Diphenyl (2-chloro­benzyl­amido)­phosphate

Pourayoubi, M.; Zargaran, P.; Rheingold, A.L.; Golen, J.A.

doi:10.1107/S160053681004955X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page o5

https://doi.org/10.1107/S160053681004955X

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Diphenyl (2-chlorobenzylamido)phosphate

Mehrdad Pourayoubi,^a ^* Poorya Zargaran,^a Arnold L. Rheingold ^b and James A. Golen ^b

^aDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad, 91779, Iran, and ^bDepartment of Chemistry, University of California, San Diego, 9500 Gilman, Drive, La Jolla, CA 92093, USA
^*Correspondence e-mail: mehrdad_pourayoubi@yahoo.com

(Received 21 November 2010; accepted 26 November 2010; online 4 December 2010)

In the title compound, C₁₉H₁₇ClNO₃P, the P atom exhibits a distorted tetrahedral configuration. In the crystal, pairs of intermolecular N—H⋯O(P) hydrogen bonds form centrosymmetric dimers.

Related literature

For related structures, see: Pourayoubi & Zargaran (2010 ); Pourayoubi et al. (2010 ).

Experimental

Crystal data

C₁₉H₁₇ClNO₃P
M_r = 373.76
Triclinic, $[P \overline 1]$
a = 8.6178 (5) Å
b = 9.5901 (6) Å
c = 12.1543 (7) Å
α = 107.609 (1)°
β = 93.882 (1)°
γ = 110.036 (1)°
V = 882.86 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 100 K
0.40 × 0.35 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.881, T_max = 0.923
13560 measured reflections
3982 independent reflections
3681 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.086
S = 1.02
3982 reflections
230 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.80 (2)	2.08 (2)	2.8703 (15)	172.2 (19)
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681004955X/lh5173sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681004955X/lh5173Isup2.hkl

checkCIF report

Comment top

In our previous works, the crystal structures of some amidophosphoric acid ester compounds having the P(O)(OC₆H₅)₂ phosphoester moiety have been reported (Pourayoubi et al., 2010; Pourayoubi & Zargaran, 2010). Herein, we report the synthesis and crystal structure of the title amidophosphoric acid ester.

The molecular structure of the title compound is shown in Fig. 1. The P atom has a distorted tetrahedral configuration with the bond angles in the range of 98.03 (5)° [O2–P1–O3] to 116.37 (6)° [O1–P1–O2]. In the crystal structure, pairs of intermolecular N-H···O(P) hydrogen bonds form centrosymmetric dimers.

Related literature top

For related structures, see: Pourayoubi & Zargaran (2010); Pourayoubi et al. (2010).

Experimental top

To a solution of (C₆H₅O)₂P(O)Cl in chloroform, a solution of 2-chlorobenzylamine (1:2 mole ratio) in chloroform was added at 273 K. After 4 h stirring, the solvent was removed and product was washed with distilled water and recrystallized from CH₃CN at room temperature. IR (KBr, cm^-1): 3206.6, 3065.7, 2909.2, 2715.0, 1947.0, 1591.1, 1486.9, 1456.4, 1257.1, 1198.0, 1131.5, 1016.5, 940.3, 756.3, 686.0.

Structure description top

For related structures, see: Pourayoubi & Zargaran (2010); Pourayoubi et al. (2010).

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound. Ellipsoids are given at the 50% probability level.

Diphenyl (2-chlorobenzylamido)phosphate top

Crystal data top

C₁₉H₁₇ClNO₃P	Z = 2
M_r = 373.76	F(000) = 388
Triclinic, P1	D_x = 1.406 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6178 (5) Å	Cell parameters from 9988 reflections
b = 9.5901 (6) Å	θ = 2.4–28.0°
c = 12.1543 (7) Å	µ = 0.33 mm⁻¹
α = 107.609 (1)°	T = 100 K
β = 93.882 (1)°	Block, colourless
γ = 110.036 (1)°	0.40 × 0.35 × 0.25 mm
V = 882.86 (9) Å³

Data collection top

Bruker APEXII CCD diffractometer	3982 independent reflections
Radiation source: fine-focus sealed tube	3681 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
φ and ω scans	θ_max = 28.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→10
T_min = 0.881, T_max = 0.923	k = −11→12
13560 measured reflections	l = −15→11

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0396P)² + 0.4993P] where P = (F_o² + 2F_c²)/3
3982 reflections	(Δ/σ)_max = 0.004
230 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₁₉H₁₇ClNO₃P	γ = 110.036 (1)°
M_r = 373.76	V = 882.86 (9) Å³
Triclinic, P1	Z = 2
a = 8.6178 (5) Å	Mo Kα radiation
b = 9.5901 (6) Å	µ = 0.33 mm⁻¹
c = 12.1543 (7) Å	T = 100 K
α = 107.609 (1)°	0.40 × 0.35 × 0.25 mm
β = 93.882 (1)°

Data collection top

Bruker APEXII CCD diffractometer	3982 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3681 reflections with I > 2σ(I)
T_min = 0.881, T_max = 0.923	R_int = 0.026
13560 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.28 e Å⁻³
3982 reflections	Δρ_min = −0.44 e Å⁻³
230 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	1.12274 (4)	0.65811 (4)	0.77058 (3)	0.02847 (10)
P1	0.49017 (4)	0.15695 (4)	0.67814 (3)	0.01573 (9)
O1	0.35884 (12)	0.01133 (11)	0.59500 (8)	0.0201 (2)
O2	0.44078 (12)	0.30686 (11)	0.72227 (8)	0.01837 (19)
O3	0.53917 (12)	0.14595 (11)	0.80359 (8)	0.0184 (2)
N1	0.65627 (15)	0.21809 (13)	0.62570 (10)	0.0194 (2)
C1	0.97088 (17)	0.61883 (16)	0.65109 (11)	0.0190 (3)
C2	1.00000 (19)	0.72582 (16)	0.59229 (13)	0.0244 (3)
H2A	1.1015	0.8170	0.6159	0.029*
C3	0.8788 (2)	0.69789 (18)	0.49836 (13)	0.0276 (3)
H3A	0.8965	0.7708	0.4577	0.033*
C4	0.7317 (2)	0.56346 (18)	0.46398 (13)	0.0262 (3)
H4A	0.6485	0.5443	0.3999	0.031*
C5	0.70658 (17)	0.45701 (16)	0.52345 (12)	0.0207 (3)
H5A	0.6058	0.3650	0.4989	0.025*
C6	0.82539 (16)	0.48181 (15)	0.61804 (11)	0.0167 (2)
C7	0.80201 (17)	0.36547 (15)	0.68278 (11)	0.0188 (3)
H7A	0.9043	0.3410	0.6882	0.023*
H7B	0.7890	0.4157	0.7639	0.023*
C8	0.32185 (16)	0.31673 (15)	0.79467 (11)	0.0170 (3)
C9	0.35893 (18)	0.46128 (16)	0.88220 (12)	0.0206 (3)
H9A	0.4608	0.5481	0.8920	0.025*
C10	0.24451 (19)	0.47717 (17)	0.95549 (12)	0.0232 (3)
H10A	0.2686	0.5755	1.0163	0.028*
C11	0.09537 (19)	0.35066 (17)	0.94059 (13)	0.0235 (3)
H11A	0.0181	0.3619	0.9915	0.028*
C12	0.05959 (18)	0.20772 (17)	0.85097 (13)	0.0241 (3)
H12A	−0.0430	0.1213	0.8402	0.029*
C13	0.17259 (18)	0.18976 (16)	0.77676 (12)	0.0215 (3)
H13A	0.1478	0.0921	0.7149	0.026*
C14	0.60296 (16)	0.03684 (15)	0.82152 (12)	0.0177 (3)
C15	0.60994 (18)	−0.08832 (16)	0.73025 (13)	0.0233 (3)
H15A	0.5699	−0.1047	0.6508	0.028*
C16	0.67701 (19)	−0.18925 (17)	0.75786 (14)	0.0277 (3)
H16A	0.6826	−0.2756	0.6965	0.033*
C17	0.7356 (2)	−0.16551 (18)	0.87353 (15)	0.0287 (3)
H17A	0.7817	−0.2348	0.8913	0.034*
C18	0.7269 (2)	−0.03992 (19)	0.96360 (14)	0.0278 (3)
H18A	0.7667	−0.0235	1.0431	0.033*
C19	0.65988 (18)	0.06176 (16)	0.93767 (12)	0.0214 (3)
H19A	0.6533	0.1475	0.9991	0.026*
H1N	0.661 (2)	0.160 (2)	0.5644 (18)	0.031 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.02121 (18)	0.0312 (2)	0.02217 (17)	0.00205 (14)	−0.00251 (13)	0.00503 (14)
P1	0.01745 (17)	0.01436 (16)	0.01548 (16)	0.00594 (13)	0.00454 (12)	0.00518 (12)
O1	0.0195 (5)	0.0182 (5)	0.0192 (4)	0.0047 (4)	0.0049 (4)	0.0043 (4)
O2	0.0209 (5)	0.0169 (4)	0.0210 (4)	0.0091 (4)	0.0081 (4)	0.0086 (4)
O3	0.0242 (5)	0.0170 (4)	0.0164 (4)	0.0107 (4)	0.0044 (4)	0.0056 (3)
N1	0.0207 (6)	0.0157 (5)	0.0184 (5)	0.0048 (4)	0.0074 (5)	0.0029 (4)
C1	0.0186 (6)	0.0199 (6)	0.0170 (6)	0.0080 (5)	0.0041 (5)	0.0036 (5)
C2	0.0262 (7)	0.0184 (6)	0.0290 (7)	0.0072 (6)	0.0116 (6)	0.0088 (5)
C3	0.0369 (8)	0.0268 (7)	0.0302 (7)	0.0179 (7)	0.0142 (7)	0.0170 (6)
C4	0.0302 (8)	0.0322 (8)	0.0235 (7)	0.0178 (6)	0.0053 (6)	0.0128 (6)
C5	0.0198 (6)	0.0218 (6)	0.0201 (6)	0.0088 (5)	0.0032 (5)	0.0059 (5)
C6	0.0181 (6)	0.0166 (6)	0.0166 (6)	0.0086 (5)	0.0054 (5)	0.0049 (5)
C7	0.0178 (6)	0.0189 (6)	0.0188 (6)	0.0054 (5)	0.0025 (5)	0.0072 (5)
C8	0.0190 (6)	0.0198 (6)	0.0173 (6)	0.0109 (5)	0.0048 (5)	0.0091 (5)
C9	0.0211 (7)	0.0179 (6)	0.0223 (6)	0.0072 (5)	0.0035 (5)	0.0068 (5)
C10	0.0289 (7)	0.0217 (7)	0.0209 (6)	0.0132 (6)	0.0057 (6)	0.0056 (5)
C11	0.0259 (7)	0.0295 (7)	0.0249 (7)	0.0171 (6)	0.0107 (6)	0.0140 (6)
C12	0.0199 (7)	0.0238 (7)	0.0315 (7)	0.0085 (5)	0.0084 (6)	0.0125 (6)
C13	0.0217 (7)	0.0185 (6)	0.0238 (7)	0.0085 (5)	0.0050 (5)	0.0056 (5)
C14	0.0161 (6)	0.0162 (6)	0.0225 (6)	0.0057 (5)	0.0050 (5)	0.0092 (5)
C15	0.0257 (7)	0.0201 (6)	0.0231 (7)	0.0103 (6)	0.0016 (5)	0.0049 (5)
C16	0.0281 (8)	0.0198 (7)	0.0352 (8)	0.0120 (6)	0.0052 (6)	0.0066 (6)
C17	0.0272 (8)	0.0265 (7)	0.0410 (9)	0.0138 (6)	0.0075 (7)	0.0193 (7)
C18	0.0297 (8)	0.0339 (8)	0.0279 (7)	0.0142 (6)	0.0068 (6)	0.0190 (6)
C19	0.0230 (7)	0.0229 (7)	0.0214 (6)	0.0094 (5)	0.0080 (5)	0.0102 (5)

Geometric parameters (Å, º) top

Cl1—C1	1.7429 (14)	C8—C9	1.3834 (18)
P1—O1	1.4699 (10)	C8—C13	1.3831 (19)
P1—O2	1.5872 (9)	C9—C10	1.389 (2)
P1—O3	1.5984 (9)	C9—H9A	0.9500
P1—N1	1.6042 (12)	C10—C11	1.387 (2)
O2—C8	1.4043 (15)	C10—H10A	0.9500
O3—C14	1.4002 (15)	C11—C12	1.386 (2)
N1—C7	1.4591 (17)	C11—H11A	0.9500
N1—H1N	0.80 (2)	C12—C13	1.390 (2)
C1—C2	1.3850 (19)	C12—H12A	0.9500
C1—C6	1.3942 (18)	C13—H13A	0.9500
C2—C3	1.389 (2)	C14—C19	1.3829 (19)
C2—H2A	0.9500	C14—C15	1.3884 (19)
C3—C4	1.388 (2)	C15—C16	1.392 (2)
C3—H3A	0.9500	C15—H15A	0.9500
C4—C5	1.388 (2)	C16—C17	1.384 (2)
C4—H4A	0.9500	C16—H16A	0.9500
C5—C6	1.3910 (18)	C17—C18	1.389 (2)
C5—H5A	0.9500	C17—H17A	0.9500
C6—C7	1.5175 (17)	C18—C19	1.389 (2)
C7—H7A	0.9900	C18—H18A	0.9500
C7—H7B	0.9900	C19—H19A	0.9500

O1—P1—O2	116.37 (6)	C9—C8—O2	116.66 (12)
O1—P1—O3	113.92 (5)	C13—C8—O2	121.59 (12)
O2—P1—O3	98.03 (5)	C8—C9—C10	118.77 (13)
O1—P1—N1	113.05 (6)	C8—C9—H9A	120.6
O2—P1—N1	104.00 (6)	C10—C9—H9A	120.6
O3—P1—N1	110.13 (6)	C11—C10—C9	120.55 (13)
C8—O2—P1	123.42 (8)	C11—C10—H10A	119.7
C14—O3—P1	124.66 (8)	C9—C10—H10A	119.7
C7—N1—P1	125.99 (9)	C12—C11—C10	119.65 (13)
C7—N1—H1N	117.4 (14)	C12—C11—H11A	120.2
P1—N1—H1N	116.5 (14)	C10—C11—H11A	120.2
C2—C1—C6	122.43 (13)	C11—C12—C13	120.56 (14)
C2—C1—Cl1	118.35 (11)	C11—C12—H12A	119.7
C6—C1—Cl1	119.22 (10)	C13—C12—H12A	119.7
C1—C2—C3	119.07 (13)	C8—C13—C12	118.73 (13)
C1—C2—H2A	120.5	C8—C13—H13A	120.6
C3—C2—H2A	120.5	C12—C13—H13A	120.6
C4—C3—C2	119.95 (13)	C19—C14—C15	121.49 (12)
C4—C3—H3A	120.0	C19—C14—O3	115.36 (11)
C2—C3—H3A	120.0	C15—C14—O3	123.15 (12)
C3—C4—C5	119.83 (14)	C14—C15—C16	118.46 (13)
C3—C4—H4A	120.1	C14—C15—H15A	120.8
C5—C4—H4A	120.1	C16—C15—H15A	120.8
C4—C5—C6	121.60 (13)	C17—C16—C15	120.86 (14)
C4—C5—H5A	119.2	C17—C16—H16A	119.6
C6—C5—H5A	119.2	C15—C16—H16A	119.6
C5—C6—C1	117.10 (12)	C16—C17—C18	119.76 (13)
C5—C6—C7	122.47 (12)	C16—C17—H17A	120.1
C1—C6—C7	120.42 (12)	C18—C17—H17A	120.1
N1—C7—C6	113.03 (11)	C19—C18—C17	120.15 (14)
N1—C7—H7A	109.0	C19—C18—H18A	119.9
C6—C7—H7A	109.0	C17—C18—H18A	119.9
N1—C7—H7B	109.0	C14—C19—C18	119.28 (13)
C6—C7—H7B	109.0	C14—C19—H19A	120.4
H7A—C7—H7B	107.8	C18—C19—H19A	120.4
C9—C8—C13	121.71 (13)

O1—P1—O2—C8	67.62 (11)	C1—C6—C7—N1	−171.04 (11)
O3—P1—O2—C8	−54.18 (10)	P1—O2—C8—C9	140.36 (10)
N1—P1—O2—C8	−167.34 (10)	P1—O2—C8—C13	−41.74 (16)
O1—P1—O3—C14	59.85 (11)	C13—C8—C9—C10	1.6 (2)
O2—P1—O3—C14	−176.56 (10)	O2—C8—C9—C10	179.53 (11)
N1—P1—O3—C14	−68.38 (11)	C8—C9—C10—C11	−0.4 (2)
O1—P1—N1—C7	174.57 (10)	C9—C10—C11—C12	−0.7 (2)
O2—P1—N1—C7	47.45 (12)	C10—C11—C12—C13	0.6 (2)
O3—P1—N1—C7	−56.72 (12)	C9—C8—C13—C12	−1.7 (2)
C6—C1—C2—C3	1.3 (2)	O2—C8—C13—C12	−179.47 (12)
Cl1—C1—C2—C3	−178.73 (11)	C11—C12—C13—C8	0.5 (2)
C1—C2—C3—C4	−0.6 (2)	P1—O3—C14—C19	171.04 (10)
C2—C3—C4—C5	−0.2 (2)	P1—O3—C14—C15	−8.87 (18)
C3—C4—C5—C6	0.4 (2)	C19—C14—C15—C16	−0.4 (2)
C4—C5—C6—C1	0.29 (19)	O3—C14—C15—C16	179.53 (13)
C4—C5—C6—C7	−178.79 (12)	C14—C15—C16—C17	−0.1 (2)
C2—C1—C6—C5	−1.16 (19)	C15—C16—C17—C18	0.4 (2)
Cl1—C1—C6—C5	178.91 (10)	C16—C17—C18—C19	−0.2 (2)
C2—C1—C6—C7	177.94 (12)	C15—C14—C19—C18	0.5 (2)
Cl1—C1—C6—C7	−1.99 (17)	O3—C14—C19—C18	−179.36 (12)
P1—N1—C7—C6	−113.96 (12)	C17—C18—C19—C14	−0.3 (2)
C5—C6—C7—N1	8.01 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.80 (2)	2.08 (2)	2.8703 (15)	172.2 (19)

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₇ClNO₃P
M_r	373.76
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.6178 (5), 9.5901 (6), 12.1543 (7)
α, β, γ (°)	107.609 (1), 93.882 (1), 110.036 (1)
V (Å³)	882.86 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.40 × 0.35 × 0.25

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.881, 0.923
No. of measured, independent and observed [I > 2σ(I)] reflections	13560, 3982, 3681
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.086, 1.02
No. of reflections	3982
No. of parameters	230
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.44

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.80 (2)	2.08 (2)	2.8703 (15)	172.2 (19)

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

The authors wish to thank Ferdowsi University of Mashhad for the Research University Grant (No. 15144/2) and Bruker AXS Inc. (Madison, WI).

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Pourayoubi, M., Eshtiagh-Hosseini, H., Zargaran, P. & Divjakovic, V. (2010). Acta Cryst. E66, o204. Web of Science CSD CrossRef IUCr Journals Google Scholar
Pourayoubi, M. & Zargaran, P. (2010). Acta Cryst. E66, o3273–o3274. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar