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The crystal structure of the title compound, [CuCl(C
6H
5O
2)]
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 Cu
2Cl
2 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.
Supporting information
CCDC reference: 636723
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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)]-µ
3-chloro]
top
Crystal data top
[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) Å3 | Needle, orange |
Z = 2 | 0.20 × 0.08 × 0.06 mm |
Data collection top
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 top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.112 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0667P)2 + 0.1373P] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
Cu1—N1 | 1.976 (5) | C3—C4 | 1.389 (8) |
Cu1—Cl1i | 2.3432 (13) | C3—C6 | 1.495 (9) |
Cu1—Cl1 | 2.4831 (18) | C4—C5 | 1.351 (7) |
Cu1—Cu1i | 2.8851 (15) | C4—C3iii | 1.389 (8) |
Cu1—Cu1ii | 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—C1iii | 1.486 (8) | C6—O2 | 1.365 (8) |
C1—C2 | 1.362 (10) | C6—C6iii | 1.396 (16) |
C1—C1iii | 1.597 (15) | O2—C6iii | 1.365 (8) |
C1—H1A | 0.9600 | O2—H2 | 0.87 (2) |
C2—C3 | 1.389 (9) | Cl1—Cu1i | 2.3432 (13) |
C2—H2A | 0.9601 | Cl1—Cu1ii | 2.3432 (13) |
| | | |
N1—Cu1—Cl1i | 116.43 (8) | C2iv—C2—C3iii | 138.6 (3) |
N1—Cu1—Cl1ii | 116.43 (7) | C1—C2—H2A | 121.0 |
Cl1i—Cu1—Cl1ii | 105.58 (7) | C3—C2—H2A | 120.1 |
N1—Cu1—Cl1 | 104.35 (15) | C2iv—C2—H2A | 68.6 |
Cl1i—Cu1—Cl1 | 106.64 (4) | C2iii—C2—H2A | 111.4 |
Cl1ii—Cu1—Cl1 | 106.64 (4) | C3iii—C2—H2A | 123.1 |
N1—Cu1—Cu1i | 125.08 (9) | C3iii—C3—C2 | 107.1 (5) |
Cl1i—Cu1—Cu1i | 55.55 (4) | C2—C3—C4 | 119.1 (6) |
Cl1ii—Cu1—Cu1i | 117.68 (5) | C2—C3—C6 | 120.7 (6) |
Cl1—Cu1—Cu1i | 51.09 (4) | C4—C3—C6 | 120.2 (6) |
N1—Cu1—Cu1ii | 125.08 (9) | C2—C3—C6iii | 127.2 (5) |
Cl1i—Cu1—Cu1ii | 117.68 (5) | C4—C3—C6iii | 95.9 (5) |
Cl1ii—Cu1—Cu1ii | 55.55 (4) | C6—C3—C2iii | 116.6 (5) |
Cl1—Cu1—Cu1ii | 51.09 (4) | C5—C4—C3iii | 116.3 (5) |
Cu1i—Cu1—Cu1ii | 80.60 (6) | C5—C4—C3 | 116.3 (5) |
C5—N1—C1 | 109.7 (4) | C5—C4—H4A | 122.1 |
C5—N1—C1iii | 109.7 (4) | C3iii—C4—H4A | 102.7 |
C1—N1—C1iii | 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 |
C1iii—N1—Cu1 | 114.5 (4) | C4—C5—H5A | 119.4 |
C2—C1—N1 | 120.7 (6) | O1—C6—O2 | 127.0 (6) |
C2—C1—C1iii | 96.7 (5) | O1—C6—C3 | 118.0 (7) |
N1—C1—C1iii | 57.5 (3) | O2—C6—C3 | 114.0 (6) |
C2—C1—H1A | 119.3 | O1—C6—C3iii | 127.6 (6) |
N1—C1—H1A | 120.0 | O2—C6—C3iii | 91.4 (5) |
C1iii—C1—H1A | 116.8 | C6iii—C6—C3iii | 50.0 (3) |
C1—C2—C3 | 118.9 (6) | O1iv—O1—C6 | 116.2 (5) |
C1—C2—C2iv | 96.7 (5) | C6iii—O2—H2 | 106 (5) |
C3—C2—C2iv | 107.1 (4) | C6—O2—H2 | 106 (5) |
C1—C2—C2iii | 83.3 (5) | Cu1i—Cl1—Cu1ii | 105.58 (7) |
C3—C2—C2iii | 72.9 (4) | Cu1i—Cl1—Cu1 | 73.36 (4) |
C2iv—C2—C2iii | 180.0 (4) | Cu1ii—Cl1—Cu1 | 73.36 (4) |
C1—C2—C3iii | 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. |
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