Abstract
The formulation that the title compound, C18H18N2O4S2, adopts is a zwitterionic core with the charge separated to the sulfilimine S and N atoms and is supported by the two different S—N bond distances about the sulfinimine N atom [1.594 (2) and 1.631 (2) Å, respectively] that are typical for such bonds. The notably unusual bond is S—N(oxazolidinone) [1.692 (2) Å] that is longer than a typical S—N bond [1.603 (18) Å, Mogul analysis; Macrae et al. (2008 ▸). J. Appl. Cryst. 41, 466–470]. The bond-angle sum about sulfilimine sulfur (308.35°) reflects the trigonal–pyramidal geometry of this atom. Two of the angles are less than 100°. Despite the pyramidalization of this sulfur, there are no significant intermolecular interactions, beyond usual van der Waals contacts, in the crystal packing.
Keywords: oxazolidinone, vinyl sulfonamide, crystal structure
Related literature
Oxazolidinone sulfilimines are synthesized as precursors of vinyl sulfilimines which are used in the γ-lactamization reaction to generate chiral pyrrolidinones with medicinal chemistry interest. For the synthesis, see: Celentano & Colonna (1998 ▸); Silveira & Marino (2013 ▸). For sulfonyl oxazolidinone structures, see: Barbey et al. (2012 ▸); Berredjem et al. (2010 ▸); Bonnaud et al. (1987 ▸); Dewynter et al. (1997 ▸). For related vinyl sulfonamide chemistry, see: Silveira et al. (2013 ▸). For related oxazolidinone sulfinime structures, see: Silveira et al. (2012 ▸, 2014 ▸). For the Hooft parameter, see: Hooft et al. (2008 ▸).
Experimental
Crystal data
C18H18N2O4S2
M r = 390.46
Orthorhombic,
a = 6.8841 (1) Å
b = 12.2326 (2) Å
c = 20.1911 (4) Å
V = 1700.30 (5) Å3
Z = 4
Cu Kα radiation
μ = 3.09 mm−1
T = 100 K
0.42 × 0.40 × 0.34 mm
Data collection
Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Krause et al., 2015 ▸) T min = 0.701, T max = 0.929
11963 measured reflections
3004 independent reflections
2984 reflections with I > 2σ(I)
R int = 0.032
Refinement
R[F 2 > 2σ(F 2)] = 0.028
wR(F 2) = 0.070
S = 1.11
3004 reflections
237 parameters
H-atom parameters constrained
Δρmax = 0.29 e Å−3
Δρmin = −0.36 e Å−3
Absolute structure: Flack x determined using 1183 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▸)
Absolute structure parameter: 0.052 (4)
Data collection: APEX2 (Bruker, 2007 ▸); cell refinement: APEX2 and SAINT (Bruker, 2007 ▸); data reduction: SAINT and XPREP (Bruker, 2007 ▸); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▸); software used to prepare material for publication: XCIF (Sheldrick, 2008 ▸) and publCIF (Westrip, 2010 ▸).
Supplementary Material
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989015024779/nk2234sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015024779/nk2234Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015024779/nk2234Isup3.cml
. DOI: 10.1107/S2056989015024779/nk2234fig1.tif
Labeling diagram of the title compound. Atomic displacement ellipsoids depicted at the 50% probability level. Hydrogen atoms depicted as spheres of an arbitrary radius.
CCDC reference: 1444186
Additional supporting information: crystallographic information; 3D view; checkCIF report
Table 1. Selected geometric parameters (Å, °).
| S1—N2 | 1.594 (2) |
| S1—N1 | 1.692 (2) |
| S1—C11 | 1.782 (3) |
| S2—O4 | 1.4430 (19) |
| S2—O3 | 1.451 (2) |
| S2—N2 | 1.631 (2) |
| S2—C12 | 1.768 (2) |
| N2—S1—N1 | 110.58 (11) |
| N2—S1—C11 | 99.43 (12) |
| N1—S1—C11 | 98.34 (11) |
| O4—S2—O3 | 117.24 (12) |
| O4—S2—N2 | 106.79 (12) |
| O3—S2—N2 | 112.27 (11) |
| O4—S2—C12 | 107.93 (11) |
| O3—S2—C12 | 108.03 (12) |
| N2—S2—C12 | 103.67 (12) |
Acknowledgments
GPS thanks Professor Joseph Marino at Notre Dame for financial support.
supplementary crystallographic information
S1. Commentary
Oxazolidinone sulfilimines are synthesized as precursors of vinyl sulfilimines which are used in the γ-lactamization reaction (Silveira & Marino, 2013) to generate chiral pyrrolidinones with medicinal chemistry interest. This compound represents one of only five other oxazolidinone compounds that incorporate an N—S—N backbone (Barbey et al., 2012; Berredjem et al., 2010; Bonnaud et al., 1987; Dewynter et al., 1997). It is the only reported structure that does not have a sulfonyl bridging the oxazolidinone ring to the second nitrogen atom. Related sulfur-containing oxazolidinones have been reported previously by us (Silveira et al., 2012; 2014). We have also reported a related sulfur-containing indole as a precursor of physostigmine alkaloid·(Silveira et al., 2013).
S2. Synthesis and crystallization
Following literature preparative methods (Celentano et al., 1998; Silveira & Marino, 2013): chloramine-T (951 mg, 4.18 mmol) and hexadecyltributylphosphonium bromide (100 mg, 0.20 mmol) were added to a solution of oxazolidinone sulfide (840 mg, 3.80 mmol) in toluene (25 ml) at 295 K. After overnight stirring, ethyl acetate (25 ml) was added and the mixture washed (2 x 30 ml water; 1 x 30 ml brine), dried over anhydrous sodium sulfate, filtered, and the mixture of solvents rota-evaporated at reduced pressure. To the resulting dry, crude product, silica gel (6 g) and methylene chloride (5 ml) were added and this slurry was rota-evaporated to yield the crude product on silica. This mixture was separated and purified through flash chromatography with elution (70% ethyl acetate / 30% hexanes). After slow evaporation of the ethyl acetate / hexanes elutant, the more polar sulfilimine was obtained as white crystals (688 mg). Two sulfilimine diasterioisomers were obtained in a ratio of 2.5:1 (total of 65% yield).
S3. Refinement details
The structure was modeled routinely with all non-hydrogen atoms included with an anistropic model. Hydrogen atoms were included in calculated positions riding on the atom to which they are bonded (C—H = 0.99 Å for methyl, 0.95 Å for methyne and aromatic. Uiso(H) was set = 1.5Ueq(C) for methyl and 1.2Ueq(C) for all others.
The absolute configuration from synthesis was confirmed by comparison of intensities of Friedel pairs of reflections yielding a Flack x parameter = 0.052 (4) (Parsons et al., 2013) and a Hooft y parameter = 0.050 (6) (Hooft et al., 2008).
Figures
Fig. 1.
Labeling diagram of the title compound. Atomic displacement ellipsoids depicted at the 50% probability level. Hydrogen atoms depicted as spheres of an arbitrary radius.
Crystal data
| C18H18N2O4S2 | Dx = 1.525 Mg m−3 |
| Mr = 390.46 | Cu Kα radiation, λ = 1.54178 Å |
| Orthorhombic, P212121 | Cell parameters from 9988 reflections |
| a = 6.8841 (1) Å | θ = 4.2–69.2° |
| b = 12.2326 (2) Å | µ = 3.09 mm−1 |
| c = 20.1911 (4) Å | T = 100 K |
| V = 1700.30 (5) Å3 | Parallelepiped, clear colorless |
| Z = 4 | 0.42 × 0.40 × 0.34 mm |
| F(000) = 816 |
Data collection
| Bruker SMART APEX CCD diffractometer | 3004 independent reflections |
| Radiation source: fine-focus sealed tube, Siemens KFFCU2K-90 | 2984 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.032 |
| Detector resolution: 8.33 pixels mm-1 | θmax = 69.5°, θmin = 4.2° |
| φ and ω scans | h = −8→8 |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | k = −14→14 |
| Tmin = 0.701, Tmax = 0.929 | l = −24→22 |
| 11963 measured reflections |
Refinement
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.028 | H-atom parameters constrained |
| wR(F2) = 0.070 | w = 1/[σ2(Fo2) + (0.0405P)2 + 0.5066P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.11 | (Δ/σ)max = 0.001 |
| 3004 reflections | Δρmax = 0.29 e Å−3 |
| 237 parameters | Δρmin = −0.36 e Å−3 |
| 0 restraints | Absolute structure: Flack x determined using 1183 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
| Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.052 (4) |
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)
| x | y | z | Uiso*/Ueq | ||
| S1 | 0.45871 (9) | 0.55630 (5) | 0.77781 (3) | 0.00978 (15) | |
| S2 | 0.67201 (9) | 0.69687 (5) | 0.85264 (3) | 0.01185 (16) | |
| O1 | 0.3825 (3) | 0.25928 (14) | 0.82183 (9) | 0.0148 (4) | |
| O2 | 0.6694 (3) | 0.34297 (15) | 0.80444 (9) | 0.0176 (4) | |
| O3 | 0.8276 (3) | 0.63677 (15) | 0.82056 (9) | 0.0175 (4) | |
| O4 | 0.6751 (3) | 0.81443 (15) | 0.84687 (9) | 0.0185 (4) | |
| N1 | 0.3831 (3) | 0.44084 (18) | 0.81606 (11) | 0.0127 (5) | |
| N2 | 0.4579 (3) | 0.65675 (17) | 0.82812 (11) | 0.0132 (5) | |
| C1 | 0.4975 (4) | 0.3476 (2) | 0.81239 (12) | 0.0129 (5) | |
| C2 | 0.1767 (4) | 0.2920 (2) | 0.82310 (13) | 0.0136 (5) | |
| H2 | 0.1106 | 0.2809 | 0.7795 | 0.016* | |
| C3 | 0.0725 (4) | 0.2347 (2) | 0.87983 (13) | 0.0148 (6) | |
| H3A | −0.0688 | 0.2299 | 0.8713 | 0.018* | |
| H3B | 0.1246 | 0.1601 | 0.8867 | 0.018* | |
| C4 | 0.1142 (4) | 0.3068 (2) | 0.93859 (13) | 0.0124 (5) | |
| C5 | 0.0916 (4) | 0.2842 (2) | 1.00541 (13) | 0.0140 (6) | |
| H5 | 0.0423 | 0.2157 | 1.0198 | 0.017* | |
| C6 | 0.1431 (4) | 0.3648 (2) | 1.05088 (13) | 0.0161 (6) | |
| H6 | 0.1258 | 0.3512 | 1.0968 | 0.019* | |
| C7 | 0.2188 (4) | 0.4644 (2) | 1.03076 (14) | 0.0157 (6) | |
| H7 | 0.2569 | 0.5170 | 1.0628 | 0.019* | |
| C8 | 0.2393 (4) | 0.4875 (2) | 0.96324 (14) | 0.0141 (5) | |
| H8 | 0.2899 | 0.5558 | 0.9488 | 0.017* | |
| C9 | 0.1843 (4) | 0.4088 (2) | 0.91814 (13) | 0.0117 (5) | |
| C10 | 0.1900 (4) | 0.41298 (19) | 0.84277 (13) | 0.0116 (5) | |
| H10 | 0.0833 | 0.4584 | 0.8234 | 0.014* | |
| C11 | 0.2421 (4) | 0.5860 (2) | 0.73290 (13) | 0.0149 (6) | |
| H11A | 0.1358 | 0.5997 | 0.7641 | 0.022* | |
| H11B | 0.2089 | 0.5237 | 0.7046 | 0.022* | |
| H11C | 0.2627 | 0.6510 | 0.7054 | 0.022* | |
| C12 | 0.6749 (4) | 0.6636 (2) | 0.93784 (12) | 0.0112 (5) | |
| C13 | 0.6177 (4) | 0.7407 (2) | 0.98430 (13) | 0.0136 (5) | |
| H13 | 0.5750 | 0.8110 | 0.9706 | 0.016* | |
| C14 | 0.6237 (4) | 0.7138 (2) | 1.05134 (13) | 0.0153 (6) | |
| H14 | 0.5858 | 0.7664 | 1.0834 | 0.018* | |
| C15 | 0.6846 (4) | 0.6107 (2) | 1.07178 (13) | 0.0157 (5) | |
| C16 | 0.7366 (4) | 0.5341 (2) | 1.02403 (14) | 0.0152 (6) | |
| H16 | 0.7745 | 0.4628 | 1.0376 | 0.018* | |
| C17 | 0.7344 (4) | 0.5596 (2) | 0.95710 (14) | 0.0147 (5) | |
| H17 | 0.7727 | 0.5071 | 0.9250 | 0.018* | |
| C18 | 0.6940 (5) | 0.5854 (2) | 1.14496 (14) | 0.0231 (6) | |
| H18A | 0.7504 | 0.5126 | 1.1514 | 0.035* | |
| H18B | 0.5628 | 0.5871 | 1.1637 | 0.035* | |
| H18C | 0.7752 | 0.6400 | 1.1672 | 0.035* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0116 (3) | 0.0111 (3) | 0.0066 (3) | −0.0007 (2) | 0.0007 (2) | 0.0007 (2) |
| S2 | 0.0124 (3) | 0.0139 (3) | 0.0093 (3) | −0.0022 (2) | 0.0002 (2) | −0.0003 (2) |
| O1 | 0.0189 (10) | 0.0105 (8) | 0.0151 (9) | 0.0019 (7) | 0.0014 (7) | −0.0003 (7) |
| O2 | 0.0161 (9) | 0.0186 (9) | 0.0179 (9) | 0.0046 (8) | 0.0011 (8) | 0.0004 (8) |
| O3 | 0.0116 (9) | 0.0269 (10) | 0.0140 (9) | −0.0032 (8) | 0.0015 (8) | −0.0017 (8) |
| O4 | 0.0251 (10) | 0.0161 (9) | 0.0143 (9) | −0.0067 (8) | −0.0028 (8) | 0.0036 (7) |
| N1 | 0.0141 (11) | 0.0108 (10) | 0.0133 (10) | 0.0016 (9) | 0.0039 (9) | 0.0032 (9) |
| N2 | 0.0135 (11) | 0.0141 (10) | 0.0118 (10) | 0.0004 (9) | 0.0001 (9) | −0.0013 (9) |
| C1 | 0.0170 (14) | 0.0137 (12) | 0.0080 (12) | 0.0023 (10) | 0.0010 (10) | −0.0015 (10) |
| C2 | 0.0157 (13) | 0.0129 (12) | 0.0121 (12) | −0.0016 (11) | −0.0025 (11) | 0.0014 (10) |
| C3 | 0.0173 (14) | 0.0137 (12) | 0.0134 (13) | −0.0036 (10) | −0.0014 (11) | 0.0008 (11) |
| C4 | 0.0116 (11) | 0.0133 (12) | 0.0121 (12) | 0.0020 (10) | −0.0014 (10) | 0.0006 (11) |
| C5 | 0.0109 (12) | 0.0164 (13) | 0.0149 (13) | 0.0002 (10) | 0.0010 (10) | 0.0059 (10) |
| C6 | 0.0122 (13) | 0.0256 (14) | 0.0106 (12) | 0.0041 (11) | 0.0015 (10) | 0.0017 (11) |
| C7 | 0.0107 (13) | 0.0218 (13) | 0.0145 (13) | 0.0024 (10) | −0.0001 (10) | −0.0054 (11) |
| C8 | 0.0114 (12) | 0.0135 (12) | 0.0174 (13) | 0.0023 (10) | 0.0033 (10) | −0.0010 (11) |
| C9 | 0.0090 (11) | 0.0148 (12) | 0.0111 (12) | 0.0030 (10) | 0.0025 (11) | 0.0023 (10) |
| C10 | 0.0112 (12) | 0.0120 (12) | 0.0117 (12) | 0.0003 (9) | 0.0010 (11) | 0.0030 (9) |
| C11 | 0.0168 (13) | 0.0158 (12) | 0.0122 (13) | −0.0026 (10) | −0.0057 (10) | 0.0050 (10) |
| C12 | 0.0087 (11) | 0.0168 (12) | 0.0080 (11) | −0.0023 (10) | −0.0023 (10) | 0.0024 (9) |
| C13 | 0.0106 (12) | 0.0158 (12) | 0.0142 (13) | −0.0013 (10) | −0.0004 (10) | 0.0011 (11) |
| C14 | 0.0116 (12) | 0.0215 (13) | 0.0127 (12) | −0.0028 (10) | 0.0013 (10) | −0.0013 (10) |
| C15 | 0.0111 (12) | 0.0223 (13) | 0.0136 (13) | −0.0054 (11) | −0.0024 (11) | 0.0031 (11) |
| C16 | 0.0107 (12) | 0.0156 (12) | 0.0192 (13) | −0.0008 (10) | −0.0024 (10) | 0.0050 (11) |
| C17 | 0.0103 (12) | 0.0158 (12) | 0.0180 (13) | −0.0003 (10) | 0.0015 (10) | −0.0028 (11) |
| C18 | 0.0263 (16) | 0.0287 (15) | 0.0144 (13) | −0.0091 (12) | −0.0016 (13) | 0.0049 (11) |
Geometric parameters (Å, º)
| S1—N2 | 1.594 (2) | C7—C8 | 1.399 (4) |
| S1—N1 | 1.692 (2) | C7—H7 | 0.9500 |
| S1—C11 | 1.782 (3) | C8—C9 | 1.378 (4) |
| S2—O4 | 1.4430 (19) | C8—H8 | 0.9500 |
| S2—O3 | 1.451 (2) | C9—C10 | 1.523 (3) |
| S2—N2 | 1.631 (2) | C10—H10 | 1.0000 |
| S2—C12 | 1.768 (2) | C11—H11A | 0.9800 |
| O1—C1 | 1.353 (3) | C11—H11B | 0.9800 |
| O1—C2 | 1.472 (3) | C11—H11C | 0.9800 |
| O2—C1 | 1.195 (3) | C12—C13 | 1.387 (4) |
| N1—C1 | 1.388 (3) | C12—C17 | 1.392 (4) |
| N1—C10 | 1.475 (3) | C13—C14 | 1.394 (4) |
| C2—C3 | 1.522 (4) | C13—H13 | 0.9500 |
| C2—C10 | 1.535 (3) | C14—C15 | 1.391 (4) |
| C2—H2 | 1.0000 | C14—H14 | 0.9500 |
| C3—C4 | 1.506 (4) | C15—C16 | 1.392 (4) |
| C3—H3A | 0.9900 | C15—C18 | 1.511 (4) |
| C3—H3B | 0.9900 | C16—C17 | 1.387 (4) |
| C4—C5 | 1.386 (4) | C16—H16 | 0.9500 |
| C4—C9 | 1.400 (4) | C17—H17 | 0.9500 |
| C5—C6 | 1.393 (4) | C18—H18A | 0.9800 |
| C5—H5 | 0.9500 | C18—H18B | 0.9800 |
| C6—C7 | 1.386 (4) | C18—H18C | 0.9800 |
| C6—H6 | 0.9500 | ||
| N2—S1—N1 | 110.58 (11) | C9—C8—H8 | 120.8 |
| N2—S1—C11 | 99.43 (12) | C7—C8—H8 | 120.8 |
| N1—S1—C11 | 98.34 (11) | C8—C9—C4 | 121.5 (2) |
| O4—S2—O3 | 117.24 (12) | C8—C9—C10 | 129.0 (2) |
| O4—S2—N2 | 106.79 (12) | C4—C9—C10 | 109.5 (2) |
| O3—S2—N2 | 112.27 (11) | N1—C10—C9 | 113.4 (2) |
| O4—S2—C12 | 107.93 (11) | N1—C10—C2 | 100.5 (2) |
| O3—S2—C12 | 108.03 (12) | C9—C10—C2 | 103.0 (2) |
| N2—S2—C12 | 103.67 (12) | N1—C10—H10 | 113.0 |
| C1—O1—C2 | 110.39 (19) | C9—C10—H10 | 113.0 |
| C1—N1—C10 | 110.0 (2) | C2—C10—H10 | 113.0 |
| C1—N1—S1 | 119.14 (18) | S1—C11—H11A | 109.5 |
| C10—N1—S1 | 129.59 (17) | S1—C11—H11B | 109.5 |
| S1—N2—S2 | 114.97 (13) | H11A—C11—H11B | 109.5 |
| O2—C1—O1 | 124.1 (2) | S1—C11—H11C | 109.5 |
| O2—C1—N1 | 127.5 (2) | H11A—C11—H11C | 109.5 |
| O1—C1—N1 | 108.5 (2) | H11B—C11—H11C | 109.5 |
| O1—C2—C3 | 110.0 (2) | C13—C12—C17 | 121.0 (2) |
| O1—C2—C10 | 102.1 (2) | C13—C12—S2 | 119.9 (2) |
| C3—C2—C10 | 106.1 (2) | C17—C12—S2 | 119.0 (2) |
| O1—C2—H2 | 112.7 | C12—C13—C14 | 119.2 (2) |
| C3—C2—H2 | 112.7 | C12—C13—H13 | 120.4 |
| C10—C2—H2 | 112.7 | C14—C13—H13 | 120.4 |
| C4—C3—C2 | 103.5 (2) | C15—C14—C13 | 120.7 (3) |
| C4—C3—H3A | 111.1 | C15—C14—H14 | 119.6 |
| C2—C3—H3A | 111.1 | C13—C14—H14 | 119.6 |
| C4—C3—H3B | 111.1 | C14—C15—C16 | 118.9 (2) |
| C2—C3—H3B | 111.1 | C14—C15—C18 | 119.3 (3) |
| H3A—C3—H3B | 109.0 | C16—C15—C18 | 121.9 (3) |
| C5—C4—C9 | 120.2 (2) | C17—C16—C15 | 121.3 (2) |
| C5—C4—C3 | 128.9 (2) | C17—C16—H16 | 119.3 |
| C9—C4—C3 | 110.8 (2) | C15—C16—H16 | 119.3 |
| C4—C5—C6 | 118.1 (2) | C16—C17—C12 | 118.8 (2) |
| C4—C5—H5 | 120.9 | C16—C17—H17 | 120.6 |
| C6—C5—H5 | 120.9 | C12—C17—H17 | 120.6 |
| C7—C6—C5 | 121.6 (2) | C15—C18—H18A | 109.5 |
| C7—C6—H6 | 119.2 | C15—C18—H18B | 109.5 |
| C5—C6—H6 | 119.2 | H18A—C18—H18B | 109.5 |
| C6—C7—C8 | 120.1 (3) | C15—C18—H18C | 109.5 |
| C6—C7—H7 | 120.0 | H18A—C18—H18C | 109.5 |
| C8—C7—H7 | 120.0 | H18B—C18—H18C | 109.5 |
| C9—C8—C7 | 118.3 (2) |
Footnotes
Supporting information for this paper is available from the IUCr electronic archives (Reference: NK2234).
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989015024779/nk2234sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015024779/nk2234Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015024779/nk2234Isup3.cml
. DOI: 10.1107/S2056989015024779/nk2234fig1.tif
Labeling diagram of the title compound. Atomic displacement ellipsoids depicted at the 50% probability level. Hydrogen atoms depicted as spheres of an arbitrary radius.
CCDC reference: 1444186
Additional supporting information: crystallographic information; 3D view; checkCIF report