Bis{μ-N-[bis­(hydroxy­methyl)(oxidomethyl)methyl]glycinato}bis[dimethyl­tin(IV)] dioxane hemisolvate

The title complex, [Sn₂(CH₃)₄(C₆H₁₁NO₅)₂]·0.5C₄H₈O₂, comprises the centrosymmetric cyclic dimeric Sn^IV complex and an uncoordinated, partially occupied, centrosymmetric dioxane mol­ecule. Each Sn^IV atom has a distorted octa­hedral six-coordinate configuration formed by the tridentate tricine ligand, one bridging O atom and two methyl groups. Within the cyclic dimer, the Sn...Sn separation is 3.6574 (4) Å. All H atoms of the NH and OH groups are involved in inter­molecular hydrogen bonds with the O atoms as acceptors. There are also important weak inter­molecular C—H...O hydrogen bonds, which link the mol­ecules of the dimer and dioxane into an infinite three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in solvent or counterion
• R factor = 0.027
• wR factor = 0.088
• Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT411_ALERT_2_B Short Inter H...H Contact  H6B    ..  H10A    ..       1.98 Ang.
PLAT411_ALERT_2_B Short Inter H...H Contact  H6B    ..  H10B    ..       2.00 Ang.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         C9
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........         O6
PLAT413_ALERT_2_C Short Inter XH3 .. XHn     H1A    ..  H9A     ..       2.11 Ang.

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

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

Bis{µ-N-[bis(hydroxymethyl)(oxidomethyl)methyl]glycinato}[dimethyltin(IV)] dioxane hemisolvate

Crystal data

[Sn2(CH3)4(C6H11NO5)2]·0.5C4H8O2	F(000) = 696
Mr = 695.88	Dx = 1.764 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 11611 reflections
a = 8.1343 (4) Å	θ = 2.1–25.1°
b = 8.3520 (4) Å	µ = 1.96 mm^−1
c = 19.3060 (9) Å	T = 296 K
β = 92.615 (1)°	Block, white
V = 1310.24 (11) Å^3	0.37 × 0.27 × 0.14 mm
Z = 2

Data collection

Bruker APEX-II area-detector diffractometer	2325 independent reflections
Radiation source: fine-focus sealed tube	2198 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
φ and ω scans	θmax = 25.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→9
Tmin = 0.476, Tmax = 0.760	k = −9→9
11611 measured reflections	l = −23→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.088	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.058P)^2 + 3.0289P] where P = (Fo^2 + 2Fc^2)/3
2325 reflections	(Δ/σ)max = 0.001
167 parameters	Δρmax = 0.94 e Å^−3
3 restraints	Δρmin = −0.59 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Sn1	1.09451 (3)	1.09214 (3)	0.077980 (12)	0.02747 (13)
N1	1.0453 (4)	0.9515 (4)	0.17638 (15)	0.0263 (6)
H1	1.1416	0.9010	0.1884	0.032*
O1	1.2258 (4)	1.2148 (4)	0.18420 (15)	0.0419 (7)
O2	1.1459 (4)	1.2845 (4)	0.28882 (16)	0.0461 (8)
O3	0.9592 (4)	0.8964 (3)	0.04185 (13)	0.0303 (6)
O4	0.6356 (4)	0.7689 (4)	0.13439 (19)	0.0512 (8)
H4	0.5450	0.7813	0.1506	0.077*
O5	0.9288 (4)	0.7187 (4)	0.28071 (15)	0.0465 (8)
H5	1.0194	0.7144	0.3010	0.070*
O6	0.4159 (18)	0.5078 (17)	0.0494 (9)	0.182 (9)	0.50
C1	0.9348 (7)	1.2906 (6)	0.0831 (3)	0.0535 (13)
H1A	0.8315	1.2655	0.0596	0.080*
H1B	0.9832	1.3813	0.0614	0.080*
H1C	0.9171	1.3152	0.1308	0.080*
C2	1.3360 (5)	1.0323 (7)	0.0565 (3)	0.0491 (11)
H2A	1.3420	0.9202	0.0460	0.074*
H2B	1.4074	1.0559	0.0961	0.074*
H2C	1.3695	1.0933	0.0174	0.074*
C3	1.1392 (5)	1.1987 (5)	0.2358 (2)	0.0333 (8)
C4	1.0154 (5)	1.0620 (5)	0.2339 (2)	0.0359 (9)
H4A	1.0238	1.0041	0.2775	0.043*
H4B	0.9048	1.1052	0.2283	0.043*
C5	0.9226 (4)	0.8203 (4)	0.16089 (18)	0.0261 (7)
C6	0.9582 (5)	0.7635 (4)	0.08794 (19)	0.0288 (8)
H6A	1.0641	0.7100	0.0886	0.035*
H6B	0.8746	0.6874	0.0720	0.035*
C7	0.7471 (5)	0.8870 (5)	0.1626 (2)	0.0351 (9)
H7A	0.7209	0.9116	0.2100	0.042*
H7B	0.7379	0.9846	0.1355	0.042*
C8	0.9439 (5)	0.6769 (5)	0.21021 (19)	0.0338 (8)
H8A	0.8619	0.5966	0.1975	0.041*
H8B	1.0515	0.6298	0.2046	0.041*
C9	0.5792 (19)	0.449 (2)	0.0573 (10)	0.112 (6)	0.50
H9A	0.5832	0.3358	0.0456	0.134*	0.50
H9B	0.6219	0.4626	0.1047	0.134*	0.50
C10	0.6767 (17)	0.546 (2)	0.0080 (6)	0.092 (5)	0.50
H10A	0.6670	0.6609	0.0153	0.111*	0.50
H10B	0.7915	0.5152	0.0076	0.111*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.03393 (19)	0.02176 (18)	0.02725 (18)	0.00058 (9)	0.00722 (11)	0.00122 (9)
N1	0.0289 (15)	0.0240 (15)	0.0264 (15)	0.0014 (13)	0.0049 (12)	−0.0010 (13)
O1	0.0489 (17)	0.0431 (17)	0.0339 (15)	−0.0145 (14)	0.0056 (13)	−0.0032 (13)
O2	0.0430 (17)	0.0516 (19)	0.0441 (17)	−0.0070 (14)	0.0075 (13)	−0.0233 (15)
O3	0.0476 (16)	0.0233 (14)	0.0203 (13)	−0.0064 (11)	0.0044 (11)	0.0033 (10)
O4	0.0361 (16)	0.057 (2)	0.061 (2)	−0.0075 (15)	0.0077 (14)	−0.0009 (17)
O5	0.0591 (19)	0.0548 (19)	0.0261 (14)	−0.0055 (16)	0.0084 (13)	0.0107 (14)
O6	0.147 (13)	0.103 (10)	0.28 (2)	−0.040 (10)	−0.136 (14)	0.047 (13)
C1	0.081 (4)	0.037 (2)	0.042 (2)	0.024 (2)	0.004 (2)	−0.006 (2)
C2	0.035 (2)	0.067 (3)	0.046 (2)	0.009 (2)	0.0087 (18)	−0.004 (2)
C3	0.035 (2)	0.035 (2)	0.0296 (19)	0.0019 (17)	0.0021 (15)	−0.0054 (16)
C4	0.044 (2)	0.038 (2)	0.0259 (19)	−0.0046 (18)	0.0126 (17)	−0.0092 (16)
C5	0.0304 (18)	0.0237 (18)	0.0245 (17)	−0.0002 (14)	0.0052 (14)	0.0005 (14)
C6	0.0358 (19)	0.0212 (18)	0.0298 (19)	−0.0015 (15)	0.0066 (15)	0.0015 (14)
C7	0.034 (2)	0.036 (2)	0.036 (2)	−0.0014 (17)	0.0078 (17)	0.0011 (17)
C8	0.040 (2)	0.033 (2)	0.0286 (19)	−0.0027 (17)	0.0036 (16)	0.0057 (16)
C9	0.118 (16)	0.097 (12)	0.121 (14)	0.000 (11)	0.022 (12)	−0.018 (12)
C10	0.071 (9)	0.141 (14)	0.065 (8)	0.017 (9)	0.010 (7)	−0.001 (9)

Geometric parameters (Å, º)

Sn1—C1	2.111 (4)	C2—H2A	0.9600
Sn1—C2	2.087 (4)	C2—H2B	0.9600
Sn1—N1	2.284 (3)	C2—H2C	0.9600
Sn1—O1	2.489 (3)	C3—C4	1.521 (6)
Sn1—O3	2.074 (3)	C4—H4A	0.9700
Sn1—O3^i	2.337 (3)	C4—H4B	0.9700
N1—C4	1.473 (5)	C5—C6	1.526 (5)
N1—C5	1.503 (5)	C5—C7	1.534 (5)
N1—H1	0.9100	C5—C8	1.535 (5)
O1—C3	1.253 (5)	C6—H6A	0.9700
O2—C3	1.249 (5)	C6—H6B	0.9700
O3—C6	1.423 (4)	C7—H7A	0.9700
O4—C7	1.431 (5)	C7—H7B	0.9700
O4—H4	0.8200	C8—H8A	0.9700
O5—C8	1.416 (5)	C8—H8B	0.9700
O5—H5	0.8200	C9—C10	1.508 (10)
O6—C10^ii	1.386 (9)	C9—H9A	0.9700
O6—C9	1.419 (10)	C9—H9B	0.9700
C1—H1A	0.9600	C10—H10A	0.9700
C1—H1B	0.9600	C10—H10B	0.9700
C1—H1C	0.9600
C2—Sn1—C1	141.7 (2)	C1—Sn1—O3^i	85.81 (15)
Sn1—C1—H1A	109.5	C2—Sn1—N1	104.16 (17)
Sn1—C1—H1B	109.5	C2—Sn1—O1	83.70 (16)
Sn1—C1—H1C	109.5	C2—Sn1—O3^i	87.02 (15)
Sn1—C2—H2A	109.5	C3—C4—H4A	109.5
Sn1—C2—H2B	109.5	C3—C4—H4B	109.5
Sn1—C2—H2C	109.5	C3—O1—Sn1	112.0 (3)
Sn1—N1—H1	105.6	C4—N1—C5	118.4 (3)
N1—Sn1—O1	67.12 (10)	C4—N1—H1	105.6
N1—Sn1—O3^i	144.34 (10)	C4—N1—Sn1	110.3 (2)
N1—C4—C3	110.8 (3)	C5—C6—H6A	109.7
N1—C4—H4A	109.5	C5—C6—H6B	109.7
N1—C4—H4B	109.5	C5—C7—H7A	110.0
N1—C5—C6	105.0 (3)	C5—C7—H7B	110.0
N1—C5—C7	109.9 (3)	C5—C8—H8A	109.0
N1—C5—C8	113.0 (3)	C5—C8—H8B	109.0
O1—C3—C4	117.2 (3)	C5—N1—H1	105.6
O2—C3—C4	117.0 (4)	C5—N1—Sn1	110.4 (2)
O2—C3—O1	125.8 (4)	C6—C5—C7	110.4 (3)
O3—C6—C5	109.9 (3)	C6—C5—C8	108.0 (3)
O3—C6—H6A	109.7	C6—O3—Sn1	115.0 (2)
O3—C6—H6B	109.7	C6—O3—Sn1^i	130.2 (2)
O3—Sn1—C1	108.46 (18)	C7—C5—C8	110.4 (3)
O3—Sn1—C2	103.53 (18)	C7—O4—H4	109.5
O3—Sn1—N1	76.35 (10)	C8—O5—H5	109.5
O3—Sn1—O1	143.39 (10)	C9—C10—H10A	113.2
O3^i—Sn1—O1	148.51 (9)	C9—C10—H10B	113.2
O3—Sn1—O3^i	68.09 (10)	C10—C9—H9A	110.7
Sn1—O3—Sn1^i	111.91 (10)	C10—C9—H9B	110.7
O4—C7—C5	108.4 (3)	C10^ii—O6—C9	116.4 (18)
O4—C7—H7A	110.0	H10A—C10—H10B	110.5
O4—C7—H7B	110.0	H1A—C1—H1B	109.5
O5—C8—C5	113.1 (3)	H1A—C1—H1C	109.5
O5—C8—H8A	109.0	H1B—C1—H1C	109.5
O5—C8—H8B	109.0	H2A—C2—H2B	109.5
O6^ii—C10—C9	92.6 (13)	H2A—C2—H2C	109.5
O6^ii—C10—H10A	113.2	H2B—C2—H2C	109.5
O6^ii—C10—H10B	113.2	H4A—C4—H4B	108.1
O6—C9—C10	105.0 (14)	H6A—C6—H6B	108.2
O6—C9—H9A	110.7	H7A—C7—H7B	108.4
O6—C9—H9B	110.7	H8A—C8—H8B	107.8
C1—Sn1—N1	103.47 (16)	H9A—C9—H9B	108.8
C1—Sn1—O1	83.09 (16)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^iii	0.91	2.01	2.924 (5)	178
O4—H4···O2^iv	0.82	1.99	2.787 (5)	165
O5—H5···O1^iii	0.82	2.08	2.860 (5)	159
C10—H10A···O4	0.97	2.49	3.097 (1)	120

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