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The self-assembly reaction of (+)-dibenzoyltartaric acid (
D-H
2DBTA) with 2,2′-bipyridine (bpy) and Mn(CH
3CO
2)
2·4H
2O yielded a new coordination polymer, namely,
catena-poly[[[diaqua(2,2′-bipyridine-κ
2N,
N′)manganese(II)]-μ-2,3-bis(benzoyloxy)butanedioato-κ
2O2:
O3] dihydrate], {[Mn(C
18H
12O
8)(C
10H
8N
2)(H
2O)
2]·2H
2O}
n or {[Mn(DBTA)(bpy)(H
2O)
2]·2H
2O}
n, (I). Complex (I) has been characterized by elemental analysis, IR spectroscopy, thermogravimetric analysis (TGA) and single-crystal and powder X-ray diffraction. It crystallizes in the orthorhombic space group
P2
12
12
1. In the complex, the Mn
2+ cation displays a distorted octahedral {MnO
4N
2} geometry, formed from two carboxylate O atoms of two DBTA
2− ligands, two
cis-oriented N atoms from one chelating 2,2′-bipyridine ligand and two
trans-oriented O atoms from coordinated water molecules. The polymer displays a 1D chain with an Mn
Mn distance of 9.428 (1) Å. Due to the presence of flexible polycarboxylate and rigid bipyridyl ligands in the molecular structure, a high thermal stability of the complex is attained. The magnetic properties of (I) were analyzed based on the mononuclear Mn
2+ model due to the long intramolecular Mn
Mn distance. The zero field splitting (ZFS) contribution in the high-spin Mn
2+ cation is almost negligible and there are weak antiferromagnetic couplings between 1D chains [
zJ′ = −0.062 (5) cm
−1], corresponding to an intermolecular Mn
Mn distance of 7.860 (2) Å.
Supporting information
CCDC reference: 2115561
Data collection: HKL-2000 (Zbyszek & Wladek, 1997); cell refinement: XDS CORRECT (Kabsch, 2010); data reduction: XDS INTEGRATE (Kabsch, 2010); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b).
catena-Poly[[[diaqua(2,2'-bipyridine-
κ2N,
N')manganese(II)]-µ-2,3-bis(benzoyloxy)butanedioato-
κ2O2:
O3]
dihydrate]
top
Crystal data top
[Mn(C18H12O8)(C10H8N2)(H2O)2]·2H2O | Dx = 1.441 Mg m−3 |
Mr = 639.46 | Synchrotron radiation, λ = 0.750 Å |
Orthorhombic, P212121 | Cell parameters from 49038 reflections |
a = 7.8600 (16) Å | θ = 1.5–31.0° |
b = 16.2330 (9) Å | µ = 0.59 mm−1 |
c = 23.103 (2) Å | T = 100 K |
V = 2947.7 (7) Å3 | Block, yellow |
Z = 4 | 0.30 × 0.20 × 0.20 mm |
F(000) = 1324 | |
Data collection top
Mardtb with mar165 CCD diffractometer | 7919 independent reflections |
Radiation source: BSRF, beamline 3W1A | 7592 reflections with I > 2σ(I) |
Detector resolution: 0.079 pixels mm-1 | Rint = 0.043 |
phi scan | θmax = 30.9°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2008) | h = −10→10 |
Tmin = 0.709, Tmax = 0.746 | k = −22→22 |
55869 measured reflections | l = −31→31 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.042 | w = 1/[σ2(Fo2) + (0.050P)2 + 2.5P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.111 | (Δ/σ)max = 0.001 |
S = 1.04 | Δρmax = 0.86 e Å−3 |
7919 reflections | Δρmin = −0.81 e Å−3 |
396 parameters | Absolute structure: Flack x determined using 3225 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
0 restraints | Absolute structure parameter: 0.005 (3) |
Primary atom site location: dual | |
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. Multi-scan program SADABS was used for absorption correction
(Sheldrick, 2008). The structures were solved by the direct method and refined
by the full-matrix least squares
method on F2 using the SHELXS2018 (Sheldrick, 2015). All the
non-H atoms were refined anisotropically. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.6801 (4) | 0.35400 (18) | 0.88298 (12) | 0.0199 (5) | |
C2 | 0.8440 (4) | 0.36044 (17) | 0.91469 (11) | 0.0180 (5) | |
C3 | 0.9946 (4) | 0.3849 (2) | 0.88758 (13) | 0.0257 (6) | |
H3 | 0.9926 | 0.4020 | 0.8482 | 0.031* | |
C4 | 1.1483 (4) | 0.3845 (2) | 0.91804 (14) | 0.0296 (7) | |
H4 | 1.2505 | 0.4010 | 0.8994 | 0.036* | |
C5 | 1.1510 (4) | 0.3598 (2) | 0.97540 (14) | 0.0267 (6) | |
H5 | 1.2558 | 0.3591 | 0.9959 | 0.032* | |
C6 | 1.0018 (4) | 0.33601 (18) | 1.00333 (13) | 0.0220 (6) | |
H6 | 1.0046 | 0.3197 | 1.0428 | 0.026* | |
C7 | 0.8486 (4) | 0.33633 (18) | 0.97308 (12) | 0.0190 (5) | |
H7 | 0.7467 | 0.3202 | 0.9920 | 0.023* | |
C8 | 0.5874 (4) | 0.30870 (15) | 0.75124 (11) | 0.0169 (5) | |
C9 | 0.5440 (4) | 0.37940 (14) | 0.79317 (10) | 0.0158 (4) | |
H9A | 0.4401 | 0.3645 | 0.8159 | 0.019* | |
C10 | 0.5106 (4) | 0.45915 (15) | 0.75943 (11) | 0.0162 (5) | |
H10 | 0.4196 | 0.4491 | 0.7300 | 0.019* | |
C11 | 0.4551 (5) | 0.53015 (16) | 0.79991 (11) | 0.0216 (5) | |
C12 | 0.6547 (3) | 0.53885 (16) | 0.68964 (11) | 0.0138 (4) | |
C13 | 0.9751 (4) | 0.5401 (2) | 0.69427 (14) | 0.0277 (6) | |
H13 | 0.9733 | 0.4975 | 0.7225 | 0.033* | |
C14 | 0.8232 (3) | 0.56918 (16) | 0.67063 (11) | 0.0144 (4) | |
C15 | 1.1287 (4) | 0.5736 (3) | 0.67637 (18) | 0.0386 (9) | |
H15 | 1.2320 | 0.5545 | 0.6930 | 0.046* | |
C16 | 1.1331 (4) | 0.6350 (2) | 0.63436 (16) | 0.0317 (7) | |
H16 | 1.2388 | 0.6579 | 0.6226 | 0.038* | |
C17 | 0.9835 (4) | 0.6625 (2) | 0.60976 (15) | 0.0303 (7) | |
H17 | 0.9863 | 0.7033 | 0.5803 | 0.036* | |
C18 | 0.8279 (4) | 0.63035 (19) | 0.62826 (13) | 0.0229 (6) | |
H18 | 0.7248 | 0.6502 | 0.6119 | 0.027* | |
C19 | 0.4632 (5) | 0.38398 (18) | 0.59209 (13) | 0.0306 (7) | |
H19 | 0.4640 | 0.3998 | 0.6317 | 0.037* | |
C20 | 0.4639 (8) | 0.4451 (2) | 0.55046 (16) | 0.0472 (11) | |
H20 | 0.4628 | 0.5017 | 0.5612 | 0.057* | |
C21 | 0.4663 (9) | 0.4220 (2) | 0.49276 (17) | 0.0615 (16) | |
H21 | 0.4713 | 0.4625 | 0.4632 | 0.074* | |
C22 | 0.4611 (8) | 0.3389 (3) | 0.47868 (15) | 0.0495 (11) | |
H22 | 0.4587 | 0.3220 | 0.4393 | 0.059* | |
C23 | 0.4596 (5) | 0.28034 (19) | 0.52309 (12) | 0.0268 (6) | |
C24 | 0.4591 (5) | 0.18962 (19) | 0.51186 (12) | 0.0260 (6) | |
C25 | 0.4709 (7) | 0.1573 (2) | 0.45609 (14) | 0.0437 (10) | |
H25 | 0.4792 | 0.1927 | 0.4235 | 0.052* | |
C26 | 0.4703 (7) | 0.0716 (3) | 0.44913 (16) | 0.0495 (11) | |
H26 | 0.4785 | 0.0480 | 0.4116 | 0.059* | |
C27 | 0.4576 (7) | 0.0221 (2) | 0.49719 (16) | 0.0459 (10) | |
H27 | 0.4570 | −0.0362 | 0.4935 | 0.055* | |
C28 | 0.4458 (7) | 0.0589 (2) | 0.55099 (14) | 0.0412 (9) | |
H28 | 0.4357 | 0.0245 | 0.5841 | 0.049* | |
Mn1 | 0.45461 (6) | 0.20347 (2) | 0.64733 (2) | 0.01842 (11) | |
N1 | 0.4616 (4) | 0.30312 (15) | 0.57917 (10) | 0.0224 (5) | |
N2 | 0.4479 (5) | 0.14086 (16) | 0.55878 (11) | 0.0291 (6) | |
O1 | 0.3069 (3) | 0.52435 (13) | 0.82011 (10) | 0.0296 (5) | |
O2 | 0.5641 (4) | 0.58649 (13) | 0.80903 (10) | 0.0304 (5) | |
O3 | 0.6675 (2) | 0.47900 (11) | 0.73030 (8) | 0.0144 (3) | |
O4 | 0.5203 (3) | 0.56348 (14) | 0.67142 (10) | 0.0239 (4) | |
O5 | 0.6829 (3) | 0.39501 (12) | 0.83244 (8) | 0.0203 (4) | |
O6 | 0.5571 (3) | 0.3158 (2) | 0.90007 (11) | 0.0436 (8) | |
O7 | 0.7286 (3) | 0.27436 (14) | 0.75475 (10) | 0.0266 (5) | |
O8 | 0.4698 (3) | 0.29230 (12) | 0.71571 (8) | 0.0219 (4) | |
O9 | 0.7362 (3) | 0.18918 (14) | 0.65257 (11) | 0.0267 (5) | |
H9B | 0.753 (6) | 0.213 (3) | 0.685 (2) | 0.036 (11)* | |
H9C | 0.745 (7) | 0.140 (3) | 0.659 (2) | 0.048 (14)* | |
O10 | 0.1762 (4) | 0.2176 (2) | 0.65488 (13) | 0.0516 (8) | |
H10A | 0.1328 | 0.2534 | 0.6773 | 0.062* | |
H10B | 0.2085 | 0.2356 | 0.6221 | 0.062* | |
O12 | 0.0623 (5) | 0.0663 (2) | 0.65920 (15) | 0.0547 (8) | |
H12A | 0.0948 | 0.1136 | 0.6479 | 0.066* | |
H12B | 0.1536 | 0.0498 | 0.6752 | 0.066* | |
O11 | 0.0711 (5) | 0.3090 (5) | 0.7435 (3) | 0.160 (4) | |
H11A | −0.0096 | 0.2870 | 0.7624 | 0.193* | |
H11B | 0.0696 | 0.3603 | 0.7357 | 0.193* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0233 (13) | 0.0209 (12) | 0.0155 (12) | 0.0047 (11) | 0.0055 (10) | 0.0054 (10) |
C2 | 0.0225 (13) | 0.0162 (11) | 0.0152 (11) | 0.0021 (10) | 0.0052 (10) | 0.0005 (9) |
C3 | 0.0287 (16) | 0.0317 (15) | 0.0168 (11) | −0.0061 (12) | 0.0066 (10) | −0.0017 (11) |
C4 | 0.0256 (15) | 0.0365 (17) | 0.0268 (15) | −0.0089 (13) | 0.0070 (12) | −0.0050 (13) |
C5 | 0.0237 (14) | 0.0275 (15) | 0.0290 (15) | 0.0018 (12) | −0.0027 (12) | −0.0044 (12) |
C6 | 0.0270 (14) | 0.0194 (12) | 0.0196 (12) | 0.0053 (10) | 0.0003 (10) | 0.0006 (10) |
C7 | 0.0222 (13) | 0.0182 (12) | 0.0167 (12) | 0.0039 (10) | 0.0051 (10) | 0.0039 (9) |
C8 | 0.0263 (13) | 0.0096 (11) | 0.0147 (10) | −0.0004 (9) | −0.0005 (9) | 0.0025 (8) |
C9 | 0.0264 (12) | 0.0099 (9) | 0.0110 (9) | −0.0024 (10) | 0.0011 (10) | 0.0010 (8) |
C10 | 0.0228 (12) | 0.0108 (10) | 0.0149 (11) | −0.0005 (9) | 0.0073 (9) | 0.0015 (8) |
C11 | 0.0393 (15) | 0.0113 (10) | 0.0143 (11) | 0.0020 (12) | 0.0109 (12) | 0.0026 (8) |
C12 | 0.0147 (11) | 0.0130 (11) | 0.0136 (10) | 0.0002 (9) | 0.0002 (9) | 0.0030 (8) |
C13 | 0.0142 (12) | 0.0394 (17) | 0.0294 (14) | 0.0042 (12) | −0.0011 (11) | 0.0104 (12) |
C14 | 0.0115 (10) | 0.0176 (11) | 0.0140 (10) | −0.0003 (9) | −0.0002 (9) | 0.0010 (9) |
C15 | 0.0135 (13) | 0.056 (2) | 0.046 (2) | 0.0007 (15) | −0.0036 (13) | 0.0099 (18) |
C16 | 0.0164 (13) | 0.0425 (19) | 0.0363 (17) | −0.0112 (13) | 0.0061 (12) | −0.0027 (14) |
C17 | 0.0266 (16) | 0.0321 (16) | 0.0324 (15) | −0.0117 (13) | 0.0044 (12) | 0.0105 (13) |
C18 | 0.0151 (12) | 0.0267 (14) | 0.0268 (13) | −0.0052 (11) | −0.0029 (10) | 0.0111 (11) |
C19 | 0.052 (2) | 0.0179 (13) | 0.0218 (13) | 0.0026 (15) | 0.0022 (14) | 0.0033 (10) |
C20 | 0.092 (3) | 0.0205 (15) | 0.0290 (16) | 0.009 (2) | 0.005 (2) | 0.0068 (12) |
C21 | 0.129 (5) | 0.0297 (18) | 0.0260 (17) | 0.019 (3) | 0.007 (2) | 0.0145 (14) |
C22 | 0.094 (4) | 0.0364 (19) | 0.0175 (14) | 0.015 (2) | 0.003 (2) | 0.0066 (13) |
C23 | 0.0392 (16) | 0.0258 (14) | 0.0156 (11) | 0.0000 (14) | 0.0010 (12) | 0.0021 (10) |
C24 | 0.0351 (15) | 0.0275 (14) | 0.0153 (11) | −0.0071 (13) | 0.0012 (11) | −0.0018 (10) |
C25 | 0.076 (3) | 0.0380 (19) | 0.0175 (14) | −0.011 (2) | 0.0054 (17) | −0.0052 (12) |
C26 | 0.085 (3) | 0.041 (2) | 0.0221 (15) | −0.018 (2) | 0.0085 (19) | −0.0146 (14) |
C27 | 0.081 (3) | 0.0274 (16) | 0.0297 (16) | −0.015 (2) | 0.005 (2) | −0.0129 (13) |
C28 | 0.080 (3) | 0.0208 (14) | 0.0229 (14) | −0.0156 (19) | 0.0043 (18) | −0.0048 (11) |
Mn1 | 0.0315 (2) | 0.01179 (17) | 0.01201 (16) | −0.00413 (17) | 0.00102 (16) | −0.00020 (13) |
N1 | 0.0342 (13) | 0.0179 (10) | 0.0152 (10) | −0.0013 (12) | −0.0005 (10) | 0.0009 (8) |
N2 | 0.0524 (17) | 0.0192 (11) | 0.0157 (10) | −0.0101 (13) | 0.0016 (12) | −0.0017 (9) |
O1 | 0.0446 (14) | 0.0152 (9) | 0.0291 (11) | 0.0043 (9) | 0.0200 (10) | 0.0030 (8) |
O2 | 0.0522 (15) | 0.0138 (9) | 0.0253 (10) | −0.0060 (10) | 0.0150 (11) | −0.0048 (8) |
O3 | 0.0172 (8) | 0.0130 (8) | 0.0130 (8) | 0.0010 (7) | 0.0028 (7) | 0.0032 (6) |
O4 | 0.0112 (9) | 0.0277 (10) | 0.0328 (11) | −0.0001 (8) | 0.0004 (8) | 0.0145 (9) |
O5 | 0.0341 (11) | 0.0153 (9) | 0.0116 (8) | −0.0088 (8) | −0.0019 (8) | 0.0020 (7) |
O6 | 0.0190 (10) | 0.076 (2) | 0.0360 (13) | −0.0046 (12) | −0.0007 (10) | 0.0379 (13) |
O7 | 0.0282 (11) | 0.0224 (10) | 0.0292 (11) | 0.0062 (9) | −0.0068 (9) | −0.0064 (8) |
O8 | 0.0301 (10) | 0.0162 (8) | 0.0194 (8) | 0.0033 (9) | −0.0075 (8) | −0.0052 (7) |
O9 | 0.0363 (12) | 0.0170 (10) | 0.0269 (11) | 0.0013 (9) | 0.0089 (10) | −0.0008 (9) |
O10 | 0.0310 (13) | 0.088 (3) | 0.0363 (14) | −0.0164 (15) | −0.0018 (11) | 0.0070 (16) |
O12 | 0.0506 (18) | 0.0461 (17) | 0.067 (2) | 0.0069 (15) | −0.0061 (17) | 0.0064 (15) |
O11 | 0.029 (2) | 0.238 (9) | 0.215 (7) | −0.011 (3) | 0.016 (3) | −0.136 (7) |
Geometric parameters (Å, º) top
C1—O6 | 1.214 (4) | C18—H18 | 0.9500 |
C1—O5 | 1.344 (3) | C19—N1 | 1.346 (4) |
C1—C2 | 1.486 (4) | C19—C20 | 1.382 (4) |
C2—C3 | 1.397 (4) | C19—H19 | 0.9500 |
C2—C7 | 1.405 (4) | C20—C21 | 1.385 (5) |
C3—C4 | 1.398 (5) | C20—H20 | 0.9500 |
C3—H3 | 0.9500 | C21—C22 | 1.388 (6) |
C4—C5 | 1.384 (5) | C21—H21 | 0.9500 |
C4—H4 | 0.9500 | C22—C23 | 1.399 (4) |
C5—C6 | 1.393 (4) | C22—H22 | 0.9500 |
C5—H5 | 0.9500 | C23—N1 | 1.347 (3) |
C6—C7 | 1.392 (4) | C23—C24 | 1.495 (4) |
C6—H6 | 0.9500 | C24—N2 | 1.345 (4) |
C7—H7 | 0.9500 | C24—C25 | 1.394 (4) |
C8—O7 | 1.244 (4) | C25—C26 | 1.400 (6) |
C8—O8 | 1.265 (3) | C25—H25 | 0.9500 |
C8—C9 | 1.540 (3) | C26—C27 | 1.375 (6) |
C9—O5 | 1.443 (3) | C26—H26 | 0.9500 |
C9—C10 | 1.534 (3) | C27—C28 | 1.382 (4) |
C9—H9A | 1.0000 | C27—H27 | 0.9500 |
C10—O3 | 1.441 (3) | C28—N2 | 1.343 (4) |
C10—C11 | 1.547 (3) | C28—H28 | 0.9500 |
C10—H10 | 1.0000 | Mn1—O8 | 2.1423 (19) |
C11—O1 | 1.258 (4) | Mn1—O2i | 2.155 (2) |
C11—O2 | 1.271 (4) | Mn1—O10 | 2.207 (3) |
C12—O4 | 1.205 (3) | Mn1—O9 | 2.229 (3) |
C12—O3 | 1.355 (3) | Mn1—N1 | 2.258 (2) |
C12—C14 | 1.480 (3) | Mn1—N2 | 2.285 (2) |
C13—C15 | 1.388 (5) | Mn1—H10B | 2.0858 |
C13—C14 | 1.395 (4) | O2—Mn1ii | 2.155 (2) |
C13—H13 | 0.9500 | O9—H9B | 0.85 (5) |
C14—C18 | 1.395 (4) | O9—H9C | 0.82 (5) |
C15—C16 | 1.391 (6) | O10—H10A | 0.8504 |
C15—H15 | 0.9500 | O10—H10B | 0.8498 |
C16—C17 | 1.380 (5) | O12—H12A | 0.8507 |
C16—H16 | 0.9500 | O12—H12B | 0.8501 |
C17—C18 | 1.397 (4) | O11—H11A | 0.8497 |
C17—H17 | 0.9500 | O11—H11B | 0.8508 |
| | | |
O6—C1—O5 | 123.3 (3) | C21—C20—H20 | 120.8 |
O6—C1—C2 | 124.5 (3) | C20—C21—C22 | 119.3 (3) |
O5—C1—C2 | 112.3 (2) | C20—C21—H21 | 120.4 |
C3—C2—C7 | 119.2 (3) | C22—C21—H21 | 120.4 |
C3—C2—C1 | 122.3 (2) | C21—C22—C23 | 119.3 (3) |
C7—C2—C1 | 118.4 (3) | C21—C22—H22 | 120.4 |
C2—C3—C4 | 120.3 (3) | C23—C22—H22 | 120.4 |
C2—C3—H3 | 119.8 | N1—C23—C22 | 121.2 (3) |
C4—C3—H3 | 119.8 | N1—C23—C24 | 115.9 (2) |
C5—C4—C3 | 119.8 (3) | C22—C23—C24 | 122.8 (3) |
C5—C4—H4 | 120.1 | N2—C24—C25 | 121.9 (3) |
C3—C4—H4 | 120.1 | N2—C24—C23 | 116.1 (2) |
C4—C5—C6 | 120.7 (3) | C25—C24—C23 | 122.1 (3) |
C4—C5—H5 | 119.7 | C24—C25—C26 | 118.7 (3) |
C6—C5—H5 | 119.7 | C24—C25—H25 | 120.7 |
C7—C6—C5 | 119.6 (3) | C26—C25—H25 | 120.7 |
C7—C6—H6 | 120.2 | C27—C26—C25 | 119.3 (3) |
C5—C6—H6 | 120.2 | C27—C26—H26 | 120.4 |
C6—C7—C2 | 120.3 (3) | C25—C26—H26 | 120.4 |
C6—C7—H7 | 119.8 | C26—C27—C28 | 118.6 (3) |
C2—C7—H7 | 119.8 | C26—C27—H27 | 120.7 |
O7—C8—O8 | 126.9 (3) | C28—C27—H27 | 120.7 |
O7—C8—C9 | 119.4 (2) | N2—C28—C27 | 123.2 (3) |
O8—C8—C9 | 113.8 (2) | N2—C28—H28 | 118.4 |
O5—C9—C10 | 107.5 (2) | C27—C28—H28 | 118.4 |
O5—C9—C8 | 111.0 (2) | O8—Mn1—O2i | 104.59 (8) |
C10—C9—C8 | 110.32 (19) | O8—Mn1—O10 | 85.83 (11) |
O5—C9—H9A | 109.3 | O2i—Mn1—O10 | 89.23 (12) |
C10—C9—H9A | 109.3 | O8—Mn1—O9 | 88.54 (9) |
C8—C9—H9A | 109.3 | O2i—Mn1—O9 | 87.18 (10) |
O3—C10—C9 | 106.2 (2) | O10—Mn1—O9 | 172.35 (10) |
O3—C10—C11 | 110.9 (2) | O8—Mn1—N1 | 91.76 (8) |
C9—C10—C11 | 111.7 (2) | O2i—Mn1—N1 | 163.56 (9) |
O3—C10—H10 | 109.3 | O10—Mn1—N1 | 90.29 (12) |
C9—C10—H10 | 109.3 | O9—Mn1—N1 | 95.07 (10) |
C11—C10—H10 | 109.3 | O8—Mn1—N2 | 163.93 (9) |
O1—C11—O2 | 128.1 (3) | O2i—Mn1—N2 | 91.45 (9) |
O1—C11—C10 | 115.4 (3) | O10—Mn1—N2 | 95.39 (13) |
O2—C11—C10 | 116.5 (3) | O9—Mn1—N2 | 91.45 (11) |
O4—C12—O3 | 123.1 (2) | N1—Mn1—N2 | 72.23 (9) |
O4—C12—C14 | 124.8 (2) | O8—Mn1—H10B | 95.1 |
O3—C12—C14 | 112.2 (2) | O2i—Mn1—H10B | 106.7 |
C15—C13—C14 | 119.7 (3) | O10—Mn1—H10B | 22.6 |
C15—C13—H13 | 120.2 | O9—Mn1—H10B | 164.2 |
C14—C13—H13 | 120.2 | N1—Mn1—H10B | 69.5 |
C18—C14—C13 | 119.6 (3) | N2—Mn1—H10B | 80.8 |
C18—C14—C12 | 117.9 (2) | C19—N1—C23 | 118.7 (2) |
C13—C14—C12 | 122.5 (2) | C19—N1—Mn1 | 122.96 (19) |
C13—C15—C16 | 120.7 (3) | C23—N1—Mn1 | 118.28 (19) |
C13—C15—H15 | 119.7 | C28—N2—C24 | 118.4 (3) |
C16—C15—H15 | 119.7 | C28—N2—Mn1 | 124.1 (2) |
C17—C16—C15 | 119.9 (3) | C24—N2—Mn1 | 117.28 (19) |
C17—C16—H16 | 120.1 | C11—O2—Mn1ii | 131.7 (2) |
C15—C16—H16 | 120.1 | C12—O3—C10 | 114.8 (2) |
C16—C17—C18 | 119.9 (3) | C1—O5—C9 | 116.5 (2) |
C16—C17—H17 | 120.0 | C8—O8—Mn1 | 131.38 (19) |
C18—C17—H17 | 120.0 | Mn1—O9—H9B | 99 (3) |
C14—C18—C17 | 120.2 (3) | Mn1—O9—H9C | 101 (4) |
C14—C18—H18 | 119.9 | H9B—O9—H9C | 105 (5) |
C17—C18—H18 | 119.9 | Mn1—O10—H10A | 121.1 |
N1—C19—C20 | 123.1 (3) | Mn1—O10—H10B | 70.7 |
N1—C19—H19 | 118.4 | H10A—O10—H10B | 115.2 |
C20—C19—H19 | 118.4 | H12A—O12—H12B | 99.5 |
C19—C20—C21 | 118.3 (3) | H11A—O11—H11B | 120.7 |
C19—C20—H20 | 120.8 | | |
| | | |
O6—C1—C2—C3 | 162.1 (3) | C19—C20—C21—C22 | 2.5 (10) |
O5—C1—C2—C3 | −17.4 (4) | C20—C21—C22—C23 | −2.2 (10) |
O6—C1—C2—C7 | −14.1 (5) | C21—C22—C23—N1 | 0.6 (8) |
O5—C1—C2—C7 | 166.4 (2) | C21—C22—C23—C24 | −178.3 (5) |
C7—C2—C3—C4 | 0.7 (5) | N1—C23—C24—N2 | 4.7 (5) |
C1—C2—C3—C4 | −175.4 (3) | C22—C23—C24—N2 | −176.4 (4) |
C2—C3—C4—C5 | −0.1 (5) | N1—C23—C24—C25 | −174.7 (4) |
C3—C4—C5—C6 | −0.5 (5) | C22—C23—C24—C25 | 4.2 (7) |
C4—C5—C6—C7 | 0.6 (5) | N2—C24—C25—C26 | 0.3 (7) |
C5—C6—C7—C2 | 0.0 (4) | C23—C24—C25—C26 | 179.7 (4) |
C3—C2—C7—C6 | −0.7 (4) | C24—C25—C26—C27 | 0.2 (8) |
C1—C2—C7—C6 | 175.6 (3) | C25—C26—C27—C28 | 0.0 (9) |
O7—C8—C9—O5 | −0.3 (3) | C26—C27—C28—N2 | −0.8 (9) |
O8—C8—C9—O5 | 180.0 (2) | C20—C19—N1—C23 | −0.3 (6) |
O7—C8—C9—C10 | 118.8 (3) | C20—C19—N1—Mn1 | −178.6 (4) |
O8—C8—C9—C10 | −60.9 (3) | C22—C23—N1—C19 | 0.7 (6) |
O5—C9—C10—O3 | 58.5 (2) | C24—C23—N1—C19 | 179.6 (3) |
C8—C9—C10—O3 | −62.6 (3) | C22—C23—N1—Mn1 | 179.0 (4) |
O5—C9—C10—C11 | −62.5 (3) | C24—C23—N1—Mn1 | −2.1 (4) |
C8—C9—C10—C11 | 176.3 (2) | C27—C28—N2—C24 | 1.2 (8) |
O3—C10—C11—O1 | 169.2 (2) | C27—C28—N2—Mn1 | −173.8 (4) |
C9—C10—C11—O1 | −72.5 (3) | C25—C24—N2—C28 | −0.9 (6) |
O3—C10—C11—O2 | −11.3 (3) | C23—C24—N2—C28 | 179.6 (4) |
C9—C10—C11—O2 | 107.0 (3) | C25—C24—N2—Mn1 | 174.4 (3) |
C15—C13—C14—C18 | 1.5 (5) | C23—C24—N2—Mn1 | −5.1 (4) |
C15—C13—C14—C12 | −177.2 (3) | O1—C11—O2—Mn1ii | −8.5 (5) |
O4—C12—C14—C18 | −0.5 (4) | C10—C11—O2—Mn1ii | 172.10 (18) |
O3—C12—C14—C18 | 179.2 (2) | O4—C12—O3—C10 | −12.8 (4) |
O4—C12—C14—C13 | 178.2 (3) | C14—C12—O3—C10 | 167.4 (2) |
O3—C12—C14—C13 | −2.1 (4) | C9—C10—O3—C12 | 168.1 (2) |
C14—C13—C15—C16 | −1.2 (6) | C11—C10—O3—C12 | −70.3 (3) |
C13—C15—C16—C17 | −0.5 (6) | O6—C1—O5—C9 | −11.5 (4) |
C15—C16—C17—C18 | 1.8 (6) | C2—C1—O5—C9 | 168.0 (2) |
C13—C14—C18—C17 | −0.2 (5) | C10—C9—O5—C1 | 147.8 (2) |
C12—C14—C18—C17 | 178.5 (3) | C8—C9—O5—C1 | −91.4 (3) |
C16—C17—C18—C14 | −1.4 (5) | O7—C8—O8—Mn1 | −0.5 (4) |
N1—C19—C20—C21 | −1.3 (8) | C9—C8—O8—Mn1 | 179.16 (16) |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, y+1/2, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O11—H11A···O7iii | 0.85 | 2.08 | 2.763 (5) | 138 |
O12—H12B···O2i | 0.85 | 2.33 | 3.044 (5) | 142 |
O12—H12A···O10 | 0.85 | 1.81 | 2.616 (5) | 157 |
O10—H10A···O11 | 0.85 | 1.84 | 2.660 (7) | 161 |
O9—H9C···O1i | 0.82 (5) | 1.97 (5) | 2.770 (3) | 163 (5) |
O9—H9B···O7 | 0.85 (5) | 1.91 (5) | 2.736 (3) | 165 (5) |
C19—H19···O8 | 0.95 | 2.61 | 3.221 (4) | 122 |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (iii) x−1, y, z. |
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