organic compounds
(E)-1-(Pyridin-4-yl)propan-1-one oxime
aInstitute of Pharmaceutical Sciences, Department of Pharmaceutical and Medicinal Chemistry, Eberhard Karls Universität Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany, bDepartment of Organic Chemistry, Johannes Gutenberg University Mainz, Duesbergweg 10-14, D-55099 Mainz, Germany, and cInstitute of Pharmaceutical Sciences, Department of Pharmaceutical and Medicinal Chemistry, Eberhard Karls Universität Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany
*Correspondence e-mail: pierre.koch@uni-tuebingen.de
The 8H10N2O, contains two crystallographically independent molecules of slightly different conformation, which are linked via an intermolecular O—H⋯N hydrogen bond. The dihedral angle between the pyridine ring and the oxime plane of molecule A [2.09 (19)°] is smaller than in molecule B [16.50 (18)°].
of the title compound, CKeywords: crystal structure; oxime; pyridine.
CCDC reference: 1480517
Structure description
The title compound, C8H10N2O, was synthesized by the reaction of 4-propionylpyridine and hydroxylamine. The contains two crystallographically independent molecules (A and B, Fig. 1) of slightly different conformation, which are linked via an intermolecular O—H⋯N hydrogen bond (Table 1). The dihedral angle between the pyridine ring and the oxime plane of molecule A [2.09 (19)°] is smaller than in molecule B [16.50 (18)°]. Both molecules are in an E orientation.
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In the crystal, each A molecule is connected with two B molecules and vice versa via further O—H⋯N hydrogen bonds, resulting in a zigzag chain parallel to the c axis.
Synthesis and crystallization
An aqueous solution of sodium hydroxide (20%, 20 ml) was added to hydroxylamine hydrochloride (3.70 g, 53.27 mmol) in water (50 ml). After addition of 4-propionylpyridine (5.72 g, 44.39 mmol) at 273 K, the reaction was stirred for 2.5 h at 298 K. Then, the product was extracted by ethyl acetate and the solvent was evaporated under reduced pressure. The title compound was obtained by crystallization in hot ethanol as white crystals in 87% yield. 1H NMR (400 MHz, DMSO-d6): δ 1.03 (t, 3J = 7.6 Hz, 3H, CH3), 2.71 (q, 3J = 7.6 Hz, 2H, CH2), 7.60 (d, 3J = 5.3 Hz, 2H, CH), 8.58 (d, 3J = 5.2 Hz, 2H, CH), 11.68 (s, 1H, OH); 13C-{1H}-NMR (100 MHz, DMSO-d6): δ 10.6, 17.7, 120.0, 142.9, 150.0, 156.2. For a similar preparation of the title compound, see Huang et al. (2008).
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1480517
10.1107/S2414314616008038/bt4011sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616008038/bt4011Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616008038/bt4011Isup3.cml
Crystal data, data collection and structure
details are summarized in Table 2. All H atoms were found in a difference map. Those bonded to C atoms were ideally positioned and refined as riding on their parent atoms, with aromatic C—H = 0.94 Å, methylene C—H = 0.98 Å and methyl C—H = 0.97 Å, and with Uiso(H) = 1.5Ueq(C) for methyl H atoms or 1.2Ueq(C) otherwise. The positions of the H atoms bonded to O atoms were taken from a difference map and they were refined as riding on their parent atoms, with Uiso(H) = 1.5Ueq(O).An aqueous solution of sodium hydroxide (20%, 20 ml) was added to hydroxylamine hydrochloride (3.70 g, 53.27 mmol) in water (50 ml). After addition of 4-propionylpyridine (5.72 g, 44.39 mmol) at 273 K, the reaction was stirred for 2.5 h at 298 K. Then, the product was extracted by ethyl acetate and the solvent was evaporated under reduced pressure. Pure compound was obtained by crystallization in hot ethanol as white crystals in 87% yield. 1H NMR (400 MHz, DMSO-d6): δ 1.03 (t, 3J = 7.6 Hz, 3H, CH3), 2.71 (q, 3J = 7.6 Hz, 2H, CH2), 7.60 (d, 3J = 5.3 Hz, 2H, CH), 8.58 (d, 3J = 5.2 Hz, 2H, CH), 11.68 (s, 1H, OH); 13C-{1H}-NMR (100 MHz, DMSO-d6): δ 10.6, 17.7, 120.0, 142.9, 150.0, 156.2. For a similar preparation of the title compound, see Huang et al. (2008).
The title compound, C8H10N2O, was synthesized by the reaction of 4-propionylpyridine and hydroxylamine. The
contains two crystallographically independent molecules (A and B, Fig. 1) of slightly different conformation, which are linked via an intermolecular O—H···N hydrogen bond (Table 1). The dihedral angle between the pyridine ring and the oxime plane of molecule A [2.09 (19)°] is smaller than in molecule B [16.50 (18)°]. Both molecules are in an E orientation.In the crystal, each A molecule is connected with two B molecules and vice versa via further O—H···N hydrogen bonds, resulting in a zigzag chain parallel to the c axis.
Data collection: X-AREA (Stoe & Cie, 2011); cell
X-AREA (Stoe & Cie, 2011); data reduction: X-RED (Stoe & Cie, 2011); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: XP (Sheldrick, 2015); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015).Fig. 1. The molecular structure of the title compound, showing the atom labelling and displacement ellipsoids drawn at the 50% probability level. |
C8H10N2O | Dx = 1.243 Mg m−3 |
Mr = 150.18 | Cu Kα radiation, λ = 1.54178 Å |
Orthorhombic, P212121 | Cell parameters from 42392 reflections |
a = 7.9149 (3) Å | θ = 4.1–68.6° |
b = 9.3676 (4) Å | µ = 0.69 mm−1 |
c = 21.6431 (8) Å | T = 213 K |
V = 1604.70 (11) Å3 | Plate, colourless |
Z = 8 | 0.70 × 0.40 × 0.20 mm |
F(000) = 640 |
Stoe IPDS 2T diffractometer | 2797 independent reflections |
Radiation source: Incoatec microSource Cu | 2734 reflections with I > 2σ(I) |
X-ray mirror monochromator | Rint = 0.030 |
Detector resolution: 6.67 pixels mm-1 | θmax = 67.5°, θmin = 4.1° |
rotation method scans | h = −9→9 |
Absorption correction: integration (X-RED; Stoe & Cie, 2011) | k = −11→11 |
Tmin = 0.684, Tmax = 0.888 | l = −25→24 |
15705 measured reflections |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.031 | w = 1/[σ2(Fo2) + (0.0476P)2 + 0.2424P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.088 | (Δ/σ)max = 0.001 |
S = 1.12 | Δρmax = 0.14 e Å−3 |
2797 reflections | Δρmin = −0.15 e Å−3 |
201 parameters | Absolute structure: Flack x determined using 1114 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004) |
0 restraints | Absolute structure parameter: 0.01 (6) |
C8H10N2O | V = 1604.70 (11) Å3 |
Mr = 150.18 | Z = 8 |
Orthorhombic, P212121 | Cu Kα radiation |
a = 7.9149 (3) Å | µ = 0.69 mm−1 |
b = 9.3676 (4) Å | T = 213 K |
c = 21.6431 (8) Å | 0.70 × 0.40 × 0.20 mm |
Stoe IPDS 2T diffractometer | 2797 independent reflections |
Absorption correction: integration (X-RED; Stoe & Cie, 2011) | 2734 reflections with I > 2σ(I) |
Tmin = 0.684, Tmax = 0.888 | Rint = 0.030 |
15705 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | H-atom parameters constrained |
wR(F2) = 0.088 | Δρmax = 0.14 e Å−3 |
S = 1.12 | Δρmin = −0.15 e Å−3 |
2797 reflections | Absolute structure: Flack x determined using 1114 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004) |
201 parameters | Absolute structure parameter: 0.01 (6) |
0 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
C1A | 0.4400 (3) | 0.8985 (2) | 0.69902 (8) | 0.0352 (4) | |
C2A | 0.4013 (3) | 1.0058 (2) | 0.74113 (10) | 0.0463 (5) | |
H2A | 0.4815 | 1.0766 | 0.7505 | 0.056* | |
C3A | 0.2444 (3) | 1.0079 (3) | 0.76919 (10) | 0.0507 (6) | |
H3A | 0.2219 | 1.0809 | 0.7979 | 0.061* | |
N4A | 0.1234 (2) | 0.9129 (2) | 0.75800 (9) | 0.0475 (4) | |
C5A | 0.1604 (3) | 0.8092 (2) | 0.71751 (10) | 0.0458 (5) | |
H5A | 0.0769 | 0.7407 | 0.7089 | 0.055* | |
C6A | 0.3135 (3) | 0.7972 (2) | 0.68773 (9) | 0.0409 (4) | |
H6A | 0.3329 | 0.7217 | 0.6600 | 0.049* | |
C7A | 0.6061 (3) | 0.8934 (2) | 0.66701 (8) | 0.0359 (4) | |
C8A | 0.7356 (3) | 1.0078 (2) | 0.67723 (9) | 0.0401 (5) | |
H8A | 0.8478 | 0.9702 | 0.6671 | 0.048* | |
H8B | 0.7358 | 1.0350 | 0.7209 | 0.048* | |
C9A | 0.7009 (4) | 1.1392 (3) | 0.63795 (11) | 0.0576 (6) | |
H9A | 0.7926 | 1.2069 | 0.6428 | 0.086* | |
H9B | 0.5958 | 1.1830 | 0.6511 | 0.086* | |
H9C | 0.6921 | 1.1114 | 0.5949 | 0.086* | |
N10A | 0.6241 (2) | 0.7873 (2) | 0.62925 (8) | 0.0441 (4) | |
O11A | 0.7815 (2) | 0.78887 (17) | 0.60004 (7) | 0.0515 (4) | |
H11A | 0.7795 | 0.6997 | 0.5702 | 0.077* | |
C1B | 0.7775 (2) | 0.3235 (2) | 0.44265 (8) | 0.0339 (4) | |
C2B | 0.6914 (3) | 0.4473 (2) | 0.42528 (9) | 0.0403 (5) | |
H2B | 0.6315 | 0.4502 | 0.3878 | 0.048* | |
C3B | 0.6946 (3) | 0.5650 (2) | 0.46333 (10) | 0.0462 (5) | |
H3B | 0.6366 | 0.6475 | 0.4506 | 0.055* | |
N4B | 0.7761 (2) | 0.56832 (19) | 0.51765 (8) | 0.0454 (4) | |
C5B | 0.8581 (3) | 0.4508 (2) | 0.53451 (10) | 0.0439 (5) | |
H5B | 0.9157 | 0.4512 | 0.5725 | 0.053* | |
C6B | 0.8631 (3) | 0.3273 (2) | 0.49901 (9) | 0.0398 (4) | |
H6B | 0.9236 | 0.2471 | 0.5128 | 0.048* | |
C7B | 0.7755 (2) | 0.1927 (2) | 0.40380 (8) | 0.0344 (4) | |
C8B | 0.8959 (2) | 0.0715 (2) | 0.41461 (9) | 0.0391 (4) | |
H8C | 0.9967 | 0.1076 | 0.4358 | 0.047* | |
H8D | 0.9316 | 0.0324 | 0.3747 | 0.047* | |
C9B | 0.8171 (3) | −0.0472 (2) | 0.45324 (11) | 0.0487 (5) | |
H9D | 0.7127 | −0.0783 | 0.4340 | 0.073* | |
H9E | 0.7936 | −0.0117 | 0.4945 | 0.073* | |
H9F | 0.8949 | −0.1270 | 0.4558 | 0.073* | |
N10B | 0.6582 (2) | 0.19141 (18) | 0.36239 (8) | 0.0404 (4) | |
O11B | 0.6592 (2) | 0.06524 (17) | 0.32787 (7) | 0.0495 (4) | |
H11B | 0.5572 | 0.0810 | 0.2998 | 0.074* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1A | 0.0400 (10) | 0.0344 (10) | 0.0313 (9) | 0.0014 (8) | −0.0010 (8) | 0.0027 (7) |
C2A | 0.0467 (12) | 0.0458 (12) | 0.0463 (11) | −0.0048 (9) | 0.0032 (9) | −0.0100 (9) |
C3A | 0.0525 (13) | 0.0518 (12) | 0.0477 (12) | −0.0006 (10) | 0.0092 (10) | −0.0078 (10) |
N4A | 0.0448 (10) | 0.0517 (10) | 0.0459 (9) | 0.0019 (8) | 0.0059 (8) | 0.0071 (8) |
C5A | 0.0432 (12) | 0.0435 (11) | 0.0506 (11) | −0.0044 (10) | −0.0005 (9) | 0.0060 (10) |
C6A | 0.0447 (11) | 0.0369 (10) | 0.0412 (10) | −0.0004 (9) | −0.0011 (9) | 0.0005 (9) |
C7A | 0.0408 (10) | 0.0349 (10) | 0.0321 (9) | 0.0019 (8) | −0.0019 (8) | 0.0008 (8) |
C8A | 0.0370 (10) | 0.0433 (11) | 0.0402 (10) | 0.0006 (8) | −0.0026 (8) | −0.0072 (8) |
C9A | 0.0737 (16) | 0.0494 (12) | 0.0498 (12) | −0.0184 (12) | −0.0048 (12) | 0.0044 (10) |
N10A | 0.0474 (10) | 0.0413 (9) | 0.0435 (9) | −0.0013 (8) | 0.0098 (8) | −0.0044 (8) |
O11A | 0.0491 (9) | 0.0512 (9) | 0.0543 (9) | −0.0032 (7) | 0.0163 (7) | −0.0141 (7) |
C1B | 0.0308 (9) | 0.0345 (9) | 0.0363 (9) | −0.0022 (8) | 0.0039 (7) | 0.0006 (8) |
C2B | 0.0442 (11) | 0.0369 (10) | 0.0399 (10) | 0.0004 (9) | 0.0011 (9) | 0.0037 (8) |
C3B | 0.0547 (12) | 0.0325 (10) | 0.0515 (12) | 0.0013 (10) | 0.0074 (10) | 0.0023 (9) |
N4B | 0.0482 (10) | 0.0390 (9) | 0.0490 (10) | −0.0052 (8) | 0.0103 (8) | −0.0063 (7) |
C5B | 0.0401 (10) | 0.0487 (12) | 0.0430 (11) | −0.0042 (9) | 0.0004 (9) | −0.0078 (9) |
C6B | 0.0361 (10) | 0.0410 (10) | 0.0424 (10) | 0.0013 (9) | −0.0020 (8) | −0.0027 (8) |
C7B | 0.0327 (9) | 0.0361 (9) | 0.0343 (9) | −0.0011 (8) | 0.0010 (7) | −0.0003 (8) |
C8B | 0.0364 (10) | 0.0385 (10) | 0.0423 (10) | 0.0040 (8) | −0.0016 (8) | −0.0061 (8) |
C9B | 0.0537 (13) | 0.0387 (11) | 0.0537 (12) | 0.0045 (10) | −0.0024 (10) | 0.0012 (9) |
N10B | 0.0420 (9) | 0.0391 (9) | 0.0400 (8) | 0.0017 (8) | −0.0030 (7) | −0.0055 (7) |
O11B | 0.0524 (9) | 0.0488 (8) | 0.0474 (8) | 0.0067 (7) | −0.0113 (7) | −0.0158 (7) |
C1A—C2A | 1.391 (3) | C1B—C6B | 1.396 (3) |
C1A—C6A | 1.400 (3) | C1B—C2B | 1.397 (3) |
C1A—C7A | 1.487 (3) | C1B—C7B | 1.486 (3) |
C2A—C3A | 1.383 (3) | C2B—C3B | 1.377 (3) |
C2A—H2A | 0.9400 | C2B—H2B | 0.9400 |
C3A—N4A | 1.330 (3) | C3B—N4B | 1.341 (3) |
C3A—H3A | 0.9400 | C3B—H3B | 0.9400 |
N4A—C5A | 1.340 (3) | N4B—C5B | 1.329 (3) |
C5A—C6A | 1.377 (3) | C5B—C6B | 1.389 (3) |
C5A—H5A | 0.9400 | C5B—H5B | 0.9400 |
C6A—H6A | 0.9400 | C6B—H6B | 0.9400 |
C7A—N10A | 1.294 (3) | C7B—N10B | 1.290 (2) |
C7A—C8A | 1.499 (3) | C7B—C8B | 1.501 (3) |
C8A—C9A | 1.521 (3) | C8B—C9B | 1.525 (3) |
C8A—H8A | 0.9800 | C8B—H8C | 0.9800 |
C8A—H8B | 0.9800 | C8B—H8D | 0.9800 |
C9A—H9A | 0.9700 | C9B—H9D | 0.9700 |
C9A—H9B | 0.9700 | C9B—H9E | 0.9700 |
C9A—H9C | 0.9700 | C9B—H9F | 0.9700 |
N10A—O11A | 1.397 (2) | N10B—O11B | 1.398 (2) |
O11A—H11A | 1.0560 | O11B—H11B | 1.0215 |
C2A—C1A—C6A | 116.51 (19) | C6B—C1B—C2B | 116.79 (18) |
C2A—C1A—C7A | 121.52 (18) | C6B—C1B—C7B | 121.40 (17) |
C6A—C1A—C7A | 121.96 (17) | C2B—C1B—C7B | 121.80 (17) |
C3A—C2A—C1A | 119.7 (2) | C3B—C2B—C1B | 119.67 (19) |
C3A—C2A—H2A | 120.1 | C3B—C2B—H2B | 120.2 |
C1A—C2A—H2A | 120.1 | C1B—C2B—H2B | 120.2 |
N4A—C3A—C2A | 123.9 (2) | N4B—C3B—C2B | 123.5 (2) |
N4A—C3A—H3A | 118.1 | N4B—C3B—H3B | 118.3 |
C2A—C3A—H3A | 118.1 | C2B—C3B—H3B | 118.3 |
C3A—N4A—C5A | 116.54 (19) | C5B—N4B—C3B | 117.15 (18) |
N4A—C5A—C6A | 123.9 (2) | N4B—C5B—C6B | 123.5 (2) |
N4A—C5A—H5A | 118.1 | N4B—C5B—H5B | 118.3 |
C6A—C5A—H5A | 118.1 | C6B—C5B—H5B | 118.3 |
C5A—C6A—C1A | 119.48 (19) | C5B—C6B—C1B | 119.41 (19) |
C5A—C6A—H6A | 120.3 | C5B—C6B—H6B | 120.3 |
C1A—C6A—H6A | 120.3 | C1B—C6B—H6B | 120.3 |
N10A—C7A—C1A | 114.60 (17) | N10B—C7B—C1B | 114.11 (17) |
N10A—C7A—C8A | 124.50 (18) | N10B—C7B—C8B | 123.93 (17) |
C1A—C7A—C8A | 120.86 (17) | C1B—C7B—C8B | 121.91 (16) |
C7A—C8A—C9A | 111.87 (17) | C7B—C8B—C9B | 112.16 (17) |
C7A—C8A—H8A | 109.2 | C7B—C8B—H8C | 109.2 |
C9A—C8A—H8A | 109.2 | C9B—C8B—H8C | 109.2 |
C7A—C8A—H8B | 109.2 | C7B—C8B—H8D | 109.2 |
C9A—C8A—H8B | 109.2 | C9B—C8B—H8D | 109.2 |
H8A—C8A—H8B | 107.9 | H8C—C8B—H8D | 107.9 |
C8A—C9A—H9A | 109.5 | C8B—C9B—H9D | 109.5 |
C8A—C9A—H9B | 109.5 | C8B—C9B—H9E | 109.5 |
H9A—C9A—H9B | 109.5 | H9D—C9B—H9E | 109.5 |
C8A—C9A—H9C | 109.5 | C8B—C9B—H9F | 109.5 |
H9A—C9A—H9C | 109.5 | H9D—C9B—H9F | 109.5 |
H9B—C9A—H9C | 109.5 | H9E—C9B—H9F | 109.5 |
C7A—N10A—O11A | 112.09 (17) | C7B—N10B—O11B | 112.01 (16) |
N10A—O11A—H11A | 104.8 | N10B—O11B—H11B | 101.0 |
C6A—C1A—C2A—C3A | 0.0 (3) | C6B—C1B—C2B—C3B | 0.2 (3) |
C7A—C1A—C2A—C3A | 179.00 (19) | C7B—C1B—C2B—C3B | 178.90 (18) |
C1A—C2A—C3A—N4A | −0.8 (4) | C1B—C2B—C3B—N4B | −0.5 (3) |
C2A—C3A—N4A—C5A | 0.9 (3) | C2B—C3B—N4B—C5B | 0.4 (3) |
C3A—N4A—C5A—C6A | −0.2 (3) | C3B—N4B—C5B—C6B | 0.1 (3) |
N4A—C5A—C6A—C1A | −0.6 (3) | N4B—C5B—C6B—C1B | −0.5 (3) |
C2A—C1A—C6A—C5A | 0.7 (3) | C2B—C1B—C6B—C5B | 0.3 (3) |
C7A—C1A—C6A—C5A | −178.33 (18) | C7B—C1B—C6B—C5B | −178.43 (19) |
C2A—C1A—C7A—N10A | 179.88 (19) | C6B—C1B—C7B—N10B | 162.62 (18) |
C6A—C1A—C7A—N10A | −1.2 (3) | C2B—C1B—C7B—N10B | −16.1 (3) |
C2A—C1A—C7A—C8A | −2.5 (3) | C6B—C1B—C7B—C8B | −14.8 (3) |
C6A—C1A—C7A—C8A | 176.47 (18) | C2B—C1B—C7B—C8B | 166.50 (18) |
N10A—C7A—C8A—C9A | 95.8 (2) | N10B—C7B—C8B—C9B | −80.2 (2) |
C1A—C7A—C8A—C9A | −81.6 (2) | C1B—C7B—C8B—C9B | 97.0 (2) |
C1A—C7A—N10A—O11A | 179.33 (16) | C1B—C7B—N10B—O11B | −178.80 (15) |
C8A—C7A—N10A—O11A | 1.8 (3) | C8B—C7B—N10B—O11B | −1.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O11A—H11A···N4B | 1.06 | 1.68 | 2.729 (2) | 175 |
O11B—H11B···N4Ai | 1.02 | 1.69 | 2.708 (2) | 172 |
Symmetry code: (i) −x+1/2, −y+1, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O11A—H11A···N4B | 1.06 | 1.68 | 2.729 (2) | 175.0 |
O11B—H11B···N4Ai | 1.02 | 1.69 | 2.708 (2) | 172.1 |
Symmetry code: (i) −x+1/2, −y+1, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C8H10N2O |
Mr | 150.18 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 213 |
a, b, c (Å) | 7.9149 (3), 9.3676 (4), 21.6431 (8) |
V (Å3) | 1604.70 (11) |
Z | 8 |
Radiation type | Cu Kα |
µ (mm−1) | 0.69 |
Crystal size (mm) | 0.70 × 0.40 × 0.20 |
Data collection | |
Diffractometer | Stoe IPDS 2T |
Absorption correction | Integration (X-RED; Stoe & Cie, 2011) |
Tmin, Tmax | 0.684, 0.888 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15705, 2797, 2734 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.599 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.088, 1.12 |
No. of reflections | 2797 |
No. of parameters | 201 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.14, −0.15 |
Absolute structure | Flack x determined using 1114 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004) |
Absolute structure parameter | 0.01 (6) |
Computer programs: X-AREA (Stoe & Cie, 2011), X-RED (Stoe & Cie, 2011), SIR2004 (Burla et al., 2005), SHELXL2013 (Sheldrick, 2015), XP (Sheldrick, 2015).
References
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Huang, K., Merced, F. G., Ortiz-Marciales, M., Meléndez, H. J., Correa, W. & De Jesús, M. (2008). J. Org. Chem. 73, 4017–4026. CrossRef PubMed CAS Google Scholar
Parsons, S. & Flack, H. (2004). Acta Cryst. A60, s61. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Stoe & Cie (2011). X-RED and X-AREA. Stoe & Cie, Darmstadt, Germany. Google Scholar
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