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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3344
https://doi.org/10.1107/S1600536811047799

10-Ethyl-10H-pheno­thia­zine-3-carbaldehyde

Dao-Hui Yu,a Jian-Qing Wang,a Lin Konga* and Zhao-di Liua

aDepartment of Chemistry, Anhui University, Hefei 230039, People's Republic of China, and Key Laboratory of Functional Inorganic Materials, Chemistry, Hefei 230039, People's Republic of China
*Correspondence e-mail: kong_lin2009@126.com

(Received 26 October 2011; accepted 10 November 2011; online 19 November 2011)

In the title mol­ecule, C15H13NOS, the two benzene rings of the tricyclic fused-ring system are inclined at 21.1 (1)°. In the crystal, weak C—H⋯O hydrogen bonds link the mol­ecules into chains along [001]. The crystal packing also exhibits π–π inter­actions with a distance of 3.801 (5) Å between the centroids of the benzene rings of neighbouring mol­ecules.

Related literature

For related structures, see: Chu & Van der Helm (1975[Chu, S. S. C. & Van der Helm, D. (1975). Acta Cryst. B31, 1179-1183.]); Hdii et al. (1998[Hdii, F., Reboul, J.-P., Barbe, J., Siri, D. & Pèpe, G. (1998). Acta Cryst. C54, 1151-1152.]); Li et al. (2009a[Li, D. M., Lv, L. F., Sun, P. P., Zhou, W., Wang, P., Wu, J. Y., Kan, Y. H., Zhou, H. P. & Tian, Y. P. (2009a). Dyes Pigments, 83, 180-186.],b[Li, D. M., Hu, R. T., Zhou, W., Sun, P. P., Kan, Y. H., Tian, Y. P., Zhou, H. P., Wu, J. Y., Tao, X. T. & Jiang, M. H. (2009b). Eur. J. Inorg. Chem. pp. 2664-2672.]).

[Scheme 1]

Experimental

Crystal data

  • C15H13NOS

  • Mr = 255.32

  • Orthorhombic, P b c a

  • a = 8.0867 (1) Å

  • b = 15.3271 (3) Å

  • c = 20.3369 (4) Å

  • V = 2520.67 (8) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.24 mm−1

  • T = 296 K

  • 0.20 × 0.10 × 0.10 mm
Data collection

  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.953, Tmax = 0.976

  • 17210 measured reflections

  • 2225 independent reflections

  • 1909 reflections with I > 2σ(I)

  • Rint = 0.028
Refinement

  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.109

  • S = 1.08

  • 2225 reflections

  • 167 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.40 e Å−3

  • Δρmin = −0.42 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C14—H14A⋯O1i 0.97 2.64 3.563 (3) 158
Symmetry code: (i) [-x+{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811047799/cv5184sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811047799/cv5184Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811047799/cv5184Isup3.cml

checkCIF report


Comment top

The title compound (I) is often used as intermediate in the synthesis of organic compounds with optical properties (Li et al., 2009a, b). Herewith we present its crystal structure.

In (I) (Fig.1), two benzene rings form the dihedral angles of 10.0 (8)° and 12.0 (8)°, respectively, with the thiomorpholine mean plane. The folding of the molecule is characterized by dihedral angle formed by two benzene rings, which is 21.1 (1) °. In the related compounds, 10-ethylphenothiazine (Chu et al., 1975) and 10-ethyl-3-nitrophenothiazine (Hdii et al., 1998), the corresponding dihedral angle is 44.9 (1) and 22.8 (1) °, respectively, showing that any substitution added to benzene ring flattens the tricycle. This tendency also observed in the structure of (E)-3-(10-ethyl-10H-phenothiazin-3-yl)acrylic acid (Li et al., 2009b), where these dihedral angles in two independent molecules are 25.3 (9) ° and 29.8 (8) °, respectively. The ethyl group in (I) is almost orthogonal to the thiazine ring, the torsion angle C6–N1—Cl4–C15 is 85.6 (1)°. While in 10-ethylphenothiazine (Chu et al., 1975), the corresponding angle is 146.1 (4) °, and in 10-ethyl-3-nitrophenothiazine (Hon et al., 1998) this angle is -84.9 (2)°. The aldehyde group is almost coplanar with its attached phenyl ring, the torsion angle C12–C11–C13–O1 being -2.59 °.

In the crystal, weak intermolecular C—H···O hydrogen bonds (Table 1) link molecules into chains along [001]. The crystal packing exhibits π···π interactions with the distance of 3.801 (5) Å between the centroids of benzene rings from the neighbouring molecules.

Related literature top

For the related structures, see: Chu & Van der Helm (1975); Hdii et al. (1998); Li et al. (2009a,b).

Experimental top

NaH (4.08 g, 0.17 mol) and DMF (5 ml) were added to a three-necked flask equipped with a magnetic stirrer and a reflux condenser, and then phenothiazine (20.0 g, 0.1 mol), DMF (10 ml) were added dropwisely (about 30 min), refluxed for another 20 min. Then C2 H5Br (17 ml) was dropped into the mixture and refluxed for 2 h with TLC detection. The pH of the solution was adjusted to acidic with hydrochloric acid then extracted with 500 ml of ethyl acetate, washed three times with distilled water, and dried with anhydrous magnesium sulfate. It was then filtered and concentrated to produce 18.2 g needle crystals in 80% yield.

N-ethyl-phenothiazine (11.35 g, 0.05 mol) and DMF (39 ml) were added to a three-necked flask in ice equipped with a magnetic stirrer and a reflux condenser, then POCl3 (92 ml) was added dropwisely (about 30 min), the mixture was refluxed for 1 h. Then the mixture was poured into ice to get light yellow solid. The pH of the mixture was adjusted to neutral with NaOH and extracted three times with 150 ml of ethyl acetate. The organic layer was washed with distilled water and then saturated brine. The organic extracts were dried with anhydrous magnesium sulfate. The solvent was removed in vacuo. The residue was purified by column chromatography on silica gel with petroleum ether as eluent to give 7.6 g titled compound as a yellow solid in 60% yield. 1H NMR (400 MHz, CDCl3) 7.569 (s, 1H), 7.157 (t, 1H), 7.097 (d, J = 7.8 Hz, 1H), 6.912 (d, J = 6.4 Hz, 1H), 6.896 (d, J = 6.2 Hz, 1H), 3.974 (q, 2H), 1.447 (t,3H). 13C NMR (100 MHz). 89, 42.47, 114.40, 115.58, 123.30, 123.56, 124.51, 127.49, 127.59, 128.25, 130.16, 131.04, 189.98.

Refinement top

The methine H atoms was located on a difference map and isotropically refined. All the rest H atoms were placed in geometrically idealized positions (C—H = 0.93 - 0.97 Å) and constrained to ride on their parent atoms, with Uiso(H) = 1.2-1.5 Ueq(C).

Structure description top

The title compound (I) is often used as intermediate in the synthesis of organic compounds with optical properties (Li et al., 2009a, b). Herewith we present its crystal structure.

In (I) (Fig.1), two benzene rings form the dihedral angles of 10.0 (8)° and 12.0 (8)°, respectively, with the thiomorpholine mean plane. The folding of the molecule is characterized by dihedral angle formed by two benzene rings, which is 21.1 (1) °. In the related compounds, 10-ethylphenothiazine (Chu et al., 1975) and 10-ethyl-3-nitrophenothiazine (Hdii et al., 1998), the corresponding dihedral angle is 44.9 (1) and 22.8 (1) °, respectively, showing that any substitution added to benzene ring flattens the tricycle. This tendency also observed in the structure of (E)-3-(10-ethyl-10H-phenothiazin-3-yl)acrylic acid (Li et al., 2009b), where these dihedral angles in two independent molecules are 25.3 (9) ° and 29.8 (8) °, respectively. The ethyl group in (I) is almost orthogonal to the thiazine ring, the torsion angle C6–N1—Cl4–C15 is 85.6 (1)°. While in 10-ethylphenothiazine (Chu et al., 1975), the corresponding angle is 146.1 (4) °, and in 10-ethyl-3-nitrophenothiazine (Hon et al., 1998) this angle is -84.9 (2)°. The aldehyde group is almost coplanar with its attached phenyl ring, the torsion angle C12–C11–C13–O1 being -2.59 °.

In the crystal, weak intermolecular C—H···O hydrogen bonds (Table 1) link molecules into chains along [001]. The crystal packing exhibits π···π interactions with the distance of 3.801 (5) Å between the centroids of benzene rings from the neighbouring molecules.

For the related structures, see: Chu & Van der Helm (1975); Hdii et al. (1998); Li et al. (2009a,b).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. : The molecular structure of the title molecule with 50% probability displacement ellipsoids.
10-Ethyl-10H-phenothiazine-3-carbaldehyde top
Crystal data top
C15H13NOSF(000) = 1072
Mr = 255.32Dx = 1.346 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 7387 reflections
a = 8.0867 (1) Åθ = 2.7–27.1°
b = 15.3271 (3) ŵ = 0.24 mm−1
c = 20.3369 (4) ÅT = 296 K
V = 2520.67 (8) Å3Needle, yellow
Z = 80.20 × 0.10 × 0.10 mm
Data collection top
Bruker SMART APEX
diffractometer		2225 independent reflections
Radiation source: fine-focus sealed tube1909 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
phi and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −9→9
Tmin = 0.953, Tmax = 0.976k = −17→18
17210 measured reflectionsl = −22→24
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.109 w = 1/[σ2(Fo2) + (0.048P)2 + 1.0328P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.030
2225 reflectionsΔρmax = 0.40 e Å−3
167 parametersΔρmin = −0.42 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0062 (8)
Crystal data top
C15H13NOSV = 2520.67 (8) Å3
Mr = 255.32Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 8.0867 (1) ŵ = 0.24 mm−1
b = 15.3271 (3) ÅT = 296 K
c = 20.3369 (4) Å0.20 × 0.10 × 0.10 mm
Data collection top
Bruker SMART APEX
diffractometer		2225 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1909 reflections with I > 2σ(I)
Tmin = 0.953, Tmax = 0.976Rint = 0.028
17210 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.109H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.40 e Å−3
2225 reflectionsΔρmin = −0.42 e Å−3
167 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.24520 (8)0.67345 (3)0.06193 (3)0.0654 (2)
C60.0560 (2)0.57828 (11)0.14810 (8)0.0434 (4)
N10.13723 (18)0.50268 (9)0.12517 (7)0.0460 (4)
C10.0870 (2)0.66009 (11)0.12020 (9)0.0473 (4)
C80.1974 (2)0.49538 (11)0.06126 (8)0.0415 (4)
O10.4535 (2)0.53800 (12)−0.16387 (7)0.0733 (4)
C120.3099 (2)0.56256 (12)−0.03694 (9)0.0480 (4)
H120.33710.6129−0.06010.058*
C110.3359 (2)0.48174 (13)−0.06591 (8)0.0488 (4)
C140.1335 (2)0.42393 (12)0.16677 (10)0.0541 (5)
H14A0.13980.44190.21240.065*
H14B0.23130.38940.15740.065*
C70.2448 (2)0.56995 (11)0.02515 (9)0.0434 (4)
C20.0052 (3)0.73369 (13)0.14222 (10)0.0583 (5)
H20.02470.78710.12190.070*
C5−0.0556 (2)0.57511 (13)0.20039 (10)0.0554 (5)
H5−0.07860.52190.22040.066*
C130.4132 (3)0.47568 (17)−0.13082 (10)0.0598 (5)
C90.2197 (2)0.41474 (12)0.03065 (10)0.0506 (5)
H90.18690.36430.05250.061*
C100.2888 (2)0.40786 (13)−0.03095 (10)0.0540 (5)
H100.30430.3530−0.04950.065*
C15−0.0183 (3)0.36605 (15)0.15823 (12)0.0694 (6)
H15A−0.11530.39760.17140.104*
H15B−0.00680.31480.18500.104*
H15C−0.02820.34920.11290.104*
C4−0.1325 (3)0.64997 (17)0.22290 (11)0.0677 (6)
H4−0.20440.64650.25850.081*
C3−0.1046 (3)0.72895 (16)0.19376 (11)0.0679 (6)
H3−0.15900.77870.20850.081*
H130.429 (4)0.4148 (18)−0.1460 (14)0.102*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0860 (4)0.0370 (3)0.0734 (4)−0.0115 (2)0.0224 (3)−0.0011 (2)
C60.0406 (9)0.0475 (10)0.0421 (9)0.0007 (7)−0.0072 (7)0.0005 (7)
N10.0503 (8)0.0407 (8)0.0471 (8)0.0021 (6)0.0024 (7)0.0102 (6)
C10.0509 (10)0.0449 (10)0.0461 (10)0.0015 (8)−0.0072 (8)−0.0011 (8)
C80.0400 (8)0.0382 (9)0.0464 (9)−0.0009 (7)−0.0030 (7)0.0056 (7)
O10.0770 (10)0.0945 (12)0.0485 (8)−0.0086 (9)0.0078 (7)−0.0013 (8)
C120.0490 (10)0.0496 (10)0.0455 (10)−0.0053 (8)−0.0021 (8)0.0086 (8)
C110.0427 (10)0.0585 (12)0.0453 (10)0.0012 (8)−0.0057 (7)−0.0019 (8)
C140.0547 (11)0.0518 (11)0.0558 (11)0.0035 (9)−0.0008 (9)0.0213 (8)
C70.0452 (10)0.0373 (9)0.0476 (10)−0.0012 (7)−0.0013 (8)0.0041 (7)
C20.0629 (12)0.0484 (11)0.0635 (12)0.0078 (9)−0.0119 (10)−0.0070 (9)
C50.0503 (10)0.0677 (13)0.0481 (10)−0.0041 (9)−0.0001 (9)0.0016 (9)
C130.0505 (11)0.0781 (15)0.0508 (11)0.0003 (11)−0.0066 (9)−0.0080 (11)
C90.0541 (11)0.0371 (9)0.0607 (12)−0.0007 (8)0.0000 (9)0.0055 (8)
C100.0545 (11)0.0474 (11)0.0600 (12)0.0036 (9)−0.0063 (9)−0.0085 (9)
C150.0670 (13)0.0598 (13)0.0813 (15)−0.0072 (10)0.0038 (11)0.0263 (11)
C40.0539 (12)0.0902 (17)0.0589 (12)0.0050 (11)0.0047 (10)−0.0172 (12)
C30.0597 (12)0.0707 (14)0.0732 (14)0.0152 (11)−0.0059 (11)−0.0206 (12)
Geometric parameters (Å, º) top
S1—C71.7538 (18)C14—H14A0.9700
S1—C11.756 (2)C14—H14B0.9700
C6—C51.396 (3)C2—C31.376 (3)
C6—C11.399 (2)C2—H20.9300
C6—N11.411 (2)C5—C41.383 (3)
N1—C81.392 (2)C5—H50.9300
N1—C141.474 (2)C13—H130.99 (3)
C1—C21.382 (3)C9—C101.376 (3)
C8—C91.396 (3)C9—H90.9300
C8—C71.412 (2)C10—H100.9300
O1—C131.212 (3)C15—H15A0.9600
C12—C71.372 (3)C15—H15B0.9600
C12—C111.388 (3)C15—H15C0.9600
C12—H120.9300C4—C31.366 (3)
C11—C101.390 (3)C4—H40.9300
C11—C131.463 (3)C3—H30.9300
C14—C151.524 (3)
C7—S1—C1100.44 (8)C3—C2—C1120.8 (2)
C5—C6—C1117.13 (17)C3—C2—H2119.6
C5—C6—N1121.61 (16)C1—C2—H2119.6
C1—C6—N1121.24 (16)C4—C5—C6120.93 (19)
C8—N1—C6122.48 (14)C4—C5—H5119.5
C8—N1—C14118.49 (15)C6—C5—H5119.5
C6—N1—C14118.24 (15)O1—C13—C11124.4 (2)
C2—C1—C6120.97 (18)O1—C13—H13122.3 (17)
C2—C1—S1118.17 (15)C11—C13—H13113.3 (17)
C6—C1—S1120.58 (14)C10—C9—C8121.78 (17)
N1—C8—C9122.20 (15)C10—C9—H9119.1
N1—C8—C7121.03 (15)C8—C9—H9119.1
C9—C8—C7116.73 (16)C9—C10—C11120.97 (18)
C7—C12—C11121.50 (17)C9—C10—H10119.5
C7—C12—H12119.3C11—C10—H10119.5
C11—C12—H12119.3C14—C15—H15A109.5
C12—C11—C10117.92 (17)C14—C15—H15B109.5
C12—C11—C13120.29 (19)H15A—C15—H15B109.5
C10—C11—C13121.78 (19)C14—C15—H15C109.5
N1—C14—C15115.30 (16)H15A—C15—H15C109.5
N1—C14—H14A108.4H15B—C15—H15C109.5
C15—C14—H14A108.4C3—C4—C5121.2 (2)
N1—C14—H14B108.4C3—C4—H4119.4
C15—C14—H14B108.4C5—C4—H4119.4
H14A—C14—H14B107.5C4—C3—C2118.9 (2)
C12—C7—C8121.06 (16)C4—C3—H3120.5
C12—C7—S1117.80 (13)C2—C3—H3120.5
C8—C7—S1120.72 (14)
C5—C6—N1—C8155.35 (17)N1—C8—C7—C12177.55 (16)
C1—C6—N1—C8−26.1 (2)C9—C8—C7—C12−0.1 (3)
C5—C6—N1—C14−14.3 (2)N1—C8—C7—S15.2 (2)
C1—C6—N1—C14164.21 (16)C9—C8—C7—S1−172.52 (13)
C5—C6—C1—C2−2.4 (3)C1—S1—C7—C12157.90 (15)
N1—C6—C1—C2179.03 (16)C1—S1—C7—C8−29.47 (16)
C5—C6—C1—S1171.37 (14)C6—C1—C2—C32.3 (3)
N1—C6—C1—S1−7.2 (2)S1—C1—C2—C3−171.58 (16)
C7—S1—C1—C2−155.68 (15)C1—C6—C5—C40.5 (3)
C7—S1—C1—C630.42 (16)N1—C6—C5—C4179.09 (17)
C6—N1—C8—C9−155.31 (17)C12—C11—C13—O1−2.6 (3)
C14—N1—C8—C914.4 (3)C10—C11—C13—O1178.44 (19)
C6—N1—C8—C727.1 (2)N1—C8—C9—C10−175.86 (17)
C14—N1—C8—C7−163.21 (16)C7—C8—C9—C101.8 (3)
C7—C12—C11—C102.1 (3)C8—C9—C10—C11−1.5 (3)
C7—C12—C11—C13−176.89 (17)C12—C11—C10—C9−0.5 (3)
C8—N1—C14—C15−84.5 (2)C13—C11—C10—C9178.53 (18)
C6—N1—C14—C1585.6 (2)C6—C5—C4—C31.5 (3)
C11—C12—C7—C8−1.8 (3)C5—C4—C3—C2−1.6 (3)
C11—C12—C7—S1170.76 (14)C1—C2—C3—C4−0.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14A···O1i0.972.643.563 (3)158
Symmetry code: (i) −x+1/2, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formulaC15H13NOS
Mr255.32
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)296
a, b, c (Å)8.0867 (1), 15.3271 (3), 20.3369 (4)
V (Å3)2520.67 (8)
Z8
Radiation typeMo Kα
µ (mm−1)0.24
Crystal size (mm)0.20 × 0.10 × 0.10
Data collection
DiffractometerBruker SMART APEX
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.953, 0.976
No. of measured, independent and
observed [I > 2σ(I)] reflections		17210, 2225, 1909
Rint0.028
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.109, 1.08
No. of reflections2225
No. of parameters167
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.40, −0.42

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14A···O1i0.972.643.563 (3)158.3
Symmetry code: (i) −x+1/2, −y+1, z+1/2.
 

Acknowledgements

We gratefully acknowledge the NSFC (grant Nos. 21071001, 50873001 and 20875001), the Science and Technological Fund of Anhui Province for Outstanding Youth (grant No. 10040606Y22) and the 211 Project of Anhui University for supporting this study.

References

First citationBruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationChu, S. S. C. & Van der Helm, D. (1975). Acta Cryst. B31, 1179–1183.  CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
 First citationHdii, F., Reboul, J.-P., Barbe, J., Siri, D. & Pèpe, G. (1998). Acta Cryst. C54, 1151–1152.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationLi, D. M., Hu, R. T., Zhou, W., Sun, P. P., Kan, Y. H., Tian, Y. P., Zhou, H. P., Wu, J. Y., Tao, X. T. & Jiang, M. H. (2009b). Eur. J. Inorg. Chem. pp. 2664–2672.  Web of Science CSD CrossRef Google Scholar
 First citationLi, D. M., Lv, L. F., Sun, P. P., Zhou, W., Wang, P., Wu, J. Y., Kan, Y. H., Zhou, H. P. & Tian, Y. P. (2009a). Dyes Pigments, 83, 180–186.  Web of Science CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3344
https://doi.org/10.1107/S1600536811047799
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