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

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ISSN: 2056-9890

(3S,4Z)-3-Chloro-1-methyl-4-[(2E)-(3-methyl­benzyl­­idene)hydrazinyl­­idene]-3,4-di­hydro-1H-2,1-benzo­thia­zine 2,2-dioxide

aMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore, Pakistan, bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan, and cApplied Chemistry Research Center, PCSIR Laboratories Complex, Lahore, Pakistan
*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 28 December 2011; accepted 31 December 2011; online 11 January 2012)

In the title compound, C17H16ClN3O2S, the dihedral angle between the benzene rings is 7.75 (13)°. The thia­zine ring adopts an envelope conformation with the S atom as the flap at a distance of 0.813 (2) Å from the plane through the other five atoms. In the crystal, C—H⋯O hydrogen bonds link the mol­ecules into chains propagating in [100].

Related literature

For related structures, see: Shafiq et al. (2011a[Shafiq, M., Khan, I. U., Arshad, M. N. & Siddiqui, W. A. (2011a). Asian J. Chem. 23, 2101-2106.],b[Shafiq, M., Khan, I. U., Zia-ur-Rehman, M., Arshad, M. N. & Asiri, A. M. (2011b). Acta Cryst. E67, o2038.],c[Shafiq, M., Khan, I. U., Zia-ur-Rehman, M., Arshad, M. N. & Asiri, A. M. (2011c). Acta Cryst. E67, o2092.]). For further synthetic details, see: Shafiq et al. (2011d[Shafiq, M., Zia-ur-Rehman, M., Khan, I. U., Arshad, M. N. & Khan, S. A. (2011d). J. Chil. Chem. Soc. 56, 527-531.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C17H16ClN3O2S

  • Mr = 361.84

  • Orthorhombic, P 21 21 21

  • a = 8.7734 (2) Å

  • b = 11.1271 (2) Å

  • c = 17.9423 (3) Å

  • V = 1751.57 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.35 mm−1

  • T = 296 K

  • 0.26 × 0.18 × 0.12 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.930, Tmax = 0.960

  • 17152 measured reflections

  • 4265 independent reflections

  • 3478 reflections with I > 2σ(I)

  • Rint = 0.029

Refinement
  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.088

  • S = 1.03

  • 4265 reflections

  • 219 parameters

  • H-atom parameters constrained

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.27 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1788 Friedel pairs

  • Flack parameter: 0.47 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C4—H4⋯O2i 0.93 2.57 3.469 (3) 163
C10—H10⋯O1ii 0.93 2.53 3.300 (3) 140
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) x+1, y, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON.

Supporting information


Comment top

The title compound (I), (Fig. 1) has been synthesized in continuation of our studies of Schiff bases (Shafiq et al., 2011a,b,c).

In (I), the benzene rings A (C1—C6) and B (C11—C16) are planar with r. m. s. deviation of 0.0033 and 0.0002 Å, respectively. The dihedral angle between A/B is 7.75 (13)°. The central group C (N2/N3/C10) is of course planar. The dihedral angle between A/C and B/C is 6.02 (19) and 5.11 (21)°, respectively. The thiazine ring D (C1/C6/C9/C8/S1/N1) is in the nvelope form, with the maximum puckering amplitude (Cremer & Pople, 1975), Q = 0.5707 (16) Å. The molecules form one-dimensional polymeric chains extending along the a-axis due to H-bonding of C—H···O type (Table 1).

Related literature top

For related structures, see: Shafiq et al. (2011a,b,c). For further synthetic details, see: Shafiq et al. (2011d). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

Schiff base derivative of (4Z)-4-hydrazinylidene-1-methyl-3,4-dihydro -1H-2,1-benzothiazine 2,2-dioxide and 3-methylbenzaldehyde was prepared using the method reported previously (Shafiq et al. 2011d). The chlorination of the schiff base was undertaken using N-chloro succinimide and dibenzoylperoxide (Shafiq et al., 2011a). The crude product was re-crystallized from ethyl acetate to yield orange needles of (I).

Refinement top

The H-atoms were positioned geometrically (C–H = 0.93–0.96 Å) and refined as riding with Uiso(H) = xUeq(C), where x = 1.5 for methyl and x = 1.2 for aryl H-atoms.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. View of the title compound with displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. The partial packing showing chains extending along the [100] direction.
(3S,4Z)-3-Chloro-1-methyl-4-[(2E)-(3- methylbenzylidene)hydrazinylidene]-3,4-dihydro-1H-2,1-benzothiazine 2,2-dioxide top
Crystal data top
C17H16ClN3O2SF(000) = 752
Mr = 361.84Dx = 1.372 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 2106 reflections
a = 8.7734 (2) Åθ = 1.4–25.3°
b = 11.1271 (2) ŵ = 0.35 mm1
c = 17.9423 (3) ÅT = 296 K
V = 1751.57 (6) Å3Needle, orange
Z = 40.26 × 0.18 × 0.12 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
4265 independent reflections
Radiation source: fine-focus sealed tube3478 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
Detector resolution: 7.50 pixels mm-1θmax = 28.3°, θmin = 2.2°
ω scansh = 1011
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1414
Tmin = 0.930, Tmax = 0.960l = 2323
17152 measured reflections
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)] = 0.036H-atom parameters constrained
wR(F2) = 0.088 w = 1/[σ2(Fo2) + (0.041P)2 + 0.2645P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
4265 reflectionsΔρmax = 0.24 e Å3
219 parametersΔρmin = 0.27 e Å3
0 restraintsAbsolute structure: Flack (1983), 1788 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.47 (6)
Crystal data top
C17H16ClN3O2SV = 1751.57 (6) Å3
Mr = 361.84Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.7734 (2) ŵ = 0.35 mm1
b = 11.1271 (2) ÅT = 296 K
c = 17.9423 (3) Å0.26 × 0.18 × 0.12 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
4265 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
3478 reflections with I > 2σ(I)
Tmin = 0.930, Tmax = 0.960Rint = 0.029
17152 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.088Δρmax = 0.24 e Å3
S = 1.03Δρmin = 0.27 e Å3
4265 reflectionsAbsolute structure: Flack (1983), 1788 Friedel pairs
219 parametersAbsolute structure parameter: 0.47 (6)
0 restraints
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
Cl10.16886 (7)0.16151 (6)0.00310 (3)0.0619 (2)
S10.10071 (6)0.09643 (5)0.15565 (3)0.0411 (2)
O10.04053 (18)0.05118 (15)0.12847 (9)0.0559 (6)
O20.17040 (19)0.04041 (14)0.21814 (8)0.0524 (5)
N10.0827 (2)0.23974 (17)0.16940 (11)0.0453 (6)
N20.5175 (2)0.13115 (15)0.09335 (10)0.0410 (5)
N30.5229 (2)0.03374 (16)0.04310 (10)0.0467 (6)
C10.2182 (3)0.30519 (17)0.18673 (11)0.0381 (6)
C20.2065 (3)0.4082 (2)0.22991 (13)0.0523 (8)
C30.3334 (3)0.4739 (2)0.24869 (13)0.0531 (8)
C40.4751 (3)0.4373 (2)0.22482 (12)0.0499 (8)
C50.4885 (3)0.3360 (2)0.18144 (11)0.0422 (7)
C60.3614 (2)0.26764 (17)0.16138 (10)0.0338 (6)
C70.0609 (3)0.3020 (3)0.15644 (19)0.0690 (10)
C80.2429 (2)0.09333 (19)0.08520 (10)0.0380 (6)
C90.3815 (2)0.16115 (17)0.11258 (10)0.0339 (6)
C100.6581 (3)0.01494 (19)0.02078 (12)0.0455 (7)
C110.6974 (3)0.07862 (19)0.03287 (12)0.0464 (7)
C120.5872 (3)0.1500 (3)0.06694 (14)0.0668 (10)
C130.6332 (4)0.2383 (3)0.11655 (18)0.0808 (13)
C140.7839 (4)0.2554 (2)0.13190 (16)0.0751 (12)
C150.8968 (3)0.1863 (2)0.09916 (14)0.0588 (8)
C160.8497 (3)0.0975 (2)0.04930 (12)0.0513 (8)
C171.0632 (4)0.2042 (3)0.11637 (18)0.0803 (11)
H20.111200.433260.246420.0628*
H30.323560.542970.277480.0637*
H40.561410.480920.237990.0598*
H50.584470.312470.165040.0506*
H7A0.105580.323860.203370.1034*
H7B0.129310.250070.129850.1034*
H7C0.042560.373180.127550.1034*
H80.271040.009840.074530.0456*
H100.735770.063100.039510.0545*
H120.484350.138580.056560.0802*
H130.560530.286410.139630.0969*
H140.811720.315400.165350.0899*
H160.922770.049560.026400.0616*
H17A1.094540.282290.099560.1203*
H17B1.122130.143730.091340.1203*
H17C1.079070.198010.169170.1203*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0545 (4)0.0921 (4)0.0390 (3)0.0107 (3)0.0091 (3)0.0114 (3)
S10.0304 (3)0.0494 (3)0.0434 (3)0.0036 (2)0.0022 (2)0.0065 (2)
O10.0360 (10)0.0662 (10)0.0655 (10)0.0139 (8)0.0005 (8)0.0038 (8)
O20.0459 (10)0.0616 (9)0.0497 (8)0.0011 (8)0.0023 (8)0.0190 (7)
N10.0253 (10)0.0544 (10)0.0561 (11)0.0053 (8)0.0001 (8)0.0009 (8)
N20.0357 (10)0.0437 (9)0.0435 (9)0.0038 (8)0.0036 (8)0.0065 (7)
N30.0414 (12)0.0459 (10)0.0527 (10)0.0009 (9)0.0088 (9)0.0098 (8)
C10.0322 (11)0.0447 (11)0.0374 (10)0.0049 (9)0.0006 (8)0.0003 (8)
C20.0417 (13)0.0592 (13)0.0561 (13)0.0133 (12)0.0043 (11)0.0130 (12)
C30.0569 (17)0.0487 (12)0.0537 (12)0.0045 (12)0.0028 (12)0.0115 (10)
C40.0488 (15)0.0507 (12)0.0501 (12)0.0065 (11)0.0107 (11)0.0038 (10)
C50.0331 (12)0.0520 (12)0.0414 (10)0.0031 (10)0.0002 (9)0.0009 (9)
C60.0301 (11)0.0399 (9)0.0315 (9)0.0022 (8)0.0007 (8)0.0017 (8)
C70.0372 (15)0.0779 (19)0.092 (2)0.0183 (12)0.0136 (14)0.0157 (17)
C80.0340 (11)0.0412 (10)0.0389 (10)0.0015 (9)0.0017 (9)0.0008 (9)
C90.0285 (11)0.0386 (9)0.0347 (9)0.0022 (9)0.0005 (8)0.0035 (8)
C100.0416 (13)0.0473 (12)0.0475 (11)0.0076 (10)0.0017 (10)0.0071 (9)
C110.0489 (14)0.0422 (11)0.0481 (11)0.0029 (11)0.0066 (10)0.0052 (9)
C120.0661 (18)0.0677 (16)0.0667 (16)0.0120 (15)0.0121 (14)0.0195 (14)
C130.093 (3)0.0663 (17)0.083 (2)0.0196 (17)0.0097 (18)0.0307 (15)
C140.110 (3)0.0500 (14)0.0652 (16)0.0004 (17)0.0260 (17)0.0173 (12)
C150.0755 (18)0.0493 (13)0.0516 (12)0.0193 (14)0.0202 (14)0.0017 (10)
C160.0553 (15)0.0465 (12)0.0521 (12)0.0091 (12)0.0076 (11)0.0046 (10)
C170.084 (2)0.080 (2)0.0770 (19)0.0358 (17)0.0277 (17)0.0024 (16)
Geometric parameters (Å, º) top
Cl1—C81.7797 (19)C12—C131.386 (4)
S1—O11.4237 (17)C13—C141.364 (5)
S1—O21.4211 (16)C14—C151.385 (4)
S1—N11.621 (2)C15—C161.396 (3)
S1—C81.7763 (19)C15—C171.505 (4)
N1—C11.428 (3)C2—H20.9300
N1—C71.457 (3)C3—H30.9300
N2—N31.411 (2)C4—H40.9300
N2—C91.286 (2)C5—H50.9300
N3—C101.269 (3)C7—H7A0.9600
C1—C21.387 (3)C7—H7B0.9600
C1—C61.400 (3)C7—H7C0.9600
C2—C31.374 (4)C8—H80.9800
C3—C41.377 (4)C10—H100.9300
C4—C51.375 (3)C12—H120.9300
C5—C61.397 (3)C13—H130.9300
C6—C91.484 (3)C14—H140.9300
C8—C91.513 (3)C16—H160.9300
C10—C111.459 (3)C17—H17A0.9600
C11—C121.393 (4)C17—H17B0.9600
C11—C161.384 (4)C17—H17C0.9600
O1—S1—O2119.32 (10)C16—C15—C17120.8 (2)
O1—S1—N1108.37 (10)C11—C16—C15122.0 (2)
O1—S1—C8111.14 (9)C1—C2—H2119.00
O2—S1—N1110.69 (10)C3—C2—H2119.00
O2—S1—C8104.52 (9)C2—C3—H3120.00
N1—S1—C8101.29 (10)C4—C3—H3120.00
S1—N1—C1116.97 (14)C3—C4—H4120.00
S1—N1—C7121.86 (17)C5—C4—H4120.00
C1—N1—C7120.8 (2)C4—C5—H5119.00
N3—N2—C9113.71 (16)C6—C5—H5119.00
N2—N3—C10111.08 (17)N1—C7—H7A109.00
N1—C1—C2118.8 (2)N1—C7—H7B110.00
N1—C1—C6121.60 (17)N1—C7—H7C109.00
C2—C1—C6119.6 (2)H7A—C7—H7B109.00
C1—C2—C3121.1 (2)H7A—C7—H7C109.00
C2—C3—C4119.9 (2)H7B—C7—H7C109.00
C3—C4—C5119.7 (2)Cl1—C8—H8110.00
C4—C5—C6121.6 (2)S1—C8—H8110.00
C1—C6—C5118.04 (18)C9—C8—H8109.00
C1—C6—C9122.46 (17)N3—C10—H10118.00
C5—C6—C9119.47 (17)C11—C10—H10118.00
Cl1—C8—S1108.93 (10)C11—C12—H12121.00
Cl1—C8—C9110.45 (14)C13—C12—H12121.00
S1—C8—C9108.89 (13)C12—C13—H13120.00
N2—C9—C6118.41 (16)C14—C13—H13120.00
N2—C9—C8121.94 (17)C13—C14—H14119.00
C6—C9—C8119.63 (15)C15—C14—H14119.00
N3—C10—C11123.1 (2)C11—C16—H16119.00
C10—C11—C12122.2 (2)C15—C16—H16119.00
C10—C11—C16118.5 (2)C15—C17—H17A109.00
C12—C11—C16119.4 (2)C15—C17—H17B109.00
C11—C12—C13119.0 (3)C15—C17—H17C109.00
C12—C13—C14120.7 (3)H17A—C17—H17B109.00
C13—C14—C15122.0 (3)H17A—C17—H17C109.00
C14—C15—C16117.0 (2)H17B—C17—H17C109.00
C14—C15—C17122.2 (2)
O1—S1—N1—C1171.41 (15)C1—C2—C3—C40.3 (3)
O1—S1—N1—C71.7 (2)C2—C3—C4—C50.9 (3)
O2—S1—N1—C155.99 (18)C3—C4—C5—C60.8 (3)
O2—S1—N1—C7130.9 (2)C4—C5—C6—C10.1 (3)
C8—S1—N1—C154.42 (17)C4—C5—C6—C9178.17 (19)
C8—S1—N1—C7118.7 (2)C1—C6—C9—N2178.30 (18)
O1—S1—C8—Cl149.97 (14)C1—C6—C9—C83.4 (3)
O1—S1—C8—C9170.49 (13)C5—C6—C9—N23.7 (3)
O2—S1—C8—Cl1179.94 (12)C5—C6—C9—C8174.64 (17)
O2—S1—C8—C959.54 (15)Cl1—C8—C9—N293.1 (2)
N1—S1—C8—Cl164.97 (12)Cl1—C8—C9—C685.20 (18)
N1—S1—C8—C955.54 (15)S1—C8—C9—N2147.38 (16)
S1—N1—C1—C2151.50 (17)S1—C8—C9—C634.4 (2)
S1—N1—C1—C628.4 (3)N3—C10—C11—C123.8 (4)
C7—N1—C1—C235.3 (3)N3—C10—C11—C16175.3 (2)
C7—N1—C1—C6144.8 (2)C10—C11—C12—C13179.1 (2)
C9—N2—N3—C10174.07 (18)C16—C11—C12—C130.0 (4)
N3—N2—C9—C6176.04 (16)C10—C11—C16—C15179.1 (2)
N3—N2—C9—C82.2 (3)C12—C11—C16—C150.0 (3)
N2—N3—C10—C11178.60 (19)C11—C12—C13—C140.0 (4)
N1—C1—C2—C3179.5 (2)C12—C13—C14—C150.0 (5)
C6—C1—C2—C30.4 (3)C13—C14—C15—C160.0 (4)
N1—C1—C6—C5179.34 (18)C13—C14—C15—C17179.5 (3)
N1—C1—C6—C92.6 (3)C14—C15—C16—C110.0 (3)
C2—C1—C6—C50.5 (3)C17—C15—C16—C11179.6 (2)
C2—C1—C6—C9177.55 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O2i0.932.573.469 (3)163
C10—H10···O1ii0.932.533.300 (3)140
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC17H16ClN3O2S
Mr361.84
Crystal system, space groupOrthorhombic, P212121
Temperature (K)296
a, b, c (Å)8.7734 (2), 11.1271 (2), 17.9423 (3)
V3)1751.57 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.35
Crystal size (mm)0.26 × 0.18 × 0.12
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.930, 0.960
No. of measured, independent and
observed [I > 2σ(I)] reflections
17152, 4265, 3478
Rint0.029
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.088, 1.03
No. of reflections4265
No. of parameters219
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.24, 0.27
Absolute structureFlack (1983), 1788 Friedel pairs
Absolute structure parameter0.47 (6)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O2i0.932.573.469 (3)163
C10—H10···O1ii0.932.533.300 (3)140
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+1, y, z.
 

Acknowledgements

MS gratefully acknowledges the Higher Education Commission, Islamabad, Pakistan, for providing a scholarship under the Indigenous PhD Program (PIN 042–120567-PS2–276).

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