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With the new semi-rigid V-shaped bidentate pyridyl amide com­pound 5-methyl-N,N′-bis­(pyridin-4-yl)benzene-1,3-dicarboxamide (L) as an auxiliary ligand and the FeII ion as the metal centre, one mononuclear com­plex, bis­(methanol-κO)bis­[5-methyl-N,N′-bis­(pyridin-4-yl)benzene-1,3-dicarboxamide-κN]bis­(thio­cyanato-κN)iron(II), [Fe(SCN)2(C19H16N4O2)2(CH3OH)2] (1), and one two-dimensional coordination polymer, catena-poly[[[bis­(thio­cyanato-κN)iron(II)]-bis­[μ-5-methyl-N,N′-bis­(pyridin-4-yl)benzene-1,3-dicarboxamide-κ2N:N′]] methanol disolvate dihydrate], {[Fe(SCN)2(C19H16N4O2)2]·2CH3OH·2H2O}n (2), were prepared by slow evaporation and H-tube diffusion methods, respectively, indicating the effect of the method of crystallization on the structure type of the target product. Both com­plexes have been structurally characterized by elemental analysis, IR spectroscopy and single-crystal X-ray crystallography. The single-crystal X-ray diffraction analysis shows that L functions as a monodentate ligand in mononuclear 1, while it coordinates in a bidentate manner to two inde­­pendent Fe(SCN)2 units in com­plex 2, with a different conformation from that in 1 and the ligands point in two almost orthogonal directions, therefore leading to a two-dimensional grid-like network. Investigation of the magnetic properties reveals the always high-spin state of the FeII centre over the whole temperature range in 1 and a gradual thermally-induced incom­plete spin crossover (SCO) behaviour below 150 K in 2, demonstrating the influence of the different coordination fields on the spin properties of the metal ions. The current results provide useful information for the rational design of functional com­plexes with different structure dimensionalities by employing different conformations of the ligand and different crystallization methods.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229620004854/lf3116sup1.cif
Contains datablocks mono, 2D, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620004854/lf3116monosup2.hkl
Contains datablock mono

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620004854/lf31162Dsup3.hkl
Contains datablock 2D

CCDC references: 1986239; 1986240

Computing details top

For both structures, data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Bis(methanol-κO)bis[5-methyl-N,N'-bis(pyridin-4-yl)benzene-1,3-dicarboxamide-κN]bis(thiocyanato-κN)iron(II) (mono) top
Crystal data top
[Fe(SCN)2(C19H16N4O2)2(CH4O)2]Z = 1
Mr = 900.81F(000) = 468
Triclinic, P1Dx = 1.496 Mg m3
a = 9.0061 (7) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.3811 (8) ÅCell parameters from 2433 reflections
c = 11.6830 (9) Åθ = 2.9–28.9°
α = 82.848 (7)°µ = 0.55 mm1
β = 84.322 (7)°T = 293 K
γ = 67.522 (8)°Block, pale-yellow
V = 999.87 (15) Å30.15 × 0.11 × 0.09 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
2889 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
φ and ω scansθmax = 25.0°, θmin = 2.9°
Absorption correction: multi-scanh = 1010
Tmin = 0.851, Tmax = 1.000k = 1210
6227 measured reflectionsl = 1313
3530 independent reflections
Refinement top
Refinement on F21 restraint
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.111 w = 1/[σ2(Fo2) + (0.0511P)2 + 0.4901P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
3530 reflectionsΔρmax = 0.47 e Å3
277 parametersΔρmin = 0.30 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Single crystals of complexes 1 and 2 for X-ray diffraction analysis with suitable dimensions were mounted on a glass rod, and the crystal data were collected on a Bruker APEX2 CCD diffractometer with a Mo Kα sealed tube (λ = 0.71073 Å), using the ω scan mode. The data for complex 1 was collected at room temperature, while that for complex 2 was collected at 130 K. The structures were solved using the direct method and expanded using Fourier difference techniques with the SHELXTL-2018 program package (Sheldrick, 2015). The non-hydrogen atoms were refined anisotropically with anisotropic displacement coefficients.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Fe10.0000000.0000000.0000000.03167 (17)
S10.27502 (11)0.45716 (8)0.18595 (7)0.0496 (2)
O10.2451 (2)0.07940 (18)0.06982 (16)0.0404 (5)
H1A0.2830890.0240000.1099990.048*
O20.0801 (3)0.2137 (2)0.55904 (17)0.0587 (6)
O30.3961 (4)0.7426 (3)0.58814 (19)0.0774 (9)
N10.0508 (3)0.1976 (2)0.1020 (2)0.0416 (6)
N20.0686 (3)0.0801 (2)0.14304 (18)0.0341 (5)
N30.1774 (3)0.2877 (2)0.38949 (19)0.0389 (6)
H3A0.2280060.3403170.3595400.047*
N40.3479 (3)0.7185 (2)0.40763 (19)0.0377 (5)
H40.2993010.6823950.3691850.045*
N50.5832 (3)0.9527 (2)0.2021 (2)0.0478 (6)
C10.1411 (4)0.3058 (3)0.1376 (2)0.0384 (7)
C20.0295 (3)0.0583 (3)0.2549 (2)0.0367 (6)
H20.0238920.0029100.2756170.044*
C30.0625 (3)0.1200 (3)0.3422 (2)0.0356 (6)
H30.0319110.1009700.4187760.043*
C40.1427 (3)0.2111 (2)0.3125 (2)0.0316 (6)
C50.1891 (3)0.2295 (3)0.1969 (2)0.0408 (7)
H50.2466890.2868730.1736990.049*
C60.1506 (3)0.1639 (3)0.1171 (2)0.0400 (7)
H60.1834150.1783840.0401590.048*
C70.1416 (3)0.2901 (3)0.5054 (2)0.0345 (6)
C80.1815 (3)0.3924 (3)0.5650 (2)0.0298 (6)
C90.1582 (3)0.3836 (3)0.6842 (2)0.0317 (6)
H90.1160790.3193210.7210960.038*
C100.1960 (3)0.4676 (3)0.7496 (2)0.0341 (6)
C110.1728 (4)0.4559 (3)0.8799 (2)0.0523 (8)
H11A0.1234310.3890790.9045190.079*
H11B0.1047830.5455140.9046760.079*
H11C0.2753610.4255130.9130920.079*
C120.2577 (3)0.5628 (3)0.6923 (2)0.0359 (6)
H120.2858750.6187010.7353300.043*
C130.2787 (3)0.5775 (3)0.5732 (2)0.0323 (6)
C140.2412 (3)0.4909 (3)0.5090 (2)0.0321 (6)
H140.2559090.4985830.4288440.039*
C150.3448 (3)0.6869 (3)0.5243 (2)0.0406 (7)
C160.4216 (3)0.8037 (3)0.3431 (2)0.0366 (6)
C170.4890 (3)0.8844 (3)0.3901 (3)0.0443 (7)
H170.4807190.8908130.4693000.053*
C180.5680 (4)0.9543 (3)0.3165 (3)0.0468 (7)
H180.6140691.0065290.3489620.056*
C190.5109 (4)0.8810 (3)0.1578 (3)0.0509 (8)
H190.5144050.8818720.0779440.061*
C200.4318 (4)0.8061 (3)0.2243 (3)0.0477 (7)
H200.3846610.7567250.1891300.057*
C210.3411 (4)0.2203 (3)0.0934 (3)0.0598 (9)
H21A0.2743320.2744670.0861790.090*
H21B0.3892420.2205750.1704680.090*
H21C0.4240770.2603940.0392520.090*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0437 (3)0.0343 (3)0.0252 (3)0.0241 (3)0.0004 (2)0.0031 (2)
S10.0743 (6)0.0378 (4)0.0416 (5)0.0275 (4)0.0082 (4)0.0030 (3)
O10.0477 (11)0.0408 (10)0.0401 (11)0.0268 (9)0.0094 (9)0.0066 (9)
O20.1046 (18)0.0709 (14)0.0314 (11)0.0681 (15)0.0087 (11)0.0025 (10)
O30.141 (2)0.1020 (19)0.0393 (13)0.1011 (19)0.0178 (14)0.0242 (13)
N10.0565 (16)0.0399 (14)0.0366 (14)0.0287 (13)0.0039 (12)0.0028 (11)
N20.0420 (13)0.0365 (12)0.0293 (12)0.0206 (10)0.0008 (10)0.0046 (9)
N30.0552 (15)0.0436 (13)0.0324 (13)0.0340 (12)0.0041 (11)0.0110 (10)
N40.0452 (14)0.0424 (12)0.0364 (13)0.0293 (11)0.0027 (11)0.0007 (10)
N50.0484 (15)0.0451 (14)0.0565 (17)0.0278 (12)0.0015 (12)0.0020 (12)
C10.0586 (19)0.0483 (17)0.0246 (14)0.0389 (16)0.0035 (13)0.0049 (13)
C20.0418 (16)0.0379 (14)0.0392 (16)0.0245 (13)0.0007 (12)0.0052 (12)
C30.0470 (16)0.0378 (14)0.0284 (14)0.0234 (13)0.0014 (12)0.0031 (11)
C40.0358 (14)0.0296 (13)0.0328 (15)0.0142 (11)0.0036 (11)0.0074 (11)
C50.0535 (18)0.0437 (15)0.0389 (16)0.0334 (14)0.0075 (14)0.0114 (13)
C60.0556 (18)0.0455 (16)0.0301 (15)0.0317 (14)0.0044 (13)0.0083 (12)
C70.0410 (15)0.0349 (14)0.0326 (15)0.0190 (12)0.0061 (12)0.0024 (11)
C80.0312 (13)0.0325 (13)0.0279 (14)0.0137 (11)0.0027 (11)0.0042 (11)
C90.0365 (14)0.0305 (13)0.0293 (14)0.0151 (11)0.0000 (11)0.0001 (11)
C100.0409 (15)0.0357 (14)0.0257 (14)0.0148 (12)0.0000 (12)0.0037 (11)
C110.084 (2)0.0535 (18)0.0295 (16)0.0364 (18)0.0030 (15)0.0083 (14)
C120.0447 (16)0.0388 (14)0.0300 (15)0.0203 (13)0.0011 (12)0.0113 (12)
C130.0366 (14)0.0339 (13)0.0287 (14)0.0163 (12)0.0022 (11)0.0050 (11)
C140.0415 (15)0.0366 (14)0.0224 (13)0.0195 (12)0.0016 (11)0.0020 (11)
C150.0495 (17)0.0427 (15)0.0388 (16)0.0278 (14)0.0110 (13)0.0130 (13)
C160.0338 (15)0.0357 (14)0.0419 (16)0.0166 (12)0.0008 (12)0.0004 (12)
C170.0488 (17)0.0433 (16)0.0479 (18)0.0257 (14)0.0049 (14)0.0085 (13)
C180.0512 (18)0.0431 (16)0.056 (2)0.0290 (15)0.0024 (15)0.0069 (14)
C190.058 (2)0.0611 (19)0.0421 (18)0.0351 (17)0.0044 (15)0.0071 (15)
C200.0552 (19)0.0580 (18)0.0435 (18)0.0376 (16)0.0088 (14)0.0039 (14)
C210.074 (2)0.0573 (19)0.054 (2)0.0327 (18)0.0127 (18)0.0127 (16)
Geometric parameters (Å, º) top
Fe1—N1i2.150 (2)C5—H50.9300
Fe1—N12.150 (2)C6—H60.9300
Fe1—O1i2.1535 (18)C7—C81.506 (3)
Fe1—O12.1535 (18)C8—C91.384 (3)
Fe1—N2i2.193 (2)C8—C141.395 (3)
Fe1—N22.193 (2)C9—C101.381 (3)
S1—C11.645 (3)C9—H90.9300
O1—C211.431 (4)C10—C121.383 (3)
O1—H1A0.8482C10—C111.511 (4)
O2—C71.213 (3)C11—H11A0.9600
O3—C151.218 (3)C11—H11B0.9600
N1—C11.161 (4)C11—H11C0.9600
N2—C61.332 (3)C12—C131.384 (4)
N2—C21.334 (3)C12—H120.9300
N3—C71.361 (3)C13—C141.392 (3)
N3—C41.401 (3)C13—C151.502 (3)
N3—H3A0.8600C14—H140.9300
N4—C151.361 (3)C16—C201.380 (4)
N4—C161.406 (3)C16—C171.392 (4)
N4—H40.8600C17—C181.375 (4)
N5—C181.331 (4)C17—H170.9300
N5—C191.333 (4)C18—H180.9300
C2—C31.381 (4)C19—C201.371 (4)
C2—H20.9300C19—H190.9300
C3—C41.389 (3)C20—H200.9300
C3—H30.9300C21—H21A0.9600
C4—C51.386 (4)C21—H21B0.9600
C5—C61.363 (4)C21—H21C0.9600
N1i—Fe1—N1180.0C9—C8—C14119.3 (2)
N1i—Fe1—O1i92.01 (8)C9—C8—C7115.9 (2)
N1—Fe1—O1i87.99 (8)C14—C8—C7124.7 (2)
N1i—Fe1—O187.99 (8)C10—C9—C8121.8 (2)
N1—Fe1—O192.01 (8)C10—C9—H9119.1
O1i—Fe1—O1180.0C8—C9—H9119.1
N1i—Fe1—N2i89.09 (8)C9—C10—C12117.9 (2)
N1—Fe1—N2i90.92 (8)C9—C10—C11121.5 (2)
O1i—Fe1—N2i88.57 (7)C12—C10—C11120.6 (2)
O1—Fe1—N2i91.43 (7)C10—C11—H11A109.5
N1i—Fe1—N290.92 (8)C10—C11—H11B109.5
N1—Fe1—N289.08 (8)H11A—C11—H11B109.5
O1i—Fe1—N291.43 (7)C10—C11—H11C109.5
O1—Fe1—N288.57 (7)H11A—C11—H11C109.5
N2i—Fe1—N2180.0H11B—C11—H11C109.5
C21—O1—Fe1127.55 (17)C10—C12—C13122.2 (2)
C21—O1—H1A109.3C10—C12—H12118.9
Fe1—O1—H1A119.6C13—C12—H12118.9
C1—N1—Fe1150.8 (2)C12—C13—C14118.9 (2)
C6—N2—C2116.0 (2)C12—C13—C15115.6 (2)
C6—N2—Fe1117.87 (17)C14—C13—C15125.4 (2)
C2—N2—Fe1126.06 (16)C13—C14—C8119.9 (2)
C7—N3—C4128.7 (2)C13—C14—H14120.1
C7—N3—H3A115.7C8—C14—H14120.1
C4—N3—H3A115.7O3—C15—N4122.0 (2)
C15—N4—C16127.2 (2)O3—C15—C13120.1 (3)
C15—N4—H4116.4N4—C15—C13117.9 (2)
C16—N4—H4116.4C20—C16—C17117.0 (2)
C18—N5—C19116.2 (2)C20—C16—N4118.1 (2)
N1—C1—S1177.7 (2)C17—C16—N4124.9 (3)
N2—C2—C3124.7 (2)C18—C17—C16118.4 (3)
N2—C2—H2117.7C18—C17—H17120.8
C3—C2—H2117.7C16—C17—H17120.8
C2—C3—C4118.2 (2)N5—C18—C17124.8 (3)
C2—C3—H3120.9N5—C18—H18117.6
C4—C3—H3120.9C17—C18—H18117.6
C5—C4—C3117.1 (2)N5—C19—C20123.3 (3)
C5—C4—N3117.6 (2)N5—C19—H19118.4
C3—C4—N3125.3 (2)C20—C19—H19118.4
C6—C5—C4120.2 (2)C19—C20—C16120.3 (3)
C6—C5—H5119.9C19—C20—H20119.9
C4—C5—H5119.9C16—C20—H20119.9
N2—C6—C5123.7 (2)O1—C21—H21A109.4
N2—C6—H6118.2O1—C21—H21B109.5
C5—C6—H6118.2H21A—C21—H21B109.5
O2—C7—N3122.0 (2)O1—C21—H21C109.5
O2—C7—C8121.0 (2)H21A—C21—H21C109.5
N3—C7—C8117.1 (2)H21B—C21—H21C109.5
C6—N2—C2—C32.6 (4)C11—C10—C12—C13179.2 (3)
Fe1—N2—C2—C3174.1 (2)C10—C12—C13—C142.0 (4)
N2—C2—C3—C40.2 (4)C10—C12—C13—C15179.2 (3)
C2—C3—C4—C52.3 (4)C12—C13—C14—C80.8 (4)
C2—C3—C4—N3176.3 (2)C15—C13—C14—C8179.5 (3)
C7—N3—C4—C5178.5 (3)C9—C8—C14—C130.9 (4)
C7—N3—C4—C30.1 (5)C7—C8—C14—C13178.0 (2)
C3—C4—C5—C62.4 (4)C16—N4—C15—O37.1 (5)
N3—C4—C5—C6176.3 (3)C16—N4—C15—C13171.6 (2)
C2—N2—C6—C52.4 (4)C12—C13—C15—O39.8 (4)
Fe1—N2—C6—C5174.5 (2)C14—C13—C15—O3169.0 (3)
C4—C5—C6—N20.0 (5)C12—C13—C15—N4171.5 (2)
C4—N3—C7—O25.0 (5)C14—C13—C15—N49.7 (4)
C4—N3—C7—C8174.9 (2)C15—N4—C16—C20170.5 (3)
O2—C7—C8—C96.0 (4)C15—N4—C16—C178.0 (4)
N3—C7—C8—C9174.1 (2)C20—C16—C17—C183.5 (4)
O2—C7—C8—C14175.1 (3)N4—C16—C17—C18175.1 (3)
N3—C7—C8—C144.8 (4)C19—N5—C18—C172.3 (5)
C14—C8—C9—C101.5 (4)C16—C17—C18—N51.1 (5)
C7—C8—C9—C10177.5 (2)C18—N5—C19—C203.4 (5)
C8—C9—C10—C120.3 (4)N5—C19—C20—C161.0 (5)
C8—C9—C10—C11179.0 (3)C17—C16—C20—C192.5 (4)
C9—C10—C12—C131.4 (4)N4—C16—C20—C19176.1 (3)
Symmetry code: (i) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C20—H20···S1ii0.932.763.612 (3)153
C17—H17···O30.932.242.816 (4)119
C5—H5···S1ii0.932.793.605 (3)147
C3—H3···O20.932.292.864 (3)119
N4—H4···S1ii0.862.803.590 (2)154
O1—H1A···N5iii0.851.842.662 (3)163
N4—H4···S1ii0.862.803.590 (2)154
C3—H3···O20.932.292.864 (3)119
C5—H5···S1ii0.932.793.605 (3)147
C17—H17···O30.932.242.816 (4)119
C20—H20···S1ii0.932.763.612 (3)153
O1—H1A···N5iii0.851.842.662 (3)163
O1—H1A···N5iii0.851.842.662 (3)163
N4—H4···S1ii0.862.803.590 (2)154
C3—H3···O20.932.292.864 (3)119
C5—H5···S1ii0.932.793.605 (3)147
C17—H17···O30.932.242.816 (4)119
C20—H20···S1ii0.932.763.612 (3)153
O1—H1A···N5iii0.851.842.662 (3)163
N3—H3A···S1ii0.862.863.639 (2)152
N4—H4···S1ii0.862.803.590 (2)154
C3—H3···O20.932.292.864 (3)119
C5—H5···S1ii0.932.793.605 (3)147
C17—H17···O30.932.242.816 (4)119
C20—H20···S1ii0.932.763.612 (3)153
Symmetry codes: (ii) x, y+1, z; (iii) x1, y1, z.
catena-Poly[[[bis(thiocyanato-κN)iron(II)]-bis[µ-5-methyl-N,N'-bis(pyridin-4-yl)benzene-1,3-dicarboxamide-κ2N:N']] methanol disolvate dihydrate] (2D) top
Crystal data top
[Fe(SCN)2(C19H16N4O2)2]·2CH4O·2H2OF(000) = 976
Mr = 936.84Dx = 1.434 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 8.3685 (5) ÅCell parameters from 3211 reflections
b = 17.9701 (10) Åθ = 3.0–29.1°
c = 14.8291 (11) ŵ = 0.51 mm1
β = 103.411 (7)°T = 130 K
V = 2169.2 (2) Å3Block, gold-yellow
Z = 20.23 × 0.19 × 0.12 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
3115 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.027
φ and ω scansθmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scanh = 89
Tmin = 0.782, Tmax = 1.000k = 2021
8931 measured reflectionsl = 1717
3811 independent reflections
Refinement top
Refinement on F24 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.064H-atom parameters constrained
wR(F2) = 0.169 w = 1/[σ2(Fo2) + (0.0707P)2 + 6.4322P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.027
3811 reflectionsΔρmax = 2.06 e Å3
288 parametersΔρmin = 1.11 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Single crystals of complexes 1 and 2 for X-ray diffraction analysis with suitable dimensions were mounted on a glass rod, and the crystal data were collected on a Bruker APEX2 CCD diffractometer with a Mo Kα sealed tube (λ = 0.71073 Å), using the ω scan mode. The data for complex 1 was collected at room temperature, while that for complex 2 was collected at 130 K. The structures were solved using the direct method and expanded using Fourier difference techniques with the SHELXTL-2018 program package (Sheldrick, 2015). The non-hydrogen atoms were refined anisotropically with anisotropic displacement coefficients

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Fe10.5000000.0000000.5000000.0170 (2)
S10.1647 (2)0.15825 (9)0.34619 (10)0.0582 (5)
O10.1135 (3)0.08237 (14)0.92755 (19)0.0256 (6)
O20.4002 (4)0.23954 (16)1.1060 (2)0.0322 (7)
O30.3237 (5)0.2284 (2)0.2799 (3)0.0602 (11)
H30.3527850.2389120.2307550.072*
O40.0956 (5)0.20151 (19)0.8785 (3)0.0588 (11)
H4A0.0064790.2075780.8743580.071*
H4B0.1401940.2432000.8690410.071*
N10.3574 (4)0.06355 (18)0.4275 (2)0.0228 (7)
N20.2970 (4)0.00787 (17)0.6273 (2)0.0203 (7)
N30.0588 (4)0.03568 (17)0.8763 (2)0.0216 (7)
H3A0.0814000.0816020.8898850.026*
N40.6508 (4)0.20037 (18)1.0881 (2)0.0232 (7)
H40.7105150.1611191.0907880.028*
N50.8839 (4)0.39530 (17)1.0320 (2)0.0219 (7)
C10.2773 (5)0.1025 (3)0.3939 (3)0.0314 (10)
C20.2043 (5)0.0688 (2)0.6473 (3)0.0271 (9)
H20.2209060.1071290.6040820.033*
C30.0864 (5)0.0783 (2)0.7275 (3)0.0262 (9)
H3B0.0259660.1222060.7379130.031*
C40.0577 (5)0.0218 (2)0.7933 (3)0.0205 (8)
C50.1489 (5)0.0431 (2)0.7724 (3)0.0219 (8)
H50.1310700.0832680.8130470.026*
C60.2662 (5)0.0470 (2)0.6903 (3)0.0217 (8)
H60.3279250.0903460.6777090.026*
C70.2700 (5)0.0135 (2)1.0168 (2)0.0198 (8)
C80.3102 (5)0.0886 (2)1.0295 (3)0.0215 (8)
H80.2459240.1245000.9929870.026*
C90.4475 (5)0.1092 (2)1.0972 (3)0.0215 (8)
C100.5393 (5)0.0567 (2)1.1553 (3)0.0229 (8)
H100.6317820.0714161.1996010.028*
C110.4945 (5)0.0179 (2)1.1478 (3)0.0224 (8)
C120.3608 (5)0.0388 (2)1.0775 (3)0.0212 (8)
H120.3311720.0887071.0707970.025*
C130.1400 (4)0.0158 (2)0.9377 (2)0.0199 (8)
C140.4955 (5)0.1896 (2)1.0996 (3)0.0229 (9)
C150.7244 (5)0.2670 (2)1.0724 (3)0.0220 (8)
C160.6493 (5)0.3360 (2)1.0673 (3)0.0234 (8)
H160.5439690.3407601.0771330.028*
C170.7324 (5)0.3971 (2)1.0475 (3)0.0239 (8)
H170.6802180.4430661.0446000.029*
C180.9532 (5)0.3281 (2)1.0351 (3)0.0297 (10)
H181.0569280.3247481.0227240.036*
C190.8809 (5)0.2641 (2)1.0552 (3)0.0312 (10)
H190.9357240.2188501.0574630.037*
C210.1677 (8)0.2512 (5)0.2908 (5)0.076 (2)
H21A0.1641100.2472620.3548400.114*
H21B0.0845470.2199080.2540410.114*
H21C0.1484990.3019010.2708320.114*
C200.5866 (5)0.0743 (2)1.2144 (3)0.0300 (10)
H20A0.6922070.0545541.2443740.045*
H20B0.6009040.1187961.1814000.045*
H20C0.5257600.0855821.2601890.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0180 (4)0.0137 (4)0.0189 (4)0.0019 (3)0.0032 (3)0.0002 (3)
S10.0662 (9)0.0683 (10)0.0414 (7)0.0394 (8)0.0154 (7)0.0018 (7)
O10.0259 (15)0.0176 (14)0.0296 (15)0.0039 (12)0.0010 (12)0.0003 (11)
O20.0322 (17)0.0246 (16)0.0441 (18)0.0064 (14)0.0180 (14)0.0057 (13)
O30.056 (2)0.062 (3)0.068 (3)0.001 (2)0.025 (2)0.006 (2)
O40.084 (3)0.0266 (18)0.056 (2)0.0053 (19)0.004 (2)0.0004 (16)
N10.0253 (17)0.0195 (17)0.0238 (17)0.0002 (15)0.0065 (14)0.0022 (14)
N20.0205 (16)0.0159 (16)0.0238 (17)0.0013 (13)0.0042 (13)0.0015 (13)
N30.0248 (17)0.0155 (16)0.0221 (17)0.0048 (14)0.0007 (14)0.0015 (13)
N40.0244 (17)0.0156 (16)0.0302 (18)0.0047 (14)0.0072 (14)0.0009 (13)
N50.0243 (17)0.0167 (16)0.0245 (17)0.0019 (14)0.0052 (14)0.0022 (13)
C10.031 (2)0.040 (3)0.021 (2)0.005 (2)0.0009 (18)0.0063 (19)
C20.030 (2)0.021 (2)0.028 (2)0.0043 (18)0.0016 (17)0.0062 (17)
C30.027 (2)0.020 (2)0.029 (2)0.0042 (17)0.0018 (17)0.0025 (17)
C40.0192 (19)0.0195 (19)0.0227 (19)0.0001 (16)0.0045 (16)0.0012 (15)
C50.024 (2)0.0196 (19)0.022 (2)0.0012 (16)0.0048 (16)0.0026 (15)
C60.0220 (19)0.0182 (19)0.023 (2)0.0036 (16)0.0027 (16)0.0030 (15)
C70.0201 (19)0.023 (2)0.0169 (18)0.0038 (16)0.0051 (15)0.0009 (15)
C80.0226 (19)0.023 (2)0.0190 (19)0.0046 (17)0.0052 (16)0.0022 (16)
C90.0226 (19)0.023 (2)0.0208 (19)0.0069 (17)0.0098 (16)0.0026 (16)
C100.0216 (19)0.031 (2)0.0159 (18)0.0067 (17)0.0038 (15)0.0004 (16)
C110.022 (2)0.026 (2)0.0197 (19)0.0044 (17)0.0077 (16)0.0026 (16)
C120.023 (2)0.022 (2)0.0208 (19)0.0053 (16)0.0096 (16)0.0010 (16)
C130.0181 (19)0.024 (2)0.0188 (19)0.0026 (16)0.0061 (15)0.0002 (15)
C140.027 (2)0.024 (2)0.0175 (18)0.0084 (18)0.0047 (16)0.0023 (15)
C150.024 (2)0.021 (2)0.0202 (19)0.0055 (17)0.0035 (16)0.0007 (15)
C160.023 (2)0.0201 (19)0.029 (2)0.0002 (16)0.0090 (17)0.0018 (16)
C170.024 (2)0.0183 (19)0.029 (2)0.0004 (17)0.0047 (17)0.0009 (16)
C180.024 (2)0.021 (2)0.047 (3)0.0029 (18)0.0133 (19)0.0017 (19)
C190.026 (2)0.018 (2)0.051 (3)0.0011 (17)0.011 (2)0.0063 (19)
C210.061 (4)0.095 (5)0.081 (5)0.012 (4)0.035 (4)0.001 (4)
C200.028 (2)0.033 (2)0.026 (2)0.0043 (19)0.0015 (18)0.0067 (18)
Geometric parameters (Å, º) top
Fe1—N1i2.116 (3)C5—C61.377 (5)
Fe1—N12.117 (3)C5—H50.9300
Fe1—N5ii2.219 (3)C6—H60.9300
Fe1—N5iii2.219 (3)C7—C81.392 (5)
Fe1—N22.232 (3)C7—C121.398 (5)
Fe1—N2i2.232 (3)C7—C131.499 (5)
S1—C11.643 (5)C8—C91.389 (5)
O1—C131.220 (5)C8—H80.9300
O2—C141.218 (5)C9—C101.384 (6)
O3—C211.412 (7)C9—C141.499 (5)
O3—H30.8421C10—C111.389 (6)
O4—H4A0.8493C10—H100.9300
O4—H4B0.8626C11—C121.392 (5)
N1—C11.159 (5)C11—C201.497 (5)
N2—C21.334 (5)C12—H120.9300
N2—C61.341 (5)C15—C161.385 (5)
N3—C131.364 (5)C15—C191.392 (6)
N3—C41.404 (5)C16—C171.367 (6)
N3—H3A0.8600C16—H160.9300
N4—C141.363 (5)C17—H170.9300
N4—C151.390 (5)C18—C191.365 (6)
N4—H40.8600C18—H180.9300
N5—C181.336 (5)C19—H190.9300
N5—C171.340 (5)C21—H21A0.9600
C2—C31.369 (6)C21—H21B0.9600
C2—H20.9300C21—H21C0.9600
C3—C41.390 (5)C20—H20A0.9600
C3—H3B0.9300C20—H20B0.9600
C4—C51.389 (5)C20—H20C0.9600
N1i—Fe1—N1180.0C9—C8—C7119.3 (4)
N1i—Fe1—N5ii91.28 (12)C9—C8—H8120.3
N1—Fe1—N5ii88.72 (12)C7—C8—H8120.3
N1i—Fe1—N5iii88.72 (12)C10—C9—C8121.0 (4)
N1—Fe1—N5iii91.28 (12)C10—C9—C14122.4 (4)
N5ii—Fe1—N5iii180.0C8—C9—C14116.5 (4)
N1i—Fe1—N290.70 (12)C9—C10—C11120.5 (4)
N1—Fe1—N289.30 (12)C9—C10—H10119.7
N5ii—Fe1—N292.90 (11)C11—C10—H10119.7
N5iii—Fe1—N287.10 (11)C10—C11—C12118.3 (4)
N1i—Fe1—N2i89.30 (12)C10—C11—C20120.8 (4)
N1—Fe1—N2i90.70 (12)C12—C11—C20120.9 (4)
N5ii—Fe1—N2i87.10 (11)C11—C12—C7121.6 (4)
N5iii—Fe1—N2i92.90 (11)C11—C12—H12119.2
N2—Fe1—N2i180.0C7—C12—H12119.2
C21—O3—H3119.6O1—C13—N3122.3 (3)
H4A—O4—H4B110.0O1—C13—C7121.3 (3)
C1—N1—Fe1174.3 (3)N3—C13—C7116.3 (3)
C2—N2—C6116.1 (3)O2—C14—N4124.5 (4)
C2—N2—Fe1122.0 (3)O2—C14—C9122.3 (4)
C6—N2—Fe1121.9 (2)N4—C14—C9113.1 (3)
C13—N3—C4127.0 (3)C16—C15—N4124.6 (4)
C13—N3—H3A116.5C16—C15—C19117.3 (4)
C4—N3—H3A116.5N4—C15—C19118.0 (4)
C14—N4—C15127.9 (3)C17—C16—C15119.0 (4)
C14—N4—H4116.0C17—C16—H16120.5
C15—N4—H4116.0C15—C16—H16120.5
C18—N5—C17115.9 (3)N5—C17—C16124.4 (4)
C18—N5—Fe1iv124.4 (3)N5—C17—H17117.8
C17—N5—Fe1iv119.6 (3)C16—C17—H17117.8
N1—C1—S1179.5 (4)N5—C18—C19124.0 (4)
N2—C2—C3124.1 (4)N5—C18—H18118.0
N2—C2—H2117.9C19—C18—H18118.0
C3—C2—H2117.9C18—C19—C15119.5 (4)
C2—C3—C4119.4 (4)C18—C19—H19120.3
C2—C3—H3B120.3C15—C19—H19120.3
C4—C3—H3B120.3O3—C21—H21A109.5
C5—C4—C3117.4 (3)O3—C21—H21B109.5
C5—C4—N3125.4 (3)H21A—C21—H21B109.5
C3—C4—N3117.2 (3)O3—C21—H21C109.5
C6—C5—C4118.8 (4)H21A—C21—H21C109.5
C6—C5—H5120.6H21B—C21—H21C109.5
C4—C5—H5120.6C11—C20—H20A109.5
N2—C6—C5124.2 (4)C11—C20—H20B109.5
N2—C6—H6117.9H20A—C20—H20B109.5
C5—C6—H6117.9C11—C20—H20C109.5
C8—C7—C12119.1 (3)H20A—C20—H20C109.5
C8—C7—C13123.7 (3)H20B—C20—H20C109.5
C12—C7—C13117.1 (3)
C6—N2—C2—C31.8 (6)C4—N3—C13—O12.9 (6)
Fe1—N2—C2—C3175.2 (3)C4—N3—C13—C7174.5 (3)
N2—C2—C3—C40.5 (7)C8—C7—C13—O1177.1 (4)
C2—C3—C4—C51.8 (6)C12—C7—C13—O10.9 (5)
C2—C3—C4—N3177.0 (4)C8—C7—C13—N30.3 (5)
C13—N3—C4—C521.4 (6)C12—C7—C13—N3176.5 (3)
C13—N3—C4—C3160.0 (4)C15—N4—C14—O26.8 (6)
C3—C4—C5—C62.6 (6)C15—N4—C14—C9169.1 (4)
N3—C4—C5—C6176.0 (4)C10—C9—C14—O2128.8 (4)
C2—N2—C6—C50.9 (6)C8—C9—C14—O255.0 (5)
Fe1—N2—C6—C5176.1 (3)C10—C9—C14—N455.2 (5)
C4—C5—C6—N21.3 (6)C8—C9—C14—N4121.0 (4)
C12—C7—C8—C95.2 (6)C14—N4—C15—C161.1 (6)
C13—C7—C8—C9171.0 (3)C14—N4—C15—C19174.9 (4)
C7—C8—C9—C103.4 (6)N4—C15—C16—C17177.2 (4)
C7—C8—C9—C14172.9 (3)C19—C15—C16—C171.1 (6)
C8—C9—C10—C111.0 (6)C18—N5—C17—C161.2 (6)
C14—C9—C10—C11177.0 (4)Fe1iv—N5—C17—C16179.7 (3)
C9—C10—C11—C123.4 (6)C15—C16—C17—N50.3 (6)
C9—C10—C11—C20175.9 (4)C17—N5—C18—C191.9 (6)
C10—C11—C12—C71.6 (6)Fe1iv—N5—C18—C19179.7 (3)
C20—C11—C12—C7177.7 (4)N5—C18—C19—C151.1 (7)
C8—C7—C12—C112.7 (6)C16—C15—C19—C180.5 (6)
C13—C7—C12—C11173.7 (3)N4—C15—C19—C18176.8 (4)
Symmetry codes: (i) x1, y, z+1; (ii) x3/2, y+1/2, z1/2; (iii) x+1/2, y1/2, z+3/2; (iv) x+1/2, y+1/2, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4B···S1v0.862.483.324 (4)165
O4—H4A···O3vi0.852.092.712 (6)129
O4—H4B···S1v0.862.483.324 (4)165
O4—H4A···O3vi0.852.092.712 (6)129
O4—H4A···O3vi0.852.092.712 (6)129
O4—H4B···S1v0.862.483.324 (4)165
N3—H3A···O40.862.172.995 (5)162
N4—H4···O1vii0.862.112.942 (4)164
C3—H3B···O40.932.543.263 (5)135
C5—H5···O10.932.342.876 (5)117
C6—H6···O3viii0.932.563.340 (6)142
C16—H16···O20.932.282.870 (5)121
C17—H17···N1iv0.932.603.162 (5)119
C18—H18···N1ix0.932.653.166 (5)116
C19—H19···O1vii0.932.513.274 (5)140
C21—H21B···S10.962.963.502 (7)117
O4—H4A···O3vi0.852.092.712 (6)129
O4—H4B···S1v0.862.483.324 (4)165
N3—H3A···O40.862.172.995 (5)162
N4—H4···O1vii0.862.112.942 (4)164
C3—H3B···O40.932.543.263 (5)135
C5—H5···O10.932.342.876 (5)117
C6—H6···O3viii0.932.563.340 (6)142
C16—H16···O20.932.282.870 (5)121
C17—H17···N1iv0.932.603.162 (5)119
C18—H18···N1ix0.932.653.166 (5)116
C19—H19···O1vii0.932.513.274 (5)140
C21—H21B···S10.962.963.502 (7)117
O4—H4A···O3vi0.852.092.712 (6)129
O4—H4B···S1v0.862.483.324 (4)165
N3—H3A···O40.862.172.995 (5)162
N4—H4···O1vii0.862.112.942 (4)164
C3—H3B···O40.932.543.263 (5)135
C5—H5···O10.932.342.876 (5)117
C6—H6···O3viii0.932.563.340 (6)142
C16—H16···O20.932.282.870 (5)121
C17—H17···N1iv0.932.603.162 (5)119
C18—H18···N1ix0.932.653.166 (5)116
C19—H19···O1vii0.932.513.274 (5)140
C21—H21B···S10.962.963.502 (7)117
O4—H4A···O3vi0.852.092.712 (6)129
O4—H4B···S1v0.862.483.324 (4)165
N3—H3A···O40.862.172.995 (5)162
N4—H4···O1vii0.862.112.942 (4)164
C3—H3B···O40.932.543.263 (5)135
C5—H5···O10.932.342.876 (5)117
C6—H6···O3viii0.932.563.340 (6)142
C16—H16···O20.932.282.870 (5)121
C17—H17···N1iv0.932.603.162 (5)119
C18—H18···N1ix0.932.653.166 (5)116
C19—H19···O1vii0.932.513.274 (5)140
C21—H21B···S10.962.963.502 (7)117
O3—H3···O2x0.841.982.805 (5)166
Symmetry codes: (iv) x+1/2, y+1/2, z+3/2; (v) x+1/2, y+1/2, z+1/2; (vi) x1/2, y+1/2, z+1/2; (vii) x+1, y, z+2; (viii) x, y, z+1; (ix) x+3/2, y+1/2, z+1/2; (x) x, y, z1.
Selected hydrogen bond parameters (Å, °) for complexes 1 and 2 top
Complex 1
D—H···AH···AD···AD—H···A
O1—H1A···N5#31.842.662 (3)163.0
Complex 2
N3—H3A···O42.172.995 (5)161.6
N4—H4···O1#72.112.942 (4)164.1
O4—H4B···S1#52.483.324 (4)164.5
O3—H3···O2#101.982.805 (5)166.3
Symmetry codes for 1: (#3) x-1, y-1, z; symmetry codes for 2: (#5) x+1/2, -y+1/2, z+1/2; (#7) -x+1, -y, -z+2; (#10) x, y, z-1.
 

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