The synthesis and crystal structure (100 K) of the title compound, [Fe(C10H11BrN3OS)2]NO3·H2O, is reported. The asymmetric unit consists of an octahedral [FeIII(HL)2]+ cation, where HL− is H-5-Br-thsa-Et or 5-bromosalicylaldehyde 4-ethylthiosemicarbazonate(1−) {systematic name: 4-bromo-2-[(4-ethylthiosemicarbazidoidene)methyl]phenolate}, a nitrate anion and a noncoordinated water molecule. Each HL− ligand binds via the thione S, the imine N and the phenolate O atom, resulting in an FeIIIS2N2O2 chromophore. The ligands are orientated in two perpendicular planes, with the O and S atoms in cis and the N atoms in trans positions. This [Fe(HL)2](anion)·H2O compound contains the first known cationic FeIII entity containing two salicylaldehyde thiosemicarbazone derivatives. The FeIII ion is in the high-spin state at 100 K. In addition, a comparative IR spectroscopic study of the free ligand and the ferric complex is presented, demonstrating that such an analysis provides a quick identification of the degree of deprotonation and the coordination mode of the ligand in this class of metal compounds. The variable-temperature magnetic susceptibility measurements (5–320 K) are consistent with the presence of a high-spin FeIII ion with a zero-field splitting D = 0.439 (1) cm−1.
Supporting information
CCDC reference: 2129820
Data collection: CrystalClear-SM Expert (Rigaku, 2013); cell refinement: CrysAlis PRO (Rigaku OD, 2021); data reduction: CrysAlis PRO (Rigaku OD, 2021); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009) and
ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
Bis[4-bromo-2-({[(ethylcarbamothioyl)amino]imino}methyl)phenolato-
κ3O,
N1,
S]ferrate(III) nitrate monohydrate
top
Crystal data top
[Fe(C10H11BrN3OS)2]NO3·H2O[+solvent] | Dx = 1.736 Mg m−3 |
Mr = 738.25 | Mo Kα radiation, λ = 0.71075 Å |
Orthorhombic, Pnna | Cell parameters from 13504 reflections |
a = 12.3595 (3) Å | θ = 2.6–27.5° |
b = 23.2686 (6) Å | µ = 3.56 mm−1 |
c = 19.6406 (6) Å | T = 100 K |
V = 5648.4 (3) Å3 | Lath, dark green |
Z = 8 | 0.19 × 0.01 × 0.01 mm |
F(000) = 2952 | |
Data collection top
Rigaku FRE+ diffractometer equipped with HF Varimax confocal
mirrors and an AFC12 goniometer and HG Saturn 724+ detector | 6477 independent reflections |
Radiation source: Rotating Anode, Rigaku FRE+ | 4297 reflections with I > 2σ(I) |
Confocal mirrors, HF Varimax monochromator | Rint = 0.088 |
Detector resolution: 28.5714 pixels mm-1 | θmax = 27.5°, θmin = 2.1° |
profile data from ω–scans | h = −15→16 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2021) | k = −30→28 |
Tmin = 0.740, Tmax = 1.000 | l = −25→22 |
36848 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.057 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.130 | w = 1/[σ2(Fo2) + (0.0514P)2 + 12.8609P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.001 |
6477 reflections | Δρmax = 0.68 e Å−3 |
360 parameters | Δρmin = −0.78 e Å−3 |
6 restraints | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. H-atoms bonded to N-atoms were located in the difference map and refined with
the riding model. All N—H atom pairs were refined with an equal distance
geometric restraint. The solvent water molecule was refined as a rigid body
group. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Br11 | 1.13632 (5) | 0.95165 (3) | 0.48873 (4) | 0.0628 (3) | |
Br21 | 0.40926 (4) | 0.48998 (2) | 0.39309 (3) | 0.03039 (15) | |
Fe1 | 0.73206 (5) | 0.71905 (3) | 0.57014 (4) | 0.02070 (17) | |
S11 | 0.74079 (10) | 0.63438 (5) | 0.64326 (7) | 0.0263 (3) | |
S21 | 0.68261 (10) | 0.79079 (5) | 0.65684 (7) | 0.0281 (3) | |
O11 | 0.7817 (3) | 0.77756 (15) | 0.50614 (18) | 0.0292 (8) | |
O21 | 0.7228 (3) | 0.66978 (15) | 0.49042 (18) | 0.0283 (8) | |
N11 | 0.8946 (3) | 0.72721 (17) | 0.6116 (2) | 0.0214 (9) | |
N12 | 0.9239 (3) | 0.69112 (19) | 0.6653 (2) | 0.0289 (10) | |
H12 | 0.983 (3) | 0.700 (2) | 0.687 (2) | 0.035* | |
N13 | 0.8917 (3) | 0.61777 (19) | 0.7379 (2) | 0.0296 (10) | |
H13 | 0.955 (3) | 0.623 (2) | 0.757 (3) | 0.035* | |
N21 | 0.5579 (3) | 0.71085 (16) | 0.5705 (2) | 0.0201 (9) | |
N22 | 0.4980 (3) | 0.74451 (18) | 0.6141 (2) | 0.0257 (10) | |
H22 | 0.429 (3) | 0.738 (2) | 0.619 (3) | 0.031* | |
N23 | 0.4797 (3) | 0.81161 (18) | 0.6965 (2) | 0.0263 (10) | |
H23 | 0.411 (3) | 0.806 (2) | 0.691 (3) | 0.032* | |
C11 | 0.9498 (4) | 0.8108 (2) | 0.5479 (3) | 0.0256 (11) | |
C12 | 0.8607 (4) | 0.8145 (2) | 0.5051 (3) | 0.0244 (11) | |
C13 | 0.8551 (4) | 0.8600 (2) | 0.4577 (3) | 0.0290 (12) | |
H13A | 0.794568 | 0.862823 | 0.428075 | 0.035* | |
C14 | 0.9363 (4) | 0.9000 (2) | 0.4539 (3) | 0.0347 (13) | |
H14 | 0.931037 | 0.930904 | 0.422416 | 0.042* | |
C15 | 1.0260 (4) | 0.8955 (2) | 0.4958 (3) | 0.0338 (13) | |
C16 | 1.0352 (4) | 0.8516 (2) | 0.5418 (3) | 0.0323 (13) | |
H16 | 1.097990 | 0.848317 | 0.569491 | 0.039* | |
C17 | 0.9642 (4) | 0.7670 (2) | 0.5979 (3) | 0.0250 (11) | |
H17 | 1.029907 | 0.767082 | 0.622988 | 0.030* | |
C18 | 0.8578 (4) | 0.6481 (2) | 0.6849 (3) | 0.0235 (11) | |
C19 | 0.8305 (5) | 0.5714 (2) | 0.7686 (3) | 0.0325 (13) | |
H19A | 0.833418 | 0.537044 | 0.738868 | 0.039* | |
H19B | 0.753821 | 0.582947 | 0.773507 | 0.039* | |
C21 | 0.5442 (4) | 0.63170 (19) | 0.4908 (2) | 0.0196 (10) | |
C22 | 0.6527 (4) | 0.6310 (2) | 0.4691 (2) | 0.0240 (11) | |
C23 | 0.6846 (4) | 0.5885 (2) | 0.4228 (3) | 0.0340 (13) | |
H23A | 0.757209 | 0.587862 | 0.407000 | 0.041* | |
C24 | 0.6126 (4) | 0.5476 (2) | 0.3998 (3) | 0.0344 (13) | |
H24 | 0.635727 | 0.519082 | 0.368365 | 0.041* | |
C25 | 0.5073 (4) | 0.5480 (2) | 0.4224 (3) | 0.0247 (11) | |
C26 | 0.4721 (4) | 0.5895 (2) | 0.4658 (3) | 0.0237 (11) | |
H26 | 0.398377 | 0.590122 | 0.479458 | 0.028* | |
C27 | 0.5019 (4) | 0.67281 (19) | 0.5378 (2) | 0.0218 (11) | |
H27 | 0.426046 | 0.672161 | 0.545748 | 0.026* | |
C28 | 0.5462 (4) | 0.7824 (2) | 0.6566 (2) | 0.0227 (11) | |
C29 | 0.5135 (4) | 0.8538 (2) | 0.7462 (3) | 0.0332 (13) | |
H29A | 0.585645 | 0.842911 | 0.764023 | 0.040* | |
H29B | 0.462069 | 0.853351 | 0.784844 | 0.040* | |
C110 | 0.8767 (6) | 0.5569 (3) | 0.8375 (4) | 0.062 (2) | |
H11A | 0.952479 | 0.545279 | 0.832449 | 0.092* | |
H11B | 0.835241 | 0.525371 | 0.857747 | 0.092* | |
H11C | 0.872465 | 0.590771 | 0.867077 | 0.092* | |
C210 | 0.5192 (6) | 0.9129 (3) | 0.7180 (3) | 0.0533 (18) | |
H21A | 0.569115 | 0.913513 | 0.679198 | 0.080* | |
H21B | 0.545244 | 0.939345 | 0.753204 | 0.080* | |
H21C | 0.447095 | 0.924889 | 0.702894 | 0.080* | |
O101 | 0.7818 (3) | 0.7444 (2) | 0.3686 (2) | 0.0540 (12) | |
H10A | 0.751602 | 0.725563 | 0.336775 | 0.081* | |
H10B | 0.749073 | 0.733786 | 0.404481 | 0.081* | |
O201 | 1.2660 (4) | 0.6526 (2) | 0.7620 (3) | 0.0714 (15) | |
O202 | 1.1333 (4) | 0.6918 (3) | 0.7100 (3) | 0.089 (2) | |
O203 | 1.1007 (4) | 0.6406 (3) | 0.7980 (2) | 0.0736 (17) | |
N201 | 1.1666 (4) | 0.6618 (2) | 0.7581 (3) | 0.0460 (13) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br11 | 0.0369 (4) | 0.0510 (4) | 0.1004 (6) | −0.0233 (3) | −0.0197 (4) | 0.0426 (4) |
Br21 | 0.0335 (3) | 0.0198 (2) | 0.0379 (3) | −0.0054 (2) | −0.0136 (3) | −0.0019 (2) |
Fe1 | 0.0152 (3) | 0.0184 (4) | 0.0284 (4) | −0.0044 (3) | −0.0018 (3) | −0.0002 (3) |
S11 | 0.0205 (6) | 0.0234 (7) | 0.0348 (7) | −0.0046 (5) | −0.0026 (6) | 0.0014 (5) |
S21 | 0.0193 (6) | 0.0255 (7) | 0.0394 (8) | −0.0027 (5) | −0.0049 (6) | −0.0095 (6) |
O11 | 0.0213 (18) | 0.038 (2) | 0.028 (2) | −0.0125 (16) | −0.0058 (16) | 0.0004 (16) |
O21 | 0.0230 (19) | 0.031 (2) | 0.030 (2) | −0.0085 (15) | 0.0049 (16) | −0.0068 (16) |
N11 | 0.017 (2) | 0.022 (2) | 0.025 (2) | −0.0014 (16) | 0.0023 (18) | 0.0014 (17) |
N12 | 0.022 (2) | 0.030 (2) | 0.035 (3) | −0.0082 (19) | −0.008 (2) | 0.0061 (19) |
N13 | 0.024 (2) | 0.028 (2) | 0.036 (3) | −0.0020 (19) | −0.004 (2) | 0.006 (2) |
N21 | 0.018 (2) | 0.017 (2) | 0.026 (2) | 0.0008 (16) | −0.0008 (18) | 0.0010 (16) |
N22 | 0.018 (2) | 0.026 (2) | 0.033 (3) | −0.0015 (18) | 0.002 (2) | −0.0062 (19) |
N23 | 0.018 (2) | 0.031 (2) | 0.030 (3) | 0.0014 (18) | −0.005 (2) | −0.0043 (19) |
C11 | 0.021 (3) | 0.021 (3) | 0.035 (3) | 0.000 (2) | 0.003 (2) | 0.001 (2) |
C12 | 0.023 (3) | 0.024 (3) | 0.027 (3) | −0.002 (2) | 0.005 (2) | −0.002 (2) |
C13 | 0.027 (3) | 0.032 (3) | 0.028 (3) | −0.001 (2) | −0.006 (2) | 0.003 (2) |
C14 | 0.032 (3) | 0.029 (3) | 0.043 (3) | 0.000 (2) | 0.002 (3) | 0.009 (2) |
C15 | 0.023 (3) | 0.030 (3) | 0.048 (4) | −0.004 (2) | 0.003 (3) | 0.009 (3) |
C16 | 0.024 (3) | 0.029 (3) | 0.044 (4) | −0.004 (2) | −0.005 (3) | 0.008 (2) |
C17 | 0.016 (2) | 0.026 (3) | 0.032 (3) | −0.004 (2) | 0.000 (2) | −0.001 (2) |
C18 | 0.026 (3) | 0.019 (3) | 0.026 (3) | 0.001 (2) | 0.004 (2) | 0.001 (2) |
C19 | 0.037 (3) | 0.022 (3) | 0.038 (3) | −0.004 (2) | 0.004 (3) | 0.004 (2) |
C21 | 0.019 (2) | 0.014 (2) | 0.025 (3) | −0.0010 (18) | −0.007 (2) | 0.0025 (19) |
C22 | 0.028 (3) | 0.026 (3) | 0.018 (3) | −0.005 (2) | −0.004 (2) | 0.000 (2) |
C23 | 0.027 (3) | 0.033 (3) | 0.041 (3) | −0.006 (2) | 0.002 (3) | −0.012 (3) |
C24 | 0.037 (3) | 0.028 (3) | 0.038 (3) | −0.005 (2) | −0.002 (3) | −0.012 (2) |
C25 | 0.022 (3) | 0.021 (3) | 0.031 (3) | −0.007 (2) | −0.012 (2) | 0.003 (2) |
C26 | 0.015 (2) | 0.019 (3) | 0.037 (3) | 0.0011 (19) | −0.011 (2) | 0.004 (2) |
C27 | 0.015 (2) | 0.020 (3) | 0.031 (3) | −0.0004 (19) | −0.005 (2) | 0.005 (2) |
C28 | 0.023 (3) | 0.021 (3) | 0.024 (3) | 0.001 (2) | −0.002 (2) | 0.002 (2) |
C29 | 0.027 (3) | 0.038 (3) | 0.034 (3) | 0.000 (2) | −0.006 (3) | −0.010 (2) |
C110 | 0.068 (5) | 0.057 (5) | 0.059 (5) | −0.025 (4) | −0.006 (4) | 0.023 (4) |
C210 | 0.058 (4) | 0.046 (4) | 0.056 (4) | −0.006 (3) | −0.007 (4) | −0.013 (3) |
O101 | 0.032 (2) | 0.093 (4) | 0.037 (2) | −0.016 (2) | 0.003 (2) | −0.006 (3) |
O201 | 0.029 (3) | 0.094 (4) | 0.091 (4) | −0.005 (3) | −0.011 (3) | 0.008 (3) |
O202 | 0.029 (3) | 0.147 (5) | 0.091 (4) | −0.023 (3) | −0.014 (3) | 0.074 (4) |
O203 | 0.045 (3) | 0.124 (5) | 0.052 (3) | −0.024 (3) | 0.001 (2) | 0.032 (3) |
N201 | 0.034 (3) | 0.058 (4) | 0.046 (3) | −0.014 (3) | −0.010 (3) | 0.004 (3) |
Geometric parameters (Å, º) top
Br11—C15 | 1.894 (5) | C14—C15 | 1.385 (8) |
Br21—C25 | 1.903 (5) | C15—C16 | 1.369 (7) |
Fe1—S11 | 2.4404 (15) | C16—H16 | 0.9500 |
Fe1—S21 | 2.4615 (14) | C17—H17 | 0.9500 |
Fe1—O11 | 1.952 (3) | C19—H19A | 0.9900 |
Fe1—O21 | 1.944 (3) | C19—H19B | 0.9900 |
Fe1—N11 | 2.176 (4) | C19—C110 | 1.506 (8) |
Fe1—N21 | 2.161 (4) | C21—C22 | 1.407 (7) |
S11—C18 | 1.692 (5) | C21—C26 | 1.414 (6) |
S21—C28 | 1.698 (5) | C21—C27 | 1.429 (7) |
O11—C12 | 1.302 (6) | C22—C23 | 1.399 (7) |
O21—C22 | 1.320 (6) | C23—H23A | 0.9500 |
N11—N12 | 1.396 (6) | C23—C24 | 1.381 (7) |
N11—C17 | 1.293 (6) | C24—H24 | 0.9500 |
N12—H12 | 0.87 (3) | C24—C25 | 1.374 (7) |
N12—C18 | 1.349 (6) | C25—C26 | 1.360 (7) |
N13—H13 | 0.88 (3) | C26—H26 | 0.9500 |
N13—C18 | 1.325 (6) | C27—H27 | 0.9500 |
N13—C19 | 1.449 (6) | C29—H29A | 0.9900 |
N21—N22 | 1.376 (5) | C29—H29B | 0.9900 |
N21—C27 | 1.295 (6) | C29—C210 | 1.486 (8) |
N22—H22 | 0.87 (3) | C110—H11A | 0.9800 |
N22—C28 | 1.352 (6) | C110—H11B | 0.9800 |
N23—H23 | 0.87 (3) | C110—H11C | 0.9800 |
N23—C28 | 1.322 (6) | C210—H21A | 0.9800 |
N23—C29 | 1.446 (6) | C210—H21B | 0.9800 |
C11—C12 | 1.388 (7) | C210—H21C | 0.9800 |
C11—C16 | 1.424 (7) | O101—H10A | 0.8498 |
C11—C17 | 1.426 (7) | O101—H10B | 0.8487 |
C12—C13 | 1.411 (7) | O201—N201 | 1.249 (6) |
C13—H13A | 0.9500 | O202—N201 | 1.246 (7) |
C13—C14 | 1.372 (7) | O203—N201 | 1.232 (6) |
C14—H14 | 0.9500 | | |
| | | |
S11—Fe1—S21 | 98.70 (5) | C11—C17—H17 | 117.5 |
O11—Fe1—S11 | 158.16 (11) | N12—C18—S11 | 121.3 (4) |
O11—Fe1—S21 | 92.89 (11) | N13—C18—S11 | 123.3 (4) |
O11—Fe1—N11 | 83.71 (14) | N13—C18—N12 | 115.4 (5) |
O11—Fe1—N21 | 112.13 (14) | N13—C19—H19A | 109.7 |
O21—Fe1—S11 | 90.03 (11) | N13—C19—H19B | 109.7 |
O21—Fe1—S21 | 160.48 (11) | N13—C19—C110 | 110.0 (5) |
O21—Fe1—O11 | 84.89 (15) | H19A—C19—H19B | 108.2 |
O21—Fe1—N11 | 114.03 (15) | C110—C19—H19A | 109.7 |
O21—Fe1—N21 | 83.82 (14) | C110—C19—H19B | 109.7 |
N11—Fe1—S11 | 79.00 (11) | C22—C21—C26 | 119.2 (4) |
N11—Fe1—S21 | 84.89 (11) | C22—C21—C27 | 123.5 (4) |
N21—Fe1—S11 | 88.32 (11) | C26—C21—C27 | 117.3 (4) |
N21—Fe1—S21 | 79.05 (11) | O21—C22—C21 | 121.5 (4) |
N21—Fe1—N11 | 157.80 (15) | O21—C22—C23 | 120.3 (5) |
C18—S11—Fe1 | 99.81 (17) | C23—C22—C21 | 118.2 (4) |
C28—S21—Fe1 | 99.60 (17) | C22—C23—H23A | 119.4 |
C12—O11—Fe1 | 134.9 (3) | C24—C23—C22 | 121.2 (5) |
C22—O21—Fe1 | 134.2 (3) | C24—C23—H23A | 119.4 |
N12—N11—Fe1 | 118.0 (3) | C23—C24—H24 | 120.0 |
C17—N11—Fe1 | 126.8 (3) | C25—C24—C23 | 120.0 (5) |
C17—N11—N12 | 114.6 (4) | C25—C24—H24 | 120.0 |
N11—N12—H12 | 117 (4) | C24—C25—Br21 | 120.0 (4) |
C18—N12—N11 | 120.4 (4) | C26—C25—Br21 | 119.3 (4) |
C18—N12—H12 | 123 (4) | C26—C25—C24 | 120.7 (5) |
C18—N13—H13 | 123 (4) | C21—C26—H26 | 119.7 |
C18—N13—C19 | 123.9 (4) | C25—C26—C21 | 120.6 (5) |
C19—N13—H13 | 113 (4) | C25—C26—H26 | 119.7 |
N22—N21—Fe1 | 119.2 (3) | N21—C27—C21 | 125.6 (4) |
C27—N21—Fe1 | 126.3 (3) | N21—C27—H27 | 117.2 |
C27—N21—N22 | 114.2 (4) | C21—C27—H27 | 117.2 |
N21—N22—H22 | 120 (4) | N22—C28—S21 | 120.9 (4) |
C28—N22—N21 | 121.2 (4) | N23—C28—S21 | 123.8 (4) |
C28—N22—H22 | 118 (4) | N23—C28—N22 | 115.3 (4) |
C28—N23—H23 | 118 (4) | N23—C29—H29A | 109.0 |
C28—N23—C29 | 124.7 (4) | N23—C29—H29B | 109.0 |
C29—N23—H23 | 117 (4) | N23—C29—C210 | 112.9 (5) |
C12—C11—C16 | 119.7 (5) | H29A—C29—H29B | 107.8 |
C12—C11—C17 | 124.1 (5) | C210—C29—H29A | 109.0 |
C16—C11—C17 | 116.2 (5) | C210—C29—H29B | 109.0 |
O11—C12—C11 | 123.0 (5) | C19—C110—H11A | 109.5 |
O11—C12—C13 | 117.9 (5) | C19—C110—H11B | 109.5 |
C11—C12—C13 | 119.0 (5) | C19—C110—H11C | 109.5 |
C12—C13—H13A | 119.7 | H11A—C110—H11B | 109.5 |
C14—C13—C12 | 120.6 (5) | H11A—C110—H11C | 109.5 |
C14—C13—H13A | 119.7 | H11B—C110—H11C | 109.5 |
C13—C14—H14 | 120.0 | C29—C210—H21A | 109.5 |
C13—C14—C15 | 120.1 (5) | C29—C210—H21B | 109.5 |
C15—C14—H14 | 120.0 | C29—C210—H21C | 109.5 |
C14—C15—Br11 | 118.7 (4) | H21A—C210—H21B | 109.5 |
C16—C15—Br11 | 120.3 (4) | H21A—C210—H21C | 109.5 |
C16—C15—C14 | 121.1 (5) | H21B—C210—H21C | 109.5 |
C11—C16—H16 | 120.3 | H10A—O101—H10B | 104.6 |
C15—C16—C11 | 119.4 (5) | O202—N201—O201 | 117.9 (5) |
C15—C16—H16 | 120.3 | O203—N201—O201 | 122.9 (6) |
N11—C17—C11 | 124.9 (5) | O203—N201—O202 | 119.2 (5) |
N11—C17—H17 | 117.5 | | |
| | | |
Br11—C15—C16—C11 | 178.1 (4) | C14—C15—C16—C11 | −1.7 (9) |
Br21—C25—C26—C21 | 177.3 (3) | C16—C11—C12—O11 | 177.5 (5) |
Fe1—S11—C18—N12 | −9.9 (4) | C16—C11—C12—C13 | −1.9 (7) |
Fe1—S11—C18—N13 | 170.6 (4) | C16—C11—C17—N11 | 178.4 (5) |
Fe1—S21—C28—N22 | −1.4 (4) | C17—N11—N12—C18 | 179.7 (4) |
Fe1—S21—C28—N23 | 179.1 (4) | C17—C11—C12—O11 | −0.9 (8) |
Fe1—O11—C12—C11 | 16.4 (8) | C17—C11—C12—C13 | 179.7 (5) |
Fe1—O11—C12—C13 | −164.2 (4) | C17—C11—C16—C15 | −178.7 (5) |
Fe1—O21—C22—C21 | 23.7 (7) | C18—N13—C19—C110 | −165.0 (5) |
Fe1—O21—C22—C23 | −157.4 (4) | C19—N13—C18—S11 | −3.1 (7) |
Fe1—N11—N12—C18 | 7.9 (6) | C19—N13—C18—N12 | 177.3 (5) |
Fe1—N11—C17—C11 | −5.6 (7) | C21—C22—C23—C24 | −1.1 (8) |
Fe1—N21—N22—C28 | −0.2 (6) | C22—C21—C26—C25 | 1.3 (7) |
Fe1—N21—C27—C21 | −5.3 (7) | C22—C21—C27—N21 | −6.3 (8) |
O11—C12—C13—C14 | −179.6 (5) | C22—C23—C24—C25 | −0.1 (9) |
O21—C22—C23—C24 | 180.0 (5) | C23—C24—C25—Br21 | −177.9 (4) |
N11—N12—C18—S11 | 2.8 (7) | C23—C24—C25—C26 | 2.0 (8) |
N11—N12—C18—N13 | −177.6 (4) | C24—C25—C26—C21 | −2.6 (7) |
N12—N11—C17—C11 | −176.5 (5) | C26—C21—C22—O21 | 179.4 (4) |
N21—N22—C28—S21 | 1.2 (6) | C26—C21—C22—C23 | 0.5 (7) |
N21—N22—C28—N23 | −179.2 (4) | C26—C21—C27—N21 | 173.1 (4) |
N22—N21—C27—C21 | −178.5 (4) | C27—N21—N22—C28 | 173.6 (4) |
C11—C12—C13—C14 | −0.2 (8) | C27—C21—C22—O21 | −1.2 (7) |
C12—C11—C16—C15 | 2.8 (8) | C27—C21—C22—C23 | 179.9 (5) |
C12—C11—C17—N11 | −3.2 (8) | C27—C21—C26—C25 | −178.1 (4) |
C12—C13—C14—C15 | 1.3 (8) | C28—N23—C29—C210 | 90.3 (6) |
C13—C14—C15—Br11 | 179.8 (4) | C29—N23—C28—S21 | −1.2 (7) |
C13—C14—C15—C16 | −0.4 (9) | C29—N23—C28—N22 | 179.3 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N12—H12···O202 | 0.87 (3) | 1.92 (4) | 2.733 (6) | 155 (5) |
N13—H13···O203 | 0.88 (3) | 2.02 (3) | 2.890 (6) | 176 (5) |
N22—H22···O101i | 0.87 (3) | 1.85 (3) | 2.695 (6) | 166 (5) |
N23—H23···O201ii | 0.87 (3) | 2.23 (4) | 2.887 (6) | 133 (4) |
O101—H10A···O202i | 0.85 | 1.90 | 2.692 (6) | 155 |
O101—H10B···O11 | 0.85 | 2.28 | 2.809 (6) | 121 |
Symmetry codes: (i) x−1/2, y, −z+1; (ii) x−1, −y+3/2, −z+3/2. |