2-[(2-Amino­phen­yl)sulfan­yl]-N-(4-meth­oxy­phen­yl)acetamide

Murtaza, S.; Tahir, M.N.; Tariq, J.; Abbas, A.; Kausar, N.

doi:10.1107/S1600536812024178

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1968

doi:10.1107/S1600536812024178

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2-[(2-Aminophenyl)sulfanyl]-N-(4-methoxyphenyl)acetamide

Shahzad Murtaza,^a M. Nawaz Tahir,^b ^* Javaria Tariq,^a Aadil Abbas ^a and Naghmana Kausar ^a

^aDepartment of Chemistry, University of Gujrat, Hafiz Hayat Campus, Gujrat, Pakistan, and ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 26 May 2012; accepted 27 May 2012; online 31 May 2012)

In the title compound, C₁₅H₁₆N₂O₂S, the dihedral angle between the 4-methoxyaniline and 2-aminobenzenethiole fragments is 35.60 (9)°. A short intramolecular N—H⋯S contact leads to an S(5) ring. In the crystal, molecules are consolidated in the form of polymeric chains along [010] as a result of N—H⋯O hydrogen bonds, which generate R₃²(18) and R₄³(22) loops. The polymeric chains are interlinked through C—H⋯O interaction and complete R₂²(8) ring motifs.

Related literature

For a related structure, see: Haisa et al. (1980 ). For hydrogen-bond motif notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₅H₁₆N₂O₂S
M_r = 288.36
Monoclinic, P 2₁ /c
a = 12.9935 (16) Å
b = 4.7990 (4) Å
c = 23.433 (3) Å
β = 95.506 (7)°
V = 1454.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.25 × 0.14 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.965, T_max = 0.975
11532 measured reflections
2845 independent reflections
1525 reflections with I > 2σ(I)
R_int = 0.060

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.121
S = 1.01
2845 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯S1	0.86	2.60	3.004 (3)	110
N1—H1⋯O2ⁱ	0.86	2.00	2.848 (3)	170
N2—H2A⋯O2ⁱⁱ	0.86	2.38	3.200 (3)	161
C3—H3⋯O1ⁱⁱⁱ	0.93	2.47	3.393 (5)	170
Symmetry codes: (i) x, y+1, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x, -y+1, -z.

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: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812024178/hb6821sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812024178/hb6821Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812024178/hb6821Isup3.cml

checkCIF report

Comment top

The title compound (I), (Fig. 1) has been synthesized to check its biological application as antimicrobial agent owing to the concept that amide moiety is an important part of different drugs.

The crystal structure of N-(4-methoxyphenyl)acetamide (Haisa et al., 1980) has been published which is related to the title compound (I, Fig. 1).

In (I), the 4-methoxyanilinic and 2-aminobenzenethiolic groups A (C1–C7/N1/O1) and B (C10—C15/N2/S1) are almost planar with r. m. s. deviation of 0.0150 Å and 0.0134 Å, respectively. The dihedral angle between A/B is 35.60 (9)°. The central acetamide moiety C (C8/C9/O2) is of course planar. The dihedral angle between A/C and B/C is 48.43 (10)° and 78.07 (8)°, respectively. There exist S(5) ring motif (Bernstein et al., 1995) due to H-bonding of N—H···S type (Table 1, Fig. 2). The molecules are stabilized in the form of one-dimensional polymeric network due to H-bondings (Table 1, Fig. 2) of N—H···O type. There exist R₃²(18) and R₄³(22) ring motifs in the polymeric network when three and four molecules respectively, are connected with each other.

Related literature top

For a related structure, see: Haisa et al. (1980). For hydrogen-bond motif notation, see: Bernstein et al. (1995). [ok as edited?]

Experimental top

2-Aminobenzothiol (0.125 g, 0.5 mmol) was dissolved in anhydrous diethylether (10 ml) and NaH (0.024 g, 1 mmol) was added to it at temperature 273–278 K. A separately prepared solution of 2-chloro-N-(4-methoxyphenyl)acetamide (0.1 g, 0.5 mmol) in anhydrous diethylether (10 ml) was added drop wise to above mixture. The mixture was stirred for 4 h and solvent was evaporated to get greyish crystals of (I). m.p. 400 K

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

	Fig. 1. View of the title compound with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The partial packing, which shows that molecules form polymeric chains with various ring motifs. The H-atoms not involved in H-bondings are omitted for clarity.

2-[(2-Aminophenyl)sulfanyl]-N-(4-methoxyphenyl)acetamide top

Crystal data top

C₁₅H₁₆N₂O₂S	F(000) = 608
M_r = 288.36	D_x = 1.317 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1525 reflections
a = 12.9935 (16) Å	θ = 1.6–26.0°
b = 4.7990 (4) Å	µ = 0.23 mm⁻¹
c = 23.433 (3) Å	T = 296 K
β = 95.506 (7)°	Needle, gray
V = 1454.4 (3) Å³	0.25 × 0.14 × 0.12 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	2845 independent reflections
Radiation source: fine-focus sealed tube	1525 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
Detector resolution: 7.80 pixels mm^-1	θ_max = 26.0°, θ_min = 1.6°
ω scans	h = −16→16
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −5→5
T_min = 0.965, T_max = 0.975	l = −27→28
11532 measured reflections

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0435P)² + 0.1361P] where P = (F_o² + 2F_c²)/3
2845 reflections	(Δ/σ)_max < 0.001
182 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₅H₁₆N₂O₂S	V = 1454.4 (3) Å³
M_r = 288.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.9935 (16) Å	µ = 0.23 mm⁻¹
b = 4.7990 (4) Å	T = 296 K
c = 23.433 (3) Å	0.25 × 0.14 × 0.12 mm
β = 95.506 (7)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2845 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1525 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.975	R_int = 0.060
11532 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.01	Δρ_max = 0.18 e Å⁻³
2845 reflections	Δρ_min = −0.20 e Å⁻³
182 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.67008 (6)	0.17005 (14)	0.17482 (3)	0.0513 (3)
O1	0.06467 (19)	0.2484 (5)	−0.05402 (11)	0.0942 (11)
O2	0.48924 (15)	0.0421 (3)	0.09749 (9)	0.0565 (8)
N1	0.43663 (19)	0.4757 (4)	0.07298 (10)	0.0480 (9)
N2	0.5848 (2)	0.4083 (5)	0.27906 (12)	0.0763 (12)
C1	0.3429 (2)	0.4077 (5)	0.03984 (12)	0.0423 (10)
C2	0.2538 (3)	0.5466 (6)	0.04982 (14)	0.0578 (11)
C3	0.1626 (3)	0.4868 (7)	0.01822 (16)	0.0750 (14)
C4	0.1593 (3)	0.2887 (7)	−0.02452 (14)	0.0590 (12)
C5	0.2468 (3)	0.1500 (6)	−0.03442 (13)	0.0569 (11)
C6	0.3386 (2)	0.2099 (6)	−0.00259 (12)	0.0496 (11)
C7	0.0533 (3)	0.0393 (9)	−0.09623 (17)	0.1020 (17)
C8	0.5023 (2)	0.2953 (5)	0.09956 (11)	0.0423 (10)
C9	0.5937 (2)	0.4227 (5)	0.13308 (13)	0.0606 (11)
C10	0.7332 (2)	0.4001 (5)	0.22519 (13)	0.0467 (11)
C11	0.6839 (3)	0.4890 (6)	0.27227 (14)	0.0520 (11)
C12	0.7355 (3)	0.6709 (7)	0.31078 (15)	0.0743 (14)
C13	0.8316 (3)	0.7639 (7)	0.30315 (18)	0.0838 (17)
C14	0.8816 (3)	0.6776 (7)	0.25769 (19)	0.0842 (16)
C15	0.8321 (3)	0.4935 (7)	0.21861 (16)	0.0654 (14)
H1	0.45235	0.64944	0.07614	0.0576*
H2	0.25569	0.68219	0.07826	0.0696*
H2A	0.55421	0.47092	0.30741	0.0916*
H2B	0.55300	0.29502	0.25497	0.0916*
H3	0.10255	0.58008	0.02558	0.0897*
H5	0.24472	0.01413	−0.06280	0.0680*
H6	0.39837	0.11528	−0.00991	0.0595*
H7A	0.07153	−0.13793	−0.07913	0.1529*
H7B	0.09784	0.07889	−0.12562	0.1529*
H7C	−0.01719	0.03419	−0.11275	0.1529*
H9A	0.57022	0.56384	0.15846	0.0724*
H9B	0.63654	0.51361	0.10692	0.0724*
H12	0.70365	0.73062	0.34250	0.0890*
H13	0.86413	0.88868	0.32937	0.1003*
H14	0.94784	0.74134	0.25299	0.1009*
H15	0.86569	0.43201	0.18764	0.0783*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0592 (5)	0.0369 (4)	0.0572 (5)	0.0064 (4)	0.0021 (4)	−0.0061 (4)
O1	0.0605 (17)	0.114 (2)	0.103 (2)	0.0024 (14)	−0.0178 (16)	−0.0410 (17)
O2	0.0715 (15)	0.0257 (10)	0.0700 (15)	−0.0040 (9)	−0.0054 (12)	−0.0028 (10)
N1	0.0592 (17)	0.0250 (12)	0.0578 (17)	−0.0080 (11)	−0.0050 (14)	−0.0015 (11)
N2	0.073 (2)	0.086 (2)	0.074 (2)	−0.0108 (16)	0.0276 (17)	−0.0247 (16)
C1	0.054 (2)	0.0314 (15)	0.0412 (18)	−0.0073 (14)	0.0034 (15)	0.0019 (13)
C2	0.065 (2)	0.0463 (18)	0.061 (2)	0.0043 (17)	0.0005 (19)	−0.0163 (16)
C3	0.056 (2)	0.080 (2)	0.088 (3)	0.0132 (19)	0.002 (2)	−0.027 (2)
C4	0.050 (2)	0.062 (2)	0.063 (2)	−0.0052 (17)	−0.0051 (18)	−0.0093 (18)
C5	0.062 (2)	0.0558 (19)	0.053 (2)	−0.0040 (17)	0.0063 (18)	−0.0160 (17)
C6	0.0485 (19)	0.0511 (17)	0.0498 (19)	−0.0019 (15)	0.0082 (16)	−0.0111 (16)
C7	0.091 (3)	0.112 (3)	0.097 (3)	−0.015 (3)	−0.022 (2)	−0.035 (3)
C8	0.055 (2)	0.0301 (15)	0.0423 (18)	−0.0035 (14)	0.0069 (15)	−0.0016 (14)
C9	0.073 (2)	0.0386 (17)	0.066 (2)	−0.0118 (15)	−0.0146 (19)	0.0056 (16)
C10	0.0467 (19)	0.0360 (16)	0.056 (2)	0.0069 (13)	−0.0020 (16)	−0.0011 (14)
C11	0.058 (2)	0.0446 (17)	0.052 (2)	0.0073 (16)	−0.0016 (18)	−0.0048 (16)
C12	0.086 (3)	0.074 (2)	0.061 (2)	−0.003 (2)	−0.002 (2)	−0.017 (2)
C13	0.084 (3)	0.072 (3)	0.089 (3)	0.001 (2)	−0.024 (3)	−0.021 (2)
C14	0.054 (2)	0.072 (2)	0.122 (4)	−0.010 (2)	−0.015 (2)	−0.006 (3)
C15	0.051 (2)	0.064 (2)	0.081 (3)	0.0049 (18)	0.005 (2)	−0.003 (2)

Geometric parameters (Å, º) top

S1—C9	1.796 (3)	C10—C11	1.395 (4)
S1—C10	1.760 (3)	C11—C12	1.382 (5)
O1—C4	1.365 (5)	C12—C13	1.354 (5)
O1—C7	1.407 (5)	C13—C14	1.364 (6)
O2—C8	1.227 (3)	C14—C15	1.386 (5)
N1—C1	1.418 (4)	C2—H2	0.9300
N1—C8	1.328 (3)	C3—H3	0.9300
N2—C11	1.369 (5)	C5—H5	0.9300
N1—H1	0.8600	C6—H6	0.9300
N2—H2A	0.8600	C7—H7A	0.9600
N2—H2B	0.8600	C7—H7B	0.9600
C1—C2	1.375 (4)	C7—H7C	0.9600
C1—C6	1.372 (4)	C9—H9A	0.9700
C2—C3	1.366 (5)	C9—H9B	0.9700
C3—C4	1.379 (5)	C12—H12	0.9300
C4—C5	1.357 (5)	C13—H13	0.9300
C5—C6	1.375 (5)	C14—H14	0.9300
C8—C9	1.491 (4)	C15—H15	0.9300
C10—C15	1.384 (5)

C9—S1—C10	98.01 (12)	C13—C14—C15	119.0 (4)
C4—O1—C7	119.1 (3)	C10—C15—C14	120.7 (3)
C1—N1—C8	125.9 (2)	C1—C2—H2	120.00
C8—N1—H1	117.00	C3—C2—H2	120.00
C1—N1—H1	117.00	C2—C3—H3	120.00
C11—N2—H2A	120.00	C4—C3—H3	120.00
H2A—N2—H2B	120.00	C4—C5—H5	120.00
C11—N2—H2B	120.00	C6—C5—H5	120.00
N1—C1—C6	122.0 (2)	C1—C6—H6	120.00
N1—C1—C2	119.2 (2)	C5—C6—H6	120.00
C2—C1—C6	118.8 (3)	O1—C7—H7A	109.00
C1—C2—C3	120.4 (3)	O1—C7—H7B	109.00
C2—C3—C4	120.2 (3)	O1—C7—H7C	109.00
C3—C4—C5	119.6 (3)	H7A—C7—H7B	109.00
O1—C4—C3	115.4 (3)	H7A—C7—H7C	109.00
O1—C4—C5	124.9 (3)	H7B—C7—H7C	109.00
C4—C5—C6	120.2 (3)	S1—C9—H9A	109.00
C1—C6—C5	120.7 (3)	S1—C9—H9B	109.00
O2—C8—N1	123.2 (2)	C8—C9—H9A	109.00
O2—C8—C9	121.8 (2)	C8—C9—H9B	109.00
N1—C8—C9	115.0 (2)	H9A—C9—H9B	108.00
S1—C9—C8	112.38 (17)	C11—C12—H12	119.00
S1—C10—C15	120.4 (2)	C13—C12—H12	119.00
C11—C10—C15	119.4 (3)	C12—C13—H13	119.00
S1—C10—C11	120.2 (2)	C14—C13—H13	119.00
N2—C11—C12	120.4 (3)	C13—C14—H14	121.00
C10—C11—C12	118.6 (3)	C15—C14—H14	121.00
N2—C11—C10	120.9 (3)	C10—C15—H15	120.00
C11—C12—C13	121.2 (3)	C14—C15—H15	120.00
C12—C13—C14	121.2 (4)

C10—S1—C9—C8	−158.8 (2)	O1—C4—C5—C6	179.1 (3)
C9—S1—C10—C11	82.1 (2)	C3—C4—C5—C6	−1.0 (5)
C9—S1—C10—C15	−98.1 (3)	C4—C5—C6—C1	0.7 (5)
C7—O1—C4—C3	−176.6 (3)	O2—C8—C9—S1	−6.7 (3)
C7—O1—C4—C5	3.3 (5)	N1—C8—C9—S1	172.7 (2)
C8—N1—C1—C2	131.0 (3)	S1—C10—C11—N2	−2.5 (4)
C8—N1—C1—C6	−50.0 (4)	S1—C10—C11—C12	−179.6 (2)
C1—N1—C8—O2	1.2 (4)	C15—C10—C11—N2	177.8 (3)
C1—N1—C8—C9	−178.2 (2)	C15—C10—C11—C12	0.6 (4)
N1—C1—C2—C3	179.5 (3)	S1—C10—C15—C14	179.1 (3)
C6—C1—C2—C3	0.4 (4)	C11—C10—C15—C14	−1.1 (5)
N1—C1—C6—C5	−179.4 (3)	N2—C11—C12—C13	−176.7 (3)
C2—C1—C6—C5	−0.4 (4)	C10—C11—C12—C13	0.5 (5)
C1—C2—C3—C4	−0.8 (5)	C11—C12—C13—C14	−1.1 (6)
C2—C3—C4—O1	−179.0 (3)	C12—C13—C14—C15	0.6 (6)
C2—C3—C4—C5	1.1 (5)	C13—C14—C15—C10	0.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···S1	0.86	2.60	3.004 (3)	110
N1—H1···O2ⁱ	0.86	2.00	2.848 (3)	170
N2—H2A···O2ⁱⁱ	0.86	2.38	3.200 (3)	161
C3—H3···O1ⁱⁱⁱ	0.93	2.47	3.393 (5)	170

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₆N₂O₂S
M_r	288.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	12.9935 (16), 4.7990 (4), 23.433 (3)
β (°)	95.506 (7)
V (Å³)	1454.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.25 × 0.14 × 0.12

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.965, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	11532, 2845, 1525
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.121, 1.01
No. of reflections	2845
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.20

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···A	D—H	H···A	D···A	D—H···A
N2—H2B···S1	0.86	2.60	3.004 (3)	110
N1—H1···O2ⁱ	0.86	2.00	2.848 (3)	170
N2—H2A···O2ⁱⁱ	0.86	2.38	3.200 (3)	161
C3—H3···O1ⁱⁱⁱ	0.93	2.47	3.393 (5)	170

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

Acknowledgements

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. The authors also acknowledge the technical support provided by Syed Muhammad Hussain Rizvi of Bana International, Karachi, Pakistan.

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