(RP,RP)-Bis[(3-menthyloxy)(phenyl)­phosphino­yl] disulfide

Xu, Z.-Y.; Zhao, C.-Q.

doi:10.1107/S1600536811038165

organic compounds

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Volume 67| Part 10| October 2011| Page o2802

https://doi.org/10.1107/S1600536811038165

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(R_P,R_P)-Bis[(3-menthyloxy)(phenyl)phosphinoyl] disulfide

Zhong-Yuan Xu ^a and Chang-Qiu Zhao ^a ^*

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: literabc@hotmail.com

(Received 6 September 2011; accepted 19 September 2011; online 30 September 2011)

The molecule of the title compound, C₃₂H₄₈O₄P₂S₂, has 2 symmetry, the mid-point of the S—S bond being located on a twofold rotation axis. The two tetrahedral P units are linked by a S—S bond with a P—S—S—P torsion angle is 131.19 (6)°. The dihedral angle between two phenyl rings is 12.66 (13)°. The cyclohexane ring of the menthoxyl group displays a chair conformation. Weak intermolecular C—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For general background to chiral phosphorus compounds, see: Perlikowska & Daran (2004 ).

Experimental

Crystal data

C₃₂H₄₈O₄P₂S₂
M_r = 622.76
Orthorhombic, P 2₁ 2₁ 2
a = 9.9910 (9) Å
b = 18.9100 (17) Å
c = 8.9747 (7) Å
V = 1695.6 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 298 K
0.40 × 0.28 × 0.16 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.895, T_max = 0.956
7818 measured reflections
2989 independent reflections
2141 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.080
S = 0.91
2989 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.16 e Å⁻³
Absolute structure: Flack (1983 ), 1736 Friedel pairs
Flack parameter: −0.10 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6B⋯O2ⁱ	0.97	2.59	3.527 (3)	162
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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/S1600536811038165/xu5323sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811038165/xu5323Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811038165/xu5323Isup3.cml

checkCIF report

Comment top

Chiral phosphorus compounds have been widely used in both chemistry and biology (Perlikowska & Daran, 2004). The P-chiral title compound was synthesized by (R_p)-O-menthyl phenylphosphonothioate and sulfuryl chloride. The fully extended substituents phenyl, menthoxy link to phosphorus atom, and the two phosphorus atoms are connected by dithio bond to form two similar P-centered irregular tetrahedrons. The angle of O2—P—S1 and O1—P—S1 are 113.31 (9) ° and 95.11 (7) °. Intermolecular C6—H6···O2 hydrogen bonds is observed in the crystal structure (Table 1).

Related literature top

For general background to chiral phosphorus compounds, see: Perlikowska & Daran (2004).

Experimental top

Sulfuryl chloride (0.3 mmol) was added to a stirred ether solution of (R_p)-O-menthyl phenylphosphonothioate (0.6 mmol) in a Schlenk tube under nitrogen, and the mixture was stirred for 4 h at 273 K. After washing with water and removing solvents, the resulting residue was purified by preparative TLC on silica gel to afford optically pure product. The crystal suit for X-ray diffraction was obtained from recrystallization with ethyl ether.

Structure description top

For general background to chiral phosphorus compounds, see: Perlikowska & Daran (2004).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 compound. H atoms have been omitted for clarity.

(R_P,R_P)-Bis[(2-isopropyl-5- methylcyclohexyloxy)(phenyl)phosphinoyl] disulfide top

Crystal data top

C₃₂H₄₈O₄P₂S₂	F(000) = 668
M_r = 622.76	D_x = 1.220 Mg m⁻³
Orthorhombic, P2₁2₁2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2ab	Cell parameters from 1878 reflections
a = 9.9910 (9) Å	θ = 3.1–22.1°
b = 18.9100 (17) Å	µ = 0.28 mm⁻¹
c = 8.9747 (7) Å	T = 298 K
V = 1695.6 (3) Å³	Block, colorless
Z = 2	0.40 × 0.28 × 0.16 mm

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2989 independent reflections
Radiation source: fine-focus sealed tube	2141 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
φ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→9
T_min = 0.895, T_max = 0.956	k = −15→22
7818 measured reflections	l = −10→10

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.080	w = 1/[σ²(F_o²) + (0.0327P)²] where P = (F_o² + 2F_c²)/3
S = 0.91	(Δ/σ)_max = 0.001
2989 reflections	Δρ_max = 0.33 e Å⁻³
184 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1736 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.10 (10)

Crystal data top

C₃₂H₄₈O₄P₂S₂	V = 1695.6 (3) Å³
M_r = 622.76	Z = 2
Orthorhombic, P2₁2₁2	Mo Kα radiation
a = 9.9910 (9) Å	µ = 0.28 mm⁻¹
b = 18.9100 (17) Å	T = 298 K
c = 8.9747 (7) Å	0.40 × 0.28 × 0.16 mm

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2989 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2141 reflections with I > 2σ(I)
T_min = 0.895, T_max = 0.956	R_int = 0.043
7818 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.080	Δρ_max = 0.33 e Å⁻³
S = 0.91	Δρ_min = −0.16 e Å⁻³
2989 reflections	Absolute structure: Flack (1983), 1736 Friedel pairs
184 parameters	Absolute structure parameter: −0.10 (10)
0 restraints

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
P1	0.89547 (8)	0.39154 (4)	0.02808 (9)	0.0522 (2)
S1	1.05009 (7)	0.45208 (4)	−0.06827 (9)	0.0569 (2)
O1	0.97493 (16)	0.31924 (8)	0.0227 (2)	0.0530 (5)
O2	0.76990 (17)	0.39533 (10)	−0.0544 (2)	0.0674 (6)
C1	0.8604 (3)	0.13924 (16)	0.1576 (4)	0.0695 (10)
H1	0.7641	0.1447	0.1399	0.083*
C2	0.9227 (3)	0.21278 (15)	0.1605 (3)	0.0606 (9)
H2A	0.8801	0.2408	0.2376	0.073*
H2B	1.0171	0.2089	0.1847	0.073*
C3	0.9073 (3)	0.24950 (13)	0.0128 (3)	0.0479 (7)
H3	0.8118	0.2572	−0.0061	0.057*
C4	0.9659 (3)	0.20881 (14)	−0.1165 (3)	0.0494 (7)
H4	1.0612	0.2021	−0.0953	0.059*
C5	0.9012 (3)	0.13521 (15)	−0.1183 (4)	0.0633 (9)
H5A	0.8066	0.1399	−0.1405	0.076*
H5B	0.9417	0.1071	−0.1966	0.076*
C6	0.9178 (3)	0.09692 (14)	0.0308 (4)	0.0694 (9)
H6A	0.8732	0.0514	0.0259	0.083*
H6B	1.0122	0.0885	0.0490	0.083*
C7	0.8786 (5)	0.10092 (19)	0.3060 (5)	0.1305 (18)
H7A	0.8379	0.0550	0.3005	0.196*
H7B	0.8371	0.1278	0.3841	0.196*
H7C	0.9724	0.0958	0.3268	0.196*
C8	0.9561 (3)	0.24793 (17)	−0.2669 (3)	0.0649 (9)
H8	0.9846	0.2967	−0.2479	0.078*
C9	0.8146 (3)	0.2525 (2)	−0.3295 (4)	0.0916 (12)
H9A	0.8159	0.2785	−0.4214	0.137*
H9B	0.7577	0.2762	−0.2592	0.137*
H9C	0.7811	0.2057	−0.3473	0.137*
C10	1.0536 (4)	0.2180 (2)	−0.3807 (4)	0.0975 (12)
H10A	1.1426	0.2190	−0.3404	0.146*
H10B	1.0505	0.2461	−0.4698	0.146*
H10C	1.0293	0.1701	−0.4037	0.146*
C11	0.8768 (3)	0.41490 (14)	0.2192 (3)	0.0553 (8)
C12	0.9730 (3)	0.39822 (16)	0.3243 (4)	0.0703 (9)
H12	1.0529	0.3774	0.2941	0.084*
C13	0.9515 (5)	0.41225 (17)	0.4747 (4)	0.0896 (11)
H13	1.0163	0.4012	0.5454	0.108*
C14	0.8321 (5)	0.4428 (2)	0.5164 (5)	0.0997 (13)
H14	0.8155	0.4510	0.6169	0.120*
C15	0.7377 (4)	0.4614 (2)	0.4142 (5)	0.0967 (13)
H15	0.6592	0.4836	0.4444	0.116*
C16	0.7594 (3)	0.44701 (18)	0.2661 (4)	0.0765 (10)
H16	0.6944	0.4590	0.1963	0.092*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0510 (4)	0.0433 (4)	0.0622 (6)	−0.0001 (3)	0.0007 (4)	−0.0039 (4)
S1	0.0600 (5)	0.0421 (4)	0.0685 (6)	0.0028 (4)	0.0114 (4)	−0.0015 (4)
O1	0.0520 (10)	0.0356 (10)	0.0714 (14)	−0.0035 (8)	−0.0013 (10)	−0.0056 (10)
O2	0.0521 (12)	0.0702 (13)	0.0800 (17)	0.0056 (10)	−0.0127 (11)	−0.0062 (14)
C1	0.081 (3)	0.057 (2)	0.070 (2)	−0.0237 (17)	−0.0024 (19)	0.002 (2)
C2	0.069 (2)	0.0560 (19)	0.057 (2)	−0.0117 (16)	−0.0014 (16)	−0.0027 (17)
C3	0.0434 (14)	0.0371 (14)	0.063 (2)	−0.0067 (12)	−0.0046 (15)	−0.0061 (15)
C4	0.0423 (16)	0.0451 (16)	0.061 (2)	0.0016 (14)	−0.0003 (15)	−0.0056 (15)
C5	0.065 (2)	0.0479 (19)	0.076 (2)	−0.0032 (16)	0.0040 (19)	−0.0192 (18)
C6	0.0625 (19)	0.0420 (17)	0.104 (3)	−0.0090 (15)	−0.011 (2)	0.003 (2)
C7	0.202 (5)	0.096 (3)	0.093 (3)	−0.056 (4)	−0.014 (3)	0.035 (3)
C8	0.076 (2)	0.060 (2)	0.059 (2)	−0.0048 (19)	−0.0015 (19)	−0.0016 (18)
C9	0.082 (3)	0.114 (3)	0.079 (3)	0.001 (2)	−0.016 (2)	0.018 (3)
C10	0.092 (3)	0.131 (3)	0.070 (2)	0.004 (2)	0.025 (2)	−0.004 (2)
C11	0.059 (2)	0.0455 (18)	0.061 (2)	−0.0014 (16)	0.0015 (17)	0.0014 (15)
C12	0.088 (2)	0.058 (2)	0.065 (2)	0.0027 (19)	0.001 (2)	−0.0030 (19)
C13	0.128 (3)	0.074 (2)	0.066 (3)	0.000 (2)	−0.009 (3)	0.003 (2)
C14	0.139 (4)	0.086 (3)	0.074 (3)	−0.011 (3)	0.031 (3)	−0.012 (3)
C15	0.096 (3)	0.104 (3)	0.090 (4)	0.009 (3)	0.030 (3)	−0.028 (3)
C16	0.072 (2)	0.075 (2)	0.082 (3)	0.009 (2)	0.0082 (19)	−0.017 (2)

Geometric parameters (Å, º) top

P1—O2	1.4583 (19)	C7—H7A	0.9600
P1—O1	1.5817 (17)	C7—H7B	0.9600
P1—C11	1.781 (3)	C7—H7C	0.9600
P1—S1	2.1083 (10)	C8—C10	1.520 (4)
S1—S1ⁱ	2.0703 (14)	C8—C9	1.524 (4)
O1—C3	1.484 (3)	C8—H8	0.9800
C1—C6	1.505 (4)	C9—H9A	0.9600
C1—C2	1.524 (4)	C9—H9B	0.9600
C1—C7	1.528 (4)	C9—H9C	0.9600
C1—H1	0.9800	C10—H10A	0.9600
C2—C3	1.505 (4)	C10—H10B	0.9600
C2—H2A	0.9700	C10—H10C	0.9600
C2—H2B	0.9700	C11—C12	1.383 (4)
C3—C4	1.510 (4)	C11—C16	1.387 (4)
C3—H3	0.9800	C12—C13	1.392 (5)
C4—C5	1.535 (4)	C12—H12	0.9300
C4—C8	1.542 (4)	C13—C14	1.378 (5)
C4—H4	0.9800	C13—H13	0.9300
C5—C6	1.530 (4)	C14—C15	1.361 (5)
C5—H5A	0.9700	C14—H14	0.9300
C5—H5B	0.9700	C15—C16	1.374 (5)
C6—H6A	0.9700	C15—H15	0.9300
C6—H6B	0.9700	C16—H16	0.9300

O2—P1—O1	117.31 (11)	H6A—C6—H6B	108.0
O2—P1—C11	112.74 (14)	C1—C7—H7A	109.5
O1—P1—C11	107.23 (13)	C1—C7—H7B	109.5
O2—P1—S1	113.30 (10)	H7A—C7—H7B	109.5
O1—P1—S1	95.12 (7)	C1—C7—H7C	109.5
C11—P1—S1	109.70 (10)	H7A—C7—H7C	109.5
S1ⁱ—S1—P1	96.96 (5)	H7B—C7—H7C	109.5
C3—O1—P1	122.78 (15)	C10—C8—C9	111.6 (3)
C6—C1—C2	110.0 (3)	C10—C8—C4	111.7 (3)
C6—C1—C7	111.2 (3)	C9—C8—C4	114.1 (3)
C2—C1—C7	111.6 (3)	C10—C8—H8	106.3
C6—C1—H1	107.9	C9—C8—H8	106.3
C2—C1—H1	107.9	C4—C8—H8	106.3
C7—C1—H1	107.9	C8—C9—H9A	109.5
C3—C2—C1	111.3 (2)	C8—C9—H9B	109.5
C3—C2—H2A	109.4	H9A—C9—H9B	109.5
C1—C2—H2A	109.4	C8—C9—H9C	109.5
C3—C2—H2B	109.4	H9A—C9—H9C	109.5
C1—C2—H2B	109.4	H9B—C9—H9C	109.5
H2A—C2—H2B	108.0	C8—C10—H10A	109.5
O1—C3—C2	108.1 (2)	C8—C10—H10B	109.5
O1—C3—C4	108.8 (2)	H10A—C10—H10B	109.5
C2—C3—C4	113.7 (2)	C8—C10—H10C	109.5
O1—C3—H3	108.7	H10A—C10—H10C	109.5
C2—C3—H3	108.7	H10B—C10—H10C	109.5
C4—C3—H3	108.7	C12—C11—C16	118.8 (3)
C3—C4—C5	107.9 (2)	C12—C11—P1	121.8 (2)
C3—C4—C8	113.8 (2)	C16—C11—P1	119.3 (3)
C5—C4—C8	113.5 (3)	C11—C12—C13	120.6 (3)
C3—C4—H4	107.1	C11—C12—H12	119.7
C5—C4—H4	107.1	C13—C12—H12	119.7
C8—C4—H4	107.1	C14—C13—C12	118.5 (4)
C6—C5—C4	112.0 (2)	C14—C13—H13	120.7
C6—C5—H5A	109.2	C12—C13—H13	120.7
C4—C5—H5A	109.2	C15—C14—C13	121.6 (4)
C6—C5—H5B	109.2	C15—C14—H14	119.2
C4—C5—H5B	109.2	C13—C14—H14	119.2
H5A—C5—H5B	107.9	C14—C15—C16	119.5 (4)
C1—C6—C5	111.6 (2)	C14—C15—H15	120.3
C1—C6—H6A	109.3	C16—C15—H15	120.3
C5—C6—H6A	109.3	C15—C16—C11	120.9 (4)
C1—C6—H6B	109.3	C15—C16—H16	119.6
C5—C6—H6B	109.3	C11—C16—H16	119.6

O2—P1—S1—S1ⁱ	56.22 (9)	C4—C5—C6—C1	57.2 (3)
O1—P1—S1—S1ⁱ	178.92 (8)	C3—C4—C8—C10	161.2 (3)
C11—P1—S1—S1ⁱ	−70.73 (11)	C5—C4—C8—C10	−74.9 (3)
O2—P1—O1—C3	−33.0 (3)	C3—C4—C8—C9	−71.2 (3)
C11—P1—O1—C3	95.0 (2)	C5—C4—C8—C9	52.8 (4)
S1—P1—O1—C3	−152.5 (2)	O2—P1—C11—C12	163.5 (2)
C6—C1—C2—C3	54.6 (4)	O1—P1—C11—C12	32.9 (3)
C7—C1—C2—C3	178.6 (3)	S1—P1—C11—C12	−69.2 (3)
P1—O1—C3—C2	−108.6 (2)	O2—P1—C11—C16	−12.7 (3)
P1—O1—C3—C4	127.4 (2)	O1—P1—C11—C16	−143.3 (2)
C1—C2—C3—O1	−177.8 (2)	S1—P1—C11—C16	114.6 (2)
C1—C2—C3—C4	−56.8 (3)	C16—C11—C12—C13	1.1 (5)
O1—C3—C4—C5	176.3 (2)	P1—C11—C12—C13	−175.1 (2)
C2—C3—C4—C5	55.8 (3)	C11—C12—C13—C14	0.2 (5)
O1—C3—C4—C8	−56.8 (3)	C12—C13—C14—C15	−2.1 (6)
C2—C3—C4—C8	−177.3 (2)	C13—C14—C15—C16	2.5 (7)
C3—C4—C5—C6	−55.2 (3)	C14—C15—C16—C11	−1.0 (6)
C8—C4—C5—C6	177.7 (3)	C12—C11—C16—C15	−0.8 (5)
C2—C1—C6—C5	−55.2 (3)	P1—C11—C16—C15	175.5 (3)
C7—C1—C6—C5	−179.5 (3)

Symmetry code: (i) −x+2, −y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6B···O2ⁱⁱ	0.97	2.59	3.527 (3)	162

Symmetry code: (ii) x+1/2, −y+1/2, −z.

Experimental details

Crystal data
Chemical formula	C₃₂H₄₈O₄P₂S₂
M_r	622.76
Crystal system, space group	Orthorhombic, P2₁2₁2
Temperature (K)	298
a, b, c (Å)	9.9910 (9), 18.9100 (17), 8.9747 (7)
V (Å³)	1695.6 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.40 × 0.28 × 0.16

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.895, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	7818, 2989, 2141
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.080, 0.91
No. of reflections	2989
No. of parameters	184
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.16
Absolute structure	Flack (1983), 1736 Friedel pairs
Absolute structure parameter	−0.10 (10)

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), 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
C6—H6B···O2ⁱ	0.97	2.59	3.527 (3)	161.6

Symmetry code: (i) x+1/2, −y+1/2, −z.

Acknowledgements

We acknowledge financial support by the Natural Science Foundation of China (No. 20772055).

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Perlikowska, W. & Daran, I. C. (2004). Tetrahedron Asymmetry, 15, 3519–3529. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar