C5—H1c5	0.96
N2—N3	1.1269 (10)	C5—H2c5	0.96
C1—C2ⁱ	1.3944 (11)	C5—H3c5	0.96

C2—O1—C4	116.60 (5)	C2—C3—H1c3	120
N2—N1—C1	115.40 (7)	O1—C4—O2	122.32 (7)
N1—N2—N3	173.01 (9)	O1—C4—C5	110.16 (6)
N1—C1—C2ⁱ	116.58 (7)	O2—C4—C5	127.51 (6)
N1—C1—C3	124.83 (7)	C4—C5—H1c5	109.47
C2ⁱ—C1—C3	118.59 (7)	C4—C5—H2c5	109.47
O1—C2—C1ⁱ	119.80 (7)	C4—C5—H3c5	109.47
O1—C2—C3	118.66 (7)	H1c5—C5—H2c5	109.47
C1ⁱ—C2—C3	121.42 (7)	H1c5—C5—H3c5	109.47
C1—C3—C2	120.00 (7)	H2c5—C5—H3c5	109.47
C1—C3—H1c3	120

Symmetry code: (i) −x+1, −y, −z.

(II) 2,5-Diazido-1,4-phenylene dibutyrate top

Crystal data top

C₁₄H₁₆N₆O₄	F(000) = 348
M_r = 332.3	D_x = 1.361 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7352 reflections
a = 11.5875 (19) Å	θ = 2.7–27.0°
b = 5.1485 (8) Å	µ = 0.10 mm⁻¹
c = 14.327 (2) Å	T = 100 K
β = 108.496 (5)°	Rod, light-yellow
V = 810.6 (2) Å³	0.65 × 0.25 × 0.08 mm
Z = 2

Data collection top

Bruker Kappa APEXII CCD diffractometer	1781 independent reflections
Radiation source: X-ray tube	1211 reflections with I > 3σ(I)
Graphite monochromator	R_int = 0.043
ω and φ scans	θ_max = 28.1°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2013)	h = −13→14
T_min = 0.97, T_max = 0.99	k = −6→6
17268 measured reflections	l = −17→18

Refinement top

Refinement on F	32 constraints
R[F > 3σ(F)] = 0.042	H-atom parameters constrained
wR(F) = 0.048	Weighting scheme based on measured s.u.'s w = 1/(σ²(F) + 0.0001F²)
S = 2.15	(Δ/σ)_max = 0.005
1781 reflections	Δρ_max = 0.26 e Å⁻³
109 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints

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

	x	y	z	U_iso*/U_eq
O1	0.28390 (9)	0.01294 (17)	0.04347 (7)	0.0217 (4)
O2	0.33949 (10)	−0.32997 (19)	0.14715 (7)	0.0269 (4)
N1	0.68785 (12)	0.3626 (2)	0.07891 (8)	0.0224 (5)
N2	0.67449 (11)	0.5255 (2)	0.13953 (9)	0.0225 (5)
N3	0.67447 (13)	0.6825 (2)	0.19484 (9)	0.0296 (5)
C1	0.58925 (14)	0.1863 (2)	0.04072 (10)	0.0177 (5)
C2	0.39470 (14)	0.0013 (3)	0.02402 (10)	0.0181 (5)
C3	0.48219 (14)	0.1877 (3)	0.06446 (10)	0.0190 (5)
C4	0.26254 (15)	−0.1781 (3)	0.10334 (10)	0.0214 (6)
C5	0.13432 (15)	−0.1622 (3)	0.10373 (11)	0.0265 (6)
C6	0.10348 (15)	−0.3423 (3)	0.17548 (11)	0.0303 (6)
C7	−0.02989 (17)	−0.3320 (4)	0.16734 (13)	0.0411 (7)
H1c3	0.468982	0.31648	0.108459	0.0228*
H1c5	0.080047	−0.194143	0.038568	0.0318*
H2c5	0.116086	0.013496	0.116656	0.0318*
H1c6	0.152049	−0.298391	0.241353	0.0364*
H2c6	0.125093	−0.51698	0.164467	0.0364*
H1c7	−0.045158	−0.450116	0.21394	0.0493*
H2c7	−0.050726	−0.158801	0.180958	0.0493*
H3c7	−0.078376	−0.380637	0.101973	0.0493*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0263 (7)	0.0157 (5)	0.0273 (6)	0.0017 (5)	0.0143 (5)	0.0033 (4)
O2	0.0324 (7)	0.0217 (6)	0.0303 (6)	0.0055 (5)	0.0150 (5)	0.0053 (5)
N1	0.0290 (9)	0.0153 (6)	0.0251 (7)	−0.0013 (6)	0.0114 (6)	−0.0036 (6)
N2	0.0264 (9)	0.0159 (6)	0.0247 (7)	−0.0015 (6)	0.0072 (6)	0.0037 (6)
N3	0.0397 (10)	0.0189 (7)	0.0297 (7)	−0.0022 (6)	0.0101 (7)	−0.0052 (6)
C1	0.0231 (10)	0.0108 (7)	0.0194 (7)	−0.0002 (6)	0.0069 (7)	0.0020 (6)
C2	0.0218 (10)	0.0148 (7)	0.0208 (8)	0.0040 (7)	0.0109 (7)	0.0048 (6)
C3	0.0283 (10)	0.0112 (7)	0.0189 (8)	0.0023 (6)	0.0095 (7)	0.0016 (6)
C4	0.0309 (11)	0.0135 (7)	0.0225 (8)	−0.0025 (7)	0.0124 (7)	−0.0029 (6)
C5	0.0286 (11)	0.0212 (8)	0.0320 (9)	0.0005 (7)	0.0131 (7)	0.0019 (7)
C6	0.0338 (11)	0.0259 (9)	0.0356 (9)	−0.0051 (8)	0.0173 (8)	0.0004 (7)
C7	0.0376 (12)	0.0516 (12)	0.0386 (11)	−0.0118 (9)	0.0184 (9)	0.0030 (9)

Geometric parameters (Å, º) top

O1—C2	1.399 (2)	C4—C5	1.490 (3)
O1—C4	1.3780 (19)	C5—C6	1.509 (2)
O2—C4	1.2023 (17)	C5—H1c5	0.96
N1—N2	1.2518 (18)	C5—H2c5	0.96
N1—C1	1.4257 (18)	C6—C7	1.513 (3)
N2—N3	1.1318 (18)	C6—H1c6	0.96
C1—C2ⁱ	1.392 (2)	C6—H2c6	0.96
C1—C3	1.387 (2)	C7—H1c7	0.96
C2—C3	1.3825 (19)	C7—H2c7	0.96
C3—H1c3	0.96	C7—H3c7	0.96

C2—O1—C4	116.81 (11)	C4—C5—H2c5	109.47
N2—N1—C1	115.62 (14)	C6—C5—H1c5	109.47
N1—N2—N3	172.59 (16)	C6—C5—H2c5	109.47
N1—C1—C2ⁱ	115.94 (15)	H1c5—C5—H2c5	103.47
N1—C1—C3	124.96 (13)	C5—C6—C7	112.50 (13)
C2ⁱ—C1—C3	119.09 (13)	C5—C6—H1c6	109.47
O1—C2—C1ⁱ	119.18 (12)	C5—C6—H2c6	109.47
O1—C2—C3	118.96 (13)	C7—C6—H1c6	109.47
C1ⁱ—C2—C3	121.71 (15)	C7—C6—H2c6	109.47
C1—C3—C2	119.20 (14)	H1c6—C6—H2c6	106.26
C1—C3—H1c3	120.4	C6—C7—H1c7	109.47
C2—C3—H1c3	120.4	C6—C7—H2c7	109.47
O1—C4—O2	122.63 (16)	C6—C7—H3c7	109.47
O1—C4—C5	109.84 (12)	H1c7—C7—H2c7	109.47
O2—C4—C5	127.53 (15)	H1c7—C7—H3c7	109.47
C4—C5—C6	114.88 (12)	H2c7—C7—H3c7	109.47
C4—C5—H1c5	109.47

Symmetry code: (i) −x+1, −y, −z.

Acknowledgements

The X-ray centre of the Vienna University of Technology is acknowledged for providing access to the single-crystal diffractometer.

References

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Volume 70| Part 7| July 2014| Pages 39-42

https://doi.org/10.1107/S1600536814013762

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

Crystal structures of 2,5-di­azido-1,4-phenyl­ene di­acetate and 2,5-di­azido-1,4-phenyl­ene dibutyrate

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

Acknowledgements

References

research communications

Crystal structures of 2,5-diazido-1,4-phenylene diacetate and 2,5-diazido-1,4-phenylene dibutyrate

3. Supramolecular features