Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0021889807040149/db5028sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0021889807040149/db5028hs_32ksup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0021889807040149/db5028hs_15ksup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0021889807040149/db5028ls_15ksup4.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S0021889807040149/db5028sup5.pdf |
CCDC references: 671655; 671656; 671657
For all compounds, data collection: CRYSALIS Oxford Diffraction (2004); cell refinement: CRYSALIS Oxford Diffraction (2004); data reduction: CRYSALIS Oxford Diffraction (2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990). Program(s) used to refine structure: SHELXL97 (Sheldrick, 1997)' for hs_32k; SHELXL97 (Sheldrick, 1997) for hs_15k, ls_15k.
C26H16FeN6S2 | F(000) = 1088 |
Mr = 532.42 | Dx = 1.571 Mg m−3 |
Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2n 2ab | Cell parameters from 18028 reflections |
a = 13.1928 (4) Å | θ = 3.5–34.8° |
b = 9.9503 (3) Å | µ = 0.89 mm−1 |
c = 17.1498 (8) Å | T = 32 K |
V = 2251.29 (14) Å3 | Block, purple |
Z = 4 | 0.15 × 0.10 × 0.05 mm |
Oxford Xcalibur CCD diffractometer | 4045 independent reflections |
Radiation source: fine-focus sealed tube | 2423 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
ω scans | θmax = 34.8°, θmin = 3.5° |
Absorption correction: gaussian Absorption correction were performed using CRYSALIS Oxford Diffraction (2004) | h = 0→20 |
Tmin = 0.90, Tmax = 0.95 | k = 0→15 |
18028 measured reflections | l = 0→22 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.91 | w = 1/[σ2(Fo2) + (0.0644P)2] where P = (Fo2 + 2Fc2)/3 |
4045 reflections | (Δ/σ)max < 0.001 |
191 parameters | Δρmax = 1.14 e Å−3 |
0 restraints | Δρmin = −0.41 e Å−3 |
C26H16FeN6S2 | V = 2251.29 (14) Å3 |
Mr = 532.42 | Z = 4 |
Orthorhombic, Pbcn | Mo Kα radiation |
a = 13.1928 (4) Å | µ = 0.89 mm−1 |
b = 9.9503 (3) Å | T = 32 K |
c = 17.1498 (8) Å | 0.15 × 0.10 × 0.05 mm |
Oxford Xcalibur CCD diffractometer | 4045 independent reflections |
Absorption correction: gaussian Absorption correction were performed using CRYSALIS Oxford Diffraction (2004) | 2423 reflections with I > 2σ(I) |
Tmin = 0.90, Tmax = 0.95 | Rint = 0.055 |
18028 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.108 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.91 | Δρmax = 1.14 e Å−3 |
4045 reflections | Δρmin = −0.41 e Å−3 |
191 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 | ||
Fe1 | 0.0000 | 0.17477 (3) | 0.2500 | 0.01199 (10) | |
N20 | 0.04161 (13) | 0.31625 (15) | 0.33376 (10) | 0.0175 (4) | |
C21 | 0.08609 (14) | 0.38685 (18) | 0.37576 (12) | 0.0149 (4) | |
S22 | 0.14811 (4) | 0.48490 (4) | 0.43526 (3) | 0.01700 (12) | |
N1 | −0.00196 (12) | 0.01594 (14) | 0.16020 (10) | 0.0139 (3) | |
N2 | 0.16106 (11) | 0.13292 (15) | 0.22730 (10) | 0.0126 (3) | |
C1 | 0.09108 (13) | −0.03007 (17) | 0.13894 (11) | 0.0128 (4) | |
C2 | 0.17808 (14) | 0.03191 (17) | 0.17541 (11) | 0.0131 (4) | |
C3 | −0.08241 (14) | −0.03712 (18) | 0.12497 (13) | 0.0166 (4) | |
C4 | −0.07546 (15) | −0.14000 (19) | 0.06945 (13) | 0.0193 (4) | |
C5 | 0.01788 (15) | −0.19010 (19) | 0.04988 (13) | 0.0179 (4) | |
C6 | 0.10573 (15) | −0.13383 (18) | 0.08458 (12) | 0.0156 (4) | |
C7 | 0.20599 (14) | −0.17839 (18) | 0.06693 (12) | 0.0154 (4) | |
C8 | 0.28803 (15) | −0.12095 (19) | 0.10118 (12) | 0.0158 (4) | |
C9 | 0.27634 (14) | −0.01291 (17) | 0.15613 (12) | 0.0140 (4) | |
C10 | 0.35881 (15) | 0.05122 (19) | 0.19223 (12) | 0.0158 (4) | |
C11 | 0.34114 (15) | 0.15284 (18) | 0.24475 (12) | 0.0165 (4) | |
C12 | 0.24110 (15) | 0.19048 (17) | 0.26060 (12) | 0.0147 (4) | |
H3 | −0.1482 (17) | −0.002 (2) | 0.1361 (15) | 0.021 (6)* | |
H4 | −0.1375 (19) | −0.175 (2) | 0.0470 (15) | 0.028 (7)* | |
H5 | 0.0269 (16) | −0.264 (3) | 0.0150 (14) | 0.024 (6)* | |
H7 | 0.2166 (16) | −0.251 (2) | 0.0307 (13) | 0.018 (6)* | |
H8 | 0.3567 (17) | −0.148 (2) | 0.0883 (13) | 0.019 (6)* | |
H10 | 0.4241 (18) | 0.027 (2) | 0.1783 (13) | 0.021 (6)* | |
H11 | 0.3978 (17) | 0.198 (2) | 0.2696 (12) | 0.012 (5)* | |
H12 | 0.2267 (15) | 0.258 (2) | 0.2974 (12) | 0.014 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.01190 (17) | 0.01127 (16) | 0.0128 (2) | 0.000 | −0.00035 (15) | 0.000 |
N20 | 0.0180 (8) | 0.0162 (7) | 0.0182 (10) | 0.0011 (6) | 0.0008 (7) | 0.0005 (7) |
C21 | 0.0156 (9) | 0.0147 (8) | 0.0144 (11) | 0.0013 (7) | 0.0011 (7) | 0.0028 (7) |
S22 | 0.0194 (2) | 0.0156 (2) | 0.0160 (3) | −0.00136 (17) | −0.00189 (19) | −0.00020 (19) |
N1 | 0.0143 (7) | 0.0126 (6) | 0.0148 (9) | −0.0001 (6) | 0.0008 (6) | −0.0002 (6) |
N2 | 0.0147 (7) | 0.0105 (6) | 0.0124 (9) | 0.0006 (5) | 0.0011 (6) | 0.0011 (6) |
C1 | 0.0156 (8) | 0.0099 (7) | 0.0128 (11) | 0.0005 (6) | 0.0005 (7) | 0.0012 (7) |
C2 | 0.0150 (8) | 0.0122 (8) | 0.0121 (11) | −0.0003 (6) | 0.0003 (7) | 0.0030 (7) |
C3 | 0.0144 (9) | 0.0151 (8) | 0.0202 (12) | 0.0006 (7) | −0.0004 (8) | −0.0022 (8) |
C4 | 0.0187 (10) | 0.0173 (8) | 0.0218 (12) | −0.0027 (7) | −0.0025 (8) | −0.0037 (8) |
C5 | 0.0224 (10) | 0.0149 (8) | 0.0163 (12) | −0.0012 (7) | −0.0001 (7) | −0.0052 (8) |
C6 | 0.0202 (9) | 0.0109 (7) | 0.0157 (11) | 0.0003 (7) | 0.0014 (7) | 0.0012 (7) |
C7 | 0.0181 (9) | 0.0139 (8) | 0.0142 (11) | 0.0020 (7) | 0.0035 (7) | −0.0001 (8) |
C8 | 0.0177 (9) | 0.0154 (8) | 0.0142 (12) | 0.0019 (7) | 0.0029 (7) | 0.0006 (7) |
C9 | 0.0176 (9) | 0.0121 (7) | 0.0122 (10) | 0.0012 (7) | 0.0010 (7) | 0.0028 (7) |
C10 | 0.0143 (9) | 0.0162 (8) | 0.0167 (12) | 0.0020 (7) | 0.0008 (8) | 0.0036 (7) |
C11 | 0.0184 (9) | 0.0154 (8) | 0.0155 (11) | −0.0020 (7) | −0.0036 (8) | 0.0031 (8) |
C12 | 0.0170 (8) | 0.0121 (7) | 0.0150 (11) | 0.0003 (6) | 0.0001 (7) | −0.0008 (8) |
Fe1—N20 | 2.0848 (17) | C3—H3 | 0.95 (2) |
Fe1—N20i | 2.0848 (17) | C4—C5 | 1.370 (3) |
Fe1—N2i | 2.2000 (15) | C4—H4 | 0.97 (2) |
Fe1—N2 | 2.2000 (15) | C5—C6 | 1.418 (3) |
Fe1—N1 | 2.2068 (16) | C5—H5 | 0.95 (2) |
Fe1—N1i | 2.2068 (16) | C6—C7 | 1.428 (3) |
N20—C21 | 1.165 (3) | C7—C8 | 1.358 (3) |
C21—S22 | 1.632 (2) | C7—H7 | 0.96 (2) |
N1—C3 | 1.331 (2) | C8—C9 | 1.438 (3) |
N1—C1 | 1.360 (2) | C8—H8 | 0.97 (2) |
N2—C12 | 1.330 (2) | C9—C10 | 1.405 (3) |
N2—C2 | 1.361 (2) | C10—C11 | 1.374 (3) |
C1—C6 | 1.404 (3) | C10—H10 | 0.93 (2) |
C1—C2 | 1.445 (3) | C11—C12 | 1.399 (3) |
C2—C9 | 1.410 (3) | C11—H11 | 0.97 (2) |
C3—C4 | 1.401 (3) | C12—H12 | 0.94 (2) |
N20—Fe1—N20i | 95.06 (9) | N1—C3—H3 | 119.3 (14) |
N20—Fe1—N2i | 105.08 (6) | C4—C3—H3 | 117.6 (14) |
N20i—Fe1—N2i | 89.74 (6) | C5—C4—C3 | 119.41 (18) |
N20—Fe1—N2 | 89.74 (6) | C5—C4—H4 | 122.1 (14) |
N20i—Fe1—N2 | 105.08 (6) | C3—C4—H4 | 118.5 (14) |
N2i—Fe1—N2 | 158.18 (8) | C4—C5—C6 | 119.22 (18) |
N20—Fe1—N1 | 165.35 (6) | C4—C5—H5 | 123.0 (13) |
N20i—Fe1—N1 | 89.98 (6) | C6—C5—H5 | 117.7 (13) |
N2i—Fe1—N1 | 88.66 (6) | C1—C6—C5 | 117.16 (18) |
N2—Fe1—N1 | 75.66 (6) | C1—C6—C7 | 119.77 (18) |
N20—Fe1—N1i | 89.98 (6) | C5—C6—C7 | 123.07 (18) |
N20i—Fe1—N1i | 165.35 (6) | C8—C7—C6 | 121.08 (18) |
N2i—Fe1—N1i | 75.66 (6) | C8—C7—H7 | 118.6 (13) |
N2—Fe1—N1i | 88.66 (6) | C6—C7—H7 | 120.3 (13) |
N1—Fe1—N1i | 88.53 (8) | C7—C8—C9 | 120.85 (18) |
C21—N20—Fe1 | 165.01 (16) | C7—C8—H8 | 122.1 (13) |
N20—C21—S22 | 179.5 (2) | C9—C8—H8 | 117.0 (13) |
C3—N1—C1 | 117.69 (16) | C10—C9—C2 | 117.70 (17) |
C3—N1—Fe1 | 127.62 (13) | C10—C9—C8 | 123.04 (17) |
C1—N1—Fe1 | 114.68 (12) | C2—C9—C8 | 119.26 (17) |
C12—N2—C2 | 117.89 (16) | C11—C10—C9 | 119.45 (18) |
C12—N2—Fe1 | 127.54 (13) | C11—C10—H10 | 121.2 (14) |
C2—N2—Fe1 | 114.50 (12) | C9—C10—H10 | 119.3 (14) |
N1—C1—C6 | 123.34 (17) | C10—C11—C12 | 118.98 (18) |
N1—C1—C2 | 117.20 (16) | C10—C11—H11 | 119.8 (13) |
C6—C1—C2 | 119.45 (17) | C12—C11—H11 | 121.2 (13) |
N2—C2—C9 | 122.58 (17) | N2—C12—C11 | 123.40 (18) |
N2—C2—C1 | 117.85 (16) | N2—C12—H12 | 115.8 (12) |
C9—C2—C1 | 119.57 (17) | C11—C12—H12 | 120.7 (13) |
N1—C3—C4 | 123.11 (18) |
Symmetry code: (i) −x, y, −z+1/2. |
C26H16FeN6S2 | F(000) = 1088 |
Mr = 532.42 | Dx = 1.573 Mg m−3 |
Orthorhombic, Pbcn | Synchrotron radiation, λ = 0.71 Å |
Hall symbol: -P 2n 2ab | Cell parameters from 23123 reflections |
a = 13.185 (1) Å | θ = 3.9–45.5° |
b = 9.948 (1) Å | µ = 0.89 mm−1 |
c = 17.135 (1) Å | T = 15 K |
V = 2247.5 (5) Å3 | Block, purple |
Z = 4 | 0.24 × 0.22 × 0.21 mm |
KUMA KM6 diffractometer | 7259 independent reflections |
Radiation source: synchrotron | 5353 reflections with I > 2σ(I) |
Si monochromator | Rint = 0.021 |
phi scans | θmax = 45.5°, θmin = 3.9° |
Absorption correction: gaussian Absorption correction were performed using CRYSALIS Oxford Diffraction (2004) | h = 0→26 |
Tmin = 0.809, Tmax = 0.827 | k = 0→19 |
23123 measured reflections | l = 0→31 |
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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.200 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.1359P)2 + 0.8177P] where P = (Fo2 + 2Fc2)/3 |
7259 reflections | (Δ/σ)max = 0.001 |
191 parameters | Δρmax = 5.60 e Å−3 |
0 restraints | Δρmin = −1.93 e Å−3 |
C26H16FeN6S2 | V = 2247.5 (5) Å3 |
Mr = 532.42 | Z = 4 |
Orthorhombic, Pbcn | Synchrotron radiation, λ = 0.71 Å |
a = 13.185 (1) Å | µ = 0.89 mm−1 |
b = 9.948 (1) Å | T = 15 K |
c = 17.135 (1) Å | 0.24 × 0.22 × 0.21 mm |
KUMA KM6 diffractometer | 7259 independent reflections |
Absorption correction: gaussian Absorption correction were performed using CRYSALIS Oxford Diffraction (2004) | 5353 reflections with I > 2σ(I) |
Tmin = 0.809, Tmax = 0.827 | Rint = 0.021 |
23123 measured reflections |
R[F2 > 2σ(F2)] = 0.064 | 0 restraints |
wR(F2) = 0.200 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 5.60 e Å−3 |
7259 reflections | Δρmin = −1.93 e Å−3 |
191 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 | ||
Fe | 0.5000 | 0.17576 (3) | 0.2500 | 0.01252 (7) | |
N | 0.54159 (11) | 0.31708 (13) | 0.16616 (8) | 0.01732 (19) | |
C | 0.58648 (10) | 0.38766 (14) | 0.12380 (8) | 0.01546 (19) | |
S | 0.64840 (3) | 0.48547 (4) | 0.06459 (2) | 0.01692 (8) | |
N1 | 0.49823 (9) | 0.01611 (12) | 0.34018 (7) | 0.01384 (17) | |
N2 | 0.66122 (9) | 0.13359 (12) | 0.27274 (7) | 0.01388 (16) | |
C1 | 0.59118 (10) | −0.02973 (13) | 0.36080 (8) | 0.01366 (18) | |
C2 | 0.67808 (10) | 0.03233 (13) | 0.32461 (8) | 0.01347 (18) | |
C3 | 0.41777 (11) | −0.03666 (15) | 0.37523 (9) | 0.0163 (2) | |
C4 | 0.42469 (12) | −0.14032 (16) | 0.43086 (9) | 0.0184 (2) | |
C5 | 0.51841 (12) | −0.19038 (16) | 0.45028 (10) | 0.0175 (2) | |
C6 | 0.60559 (11) | −0.13361 (14) | 0.41545 (8) | 0.01470 (19) | |
C7 | 0.70644 (12) | −0.17905 (14) | 0.43319 (9) | 0.0161 (2) | |
C8 | 0.78828 (11) | −0.12137 (14) | 0.39845 (8) | 0.0159 (2) | |
C9 | 0.77627 (10) | −0.01273 (13) | 0.34373 (8) | 0.01442 (18) | |
C10 | 0.85929 (11) | 0.05143 (15) | 0.30762 (9) | 0.0162 (2) | |
C11 | 0.84118 (11) | 0.15326 (16) | 0.25476 (8) | 0.0160 (2) | |
C12 | 0.74111 (11) | 0.19118 (14) | 0.23913 (9) | 0.01548 (19) | |
H5 | 0.529 (3) | −0.266 (4) | 0.485 (2) | 0.030 (8)* | |
H7 | 0.709 (2) | −0.245 (3) | 0.4697 (18) | 0.022 (7)* | |
H8 | 0.858 (2) | −0.147 (3) | 0.4122 (19) | 0.021 (7)* | |
H10 | 0.928 (3) | 0.027 (3) | 0.322 (2) | 0.028 (8)* | |
H11 | 0.900 (2) | 0.197 (3) | 0.2332 (17) | 0.015 (6)* | |
H12 | 0.728 (3) | 0.256 (4) | 0.200 (2) | 0.031 (8)* | |
H3 | 0.356 (3) | −0.005 (4) | 0.365 (2) | 0.036 (9)* | |
H4 | 0.363 (3) | −0.175 (4) | 0.453 (2) | 0.033 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe | 0.01479 (11) | 0.01327 (11) | 0.00950 (12) | 0.000 | 0.00030 (7) | 0.000 |
N | 0.0192 (4) | 0.0184 (5) | 0.0144 (5) | 0.0002 (4) | 0.0011 (4) | 0.0020 (3) |
C | 0.0173 (5) | 0.0165 (4) | 0.0125 (5) | 0.0005 (4) | 0.0006 (4) | 0.0005 (3) |
S | 0.02005 (15) | 0.01729 (14) | 0.01341 (15) | −0.00135 (10) | 0.00137 (10) | 0.00085 (9) |
N1 | 0.0156 (4) | 0.0142 (4) | 0.0117 (4) | −0.0001 (3) | 0.0003 (3) | 0.0019 (3) |
N2 | 0.0163 (4) | 0.0145 (4) | 0.0108 (4) | 0.0014 (3) | 0.0000 (3) | 0.0009 (3) |
C1 | 0.0156 (4) | 0.0148 (4) | 0.0106 (4) | 0.0004 (3) | −0.0009 (3) | 0.0006 (3) |
C2 | 0.0151 (4) | 0.0144 (4) | 0.0109 (4) | 0.0012 (3) | −0.0002 (3) | 0.0000 (3) |
C3 | 0.0163 (4) | 0.0177 (5) | 0.0148 (5) | 0.0001 (4) | 0.0005 (4) | 0.0031 (4) |
C4 | 0.0183 (5) | 0.0192 (5) | 0.0175 (6) | −0.0023 (4) | 0.0008 (4) | 0.0043 (4) |
C5 | 0.0182 (5) | 0.0188 (5) | 0.0155 (5) | −0.0005 (4) | −0.0004 (4) | 0.0047 (4) |
C6 | 0.0167 (4) | 0.0152 (4) | 0.0122 (4) | 0.0000 (4) | −0.0013 (4) | 0.0020 (3) |
C7 | 0.0178 (5) | 0.0171 (5) | 0.0132 (5) | 0.0001 (4) | −0.0007 (4) | 0.0027 (3) |
C8 | 0.0171 (5) | 0.0174 (5) | 0.0131 (5) | 0.0005 (4) | −0.0013 (4) | 0.0014 (3) |
C9 | 0.0159 (4) | 0.0151 (4) | 0.0123 (5) | 0.0012 (3) | −0.0001 (3) | 0.0000 (3) |
C10 | 0.0161 (4) | 0.0181 (5) | 0.0145 (5) | 0.0015 (4) | 0.0000 (4) | 0.0004 (4) |
C11 | 0.0162 (4) | 0.0180 (5) | 0.0137 (5) | 0.0003 (4) | 0.0017 (4) | 0.0013 (4) |
C12 | 0.0162 (5) | 0.0159 (4) | 0.0143 (5) | −0.0005 (4) | 0.0009 (4) | 0.0014 (3) |
Fe—Ni | 2.0835 (13) | C3—H3 | 0.89 (4) |
Fe—N | 2.0835 (13) | C4—C5 | 1.373 (2) |
Fe—N2 | 2.2014 (12) | C4—H4 | 0.97 (4) |
Fe—N2i | 2.2014 (12) | C5—C6 | 1.413 (2) |
Fe—N1i | 2.2160 (12) | C5—H5 | 0.97 (4) |
Fe—N1 | 2.2160 (12) | C6—C7 | 1.437 (2) |
N—C | 1.1706 (19) | C7—C8 | 1.359 (2) |
C—S | 1.6256 (14) | C7—H7 | 0.91 (3) |
N1—C3 | 1.3273 (18) | C8—C9 | 1.4394 (19) |
N1—C1 | 1.3546 (17) | C8—H8 | 0.98 (3) |
N2—C12 | 1.3301 (19) | C9—C10 | 1.410 (2) |
N2—C2 | 1.3616 (18) | C10—C11 | 1.380 (2) |
C1—C6 | 1.4074 (18) | C10—H10 | 0.97 (4) |
C1—C2 | 1.4417 (19) | C11—C12 | 1.398 (2) |
C2—C9 | 1.4088 (19) | C11—H11 | 0.97 (3) |
C3—C4 | 1.407 (2) | C12—H12 | 0.95 (3) |
Ni—Fe—N | 95.13 (8) | N1—C3—H3 | 120 (3) |
Ni—Fe—N2 | 105.11 (5) | C4—C3—H3 | 117 (3) |
N—Fe—N2 | 89.80 (5) | C5—C4—C3 | 119.23 (14) |
Ni—Fe—N2i | 89.80 (5) | C5—C4—H4 | 122 (2) |
N—Fe—N2i | 105.11 (5) | C3—C4—H4 | 118 (2) |
N2—Fe—N2i | 158.03 (6) | C4—C5—C6 | 118.99 (13) |
Ni—Fe—N1i | 165.28 (5) | C4—C5—H5 | 124 (2) |
N—Fe—N1i | 90.00 (5) | C6—C5—H5 | 117 (2) |
N2—Fe—N1i | 88.66 (4) | C1—C6—C5 | 117.69 (13) |
N2i—Fe—N1i | 75.53 (4) | C1—C6—C7 | 119.78 (13) |
Ni—Fe—N1 | 90.00 (5) | C5—C6—C7 | 122.53 (13) |
N—Fe—N1 | 165.28 (5) | C8—C7—C6 | 120.60 (13) |
N2—Fe—N1 | 75.53 (4) | C8—C7—H7 | 125 (2) |
N2i—Fe—N1 | 88.66 (4) | C6—C7—H7 | 114 (2) |
N1i—Fe—N1 | 88.44 (7) | C7—C8—C9 | 120.99 (13) |
C—N—Fe | 164.88 (13) | C7—C8—H8 | 121.7 (19) |
N—C—S | 179.68 (15) | C9—C8—H8 | 117.1 (19) |
C3—N1—C1 | 118.16 (12) | C2—C9—C10 | 117.86 (12) |
C3—N1—Fe | 127.40 (9) | C2—C9—C8 | 119.44 (12) |
C1—N1—Fe | 114.44 (9) | C10—C9—C8 | 122.71 (12) |
C12—N2—C2 | 118.16 (12) | C11—C10—C9 | 119.08 (13) |
C12—N2—Fe | 127.29 (10) | C11—C10—H10 | 121 (2) |
C2—N2—Fe | 114.46 (9) | C9—C10—H10 | 120 (2) |
N1—C1—C6 | 122.88 (12) | C10—C11—C12 | 119.15 (13) |
N1—C1—C2 | 117.55 (11) | C10—C11—H11 | 116.5 (18) |
C6—C1—C2 | 119.57 (12) | C12—C11—H11 | 124.3 (18) |
N2—C2—C9 | 122.50 (12) | N2—C12—C11 | 123.24 (13) |
N2—C2—C1 | 117.90 (12) | N2—C12—H12 | 117 (2) |
C9—C2—C1 | 119.60 (12) | C11—C12—H12 | 120 (2) |
N1—C3—C4 | 122.99 (13) |
Symmetry code: (i) −x+1, y, −z+1/2. |
C26H16FeN6S2 | F(000) = 1088 |
Mr = 532.42 | Dx = 1.618 Mg m−3 |
Orthorhombic, Pbcn | Synchrotron radiation, λ = 0.71 Å |
Hall symbol: -P 2n 2ab | Cell parameters from 23007 reflections |
a = 12.762 (1) Å | θ = 4.0–45.3° |
b = 10.024 (1) Å | µ = 0.91 mm−1 |
c = 17.090 (1) Å | T = 15 K |
V = 2186.2 (3) Å3 | Block, purple |
Z = 4 | 0.24 × 0.22 × 0.21 mm |
KUMA KM6 diffractometer | 7122 independent reflections |
Radiation source: synchrotron | 5377 reflections with I > 2σ(I) |
Si monochromator | Rint = 0.019 |
phi scans | θmax = 45.3°, θmin = 4.0° |
Absorption correction: gaussian Absorption correction were performed using CRYSALIS Oxford Diffraction (2004) | h = 0→25 |
Tmin = 0.808, Tmax = 0.830 | k = 0→20 |
23007 measured reflections | l = 0→31 |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.148 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.1061P)2 + 0.2257P] where P = (Fo2 + 2Fc2)/3 |
7122 reflections | (Δ/σ)max = 0.001 |
191 parameters | Δρmax = 3.66 e Å−3 |
0 restraints | Δρmin = −0.73 e Å−3 |
C26H16FeN6S2 | V = 2186.2 (3) Å3 |
Mr = 532.42 | Z = 4 |
Orthorhombic, Pbcn | Synchrotron radiation, λ = 0.71 Å |
a = 12.762 (1) Å | µ = 0.91 mm−1 |
b = 10.024 (1) Å | T = 15 K |
c = 17.090 (1) Å | 0.24 × 0.22 × 0.21 mm |
KUMA KM6 diffractometer | 7122 independent reflections |
Absorption correction: gaussian Absorption correction were performed using CRYSALIS Oxford Diffraction (2004) | 5377 reflections with I > 2σ(I) |
Tmin = 0.808, Tmax = 0.830 | Rint = 0.019 |
23007 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.148 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 3.66 e Å−3 |
7122 reflections | Δρmin = −0.73 e Å−3 |
191 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 | ||
Fe | 0.5000 | 0.14734 (2) | 0.2500 | 0.01108 (5) | |
N | 0.52856 (8) | 0.28326 (10) | 0.17235 (6) | 0.01507 (14) | |
C | 0.56909 (8) | 0.36224 (10) | 0.13155 (7) | 0.01454 (15) | |
S | 0.62638 (2) | 0.47174 (3) | 0.074878 (18) | 0.01562 (6) | |
N1 | 0.48795 (7) | 0.01028 (9) | 0.33294 (6) | 0.01242 (12) | |
N2 | 0.65193 (7) | 0.13266 (9) | 0.27546 (5) | 0.01219 (12) | |
C1 | 0.58258 (7) | −0.03021 (10) | 0.36135 (6) | 0.01236 (14) | |
C2 | 0.67223 (8) | 0.03504 (10) | 0.32915 (6) | 0.01224 (13) | |
C3 | 0.40256 (8) | −0.04384 (11) | 0.36486 (7) | 0.01521 (15) | |
C4 | 0.40741 (9) | −0.14209 (12) | 0.42327 (8) | 0.01728 (17) | |
C5 | 0.50314 (9) | −0.18715 (12) | 0.44977 (8) | 0.01656 (17) | |
C6 | 0.59481 (8) | −0.12900 (10) | 0.41889 (6) | 0.01369 (14) | |
C7 | 0.69873 (9) | −0.16625 (11) | 0.44212 (7) | 0.01562 (15) | |
C8 | 0.78465 (8) | −0.10668 (11) | 0.41029 (7) | 0.01526 (16) | |
C9 | 0.77361 (8) | −0.00208 (10) | 0.35304 (6) | 0.01330 (14) | |
C10 | 0.85878 (8) | 0.06613 (11) | 0.31868 (7) | 0.01574 (16) | |
C11 | 0.83805 (8) | 0.16439 (12) | 0.26436 (7) | 0.01582 (16) | |
C12 | 0.73406 (8) | 0.19607 (11) | 0.24471 (6) | 0.01400 (15) | |
H3 | 0.335 (2) | −0.018 (2) | 0.3497 (16) | 0.025 (6)* | |
H4 | 0.340 (2) | −0.173 (3) | 0.4401 (15) | 0.022 (6)* | |
H5 | 0.5100 (16) | −0.249 (3) | 0.4890 (15) | 0.018 (5)* | |
H7 | 0.7064 (18) | −0.240 (3) | 0.4812 (14) | 0.021 (5)* | |
H8 | 0.8557 (17) | −0.132 (2) | 0.4239 (13) | 0.011 (4)* | |
H10 | 0.926 (2) | 0.052 (3) | 0.3329 (16) | 0.028 (6)* | |
H11 | 0.8968 (19) | 0.205 (2) | 0.2409 (13) | 0.014 (5)* | |
H12 | 0.7199 (18) | 0.261 (2) | 0.2059 (14) | 0.018 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe | 0.01078 (8) | 0.01042 (8) | 0.01204 (9) | 0.000 | −0.00013 (5) | 0.000 |
N | 0.0154 (3) | 0.0135 (3) | 0.0163 (4) | 0.0003 (2) | 0.0002 (3) | 0.0012 (2) |
C | 0.0145 (3) | 0.0134 (3) | 0.0157 (4) | 0.0009 (3) | −0.0002 (3) | 0.0007 (3) |
S | 0.01643 (10) | 0.01413 (10) | 0.01630 (12) | −0.00044 (7) | 0.00094 (8) | 0.00163 (7) |
N1 | 0.0113 (3) | 0.0118 (3) | 0.0141 (3) | −0.0003 (2) | −0.0006 (2) | 0.0018 (2) |
N2 | 0.0129 (3) | 0.0114 (3) | 0.0123 (3) | 0.0000 (2) | −0.0003 (2) | 0.0004 (2) |
C1 | 0.0118 (3) | 0.0112 (3) | 0.0141 (4) | −0.0002 (2) | −0.0008 (3) | 0.0007 (2) |
C2 | 0.0114 (3) | 0.0117 (3) | 0.0136 (4) | −0.0001 (2) | −0.0005 (2) | 0.0007 (2) |
C3 | 0.0121 (3) | 0.0153 (3) | 0.0183 (4) | −0.0003 (3) | −0.0002 (3) | 0.0030 (3) |
C4 | 0.0133 (3) | 0.0182 (4) | 0.0203 (5) | −0.0017 (3) | 0.0004 (3) | 0.0055 (3) |
C5 | 0.0159 (3) | 0.0159 (4) | 0.0178 (4) | −0.0010 (3) | −0.0007 (3) | 0.0053 (3) |
C6 | 0.0130 (3) | 0.0136 (3) | 0.0144 (4) | 0.0003 (3) | −0.0013 (3) | 0.0024 (3) |
C7 | 0.0145 (3) | 0.0153 (4) | 0.0171 (4) | 0.0000 (3) | −0.0019 (3) | 0.0039 (3) |
C8 | 0.0134 (3) | 0.0153 (4) | 0.0171 (4) | 0.0011 (3) | −0.0021 (3) | 0.0024 (3) |
C9 | 0.0121 (3) | 0.0130 (3) | 0.0148 (4) | 0.0008 (2) | −0.0013 (3) | 0.0007 (3) |
C10 | 0.0120 (3) | 0.0170 (4) | 0.0182 (4) | −0.0004 (3) | −0.0009 (3) | 0.0013 (3) |
C11 | 0.0125 (3) | 0.0162 (4) | 0.0188 (4) | −0.0008 (3) | 0.0003 (3) | 0.0020 (3) |
C12 | 0.0125 (3) | 0.0138 (3) | 0.0157 (4) | −0.0007 (3) | −0.0003 (3) | 0.0018 (3) |
Fe—Ni | 1.9365 (10) | C3—H3 | 0.93 (3) |
Fe—N | 1.9365 (10) | C4—C5 | 1.3790 (16) |
Fe—N1i | 1.9800 (9) | C4—H4 | 0.96 (3) |
Fe—N1 | 1.9800 (9) | C5—C6 | 1.4096 (15) |
Fe—N2i | 1.9926 (9) | C5—H5 | 0.92 (3) |
Fe—N2 | 1.9926 (9) | C6—C7 | 1.4339 (15) |
N—C | 1.1749 (15) | C7—C8 | 1.3619 (16) |
C—S | 1.6363 (11) | C7—H7 | 1.00 (2) |
N1—C3 | 1.3340 (14) | C8—C9 | 1.4409 (15) |
N1—C1 | 1.3635 (13) | C8—H8 | 0.97 (2) |
N2—C12 | 1.3337 (14) | C9—C10 | 1.4120 (15) |
N2—C2 | 1.3662 (14) | C10—C11 | 1.3791 (16) |
C1—C6 | 1.4043 (15) | C10—H10 | 0.90 (3) |
C1—C2 | 1.4282 (14) | C11—C12 | 1.4053 (15) |
C2—C9 | 1.4069 (14) | C11—H11 | 0.94 (2) |
C3—C4 | 1.4036 (16) | C12—H12 | 0.94 (2) |
Ni—Fe—N | 90.57 (6) | N1—C3—H3 | 121.7 (16) |
Ni—Fe—N1i | 173.40 (4) | C4—C3—H3 | 115.6 (16) |
N—Fe—N1i | 89.02 (4) | C5—C4—C3 | 120.16 (10) |
Ni—Fe—N1 | 89.02 (4) | C5—C4—H4 | 126.1 (15) |
N—Fe—N1 | 173.40 (4) | C3—C4—H4 | 113.7 (15) |
N1i—Fe—N1 | 92.13 (6) | C4—C5—C6 | 118.48 (10) |
Ni—Fe—N2i | 91.05 (4) | C4—C5—H5 | 123.1 (13) |
N—Fe—N2i | 94.90 (4) | C6—C5—H5 | 118.3 (13) |
N1i—Fe—N2i | 82.42 (4) | C1—C6—C5 | 117.49 (9) |
N1—Fe—N2i | 91.69 (4) | C1—C6—C7 | 118.70 (10) |
Ni—Fe—N2 | 94.90 (4) | C5—C6—C7 | 123.80 (10) |
N—Fe—N2 | 91.05 (4) | C8—C7—C6 | 121.32 (10) |
N1i—Fe—N2 | 91.69 (4) | C8—C7—H7 | 120.7 (13) |
N1—Fe—N2 | 82.42 (4) | C6—C7—H7 | 117.9 (13) |
N2i—Fe—N2 | 171.53 (5) | C7—C8—C9 | 120.77 (10) |
C—N—Fe | 164.49 (9) | C7—C8—H8 | 123.0 (13) |
N—C—S | 179.58 (11) | C9—C8—H8 | 116.3 (13) |
C3—N1—C1 | 117.19 (9) | C2—C9—C10 | 117.33 (10) |
C3—N1—Fe | 129.67 (7) | C2—C9—C8 | 118.65 (9) |
C1—N1—Fe | 113.12 (7) | C10—C9—C8 | 124.02 (9) |
C12—N2—C2 | 117.19 (9) | C11—C10—C9 | 118.56 (10) |
C12—N2—Fe | 130.05 (7) | C11—C10—H10 | 118.5 (18) |
C2—N2—Fe | 112.58 (7) | C9—C10—H10 | 122.8 (18) |
N1—C1—C6 | 123.90 (9) | C10—C11—C12 | 120.23 (10) |
N1—C1—C2 | 115.85 (9) | C10—C11—H11 | 116.2 (15) |
C6—C1—C2 | 120.26 (9) | C12—C11—H11 | 123.5 (15) |
N2—C2—C9 | 123.97 (9) | N2—C12—C11 | 122.71 (10) |
N2—C2—C1 | 115.78 (9) | N2—C12—H12 | 116.9 (14) |
C9—C2—C1 | 120.25 (9) | C11—C12—H12 | 120.2 (14) |
N1—C3—C4 | 122.69 (10) |
Symmetry code: (i) −x+1, y, −z+1/2. |
Experimental details
(hs_32k) | (hs_15k) | (ls_15k) | |
Crystal data | |||
Chemical formula | C26H16FeN6S2 | C26H16FeN6S2 | C26H16FeN6S2 |
Mr | 532.42 | 532.42 | 532.42 |
Crystal system, space group | Orthorhombic, Pbcn | Orthorhombic, Pbcn | Orthorhombic, Pbcn |
Temperature (K) | 32 | 15 | 15 |
a, b, c (Å) | 13.1928 (4), 9.9503 (3), 17.1498 (8) | 13.185 (1), 9.948 (1), 17.135 (1) | 12.762 (1), 10.024 (1), 17.090 (1) |
V (Å3) | 2251.29 (14) | 2247.5 (5) | 2186.2 (3) |
Z | 4 | 4 | 4 |
Radiation type | Mo Kα | Synchrotron, λ = 0.71 Å | Synchrotron, λ = 0.71 Å |
µ (mm−1) | 0.89 | 0.89 | 0.91 |
Crystal size (mm) | 0.15 × 0.10 × 0.05 | 0.24 × 0.22 × 0.21 | 0.24 × 0.22 × 0.21 |
Data collection | |||
Diffractometer | Oxford Xcalibur CCD diffractometer | KUMA KM6 diffractometer | KUMA KM6 diffractometer |
Absorption correction | Gaussian Absorption correction were performed using CRYSALIS Oxford Diffraction (2004) | Gaussian Absorption correction were performed using CRYSALIS Oxford Diffraction (2004) | Gaussian Absorption correction were performed using CRYSALIS Oxford Diffraction (2004) |
Tmin, Tmax | 0.90, 0.95 | 0.809, 0.827 | 0.808, 0.830 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18028, 4045, 2423 | 23123, 7259, 5353 | 23007, 7122, 5377 |
Rint | 0.055 | 0.021 | 0.019 |
(sin θ/λ)max (Å−1) | 0.804 | 1.004 | 1.001 |
Refinement | |||
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.108, 0.91 | 0.064, 0.200, 1.07 | 0.049, 0.148, 1.03 |
No. of reflections | 4045 | 7259 | 7122 |
No. of parameters | 191 | 191 | 191 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.14, −0.41 | 5.60, −1.93 | 3.66, −0.73 |
Computer programs: CRYSALIS Oxford Diffraction (2004), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997)', SHELXL97 (Sheldrick, 1997).
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