Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100013093/bm1421sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100013093/bm1421Isup2.hkl |
CCDC reference: 158221
Compound (I) was prepared by adding a warm solution of 1,10-phenanthroline (0.4488 g, 2.46 mmol) in water (50 ml), with stirring, to a warm clear solution of [Fe(sac)24H2O]·2H2O (0.4386 g, 0.83 mmol) in water (30 ml). A deep red solution formed; it was stirred for some time, and then left to stand. Fine red crystals formed after four weeks. These were separated, washed with 10 ml of cold distilled water and dried in air at room temperature. Elemental analyses, performed by the microanalytical services of the Department of Chemistry, University of Durham both before and after the crystal structure determination, indicated an average composition of [Fe(phen)3](sac)2.sacH·3H2O; found: C 57.18, H 3.72, N 10.66%; calculated for C57H43FeN9O12S3: C 57.15, H 3.62, N 10.52%. It is therefore probable that other material is present containing less water of crystallization than found in the crystals whose X-ray structure was determined in this work. Magnetic measurements were performed on a Johnson-Matthey-Evans magnetic susceptibility balance; the complex was shown to be diamagnetic.
All water H atoms and the amino H atom on the free saccharin molecule were refined. Other H atoms were treated as riding (C—H = 0.93 Å). Query.
Data collection: SMART-NT (Bruker, 1998); cell refinement: SMART-NT; data reduction: SAINT-NT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-NT (Bruker, 1998).
[Fe(C12H8N2)3](C7H4NO3S)2·C7H5NO3S·6H2O | F(000) = 2592 |
Mr = 1252.08 | Dx = 1.572 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 16.113 (4) Å | Cell parameters from 869 reflections |
b = 19.079 (5) Å | θ = 10.2–21.5° |
c = 17.227 (4) Å | µ = 0.49 mm−1 |
β = 92.873 (5)° | T = 120 K |
V = 5289 (2) Å3 | Rectangular plate, red |
Z = 4 | 0.48 × 0.19 × 0.10 mm |
Bruker SMART-CCD diffractometer | 14753 independent reflections |
Radiation source: fine-focus sealed tube | 7374 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.115 |
ω scans | θmax = 30.5°, θmin = 1.6° |
Absorption correction: integration (SHELXTL-NT; Bruker, 1998) | h = −22→20 |
Tmin = 0.830, Tmax = 0.954 | k = −26→26 |
47439 measured reflections | l = −24→24 |
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) = 0.145 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0583P)2 + 0.6223P] where P = (Fo2 + 2Fc2)/3 |
14753 reflections | (Δ/σ)max = 0.001 |
812 parameters | Δρmax = 0.52 e Å−3 |
18 restraints | Δρmin = −0.70 e Å−3 |
[Fe(C12H8N2)3](C7H4NO3S)2·C7H5NO3S·6H2O | V = 5289 (2) Å3 |
Mr = 1252.08 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 16.113 (4) Å | µ = 0.49 mm−1 |
b = 19.079 (5) Å | T = 120 K |
c = 17.227 (4) Å | 0.48 × 0.19 × 0.10 mm |
β = 92.873 (5)° |
Bruker SMART-CCD diffractometer | 14753 independent reflections |
Absorption correction: integration (SHELXTL-NT; Bruker, 1998) | 7374 reflections with I > 2σ(I) |
Tmin = 0.830, Tmax = 0.954 | Rint = 0.115 |
47439 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | 18 restraints |
wR(F2) = 0.145 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | Δρmax = 0.52 e Å−3 |
14753 reflections | Δρmin = −0.70 e Å−3 |
812 parameters |
Experimental. The detector was positioned at 2θ = -26° at a distance of 45 mm from the crystal. Data collection was carried out using ω scans, 0.3° wide 10 secs frames, starting at 3 different ϕ positions in order to cover a hemisphere. |
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 | ||
Fe1 | 0.52163 (3) | 0.24308 (2) | 0.54286 (2) | 0.01375 (11) | |
N1 | 0.48774 (16) | 0.30757 (14) | 0.45813 (14) | 0.0159 (6) | |
C1 | 0.4952 (2) | 0.30126 (18) | 0.38174 (18) | 0.0184 (7) | |
H1A | 0.5184 | 0.2605 | 0.3627 | 0.022* | |
C2 | 0.4696 (2) | 0.35343 (19) | 0.32946 (19) | 0.0206 (8) | |
H2A | 0.4767 | 0.3472 | 0.2767 | 0.025* | |
C3 | 0.4342 (2) | 0.41348 (19) | 0.35485 (19) | 0.0210 (8) | |
H3A | 0.4163 | 0.4480 | 0.3198 | 0.025* | |
C4 | 0.4252 (2) | 0.42246 (18) | 0.43517 (18) | 0.0175 (7) | |
C5 | 0.3899 (2) | 0.48258 (19) | 0.4694 (2) | 0.0243 (8) | |
H5B | 0.3687 | 0.5184 | 0.4376 | 0.029* | |
C6 | 0.3865 (2) | 0.48868 (19) | 0.5476 (2) | 0.0237 (8) | |
H6A | 0.3616 | 0.5279 | 0.5686 | 0.028* | |
C7 | 0.4206 (2) | 0.43578 (18) | 0.59782 (18) | 0.0188 (7) | |
C8 | 0.4250 (2) | 0.44084 (19) | 0.67953 (19) | 0.0226 (8) | |
H8A | 0.4025 | 0.4793 | 0.7042 | 0.027* | |
C9 | 0.4629 (2) | 0.38812 (18) | 0.72189 (19) | 0.0219 (8) | |
H9A | 0.4677 | 0.3912 | 0.7758 | 0.026* | |
C10 | 0.4941 (2) | 0.33032 (18) | 0.68477 (18) | 0.0179 (7) | |
H10A | 0.5196 | 0.2953 | 0.7150 | 0.021* | |
N2 | 0.48953 (16) | 0.32216 (14) | 0.60776 (14) | 0.0157 (6) | |
C11 | 0.45404 (19) | 0.37585 (17) | 0.56550 (18) | 0.0154 (7) | |
C12 | 0.45482 (19) | 0.36833 (17) | 0.48390 (18) | 0.0163 (7) | |
N3 | 0.40924 (16) | 0.20186 (14) | 0.54246 (14) | 0.0151 (6) | |
C13 | 0.3414 (2) | 0.22384 (18) | 0.57630 (18) | 0.0192 (7) | |
H13A | 0.3440 | 0.2654 | 0.6044 | 0.023* | |
C14 | 0.2667 (2) | 0.1869 (2) | 0.57116 (19) | 0.0236 (8) | |
H14A | 0.2208 | 0.2041 | 0.5956 | 0.028* | |
C15 | 0.2607 (2) | 0.12618 (18) | 0.53080 (19) | 0.0206 (8) | |
H15A | 0.2108 | 0.1017 | 0.5272 | 0.025* | |
C16 | 0.3307 (2) | 0.10048 (18) | 0.49437 (18) | 0.0175 (7) | |
C17 | 0.3315 (2) | 0.03785 (18) | 0.44892 (19) | 0.0226 (8) | |
H17A | 0.2836 | 0.0107 | 0.4435 | 0.027* | |
C18 | 0.4002 (2) | 0.01743 (19) | 0.41390 (19) | 0.0230 (8) | |
H18A | 0.3990 | −0.0237 | 0.3848 | 0.028* | |
C19 | 0.4753 (2) | 0.05772 (17) | 0.42043 (18) | 0.0176 (7) | |
C20 | 0.5487 (2) | 0.04083 (19) | 0.38436 (19) | 0.0216 (8) | |
H20A | 0.5516 | 0.0006 | 0.3542 | 0.026* | |
C21 | 0.6160 (2) | 0.08420 (18) | 0.39404 (19) | 0.0223 (8) | |
H21A | 0.6651 | 0.0734 | 0.3704 | 0.027* | |
C22 | 0.6113 (2) | 0.14416 (18) | 0.43894 (18) | 0.0180 (7) | |
H22A | 0.6581 | 0.1725 | 0.4451 | 0.022* | |
N4 | 0.54250 (16) | 0.16316 (14) | 0.47379 (14) | 0.0148 (6) | |
C23 | 0.47567 (19) | 0.11937 (17) | 0.46471 (17) | 0.0147 (7) | |
C24 | 0.40288 (19) | 0.14099 (17) | 0.50169 (17) | 0.0145 (7) | |
N5 | 0.56186 (16) | 0.18701 (14) | 0.63259 (14) | 0.0135 (6) | |
C25 | 0.5201 (2) | 0.14570 (17) | 0.67989 (18) | 0.0188 (7) | |
H25A | 0.4631 | 0.1406 | 0.6708 | 0.023* | |
C26 | 0.5592 (2) | 0.10987 (17) | 0.74241 (18) | 0.0189 (7) | |
H26A | 0.5280 | 0.0821 | 0.7743 | 0.023* | |
C27 | 0.6427 (2) | 0.11561 (18) | 0.75665 (18) | 0.0196 (7) | |
H27A | 0.6688 | 0.0923 | 0.7985 | 0.024* | |
C28 | 0.6889 (2) | 0.15707 (18) | 0.70748 (18) | 0.0182 (7) | |
C29 | 0.7770 (2) | 0.16672 (18) | 0.71560 (19) | 0.0222 (8) | |
H29A | 0.8071 | 0.1437 | 0.7553 | 0.027* | |
C30 | 0.8169 (2) | 0.20836 (18) | 0.66702 (19) | 0.0211 (8) | |
H30A | 0.8745 | 0.2122 | 0.6728 | 0.025* | |
C31 | 0.77325 (19) | 0.24695 (18) | 0.60652 (18) | 0.0174 (7) | |
C32 | 0.8105 (2) | 0.29269 (18) | 0.55613 (19) | 0.0215 (8) | |
H32A | 0.8678 | 0.2993 | 0.5589 | 0.026* | |
C33 | 0.7611 (2) | 0.32784 (19) | 0.50230 (19) | 0.0221 (8) | |
H33A | 0.7848 | 0.3596 | 0.4689 | 0.026* | |
C34 | 0.6759 (2) | 0.31651 (18) | 0.49703 (18) | 0.0198 (7) | |
H34A | 0.6439 | 0.3410 | 0.4596 | 0.024* | |
N6 | 0.63808 (16) | 0.27221 (14) | 0.54319 (14) | 0.0152 (6) | |
C35 | 0.68753 (19) | 0.23848 (17) | 0.59791 (17) | 0.0147 (7) | |
C36 | 0.64497 (19) | 0.19251 (17) | 0.64705 (17) | 0.0143 (7) | |
N7 | 0.29673 (18) | −0.00231 (16) | 0.84201 (16) | 0.0242 (7) | |
C37 | 0.3573 (2) | 0.01256 (18) | 0.89624 (19) | 0.0193 (7) | |
O1 | 0.37995 (15) | −0.02634 (12) | 0.95100 (13) | 0.0235 (5) | |
C38 | 0.3956 (2) | 0.08361 (18) | 0.88669 (18) | 0.0165 (7) | |
C39 | 0.4582 (2) | 0.11577 (19) | 0.93168 (19) | 0.0200 (7) | |
H39A | 0.4862 | 0.0920 | 0.9722 | 0.024* | |
C40 | 0.4778 (2) | 0.18382 (19) | 0.91465 (19) | 0.0243 (8) | |
H40A | 0.5201 | 0.2060 | 0.9439 | 0.029* | |
C41 | 0.4361 (2) | 0.22044 (19) | 0.85501 (19) | 0.0238 (8) | |
H41A | 0.4499 | 0.2669 | 0.8458 | 0.029* | |
C42 | 0.3739 (2) | 0.18806 (19) | 0.80888 (19) | 0.0214 (8) | |
H42A | 0.3459 | 0.2117 | 0.7683 | 0.026* | |
C43 | 0.3559 (2) | 0.12010 (19) | 0.82593 (18) | 0.0193 (7) | |
S1 | 0.28134 (5) | 0.06220 (5) | 0.78363 (5) | 0.0230 (2) | |
O2 | 0.30215 (16) | 0.04516 (14) | 0.70548 (13) | 0.0310 (6) | |
O3 | 0.19901 (15) | 0.09069 (14) | 0.79033 (15) | 0.0308 (6) | |
N8 | 0.74313 (19) | 0.36323 (16) | 0.79381 (16) | 0.0218 (7) | |
H8N | 0.701 (3) | 0.339 (2) | 0.816 (3) | 0.057 (14)* | |
C44 | 0.8238 (2) | 0.34047 (18) | 0.80033 (18) | 0.0190 (7) | |
O4 | 0.84977 (14) | 0.29645 (13) | 0.84588 (13) | 0.0226 (5) | |
C45 | 0.8730 (2) | 0.37726 (17) | 0.74232 (18) | 0.0184 (7) | |
C46 | 0.9562 (2) | 0.36890 (19) | 0.7294 (2) | 0.0230 (8) | |
H46A | 0.9890 | 0.3382 | 0.7595 | 0.028* | |
C47 | 0.9895 (2) | 0.40754 (19) | 0.6703 (2) | 0.0245 (8) | |
H47A | 1.0457 | 0.4032 | 0.6611 | 0.029* | |
C48 | 0.9400 (2) | 0.45258 (18) | 0.62465 (19) | 0.0228 (8) | |
H48A | 0.9636 | 0.4778 | 0.5852 | 0.027* | |
C49 | 0.8565 (2) | 0.46074 (18) | 0.63656 (19) | 0.0215 (8) | |
H49A | 0.8231 | 0.4906 | 0.6058 | 0.026* | |
C50 | 0.8250 (2) | 0.42274 (17) | 0.69595 (18) | 0.0169 (7) | |
S2 | 0.72285 (5) | 0.42219 (5) | 0.72614 (5) | 0.01966 (19) | |
O5 | 0.70229 (15) | 0.48753 (13) | 0.75978 (14) | 0.0274 (6) | |
O6 | 0.66567 (15) | 0.39484 (13) | 0.66736 (13) | 0.0265 (6) | |
N9 | 0.42304 (17) | 0.33972 (15) | 0.99403 (16) | 0.0219 (6) | |
C51 | 0.4967 (2) | 0.36627 (18) | 0.97701 (19) | 0.0191 (7) | |
O7 | 0.56490 (14) | 0.33866 (13) | 0.99665 (13) | 0.0231 (6) | |
C52 | 0.4920 (2) | 0.43249 (18) | 0.93115 (18) | 0.0175 (7) | |
C53 | 0.5557 (2) | 0.47344 (18) | 0.90557 (18) | 0.0208 (8) | |
H53A | 0.6109 | 0.4606 | 0.9153 | 0.025* | |
C54 | 0.5353 (2) | 0.53413 (19) | 0.86511 (19) | 0.0250 (8) | |
H54A | 0.5774 | 0.5627 | 0.8478 | 0.030* | |
C55 | 0.4530 (2) | 0.55290 (19) | 0.84999 (19) | 0.0259 (8) | |
H55A | 0.4408 | 0.5941 | 0.8229 | 0.031* | |
C56 | 0.3886 (2) | 0.51171 (18) | 0.87422 (18) | 0.0213 (8) | |
H56A | 0.3333 | 0.5236 | 0.8632 | 0.026* | |
C57 | 0.4105 (2) | 0.45236 (18) | 0.91538 (18) | 0.0177 (7) | |
S3 | 0.34868 (5) | 0.38661 (5) | 0.95553 (5) | 0.0209 (2) | |
O8 | 0.29725 (14) | 0.41467 (13) | 1.01375 (14) | 0.0270 (6) | |
O9 | 0.30438 (15) | 0.34905 (13) | 0.89333 (14) | 0.0292 (6) | |
O10 | 0.73902 (18) | 0.18541 (15) | 0.90609 (16) | 0.0356 (7) | |
H1W | 0.779 (3) | 0.218 (2) | 0.908 (2) | 0.093 (14)* | |
H2W | 0.731 (3) | 0.174 (3) | 0.9557 (9) | 0.093 (14)* | |
O11 | 0.63066 (16) | 0.29071 (14) | 0.86289 (15) | 0.0297 (6) | |
H3W | 0.658 (3) | 0.2500 (14) | 0.872 (2) | 0.072 (12)* | |
H4W | 0.612 (3) | 0.305 (2) | 0.9085 (12) | 0.072 (12)* | |
O12 | 0.7536 (2) | 0.17201 (19) | 0.23007 (18) | 0.0532 (9) | |
H5W | 0.750 (4) | 0.1333 (16) | 0.200 (2) | 0.119 (18)* | |
H6W | 0.747 (4) | 0.158 (3) | 0.2792 (11) | 0.119 (18)* | |
O13 | 0.3036 (2) | −0.15423 (15) | 0.94486 (19) | 0.0460 (8) | |
H7W | 0.321 (2) | −0.1095 (7) | 0.952 (3) | 0.070 (12)* | |
H8W | 0.3500 (14) | −0.1795 (16) | 0.939 (3) | 0.070 (12)* | |
O14 | 0.0632 (2) | 0.26506 (15) | 0.60654 (16) | 0.0430 (8) | |
H9W | 0.063 (4) | 0.2295 (15) | 0.5721 (18) | 0.094 (15)* | |
H10W | 0.073 (4) | 0.245 (2) | 0.6537 (11) | 0.094 (15)* | |
O15 | 0.13016 (17) | 0.22951 (16) | 0.75558 (16) | 0.0372 (7) | |
H11W | 0.154 (2) | 0.1878 (8) | 0.767 (3) | 0.056 (10)* | |
H12W | 0.1712 (15) | 0.2614 (13) | 0.759 (3) | 0.056 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0119 (2) | 0.0182 (3) | 0.0109 (2) | −0.00072 (19) | −0.00246 (16) | −0.0003 (2) |
N1 | 0.0118 (14) | 0.0219 (16) | 0.0137 (13) | −0.0011 (12) | −0.0014 (10) | −0.0022 (12) |
C1 | 0.0146 (18) | 0.026 (2) | 0.0137 (16) | −0.0027 (14) | −0.0041 (13) | −0.0037 (15) |
C2 | 0.0192 (19) | 0.030 (2) | 0.0119 (16) | −0.0045 (15) | −0.0051 (13) | 0.0039 (15) |
C3 | 0.0170 (18) | 0.027 (2) | 0.0179 (17) | −0.0020 (15) | −0.0066 (13) | 0.0070 (15) |
C4 | 0.0127 (17) | 0.0223 (19) | 0.0169 (16) | −0.0020 (14) | −0.0052 (13) | 0.0010 (14) |
C5 | 0.021 (2) | 0.026 (2) | 0.0256 (19) | 0.0021 (15) | −0.0083 (14) | 0.0068 (16) |
C6 | 0.024 (2) | 0.020 (2) | 0.0269 (19) | 0.0054 (15) | −0.0016 (15) | −0.0006 (15) |
C7 | 0.0154 (18) | 0.0223 (19) | 0.0185 (17) | −0.0021 (14) | −0.0013 (13) | −0.0016 (15) |
C8 | 0.0220 (19) | 0.024 (2) | 0.0222 (18) | 0.0004 (15) | 0.0039 (14) | −0.0073 (15) |
C9 | 0.027 (2) | 0.024 (2) | 0.0139 (16) | −0.0035 (16) | −0.0005 (14) | −0.0043 (15) |
C10 | 0.0191 (18) | 0.0214 (19) | 0.0127 (16) | −0.0006 (14) | −0.0026 (13) | −0.0008 (14) |
N2 | 0.0114 (14) | 0.0211 (16) | 0.0144 (13) | −0.0041 (11) | −0.0024 (10) | 0.0014 (12) |
C11 | 0.0114 (17) | 0.0181 (18) | 0.0163 (16) | −0.0038 (13) | −0.0023 (12) | −0.0014 (14) |
C12 | 0.0110 (17) | 0.0209 (19) | 0.0166 (16) | −0.0062 (13) | −0.0028 (12) | 0.0005 (14) |
N3 | 0.0151 (15) | 0.0175 (15) | 0.0123 (13) | 0.0035 (11) | −0.0036 (11) | 0.0019 (11) |
C13 | 0.0172 (18) | 0.024 (2) | 0.0164 (16) | 0.0037 (14) | −0.0019 (13) | −0.0008 (14) |
C14 | 0.0179 (19) | 0.031 (2) | 0.0218 (18) | 0.0032 (16) | 0.0026 (14) | 0.0027 (16) |
C15 | 0.0134 (18) | 0.028 (2) | 0.0204 (18) | −0.0039 (15) | −0.0027 (13) | 0.0072 (15) |
C16 | 0.0151 (17) | 0.0211 (19) | 0.0157 (16) | −0.0020 (14) | −0.0039 (13) | 0.0067 (14) |
C17 | 0.0208 (19) | 0.023 (2) | 0.0236 (18) | −0.0067 (15) | −0.0046 (14) | 0.0012 (15) |
C18 | 0.027 (2) | 0.0204 (19) | 0.0214 (18) | −0.0032 (15) | −0.0044 (15) | −0.0038 (15) |
C19 | 0.0195 (18) | 0.0202 (19) | 0.0125 (16) | −0.0002 (14) | −0.0048 (13) | 0.0007 (14) |
C20 | 0.024 (2) | 0.023 (2) | 0.0185 (17) | 0.0009 (15) | −0.0016 (14) | −0.0054 (15) |
C21 | 0.0182 (19) | 0.029 (2) | 0.0196 (17) | 0.0058 (15) | −0.0014 (14) | −0.0015 (16) |
C22 | 0.0110 (17) | 0.0230 (19) | 0.0196 (17) | −0.0010 (14) | −0.0033 (13) | −0.0019 (15) |
N4 | 0.0119 (14) | 0.0199 (15) | 0.0123 (13) | 0.0022 (11) | −0.0026 (10) | 0.0033 (11) |
C23 | 0.0144 (17) | 0.0177 (17) | 0.0114 (15) | 0.0012 (14) | −0.0041 (12) | 0.0027 (13) |
C24 | 0.0144 (17) | 0.0179 (18) | 0.0108 (15) | −0.0004 (13) | −0.0037 (12) | 0.0039 (13) |
N5 | 0.0147 (14) | 0.0137 (14) | 0.0120 (13) | 0.0010 (11) | −0.0006 (10) | −0.0025 (11) |
C25 | 0.0199 (19) | 0.0182 (18) | 0.0179 (17) | 0.0004 (14) | −0.0014 (13) | −0.0009 (14) |
C26 | 0.024 (2) | 0.0171 (18) | 0.0158 (16) | −0.0012 (14) | 0.0016 (14) | 0.0003 (14) |
C27 | 0.0228 (19) | 0.0209 (19) | 0.0146 (16) | 0.0035 (15) | −0.0044 (13) | 0.0050 (14) |
C28 | 0.0185 (18) | 0.0209 (19) | 0.0144 (16) | 0.0033 (14) | −0.0055 (13) | −0.0027 (14) |
C29 | 0.0186 (19) | 0.026 (2) | 0.0206 (18) | 0.0046 (15) | −0.0087 (14) | 0.0012 (16) |
C30 | 0.0137 (18) | 0.024 (2) | 0.0246 (19) | −0.0005 (14) | −0.0045 (14) | −0.0050 (16) |
C31 | 0.0131 (17) | 0.0196 (18) | 0.0190 (16) | 0.0019 (14) | −0.0041 (12) | −0.0067 (15) |
C32 | 0.0151 (18) | 0.028 (2) | 0.0214 (18) | −0.0063 (15) | 0.0006 (14) | −0.0062 (16) |
C33 | 0.0202 (19) | 0.029 (2) | 0.0175 (17) | −0.0082 (15) | 0.0026 (14) | 0.0016 (15) |
C34 | 0.0218 (19) | 0.0236 (19) | 0.0138 (16) | −0.0027 (15) | −0.0021 (13) | 0.0012 (14) |
N6 | 0.0157 (15) | 0.0180 (15) | 0.0118 (13) | −0.0015 (11) | −0.0017 (11) | 0.0007 (11) |
C35 | 0.0155 (17) | 0.0164 (17) | 0.0119 (15) | 0.0013 (13) | −0.0009 (12) | −0.0031 (13) |
C36 | 0.0133 (17) | 0.0159 (17) | 0.0133 (15) | −0.0001 (13) | −0.0018 (12) | −0.0042 (13) |
N7 | 0.0201 (17) | 0.0269 (17) | 0.0253 (16) | −0.0046 (13) | −0.0016 (12) | −0.0018 (13) |
C37 | 0.0156 (18) | 0.024 (2) | 0.0184 (17) | 0.0004 (14) | 0.0038 (13) | −0.0047 (15) |
O1 | 0.0242 (14) | 0.0240 (14) | 0.0221 (13) | −0.0001 (11) | 0.0011 (10) | 0.0061 (11) |
C38 | 0.0151 (17) | 0.0202 (18) | 0.0143 (16) | 0.0029 (14) | 0.0033 (13) | 0.0002 (14) |
C39 | 0.0162 (18) | 0.029 (2) | 0.0142 (16) | 0.0008 (15) | −0.0003 (13) | −0.0043 (15) |
C40 | 0.026 (2) | 0.029 (2) | 0.0184 (18) | −0.0041 (16) | 0.0015 (15) | −0.0050 (16) |
C41 | 0.027 (2) | 0.022 (2) | 0.0225 (18) | −0.0002 (16) | 0.0060 (15) | 0.0021 (15) |
C42 | 0.0198 (19) | 0.028 (2) | 0.0167 (17) | 0.0028 (15) | 0.0017 (14) | 0.0032 (15) |
C43 | 0.0152 (18) | 0.028 (2) | 0.0143 (16) | 0.0064 (15) | −0.0001 (13) | −0.0013 (15) |
S1 | 0.0174 (5) | 0.0303 (5) | 0.0207 (4) | −0.0009 (4) | −0.0037 (3) | −0.0013 (4) |
O2 | 0.0321 (15) | 0.0440 (17) | 0.0163 (12) | 0.0030 (13) | −0.0035 (11) | −0.0062 (12) |
O3 | 0.0138 (13) | 0.0419 (17) | 0.0361 (15) | 0.0017 (11) | −0.0036 (11) | 0.0013 (13) |
N8 | 0.0166 (16) | 0.0294 (18) | 0.0193 (15) | 0.0018 (13) | 0.0003 (12) | 0.0074 (13) |
C44 | 0.0201 (19) | 0.0222 (19) | 0.0144 (16) | −0.0021 (15) | −0.0009 (13) | −0.0005 (15) |
O4 | 0.0220 (14) | 0.0286 (15) | 0.0166 (12) | 0.0018 (11) | −0.0040 (10) | 0.0020 (11) |
C45 | 0.0220 (19) | 0.0198 (19) | 0.0131 (16) | 0.0016 (14) | −0.0009 (13) | −0.0022 (14) |
C46 | 0.0193 (19) | 0.026 (2) | 0.0233 (18) | 0.0008 (15) | −0.0003 (14) | −0.0024 (16) |
C47 | 0.0201 (19) | 0.027 (2) | 0.0273 (19) | −0.0020 (15) | 0.0047 (15) | −0.0048 (16) |
C48 | 0.031 (2) | 0.021 (2) | 0.0175 (17) | −0.0070 (16) | 0.0072 (15) | −0.0057 (15) |
C49 | 0.028 (2) | 0.0199 (19) | 0.0163 (17) | −0.0027 (15) | −0.0034 (14) | −0.0022 (14) |
C50 | 0.0163 (18) | 0.0202 (19) | 0.0138 (16) | −0.0015 (14) | −0.0041 (13) | −0.0058 (14) |
S2 | 0.0165 (4) | 0.0248 (5) | 0.0173 (4) | 0.0011 (4) | −0.0032 (3) | 0.0025 (4) |
O5 | 0.0256 (14) | 0.0275 (15) | 0.0290 (14) | 0.0049 (11) | −0.0005 (11) | −0.0008 (11) |
O6 | 0.0217 (14) | 0.0338 (15) | 0.0229 (13) | −0.0055 (11) | −0.0098 (10) | 0.0041 (11) |
N9 | 0.0170 (16) | 0.0228 (17) | 0.0257 (16) | 0.0021 (12) | −0.0007 (12) | 0.0015 (13) |
C51 | 0.0177 (19) | 0.0224 (19) | 0.0171 (17) | 0.0009 (15) | 0.0001 (13) | −0.0056 (14) |
O7 | 0.0163 (13) | 0.0295 (15) | 0.0231 (13) | 0.0038 (10) | −0.0033 (10) | 0.0010 (11) |
C52 | 0.0153 (17) | 0.0229 (19) | 0.0140 (16) | 0.0013 (14) | −0.0031 (12) | −0.0049 (14) |
C53 | 0.0161 (18) | 0.027 (2) | 0.0189 (17) | −0.0020 (15) | −0.0042 (13) | −0.0069 (15) |
C54 | 0.030 (2) | 0.028 (2) | 0.0175 (17) | −0.0056 (17) | 0.0032 (15) | 0.0028 (16) |
C55 | 0.036 (2) | 0.026 (2) | 0.0148 (17) | 0.0065 (17) | −0.0046 (15) | 0.0017 (15) |
C56 | 0.0196 (19) | 0.028 (2) | 0.0161 (17) | 0.0058 (15) | −0.0042 (13) | −0.0032 (15) |
C57 | 0.0168 (18) | 0.0237 (19) | 0.0125 (16) | 0.0011 (14) | −0.0016 (13) | −0.0045 (14) |
S3 | 0.0135 (4) | 0.0238 (5) | 0.0249 (4) | 0.0012 (4) | −0.0018 (3) | −0.0032 (4) |
O8 | 0.0185 (14) | 0.0334 (15) | 0.0294 (14) | 0.0049 (11) | 0.0038 (10) | −0.0024 (12) |
O9 | 0.0193 (14) | 0.0354 (16) | 0.0322 (14) | −0.0026 (11) | −0.0071 (11) | −0.0078 (12) |
O10 | 0.0377 (18) | 0.0348 (17) | 0.0342 (15) | −0.0002 (14) | 0.0005 (13) | −0.0025 (13) |
O11 | 0.0264 (15) | 0.0357 (17) | 0.0277 (14) | −0.0008 (12) | 0.0067 (11) | 0.0041 (12) |
O12 | 0.045 (2) | 0.072 (2) | 0.0406 (19) | 0.0143 (18) | −0.0118 (16) | −0.0170 (17) |
O13 | 0.059 (2) | 0.0276 (17) | 0.0519 (19) | −0.0118 (15) | 0.0072 (17) | −0.0028 (15) |
O14 | 0.060 (2) | 0.0340 (17) | 0.0343 (17) | 0.0073 (15) | −0.0074 (15) | −0.0071 (13) |
O15 | 0.0290 (16) | 0.0480 (19) | 0.0346 (16) | 0.0001 (13) | 0.0015 (12) | 0.0035 (15) |
Fe1—N1 | 1.965 (3) | C32—H32A | 0.9300 |
Fe1—N2 | 1.963 (3) | C33—C34 | 1.388 (5) |
Fe1—N3 | 1.974 (3) | C33—H33A | 0.9300 |
Fe1—N4 | 1.973 (3) | C34—N6 | 1.329 (4) |
Fe1—N5 | 1.963 (3) | C34—H34A | 0.9300 |
Fe1—N6 | 1.957 (3) | N6—C35 | 1.365 (4) |
N1—C1 | 1.333 (4) | C35—C36 | 1.419 (4) |
N1—C12 | 1.359 (4) | N7—C37 | 1.347 (4) |
C1—C2 | 1.391 (5) | N7—S1 | 1.601 (3) |
C1—H1A | 0.9300 | C37—O1 | 1.241 (4) |
C2—C3 | 1.362 (5) | C37—C38 | 1.502 (5) |
C2—H2A | 0.9300 | C38—C39 | 1.385 (5) |
C3—C4 | 1.409 (4) | C38—C43 | 1.386 (4) |
C3—H3A | 0.9300 | C39—C40 | 1.371 (5) |
C4—C12 | 1.400 (4) | C39—H39A | 0.9300 |
C4—C5 | 1.421 (5) | C40—C41 | 1.388 (5) |
C5—C6 | 1.356 (5) | C40—H40A | 0.9300 |
C5—H5B | 0.9300 | C41—C42 | 1.392 (5) |
C6—C7 | 1.422 (5) | C41—H41A | 0.9300 |
C6—H6A | 0.9300 | C42—C43 | 1.364 (5) |
C7—C11 | 1.392 (5) | C42—H42A | 0.9300 |
C7—C8 | 1.409 (5) | C43—S1 | 1.763 (4) |
C8—C9 | 1.369 (5) | S1—O2 | 1.441 (2) |
C8—H8A | 0.9300 | S1—O3 | 1.444 (3) |
C9—C10 | 1.382 (5) | N8—C44 | 1.370 (4) |
C9—H9A | 0.9300 | N8—S2 | 1.641 (3) |
C10—N2 | 1.334 (4) | N8—H8N | 0.92 (5) |
C10—H10A | 0.9300 | C44—O4 | 1.210 (4) |
N2—C11 | 1.366 (4) | C44—C45 | 1.483 (5) |
C11—C12 | 1.414 (4) | C45—C46 | 1.378 (5) |
N3—C13 | 1.332 (4) | C45—C50 | 1.388 (5) |
N3—C24 | 1.359 (4) | C46—C47 | 1.387 (5) |
C13—C14 | 1.394 (5) | C46—H46A | 0.9300 |
C13—H13A | 0.9300 | C47—C48 | 1.390 (5) |
C14—C15 | 1.352 (5) | C47—H47A | 0.9300 |
C14—H14A | 0.9300 | C48—C49 | 1.380 (5) |
C15—C16 | 1.406 (5) | C48—H48A | 0.9300 |
C15—H15A | 0.9300 | C49—C50 | 1.372 (5) |
C16—C24 | 1.397 (4) | C49—H49A | 0.9300 |
C16—C17 | 1.429 (5) | C50—S2 | 1.751 (3) |
C17—C18 | 1.345 (5) | S2—O5 | 1.421 (3) |
C17—H17A | 0.9300 | S2—O6 | 1.433 (2) |
C18—C19 | 1.433 (5) | N9—C51 | 1.336 (4) |
C18—H18A | 0.9300 | N9—S3 | 1.611 (3) |
C19—C20 | 1.401 (5) | C51—O7 | 1.250 (4) |
C19—C23 | 1.402 (4) | C51—C52 | 1.490 (5) |
C20—C21 | 1.368 (5) | C52—C57 | 1.379 (4) |
C20—H20A | 0.9300 | C52—C53 | 1.381 (5) |
C21—C22 | 1.385 (5) | C53—C54 | 1.383 (5) |
C21—H21A | 0.9300 | C53—H53A | 0.9300 |
C22—N4 | 1.337 (4) | C54—C55 | 1.385 (5) |
C22—H22A | 0.9300 | C54—H54A | 0.9300 |
N4—C23 | 1.366 (4) | C55—C56 | 1.383 (5) |
C23—C24 | 1.423 (4) | C55—H55A | 0.9300 |
N5—C25 | 1.339 (4) | C56—C57 | 1.373 (5) |
N5—C36 | 1.354 (4) | C56—H56A | 0.9300 |
C25—C26 | 1.399 (5) | C57—S3 | 1.765 (3) |
C25—H25A | 0.9300 | S3—O8 | 1.436 (2) |
C26—C27 | 1.360 (5) | S3—O9 | 1.447 (2) |
C26—H26A | 0.9300 | O10—H1W | 0.900 (5) |
C27—C28 | 1.400 (5) | O10—H2W | 0.900 (5) |
C27—H27A | 0.9300 | O11—H3W | 0.899 (5) |
C28—C36 | 1.403 (4) | O11—H4W | 0.898 (5) |
C28—C29 | 1.431 (5) | O12—H5W | 0.900 (5) |
C29—C30 | 1.342 (5) | O12—H6W | 0.898 (5) |
C29—H29A | 0.9300 | O13—H7W | 0.902 (5) |
C30—C31 | 1.432 (5) | O13—H8W | 0.902 (5) |
C30—H30A | 0.9300 | O14—H9W | 0.901 (5) |
C31—C32 | 1.389 (5) | O14—H10W | 0.900 (5) |
C31—C35 | 1.391 (4) | O15—H11W | 0.899 (5) |
C32—C33 | 1.367 (5) | O15—H12W | 0.898 (5) |
N1—Fe1—N2 | 82.55 (11) | C29—C30—C31 | 121.6 (3) |
N1—Fe1—N3 | 91.50 (11) | C29—C30—H30A | 119.2 |
N1—Fe1—N4 | 94.89 (11) | C31—C30—H30A | 119.2 |
N1—Fe1—N5 | 173.96 (11) | C32—C31—C35 | 117.7 (3) |
N1—Fe1—N6 | 93.15 (11) | C32—C31—C30 | 124.5 (3) |
N2—Fe1—N3 | 92.31 (11) | C35—C31—C30 | 117.9 (3) |
N2—Fe1—N4 | 174.42 (11) | C33—C32—C31 | 118.5 (3) |
N2—Fe1—N5 | 93.23 (11) | C33—C32—H32A | 120.8 |
N2—Fe1—N6 | 93.44 (11) | C31—C32—H32A | 120.8 |
N3—Fe1—N4 | 82.77 (11) | C32—C33—C34 | 120.6 (3) |
N3—Fe1—N5 | 93.00 (11) | C32—C33—H33A | 119.7 |
N3—Fe1—N6 | 173.03 (11) | C34—C33—H33A | 119.7 |
N4—Fe1—N5 | 89.67 (10) | N6—C34—C33 | 122.8 (3) |
N4—Fe1—N6 | 91.66 (11) | N6—C34—H34A | 118.6 |
N5—Fe1—N6 | 82.75 (11) | C33—C34—H34A | 118.6 |
C1—N1—C12 | 117.1 (3) | C34—N6—C35 | 116.3 (3) |
C1—N1—Fe1 | 129.9 (2) | C34—N6—Fe1 | 130.3 (2) |
C12—N1—Fe1 | 113.0 (2) | C35—N6—Fe1 | 113.2 (2) |
N1—C1—C2 | 122.4 (3) | N6—C35—C31 | 124.1 (3) |
N1—C1—H1A | 118.8 | N6—C35—C36 | 114.9 (3) |
C2—C1—H1A | 118.8 | C31—C35—C36 | 121.0 (3) |
C3—C2—C1 | 120.6 (3) | N5—C36—C28 | 123.8 (3) |
C3—C2—H2A | 119.7 | N5—C36—C35 | 116.2 (3) |
C1—C2—H2A | 119.7 | C28—C36—C35 | 120.0 (3) |
C2—C3—C4 | 118.9 (3) | C37—N7—S1 | 111.0 (2) |
C2—C3—H3A | 120.5 | O1—C37—N7 | 125.2 (3) |
C4—C3—H3A | 120.5 | O1—C37—C38 | 121.1 (3) |
C12—C4—C3 | 116.7 (3) | N7—C37—C38 | 113.7 (3) |
C12—C4—C5 | 118.6 (3) | C39—C38—C43 | 119.7 (3) |
C3—C4—C5 | 124.7 (3) | C39—C38—C37 | 129.1 (3) |
C6—C5—C4 | 121.2 (3) | C43—C38—C37 | 111.1 (3) |
C6—C5—H5B | 119.4 | C40—C39—C38 | 117.9 (3) |
C4—C5—H5B | 119.4 | C40—C39—H39A | 121.0 |
C5—C6—C7 | 120.7 (3) | C38—C39—H39A | 121.0 |
C5—C6—H6A | 119.7 | C39—C40—C41 | 121.8 (3) |
C7—C6—H6A | 119.7 | C39—C40—H40A | 119.1 |
C11—C7—C8 | 117.1 (3) | C41—C40—H40A | 119.1 |
C11—C7—C6 | 119.0 (3) | C40—C41—C42 | 120.5 (3) |
C8—C7—C6 | 123.9 (3) | C40—C41—H41A | 119.8 |
C9—C8—C7 | 118.7 (3) | C42—C41—H41A | 119.8 |
C9—C8—H8A | 120.6 | C43—C42—C41 | 117.0 (3) |
C7—C8—H8A | 120.6 | C43—C42—H42A | 121.5 |
C8—C9—C10 | 120.2 (3) | C41—C42—H42A | 121.5 |
C8—C9—H9A | 119.9 | C42—C43—C38 | 123.0 (3) |
C10—C9—H9A | 119.9 | C42—C43—S1 | 130.9 (3) |
N2—C10—C9 | 123.4 (3) | C38—C43—S1 | 106.0 (3) |
N2—C10—H10A | 118.3 | O2—S1—O3 | 114.67 (15) |
C9—C10—H10A | 118.3 | O2—S1—N7 | 112.18 (16) |
C10—N2—C11 | 116.3 (3) | O3—S1—N7 | 110.69 (16) |
C10—N2—Fe1 | 130.8 (2) | O2—S1—C43 | 109.99 (16) |
C11—N2—Fe1 | 112.8 (2) | O3—S1—C43 | 109.95 (16) |
N2—C11—C7 | 124.3 (3) | N7—S1—C43 | 98.12 (15) |
N2—C11—C12 | 115.4 (3) | C44—N8—S2 | 115.5 (2) |
C7—C11—C12 | 120.3 (3) | C44—N8—H8N | 122 (3) |
N1—C12—C4 | 124.1 (3) | S2—N8—H8N | 121 (3) |
N1—C12—C11 | 115.8 (3) | O4—C44—N8 | 124.7 (3) |
C4—C12—C11 | 120.1 (3) | O4—C44—C45 | 125.9 (3) |
C13—N3—C24 | 116.9 (3) | N8—C44—C45 | 109.4 (3) |
C13—N3—Fe1 | 130.2 (2) | C46—C45—C50 | 119.8 (3) |
C24—N3—Fe1 | 112.8 (2) | C46—C45—C44 | 127.6 (3) |
N3—C13—C14 | 122.5 (3) | C50—C45—C44 | 112.5 (3) |
N3—C13—H13A | 118.7 | C45—C46—C47 | 118.2 (3) |
C14—C13—H13A | 118.7 | C45—C46—H46A | 120.9 |
C15—C14—C13 | 120.3 (3) | C47—C46—H46A | 120.9 |
C15—C14—H14A | 119.8 | C46—C47—C48 | 120.8 (3) |
C13—C14—H14A | 119.8 | C46—C47—H47A | 119.6 |
C14—C15—C16 | 119.3 (3) | C48—C47—H47A | 119.6 |
C14—C15—H15A | 120.3 | C49—C48—C47 | 121.5 (3) |
C16—C15—H15A | 120.3 | C49—C48—H48A | 119.3 |
C24—C16—C15 | 116.7 (3) | C47—C48—H48A | 119.3 |
C24—C16—C17 | 118.8 (3) | C50—C49—C48 | 116.8 (3) |
C15—C16—C17 | 124.4 (3) | C50—C49—H49A | 121.6 |
C18—C17—C16 | 121.2 (3) | C48—C49—H49A | 121.6 |
C18—C17—H17A | 119.4 | C49—C50—C45 | 122.9 (3) |
C16—C17—H17A | 119.4 | C49—C50—S2 | 127.8 (3) |
C17—C18—C19 | 121.4 (3) | C45—C50—S2 | 109.3 (2) |
C17—C18—H18A | 119.3 | O5—S2—O6 | 116.93 (15) |
C19—C18—H18A | 119.3 | O5—S2—N8 | 110.72 (15) |
C20—C19—C23 | 117.0 (3) | O6—S2—N8 | 110.52 (16) |
C20—C19—C18 | 124.7 (3) | O5—S2—C50 | 110.96 (16) |
C23—C19—C18 | 118.3 (3) | O6—S2—C50 | 111.91 (15) |
C21—C20—C19 | 119.3 (3) | N8—S2—C50 | 93.35 (16) |
C21—C20—H20A | 120.4 | C51—N9—S3 | 110.4 (2) |
C19—C20—H20A | 120.4 | O7—C51—N9 | 124.0 (3) |
C20—C21—C22 | 120.1 (3) | O7—C51—C52 | 121.4 (3) |
C20—C21—H21A | 119.9 | N9—C51—C52 | 114.6 (3) |
C22—C21—H21A | 119.9 | C57—C52—C53 | 119.8 (3) |
N4—C22—C21 | 123.0 (3) | C57—C52—C51 | 111.1 (3) |
N4—C22—H22A | 118.5 | C53—C52—C51 | 129.1 (3) |
C21—C22—H22A | 118.5 | C52—C53—C54 | 118.2 (3) |
C22—N4—C23 | 116.7 (3) | C52—C53—H53A | 120.9 |
C22—N4—Fe1 | 130.6 (2) | C54—C53—H53A | 120.9 |
C23—N4—Fe1 | 112.6 (2) | C53—C54—C55 | 120.8 (3) |
N4—C23—C19 | 123.9 (3) | C53—C54—H54A | 119.6 |
N4—C23—C24 | 115.7 (3) | C55—C54—H54A | 119.6 |
C19—C23—C24 | 120.4 (3) | C56—C55—C54 | 121.5 (3) |
N3—C24—C16 | 124.1 (3) | C56—C55—H55A | 119.3 |
N3—C24—C23 | 115.9 (3) | C54—C55—H55A | 119.3 |
C16—C24—C23 | 120.0 (3) | C57—C56—C55 | 116.5 (3) |
C25—N5—C36 | 117.1 (3) | C57—C56—H56A | 121.7 |
C25—N5—Fe1 | 130.1 (2) | C55—C56—H56A | 121.7 |
C36—N5—Fe1 | 112.8 (2) | C56—C57—C52 | 123.1 (3) |
N5—C25—C26 | 122.4 (3) | C56—C57—S3 | 130.7 (3) |
N5—C25—H25A | 118.8 | C52—C57—S3 | 106.1 (2) |
C26—C25—H25A | 118.8 | O8—S3—O9 | 114.92 (15) |
C27—C26—C25 | 120.2 (3) | O8—S3—N9 | 111.26 (15) |
C27—C26—H26A | 119.9 | O9—S3—N9 | 111.03 (16) |
C25—C26—H26A | 119.9 | O8—S3—C57 | 111.45 (16) |
C26—C27—C28 | 119.2 (3) | O9—S3—C57 | 109.21 (15) |
C26—C27—H27A | 120.4 | N9—S3—C57 | 97.64 (15) |
C28—C27—H27A | 120.4 | H1W—O10—H2W | 106.1 (8) |
C27—C28—C36 | 117.2 (3) | H3W—O11—H4W | 106.5 (8) |
C27—C28—C29 | 124.6 (3) | H5W—O12—H6W | 106.5 (8) |
C36—C28—C29 | 118.1 (3) | H7W—O13—H8W | 105.8 (8) |
C30—C29—C28 | 121.3 (3) | H9W—O14—H10W | 106.0 (8) |
C30—C29—H29A | 119.3 | H11W—O15—H12W | 106.6 (8) |
C28—C29—H29A | 119.3 | ||
N6—Fe1—N1—C1 | 79.4 (3) | Fe1—N5—C25—C26 | −179.2 (2) |
N2—Fe1—N1—C1 | 172.5 (3) | N5—C25—C26—C27 | −0.7 (5) |
N5—Fe1—N1—C1 | 126.5 (10) | C25—C26—C27—C28 | −0.7 (5) |
N4—Fe1—N1—C1 | −12.5 (3) | C26—C27—C28—C36 | 2.0 (5) |
N3—Fe1—N1—C1 | −95.4 (3) | C26—C27—C28—C29 | −179.2 (3) |
N6—Fe1—N1—C12 | −97.8 (2) | C27—C28—C29—C30 | −178.8 (3) |
N2—Fe1—N1—C12 | −4.8 (2) | C36—C28—C29—C30 | 0.0 (5) |
N5—Fe1—N1—C12 | −50.7 (11) | C28—C29—C30—C31 | 2.2 (5) |
N4—Fe1—N1—C12 | 170.2 (2) | C29—C30—C31—C32 | 177.7 (3) |
N3—Fe1—N1—C12 | 87.4 (2) | C29—C30—C31—C35 | −1.8 (5) |
C12—N1—C1—C2 | −1.0 (4) | C35—C31—C32—C33 | 1.4 (5) |
Fe1—N1—C1—C2 | −178.2 (2) | C30—C31—C32—C33 | −178.1 (3) |
N1—C1—C2—C3 | −1.0 (5) | C31—C32—C33—C34 | −1.7 (5) |
C1—C2—C3—C4 | 1.0 (5) | C32—C33—C34—N6 | 0.4 (5) |
C2—C3—C4—C12 | 0.9 (5) | C33—C34—N6—C35 | 1.0 (5) |
C2—C3—C4—C5 | 179.6 (3) | C33—C34—N6—Fe1 | −175.6 (2) |
C12—C4—C5—C6 | 1.5 (5) | N2—Fe1—N6—C34 | −86.6 (3) |
C3—C4—C5—C6 | −177.2 (3) | N5—Fe1—N6—C34 | −179.4 (3) |
C4—C5—C6—C7 | 1.9 (5) | N1—Fe1—N6—C34 | −3.9 (3) |
C5—C6—C7—C11 | −3.1 (5) | N4—Fe1—N6—C34 | 91.1 (3) |
C5—C6—C7—C8 | 175.1 (3) | N3—Fe1—N6—C34 | 127.9 (8) |
C11—C7—C8—C9 | 1.4 (5) | N2—Fe1—N6—C35 | 96.7 (2) |
C6—C7—C8—C9 | −176.8 (3) | N5—Fe1—N6—C35 | 3.9 (2) |
C7—C8—C9—C10 | −1.8 (5) | N1—Fe1—N6—C35 | 179.4 (2) |
C8—C9—C10—N2 | 0.0 (5) | N4—Fe1—N6—C35 | −85.6 (2) |
C9—C10—N2—C11 | 2.1 (5) | N3—Fe1—N6—C35 | −48.8 (10) |
C9—C10—N2—Fe1 | −175.1 (2) | C34—N6—C35—C31 | −1.2 (5) |
N6—Fe1—N2—C10 | −83.9 (3) | Fe1—N6—C35—C31 | 176.0 (2) |
N5—Fe1—N2—C10 | −0.9 (3) | C34—N6—C35—C36 | 179.0 (3) |
N1—Fe1—N2—C10 | −176.6 (3) | Fe1—N6—C35—C36 | −3.8 (3) |
N4—Fe1—N2—C10 | 120.3 (11) | C32—C31—C35—N6 | 0.0 (5) |
N3—Fe1—N2—C10 | 92.2 (3) | C30—C31—C35—N6 | 179.6 (3) |
N6—Fe1—N2—C11 | 98.8 (2) | C32—C31—C35—C36 | 179.8 (3) |
N5—Fe1—N2—C11 | −178.3 (2) | C30—C31—C35—C36 | −0.6 (5) |
N1—Fe1—N2—C11 | 6.1 (2) | C25—N5—C36—C28 | 0.8 (4) |
N4—Fe1—N2—C11 | −57.0 (12) | Fe1—N5—C36—C28 | −179.4 (3) |
N3—Fe1—N2—C11 | −85.1 (2) | C25—N5—C36—C35 | −177.9 (3) |
C10—N2—C11—C7 | −2.4 (5) | Fe1—N5—C36—C35 | 2.0 (3) |
Fe1—N2—C11—C7 | 175.3 (3) | C27—C28—C36—N5 | −2.1 (5) |
C10—N2—C11—C12 | 175.9 (3) | C29—C28—C36—N5 | 179.0 (3) |
Fe1—N2—C11—C12 | −6.4 (3) | C27—C28—C36—C35 | 176.4 (3) |
C8—C7—C11—N2 | 0.7 (5) | C29—C28—C36—C35 | −2.4 (5) |
C6—C7—C11—N2 | 179.0 (3) | N6—C35—C36—N5 | 1.2 (4) |
C8—C7—C11—C12 | −177.5 (3) | C31—C35—C36—N5 | −178.6 (3) |
C6—C7—C11—C12 | 0.7 (5) | N6—C35—C36—C28 | −177.5 (3) |
C1—N1—C12—C4 | 3.1 (5) | C31—C35—C36—C28 | 2.7 (5) |
Fe1—N1—C12—C4 | −179.3 (2) | S1—N7—C37—O1 | 176.7 (3) |
C1—N1—C12—C11 | −175.0 (3) | S1—N7—C37—C38 | −1.6 (4) |
Fe1—N1—C12—C11 | 2.7 (3) | O1—C37—C38—C39 | 1.1 (5) |
C3—C4—C12—N1 | −3.0 (5) | N7—C37—C38—C39 | 179.5 (3) |
C5—C4—C12—N1 | 178.2 (3) | O1—C37—C38—C43 | −174.8 (3) |
C3—C4—C12—C11 | 174.9 (3) | N7—C37—C38—C43 | 3.6 (4) |
C5—C4—C12—C11 | −3.9 (5) | C43—C38—C39—C40 | 1.0 (5) |
N2—C11—C12—N1 | 2.5 (4) | C37—C38—C39—C40 | −174.6 (3) |
C7—C11—C12—N1 | −179.1 (3) | C38—C39—C40—C41 | 0.7 (5) |
N2—C11—C12—C4 | −175.7 (3) | C39—C40—C41—C42 | −1.7 (5) |
C7—C11—C12—C4 | 2.7 (5) | C40—C41—C42—C43 | 0.8 (5) |
N6—Fe1—N3—C13 | 145.1 (8) | C41—C42—C43—C38 | 0.9 (5) |
N2—Fe1—N3—C13 | −0.4 (3) | C41—C42—C43—S1 | 178.5 (3) |
N5—Fe1—N3—C13 | 92.9 (3) | C39—C38—C43—C42 | −1.9 (5) |
N1—Fe1—N3—C13 | −83.0 (3) | C37—C38—C43—C42 | 174.5 (3) |
N4—Fe1—N3—C13 | −177.8 (3) | C39—C38—C43—S1 | −179.9 (2) |
N6—Fe1—N3—C24 | −33.7 (10) | C37—C38—C43—S1 | −3.6 (3) |
N2—Fe1—N3—C24 | −179.3 (2) | C37—N7—S1—O2 | 115.1 (2) |
N5—Fe1—N3—C24 | −85.9 (2) | C37—N7—S1—O3 | −115.4 (2) |
N1—Fe1—N3—C24 | 98.1 (2) | C37—N7—S1—C43 | −0.5 (3) |
N4—Fe1—N3—C24 | 3.4 (2) | C42—C43—S1—O2 | 67.4 (4) |
C24—N3—C13—C14 | 0.2 (5) | C38—C43—S1—O2 | −114.7 (2) |
Fe1—N3—C13—C14 | −178.6 (2) | C42—C43—S1—O3 | −59.8 (4) |
N3—C13—C14—C15 | 0.1 (5) | C38—C43—S1—O3 | 118.1 (2) |
C13—C14—C15—C16 | 0.3 (5) | C42—C43—S1—N7 | −175.3 (3) |
C14—C15—C16—C24 | −0.9 (5) | C38—C43—S1—N7 | 2.5 (3) |
C14—C15—C16—C17 | −178.7 (3) | S2—N8—C44—O4 | −178.7 (3) |
C24—C16—C17—C18 | 0.4 (5) | S2—N8—C44—C45 | 0.4 (4) |
C15—C16—C17—C18 | 178.1 (3) | O4—C44—C45—C46 | −0.3 (6) |
C16—C17—C18—C19 | −0.3 (5) | N8—C44—C45—C46 | −179.3 (3) |
C17—C18—C19—C20 | −178.5 (3) | O4—C44—C45—C50 | 177.3 (3) |
C17—C18—C19—C23 | 0.2 (5) | N8—C44—C45—C50 | −1.7 (4) |
C23—C19—C20—C21 | 0.3 (5) | C50—C45—C46—C47 | 0.8 (5) |
C18—C19—C20—C21 | 178.9 (3) | C44—C45—C46—C47 | 178.3 (3) |
C19—C20—C21—C22 | −0.2 (5) | C45—C46—C47—C48 | −1.0 (5) |
C20—C21—C22—N4 | −0.7 (5) | C46—C47—C48—C49 | 0.3 (5) |
C21—C22—N4—C23 | 1.4 (5) | C47—C48—C49—C50 | 0.5 (5) |
C21—C22—N4—Fe1 | 177.5 (2) | C48—C49—C50—C45 | −0.7 (5) |
N6—Fe1—N4—C22 | −4.3 (3) | C48—C49—C50—S2 | 179.3 (3) |
N2—Fe1—N4—C22 | 151.5 (10) | C46—C45—C50—C49 | 0.0 (5) |
N5—Fe1—N4—C22 | −87.1 (3) | C44—C45—C50—C49 | −177.8 (3) |
N1—Fe1—N4—C22 | 89.0 (3) | C46—C45—C50—S2 | 180.0 (3) |
N3—Fe1—N4—C22 | 179.9 (3) | C44—C45—C50—S2 | 2.2 (3) |
N6—Fe1—N4—C23 | 171.9 (2) | C44—N8—S2—O5 | −113.2 (3) |
N2—Fe1—N4—C23 | −32.3 (12) | C44—N8—S2—O6 | 115.6 (3) |
N5—Fe1—N4—C23 | 89.2 (2) | C44—N8—S2—C50 | 0.7 (3) |
N1—Fe1—N4—C23 | −94.8 (2) | C49—C50—S2—O5 | −68.0 (3) |
N3—Fe1—N4—C23 | −3.9 (2) | C45—C50—S2—O5 | 112.0 (2) |
C22—N4—C23—C19 | −1.3 (4) | C49—C50—S2—O6 | 64.6 (3) |
Fe1—N4—C23—C19 | −178.1 (2) | C45—C50—S2—O6 | −115.4 (2) |
C22—N4—C23—C24 | −179.4 (3) | C49—C50—S2—N8 | 178.3 (3) |
Fe1—N4—C23—C24 | 3.8 (3) | C45—C50—S2—N8 | −1.7 (3) |
C20—C19—C23—N4 | 0.5 (5) | S3—N9—C51—O7 | −176.8 (3) |
C18—C19—C23—N4 | −178.3 (3) | S3—N9—C51—C52 | 2.6 (4) |
C20—C19—C23—C24 | 178.5 (3) | O7—C51—C52—C57 | 179.1 (3) |
C18—C19—C23—C24 | −0.2 (4) | N9—C51—C52—C57 | −0.4 (4) |
C13—N3—C24—C16 | −0.9 (4) | O7—C51—C52—C53 | −1.8 (5) |
Fe1—N3—C24—C16 | 178.1 (2) | N9—C51—C52—C53 | 178.8 (3) |
C13—N3—C24—C23 | 178.7 (3) | C57—C52—C53—C54 | 0.6 (5) |
Fe1—N3—C24—C23 | −2.3 (3) | C51—C52—C53—C54 | −178.5 (3) |
C15—C16—C24—N3 | 1.3 (5) | C52—C53—C54—C55 | −0.7 (5) |
C17—C16—C24—N3 | 179.1 (3) | C53—C54—C55—C56 | −0.4 (5) |
C15—C16—C24—C23 | −178.3 (3) | C54—C55—C56—C57 | 1.4 (5) |
C17—C16—C24—C23 | −0.5 (4) | C55—C56—C57—C52 | −1.5 (5) |
N4—C23—C24—N3 | −1.0 (4) | C55—C56—C57—S3 | −179.5 (3) |
C19—C23—C24—N3 | −179.2 (3) | C53—C52—C57—C56 | 0.5 (5) |
N4—C23—C24—C16 | 178.6 (3) | C51—C52—C57—C56 | 179.7 (3) |
C19—C23—C24—C16 | 0.4 (4) | C53—C52—C57—S3 | 178.9 (2) |
N6—Fe1—N5—C25 | 176.7 (3) | C51—C52—C57—S3 | −1.8 (3) |
N2—Fe1—N5—C25 | 83.6 (3) | C51—N9—S3—O8 | −119.9 (2) |
N1—Fe1—N5—C25 | 129.2 (10) | C51—N9—S3—O9 | 110.8 (2) |
N4—Fe1—N5—C25 | −91.6 (3) | C51—N9—S3—C57 | −3.3 (3) |
N3—Fe1—N5—C25 | −8.9 (3) | C56—C57—S3—O8 | −62.3 (3) |
N6—Fe1—N5—C36 | −3.2 (2) | C52—C57—S3—O8 | 119.5 (2) |
N2—Fe1—N5—C36 | −96.3 (2) | C56—C57—S3—O9 | 65.8 (3) |
N1—Fe1—N5—C36 | −50.7 (11) | C52—C57—S3—O9 | −112.5 (2) |
N4—Fe1—N5—C36 | 88.5 (2) | C56—C57—S3—N9 | −178.7 (3) |
N3—Fe1—N5—C36 | 171.3 (2) | C52—C57—S3—N9 | 3.0 (2) |
C36—N5—C25—C26 | 0.7 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N8—H8N···O11 | 0.92 (5) | 1.70 (5) | 2.614 (4) | 174 (4) |
O10—H1W···O4 | 0.89 (4) | 2.19 (2) | 2.989 (4) | 148 (4) |
O10—H2W···O13i | 0.90 (3) | 1.87 (3) | 2.756 (4) | 171 (5) |
O11—H3W···O10 | 0.90 (3) | 1.87 (4) | 2.740 (4) | 161 (5) |
O11—H4W···O7 | 0.90 (3) | 1.85 (3) | 2.741 (3) | 174 (4) |
O12—H5W···N7ii | 0.90 (3) | 2.70 (2) | 3.547 (5) | 157 (5) |
O12—H6W···O9iii | 0.90 (3) | 2.13 (4) | 2.917 (4) | 146 (5) |
O13—H7W···O1 | 0.90 (3) | 1.85 (2) | 2.732 (4) | 164 (4) |
O13—H8W···O14iv | 0.90 (3) | 1.95 (2) | 2.820 (5) | 163 (5) |
O14—H9W···O7v | 0.90 (3) | 1.84 (3) | 2.740 (4) | 176 (4) |
O14—H10W···O15 | 0.90 (3) | 1.97 (2) | 2.817 (4) | 157 (5) |
O15—H11W···O3 | 0.90 (3) | 2.02 (2) | 2.922 (4) | 176 (3) |
O15—H12W···O12vi | 0.90 (3) | 1.92 (2) | 2.787 (4) | 161 (4) |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x+1, −y, −z+1; (iii) x+1/2, −y+1/2, z−1/2; (iv) −x+1/2, y−1/2, −z+3/2; (v) x−1/2, −y+1/2, z−1/2; (vi) x−1/2, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Fe(C12H8N2)3](C7H4NO3S)2·C7H5NO3S·6H2O |
Mr | 1252.08 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 120 |
a, b, c (Å) | 16.113 (4), 19.079 (5), 17.227 (4) |
β (°) | 92.873 (5) |
V (Å3) | 5289 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.49 |
Crystal size (mm) | 0.48 × 0.19 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART-CCD diffractometer |
Absorption correction | Integration (SHELXTL-NT; Bruker, 1998) |
Tmin, Tmax | 0.830, 0.954 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 47439, 14753, 7374 |
Rint | 0.115 |
(sin θ/λ)max (Å−1) | 0.713 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.145, 0.99 |
No. of reflections | 14753 |
No. of parameters | 812 |
No. of restraints | 18 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.52, −0.70 |
Computer programs: SMART-NT (Bruker, 1998), SMART-NT, SAINT-NT (Bruker, 1998), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL-NT (Bruker, 1998).
Fe1—N1 | 1.965 (3) | Fe1—N4 | 1.973 (3) |
Fe1—N2 | 1.963 (3) | Fe1—N5 | 1.963 (3) |
Fe1—N3 | 1.974 (3) | Fe1—N6 | 1.957 (3) |
N1—Fe1—N2 | 82.55 (11) | N2—Fe1—N6 | 93.44 (11) |
N1—Fe1—N3 | 91.50 (11) | N3—Fe1—N4 | 82.77 (11) |
N1—Fe1—N4 | 94.89 (11) | N3—Fe1—N5 | 93.00 (11) |
N1—Fe1—N5 | 173.96 (11) | N3—Fe1—N6 | 173.03 (11) |
N1—Fe1—N6 | 93.15 (11) | N4—Fe1—N5 | 89.67 (10) |
N2—Fe1—N3 | 92.31 (11) | N4—Fe1—N6 | 91.66 (11) |
N2—Fe1—N4 | 174.42 (11) | N5—Fe1—N6 | 82.75 (11) |
N2—Fe1—N5 | 93.23 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
N8—H8N···O11 | 0.92 (5) | 1.70 (5) | 2.614 (4) | 174 (4) |
O10—H1W···O4 | 0.89 (4) | 2.19 (2) | 2.989 (4) | 148 (4) |
O10—H2W···O13i | 0.90 (3) | 1.87 (3) | 2.756 (4) | 171 (5) |
O11—H3W···O10 | 0.90 (3) | 1.87 (4) | 2.740 (4) | 161 (5) |
O11—H4W···O7 | 0.90 (3) | 1.85 (3) | 2.741 (3) | 174 (4) |
O12—H5W···N7ii | 0.90 (3) | 2.70 (2) | 3.547 (5) | 157 (5) |
O12—H6W···O9iii | 0.90 (3) | 2.13 (4) | 2.917 (4) | 146 (5) |
O13—H7W···O1 | 0.90 (3) | 1.85 (2) | 2.732 (4) | 164 (4) |
O13—H8W···O14iv | 0.90 (3) | 1.95 (2) | 2.820 (5) | 163 (5) |
O14—H9W···O7v | 0.90 (3) | 1.84 (3) | 2.740 (4) | 176 (4) |
O14—H10W···O15 | 0.90 (3) | 1.97 (2) | 2.817 (4) | 157 (5) |
O15—H11W···O3 | 0.90 (3) | 2.02 (2) | 2.922 (4) | 176 (3) |
O15—H12W···O12vi | 0.90 (3) | 1.92 (2) | 2.787 (4) | 161 (4) |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x+1, −y, −z+1; (iii) x+1/2, −y+1/2, z−1/2; (iv) −x+1/2, y−1/2, −z+3/2; (v) x−1/2, −y+1/2, z−1/2; (vi) x−1/2, −y+1/2, z+1/2. |
In our earlier papers on metal-saccharinate complexes with the bidentate ligands 2,2'-bipyridine (bipy) or phen present (Dillon et al., 1999; Deng et al., 2000), we summarized previous work on these systems, including examples with all the saccharinate ligands attached to the metal (Hergold-Brundic et al., 1989) and ones where saccharinate is present only as the counter-ion (Ainscough et al., 1990; Li, Chen et al., 1993; Li, Wei et al., 1993). The only structures reported for iron(II) complexes of saccharin are those of the parent compound, [Fe(sac)2(H2O)4]·2H2O (Haider et al., 1983), and of the phen complex [Fe(phen)3](sac)2·4H2O (Li, Wei et al., 1993?). In the present work, we report the structure of another tris(1,10-phenanthroline)iron(II) complex, (I), with two saccharinate anions and one free saccharin molecule present, as well as six waters of crystallization. The compound has been confirmed as diamagnetic iron(II) (d6 low spin) by magnetic measurements, which clearly eliminates the alternative possibility of an iron(III) complex with three saccharinate anions. Such a d5 complex, if low spin, would be paramagnetic, with one unpaired electron present, while a high spin species would have five unpaired electrons. Low spin would be expected in any case, from the position of phen in the spectrochemical series. \sch
The structure of the title compound consists of slightly distorted octahedral [Fe(phen)3]2+ cations, with two saccharinate anions, a free saccharin molecule and six water molecules. The Fe—N distances (Table 1) are quite similar within each of the bidentate phen ligands, although the bonds are slightly longer to N3 and N4 than to the other four N atoms; the average Fe—N bond length is 1.966 Å. This compares well, for example, with the mean distance of 1.97 Å in l-[Fe(phen)3]bis[Sb(III)d-tartrate]·8H2O (Zalkin et al., 1973), 1.973 Å in [Fe(phen)3]I2·2H2O (Johansson et al., 1978) and 1.980 Å in [Fe(phen)3](sac)2·4H2O (Li, Wei et al., 1993?). The central Fe in (I) is very close to co-planarity with the four surrounding N atoms; the largest deviation is 0.014 (1) Å from the plane defined by N2, N3, N4 and N6. This compares with more significant deviations of 0.06, 0.03 and 0.008 Å in the structure of [Fe(phen)3](sac)2·4H2O (Li, Wei et al., 1993?).
The hydrogen-bonding geometry of (I) is shown in Table 2 and displayed in Fig. 2. There is a strong, essentially linear, hydrogen bond between H8 (on N8) in the saccharin molecule to O11 of a water molecule, with a distance of 1.70 (5) Å and a bond angle at H of 174 (4)°. The carbonyl oxygen O7 in one of the saccharinate anions appears to form linear hydrogen bonds with both H4W and H9W on adjacent water molecules, with distances and angles shown in Table 2. There is also a linear hydrogen bond between O3 on S1 in the second saccharinate anion and H11W (see Table 2). A shorter contact between the carbonyl oxygen O1 and H7W in this ion is also found at 1.853 (13) Å, but at a slightly less favourable angle of 164 (4)°. Other weaker hydrogen bonds between either the free saccharin molecule or a saccharinate anion and a water molecule are tabulated in Table 2, as well as hydrogen bonds between water molecules.
The overall hydrogen-bond scheme can be described as a three-dimensional network formed by the saccharinate anions, the free saccharin molecule and the water molecules. This network, shown in Fig. 3, leaves channels along the b axis where the cations reside.