data reports 2. Experimental 2.1. Crystal data ISSN 1600-5368
Crystal structure of bis(allylammonium) oxalate
˚3 V = 3296.5 (3) A Z = 12 Mo K radiation = 0.10 mm1 T = 100 K 0.25 0.15 0.10 mm
2C3H8N+C2O4 Mr = 204.23 Monoclinic, P21 =n ˚ a = 6.7060 (3) A ˚ b = 12.1364 (10) A ˚ c = 40.6017 (16) A = 93.969 (4)
. Błazej Dziuk, Bartosz Zarychta* and Krzysztof Ejsmont
2.2. Data collection
Faculty of Chemistry, University of Opole, Oleska 48, 45-052 Opole, Poland. *Correspondence e-mail: [email protected]
Oxford Diffraction Xcalibur CCD diffractometer 21821 measured reflections
6460 independent reflections 4306 reflections with I > 2(I) Rint = 0.036
Received 22 October 2014; accepted 27 October 2014
2.3. Refinement Edited by H. Stoeckli-Evans, University of Neuchaˆtel, Switzerland
The title salt, 2C3H8N+C2O42, crystallized with six independent allylammonium cations and three independent oxalate dianions in the asymmetric unit. One of the oxalate dianions is nearly planar [dihedral angle between CO2 planes = 1.91 (19) ], while the other two are twisted with angles of 11.3 (3) and 26.09 (13) . One cation has a synperiplanar (cis) conformation with an N—C—C—C torsion angle of 0.9 (3) , whereas the five remaining cations are characterized by gauche arrangements, with the N—C—C—C torsion angles ranging from 115.9 (12) to 128.8 (3) . One of the allylammonium cations is positionally disordered (fixed occupancy ratio = 0.45:0.55). In the crystal, the cations and anions are connected by a number of strong N—H O and N— H (O,O) hydrogen bonds, forming layers parallel to (001), with the vinyl groups protruding into the space between the layers. Keywords: crystal structure; allylammonium; oxalate; dication; hydrogen bonding. CCDC reference: 1031212
1. Related literature For the crystal structures of oxalic acid salts with aliphatic amines, see: Dziuk et al. (2014a,b); Braga et al. (2013); Ejsmont & Zaleski (2006a,b); Ejsmont (2006, 2007). For the crystal structures of salts with disordered allylammonium cations, see: Płowas´ et al. (2010); Zarychta et al. (2007).
R[F 2 > 2(F 2)] = 0.053 wR(F 2) = 0.132 S = 1.03 6460 reflections 397 parameters
38 restraints H-atom parameters constrained ˚ 3 max = 0.57 e A ˚ 3 min = 0.44 e A
Table 1 ˚ , ). Hydrogen-bond geometry (A D—H A
D—H
H A
D A
D—H A
N1—H1A O10 N1—H1A O12 N1—H1B O9i N1—H1C O11ii N2—H2A O6iii N2—H2A O8iii N2—H2B O1iv N2—H2C O7 N3—H3A O4 N3—H3B O6iii N3—H3C O5 N3—H3C O7 N4—H4A O2 N4—H4A O4 N4—H4B O5iii N4—H4C O3iii N5—H5A O8v N5—H5B O2i N5—H5C O1 N6—H6A O10vi N6—H6B O11 N6—H6C O12iii
0.89 0.89 0.89 0.89 0.89 0.89 0.89 0.89 0.89 0.89 0.89 0.89 0.89 0.89 0.89 0.89 0.89 0.89 0.89 0.89 0.89 0.89
2.02 2.30 1.89 1.92 2.32 2.02 1.92 1.89 1.94 1.89 2.12 2.13 2.18 2.10 1.89 1.84 1.83 1.93 2.09 1.85 2.04 1.92
2.829 (2) 2.905 (2) 2.768 (2) 2.801 (2) 2.890 (2) 2.838 (2) 2.797 (2) 2.773 (2) 2.737 (2) 2.759 (2) 2.847 (2) 2.885 (2) 2.887 (2) 2.831 (2) 2.769 (2) 2.728 (2) 2.701 (2) 2.762 (2) 2.945 (2) 2.720 (2) 2.900 (2) 2.744 (2)
150 125 167 169 122 152 168 172 148 165 138 142 135 139 172 176 165 156 162 166 163 153
Symmetry codes: (i) x 1; y; z; (ii) x þ 12; y þ 12; z þ 12; (iii) x þ 1; y; z; (iv) x; y 1; z; (v) x; y þ 1; z; (vi) x þ 32; y 12; z þ 12.
Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2013.
Supporting information for this paper is available from the IUCr electronic archives (Reference: SU5011).
Acta Cryst. (2014). E70, o1229–o1230
doi:10.1107/S1600536814023617
Dziuk et al.
o1229
data reports References Braga, D., Chelazzi, L., Ciabatti, I. & Grepioni, F. (2013). New J. Chem. 37, 97– 104. Dziuk, B., Zarychta, B. & Ejsmont, K. (2014a). Acta Cryst. E70, o852. Dziuk, B., Zarychta, B. & Ejsmont, K. (2014b). Acta Cryst. E70, o917–o918. Ejsmont, K. (2006). Acta Cryst. E62, o5852–o5854. Ejsmont, K. (2007). Acta Cryst. E63, o107–o109. Ejsmont, K. & Zaleski, J. (2006a). Acta Cryst. E62, o3879–o3880.
o1230
Dziuk et al.
2C3H8N+C2O4
Ejsmont, K. & Zaleski, J. (2006b). Acta Cryst. E62, o2512–o2513. Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England. Płowas´, I., Białon´ska, A., Jakubas, R., Bator, G., Zarychta, B. & Baran, J. (2010). Chem. Phys. 375, 16–25. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Spek, A. L. (2009). Acta Cryst. D65, 148–155. Zarychta, B., Bujak, M. & Zaleski, J. (2007). Z. Naturforsch. Teil B, 62, 44–50.
Acta Cryst. (2014). E70, o1229–o1230
supporting information
supporting information Acta Cryst. (2014). E70, o1229–o1230
[doi:10.1107/S1600536814023617]
Crystal structure of bis(allylammonium) oxalate Błażej Dziuk, Bartosz Zarychta and Krzysztof Ejsmont S1. Comment The crystal structure of the title salt is illustrated in Fig. 1. It crystallized with six independent allylammonium cations and three independent oxalate dianions in the asymmetric unit. This is in contrast to the structure of a ethylammonium oxalate hemihydrate where the oxalate is present as a monoanion (Ejsmont & Zaleski, 2006a). The geometry of the anions and cations is alternated. One of oxalate anion is nearly planar with the O5–C21–C22–O8 torsion angle being 179.22 (19)°, while the two remaining oxalate anions are twisted along the C19–C20 and C23–C24 bonds by -154.87 (19)° and 168.12 (19)°. The N3 cation has a syn-periplanar (cis) conformation with the N–C–C–C torsion angle of 0.9 (3)°, whereas the five remaining cations are characterized by a gauche arrangement, with torsion angles ranging from 115.9 (12) to 128.8 (3)° for the N6 and N4 cations, respectively. Moreover one allylammonium cation is disordered, with a similar type of disorder as in the structures of (C3H5NH3)3 [SbBr6] (Płowaś et al., 2010) and (C3H5NH3)2SbCl5.(C3H5NH3)Cl (Zarychta et al., 2007). In the crystal, each anion is hydrogen bonded to two cations via N-H···O hydrogen bonds (Table 1 and Fig. 2) forming layers parallel to (001), separated by ca. 7.9 Å. The space is occupied by the vinyl groups of the allylammonium cations (Fig. 2 and Table 1). S2. Experimental Crystals were grown at room temperature by slow evaporation of an aqueous solution containing allylamine and oxalic acid in a 1:1 stoichiometric ratio. S3. Refinement All H atoms were positioned geometrically and treated as riding on their parent atoms, with N–H = 0.89 Å, C—H = 0.93 - 0.97 Å and with Uiso(H) = 1.5Ueq(N,C-methyl) and = 1.2Ueq(C) for other H atoms. One of the allylammonium cations is positionally disorded and atoms C17A/C17B and C18A/C18B were refined with a fixed occupany ratio of 0.45:0.55.
Acta Cryst. (2014). E70, o1229–o1230
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supporting information
Figure 1 The molecular structure of the asymmetric unit of the title salt, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. One of the allylammonium cations is positionally disorded and only the major components, atoms C17B and C18B, are shown for clarity.
Acta Cryst. (2014). E70, o1229–o1230
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Figure 2 The crystal packing viewed along the b axis of the title salt. The hydrogen bonds are shown as dashed lines (see Table 1 for details). Bis(allylammonium) oxalate Crystal data 2C3H8N+·C2O4− Mr = 204.23 Monoclinic, P21/n a = 6.7060 (3) Å b = 12.1364 (10) Å c = 40.6017 (16) Å β = 93.969 (4)° V = 3296.5 (3) Å3 Z = 12
F(000) = 1320 Dx = 1.235 Mg m−3 Mo Kα radiation, λ = 0.71073 Å Cell parameters from 21821 reflections θ = 3.0–26.0° µ = 0.10 mm−1 T = 100 K Block, colourless 0.25 × 0.15 × 0.10 mm
Data collection Oxford Diffraction Xcalibur CCD diffractometer Radiation source: fine-focus sealed tube Graphite monochromator ω scan 21821 measured reflections 6460 independent reflections
4306 reflections with I > 2σ(I) Rint = 0.036 θmax = 26.0°, θmin = 3.0° h = −8→8 k = −14→13 l = −49→47
Refinement Refinement on F2 Least-squares matrix: full R[F2 > 2σ(F2)] = 0.053 wR(F2) = 0.132 S = 1.03
Acta Cryst. (2014). E70, o1229–o1230
6460 reflections 397 parameters 38 restraints Hydrogen site location: inferred from neighbouring sites
sup-3
supporting information (Δ/σ)max < 0.001 Δρmax = 0.57 e Å−3 Δρmin = −0.44 e Å−3
H-atom parameters constrained w = 1/[σ2(Fo2) + (0.0677P)2] where P = (Fo2 + 2Fc2)/3 Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
N1 H1A H1B H1C C1 H1D H1E C2 H2D C3 H3D H3E N2 H2A H2B H2C C4 H4D H4E C5 H5D C6 H6D H6E N3 H3A H3B H3C C7 H7A H7B C8 H8A C9 H9A H9B
x
y
z
Uiso*/Ueq
0.0693 (2) 0.1840 −0.0319 0.0549 0.0706 (3) 0.0888 0.1825 −0.1179 (4) −0.2376 −0.1275 (4) −0.0108 −0.2511 0.9169 (2) 1.0339 0.8945 0.8199 0.9211 (3) 1.0297 0.9463 0.7292 (3) 0.6114 0.7165 (4) 0.8317 0.5923 0.7745 (2) 0.7731 0.8881 0.6716 0.7589 (3) 0.8698 0.6364 0.7597 (3) 0.7520 0.7701 (4) 0.7781 0.7694
0.39719 (14) 0.3626 0.3503 0.4530 0.43979 (19) 0.3789 0.4898 0.4984 (2) 0.4615 0.5981 (2) 0.6375 0.6297 0.04985 (13) 0.0818 −0.0030 0.0999 0.00129 (18) −0.0514 0.0591 −0.0550 (2) −0.0148 −0.1577 (2) −0.1999 −0.1882 0.40896 (13) 0.4511 0.3709 0.3625 0.47910 (18) 0.5306 0.5216 0.4167 (2) 0.4582 0.3098 (2) 0.2642 0.2793
0.24556 (4) 0.2509 0.2469 0.2594 0.21148 (5) 0.1965 0.2101 0.20118 (6) 0.2035 0.18910 (7) 0.1864 0.1832 0.07308 (4) 0.0786 0.0876 0.0731 0.03964 (5) 0.0395 0.0239 0.02916 (6) 0.0298 0.01908 (6) 0.0182 0.0129 0.05764 (4) 0.0756 0.0582 0.0571 0.02790 (6) 0.0290 0.0278 −0.00353 (6) −0.0228 −0.00713 (6) 0.0113 −0.0282
0.0168 (4) 0.025* 0.025* 0.025* 0.0233 (5) 0.028* 0.028* 0.0286 (6) 0.034* 0.0423 (7) 0.051* 0.051* 0.0146 (4) 0.022* 0.022* 0.022* 0.0197 (5) 0.024* 0.024* 0.0247 (5) 0.030* 0.0354 (7) 0.042* 0.042* 0.0159 (4) 0.024* 0.024* 0.024* 0.0262 (6) 0.031* 0.031* 0.0303 (6) 0.036* 0.0319 (6) 0.038* 0.038*
Acta Cryst. (2014). E70, o1229–o1230
Occ. (
Crystal structure of bis(allylammonium) oxalate
˚3 V = 3296.5 (3) A Z = 12 Mo K radiation = 0.10 mm1 T = 100 K 0.25 0.15 0.10 mm
2C3H8N+C2O4 Mr = 204.23 Monoclinic, P21 =n ˚ a = 6.7060 (3) A ˚ b = 12.1364 (10) A ˚ c = 40.6017 (16) A = 93.969 (4)
. Błazej Dziuk, Bartosz Zarychta* and Krzysztof Ejsmont
2.2. Data collection
Faculty of Chemistry, University of Opole, Oleska 48, 45-052 Opole, Poland. *Correspondence e-mail: [email protected]
Oxford Diffraction Xcalibur CCD diffractometer 21821 measured reflections
6460 independent reflections 4306 reflections with I > 2(I) Rint = 0.036
Received 22 October 2014; accepted 27 October 2014
2.3. Refinement Edited by H. Stoeckli-Evans, University of Neuchaˆtel, Switzerland
The title salt, 2C3H8N+C2O42, crystallized with six independent allylammonium cations and three independent oxalate dianions in the asymmetric unit. One of the oxalate dianions is nearly planar [dihedral angle between CO2 planes = 1.91 (19) ], while the other two are twisted with angles of 11.3 (3) and 26.09 (13) . One cation has a synperiplanar (cis) conformation with an N—C—C—C torsion angle of 0.9 (3) , whereas the five remaining cations are characterized by gauche arrangements, with the N—C—C—C torsion angles ranging from 115.9 (12) to 128.8 (3) . One of the allylammonium cations is positionally disordered (fixed occupancy ratio = 0.45:0.55). In the crystal, the cations and anions are connected by a number of strong N—H O and N— H (O,O) hydrogen bonds, forming layers parallel to (001), with the vinyl groups protruding into the space between the layers. Keywords: crystal structure; allylammonium; oxalate; dication; hydrogen bonding. CCDC reference: 1031212
1. Related literature For the crystal structures of oxalic acid salts with aliphatic amines, see: Dziuk et al. (2014a,b); Braga et al. (2013); Ejsmont & Zaleski (2006a,b); Ejsmont (2006, 2007). For the crystal structures of salts with disordered allylammonium cations, see: Płowas´ et al. (2010); Zarychta et al. (2007).
R[F 2 > 2(F 2)] = 0.053 wR(F 2) = 0.132 S = 1.03 6460 reflections 397 parameters
38 restraints H-atom parameters constrained ˚ 3 max = 0.57 e A ˚ 3 min = 0.44 e A
Table 1 ˚ , ). Hydrogen-bond geometry (A D—H A
D—H
H A
D A
D—H A
N1—H1A O10 N1—H1A O12 N1—H1B O9i N1—H1C O11ii N2—H2A O6iii N2—H2A O8iii N2—H2B O1iv N2—H2C O7 N3—H3A O4 N3—H3B O6iii N3—H3C O5 N3—H3C O7 N4—H4A O2 N4—H4A O4 N4—H4B O5iii N4—H4C O3iii N5—H5A O8v N5—H5B O2i N5—H5C O1 N6—H6A O10vi N6—H6B O11 N6—H6C O12iii
0.89 0.89 0.89 0.89 0.89 0.89 0.89 0.89 0.89 0.89 0.89 0.89 0.89 0.89 0.89 0.89 0.89 0.89 0.89 0.89 0.89 0.89
2.02 2.30 1.89 1.92 2.32 2.02 1.92 1.89 1.94 1.89 2.12 2.13 2.18 2.10 1.89 1.84 1.83 1.93 2.09 1.85 2.04 1.92
2.829 (2) 2.905 (2) 2.768 (2) 2.801 (2) 2.890 (2) 2.838 (2) 2.797 (2) 2.773 (2) 2.737 (2) 2.759 (2) 2.847 (2) 2.885 (2) 2.887 (2) 2.831 (2) 2.769 (2) 2.728 (2) 2.701 (2) 2.762 (2) 2.945 (2) 2.720 (2) 2.900 (2) 2.744 (2)
150 125 167 169 122 152 168 172 148 165 138 142 135 139 172 176 165 156 162 166 163 153
Symmetry codes: (i) x 1; y; z; (ii) x þ 12; y þ 12; z þ 12; (iii) x þ 1; y; z; (iv) x; y 1; z; (v) x; y þ 1; z; (vi) x þ 32; y 12; z þ 12.
Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2013.
Supporting information for this paper is available from the IUCr electronic archives (Reference: SU5011).
Acta Cryst. (2014). E70, o1229–o1230
doi:10.1107/S1600536814023617
Dziuk et al.
o1229
data reports References Braga, D., Chelazzi, L., Ciabatti, I. & Grepioni, F. (2013). New J. Chem. 37, 97– 104. Dziuk, B., Zarychta, B. & Ejsmont, K. (2014a). Acta Cryst. E70, o852. Dziuk, B., Zarychta, B. & Ejsmont, K. (2014b). Acta Cryst. E70, o917–o918. Ejsmont, K. (2006). Acta Cryst. E62, o5852–o5854. Ejsmont, K. (2007). Acta Cryst. E63, o107–o109. Ejsmont, K. & Zaleski, J. (2006a). Acta Cryst. E62, o3879–o3880.
o1230
Dziuk et al.
2C3H8N+C2O4
Ejsmont, K. & Zaleski, J. (2006b). Acta Cryst. E62, o2512–o2513. Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England. Płowas´, I., Białon´ska, A., Jakubas, R., Bator, G., Zarychta, B. & Baran, J. (2010). Chem. Phys. 375, 16–25. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Spek, A. L. (2009). Acta Cryst. D65, 148–155. Zarychta, B., Bujak, M. & Zaleski, J. (2007). Z. Naturforsch. Teil B, 62, 44–50.
Acta Cryst. (2014). E70, o1229–o1230
supporting information
supporting information Acta Cryst. (2014). E70, o1229–o1230
[doi:10.1107/S1600536814023617]
Crystal structure of bis(allylammonium) oxalate Błażej Dziuk, Bartosz Zarychta and Krzysztof Ejsmont S1. Comment The crystal structure of the title salt is illustrated in Fig. 1. It crystallized with six independent allylammonium cations and three independent oxalate dianions in the asymmetric unit. This is in contrast to the structure of a ethylammonium oxalate hemihydrate where the oxalate is present as a monoanion (Ejsmont & Zaleski, 2006a). The geometry of the anions and cations is alternated. One of oxalate anion is nearly planar with the O5–C21–C22–O8 torsion angle being 179.22 (19)°, while the two remaining oxalate anions are twisted along the C19–C20 and C23–C24 bonds by -154.87 (19)° and 168.12 (19)°. The N3 cation has a syn-periplanar (cis) conformation with the N–C–C–C torsion angle of 0.9 (3)°, whereas the five remaining cations are characterized by a gauche arrangement, with torsion angles ranging from 115.9 (12) to 128.8 (3)° for the N6 and N4 cations, respectively. Moreover one allylammonium cation is disordered, with a similar type of disorder as in the structures of (C3H5NH3)3 [SbBr6] (Płowaś et al., 2010) and (C3H5NH3)2SbCl5.(C3H5NH3)Cl (Zarychta et al., 2007). In the crystal, each anion is hydrogen bonded to two cations via N-H···O hydrogen bonds (Table 1 and Fig. 2) forming layers parallel to (001), separated by ca. 7.9 Å. The space is occupied by the vinyl groups of the allylammonium cations (Fig. 2 and Table 1). S2. Experimental Crystals were grown at room temperature by slow evaporation of an aqueous solution containing allylamine and oxalic acid in a 1:1 stoichiometric ratio. S3. Refinement All H atoms were positioned geometrically and treated as riding on their parent atoms, with N–H = 0.89 Å, C—H = 0.93 - 0.97 Å and with Uiso(H) = 1.5Ueq(N,C-methyl) and = 1.2Ueq(C) for other H atoms. One of the allylammonium cations is positionally disorded and atoms C17A/C17B and C18A/C18B were refined with a fixed occupany ratio of 0.45:0.55.
Acta Cryst. (2014). E70, o1229–o1230
sup-1
supporting information
Figure 1 The molecular structure of the asymmetric unit of the title salt, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. One of the allylammonium cations is positionally disorded and only the major components, atoms C17B and C18B, are shown for clarity.
Acta Cryst. (2014). E70, o1229–o1230
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supporting information
Figure 2 The crystal packing viewed along the b axis of the title salt. The hydrogen bonds are shown as dashed lines (see Table 1 for details). Bis(allylammonium) oxalate Crystal data 2C3H8N+·C2O4− Mr = 204.23 Monoclinic, P21/n a = 6.7060 (3) Å b = 12.1364 (10) Å c = 40.6017 (16) Å β = 93.969 (4)° V = 3296.5 (3) Å3 Z = 12
F(000) = 1320 Dx = 1.235 Mg m−3 Mo Kα radiation, λ = 0.71073 Å Cell parameters from 21821 reflections θ = 3.0–26.0° µ = 0.10 mm−1 T = 100 K Block, colourless 0.25 × 0.15 × 0.10 mm
Data collection Oxford Diffraction Xcalibur CCD diffractometer Radiation source: fine-focus sealed tube Graphite monochromator ω scan 21821 measured reflections 6460 independent reflections
4306 reflections with I > 2σ(I) Rint = 0.036 θmax = 26.0°, θmin = 3.0° h = −8→8 k = −14→13 l = −49→47
Refinement Refinement on F2 Least-squares matrix: full R[F2 > 2σ(F2)] = 0.053 wR(F2) = 0.132 S = 1.03
Acta Cryst. (2014). E70, o1229–o1230
6460 reflections 397 parameters 38 restraints Hydrogen site location: inferred from neighbouring sites
sup-3
supporting information (Δ/σ)max < 0.001 Δρmax = 0.57 e Å−3 Δρmin = −0.44 e Å−3
H-atom parameters constrained w = 1/[σ2(Fo2) + (0.0677P)2] where P = (Fo2 + 2Fc2)/3 Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
N1 H1A H1B H1C C1 H1D H1E C2 H2D C3 H3D H3E N2 H2A H2B H2C C4 H4D H4E C5 H5D C6 H6D H6E N3 H3A H3B H3C C7 H7A H7B C8 H8A C9 H9A H9B
x
y
z
Uiso*/Ueq
0.0693 (2) 0.1840 −0.0319 0.0549 0.0706 (3) 0.0888 0.1825 −0.1179 (4) −0.2376 −0.1275 (4) −0.0108 −0.2511 0.9169 (2) 1.0339 0.8945 0.8199 0.9211 (3) 1.0297 0.9463 0.7292 (3) 0.6114 0.7165 (4) 0.8317 0.5923 0.7745 (2) 0.7731 0.8881 0.6716 0.7589 (3) 0.8698 0.6364 0.7597 (3) 0.7520 0.7701 (4) 0.7781 0.7694
0.39719 (14) 0.3626 0.3503 0.4530 0.43979 (19) 0.3789 0.4898 0.4984 (2) 0.4615 0.5981 (2) 0.6375 0.6297 0.04985 (13) 0.0818 −0.0030 0.0999 0.00129 (18) −0.0514 0.0591 −0.0550 (2) −0.0148 −0.1577 (2) −0.1999 −0.1882 0.40896 (13) 0.4511 0.3709 0.3625 0.47910 (18) 0.5306 0.5216 0.4167 (2) 0.4582 0.3098 (2) 0.2642 0.2793
0.24556 (4) 0.2509 0.2469 0.2594 0.21148 (5) 0.1965 0.2101 0.20118 (6) 0.2035 0.18910 (7) 0.1864 0.1832 0.07308 (4) 0.0786 0.0876 0.0731 0.03964 (5) 0.0395 0.0239 0.02916 (6) 0.0298 0.01908 (6) 0.0182 0.0129 0.05764 (4) 0.0756 0.0582 0.0571 0.02790 (6) 0.0290 0.0278 −0.00353 (6) −0.0228 −0.00713 (6) 0.0113 −0.0282
0.0168 (4) 0.025* 0.025* 0.025* 0.0233 (5) 0.028* 0.028* 0.0286 (6) 0.034* 0.0423 (7) 0.051* 0.051* 0.0146 (4) 0.022* 0.022* 0.022* 0.0197 (5) 0.024* 0.024* 0.0247 (5) 0.030* 0.0354 (7) 0.042* 0.042* 0.0159 (4) 0.024* 0.024* 0.024* 0.0262 (6) 0.031* 0.031* 0.0303 (6) 0.036* 0.0319 (6) 0.038* 0.038*
Acta Cryst. (2014). E70, o1229–o1230
Occ. (
