catena-Poly[[(5-bromo­pyridine-3-carboxyl­ato-κ²O,O′)dibutyl­tin(IV)]-μ-5-bromo­pyridine-3-carboxyl­ato-κ²O,O′:κN]

The title compound, [Sn(C₄H₉)₂(C₆H₃BrNO₂)₂]_n, displays an infinite chain structure owing to the presence of Sn—N bridges between adjacent monomer units. The Sn centre has a distorted penta­gonal–bipyramidal geometry defined by a C₂NO₄ donor set with the C atoms occupying axial positions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.035
• wR factor = 0.091
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.283     0.494
            Tmin and Tmax expected:      0.218     0.440
            RR =      1.157
            Please check that your absorption correction is appropriate.
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large .......       1.13
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.89
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.69 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.891
            Tmax scaled      0.440 Tmin scaled      0.252
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   3 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
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

catena-Poly[[(5-bromopyridine-3-carboxylato-κ²O,O')dibutyltin(IV)]- µ-5-bromopyridine-3-carboxylato-κ²O,O':κN]

Crystal data

[Sn(C4H9)2(C6H3BrNO2)2]	Z = 2
Mr = 634.92	F(000) = 620
Triclinic, P1	Dx = 1.811 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.068 (2) Å	Cell parameters from 2410 reflections
b = 10.044 (3) Å	θ = 2.8–26.9°
c = 15.158 (4) Å	µ = 4.56 mm^−1
α = 76.001 (4)°	T = 293 K
β = 80.659 (4)°	Block, colorless
γ = 79.932 (4)°	0.37 × 0.29 × 0.18 mm
V = 1164.2 (6) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	4051 independent reflections
Radiation source: fine-focus sealed tube	3251 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.283, Tmax = 0.494	k = −11→9
6141 measured reflections	l = −18→17

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.091	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0476P)^2] where P = (Fo^2 + 2Fc^2)/3
4051 reflections	(Δ/σ)max = 0.001
262 parameters	Δρmax = 0.82 e Å^−3
0 restraints	Δρmin = −0.62 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
Sn1	0.64737 (4)	0.10972 (3)	0.71872 (2)	0.03436 (12)
Br1	−0.12033 (7)	0.69213 (5)	0.57549 (4)	0.05397 (17)
Br2	1.27152 (10)	−0.55668 (8)	0.89918 (5)	0.1041 (3)
N1	−0.1273 (4)	0.2762 (4)	0.6782 (3)	0.0389 (9)
N2	0.7715 (8)	−0.5315 (5)	0.8677 (4)	0.0823 (17)
O1	0.3735 (3)	0.1229 (3)	0.7095 (2)	0.0424 (8)
O2	0.4536 (4)	0.3301 (3)	0.6633 (2)	0.0443 (8)
O3	0.6253 (4)	−0.1108 (3)	0.7785 (2)	0.0455 (8)
O4	0.8865 (4)	−0.0655 (3)	0.7620 (2)	0.0436 (8)
C1	0.3418 (5)	0.2524 (5)	0.6808 (3)	0.0388 (11)
C2	0.0359 (5)	0.2278 (4)	0.6891 (3)	0.0387 (11)
H2	0.0661	0.1334	0.7117	0.046*
C3	0.1609 (5)	0.3131 (4)	0.6679 (3)	0.0336 (10)
C4	0.1167 (6)	0.4525 (5)	0.6350 (3)	0.0387 (11)
H4	0.1978	0.5124	0.6208	0.046*
C5	−0.0513 (5)	0.5022 (4)	0.6232 (3)	0.0371 (10)
C6	−0.1694 (6)	0.4114 (5)	0.6456 (3)	0.0434 (12)
H6	−0.2820	0.4458	0.6377	0.052*
C7	0.7817 (6)	−0.1498 (4)	0.7855 (3)	0.0387 (11)
C8	0.7265 (8)	−0.3950 (5)	0.8379 (4)	0.0628 (16)
H8	0.6150	−0.3628	0.8265	0.075*
C9	0.8381 (6)	−0.2998 (5)	0.8232 (3)	0.0423 (11)
C10	1.0036 (6)	−0.3453 (5)	0.8409 (3)	0.0465 (12)
H10	1.0816	−0.2835	0.8312	0.056*
C11	1.0488 (8)	−0.4845 (6)	0.8734 (4)	0.0594 (15)
C12	0.9317 (10)	−0.5730 (6)	0.8854 (4)	0.0762 (19)
H12	0.9655	−0.6671	0.9070	0.091*
C13	0.7249 (6)	0.0767 (5)	0.5837 (3)	0.0539 (13)
H13A	0.8472	0.0731	0.5721	0.065*
H13B	0.7004	−0.0144	0.5836	0.065*
C14	0.6528 (7)	0.1760 (6)	0.5041 (4)	0.0594 (14)
H14A	0.6864	0.2660	0.4988	0.071*
H14B	0.5299	0.1860	0.5159	0.071*
C15	0.7095 (8)	0.1312 (7)	0.4136 (4)	0.0750 (18)
H15A	0.8323	0.1212	0.4017	0.090*
H15B	0.6757	0.0413	0.4188	0.090*
C16	0.6374 (9)	0.2307 (8)	0.3346 (4)	0.091 (2)
H16A	0.5158	0.2396	0.3452	0.137*
H16B	0.6773	0.1972	0.2797	0.137*
H16C	0.6726	0.3194	0.3280	0.137*
C17	0.6013 (5)	0.1683 (4)	0.8466 (3)	0.0402 (11)
H17A	0.6032	0.2674	0.8350	0.048*
H17B	0.4874	0.1518	0.8740	0.048*
C18	0.7226 (6)	0.0967 (5)	0.9171 (3)	0.0459 (12)
H18A	0.7277	−0.0029	0.9269	0.055*
H18B	0.8356	0.1197	0.8933	0.055*
C19	0.6674 (7)	0.1397 (6)	1.0081 (3)	0.0574 (14)
H19A	0.6607	0.2395	0.9980	0.069*
H19B	0.5550	0.1157	1.0322	0.069*
C20	0.7870 (8)	0.0715 (7)	1.0776 (4)	0.0795 (19)
H20A	0.7930	−0.0274	1.0885	0.119*
H20B	0.7466	0.1012	1.1339	0.119*
H20C	0.8979	0.0970	1.0549	0.119*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.02618 (17)	0.03606 (19)	0.0399 (2)	−0.00378 (12)	−0.00617 (13)	−0.00564 (13)
Br1	0.0561 (3)	0.0395 (3)	0.0597 (4)	0.0033 (2)	−0.0096 (3)	−0.0039 (2)
Br2	0.0906 (5)	0.0988 (6)	0.0891 (6)	0.0541 (4)	−0.0101 (4)	−0.0047 (4)
N1	0.029 (2)	0.037 (2)	0.049 (2)	−0.0043 (16)	−0.0075 (17)	−0.0051 (17)
N2	0.120 (5)	0.040 (3)	0.088 (4)	−0.027 (3)	−0.031 (4)	0.004 (3)
O1	0.0271 (16)	0.0404 (19)	0.057 (2)	−0.0028 (13)	−0.0102 (14)	−0.0045 (15)
O2	0.0292 (17)	0.0494 (19)	0.053 (2)	−0.0095 (15)	−0.0044 (14)	−0.0063 (15)
O3	0.0351 (18)	0.0362 (17)	0.061 (2)	−0.0046 (14)	−0.0061 (16)	−0.0035 (15)
O4	0.0389 (18)	0.0340 (17)	0.055 (2)	−0.0044 (14)	−0.0055 (15)	−0.0053 (14)
C1	0.030 (2)	0.049 (3)	0.035 (3)	−0.006 (2)	−0.0030 (19)	−0.008 (2)
C2	0.033 (3)	0.040 (3)	0.041 (3)	−0.003 (2)	−0.006 (2)	−0.005 (2)
C3	0.030 (2)	0.039 (2)	0.030 (2)	−0.0040 (19)	−0.0049 (18)	−0.0030 (18)
C4	0.033 (2)	0.047 (3)	0.038 (3)	−0.012 (2)	0.000 (2)	−0.012 (2)
C5	0.034 (2)	0.038 (2)	0.038 (3)	−0.001 (2)	−0.007 (2)	−0.0069 (19)
C6	0.026 (2)	0.050 (3)	0.052 (3)	0.002 (2)	−0.007 (2)	−0.010 (2)
C7	0.044 (3)	0.036 (2)	0.038 (3)	−0.004 (2)	−0.008 (2)	−0.0106 (19)
C8	0.083 (4)	0.049 (3)	0.062 (4)	−0.019 (3)	−0.028 (3)	−0.003 (3)
C9	0.052 (3)	0.036 (3)	0.039 (3)	−0.005 (2)	−0.009 (2)	−0.009 (2)
C10	0.056 (3)	0.036 (3)	0.042 (3)	0.008 (2)	−0.001 (2)	−0.011 (2)
C11	0.077 (4)	0.052 (3)	0.040 (3)	0.015 (3)	−0.005 (3)	−0.012 (2)
C12	0.125 (6)	0.037 (3)	0.058 (4)	0.005 (4)	−0.020 (4)	0.000 (3)
C13	0.049 (3)	0.063 (3)	0.051 (3)	−0.005 (3)	0.000 (2)	−0.020 (3)
C14	0.057 (3)	0.074 (4)	0.048 (3)	−0.008 (3)	−0.005 (3)	−0.018 (3)
C15	0.068 (4)	0.110 (5)	0.054 (4)	−0.022 (4)	0.002 (3)	−0.032 (3)
C16	0.088 (5)	0.143 (6)	0.052 (4)	−0.042 (5)	−0.004 (4)	−0.026 (4)
C17	0.035 (2)	0.041 (3)	0.044 (3)	−0.003 (2)	0.000 (2)	−0.013 (2)
C18	0.038 (3)	0.054 (3)	0.046 (3)	−0.004 (2)	−0.007 (2)	−0.012 (2)
C19	0.054 (3)	0.076 (4)	0.045 (3)	−0.015 (3)	−0.002 (3)	−0.017 (3)
C20	0.084 (5)	0.115 (5)	0.044 (4)	−0.031 (4)	−0.014 (3)	−0.009 (3)

Geometric parameters (Å, º)

Sn1—C13	2.128 (5)	C9—C10	1.381 (6)
Sn1—C17	2.117 (5)	C10—C11	1.371 (6)
Sn1—O1	2.215 (3)	C10—H10	0.9300
Sn1—O2	2.523 (3)	C11—C12	1.369 (9)
Sn1—O3	2.207 (3)	C12—H12	0.9300
Sn1—O4	2.432 (3)	C13—C14	1.493 (7)
Sn1—N1^i	2.585 (3)	C13—H13A	0.9700
Br1—C5	1.888 (4)	C13—H13B	0.9700
Br2—C11	1.882 (6)	C14—C15	1.523 (7)
N1—C6	1.331 (5)	C14—H14A	0.9700
N1—C2	1.343 (5)	C14—H14B	0.9700
N1—Sn1^ii	2.585 (3)	C15—C16	1.487 (8)
N2—C12	1.336 (8)	C15—H15A	0.9700
N2—C8	1.340 (6)	C15—H15B	0.9700
O1—C1	1.262 (5)	C16—H16A	0.9600
O2—C1	1.250 (5)	C16—H16B	0.9600
O3—C7	1.268 (5)	C16—H16C	0.9600
O4—C7	1.251 (5)	C17—C18	1.530 (6)
C1—C3	1.504 (6)	C17—H17A	0.9700
C2—C3	1.385 (6)	C17—H17B	0.9700
C2—H2	0.9300	C18—C19	1.518 (7)
C3—C4	1.372 (6)	C18—H18A	0.9700
C4—C5	1.384 (6)	C18—H18B	0.9700
C4—H4	0.9300	C19—C20	1.504 (7)
C5—C6	1.379 (6)	C19—H19A	0.9700
C6—H6	0.9300	C19—H19B	0.9700
C7—C9	1.495 (6)	C20—H20A	0.9600
C8—C9	1.380 (7)	C20—H20B	0.9600
C8—H8	0.9300	C20—H20C	0.9600
C13—Sn1—O1	94.01 (16)	C11—C10—H10	121.2
C13—Sn1—O2	92.70 (15)	C9—C10—H10	121.2
C13—Sn1—O3	93.56 (16)	C12—C11—C10	119.7 (6)
C13—Sn1—O4	85.72 (15)	C12—C11—Br2	119.4 (4)
C17—Sn1—O1	93.09 (14)	C10—C11—Br2	120.9 (5)
C17—Sn1—O2	85.41 (14)	N2—C12—C11	123.7 (5)
C17—Sn1—O3	94.58 (15)	N2—C12—H12	118.2
C17—Sn1—O4	93.71 (14)	C11—C12—H12	118.2
C17—Sn1—C13	169.80 (18)	C14—C13—Sn1	120.1 (4)
O1—Sn1—O2	54.98 (10)	C14—C13—H13A	107.3
O1—Sn1—O3	82.86 (11)	Sn1—C13—H13A	107.3
O1—Sn1—O4	138.91 (10)	C14—C13—H13B	107.3
O2—Sn1—O3	137.70 (10)	Sn1—C13—H13B	107.3
O2—Sn1—O4	166.07 (9)	H13A—C13—H13B	106.9
O3—Sn1—O4	56.22 (10)	C13—C14—C15	113.6 (5)
C13—Sn1—N1^i	85.08 (16)	C13—C14—H14A	108.8
C17—Sn1—N1^i	84.73 (15)	C15—C14—H14A	108.9
O1—Sn1—N1^i	137.34 (11)	C13—C14—H14B	108.9
O2—Sn1—N1^i	82.41 (10)	C15—C14—H14B	108.9
O3—Sn1—N1^i	139.80 (11)	H14A—C14—H14B	107.7
O4—Sn1—N1^i	83.66 (11)	C16—C15—C14	113.2 (6)
C6—N1—C2	118.3 (4)	C16—C15—H15A	108.9
C2—N1—Sn1^ii	120.6 (3)	C14—C15—H15A	108.9
C6—N1—Sn1^ii	121.1 (3)	C16—C15—H15B	108.9
C12—N2—C8	116.5 (5)	C14—C15—H15B	108.9
C1—O1—Sn1	98.1 (2)	H15A—C15—H15B	107.7
C1—O2—Sn1	84.2 (3)	C15—C16—H16A	109.5
C7—O3—Sn1	96.2 (3)	C15—C16—H16B	109.5
C7—O4—Sn1	86.3 (3)	H16A—C16—H16B	109.5
O2—C1—O1	122.7 (4)	C15—C16—H16C	109.5
O2—C1—C3	119.8 (4)	H16A—C16—H16C	109.5
O1—C1—C3	117.5 (4)	H16B—C16—H16C	109.5
N1—C2—C3	122.6 (4)	C18—C17—Sn1	117.4 (3)
N1—C2—H2	118.7	C18—C17—H17A	107.9
C3—C2—H2	118.7	Sn1—C17—H17A	107.9
C4—C3—C2	118.8 (4)	C18—C17—H17B	107.9
C4—C3—C1	121.1 (4)	Sn1—C17—H17B	107.9
C2—C3—C1	120.0 (4)	H17A—C17—H17B	107.2
C3—C4—C5	118.6 (4)	C19—C18—C17	112.1 (4)
C3—C4—H4	120.7	C19—C18—H18A	109.2
C5—C4—H4	120.7	C17—C18—H18A	109.2
C6—C5—C4	119.6 (4)	C19—C18—H18B	109.2
C6—C5—Br1	119.6 (3)	C17—C18—H18B	109.2
C4—C5—Br1	120.8 (3)	H18A—C18—H18B	107.9
N1—C6—C5	122.1 (4)	C20—C19—C18	112.6 (5)
N1—C6—H6	118.9	C20—C19—H19A	109.1
C5—C6—H6	118.9	C18—C19—H19A	109.1
O4—C7—O3	121.3 (4)	C20—C19—H19B	109.1
O4—C7—C9	120.6 (4)	C18—C19—H19B	109.1
O3—C7—C9	118.1 (4)	H19A—C19—H19B	107.8
N2—C8—C9	123.1 (5)	C19—C20—H20A	109.5
N2—C8—H8	118.5	C19—C20—H20B	109.5
C9—C8—H8	118.5	H20A—C20—H20B	109.5
C8—C9—C10	119.4 (4)	C19—C20—H20C	109.5
C8—C9—C7	120.3 (4)	H20A—C20—H20C	109.5
C10—C9—C7	120.3 (4)	H20B—C20—H20C	109.5
C11—C10—C9	117.7 (5)

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