(Dimethyl sulfoxide-κO)[3-hydr­oxy-2-hydroxy­methyl-2-(3-meth­oxy-2-oxido­benzyl­ideneamino-κ2O2,N)propanolato-κO]dioxomolybdenum(VI). Corrigendum

Sui, Y.; Fang, X.-N.; Luo, Q.-Y.; Chen, H.-M.; Zhou, M.-Q.

doi:10.1107/S1600536810007476

addenda and errata

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page e23

https://doi.org/10.1107/S1600536810007476

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(Dimethyl sulfoxide-κO)[3-hydroxy-2-hydroxymethyl-2-(3-methoxy-2-oxidobenzylideneamino-κ²O²,N)propanolato-κO]dioxomolybdenum(VI). Corrigendum

Yan Sui,^a Xiao-Niu Fang,^a ^* Qiu-Yan Luo,^a Hong-Mei Chen ^a and Meng-Qiang Zhou ^a

^aJiangXi Province Key Laboratory of Coordination Chemistry, College of Chemistry & Chemical Engineering, JingGangShan University, 343009 Ji'an, JiangXi, People's Republic of China
^*Correspondence e-mail: ysui@163.com

(Received 19 February 2010; accepted 26 February 2010; online 14 April 2010)

The crystal structure of the title compound in the paper by Sui, Fang, Luo, Chen & Zhou [Acta Cryst. (2006), E62, m1994–m1996] has been rerefined to allow for identification of a disordered dimethyl sulfoxide ligand.

The structure reported by Sui et al. (2006) has been rerefined. The compound was originally determined by Rao et al. [J. Chem. Soc. Dalton Trans. (1998), 2383] and has been redetermined here to a significantly higher precision of the lattice parameters [a = 14.3130 (7) Å, b = 9.2596 (5) Å and c = 14.8563 (7) Å here versus a = 14.305 (3) Å, b = 9.249 (2) Å and c = 14.860 (3) Å reported by Rao et al.], bond lengths and s.u. values [e.g. Mo1—O6 = 1.6937 (17) Å here versus Mo1—O6 1.697 (4) Å reported by Rao et al.; R = 0.022 here versus R = 0.050 reported by Rao et al.]. The results of the current redetermination allow the identification of a disordered dimethyl sulfoxide ligand and a clarification of the nature of the intra- and intermolecular hydrogen bonding.

2. Experimental

2.1.1. Crystal data

[Mo(C₁₂H₁₅NO₅)O₂(C₂H₆OS)]
M_r = 459.32
Monoclinic, P 2₁ /n
a = 14.3130 (7) Å
b = 9.2596 (5) Å
c = 14.8563 (7) Å
β = 115.324 (1)°
V = 1779.74 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.90 mm⁻¹
T = 295 K
0.56 × 0.39 × 0.35 mm

2.1.2. Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.632, T_max = 0.746
10668 measured reflections
3278 independent reflections
3056 reflections with I > 2σ(I)
R_int = 0.024

2.1.3. Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.064
S = 1.07
3278 reflections
259 parameters
40 restraints
H-atom parameters constrained
Δρ_max = 0.36 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
C1—H1⋯O5	0.93	2.22	2.874 (3)	127
C14—H14E⋯O7ⁱ	0.96	2.45	3.343 (4)	154
C8—H8A⋯O6ⁱⁱ	0.96	2.54	3.475 (4)	164
C11—H11A⋯O7ⁱⁱⁱ	0.97	2.57	3.534 (3)	170
O5—H5A⋯O1ⁱⁱⁱ	0.82	2.02	2.834 (2)	175
O5—H5A⋯O2ⁱⁱⁱ	0.82	2.53	2.970 (2)	115
O4—H4⋯O3^iv	0.82	1.99	2.801 (2)	171
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{5\over 2}}]$ ; (ii) x, y-1, z; (iii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iv) -x+1, -y+2, -z+2.

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: APEX2 (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL97 (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810007476/ng9064sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810007476/ng9064Isup2.hkl

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: APEX2 (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL97 (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

(Dimethyl sulfoxide-κO)[3-hydroxy-2-hydroxymethyl-2-(3-methoxy-2- oxidobenzylideneamino-κ²O²,N)propanolato-κO]dioxomolybdenum(VI) top

Crystal data top

[Mo(C₁₂H₁₅NO₅)O₂(C₂H₆OS)]	F(000) = 936
M_r = 459.32	D_x = 1.714 Mg m⁻³
Monoclinic, P2₁/n	Melting point = 454–456 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 14.3130 (7) Å	Cell parameters from 11097 reflections
b = 9.2596 (5) Å	θ = 2.6–26.0°
c = 14.8563 (7) Å	µ = 0.90 mm⁻¹
β = 115.324 (1)°	T = 295 K
V = 1779.74 (15) Å³	Block, yellow
Z = 4	0.56 × 0.39 × 0.35 mm

Data collection top

Bruker APEXII area-detector diffractometer	3278 independent reflections
Radiation source: fine-focus sealed tube	3056 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
φ and ω scan	θ_max = 25.5°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −17→16
T_min = 0.632, T_max = 0.746	k = −11→10
10668 measured reflections	l = −17→17

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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.064	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0347P)² + 0.9103P] where P = (F_o² + 2F_c²)/3
3278 reflections	(Δ/σ)_max = 0.002
259 parameters	Δρ_max = 0.36 e Å⁻³
40 restraints	Δρ_min = −0.44 e Å⁻³

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	Occ. (<1)
C1	0.61630 (15)	0.7171 (2)	0.82021 (14)	0.0306 (4)
H1	0.5551	0.7275	0.7628	0.037*
C2	0.67331 (15)	0.5841 (2)	0.83147 (14)	0.0296 (4)
C3	0.76286 (15)	0.5507 (2)	0.91746 (14)	0.0290 (4)
C4	0.81292 (15)	0.4178 (2)	0.92185 (15)	0.0320 (4)
C5	0.77698 (17)	0.3257 (2)	0.84100 (16)	0.0353 (5)
H5	0.8110	0.2390	0.8441	0.042*
C6	0.69022 (17)	0.3620 (2)	0.75494 (16)	0.0382 (5)
H6	0.6675	0.3005	0.7002	0.046*
C7	0.63806 (16)	0.4877 (2)	0.75039 (15)	0.0358 (5)
H7	0.5788	0.5097	0.6932	0.043*
C8	0.9572 (2)	0.2667 (3)	1.0142 (2)	0.0606 (8)
H8A	0.9176	0.1814	1.0104	0.091*
H8B	1.0184	0.2670	1.0760	0.091*
H8C	0.9764	0.2679	0.9597	0.091*
C9	0.57775 (15)	0.9537 (2)	0.85896 (14)	0.0315 (4)
C10	0.64007 (17)	1.0616 (2)	0.94075 (15)	0.0370 (5)
H10A	0.6914	1.1084	0.9242	0.044*
H10B	0.5944	1.1355	0.9457	0.044*
C11	0.47619 (16)	0.9150 (2)	0.86463 (17)	0.0376 (5)
H11A	0.4393	0.8422	0.8152	0.045*
H11B	0.4904	0.8766	0.9300	0.045*
C12	0.55921 (17)	1.0195 (2)	0.75826 (15)	0.0379 (5)
H12A	0.5287	1.1146	0.7523	0.045*
H12B	0.6247	1.0302	0.7542	0.045*
Mo1	0.779330 (13)	0.829629 (19)	1.036557 (12)	0.03081 (8)
N1	0.64298 (13)	0.82184 (17)	0.88262 (12)	0.0280 (3)
O1	0.89683 (12)	0.39109 (19)	1.00918 (11)	0.0467 (4)
O2	0.80380 (11)	0.63679 (17)	0.99656 (10)	0.0384 (3)
O3	0.68969 (11)	0.98850 (16)	1.03313 (10)	0.0350 (3)
O4	0.41554 (14)	1.0420 (2)	0.84657 (14)	0.0535 (4)
H4	0.3791	1.0373	0.8766	0.080*
O5	0.49290 (16)	0.9313 (2)	0.67962 (12)	0.0589 (5)
H5A	0.4619	0.9810	0.6300	0.088*
O6	0.85527 (13)	0.92141 (19)	0.99470 (13)	0.0498 (4)
O7	0.84674 (14)	0.82180 (19)	1.16266 (12)	0.0506 (4)
O8	0.65402 (13)	0.69377 (18)	1.06088 (12)	0.0463 (4)
C13	0.7091 (3)	0.4309 (4)	1.1317 (3)	0.0645 (9)	0.9402 (18)
H13D	0.6536	0.3982	1.0710	0.077*	0.9402 (18)
H13E	0.7147	0.3685	1.1854	0.077*	0.9402 (18)
H13F	0.7727	0.4291	1.1247	0.077*	0.9402 (18)
C14	0.5638 (3)	0.5787 (5)	1.1629 (3)	0.0811 (10)	0.9402 (18)
H14D	0.5338	0.6697	1.1671	0.097*	0.9402 (18)
H14E	0.5749	0.5216	1.2205	0.097*	0.9402 (18)
H14F	0.5179	0.5285	1.1040	0.097*	0.9402 (18)
C13A	0.662 (5)	0.419 (7)	1.110 (4)	0.056 (6)	0.0598 (18)
H13A	0.6969	0.4216	1.0676	0.068*	0.0598 (18)
H13B	0.6114	0.3433	1.0892	0.068*	0.0598 (18)
H13C	0.7112	0.4022	1.1776	0.068*	0.0598 (18)
C14A	0.630 (4)	0.631 (6)	1.219 (4)	0.059 (4)	0.0598 (18)
H14A	0.6970	0.5990	1.2657	0.071*	0.0598 (18)
H14B	0.5784	0.5938	1.2383	0.071*	0.0598 (18)
H14C	0.6276	0.7345	1.2184	0.071*	0.0598 (18)
S1	0.68357 (6)	0.60903 (8)	1.15748 (5)	0.0488 (2)	0.9402 (18)
S1A	0.6059 (10)	0.5697 (14)	1.1039 (9)	0.060 (2)	0.0598 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0303 (10)	0.0313 (11)	0.0266 (9)	−0.0003 (8)	0.0087 (8)	0.0030 (8)
C2	0.0318 (10)	0.0281 (10)	0.0271 (9)	−0.0020 (8)	0.0109 (8)	−0.0002 (8)
C3	0.0321 (9)	0.0269 (10)	0.0269 (9)	−0.0024 (8)	0.0117 (8)	−0.0043 (8)
C4	0.0308 (10)	0.0318 (11)	0.0305 (10)	0.0006 (8)	0.0103 (8)	−0.0035 (8)
C5	0.0393 (11)	0.0292 (12)	0.0380 (11)	0.0002 (8)	0.0172 (9)	−0.0064 (8)
C6	0.0452 (12)	0.0334 (12)	0.0323 (11)	−0.0064 (9)	0.0132 (9)	−0.0115 (9)
C7	0.0364 (11)	0.0349 (12)	0.0287 (10)	−0.0050 (9)	0.0069 (8)	−0.0028 (9)
C8	0.0528 (15)	0.0461 (16)	0.0591 (16)	0.0222 (12)	0.0011 (12)	−0.0087 (13)
C9	0.0351 (10)	0.0262 (10)	0.0321 (10)	0.0046 (8)	0.0133 (8)	0.0039 (8)
C10	0.0439 (12)	0.0265 (11)	0.0379 (11)	0.0037 (9)	0.0150 (9)	0.0025 (9)
C11	0.0373 (11)	0.0373 (12)	0.0394 (11)	0.0064 (9)	0.0176 (9)	0.0053 (9)
C12	0.0444 (12)	0.0319 (12)	0.0356 (11)	0.0045 (9)	0.0154 (9)	0.0078 (9)
Mo1	0.03081 (12)	0.02818 (12)	0.02761 (12)	0.00253 (6)	0.00691 (8)	−0.00596 (6)
N1	0.0285 (8)	0.0256 (9)	0.0286 (8)	0.0023 (6)	0.0110 (7)	0.0026 (6)
O1	0.0446 (9)	0.0392 (9)	0.0382 (8)	0.0160 (7)	0.0006 (7)	−0.0099 (7)
O2	0.0379 (8)	0.0342 (8)	0.0292 (7)	0.0085 (6)	0.0012 (6)	−0.0102 (6)
O3	0.0410 (8)	0.0293 (8)	0.0324 (7)	0.0061 (6)	0.0135 (6)	−0.0027 (6)
O4	0.0528 (10)	0.0543 (11)	0.0618 (11)	0.0231 (8)	0.0326 (9)	0.0136 (9)
O5	0.0757 (12)	0.0455 (11)	0.0326 (8)	−0.0047 (9)	0.0014 (8)	0.0095 (7)
O6	0.0439 (9)	0.0449 (10)	0.0640 (11)	−0.0054 (7)	0.0264 (8)	−0.0097 (8)
O7	0.0563 (10)	0.0460 (11)	0.0318 (8)	0.0119 (7)	0.0021 (7)	−0.0098 (7)
O8	0.0544 (9)	0.0405 (9)	0.0445 (9)	0.0027 (7)	0.0215 (8)	0.0132 (7)
C13	0.077 (2)	0.0439 (13)	0.071 (2)	0.0125 (18)	0.0298 (19)	0.0151 (15)
C14	0.0865 (18)	0.083 (2)	0.095 (2)	0.0244 (18)	0.059 (2)	0.043 (2)
C13A	0.069 (9)	0.049 (9)	0.050 (9)	0.002 (9)	0.025 (8)	0.014 (8)
C14A	0.071 (5)	0.057 (5)	0.058 (5)	0.007 (5)	0.036 (5)	0.024 (5)
S1	0.0633 (4)	0.0416 (4)	0.0375 (3)	−0.0005 (3)	0.0177 (3)	0.0088 (3)
S1A	0.068 (3)	0.053 (3)	0.054 (3)	0.003 (3)	0.022 (3)	0.015 (3)

Geometric parameters (Å, º) top

C1—N1	1.282 (3)	C12—H12A	0.9700
C1—C2	1.448 (3)	C12—H12B	0.9700
C1—H1	0.9300	Mo1—O6	1.6937 (17)
C2—C3	1.403 (3)	Mo1—O7	1.7028 (16)
C2—C7	1.407 (3)	Mo1—O3	1.9383 (14)
C3—O2	1.331 (2)	Mo1—O2	1.9602 (15)
C3—C4	1.411 (3)	Mo1—N1	2.2861 (17)
C4—O1	1.362 (2)	Mo1—O8	2.3419 (17)
C4—C5	1.381 (3)	O4—H4	0.8200
C5—C6	1.390 (3)	O5—H5A	0.8200
C5—H5	0.9300	O8—S1	1.5280 (17)
C6—C7	1.369 (3)	O8—S1A	1.606 (12)
C6—H6	0.9300	C13—S1	1.767 (4)
C7—H7	0.9300	C13—H13D	0.9600
C8—O1	1.422 (3)	C13—H13E	0.9600
C8—H8A	0.9600	C13—H13F	0.9600
C8—H8B	0.9600	C14—S1	1.772 (4)
C8—H8C	0.9600	C14—H14D	0.9600
C9—N1	1.485 (2)	C14—H14E	0.9600
C9—C12	1.530 (3)	C14—H14F	0.9600
C9—C10	1.531 (3)	C13A—S1A	1.59 (6)
C9—C11	1.534 (3)	C13A—H13A	0.9600
C10—O3	1.419 (2)	C13A—H13B	0.9600
C10—H10A	0.9700	C13A—H13C	0.9600
C10—H10B	0.9700	C14A—S1A	1.69 (5)
C11—O4	1.417 (3)	C14A—H14A	0.9600
C11—H11A	0.9700	C14A—H14B	0.9600
C11—H11B	0.9700	C14A—H14C	0.9600
C12—O5	1.409 (3)

N1—C1—C2	125.56 (18)	O5—C12—H12B	109.5
N1—C1—H1	117.2	C9—C12—H12B	109.5
C2—C1—H1	117.2	H12A—C12—H12B	108.1
C3—C2—C7	119.53 (19)	O6—Mo1—O7	105.95 (9)
C3—C2—C1	122.88 (18)	O6—Mo1—O3	97.53 (7)
C7—C2—C1	117.55 (18)	O7—Mo1—O3	96.80 (7)
O2—C3—C2	123.88 (18)	O6—Mo1—O2	96.88 (8)
O2—C3—C4	117.29 (17)	O7—Mo1—O2	101.78 (7)
C2—C3—C4	118.83 (18)	O3—Mo1—O2	152.32 (6)
O1—C4—C5	124.42 (19)	O6—Mo1—N1	93.20 (7)
O1—C4—C3	115.21 (17)	O7—Mo1—N1	159.85 (8)
C5—C4—C3	120.36 (19)	O3—Mo1—N1	74.06 (6)
C4—C5—C6	120.3 (2)	O2—Mo1—N1	81.65 (6)
C4—C5—H5	119.8	O6—Mo1—O8	168.61 (7)
C6—C5—H5	119.8	O7—Mo1—O8	85.31 (8)
C7—C6—C5	120.31 (19)	O3—Mo1—O8	82.51 (6)
C7—C6—H6	119.8	O2—Mo1—O8	78.78 (7)
C5—C6—H6	119.8	N1—Mo1—O8	75.82 (6)
C6—C7—C2	120.55 (19)	C1—N1—C9	119.23 (17)
C6—C7—H7	119.7	C1—N1—Mo1	127.61 (14)
C2—C7—H7	119.7	C9—N1—Mo1	113.08 (12)
O1—C8—H8A	109.5	C4—O1—C8	117.75 (18)
O1—C8—H8B	109.5	C3—O2—Mo1	138.18 (13)
H8A—C8—H8B	109.5	C10—O3—Mo1	116.08 (12)
O1—C8—H8C	109.5	C11—O4—H4	109.5
H8A—C8—H8C	109.5	C12—O5—H5A	109.5
H8B—C8—H8C	109.5	S1—O8—S1A	41.6 (5)
N1—C9—C12	112.79 (16)	S1—O8—Mo1	119.88 (10)
N1—C9—C10	104.78 (15)	S1A—O8—Mo1	158.9 (5)
C12—C9—C10	108.35 (17)	S1A—C13A—H13A	109.5
N1—C9—C11	108.02 (16)	S1A—C13A—H13B	109.5
C12—C9—C11	112.00 (17)	H13A—C13A—H13B	109.5
C10—C9—C11	110.68 (17)	S1A—C13A—H13C	109.5
O3—C10—C9	109.68 (17)	H13A—C13A—H13C	109.5
O3—C10—H10A	109.7	H13B—C13A—H13C	109.5
C9—C10—H10A	109.7	S1A—C14A—H14A	109.5
O3—C10—H10B	109.7	S1A—C14A—H14B	109.5
C9—C10—H10B	109.7	H14A—C14A—H14B	109.5
H10A—C10—H10B	108.2	S1A—C14A—H14C	109.5
O4—C11—C9	108.29 (18)	H14A—C14A—H14C	109.5
O4—C11—H11A	110.0	H14B—C14A—H14C	109.5
C9—C11—H11A	110.0	O8—S1—C13	106.01 (15)
O4—C11—H11B	110.0	O8—S1—C14	103.85 (14)
C9—C11—H11B	110.0	C13—S1—C14	98.9 (2)
H11A—C11—H11B	108.4	C13A—S1A—O8	111 (2)
O5—C12—C9	110.72 (18)	C13A—S1A—C14A	111 (3)
O5—C12—H12A	109.5	O8—S1A—C14A	103 (2)
C9—C12—H12A	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O4	0.97	2.50	2.911 (3)	105
C1—H1···O5	0.93	2.22	2.874 (3)	127
C14—H14E···O7ⁱ	0.96	2.45	3.343 (4)	154
C8—H8A···O6ⁱⁱ	0.96	2.54	3.475 (4)	164
C11—H11A···O7ⁱⁱⁱ	0.97	2.57	3.534 (3)	170
O5—H5A···O1ⁱⁱⁱ	0.82	2.02	2.834 (2)	175
O5—H5A···O2ⁱⁱⁱ	0.82	2.53	2.970 (2)	115
O4—H4···O3^iv	0.82	1.99	2.801 (2)	171

Symmetry codes: (i) −x+3/2, y−1/2, −z+5/2; (ii) x, y−1, z; (iii) x−1/2, −y+3/2, z−1/2; (iv) −x+1, −y+2, −z+2.

References

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