Eth­oxy­carbonyl­methyl 3-(4-chloro­benzyl­idene)dithio­carbazate

Tabatabaee, M.; Sharif, M.A.; Khalili, R.; Parvez, M.

doi:10.1107/S160053681003549X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2545

doi:10.1107/S160053681003549X

Open

access

Ethoxycarbonylmethyl 3-(4-chlorobenzylidene)dithiocarbazate

Masoumeh Tabatabaee,^a ^* Mahboubeh A. Sharif,^b Robabeh Khalili ^c and Masood Parvez ^d

^aScientific Society of Nanotechnology, Islamic Azad University, Yazd Branch, Yazd, Iran, ^bDepartment of Chemistry, Islamic Azad University, Qom Branch, Qom, Iran, ^cDepartment of Chemistry, Islamic Azad University, Yazd Branch, Yazd, Iran, and ^dDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
^*Correspondence e-mail: tabatabaee45m@yahoo.com

(Received 28 August 2010; accepted 2 September 2010; online 11 September 2010)

Molecules of the title compound, C₁₂H₁₃ClN₂O₂S₂, are linked into centrosymmetric dimers by pairs of intermolecular N—H⋯S hydrogen bonds. In the crystal structure, there are π–π stacking interactions between symmetry-related benzene rings with a centroid–centroid distance of 3.7305 (13) Å, a perpendicular distance between the planes of 3.2851 (9) Å and a slippage of 1.768 Å. The structure is further stabilized by weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For the biological activity of related compounds, see: Gülerman et al. (2001 ); Duran et al. (2002 ). For related structures, see: Tabatabaee et al. (2006 , 2007 , 2008 , 2009 ).

Experimental

Crystal data

C₁₂H₁₃ClN₂O₂S₂
M_r = 316.81
Triclinic, $[P \overline 1]$
a = 7.3425 (3) Å
b = 10.3894 (4) Å
c = 10.6457 (5) Å
α = 116.535 (2)°
β = 95.049 (2)°
γ = 94.955 (2)°
V = 716.50 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.56 mm⁻¹
T = 173 K
0.12 × 0.08 × 0.06 mm

Data collection

Nonius KappaCCD diffractometer with APEXII CCD
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ) T_min = 0.936, T_max = 0.967
12341 measured reflections
3996 independent reflections
3361 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.104
S = 1.09
3996 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯S1ⁱ	0.88	2.52	3.3669 (17)	161
C3—H3⋯O1ⁱⁱ	0.95	2.48	3.410 (2)	166
C9—H9B⋯O1ⁱⁱⁱ	0.99	2.55	3.153 (3)	119
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x+1, -y+1, -z+1; (iii) -x, -y+1, -z.

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681003549X/lh5124sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681003549X/lh5124Isup2.hkl

checkCIF report

Comment top

Thiones of nitrogen-containing heterocycles have attracted the attention of researchers in recent years because of their synthetic possibilities and useful properties. Several compounds containing sulfur and nitrogen atoms are anti-inflammatory, sedative, antibacterial, antiviral, or antitumor and synthesis of the corresponding iminic compounds could be of interest from the viewpoint of chemical reactivity and biological activity (Gülerman et al., 2001; Duran et al., 2002). In a sequence of studies, we have investigated the synthesis and crystal structures of several Schiff bases derived from 4-amino-5-methyl-2H-1,2,4-triazole-3(4H)-thione (AMTT) and 4-amino-6-methyl-3-thio-3,4-dihydro-1,2,4-triazin-5(2H)-one (AMTTO) (Tabatabaee et al., 2006; 2007; 2008; 2009). Here, we report our results for the synthesis and crystal structure of a new iminic compounds derived from N-aminorhodanine, (I).

In the title molecule (Fig. 1) bond distances and angles are unexceptional and agree with the corresponding bond distances and angles reported in the related compounds (Tabatabaee et al., 2006; 2007; 2008; 2009). In the solid state, intermolecular N—H···S hydrogen bonds in the title compound link the molecules lying about inversion centers leading to centrosymmetric dimers (Tab. 1 & Fig. 2). Moreover, the benzene rings C1–C6 and C1ⁱ–C6ⁱ (ⁱ= 2 - x, 1 - y, 1 - z) show π-π stacking interactions (Fig. 3) with centroid-centroid distance 3.7305 (13) Å, the angle between the planes 0 °; the perpendicular distance between the planes 3.2851 (9) Å and the slippage 1.768 Å. The structure is further stabilized by intermolecular hydrogen bonding of C—H···O type (Tab. 1); unit cell packing showing hydrogen bonding interactions has been presented in Figure 4.

Related literature top

For the biological activity of related compounds, see: Gülerman et al. (2001); Duran et al. (2002). For related structures, see: Tabatabaee et al. (2006, 2007, 2008, 2009).

Experimental top

A solution of N-aminorhodanine (5 mmol) in EtOH (20 ml) was treated with 2-chlorobenzaldehyde (5 mmol) and the resulting mixture was acidified with 37% hydrochloric acid (0.2 ml). The reaction mixture was refluxed for 8 h. After completion of the reaction, the solid residue was filtered, washed with cold ethanol (10 ml) and recrystallized from EtOH.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP-3 (Farrugia, 1997) drawing of the title compound with displacement ellipsoids plotted at 50% probability level.
	Fig. 2. Dimeric arrangement of the title compound formed by intermolecular N—H···S hydrogen bonds and shown as dashed lines. S1a is related by the symmetry code (1-x, 2-y, 1-z).
	Fig. 3. Representation of π-π stacking interactions in the crystal structure of the title compound
	Fig. 4. Unit cell packing of the title compound showing hydrogen bonding interactions as dashed lines.

Ethoxycarbonylmethyl 3-(4-chlorobenzylidene)dithiocarbazate top

Crystal data top

C₁₂H₁₃ClN₂O₂S₂	Z = 2
M_r = 316.81	F(000) = 328
Triclinic, P1	D_x = 1.468 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3425 (3) Å	Cell parameters from 3737 reflections
b = 10.3894 (4) Å	θ = 1.0–29.6°
c = 10.6457 (5) Å	µ = 0.56 mm⁻¹
α = 116.535 (2)°	T = 173 K
β = 95.049 (2)°	Block, colorless
γ = 94.955 (2)°	0.12 × 0.08 × 0.06 mm
V = 716.50 (5) Å³

Data collection top

Nonius KappaCCD diffractometer with APEXII CCD	3996 independent reflections
Radiation source: fine-focus sealed tube	3361 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω and ϕ scans	θ_max = 29.7°, θ_min = 2.2°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −10→10
T_min = 0.936, T_max = 0.967	k = −14→14
12341 measured reflections	l = −14→14

Refinement top

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)] = 0.045	Hydrogen site location: difference Fourier map
wR(F²) = 0.104	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0252P)² + 0.6628P] where P = (F_o² + 2F_c²)/3
3996 reflections	(Δ/σ)_max < 0.001
173 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₂H₁₃ClN₂O₂S₂	γ = 94.955 (2)°
M_r = 316.81	V = 716.50 (5) Å³
Triclinic, P1	Z = 2
a = 7.3425 (3) Å	Mo Kα radiation
b = 10.3894 (4) Å	µ = 0.56 mm⁻¹
c = 10.6457 (5) Å	T = 173 K
α = 116.535 (2)°	0.12 × 0.08 × 0.06 mm
β = 95.049 (2)°

Data collection top

Nonius KappaCCD diffractometer with APEXII CCD	3996 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	3361 reflections with I > 2σ(I)
T_min = 0.936, T_max = 0.967	R_int = 0.031
12341 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.09	Δρ_max = 0.47 e Å⁻³
3996 reflections	Δρ_min = −0.26 e Å⁻³
173 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

	x	y	z	U_iso*/U_eq
Cl1	0.89852 (9)	0.10405 (6)	0.44205 (7)	0.04491 (16)
S1	0.37647 (8)	0.94428 (5)	0.28183 (6)	0.03285 (14)
S2	0.37807 (7)	0.61903 (5)	0.12742 (5)	0.02750 (12)
O1	−0.0267 (2)	0.65882 (18)	0.13349 (16)	0.0355 (3)
O2	−0.0309 (2)	0.76565 (17)	−0.00860 (17)	0.0348 (3)
N1	0.5839 (2)	0.65588 (17)	0.36811 (18)	0.0251 (3)
N2	0.5413 (2)	0.78764 (17)	0.38235 (17)	0.0259 (3)
H2N	0.5813	0.8681	0.4610	0.031*
C1	0.7182 (2)	0.5188 (2)	0.4706 (2)	0.0224 (3)
C2	0.8110 (3)	0.5168 (2)	0.5894 (2)	0.0260 (4)
H2	0.8383	0.6039	0.6763	0.031*
C3	0.8640 (3)	0.3890 (2)	0.5824 (2)	0.0280 (4)
H3	0.9271	0.3880	0.6637	0.034*
C4	0.8236 (3)	0.2634 (2)	0.4555 (2)	0.0292 (4)
C5	0.7266 (3)	0.2612 (2)	0.3364 (2)	0.0306 (4)
H5	0.6973	0.1733	0.2505	0.037*
C6	0.6734 (3)	0.3889 (2)	0.3448 (2)	0.0263 (4)
H6	0.6057	0.3884	0.2642	0.032*
C7	0.6691 (3)	0.6550 (2)	0.4777 (2)	0.0244 (4)
H7	0.7005	0.7428	0.5636	0.029*
C8	0.4379 (3)	0.7910 (2)	0.2744 (2)	0.0238 (4)
C9	0.2345 (3)	0.6622 (2)	0.0105 (2)	0.0291 (4)
H9A	0.2984	0.7477	0.0061	0.035*
H9B	0.2172	0.5795	−0.0861	0.035*
C10	0.0471 (3)	0.6945 (2)	0.0554 (2)	0.0281 (4)
C11	−0.2133 (3)	0.8016 (3)	0.0258 (3)	0.0419 (5)
H11A	−0.2092	0.8571	0.1298	0.050*
H11B	−0.3024	0.7118	−0.0090	0.050*
C12	−0.2709 (4)	0.8910 (3)	−0.0444 (3)	0.0506 (6)
H12A	−0.3951	0.9147	−0.0251	0.061*
H12B	−0.2716	0.8359	−0.1470	0.061*
H12C	−0.1839	0.9809	−0.0071	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0472 (3)	0.0344 (3)	0.0633 (4)	0.0143 (2)	0.0028 (3)	0.0306 (3)
S1	0.0483 (3)	0.0196 (2)	0.0283 (3)	0.0074 (2)	−0.0043 (2)	0.01017 (19)
S2	0.0359 (3)	0.0192 (2)	0.0239 (2)	0.00528 (18)	0.00303 (19)	0.00682 (18)
O1	0.0363 (8)	0.0418 (9)	0.0338 (8)	0.0012 (7)	0.0033 (6)	0.0230 (7)
O2	0.0362 (8)	0.0390 (8)	0.0361 (8)	0.0066 (7)	0.0033 (6)	0.0233 (7)
N1	0.0275 (8)	0.0193 (7)	0.0301 (8)	0.0055 (6)	0.0036 (6)	0.0124 (7)
N2	0.0331 (9)	0.0173 (7)	0.0253 (8)	0.0037 (6)	0.0000 (6)	0.0087 (6)
C1	0.0212 (8)	0.0232 (8)	0.0266 (9)	0.0048 (7)	0.0044 (7)	0.0143 (7)
C2	0.0254 (9)	0.0293 (9)	0.0253 (9)	0.0058 (7)	0.0051 (7)	0.0136 (8)
C3	0.0243 (9)	0.0367 (10)	0.0311 (10)	0.0070 (8)	0.0045 (7)	0.0219 (9)
C4	0.0263 (9)	0.0290 (10)	0.0405 (11)	0.0073 (8)	0.0071 (8)	0.0223 (9)
C5	0.0365 (11)	0.0243 (9)	0.0306 (10)	0.0066 (8)	0.0039 (8)	0.0121 (8)
C6	0.0293 (9)	0.0270 (9)	0.0251 (9)	0.0046 (7)	0.0013 (7)	0.0144 (8)
C7	0.0238 (8)	0.0215 (8)	0.0268 (9)	0.0047 (7)	0.0048 (7)	0.0098 (7)
C8	0.0274 (9)	0.0207 (8)	0.0239 (9)	0.0030 (7)	0.0045 (7)	0.0108 (7)
C9	0.0361 (10)	0.0271 (9)	0.0215 (9)	0.0003 (8)	0.0013 (8)	0.0098 (8)
C10	0.0336 (10)	0.0238 (9)	0.0237 (9)	−0.0009 (8)	−0.0020 (8)	0.0099 (8)
C11	0.0372 (12)	0.0431 (13)	0.0504 (14)	0.0093 (10)	0.0063 (10)	0.0252 (12)
C12	0.0539 (16)	0.0440 (14)	0.0556 (16)	0.0164 (12)	0.0016 (13)	0.0237 (13)

Geometric parameters (Å, º) top

Cl1—C4	1.739 (2)	C3—C4	1.380 (3)
S1—C8	1.6618 (19)	C3—H3	0.9500
S2—C8	1.7548 (19)	C4—C5	1.389 (3)
S2—C9	1.792 (2)	C5—C6	1.382 (3)
O1—C10	1.201 (2)	C5—H5	0.9500
O2—C10	1.339 (2)	C6—H6	0.9500
O2—C11	1.455 (3)	C7—H7	0.9500
N1—C7	1.279 (2)	C9—C10	1.513 (3)
N1—N2	1.375 (2)	C9—H9A	0.9900
N2—C8	1.337 (2)	C9—H9B	0.9900
N2—H2N	0.8800	C11—C12	1.493 (3)
C1—C2	1.392 (2)	C11—H11A	0.9900
C1—C6	1.398 (3)	C11—H11B	0.9900
C1—C7	1.462 (2)	C12—H12A	0.9800
C2—C3	1.388 (3)	C12—H12B	0.9800
C2—H2	0.9500	C12—H12C	0.9800

C8—S2—C9	100.82 (9)	C1—C7—H7	120.1
C10—O2—C11	115.16 (17)	N2—C8—S1	122.37 (14)
C7—N1—N2	116.85 (16)	N2—C8—S2	112.84 (13)
C8—N2—N1	118.65 (16)	S1—C8—S2	124.78 (11)
C8—N2—H2N	120.7	C10—C9—S2	113.36 (14)
N1—N2—H2N	120.7	C10—C9—H9A	108.9
C2—C1—C6	119.06 (17)	S2—C9—H9A	108.9
C2—C1—C7	120.29 (17)	C10—C9—H9B	108.9
C6—C1—C7	120.66 (16)	S2—C9—H9B	108.9
C3—C2—C1	120.73 (18)	H9A—C9—H9B	107.7
C3—C2—H2	119.6	O1—C10—O2	123.7 (2)
C1—C2—H2	119.6	O1—C10—C9	126.00 (19)
C4—C3—C2	118.96 (18)	O2—C10—C9	110.25 (17)
C4—C3—H3	120.5	O2—C11—C12	107.7 (2)
C2—C3—H3	120.5	O2—C11—H11A	110.2
C3—C4—C5	121.55 (18)	C12—C11—H11A	110.2
C3—C4—Cl1	119.71 (15)	O2—C11—H11B	110.2
C5—C4—Cl1	118.73 (16)	C12—C11—H11B	110.2
C6—C5—C4	119.01 (19)	H11A—C11—H11B	108.5
C6—C5—H5	120.5	C11—C12—H12A	109.5
C4—C5—H5	120.5	C11—C12—H12B	109.5
C5—C6—C1	120.63 (17)	H12A—C12—H12B	109.5
C5—C6—H6	119.7	C11—C12—H12C	109.5
C1—C6—H6	119.7	H12A—C12—H12C	109.5
N1—C7—C1	119.89 (17)	H12B—C12—H12C	109.5
N1—C7—H7	120.1

C7—N1—N2—C8	−174.09 (18)	C2—C1—C7—N1	−179.95 (18)
C6—C1—C2—C3	2.1 (3)	C6—C1—C7—N1	0.2 (3)
C7—C1—C2—C3	−177.71 (18)	N1—N2—C8—S1	179.15 (14)
C1—C2—C3—C4	0.1 (3)	N1—N2—C8—S2	−1.3 (2)
C2—C3—C4—C5	−1.9 (3)	C9—S2—C8—N2	177.22 (15)
C2—C3—C4—Cl1	176.88 (15)	C9—S2—C8—S1	−3.25 (16)
C3—C4—C5—C6	1.5 (3)	C8—S2—C9—C10	−73.08 (15)
Cl1—C4—C5—C6	−177.31 (16)	C11—O2—C10—O1	1.6 (3)
C4—C5—C6—C1	0.8 (3)	C11—O2—C10—C9	179.48 (17)
C2—C1—C6—C5	−2.6 (3)	S2—C9—C10—O1	−20.3 (3)
C7—C1—C6—C5	177.28 (18)	S2—C9—C10—O2	161.95 (14)
N2—N1—C7—C1	179.74 (16)	C10—O2—C11—C12	175.16 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···S1ⁱ	0.88	2.52	3.3669 (17)	161
C3—H3···O1ⁱⁱ	0.95	2.48	3.410 (2)	166
C9—H9B···O1ⁱⁱⁱ	0.99	2.55	3.153 (3)	119
C9—H9A···S1	0.99	2.69	3.066 (2)	103

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₃ClN₂O₂S₂
M_r	316.81
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.3425 (3), 10.3894 (4), 10.6457 (5)
α, β, γ (°)	116.535 (2), 95.049 (2), 94.955 (2)
V (Å³)	716.50 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.56
Crystal size (mm)	0.12 × 0.08 × 0.06

Data collection
Diffractometer	Nonius KappaCCD diffractometer with APEXII CCD
Absorption correction	Multi-scan (SORTAV; Blessing, 1997)
T_min, T_max	0.936, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	12341, 3996, 3361
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.697

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.104, 1.09
No. of reflections	3996
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.26

Computer programs: COLLECT (Hooft, 1998), DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···S1ⁱ	0.88	2.52	3.3669 (17)	161
C3—H3···O1ⁱⁱ	0.95	2.48	3.410 (2)	166
C9—H9B···O1ⁱⁱⁱ	0.99	2.55	3.153 (3)	119
C9—H9A···S1	0.99	2.69	3.066 (2)	103

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z.

Acknowledgements

The authors are grateful to Scientific Society of Nanotechnology, Islamic Azad University, Yazd Branch, for support of this work.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. CrossRef Web of Science IUCr Journals Google Scholar
Blessing, R. H. (1997). J. Appl. Cryst. 30, 421–426. CrossRef CAS Web of Science IUCr Journals Google Scholar
Duran, A., Doğan, H. N. & Rollas, S. (2002). Farmaco, 57, 559–564. Web of Science CrossRef PubMed CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Gülerman, N. N., Doğan, H. N., Rollas, S., Johansson, C. & Çelik, C. (2001). Farmaco, 56, 953–958. Web of Science PubMed Google Scholar
Hooft, R. (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tabatabaee, M., Ghassemzadeh, M., Sadeghi, A., Shahriary, M. & Neumüller, B. (2009). Z. Anorg. Allg. Chem. 635, 120–124. Web of Science CSD CrossRef CAS Google Scholar
Tabatabaee, M., Ghassemzadeh, M. & Soleimani, N. (2008). Anal. Sci. 24, x173–x174. CAS Google Scholar
Tabatabaee, M., Ghassemzadeh, M., Zarabi, Heravi, M. M., AnaryAbbasinejad, M. & Neumüller, B. (2007). Phosphorus Sulfur Silion Relat. Elem. 182, 677–686. Web of Science CSD CrossRef CAS Google Scholar
Tabatabaee, M., Ghassemzadeh, M., Zarabi, B. & Neumüller, B. (2006). Z. Naturforsch. Teil B. 61, 1421–1425. CAS Google Scholar