data reports
ISSN 2056-9890
Crystal structure of N-[4-amino-5-cyano6-(methylsulfanyl)pyridin-2-yl]acetamide hemihydrate Mehmet Akkurt,a Kyle S. Knight,b Shaaban K. Mohamed,c,d Bahgat R. M. Husseine and Mustafa R. Albayatif*
2. Experimental 2.1. Crystal data = 82.136 (11) ˚3 V = 1075.4 (7) A Z=4 Mo K radiation = 0.29 mm1 T = 200 K 0.40 0.40 0.40 mm
a
Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, bDepartment of Chemistry, The University of Tennessee at Chattanooga, Chattanooga, TN 37403, USA, cChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, dChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, eChemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt, and fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq. *Correspondence e-mail: [email protected]
C9H10N4OS0.5H2O Mr = 231.28 Triclinic, P1 ˚ a = 8.229 (3) A ˚ b = 10.181 (4) A ˚ c = 13.198 (5) A = 84.221 (10) = 80.036 (10)
Received 4 February 2015; accepted 6 February 2015
2.2. Data collection
Edited by H. Stoeckli-Evans, University of Neuchaˆtel, Switzerland
Bruker SMART X2S benchtop diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009) Tmin = 0.813, Tmax = 1.000
The title compound, C9H10N4OS0.5H2O, crystallizes with two independent molecules (A and B) in the asymmetric unit, together with a water molecule of crystallization. The acetamide moiety, which has an extended conformation, is inclined to the pyridine ring by 7.95 (16) in molecule A and by 1.77 (16) in molecule B. In the crystal, the A and B molecules are linked by two N—H Ocarbonyl hydrogen bonds, forming a dimer. The dimers are linked via N— H N hydrogen bonds, forming ribbons that are linked by N—H Owater hydrogen bonds to form sheets parallel to (110). The sheets are linked by O—H N hydrogen bonds, forming slabs, and between the slabs there are weak slipped parallel – interactions [inter-centroid distance = ˚ , interplanar distance = 3.3505 (11) A ˚ and slippage 3.734 (2) A ˚ = 1.648 A], forming a three-dimensional structure. Keywords: crystal structure; poly-functional pyridines; acetamide; disorder; hydrogen bonding. CCDC reference: 1048267
2.3. Refinement R[F 2 > 2(F 2)] = 0.052 wR(F 2) = 0.150 S = 1.03 3775 reflections 305 parameters 9 restraints
H atoms treated by a mixture of independent and constrained refinement ˚ 3 max = 0.63 e A ˚ 3 min = 0.31 e A
Table 1 ˚ , ). Hydrogen-bond geometry (A D—H A
D—H
H A
D A
D—H A
N3—H3AN O2 N7—H7BN O1 N3—H3BN N8i N7—H7AN N4ii N2—H2N O3A N2—H2N O3B N6—H6N O3Aiii N6—H6N O3Biii O3A—H3A2 N7iv O3B—H3B1 N5v
0.88 0.88 0.88 0.88 0.88 0.88 0.88 0.88 0.85 (2) 0.85 (2)
2.00 1.99 2.33 2.38 2.12 2.21 2.26 2.19 2.36 (6) 2.57 (6)
2.870 (3) 2.860 (3) 3.080 (4) 3.116 (4) 2.984 (10) 3.079 (9) 3.138 (10) 3.051 (9) 3.083 (12) 3.239 (8)
169 170 143 142 166 172 173 166 143 (9) 137 (8)
Symmetry codes: (i) x þ 1; y 1; z; (ii) x 1; y þ 1; z; (iii) x; y; z þ 1; (iv) x þ 1; y þ 1; z; (v) x; y; z 1.
1. Related literature For various applications of polyfunctional pyridines, see: Knyazhanskii et al. (1996); Kurfurst et al. (1989); Enyedy et al. (2003); Arora & Knaus (1999); Kim et al. 2004); Pillai et al. (2003).
Acta Cryst. (2015). E71, o171–o172
19554 measured reflections 3775 independent reflections 2517 reflections with I > 2(I) Rint = 0.066
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics:
doi:10.1107/S205698901500256X
Akkurt et al.
o171
data reports PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 and PLATON.
Acknowledgements We are grateful to the University of Tennessee and Sohag University for supporting this study. Supporting information for this paper is available from the IUCr electronic archives (Reference: SU5077).
References
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Enyedy, I. J., Sakamuri, S., Zaman, W. A., Johnson, K. M. & Wang, S. (2003). Bioorg. Med. Chem. Lett. 13, 513–517. Kim, B. Y., Ahn, J. B., Lee, H. W., Kang, S. K., Lee, J. H., Shin, J. S., Ahn, S. K., Hong, C. I. & Yoon, S. S. (2004). Eur. J. Med. Chem. 39, 433–447. Knyazhanskii, M. I., Makarova, N. I., Olekhmovich, E. P. & Kharlanov, A. (1996). Zh. Org. Khim. 32, 1097–1103. Kurfu¨rst, A., Lhota´k, P., Petru˚, M. & Kuthan, J. (1989). Collect. Czech. Chem. Commun. 54, 462–472. Pillai, A. D., Rathod, P. D., Franklin, P. X., Patel, M., Nivsarkar, M., Vasu, K. K., Padh, H. & Sudarsanam, V. (2003). Biochem. Biophys. Res. Commun. 301, 183–186. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Spek, A. L. (2009). Acta Cryst. D65, 148–155.
Arora, V. K. & Knaus, E. E. (1999). J. Heterocycl. Chem. 36, 201–203.
o172
Akkurt et al.
C9H10N4OS0.5H2O
Acta Cryst. (2015). E71, o171–o172
supporting information
supporting information Acta Cryst. (2015). E71, o171–o172
[doi:10.1107/S205698901500256X]
Crystal structure of N-[4-amino-5-cyano-6-(methylsulfanyl)pyridin-2yl]acetamide hemihydrate Mehmet Akkurt, Kyle S. Knight, Shaaban K. Mohamed, Bahgat R. M. Hussein and Mustafa R. Albayati S1. Comment Poly-functional pyridines are an interesting class of compounds due to their optical properties (Knyazhanskii et al., 1996; Kurfurst et al., 1989), and their biological activities (Enyedy et al., 2003), such as anticonvulsants (Arora et al., 1999), antihistaminic reagents (Kim et al., 2004), and cardivascular disorder treatments (Pillai et al., 2003). In view of such facts we herein report on the synthesis and crystal structure of the new title poly-functional pyridine compound. The asymmetric unit of the title compound, Fig. 1, contains two independent title molecules (A and B) and one water molecule. In molecule A the dihedral angle between the pyridine ring (N1/C1–C5) and the acetamide moiety (O1/N2(C7/C8) is 7.95 (16)°, while in molecule B the corresponding angle, involving the pyridine ring (N5/C10-C14) and actemide moiety (O2/N2/C7/C8), is 1.77 (16)°. In the crystal, the A and B molecules are linked by two N-H···Ocarbonyl hydrogen bonds forming a dimer (Table 1 and Fig. 1). The dimers are linked via N-H···N hydrogen bonds forming ribbons that are linked by N-H···Owater hydrogen bonds to form sheets parallel to (110); see Table 1. The sheets are linked by O-H···N hydrogen bonds forming slabs (Table 1). Between the slabs there are weak slipped parallel π-π interactions forming a three-dimensional structure, Fig. 2 [intercentroid distance Cg1···Cg1i = 3.734 (2) Å, inter-planar distance = 3.351 (1) Å, slippage = 1.648 Å; Cg1 is the centroid of ring N5/C10-C14 (molecule B); symmetry code: (i) -x, -y+1, -z+1]. S2. Experimental A solution of 0.5 g (2.7 mmol) of 4,6-diamino-3-cyano-2-methylthiopyridine-2(1H)-thione in 30 ml glacial acetic acid was refluxed for 3 h. The reaction mixture was allowed to cool and it was then poured into 100 ml of ice cold water. The formed precipitate was collected and dried under vacuum. Yellow crystals, suitable for X-ray analysis, were obtained by recrystallization of the solid product from ethanol (yield: 92%; m.p.: 523–525 K). S3. Refinement The water molecule O3 is disordered over two positions (O3A/O3B) and was refined with an occupancy ratio of 0.5:0.5. The H atoms were included in calculated positions (calc-OH in WinGX; Farrugia, 2012 and refined with distance restraints: O—H = 0.84 (2) Å and H···H = 1.35 (2) Å with Uiso(H) = 1.5Ueq(O). The C and N-bound H atoms were placed in calculated positions and treated as riding atoms: C—H = 0.95 - 0.98 Å and N—H = 0.88 Å, with Uiso(H) = 1.5Ueq(C) for methyl H atoms and = 1.2Ueq(N,C) for other H atoms.
Acta Cryst. (2015). E71, o171–o172
sup-1
supporting information
Figure 1 Molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. The N—H···O hydrogen bonds are shown as dashed lines (see Table 1 for details).
Acta Cryst. (2015). E71, o171–o172
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supporting information
Figure 2 View along the c axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1 for details; H atoms not involved in hydrogen bonding have been omitted for clarity). N-[4-Amino-5-cyano-6-(methylsulfanyl)pyridin-2-yl]acetamide hemihydrate Crystal data C9H10N4OS·0.5H2O Mr = 231.28 Triclinic, P1 a = 8.229 (3) Å b = 10.181 (4) Å c = 13.198 (5) Å α = 84.221 (10)° β = 80.036 (10)° γ = 82.136 (11)° V = 1075.4 (7) Å3 Acta Cryst. (2015). E71, o171–o172
Z=4 F(000) = 484 Dx = 1.428 Mg m−3 Mo Kα radiation, λ = 0.71073 Å Cell parameters from 4579 reflections θ = 2.5–25.1° µ = 0.29 mm−1 T = 200 K Block, yellow 0.40 × 0.40 × 0.40 mm
sup-3
supporting information Data collection Bruker SMART X2S benchtop diffractometer Radiation source: XOS X-beam microfocus source Doubly curved silicon crystal monochromator ω scans Absorption correction: multi-scan (SADABS; Bruker, 2009) Tmin = 0.813, Tmax = 1.000
19554 measured reflections 3775 independent reflections 2517 reflections with I > 2σ(I) Rint = 0.066 θmax = 25.2°, θmin = 2.5° h = −9→9 k = −12→12 l = −15→15
Refinement Refinement on F2 Least-squares matrix: full R[F2 > 2σ(F2)] = 0.052 wR(F2) = 0.150 S = 1.03 3775 reflections 305 parameters 9 restraints Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map Hydrogen site location: mixed H atoms treated by a mixture of independent and constrained refinement w = 1/[σ2(Fo2) + (0.0859P)2 + 0.1759P] where P = (Fo2 + 2Fc2)/3 (Δ/σ)max = 0.001 Δρmax = 0.63 e Å−3 Δρmin = −0.31 e Å−3
Special details 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)
S1 O1 N1 N2 H2N N3 H3AN H3BN N4 C1 C2 H2 C3 C4 C5 C6 H6A H6B H6C
x
y
z
Uiso*/Ueq
0.84898 (9) 0.3621 (3) 0.6422 (3) 0.4586 (3) 0.4539 0.7191 (3) 0.6676 0.7858 0.9584 (4) 0.5671 (3) 0.5899 (3) 0.5348 0.6957 (3) 0.7727 (3) 0.7434 (3) 0.7793 (4) 0.8123 0.6579 0.8295
−0.09268 (8) 0.3985 (2) 0.1137 (2) 0.2943 (2) 0.3015 0.0201 (3) 0.0723 −0.0510 −0.2438 (3) 0.1876 (3) 0.1621 (3) 0.2200 0.0492 (3) −0.0312 (3) 0.0062 (3) −0.0068 (3) 0.0831 −0.0013 −0.0553
−0.11814 (5) 0.14350 (16) −0.04595 (17) −0.00302 (17) −0.0695 0.25778 (18) 0.3056 0.2744 0.1290 (2) 0.0309 (2) 0.1320 (2) 0.1827 0.1588 (2) 0.0799 (2) −0.0213 (2) −0.2309 (2) −0.2403 −0.2227 −0.2914
0.0324 (2) 0.0444 (6) 0.0243 (5) 0.0263 (6) 0.032* 0.0369 (7) 0.044* 0.044* 0.0453 (7) 0.0234 (6) 0.0267 (7) 0.032* 0.0263 (7) 0.0224 (6) 0.0229 (6) 0.0440 (9) 0.066* 0.066* 0.066*
Acta Cryst. (2015). E71, o171–o172
Occ. (
ISSN 2056-9890
Crystal structure of N-[4-amino-5-cyano6-(methylsulfanyl)pyridin-2-yl]acetamide hemihydrate Mehmet Akkurt,a Kyle S. Knight,b Shaaban K. Mohamed,c,d Bahgat R. M. Husseine and Mustafa R. Albayatif*
2. Experimental 2.1. Crystal data = 82.136 (11) ˚3 V = 1075.4 (7) A Z=4 Mo K radiation = 0.29 mm1 T = 200 K 0.40 0.40 0.40 mm
a
Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, bDepartment of Chemistry, The University of Tennessee at Chattanooga, Chattanooga, TN 37403, USA, cChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, dChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, eChemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt, and fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq. *Correspondence e-mail: [email protected]
C9H10N4OS0.5H2O Mr = 231.28 Triclinic, P1 ˚ a = 8.229 (3) A ˚ b = 10.181 (4) A ˚ c = 13.198 (5) A = 84.221 (10) = 80.036 (10)
Received 4 February 2015; accepted 6 February 2015
2.2. Data collection
Edited by H. Stoeckli-Evans, University of Neuchaˆtel, Switzerland
Bruker SMART X2S benchtop diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009) Tmin = 0.813, Tmax = 1.000
The title compound, C9H10N4OS0.5H2O, crystallizes with two independent molecules (A and B) in the asymmetric unit, together with a water molecule of crystallization. The acetamide moiety, which has an extended conformation, is inclined to the pyridine ring by 7.95 (16) in molecule A and by 1.77 (16) in molecule B. In the crystal, the A and B molecules are linked by two N—H Ocarbonyl hydrogen bonds, forming a dimer. The dimers are linked via N— H N hydrogen bonds, forming ribbons that are linked by N—H Owater hydrogen bonds to form sheets parallel to (110). The sheets are linked by O—H N hydrogen bonds, forming slabs, and between the slabs there are weak slipped parallel – interactions [inter-centroid distance = ˚ , interplanar distance = 3.3505 (11) A ˚ and slippage 3.734 (2) A ˚ = 1.648 A], forming a three-dimensional structure. Keywords: crystal structure; poly-functional pyridines; acetamide; disorder; hydrogen bonding. CCDC reference: 1048267
2.3. Refinement R[F 2 > 2(F 2)] = 0.052 wR(F 2) = 0.150 S = 1.03 3775 reflections 305 parameters 9 restraints
H atoms treated by a mixture of independent and constrained refinement ˚ 3 max = 0.63 e A ˚ 3 min = 0.31 e A
Table 1 ˚ , ). Hydrogen-bond geometry (A D—H A
D—H
H A
D A
D—H A
N3—H3AN O2 N7—H7BN O1 N3—H3BN N8i N7—H7AN N4ii N2—H2N O3A N2—H2N O3B N6—H6N O3Aiii N6—H6N O3Biii O3A—H3A2 N7iv O3B—H3B1 N5v
0.88 0.88 0.88 0.88 0.88 0.88 0.88 0.88 0.85 (2) 0.85 (2)
2.00 1.99 2.33 2.38 2.12 2.21 2.26 2.19 2.36 (6) 2.57 (6)
2.870 (3) 2.860 (3) 3.080 (4) 3.116 (4) 2.984 (10) 3.079 (9) 3.138 (10) 3.051 (9) 3.083 (12) 3.239 (8)
169 170 143 142 166 172 173 166 143 (9) 137 (8)
Symmetry codes: (i) x þ 1; y 1; z; (ii) x 1; y þ 1; z; (iii) x; y; z þ 1; (iv) x þ 1; y þ 1; z; (v) x; y; z 1.
1. Related literature For various applications of polyfunctional pyridines, see: Knyazhanskii et al. (1996); Kurfurst et al. (1989); Enyedy et al. (2003); Arora & Knaus (1999); Kim et al. 2004); Pillai et al. (2003).
Acta Cryst. (2015). E71, o171–o172
19554 measured reflections 3775 independent reflections 2517 reflections with I > 2(I) Rint = 0.066
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics:
doi:10.1107/S205698901500256X
Akkurt et al.
o171
data reports PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 and PLATON.
Acknowledgements We are grateful to the University of Tennessee and Sohag University for supporting this study. Supporting information for this paper is available from the IUCr electronic archives (Reference: SU5077).
References
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Enyedy, I. J., Sakamuri, S., Zaman, W. A., Johnson, K. M. & Wang, S. (2003). Bioorg. Med. Chem. Lett. 13, 513–517. Kim, B. Y., Ahn, J. B., Lee, H. W., Kang, S. K., Lee, J. H., Shin, J. S., Ahn, S. K., Hong, C. I. & Yoon, S. S. (2004). Eur. J. Med. Chem. 39, 433–447. Knyazhanskii, M. I., Makarova, N. I., Olekhmovich, E. P. & Kharlanov, A. (1996). Zh. Org. Khim. 32, 1097–1103. Kurfu¨rst, A., Lhota´k, P., Petru˚, M. & Kuthan, J. (1989). Collect. Czech. Chem. Commun. 54, 462–472. Pillai, A. D., Rathod, P. D., Franklin, P. X., Patel, M., Nivsarkar, M., Vasu, K. K., Padh, H. & Sudarsanam, V. (2003). Biochem. Biophys. Res. Commun. 301, 183–186. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Spek, A. L. (2009). Acta Cryst. D65, 148–155.
Arora, V. K. & Knaus, E. E. (1999). J. Heterocycl. Chem. 36, 201–203.
o172
Akkurt et al.
C9H10N4OS0.5H2O
Acta Cryst. (2015). E71, o171–o172
supporting information
supporting information Acta Cryst. (2015). E71, o171–o172
[doi:10.1107/S205698901500256X]
Crystal structure of N-[4-amino-5-cyano-6-(methylsulfanyl)pyridin-2yl]acetamide hemihydrate Mehmet Akkurt, Kyle S. Knight, Shaaban K. Mohamed, Bahgat R. M. Hussein and Mustafa R. Albayati S1. Comment Poly-functional pyridines are an interesting class of compounds due to their optical properties (Knyazhanskii et al., 1996; Kurfurst et al., 1989), and their biological activities (Enyedy et al., 2003), such as anticonvulsants (Arora et al., 1999), antihistaminic reagents (Kim et al., 2004), and cardivascular disorder treatments (Pillai et al., 2003). In view of such facts we herein report on the synthesis and crystal structure of the new title poly-functional pyridine compound. The asymmetric unit of the title compound, Fig. 1, contains two independent title molecules (A and B) and one water molecule. In molecule A the dihedral angle between the pyridine ring (N1/C1–C5) and the acetamide moiety (O1/N2(C7/C8) is 7.95 (16)°, while in molecule B the corresponding angle, involving the pyridine ring (N5/C10-C14) and actemide moiety (O2/N2/C7/C8), is 1.77 (16)°. In the crystal, the A and B molecules are linked by two N-H···Ocarbonyl hydrogen bonds forming a dimer (Table 1 and Fig. 1). The dimers are linked via N-H···N hydrogen bonds forming ribbons that are linked by N-H···Owater hydrogen bonds to form sheets parallel to (110); see Table 1. The sheets are linked by O-H···N hydrogen bonds forming slabs (Table 1). Between the slabs there are weak slipped parallel π-π interactions forming a three-dimensional structure, Fig. 2 [intercentroid distance Cg1···Cg1i = 3.734 (2) Å, inter-planar distance = 3.351 (1) Å, slippage = 1.648 Å; Cg1 is the centroid of ring N5/C10-C14 (molecule B); symmetry code: (i) -x, -y+1, -z+1]. S2. Experimental A solution of 0.5 g (2.7 mmol) of 4,6-diamino-3-cyano-2-methylthiopyridine-2(1H)-thione in 30 ml glacial acetic acid was refluxed for 3 h. The reaction mixture was allowed to cool and it was then poured into 100 ml of ice cold water. The formed precipitate was collected and dried under vacuum. Yellow crystals, suitable for X-ray analysis, were obtained by recrystallization of the solid product from ethanol (yield: 92%; m.p.: 523–525 K). S3. Refinement The water molecule O3 is disordered over two positions (O3A/O3B) and was refined with an occupancy ratio of 0.5:0.5. The H atoms were included in calculated positions (calc-OH in WinGX; Farrugia, 2012 and refined with distance restraints: O—H = 0.84 (2) Å and H···H = 1.35 (2) Å with Uiso(H) = 1.5Ueq(O). The C and N-bound H atoms were placed in calculated positions and treated as riding atoms: C—H = 0.95 - 0.98 Å and N—H = 0.88 Å, with Uiso(H) = 1.5Ueq(C) for methyl H atoms and = 1.2Ueq(N,C) for other H atoms.
Acta Cryst. (2015). E71, o171–o172
sup-1
supporting information
Figure 1 Molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. The N—H···O hydrogen bonds are shown as dashed lines (see Table 1 for details).
Acta Cryst. (2015). E71, o171–o172
sup-2
supporting information
Figure 2 View along the c axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1 for details; H atoms not involved in hydrogen bonding have been omitted for clarity). N-[4-Amino-5-cyano-6-(methylsulfanyl)pyridin-2-yl]acetamide hemihydrate Crystal data C9H10N4OS·0.5H2O Mr = 231.28 Triclinic, P1 a = 8.229 (3) Å b = 10.181 (4) Å c = 13.198 (5) Å α = 84.221 (10)° β = 80.036 (10)° γ = 82.136 (11)° V = 1075.4 (7) Å3 Acta Cryst. (2015). E71, o171–o172
Z=4 F(000) = 484 Dx = 1.428 Mg m−3 Mo Kα radiation, λ = 0.71073 Å Cell parameters from 4579 reflections θ = 2.5–25.1° µ = 0.29 mm−1 T = 200 K Block, yellow 0.40 × 0.40 × 0.40 mm
sup-3
supporting information Data collection Bruker SMART X2S benchtop diffractometer Radiation source: XOS X-beam microfocus source Doubly curved silicon crystal monochromator ω scans Absorption correction: multi-scan (SADABS; Bruker, 2009) Tmin = 0.813, Tmax = 1.000
19554 measured reflections 3775 independent reflections 2517 reflections with I > 2σ(I) Rint = 0.066 θmax = 25.2°, θmin = 2.5° h = −9→9 k = −12→12 l = −15→15
Refinement Refinement on F2 Least-squares matrix: full R[F2 > 2σ(F2)] = 0.052 wR(F2) = 0.150 S = 1.03 3775 reflections 305 parameters 9 restraints Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map Hydrogen site location: mixed H atoms treated by a mixture of independent and constrained refinement w = 1/[σ2(Fo2) + (0.0859P)2 + 0.1759P] where P = (Fo2 + 2Fc2)/3 (Δ/σ)max = 0.001 Δρmax = 0.63 e Å−3 Δρmin = −0.31 e Å−3
Special details 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)
S1 O1 N1 N2 H2N N3 H3AN H3BN N4 C1 C2 H2 C3 C4 C5 C6 H6A H6B H6C
x
y
z
Uiso*/Ueq
0.84898 (9) 0.3621 (3) 0.6422 (3) 0.4586 (3) 0.4539 0.7191 (3) 0.6676 0.7858 0.9584 (4) 0.5671 (3) 0.5899 (3) 0.5348 0.6957 (3) 0.7727 (3) 0.7434 (3) 0.7793 (4) 0.8123 0.6579 0.8295
−0.09268 (8) 0.3985 (2) 0.1137 (2) 0.2943 (2) 0.3015 0.0201 (3) 0.0723 −0.0510 −0.2438 (3) 0.1876 (3) 0.1621 (3) 0.2200 0.0492 (3) −0.0312 (3) 0.0062 (3) −0.0068 (3) 0.0831 −0.0013 −0.0553
−0.11814 (5) 0.14350 (16) −0.04595 (17) −0.00302 (17) −0.0695 0.25778 (18) 0.3056 0.2744 0.1290 (2) 0.0309 (2) 0.1320 (2) 0.1827 0.1588 (2) 0.0799 (2) −0.0213 (2) −0.2309 (2) −0.2403 −0.2227 −0.2914
0.0324 (2) 0.0444 (6) 0.0243 (5) 0.0263 (6) 0.032* 0.0369 (7) 0.044* 0.044* 0.0453 (7) 0.0234 (6) 0.0267 (7) 0.032* 0.0263 (7) 0.0224 (6) 0.0229 (6) 0.0440 (9) 0.066* 0.066* 0.066*
Acta Cryst. (2015). E71, o171–o172
Occ. (
