(2,2′-Bipyridine N,N′-dioxide-κ²O,O′)dibromo­mercury(II)

The title compound, [HgBr₂(C₁₀H₈N₂O₂)], has an Hg atom surrounded by two Br atoms and two O atoms from a chelating BipyO₂ ligand (BipyO₂ is 2,2′-bipyridine N,N′-dioxide), forming a severely distorted tetrahedron. In addition, two weak Hg...Br bonds link these complexes into a chain.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.018 Å
• R factor = 0.042
• wR factor = 0.113
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         18
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.11 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Materials Studio (Accelrys, 2001) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

(2,2'-Bipyridine N,N'-dioxide-κ²O,O')dibromo-mercury(II)

Crystal data

[Hg(Br)2(C10H8N2O2)]	F(000) = 992
Mr = 548.59	Dx = 2.816 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2815 reflections
a = 9.826 (3) Å	θ = 2.3–23.1°
b = 8.235 (2) Å	µ = 18.06 mm^−1
c = 16.073 (5) Å	T = 295 K
β = 95.857 (5)°	Plate, colorless
V = 1293.8 (7) Å^3	0.22 × 0.10 × 0.04 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2292 independent reflections
Radiation source: fine-focus sealed tube	1618 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.068
Detector resolution: 8.33 pixels mm^-1	θmax = 25.0°, θmin = 2.6°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −9→9
Tmin = 0.138, Tmax = 0.531	l = −19→19
10469 measured reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.113	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.001P)^2 + 2.15P] where P = (max(Fo^2,0) + 2Fc^2)/3
2292 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.72 e Å^−3
0 restraints	Δρmin = −0.93 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
Hg1	0.04946 (5)	0.25732 (5)	0.03900 (3)	0.0590 (2)
Br1	0.19745 (13)	0.42213 (14)	−0.04052 (7)	0.0665 (4)
Br2	−0.14872 (12)	0.09291 (14)	0.06520 (8)	0.0656 (4)
O1	0.1012 (7)	0.4220 (7)	0.1660 (4)	0.0511 (17)
O2	0.2186 (8)	0.1111 (7)	0.1325 (4)	0.0541 (18)
N1	0.0862 (9)	0.3466 (9)	0.2362 (5)	0.047 (2)
N2	0.3247 (9)	0.1951 (10)	0.1634 (5)	0.046 (2)
C1	−0.0331 (12)	0.3538 (13)	0.2685 (8)	0.059 (3)
H1	−0.1059	0.4077	0.2390	0.071*
C2	−0.0516 (15)	0.2849 (15)	0.3431 (9)	0.074 (4)
H2	−0.1361	0.2907	0.3644	0.089*
C3	0.0539 (16)	0.2083 (15)	0.3857 (8)	0.073 (4)
H3	0.0422	0.1604	0.4369	0.088*
C4	0.1829 (13)	0.1992 (13)	0.3539 (7)	0.058 (3)
H4	0.2570	0.1482	0.3837	0.070*
C5	0.1940 (11)	0.2681 (11)	0.2781 (6)	0.043 (2)
C6	0.3218 (12)	0.2709 (11)	0.2398 (7)	0.048 (3)
C7	0.4361 (11)	0.3439 (13)	0.2751 (8)	0.060 (3)
H7	0.4356	0.3919	0.3274	0.072*
C8	0.5534 (13)	0.3489 (16)	0.2353 (10)	0.080 (4)
H8	0.6318	0.3981	0.2611	0.097*
C9	0.5545 (14)	0.2823 (16)	0.1591 (11)	0.077 (4)
H9	0.6316	0.2894	0.1302	0.093*
C10	0.4403 (16)	0.2047 (13)	0.1253 (8)	0.068 (4)
H10	0.4419	0.1556	0.0733	0.081*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Hg1	0.0602 (3)	0.0612 (3)	0.0550 (3)	−0.0043 (2)	0.0019 (2)	0.0020 (2)
Br1	0.0778 (9)	0.0613 (7)	0.0630 (7)	0.0043 (6)	0.0192 (6)	0.0066 (6)
Br2	0.0550 (7)	0.0595 (7)	0.0823 (8)	0.0004 (6)	0.0072 (6)	−0.0065 (6)
O1	0.053 (4)	0.045 (4)	0.055 (4)	0.009 (3)	0.007 (3)	0.007 (3)
O2	0.065 (5)	0.039 (3)	0.058 (4)	−0.006 (4)	0.004 (4)	−0.003 (3)
N1	0.047 (6)	0.039 (4)	0.053 (5)	0.001 (4)	−0.003 (4)	−0.008 (4)
N2	0.045 (6)	0.044 (4)	0.050 (5)	0.015 (4)	0.009 (4)	0.009 (4)
C1	0.041 (7)	0.060 (7)	0.077 (8)	0.005 (5)	0.007 (6)	0.002 (6)
C2	0.055 (9)	0.081 (8)	0.088 (10)	−0.007 (7)	0.014 (7)	0.013 (8)
C3	0.096 (12)	0.071 (7)	0.061 (8)	−0.008 (8)	0.042 (8)	−0.002 (6)
C4	0.058 (8)	0.060 (6)	0.057 (7)	0.010 (6)	0.005 (6)	−0.001 (5)
C5	0.050 (6)	0.039 (5)	0.041 (5)	−0.011 (5)	0.005 (5)	−0.013 (4)
C6	0.051 (7)	0.044 (5)	0.050 (6)	0.010 (5)	0.006 (5)	0.005 (5)
C7	0.038 (7)	0.060 (7)	0.081 (8)	0.012 (5)	−0.002 (6)	−0.013 (6)
C8	0.046 (8)	0.086 (9)	0.109 (11)	0.011 (7)	0.005 (8)	−0.013 (8)
C9	0.040 (8)	0.089 (9)	0.108 (11)	0.016 (7)	0.030 (8)	0.010 (9)
C10	0.091 (11)	0.051 (6)	0.065 (8)	0.026 (7)	0.025 (8)	0.004 (6)

Geometric parameters (Å, º)

Hg1—O2	2.442 (7)	C2—H2	0.9300
Hg1—Br2	2.4432 (14)	C3—C4	1.417 (16)
Hg1—Br1	2.4433 (13)	C3—H3	0.9300
Hg1—O1	2.460 (7)	C4—C5	1.358 (15)
Hg1—Br2^i	3.5226 (14)	C4—H4	0.9300
Hg1—Br1^ii	3.5871 (15)	C5—C6	1.454 (15)
O1—N1	1.310 (10)	C6—C7	1.347 (15)
O2—N2	1.306 (10)	C7—C8	1.375 (16)
N1—C1	1.330 (13)	C7—H7	0.9300
N1—C5	1.359 (13)	C8—C9	1.344 (19)
N2—C10	1.346 (15)	C8—H8	0.9300
N2—C6	1.381 (14)	C9—C10	1.355 (19)
C1—C2	1.356 (17)	C9—H9	0.9300
C1—H1	0.9300	C10—H10	0.9300
C2—C3	1.341 (19)
O2—Hg1—Br2	97.17 (17)	C3—C2—C1	118.8 (13)
O2—Hg1—Br1	101.08 (17)	C3—C2—H2	120.6
Br2—Hg1—Br1	157.72 (5)	C1—C2—H2	120.6
O2—Hg1—O1	72.0 (2)	C2—C3—C4	121.0 (12)
Br2—Hg1—O1	105.28 (17)	C2—C3—H3	119.5
Br1—Hg1—O1	92.52 (16)	C4—C3—H3	119.5
O2—Hg1—Br2^i	71.63 (15)	C5—C4—C3	117.3 (11)
Br2—Hg1—Br2^i	83.82 (4)	C5—C4—H4	121.4
Br1—Hg1—Br2^i	89.87 (4)	C3—C4—H4	121.4
O1—Hg1—Br2^i	143.33 (15)	C4—C5—N1	120.9 (10)
O2—Hg1—Br1^ii	140.99 (16)	C4—C5—C6	122.5 (10)
Br2—Hg1—Br1^ii	81.68 (4)	N1—C5—C6	116.4 (9)
Br1—Hg1—Br1^ii	91.93 (4)	C7—C6—N2	118.9 (10)
O1—Hg1—Br1^ii	70.81 (15)	C7—C6—C5	123.2 (10)
Br2^i—Hg1—Br1^ii	145.70 (3)	N2—C6—C5	117.8 (9)
Hg1—Br1—Hg1^ii	88.07 (4)	C6—C7—C8	121.4 (12)
Hg1—Br2—Hg1^i	96.18 (4)	C6—C7—H7	119.3
N1—O1—Hg1	114.9 (5)	C8—C7—H7	119.3
N2—O2—Hg1	116.1 (5)	C9—C8—C7	119.8 (13)
O1—N1—C1	119.7 (9)	C9—C8—H8	120.1
O1—N1—C5	120.1 (9)	C7—C8—H8	120.1
C1—N1—C5	120.0 (10)	C8—C9—C10	118.3 (12)
O2—N2—C10	122.4 (10)	C8—C9—H9	120.8
O2—N2—C6	119.3 (9)	C10—C9—H9	120.8
C10—N2—C6	118.2 (10)	N2—C10—C9	123.2 (12)
N1—C1—C2	122.0 (11)	N2—C10—H10	118.4
N1—C1—H1	119.0	C9—C10—H10	118.4
C2—C1—H1	119.0
O2—Hg1—Br1—Hg1^ii	−143.02 (16)	C5—N1—C1—C2	0.2 (16)
Br2—Hg1—Br1—Hg1^ii	72.57 (11)	N1—C1—C2—C3	0.5 (19)
O1—Hg1—Br1—Hg1^ii	−70.87 (15)	C1—C2—C3—C4	0 (2)
Br2^i—Hg1—Br1—Hg1^ii	145.74 (3)	C2—C3—C4—C5	−1.4 (18)
Br1^ii—Hg1—Br1—Hg1^ii	0.0	C3—C4—C5—N1	2.0 (15)
O2—Hg1—Br1—Br2^ii	−128.06 (16)	C3—C4—C5—C6	178.2 (9)
O2—Hg1—Br2—Hg1^i	−70.54 (16)	O1—N1—C5—C4	175.2 (9)
Br1—Hg1—Br2—Hg1^i	74.32 (11)	C1—N1—C5—C4	−1.5 (14)
O1—Hg1—Br2—Hg1^i	−143.78 (15)	O1—N1—C5—C6	−1.2 (12)
Br2^i—Hg1—Br2—Hg1^i	0.0	C1—N1—C5—C6	−177.9 (9)
Br1^ii—Hg1—Br2—Hg1^i	148.82 (4)	O2—N2—C6—C7	173.6 (9)
O2—Hg1—O1—N1	−54.2 (6)	C10—N2—C6—C7	−3.3 (14)
Br2—Hg1—O1—N1	38.5 (6)	O2—N2—C6—C5	−6.6 (12)
Br1—Hg1—O1—N1	−155.0 (6)	C10—N2—C6—C5	176.4 (9)
Br2^i—Hg1—O1—N1	−61.8 (7)	C4—C5—C6—C7	−60.6 (14)
Br1^ii—Hg1—O1—N1	113.8 (6)	N1—C5—C6—C7	115.8 (11)
Br2—Hg1—O2—N2	−152.8 (6)	C4—C5—C6—N2	119.7 (11)
Br1—Hg1—O2—N2	40.1 (6)	N1—C5—C6—N2	−63.9 (11)
O1—Hg1—O2—N2	−49.0 (6)	N2—C6—C7—C8	2.2 (16)
Br2^i—Hg1—O2—N2	126.2 (6)	C5—C6—C7—C8	−177.6 (11)
Br1^ii—Hg1—O2—N2	−67.2 (7)	C6—C7—C8—C9	1 (2)
Hg1—O1—N1—C1	−91.7 (9)	C7—C8—C9—C10	−3 (2)
Hg1—O1—N1—C5	91.6 (8)	O2—N2—C10—C9	−175.5 (10)
Hg1—O2—N2—C10	−90.6 (9)	C6—N2—C10—C9	1.3 (16)
Hg1—O2—N2—C6	92.6 (8)	C8—C9—C10—N2	2 (2)
O1—N1—C1—C2	−176.5 (10)

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