N,N′-Bis(2,3-dimethoxy­benzyl­idene)propane-1,3-diamine

Fejfarová, K.; Dehno Khalaji, A.; Dušek, M.

doi:10.1107/S1600536809031651

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2288

doi:10.1107/S1600536809031651

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N,N′-Bis(2,3-dimethoxybenzylidene)propane-1,3-diamine

Karla Fejfarová,^a Aliakbar Dehno Khalaji ^b and Michal Dušek ^a ^*

^aInstitute of Physics of the ASCR, Na Slovance 2, 182 21 Prague 8, Czech Republic, and ^bDepartment of Chemistry, Faculty of Science, Golestan University, Gorgan, Iran
^*Correspondence e-mail: dusek@fzu.cz

(Received 10 August 2009; accepted 11 August 2009; online 29 August 2009)

The title compound, C₂₁H₂₆N₂O₄, adopts an E configuration with respect to the azomethine C=N bonds. The dihedral angle between the two rings is 8.16 (8)°. The crystal structure is stabilized by weak intermolecular C—H⋯O interactions.

Related literature

For the chemistry of Schiff base derivatives, see: Morshedi et al. (2009a ,b ); Dehno Khalaji et al. (2009 ); Khalaji et al. (2007 ); Wang (2008 ); Fun et al. (2008 ). For their applications, see: Ardizzoia et al. (2009 ); Gao et al. (2003 ). For the extinction correction, see: Becker & Coppens (1974 ).

Experimental

Crystal data

C₂₁H₂₆N₂O₄
M_r = 370.4
Orthorhombic, P n a 2₁
a = 15.3079 (3) Å
b = 9.2915 (2) Å
c = 13.8059 (3) Å
V = 1963.66 (7) Å³
Z = 4
Cu Kα radiation
μ = 0.71 mm⁻¹
T = 120 K
0.51 × 0.31 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector
Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis Pro. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.628, T_max = 0.871
26538 measured reflections
1623 independent reflections
1616 reflections with I > 3σ(I)
R_int = 0.021
θ_max = 62.4°

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.077
S = 1.97
1623 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.10 e Å⁻³
Δρ_min = −0.09 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O4ⁱ	0.96	2.59	3.411 (2)	143
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis Pro (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis Pro. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ); program(s) used to refine structure: JANA2006 (Petříček et al., 2007 ); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: JANA2006.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809031651/bt5030sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809031651/bt5030Isup2.hkl

checkCIF report

Comment top

Schiff bases range among the most chelating ligands found in the field of coordination chemistry (Morshedi et al., 2009a,b). Their compounds with transition metals have wide applications in the field of magnetism (Gao et al., 2003) and catalysis (Ardizzoia et al., 2009). The title compound has been studied as an extension of our work on the structural characterization of bidentate Schiff base compounds with di- and trimethoxy benzaldehyde (Khalaji et al., 2007 and Dehno Khalaji et al., 2009).

The molecule of the title compound is shown in Fig.1. All bond lengths and angles are comparable with those observed in similar compounds (Khalaji et al., 2007 and Dehno Khalaji et al., 2009). The C7=N1 and C11=N2 bond lengths of 1.264 (2) and 1.263 (2) Å, respectively, conform to the value for a double bonds while C8—N1 and C10—N2 bond lengths of 1.458 (2) and 1.458 (2) Å, respectively, conform to the value for single bonds. The molecule displays an E configuration around the C=N double bond. The azomethine groups are coplanar with the aromatic rings. The dihedral angle between two phenyl rings is 8.16 (8)°. The neigbouring molecules are interconnected by C—H···O hydrogen bonds to infinite chains. These chains are linked by C—H···π interactions into sheets (Fig. 2).

Related literature top

For the chemistry of Schiff base derivatives, see: Morshedi et al. (2009a,b); Dehno Khalaji et al. (2009); Khalaji et al. (2007); Wang (2008); Fun et al. (2008). For their applications, see: Ardizzoia et al. (2009); Gao et al. (2003).

For related literature, see: Becker & Coppens (1974).

Experimental top

2,3-Dimethoxybenzaldehyde (0.2 mmol) and 1,3-propanediamine (0.1 mmol) were dissolved in ethanol (50 ml). The mixture was stirred at room temperature for 1 h to give a clear solution. Suitable crystals of the title compound for X-ray study were formed by slow evaporation of the solvent over 8 days at room temperature (Yield 85%).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: JANA2006 (Petříček et al., 2007); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: JANA2006 (Petříček et al., 2007).

Figures top

	Fig. 1. The molecular structure of the title compound with atom-labeling scheme, with hydrogen bond shown as a dashed line. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry codes: (i) 0.5 - x, 1/2 + y, z - 1/2]
	Fig. 2. The packing of (I) viewed along b, with hydrogen bonds shown as blue dashed lines and C—H···π interaction as red dashed lines.

N,N'-Bis(2,3-dimethoxybenzylidene)propane-1,3-diamine top

Crystal data top

C₂₁H₂₆N₂O₄	F(000) = 792
M_r = 370.4	D_x = 1.253 Mg m⁻³
Orthorhombic, Pna2₁	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2c -2n	Cell parameters from 24214 reflections
a = 15.3079 (3) Å	θ = 3.2–62.3°
b = 9.2915 (2) Å	µ = 0.71 mm⁻¹
c = 13.8059 (3) Å	T = 120 K
V = 1963.66 (7) Å³	Irregular shape, colorless
Z = 4	0.51 × 0.31 × 0.20 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector	1623 independent reflections
Radiation source: X-ray tube	1616 reflections with I > 3σ(I)
Mirror monochromator	R_int = 0.021
Detector resolution: 20.7567 pixels mm^-1	θ_max = 62.4°, θ_min = 5.6°
Rotation method data acquisition using ω scans	h = −17→17
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −10→10
T_min = 0.628, T_max = 0.871	l = −15→15
26538 measured reflections

Refinement top

Refinement on F²	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.025	Weighting scheme based on measured s.u.'s w = 1/[σ²(I) + 0.0016I²]
wR(F²) = 0.077	(Δ/σ)_max = 0.038
S = 1.97	Δρ_max = 0.10 e Å⁻³
1623 reflections	Δρ_min = −0.09 e Å⁻³
244 parameters	Extinction correction: B–C type 1 Lorentzian isotropic (Becker & Coppens, 1974)
0 restraints	Extinction coefficient: 2800 (1000)
105 constraints

Crystal data top

C₂₁H₂₆N₂O₄	V = 1963.66 (7) Å³
M_r = 370.4	Z = 4
Orthorhombic, Pna2₁	Cu Kα radiation
a = 15.3079 (3) Å	µ = 0.71 mm⁻¹
b = 9.2915 (2) Å	T = 120 K
c = 13.8059 (3) Å	0.51 × 0.31 × 0.20 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector	1623 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	1616 reflections with I > 3σ(I)
T_min = 0.628, T_max = 0.871	R_int = 0.021
26538 measured reflections	θ_max = 62.4°

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.077	H-atom parameters constrained
S = 1.97	Δρ_max = 0.10 e Å⁻³
1623 reflections	Δρ_min = −0.09 e Å⁻³
244 parameters

Special details top

Experimental. CrysAlisPro (Oxford Diffraction, 2009) Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F² for refinement carried out on F and F², respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.

The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

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

	x	y	z	U_iso*/U_eq
O1	0.26797 (8)	0.00499 (13)	0.18586 (12)	0.0306 (4)
O2	0.18047 (7)	−0.18392 (11)	0.07546 (13)	0.0282 (3)
O3	0.46602 (7)	0.01788 (12)	0.27381 (11)	0.0315 (4)
O4	0.57090 (7)	−0.12117 (13)	0.40069 (13)	0.0348 (4)
N1	0.22853 (8)	0.43567 (14)	0.17846 (14)	0.0279 (4)
N2	0.46937 (8)	0.45543 (14)	0.24531 (14)	0.0281 (4)
C1	0.18698 (9)	0.20195 (17)	0.11887 (15)	0.0239 (4)
C2	0.20316 (10)	0.05443 (16)	0.12523 (15)	0.0239 (4)
C3	0.16066 (9)	−0.04171 (17)	0.06289 (16)	0.0246 (4)
C4	0.10498 (10)	0.01093 (17)	−0.00881 (15)	0.0274 (5)
C5	0.09133 (10)	0.15967 (17)	−0.01601 (15)	0.0292 (5)
C6	0.13056 (11)	0.25368 (17)	0.04693 (16)	0.0272 (5)
C7	0.23004 (10)	0.30040 (17)	0.18825 (14)	0.0246 (4)
C8	0.27152 (10)	0.52016 (17)	0.25365 (14)	0.0263 (5)
C9	0.34446 (10)	0.61189 (16)	0.21099 (14)	0.0262 (5)
C10	0.41895 (11)	0.52360 (17)	0.16833 (15)	0.0277 (5)
C11	0.47382 (10)	0.31972 (17)	0.24671 (15)	0.0253 (5)
C12	0.52555 (9)	0.24424 (17)	0.32177 (14)	0.0244 (4)
C13	0.52359 (10)	0.09464 (17)	0.32989 (15)	0.0249 (4)
C14	0.57636 (10)	0.02498 (19)	0.39893 (16)	0.0275 (5)
C15	0.62910 (10)	0.10661 (19)	0.46004 (15)	0.0301 (5)
C16	0.62956 (11)	0.25595 (19)	0.45242 (15)	0.0303 (5)
C17	0.57829 (10)	0.32443 (18)	0.38485 (15)	0.0272 (5)
C18	0.23861 (13)	−0.0640 (2)	0.27226 (15)	0.0402 (6)
C19	0.14018 (12)	−0.28468 (19)	0.01141 (16)	0.0327 (5)
C20	0.50416 (12)	−0.0730 (2)	0.20153 (18)	0.0396 (6)
C21	0.62707 (12)	−0.1948 (2)	0.46665 (17)	0.0400 (6)
H4	0.076366	−0.053919	−0.052675	0.0329*
H5	0.053814	0.196398	−0.065946	0.035*
H6	0.119366	0.355051	0.041722	0.0327*
H7	0.260269	0.26004	0.242784	0.0295*
H8a	0.295303	0.456715	0.301782	0.0315*
H8b	0.229431	0.581308	0.284681	0.0315*
H9a	0.32086	0.674064	0.162003	0.0314*
H9b	0.366972	0.675138	0.259983	0.0314*
H10a	0.395548	0.450955	0.126235	0.0333*
H10b	0.456428	0.58522	0.131065	0.0333*
H11	0.443276	0.264808	0.198515	0.0303*
H15	0.66515	0.059858	0.507446	0.0361*
H16	0.666035	0.31172	0.494737	0.0364*
H17	0.5786	0.427575	0.380869	0.0327*
H18a	0.288071	−0.09841	0.308189	0.0482*
H18b	0.206536	0.003592	0.311013	0.0482*
H18c	0.201483	−0.14353	0.255709	0.0482*
H19a	0.156576	−0.380645	0.029678	0.0393*
H19b	0.077848	−0.274903	0.015211	0.0393*
H19c	0.159047	−0.266242	−0.053739	0.0393*
H20a	0.4592	−0.108672	0.159426	0.0475*
H20b	0.545747	−0.018776	0.164399	0.0475*
H20c	0.533122	−0.15241	0.23229	0.0475*
H21a	0.615974	−0.296407	0.463211	0.0479*
H21b	0.686855	−0.176274	0.449786	0.0479*
H21c	0.616154	−0.16141	0.531323	0.0479*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0289 (6)	0.0321 (7)	0.0309 (6)	0.0034 (4)	−0.0083 (5)	0.0007 (5)
O2	0.0280 (6)	0.0220 (6)	0.0346 (6)	−0.0006 (4)	−0.0038 (5)	−0.0025 (5)
O3	0.0245 (6)	0.0338 (6)	0.0362 (7)	−0.0033 (4)	−0.0073 (5)	−0.0013 (5)
O4	0.0298 (6)	0.0339 (6)	0.0405 (7)	−0.0035 (4)	−0.0091 (5)	0.0143 (6)
N1	0.0261 (7)	0.0265 (7)	0.0310 (8)	0.0016 (5)	−0.0001 (6)	−0.0017 (6)
N2	0.0267 (7)	0.0287 (7)	0.0288 (7)	0.0025 (5)	0.0028 (6)	−0.0020 (6)
C1	0.0185 (7)	0.0264 (8)	0.0268 (8)	0.0012 (6)	0.0048 (6)	−0.0005 (7)
C2	0.0185 (7)	0.0281 (8)	0.0250 (8)	0.0017 (6)	0.0011 (6)	−0.0002 (6)
C3	0.0194 (7)	0.0245 (8)	0.0298 (8)	−0.0010 (5)	0.0052 (7)	−0.0003 (7)
C4	0.0179 (7)	0.0347 (9)	0.0297 (9)	−0.0020 (6)	0.0000 (7)	−0.0032 (7)
C5	0.0225 (8)	0.0348 (8)	0.0303 (10)	0.0045 (6)	−0.0027 (7)	0.0020 (7)
C6	0.0237 (8)	0.0259 (8)	0.0322 (8)	0.0035 (6)	0.0025 (6)	0.0011 (7)
C7	0.0219 (7)	0.0269 (8)	0.0250 (8)	0.0005 (6)	0.0021 (6)	−0.0006 (6)
C8	0.0286 (9)	0.0236 (7)	0.0266 (8)	0.0038 (6)	0.0008 (7)	−0.0028 (7)
C9	0.0308 (8)	0.0219 (8)	0.0258 (8)	0.0023 (6)	0.0002 (6)	−0.0004 (6)
C10	0.0306 (9)	0.0268 (8)	0.0257 (8)	0.0014 (6)	0.0025 (7)	0.0002 (7)
C11	0.0214 (8)	0.0302 (8)	0.0243 (8)	0.0007 (5)	0.0019 (6)	−0.0039 (7)
C12	0.0184 (7)	0.0313 (8)	0.0236 (8)	0.0013 (5)	0.0046 (6)	−0.0018 (7)
C13	0.0181 (7)	0.0327 (8)	0.0241 (8)	−0.0017 (6)	0.0010 (6)	−0.0002 (7)
C14	0.0213 (7)	0.0355 (8)	0.0256 (8)	−0.0001 (6)	0.0033 (6)	0.0032 (7)
C15	0.0198 (7)	0.0461 (10)	0.0243 (8)	0.0018 (7)	−0.0018 (6)	0.0025 (7)
C16	0.0229 (8)	0.0417 (9)	0.0264 (9)	0.0008 (6)	0.0011 (6)	−0.0086 (8)
C17	0.0195 (8)	0.0334 (9)	0.0289 (9)	0.0016 (6)	0.0038 (6)	−0.0073 (7)
C18	0.0560 (12)	0.0369 (10)	0.0277 (9)	0.0151 (8)	0.0010 (8)	0.0018 (7)
C19	0.0338 (9)	0.0256 (8)	0.0388 (9)	−0.0044 (7)	−0.0058 (7)	−0.0029 (7)
C20	0.0442 (10)	0.0393 (9)	0.0352 (10)	−0.0108 (8)	−0.0042 (8)	−0.0069 (8)
C21	0.0356 (10)	0.0442 (10)	0.0401 (10)	0.0030 (7)	−0.0057 (8)	0.0177 (9)

Geometric parameters (Å, º) top

O1—C2	1.377 (2)	C9—H9a	0.96
O1—C18	1.427 (2)	C9—H9b	0.96
O2—C3	1.3668 (18)	C10—H10a	0.96
O2—C19	1.428 (2)	C10—H10b	0.96
O3—C13	1.373 (2)	C11—C12	1.481 (3)
O3—C20	1.432 (3)	C11—H11	0.96
O4—C14	1.361 (2)	C12—C13	1.395 (2)
O4—C21	1.427 (3)	C12—C17	1.402 (2)
N1—C7	1.264 (2)	C13—C14	1.407 (3)
N1—C8	1.458 (2)	C14—C15	1.392 (3)
N2—C10	1.458 (2)	C15—C16	1.392 (2)
N2—C11	1.263 (2)	C15—H15	0.96
C1—C2	1.396 (2)	C16—C17	1.375 (3)
C1—C6	1.401 (3)	C16—H16	0.96
C1—C7	1.479 (2)	C17—H17	0.96
C2—C3	1.401 (2)	C18—H18a	0.96
C3—C4	1.395 (3)	C18—H18b	0.96
C4—C5	1.401 (2)	C18—H18c	0.96
C4—H4	0.96	C19—H19a	0.96
C5—C6	1.371 (3)	C19—H19b	0.96
C5—H5	0.96	C19—H19c	0.96
C6—H6	0.96	C20—H20a	0.96
C7—H7	0.96	C20—H20b	0.96
C8—C9	1.523 (2)	C20—H20c	0.96
C8—H8a	0.96	C21—H21a	0.96
C8—H8b	0.96	C21—H21b	0.96
C9—C10	1.523 (2)	C21—H21c	0.96

C2—O1—C18	115.54 (13)	N2—C11—C12	120.82 (17)
C3—O2—C19	117.35 (15)	N2—C11—H11	119.5897
C13—O3—C20	115.95 (13)	C12—C11—H11	119.5889
C14—O4—C21	116.94 (15)	C11—C12—C13	121.11 (15)
C7—N1—C8	116.79 (16)	C11—C12—C17	119.41 (14)
C10—N2—C11	118.25 (16)	C13—C12—C17	119.48 (16)
C2—C1—C6	119.40 (16)	O3—C13—C12	119.09 (15)
C2—C1—C7	119.17 (16)	O3—C13—C14	120.77 (15)
C6—C1—C7	121.43 (14)	C12—C13—C14	120.03 (16)
O1—C2—C1	119.59 (15)	O4—C14—C13	115.84 (16)
O1—C2—C3	119.70 (13)	O4—C14—C15	124.64 (17)
C1—C2—C3	120.35 (16)	C13—C14—C15	119.52 (16)
O2—C3—C2	115.82 (16)	C14—C15—C16	120.02 (17)
O2—C3—C4	124.38 (16)	C14—C15—H15	119.9905
C2—C3—C4	119.75 (14)	C16—C15—H15	119.9904
C3—C4—C5	119.16 (16)	C15—C16—C17	120.65 (17)
C3—C4—H4	120.42	C15—C16—H16	119.6771
C5—C4—H4	120.4205	C17—C16—H16	119.6769
C4—C5—C6	121.22 (17)	C12—C17—C16	120.28 (15)
C4—C5—H5	119.3896	C12—C17—H17	119.8593
C6—C5—H5	119.3903	C16—C17—H17	119.8611
C1—C6—C5	120.05 (15)	O1—C18—H18a	109.4709
C1—C6—H6	119.9753	O1—C18—H18b	109.4711
C5—C6—H6	119.9765	O1—C18—H18c	109.4709
N1—C7—C1	122.50 (17)	H18a—C18—H18b	109.4714
N1—C7—H7	118.7511	H18a—C18—H18c	109.4717
C1—C7—H7	118.7506	H18b—C18—H18c	109.4712
N1—C8—C9	110.91 (16)	O2—C19—H19a	109.4712
N1—C8—H8a	109.4708	O2—C19—H19b	109.4713
N1—C8—H8b	109.4707	O2—C19—H19c	109.4707
C9—C8—H8a	109.4715	H19a—C19—H19b	109.4714
C9—C8—H8b	109.4712	H19a—C19—H19c	109.4716
H8a—C8—H8b	107.9975	H19b—C19—H19c	109.4711
C8—C9—C10	113.38 (13)	O3—C20—H20a	109.4712
C8—C9—H9a	109.4711	O3—C20—H20b	109.4716
C8—C9—H9b	109.471	O3—C20—H20c	109.4718
C10—C9—H9a	109.4708	H20a—C20—H20b	109.471
C10—C9—H9b	109.4724	H20a—C20—H20c	109.4707
H9a—C9—H9b	105.2553	H20b—C20—H20c	109.4711
N2—C10—C9	110.39 (16)	O4—C21—H21a	109.4718
N2—C10—H10a	109.4708	O4—C21—H21b	109.4707
N2—C10—H10b	109.4703	O4—C21—H21c	109.4713
C9—C10—H10a	109.472	H21a—C21—H21b	109.4709
C9—C10—H10b	109.4717	H21a—C21—H21c	109.4715
H10a—C10—H10b	108.5415	H21b—C21—H21c	109.4711

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O4ⁱ	0.96	2.59	3.411 (2)	143

Symmetry code: (i) −x+1/2, y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₆N₂O₄
M_r	370.4
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	120
a, b, c (Å)	15.3079 (3), 9.2915 (2), 13.8059 (3)
V (Å³)	1963.66 (7)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.71
Crystal size (mm)	0.51 × 0.31 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.628, 0.871
No. of measured, independent and observed [I > 3σ(I)] reflections	26538, 1623, 1616
R_int	0.021
θ_max (°)	62.4
(sin θ/λ)_max (Å⁻¹)	0.575

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.077, 1.97
No. of reflections	1623
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.10, −0.09

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SIR2002 (Burla et al., 2003), JANA2006 (Petříček et al., 2007), DIAMOND (Brandenburg & Putz, 2005).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O4ⁱ	0.96	2.59	3.411 (2)	143

Symmetry code: (i) −x+1/2, y+1/2, z−1/2.

Acknowledgements

We acknowledge Golestan University (GU) for partial support of this work, the institutional research plan No. AVOZ10100521 of the Institute of Physics and the Praemium Academiae project of the Academy of Sciences of the Czech Republic.

References

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