In the cation of the title compound, [Mn(C
9H
7NO
3)(C
12H
10N
2)
2(H
2O)]ClO
4·3H
2O, the Mn
II atom is coordinated by two O atoms, one from a hippurate ligand and the other from a coordinated water molecule, and four N atoms from two 1,10-phenanthroline ligands. In the crystal structure, the cations and water molecules are linked by intra- and intermolecular hydrogen bonds, forming
R64(12) rings; these rings are further connected by intermolecular hydrogen bonds and C—H
π interactions into a three-dimensional supramolecular framework.
Supporting information
CCDC reference: 624917
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- Disorder in solvent or counterion
- R factor = 0.049
- wR factor = 0.142
- Data-to-parameter ratio = 17.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C18
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C21
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl1
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 33.00 Perc.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXS97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2003); software used to prepare material for publication: SHELXTL.
Aqua(hippurato)bis(1,10-phenanthroline)manganese(II) perchlorate trihydrate
top
Crystal data top
[Mn(C9H7NO3)(C12H10N2)2(H2O)]ClO4·3H2O | F(000) = 1580 |
Mr = 765.03 | Dx = 1.436 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3200 reflections |
a = 14.1328 (12) Å | θ = 1.0–27.5° |
b = 16.0110 (14) Å | µ = 0.52 mm−1 |
c = 16.8357 (14) Å | T = 298 K |
β = 111.774 (1)° | Needle, yellow |
V = 3537.8 (5) Å3 | 0.45 × 0.24 × 0.22 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD APEXII diffractometer | 8777 independent reflections |
Radiation source: fine-focus sealed tube | 4663 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
Detector resolution: 8.35 pixels mm-1 | θmax = 28.6°, θmin = 2.4° |
ω scans | h = −18→18 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −21→17 |
Tmin = 0.856, Tmax = 0.885 | l = −22→22 |
25123 measured reflections | |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0595P)2 + 0.3436P] where P = (Fo2 + 2Fc2)/3 |
8777 reflections | (Δ/σ)max = 0.001 |
497 parameters | Δρmax = 0.36 e Å−3 |
80 restraints | Δρmin = −0.39 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 | Occ. (<1) |
Mn1 | 0.34418 (3) | 0.73675 (2) | 0.46202 (2) | 0.05019 (14) | |
Cl1 | 0.23885 (7) | 0.97709 (6) | 0.71820 (5) | 0.0776 (3) | |
O1 | 0.22911 (13) | 0.65692 (11) | 0.47224 (12) | 0.0583 (5) | |
N1 | 0.47690 (16) | 0.83000 (14) | 0.49398 (14) | 0.0570 (6) | |
N4 | 0.30066 (18) | 0.75629 (14) | 0.31814 (14) | 0.0582 (6) | |
N2 | 0.4042 (2) | 0.76001 (15) | 0.60636 (14) | 0.0628 (6) | |
N5 | 0.13892 (16) | 0.46531 (13) | 0.53121 (13) | 0.0540 (6) | |
H5A | 0.1622 | 0.4472 | 0.5830 | 0.065* | |
C26 | 0.1429 (2) | 0.55307 (17) | 0.51593 (19) | 0.0583 (7) | |
H26B | 0.1448 | 0.5830 | 0.5666 | 0.070* | |
H26A | 0.0806 | 0.5689 | 0.4695 | 0.070* | |
C24 | 0.2319 (2) | 0.81775 (18) | 0.28318 (17) | 0.0571 (7) | |
C25 | 0.2320 (2) | 0.58129 (16) | 0.49389 (16) | 0.0493 (6) | |
C12 | 0.51674 (19) | 0.85573 (17) | 0.57719 (17) | 0.0548 (7) | |
O2 | 0.30107 (15) | 0.53167 (12) | 0.49865 (15) | 0.0755 (6) | |
O1W | 0.42924 (16) | 0.62822 (12) | 0.45936 (16) | 0.0837 (7) | |
C11 | 0.4788 (2) | 0.81806 (17) | 0.63656 (16) | 0.0556 (7) | |
C23 | 0.19232 (19) | 0.86251 (17) | 0.33828 (18) | 0.0573 (7) | |
N3 | 0.22755 (16) | 0.84083 (13) | 0.42207 (14) | 0.0544 (5) | |
C28 | 0.1022 (2) | 0.32130 (16) | 0.49154 (16) | 0.0507 (6) | |
C4 | 0.5937 (2) | 0.9167 (2) | 0.6060 (2) | 0.0706 (8) | |
C7 | 0.5210 (2) | 0.8407 (2) | 0.72346 (19) | 0.0716 (9) | |
O3 | 0.06351 (18) | 0.43420 (13) | 0.39251 (13) | 0.0818 (7) | |
C27 | 0.09991 (19) | 0.41106 (17) | 0.46715 (17) | 0.0531 (7) | |
C9 | 0.4146 (4) | 0.7384 (3) | 0.7500 (2) | 0.0972 (12) | |
H9 | 0.3929 | 0.7086 | 0.7875 | 0.117* | |
C33 | 0.0231 (3) | 0.2695 (2) | 0.44476 (19) | 0.0708 (9) | |
H33 | −0.0318 | 0.2909 | 0.3992 | 0.085* | |
C16 | 0.1981 (3) | 0.8394 (3) | 0.1959 (2) | 0.0818 (10) | |
C8 | 0.4859 (3) | 0.7982 (3) | 0.7794 (2) | 0.0934 (12) | |
H8 | 0.5119 | 0.8114 | 0.8374 | 0.112* | |
C14 | 0.3064 (4) | 0.7317 (3) | 0.1798 (3) | 0.1023 (13) | |
H14 | 0.3328 | 0.7010 | 0.1459 | 0.123* | |
C29 | 0.1829 (2) | 0.28810 (19) | 0.55800 (19) | 0.0665 (8) | |
H29 | 0.2367 | 0.3224 | 0.5899 | 0.080* | |
C5 | 0.6309 (3) | 0.9404 (3) | 0.6937 (3) | 0.0951 (12) | |
H5 | 0.6804 | 0.9818 | 0.7127 | 0.114* | |
C13 | 0.3368 (3) | 0.7146 (2) | 0.2674 (2) | 0.0786 (9) | |
H13 | 0.3841 | 0.6723 | 0.2909 | 0.094* | |
C22 | 0.1904 (3) | 0.8813 (2) | 0.4730 (2) | 0.0779 (9) | |
H22 | 0.2145 | 0.8673 | 0.5307 | 0.094* | |
C19 | 0.1195 (2) | 0.9254 (2) | 0.3046 (2) | 0.0797 (10) | |
C1 | 0.5147 (2) | 0.8635 (2) | 0.4396 (2) | 0.0723 (9) | |
H1 | 0.4884 | 0.8459 | 0.3830 | 0.087* | |
C10 | 0.3737 (3) | 0.7216 (2) | 0.6625 (2) | 0.0855 (10) | |
H10 | 0.3226 | 0.6816 | 0.6426 | 0.103* | |
O4W | 0.57351 (18) | 0.68194 (16) | 0.27317 (15) | 0.0989 (8) | |
O3W | −0.0530 (2) | 0.35671 (15) | 0.24267 (14) | 0.1009 (8) | |
O2W | 0.59156 (17) | 0.60493 (16) | 0.42477 (17) | 0.1032 (9) | |
C30 | 0.1847 (3) | 0.2044 (2) | 0.5778 (2) | 0.0903 (11) | |
H30 | 0.2400 | 0.1824 | 0.6225 | 0.108* | |
C2 | 0.5914 (3) | 0.9236 (2) | 0.4629 (2) | 0.0844 (10) | |
H2 | 0.6157 | 0.9454 | 0.4229 | 0.101* | |
C18 | 0.0875 (3) | 0.9445 (3) | 0.2150 (3) | 0.1182 (16) | |
H18 | 0.0394 | 0.9863 | 0.1919 | 0.142* | |
C3 | 0.6298 (2) | 0.9495 (2) | 0.5455 (3) | 0.0884 (11) | |
H3 | 0.6809 | 0.9898 | 0.5622 | 0.106* | |
C32 | 0.0255 (3) | 0.1858 (2) | 0.4657 (2) | 0.0985 (13) | |
H32 | −0.0279 | 0.1509 | 0.4345 | 0.118* | |
C15 | 0.2388 (4) | 0.7929 (3) | 0.1454 (2) | 0.1059 (14) | |
H15 | 0.2187 | 0.8048 | 0.0874 | 0.127* | |
C21 | 0.1174 (3) | 0.9435 (2) | 0.4440 (3) | 0.1084 (14) | |
H21 | 0.0926 | 0.9696 | 0.4817 | 0.130* | |
C20 | 0.0824 (3) | 0.9660 (2) | 0.3608 (3) | 0.1045 (13) | |
H20 | 0.0340 | 1.0082 | 0.3410 | 0.125* | |
C17 | 0.1249 (4) | 0.9040 (3) | 0.1642 (3) | 0.1128 (16) | |
H17 | 0.1026 | 0.9182 | 0.1067 | 0.135* | |
C6 | 0.5966 (3) | 0.9047 (3) | 0.7495 (2) | 0.0978 (12) | |
H6 | 0.6224 | 0.9218 | 0.8063 | 0.117* | |
C31 | 0.1063 (4) | 0.1543 (2) | 0.5324 (3) | 0.1073 (13) | |
H31 | 0.1073 | 0.0981 | 0.5465 | 0.129* | |
O5A | 0.2374 (6) | 1.0552 (3) | 0.7579 (3) | 0.161 (3) | 0.731 (9) |
O4A | 0.1418 (3) | 0.9594 (4) | 0.6578 (3) | 0.129 (2) | 0.731 (9) |
O6A | 0.3052 (4) | 0.9858 (5) | 0.6723 (3) | 0.141 (2) | 0.731 (9) |
O7A | 0.2740 (6) | 0.9165 (3) | 0.7793 (3) | 0.136 (2) | 0.731 (9) |
O4B | 0.2660 (14) | 1.0247 (9) | 0.6654 (9) | 0.151 (7) | 0.269 (9) |
O5B | 0.1838 (12) | 1.0118 (13) | 0.7621 (10) | 0.192 (9) | 0.269 (9) |
O6B | 0.1933 (14) | 0.8999 (8) | 0.6835 (8) | 0.141 (6) | 0.269 (9) |
O7B | 0.3311 (8) | 0.9493 (10) | 0.7845 (7) | 0.110 (5) | 0.269 (9) |
H1B | 0.4019 | 0.5834 | 0.4738 | 0.164* | |
H1A | 0.4847 | 0.6113 | 0.4497 | 0.164* | |
H2B | 0.6309 | 0.5590 | 0.4392 | 0.164* | |
H2A | 0.5829 | 0.6161 | 0.3704 | 0.164* | |
H4B | 0.5840 | 0.7361 | 0.2795 | 0.164* | |
H3B | −0.0165 | 0.3822 | 0.2921 | 0.164* | |
H4A | 0.6268 | 0.6659 | 0.2578 | 0.164* | |
H3A | −0.1042 | 0.3943 | 0.2288 | 0.164* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Mn1 | 0.0598 (3) | 0.0443 (3) | 0.0499 (2) | −0.00426 (18) | 0.02434 (19) | 0.00121 (18) |
Cl1 | 0.0813 (6) | 0.0795 (6) | 0.0672 (5) | −0.0049 (4) | 0.0219 (4) | 0.0133 (5) |
O1 | 0.0622 (11) | 0.0429 (11) | 0.0748 (12) | −0.0012 (9) | 0.0311 (10) | 0.0095 (9) |
N1 | 0.0587 (13) | 0.0578 (15) | 0.0563 (14) | −0.0071 (11) | 0.0234 (11) | −0.0016 (11) |
N4 | 0.0682 (15) | 0.0610 (16) | 0.0517 (13) | −0.0122 (12) | 0.0296 (12) | −0.0051 (11) |
N2 | 0.0799 (17) | 0.0600 (16) | 0.0507 (13) | −0.0028 (13) | 0.0269 (12) | 0.0026 (11) |
N5 | 0.0649 (14) | 0.0453 (14) | 0.0516 (13) | −0.0132 (10) | 0.0214 (11) | 0.0003 (10) |
C26 | 0.0653 (17) | 0.0449 (17) | 0.0709 (18) | −0.0069 (13) | 0.0324 (15) | −0.0019 (13) |
C24 | 0.0546 (16) | 0.0631 (19) | 0.0493 (16) | −0.0204 (14) | 0.0144 (13) | 0.0031 (14) |
C25 | 0.0564 (16) | 0.0406 (16) | 0.0505 (15) | −0.0014 (12) | 0.0195 (12) | 0.0015 (12) |
C12 | 0.0499 (15) | 0.0494 (17) | 0.0587 (17) | 0.0060 (12) | 0.0129 (13) | −0.0059 (13) |
O2 | 0.0738 (13) | 0.0516 (12) | 0.1163 (17) | 0.0112 (10) | 0.0529 (13) | 0.0238 (11) |
O1W | 0.0847 (15) | 0.0566 (13) | 0.135 (2) | 0.0093 (11) | 0.0699 (15) | 0.0130 (12) |
C11 | 0.0605 (16) | 0.0525 (18) | 0.0488 (15) | 0.0108 (14) | 0.0142 (13) | −0.0016 (13) |
C23 | 0.0498 (15) | 0.0540 (18) | 0.0667 (18) | −0.0092 (13) | 0.0199 (14) | 0.0102 (14) |
N3 | 0.0652 (14) | 0.0460 (13) | 0.0598 (14) | −0.0022 (11) | 0.0323 (12) | 0.0017 (11) |
C28 | 0.0587 (16) | 0.0483 (16) | 0.0517 (15) | −0.0104 (13) | 0.0282 (13) | −0.0044 (12) |
C4 | 0.0581 (18) | 0.065 (2) | 0.078 (2) | −0.0024 (15) | 0.0133 (16) | −0.0079 (17) |
C7 | 0.080 (2) | 0.072 (2) | 0.0505 (18) | 0.0165 (18) | 0.0094 (16) | −0.0062 (16) |
O3 | 0.1086 (17) | 0.0688 (15) | 0.0521 (12) | −0.0079 (12) | 0.0112 (11) | 0.0065 (11) |
C27 | 0.0548 (15) | 0.0541 (18) | 0.0517 (16) | −0.0061 (13) | 0.0211 (13) | 0.0021 (13) |
C9 | 0.144 (4) | 0.099 (3) | 0.060 (2) | 0.006 (3) | 0.051 (2) | 0.012 (2) |
C33 | 0.085 (2) | 0.067 (2) | 0.0584 (18) | −0.0214 (17) | 0.0242 (16) | −0.0063 (15) |
C16 | 0.080 (2) | 0.105 (3) | 0.0505 (19) | −0.030 (2) | 0.0132 (17) | 0.0073 (19) |
C8 | 0.131 (3) | 0.092 (3) | 0.0491 (19) | 0.019 (3) | 0.024 (2) | −0.0004 (19) |
C14 | 0.130 (4) | 0.124 (4) | 0.074 (3) | −0.037 (3) | 0.062 (3) | −0.029 (2) |
C29 | 0.0675 (19) | 0.058 (2) | 0.073 (2) | −0.0047 (15) | 0.0239 (16) | 0.0007 (15) |
C5 | 0.083 (2) | 0.099 (3) | 0.082 (3) | −0.018 (2) | 0.005 (2) | −0.027 (2) |
C13 | 0.096 (2) | 0.084 (2) | 0.071 (2) | −0.0146 (19) | 0.0489 (19) | −0.0174 (18) |
C22 | 0.102 (3) | 0.059 (2) | 0.092 (2) | 0.0085 (18) | 0.058 (2) | 0.0039 (17) |
C19 | 0.0592 (19) | 0.069 (2) | 0.101 (3) | 0.0014 (16) | 0.0186 (19) | 0.023 (2) |
C1 | 0.077 (2) | 0.075 (2) | 0.071 (2) | −0.0194 (17) | 0.0347 (17) | −0.0065 (16) |
C10 | 0.120 (3) | 0.085 (3) | 0.062 (2) | −0.014 (2) | 0.047 (2) | 0.0040 (17) |
O4W | 0.1006 (17) | 0.111 (2) | 0.0916 (16) | 0.0294 (15) | 0.0437 (14) | 0.0281 (15) |
O3W | 0.126 (2) | 0.0917 (18) | 0.0632 (14) | 0.0122 (15) | 0.0093 (14) | −0.0117 (12) |
O2W | 0.0884 (16) | 0.1063 (19) | 0.145 (2) | 0.0433 (14) | 0.0775 (16) | 0.0619 (17) |
C30 | 0.108 (3) | 0.060 (2) | 0.095 (3) | 0.011 (2) | 0.028 (2) | 0.011 (2) |
C2 | 0.079 (2) | 0.085 (3) | 0.098 (3) | −0.0245 (19) | 0.044 (2) | −0.003 (2) |
C18 | 0.079 (3) | 0.127 (4) | 0.115 (4) | 0.010 (3) | −0.002 (3) | 0.058 (3) |
C3 | 0.067 (2) | 0.082 (3) | 0.113 (3) | −0.0231 (18) | 0.030 (2) | −0.015 (2) |
C32 | 0.144 (4) | 0.067 (3) | 0.078 (2) | −0.053 (2) | 0.033 (2) | −0.017 (2) |
C15 | 0.123 (4) | 0.141 (4) | 0.052 (2) | −0.052 (3) | 0.030 (2) | −0.009 (2) |
C21 | 0.127 (3) | 0.076 (3) | 0.158 (4) | 0.025 (3) | 0.093 (3) | 0.008 (3) |
C20 | 0.082 (3) | 0.078 (3) | 0.161 (4) | 0.024 (2) | 0.053 (3) | 0.029 (3) |
C17 | 0.100 (3) | 0.141 (4) | 0.068 (3) | −0.014 (3) | −0.003 (2) | 0.037 (3) |
C6 | 0.104 (3) | 0.104 (3) | 0.061 (2) | −0.002 (2) | 0.002 (2) | −0.026 (2) |
C31 | 0.173 (4) | 0.056 (2) | 0.090 (3) | −0.015 (3) | 0.046 (3) | 0.000 (2) |
O5A | 0.228 (6) | 0.090 (3) | 0.156 (5) | −0.004 (4) | 0.062 (4) | −0.048 (3) |
O4A | 0.079 (3) | 0.166 (5) | 0.112 (3) | −0.026 (3) | 0.003 (2) | −0.019 (3) |
O6A | 0.128 (4) | 0.193 (6) | 0.135 (4) | −0.013 (4) | 0.088 (3) | 0.026 (4) |
O7A | 0.190 (5) | 0.112 (4) | 0.097 (3) | 0.013 (4) | 0.044 (4) | 0.048 (3) |
O4B | 0.176 (11) | 0.131 (9) | 0.135 (9) | −0.025 (7) | 0.048 (7) | 0.067 (7) |
O5B | 0.176 (11) | 0.212 (13) | 0.215 (12) | 0.012 (8) | 0.106 (9) | −0.035 (9) |
O6B | 0.164 (10) | 0.146 (10) | 0.120 (9) | −0.069 (7) | 0.062 (7) | −0.034 (7) |
O7B | 0.092 (7) | 0.133 (9) | 0.088 (7) | 0.006 (6) | 0.014 (5) | 0.004 (6) |
Geometric parameters (Å, º) top
Mn1—O1W | 2.123 (2) | C9—C8 | 1.345 (5) |
Mn1—O1 | 2.1249 (17) | C9—C10 | 1.394 (5) |
Mn1—N3 | 2.264 (2) | C9—H9 | 0.9300 |
Mn1—N2 | 2.288 (2) | C33—C32 | 1.383 (5) |
Mn1—N4 | 2.289 (2) | C33—H33 | 0.9300 |
Mn1—N1 | 2.300 (2) | C16—C15 | 1.403 (6) |
Cl1—O4B | 1.331 (9) | C16—C17 | 1.419 (6) |
Cl1—O7A | 1.365 (4) | C8—H8 | 0.9300 |
Cl1—O5B | 1.374 (8) | C14—C15 | 1.341 (6) |
Cl1—O4A | 1.400 (3) | C14—C13 | 1.402 (5) |
Cl1—O6B | 1.415 (8) | C14—H14 | 0.9300 |
Cl1—O5A | 1.422 (4) | C29—C30 | 1.378 (4) |
Cl1—O6A | 1.426 (4) | C29—H29 | 0.9300 |
Cl1—O7B | 1.436 (7) | C5—C6 | 1.335 (5) |
O1—C25 | 1.261 (3) | C5—H5 | 0.9300 |
N1—C1 | 1.332 (3) | C13—H13 | 0.9300 |
N1—C12 | 1.365 (3) | C22—C21 | 1.387 (5) |
N4—C13 | 1.326 (4) | C22—H22 | 0.9300 |
N4—C24 | 1.355 (4) | C19—C20 | 1.401 (5) |
N2—C10 | 1.327 (4) | C19—C18 | 1.438 (5) |
N2—C11 | 1.355 (4) | C1—C2 | 1.392 (4) |
N5—C27 | 1.334 (3) | C1—H1 | 0.9300 |
N5—C26 | 1.433 (3) | C10—H10 | 0.9300 |
N5—H5A | 0.8600 | O4W—H4B | 0.8797 |
C26—C25 | 1.507 (3) | O4W—H4A | 0.9192 |
C26—H26B | 0.9700 | O3W—H3B | 0.8986 |
C26—H26A | 0.9700 | O3W—H3A | 0.9027 |
C24—C16 | 1.410 (4) | O2W—H2B | 0.8993 |
C24—C23 | 1.439 (4) | O2W—H2A | 0.8948 |
C25—O2 | 1.238 (3) | C30—C31 | 1.352 (5) |
C12—C4 | 1.407 (4) | C30—H30 | 0.9300 |
C12—C11 | 1.431 (4) | C2—C3 | 1.357 (5) |
O1W—H1B | 0.8908 | C2—H2 | 0.9300 |
O1W—H1A | 0.8992 | C18—C17 | 1.329 (6) |
C11—C7 | 1.407 (4) | C18—H18 | 0.9300 |
C23—N3 | 1.355 (3) | C3—H3 | 0.9300 |
C23—C19 | 1.401 (4) | C32—C31 | 1.366 (5) |
N3—C22 | 1.328 (3) | C32—H32 | 0.9300 |
C28—C29 | 1.374 (4) | C15—H15 | 0.9300 |
C28—C33 | 1.380 (4) | C21—C20 | 1.349 (6) |
C28—C27 | 1.492 (4) | C21—H21 | 0.9300 |
C4—C3 | 1.399 (5) | C20—H20 | 0.9300 |
C4—C5 | 1.423 (5) | C17—H17 | 0.9300 |
C7—C8 | 1.393 (5) | C6—H6 | 0.9300 |
C7—C6 | 1.427 (5) | C31—H31 | 0.9300 |
O3—C27 | 1.225 (3) | | |
| | | |
O1W—Mn1—O1 | 88.04 (7) | O3—C27—N5 | 121.5 (3) |
O1W—Mn1—N3 | 162.17 (9) | O3—C27—C28 | 122.1 (3) |
O1—Mn1—N3 | 88.40 (7) | N5—C27—C28 | 116.4 (2) |
O1W—Mn1—N2 | 99.55 (9) | C8—C9—C10 | 119.1 (3) |
O1—Mn1—N2 | 90.30 (8) | C8—C9—H9 | 120.4 |
N3—Mn1—N2 | 97.93 (8) | C10—C9—H9 | 120.4 |
O1W—Mn1—N4 | 91.24 (9) | C28—C33—C32 | 119.9 (3) |
O1—Mn1—N4 | 104.75 (7) | C28—C33—H33 | 120.1 |
N3—Mn1—N4 | 72.82 (8) | C32—C33—H33 | 120.1 |
N2—Mn1—N4 | 161.82 (9) | C15—C16—C24 | 116.4 (4) |
O1W—Mn1—N1 | 96.74 (8) | C15—C16—C17 | 124.3 (4) |
O1—Mn1—N1 | 162.53 (8) | C24—C16—C17 | 119.2 (4) |
N3—Mn1—N1 | 91.85 (8) | C9—C8—C7 | 120.3 (3) |
N2—Mn1—N1 | 72.36 (8) | C9—C8—H8 | 119.9 |
N4—Mn1—N1 | 91.98 (8) | C7—C8—H8 | 119.9 |
O4B—Cl1—O5B | 119.3 (8) | C15—C14—C13 | 119.2 (4) |
O7A—Cl1—O4A | 112.8 (3) | C15—C14—H14 | 120.4 |
O4B—Cl1—O6B | 115.1 (8) | C13—C14—H14 | 120.4 |
O5B—Cl1—O6B | 108.2 (8) | C28—C29—C30 | 120.6 (3) |
O7A—Cl1—O5A | 109.6 (3) | C28—C29—H29 | 119.7 |
O4A—Cl1—O5A | 109.7 (3) | C30—C29—H29 | 119.7 |
O7A—Cl1—O6A | 110.4 (3) | C6—C5—C4 | 121.7 (4) |
O4A—Cl1—O6A | 106.9 (3) | C6—C5—H5 | 119.2 |
O5A—Cl1—O6A | 107.2 (4) | C4—C5—H5 | 119.2 |
O4B—Cl1—O7B | 107.0 (7) | N4—C13—C14 | 122.5 (4) |
O5B—Cl1—O7B | 103.8 (8) | N4—C13—H13 | 118.7 |
O6B—Cl1—O7B | 101.1 (7) | C14—C13—H13 | 118.7 |
C25—O1—Mn1 | 131.12 (17) | N3—C22—C21 | 122.9 (3) |
C1—N1—C12 | 117.7 (2) | N3—C22—H22 | 118.5 |
C1—N1—Mn1 | 126.96 (19) | C21—C22—H22 | 118.5 |
C12—N1—Mn1 | 115.22 (17) | C23—C19—C20 | 117.6 (3) |
C13—N4—C24 | 118.1 (3) | C23—C19—C18 | 118.4 (4) |
C13—N4—Mn1 | 126.6 (2) | C20—C19—C18 | 124.0 (4) |
C24—N4—Mn1 | 115.27 (17) | N1—C1—C2 | 123.6 (3) |
C10—N2—C11 | 117.6 (3) | N1—C1—H1 | 118.2 |
C10—N2—Mn1 | 126.2 (2) | C2—C1—H1 | 118.2 |
C11—N2—Mn1 | 116.12 (17) | N2—C10—C9 | 123.1 (4) |
C27—N5—C26 | 121.7 (2) | N2—C10—H10 | 118.4 |
C27—N5—H5A | 119.2 | C9—C10—H10 | 118.4 |
C26—N5—H5A | 119.2 | H4B—O4W—H4A | 100.9 |
N5—C26—C25 | 115.5 (2) | H3B—O3W—H3A | 93.8 |
N5—C26—H26B | 108.4 | H2B—O2W—H2A | 106.0 |
C25—C26—H26B | 108.4 | C31—C30—C29 | 120.1 (3) |
N5—C26—H26A | 108.4 | C31—C30—H30 | 120.0 |
C25—C26—H26A | 108.4 | C29—C30—H30 | 120.0 |
H26B—C26—H26A | 107.5 | C3—C2—C1 | 118.2 (3) |
N4—C24—C16 | 122.8 (3) | C3—C2—H2 | 120.9 |
N4—C24—C23 | 118.0 (2) | C1—C2—H2 | 120.9 |
C16—C24—C23 | 119.2 (3) | C17—C18—C19 | 121.6 (4) |
O2—C25—O1 | 125.1 (2) | C17—C18—H18 | 119.2 |
O2—C25—C26 | 120.1 (2) | C19—C18—H18 | 119.2 |
O1—C25—C26 | 114.8 (2) | C2—C3—C4 | 121.1 (3) |
N1—C12—C4 | 122.3 (3) | C2—C3—H3 | 119.5 |
N1—C12—C11 | 118.1 (2) | C4—C3—H3 | 119.5 |
C4—C12—C11 | 119.6 (3) | C31—C32—C33 | 120.1 (3) |
Mn1—O1W—H1B | 110.3 | C31—C32—H32 | 119.9 |
Mn1—O1W—H1A | 142.1 | C33—C32—H32 | 119.9 |
H1B—O1W—H1A | 107.6 | C14—C15—C16 | 120.8 (4) |
N2—C11—C7 | 122.5 (3) | C14—C15—H15 | 119.6 |
N2—C11—C12 | 117.9 (2) | C16—C15—H15 | 119.6 |
C7—C11—C12 | 119.6 (3) | C20—C21—C22 | 119.7 (4) |
N3—C23—C19 | 122.4 (3) | C20—C21—H21 | 120.1 |
N3—C23—C24 | 117.6 (2) | C22—C21—H21 | 120.1 |
C19—C23—C24 | 120.0 (3) | C21—C20—C19 | 119.5 (4) |
C22—N3—C23 | 117.8 (3) | C21—C20—H20 | 120.3 |
C22—N3—Mn1 | 125.9 (2) | C19—C20—H20 | 120.3 |
C23—N3—Mn1 | 116.34 (18) | C18—C17—C16 | 121.5 (4) |
C29—C28—C33 | 119.0 (3) | C18—C17—H17 | 119.2 |
C29—C28—C27 | 121.6 (2) | C16—C17—H17 | 119.2 |
C33—C28—C27 | 119.4 (3) | C5—C6—C7 | 121.2 (3) |
C3—C4—C12 | 117.0 (3) | C5—C6—H6 | 119.4 |
C3—C4—C5 | 124.1 (3) | C7—C6—H6 | 119.4 |
C12—C4—C5 | 118.9 (3) | C30—C31—C32 | 120.4 (4) |
C8—C7—C11 | 117.3 (3) | C30—C31—H31 | 119.8 |
C8—C7—C6 | 123.8 (3) | C32—C31—H31 | 119.8 |
C11—C7—C6 | 118.9 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1B···O2 | 0.90 | 1.83 | 2.645 (3) | 152 |
O2W—H2B···O2i | 0.90 | 1.84 | 2.701 (3) | 160 |
O3W—H3B···O3 | 0.90 | 1.85 | 2.745 (3) | 178 |
O1W—H1A···O2W | 0.90 | 1.71 | 2.595 (4) | 166 |
O2W—H2A···O4W | 0.90 | 1.90 | 2.760 (4) | 158 |
O4W—H4B···O3Wii | 0.88 | 1.98 | 2.816 (4) | 157 |
C3—H3···Cg1iii | 0.93 | 2.75 | 3.680 (4) | 174 |
C5—H5···Cg2iii | 0.93 | 3.04 | 3.961 (5) | 172 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1/2, y+1/2, −z+1/2; (iii) −x+1, −y+2, −z+1. |