Tri-n-but­yl(5-chloro-6-hydroxy­pyridine-3-carboxyl­ato)tin(IV)

The crystal structure of the title complex, [Sn(C₄H₉)₃(C₆H₃ClNO₃)], possesses an infinite two-dimensional polymeric chain structure in the solid state, resulting from strong inter­molecular N—H...O hydrogen bonds. The Sn atom is five-coordinate with a distorted trigonal bipyramidal geometry.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.010 Å
• Disorder in main residue
• R factor = 0.042
• wR factor = 0.117
• Data-to-parameter ratio = 16.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.02
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C5
PLAT301_ALERT_3_C Main Residue  Disorder .........................       7.00 Perc.
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10
PLAT726_ALERT_1_C H...A   Calc     1.93000, Rep     1.95000 Dev...       0.02 Ang.
              H1   -O2      1.555   3.556

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _reflns_number_total               3815
           Count of symmetry unique reflns         2194
           Completeness (_total/calc)            173.88%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1621
           Fraction of Friedel pairs measured     0.739
           Are heavy atom types Z>Si present        yes

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

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


checkCIF publication errors

Alert level A
PUBL022_ALERT_1_A There is a mismatched ~ on line 113
              The crystal structure of the title complex, [Sn(C~4~H~9)~3~(C~6~H~3~ClNO~3~)],
              If you require a ~ then it should be escaped
              with a \, i.e. \~
              Otherwise there must be a matching closing ~, e.g. C~2~H~4~

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Tri-n-butyl(5-chloro-6-hydroxypyridine-3-carboxylato)tin(IV)

Crystal data

[Sn(C4H9)3(C6H3ClNO3)]	F(000) = 944
Mr = 462.57	Dx = 1.424 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3993 reflections
a = 8.825 (2) Å	θ = 2.5–26.3°
b = 10.823 (3) Å	µ = 1.32 mm^−1
c = 22.592 (6) Å	T = 298 K
V = 2157.9 (10) Å^3	Block, colorless
Z = 4	0.38 × 0.24 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3815 independent reflections
Radiation source: fine-focus sealed tube	2876 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.634, Tmax = 0.807	k = −10→12
11314 measured reflections	l = −23→26

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.117	w = 1/[σ^2(Fo^2) + (0.0634P)^2 + 1.3585P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.002
3815 reflections	Δρmax = 1.30 e Å^−3
226 parameters	Δρmin = −0.65 e Å^−3
492 restraints	Absolute structure: Flack (1983), 2193 Friedel Pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.05 (5)

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	0.15184 (4)	0.49754 (4)	0.870983 (17)	0.04879 (16)
Cl1	0.2710 (3)	1.1323 (2)	0.96393 (11)	0.1002 (9)
N1	0.0647 (8)	1.0990 (5)	0.8117 (3)	0.0572 (15)
H1	0.0242	1.1460	0.7854	0.069*
O1	0.1838 (5)	0.6941 (4)	0.8707 (2)	0.0525 (11)
O2	0.0658 (7)	0.7190 (4)	0.7844 (2)	0.0710 (15)
O3	0.1066 (7)	1.2660 (4)	0.8694 (3)	0.0738 (16)
C1	0.1262 (9)	0.7595 (6)	0.8291 (3)	0.0555 (13)
C2	0.0680 (8)	0.9742 (5)	0.8009 (3)	0.0521 (14)
H2	0.0265	0.9442	0.7659	0.063*
C3	0.1290 (9)	0.8954 (6)	0.8392 (3)	0.0519 (13)
C4	0.1972 (10)	0.9468 (7)	0.8915 (3)	0.0544 (14)
H4	0.2445	0.8955	0.9189	0.065*
C5	0.1919 (9)	1.0690 (6)	0.9006 (3)	0.0489 (15)
C6	0.1210 (8)	1.1530 (6)	0.8612 (3)	0.0485 (14)
C7	−0.0889 (7)	0.5023 (7)	0.8790 (3)	0.0623 (12)
H7A	−0.1325	0.5020	0.8395	0.075*
H7B	−0.1218	0.4273	0.8987	0.075*
C8	−0.1522 (8)	0.6131 (7)	0.9128 (4)	0.0684 (14)
H8A	−0.1071	0.6150	0.9519	0.082*
H8B	−0.1226	0.6882	0.8924	0.082*
C9	−0.3214 (8)	0.6116 (7)	0.9191 (4)	0.0760 (17)
H9A	−0.3513	0.5394	0.9417	0.091*
H9B	−0.3672	0.6054	0.8802	0.091*
C10	−0.3802 (11)	0.7274 (8)	0.9500 (4)	0.095 (3)
H10A	−0.4887	0.7242	0.9522	0.142*
H10B	−0.3499	0.7992	0.9280	0.142*
H10C	−0.3389	0.7317	0.9893	0.142*
C11	0.2723 (8)	0.4756 (7)	0.9527 (3)	0.0667 (14)
H11A	0.3510	0.4141	0.9469	0.080*
H11B	0.3219	0.5531	0.9620	0.080*
C12	0.1778 (9)	0.4376 (7)	1.0049 (3)	0.0643 (15)
H12A	0.1217	0.3635	0.9947	0.077*
H12B	0.1047	0.5024	1.0132	0.077*
C13	0.2694 (10)	0.4130 (8)	1.0605 (3)	0.0778 (19)
H13A	0.3469	0.3524	1.0512	0.093*
H13B	0.3207	0.4887	1.0717	0.093*
C14	0.1820 (12)	0.3679 (12)	1.1121 (4)	0.115 (3)
H14A	0.2491	0.3563	1.1451	0.173*
H14B	0.1344	0.2908	1.1024	0.173*
H14C	0.1058	0.4276	1.1224	0.173*
C15	0.2780 (9)	0.4556 (7)	0.7938 (3)	0.0678 (15)
H15A	0.2191	0.4008	0.7688	0.081*
H15B	0.2964	0.5311	0.7718	0.081*
C16	0.4281 (10)	0.3949 (8)	0.8082 (4)	0.0819 (17)
H16A	0.4082	0.3201	0.8305	0.098*
H16B	0.4852	0.4501	0.8336	0.098*
C17	0.5266 (10)	0.3616 (9)	0.7552 (4)	0.0929 (18)	0.80
H17A	0.5586	0.4379	0.7364	0.112*	0.80
H17B	0.6170	0.3209	0.7699	0.112*	0.80
C18	0.4596 (17)	0.2836 (13)	0.7104 (6)	0.117 (4)	0.80
H18A	0.5295	0.2736	0.6782	0.176*	0.80
H18B	0.3680	0.3210	0.6961	0.176*	0.80
H18C	0.4367	0.2042	0.7272	0.176*	0.80
C17'	0.5266 (10)	0.3616 (9)	0.7552 (4)	0.0929 (18)	0.20
H17C	0.6330	0.3672	0.7657	0.112*	0.20
H17D	0.5072	0.4180	0.7227	0.112*	0.20
C18'	0.486 (5)	0.227 (2)	0.7368 (18)	0.092 (5)	0.20
H18D	0.5437	0.2038	0.7025	0.139*	0.20
H18E	0.3797	0.2216	0.7279	0.139*	0.20
H18F	0.5093	0.1713	0.7688	0.139*	0.20

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.0593 (2)	0.0281 (2)	0.0589 (3)	0.0017 (3)	0.0035 (2)	−0.0010 (3)
Cl1	0.152 (2)	0.0528 (12)	0.0955 (17)	0.0066 (14)	−0.0568 (17)	−0.0222 (11)
N1	0.081 (4)	0.037 (3)	0.053 (4)	0.003 (3)	−0.010 (3)	0.007 (3)
O1	0.069 (3)	0.024 (2)	0.065 (3)	−0.001 (2)	0.001 (3)	0.001 (2)
O2	0.102 (4)	0.047 (3)	0.065 (3)	−0.006 (3)	−0.023 (3)	−0.016 (2)
O3	0.102 (4)	0.021 (2)	0.098 (4)	0.006 (2)	−0.010 (4)	0.003 (2)
C1	0.064 (3)	0.042 (2)	0.060 (3)	−0.003 (2)	0.002 (2)	0.000 (2)
C2	0.062 (3)	0.038 (3)	0.056 (3)	−0.007 (3)	−0.003 (3)	0.002 (2)
C3	0.060 (3)	0.041 (3)	0.055 (3)	−0.002 (2)	0.000 (3)	0.003 (2)
C4	0.063 (3)	0.042 (3)	0.058 (3)	0.001 (3)	−0.005 (3)	0.003 (2)
C5	0.062 (3)	0.027 (3)	0.057 (3)	−0.001 (3)	−0.010 (3)	0.004 (3)
C6	0.062 (3)	0.029 (3)	0.055 (3)	−0.006 (2)	0.000 (3)	0.009 (2)
C7	0.066 (2)	0.051 (2)	0.070 (3)	0.003 (3)	0.003 (2)	−0.001 (3)
C8	0.070 (3)	0.059 (3)	0.077 (3)	0.002 (3)	0.004 (3)	0.001 (2)
C9	0.075 (3)	0.066 (3)	0.087 (3)	0.001 (3)	0.003 (3)	0.003 (3)
C10	0.093 (5)	0.091 (5)	0.100 (5)	0.014 (5)	0.020 (5)	−0.019 (4)
C11	0.066 (2)	0.062 (3)	0.072 (3)	−0.001 (2)	0.000 (2)	−0.002 (2)
C12	0.071 (3)	0.056 (3)	0.066 (3)	−0.003 (3)	−0.002 (3)	−0.001 (3)
C13	0.080 (4)	0.078 (4)	0.075 (4)	0.001 (3)	−0.007 (4)	0.005 (3)
C14	0.117 (7)	0.156 (8)	0.072 (5)	−0.005 (7)	−0.011 (6)	0.010 (6)
C15	0.075 (3)	0.059 (3)	0.070 (3)	0.004 (3)	0.005 (3)	−0.006 (3)
C16	0.079 (3)	0.084 (3)	0.083 (3)	0.005 (3)	0.006 (3)	−0.013 (3)
C17	0.087 (3)	0.098 (4)	0.094 (4)	0.010 (3)	0.007 (3)	−0.009 (3)
C18	0.111 (7)	0.124 (7)	0.116 (8)	0.032 (7)	0.001 (7)	−0.036 (6)
C17'	0.087 (3)	0.098 (4)	0.094 (4)	0.010 (3)	0.007 (3)	−0.009 (3)
C18'	0.096 (9)	0.089 (10)	0.092 (10)	0.014 (9)	0.001 (9)	−0.012 (9)

Geometric parameters (Å, º)

Sn1—C15	2.119 (7)	C10—H10B	0.9600
Sn1—C7	2.133 (6)	C10—H10C	0.9600
Sn1—C11	2.143 (7)	C11—C12	1.502 (9)
Sn1—O1	2.146 (4)	C11—H11A	0.9700
Sn1—O3^i	2.537 (4)	C11—H11B	0.9700
Cl1—C5	1.733 (7)	C12—C13	1.517 (9)
N1—C6	1.355 (9)	C12—H12A	0.9700
N1—C2	1.373 (8)	C12—H12B	0.9700
N1—H1	0.8600	C13—C14	1.482 (11)
O1—C1	1.281 (8)	C13—H13A	0.9700
O2—C1	1.223 (8)	C13—H13B	0.9700
O3—C6	1.243 (8)	C14—H14A	0.9600
O3—Sn1^ii	2.537 (4)	C14—H14B	0.9600
C1—C3	1.489 (8)	C14—H14C	0.9600
C2—C3	1.329 (9)	C15—C16	1.515 (10)
C2—H2	0.9300	C15—H15A	0.9700
C3—C4	1.439 (10)	C15—H15B	0.9700
C4—C5	1.339 (8)	C16—C17	1.522 (10)
C4—H4	0.9300	C16—H16A	0.9700
C5—C6	1.419 (9)	C16—H16B	0.9700
C7—C8	1.528 (9)	C17—C18	1.445 (12)
C7—H7A	0.9700	C17—H17A	0.9700
C7—H7B	0.9700	C17—H17B	0.9700
C8—C9	1.500 (10)	C18—H18A	0.9600
C8—H8A	0.9700	C18—H18B	0.9600
C8—H8B	0.9700	C18—H18C	0.9600
C9—C10	1.525 (9)	C18'—H18D	0.9600
C9—H9A	0.9700	C18'—H18E	0.9600
C9—H9B	0.9700	C18'—H18F	0.9600
C10—H10A	0.9600
C15—Sn1—C7	126.7 (3)	C9—C10—H10C	109.5
C15—Sn1—C11	115.1 (3)	H10A—C10—H10C	109.5
C7—Sn1—C11	115.1 (3)	H10B—C10—H10C	109.5
C15—Sn1—O1	98.1 (2)	C12—C11—Sn1	115.5 (5)
C7—Sn1—O1	96.2 (2)	C12—C11—H11A	108.4
C11—Sn1—O1	92.7 (3)	Sn1—C11—H11A	108.4
C15—Sn1—O3^i	81.9 (2)	C12—C11—H11B	108.4
C7—Sn1—O3^i	82.4 (2)	Sn1—C11—H11B	108.4
C11—Sn1—O3^i	88.9 (3)	H11A—C11—H11B	107.5
O1—Sn1—O3^i	178.21 (19)	C11—C12—C13	113.7 (6)
C6—N1—C2	124.3 (6)	C11—C12—H12A	108.8
C6—N1—H1	117.8	C13—C12—H12A	108.8
C2—N1—H1	117.8	C11—C12—H12B	108.8
C1—O1—Sn1	119.8 (4)	C13—C12—H12B	108.8
C6—O3—Sn1^ii	163.2 (5)	H12A—C12—H12B	107.7
O2—C1—O1	125.5 (6)	C14—C13—C12	115.6 (7)
O2—C1—C3	119.2 (7)	C14—C13—H13A	108.4
O1—C1—C3	115.3 (6)	C12—C13—H13A	108.4
C3—C2—N1	121.6 (6)	C14—C13—H13B	108.4
C3—C2—H2	119.2	C12—C13—H13B	108.4
N1—C2—H2	119.2	H13A—C13—H13B	107.4
C2—C3—C4	117.2 (6)	C13—C14—H14A	109.5
C2—C3—C1	121.9 (7)	C13—C14—H14B	109.5
C4—C3—C1	120.9 (7)	H14A—C14—H14B	109.5
C5—C4—C3	119.5 (7)	C13—C14—H14C	109.5
C5—C4—H4	120.2	H14A—C14—H14C	109.5
C3—C4—H4	120.2	H14B—C14—H14C	109.5
C4—C5—C6	123.5 (8)	C16—C15—Sn1	112.0 (5)
C4—C5—Cl1	120.2 (6)	C16—C15—H15A	109.2
C6—C5—Cl1	116.3 (5)	Sn1—C15—H15A	109.2
O3—C6—N1	120.7 (6)	C16—C15—H15B	109.2
O3—C6—C5	125.5 (7)	Sn1—C15—H15B	109.2
N1—C6—C5	113.8 (6)	H15A—C15—H15B	107.9
C8—C7—Sn1	115.2 (5)	C15—C16—C17	115.7 (7)
C8—C7—H7A	108.5	C15—C16—H16A	108.4
Sn1—C7—H7A	108.5	C17—C16—H16A	108.4
C8—C7—H7B	108.5	C15—C16—H16B	108.4
Sn1—C7—H7B	108.5	C17—C16—H16B	108.4
H7A—C7—H7B	107.5	H16A—C16—H16B	107.4
C9—C8—C7	113.8 (6)	C18—C17—C16	117.1 (9)
C9—C8—H8A	108.8	C18—C17—H17A	108.0
C7—C8—H8A	108.8	C16—C17—H17A	108.0
C9—C8—H8B	108.8	C18—C17—H17B	108.0
C7—C8—H8B	108.8	C16—C17—H17B	108.0
H8A—C8—H8B	107.7	H17A—C17—H17B	107.3
C8—C9—C10	111.9 (7)	C17—C18—H18A	109.5
C8—C9—H9A	109.2	C17—C18—H18B	109.5
C10—C9—H9A	109.2	H18A—C18—H18B	109.5
C8—C9—H9B	109.2	C17—C18—H18C	109.5
C10—C9—H9B	109.2	H18A—C18—H18C	109.5
H9A—C9—H9B	107.9	H18B—C18—H18C	109.5
C9—C10—H10A	109.5	H18D—C18'—H18E	109.5
C9—C10—H10B	109.5	H18D—C18'—H18F	109.5
H10A—C10—H10B	109.5	H18E—C18'—H18F	109.5

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^iii	0.86	1.95	2.781 (8)	167

Symmetry code: (iii) −x, y+1/2, −z+3/2.