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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 8| August 2012| Pages o2445-o2446
https://doi.org/10.1107/S1600536812031212

2-[(4-Meth­­oxy-2-nitro­phen­yl)imino­meth­yl]phenol

Aliakbar Dehno Khalaji,a Mahsa Nikookar,a Karla Fejfarováb* and Michal Dušekb

aDepartment of Chemistry, Faculty of Science, Golestan University, Gorgan, Iran, and bInstitute of Physics ASCR, v.v.i., Na Slovance 2, 182 21 Prague 8, Czech Republic
*Correspondence e-mail: fejfarov@fzu.cz

(Received 5 July 2012; accepted 9 July 2012; online 14 July 2012)

The crystal structure of the title compound, C14H12N2O4, contains four crystallographically independent mol­ecules in the asymmetric unit. All the mol­ecules have similar conformations; the dihedral angles between the aromatic rings are 33.1 (1), 33.76 (9), 31.41 (9) and 32.56 (10)°. Intra­molecular O—H⋯N hydrogen bonds form S(6) ring motifs in each molecule. In the crystal, there are two pairs of pseudo-inversion-related mol­ecules. Along the c axis, mol­ecules are stacked with π–π inter­actions between the 2-hy­droxy­phenyl and 4-meth­oxy-2-nitro­phenyl rings [centroid–centroid distances = 3.5441 (12)–3.7698 (12) Å].

Related literature

For related structures, see: Akkurt et al. (2008[Akkurt, M., Jarrahpour, A., Aye, M., Gençaslan, M. & Büyükgüngör, O. (2008). Acta Cryst. E64, o2087.]); Fejfarová et al. (2010[Fejfarová, K., Khalaji, A. D. & Dušek, M. (2010). Acta Cryst. E66, o2874.]); Fun et al. (2009[Fun, H.-K., Kia, R., Kargar, H. & Jamshidvand, A. (2009). Acta Cryst. E65, o706.]); Kargar et al. (2012[Kargar, H., Sharafi, Z., Kia, R. & Tahir, M. N. (2012). Acta Cryst. E68, o1036.]); Keleşoğlu et al. (2009[Keleşoğlu, Z., Büyükgüngör, O., Albayrak, Ç. & Odabaşoğlu, M. (2009). Acta Cryst. E65, o2055.]); Khalaji et al. (2007[Khalaji, A. D., Slawin, A. M. Z. & Woollins, J. D. (2007). Acta Cryst. E63, o4257.]); Özek et al. (2009[Özek, A., Albayrak, Ç. & Büyükgüngör, O. (2009). Acta Cryst. E65, o2705.]); Tanak et al. (2009[Tanak, H., Erşahin, F., Ağar, E., Yavuz, M. & Büyükgüngör, O. (2009). Acta Cryst. E65, o2291.]). For the extinction correction, see: Becker & Coppens (1974[Becker, P. J. & Coppens, P. (1974). Acta Cryst. A30, 129-147.]).

[Scheme 1]

Experimental

Crystal data

  • C14H12N2O4

  • Mr = 272.3

  • Monoclinic, P 21

  • a = 16.8655 (2) Å

  • b = 21.0838 (5) Å

  • c = 7.0741 (5) Å

  • β = 90.817 (2)°

  • V = 2515.22 (19) Å3

  • Z = 8

  • Cu Kα radiation

  • μ = 0.9 mm−1

  • T = 120 K

  • 0.25 × 0.20 × 0.16 mm
Data collection

  • Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]) Tmin = 0.851, Tmax = 1

  • 19454 measured reflections

  • 7375 independent reflections

  • 6684 reflections with I > 3σ(I)

  • Rint = 0.024
Refinement

  • R[F2 > 3σ(F2)] = 0.033

  • wR(F2) = 0.087

  • S = 1.38

  • 7375 reflections

  • 735 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.12 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2778 Friedel pairs

  • Flack parameter: −0.06 (15)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O104—H104o⋯N102 0.86 (3) 1.81 (3) 2.593 (2) 150 (3)
O204—H204o⋯N202 0.88 (3) 1.81 (3) 2.599 (2) 148 (3)
O304—H304o⋯N302 0.92 (3) 1.76 (3) 2.593 (2) 148 (3)
O404—H404o⋯N402 0.90 (3) 1.79 (3) 2.598 (2) 148 (3)

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003[Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.]); program(s) used to refine structure: JANA2006 (Petříček et al., 2006[Petříček, V., Dušek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Praha, Czech Republic.]); molecular graphics: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: JANA2006.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812031212/fk2064sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812031212/fk2064Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812031212/fk2064Isup3.cml

checkCIF report


Comment top

The present work is part of a structural study of Schiff bases (Khalaji et al., 2007; Fejfarová et al., 2010). The crystal structure contains four crystallographically independent molecules (A–D) in the asymmetric unit (Fig. 1 and 2). All the molecules have similar conformations, the dihedral angles between the two aromatic rings are 33.1 (1)°, 33.76 (9)°, 31.41 (9)°, and 32.56 (10)°. The azomethine functional groups are co-planar with the adjacent benzene rings. The dihedral angles between the planes of the benzene ring and the plane defined by C(aromatic)—C=N atoms are 2.8 (2)°, 1.50 (18)°, 3.19 (19)°, and 2.7 (2)°. The methoxy groups are almost coplanar with the adjacent benzene rings as can be seen from the torsion angles Cx03—Cx04—Ox03—Cx07 (x = 1–4 for molecules A–D) of -174.57 (19)°, -176.30 (17)°, 174.10 (17)°, and 176.27 (17)°, respectively. The average of C═N and C—N bond lengths of 1.286 and 1.407 Å agree well with the corresponding distances in other Schiff bases (Akkurt et al., 2008; Fun et al., 2009; Kargar et al., 2012; Keleşoğlu et al., 2009; Özek et al., 2009; Tanak et al., 2009.

In the crystal, there are two pairs (A+C, B+D) of pseudo inversion-related molecules. The phenol H atoms form strong intramolecular Ox04—H···Nx02 hydrogen bonds with the imine N atoms, generating S(6) ring motifs. Along the c axis, the molecules are stacked with π-π interactions between the 2-hydroxyphenyl and 4-methoxy-2-nitrophenyl rings of A+B and C+D pairs [centroid-centroid distances in the range of 3.5441 (12)Å – 3.7698 (12) Å] (Figure 3).

Related literature top

For related structures, see: Akkurt et al. (2008); Fejfarová et al. (2010); Fun et al. (2009); Kargar et al. (2012); Keleşoğlu et al. (2009); Khalaji et al. (2007); Özek et al. (2009); Tanak et al. (2009). For the extinction correction, see: Becker & Coppens (1974).

Experimental top

To a stirred solution of the salicylaldehyde (0.2 mmol, in 5 ml of methanol) was added 4-methoxy-2-nitroaniline (0.2 mmol) in 10 ml of methanol and the mixture was stirred for 1 h in air at 323 K and was then left at room temperature for several days without disturbance yielding suitable crystals of the title compound that subsequently were filtered off and washed with Et2O. Yield: 88%. Yellow crystals. Anal. Calc. for C14H12N2O4: C, 61.76; H, 4.44; N, 10.29%. Found: C, 61.70; H, 4.51; N, 10.38%.

Refinement top

Hydrogen atoms attached to carbons were kept in ideal positions with C–H distance 0.96 Å during the refinement. The methyl H atoms were allowed to rotate freely about the adjacent C—O bonds. The hydroxyl hydrogen atoms were found in difference Fourier maps and their coordinates were refined freely. The isotropic atomic displacement parameters of hydrogen atoms were set to 1.5Ueq (methyl and hydroxyl groups) or 1.2Ueq of the parent atom. Reflections -1 19 - 5 and 1 18 - 5 were omitted in last cycles of refinement as outliers.

Structure description top

The present work is part of a structural study of Schiff bases (Khalaji et al., 2007; Fejfarová et al., 2010). The crystal structure contains four crystallographically independent molecules (A–D) in the asymmetric unit (Fig. 1 and 2). All the molecules have similar conformations, the dihedral angles between the two aromatic rings are 33.1 (1)°, 33.76 (9)°, 31.41 (9)°, and 32.56 (10)°. The azomethine functional groups are co-planar with the adjacent benzene rings. The dihedral angles between the planes of the benzene ring and the plane defined by C(aromatic)—C=N atoms are 2.8 (2)°, 1.50 (18)°, 3.19 (19)°, and 2.7 (2)°. The methoxy groups are almost coplanar with the adjacent benzene rings as can be seen from the torsion angles Cx03—Cx04—Ox03—Cx07 (x = 1–4 for molecules A–D) of -174.57 (19)°, -176.30 (17)°, 174.10 (17)°, and 176.27 (17)°, respectively. The average of C═N and C—N bond lengths of 1.286 and 1.407 Å agree well with the corresponding distances in other Schiff bases (Akkurt et al., 2008; Fun et al., 2009; Kargar et al., 2012; Keleşoğlu et al., 2009; Özek et al., 2009; Tanak et al., 2009.

In the crystal, there are two pairs (A+C, B+D) of pseudo inversion-related molecules. The phenol H atoms form strong intramolecular Ox04—H···Nx02 hydrogen bonds with the imine N atoms, generating S(6) ring motifs. Along the c axis, the molecules are stacked with π-π interactions between the 2-hydroxyphenyl and 4-methoxy-2-nitrophenyl rings of A+B and C+D pairs [centroid-centroid distances in the range of 3.5441 (12)Å – 3.7698 (12) Å] (Figure 3).

For related structures, see: Akkurt et al. (2008); Fejfarová et al. (2010); Fun et al. (2009); Kargar et al. (2012); Keleşoğlu et al. (2009); Khalaji et al. (2007); Özek et al. (2009); Tanak et al. (2009). For the extinction correction, see: Becker & Coppens (1974).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: JANA2006 (Petříček et al., 2006); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: JANA2006 (Petříček et al., 2006).

Figures top
[Figure 1] Fig. 1. Molecules A and C of the title compound. Displacement ellipsoids are shown at the 50% probability level. Hydrogen bonds are drawn as dashed lines.
[Figure 2] Fig. 2. Molecules B and D of the title compound. Displacement ellipsoids are shown at the 50% probability level. Hydrogen bonds are drawn as dashed lines.
[Figure 3] Fig. 3. Packing of molecules viewed along c-axis. [red: A, blue: B, orange: C, cyan: D]
2-[(4-Methoxy-2-nitrophenyl)iminomethyl]phenol top
Crystal data top
C14H12N2O4F(000) = 1136
Mr = 272.3Dx = 1.438 Mg m−3
Monoclinic, P21Cu Kα radiation, λ = 1.5418 Å
Hall symbol: P 2ybCell parameters from 12919 reflections
a = 16.8655 (2) Åθ = 3.4–67.6°
b = 21.0838 (5) ŵ = 0.9 mm−1
c = 7.0741 (5) ÅT = 120 K
β = 90.817 (2)°Prism, yellow
V = 2515.22 (19) Å30.25 × 0.20 × 0.16 mm
Z = 8
Data collection top
Agilent Xcalibur
diffractometer with an Atlas (Gemini ultra Cu) detector		7375 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source6684 reflections with I > 3σ(I)
Mirror monochromatorRint = 0.024
Detector resolution: 10.3784 pixels mm-1θmax = 67.1°, θmin = 3.4°
Rotation method data acquisition using ω scansh = −20→20
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)		k = −25→19
Tmin = 0.851, Tmax = 1l = −8→8
19454 measured reflections
Refinement top
Refinement on F2Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0016I2)
R[F > 3σ(F)] = 0.033(Δ/σ)max = 0.040
wR(F) = 0.087Δρmax = 0.15 e Å−3
S = 1.38Δρmin = −0.12 e Å−3
7375 reflectionsExtinction correction: Becker & Coppens (1974), B-C type 1 Lorentzian isotropic
735 parametersExtinction coefficient: 23 (3)
0 restraintsAbsolute structure: Flack (1983), 2778 Friedel pairs
181 constraintsAbsolute structure parameter: −0.06 (15)
H atoms treated by a mixture of independent and constrained refinement
Crystal data top
C14H12N2O4V = 2515.22 (19) Å3
Mr = 272.3Z = 8
Monoclinic, P21Cu Kα radiation
a = 16.8655 (2) ŵ = 0.9 mm−1
b = 21.0838 (5) ÅT = 120 K
c = 7.0741 (5) Å0.25 × 0.20 × 0.16 mm
β = 90.817 (2)°
Data collection top
Agilent Xcalibur
diffractometer with an Atlas (Gemini ultra Cu) detector		7375 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)		6684 reflections with I > 3σ(I)
Tmin = 0.851, Tmax = 1Rint = 0.024
19454 measured reflections
Refinement top
R[F > 3σ(F)] = 0.033H atoms treated by a mixture of independent and constrained refinement
wR(F) = 0.087Δρmax = 0.15 e Å−3
S = 1.38Δρmin = −0.12 e Å−3
7375 reflectionsAbsolute structure: Flack (1983), 2778 Friedel pairs
735 parametersAbsolute structure parameter: −0.06 (15)
0 restraints
Special details top

Experimental. CrysAlis PRO (Agilent, 2012) 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
xyzUiso*/Ueq
O1010.75197 (9)0.40161 (8)0.2684 (2)0.0325 (5)
O1020.73997 (10)0.47881 (8)0.0692 (3)0.0418 (5)
O1030.44321 (9)0.47415 (8)0.0226 (2)0.0353 (5)
O1040.84363 (9)0.28817 (7)−0.0391 (2)0.0295 (4)
O2010.62031 (12)0.09153 (10)0.5791 (4)0.0695 (8)
O2020.60210 (9)0.17182 (8)0.7624 (2)0.0325 (5)
O2030.91500 (8)0.10142 (7)0.5481 (2)0.0290 (4)
O2040.51076 (9)0.28366 (7)0.4491 (2)0.0267 (4)
O3010.12187 (11)0.09018 (9)0.1065 (3)0.0560 (7)
O3020.09907 (9)0.17300 (7)−0.0624 (2)0.0313 (5)
O3030.41587 (8)0.10577 (7)0.1458 (2)0.0283 (4)
O3040.00811 (9)0.28192 (7)0.2504 (2)0.0286 (4)
O4010.23694 (9)0.48015 (8)0.6054 (3)0.0401 (5)
O4020.25409 (8)0.39560 (7)0.4393 (2)0.0303 (4)
O403−0.05477 (8)0.46909 (7)0.6735 (2)0.0283 (4)
O4040.34982 (9)0.28420 (7)0.7316 (2)0.0295 (4)
N1010.71506 (10)0.43047 (8)0.1454 (2)0.0252 (5)
N1020.69505 (10)0.30308 (8)0.0389 (2)0.0231 (5)
N2010.64206 (10)0.14142 (9)0.6521 (2)0.0281 (5)
N2020.65943 (9)0.26907 (8)0.5403 (2)0.0212 (5)
N3010.14073 (10)0.14177 (8)0.0458 (2)0.0263 (5)
N3020.15641 (9)0.26977 (8)0.1656 (2)0.0219 (5)
N4010.21568 (10)0.42781 (8)0.5491 (2)0.0235 (5)
N4020.19913 (10)0.29979 (8)0.6657 (2)0.0219 (5)
C1010.62753 (12)0.34198 (10)0.0459 (2)0.0226 (6)
C1020.63683 (12)0.40674 (10)0.0865 (2)0.0228 (5)
C1030.57583 (12)0.45023 (10)0.0748 (3)0.0250 (6)
C1040.50037 (12)0.42838 (11)0.0271 (3)0.0269 (6)
C1050.48848 (12)0.36469 (11)−0.0147 (3)0.0283 (6)
C1060.55178 (12)0.32283 (11)−0.0075 (3)0.0256 (6)
C1070.36311 (14)0.45354 (14)−0.0091 (4)0.0463 (8)
C1080.69080 (12)0.24352 (10)0.0766 (3)0.0231 (6)
C1090.75967 (12)0.20240 (10)0.0614 (3)0.0233 (6)
C1100.83385 (12)0.22653 (10)0.0064 (3)0.0249 (6)
C1110.89955 (14)0.18668 (11)0.0031 (3)0.0315 (7)
C1120.89183 (15)0.12361 (11)0.0522 (3)0.0349 (7)
C1130.81873 (15)0.09888 (11)0.1029 (3)0.0345 (7)
C1140.75348 (14)0.13811 (10)0.1074 (3)0.0288 (6)
C2010.72755 (11)0.23065 (10)0.5557 (2)0.0211 (5)
C2020.71981 (11)0.16640 (10)0.5997 (2)0.0220 (5)
C2030.78191 (12)0.12391 (10)0.5954 (3)0.0231 (5)
C2040.85700 (12)0.14623 (10)0.5498 (3)0.0235 (5)
C2050.86774 (12)0.21004 (10)0.5059 (3)0.0243 (6)
C2060.80306 (12)0.25102 (10)0.5070 (3)0.0233 (6)
C2070.99420 (13)0.12213 (11)0.5134 (3)0.0344 (7)
C2080.66305 (12)0.32867 (9)0.5764 (2)0.0212 (5)
C2090.59460 (12)0.36982 (9)0.5515 (2)0.0215 (5)
C2100.52078 (12)0.34580 (10)0.4906 (3)0.0225 (5)
C2110.45560 (13)0.38634 (10)0.4734 (3)0.0273 (6)
C2120.46387 (14)0.44984 (11)0.5144 (3)0.0294 (6)
C2130.53661 (13)0.47458 (10)0.5748 (3)0.0292 (6)
C2140.60111 (13)0.43468 (10)0.5936 (3)0.0258 (6)
C3010.22495 (12)0.23216 (10)0.1496 (2)0.0222 (5)
C3020.21824 (11)0.16775 (10)0.1029 (2)0.0219 (5)
C3030.28126 (12)0.12637 (10)0.1048 (3)0.0235 (6)
C3040.35633 (11)0.14957 (10)0.1511 (2)0.0227 (5)
C3050.36609 (12)0.21300 (10)0.1999 (3)0.0248 (6)
C3060.30082 (12)0.25293 (10)0.2010 (3)0.0246 (6)
C3070.49501 (13)0.12832 (11)0.1742 (3)0.0331 (7)
C3080.15887 (12)0.32986 (10)0.1339 (2)0.0225 (6)
C3090.09020 (12)0.36993 (10)0.1613 (3)0.0230 (6)
C3100.01678 (12)0.34448 (10)0.2162 (3)0.0231 (6)
C311−0.04890 (13)0.38389 (10)0.2325 (3)0.0275 (6)
C312−0.04221 (14)0.44799 (11)0.2012 (3)0.0315 (6)
C3130.03044 (14)0.47442 (11)0.1530 (3)0.0321 (6)
C3140.09536 (14)0.43544 (10)0.1301 (3)0.0285 (6)
C4010.13152 (12)0.33874 (10)0.6584 (2)0.0214 (5)
C4020.13938 (11)0.40338 (10)0.6143 (2)0.0205 (5)
C4030.07786 (11)0.44609 (10)0.6232 (3)0.0221 (5)
C4040.00308 (12)0.42425 (10)0.6733 (3)0.0238 (6)
C405−0.00726 (12)0.36086 (10)0.7203 (3)0.0242 (6)
C4060.05651 (12)0.31940 (10)0.7147 (3)0.0236 (6)
C407−0.13379 (13)0.44822 (11)0.7128 (3)0.0328 (7)
C4080.19402 (12)0.24032 (10)0.6266 (3)0.0225 (6)
C4090.26229 (12)0.19855 (9)0.6426 (3)0.0227 (6)
C4100.33761 (12)0.22219 (10)0.6938 (3)0.0246 (6)
C4110.40245 (13)0.18123 (11)0.7024 (3)0.0284 (6)
C4120.39276 (14)0.11775 (11)0.6651 (3)0.0319 (6)
C4130.31855 (14)0.09349 (11)0.6156 (3)0.0328 (7)
C4140.25409 (13)0.13381 (10)0.6036 (3)0.0275 (6)
H1030.5852370.4944170.0989540.03*
H1050.4364460.349691−0.0485730.0339*
H1060.5429410.279209−0.0405260.0308*
H107a0.3496170.4222740.0837060.0694*
H107b0.3581460.435414−0.1331740.0694*
H107c0.327940.4891440.0010040.0694*
H1080.6411740.2258440.1154510.0277*
H1110.9502220.203014−0.0333350.0378*
H1120.937540.0964860.0512630.0418*
H1130.8137740.0547950.1344830.0414*
H1140.7030240.1210680.142640.0346*
H2030.7735850.0798670.6233590.0277*
H2050.919440.2256470.4750560.0291*
H2060.8107560.2946620.4731750.0279*
H207a1.0287740.0860130.5086410.0517*
H207b0.9956110.1443280.3950290.0517*
H207c1.0113790.1499470.6133180.0517*
H2080.7122290.34650.6210550.0254*
H2110.4050490.3699380.4329010.0327*
H2120.4189020.4774880.5013070.0353*
H2130.5417650.5189390.602940.0351*
H2140.6511510.4515240.636170.031*
H3030.2736380.0823590.0748440.0282*
H3050.4177520.2290550.2326250.0298*
H3060.3080430.2963460.2382930.0296*
H307a0.5315770.0938270.1596680.0497*
H307b0.506160.1606430.0827650.0497*
H307c0.5004750.1456410.2991980.0497*
H3080.2073230.3485470.0911770.027*
H311−0.0992480.36620.2658640.033*
H312−0.0879530.4747430.2125430.0378*
H3130.0353350.5194070.1358970.0386*
H3140.1448880.4535170.0921360.0341*
H4030.0863170.4901230.5953990.0265*
H405−0.0585160.3457470.7567740.0291*
H4060.0486890.2759750.7506930.0283*
H407a−0.1696370.4834570.7021990.0492*
H407b−0.1491660.4159570.6238040.0492*
H407c−0.135470.4312890.8386420.0492*
H4080.1439040.2231430.5858640.027*
H4110.4540870.197460.734580.0341*
H4120.4376270.0898160.6733080.0382*
H4130.3122130.0490570.5898970.0393*
H4140.2030290.1171910.5679730.033*
H104o0.7988 (18)0.3068 (15)−0.021 (4)0.0442*
H204o0.5554 (17)0.2640 (14)0.477 (4)0.04*
H304o0.0559 (18)0.2624 (14)0.227 (4)0.0429*
H404o0.3030 (18)0.3046 (15)0.716 (4)0.0442*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1010.0300 (7)0.0356 (9)0.0317 (7)−0.0009 (7)−0.0051 (6)0.0042 (7)
O1020.0340 (8)0.0241 (9)0.0675 (11)−0.0051 (7)0.0032 (7)0.0137 (8)
O1030.0268 (7)0.0371 (9)0.0421 (8)0.0079 (7)0.0018 (6)0.0058 (7)
O1040.0289 (7)0.0236 (8)0.0361 (8)−0.0032 (6)0.0050 (6)−0.0027 (6)
O2010.0451 (11)0.0350 (11)0.129 (2)−0.0194 (9)0.0263 (12)−0.0368 (12)
O2020.0276 (7)0.0353 (9)0.0348 (7)0.0009 (7)0.0082 (6)−0.0014 (7)
O2030.0239 (7)0.0248 (8)0.0383 (8)0.0033 (6)0.0005 (5)−0.0023 (6)
O2040.0271 (7)0.0183 (7)0.0346 (7)−0.0015 (6)−0.0037 (6)−0.0005 (6)
O3010.0380 (9)0.0309 (10)0.0987 (15)−0.0136 (8)−0.0127 (9)0.0267 (10)
O3020.0289 (7)0.0313 (9)0.0336 (7)−0.0014 (6)−0.0066 (6)0.0010 (6)
O3030.0243 (7)0.0243 (8)0.0364 (7)0.0028 (6)0.0013 (5)0.0041 (6)
O3040.0288 (7)0.0189 (8)0.0381 (8)−0.0035 (6)0.0052 (6)−0.0026 (6)
O4010.0364 (8)0.0198 (8)0.0643 (10)−0.0075 (7)0.0074 (7)−0.0083 (8)
O4020.0279 (7)0.0298 (8)0.0335 (7)0.0019 (6)0.0063 (6)−0.0027 (6)
O4030.0229 (7)0.0236 (8)0.0384 (7)0.0054 (6)0.0025 (5)−0.0035 (6)
O4040.0279 (7)0.0222 (8)0.0383 (8)−0.0007 (6)−0.0015 (6)0.0021 (6)
N1010.0276 (8)0.0192 (9)0.0290 (8)0.0009 (7)0.0048 (7)−0.0026 (7)
N1020.0275 (8)0.0215 (9)0.0202 (7)0.0006 (7)0.0015 (6)−0.0008 (6)
N2010.0258 (9)0.0199 (9)0.0388 (9)−0.0021 (7)0.0029 (7)0.0007 (7)
N2020.0244 (8)0.0195 (9)0.0197 (7)−0.0003 (7)0.0021 (6)0.0004 (6)
N3010.0257 (9)0.0201 (9)0.0331 (9)−0.0017 (7)0.0006 (7)0.0004 (7)
N3020.0252 (8)0.0196 (9)0.0210 (7)0.0006 (7)−0.0005 (6)−0.0014 (6)
N4010.0243 (8)0.0184 (9)0.0277 (8)0.0004 (7)−0.0003 (6)0.0027 (7)
N4020.0249 (8)0.0189 (9)0.0220 (7)0.0020 (7)0.0015 (6)0.0023 (6)
C1010.0274 (10)0.0222 (11)0.0181 (8)−0.0006 (8)0.0035 (7)0.0019 (7)
C1020.0267 (9)0.0239 (11)0.0178 (8)−0.0007 (8)0.0011 (7)0.0017 (7)
C1030.0298 (10)0.0218 (11)0.0235 (9)0.0026 (8)0.0041 (7)0.0030 (8)
C1040.0273 (10)0.0318 (12)0.0218 (9)0.0073 (9)0.0029 (8)0.0052 (8)
C1050.0256 (10)0.0364 (13)0.0228 (9)−0.0030 (9)−0.0009 (7)0.0027 (8)
C1060.0283 (10)0.0274 (11)0.0213 (9)−0.0029 (9)0.0009 (7)−0.0005 (8)
C1070.0274 (12)0.0528 (17)0.0588 (15)0.0084 (11)0.0010 (10)0.0112 (13)
C1080.0266 (10)0.0225 (11)0.0200 (8)−0.0032 (8)−0.0006 (7)−0.0017 (8)
C1090.0320 (10)0.0212 (11)0.0168 (8)0.0001 (8)−0.0009 (7)−0.0032 (7)
C1100.0300 (10)0.0249 (11)0.0197 (8)−0.0015 (8)−0.0010 (7)−0.0062 (7)
C1110.0319 (11)0.0365 (13)0.0261 (10)0.0031 (9)−0.0018 (8)−0.0113 (9)
C1120.0454 (13)0.0328 (13)0.0262 (10)0.0136 (10)−0.0056 (9)−0.0087 (9)
C1130.0542 (14)0.0233 (11)0.0258 (10)0.0059 (10)−0.0035 (9)−0.0026 (8)
C1140.0420 (12)0.0208 (11)0.0236 (9)−0.0014 (9)−0.0004 (8)0.0007 (8)
C2010.0245 (9)0.0214 (10)0.0174 (8)−0.0003 (8)−0.0002 (7)−0.0017 (7)
C2020.0238 (9)0.0218 (10)0.0206 (8)−0.0023 (8)0.0020 (7)−0.0034 (7)
C2030.0288 (10)0.0173 (10)0.0231 (9)−0.0010 (8)0.0012 (7)−0.0011 (7)
C2040.0256 (10)0.0245 (11)0.0203 (8)0.0033 (8)−0.0017 (7)−0.0037 (8)
C2050.0246 (10)0.0249 (11)0.0234 (9)−0.0019 (8)0.0006 (7)−0.0009 (8)
C2060.0264 (10)0.0216 (11)0.0219 (9)−0.0021 (8)0.0012 (7)0.0002 (7)
C2070.0243 (10)0.0339 (13)0.0452 (12)0.0014 (9)−0.0002 (9)−0.0069 (10)
C2080.0242 (9)0.0210 (10)0.0185 (8)−0.0033 (8)0.0026 (7)0.0010 (7)
C2090.0282 (10)0.0189 (10)0.0176 (8)0.0002 (8)0.0040 (7)0.0024 (7)
C2100.0286 (10)0.0201 (10)0.0189 (8)−0.0003 (8)0.0016 (7)0.0012 (7)
C2110.0288 (10)0.0289 (11)0.0242 (9)0.0028 (9)0.0026 (7)0.0055 (8)
C2120.0378 (12)0.0251 (11)0.0254 (9)0.0082 (9)0.0057 (8)0.0040 (8)
C2130.0451 (12)0.0172 (10)0.0256 (9)0.0020 (9)0.0094 (8)0.0021 (8)
C2140.0338 (11)0.0217 (11)0.0221 (9)−0.0031 (8)0.0030 (8)0.0002 (8)
C3010.0274 (10)0.0213 (10)0.0179 (8)0.0007 (8)0.0019 (7)0.0006 (7)
C3020.0237 (9)0.0218 (10)0.0202 (8)−0.0025 (8)0.0022 (7)0.0039 (7)
C3030.0298 (10)0.0194 (10)0.0213 (8)−0.0002 (8)0.0022 (7)0.0025 (8)
C3040.0244 (9)0.0254 (11)0.0182 (8)0.0014 (8)0.0023 (7)0.0053 (7)
C3050.0244 (10)0.0278 (11)0.0222 (8)−0.0024 (9)0.0001 (7)0.0002 (8)
C3060.0300 (10)0.0218 (11)0.0221 (9)−0.0039 (8)0.0000 (7)−0.0019 (7)
C3070.0240 (10)0.0324 (13)0.0430 (12)0.0006 (9)0.0027 (9)0.0079 (9)
C3080.0254 (9)0.0240 (11)0.0181 (8)−0.0030 (8)−0.0002 (7)−0.0002 (7)
C3090.0307 (10)0.0202 (10)0.0180 (8)0.0001 (8)−0.0019 (7)−0.0003 (7)
C3100.0302 (10)0.0200 (10)0.0190 (8)−0.0009 (8)−0.0016 (7)−0.0008 (7)
C3110.0282 (10)0.0302 (12)0.0241 (9)0.0019 (9)−0.0009 (8)−0.0037 (8)
C3120.0408 (12)0.0298 (12)0.0238 (9)0.0124 (10)−0.0039 (8)−0.0015 (8)
C3130.0499 (13)0.0181 (11)0.0284 (10)0.0052 (10)−0.0004 (9)0.0019 (8)
C3140.0380 (11)0.0229 (11)0.0244 (9)−0.0031 (9)0.0004 (8)0.0030 (8)
C4010.0255 (9)0.0200 (10)0.0185 (8)0.0009 (8)−0.0018 (7)−0.0011 (7)
C4020.0249 (9)0.0194 (10)0.0171 (8)−0.0019 (8)−0.0001 (7)−0.0014 (7)
C4030.0261 (10)0.0178 (10)0.0224 (8)0.0019 (8)−0.0006 (7)−0.0026 (7)
C4040.0238 (10)0.0256 (11)0.0220 (9)0.0033 (8)−0.0005 (7)−0.0044 (8)
C4050.0244 (10)0.0263 (11)0.0221 (9)−0.0018 (8)0.0017 (7)−0.0005 (8)
C4060.0284 (10)0.0212 (10)0.0211 (9)−0.0004 (8)0.0021 (7)0.0015 (7)
C4070.0233 (10)0.0327 (13)0.0426 (12)0.0016 (9)0.0027 (9)−0.0070 (10)
C4080.0270 (10)0.0205 (10)0.0202 (8)−0.0013 (8)0.0039 (7)0.0028 (7)
C4090.0317 (11)0.0188 (10)0.0178 (8)0.0032 (8)0.0032 (7)0.0044 (7)
C4100.0300 (10)0.0232 (11)0.0207 (8)0.0007 (8)0.0053 (7)0.0052 (7)
C4110.0298 (11)0.0308 (12)0.0246 (9)0.0065 (9)0.0046 (8)0.0052 (8)
C4120.0396 (12)0.0303 (12)0.0259 (10)0.0147 (10)0.0088 (8)0.0063 (9)
C4130.0497 (13)0.0208 (11)0.0280 (10)0.0071 (10)0.0081 (9)−0.0013 (8)
C4140.0358 (11)0.0224 (11)0.0244 (9)0.0017 (9)0.0037 (8)0.0003 (8)
Geometric parameters (Å, º) top
O101—N1011.225 (2)C205—C2061.392 (3)
O102—N1011.230 (2)C205—H2050.96
O103—C1041.364 (3)C206—H2060.96
O103—C1071.434 (3)C207—H207a0.96
O104—C1101.350 (3)C207—H207b0.96
O104—H104o0.86 (3)C207—H207c0.96
O201—N2011.226 (3)C208—C2091.453 (3)
O202—N2011.220 (2)C208—H2080.96
O203—C2041.360 (2)C209—C2101.406 (3)
O203—C2071.430 (3)C209—C2141.403 (3)
O204—C2101.353 (2)C210—C2111.397 (3)
O204—H204o0.88 (3)C211—C2121.376 (3)
O301—N3011.214 (3)C211—H2110.96
O302—N3011.224 (2)C212—C2131.394 (3)
O303—C3041.365 (2)C212—H2120.96
O303—C3071.428 (3)C213—C2141.380 (3)
O304—C3101.349 (2)C213—H2130.96
O304—H304o0.92 (3)C214—H2140.96
O401—N4011.225 (2)C301—C3021.402 (3)
O402—N4011.224 (2)C301—C3061.396 (3)
O403—C4041.358 (2)C302—C3031.375 (3)
O403—C4071.434 (3)C303—C3041.392 (3)
O404—C4101.350 (3)C303—H3030.96
O404—H404o0.90 (3)C304—C3051.390 (3)
N101—C1021.466 (3)C305—C3061.386 (3)
N102—C1011.405 (3)C305—H3050.96
N102—C1081.286 (3)C306—H3060.96
N201—C2021.466 (3)C307—H307a0.96
N202—C2011.409 (3)C307—H307b0.96
N202—C2081.284 (3)C307—H307c0.96
N301—C3021.469 (3)C308—C3091.449 (3)
N302—C3011.408 (3)C308—H3080.96
N302—C3081.287 (3)C309—C3101.409 (3)
N401—C4021.467 (2)C309—C3141.402 (3)
N402—C4011.406 (3)C310—C3111.391 (3)
N402—C4081.287 (3)C311—C3121.374 (3)
C101—C1021.404 (3)C311—H3110.96
C101—C1061.387 (3)C312—C3131.393 (3)
C102—C1031.380 (3)C312—H3120.96
C103—C1041.390 (3)C313—C3141.380 (3)
C103—H1030.96C313—H3130.96
C104—C1051.389 (3)C314—H3140.96
C105—C1061.386 (3)C401—C4021.405 (3)
C105—H1050.96C401—C4061.393 (3)
C106—H1060.96C402—C4031.376 (3)
C107—H107a0.96C403—C4041.393 (3)
C107—H107b0.96C403—H4030.96
C107—H107c0.96C404—C4051.389 (3)
C108—C1091.455 (3)C405—C4061.387 (3)
C108—H1080.96C405—H4050.96
C109—C1101.410 (3)C406—H4060.96
C109—C1141.398 (3)C407—H407a0.96
C110—C1111.391 (3)C407—H407b0.96
C111—C1121.381 (3)C407—H407c0.96
C111—H1110.96C408—C4091.453 (3)
C112—C1131.390 (3)C408—H4080.96
C112—H1120.96C409—C4101.407 (3)
C113—C1141.377 (3)C409—C4141.399 (3)
C113—H1130.96C410—C4111.394 (3)
C114—H1140.96C411—C4121.373 (3)
C201—C2021.396 (3)C411—H4110.96
C201—C2061.392 (3)C412—C4131.392 (3)
C202—C2031.379 (3)C412—H4120.96
C203—C2041.393 (3)C413—C4141.382 (3)
C203—H2030.96C413—H4130.96
C204—C2051.393 (3)C414—H4140.96
C104—O103—C107116.95 (19)C210—C211—C212120.0 (2)
C110—O104—H104o107 (2)C210—C211—H211120.01
C204—O203—C207117.60 (16)C212—C211—H211120.01
C210—O204—H204o107.8 (19)C211—C212—C213121.0 (2)
C304—O303—C307117.21 (16)C211—C212—H212119.52
C310—O304—H304o107.9 (19)C213—C212—H212119.52
C404—O403—C407117.14 (16)C212—C213—C214119.4 (2)
C410—O404—H404o107.8 (19)C212—C213—H213120.32
O101—N101—O102123.36 (18)C214—C213—H213120.32
O101—N101—C102118.60 (16)C209—C214—C213120.94 (19)
O102—N101—C102118.04 (16)C209—C214—H214119.53
C101—N102—C108121.01 (17)C213—C214—H214119.53
O201—N201—O202123.75 (19)N302—C301—C302120.06 (17)
O201—N201—C202117.72 (18)N302—C301—C306123.60 (18)
O202—N201—C202118.52 (17)C302—C301—C306115.84 (18)
C201—N202—C208120.74 (17)N301—C302—C301119.65 (17)
O301—N301—O302123.54 (18)N301—C302—C303116.81 (18)
O301—N301—C302118.27 (17)C301—C302—C303123.54 (18)
O302—N301—C302118.18 (16)C302—C303—C304118.67 (19)
C301—N302—C308120.78 (17)C302—C303—H303120.67
O401—N401—O402123.44 (17)C304—C303—H303120.67
O401—N401—C402117.91 (16)O303—C304—C303115.01 (18)
O402—N401—C402118.64 (16)O303—C304—C305124.95 (17)
C401—N402—C408120.64 (17)C303—C304—C305120.03 (19)
N102—C101—C102119.14 (17)C304—C305—C306119.63 (19)
N102—C101—C106124.35 (18)C304—C305—H305120.19
C102—C101—C106116.02 (18)C306—C305—H305120.19
N101—C102—C101119.18 (17)C301—C306—C305122.24 (19)
N101—C102—C103117.24 (18)C301—C306—H306118.88
C101—C102—C103123.59 (18)C305—C306—H306118.88
C102—C103—C104118.3 (2)O303—C307—H307a109.47
C102—C103—H103120.87O303—C307—H307b109.47
C104—C103—H103120.87O303—C307—H307c109.47
O103—C104—C103114.54 (19)H307a—C307—H307b109.47
O103—C104—C105125.39 (19)H307a—C307—H307c109.47
C103—C104—C105120.1 (2)H307b—C307—H307c109.47
C104—C105—C106119.94 (19)N302—C308—C309121.52 (18)
C104—C105—H105120.03N302—C308—H308119.24
C106—C105—H105120.03C309—C308—H308119.24
C101—C106—C105122.1 (2)C308—C309—C310121.47 (18)
C101—C106—H106118.97C308—C309—C314120.14 (19)
C105—C106—H106118.97C310—C309—C314118.38 (19)
O103—C107—H107a109.47O304—C310—C309121.30 (18)
O103—C107—H107b109.47O304—C310—C311118.73 (18)
O103—C107—H107c109.47C309—C310—C311119.96 (19)
H107a—C107—H107b109.47C310—C311—C312120.5 (2)
H107a—C107—H107c109.47C310—C311—H311119.77
H107b—C107—H107c109.47C312—C311—H311119.77
N102—C108—C109121.33 (18)C311—C312—C313120.5 (2)
N102—C108—H108119.34C311—C312—H312119.76
C109—C108—H108119.34C313—C312—H312119.76
C108—C109—C110121.17 (18)C312—C313—C314119.5 (2)
C108—C109—C114119.90 (19)C312—C313—H313120.24
C110—C109—C114118.90 (19)C314—C313—H313120.24
O104—C110—C109121.68 (18)C309—C314—C313121.1 (2)
O104—C110—C111118.52 (19)C309—C314—H314119.43
C109—C110—C111119.78 (19)C313—C314—H314119.43
C110—C111—C112120.0 (2)N402—C401—C402119.72 (17)
C110—C111—H111120.02N402—C401—C406123.94 (18)
C112—C111—H111120.02C402—C401—C406115.88 (18)
C111—C112—C113120.9 (2)N401—C402—C401119.78 (17)
C111—C112—H112119.57N401—C402—C403116.75 (17)
C113—C112—H112119.57C401—C402—C403123.44 (18)
C112—C113—C114119.5 (2)C402—C403—C404118.77 (19)
C112—C113—H113120.25C402—C403—H403120.61
C114—C113—H113120.25C404—C403—H403120.61
C109—C114—C113121.0 (2)O403—C404—C403115.03 (18)
C109—C114—H114119.52O403—C404—C405125.22 (18)
C113—C114—H114119.52C403—C404—C405119.74 (19)
N202—C201—C202119.76 (17)C404—C405—C406119.97 (19)
N202—C201—C206123.46 (18)C404—C405—H405120.02
C202—C201—C206116.31 (18)C406—C405—H405120.02
N201—C202—C201119.45 (17)C401—C406—C405122.12 (19)
N201—C202—C203117.04 (18)C401—C406—H406118.94
C201—C202—C203123.50 (18)C405—C406—H406118.94
C202—C203—C204118.60 (19)O403—C407—H407a109.47
C202—C203—H203120.7O403—C407—H407b109.47
C204—C203—H203120.7O403—C407—H407c109.47
O203—C204—C203115.07 (18)H407a—C407—H407b109.47
O203—C204—C205124.95 (18)H407a—C407—H407c109.47
C203—C204—C205119.96 (18)H407b—C407—H407c109.47
C204—C205—C206119.59 (18)N402—C408—C409121.56 (18)
C204—C205—H205120.2N402—C408—H408119.22
C206—C205—H205120.2C409—C408—H408119.22
C201—C206—C205121.99 (19)C408—C409—C410121.12 (18)
C201—C206—H206119.01C408—C409—C414120.01 (18)
C205—C206—H206119.01C410—C409—C414118.86 (19)
O203—C207—H207a109.47O404—C410—C409121.93 (18)
O203—C207—H207b109.47O404—C410—C411118.29 (18)
O203—C207—H207c109.47C409—C410—C411119.77 (19)
H207a—C207—H207b109.47C410—C411—C412120.3 (2)
H207a—C207—H207c109.47C410—C411—H411119.86
H207b—C207—H207c109.47C412—C411—H411119.86
N202—C208—C209121.67 (17)C411—C412—C413120.7 (2)
N202—C208—H208119.16C411—C412—H412119.65
C209—C208—H208119.16C413—C412—H412119.65
C208—C209—C210121.37 (18)C412—C413—C414119.5 (2)
C208—C209—C214119.76 (18)C412—C413—H413120.22
C210—C209—C214118.84 (18)C414—C413—H413120.23
O204—C210—C209121.52 (18)C409—C414—C413120.8 (2)
O204—C210—C211118.56 (18)C409—C414—H414119.58
C209—C210—C211119.91 (19)C413—C414—H414119.58
C103—C104—O103—C107−174.57 (19)C303—C304—O303—C307174.10 (17)
C203—C204—O203—C207−176.30 (17)C403—C404—O403—C407176.27 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O104—H104o···N1020.86 (3)1.81 (3)2.593 (2)150 (3)
O204—H204o···N2020.88 (3)1.81 (3)2.599 (2)148 (3)
O304—H304o···N3020.92 (3)1.76 (3)2.593 (2)148 (3)
O404—H404o···N4020.90 (3)1.79 (3)2.598 (2)148 (3)

Experimental details

Crystal data
Chemical formulaC14H12N2O4
Mr272.3
Crystal system, space groupMonoclinic, P21
Temperature (K)120
a, b, c (Å)16.8655 (2), 21.0838 (5), 7.0741 (5)
β (°) 90.817 (2)
V (Å3)2515.22 (19)
Z8
Radiation typeCu Kα
µ (mm−1)0.9
Crystal size (mm)0.25 × 0.20 × 0.16
Data collection
DiffractometerAgilent Xcalibur
diffractometer with an Atlas (Gemini ultra Cu) detector
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2012)
Tmin, Tmax0.851, 1
No. of measured, independent and
observed [I > 3σ(I)] reflections		19454, 7375, 6684
Rint0.024
(sin θ/λ)max (Å−1)0.598
Refinement
R[F > 3σ(F)], wR(F), S 0.033, 0.087, 1.38
No. of reflections7375
No. of parameters735
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.15, −0.12
Absolute structureFlack (1983), 2778 Friedel pairs
Absolute structure parameter−0.06 (15)

Computer programs: CrysAlis PRO (Agilent, 2012), SIR2002 (Burla et al., 2003), JANA2006 (Petříček et al., 2006), DIAMOND (Brandenburg & Putz, 2005).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O104—H104o···N1020.86 (3)1.81 (3)2.593 (2)150 (3)
O204—H204o···N2020.88 (3)1.81 (3)2.599 (2)148 (3)
O304—H304o···N3020.92 (3)1.76 (3)2.593 (2)148 (3)
O404—H404o···N4020.90 (3)1.79 (3)2.598 (2)148 (3)
 

Acknowledgements

We acknowledge Golestan University for partial support of this work, the Institutional Research Plan No. AVOZ10100521 of the Institute of Physics, Prague, and the Praemium Academiae Project of the Academy of Sciences of the Czech Republic.

References

First citationAgilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.  Google Scholar
 First citationAkkurt, M., Jarrahpour, A., Aye, M., Gençaslan, M. & Büyükgüngör, O. (2008). Acta Cryst. E64, o2087.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationBecker, P. J. & Coppens, P. (1974). Acta Cryst. A30, 129–147.  CrossRef IUCr Journals Web of Science Google Scholar
 First citationBrandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationBurla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.  CrossRef IUCr Journals Google Scholar
 First citationFejfarová, K., Khalaji, A. D. & Dušek, M. (2010). Acta Cryst. E66, o2874.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationFun, H.-K., Kia, R., Kargar, H. & Jamshidvand, A. (2009). Acta Cryst. E65, o706.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationKargar, H., Sharafi, Z., Kia, R. & Tahir, M. N. (2012). Acta Cryst. E68, o1036.  CSD CrossRef IUCr Journals Google Scholar
 First citationKeleşoğlu, Z., Büyükgüngör, O., Albayrak, Ç. & Odabaşoğlu, M. (2009). Acta Cryst. E65, o2055.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationKhalaji, A. D., Slawin, A. M. Z. & Woollins, J. D. (2007). Acta Cryst. E63, o4257.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationÖzek, A., Albayrak, Ç. & Büyükgüngör, O. (2009). Acta Cryst. E65, o2705.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationPetříček, V., Dušek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Praha, Czech Republic.  Google Scholar
 First citationTanak, H., Erşahin, F., Ağar, E., Yavuz, M. & Büyükgüngör, O. (2009). Acta Cryst. E65, o2291.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 68| Part 8| August 2012| Pages o2445-o2446
https://doi.org/10.1107/S1600536812031212
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