Poly[[(isonicotinic acid-κN)copper(I)]-μ₃-chloro]

The crystal structure of the title compound, [CuCl(C₆H₅O₂)]_n, exhibits polymeric chains extended in the b-axis direction, with a shortest Cu...Cu distance of 2.885 (2) Å. The Cu atom is tetra­hedrally coordinated by three Cl atoms, each of which bridges three metal atoms, and the N atom of isonicotinic acid. The Cu and Cl atoms lie on mirror planes, across which the isonicotinic acid ligands are disordered. Each Cu₂Cl₂ ring is centrosymmetric. The carboxyl groups are connected by O—H...O hydrogen bonds into an infinite chain running in the [101] direction. The Cu—Cl bond distances are 2.343 (1) and 2.483 (2) Å, while Cu—N is 1.976 (5) Å.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• Disorder in main residue
• R factor = 0.038
• wR factor = 0.112
• Data-to-parameter ratio = 10.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT301_ALERT_3_B Main Residue  Disorder .........................      31.00 Perc.

Alert level C
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       9.95
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ...     366.10 Ang-3
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         N1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C6
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C4     -   C5     ...       1.35 Ang.
PLAT731_ALERT_1_C Bond    Calc     0.88(5), Rep     0.87(2) ......       2.50 su-Ra
              O2   -H2      1.555   1.555
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.40 Ratio

Alert level G
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
   1 ALERT level B = Potentially serious problem
  10 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

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

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Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Poly[[(isonicotinic acid-κN)copper(I)]-µ₃-chloro]

Crystal data

[CuCl(C6H5NO2)]	F(000) = 220
Mr = 222.10	Dx = 2.015 Mg m^−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
a = 7.109 (4) Å	Cell parameters from 3328 reflections
b = 3.732 (2) Å	θ = 1.5–26.0°
c = 14.073 (7) Å	µ = 3.29 mm^−1
β = 101.381 (6)°	T = 293 K
V = 366.1 (3) Å^3	Needle, orange
Z = 2	0.20 × 0.08 × 0.06 mm

Data collection

Bruker APEX2 CCD diffractometer	836 independent reflections
Radiation source: fine-focus sealed tube	657 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω scans	θmax = 26.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −8→8
Tmin = 0.559, Tmax = 0.827	k = −4→4
3328 measured reflections	l = −17→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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0667P)^2 + 0.1373P] where P = (Fo^2 + 2Fc^2)/3
836 reflections	(Δ/σ)max < 0.001
84 parameters	Δρmax = 0.64 e Å^−3
7 restraints	Δρmin = −0.51 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)
Cu1	0.45792 (10)	0.2500	0.42046 (5)	0.0563 (4)
N1	0.2214 (7)	0.2500	0.3195 (3)	0.0698 (19)
C1	0.2340 (10)	0.036 (2)	0.2319 (5)	0.0380 (16)	0.50
H1A	0.3523	−0.0798	0.2270	0.046*	0.50
C2	0.0777 (10)	−0.006 (2)	0.1593 (5)	0.0404 (17)	0.50
H2A	0.0903	−0.1001	0.0974	0.049*	0.50
C3	−0.1005 (10)	0.1029 (19)	0.1749 (4)	0.0343 (15)	0.50
C4	−0.1140 (7)	0.2500	0.2640 (3)	0.0396 (12)
H4A	−0.2321	0.3491	0.2755	0.047*	0.50
C5	0.0483 (8)	0.2500	0.3326 (4)	0.0424 (13)
H5A	0.0394	0.2500	0.3997	0.051*
C6	−0.2760 (11)	0.063 (2)	0.0971 (5)	0.0420 (17)	0.50
O1	−0.2582 (7)	−0.0849 (17)	0.0196 (4)	0.0589 (17)	0.50
O2	−0.4309 (7)	0.2500	0.1141 (3)	0.0854 (17)
H2	−0.514 (9)	0.2500	0.059 (3)	0.102*
Cl1	0.34135 (19)	0.2500	0.57557 (9)	0.0425 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0452 (5)	0.0629 (6)	0.0580 (5)	0.000	0.0034 (4)	0.000
N1	0.035 (3)	0.138 (6)	0.036 (3)	0.000	0.008 (2)	0.000
C1	0.035 (4)	0.037 (4)	0.043 (4)	−0.003 (3)	0.010 (3)	0.000 (3)
C2	0.043 (4)	0.040 (4)	0.040 (4)	0.003 (4)	0.015 (3)	−0.001 (3)
C3	0.036 (4)	0.036 (3)	0.032 (3)	0.002 (3)	0.011 (3)	0.006 (3)
C4	0.038 (3)	0.042 (3)	0.041 (3)	0.000	0.015 (2)	0.000
C5	0.046 (3)	0.050 (3)	0.033 (3)	0.000	0.014 (2)	0.000
C6	0.047 (4)	0.039 (4)	0.039 (4)	−0.004 (4)	0.007 (3)	0.000 (3)
O1	0.045 (3)	0.087 (5)	0.045 (3)	0.004 (3)	0.010 (2)	−0.020 (3)
O2	0.043 (2)	0.159 (5)	0.053 (2)	0.000	0.0056 (19)	0.000
Cl1	0.0459 (8)	0.0383 (7)	0.0480 (7)	0.000	0.0208 (6)	0.000

Geometric parameters (Å, º)

Cu1—N1	1.976 (5)	C3—C4	1.389 (8)
Cu1—Cl1^i	2.3432 (13)	C3—C6	1.495 (9)
Cu1—Cl1	2.4831 (18)	C4—C5	1.351 (7)
Cu1—Cu1^i	2.8851 (15)	C4—C3^iii	1.389 (8)
Cu1—Cu1^ii	2.8851 (15)	C4—H4A	0.9600
N1—C5	1.280 (7)	C5—H5A	0.9582
N1—C1	1.486 (8)	C6—O1	1.252 (9)
N1—C1^iii	1.486 (8)	C6—O2	1.365 (8)
C1—C2	1.362 (10)	C6—C6^iii	1.396 (16)
C1—C1^iii	1.597 (15)	O2—C6^iii	1.365 (8)
C1—H1A	0.9600	O2—H2	0.87 (2)
C2—C3	1.389 (9)	Cl1—Cu1^i	2.3432 (13)
C2—H2A	0.9601	Cl1—Cu1^ii	2.3432 (13)
N1—Cu1—Cl1^i	116.43 (8)	C2^iv—C2—C3^iii	138.6 (3)
N1—Cu1—Cl1^ii	116.43 (7)	C1—C2—H2A	121.0
Cl1^i—Cu1—Cl1^ii	105.58 (7)	C3—C2—H2A	120.1
N1—Cu1—Cl1	104.35 (15)	C2^iv—C2—H2A	68.6
Cl1^i—Cu1—Cl1	106.64 (4)	C2^iii—C2—H2A	111.4
Cl1^ii—Cu1—Cl1	106.64 (4)	C3^iii—C2—H2A	123.1
N1—Cu1—Cu1^i	125.08 (9)	C3^iii—C3—C2	107.1 (5)
Cl1^i—Cu1—Cu1^i	55.55 (4)	C2—C3—C4	119.1 (6)
Cl1^ii—Cu1—Cu1^i	117.68 (5)	C2—C3—C6	120.7 (6)
Cl1—Cu1—Cu1^i	51.09 (4)	C4—C3—C6	120.2 (6)
N1—Cu1—Cu1^ii	125.08 (9)	C2—C3—C6^iii	127.2 (5)
Cl1^i—Cu1—Cu1^ii	117.68 (5)	C4—C3—C6^iii	95.9 (5)
Cl1^ii—Cu1—Cu1^ii	55.55 (4)	C6—C3—C2^iii	116.6 (5)
Cl1—Cu1—Cu1^ii	51.09 (4)	C5—C4—C3^iii	116.3 (5)
Cu1^i—Cu1—Cu1^ii	80.60 (6)	C5—C4—C3	116.3 (5)
C5—N1—C1	109.7 (4)	C5—C4—H4A	122.1
C5—N1—C1^iii	109.7 (4)	C3^iii—C4—H4A	102.7
C1—N1—C1^iii	65.0 (6)	C3—C4—H4A	121.6
C5—N1—Cu1	127.0 (4)	N1—C5—C4	127.4 (5)
C1—N1—Cu1	114.5 (4)	N1—C5—H5A	113.2
C1^iii—N1—Cu1	114.5 (4)	C4—C5—H5A	119.4
C2—C1—N1	120.7 (6)	O1—C6—O2	127.0 (6)
C2—C1—C1^iii	96.7 (5)	O1—C6—C3	118.0 (7)
N1—C1—C1^iii	57.5 (3)	O2—C6—C3	114.0 (6)
C2—C1—H1A	119.3	O1—C6—C3^iii	127.6 (6)
N1—C1—H1A	120.0	O2—C6—C3^iii	91.4 (5)
C1^iii—C1—H1A	116.8	C6^iii—C6—C3^iii	50.0 (3)
C1—C2—C3	118.9 (6)	O1^iv—O1—C6	116.2 (5)
C1—C2—C2^iv	96.7 (5)	C6^iii—O2—H2	106 (5)
C3—C2—C2^iv	107.1 (4)	C6—O2—H2	106 (5)
C1—C2—C2^iii	83.3 (5)	Cu1^i—Cl1—Cu1^ii	105.58 (7)
C3—C2—C2^iii	72.9 (4)	Cu1^i—Cl1—Cu1	73.36 (4)
C2^iv—C2—C2^iii	180.0 (4)	Cu1^ii—Cl1—Cu1	73.36 (4)
C1—C2—C3^iii	105.7 (6)

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