research communications
N-[(4-methylpyridin-2-yl)carbamothioyl]benzamide
of 4-methyl-aSchool of Chemical Sciences, 11800, USM Pulau Pinang, Malaysia, and bCollege of Sciences and Arts, Rabigh, King Abdulaziz University, Saudi Arabia, and International University of Africa, Khartoum, Sudan
*Correspondence e-mail: farook@usm.my
In the title compound, C15H15N3OS, the dihedral angle between the planes of the benzene and pyridine rings is 26.86 (9)°. Intramolecular N—H⋯O and C—H⋯S hydrogen bonds both generate S(6) rings. The C=O and C=S bonds lie to opposite sides of the molecule. In the crystal, inversion dimers linked by pairs of N—H⋯S hydrogen bonds generate R22(8) loops.
Keywords: crystal structure; thiourea compounds; thiocarbonyl groups; benzamide; hydrogen bonding.
CCDC reference: 1050132
1. Chemical context
The role of benzoyl thiourea derivatives in coordination chemistry has been extensively studied and quite satisfactorily elucidated. As benzoyl thioureas have suitable C=O and C=S functional groups, they can be considered as useful chelating agents due to their ability to encapsulate metal ions into their coordinating moiety. Thiourea and its derivatives have found extensive applications in the fields of medicine, agriculture and analytical chemistry. Thioureas are also known to exhibit a wide range of biological activities including anticancer (Saeed et al., 2010a), antifungal (Saeed et al., 2010b) and as agrochemicals (Xu et al., 2003). As part of our studies in this area, we now describe the synthesis and structure of the title compound, (I).
2. Structural commentary
The title compound (Fig. 1) is a benzoyl thiourea derivative and analogous to a compound recently reported by us (Adam et al., 2014), except that the other substituent is changed to methylpyridine and the thiourea moiety is still in a para position. The dihedral angle between the planes of the benzene and pyridine rings is 26.86 (9)°. The C=O bond length of 1.225 (2) Å is comparable to that observed in N-benzoyl-N′-phenylthiourea (Hassan et al., 2008a). The C—N bond lengths are in the range 1.328 (2)–1.417 (2) Å, shorter than the normal single C—N bond length (1.469 Å), indicating partial double-bond character owing to the at the carbonylthiourea moiety.
As in most benzoyl thiourea derivatives, an intramolecular N—H⋯O hydrogen bond leads to the formation of an S(6) ring, namely, C7/N1/C8/N2/H2/O1. An intramolecular C—H⋯S interaction (C9/N2/C8/S1/H10/C10) also generates an S(6) ring (Fig. 1, Table 1).
3. Supramolecular features
In the crystal of (I), inversion dimers linked by pairs of N—H⋯S hydrogen bonds (Table 1, Fig. 2) generate (8) loops. As about the N1—C7 and N2—C8 single bonds is hindered, the C=O and C=S bonds are unlikely to align at the same side of the molecule in order to form a chelate with a metal ion.
4. Synthesis and crystallization
The title compound was prepared according to a slight modification of the method described by Hassan et al. (2008b). p-Benzoyl chloride (13 mmol) was added dropwise to a stirred acetone solution (30 ml) of ammonium thiocyanate (13 mmol). The mixture was stirred for 10 min. A solution of 2-amino-4-picoline in acetone was added and the reaction mixture was refluxed for 3 h, after which the solution was poured into a beaker containing some ice cubes. The resulting precipitate was collected by filtration, washed several times with a cold ethanol/water mixture and purified by recrystallization from an ethanol solution.
5. Refinement
Crystal data, data collection and structure . The H-atoms on the N atoms were located in a difference-Fourier map and were freely refined. All other H atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.96 Å and Uiso(H) = 1.2Ueq(aromatic C) or 1.5Ueq(methyl C).
details are summarized in Table 2Supporting information
CCDC reference: 1050132
10.1107/S2056989015003412/hb7367sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989015003412/hb7367Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015003412/hb7367Isup3.cml
The role of benzoyl thiourea derivatives in coordination chemistry has been extensively studied and quite satisfactorily elucidated. As benzoyl thioureas have suitable C=O and C=S functional groups, they can be considered as useful chelating agents due to their ability to encapsulate metal ions into their coordinating moiety. Thiourea and its derivatives have found extensive applications in the fields of medicine, agriculture and analytical chemistry. Thioureas are also known to exhibit a wide range of biological activities including anticancer (Saeed et al., 2010a), antifungal (Saeed et al., 2010b) and as agrochemicals (Xu et al., 2003). As part of our studies in this area, we now describe the synthesis and structure of the title compound, (I).
The title compound (Fig. 1) is a benzoyl thiourea derivative and analogous to a compound recently reported by us (Adam et al., 2014), except that the other substituent is changed to methylpyridine and the thiourea moiety is still in a para position. The dihedral angle between the planes of the benzene and pyridine rings is 26.86 (9)°. The C=O bond length of 1.225 (2) Å is longer than the average C=O bond length (1.200 Å) and comparable to that observed in N-benzoyl-N'-phenylthiourea (Hassan et al., 2008a). The C—N bond lengths are in the range 1.328 (2)–1.417 (2) Å, shorter than the normal single C—N bond length (1.469 Å), indicating partial double-bond character owing to the
at the carbonylthiourea moiety.As in most benzoyl thiourea derivatives, an intramolecular N—H···O hydrogen bond leads to the formation of an S(6) ring, namely, C7/N1/C8/N2/H2/O1. An intramolecular C—H···S interaction (C9/N2/C8/S1/H10/C10) also generates an S(6) ring (Fig. 1, Table 1).
In the crystal of (I), inversion dimers linked by pairs of N—H···S hydrogen bonds (Table 1, Fig. 2) generate R22(8) loops. As
about the N1—C7 and N2—C8 single bonds is hindered, the C=O and C=S bonds are unlikely to align at the same side of the molecule in order to form a chelate with a metal ion.Freshly prepared substituted p-benzoyl chloride (13 mmol) was added dropwise to a stirred acetone solution (30 ml) of ammonium thiocyanate (13 mmol). The mixture was stirred for 10 min. A solution of 2-amino-4-picoline in acetone was added and the reaction mixture was refluxed for 3 h, after which the solution was poured into a beaker containing some ice cubes. The resulting precipitate was collected by filtration, washed several times with a cold ethanol/water mixture and purified by recrystallization from an ethanol solution (Hassan et al., 2008b) as colourless plates (yield 61%).
Crystal data, data collection and structure
details are summarized in Table 2. The H-atoms on the N atoms were located in a difference-Fourier map and were fully refined. All other H atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.96 Å and Uiso(H) = 1.2Ueq(aromatic C) or 1.5Ueq(methyl C).Data collection: APEX2 (Bruker, 2005); cell
SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The molecular structure of the title compound, with 50% probability displacement ellipsoids. Hydrogen bonds are shown as dashed lines. | |
Fig. 2. The crystal packing of the title compound viewed down the c axis. Hydrogen bonds are shown as dashed lines. |
C15H15N3OS | F(000) = 600 |
Mr = 285.36 | Dx = 1.313 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3960 reflections |
a = 11.5297 (12) Å | θ = 2.4–25.9° |
b = 6.1860 (6) Å | µ = 0.22 mm−1 |
c = 20.657 (2) Å | T = 294 K |
β = 101.431 (2)° | Plate, colourless |
V = 1444.1 (3) Å3 | 0.38 × 0.34 × 0.09 mm |
Z = 4 |
Bruker APEXII CCD diffractometer | 4233 independent reflections |
Radiation source: fine-focus sealed tube | 2790 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
ϕ and ω scans | θmax = 30.1°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −16→16 |
Tmin = 0.920, Tmax = 0.981 | k = −8→8 |
15813 measured reflections | l = −29→29 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.164 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0866P)2 + 0.1249P] where P = (Fo2 + 2Fc2)/3 |
4233 reflections | (Δ/σ)max < 0.001 |
191 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C15H15N3OS | V = 1444.1 (3) Å3 |
Mr = 285.36 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.5297 (12) Å | µ = 0.22 mm−1 |
b = 6.1860 (6) Å | T = 294 K |
c = 20.657 (2) Å | 0.38 × 0.34 × 0.09 mm |
β = 101.431 (2)° |
Bruker APEXII CCD diffractometer | 4233 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 2790 reflections with I > 2σ(I) |
Tmin = 0.920, Tmax = 0.981 | Rint = 0.028 |
15813 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.164 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.27 e Å−3 |
4233 reflections | Δρmin = −0.19 e Å−3 |
191 parameters |
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.47752 (4) | 0.82687 (9) | 0.41107 (2) | 0.0655 (2) | |
O1 | 0.10758 (10) | 1.0358 (2) | 0.43058 (7) | 0.0664 (4) | |
N1 | 0.30931 (13) | 1.0520 (2) | 0.44717 (7) | 0.0489 (3) | |
N2 | 0.24183 (13) | 0.7757 (3) | 0.37524 (7) | 0.0499 (3) | |
N3 | 0.11827 (13) | 0.5315 (3) | 0.31789 (8) | 0.0656 (4) | |
C1 | 0.11290 (16) | 1.3270 (3) | 0.53813 (9) | 0.0549 (4) | |
H1A | 0.0514 | 1.2271 | 0.5317 | 0.066* | |
C2 | 0.11387 (17) | 1.4947 (3) | 0.58230 (9) | 0.0618 (5) | |
H2A | 0.0534 | 1.5049 | 0.6060 | 0.074* | |
C3 | 0.20271 (18) | 1.6472 (3) | 0.59200 (9) | 0.0585 (5) | |
C4 | 0.29222 (18) | 1.6283 (3) | 0.55643 (9) | 0.0595 (5) | |
H4A | 0.3525 | 1.7306 | 0.5622 | 0.071* | |
C5 | 0.29362 (16) | 1.4598 (3) | 0.51247 (8) | 0.0525 (4) | |
H5A | 0.3547 | 1.4492 | 0.4892 | 0.063* | |
C6 | 0.20408 (14) | 1.3073 (3) | 0.50317 (8) | 0.0463 (4) | |
C7 | 0.20039 (14) | 1.1224 (3) | 0.45721 (8) | 0.0481 (4) | |
C8 | 0.33584 (14) | 0.8813 (3) | 0.40921 (7) | 0.0456 (4) | |
C9 | 0.23136 (14) | 0.5873 (3) | 0.33544 (7) | 0.0485 (4) | |
C10 | 0.32251 (15) | 0.4763 (3) | 0.31581 (8) | 0.0546 (4) | |
H10A | 0.4004 | 0.5224 | 0.3292 | 0.065* | |
C11 | 0.29672 (18) | 0.2966 (3) | 0.27621 (8) | 0.0549 (4) | |
C12 | 0.18012 (19) | 0.2358 (4) | 0.25798 (10) | 0.0673 (5) | |
H12A | 0.1591 | 0.1146 | 0.2316 | 0.081* | |
C13 | 0.0953 (2) | 0.3570 (4) | 0.27931 (12) | 0.0766 (6) | |
H13A | 0.0167 | 0.3150 | 0.2661 | 0.092* | |
C14 | 0.2033 (3) | 1.8322 (4) | 0.64013 (11) | 0.0836 (7) | |
H14A | 0.2708 | 1.9228 | 0.6397 | 0.125* | |
H14B | 0.2073 | 1.7754 | 0.6838 | 0.125* | |
H14C | 0.1322 | 1.9156 | 0.6274 | 0.125* | |
C15 | 0.3924 (2) | 0.1738 (4) | 0.25264 (13) | 0.0834 (7) | |
H15A | 0.4636 | 0.1785 | 0.2858 | 0.125* | |
H15B | 0.4068 | 0.2380 | 0.2126 | 0.125* | |
H15C | 0.3682 | 0.0262 | 0.2443 | 0.125* | |
H1N2 | 0.181 (2) | 0.810 (4) | 0.3871 (12) | 0.083 (7)* | |
H1N1 | 0.3673 (18) | 1.100 (3) | 0.4720 (10) | 0.055 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0427 (3) | 0.0886 (4) | 0.0651 (3) | −0.0032 (2) | 0.0107 (2) | −0.0266 (2) |
O1 | 0.0437 (7) | 0.0727 (10) | 0.0793 (9) | 0.0008 (6) | 0.0035 (6) | −0.0220 (7) |
N1 | 0.0440 (7) | 0.0525 (9) | 0.0488 (7) | −0.0028 (6) | 0.0057 (6) | −0.0086 (6) |
N2 | 0.0429 (7) | 0.0548 (9) | 0.0498 (7) | 0.0016 (6) | 0.0040 (6) | −0.0088 (6) |
N3 | 0.0508 (8) | 0.0691 (11) | 0.0723 (10) | −0.0025 (8) | 0.0012 (7) | −0.0189 (8) |
C1 | 0.0478 (9) | 0.0604 (11) | 0.0555 (9) | 0.0019 (8) | 0.0083 (7) | −0.0018 (8) |
C2 | 0.0624 (11) | 0.0725 (13) | 0.0510 (9) | 0.0149 (10) | 0.0124 (8) | −0.0027 (8) |
C3 | 0.0731 (12) | 0.0516 (11) | 0.0464 (9) | 0.0149 (9) | 0.0011 (8) | 0.0002 (7) |
C4 | 0.0701 (12) | 0.0457 (10) | 0.0602 (10) | −0.0014 (9) | 0.0066 (9) | 0.0008 (8) |
C5 | 0.0597 (10) | 0.0466 (10) | 0.0520 (9) | 0.0011 (8) | 0.0127 (7) | 0.0038 (7) |
C6 | 0.0475 (8) | 0.0447 (9) | 0.0452 (8) | 0.0044 (7) | 0.0053 (6) | 0.0016 (6) |
C7 | 0.0454 (8) | 0.0494 (10) | 0.0480 (8) | 0.0005 (7) | 0.0054 (7) | −0.0004 (7) |
C8 | 0.0457 (8) | 0.0501 (9) | 0.0401 (7) | −0.0016 (7) | 0.0064 (6) | −0.0001 (6) |
C9 | 0.0495 (9) | 0.0526 (10) | 0.0407 (7) | −0.0004 (7) | 0.0029 (6) | −0.0006 (7) |
C10 | 0.0548 (10) | 0.0566 (11) | 0.0534 (9) | −0.0008 (8) | 0.0131 (7) | −0.0033 (8) |
C11 | 0.0730 (12) | 0.0469 (10) | 0.0460 (8) | 0.0014 (8) | 0.0148 (8) | 0.0007 (7) |
C12 | 0.0770 (13) | 0.0601 (12) | 0.0648 (11) | −0.0072 (10) | 0.0138 (10) | −0.0136 (9) |
C13 | 0.0624 (12) | 0.0760 (15) | 0.0862 (14) | −0.0093 (10) | 0.0022 (10) | −0.0282 (12) |
C14 | 0.114 (2) | 0.0673 (15) | 0.0669 (13) | 0.0168 (12) | 0.0112 (13) | −0.0144 (10) |
C15 | 0.0940 (17) | 0.0733 (16) | 0.0907 (16) | 0.0025 (12) | 0.0374 (14) | −0.0172 (12) |
S1—C8 | 1.6609 (16) | C4—H4A | 0.9300 |
O1—C7 | 1.225 (2) | C5—C6 | 1.384 (2) |
N1—C7 | 1.383 (2) | C5—H5A | 0.9300 |
N1—C8 | 1.385 (2) | C6—C7 | 1.482 (2) |
N1—H1N1 | 0.81 (2) | C9—C10 | 1.382 (2) |
N2—C8 | 1.339 (2) | C10—C11 | 1.377 (3) |
N2—C9 | 1.417 (2) | C10—H10A | 0.9300 |
N2—H1N2 | 0.82 (2) | C11—C12 | 1.375 (3) |
N3—C9 | 1.328 (2) | C11—C15 | 1.498 (3) |
N3—C13 | 1.337 (3) | C12—C13 | 1.373 (3) |
C1—C2 | 1.380 (3) | C12—H12A | 0.9300 |
C1—C6 | 1.394 (2) | C13—H13A | 0.9300 |
C1—H1A | 0.9300 | C14—H14A | 0.9600 |
C2—C3 | 1.378 (3) | C14—H14B | 0.9600 |
C2—H2A | 0.9300 | C14—H14C | 0.9600 |
C3—C4 | 1.385 (3) | C15—H15A | 0.9600 |
C3—C14 | 1.515 (3) | C15—H15B | 0.9600 |
C4—C5 | 1.385 (3) | C15—H15C | 0.9600 |
C7—N1—C8 | 129.34 (15) | N2—C8—S1 | 127.11 (13) |
C7—N1—H1N1 | 116.6 (14) | N1—C8—S1 | 117.91 (12) |
C8—N1—H1N1 | 112.9 (14) | N3—C9—C10 | 123.61 (16) |
C8—N2—C9 | 132.25 (15) | N3—C9—N2 | 109.77 (15) |
C8—N2—H1N2 | 111.7 (17) | C10—C9—N2 | 126.61 (15) |
C9—N2—H1N2 | 114.2 (17) | C11—C10—C9 | 119.22 (17) |
C9—N3—C13 | 116.14 (17) | C11—C10—H10A | 120.4 |
C2—C1—C6 | 120.01 (18) | C9—C10—H10A | 120.4 |
C2—C1—H1A | 120.0 | C12—C11—C10 | 117.90 (18) |
C6—C1—H1A | 120.0 | C12—C11—C15 | 121.03 (18) |
C3—C2—C1 | 121.29 (17) | C10—C11—C15 | 121.07 (19) |
C3—C2—H2A | 119.4 | C13—C12—C11 | 118.87 (19) |
C1—C2—H2A | 119.4 | C13—C12—H12A | 120.6 |
C2—C3—C4 | 118.38 (17) | C11—C12—H12A | 120.6 |
C2—C3—C14 | 121.3 (2) | N3—C13—C12 | 124.3 (2) |
C4—C3—C14 | 120.3 (2) | N3—C13—H13A | 117.9 |
C5—C4—C3 | 121.21 (18) | C12—C13—H13A | 117.9 |
C5—C4—H4A | 119.4 | C3—C14—H14A | 109.5 |
C3—C4—H4A | 119.4 | C3—C14—H14B | 109.5 |
C6—C5—C4 | 119.94 (17) | H14A—C14—H14B | 109.5 |
C6—C5—H5A | 120.0 | C3—C14—H14C | 109.5 |
C4—C5—H5A | 120.0 | H14A—C14—H14C | 109.5 |
C5—C6—C1 | 119.15 (16) | H14B—C14—H14C | 109.5 |
C5—C6—C7 | 122.77 (15) | C11—C15—H15A | 109.5 |
C1—C6—C7 | 118.08 (15) | C11—C15—H15B | 109.5 |
O1—C7—N1 | 122.22 (16) | H15A—C15—H15B | 109.5 |
O1—C7—C6 | 122.46 (15) | C11—C15—H15C | 109.5 |
N1—C7—C6 | 115.31 (15) | H15A—C15—H15C | 109.5 |
N2—C8—N1 | 114.97 (14) | H15B—C15—H15C | 109.5 |
C6—C1—C2—C3 | 1.2 (3) | C9—N2—C8—N1 | −174.80 (16) |
C1—C2—C3—C4 | −0.3 (3) | C9—N2—C8—S1 | 4.2 (3) |
C1—C2—C3—C14 | 179.57 (18) | C7—N1—C8—N2 | 3.2 (3) |
C2—C3—C4—C5 | −0.5 (3) | C7—N1—C8—S1 | −175.97 (14) |
C14—C3—C4—C5 | 179.64 (17) | C13—N3—C9—C10 | 0.3 (3) |
C3—C4—C5—C6 | 0.4 (3) | C13—N3—C9—N2 | 179.18 (18) |
C4—C5—C6—C1 | 0.5 (3) | C8—N2—C9—N3 | 173.13 (18) |
C4—C5—C6—C7 | −179.68 (16) | C8—N2—C9—C10 | −8.0 (3) |
C2—C1—C6—C5 | −1.2 (3) | N3—C9—C10—C11 | −0.4 (3) |
C2—C1—C6—C7 | 178.91 (16) | N2—C9—C10—C11 | −179.18 (16) |
C8—N1—C7—O1 | −1.1 (3) | C9—C10—C11—C12 | 0.0 (3) |
C8—N1—C7—C6 | 177.94 (15) | C9—C10—C11—C15 | 178.80 (19) |
C5—C6—C7—O1 | −152.85 (18) | C10—C11—C12—C13 | 0.7 (3) |
C1—C6—C7—O1 | 27.0 (2) | C15—C11—C12—C13 | −178.2 (2) |
C5—C6—C7—N1 | 28.1 (2) | C9—N3—C13—C12 | 0.4 (4) |
C1—C6—C7—N1 | −152.03 (16) | C11—C12—C13—N3 | −0.9 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1N2···O1 | 0.82 (2) | 1.94 (2) | 2.644 (2) | 144 (2) |
N1—H1N1···S1i | 0.81 (2) | 2.74 (2) | 3.5106 (15) | 157.8 (18) |
C10—H10A···S1 | 0.93 | 2.57 | 3.2211 (19) | 127 |
Symmetry code: (i) −x+1, −y+2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1N2···O1 | 0.82 (2) | 1.94 (2) | 2.644 (2) | 144 (2) |
N1—H1N1···S1i | 0.81 (2) | 2.74 (2) | 3.5106 (15) | 157.8 (18) |
C10—H10A···S1 | 0.93 | 2.57 | 3.2211 (19) | 127 |
Symmetry code: (i) −x+1, −y+2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C15H15N3OS |
Mr | 285.36 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 294 |
a, b, c (Å) | 11.5297 (12), 6.1860 (6), 20.657 (2) |
β (°) | 101.431 (2) |
V (Å3) | 1444.1 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.22 |
Crystal size (mm) | 0.38 × 0.34 × 0.09 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.920, 0.981 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15813, 4233, 2790 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.706 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.164, 1.05 |
No. of reflections | 4233 |
No. of parameters | 191 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.27, −0.19 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
Footnotes
‡Additional correspondence author, e-mail: nasertaha90@hotmail.com.
Acknowledgements
The authors would like to thank Universiti Sains Malaysia for a research grant (PKIMIA 846017), which partially supported this work.
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