Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807035040/cf2124sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807035040/cf2124Isup2.hkl |
CCDC reference: 657620
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.003 Å
- R factor = 0.033
- wR factor = 0.086
- Data-to-parameter ratio = 18.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.04 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.13 Ratio PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1 (2) 2.11 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
Copper(II) nitrate 2.5-hydrate (0.025 g, 0.11 mmol), terephthalic acid (0.018 g, 0.11 mmol) and 4,4'-bipyridine (0.009 g, 0.06 mmol) in DMF/ethanol/water (3 ml/3 ml/2 ml) were heated at 348 K for several days. Small, dark blue crystals were collected from the cooled solution in 70% yield.
Carbon-bound hydrogen atoms were placed at calculated positions (C—H = 0.95–0.98 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2–1.5 times Ueq(C). The water H atoms were located in a difference Fourier map and were refined with a distance restraint of O—H = 0.84 (1) Å; the displacement parameters were freely refined.
The hydrothermal reaction of copper(II) nitrate, terephthalic acid and 4,4'-bipyridine furnishes the expected copper terephthalate adduct with 4,4'-bipyridine as a 1/1 cocrystal with terephthalic acid. The compound adopts a layer structure and the terephthalic acid behaves as a guest molecule in the porous host (Baeg & Lee, 2003). With the addition of DMF in the hydrothermal synthesis, the dimensionality of the product is lowered to a ladder structure in the present study. The compound is formally (C10H8N2)(C8H4O4)2(C3H7NO)2(H2O)2Cu2; the terephthalate represents the rails of the ladder and the N-heterocycle the rungs. The copper atom is also coordinated by water and DMF in a square-pyramidal geometry. Although the ladder appears to have voids (Fig. 2), these are actually occupied by the DMF ligands of adjacent ladders, and there are no empty spaces in the crystal structure.
For the crystal structure of a copper terephthalate-4,4'-bipyridine cocrystal with terephthalic acid, see Baeg & Lee (2003).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).
[Cu2(C8H4O4)2(C10H8N2)(C3H7NO)2(H2O)2] | F(000) = 816 |
Mr = 793.71 | Dx = 1.599 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4717 reflections |
a = 10.8424 (2) Å | θ = 2.4–27.3° |
b = 14.3465 (3) Å | µ = 1.36 mm−1 |
c = 11.1929 (2) Å | T = 173 K |
β = 108.741 (1)° | Prism, blue |
V = 1648.75 (5) Å3 | 0.15 × 0.03 × 0.02 mm |
Z = 2 |
Bruker X8 APEXII diffractometer | 4415 independent reflections |
Radiation source: fine-focus sealed tube | 3131 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
φ and ω scans | θmax = 29.4°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→14 |
Tmin = 0.813, Tmax = 0.973 | k = −19→19 |
21007 measured reflections | l = −15→15 |
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)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.086 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0434P)2 + 0.0236P] where P = (Fo2 + 2Fc2)/3 |
4415 reflections | (Δ/σ)max = 0.001 |
236 parameters | Δρmax = 0.47 e Å−3 |
2 restraints | Δρmin = −0.45 e Å−3 |
[Cu2(C8H4O4)2(C10H8N2)(C3H7NO)2(H2O)2] | V = 1648.75 (5) Å3 |
Mr = 793.71 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.8424 (2) Å | µ = 1.36 mm−1 |
b = 14.3465 (3) Å | T = 173 K |
c = 11.1929 (2) Å | 0.15 × 0.03 × 0.02 mm |
β = 108.741 (1)° |
Bruker X8 APEXII diffractometer | 4415 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3131 reflections with I > 2σ(I) |
Tmin = 0.813, Tmax = 0.973 | Rint = 0.043 |
21007 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | 2 restraints |
wR(F2) = 0.086 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.47 e Å−3 |
4415 reflections | Δρmin = −0.45 e Å−3 |
236 parameters |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.53837 (2) | 0.371184 (17) | 0.64815 (2) | 0.01513 (8) | |
O1 | 0.35686 (13) | 0.37764 (9) | 0.64009 (13) | 0.0196 (3) | |
O2 | 0.27817 (13) | 0.40992 (10) | 0.43389 (12) | 0.0198 (3) | |
O3 | −0.35170 (13) | 0.37559 (10) | 0.45053 (13) | 0.0222 (3) | |
O4 | −0.27850 (13) | 0.36803 (9) | 0.66048 (13) | 0.0192 (3) | |
O5 | 0.59539 (14) | 0.34997 (10) | 0.86385 (13) | 0.0250 (3) | |
O1w | 0.55072 (14) | 0.50852 (10) | 0.65718 (13) | 0.0183 (3) | |
H1w1 | 0.6064 (19) | 0.5313 (18) | 0.629 (2) | 0.050 (9)* | |
H1w2 | 0.4812 (15) | 0.5389 (15) | 0.625 (2) | 0.037 (7)* | |
N1 | 0.52007 (16) | 0.23600 (12) | 0.59914 (15) | 0.0169 (4) | |
N2 | 0.5139 (2) | 0.37178 (13) | 1.02550 (16) | 0.0292 (4) | |
C1 | 0.6080 (2) | 0.17317 (15) | 0.66171 (18) | 0.0218 (5) | |
H1 | 0.6770 | 0.1931 | 0.7336 | 0.026* | |
C2 | 0.6031 (2) | 0.08068 (15) | 0.62679 (18) | 0.0227 (5) | |
H2 | 0.6676 | 0.0384 | 0.6747 | 0.027* | |
C3 | 0.50411 (19) | 0.04921 (14) | 0.52162 (17) | 0.0165 (4) | |
C4 | 0.4123 (2) | 0.11503 (14) | 0.45831 (19) | 0.0232 (5) | |
H4 | 0.3416 | 0.0972 | 0.3866 | 0.028* | |
C5 | 0.4237 (2) | 0.20588 (15) | 0.49936 (19) | 0.0239 (5) | |
H5 | 0.3596 | 0.2494 | 0.4543 | 0.029* | |
C6 | 0.26399 (19) | 0.39180 (13) | 0.53743 (18) | 0.0164 (4) | |
C7 | 0.12944 (18) | 0.38330 (13) | 0.54406 (18) | 0.0158 (4) | |
C8 | 0.02418 (19) | 0.39287 (14) | 0.43468 (18) | 0.0188 (4) | |
H8 | 0.0387 | 0.4034 | 0.3565 | 0.023* | |
C9 | −0.10098 (19) | 0.38726 (14) | 0.43854 (18) | 0.0196 (4) | |
H9 | −0.1722 | 0.3932 | 0.3628 | 0.024* | |
C10 | −0.12433 (19) | 0.37297 (13) | 0.55176 (18) | 0.0164 (4) | |
C11 | −0.0189 (2) | 0.36227 (15) | 0.66153 (19) | 0.0238 (5) | |
H11 | −0.0335 | 0.3517 | 0.7397 | 0.029* | |
C12 | 0.1059 (2) | 0.36693 (15) | 0.65759 (19) | 0.0231 (5) | |
H12 | 0.1771 | 0.3589 | 0.7330 | 0.028* | |
C13 | −0.26200 (19) | 0.37214 (13) | 0.55229 (19) | 0.0173 (4) | |
C14 | 0.5048 (2) | 0.35112 (15) | 0.90772 (19) | 0.0236 (5) | |
H14 | 0.4208 | 0.3358 | 0.8520 | 0.028* | |
C15 | 0.4001 (3) | 0.37555 (17) | 1.0660 (2) | 0.0390 (6) | |
H15A | 0.3244 | 0.3522 | 0.9984 | 0.058* | |
H15B | 0.3844 | 0.4401 | 1.0856 | 0.058* | |
H15C | 0.4145 | 0.3368 | 1.1414 | 0.058* | |
C16 | 0.6383 (3) | 0.3923 (2) | 1.1183 (2) | 0.0481 (7) | |
H16A | 0.7072 | 0.3867 | 1.0796 | 0.072* | |
H16B | 0.6548 | 0.3483 | 1.1887 | 0.072* | |
H16C | 0.6373 | 0.4560 | 1.1497 | 0.072* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.00697 (13) | 0.02238 (14) | 0.01633 (13) | −0.00036 (10) | 0.00415 (9) | −0.00054 (10) |
O1 | 0.0070 (7) | 0.0310 (8) | 0.0204 (7) | −0.0001 (6) | 0.0038 (6) | −0.0001 (6) |
O2 | 0.0123 (7) | 0.0279 (8) | 0.0207 (7) | −0.0020 (6) | 0.0076 (6) | 0.0006 (6) |
O3 | 0.0092 (7) | 0.0330 (9) | 0.0233 (7) | 0.0020 (6) | 0.0037 (6) | 0.0009 (6) |
O4 | 0.0108 (7) | 0.0275 (8) | 0.0207 (7) | −0.0001 (6) | 0.0070 (6) | 0.0002 (6) |
O5 | 0.0178 (8) | 0.0371 (9) | 0.0197 (7) | −0.0011 (7) | 0.0054 (6) | 0.0013 (6) |
O1w | 0.0109 (8) | 0.0234 (8) | 0.0219 (7) | −0.0002 (6) | 0.0069 (6) | 0.0013 (6) |
N1 | 0.0108 (8) | 0.0241 (9) | 0.0161 (8) | 0.0004 (7) | 0.0046 (6) | 0.0004 (7) |
N2 | 0.0340 (12) | 0.0355 (11) | 0.0175 (9) | 0.0008 (9) | 0.0075 (8) | −0.0031 (8) |
C1 | 0.0176 (11) | 0.0270 (12) | 0.0175 (10) | −0.0003 (9) | 0.0008 (8) | 0.0003 (9) |
C2 | 0.0187 (11) | 0.0243 (12) | 0.0200 (10) | 0.0020 (9) | −0.0008 (9) | 0.0021 (9) |
C3 | 0.0125 (10) | 0.0247 (11) | 0.0140 (9) | 0.0000 (8) | 0.0063 (8) | 0.0028 (8) |
C4 | 0.0154 (10) | 0.0266 (12) | 0.0217 (10) | 0.0023 (9) | −0.0024 (9) | −0.0030 (9) |
C5 | 0.0158 (11) | 0.0256 (12) | 0.0249 (11) | 0.0040 (9) | −0.0010 (9) | −0.0013 (9) |
C6 | 0.0122 (10) | 0.0158 (10) | 0.0224 (10) | −0.0008 (8) | 0.0073 (8) | −0.0017 (8) |
C7 | 0.0097 (9) | 0.0183 (10) | 0.0206 (10) | 0.0008 (8) | 0.0066 (8) | 0.0010 (8) |
C8 | 0.0147 (10) | 0.0259 (11) | 0.0174 (9) | −0.0005 (9) | 0.0075 (8) | −0.0012 (8) |
C9 | 0.0096 (9) | 0.0283 (12) | 0.0192 (10) | 0.0012 (8) | 0.0023 (8) | −0.0022 (8) |
C10 | 0.0089 (9) | 0.0180 (10) | 0.0238 (10) | −0.0001 (8) | 0.0075 (8) | −0.0007 (8) |
C11 | 0.0140 (11) | 0.0383 (13) | 0.0212 (10) | 0.0021 (9) | 0.0088 (8) | 0.0067 (9) |
C12 | 0.0109 (10) | 0.0372 (13) | 0.0199 (10) | 0.0016 (9) | 0.0031 (8) | 0.0043 (9) |
C13 | 0.0105 (9) | 0.0169 (10) | 0.0259 (10) | −0.0001 (8) | 0.0077 (8) | −0.0005 (8) |
C14 | 0.0251 (12) | 0.0275 (12) | 0.0159 (10) | −0.0003 (9) | 0.0036 (9) | 0.0012 (8) |
C15 | 0.0495 (17) | 0.0443 (16) | 0.0333 (13) | 0.0032 (13) | 0.0275 (12) | −0.0036 (11) |
C16 | 0.0508 (18) | 0.0621 (19) | 0.0228 (12) | −0.0050 (14) | −0.0001 (12) | −0.0094 (12) |
Cu1—O1 | 1.943 (1) | C3—C3iii | 1.486 (4) |
Cu1—O4i | 1.946 (1) | C4—C5 | 1.374 (3) |
Cu1—O5 | 2.312 (1) | C4—H4 | 0.950 |
Cu1—O1w | 1.975 (2) | C5—H5 | 0.950 |
Cu1—N1 | 2.008 (2) | C6—C7 | 1.489 (3) |
O1—C6 | 1.277 (2) | C7—C8 | 1.387 (3) |
O2—C6 | 1.245 (2) | C7—C12 | 1.394 (3) |
O3—C13 | 1.238 (2) | C8—C9 | 1.374 (3) |
O4—C13 | 1.281 (2) | C8—H8 | 0.950 |
O4—Cu1ii | 1.9462 (14) | C9—C10 | 1.385 (3) |
O5—C14 | 1.231 (3) | C9—H9 | 0.950 |
O1w—H1w1 | 0.83 (1) | C10—C11 | 1.392 (3) |
O1w—H1w2 | 0.84 (1) | C10—C13 | 1.495 (3) |
N1—C5 | 1.333 (3) | C11—C12 | 1.369 (3) |
N1—C1 | 1.335 (3) | C11—H11 | 0.950 |
N2—C14 | 1.324 (3) | C12—H12 | 0.950 |
N2—C16 | 1.444 (3) | C14—H14 | 0.950 |
N2—C15 | 1.445 (3) | C15—H15A | 0.980 |
C1—C2 | 1.379 (3) | C15—H15B | 0.980 |
C1—H1 | 0.950 | C15—H15C | 0.980 |
C2—C3 | 1.389 (3) | C16—H16A | 0.980 |
C2—H2 | 0.950 | C16—H16B | 0.980 |
C3—C4 | 1.390 (3) | C16—H16C | 0.980 |
O1—Cu1—O4i | 178.07 (6) | O2—C6—C7 | 118.66 (17) |
O1—Cu1—O1w | 90.33 (6) | O1—C6—C7 | 116.35 (17) |
O4i—Cu1—O1w | 88.21 (6) | C8—C7—C12 | 118.79 (18) |
O1—Cu1—N1 | 91.36 (6) | C8—C7—C6 | 119.31 (17) |
O4i—Cu1—N1 | 90.34 (6) | C12—C7—C6 | 121.90 (17) |
O1w—Cu1—N1 | 167.58 (6) | C9—C8—C7 | 120.50 (18) |
O1—Cu1—O5 | 88.96 (6) | C9—C8—H8 | 119.8 |
O4i—Cu1—O5 | 89.91 (5) | C7—C8—H8 | 119.8 |
O1w—Cu1—O5 | 94.98 (5) | C8—C9—C10 | 120.69 (18) |
N1—Cu1—O5 | 97.35 (6) | C8—C9—H9 | 119.7 |
C6—O1—Cu1 | 122.90 (13) | C10—C9—H9 | 119.7 |
C13—O4—Cu1ii | 112.40 (12) | C9—C10—C11 | 118.94 (18) |
C14—O5—Cu1 | 115.77 (13) | C9—C10—C13 | 118.77 (17) |
Cu1—O1w—H1w1 | 114.6 (19) | C11—C10—C13 | 122.27 (18) |
Cu1—O1w—H1w2 | 117.2 (17) | C12—C11—C10 | 120.41 (19) |
H1w1—O1w—H1w2 | 107 (3) | C12—C11—H11 | 119.8 |
C5—N1—C1 | 117.13 (18) | C10—C11—H11 | 119.8 |
C5—N1—Cu1 | 121.62 (14) | C11—C12—C7 | 120.65 (19) |
C1—N1—Cu1 | 121.18 (14) | C11—C12—H12 | 119.7 |
C14—N2—C16 | 121.0 (2) | C7—C12—H12 | 119.7 |
C14—N2—C15 | 121.5 (2) | O3—C13—O4 | 124.35 (18) |
C16—N2—C15 | 117.4 (2) | O3—C13—C10 | 119.09 (18) |
N1—C1—C2 | 123.03 (18) | O4—C13—C10 | 116.56 (17) |
N1—C1—H1 | 118.5 | O5—C14—N2 | 125.9 (2) |
C2—C1—H1 | 118.5 | O5—C14—H14 | 117.0 |
C1—C2—C3 | 120.10 (19) | N2—C14—H14 | 117.0 |
C1—C2—H2 | 120.0 | N2—C15—H15A | 109.5 |
C3—C2—H2 | 120.0 | N2—C15—H15B | 109.5 |
C2—C3—C4 | 116.30 (19) | H15A—C15—H15B | 109.5 |
C2—C3—C3iii | 122.3 (2) | N2—C15—H15C | 109.5 |
C4—C3—C3iii | 121.4 (2) | H15A—C15—H15C | 109.5 |
C5—C4—C3 | 120.08 (18) | H15B—C15—H15C | 109.5 |
C5—C4—H4 | 120.0 | N2—C16—H16A | 109.5 |
C3—C4—H4 | 120.0 | N2—C16—H16B | 109.5 |
N1—C5—C4 | 123.35 (19) | H16A—C16—H16B | 109.5 |
N1—C5—H5 | 118.3 | N2—C16—H16C | 109.5 |
C4—C5—H5 | 118.3 | H16A—C16—H16C | 109.5 |
O2—C6—O1 | 124.98 (18) | H16B—C16—H16C | 109.5 |
O1w—Cu1—O1—C6 | 83.52 (14) | Cu1—O1—C6—O2 | −5.7 (3) |
N1—Cu1—O1—C6 | −84.17 (15) | Cu1—O1—C6—C7 | 172.75 (12) |
O5—Cu1—O1—C6 | 178.50 (14) | O2—C6—C7—C8 | 2.0 (3) |
O1—Cu1—O5—C14 | −1.64 (15) | O1—C6—C7—C8 | −176.58 (17) |
O4i—Cu1—O5—C14 | 176.79 (15) | O2—C6—C7—C12 | −177.32 (19) |
O1w—Cu1—O5—C14 | 88.60 (15) | O1—C6—C7—C12 | 4.1 (3) |
N1—Cu1—O5—C14 | −92.88 (15) | C12—C7—C8—C9 | 0.7 (3) |
O1—Cu1—N1—C5 | 50.14 (17) | C6—C7—C8—C9 | −178.65 (18) |
O4i—Cu1—N1—C5 | −130.78 (17) | C7—C8—C9—C10 | 0.7 (3) |
O1w—Cu1—N1—C5 | −47.6 (4) | C8—C9—C10—C11 | −1.4 (3) |
O5—Cu1—N1—C5 | 139.27 (16) | C8—C9—C10—C13 | 176.95 (18) |
O1—Cu1—N1—C1 | −133.23 (16) | C9—C10—C11—C12 | 0.8 (3) |
O4i—Cu1—N1—C1 | 45.85 (16) | C13—C10—C11—C12 | −177.54 (19) |
O1w—Cu1—N1—C1 | 129.0 (3) | C10—C11—C12—C7 | 0.6 (3) |
O5—Cu1—N1—C1 | −44.10 (16) | C8—C7—C12—C11 | −1.3 (3) |
C5—N1—C1—C2 | 0.6 (3) | C6—C7—C12—C11 | 177.98 (19) |
Cu1—N1—C1—C2 | −176.20 (16) | Cu1ii—O4—C13—O3 | −1.6 (2) |
N1—C1—C2—C3 | 0.5 (3) | Cu1ii—O4—C13—C10 | 178.28 (12) |
C1—C2—C3—C4 | −1.3 (3) | C9—C10—C13—O3 | 6.6 (3) |
C1—C2—C3—C3iii | 178.7 (2) | C11—C10—C13—O3 | −175.09 (19) |
C2—C3—C4—C5 | 1.1 (3) | C9—C10—C13—O4 | −173.25 (17) |
C3iii—C3—C4—C5 | −178.9 (2) | C11—C10—C13—O4 | 5.1 (3) |
C1—N1—C5—C4 | −0.8 (3) | Cu1—O5—C14—N2 | −155.75 (18) |
Cu1—N1—C5—C4 | 175.95 (16) | C16—N2—C14—O5 | −2.5 (3) |
C3—C4—C5—N1 | 0.0 (3) | C15—N2—C14—O5 | 176.9 (2) |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) −x+1, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w1···O2iv | 0.83 (1) | 1.83 (1) | 2.658 (2) | 175 (3) |
O1w—H1w2···O3v | 0.84 (1) | 1.85 (1) | 2.684 (2) | 168 (3) |
Symmetry codes: (iv) −x+1, −y+1, −z+1; (v) −x, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Cu2(C8H4O4)2(C10H8N2)(C3H7NO)2(H2O)2] |
Mr | 793.71 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 173 |
a, b, c (Å) | 10.8424 (2), 14.3465 (3), 11.1929 (2) |
β (°) | 108.741 (1) |
V (Å3) | 1648.75 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.36 |
Crystal size (mm) | 0.15 × 0.03 × 0.02 |
Data collection | |
Diffractometer | Bruker X8 APEXII |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.813, 0.973 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21007, 4415, 3131 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.691 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.086, 1.04 |
No. of reflections | 4415 |
No. of parameters | 236 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.47, −0.45 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), publCIF (Westrip, 2007).
Cu1—O1 | 1.943 (1) | Cu1—O1w | 1.975 (2) |
Cu1—O4i | 1.946 (1) | Cu1—N1 | 2.008 (2) |
Cu1—O5 | 2.312 (1) |
Symmetry code: (i) x+1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w1···O2ii | 0.83 (1) | 1.83 (1) | 2.658 (2) | 175 (3) |
O1w—H1w2···O3iii | 0.84 (1) | 1.85 (1) | 2.684 (2) | 168 (3) |
Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z+1. |
The hydrothermal reaction of copper(II) nitrate, terephthalic acid and 4,4'-bipyridine furnishes the expected copper terephthalate adduct with 4,4'-bipyridine as a 1/1 cocrystal with terephthalic acid. The compound adopts a layer structure and the terephthalic acid behaves as a guest molecule in the porous host (Baeg & Lee, 2003). With the addition of DMF in the hydrothermal synthesis, the dimensionality of the product is lowered to a ladder structure in the present study. The compound is formally (C10H8N2)(C8H4O4)2(C3H7NO)2(H2O)2Cu2; the terephthalate represents the rails of the ladder and the N-heterocycle the rungs. The copper atom is also coordinated by water and DMF in a square-pyramidal geometry. Although the ladder appears to have voids (Fig. 2), these are actually occupied by the DMF ligands of adjacent ladders, and there are no empty spaces in the crystal structure.