Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.012 Å
- R factor = 0.058
- wR factor = 0.175
- Data-to-parameter ratio = 18.4
checkCIF/PLATON results
No syntax errors found
Alert level A
REFLT03_ALERT_3_A Reflection count > 15% excess reflns - sys abs data present?
From the CIF: _diffrn_reflns_theta_max 25.13
From the CIF: _diffrn_reflns_theta_full 25.13
From the CIF: _reflns_number_total 5698
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 4374
Completeness (_total/calc) 130.27%
| Author Response: The data were corrected for absorption by TWINABS, which corrects for
the twin components simultaneously.
|
PLAT971_ALERT_2_A Large Calcd. Non-Metal Positive Residual Density 6.33 eA-3
| Author Response: I think the alert is false alert.
|
PLAT971_ALERT_2_A Large Calcd. Non-Metal Positive Residual Density 6.06 eA-3
| Author Response: I think the alert is false alert.
|
PLAT971_ALERT_2_A Large Calcd. Non-Metal Positive Residual Density 6.06 eA-3
| Author Response: I think the alert is false alert.
|
PLAT971_ALERT_2_A Large Calcd. Non-Metal Positive Residual Density 6.04 eA-3
| Author Response: I think the alert is false alert.
|
PLAT972_ALERT_2_A Large Calcd. Non-Metal Negative Residual Density -20.83 eA-3
| Author Response: I think the alert is false alert.
|
PLAT972_ALERT_2_A Large Calcd. Non-Metal Negative Residual Density -20.01 eA-3
| Author Response: I think the alert is false alert.
|
PLAT974_ALERT_2_A Large Calcd. Negative Residual Density on Cu1 -14.31 eA-3
| Author Response: I think the alert is false alert.
|
PLAT924_ALERT_1_A The Reported and Calculated Rho(min) Differ by . 19.14 eA-3
| Author Response: I think the alert is false alert.
|
PLAT925_ALERT_1_A The Reported and Calculated Rho(max) Differ by . 4.62 eA-3
| Author Response: I think the alert is false alert.
|
PLAT926_ALERT_1_A Reported and Calculated R1 * 100.0 Differ by . -18.39
| Author Response: I think the alert is false alert.
|
PLAT927_ALERT_1_A Reported and Calculated wR2 * 100.0 Differ by . -43.99
| Author Response: I think the alert is false alert.
|
PLAT928_ALERT_1_A Reported and Calculated S value Differ by . -2.23
| Author Response: I think the alert is false alert.
|
Alert level B
PLAT972_ALERT_2_B Large Calcd. Non-Metal Negative Residual Density -3.11 eA-3
| Author Response: I think the alert is false alert.
|
PLAT972_ALERT_2_B Large Calcd. Non-Metal Negative Residual Density -3.07 eA-3
| Author Response: I think the alert is false alert.
|
PLAT972_ALERT_2_B Large Calcd. Non-Metal Negative Residual Density -2.93 eA-3
| Author Response: I think the alert is false alert.
|
PLAT972_ALERT_2_B Large Calcd. Non-Metal Negative Residual Density -2.77 eA-3
| Author Response: I think the alert is false alert.
|
PLAT972_ALERT_2_B Large Calcd. Non-Metal Negative Residual Density -2.65 eA-3
| Author Response: I think the alert is false alert.
|
PLAT972_ALERT_2_B Large Calcd. Non-Metal Negative Residual Density -2.59 eA-3
| Author Response: I think the alert is false alert.
|
PLAT021_ALERT_1_B Ratio Unique / Expected Reflections too High ... 1.30
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang .. 12
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 1
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.598 96
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density 2.49 eA-3
| Author Response: I think the alert is false alert.
|
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density 2.47 eA-3
| Author Response: I think the alert is false alert.
|
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density 2.33 eA-3
| Author Response: I think the alert is false alert.
|
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density 2.27 eA-3
| Author Response: I think the alert is false alert.
|
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density 2.15 eA-3
| Author Response: I think the alert is false alert.
|
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density 1.84 eA-3
| Author Response: I think the alert is false alert.
|
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density 1.80 eA-3
| Author Response: I think the alert is false alert.
|
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density 1.78 eA-3
| Author Response: I think the alert is false alert.
|
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density 1.75 eA-3
| Author Response: I think the alert is false alert.
|
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density 1.66 eA-3
| Author Response: I think the alert is false alert.
|
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density 1.66 eA-3
| Author Response: I think the alert is false alert.
|
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density 1.59 eA-3
| Author Response: I think the alert is false alert.
|
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density 1.58 eA-3
| Author Response: I think the alert is false alert.
|
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density 1.58 eA-3
| Author Response: I think the alert is false alert.
|
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density 1.57 eA-3
| Author Response: I think the alert is false alert.
|
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density 1.57 eA-3
| Author Response: I think the alert is false alert.
|
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density 1.55 eA-3
| Author Response: I think the alert is false alert.
|
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density -2.36 eA-3
| Author Response: I think the alert is false alert.
|
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density -2.28 eA-3
| Author Response: I think the alert is false alert.
|
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density -2.19 eA-3
| Author Response: I think the alert is false alert.
|
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density -2.19 eA-3
| Author Response: I think the alert is false alert.
|
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density -2.18 eA-3
| Author Response: I think the alert is false alert.
|
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density -2.17 eA-3
| Author Response: I think the alert is false alert.
|
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density -2.17 eA-3
| Author Response: I think the alert is false alert.
|
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density -2.12 eA-3
| Author Response: I think the alert is false alert.
|
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density -2.03 eA-3
| Author Response: I think the alert is false alert.
|
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density -2.01 eA-3
| Author Response: I think the alert is false alert.
|
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density -2.00 eA-3
| Author Response: I think the alert is false alert.
|
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density -1.98 eA-3
| Author Response: I think the alert is false alert.
|
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density -1.97 eA-3
| Author Response: I think the alert is false alert.
|
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density -1.92 eA-3
| Author Response: I think the alert is false alert.
|
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density -1.89 eA-3
| Author Response: I think the alert is false alert.
|
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density -1.88 eA-3
| Author Response: I think the alert is false alert.
|
PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 20 Ang.
Alert level G
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large. 12.08
PLAT794_ALERT_5_G Note: Tentative Bond Valency for Cu1 ....... 2.18
13 ALERT level A = In general: serious problem
7 ALERT level B = Potentially serious problem
38 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
47 ALERT type 2 Indicator that the structure model may be wrong or deficient
5 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
1 ALERT type 5 Informative message, check
Copper acetate monohydrate (2.00 g, 10 mmol) and 4-iodobenzoic acid (4.96 g, 20 mmol) were heated in aqueous ethanol (1:1, 60 ml) for 1 h. The solvent was
removed to give blue copper bis(4-iodobenzoate), which was isolated in 50%
yield. The powder and 2,2'-bipyridine (0.77 g, 5 mmol) were dissolved in
tetrahydrofuran. Crystals were isolated after several days.
H atoms were placed in calculated positions (C–H 0.95, O–H 0.84 Å) and
were included in the refinement in the riding model approximation,
with U(H) set to 1.2 to 1.5U(C,O).
The final difference Fourier map had a peak and a hole in the vicinity of I2.
The crystal studied is a non-merohedral twin with minor components in a 38.1 (3)
and 10.8 (2)% proportion. The twinned nature of the crystal structure adversely
affected the quality of the diffraction measured, and this is reflected in the
somewhat larger numbers in the weighting scheme.
Structure description
top
Copper(II) benzoate and its analogs form adducts with 2,2'-bipyridine. The
copper benzoate homolog furnishes a water-coordinated adduct (Yang et
al., 1994), as does copper p-toluate (Li et al.,
2006; Liu
et al., 2006) and copper o-toluate (He et al.,
2007). The
copper atom in Cu(H2O)(C10H8N2)(C7H4IO2)2 (Scheme I) is
chelated by the N-heterocycle and is coordinated by two monodentate
carboxylate ions and a water molecule in a square-pyramidal geometry (Fig. 1).
The apical site is occupied by the O atom of the carboxylate unit. The crystal
studied is a non-merohedral twin with minor components in a 0.381 (3) and
0.108 (2) proportion.
For related copper carboxylate–2,2'-bipyridine adducts, see: He et al.
(2007); Li et al. (2006); Liu et al.
(2006); Yang et al.
(1994).
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).
Aqua(2,2'-bipyridine-
κ2N,
N')bis(4-iodobenzoato-
κO)copper(II)
top
Crystal data top
[Cu(C7H4IO2)2(C10H8N2)(H2O)] | F(000) = 1404 |
Mr = 731.74 | Dx = 1.990 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1215 reflections |
a = 13.0571 (2) Å | θ = 2.5–24.2° |
b = 16.0724 (2) Å | µ = 3.46 mm−1 |
c = 11.9605 (2) Å | T = 100 K |
β = 103.298 (1)° | Cube, blue |
V = 2442.72 (6) Å3 | 0.30 × 0.30 × 0.30 mm |
Z = 4 | |
Data collection top
Bruker SMART APEX diffractometer | 5698 independent reflections |
Radiation source: fine-focus sealed tube | 4505 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.092 |
ω scans | θmax = 25.1°, θmin = 2.0° |
Absorption correction: multi-scan (TWINABS; Bruker, 2009) | h = −15→15 |
Tmin = 0.423, Tmax = 0.423 | k = 0→19 |
33957 measured reflections | l = 0→14 |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.175 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.087P)2 + 12.0788P] where P = (Fo2 + 2Fc2)/3 |
5698 reflections | (Δ/σ)max = 0.001 |
310 parameters | Δρmax = 1.71 e Å−3 |
0 restraints | Δρmin = −1.69 e Å−3 |
Crystal data top
[Cu(C7H4IO2)2(C10H8N2)(H2O)] | V = 2442.72 (6) Å3 |
Mr = 731.74 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.0571 (2) Å | µ = 3.46 mm−1 |
b = 16.0724 (2) Å | T = 100 K |
c = 11.9605 (2) Å | 0.30 × 0.30 × 0.30 mm |
β = 103.298 (1)° | |
Data collection top
Bruker SMART APEX diffractometer | 5698 independent reflections |
Absorption correction: multi-scan (TWINABS; Bruker, 2009) | 4505 reflections with I > 2σ(I) |
Tmin = 0.423, Tmax = 0.423 | Rint = 0.092 |
33957 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.058 | 0 restraints |
wR(F2) = 0.175 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.087P)2 + 12.0788P] where P = (Fo2 + 2Fc2)/3 |
5698 reflections | Δρmax = 1.71 e Å−3 |
310 parameters | Δρmin = −1.69 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I1 | 1.52100 (5) | 0.77933 (4) | 0.96178 (5) | 0.0307 (2) | |
I2 | 0.54254 (5) | 1.06313 (4) | 0.81444 (6) | 0.0370 (2) | |
Cu1 | 0.88404 (8) | 0.70624 (6) | 0.44393 (8) | 0.0165 (3) | |
O1 | 0.7975 (5) | 0.7791 (3) | 0.5186 (5) | 0.0189 (13) | |
O2 | 0.7765 (5) | 0.8878 (4) | 0.3970 (6) | 0.0319 (16) | |
O3 | 1.0368 (4) | 0.7208 (3) | 0.5695 (5) | 0.0182 (12) | |
O4 | 1.0982 (5) | 0.8248 (4) | 0.4776 (5) | 0.0220 (13) | |
O1W | 0.9172 (5) | 0.7943 (3) | 0.3446 (5) | 0.0203 (13) | |
H11 | 0.8773 | 0.8352 | 0.3455 | 0.030* | |
H12 | 0.9801 | 0.8092 | 0.3687 | 0.030* | |
N1 | 0.8380 (5) | 0.6058 (4) | 0.5151 (6) | 0.0162 (15) | |
N2 | 0.9245 (5) | 0.6191 (4) | 0.3416 (5) | 0.0144 (14) | |
C1 | 0.7637 (7) | 0.8513 (5) | 0.4846 (8) | 0.0215 (19) | |
C2 | 0.7064 (7) | 0.8978 (5) | 0.5618 (7) | 0.0209 (18) | |
C3 | 0.6627 (7) | 0.9757 (5) | 0.5274 (8) | 0.024 (2) | |
H3 | 0.6656 | 0.9967 | 0.4540 | 0.029* | |
C4 | 0.6158 (7) | 1.0224 (6) | 0.5975 (8) | 0.028 (2) | |
H4 | 0.5884 | 1.0759 | 0.5737 | 0.034* | |
C5 | 0.6090 (7) | 0.9913 (5) | 0.7019 (8) | 0.0236 (19) | |
C6 | 0.6510 (7) | 0.9127 (5) | 0.7390 (8) | 0.026 (2) | |
H6 | 0.6470 | 0.8919 | 0.8122 | 0.031* | |
C7 | 0.6977 (7) | 0.8665 (5) | 0.6682 (7) | 0.0219 (19) | |
H7 | 0.7245 | 0.8128 | 0.6916 | 0.026* | |
C8 | 1.1036 (7) | 0.7747 (5) | 0.5605 (7) | 0.0195 (18) | |
C9 | 1.2009 (7) | 0.7822 (5) | 0.6583 (7) | 0.0171 (17) | |
C10 | 1.2850 (7) | 0.8289 (5) | 0.6483 (7) | 0.0217 (19) | |
H10 | 1.2808 | 0.8612 | 0.5809 | 0.026* | |
C11 | 1.3773 (7) | 0.8306 (5) | 0.7346 (7) | 0.0222 (19) | |
H11A | 1.4365 | 0.8623 | 0.7263 | 0.027* | |
C12 | 1.3794 (7) | 0.7842 (5) | 0.8332 (7) | 0.0216 (19) | |
C13 | 1.2941 (7) | 0.7393 (5) | 0.8471 (8) | 0.0235 (19) | |
H13 | 1.2969 | 0.7096 | 0.9164 | 0.028* | |
C14 | 1.2052 (7) | 0.7373 (5) | 0.7612 (7) | 0.0204 (18) | |
H14 | 1.1460 | 0.7059 | 0.7703 | 0.024* | |
C15 | 0.7940 (7) | 0.6048 (5) | 0.6056 (7) | 0.0218 (19) | |
H15 | 0.7804 | 0.6566 | 0.6378 | 0.026* | |
C16 | 0.7670 (8) | 0.5324 (5) | 0.6550 (8) | 0.025 (2) | |
H16 | 0.7364 | 0.5339 | 0.7198 | 0.030* | |
C17 | 0.7866 (7) | 0.4578 (6) | 0.6057 (8) | 0.026 (2) | |
H17 | 0.7687 | 0.4068 | 0.6365 | 0.031* | |
C18 | 0.8320 (7) | 0.4570 (5) | 0.5122 (8) | 0.0230 (19) | |
H18 | 0.8456 | 0.4059 | 0.4782 | 0.028* | |
C19 | 0.8573 (6) | 0.5329 (5) | 0.4690 (7) | 0.0152 (17) | |
C20 | 0.9038 (6) | 0.5399 (5) | 0.3673 (7) | 0.0166 (17) | |
C21 | 0.9213 (7) | 0.4734 (5) | 0.3003 (8) | 0.026 (2) | |
H21 | 0.9065 | 0.4181 | 0.3200 | 0.031* | |
C22 | 0.9603 (8) | 0.4886 (6) | 0.2050 (7) | 0.026 (2) | |
H22 | 0.9734 | 0.4439 | 0.1582 | 0.031* | |
C23 | 0.9802 (7) | 0.5701 (5) | 0.1779 (8) | 0.024 (2) | |
H23 | 1.0054 | 0.5821 | 0.1112 | 0.029* | |
C24 | 0.9627 (6) | 0.6336 (5) | 0.2493 (7) | 0.0195 (18) | |
H24 | 0.9784 | 0.6892 | 0.2320 | 0.023* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.0258 (3) | 0.0370 (4) | 0.0256 (4) | 0.0053 (3) | −0.0018 (2) | −0.0007 (2) |
I2 | 0.0303 (4) | 0.0424 (4) | 0.0393 (4) | 0.0066 (3) | 0.0099 (3) | −0.0150 (3) |
Cu1 | 0.0216 (6) | 0.0126 (5) | 0.0153 (5) | −0.0010 (4) | 0.0045 (4) | 0.0007 (4) |
O1 | 0.026 (3) | 0.016 (3) | 0.015 (3) | 0.000 (2) | 0.007 (3) | −0.004 (2) |
O2 | 0.039 (4) | 0.029 (4) | 0.032 (4) | 0.010 (3) | 0.017 (3) | 0.017 (3) |
O3 | 0.017 (3) | 0.020 (3) | 0.015 (3) | −0.002 (2) | 0.000 (2) | 0.000 (2) |
O4 | 0.025 (3) | 0.021 (3) | 0.019 (3) | −0.007 (3) | 0.003 (3) | 0.008 (2) |
O1W | 0.025 (3) | 0.017 (3) | 0.018 (3) | 0.000 (2) | 0.002 (3) | 0.001 (2) |
N1 | 0.020 (4) | 0.010 (3) | 0.017 (4) | −0.003 (3) | 0.000 (3) | −0.001 (3) |
N2 | 0.016 (3) | 0.017 (4) | 0.008 (3) | 0.003 (3) | 0.000 (3) | 0.001 (3) |
C1 | 0.016 (4) | 0.020 (5) | 0.028 (5) | 0.004 (3) | 0.005 (4) | 0.007 (4) |
C2 | 0.017 (4) | 0.020 (4) | 0.025 (5) | −0.001 (3) | 0.002 (4) | 0.000 (3) |
C3 | 0.025 (5) | 0.023 (5) | 0.026 (5) | 0.000 (4) | 0.008 (4) | 0.004 (3) |
C4 | 0.022 (5) | 0.026 (5) | 0.036 (6) | 0.001 (4) | 0.006 (4) | −0.003 (4) |
C5 | 0.015 (4) | 0.026 (5) | 0.027 (5) | 0.003 (4) | −0.001 (4) | −0.011 (4) |
C6 | 0.021 (5) | 0.022 (5) | 0.036 (6) | −0.001 (4) | 0.009 (4) | 0.001 (4) |
C7 | 0.017 (4) | 0.017 (4) | 0.027 (5) | 0.001 (3) | −0.007 (4) | −0.002 (3) |
C8 | 0.023 (5) | 0.015 (4) | 0.022 (5) | 0.003 (4) | 0.008 (4) | −0.004 (3) |
C9 | 0.020 (4) | 0.019 (4) | 0.014 (4) | 0.004 (3) | 0.005 (3) | 0.002 (3) |
C10 | 0.030 (5) | 0.024 (5) | 0.013 (4) | 0.002 (4) | 0.009 (4) | 0.000 (3) |
C11 | 0.019 (4) | 0.032 (5) | 0.017 (4) | −0.005 (4) | 0.007 (4) | −0.006 (3) |
C12 | 0.029 (5) | 0.022 (4) | 0.015 (4) | 0.009 (4) | 0.007 (4) | −0.008 (3) |
C13 | 0.026 (5) | 0.019 (4) | 0.025 (5) | 0.005 (4) | 0.004 (4) | −0.001 (3) |
C14 | 0.025 (5) | 0.012 (4) | 0.024 (5) | 0.004 (3) | 0.006 (4) | −0.002 (3) |
C15 | 0.024 (5) | 0.017 (4) | 0.024 (5) | 0.000 (4) | 0.004 (4) | −0.001 (3) |
C16 | 0.034 (5) | 0.023 (5) | 0.019 (5) | −0.004 (4) | 0.008 (4) | 0.002 (3) |
C17 | 0.028 (5) | 0.027 (5) | 0.023 (5) | −0.006 (4) | 0.008 (4) | 0.006 (4) |
C18 | 0.019 (5) | 0.013 (4) | 0.037 (5) | 0.003 (3) | 0.006 (4) | 0.003 (4) |
C19 | 0.010 (4) | 0.019 (4) | 0.015 (4) | 0.004 (3) | −0.002 (3) | 0.004 (3) |
C20 | 0.016 (4) | 0.014 (4) | 0.019 (5) | 0.001 (3) | 0.000 (3) | 0.000 (3) |
C21 | 0.031 (5) | 0.017 (5) | 0.029 (5) | −0.005 (4) | 0.006 (4) | 0.002 (3) |
C22 | 0.035 (5) | 0.023 (5) | 0.020 (5) | 0.002 (4) | 0.007 (4) | −0.006 (4) |
C23 | 0.023 (5) | 0.028 (5) | 0.020 (5) | 0.002 (4) | 0.002 (4) | 0.004 (4) |
C24 | 0.019 (4) | 0.025 (5) | 0.017 (5) | 0.002 (4) | 0.009 (4) | −0.001 (3) |
Geometric parameters (Å, º) top
I1—C12 | 2.117 (9) | C8—C9 | 1.521 (12) |
I2—C5 | 2.106 (8) | C9—C10 | 1.358 (12) |
Cu1—N1 | 1.982 (7) | C9—C14 | 1.416 (11) |
Cu1—N2 | 2.009 (6) | C10—C11 | 1.395 (12) |
Cu1—O1 | 1.977 (5) | C10—H10 | 0.9500 |
Cu1—O3 | 2.216 (6) | C11—C12 | 1.390 (12) |
Cu1—O1W | 1.959 (5) | C11—H11A | 0.9500 |
O1—C1 | 1.275 (10) | C12—C13 | 1.369 (13) |
O2—C1 | 1.246 (10) | C13—C14 | 1.363 (12) |
O3—C8 | 1.251 (10) | C13—H13 | 0.9500 |
O4—C8 | 1.268 (10) | C14—H14 | 0.9500 |
O1W—H11 | 0.8400 | C15—C16 | 1.387 (12) |
O1W—H12 | 0.8400 | C15—H15 | 0.9500 |
N1—C15 | 1.338 (11) | C16—C17 | 1.386 (12) |
N1—C19 | 1.344 (10) | C16—H16 | 0.9500 |
N2—C24 | 1.332 (10) | C17—C18 | 1.380 (12) |
N2—C20 | 1.351 (10) | C17—H17 | 0.9500 |
C1—C2 | 1.513 (12) | C18—C19 | 1.394 (11) |
C2—C7 | 1.396 (12) | C18—H18 | 0.9500 |
C2—C3 | 1.397 (12) | C19—C20 | 1.484 (12) |
C3—C4 | 1.369 (12) | C20—C21 | 1.386 (12) |
C3—H3 | 0.9500 | C21—C22 | 1.373 (12) |
C4—C5 | 1.367 (13) | C21—H21 | 0.9500 |
C4—H4 | 0.9500 | C22—C23 | 1.389 (13) |
C5—C6 | 1.409 (12) | C22—H22 | 0.9500 |
C6—C7 | 1.370 (12) | C23—C24 | 1.383 (12) |
C6—H6 | 0.9500 | C23—H23 | 0.9500 |
C7—H7 | 0.9500 | C24—H24 | 0.9500 |
| | | |
O1W—Cu1—O1 | 94.3 (2) | C14—C9—C8 | 119.1 (7) |
O1W—Cu1—N1 | 168.6 (3) | C9—C10—C11 | 121.6 (8) |
O1—Cu1—N1 | 91.6 (3) | C9—C10—H10 | 119.2 |
O1W—Cu1—N2 | 90.5 (3) | C11—C10—H10 | 119.2 |
O1—Cu1—N2 | 161.0 (3) | C12—C11—C10 | 117.5 (8) |
N1—Cu1—N2 | 80.9 (3) | C12—C11—H11A | 121.3 |
O1W—Cu1—O3 | 92.6 (2) | C10—C11—H11A | 121.3 |
O1—Cu1—O3 | 98.7 (2) | C13—C12—C11 | 121.9 (8) |
N1—Cu1—O3 | 96.3 (2) | C13—C12—I1 | 119.4 (6) |
N2—Cu1—O3 | 99.5 (2) | C11—C12—I1 | 118.6 (7) |
C1—O1—Cu1 | 126.0 (5) | C14—C13—C12 | 119.8 (8) |
C8—O3—Cu1 | 123.5 (5) | C14—C13—H13 | 120.1 |
Cu1—O1W—H11 | 109.5 | C12—C13—H13 | 120.1 |
Cu1—O1W—H12 | 109.5 | C13—C14—C9 | 120.0 (8) |
H11—O1W—H12 | 109.5 | C13—C14—H14 | 120.0 |
C15—N1—C19 | 118.6 (7) | C9—C14—H14 | 120.0 |
C15—N1—Cu1 | 125.9 (5) | N1—C15—C16 | 123.6 (8) |
C19—N1—Cu1 | 115.5 (5) | N1—C15—H15 | 118.2 |
C24—N2—C20 | 119.1 (7) | C16—C15—H15 | 118.2 |
C24—N2—Cu1 | 125.7 (6) | C17—C16—C15 | 117.1 (8) |
C20—N2—Cu1 | 115.1 (5) | C17—C16—H16 | 121.5 |
O2—C1—O1 | 126.4 (8) | C15—C16—H16 | 121.5 |
O2—C1—C2 | 117.5 (7) | C18—C17—C16 | 120.6 (8) |
O1—C1—C2 | 116.1 (7) | C18—C17—H17 | 119.7 |
C7—C2—C3 | 118.5 (8) | C16—C17—H17 | 119.7 |
C7—C2—C1 | 122.2 (8) | C17—C18—C19 | 118.3 (8) |
C3—C2—C1 | 119.3 (7) | C17—C18—H18 | 120.9 |
C4—C3—C2 | 121.4 (8) | C19—C18—H18 | 120.9 |
C4—C3—H3 | 119.3 | N1—C19—C18 | 121.9 (7) |
C2—C3—H3 | 119.3 | N1—C19—C20 | 114.9 (7) |
C5—C4—C3 | 119.4 (9) | C18—C19—C20 | 123.2 (7) |
C5—C4—H4 | 120.3 | N2—C20—C21 | 121.8 (7) |
C3—C4—H4 | 120.3 | N2—C20—C19 | 113.5 (7) |
C4—C5—C6 | 120.9 (8) | C21—C20—C19 | 124.6 (7) |
C4—C5—I2 | 120.5 (7) | C22—C21—C20 | 119.0 (8) |
C6—C5—I2 | 118.6 (6) | C22—C21—H21 | 120.5 |
C7—C6—C5 | 119.2 (8) | C20—C21—H21 | 120.5 |
C7—C6—H6 | 120.4 | C21—C22—C23 | 119.1 (8) |
C5—C6—H6 | 120.4 | C21—C22—H22 | 120.4 |
C6—C7—C2 | 120.6 (8) | C23—C22—H22 | 120.4 |
C6—C7—H7 | 119.7 | C24—C23—C22 | 119.1 (8) |
C2—C7—H7 | 119.7 | C24—C23—H23 | 120.5 |
O3—C8—O4 | 126.4 (8) | C22—C23—H23 | 120.5 |
O3—C8—C9 | 117.7 (7) | N2—C24—C23 | 121.9 (8) |
O4—C8—C9 | 115.9 (7) | N2—C24—H24 | 119.0 |
C10—C9—C14 | 119.1 (8) | C23—C24—H24 | 119.0 |
C10—C9—C8 | 121.7 (7) | | |
| | | |
O1W—Cu1—O1—C1 | 13.0 (7) | Cu1—O3—C8—C9 | 174.9 (5) |
N1—Cu1—O1—C1 | −157.2 (7) | O3—C8—C9—C10 | 169.1 (8) |
N2—Cu1—O1—C1 | −91.2 (10) | O4—C8—C9—C10 | −11.3 (11) |
O3—Cu1—O1—C1 | 106.2 (7) | O3—C8—C9—C14 | −9.0 (11) |
O1W—Cu1—O3—C8 | 2.8 (6) | O4—C8—C9—C14 | 170.5 (7) |
O1—Cu1—O3—C8 | −91.9 (6) | C14—C9—C10—C11 | 3.1 (12) |
N1—Cu1—O3—C8 | 175.6 (6) | C8—C9—C10—C11 | −175.0 (7) |
N2—Cu1—O3—C8 | 93.8 (6) | C9—C10—C11—C12 | −1.6 (12) |
O1W—Cu1—N1—C15 | −138.5 (12) | C10—C11—C12—C13 | −1.0 (12) |
O1—Cu1—N1—C15 | −17.7 (7) | C10—C11—C12—I1 | 176.3 (6) |
N2—Cu1—N1—C15 | 179.8 (7) | C11—C12—C13—C14 | 2.0 (12) |
O3—Cu1—N1—C15 | 81.2 (7) | I1—C12—C13—C14 | −175.3 (6) |
O1W—Cu1—N1—C19 | 44.0 (17) | C12—C13—C14—C9 | −0.5 (12) |
O1—Cu1—N1—C19 | 164.8 (6) | C10—C9—C14—C13 | −2.1 (12) |
N2—Cu1—N1—C19 | 2.3 (6) | C8—C9—C14—C13 | 176.1 (7) |
O3—Cu1—N1—C19 | −96.3 (6) | C19—N1—C15—C16 | 0.1 (13) |
O1W—Cu1—N2—C24 | 2.9 (7) | Cu1—N1—C15—C16 | −177.3 (7) |
O1—Cu1—N2—C24 | 107.7 (9) | N1—C15—C16—C17 | −0.6 (14) |
N1—Cu1—N2—C24 | 175.3 (7) | C15—C16—C17—C18 | 0.6 (14) |
O3—Cu1—N2—C24 | −89.8 (7) | C16—C17—C18—C19 | 0.0 (14) |
O1W—Cu1—N2—C20 | −172.7 (6) | C15—N1—C19—C18 | 0.5 (12) |
O1—Cu1—N2—C20 | −68.0 (10) | Cu1—N1—C19—C18 | 178.2 (6) |
N1—Cu1—N2—C20 | −0.3 (6) | C15—N1—C19—C20 | 178.5 (7) |
O3—Cu1—N2—C20 | 94.6 (6) | Cu1—N1—C19—C20 | −3.8 (9) |
Cu1—O1—C1—O2 | 2.1 (13) | C17—C18—C19—N1 | −0.6 (13) |
Cu1—O1—C1—C2 | −175.2 (5) | C17—C18—C19—C20 | −178.4 (8) |
O2—C1—C2—C7 | −172.9 (8) | C24—N2—C20—C21 | 0.1 (12) |
O1—C1—C2—C7 | 4.7 (12) | Cu1—N2—C20—C21 | 176.0 (7) |
O2—C1—C2—C3 | 5.4 (13) | C24—N2—C20—C19 | −177.5 (7) |
O1—C1—C2—C3 | −177.0 (8) | Cu1—N2—C20—C19 | −1.5 (9) |
C7—C2—C3—C4 | 2.5 (13) | N1—C19—C20—N2 | 3.5 (11) |
C1—C2—C3—C4 | −175.9 (9) | C18—C19—C20—N2 | −178.6 (8) |
C2—C3—C4—C5 | −1.8 (14) | N1—C19—C20—C21 | −174.0 (8) |
C3—C4—C5—C6 | 1.1 (14) | C18—C19—C20—C21 | 4.0 (14) |
C3—C4—C5—I2 | 177.7 (7) | N2—C20—C21—C22 | −0.3 (14) |
C4—C5—C6—C7 | −1.1 (13) | C19—C20—C21—C22 | 176.9 (8) |
I2—C5—C6—C7 | −177.8 (7) | C20—C21—C22—C23 | −0.6 (14) |
C5—C6—C7—C2 | 1.7 (13) | C21—C22—C23—C24 | 1.6 (14) |
C3—C2—C7—C6 | −2.4 (13) | C20—N2—C24—C23 | 1.1 (13) |
C1—C2—C7—C6 | 175.9 (8) | Cu1—N2—C24—C23 | −174.4 (6) |
Cu1—O3—C8—O4 | −4.6 (12) | C22—C23—C24—N2 | −1.9 (14) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H11···O2 | 0.84 | 1.79 | 2.560 (9) | 152 |
O1w—H12···O4 | 0.84 | 1.79 | 2.575 (8) | 154 |
Experimental details
Crystal data |
Chemical formula | [Cu(C7H4IO2)2(C10H8N2)(H2O)] |
Mr | 731.74 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 13.0571 (2), 16.0724 (2), 11.9605 (2) |
β (°) | 103.298 (1) |
V (Å3) | 2442.72 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 3.46 |
Crystal size (mm) | 0.30 × 0.30 × 0.30 |
|
Data collection |
Diffractometer | Bruker SMART APEX |
Absorption correction | Multi-scan (TWINABS; Bruker, 2009) |
Tmin, Tmax | 0.423, 0.423 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 33957, 5698, 4505 |
Rint | 0.092 |
(sin θ/λ)max (Å−1) | 0.598 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.175, 1.08 |
No. of reflections | 5698 |
No. of parameters | 310 |
H-atom treatment | H-atom parameters constrained |
| w = 1/[σ2(Fo2) + (0.087P)2 + 12.0788P] where P = (Fo2 + 2Fc2)/3 |
Δρmax, Δρmin (e Å−3) | 1.71, −1.69 |
Selected bond lengths (Å) topCu1—N1 | 1.982 (7) | Cu1—O3 | 2.216 (6) |
Cu1—N2 | 2.009 (6) | Cu1—O1W | 1.959 (5) |
Cu1—O1 | 1.977 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H11···O2 | 0.84 | 1.79 | 2.560 (9) | 151.9 |
O1w—H12···O4 | 0.84 | 1.79 | 2.575 (8) | 153.9 |
Copper(II) benzoate and its analogs form adducts with 2,2'-bipyridine. The copper benzoate homolog furnishes a water-coordinated adduct (Yang et al., 1994), as does copper p-toluate (Li et al., 2006; Liu et al., 2006) and copper o-toluate (He et al., 2007). The copper atom in Cu(H2O)(C10H8N2)(C7H4IO2)2 (Scheme I) is chelated by the N-heterocycle and is coordinated by two monodentate carboxylate ions and a water molecule in a square-pyramidal geometry (Fig. 1). The apical site is occupied by the O atom of the carboxylate unit. The crystal studied is a non-merohedral twin with minor components in a 0.381 (3) and 0.108 (2) proportion.