In the title polymeric structure, {[Mn(C8H3NO6)(C12H8N2)]·H2O}n, the Mn atom adopts an octahedral geometry. The 2-nitrobenzene-1,4-dicarboxylate ligand is in a chelating–bridging mode and its two carboxylate groups are approximately perpendicular to each other. The crystal structure can be described as layers formed by a two-dimensional network of hydrogen bonds.
Supporting information
CCDC reference: 270224
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.007 Å
- R factor = 0.063
- wR factor = 0.142
- Data-to-parameter ratio = 11.2
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95
Alert level C
REFLT03_ALERT_3_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 25.00
From the CIF: _diffrn_reflns_theta_full 0.00
From the CIF: _reflns_number_total 3197
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 3379
Completeness (_total/calc) 94.61%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.95
PLAT128_ALERT_4_C Non-standard setting of Space group C2/c .... I2/a
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C6
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Poly[[[(1,10-phenanthroline)manganese(II)]-µ
3-2-nitrobenzene-1,4-
dicarboxylato] monohydrate]
top
Crystal data top
[Mn(C8H3NO6)(C12H8N2)]·H2O | F(000) = 1880 |
Mr = 462.27 | Dx = 1.600 Mg m−3 |
Monoclinic, I2/a | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -I 2ya | Cell parameters from 3483 reflections |
a = 18.515 (3) Å | θ = 2.2–26.6° |
b = 9.927 (2) Å | µ = 0.74 mm−1 |
c = 20.948 (3) Å | T = 295 K |
β = 94.659 (3)° | Block, pale yellow |
V = 3837 (1) Å3 | 0.28 × 0.18 × 0.16 mm |
Z = 8 | |
Data collection top
Bruker APEX area-detector diffractometer | 3197 independent reflections |
Radiation source: fine-focus sealed tube | 2021 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.064 |
φ and ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −21→22 |
Tmin = 0.820, Tmax = 0.891 | k = −11→8 |
7693 measured reflections | l = −24→22 |
Refinement top
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)] = 0.063 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.142 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0503P)2] where P = (Fo2 + 2Fc2)/3 |
3197 reflections | (Δ/σ)max < 0.001 |
286 parameters | Δρmax = 0.35 e Å−3 |
2 restraints | Δρmin = −0.37 e Å−3 |
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. 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Mn1 | 0.06507 (4) | 0.03268 (7) | 0.17918 (3) | 0.0344 (3) | |
N1 | −0.0256 (2) | 0.0470 (4) | 0.10043 (18) | 0.0382 (10) | |
N2 | 0.1010 (2) | 0.1839 (4) | 0.10756 (19) | 0.0398 (10) | |
N3 | 0.3879 (2) | −0.3721 (4) | 0.1436 (2) | 0.0472 (11) | |
O1 | 0.15756 (16) | −0.1022 (3) | 0.14920 (16) | 0.0443 (9) | |
O2 | 0.17238 (17) | 0.0249 (3) | 0.23499 (16) | 0.0444 (9) | |
O3 | 0.54032 (16) | −0.1955 (3) | 0.24027 (16) | 0.0452 (9) | |
O4 | 0.49302 (16) | −0.3728 (3) | 0.28361 (16) | 0.0462 (9) | |
O5 | 0.4510 (2) | −0.4035 (4) | 0.14722 (18) | 0.0625 (11) | |
O6 | 0.3417 (2) | −0.4252 (4) | 0.1072 (2) | 0.0882 (16) | |
OW1 | 0.1740 (3) | 0.2421 (5) | 0.3238 (4) | 0.136 (3) | |
C1 | −0.0877 (3) | −0.0207 (5) | 0.0964 (3) | 0.0466 (13) | |
C2 | −0.1421 (3) | −0.0012 (5) | 0.0481 (3) | 0.0542 (16) | |
C3 | −0.1337 (3) | 0.0926 (5) | 0.0027 (3) | 0.0496 (14) | |
C4 | −0.0699 (3) | 0.1687 (5) | 0.0042 (2) | 0.0412 (13) | |
C5 | −0.0545 (3) | 0.2688 (6) | −0.0421 (3) | 0.0586 (16) | |
C6 | 0.0091 (4) | 0.3360 (6) | −0.0390 (3) | 0.0700 (19) | |
C7 | 0.0643 (3) | 0.3109 (5) | 0.0116 (3) | 0.0511 (14) | |
C8 | 0.1301 (3) | 0.3774 (6) | 0.0179 (3) | 0.0692 (18) | |
C9 | 0.1794 (3) | 0.3480 (6) | 0.0670 (3) | 0.076 (2) | |
C10 | 0.1635 (3) | 0.2497 (6) | 0.1103 (3) | 0.0593 (16) | |
C11 | −0.0163 (3) | 0.1403 (4) | 0.0547 (2) | 0.0365 (12) | |
C12 | 0.0515 (3) | 0.2131 (5) | 0.0581 (2) | 0.0399 (12) | |
C13 | 0.1957 (2) | −0.0585 (5) | 0.1962 (3) | 0.0354 (12) | |
C14 | 0.2729 (2) | −0.1069 (4) | 0.2071 (2) | 0.0327 (11) | |
C15 | 0.2971 (2) | −0.2118 (4) | 0.1718 (2) | 0.0319 (11) | |
C16 | 0.3653 (2) | −0.2618 (4) | 0.1848 (2) | 0.0305 (11) | |
C17 | 0.4128 (2) | −0.2116 (4) | 0.2338 (2) | 0.0314 (11) | |
C18 | 0.3888 (2) | −0.1036 (5) | 0.2675 (2) | 0.0394 (12) | |
C19 | 0.3206 (2) | −0.0524 (4) | 0.2550 (2) | 0.0372 (12) | |
C20 | 0.4876 (2) | −0.2665 (5) | 0.2524 (2) | 0.0360 (12) | |
H1 | −0.0949 | −0.0846 | 0.1277 | 0.056* | |
H2 | −0.1842 | −0.0525 | 0.0469 | 0.065* | |
H3 | −0.1704 | 0.1068 | −0.0297 | 0.060* | |
H5 | −0.0894 | 0.2881 | −0.0753 | 0.070* | |
H6 | 0.0172 | 0.3996 | −0.0703 | 0.084* | |
H8 | 0.1405 | 0.4426 | −0.0119 | 0.083* | |
H9 | 0.2234 | 0.3934 | 0.0715 | 0.092* | |
H10 | 0.1984 | 0.2285 | 0.1431 | 0.071* | |
H15 | 0.2668 | −0.2489 | 0.1388 | 0.038* | |
H18 | 0.4197 | −0.0646 | 0.2996 | 0.047* | |
H19 | 0.3059 | 0.0202 | 0.2788 | 0.045* | |
H2W1 | 0.167 (4) | 0.163 (3) | 0.337 (3) | 0.080* | |
H1W1 | 0.1348 (18) | 0.255 (6) | 0.300 (2) | 0.080* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Mn1 | 0.0261 (4) | 0.0347 (4) | 0.0413 (5) | 0.0035 (3) | −0.0046 (3) | 0.0036 (3) |
N1 | 0.037 (2) | 0.041 (3) | 0.035 (2) | 0.0000 (19) | −0.005 (2) | 0.0049 (19) |
N2 | 0.030 (2) | 0.042 (2) | 0.047 (3) | 0.0007 (19) | 0.002 (2) | 0.009 (2) |
N3 | 0.044 (3) | 0.044 (3) | 0.053 (3) | −0.001 (2) | 0.004 (2) | −0.001 (2) |
O1 | 0.0282 (19) | 0.057 (2) | 0.046 (2) | 0.0020 (16) | −0.0097 (17) | −0.0025 (18) |
O2 | 0.033 (2) | 0.048 (2) | 0.051 (2) | 0.0090 (16) | −0.0011 (18) | −0.0046 (18) |
O3 | 0.0242 (18) | 0.044 (2) | 0.065 (2) | −0.0047 (16) | −0.0077 (18) | 0.0132 (18) |
O4 | 0.035 (2) | 0.037 (2) | 0.065 (2) | −0.0031 (15) | −0.0071 (18) | 0.0265 (18) |
O5 | 0.045 (2) | 0.069 (3) | 0.074 (3) | 0.021 (2) | 0.006 (2) | −0.020 (2) |
O6 | 0.071 (3) | 0.096 (4) | 0.092 (3) | 0.012 (3) | −0.025 (3) | −0.053 (3) |
OW1 | 0.081 (4) | 0.106 (4) | 0.209 (7) | 0.027 (4) | −0.065 (4) | −0.072 (5) |
C1 | 0.043 (3) | 0.051 (3) | 0.045 (3) | 0.005 (3) | −0.001 (3) | −0.002 (3) |
C2 | 0.046 (4) | 0.059 (4) | 0.056 (4) | 0.000 (3) | −0.007 (3) | −0.010 (3) |
C3 | 0.042 (3) | 0.059 (4) | 0.046 (3) | 0.009 (3) | −0.012 (3) | −0.009 (3) |
C4 | 0.038 (3) | 0.043 (3) | 0.041 (3) | 0.004 (2) | −0.002 (3) | −0.002 (2) |
C5 | 0.072 (4) | 0.055 (4) | 0.046 (4) | 0.013 (3) | −0.009 (3) | 0.006 (3) |
C6 | 0.095 (5) | 0.054 (4) | 0.058 (4) | −0.004 (4) | −0.012 (4) | 0.019 (3) |
C7 | 0.058 (4) | 0.049 (3) | 0.046 (3) | −0.002 (3) | 0.004 (3) | 0.006 (3) |
C8 | 0.075 (5) | 0.063 (4) | 0.070 (5) | −0.005 (3) | 0.008 (4) | 0.020 (3) |
C9 | 0.060 (4) | 0.083 (5) | 0.084 (5) | −0.019 (4) | −0.005 (4) | 0.024 (4) |
C10 | 0.042 (3) | 0.068 (4) | 0.067 (4) | −0.007 (3) | −0.002 (3) | 0.020 (3) |
C11 | 0.040 (3) | 0.031 (3) | 0.039 (3) | −0.001 (2) | 0.001 (2) | 0.001 (2) |
C12 | 0.046 (3) | 0.035 (3) | 0.039 (3) | 0.004 (2) | 0.007 (3) | 0.004 (2) |
C13 | 0.025 (3) | 0.033 (3) | 0.049 (3) | 0.006 (2) | 0.004 (2) | 0.008 (2) |
C14 | 0.028 (3) | 0.032 (3) | 0.037 (3) | 0.004 (2) | −0.002 (2) | 0.000 (2) |
C15 | 0.026 (3) | 0.036 (3) | 0.032 (3) | −0.001 (2) | −0.009 (2) | 0.000 (2) |
C16 | 0.027 (3) | 0.030 (3) | 0.035 (3) | −0.002 (2) | 0.004 (2) | 0.002 (2) |
C17 | 0.027 (2) | 0.026 (3) | 0.041 (3) | −0.008 (2) | 0.002 (2) | 0.005 (2) |
C18 | 0.027 (3) | 0.038 (3) | 0.050 (3) | −0.004 (2) | −0.014 (2) | −0.002 (2) |
C19 | 0.031 (3) | 0.032 (3) | 0.049 (3) | 0.002 (2) | 0.001 (2) | −0.007 (2) |
C20 | 0.021 (3) | 0.042 (3) | 0.044 (3) | 0.006 (2) | −0.007 (2) | −0.007 (3) |
Geometric parameters (Å, º) top
Mn1—O1 | 2.301 (3) | C7—C8 | 1.381 (7) |
Mn1—O2 | 2.223 (3) | C7—C12 | 1.408 (7) |
Mn1—O3i | 2.134 (3) | C8—C9 | 1.350 (7) |
Mn1—O4ii | 2.102 (3) | C9—C10 | 1.380 (7) |
Mn1—N1 | 2.260 (4) | C11—C12 | 1.444 (6) |
Mn1—N2 | 2.260 (4) | C13—C14 | 1.507 (6) |
N1—C1 | 1.328 (6) | C14—C15 | 1.373 (6) |
N1—C11 | 1.354 (6) | C14—C19 | 1.391 (6) |
N2—C10 | 1.325 (6) | C15—C16 | 1.365 (6) |
N2—C12 | 1.359 (5) | C16—C17 | 1.389 (6) |
N3—O5 | 1.205 (5) | C17—C18 | 1.378 (6) |
N3—O6 | 1.218 (5) | C17—C20 | 1.509 (6) |
N3—C16 | 1.476 (6) | C18—C19 | 1.367 (6) |
O1—C13 | 1.243 (5) | C1—H1 | 0.9300 |
O2—C13 | 1.260 (5) | C2—H2 | 0.9300 |
O3—C20 | 1.246 (5) | C3—H3 | 0.9300 |
O3—Mn1iii | 2.134 (3) | C5—H5 | 0.9300 |
O4—C20 | 1.241 (5) | C6—H6 | 0.9300 |
O4—Mn1ii | 2.102 (3) | C8—H8 | 0.9300 |
C1—C2 | 1.383 (6) | C9—H9 | 0.9300 |
C2—C3 | 1.350 (7) | C10—H10 | 0.9300 |
C3—C4 | 1.401 (7) | C15—H15 | 0.9300 |
C4—C11 | 1.419 (6) | C18—H18 | 0.9300 |
C4—C5 | 1.433 (7) | C19—H19 | 0.9300 |
C5—C6 | 1.350 (8) | OW1—H2W1 | 0.85 (4) |
C6—C7 | 1.435 (7) | OW1—H1W1 | 0.86 (4) |
| | | |
O4ii—Mn1—O3i | 102.0 (1) | N2—C12—C11 | 117.4 (4) |
O4ii—Mn1—O2 | 104.0 (1) | C7—C12—C11 | 120.4 (5) |
O3i—Mn1—O2 | 86.4 (1) | O1—C13—O2 | 122.5 (4) |
O4ii—Mn1—N2 | 159.2 (1) | O1—C13—C14 | 118.7 (4) |
O3i—Mn1—N2 | 89.1 (1) | O2—C13—C14 | 118.9 (4) |
O2—Mn1—N2 | 94.2 (1) | O1—C13—Mn1 | 63.0 (2) |
O4ii—Mn1—N1 | 86.9 (1) | O2—C13—Mn1 | 59.5 (2) |
O3i—Mn1—N1 | 102.0 (1) | C14—C13—Mn1 | 178.0 (4) |
O2—Mn1—N1 | 164.8 (1) | C15—C14—C19 | 117.9 (4) |
N2—Mn1—N1 | 73.4 (1) | C15—C14—C13 | 120.4 (4) |
O4ii—Mn1—O1 | 94.4 (1) | C19—C14—C13 | 121.6 (4) |
O3i—Mn1—O1 | 143.6 (1) | C16—C15—C14 | 120.4 (4) |
O2—Mn1—O1 | 58.0 (1) | C15—C16—C17 | 122.5 (4) |
N2—Mn1—O1 | 86.5 (1) | C15—C16—N3 | 117.0 (4) |
N1—Mn1—O1 | 111.3 (1) | C17—C16—N3 | 120.4 (4) |
C1—N1—C11 | 117.4 (4) | C18—C17—C16 | 116.6 (4) |
C1—N1—Mn1 | 127.0 (3) | C18—C17—C20 | 118.4 (4) |
C11—N1—Mn1 | 115.5 (3) | C16—C17—C20 | 125.0 (4) |
C10—N2—C12 | 117.4 (4) | C19—C18—C17 | 121.5 (4) |
C10—N2—Mn1 | 127.0 (3) | C18—C19—C14 | 121.1 (4) |
C12—N2—Mn1 | 115.6 (3) | O4—C20—O3 | 123.9 (4) |
O5—N3—O6 | 123.7 (5) | O4—C20—C17 | 118.4 (4) |
O5—N3—C16 | 118.3 (4) | O3—C20—C17 | 117.4 (4) |
O6—N3—C16 | 118.0 (4) | H2W1—OW1—H1W1 | 100 (6) |
C13—O1—Mn1 | 88.2 (3) | N1—C1—H1 | 118.3 |
C13—O2—Mn1 | 91.3 (3) | C2—C1—H1 | 118.3 |
C20—O3—Mn1iii | 139.5 (3) | C3—C2—H2 | 120.2 |
C20—O4—Mn1ii | 144.6 (3) | C1—C2—H2 | 120.2 |
N1—C1—C2 | 123.5 (5) | C2—C3—H3 | 120.0 |
C3—C2—C1 | 119.6 (5) | C4—C3—H3 | 120.0 |
C2—C3—C4 | 120.1 (5) | C6—C5—H5 | 119.0 |
C3—C4—C11 | 116.6 (5) | C4—C5—H5 | 119.0 |
C3—C4—C5 | 124.9 (5) | C5—C6—H6 | 119.5 |
C11—C4—C5 | 118.4 (5) | C7—C6—H6 | 119.5 |
C6—C5—C4 | 122.1 (5) | C9—C8—H8 | 119.8 |
C5—C6—C7 | 121.1 (6) | C7—C8—H8 | 119.8 |
C8—C7—C12 | 117.5 (5) | C8—C9—H9 | 120.4 |
C8—C7—C6 | 123.9 (5) | C10—C9—H9 | 120.4 |
C12—C7—C6 | 118.7 (5) | N2—C10—H10 | 118.2 |
C9—C8—C7 | 120.3 (6) | C9—C10—H10 | 118.2 |
C8—C9—C10 | 119.1 (6) | C16—C15—H15 | 119.8 |
N2—C10—C9 | 123.5 (5) | C14—C15—H15 | 119.8 |
N1—C11—C4 | 122.8 (4) | C19—C18—H18 | 119.3 |
N1—C11—C12 | 117.9 (4) | C17—C18—H18 | 119.3 |
C4—C11—C12 | 119.3 (4) | C18—C19—H19 | 119.4 |
N2—C12—C7 | 122.2 (5) | C14—C19—H19 | 119.4 |
| | | |
O4ii—Mn1—N1—C1 | 6.5 (4) | C3—C4—C11—C12 | 178.6 (4) |
O3i—Mn1—N1—C1 | −95.1 (4) | C5—C4—C11—C12 | 0.4 (7) |
O2—Mn1—N1—C1 | 142.6 (5) | C10—N2—C12—C7 | −1.2 (7) |
N2—Mn1—N1—C1 | 179.4 (4) | Mn1—N2—C12—C7 | 176.4 (4) |
O1—Mn1—N1—C1 | 100.0 (4) | C10—N2—C12—C11 | 179.3 (5) |
C13—Mn1—N1—C1 | 109.3 (4) | Mn1—N2—C12—C11 | −3.2 (5) |
O4ii—Mn1—N1—C11 | −177.3 (3) | C8—C7—C12—N2 | 0.1 (8) |
O3i—Mn1—N1—C11 | 81.1 (3) | C6—C7—C12—N2 | −179.8 (5) |
O2—Mn1—N1—C11 | −41.1 (7) | C8—C7—C12—C11 | 179.7 (5) |
N2—Mn1—N1—C11 | −4.3 (3) | C6—C7—C12—C11 | −0.3 (8) |
O1—Mn1—N1—C11 | −83.8 (3) | N1—C11—C12—N2 | −0.7 (7) |
C13—Mn1—N1—C11 | −74.4 (4) | C4—C11—C12—N2 | 179.3 (4) |
O4ii—Mn1—N2—C10 | −158.6 (4) | N1—C11—C12—C7 | 179.7 (4) |
O3i—Mn1—N2—C10 | 78.4 (5) | C4—C11—C12—C7 | −0.3 (7) |
O2—Mn1—N2—C10 | −7.9 (5) | Mn1—O1—C13—O2 | 1.1 (5) |
N1—Mn1—N2—C10 | −178.8 (5) | Mn1—O1—C13—C14 | −178.7 (4) |
O1—Mn1—N2—C10 | −65.4 (5) | Mn1—O2—C13—O1 | −1.1 (5) |
C13—Mn1—N2—C10 | −36.8 (5) | Mn1—O2—C13—C14 | 178.7 (4) |
O4ii—Mn1—N2—C12 | 24.1 (6) | O4ii—Mn1—C13—O1 | 79.5 (3) |
O3i—Mn1—N2—C12 | −98.8 (3) | O3i—Mn1—C13—O1 | −171.6 (2) |
O2—Mn1—N2—C12 | 174.9 (3) | O2—Mn1—C13—O1 | 178.9 (5) |
N1—Mn1—N2—C12 | 3.9 (3) | N2—Mn1—C13—O1 | −82.6 (3) |
O1—Mn1—N2—C12 | 117.3 (3) | N1—Mn1—C13—O1 | −18.3 (4) |
C13—Mn1—N2—C12 | 145.9 (3) | O4ii—Mn1—C13—O2 | −99.5 (3) |
O4ii—Mn1—O1—C13 | −104.3 (3) | O3i—Mn1—C13—O2 | 9.4 (3) |
O3i—Mn1—O1—C13 | 12.8 (4) | N2—Mn1—C13—O2 | 98.5 (3) |
O2—Mn1—O1—C13 | −0.6 (3) | N1—Mn1—C13—O2 | 162.8 (3) |
N2—Mn1—O1—C13 | 96.5 (3) | O1—Mn1—C13—O2 | −178.9 (5) |
N1—Mn1—O1—C13 | 167.3 (3) | O1—C13—C14—C15 | −9.8 (7) |
O4ii—Mn1—O2—C13 | 87.0 (3) | O2—C13—C14—C15 | 170.4 (4) |
O3i—Mn1—O2—C13 | −171.5 (3) | O1—C13—C14—C19 | 173.5 (4) |
N2—Mn1—O2—C13 | −82.6 (3) | O2—C13—C14—C19 | −6.3 (7) |
N1—Mn1—O2—C13 | −47.5 (6) | C19—C14—C15—C16 | 1.5 (7) |
O1—Mn1—O2—C13 | 0.6 (3) | C13—C14—C15—C16 | −175.3 (4) |
C11—N1—C1—C2 | 0.5 (7) | C14—C15—C16—C17 | 0.7 (7) |
Mn1—N1—C1—C2 | 176.7 (4) | C14—C15—C16—N3 | −178.4 (4) |
N1—C1—C2—C3 | −1.3 (8) | O5—N3—C16—C15 | 168.4 (4) |
C1—C2—C3—C4 | 0.7 (8) | O6—N3—C16—C15 | −10.7 (7) |
C2—C3—C4—C11 | 0.6 (8) | O5—N3—C16—C17 | −10.7 (7) |
C2—C3—C4—C5 | 178.7 (5) | O6—N3—C16—C17 | 170.2 (5) |
C3—C4—C5—C6 | −178.0 (6) | C15—C16—C17—C18 | −2.7 (7) |
C11—C4—C5—C6 | 0.1 (8) | N3—C16—C17—C18 | 176.3 (4) |
C4—C5—C6—C7 | −0.7 (10) | C15—C16—C17—C20 | 177.2 (4) |
C5—C6—C7—C8 | −179.2 (6) | N3—C16—C17—C20 | −3.8 (7) |
C5—C6—C7—C12 | 0.7 (9) | C16—C17—C18—C19 | 2.6 (7) |
C12—C7—C8—C9 | 0.0 (9) | C20—C17—C18—C19 | −177.3 (4) |
C6—C7—C8—C9 | 180.0 (6) | C17—C18—C19—C14 | −0.5 (8) |
C7—C8—C9—C10 | 0.8 (10) | C15—C14—C19—C18 | −1.6 (7) |
C12—N2—C10—C9 | 2.1 (9) | C13—C14—C19—C18 | 175.2 (4) |
Mn1—N2—C10—C9 | −175.1 (5) | Mn1ii—O4—C20—O3 | 179.6 (3) |
C8—C9—C10—N2 | −2.0 (10) | Mn1ii—O4—C20—C17 | 6.3 (8) |
C1—N1—C11—C4 | 0.9 (7) | Mn1iii—O3—C20—O4 | 166.3 (3) |
Mn1—N1—C11—C4 | −175.7 (3) | Mn1iii—O3—C20—C17 | −20.4 (7) |
C1—N1—C11—C12 | −179.1 (4) | C18—C17—C20—O4 | 103.5 (5) |
Mn1—N1—C11—C12 | 4.3 (6) | C16—C17—C20—O4 | −76.4 (6) |
C3—C4—C11—N1 | −1.4 (7) | C18—C17—C20—O3 | −70.2 (6) |
C5—C4—C11—N1 | −179.6 (5) | C16—C17—C20—O3 | 109.9 (5) |
Symmetry codes: (i) x−1/2, −y, z; (ii) −x+1/2, −y−1/2, −z+1/2; (iii) x+1/2, −y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
OW1—H1W1···O3i | 0.86 (4) | 2.15 (3) | 2.949 (6) | 156 (5) |
Symmetry code: (i) x−1/2, −y, z. |