In the title compound, dimethylammonium diaquabis(pyridine-2,6-dicarboxylato-κ3O2,N,O6)indate(III), (C2H8N)[In(C7H3NO4)2(H2O)2], the central InIII ion is eight-coordinated by two pyridine-2,6-dicarboxylate ligands and two water molecules. The water molecules, the dimethylammonium ion and the carboxylate O atoms interact through hydrogen bonds, forming a three-dimensional supramolecular structure.
Supporting information
CCDC reference: 604998
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.004 Å
- R factor = 0.023
- wR factor = 0.039
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.45 Ratio
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N3
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 27.48
From the CIF: _reflns_number_total 4295
Count of symmetry unique reflns 2215
Completeness (_total/calc) 193.91%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 2080
Fraction of Friedel pairs measured 0.939
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 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
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXTL.
dimethylammonium
diaquabis(pyridine-2,6-dicarboxylato-
κ3O2,
N,
O6)indium(III)
top
Crystal data top
(C2H8N)[In(C7H3NO4)2(H2O)2] | Dx = 1.869 Mg m−3 |
Mr = 527.15 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P41 | Cell parameters from Total reflections |
Hall symbol: P 4w | θ = 2.1–27.5° |
a = 9.7681 (14) Å | µ = 1.33 mm−1 |
c = 19.632 (4) Å | T = 292 K |
V = 1873.2 (5) Å3 | Block, colorless |
Z = 4 | 0.41 × 0.37 × 0.34 mm |
F(000) = 1056 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 4295 independent reflections |
Radiation source: rotor-target | 3739 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
Detector resolution: 10.0 pixels mm-1 | θmax = 27.5°, θmin = 2.1° |
ω scans | h = −12→11 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −12→12 |
Tmin = 0.546, Tmax = 0.637 | l = −25→25 |
18141 measured reflections | |
Refinement top
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)] = 0.024 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.039 | w = 1/[σ2(Fo2) + (0.0188P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.91 | (Δ/σ)max = 0.001 |
4295 reflections | Δρmax = 0.27 e Å−3 |
295 parameters | Δρmin = −0.44 e Å−3 |
2 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.012 (15) |
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 | |
C1 | 0.7245 (3) | 1.1212 (3) | 0.64094 (16) | 0.0363 (7) | |
C2 | 0.6476 (3) | 1.0113 (3) | 0.67798 (14) | 0.0305 (6) | |
C3 | 0.6739 (3) | 0.9675 (3) | 0.74386 (14) | 0.0397 (7) | |
H3 | 0.7442 | 1.0071 | 0.7690 | 0.048* | |
C4 | 0.5957 (3) | 0.8658 (3) | 0.77160 (15) | 0.0407 (7) | |
H4 | 0.6135 | 0.8343 | 0.8154 | 0.049* | |
C5 | 0.4899 (3) | 0.8102 (3) | 0.73387 (14) | 0.0356 (7) | |
H5 | 0.4346 | 0.7422 | 0.7523 | 0.043* | |
C6 | 0.4677 (3) | 0.8569 (3) | 0.66902 (13) | 0.0284 (6) | |
C7 | 0.3542 (3) | 0.8087 (3) | 0.62313 (15) | 0.0356 (7) | |
C8 | 0.6425 (3) | 1.1916 (3) | 0.41192 (15) | 0.0326 (7) | |
C9 | 0.5419 (3) | 1.2931 (3) | 0.44125 (14) | 0.0316 (6) | |
C10 | 0.5230 (3) | 1.4251 (3) | 0.41732 (16) | 0.0453 (8) | |
H10 | 0.5698 | 1.4564 | 0.3791 | 0.054* | |
C11 | 0.4326 (4) | 1.5092 (3) | 0.4518 (2) | 0.0561 (10) | |
H11 | 0.4194 | 1.5989 | 0.4373 | 0.067* | |
C12 | 0.3620 (3) | 1.4606 (3) | 0.50763 (19) | 0.0500 (9) | |
H12 | 0.3025 | 1.5170 | 0.5317 | 0.060* | |
C13 | 0.3818 (3) | 1.3261 (3) | 0.52703 (16) | 0.0349 (6) | |
C14 | 0.3048 (3) | 1.2563 (4) | 0.58396 (15) | 0.0393 (8) | |
C15 | 0.0182 (4) | 0.9603 (4) | 0.5760 (4) | 0.111 (2) | |
H15A | −0.0005 | 0.9791 | 0.6230 | 0.167* | |
H15B | −0.0565 | 0.9923 | 0.5485 | 0.167* | |
H15C | 0.1008 | 1.0064 | 0.5626 | 0.167* | |
C16 | 0.0634 (4) | 0.7711 (5) | 0.49605 (19) | 0.0863 (15) | |
H16A | 0.0733 | 0.6734 | 0.4947 | 0.129* | |
H16B | 0.1465 | 0.8133 | 0.4806 | 0.129* | |
H16C | −0.0109 | 0.7981 | 0.4670 | 0.129* | |
N1 | 0.5461 (2) | 0.9545 (2) | 0.64167 (12) | 0.0273 (6) | |
N2 | 0.4723 (2) | 1.2469 (2) | 0.49486 (11) | 0.0280 (5) | |
N3 | 0.0346 (3) | 0.8149 (4) | 0.56650 (16) | 0.0499 (8) | |
O1 | 0.3558 (2) | 0.8512 (2) | 0.56273 (11) | 0.0421 (5) | |
O2 | 0.2639 (3) | 0.7320 (2) | 0.64708 (11) | 0.0503 (6) | |
O3 | 0.6862 (2) | 1.1467 (2) | 0.58118 (11) | 0.0426 (6) | |
O4 | 0.8198 (2) | 1.1765 (2) | 0.67165 (11) | 0.0535 (6) | |
O5 | 0.6502 (2) | 1.0789 (2) | 0.44054 (11) | 0.0382 (5) | |
O6 | 0.7113 (2) | 1.2269 (2) | 0.36104 (10) | 0.0452 (5) | |
O7 | 0.2192 (2) | 1.3241 (3) | 0.61473 (12) | 0.0591 (7) | |
O8 | 0.3369 (2) | 1.1322 (2) | 0.59481 (11) | 0.0431 (5) | |
O1W | 0.6295 (3) | 0.8450 (3) | 0.51261 (13) | 0.0495 (7) | |
O2W | 0.3720 (3) | 0.9959 (3) | 0.44420 (12) | 0.0403 (6) | |
In1 | 0.50674 (3) | 1.030806 (16) | 0.533088 (16) | 0.02626 (5) | |
HW11 | 0.672 (4) | 0.801 (4) | 0.5425 (17) | 0.100 (17)* | |
HW12 | 0.655 (4) | 0.822 (3) | 0.4789 (16) | 0.029 (11)* | |
HW22 | 0.355 (4) | 0.927 (4) | 0.4299 (18) | 0.054 (13)* | |
HW21 | 0.322 (4) | 1.053 (4) | 0.4337 (18) | 0.053 (13)* | |
H32 | −0.048 (4) | 0.766 (4) | 0.5822 (18) | 0.072 (12)* | |
H31 | 0.086 (4) | 0.775 (4) | 0.593 (2) | 0.067 (13)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0273 (16) | 0.0379 (18) | 0.0435 (19) | −0.0013 (14) | 0.0033 (14) | −0.0103 (15) |
C2 | 0.0259 (15) | 0.0323 (15) | 0.0333 (17) | 0.0001 (12) | −0.0034 (12) | −0.0097 (13) |
C3 | 0.0343 (16) | 0.053 (2) | 0.0320 (18) | −0.0010 (15) | −0.0088 (13) | −0.0118 (15) |
C4 | 0.0386 (15) | 0.058 (2) | 0.0257 (18) | 0.0021 (15) | −0.0062 (13) | 0.0024 (14) |
C5 | 0.0366 (17) | 0.0417 (17) | 0.0285 (16) | −0.0017 (14) | 0.0040 (13) | 0.0060 (13) |
C6 | 0.0294 (15) | 0.0316 (15) | 0.0241 (15) | −0.0003 (12) | −0.0003 (12) | −0.0011 (12) |
C7 | 0.0342 (18) | 0.0399 (18) | 0.0326 (18) | −0.0071 (15) | 0.0002 (15) | 0.0002 (14) |
C8 | 0.0304 (17) | 0.0396 (18) | 0.0277 (16) | −0.0091 (13) | 0.0012 (13) | −0.0030 (14) |
C9 | 0.0339 (16) | 0.0314 (16) | 0.0294 (16) | −0.0051 (13) | −0.0060 (13) | 0.0046 (12) |
C10 | 0.049 (2) | 0.0382 (18) | 0.049 (2) | −0.0001 (16) | −0.0152 (16) | 0.0126 (16) |
C11 | 0.063 (2) | 0.0297 (18) | 0.076 (3) | 0.0098 (18) | −0.027 (2) | 0.0092 (18) |
C12 | 0.047 (2) | 0.0395 (18) | 0.064 (2) | 0.0215 (16) | −0.0172 (18) | −0.0131 (16) |
C13 | 0.0292 (15) | 0.0360 (14) | 0.0396 (17) | 0.0051 (12) | −0.0071 (13) | −0.0109 (17) |
C14 | 0.0267 (16) | 0.055 (2) | 0.0365 (17) | 0.0029 (15) | −0.0029 (14) | −0.0186 (15) |
C15 | 0.062 (3) | 0.054 (3) | 0.219 (6) | 0.011 (2) | −0.018 (3) | −0.034 (3) |
C16 | 0.071 (3) | 0.137 (5) | 0.052 (3) | −0.032 (3) | −0.007 (2) | −0.024 (3) |
N1 | 0.0251 (12) | 0.0324 (13) | 0.0245 (12) | −0.0019 (10) | 0.0009 (10) | −0.0011 (10) |
N2 | 0.0262 (12) | 0.0283 (12) | 0.0297 (13) | 0.0027 (10) | −0.0017 (10) | −0.0033 (10) |
N3 | 0.0390 (17) | 0.073 (2) | 0.0379 (17) | −0.0067 (17) | −0.0042 (14) | 0.0061 (16) |
O1 | 0.0430 (13) | 0.0549 (13) | 0.0285 (12) | −0.0198 (11) | −0.0092 (10) | 0.0083 (10) |
O2 | 0.0472 (13) | 0.0669 (15) | 0.0367 (14) | −0.0286 (11) | −0.0045 (11) | 0.0144 (12) |
O3 | 0.0368 (12) | 0.0467 (14) | 0.0444 (15) | −0.0124 (11) | −0.0011 (10) | 0.0035 (11) |
O4 | 0.0443 (13) | 0.0572 (15) | 0.0589 (15) | −0.0217 (12) | −0.0081 (11) | −0.0132 (12) |
O5 | 0.0408 (12) | 0.0389 (13) | 0.0348 (12) | 0.0085 (10) | 0.0158 (10) | 0.0091 (10) |
O6 | 0.0507 (13) | 0.0537 (14) | 0.0312 (11) | −0.0093 (11) | 0.0127 (10) | 0.0051 (10) |
O7 | 0.0329 (12) | 0.0828 (18) | 0.0615 (16) | 0.0144 (12) | 0.0098 (11) | −0.0310 (14) |
O8 | 0.0391 (13) | 0.0545 (15) | 0.0356 (12) | 0.0008 (11) | 0.0128 (10) | −0.0001 (10) |
O1W | 0.0797 (19) | 0.0467 (14) | 0.0222 (14) | 0.0318 (14) | 0.0055 (13) | 0.0029 (10) |
O2W | 0.0532 (16) | 0.0321 (14) | 0.0355 (13) | 0.0097 (13) | −0.0134 (12) | −0.0080 (11) |
In1 | 0.02835 (11) | 0.02746 (10) | 0.02297 (7) | 0.00098 (13) | 0.00290 (7) | 0.00217 (19) |
Geometric parameters (Å, º) top
C1—O4 | 1.234 (3) | C13—N2 | 1.333 (3) |
C1—O3 | 1.256 (4) | C13—C14 | 1.510 (4) |
C1—C2 | 1.499 (4) | C14—O7 | 1.226 (3) |
C2—N1 | 1.341 (3) | C14—O8 | 1.269 (4) |
C2—C3 | 1.386 (4) | C15—N3 | 1.442 (5) |
C3—C4 | 1.366 (4) | C15—H15A | 0.9600 |
C3—H3 | 0.9300 | C15—H15B | 0.9600 |
C4—C5 | 1.383 (4) | C15—H15C | 0.9600 |
C4—H4 | 0.9300 | C16—N3 | 1.475 (4) |
C5—C6 | 1.369 (4) | C16—H16A | 0.9600 |
C5—H5 | 0.9300 | C16—H16B | 0.9600 |
C6—N1 | 1.336 (3) | C16—H16C | 0.9600 |
C6—C7 | 1.504 (4) | N1—In1 | 2.291 (2) |
C7—O2 | 1.249 (4) | N2—In1 | 2.266 (2) |
C7—O1 | 1.257 (3) | N3—H32 | 0.99 (4) |
C8—O5 | 1.239 (3) | N3—H31 | 0.83 (4) |
C8—O6 | 1.253 (3) | O1—In1 | 2.364 (2) |
C8—C9 | 1.509 (4) | O3—In1 | 2.291 (2) |
C9—N2 | 1.331 (3) | O5—In1 | 2.3420 (19) |
C9—C10 | 1.385 (4) | O8—In1 | 2.281 (2) |
C10—C11 | 1.383 (4) | O1W—In1 | 2.212 (3) |
C10—H10 | 0.9300 | O1W—HW11 | 0.84 (4) |
C11—C12 | 1.379 (5) | O1W—HW12 | 0.74 (3) |
C11—H11 | 0.9300 | O2W—In1 | 2.212 (2) |
C12—C13 | 1.382 (4) | O2W—HW22 | 0.75 (4) |
C12—H12 | 0.9300 | O2W—HW21 | 0.77 (4) |
| | | |
O4—C1—O3 | 126.5 (3) | H16A—C16—H16C | 109.5 |
O4—C1—C2 | 117.0 (3) | H16B—C16—H16C | 109.5 |
O3—C1—C2 | 116.5 (3) | C6—N1—C2 | 120.4 (2) |
N1—C2—C3 | 120.3 (3) | C6—N1—In1 | 120.67 (18) |
N1—C2—C1 | 114.1 (3) | C2—N1—In1 | 118.96 (19) |
C3—C2—C1 | 125.5 (3) | C9—N2—C13 | 121.1 (2) |
C4—C3—C2 | 119.5 (3) | C9—N2—In1 | 120.09 (17) |
C4—C3—H3 | 120.2 | C13—N2—In1 | 118.79 (18) |
C2—C3—H3 | 120.2 | C15—N3—C16 | 115.3 (4) |
C3—C4—C5 | 119.3 (3) | C15—N3—H32 | 110 (2) |
C3—C4—H4 | 120.3 | C16—N3—H32 | 108 (2) |
C5—C4—H4 | 120.3 | C15—N3—H31 | 117 (3) |
C6—C5—C4 | 119.1 (3) | C16—N3—H31 | 110 (3) |
C6—C5—H5 | 120.5 | H32—N3—H31 | 94 (3) |
C4—C5—H5 | 120.5 | C7—O1—In1 | 119.02 (19) |
N1—C6—C5 | 121.4 (3) | C1—O3—In1 | 120.96 (19) |
N1—C6—C7 | 113.9 (2) | C8—O5—In1 | 119.58 (18) |
C5—C6—C7 | 124.7 (3) | C14—O8—In1 | 120.32 (19) |
O2—C7—O1 | 124.2 (3) | In1—O1W—HW11 | 124 (3) |
O2—C7—C6 | 118.9 (3) | In1—O1W—HW12 | 126 (3) |
O1—C7—C6 | 116.9 (3) | HW11—O1W—HW12 | 108 (4) |
O5—C8—O6 | 125.0 (3) | In1—O2W—HW22 | 125 (3) |
O5—C8—C9 | 116.8 (2) | In1—O2W—HW21 | 119 (3) |
O6—C8—C9 | 118.2 (3) | HW22—O2W—HW21 | 114 (4) |
N2—C9—C10 | 121.0 (3) | O1W—In1—O2W | 93.02 (10) |
N2—C9—C8 | 114.3 (2) | O1W—In1—N2 | 141.69 (9) |
C10—C9—C8 | 124.7 (3) | O2W—In1—N2 | 78.13 (9) |
C11—C10—C9 | 118.2 (3) | O1W—In1—O8 | 147.92 (9) |
C11—C10—H10 | 120.9 | O2W—In1—O8 | 93.05 (9) |
C9—C10—H10 | 120.9 | N2—In1—O8 | 70.33 (8) |
C12—C11—C10 | 120.3 (3) | O1W—In1—N1 | 79.11 (9) |
C12—C11—H11 | 119.9 | O2W—In1—N1 | 141.60 (9) |
C10—C11—H11 | 119.9 | N2—In1—N1 | 129.52 (8) |
C11—C12—C13 | 118.5 (3) | O8—In1—N1 | 76.65 (8) |
C11—C12—H12 | 120.8 | O1W—In1—O3 | 93.75 (10) |
C13—C12—H12 | 120.8 | O2W—In1—O3 | 148.95 (9) |
N2—C13—C12 | 120.9 (3) | N2—In1—O3 | 77.84 (8) |
N2—C13—C14 | 114.8 (2) | O8—In1—O3 | 97.07 (8) |
C12—C13—C14 | 124.3 (3) | N1—In1—O3 | 69.44 (8) |
O7—C14—O8 | 127.0 (3) | O1W—In1—O5 | 72.49 (9) |
O7—C14—C13 | 117.4 (3) | O2W—In1—O5 | 77.00 (9) |
O8—C14—C13 | 115.6 (3) | N2—In1—O5 | 69.20 (7) |
N3—C15—H15A | 109.5 | O8—In1—O5 | 139.49 (8) |
N3—C15—H15B | 109.5 | N1—In1—O5 | 133.36 (8) |
H15A—C15—H15B | 109.5 | O3—In1—O5 | 76.27 (8) |
N3—C15—H15C | 109.5 | O1W—In1—O1 | 76.95 (9) |
H15A—C15—H15C | 109.5 | O2W—In1—O1 | 73.05 (9) |
H15B—C15—H15C | 109.5 | N2—In1—O1 | 132.87 (8) |
N3—C16—H16A | 109.5 | O8—In1—O1 | 74.81 (8) |
N3—C16—H16B | 109.5 | N1—In1—O1 | 68.55 (8) |
H16A—C16—H16B | 109.5 | O3—In1—O1 | 137.96 (8) |
N3—C16—H16C | 109.5 | O5—In1—O1 | 135.46 (8) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—HW12···O2i | 0.74 (3) | 1.96 (3) | 2.698 (3) | 171 (3) |
O1W—HW11···O6ii | 0.84 (4) | 1.88 (2) | 2.721 (3) | 177 (4) |
O2W—HW21···O4iii | 0.77 (4) | 1.90 (4) | 2.661 (3) | 169 (4) |
N3—H31···O2 | 0.83 (4) | 2.07 (4) | 2.859 (4) | 158 (4) |
N3—H32···O6iv | 0.99 (4) | 1.92 (4) | 2.884 (4) | 167 (3) |
Symmetry codes: (i) y, −x+1, z−1/4; (ii) −y+2, x, z+1/4; (iii) y−1, −x+2, z−1/4; (iv) −y+1, x, z+1/4. |