Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027663/xu2271sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027663/xu2271Isup2.hkl |
CCDC reference: 654737
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.006 Å
- Disorder in main residue
- R factor = 0.066
- wR factor = 0.225
- Data-to-parameter ratio = 16.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 500 Ang. PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O4 PLAT301_ALERT_3_C Main Residue Disorder ......................... 5.00 Perc.
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 16
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For copper terephthalate adducts with 1,10-phenanthroline, see: Sun et al. (2001); Marsh (2004); Rogan et al. (2004). For a discussion on the distortion of square-planar geometries of copper carboxylates, see: Li et al. (2005). For related literature, see: Bailey & Brown (1967); Li et al. (2006).
A mixture of copper(II) hydoxide carbonate (0.203 g, 1 mmol)), terephthalic acid (0.164 g, 1 mmo1) and 4,7-dimethyl-1,10-phenanthroline (0.062 g, 0.3 mmol) and water (16 ml) was placed in a 25-ml, Teflon-lined, stainless steel Parr bomb. The bomb was heated to 453 K for 72 h. It was cooled to room temperature over 72 h to furnish several blue prismatic crystals.
The structure when refined with only the atoms comprising the (C14H14N2)(C8H4O4)Cu portion of the asymmetric refined to a satisfactory R-index but with two voids of 382 Å3, each about a center-of-inversion. As the terephthalic acid itself is a centrosymmetric molecule displaying a volume of 174.8 Å3 (Bailey & Brown, 1967), the voids of the unit cell should accommodate four terephthalic acid molecules.
The electron densities in the difference Fourier map were allowed to refine off the symmetry element, as a half-occupancy C8H6O4 molecule. The aromatic ring was refined as a rigid hexagon of 1.39 Å sides; the C–C distances were restrained to 1.50±0.01 Å and the C–O distances to 1.25±0.01 Å. The two –C—C(=O)–OH units were restrained to be nearly flat, and other distances restraints were use to ensure sensible bond angles. The temperature factors of all C– and O-atoms were restrained to equal each other. The atoms were refined isotropically.
The H-atoms were placed in calculated positions (O–H 0.82 Å and C–H 0.93 Å), and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C,O).
The final difference Fourier map had a large peak near the disordered terephthalic acid molecule.
Copper terephthalate forms adducts with 1,10-phenanthroline; the 1:1 adduct has been isolated as an anhydrous (Sun et al., 2001; Marsh, 2004) as well as a monoaqua (Rogan et al., 2004) compound in which the dicarboxylate dianion functions as a bridging entity. A 1:2 adduct is known having two monodeprotonated carboxylate groups (Li et al., 2006). Copper(II) terephthalate–dimethylphenanthroline crystallizes as a 1:0.5 cocrystal, (C14H14N2)(C8H4O4)Cu.0.5C8H6O4, the terephthalate dianion links adjacent copper atoms into a zigzag chain, the kink at the metal linkage being nearly a right angle. The metal atom shows square-planar coordination; if the long double-bonded oxygen atoms that are more than 2.5 Å away are considered, then the geometry is an octahedron. The lattice terephthalic acid molecule is disordered about a center-of-inversion; it occupies the space between chains but is not hydrogen bonded to any.
For copper terephthalate adducts with 1,10-phenanthroline, see: Sun et al. (2001); Marsh (2004); Rogan et al. (2004). For a discussion on the distortion of square-planar geometries of copper carboxylates, see: Li et al. (2005). For related literature, see: Bailey & Brown (1967); Li et al. (2006).
Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystaClear; 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).
[Cu(C8H4O4)(C14H12N2)]·0.5C8H6O4 | F(000) = 2128 |
Mr = 518.97 | Dx = 1.585 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 5331 reflections |
a = 18.764 (5) Å | θ = 2.7–27.5° |
b = 17.769 (5) Å | µ = 1.05 mm−1 |
c = 14.749 (5) Å | T = 295 K |
β = 117.841 (5)° | Prism, blue |
V = 4348 (2) Å3 | 0.33 × 0.20 × 0.08 mm |
Z = 8 |
Rigaku Mercury CCD diffractometer | 4914 independent reflections |
Radiation source: fine-focus sealed tube | 4295 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ω scans | θmax = 27.5°, θmin = 2.3° |
Absorption correction: multi-scan (CrystalStructure; Rigaku, 2000) | h = −20→24 |
Tmin = 0.828, Tmax = 0.921 | k = −23→23 |
16066 measured reflections | l = −19→19 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.066 | H-atom parameters constrained |
wR(F2) = 0.225 | w = 1/[σ2(Fo2) + (0.1414P)2 + 6.3201P] where P = (Fo2 + 2Fc2)/3 |
S = 1.15 | (Δ/σ)max = 0.001 |
4914 reflections | Δρmax = 1.41 e Å−3 |
290 parameters | Δρmin = −0.88 e Å−3 |
16 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.017 (2) |
[Cu(C8H4O4)(C14H12N2)]·0.5C8H6O4 | V = 4348 (2) Å3 |
Mr = 518.97 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 18.764 (5) Å | µ = 1.05 mm−1 |
b = 17.769 (5) Å | T = 295 K |
c = 14.749 (5) Å | 0.33 × 0.20 × 0.08 mm |
β = 117.841 (5)° |
Rigaku Mercury CCD diffractometer | 4914 independent reflections |
Absorption correction: multi-scan (CrystalStructure; Rigaku, 2000) | 4295 reflections with I > 2σ(I) |
Tmin = 0.828, Tmax = 0.921 | Rint = 0.030 |
16066 measured reflections |
R[F2 > 2σ(F2)] = 0.066 | 16 restraints |
wR(F2) = 0.225 | H-atom parameters constrained |
S = 1.15 | Δρmax = 1.41 e Å−3 |
4914 reflections | Δρmin = −0.88 e Å−3 |
290 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cu1 | 0.25030 (3) | 0.53888 (2) | 0.62123 (3) | 0.0363 (3) | |
O1 | 0.30675 (15) | 0.50921 (15) | 0.76751 (19) | 0.0415 (6) | |
O2 | 0.39382 (18) | 0.57136 (17) | 0.7350 (2) | 0.0514 (7) | |
O3 | 0.28153 (19) | 0.44917 (15) | 0.5707 (2) | 0.0483 (7) | |
O4 | 0.1733 (2) | 0.41283 (19) | 0.5821 (3) | 0.0599 (8) | |
N1 | 0.20944 (18) | 0.59243 (18) | 0.4862 (2) | 0.0375 (6) | |
N2 | 0.19708 (19) | 0.62594 (16) | 0.6513 (2) | 0.0377 (6) | |
C1 | 0.3768 (2) | 0.53507 (18) | 0.7936 (3) | 0.0376 (8) | |
C2 | 0.4409 (2) | 0.51817 (18) | 0.9015 (3) | 0.0339 (7) | |
C3 | 0.4211 (2) | 0.5079 (2) | 0.9807 (3) | 0.0395 (7) | |
H3 | 0.3679 | 0.5139 | 0.9677 | 0.047* | |
C4 | 0.4796 (2) | 0.4888 (2) | 1.0790 (3) | 0.0396 (8) | |
H4 | 0.4656 | 0.4808 | 1.1310 | 0.048* | |
C5 | 0.2296 (3) | 0.3998 (2) | 0.5624 (3) | 0.0429 (8) | |
C6 | 0.2401 (2) | 0.3225 (2) | 0.5288 (3) | 0.0400 (8) | |
C7 | 0.3078 (3) | 0.3049 (2) | 0.5186 (3) | 0.0433 (8) | |
H7 | 0.3466 | 0.3416 | 0.5305 | 0.052* | |
C8 | 0.3184 (3) | 0.2329 (2) | 0.4908 (3) | 0.0440 (8) | |
H8 | 0.3645 | 0.2213 | 0.4851 | 0.053* | |
C9 | 0.2153 (2) | 0.5730 (2) | 0.4036 (3) | 0.0455 (9) | |
H9 | 0.2374 | 0.5264 | 0.4024 | 0.055* | |
C10 | 0.1896 (3) | 0.6197 (3) | 0.3179 (3) | 0.0512 (10) | |
H10 | 0.1956 | 0.6040 | 0.2617 | 0.061* | |
C11 | 0.1557 (2) | 0.6885 (2) | 0.3155 (3) | 0.0471 (9) | |
C12 | 0.1270 (4) | 0.7387 (4) | 0.2239 (4) | 0.0724 (15) | |
H12A | 0.1454 | 0.7195 | 0.1776 | 0.109* | |
H12B | 0.1480 | 0.7885 | 0.2453 | 0.109* | |
H12C | 0.0692 | 0.7403 | 0.1899 | 0.109* | |
C13 | 0.1481 (2) | 0.7105 (2) | 0.4034 (3) | 0.0402 (8) | |
C14 | 0.1757 (2) | 0.6606 (2) | 0.4854 (3) | 0.0364 (7) | |
C15 | 0.1137 (3) | 0.7799 (2) | 0.4124 (3) | 0.0511 (10) | |
H15 | 0.0966 | 0.8147 | 0.3593 | 0.061* | |
C16 | 0.1053 (3) | 0.7962 (2) | 0.4971 (3) | 0.0529 (10) | |
H16 | 0.0818 | 0.8416 | 0.5000 | 0.063* | |
C17 | 0.1317 (2) | 0.7453 (2) | 0.5817 (3) | 0.0409 (8) | |
C18 | 0.1680 (2) | 0.67809 (19) | 0.5755 (3) | 0.0346 (7) | |
C19 | 0.1238 (3) | 0.7575 (2) | 0.6720 (3) | 0.0499 (10) | |
C20 | 0.0834 (4) | 0.8272 (3) | 0.6848 (5) | 0.0779 (17) | |
H20A | 0.0665 | 0.8184 | 0.7361 | 0.117* | |
H20B | 0.0373 | 0.8392 | 0.6208 | 0.117* | |
H20C | 0.1207 | 0.8685 | 0.7056 | 0.117* | |
C21 | 0.1524 (3) | 0.7029 (2) | 0.7462 (3) | 0.0511 (10) | |
H21 | 0.1472 | 0.7092 | 0.8054 | 0.061* | |
C22 | 0.1889 (3) | 0.6385 (2) | 0.7348 (3) | 0.0465 (9) | |
H22 | 0.2083 | 0.6029 | 0.7871 | 0.056* | |
O5 | −0.014 (2) | 0.4403 (15) | 0.4138 (17) | 0.247 (5)* | 0.50 |
H5O | −0.0152 | 0.4371 | 0.4758 | 0.297* | 0.50 |
O6 | 0.002 (3) | 0.5681 (15) | 0.422 (2) | 0.247 (5)* | 0.50 |
O7 | 0.0155 (19) | 0.5688 (17) | −0.0359 (17) | 0.247 (5)* | 0.50 |
H7O | 0.0177 | 0.5738 | −0.0973 | 0.297* | 0.50 |
O8 | −0.005 (3) | 0.4375 (16) | −0.0488 (18) | 0.247 (5)* | 0.50 |
C23 | −0.004 (3) | 0.5035 (12) | 0.2799 (17) | 0.247 (5)* | 0.50 |
C24 | 0.004 (3) | 0.4358 (12) | 0.2378 (19) | 0.247 (5)* | 0.50 |
H24 | 0.0072 | 0.3908 | 0.2715 | 0.297* | 0.50 |
C25 | 0.007 (2) | 0.4356 (12) | 0.1453 (17) | 0.247 (5)* | 0.50 |
H25 | 0.0119 | 0.3904 | 0.1171 | 0.297* | 0.50 |
C26 | 0.002 (2) | 0.5030 (12) | 0.0949 (16) | 0.247 (5)* | 0.50 |
C27 | −0.005 (2) | 0.5706 (12) | 0.1371 (18) | 0.247 (5)* | 0.50 |
H27 | −0.0086 | 0.6157 | 0.1034 | 0.297* | 0.50 |
C28 | −0.008 (2) | 0.5708 (11) | 0.2296 (18) | 0.247 (5)* | 0.50 |
H28 | −0.0133 | 0.6161 | 0.2578 | 0.297* | 0.50 |
C29 | −0.0052 (14) | 0.5040 (13) | 0.3804 (12) | 0.247 (5)* | 0.50 |
C30 | 0.0043 (13) | 0.5031 (15) | −0.0064 (11) | 0.247 (5)* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0400 (4) | 0.0313 (3) | 0.0304 (3) | 0.00531 (15) | 0.0103 (2) | −0.00028 (14) |
O1 | 0.0386 (13) | 0.0412 (13) | 0.0331 (12) | 0.0006 (11) | 0.0070 (10) | 0.0026 (11) |
O2 | 0.0572 (17) | 0.0521 (16) | 0.0401 (15) | 0.0015 (13) | 0.0189 (13) | 0.0137 (13) |
O3 | 0.0618 (18) | 0.0342 (13) | 0.0503 (16) | 0.0024 (12) | 0.0274 (14) | −0.0036 (11) |
O4 | 0.0640 (19) | 0.0554 (18) | 0.066 (2) | 0.0006 (15) | 0.0347 (17) | −0.0190 (15) |
N1 | 0.0362 (15) | 0.0403 (15) | 0.0307 (14) | 0.0066 (12) | 0.0113 (12) | −0.0007 (12) |
N2 | 0.0447 (16) | 0.0335 (14) | 0.0296 (14) | 0.0056 (12) | 0.0130 (12) | −0.0009 (11) |
C1 | 0.044 (2) | 0.0295 (16) | 0.0325 (17) | 0.0036 (13) | 0.0121 (15) | 0.0007 (12) |
C2 | 0.0324 (16) | 0.0280 (14) | 0.0324 (16) | −0.0005 (12) | 0.0077 (13) | 0.0009 (12) |
C3 | 0.0345 (17) | 0.0430 (18) | 0.0371 (17) | −0.0027 (14) | 0.0135 (14) | 0.0006 (15) |
C4 | 0.0405 (18) | 0.0426 (19) | 0.0364 (17) | −0.0049 (15) | 0.0186 (15) | 0.0020 (14) |
C5 | 0.056 (2) | 0.0376 (18) | 0.0327 (17) | 0.0049 (16) | 0.0190 (16) | −0.0020 (14) |
C6 | 0.058 (2) | 0.0342 (16) | 0.0301 (16) | 0.0034 (15) | 0.0224 (16) | −0.0017 (13) |
C7 | 0.057 (2) | 0.0391 (18) | 0.0369 (18) | −0.0057 (16) | 0.0250 (17) | −0.0035 (14) |
C8 | 0.060 (2) | 0.0399 (18) | 0.0401 (19) | 0.0023 (16) | 0.0306 (18) | −0.0016 (15) |
C9 | 0.0422 (19) | 0.051 (2) | 0.0390 (19) | 0.0100 (16) | 0.0154 (16) | −0.0019 (16) |
C10 | 0.052 (2) | 0.068 (3) | 0.0363 (19) | 0.005 (2) | 0.0221 (17) | −0.0003 (18) |
C11 | 0.046 (2) | 0.055 (2) | 0.0383 (19) | −0.0021 (17) | 0.0181 (16) | 0.0041 (17) |
C12 | 0.099 (4) | 0.078 (3) | 0.044 (2) | 0.012 (3) | 0.037 (3) | 0.018 (2) |
C13 | 0.0395 (18) | 0.0429 (18) | 0.0334 (17) | −0.0022 (15) | 0.0129 (14) | 0.0026 (14) |
C14 | 0.0354 (17) | 0.0362 (17) | 0.0337 (16) | −0.0010 (13) | 0.0130 (14) | −0.0020 (13) |
C15 | 0.063 (3) | 0.042 (2) | 0.046 (2) | 0.0090 (18) | 0.0241 (19) | 0.0124 (17) |
C16 | 0.067 (3) | 0.0343 (18) | 0.052 (2) | 0.0121 (18) | 0.024 (2) | 0.0079 (17) |
C17 | 0.049 (2) | 0.0326 (17) | 0.0380 (18) | 0.0054 (15) | 0.0178 (16) | −0.0004 (14) |
C18 | 0.0378 (17) | 0.0303 (15) | 0.0317 (16) | −0.0001 (13) | 0.0128 (13) | −0.0007 (12) |
C19 | 0.062 (2) | 0.0402 (19) | 0.046 (2) | 0.0099 (18) | 0.0236 (19) | −0.0043 (16) |
C20 | 0.118 (5) | 0.052 (3) | 0.071 (3) | 0.033 (3) | 0.051 (3) | 0.001 (2) |
C21 | 0.068 (3) | 0.050 (2) | 0.0363 (19) | 0.005 (2) | 0.0253 (19) | −0.0044 (17) |
C22 | 0.062 (2) | 0.0432 (19) | 0.0322 (17) | 0.0102 (18) | 0.0198 (17) | 0.0034 (15) |
Cu1—O1 | 1.980 (3) | C12—H12C | 0.9600 |
Cu1—O2 | 2.486 (3) | C13—C14 | 1.391 (5) |
Cu1—O3 | 1.961 (3) | C13—C15 | 1.427 (6) |
Cu1—O4 | 2.580 (4) | C14—C18 | 1.435 (5) |
Cu1—N1 | 2.009 (3) | C15—C16 | 1.360 (6) |
Cu1—N2 | 2.000 (3) | C15—H15 | 0.9300 |
Cu1—C1 | 2.543 (4) | C16—C17 | 1.430 (5) |
O1—C1 | 1.271 (5) | C16—H16 | 0.9300 |
O2—C1 | 1.234 (5) | C17—C18 | 1.398 (5) |
O3—C5 | 1.274 (5) | C17—C19 | 1.425 (6) |
O4—C5 | 1.241 (5) | C19—C21 | 1.371 (6) |
N1—C9 | 1.319 (5) | C19—C20 | 1.510 (6) |
N1—C14 | 1.365 (5) | C20—H20A | 0.9600 |
N2—C22 | 1.330 (5) | C20—H20B | 0.9600 |
N2—C18 | 1.355 (4) | C20—H20C | 0.9600 |
C1—C2 | 1.510 (5) | C21—C22 | 1.383 (6) |
C2—C4i | 1.386 (5) | C21—H21 | 0.9300 |
C2—C3 | 1.395 (5) | C22—H22 | 0.9300 |
C3—C4 | 1.391 (5) | O5—C29 | 1.275 (10) |
C3—H3 | 0.9300 | O5—H5O | 0.9300 |
C4—C2i | 1.386 (5) | O6—C29 | 1.273 (10) |
C4—H4 | 0.9300 | O7—C30 | 1.297 (10) |
C5—C6 | 1.504 (5) | O7—H7O | 0.9300 |
C6—C7 | 1.383 (6) | O8—C30 | 1.295 (10) |
C6—C8ii | 1.401 (6) | C23—C24 | 1.3900 |
C7—C8 | 1.386 (5) | C23—C28 | 1.3900 |
C7—H7 | 0.9300 | C23—C29 | 1.496 (6) |
C8—C6ii | 1.401 (6) | C24—C25 | 1.3900 |
C8—H8 | 0.9300 | C24—H24 | 0.9300 |
C9—C10 | 1.396 (6) | C25—C26 | 1.3900 |
C9—H9 | 0.9300 | C25—H25 | 0.9300 |
C10—C11 | 1.371 (6) | C26—C27 | 1.3900 |
C10—H10 | 0.9300 | C26—C30 | 1.514 (6) |
C11—C13 | 1.422 (5) | C27—C28 | 1.3900 |
C11—C12 | 1.493 (6) | C27—H27 | 0.9300 |
C12—H12A | 0.9600 | C28—H28 | 0.9300 |
C12—H12B | 0.9600 | ||
O1—Cu1—O3 | 95.4 (1) | C14—C13—C11 | 117.6 (4) |
O1—Cu1—N1 | 165.7 (1) | C14—C13—C15 | 118.0 (3) |
O1—Cu1—N2 | 91.9 (1) | C11—C13—C15 | 124.4 (4) |
O3—Cu1—N1 | 93.0 (1) | N1—C14—C13 | 123.7 (3) |
O3—Cu1—N2 | 168.9 (1) | N1—C14—C18 | 115.6 (3) |
N1—Cu1—N2 | 81.6 (1) | C13—C14—C18 | 120.7 (3) |
O3—Cu1—C1 | 93.05 (12) | C16—C15—C13 | 121.4 (4) |
O1—Cu1—C1 | 29.41 (11) | C16—C15—H15 | 119.3 |
N2—Cu1—C1 | 97.39 (12) | C13—C15—H15 | 119.3 |
N1—Cu1—C1 | 138.58 (12) | C15—C16—C17 | 121.7 (4) |
C1—O1—Cu1 | 100.7 (2) | C15—C16—H16 | 119.2 |
C5—O3—Cu1 | 104.2 (2) | C17—C16—H16 | 119.2 |
C9—N1—C14 | 117.6 (3) | C18—C17—C19 | 117.2 (3) |
C9—N1—Cu1 | 129.3 (3) | C18—C17—C16 | 117.7 (4) |
C14—N1—Cu1 | 112.9 (2) | C19—C17—C16 | 125.1 (3) |
C22—N2—C18 | 118.2 (3) | N2—C18—C17 | 123.5 (3) |
C22—N2—Cu1 | 128.4 (3) | N2—C18—C14 | 116.0 (3) |
C18—N2—Cu1 | 113.4 (2) | C17—C18—C14 | 120.5 (3) |
O2—C1—O1 | 123.1 (3) | C21—C19—C17 | 117.7 (4) |
O2—C1—C2 | 120.2 (4) | C21—C19—C20 | 120.9 (4) |
O1—C1—C2 | 116.7 (3) | C17—C19—C20 | 121.3 (4) |
O2—C1—Cu1 | 73.2 (2) | C19—C20—H20A | 109.5 |
O1—C1—Cu1 | 49.90 (17) | C19—C20—H20B | 109.5 |
C2—C1—Cu1 | 166.2 (3) | H20A—C20—H20B | 109.5 |
C4i—C2—C3 | 119.8 (3) | C19—C20—H20C | 109.5 |
C4i—C2—C1 | 119.1 (3) | H20A—C20—H20C | 109.5 |
C3—C2—C1 | 121.0 (3) | H20B—C20—H20C | 109.5 |
C4—C3—C2 | 121.0 (3) | C19—C21—C22 | 121.4 (4) |
C4—C3—H3 | 119.5 | C19—C21—H21 | 119.3 |
C2—C3—H3 | 119.5 | C22—C21—H21 | 119.3 |
C2i—C4—C3 | 119.2 (3) | N2—C22—C21 | 121.9 (4) |
C2i—C4—H4 | 120.4 | N2—C22—H22 | 119.0 |
C3—C4—H4 | 120.4 | C21—C22—H22 | 119.0 |
O4—C5—O3 | 123.1 (4) | C29—O5—H5O | 120.0 |
O4—C5—C6 | 120.3 (4) | C30—O7—H7O | 120.0 |
O3—C5—C6 | 116.6 (3) | C24—C23—C28 | 120.0 |
C7—C6—C8ii | 119.3 (3) | C24—C23—C29 | 120.2 (6) |
C7—C6—C5 | 120.8 (4) | C28—C23—C29 | 119.8 (6) |
C8ii—C6—C5 | 119.9 (3) | C23—C24—C25 | 120.0 |
C6—C7—C8 | 120.5 (4) | C23—C24—H24 | 120.0 |
C6—C7—H7 | 119.8 | C25—C24—H24 | 120.0 |
C8—C7—H7 | 119.8 | C24—C25—C26 | 120.0 |
C7—C8—C6ii | 120.2 (4) | C24—C25—H25 | 120.0 |
C7—C8—H8 | 119.9 | C26—C25—H25 | 120.0 |
C6ii—C8—H8 | 119.9 | C25—C26—C27 | 120.0 |
N1—C9—C10 | 122.5 (4) | C25—C26—C30 | 120.3 (6) |
N1—C9—H9 | 118.8 | C27—C26—C30 | 119.7 (6) |
C10—C9—H9 | 118.8 | C28—C27—C26 | 120.0 |
C11—C10—C9 | 120.9 (4) | C28—C27—H27 | 120.0 |
C11—C10—H10 | 119.6 | C26—C27—H27 | 120.0 |
C9—C10—H10 | 119.6 | C27—C28—C23 | 120.0 |
C10—C11—C13 | 117.7 (4) | C27—C28—H28 | 120.0 |
C10—C11—C12 | 121.5 (4) | C23—C28—H28 | 120.0 |
C13—C11—C12 | 120.8 (4) | O6—C29—O5 | 127.6 (10) |
C11—C12—H12A | 109.5 | O6—C29—C23 | 116.2 (9) |
C11—C12—H12B | 109.5 | O5—C29—C23 | 116.1 (9) |
H12A—C12—H12B | 109.5 | O8—C30—O7 | 131.0 (10) |
C11—C12—H12C | 109.5 | O8—C30—C26 | 114.4 (9) |
H12A—C12—H12C | 109.5 | O7—C30—C26 | 114.6 (9) |
H12B—C12—H12C | 109.5 | ||
O3—Cu1—O1—C1 | 86.5 (2) | C9—C10—C11—C12 | −179.2 (5) |
N2—Cu1—O1—C1 | −101.8 (2) | C10—C11—C13—C14 | 0.0 (5) |
N1—Cu1—O1—C1 | −39.1 (6) | C12—C11—C13—C14 | 179.5 (4) |
O1—Cu1—O3—C5 | 83.7 (3) | C10—C11—C13—C15 | −179.5 (4) |
N2—Cu1—O3—C5 | −47.5 (7) | C12—C11—C13—C15 | 0.0 (7) |
N1—Cu1—O3—C5 | −107.9 (3) | C9—N1—C14—C13 | −0.7 (5) |
C1—Cu1—O3—C5 | 113.1 (3) | Cu1—N1—C14—C13 | 175.4 (3) |
O3—Cu1—N1—C9 | −8.1 (4) | C9—N1—C14—C18 | 177.9 (3) |
O1—Cu1—N1—C9 | 117.8 (5) | Cu1—N1—C14—C18 | −6.0 (4) |
N2—Cu1—N1—C9 | −178.4 (4) | C11—C13—C14—N1 | 0.2 (5) |
C1—Cu1—N1—C9 | 89.9 (4) | C15—C13—C14—N1 | 179.7 (4) |
O3—Cu1—N1—C14 | 176.4 (2) | C11—C13—C14—C18 | −178.3 (3) |
O1—Cu1—N1—C14 | −57.7 (6) | C15—C13—C14—C18 | 1.2 (5) |
N2—Cu1—N1—C14 | 6.1 (2) | C14—C13—C15—C16 | −2.1 (6) |
C1—Cu1—N1—C14 | −85.6 (3) | C11—C13—C15—C16 | 177.4 (4) |
O3—Cu1—N2—C22 | 114.9 (7) | C13—C15—C16—C17 | 1.0 (7) |
O1—Cu1—N2—C22 | −16.6 (4) | C15—C16—C17—C18 | 1.0 (7) |
N1—Cu1—N2—C22 | 176.2 (4) | C15—C16—C17—C19 | −178.7 (4) |
C1—Cu1—N2—C22 | −45.6 (4) | C22—N2—C18—C17 | 1.8 (5) |
O3—Cu1—N2—C18 | −66.5 (7) | Cu1—N2—C18—C17 | −176.9 (3) |
O1—Cu1—N2—C18 | 162.0 (3) | C22—N2—C18—C14 | −177.8 (3) |
N1—Cu1—N2—C18 | −5.2 (2) | Cu1—N2—C18—C14 | 3.5 (4) |
C1—Cu1—N2—C18 | 133.0 (3) | C19—C17—C18—N2 | −1.7 (6) |
Cu1—O1—C1—O2 | 3.3 (4) | C16—C17—C18—N2 | 178.5 (4) |
Cu1—O1—C1—C2 | −175.6 (2) | C19—C17—C18—C14 | 177.9 (4) |
O3—Cu1—C1—O2 | 87.2 (2) | C16—C17—C18—C14 | −1.9 (6) |
O1—Cu1—C1—O2 | −177.1 (3) | N1—C14—C18—N2 | 1.8 (5) |
N2—Cu1—C1—O2 | −96.5 (2) | C13—C14—C18—N2 | −179.6 (3) |
N1—Cu1—C1—O2 | −10.8 (3) | N1—C14—C18—C17 | −177.9 (3) |
O3—Cu1—C1—O1 | −95.7 (2) | C13—C14—C18—C17 | 0.8 (5) |
N2—Cu1—C1—O1 | 80.6 (2) | C18—C17—C19—C21 | 0.3 (6) |
N1—Cu1—C1—O1 | 166.4 (2) | C16—C17—C19—C21 | −180.0 (4) |
O3—Cu1—C1—C2 | −79.0 (11) | C18—C17—C19—C20 | −178.2 (5) |
O1—Cu1—C1—C2 | 16.6 (10) | C16—C17—C19—C20 | 1.5 (7) |
N2—Cu1—C1—C2 | 97.3 (11) | C17—C19—C21—C22 | 0.9 (7) |
N1—Cu1—C1—C2 | −177.0 (10) | C20—C19—C21—C22 | 179.4 (5) |
O2—C1—C2—C4i | −29.4 (5) | C18—N2—C22—C21 | −0.5 (6) |
O1—C1—C2—C4i | 149.5 (3) | Cu1—N2—C22—C21 | 178.0 (3) |
Cu1—C1—C2—C4i | 135.3 (10) | C19—C21—C22—N2 | −0.9 (7) |
O2—C1—C2—C3 | 152.0 (4) | C28—C23—C24—C25 | 0.0 |
O1—C1—C2—C3 | −29.1 (5) | C29—C23—C24—C25 | −179 (3) |
Cu1—C1—C2—C3 | −43.3 (12) | C23—C24—C25—C26 | 0.0 |
C4i—C2—C3—C4 | −1.7 (6) | C24—C25—C26—C27 | 0.0 |
C1—C2—C3—C4 | 176.9 (3) | C24—C25—C26—C30 | −179 (3) |
C2—C3—C4—C2i | 1.7 (6) | C25—C26—C27—C28 | 0.0 |
Cu1—O3—C5—O4 | 1.4 (5) | C30—C26—C27—C28 | 179 (3) |
Cu1—O3—C5—C6 | −177.5 (3) | C26—C27—C28—C23 | 0.0 |
O4—C5—C6—C7 | −172.1 (4) | C24—C23—C28—C27 | 0.0 |
O3—C5—C6—C7 | 6.7 (5) | C29—C23—C28—C27 | 179 (3) |
O4—C5—C6—C8ii | 6.7 (6) | C24—C23—C29—O6 | 168 (2) |
O3—C5—C6—C8ii | −174.4 (3) | C28—C23—C29—O6 | −11 (2) |
C8ii—C6—C7—C8 | −0.9 (6) | C24—C23—C29—O5 | −12 (2) |
C5—C6—C7—C8 | 178.0 (3) | C28—C23—C29—O5 | 169 (2) |
C6—C7—C8—C6ii | 0.9 (6) | C25—C26—C30—O8 | 13 (2) |
C14—N1—C9—C10 | 1.0 (6) | C27—C26—C30—O8 | −166 (2) |
Cu1—N1—C9—C10 | −174.3 (3) | C25—C26—C30—O7 | −167 (2) |
N1—C9—C10—C11 | −0.8 (7) | C27—C26—C30—O7 | 14 (2) |
C9—C10—C11—C13 | 0.3 (6) |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1/2, −y+1/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Cu(C8H4O4)(C14H12N2)]·0.5C8H6O4 |
Mr | 518.97 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 295 |
a, b, c (Å) | 18.764 (5), 17.769 (5), 14.749 (5) |
β (°) | 117.841 (5) |
V (Å3) | 4348 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 1.05 |
Crystal size (mm) | 0.33 × 0.20 × 0.08 |
Data collection | |
Diffractometer | Rigaku Mercury CCD |
Absorption correction | Multi-scan (CrystalStructure; Rigaku, 2000) |
Tmin, Tmax | 0.828, 0.921 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16066, 4914, 4295 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.225, 1.15 |
No. of reflections | 4914 |
No. of parameters | 290 |
No. of restraints | 16 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.41, −0.88 |
Computer programs: CrystalClear (Rigaku, 2005), CrystalClear, CrystaClear, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), publCIF (Westrip, 2007).
Cu1—O1 | 1.980 (3) | Cu1—O4 | 2.580 (4) |
Cu1—O2 | 2.486 (3) | Cu1—N1 | 2.009 (3) |
Cu1—O3 | 1.961 (3) | Cu1—N2 | 2.000 (3) |
O1—Cu1—O3 | 95.4 (1) | O3—Cu1—N1 | 93.0 (1) |
O1—Cu1—N1 | 165.7 (1) | O3—Cu1—N2 | 168.9 (1) |
O1—Cu1—N2 | 91.9 (1) | N1—Cu1—N2 | 81.6 (1) |
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Copper terephthalate forms adducts with 1,10-phenanthroline; the 1:1 adduct has been isolated as an anhydrous (Sun et al., 2001; Marsh, 2004) as well as a monoaqua (Rogan et al., 2004) compound in which the dicarboxylate dianion functions as a bridging entity. A 1:2 adduct is known having two monodeprotonated carboxylate groups (Li et al., 2006). Copper(II) terephthalate–dimethylphenanthroline crystallizes as a 1:0.5 cocrystal, (C14H14N2)(C8H4O4)Cu.0.5C8H6O4, the terephthalate dianion links adjacent copper atoms into a zigzag chain, the kink at the metal linkage being nearly a right angle. The metal atom shows square-planar coordination; if the long double-bonded oxygen atoms that are more than 2.5 Å away are considered, then the geometry is an octahedron. The lattice terephthalic acid molecule is disordered about a center-of-inversion; it occupies the space between chains but is not hydrogen bonded to any.