Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807060217/hb2621sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807060217/hb2621Isup2.hkl |
CCDC reference: 657139
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.037
- wR factor = 0.088
- Data-to-parameter ratio = 14.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3
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 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 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 0 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
A mixture of CuSO4 (0.5 mmol), benzene-1,2-dicarboxylic acid (0.5 mmol), NaOH (1.0 mmol) and isonicotinamide (1.0 mmol) was heated in water/ethanol (20 ml, 1:1 v/v) mixture and continually stirred about 30 min at 333 K. The mixture was filtered and the filtrate was allowed to stand. One week later, blue blocks of (I) were obtained.
The water H atoms were located in a difference map and refined as riding in their as-found relative positions. The Uiso values were freely refined.
The C– and N-bound H atoms were positioned geometrically (C—H = 0.93 Å, N—H = 0.86 Å) and refined as riding with Uiso(H) = 1.2Ueq(carrier).
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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, 1997); software used to prepare material for publication: SHELXL97.
[Cu(C6H6N2O)2(C8H4O4)]·H2O | F(000) = 1004 |
Mr = 489.92 | Dx = 1.556 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3211 reflections |
a = 8.023 (2) Å | θ = 2.5–23.0° |
b = 22.903 (6) Å | µ = 1.10 mm−1 |
c = 11.473 (3) Å | T = 293 K |
β = 97.128 (3)° | Block, blue |
V = 2091.7 (9) Å3 | 0.38 × 0.16 × 0.09 mm |
Z = 4 |
Bruker APEX I CCD diffractometer | 4106 independent reflections |
Radiation source: fine-focus sealed tube | 3171 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
ω scans | θmax = 26.0°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −9→9 |
Tmin = 0.813, Tmax = 0.903 | k = −28→28 |
17837 measured reflections | l = −14→14 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.088 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0349P)2 + 0.975P] where P = (Fo2 + 2Fc2)/3 |
4106 reflections | (Δ/σ)max = 0.001 |
291 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
[Cu(C6H6N2O)2(C8H4O4)]·H2O | V = 2091.7 (9) Å3 |
Mr = 489.92 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.023 (2) Å | µ = 1.10 mm−1 |
b = 22.903 (6) Å | T = 293 K |
c = 11.473 (3) Å | 0.38 × 0.16 × 0.09 mm |
β = 97.128 (3)° |
Bruker APEX I CCD diffractometer | 4106 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | 3171 reflections with I > 2σ(I) |
Tmin = 0.813, Tmax = 0.903 | Rint = 0.047 |
17837 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.088 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.30 e Å−3 |
4106 reflections | Δρmin = −0.34 e Å−3 |
291 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.54119 (4) | 0.233735 (13) | 0.83422 (3) | 0.03007 (11) | |
O3 | 0.6678 (2) | 0.17280 (7) | 0.76335 (15) | 0.0312 (4) | |
O2 | 0.0383 (2) | −0.01116 (8) | 0.8689 (2) | 0.0481 (5) | |
O5 | 0.9281 (3) | 0.22272 (9) | 0.57311 (18) | 0.0487 (5) | |
O6 | 0.8999 (2) | 0.20366 (8) | 0.38014 (16) | 0.0364 (4) | |
OW1 | 0.7108 (3) | 0.21483 (9) | 1.0445 (2) | 0.0541 (6) | |
HW1A | 0.6272 | 0.2354 | 1.0693 | 0.068 (11)* | |
HW1B | 0.8019 | 0.2389 | 1.0644 | 0.109 (17)* | |
O4 | 0.5213 (3) | 0.20936 (9) | 0.60265 (17) | 0.0460 (5) | |
O1 | 0.9730 (2) | 0.47765 (8) | 0.6720 (2) | 0.0511 (6) | |
N4 | −0.1684 (3) | 0.05588 (10) | 0.8562 (2) | 0.0434 (6) | |
H4A | −0.2454 | 0.0300 | 0.8588 | 0.052* | |
H4B | −0.1948 | 0.0923 | 0.8505 | 0.052* | |
N1 | 0.7024 (3) | 0.29483 (9) | 0.79177 (19) | 0.0314 (5) | |
N2 | 1.1750 (3) | 0.41113 (10) | 0.6543 (2) | 0.0438 (6) | |
H2A | 1.2418 | 0.4367 | 0.6309 | 0.053* | |
H2B | 1.2055 | 0.3752 | 0.6612 | 0.053* | |
N3 | 0.3642 (3) | 0.17358 (9) | 0.85260 (19) | 0.0298 (5) | |
C13 | 0.6209 (3) | 0.17375 (11) | 0.6516 (2) | 0.0315 (6) | |
C16 | 0.6908 (4) | 0.02106 (13) | 0.5449 (3) | 0.0529 (8) | |
H16A | 0.6550 | −0.0165 | 0.5604 | 0.063* | |
C5 | 0.7409 (3) | 0.38399 (12) | 0.6910 (3) | 0.0391 (7) | |
H5A | 0.6936 | 0.4158 | 0.6487 | 0.047* | |
C4 | 1.0243 (3) | 0.42715 (12) | 0.6799 (2) | 0.0357 (6) | |
C1 | 0.8677 (3) | 0.29098 (11) | 0.8185 (2) | 0.0342 (6) | |
H1A | 0.9113 | 0.2594 | 0.8634 | 0.041* | |
C3 | 0.9141 (3) | 0.37930 (11) | 0.7179 (2) | 0.0311 (6) | |
C8 | 0.0795 (4) | 0.14272 (12) | 0.8104 (3) | 0.0423 (7) | |
H8A | −0.0303 | 0.1516 | 0.7796 | 0.051* | |
C14 | 0.6898 (3) | 0.12431 (11) | 0.5849 (2) | 0.0309 (6) | |
C18 | 0.8577 (4) | 0.08515 (12) | 0.4431 (3) | 0.0429 (7) | |
H18A | 0.9314 | 0.0908 | 0.3876 | 0.051* | |
C9 | 0.1188 (3) | 0.08828 (11) | 0.8575 (2) | 0.0301 (6) | |
C15 | 0.6331 (4) | 0.06837 (12) | 0.6035 (3) | 0.0430 (7) | |
H15A | 0.5552 | 0.0625 | 0.6560 | 0.052* | |
C10 | −0.0085 (3) | 0.03971 (12) | 0.8608 (2) | 0.0348 (6) | |
C19 | 0.8055 (3) | 0.13276 (11) | 0.5048 (2) | 0.0312 (6) | |
C2 | 0.9782 (3) | 0.33170 (11) | 0.7827 (2) | 0.0344 (6) | |
H2C | 1.0935 | 0.3271 | 0.8019 | 0.041* | |
C11 | 0.2846 (3) | 0.07746 (11) | 0.9010 (2) | 0.0346 (6) | |
H11A | 0.3159 | 0.0412 | 0.9328 | 0.042* | |
C12 | 0.4028 (3) | 0.12067 (11) | 0.8968 (2) | 0.0338 (6) | |
H12A | 0.5139 | 0.1127 | 0.9259 | 0.041* | |
C20 | 0.8826 (3) | 0.19152 (11) | 0.4871 (3) | 0.0316 (6) | |
C7 | 0.2050 (3) | 0.18376 (12) | 0.8097 (3) | 0.0424 (7) | |
H7A | 0.1772 | 0.2203 | 0.7778 | 0.051* | |
C6 | 0.6409 (3) | 0.34095 (12) | 0.7279 (3) | 0.0393 (7) | |
H6A | 0.5253 | 0.3438 | 0.7079 | 0.047* | |
C17 | 0.8012 (4) | 0.02959 (13) | 0.4637 (3) | 0.0518 (8) | |
H17A | 0.8376 | −0.0020 | 0.4228 | 0.062* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.02659 (18) | 0.02751 (18) | 0.0382 (2) | −0.00159 (14) | 0.01255 (14) | 0.00079 (14) |
O3 | 0.0280 (10) | 0.0329 (10) | 0.0340 (11) | 0.0018 (8) | 0.0089 (8) | 0.0003 (8) |
O2 | 0.0328 (12) | 0.0275 (11) | 0.0845 (16) | 0.0015 (9) | 0.0098 (11) | 0.0008 (10) |
O5 | 0.0579 (14) | 0.0435 (12) | 0.0451 (13) | −0.0152 (10) | 0.0078 (10) | −0.0065 (10) |
O6 | 0.0382 (11) | 0.0318 (10) | 0.0425 (11) | −0.0025 (8) | 0.0184 (9) | 0.0016 (9) |
OW1 | 0.0533 (14) | 0.0437 (12) | 0.0687 (16) | −0.0015 (12) | 0.0218 (12) | −0.0039 (11) |
O4 | 0.0449 (13) | 0.0430 (12) | 0.0478 (13) | 0.0133 (10) | −0.0033 (10) | 0.0019 (10) |
O1 | 0.0408 (13) | 0.0271 (11) | 0.0886 (17) | 0.0001 (9) | 0.0202 (11) | 0.0062 (11) |
N4 | 0.0260 (13) | 0.0307 (13) | 0.0737 (18) | −0.0010 (10) | 0.0072 (12) | 0.0092 (12) |
N1 | 0.0271 (12) | 0.0293 (12) | 0.0393 (13) | −0.0007 (10) | 0.0100 (10) | 0.0025 (10) |
N2 | 0.0298 (13) | 0.0299 (12) | 0.0738 (18) | −0.0033 (10) | 0.0151 (12) | 0.0074 (12) |
N3 | 0.0230 (11) | 0.0278 (11) | 0.0399 (13) | 0.0002 (9) | 0.0090 (9) | 0.0010 (10) |
C13 | 0.0240 (14) | 0.0312 (14) | 0.0401 (16) | −0.0065 (11) | 0.0070 (12) | −0.0002 (12) |
C16 | 0.064 (2) | 0.0283 (16) | 0.065 (2) | −0.0086 (15) | 0.0030 (18) | 0.0004 (15) |
C5 | 0.0317 (16) | 0.0346 (15) | 0.0520 (18) | 0.0057 (12) | 0.0092 (13) | 0.0137 (13) |
C4 | 0.0297 (15) | 0.0312 (15) | 0.0465 (17) | −0.0051 (12) | 0.0054 (12) | −0.0009 (13) |
C1 | 0.0318 (15) | 0.0286 (14) | 0.0418 (16) | 0.0027 (12) | 0.0032 (12) | 0.0055 (12) |
C3 | 0.0295 (15) | 0.0263 (13) | 0.0383 (15) | −0.0021 (11) | 0.0072 (12) | −0.0015 (11) |
C8 | 0.0250 (15) | 0.0365 (16) | 0.064 (2) | −0.0017 (12) | −0.0021 (13) | 0.0107 (14) |
C14 | 0.0294 (14) | 0.0298 (14) | 0.0331 (15) | −0.0022 (11) | 0.0018 (11) | 0.0012 (11) |
C18 | 0.0459 (18) | 0.0385 (17) | 0.0461 (18) | 0.0050 (14) | 0.0131 (14) | −0.0026 (14) |
C9 | 0.0266 (14) | 0.0265 (13) | 0.0381 (15) | −0.0005 (11) | 0.0078 (11) | 0.0004 (11) |
C15 | 0.0460 (18) | 0.0387 (17) | 0.0457 (18) | −0.0117 (14) | 0.0114 (14) | 0.0018 (14) |
C10 | 0.0304 (15) | 0.0303 (15) | 0.0444 (17) | −0.0018 (12) | 0.0069 (12) | 0.0017 (12) |
C19 | 0.0284 (15) | 0.0276 (14) | 0.0374 (15) | 0.0015 (11) | 0.0037 (12) | −0.0004 (12) |
C2 | 0.0258 (14) | 0.0317 (15) | 0.0451 (17) | −0.0001 (12) | 0.0017 (12) | 0.0017 (12) |
C11 | 0.0298 (15) | 0.0275 (14) | 0.0470 (17) | 0.0044 (11) | 0.0065 (12) | 0.0050 (12) |
C12 | 0.0229 (14) | 0.0359 (15) | 0.0429 (16) | 0.0038 (12) | 0.0053 (12) | 0.0047 (12) |
C20 | 0.0239 (14) | 0.0297 (14) | 0.0421 (17) | 0.0030 (11) | 0.0080 (12) | 0.0006 (12) |
C7 | 0.0319 (16) | 0.0289 (15) | 0.066 (2) | 0.0002 (12) | 0.0029 (14) | 0.0139 (14) |
C6 | 0.0240 (14) | 0.0426 (17) | 0.0526 (19) | 0.0024 (12) | 0.0095 (13) | 0.0123 (14) |
C17 | 0.061 (2) | 0.0308 (16) | 0.065 (2) | 0.0040 (15) | 0.0106 (17) | −0.0119 (15) |
Cu1—O6i | 1.9409 (18) | C5—C6 | 1.371 (4) |
Cu1—O3 | 1.9610 (17) | C5—C3 | 1.390 (4) |
Cu1—N1 | 2.006 (2) | C5—H5A | 0.9300 |
Cu1—N3 | 2.008 (2) | C4—C3 | 1.506 (4) |
O3—C13 | 1.291 (3) | C1—C2 | 1.384 (4) |
O2—C10 | 1.224 (3) | C1—H1A | 0.9300 |
O5—C20 | 1.237 (3) | C3—C2 | 1.382 (4) |
O6—C20 | 1.282 (3) | C8—C7 | 1.379 (4) |
O6—Cu1ii | 1.9409 (18) | C8—C9 | 1.379 (4) |
OW1—HW1A | 0.8939 | C8—H8A | 0.9300 |
OW1—HW1B | 0.9207 | C14—C15 | 1.385 (4) |
O4—C13 | 1.228 (3) | C14—C19 | 1.399 (4) |
O1—C4 | 1.227 (3) | C18—C17 | 1.381 (4) |
N4—C10 | 1.330 (3) | C18—C19 | 1.392 (4) |
N4—H4A | 0.8600 | C18—H18A | 0.9300 |
N4—H4B | 0.8600 | C9—C11 | 1.384 (4) |
N1—C1 | 1.326 (3) | C9—C10 | 1.514 (4) |
N1—C6 | 1.344 (3) | C15—H15A | 0.9300 |
N2—C4 | 1.331 (3) | C19—C20 | 1.505 (4) |
N2—H2A | 0.8600 | C2—H2C | 0.9300 |
N2—H2B | 0.8600 | C11—C12 | 1.375 (4) |
N3—C7 | 1.331 (3) | C11—H11A | 0.9300 |
N3—C12 | 1.335 (3) | C12—H12A | 0.9300 |
C13—C14 | 1.509 (4) | C7—H7A | 0.9300 |
C16—C17 | 1.377 (4) | C6—H6A | 0.9300 |
C16—C15 | 1.385 (4) | C17—H17A | 0.9300 |
C16—H16A | 0.9300 | ||
O6i—Cu1—O3 | 171.25 (8) | C9—C8—H8A | 120.4 |
O6i—Cu1—N1 | 88.08 (8) | C15—C14—C19 | 119.1 (2) |
O3—Cu1—N1 | 90.75 (8) | C15—C14—C13 | 117.9 (2) |
O6i—Cu1—N3 | 91.93 (8) | C19—C14—C13 | 123.0 (2) |
O3—Cu1—N3 | 87.98 (8) | C17—C18—C19 | 120.6 (3) |
N1—Cu1—N3 | 171.72 (9) | C17—C18—H18A | 119.7 |
C13—O3—Cu1 | 107.33 (16) | C19—C18—H18A | 119.7 |
C20—O6—Cu1ii | 123.79 (18) | C8—C9—C11 | 117.8 (2) |
HW1A—OW1—HW1B | 102.2 | C8—C9—C10 | 123.5 (2) |
C10—N4—H4A | 120.0 | C11—C9—C10 | 118.7 (2) |
C10—N4—H4B | 120.0 | C16—C15—C14 | 120.9 (3) |
H4A—N4—H4B | 120.0 | C16—C15—H15A | 119.6 |
C1—N1—C6 | 117.8 (2) | C14—C15—H15A | 119.6 |
C1—N1—Cu1 | 123.62 (18) | O2—C10—N4 | 123.6 (3) |
C6—N1—Cu1 | 118.47 (18) | O2—C10—C9 | 120.0 (2) |
C4—N2—H2A | 120.0 | N4—C10—C9 | 116.4 (2) |
C4—N2—H2B | 120.0 | C18—C19—C14 | 119.4 (2) |
H2A—N2—H2B | 120.0 | C18—C19—C20 | 118.5 (2) |
C7—N3—C12 | 117.8 (2) | C14—C19—C20 | 122.0 (2) |
C7—N3—Cu1 | 119.97 (18) | C3—C2—C1 | 118.8 (2) |
C12—N3—Cu1 | 121.91 (17) | C3—C2—H2C | 120.6 |
O4—C13—O3 | 123.9 (2) | C1—C2—H2C | 120.6 |
O4—C13—C14 | 121.7 (2) | C12—C11—C9 | 119.7 (2) |
O3—C13—C14 | 114.3 (2) | C12—C11—H11A | 120.2 |
C17—C16—C15 | 120.0 (3) | C9—C11—H11A | 120.2 |
C17—C16—H16A | 120.0 | N3—C12—C11 | 122.5 (2) |
C15—C16—H16A | 120.0 | N3—C12—H12A | 118.7 |
C6—C5—C3 | 118.9 (3) | C11—C12—H12A | 118.7 |
C6—C5—H5A | 120.6 | O5—C20—O6 | 125.6 (3) |
C3—C5—H5A | 120.6 | O5—C20—C19 | 119.7 (2) |
O1—C4—N2 | 123.3 (3) | O6—C20—C19 | 114.7 (2) |
O1—C4—C3 | 120.2 (2) | N3—C7—C8 | 123.1 (3) |
N2—C4—C3 | 116.4 (2) | N3—C7—H7A | 118.4 |
N1—C1—C2 | 123.1 (2) | C8—C7—H7A | 118.4 |
N1—C1—H1A | 118.5 | N1—C6—C5 | 123.0 (3) |
C2—C1—H1A | 118.5 | N1—C6—H6A | 118.5 |
C2—C3—C5 | 118.4 (2) | C5—C6—H6A | 118.5 |
C2—C3—C4 | 122.5 (2) | C16—C17—C18 | 119.9 (3) |
C5—C3—C4 | 119.1 (2) | C16—C17—H17A | 120.0 |
C7—C8—C9 | 119.1 (3) | C18—C17—H17A | 120.0 |
C7—C8—H8A | 120.4 | ||
N1—Cu1—O3—C13 | −81.57 (16) | C8—C9—C10—N4 | −23.4 (4) |
N3—Cu1—O3—C13 | 90.24 (16) | C11—C9—C10—N4 | 158.3 (3) |
O6i—Cu1—N1—C1 | 136.7 (2) | C17—C18—C19—C14 | −2.4 (4) |
O3—Cu1—N1—C1 | −52.0 (2) | C17—C18—C19—C20 | 174.6 (3) |
O6i—Cu1—N1—C6 | −46.6 (2) | C15—C14—C19—C18 | 1.7 (4) |
O3—Cu1—N1—C6 | 124.8 (2) | C13—C14—C19—C18 | −177.3 (3) |
O6i—Cu1—N3—C7 | 45.0 (2) | C15—C14—C19—C20 | −175.2 (3) |
O3—Cu1—N3—C7 | −126.2 (2) | C13—C14—C19—C20 | 5.8 (4) |
O6i—Cu1—N3—C12 | −141.7 (2) | C5—C3—C2—C1 | −0.3 (4) |
O3—Cu1—N3—C12 | 47.1 (2) | C4—C3—C2—C1 | 177.2 (2) |
Cu1—O3—C13—O4 | 3.4 (3) | N1—C1—C2—C3 | 1.2 (4) |
Cu1—O3—C13—C14 | −172.49 (16) | C8—C9—C11—C12 | 0.5 (4) |
C6—N1—C1—C2 | −0.7 (4) | C10—C9—C11—C12 | 178.8 (2) |
Cu1—N1—C1—C2 | 176.0 (2) | C7—N3—C12—C11 | −1.0 (4) |
C6—C5—C3—C2 | −1.1 (4) | Cu1—N3—C12—C11 | −174.5 (2) |
C6—C5—C3—C4 | −178.6 (3) | C9—C11—C12—N3 | 0.4 (4) |
O1—C4—C3—C2 | −147.1 (3) | Cu1ii—O6—C20—O5 | 12.9 (4) |
N2—C4—C3—C2 | 34.1 (4) | Cu1ii—O6—C20—C19 | −164.68 (16) |
O1—C4—C3—C5 | 30.4 (4) | C18—C19—C20—O5 | −135.5 (3) |
N2—C4—C3—C5 | −148.4 (3) | C14—C19—C20—O5 | 41.5 (4) |
O4—C13—C14—C15 | −107.9 (3) | C18—C19—C20—O6 | 42.3 (3) |
O3—C13—C14—C15 | 68.1 (3) | C14—C19—C20—O6 | −140.8 (3) |
O4—C13—C14—C19 | 71.2 (4) | C12—N3—C7—C8 | 0.9 (4) |
O3—C13—C14—C19 | −112.8 (3) | Cu1—N3—C7—C8 | 174.5 (2) |
C7—C8—C9—C11 | −0.6 (4) | C9—C8—C7—N3 | −0.1 (5) |
C7—C8—C9—C10 | −178.9 (3) | C1—N1—C6—C5 | −0.8 (4) |
C17—C16—C15—C14 | −2.5 (5) | Cu1—N1—C6—C5 | −177.7 (2) |
C19—C14—C15—C16 | 0.7 (4) | C3—C5—C6—N1 | 1.7 (4) |
C13—C14—C15—C16 | 179.8 (3) | C15—C16—C17—C18 | 1.8 (5) |
C8—C9—C10—O2 | 157.5 (3) | C19—C18—C17—C16 | 0.7 (5) |
C11—C9—C10—O2 | −20.8 (4) |
Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) x+1/2, −y+1/2, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
OW1—HW1A···O5i | 0.89 | 1.87 | 2.735 (3) | 163 |
OW1—HW1B···O4iii | 0.92 | 2.12 | 3.042 (3) | 176 |
N4—H4A···O1iv | 0.86 | 2.18 | 3.015 (3) | 165 |
N4—H4B···O3v | 0.86 | 2.31 | 3.112 (3) | 155 |
N2—H2A···O2vi | 0.86 | 2.13 | 2.946 (3) | 159 |
N2—H2B···OW1ii | 0.86 | 2.46 | 3.175 (3) | 141 |
Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) x+1/2, −y+1/2, z−1/2; (iii) x+1/2, −y+1/2, z+1/2; (iv) −x+1/2, y−1/2, −z+3/2; (v) x−1, y, z; (vi) −x+3/2, y+1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | [Cu(C6H6N2O)2(C8H4O4)]·H2O |
Mr | 489.92 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 8.023 (2), 22.903 (6), 11.473 (3) |
β (°) | 97.128 (3) |
V (Å3) | 2091.7 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.10 |
Crystal size (mm) | 0.38 × 0.16 × 0.09 |
Data collection | |
Diffractometer | Bruker APEX I CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2002) |
Tmin, Tmax | 0.813, 0.903 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17837, 4106, 3171 |
Rint | 0.047 |
(sin θ/λ)max (Å−1) | 0.618 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.088, 1.04 |
No. of reflections | 4106 |
No. of parameters | 291 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.30, −0.34 |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXL97.
Cu1—O6i | 1.9409 (18) | Cu1—N1 | 2.006 (2) |
Cu1—O3 | 1.9610 (17) | Cu1—N3 | 2.008 (2) |
Symmetry code: (i) x−1/2, −y+1/2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
OW1—HW1A···O5i | 0.89 | 1.87 | 2.735 (3) | 163 |
OW1—HW1B···O4ii | 0.92 | 2.12 | 3.042 (3) | 176 |
N4—H4A···O1iii | 0.86 | 2.18 | 3.015 (3) | 165 |
N4—H4B···O3iv | 0.86 | 2.31 | 3.112 (3) | 155 |
N2—H2A···O2v | 0.86 | 2.13 | 2.946 (3) | 159 |
N2—H2B···OW1vi | 0.86 | 2.46 | 3.175 (3) | 141 |
Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) x+1/2, −y+1/2, z+1/2; (iii) −x+1/2, y−1/2, −z+3/2; (iv) x−1, y, z; (v) −x+3/2, y+1/2, −z+3/2; (vi) x+1/2, −y+1/2, z−1/2. |
Organic amides have proved to be useful in self-assembling coordination compounds through hydrogen bonding (e.g. Bhogala et al., 2004). To augment this family, we obtained the title compound, (I), (Fig. 1), by choosing benzene-1,2-dicarboxylate, isonicotinamide and CuII as the staring materials.
Compound (I) is constructed from the basic unit [Cu(C6H6N2O)2(C8H4O4)].H2O. The CuII center shows a square planar coordination geometry, being coordinated by two N atoms of two isonicotinamide molecules and two O atoms from two benzene-1,2-dicarboxylate dianions (Table 1). Each benzene-1,2-dicarboxylate ligand bridges two CuII centers to form an infinite zigzag chain.
Hydrogen-bonding interactions generate a three-dimensional network in the crystal strcture of (I) (Table 2, Fig. 2). Thus, compound (I) can be considered as a three-dimensional supramolecular array stabilized by hydrogen-bonding interactions.