Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805039152/ng6243sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805039152/ng6243Isup2.hkl |
CCDC reference: 296617
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.005 Å
- R factor = 0.056
- wR factor = 0.131
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
1,1'-(Butane-1,4-diyl)bis-1H-benzimidazole (bbbm) was prepared according to a literature method (Xie et al., 2000). A methanol solution (5 ml) of H2pdc (16.7 mg, 0.1 mmol) was added dropwise to a methanol solution (5 ml) of Fe(ClO4)3·7H2O (23.2 mg, 0.05 mmol) and bbbm (29.0 mg, 0.1 mmol) to give a clear solution. Light-green block-like crystals (55% yield) of (I) were obtained one week later. IR (KBr, cm−1): 3081 (w), 1675 (s), 1452 (w), 1322 (s), 1167 (s), 1072 (s), 914 (m), 742 (s), 681 (m), 439 (w). Analysis calculated for C48H40Fe2N8O18: C 51.08, H 3.57, N 9.93%; found: C 51.23, H 3.47, N 9.85%.
All H atoms were placed in calculated positions and were refined isotropically, with Uiso(H) values constrained to 1.2Ueq(C,N) or 1.5Ueq(C), using a riding model with C—H = 0.93–0.97 Å. Uiso treatment for OH group?
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
(C18H20N4)[Fe(C7H3NO4)2]2·2CH4O | Z = 1 |
Mr = 1128.58 | F(000) = 580 |
Triclinic, P1 | Dx = 1.549 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.2751 (19) Å | Cell parameters from 779 reflections |
b = 11.035 (2) Å | θ = 2.1–18.0° |
c = 13.167 (3) Å | µ = 0.69 mm−1 |
α = 106.50 (3)° | T = 291 K |
β = 101.19 (3)° | Block, light-green |
γ = 103.07 (3)° | 0.20 × 0.18 × 0.17 mm |
V = 1209.6 (6) Å3 |
Bruker SMART APEX CCD area-detector diffractometer | 4764 independent reflections |
Radiation source: sealed tube | 3875 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
ϕ and ω scans | θmax = 26.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −11→11 |
Tmin = 0.875, Tmax = 0.892 | k = −13→13 |
8712 measured reflections | l = −16→16 |
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.131 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.06P)2 + 0.88P] where P = (Fo2 + 2Fc2)/3 |
4764 reflections | (Δ/σ)max < 0.001 |
344 parameters | Δρmax = 0.43 e Å−3 |
0 restraints | Δρmin = −0.74 e Å−3 |
(C18H20N4)[Fe(C7H3NO4)2]2·2CH4O | γ = 103.07 (3)° |
Mr = 1128.58 | V = 1209.6 (6) Å3 |
Triclinic, P1 | Z = 1 |
a = 9.2751 (19) Å | Mo Kα radiation |
b = 11.035 (2) Å | µ = 0.69 mm−1 |
c = 13.167 (3) Å | T = 291 K |
α = 106.50 (3)° | 0.20 × 0.18 × 0.17 mm |
β = 101.19 (3)° |
Bruker SMART APEX CCD area-detector diffractometer | 4764 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 3875 reflections with I > 2σ(I) |
Tmin = 0.875, Tmax = 0.892 | Rint = 0.046 |
8712 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.131 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.43 e Å−3 |
4764 reflections | Δρmin = −0.74 e Å−3 |
344 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 | ||
C1 | 0.6926 (4) | 1.0617 (3) | 1.0015 (3) | 0.0357 (7) | |
C2 | 0.7244 (4) | 1.0636 (4) | 1.1099 (3) | 0.0413 (8) | |
H2 | 0.6968 | 1.1225 | 1.1632 | 0.050* | |
C3 | 0.7972 (4) | 0.9767 (4) | 1.1366 (3) | 0.0442 (8) | |
H3 | 0.8200 | 0.9773 | 1.2088 | 0.053* | |
C4 | 0.8369 (4) | 0.8886 (3) | 1.0571 (3) | 0.0380 (8) | |
H4 | 0.8852 | 0.8290 | 1.0746 | 0.046* | |
C5 | 0.8032 (3) | 0.8914 (3) | 0.9518 (2) | 0.0311 (7) | |
C6 | 0.6193 (4) | 1.1504 (3) | 0.9533 (3) | 0.0351 (7) | |
C7 | 0.8393 (4) | 0.8089 (3) | 0.8531 (3) | 0.0340 (7) | |
C8 | 0.5383 (3) | 0.8588 (3) | 0.5293 (3) | 0.0295 (6) | |
H9E | 0.9205 | 0.7792 | 0.6721 | 0.035* | |
C9 | 0.5241 (4) | 0.8296 (4) | 0.4180 (3) | 0.0422 (8) | |
H9 | 0.4370 | 0.7662 | 0.3664 | 0.051* | |
C10 | 0.6420 (5) | 0.8965 (4) | 0.3834 (3) | 0.0486 (9) | |
H10 | 0.6336 | 0.8789 | 0.3087 | 0.058* | |
C11 | 0.7723 (4) | 0.9900 (3) | 0.4629 (3) | 0.0355 (7) | |
H11 | 0.8521 | 1.0359 | 0.4423 | 0.043* | |
C12 | 0.7799 (3) | 1.0128 (3) | 0.5732 (2) | 0.0284 (6) | |
C13 | 0.4284 (4) | 0.7997 (3) | 0.5859 (3) | 0.0370 (7) | |
C14 | 0.9097 (4) | 1.1072 (3) | 0.6736 (3) | 0.0359 (7) | |
C15 | 0.3360 (4) | 0.5495 (3) | 0.7372 (3) | 0.0345 (7) | |
C16 | 0.4811 (4) | 0.5538 (3) | 0.7256 (3) | 0.0394 (8) | |
H16A | 0.5247 | 0.5991 | 0.6839 | 0.047* | |
C17 | 0.5572 (4) | 0.4872 (4) | 0.7792 (3) | 0.0445 (8) | |
H17A | 0.6554 | 0.4869 | 0.7732 | 0.053* | |
C18 | 0.4937 (4) | 0.4200 (4) | 0.8424 (3) | 0.0483 (9) | |
H18A | 0.5507 | 0.3773 | 0.8781 | 0.058* | |
C19 | 0.3489 (4) | 0.4155 (3) | 0.8533 (3) | 0.0430 (8) | |
H19A | 0.3050 | 0.3695 | 0.8944 | 0.052* | |
C20 | 0.2711 (4) | 0.4834 (3) | 0.7994 (3) | 0.0353 (7) | |
C21 | 0.1078 (4) | 0.5786 (3) | 0.7354 (3) | 0.0367 (7) | |
H21A | 0.0217 | 0.6076 | 0.7215 | 0.044* | |
C22 | 0.0148 (4) | 0.4522 (3) | 0.8512 (3) | 0.0380 (7) | |
H22A | 0.0059 | 0.3598 | 0.8401 | 0.046* | |
H22B | −0.0853 | 0.4572 | 0.8173 | 0.046* | |
C23 | 0.0597 (4) | 0.5286 (3) | 0.9734 (3) | 0.0389 (8) | |
H23B | 0.0673 | 0.6209 | 0.9851 | 0.047* | |
H23A | 0.1599 | 0.5240 | 1.0078 | 0.047* | |
C24 | 0.8961 (5) | 0.6846 (4) | 0.5266 (3) | 0.0521 (9) | |
H24A | 0.8356 | 0.7248 | 0.4864 | 0.078* | |
H24B | 0.8290 | 0.6152 | 0.5409 | 0.078* | |
H24C | 0.9590 | 0.6484 | 0.4839 | 0.078* | |
Fe1 | 0.68843 (5) | 0.98165 (4) | 0.76879 (4) | 0.03254 (15) | |
N1 | 0.7338 (3) | 0.9765 (3) | 0.9268 (2) | 0.0324 (6) | |
N2 | 0.6650 (3) | 0.9485 (3) | 0.6026 (2) | 0.0295 (5) | |
N3 | 0.2277 (3) | 0.6065 (3) | 0.6977 (2) | 0.0362 (6) | |
H3E | 0.2352 | 0.6476 | 0.6494 | 0.043* | |
N4 | 0.1276 (3) | 0.5030 (3) | 0.7961 (2) | 0.0326 (6) | |
O1 | 0.6088 (3) | 1.1228 (2) | 0.84865 (17) | 0.0325 (5) | |
O2 | 0.5797 (3) | 1.2364 (3) | 1.0107 (2) | 0.0484 (6) | |
O3 | 0.7941 (3) | 0.8350 (2) | 0.76377 (19) | 0.0396 (5) | |
O4 | 0.9037 (3) | 0.7241 (3) | 0.8583 (2) | 0.0427 (6) | |
O5 | 0.4744 (3) | 0.8502 (2) | 0.69136 (18) | 0.0373 (5) | |
O6 | 0.3070 (3) | 0.7114 (3) | 0.5324 (2) | 0.0487 (6) | |
O7 | 0.8761 (3) | 1.1106 (2) | 0.76627 (18) | 0.0402 (5) | |
O8 | 1.0268 (3) | 1.1721 (3) | 0.6645 (2) | 0.0524 (7) | |
O9 | 0.9909 (3) | 0.7808 (3) | 0.6272 (2) | 0.0538 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0356 (16) | 0.0354 (17) | 0.0342 (16) | 0.0069 (13) | 0.0108 (13) | 0.0112 (13) |
C2 | 0.0405 (18) | 0.047 (2) | 0.0323 (17) | 0.0051 (15) | 0.0128 (14) | 0.0124 (15) |
C3 | 0.0421 (19) | 0.046 (2) | 0.0418 (19) | 0.0038 (16) | 0.0053 (15) | 0.0225 (16) |
C4 | 0.0377 (17) | 0.0422 (18) | 0.0394 (18) | 0.0030 (14) | 0.0069 (14) | 0.0312 (15) |
C5 | 0.0270 (14) | 0.0406 (17) | 0.0292 (15) | 0.0052 (12) | 0.0069 (12) | 0.0215 (13) |
C6 | 0.0409 (17) | 0.0252 (15) | 0.0359 (17) | 0.0071 (13) | 0.0139 (14) | 0.0054 (13) |
C7 | 0.0325 (16) | 0.0299 (16) | 0.0455 (18) | 0.0099 (13) | 0.0134 (14) | 0.0194 (14) |
C8 | 0.0271 (15) | 0.0298 (15) | 0.0368 (16) | 0.0109 (12) | 0.0124 (13) | 0.0148 (13) |
C9 | 0.0419 (18) | 0.0424 (19) | 0.0368 (18) | 0.0106 (15) | 0.0060 (15) | 0.0100 (15) |
C10 | 0.052 (2) | 0.050 (2) | 0.041 (2) | 0.0158 (18) | 0.0129 (17) | 0.0105 (17) |
C11 | 0.0394 (18) | 0.0413 (18) | 0.0358 (17) | 0.0131 (14) | 0.0209 (14) | 0.0204 (14) |
C12 | 0.0281 (14) | 0.0318 (15) | 0.0275 (14) | 0.0062 (12) | 0.0096 (12) | 0.0146 (12) |
C13 | 0.0400 (18) | 0.0363 (17) | 0.0390 (18) | 0.0075 (14) | 0.0153 (15) | 0.0196 (14) |
C14 | 0.0384 (17) | 0.0298 (16) | 0.0393 (17) | 0.0059 (13) | 0.0082 (14) | 0.0164 (14) |
C15 | 0.0407 (17) | 0.0247 (15) | 0.0427 (18) | 0.0114 (13) | 0.0228 (15) | 0.0098 (13) |
C16 | 0.0347 (17) | 0.0373 (17) | 0.051 (2) | 0.0066 (14) | 0.0281 (15) | 0.0152 (15) |
C17 | 0.0294 (16) | 0.050 (2) | 0.053 (2) | 0.0163 (15) | 0.0170 (15) | 0.0085 (17) |
C18 | 0.046 (2) | 0.042 (2) | 0.057 (2) | 0.0192 (17) | 0.0059 (17) | 0.0194 (17) |
C19 | 0.0416 (19) | 0.0343 (18) | 0.050 (2) | 0.0076 (15) | 0.0097 (16) | 0.0153 (16) |
C20 | 0.0349 (16) | 0.0340 (17) | 0.0323 (16) | 0.0074 (13) | 0.0118 (13) | 0.0052 (13) |
C21 | 0.0406 (18) | 0.0386 (18) | 0.0379 (18) | 0.0184 (15) | 0.0153 (14) | 0.0155 (14) |
C22 | 0.0333 (16) | 0.0394 (18) | 0.0431 (18) | 0.0065 (14) | 0.0181 (14) | 0.0155 (15) |
C23 | 0.0432 (19) | 0.0349 (17) | 0.0452 (19) | 0.0079 (14) | 0.0203 (16) | 0.0208 (15) |
C24 | 0.058 (2) | 0.052 (2) | 0.046 (2) | 0.0216 (19) | 0.0177 (18) | 0.0087 (18) |
Fe1 | 0.0391 (3) | 0.0327 (3) | 0.0290 (2) | 0.0134 (2) | 0.00964 (19) | 0.01289 (19) |
N1 | 0.0345 (14) | 0.0311 (13) | 0.0332 (14) | 0.0100 (11) | 0.0082 (11) | 0.0139 (11) |
N2 | 0.0291 (13) | 0.0312 (13) | 0.0297 (13) | 0.0107 (11) | 0.0092 (10) | 0.0105 (11) |
N3 | 0.0447 (16) | 0.0364 (14) | 0.0395 (15) | 0.0150 (12) | 0.0219 (13) | 0.0218 (12) |
N4 | 0.0359 (14) | 0.0328 (14) | 0.0308 (13) | 0.0076 (11) | 0.0147 (11) | 0.0117 (11) |
O1 | 0.0391 (12) | 0.0327 (11) | 0.0290 (11) | 0.0134 (9) | 0.0096 (9) | 0.0129 (9) |
O2 | 0.0469 (14) | 0.0433 (14) | 0.0588 (16) | 0.0215 (12) | 0.0301 (13) | 0.0064 (12) |
O3 | 0.0539 (14) | 0.0421 (13) | 0.0340 (12) | 0.0249 (11) | 0.0228 (11) | 0.0143 (10) |
O4 | 0.0508 (14) | 0.0512 (14) | 0.0525 (15) | 0.0354 (12) | 0.0266 (12) | 0.0331 (12) |
O5 | 0.0384 (12) | 0.0461 (13) | 0.0326 (12) | 0.0082 (10) | 0.0175 (10) | 0.0197 (10) |
O6 | 0.0441 (14) | 0.0465 (15) | 0.0488 (15) | −0.0039 (12) | 0.0109 (12) | 0.0209 (12) |
O7 | 0.0397 (12) | 0.0463 (14) | 0.0258 (11) | 0.0047 (11) | 0.0014 (9) | 0.0105 (10) |
O8 | 0.0377 (13) | 0.0490 (15) | 0.0522 (16) | −0.0105 (11) | 0.0117 (12) | 0.0091 (12) |
O9 | 0.0549 (16) | 0.0572 (17) | 0.0532 (16) | 0.0157 (13) | 0.0312 (13) | 0.0146 (13) |
C1—N1 | 1.335 (4) | C15—N3 | 1.395 (4) |
C1—C2 | 1.393 (5) | C16—C17 | 1.368 (5) |
C1—C6 | 1.520 (5) | C16—H16A | 0.9300 |
C2—C3 | 1.375 (5) | C17—C18 | 1.390 (6) |
C2—H2 | 0.9300 | C17—H17A | 0.9300 |
C3—C4 | 1.382 (5) | C18—C19 | 1.369 (5) |
C3—H3 | 0.9300 | C18—H18A | 0.9300 |
C4—C5 | 1.372 (4) | C19—C20 | 1.390 (5) |
C4—H4 | 0.9300 | C19—H19A | 0.9300 |
C5—N1 | 1.330 (4) | C20—N4 | 1.391 (4) |
C5—C7 | 1.504 (5) | C21—N3 | 1.313 (4) |
C6—O2 | 1.210 (4) | C21—N4 | 1.327 (4) |
C6—O1 | 1.303 (4) | C21—H21A | 0.9300 |
C7—O4 | 1.229 (4) | C22—N4 | 1.482 (4) |
C7—O3 | 1.303 (4) | C22—C23 | 1.511 (5) |
C8—N2 | 1.336 (4) | C22—H22A | 0.9700 |
C8—C9 | 1.380 (5) | C22—H22B | 0.9700 |
C8—C13 | 1.514 (4) | C23—C23i | 1.534 (6) |
C9—C10 | 1.403 (5) | C23—H23B | 0.9700 |
C9—H9 | 0.9300 | C23—H23A | 0.9700 |
C10—C11 | 1.397 (5) | C24—O9 | 1.407 (5) |
C10—H10 | 0.9300 | C24—H24A | 0.9600 |
C11—C12 | 1.386 (4) | C24—H24B | 0.9600 |
C11—H11 | 0.9300 | C24—H24C | 0.9600 |
C12—N2 | 1.328 (4) | Fe1—O1 | 1.992 (2) |
C12—C14 | 1.522 (5) | Fe1—O7 | 1.996 (3) |
C13—O6 | 1.233 (4) | Fe1—O5 | 2.039 (3) |
C13—O5 | 1.282 (4) | Fe1—N1 | 2.061 (3) |
C14—O8 | 1.205 (4) | Fe1—O3 | 2.066 (2) |
C14—O7 | 1.310 (4) | Fe1—N2 | 2.073 (3) |
C15—C16 | 1.376 (4) | N3—H3E | 0.8847 |
C15—C20 | 1.378 (5) | O9—H9E | 0.9628 |
N1—C1—C2 | 119.4 (3) | C15—C20—C19 | 121.5 (3) |
N1—C1—C6 | 112.1 (3) | C15—C20—N4 | 107.1 (3) |
C2—C1—C6 | 128.4 (3) | C19—C20—N4 | 131.4 (3) |
C3—C2—C1 | 118.8 (3) | N3—C21—N4 | 110.0 (3) |
C3—C2—H2 | 120.6 | N3—C21—H21A | 125.0 |
C1—C2—H2 | 120.6 | N4—C21—H21A | 125.0 |
C2—C3—C4 | 120.5 (3) | N4—C22—C23 | 112.6 (3) |
C2—C3—H3 | 119.8 | N4—C22—H22A | 109.1 |
C4—C3—H3 | 119.8 | C23—C22—H22A | 109.1 |
C5—C4—C3 | 118.2 (3) | N4—C22—H22B | 109.1 |
C5—C4—H4 | 120.9 | C23—C22—H22B | 109.1 |
C3—C4—H4 | 120.9 | H22A—C22—H22B | 107.8 |
N1—C5—C4 | 120.9 (3) | C22—C23—C23i | 110.6 (4) |
N1—C5—C7 | 111.2 (3) | C22—C23—H23B | 109.5 |
C4—C5—C7 | 127.8 (3) | C23i—C23—H23B | 109.5 |
O2—C6—O1 | 126.9 (3) | C22—C23—H23A | 109.5 |
O2—C6—C1 | 120.8 (3) | C23i—C23—H23A | 109.5 |
O1—C6—C1 | 112.3 (3) | H23B—C23—H23A | 108.1 |
O4—C7—O3 | 124.3 (3) | O9—C24—H24A | 109.5 |
O4—C7—C5 | 121.9 (3) | O9—C24—H24B | 109.5 |
O3—C7—C5 | 113.8 (3) | H24A—C24—H24B | 109.5 |
N2—C8—C9 | 119.7 (3) | O9—C24—H24C | 109.5 |
N2—C8—C13 | 111.3 (3) | H24A—C24—H24C | 109.5 |
C9—C8—C13 | 129.0 (3) | H24B—C24—H24C | 109.5 |
C8—C9—C10 | 119.4 (3) | O1—Fe1—O7 | 93.60 (10) |
C8—C9—H9 | 120.3 | O1—Fe1—O5 | 93.73 (10) |
C10—C9—H9 | 120.3 | O7—Fe1—O5 | 150.61 (9) |
C11—C10—C9 | 118.9 (3) | O1—Fe1—N1 | 76.79 (10) |
C11—C10—H10 | 120.5 | O7—Fe1—N1 | 105.10 (10) |
C9—C10—H10 | 120.5 | O5—Fe1—N1 | 104.28 (10) |
C12—C11—C10 | 118.5 (3) | O1—Fe1—O3 | 151.81 (9) |
C12—C11—H11 | 120.8 | O7—Fe1—O3 | 93.24 (10) |
C10—C11—H11 | 120.8 | O5—Fe1—O3 | 93.59 (10) |
N2—C12—C11 | 120.7 (3) | N1—Fe1—O3 | 75.03 (10) |
N2—C12—C14 | 111.2 (3) | O1—Fe1—N2 | 117.19 (10) |
C11—C12—C14 | 128.0 (3) | O7—Fe1—N2 | 75.91 (10) |
O6—C13—O5 | 125.1 (3) | O5—Fe1—N2 | 75.43 (10) |
O6—C13—C8 | 121.2 (3) | N1—Fe1—N2 | 166.01 (10) |
O5—C13—C8 | 113.7 (3) | O3—Fe1—N2 | 91.00 (10) |
O8—C14—O7 | 126.0 (3) | C5—N1—C1 | 122.2 (3) |
O8—C14—C12 | 121.6 (3) | C5—N1—Fe1 | 120.2 (2) |
O7—C14—C12 | 112.4 (3) | C1—N1—Fe1 | 117.6 (2) |
C16—C15—C20 | 122.5 (3) | C12—N2—C8 | 122.7 (3) |
C16—C15—N3 | 131.9 (3) | C12—N2—Fe1 | 118.6 (2) |
C20—C15—N3 | 105.6 (3) | C8—N2—Fe1 | 118.7 (2) |
C17—C16—C15 | 115.7 (3) | C21—N3—C15 | 109.3 (3) |
C17—C16—H16A | 122.1 | C21—N3—H3E | 125.7 |
C15—C16—H16A | 122.1 | C15—N3—H3E | 124.8 |
C16—C17—C18 | 122.7 (3) | C21—N4—C20 | 108.0 (3) |
C16—C17—H17A | 118.7 | C21—N4—C22 | 124.6 (3) |
C18—C17—H17A | 118.7 | C20—N4—C22 | 127.3 (3) |
C19—C18—C17 | 121.4 (3) | C6—O1—Fe1 | 121.2 (2) |
C19—C18—H18A | 119.3 | C7—O3—Fe1 | 119.7 (2) |
C17—C18—H18A | 119.3 | C13—O5—Fe1 | 120.5 (2) |
C18—C19—C20 | 116.3 (3) | C14—O7—Fe1 | 121.1 (2) |
C18—C19—H19A | 121.8 | C24—O9—H9E | 100.5 |
C20—C19—H19A | 121.8 | ||
N1—C1—C2—C3 | −0.2 (5) | C11—C12—N2—C8 | 0.7 (5) |
C6—C1—C2—C3 | −177.5 (3) | C14—C12—N2—C8 | −179.2 (3) |
C1—C2—C3—C4 | −0.5 (5) | C11—C12—N2—Fe1 | 177.4 (2) |
C2—C3—C4—C5 | 0.7 (5) | C14—C12—N2—Fe1 | −2.4 (3) |
C3—C4—C5—N1 | −0.2 (5) | C9—C8—N2—C12 | 0.3 (5) |
C3—C4—C5—C7 | 178.0 (3) | C13—C8—N2—C12 | 179.0 (3) |
N1—C1—C6—O2 | −177.6 (3) | C9—C8—N2—Fe1 | −176.4 (2) |
C2—C1—C6—O2 | −0.2 (5) | C13—C8—N2—Fe1 | 2.3 (3) |
N1—C1—C6—O1 | 1.5 (4) | O1—Fe1—N2—C12 | 92.2 (2) |
C2—C1—C6—O1 | 178.9 (3) | O7—Fe1—N2—C12 | 5.4 (2) |
N1—C5—C7—O4 | 179.9 (3) | O5—Fe1—N2—C12 | 178.9 (2) |
C4—C5—C7—O4 | 1.6 (5) | N1—Fe1—N2—C12 | −90.5 (5) |
N1—C5—C7—O3 | −1.0 (4) | O3—Fe1—N2—C12 | −87.6 (2) |
C4—C5—C7—O3 | −179.3 (3) | O1—Fe1—N2—C8 | −90.9 (2) |
N2—C8—C9—C10 | −1.1 (5) | O7—Fe1—N2—C8 | −177.7 (2) |
C13—C8—C9—C10 | −179.5 (3) | O5—Fe1—N2—C8 | −4.3 (2) |
C8—C9—C10—C11 | 0.9 (5) | N1—Fe1—N2—C8 | 86.4 (5) |
C9—C10—C11—C12 | 0.1 (5) | O3—Fe1—N2—C8 | 89.2 (2) |
C10—C11—C12—N2 | −0.9 (5) | N4—C21—N3—C15 | −1.5 (4) |
C10—C11—C12—C14 | 178.9 (3) | C16—C15—N3—C21 | −177.1 (4) |
N2—C8—C13—O6 | −177.4 (3) | C20—C15—N3—C21 | 1.1 (4) |
C9—C8—C13—O6 | 1.1 (5) | N3—C21—N4—C20 | 1.2 (4) |
N2—C8—C13—O5 | 2.7 (4) | N3—C21—N4—C22 | −179.7 (3) |
C9—C8—C13—O5 | −178.9 (3) | C15—C20—N4—C21 | −0.5 (4) |
N2—C12—C14—O8 | 177.8 (3) | C19—C20—N4—C21 | 178.1 (4) |
C11—C12—C14—O8 | −2.0 (5) | C15—C20—N4—C22 | −179.5 (3) |
N2—C12—C14—O7 | −4.0 (4) | C19—C20—N4—C22 | −0.9 (6) |
C11—C12—C14—O7 | 176.2 (3) | C23—C22—N4—C21 | −102.7 (4) |
C20—C15—C16—C17 | 0.4 (5) | C23—C22—N4—C20 | 76.2 (4) |
N3—C15—C16—C17 | 178.4 (4) | O2—C6—O1—Fe1 | 177.4 (3) |
C15—C16—C17—C18 | −0.5 (5) | C1—C6—O1—Fe1 | −1.6 (4) |
C16—C17—C18—C19 | 0.9 (6) | O7—Fe1—O1—C6 | −103.8 (2) |
C17—C18—C19—C20 | −1.1 (6) | O5—Fe1—O1—C6 | 104.7 (2) |
C16—C15—C20—C19 | −0.7 (5) | N1—Fe1—O1—C6 | 0.9 (2) |
N3—C15—C20—C19 | −179.2 (3) | O3—Fe1—O1—C6 | 0.0 (4) |
C16—C15—C20—N4 | 178.0 (3) | N2—Fe1—O1—C6 | −179.7 (2) |
N3—C15—C20—N4 | −0.4 (4) | O4—C7—O3—Fe1 | −179.6 (3) |
C18—C19—C20—C15 | 1.0 (5) | C5—C7—O3—Fe1 | 1.3 (4) |
C18—C19—C20—N4 | −177.4 (3) | O1—Fe1—O3—C7 | 0.1 (4) |
N4—C22—C23—C23i | −179.5 (3) | O7—Fe1—O3—C7 | 103.9 (2) |
C4—C5—N1—C1 | −0.6 (5) | O5—Fe1—O3—C7 | −104.7 (2) |
C7—C5—N1—C1 | −179.0 (3) | N1—Fe1—O3—C7 | −0.9 (2) |
C4—C5—N1—Fe1 | 178.7 (2) | N2—Fe1—O3—C7 | 179.8 (2) |
C7—C5—N1—Fe1 | 0.3 (3) | O6—C13—O5—Fe1 | 173.4 (3) |
C2—C1—N1—C5 | 0.8 (5) | C8—C13—O5—Fe1 | −6.6 (4) |
C6—C1—N1—C5 | 178.5 (3) | O1—Fe1—O5—C13 | 123.2 (2) |
C2—C1—N1—Fe1 | −178.5 (2) | O7—Fe1—O5—C13 | 19.1 (4) |
C6—C1—N1—Fe1 | −0.8 (3) | N1—Fe1—O5—C13 | −159.5 (2) |
O1—Fe1—N1—C5 | −179.3 (2) | O3—Fe1—O5—C13 | −84.0 (3) |
O7—Fe1—N1—C5 | −89.1 (2) | N2—Fe1—O5—C13 | 6.1 (2) |
O5—Fe1—N1—C5 | 90.2 (2) | O8—C14—O7—Fe1 | −172.6 (3) |
O3—Fe1—N1—C5 | 0.3 (2) | C12—C14—O7—Fe1 | 9.3 (4) |
N2—Fe1—N1—C5 | 3.2 (6) | O1—Fe1—O7—C14 | −125.4 (3) |
O1—Fe1—N1—C1 | 0.1 (2) | O5—Fe1—O7—C14 | −21.2 (4) |
O7—Fe1—N1—C1 | 90.3 (2) | N1—Fe1—O7—C14 | 157.3 (2) |
O5—Fe1—N1—C1 | −90.5 (2) | O3—Fe1—O7—C14 | 82.0 (3) |
O3—Fe1—N1—C1 | 179.6 (3) | N2—Fe1—O7—C14 | −8.2 (2) |
N2—Fe1—N1—C1 | −177.5 (4) |
Symmetry code: (i) −x, −y+1, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3E···O6 | 0.88 | 2.03 | 2.879 (4) | 161 |
O9—H9E···O3 | 0.96 | 1.91 | 2.843 (4) | 161 |
C22—H22A···O7ii | 0.97 | 2.55 | 3.460 (4) | 157 |
Symmetry code: (ii) x−1, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | (C18H20N4)[Fe(C7H3NO4)2]2·2CH4O |
Mr | 1128.58 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 291 |
a, b, c (Å) | 9.2751 (19), 11.035 (2), 13.167 (3) |
α, β, γ (°) | 106.50 (3), 101.19 (3), 103.07 (3) |
V (Å3) | 1209.6 (6) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.69 |
Crystal size (mm) | 0.20 × 0.18 × 0.17 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.875, 0.892 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8712, 4764, 3875 |
Rint | 0.046 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.131, 1.02 |
No. of reflections | 4764 |
No. of parameters | 344 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.43, −0.74 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Bruker, 2000), SHELXTL.
C1—N1 | 1.335 (4) | C20—N4 | 1.391 (4) |
C5—N1 | 1.330 (4) | C21—N3 | 1.313 (4) |
C6—O2 | 1.210 (4) | C21—N4 | 1.327 (4) |
C6—O1 | 1.303 (4) | C22—N4 | 1.482 (4) |
C7—O4 | 1.229 (4) | C24—O9 | 1.407 (5) |
C7—O3 | 1.303 (4) | Fe1—O1 | 1.992 (2) |
C8—N2 | 1.336 (4) | Fe1—O7 | 1.996 (3) |
C12—N2 | 1.328 (4) | Fe1—O5 | 2.039 (3) |
C13—O6 | 1.233 (4) | Fe1—N1 | 2.061 (3) |
C13—O5 | 1.282 (4) | Fe1—O3 | 2.066 (2) |
C14—O8 | 1.205 (4) | Fe1—N2 | 2.073 (3) |
C14—O7 | 1.310 (4) | N3—H3E | 0.8847 |
C15—N3 | 1.395 (4) | ||
O1—Fe1—O7 | 93.60 (10) | N1—Fe1—O3 | 75.03 (10) |
O1—Fe1—O5 | 93.73 (10) | O1—Fe1—N2 | 117.19 (10) |
O7—Fe1—O5 | 150.61 (9) | O7—Fe1—N2 | 75.91 (10) |
O1—Fe1—N1 | 76.79 (10) | O5—Fe1—N2 | 75.43 (10) |
O7—Fe1—N1 | 105.10 (10) | N1—Fe1—N2 | 166.01 (10) |
O5—Fe1—N1 | 104.28 (10) | O3—Fe1—N2 | 91.00 (10) |
O1—Fe1—O3 | 151.81 (9) | C5—N1—C1 | 122.2 (3) |
O7—Fe1—O3 | 93.24 (10) | C5—N1—Fe1 | 120.2 (2) |
O5—Fe1—O3 | 93.59 (10) | C1—N1—Fe1 | 117.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3E···O6 | 0.88 | 2.03 | 2.879 (4) | 161 |
O9—H9E···O3 | 0.96 | 1.91 | 2.843 (4) | 161 |
C22—H22A···O7i | 0.97 | 2.55 | 3.460 (4) | 157 |
Symmetry code: (i) x−1, y−1, z. |
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Proton transfer is one of the most important elementary processes in physics, chemistry and biochemistry, as it is the key process in important reactions such as auto ionization in water, acid–base neutralization reactions and enzyme catalysis (MacDonald et al., 2000). Extensive studies on the reaction of pyridine-2,6-dicarboxylic acid (H2pdc) with lanthanides and transition metals in the presence of Lewis bases such as pyridine-2,6-diamine (pda), 1,10-phenanthroline (phen) and creatinine (creat) have led to the isolation of proton transfer ionic complexes [pdaH]2[La2(pdc)4(H2O)4]·2H2O, [pdaH]2[Co(pdc)2]·H2O (Moghimi et al., 2002), (creatH)[Zn(pdc)(pdcH)]·4H2O (Moghimi, Sharif et al., 2005) and [Zn(pdc)2][Zn(phen)2(H2O)2]·7H2O (Moghimi, Sheshmani et al., 2005). On the other hand, the 1,1'-(butane-1,4-diyl)bis-1H-benzimidazole (bbbm) N-heterocycle as a flexible bidentate ligand affords adducts with some transition metal salts (Meng et al., 2003; Xiao et al., 2004). In this work, we selected H2pdc as the proton donor and bbbm as the proton acceptor, and successfully prepared a new proton transfer FeIII complex, (I).
Complex (I) consists of two mononuclear [Fe(pdc)2]− anions, one (H2bbbm)2+ dication and two solvent methanol moleculars (Fig. 1). The central Fe atom is hexacoordinated by two pyridine N and four carboxylate O atoms from two deprotonated H2pdc in an approximate octahedral geometry; the carboxyl group each coordinates in a monodentate fashion. The two ligands are almost perpendicular to each other.
Anions interact with the (H2bbbm)2+ dication and solvent methanol molecules to produce a hydrogen-bonded layered structure by three types of hydrogen bond (N—H···O, O—H···O and C—H···O) (Table 1 and Fig. 2). The [Fe(pdc)2]− units are linked into layers, and the space between these layers is occupied by the (H2bbbm)2+ cations. A face-to-face separation of 3.642 (2) A° between the N2-containing pyridine rings from two neighboring anions suggests the existence of π–π aromatic stacking interactions.