Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618005508/sk3685sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618005508/sk3685Isup2.hkl |
CCDC reference: 1835840
Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: publCIF (Westrip, 2010).
[Mn(C16H8N4O8)] | F(000) = 884 |
Mr = 439.20 | Dx = 1.792 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.3422 (4) Å | Cell parameters from 9920 reflections |
b = 16.4500 (8) Å | θ = 2.5–27.5° |
c = 11.8773 (5) Å | µ = 0.87 mm−1 |
β = 93.108 (2)° | T = 293 K |
V = 1627.51 (13) Å3 | Block, yellow |
Z = 4 | 0.21 × 0.18 × 0.15 mm |
Bruker D8 VENTURE PHOTON diffractometer | 3244 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.031 |
φ and ω scans | θmax = 27.6°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −10→10 |
k = −21→21 | |
22393 measured reflections | l = −15→14 |
3753 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.031 | H-atom parameters constrained |
wR(F2) = 0.084 | w = 1/[σ2(Fo2) + (0.0394P)2 + 0.9243P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
3753 reflections | Δρmax = 0.30 e Å−3 |
264 parameters | Δρmin = −0.36 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
Mn1 | 1.00156 (3) | 0.56363 (2) | 0.17925 (2) | 0.02691 (9) | |
N1 | 0.47745 (17) | 0.61064 (9) | 0.11776 (13) | 0.0300 (3) | |
H1A | 0.3909 | 0.6371 | 0.1001 | 0.036* | |
N2 | 0.73381 (17) | 0.58357 (9) | 0.15029 (13) | 0.0286 (3) | |
N3 | 0.96790 (17) | 0.68247 (9) | 0.25923 (13) | 0.0283 (3) | |
N4 | 0.91528 (18) | 0.80371 (9) | 0.32423 (13) | 0.0297 (3) | |
H4A | 0.8733 | 0.8512 | 0.3293 | 0.036* | |
O1 | 0.21031 (16) | 0.50309 (11) | 0.13295 (15) | 0.0541 (4) | |
O2 | 0.37463 (18) | 0.40264 (10) | 0.18115 (15) | 0.0511 (4) | |
O3 | 0.66409 (18) | 0.37515 (9) | 0.22286 (16) | 0.0504 (4) | |
H3 | 0.5670 | 0.3829 | 0.2148 | 0.076* | |
O4 | 0.88557 (16) | 0.44914 (8) | 0.22465 (13) | 0.0376 (3) | |
O5 | 1.0169 (2) | 0.88073 (9) | 0.51987 (12) | 0.0450 (4) | |
O6 | 1.20124 (17) | 0.78402 (9) | 0.55902 (13) | 0.0430 (4) | |
O7 | 1.2319 (2) | 0.63322 (10) | 0.50006 (14) | 0.0500 (4) | |
H7 | 1.2174 | 0.6788 | 0.5256 | 0.075* | |
O8 | 1.1452 (2) | 0.56090 (9) | 0.35227 (14) | 0.0516 (4) | |
C1 | 0.3454 (2) | 0.47588 (13) | 0.15565 (17) | 0.0357 (4) | |
C2 | 0.4861 (2) | 0.53054 (11) | 0.14972 (16) | 0.0292 (4) | |
C3 | 0.6466 (2) | 0.51509 (10) | 0.17001 (15) | 0.0278 (4) | |
C4 | 0.7387 (2) | 0.44240 (11) | 0.20821 (17) | 0.0319 (4) | |
C5 | 0.6292 (2) | 0.64095 (10) | 0.11886 (15) | 0.0267 (3) | |
C6 | 0.6667 (2) | 0.72430 (11) | 0.08298 (16) | 0.0285 (4) | |
C7 | 0.5793 (2) | 0.75560 (13) | −0.01030 (17) | 0.0372 (4) | |
H7A | 0.5006 | 0.7237 | −0.0471 | 0.045* | |
C8 | 0.6074 (3) | 0.83341 (14) | −0.04936 (19) | 0.0443 (5) | |
H8A | 0.5480 | 0.8532 | −0.1120 | 0.053* | |
C9 | 0.7227 (3) | 0.88147 (13) | 0.00409 (19) | 0.0441 (5) | |
H9A | 0.7415 | 0.9336 | −0.0223 | 0.053* | |
C10 | 0.8105 (2) | 0.85196 (12) | 0.09733 (17) | 0.0364 (4) | |
H10A | 0.8877 | 0.8849 | 0.1337 | 0.044* | |
C11 | 0.7854 (2) | 0.77349 (10) | 0.13806 (15) | 0.0277 (4) | |
C12 | 0.8843 (2) | 0.75027 (10) | 0.23927 (15) | 0.0268 (4) | |
C13 | 1.0855 (2) | 0.81509 (12) | 0.50117 (16) | 0.0339 (4) | |
C14 | 1.0233 (2) | 0.77016 (11) | 0.40019 (16) | 0.0295 (4) | |
C15 | 1.0542 (2) | 0.69432 (11) | 0.35922 (16) | 0.0289 (4) | |
C16 | 1.1485 (2) | 0.62510 (12) | 0.40453 (17) | 0.0370 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Mn1 | 0.02126 (14) | 0.01983 (14) | 0.03941 (17) | 0.00174 (10) | −0.00045 (10) | 0.00094 (10) |
N1 | 0.0189 (7) | 0.0265 (8) | 0.0441 (9) | 0.0031 (6) | −0.0036 (6) | −0.0018 (7) |
N2 | 0.0211 (7) | 0.0220 (7) | 0.0422 (9) | 0.0000 (6) | −0.0011 (6) | 0.0008 (6) |
N3 | 0.0238 (7) | 0.0231 (7) | 0.0376 (8) | 0.0025 (6) | −0.0019 (6) | −0.0020 (6) |
N4 | 0.0291 (8) | 0.0211 (7) | 0.0388 (8) | 0.0039 (6) | 0.0005 (6) | −0.0036 (6) |
O1 | 0.0196 (7) | 0.0658 (11) | 0.0769 (11) | −0.0004 (7) | 0.0040 (7) | −0.0189 (9) |
O2 | 0.0369 (8) | 0.0361 (8) | 0.0805 (11) | −0.0154 (7) | 0.0058 (8) | 0.0016 (8) |
O3 | 0.0363 (8) | 0.0257 (7) | 0.0889 (12) | −0.0051 (6) | 0.0007 (8) | 0.0100 (7) |
O4 | 0.0256 (6) | 0.0252 (7) | 0.0619 (9) | 0.0041 (5) | 0.0012 (6) | 0.0073 (6) |
O5 | 0.0575 (10) | 0.0366 (8) | 0.0409 (8) | 0.0083 (7) | 0.0017 (7) | −0.0085 (6) |
O6 | 0.0341 (7) | 0.0457 (9) | 0.0479 (8) | 0.0015 (6) | −0.0079 (6) | −0.0106 (7) |
O7 | 0.0487 (9) | 0.0429 (9) | 0.0557 (10) | 0.0125 (7) | −0.0220 (7) | −0.0079 (7) |
O8 | 0.0601 (10) | 0.0331 (8) | 0.0589 (10) | 0.0181 (7) | −0.0213 (8) | −0.0081 (7) |
C1 | 0.0257 (9) | 0.0376 (11) | 0.0440 (11) | −0.0056 (8) | 0.0054 (8) | −0.0089 (8) |
C2 | 0.0215 (8) | 0.0249 (9) | 0.0409 (10) | −0.0003 (7) | 0.0006 (7) | −0.0030 (7) |
C3 | 0.0221 (8) | 0.0220 (8) | 0.0392 (10) | −0.0017 (6) | 0.0009 (7) | −0.0015 (7) |
C4 | 0.0274 (9) | 0.0232 (9) | 0.0454 (11) | 0.0004 (7) | 0.0036 (8) | 0.0006 (7) |
C5 | 0.0209 (8) | 0.0230 (8) | 0.0358 (9) | 0.0010 (6) | −0.0024 (6) | −0.0016 (7) |
C6 | 0.0242 (8) | 0.0233 (8) | 0.0379 (10) | 0.0039 (7) | 0.0016 (7) | 0.0007 (7) |
C7 | 0.0308 (9) | 0.0361 (10) | 0.0439 (11) | 0.0022 (8) | −0.0057 (8) | 0.0035 (9) |
C8 | 0.0435 (12) | 0.0436 (12) | 0.0451 (12) | 0.0087 (9) | −0.0042 (9) | 0.0131 (9) |
C9 | 0.0499 (12) | 0.0288 (10) | 0.0536 (13) | 0.0032 (9) | 0.0029 (10) | 0.0119 (9) |
C10 | 0.0400 (10) | 0.0230 (9) | 0.0459 (11) | −0.0019 (8) | 0.0007 (8) | 0.0004 (8) |
C11 | 0.0254 (8) | 0.0215 (8) | 0.0361 (9) | 0.0037 (7) | 0.0016 (7) | −0.0006 (7) |
C12 | 0.0236 (8) | 0.0202 (8) | 0.0368 (9) | −0.0001 (6) | 0.0018 (7) | −0.0006 (7) |
C13 | 0.0308 (9) | 0.0347 (10) | 0.0366 (10) | −0.0028 (8) | 0.0041 (8) | −0.0045 (8) |
C14 | 0.0249 (8) | 0.0279 (9) | 0.0359 (9) | −0.0007 (7) | 0.0037 (7) | −0.0025 (7) |
C15 | 0.0221 (8) | 0.0274 (9) | 0.0370 (9) | 0.0008 (7) | −0.0005 (7) | −0.0024 (7) |
C16 | 0.0318 (10) | 0.0324 (10) | 0.0461 (11) | 0.0059 (8) | −0.0062 (8) | −0.0027 (8) |
Mn1—O1i | 2.1049 (15) | O5—Mn1iv | 2.1128 (14) |
Mn1—O5ii | 2.1128 (14) | O6—C13 | 1.262 (2) |
Mn1—O4 | 2.1979 (13) | O7—C16 | 1.305 (2) |
Mn1—N3 | 2.1982 (15) | O7—H7 | 0.8200 |
Mn1—N2 | 2.2654 (14) | O8—C16 | 1.225 (2) |
Mn1—O8 | 2.3225 (16) | C1—C2 | 1.484 (2) |
N1—C5 | 1.360 (2) | C2—C3 | 1.372 (2) |
N1—C2 | 1.372 (2) | C3—C4 | 1.479 (2) |
N1—H1A | 0.8600 | C5—C6 | 1.474 (2) |
N2—C5 | 1.325 (2) | C6—C7 | 1.392 (3) |
N2—C3 | 1.368 (2) | C6—C11 | 1.412 (2) |
N3—C12 | 1.330 (2) | C7—C8 | 1.386 (3) |
N3—C15 | 1.369 (2) | C7—H7A | 0.9300 |
N4—C12 | 1.353 (2) | C8—C9 | 1.374 (3) |
N4—C14 | 1.358 (2) | C8—H8A | 0.9300 |
N4—H4A | 0.8600 | C9—C10 | 1.382 (3) |
O1—C1 | 1.229 (2) | C9—H9A | 0.9300 |
O1—Mn1iii | 2.1049 (15) | C10—C11 | 1.398 (3) |
O2—C1 | 1.263 (3) | C10—H10A | 0.9300 |
O3—C4 | 1.286 (2) | C11—C12 | 1.471 (2) |
O3—H3 | 0.8200 | C13—C14 | 1.479 (3) |
O4—C4 | 1.235 (2) | C14—C15 | 1.369 (2) |
O5—C13 | 1.248 (2) | C15—C16 | 1.469 (3) |
O1i—Mn1—O5ii | 83.09 (7) | C2—C3—C4 | 133.59 (16) |
O1i—Mn1—O4 | 92.30 (6) | O4—C4—O3 | 122.63 (17) |
O5ii—Mn1—O4 | 129.79 (6) | O4—C4—C3 | 118.04 (16) |
O1i—Mn1—N3 | 131.34 (6) | O3—C4—C3 | 119.34 (17) |
O5ii—Mn1—N3 | 90.99 (6) | N2—C5—N1 | 109.86 (15) |
O4—Mn1—N3 | 126.00 (6) | N2—C5—C6 | 126.68 (15) |
O1i—Mn1—N2 | 148.40 (6) | N1—C5—C6 | 123.36 (15) |
O5ii—Mn1—N2 | 84.75 (6) | C7—C6—C11 | 118.75 (17) |
O4—Mn1—N2 | 73.60 (5) | C7—C6—C5 | 117.65 (16) |
N3—Mn1—N2 | 77.81 (5) | C11—C6—C5 | 123.60 (16) |
O1i—Mn1—O8 | 80.07 (6) | C8—C7—C6 | 121.16 (19) |
O5ii—Mn1—O8 | 138.39 (6) | C8—C7—H7A | 119.4 |
O4—Mn1—O8 | 88.81 (6) | C6—C7—H7A | 119.4 |
N3—Mn1—O8 | 72.95 (5) | C9—C8—C7 | 120.25 (19) |
N2—Mn1—O8 | 126.47 (6) | C9—C8—H8A | 119.9 |
C5—N1—C2 | 108.33 (14) | C7—C8—H8A | 119.9 |
C5—N1—H1A | 125.8 | C8—C9—C10 | 119.70 (19) |
C2—N1—H1A | 125.8 | C8—C9—H9A | 120.1 |
C5—N2—C3 | 106.67 (14) | C10—C9—H9A | 120.1 |
C5—N2—Mn1 | 140.76 (12) | C9—C10—C11 | 121.24 (19) |
C3—N2—Mn1 | 112.57 (11) | C9—C10—H10A | 119.4 |
C12—N3—C15 | 106.34 (14) | C11—C10—H10A | 119.4 |
C12—N3—Mn1 | 138.32 (12) | C10—C11—C6 | 118.89 (17) |
C15—N3—Mn1 | 115.34 (11) | C10—C11—C12 | 115.76 (16) |
C12—N4—C14 | 108.95 (15) | C6—C11—C12 | 125.32 (16) |
C12—N4—H4A | 125.5 | N3—C12—N4 | 109.57 (15) |
C14—N4—H4A | 125.5 | N3—C12—C11 | 128.97 (16) |
C1—O1—Mn1iii | 151.27 (16) | N4—C12—C11 | 121.12 (15) |
C4—O3—H3 | 109.5 | O5—C13—O6 | 126.74 (18) |
C4—O4—Mn1 | 118.96 (12) | O5—C13—C14 | 115.65 (18) |
C13—O5—Mn1iv | 125.81 (13) | O6—C13—C14 | 117.61 (17) |
C16—O7—H7 | 109.5 | N4—C14—C15 | 105.38 (16) |
C16—O8—Mn1 | 115.36 (13) | N4—C14—C13 | 121.80 (16) |
O1—C1—O2 | 124.28 (19) | C15—C14—C13 | 132.80 (18) |
O1—C1—C2 | 119.18 (19) | C14—C15—N3 | 109.75 (16) |
O2—C1—C2 | 116.51 (17) | C14—C15—C16 | 133.11 (17) |
C3—C2—N1 | 105.23 (15) | N3—C15—C16 | 116.97 (16) |
C3—C2—C1 | 130.33 (17) | O8—C16—O7 | 121.70 (18) |
N1—C2—C1 | 124.42 (16) | O8—C16—C15 | 119.05 (17) |
N2—C3—C2 | 109.91 (15) | O7—C16—C15 | 119.24 (18) |
N2—C3—C4 | 116.50 (15) | ||
Mn1iii—O1—C1—O2 | 96.8 (4) | C9—C10—C11—C12 | −178.72 (19) |
Mn1iii—O1—C1—C2 | −85.4 (4) | C7—C6—C11—C10 | 0.3 (3) |
C5—N1—C2—C3 | 0.3 (2) | C5—C6—C11—C10 | −179.61 (17) |
C5—N1—C2—C1 | −178.19 (17) | C7—C6—C11—C12 | 178.13 (18) |
O1—C1—C2—C3 | −179.6 (2) | C5—C6—C11—C12 | −1.8 (3) |
O2—C1—C2—C3 | −1.6 (3) | C15—N3—C12—N4 | −0.4 (2) |
O1—C1—C2—N1 | −1.5 (3) | Mn1—N3—C12—N4 | 179.42 (13) |
O2—C1—C2—N1 | 176.52 (18) | C15—N3—C12—C11 | 172.85 (17) |
C5—N2—C3—C2 | 0.4 (2) | Mn1—N3—C12—C11 | −7.3 (3) |
Mn1—N2—C3—C2 | −179.20 (12) | C14—N4—C12—N3 | 0.9 (2) |
C5—N2—C3—C4 | −179.12 (16) | C14—N4—C12—C11 | −172.96 (16) |
Mn1—N2—C3—C4 | 1.3 (2) | C10—C11—C12—N3 | −132.8 (2) |
N1—C2—C3—N2 | −0.4 (2) | C6—C11—C12—N3 | 49.3 (3) |
C1—C2—C3—N2 | 177.96 (19) | C10—C11—C12—N4 | 39.8 (2) |
N1—C2—C3—C4 | 179.0 (2) | C6—C11—C12—N4 | −138.15 (18) |
C1—C2—C3—C4 | −2.7 (4) | Mn1iv—O5—C13—O6 | −26.7 (3) |
Mn1—O4—C4—O3 | 173.51 (16) | Mn1iv—O5—C13—C14 | 153.52 (14) |
Mn1—O4—C4—C3 | −6.4 (2) | C12—N4—C14—C15 | −1.0 (2) |
N2—C3—C4—O4 | 3.2 (3) | C12—N4—C14—C13 | 177.94 (16) |
C2—C3—C4—O4 | −176.1 (2) | O5—C13—C14—N4 | 9.3 (3) |
N2—C3—C4—O3 | −176.66 (18) | O6—C13—C14—N4 | −170.52 (17) |
C2—C3—C4—O3 | 4.0 (3) | O5—C13—C14—C15 | −172.1 (2) |
C3—N2—C5—N1 | −0.2 (2) | O6—C13—C14—C15 | 8.1 (3) |
Mn1—N2—C5—N1 | 179.20 (14) | N4—C14—C15—N3 | 0.8 (2) |
C3—N2—C5—C6 | −176.61 (17) | C13—C14—C15—N3 | −178.01 (19) |
Mn1—N2—C5—C6 | 2.8 (3) | N4—C14—C15—C16 | −174.1 (2) |
C2—N1—C5—N2 | −0.1 (2) | C13—C14—C15—C16 | 7.1 (4) |
C2—N1—C5—C6 | 176.50 (17) | C12—N3—C15—C14 | −0.3 (2) |
N2—C5—C6—C7 | 136.9 (2) | Mn1—N3—C15—C14 | 179.88 (12) |
N1—C5—C6—C7 | −39.1 (3) | C12—N3—C15—C16 | 175.60 (16) |
N2—C5—C6—C11 | −43.2 (3) | Mn1—N3—C15—C16 | −4.3 (2) |
N1—C5—C6—C11 | 140.84 (18) | Mn1—O8—C16—O7 | −176.34 (16) |
C11—C6—C7—C8 | 0.2 (3) | Mn1—O8—C16—C15 | 4.6 (3) |
C5—C6—C7—C8 | −179.94 (19) | C14—C15—C16—O8 | 174.3 (2) |
C6—C7—C8—C9 | −0.2 (3) | N3—C15—C16—O8 | −0.4 (3) |
C7—C8—C9—C10 | −0.1 (3) | C14—C15—C16—O7 | −4.8 (3) |
C8—C9—C10—C11 | 0.6 (3) | N3—C15—C16—O7 | −179.49 (18) |
C9—C10—C11—C6 | −0.7 (3) |
Symmetry codes: (i) x+1, y, z; (ii) x, −y+3/2, z−1/2; (iii) x−1, y, z; (iv) x, −y+3/2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2 | 0.82 | 1.67 | 2.480 (2) | 172 |
O7—H7···O6 | 0.82 | 1.78 | 2.594 (2) | 170 |
N1—H1A···O6v | 0.86 | 2.08 | 2.937 (2) | 172 |
N4—H4A···O2vi | 0.86 | 2.23 | 2.913 (2) | 136 |
Symmetry codes: (v) x−1, −y+3/2, z−1/2; (vi) −x+1, y+1/2, −z+1/2. |