metal-organic compounds
In the title complex, [Mn(C6H2N3O7)2(C32H36N2O4)], the Mn atom is six-coordinated by four O atoms from the 2-[2′-(diethylcarbamoylmethoxy)-1,1′-binaphth-2-yloxy]-N,N-diethylacetamide ligand and two O atoms from two monodentate 2,4,6-trinitrophenolate (picrate) ligands. In the crystal structure, the molecule possesses a crystallographically imposed twofold axis of symmetry.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804028107/cv6404sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804028107/cv6404Isup2.hkl |
CCDC reference: 258654
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.004 Å
- R factor = 0.040
- wR factor = 0.094
- Data-to-parameter ratio = 11.4
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT241_ALERT_2_B Check High U(eq) as Compared to Neighbors for O3
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT213_ALERT_2_C Atom O4' has ADP max/min Ratio ............. 3.90 oblate PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 3.21 Ratio PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for Mn PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for N4 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C18 PLAT301_ALERT_3_C Main Residue Disorder ......................... 12.00 Perc. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C18 - C19 ... 1.36 Ang. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 38.50 Deg. O9' -N4 -O9 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 24.40 Deg. N2' -C18 -N2 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 11 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 9 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
{2-[2'-(Diethylcarbamoylmethoxy)-1,1'-binaphthyl-2-yloxy]-N,N-diethylacetamide- κ4O}(2,4,6-trinitrophenolato)manganese(II) top
Crystal data top
[Mn(C6H2N3O7)2(C32H36N2O4)] | F(000) = 2116 |
Mr = 1023.78 | Dx = 1.455 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 22.802 (4) Å | Cell parameters from 36 reflections |
b = 14.879 (2) Å | θ = 3.2–13.6° |
c = 14.635 (2) Å | µ = 0.37 mm−1 |
β = 109.69 (1)° | T = 296 K |
V = 4675.1 (14) Å3 | Block, yellow |
Z = 4 | 0.56 × 0.40 × 0.40 mm |
Data collection top
Siemens P4 diffractometer | 2312 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.015 |
Graphite monochromator | θmax = 25.3°, θmin = 1.7° |
ω scans | h = 0→27 |
Absorption correction: multi-scan (DENZO–SMN; Otwinowski & Minor, 1997) | k = 0→17 |
Tmin = 0.786, Tmax = 0.863 | l = −17→16 |
4704 measured reflections | 3 standard reflections every 97 reflections |
4245 independent reflections | intensity decay: 1.8% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.094 | w = 1/[σ2(Fo2) + (0.0478P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.82 | (Δ/σ)max = 0.001 |
4245 reflections | Δρmax = 0.35 e Å−3 |
371 parameters | Δρmin = −0.21 e Å−3 |
9 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00184 (14) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Mn | 0.5000 | 0.27437 (3) | 0.7500 | 0.05200 (19) | |
O1 | 0.48798 (8) | 0.14743 (10) | 0.84438 (12) | 0.0557 (5) | |
O2 | 0.40683 (7) | 0.23527 (11) | 0.70854 (12) | 0.0579 (5) | |
O3 | 0.49933 (11) | 0.36375 (12) | 0.64383 (16) | 0.0950 (7) | |
O6 | 0.37020 (13) | 0.71692 (15) | 0.45220 (18) | 0.1094 (8) | |
O7 | 0.45838 (13) | 0.77114 (15) | 0.54317 (17) | 0.1029 (8) | |
N1 | 0.32233 (11) | 0.17097 (15) | 0.72516 (17) | 0.0717 (7) | |
N3 | 0.42198 (16) | 0.70931 (18) | 0.5123 (2) | 0.0815 (8) | |
N4 | 0.58533 (16) | 0.5136 (3) | 0.7067 (3) | 0.0917 (9) | |
C1 | 0.52606 (11) | 0.00984 (15) | 0.79768 (17) | 0.0485 (6) | |
C2 | 0.57461 (12) | −0.05660 (16) | 0.8195 (2) | 0.0552 (7) | |
C3 | 0.57487 (13) | −0.12621 (16) | 0.7544 (2) | 0.0680 (8) | |
H3 | 0.5422 | −0.1309 | 0.6958 | 0.082* | |
C4 | 0.62291 (16) | −0.1873 (2) | 0.7767 (3) | 0.0886 (10) | |
H4 | 0.6224 | −0.2331 | 0.7332 | 0.106* | |
C5 | 0.67201 (18) | −0.1811 (2) | 0.8635 (3) | 0.0989 (12) | |
H5 | 0.7040 | −0.2233 | 0.8779 | 0.119* | |
C6 | 0.67414 (14) | −0.1148 (2) | 0.9275 (3) | 0.0845 (10) | |
H6 | 0.7077 | −0.1113 | 0.9851 | 0.101* | |
C7 | 0.62557 (13) | −0.05018 (18) | 0.9077 (2) | 0.0636 (7) | |
C8 | 0.62708 (14) | 0.0205 (2) | 0.9718 (2) | 0.0725 (8) | |
H8 | 0.6606 | 0.0250 | 1.0294 | 0.087* | |
C9 | 0.58045 (13) | 0.08305 (18) | 0.95162 (19) | 0.0649 (8) | |
H9 | 0.5819 | 0.1292 | 0.9952 | 0.078* | |
C10 | 0.53062 (11) | 0.07639 (15) | 0.86428 (18) | 0.0504 (6) | |
C11 | 0.42480 (11) | 0.12587 (16) | 0.83492 (18) | 0.0546 (7) | |
H11A | 0.4169 | 0.1403 | 0.8943 | 0.066* | |
H11B | 0.4169 | 0.0623 | 0.8215 | 0.066* | |
C12 | 0.38340 (12) | 0.18158 (17) | 0.75142 (19) | 0.0545 (7) | |
C13 | 0.28204 (13) | 0.2221 (2) | 0.6417 (2) | 0.0883 (10) | |
H13A | 0.2454 | 0.1865 | 0.6084 | 0.106* | |
H13B | 0.3042 | 0.2327 | 0.5966 | 0.106* | |
C14 | 0.26193 (17) | 0.3104 (2) | 0.6703 (3) | 0.1165 (13) | |
H14A | 0.2393 | 0.3003 | 0.7140 | 0.140* | |
H14B | 0.2357 | 0.3410 | 0.6134 | 0.140* | |
H14C | 0.2980 | 0.3466 | 0.7018 | 0.140* | |
C15 | 0.29070 (16) | 0.1164 (2) | 0.7805 (3) | 0.1021 (11) | |
H15A | 0.3180 | 0.1105 | 0.8474 | 0.122* | |
H15B | 0.2531 | 0.1469 | 0.7804 | 0.122* | |
C16 | 0.27513 (18) | 0.0287 (2) | 0.7383 (3) | 0.1203 (13) | |
H16A | 0.2530 | 0.0345 | 0.6700 | 0.144* | |
H16B | 0.2494 | −0.0019 | 0.7685 | 0.144* | |
H16C | 0.3126 | −0.0052 | 0.7482 | 0.144* | |
C17 | 0.48247 (15) | 0.44271 (18) | 0.6149 (2) | 0.0664 (8) | |
C18 | 0.42178 (15) | 0.46407 (18) | 0.5512 (2) | 0.0712 (8) | |
C19 | 0.40154 (14) | 0.5483 (2) | 0.5195 (2) | 0.0730 (8) | |
H19 | 0.3609 | 0.5577 | 0.4785 | 0.088* | |
C20 | 0.44200 (15) | 0.61858 (18) | 0.5490 (2) | 0.0635 (7) | |
C21 | 0.50161 (15) | 0.60608 (18) | 0.6105 (2) | 0.0674 (8) | |
H21 | 0.5287 | 0.6545 | 0.6302 | 0.081* | |
C22 | 0.52074 (14) | 0.52119 (19) | 0.6425 (2) | 0.0646 (7) | |
N2 | 0.3746 (2) | 0.3932 (3) | 0.5172 (4) | 0.0997 (18) | 0.882 (7) |
O4 | 0.3898 (3) | 0.3217 (3) | 0.4919 (4) | 0.1394 (19) | 0.882 (7) |
O5 | 0.32167 (19) | 0.4077 (2) | 0.5155 (3) | 0.1327 (16) | 0.882 (7) |
O8 | 0.6101 (4) | 0.5790 (4) | 0.7552 (8) | 0.135 (4) | 0.625 (18) |
O9 | 0.6126 (5) | 0.4421 (6) | 0.7171 (12) | 0.166 (5) | 0.625 (18) |
N2' | 0.3974 (15) | 0.3766 (8) | 0.509 (2) | 0.117 (15) | 0.118 (7) |
O4' | 0.4296 (11) | 0.3096 (15) | 0.535 (2) | 0.103 (10) | 0.118 (7) |
O5' | 0.3597 (14) | 0.382 (2) | 0.427 (3) | 0.18 (2) | 0.118 (7) |
O8' | 0.6222 (4) | 0.5681 (9) | 0.6928 (13) | 0.110 (5) | 0.375 (18) |
O9' | 0.5969 (7) | 0.4486 (10) | 0.7576 (10) | 0.102 (4) | 0.375 (18) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Mn | 0.0562 (4) | 0.0364 (3) | 0.0596 (4) | 0.000 | 0.0145 (3) | 0.000 |
O1 | 0.0544 (11) | 0.0397 (9) | 0.0676 (12) | 0.0023 (8) | 0.0135 (9) | −0.0018 (8) |
O2 | 0.0560 (11) | 0.0478 (10) | 0.0647 (11) | −0.0013 (9) | 0.0135 (9) | 0.0063 (9) |
O3 | 0.137 (2) | 0.0604 (13) | 0.1052 (17) | 0.0218 (13) | 0.0643 (15) | 0.0324 (12) |
O6 | 0.120 (2) | 0.0911 (17) | 0.1045 (18) | 0.0359 (16) | 0.0214 (16) | 0.0219 (15) |
O7 | 0.155 (2) | 0.0531 (13) | 0.0966 (17) | 0.0030 (15) | 0.0375 (16) | 0.0040 (13) |
N1 | 0.0533 (15) | 0.0732 (16) | 0.0828 (17) | −0.0066 (13) | 0.0153 (13) | 0.0169 (13) |
N3 | 0.110 (2) | 0.0677 (19) | 0.0681 (18) | 0.0164 (18) | 0.0319 (17) | 0.0099 (15) |
N4 | 0.096 (3) | 0.096 (2) | 0.081 (2) | 0.013 (2) | 0.027 (2) | 0.022 (2) |
C1 | 0.0496 (15) | 0.0382 (13) | 0.0580 (16) | 0.0007 (11) | 0.0184 (12) | 0.0070 (12) |
C2 | 0.0558 (17) | 0.0411 (14) | 0.0716 (18) | 0.0033 (13) | 0.0254 (15) | 0.0100 (13) |
C3 | 0.0670 (19) | 0.0478 (15) | 0.096 (2) | 0.0044 (15) | 0.0362 (17) | 0.0009 (16) |
C4 | 0.090 (3) | 0.0602 (19) | 0.132 (3) | 0.0143 (19) | 0.059 (3) | 0.002 (2) |
C5 | 0.090 (3) | 0.083 (2) | 0.135 (3) | 0.041 (2) | 0.054 (3) | 0.035 (2) |
C6 | 0.071 (2) | 0.089 (2) | 0.094 (3) | 0.0284 (19) | 0.0280 (19) | 0.035 (2) |
C7 | 0.0629 (19) | 0.0582 (17) | 0.071 (2) | 0.0102 (15) | 0.0241 (16) | 0.0207 (15) |
C8 | 0.066 (2) | 0.078 (2) | 0.0596 (19) | 0.0082 (17) | 0.0031 (15) | 0.0211 (17) |
C9 | 0.073 (2) | 0.0618 (18) | 0.0502 (17) | −0.0006 (16) | 0.0085 (16) | 0.0033 (14) |
C10 | 0.0557 (16) | 0.0384 (14) | 0.0546 (16) | 0.0028 (12) | 0.0153 (14) | 0.0077 (12) |
C11 | 0.0604 (18) | 0.0494 (14) | 0.0560 (16) | 0.0001 (13) | 0.0222 (14) | −0.0024 (13) |
C12 | 0.0574 (18) | 0.0458 (14) | 0.0568 (17) | 0.0021 (14) | 0.0147 (14) | −0.0073 (13) |
C13 | 0.0556 (18) | 0.100 (2) | 0.090 (2) | −0.0057 (18) | −0.0015 (16) | 0.016 (2) |
C14 | 0.101 (3) | 0.109 (3) | 0.140 (3) | 0.037 (2) | 0.041 (3) | 0.034 (3) |
C15 | 0.091 (3) | 0.084 (2) | 0.115 (3) | −0.002 (2) | 0.014 (2) | 0.017 (2) |
C16 | 0.107 (3) | 0.101 (3) | 0.151 (4) | −0.008 (2) | 0.041 (3) | 0.007 (3) |
C17 | 0.096 (2) | 0.0499 (17) | 0.0647 (19) | 0.0040 (17) | 0.0423 (18) | 0.0140 (15) |
C18 | 0.090 (2) | 0.0565 (18) | 0.067 (2) | −0.0131 (18) | 0.0260 (19) | 0.0062 (15) |
C19 | 0.077 (2) | 0.075 (2) | 0.0623 (19) | 0.0021 (18) | 0.0178 (16) | 0.0127 (16) |
C20 | 0.083 (2) | 0.0526 (17) | 0.0595 (18) | 0.0098 (16) | 0.0301 (17) | 0.0099 (14) |
C21 | 0.086 (2) | 0.0566 (18) | 0.0639 (18) | −0.0030 (16) | 0.0314 (17) | 0.0033 (15) |
C22 | 0.069 (2) | 0.0660 (19) | 0.0599 (18) | 0.0109 (16) | 0.0233 (16) | 0.0128 (15) |
N2 | 0.126 (4) | 0.086 (3) | 0.077 (3) | −0.030 (3) | 0.021 (4) | 0.005 (2) |
O4 | 0.168 (5) | 0.082 (3) | 0.154 (5) | −0.045 (3) | 0.034 (4) | −0.024 (3) |
O5 | 0.099 (3) | 0.158 (3) | 0.124 (3) | −0.048 (2) | 0.016 (2) | −0.002 (2) |
O8 | 0.107 (4) | 0.122 (4) | 0.143 (7) | −0.029 (3) | −0.003 (5) | 0.026 (4) |
O9 | 0.114 (7) | 0.141 (5) | 0.196 (11) | 0.057 (5) | −0.009 (6) | −0.015 (6) |
N2' | 0.19 (4) | 0.032 (17) | 0.12 (4) | −0.04 (3) | 0.06 (4) | −0.02 (2) |
O4' | 0.098 (19) | 0.042 (14) | 0.15 (3) | −0.050 (13) | 0.013 (16) | −0.018 (13) |
O5' | 0.13 (2) | 0.13 (2) | 0.19 (4) | −0.081 (19) | −0.06 (2) | 0.05 (2) |
O8' | 0.068 (5) | 0.142 (7) | 0.108 (10) | −0.019 (5) | 0.016 (5) | 0.037 (6) |
O9' | 0.085 (6) | 0.122 (8) | 0.105 (7) | 0.048 (5) | 0.039 (5) | 0.044 (6) |
Geometric parameters (Å, º) top
Mn—O3i | 2.0413 (19) | C7—C8 | 1.403 (4) |
Mn—O3 | 2.0413 (19) | C8—C9 | 1.368 (4) |
Mn—O2 | 2.0859 (17) | C8—H8 | 0.9300 |
Mn—O2i | 2.0859 (17) | C9—C10 | 1.399 (3) |
Mn—O1 | 2.4095 (16) | C9—H9 | 0.9300 |
Mn—O1i | 2.4095 (16) | C11—C12 | 1.515 (3) |
O1—C10 | 1.399 (3) | C11—H11A | 0.9700 |
O1—C11 | 1.436 (3) | C11—H11B | 0.9700 |
O2—C12 | 1.242 (3) | C13—C14 | 1.497 (4) |
O3—C17 | 1.264 (3) | C13—H13A | 0.9700 |
O6—N3 | 1.217 (3) | C13—H13B | 0.9700 |
O7—N3 | 1.219 (3) | C14—H14A | 0.9600 |
N1—C12 | 1.323 (3) | C14—H14B | 0.9600 |
N1—C13 | 1.470 (3) | C14—H14C | 0.9600 |
N1—C15 | 1.493 (4) | C15—C16 | 1.437 (4) |
N3—C20 | 1.468 (3) | C15—H15A | 0.9700 |
N4—O9' | 1.194 (11) | C15—H15B | 0.9700 |
N4—O9 | 1.216 (3) | C16—H16A | 0.9600 |
N4—O8 | 1.225 (3) | C16—H16B | 0.9600 |
N4—O8' | 1.233 (9) | C16—H16C | 0.9600 |
N4—C22 | 1.460 (4) | C17—C18 | 1.420 (4) |
C1—C10 | 1.369 (3) | C17—C22 | 1.432 (4) |
C1—C2 | 1.437 (3) | C18—C19 | 1.361 (4) |
C1—C1i | 1.498 (5) | C18—N2' | 1.466 (3) |
C2—C3 | 1.408 (3) | C18—N2 | 1.468 (3) |
C2—C7 | 1.419 (4) | C19—C20 | 1.365 (4) |
C3—C4 | 1.375 (4) | C19—H19 | 0.9300 |
C3—H3 | 0.9300 | C20—C21 | 1.367 (4) |
C4—C5 | 1.385 (4) | C21—C22 | 1.367 (3) |
C4—H4 | 0.9300 | C21—H21 | 0.9300 |
C5—C6 | 1.351 (4) | N2—O4 | 1.216 (3) |
C5—H5 | 0.9300 | N2—O5 | 1.217 (3) |
C6—C7 | 1.420 (4) | N2'—O5' | 1.220 (3) |
C6—H6 | 0.9300 | N2'—O4' | 1.220 (3) |
O3i—Mn—O3 | 98.69 (12) | C1—C10—C9 | 123.1 (2) |
O3i—Mn—O2 | 98.56 (8) | C1—C10—O1 | 121.2 (2) |
O3—Mn—O2 | 102.39 (8) | C9—C10—O1 | 115.5 (2) |
O3i—Mn—O2i | 102.39 (8) | O1—C11—C12 | 106.7 (2) |
O3—Mn—O2i | 98.56 (8) | O1—C11—H11A | 110.4 |
O2—Mn—O2i | 147.60 (9) | C12—C11—H11A | 110.4 |
O3i—Mn—O1 | 92.72 (7) | O1—C11—H11B | 110.4 |
O3—Mn—O1 | 166.88 (8) | C12—C11—H11B | 110.4 |
O2—Mn—O1 | 69.31 (6) | H11A—C11—H11B | 108.6 |
O2i—Mn—O1 | 85.18 (6) | O2—C12—N1 | 121.3 (2) |
O3i—Mn—O1i | 166.88 (7) | O2—C12—C11 | 120.1 (2) |
O3—Mn—O1i | 92.72 (7) | N1—C12—C11 | 118.5 (2) |
O2—Mn—O1i | 85.18 (6) | N1—C13—C14 | 112.7 (3) |
O2i—Mn—O1i | 69.31 (6) | N1—C13—H13A | 109.0 |
O1—Mn—O1i | 76.77 (8) | C14—C13—H13A | 109.0 |
C10—O1—C11 | 117.10 (17) | N1—C13—H13B | 109.0 |
C10—O1—Mn | 120.42 (14) | C14—C13—H13B | 109.0 |
C11—O1—Mn | 115.08 (13) | H13A—C13—H13B | 107.8 |
C12—O2—Mn | 126.99 (16) | C13—C14—H14A | 109.5 |
C17—O3—Mn | 141.63 (19) | C13—C14—H14B | 109.5 |
C12—N1—C13 | 118.8 (2) | H14A—C14—H14B | 109.5 |
C12—N1—C15 | 124.1 (2) | C13—C14—H14C | 109.5 |
C13—N1—C15 | 116.9 (2) | H14A—C14—H14C | 109.5 |
O6—N3—O7 | 124.8 (3) | H14B—C14—H14C | 109.5 |
O6—N3—C20 | 117.2 (3) | C16—C15—N1 | 110.8 (3) |
O7—N3—C20 | 118.0 (3) | C16—C15—H15A | 109.5 |
O9'—N4—O9 | 38.5 (6) | N1—C15—H15A | 109.5 |
O9'—N4—O8 | 108.7 (9) | C16—C15—H15B | 109.5 |
O9—N4—O8 | 120.4 (7) | N1—C15—H15B | 109.5 |
O9'—N4—O8' | 128.0 (9) | H15A—C15—H15B | 108.1 |
O9—N4—O8' | 104.3 (8) | C15—C16—H16A | 109.5 |
O8—N4—O8' | 50.7 (5) | C15—C16—H16B | 109.5 |
O9'—N4—C22 | 115.3 (8) | H16A—C16—H16B | 109.5 |
O9—N4—C22 | 120.7 (6) | C15—C16—H16C | 109.5 |
O8—N4—C22 | 118.6 (4) | H16A—C16—H16C | 109.5 |
O8'—N4—C22 | 116.0 (6) | H16B—C16—H16C | 109.5 |
C10—C1—C2 | 118.1 (2) | O3—C17—C18 | 123.2 (3) |
C10—C1—C1i | 120.64 (18) | O3—C17—C22 | 125.2 (3) |
C2—C1—C1i | 121.1 (2) | C18—C17—C22 | 111.7 (2) |
C3—C2—C7 | 118.4 (2) | C19—C18—C17 | 125.0 (3) |
C3—C2—C1 | 122.3 (2) | C19—C18—N2' | 129.6 (10) |
C7—C2—C1 | 119.3 (2) | C17—C18—N2' | 103.0 (10) |
C4—C3—C2 | 120.7 (3) | C19—C18—N2 | 114.8 (3) |
C4—C3—H3 | 119.7 | C17—C18—N2 | 120.2 (3) |
C2—C3—H3 | 119.7 | N2'—C18—N2 | 24.4 (16) |
C3—C4—C5 | 120.5 (3) | C18—C19—C20 | 118.8 (3) |
C3—C4—H4 | 119.8 | C18—C19—H19 | 120.6 |
C5—C4—H4 | 119.8 | C20—C19—H19 | 120.6 |
C6—C5—C4 | 120.9 (3) | C19—C20—C21 | 121.4 (3) |
C6—C5—H5 | 119.5 | C19—C20—N3 | 119.7 (3) |
C4—C5—H5 | 119.5 | C21—C20—N3 | 118.9 (3) |
C5—C6—C7 | 120.6 (3) | C22—C21—C20 | 118.9 (3) |
C5—C6—H6 | 119.7 | C22—C21—H21 | 120.6 |
C7—C6—H6 | 119.7 | C20—C21—H21 | 120.6 |
C8—C7—C2 | 119.1 (2) | C21—C22—C17 | 124.3 (3) |
C8—C7—C6 | 121.9 (3) | C21—C22—N4 | 115.4 (3) |
C2—C7—C6 | 118.9 (3) | C17—C22—N4 | 120.3 (3) |
C9—C8—C7 | 121.6 (3) | O4—N2—O5 | 122.1 (4) |
C9—C8—H8 | 119.2 | O4—N2—C18 | 118.6 (4) |
C7—C8—H8 | 119.2 | O5—N2—C18 | 119.3 (4) |
C8—C9—C10 | 118.8 (3) | O5'—N2'—O4' | 120.5 (5) |
C8—C9—H9 | 120.6 | O5'—N2'—C18 | 114 (2) |
C10—C9—H9 | 120.6 | O4'—N2'—C18 | 119.4 (19) |
O3i—Mn—O1—C10 | −124.14 (17) | C13—N1—C12—C11 | −177.5 (2) |
O3—Mn—O1—C10 | 85.3 (4) | C15—N1—C12—C11 | 8.4 (4) |
O2—Mn—O1—C10 | 137.74 (17) | O1—C11—C12—O2 | −2.2 (3) |
O2i—Mn—O1—C10 | −21.92 (16) | O1—C11—C12—N1 | 177.2 (2) |
O1i—Mn—O1—C10 | 47.93 (14) | C12—N1—C13—C14 | −91.4 (3) |
O3i—Mn—O1—C11 | 86.76 (15) | C15—N1—C13—C14 | 83.1 (3) |
O3—Mn—O1—C11 | −63.8 (4) | C12—N1—C15—C16 | −98.7 (4) |
O2—Mn—O1—C11 | −11.37 (14) | C13—N1—C15—C16 | 87.1 (4) |
O2i—Mn—O1—C11 | −171.02 (15) | Mn—O3—C17—C18 | −86.9 (4) |
O1i—Mn—O1—C11 | −101.17 (15) | Mn—O3—C17—C22 | 92.0 (4) |
O3i—Mn—O2—C12 | −78.2 (2) | O3—C17—C18—C19 | 179.0 (3) |
O3—Mn—O2—C12 | −179.17 (19) | C22—C17—C18—C19 | −0.1 (4) |
O2i—Mn—O2—C12 | 51.72 (19) | O3—C17—C18—N2' | −17.4 (19) |
O1—Mn—O2—C12 | 11.44 (18) | C22—C17—C18—N2' | 163.5 (19) |
O1i—Mn—O2—C12 | 89.1 (2) | O3—C17—C18—N2 | 1.3 (5) |
O3i—Mn—O3—C17 | −27.2 (3) | C22—C17—C18—N2 | −177.7 (3) |
O2—Mn—O3—C17 | 73.6 (4) | C17—C18—C19—C20 | 1.0 (5) |
O2i—Mn—O3—C17 | −131.3 (4) | N2'—C18—C19—C20 | −158 (2) |
O1—Mn—O3—C17 | 123.0 (4) | N2—C18—C19—C20 | 178.8 (3) |
O1i—Mn—O3—C17 | 159.2 (4) | C18—C19—C20—C21 | −1.1 (4) |
C10—C1—C2—C3 | −178.3 (2) | C18—C19—C20—N3 | 177.3 (3) |
C1i—C1—C2—C3 | −2.0 (4) | O6—N3—C20—C19 | −3.8 (4) |
C10—C1—C2—C7 | −1.0 (3) | O7—N3—C20—C19 | 177.1 (3) |
C1i—C1—C2—C7 | 175.3 (2) | O6—N3—C20—C21 | 174.7 (3) |
C7—C2—C3—C4 | 1.1 (4) | O7—N3—C20—C21 | −4.5 (4) |
C1—C2—C3—C4 | 178.4 (2) | C19—C20—C21—C22 | 0.2 (4) |
C2—C3—C4—C5 | −0.2 (5) | N3—C20—C21—C22 | −178.2 (2) |
C3—C4—C5—C6 | −0.7 (5) | C20—C21—C22—C17 | 0.8 (4) |
C4—C5—C6—C7 | 0.7 (5) | C20—C21—C22—N4 | 179.1 (3) |
C3—C2—C7—C8 | 177.9 (2) | O3—C17—C22—C21 | −179.9 (3) |
C1—C2—C7—C8 | 0.5 (4) | C18—C17—C22—C21 | −0.9 (4) |
C3—C2—C7—C6 | −1.0 (4) | O3—C17—C22—N4 | 1.9 (4) |
C1—C2—C7—C6 | −178.4 (2) | C18—C17—C22—N4 | −179.1 (3) |
C5—C6—C7—C8 | −178.7 (3) | O9'—N4—C22—C21 | 157.9 (9) |
C5—C6—C7—C2 | 0.2 (4) | O9—N4—C22—C21 | −158.7 (11) |
C2—C7—C8—C9 | 0.4 (4) | O8—N4—C22—C21 | 26.4 (10) |
C6—C7—C8—C9 | 179.3 (3) | O8'—N4—C22—C21 | −31.1 (12) |
C7—C8—C9—C10 | −0.8 (4) | O9'—N4—C22—C17 | −23.8 (10) |
C2—C1—C10—C9 | 0.7 (4) | O9—N4—C22—C17 | 19.7 (12) |
C1i—C1—C10—C9 | −175.7 (3) | O8—N4—C22—C17 | −155.2 (9) |
C2—C1—C10—O1 | 174.5 (2) | O8'—N4—C22—C17 | 147.3 (11) |
C1i—C1—C10—O1 | −1.8 (4) | C19—C18—N2—O4 | 138.8 (6) |
C8—C9—C10—C1 | 0.2 (4) | C17—C18—N2—O4 | −43.3 (8) |
C8—C9—C10—O1 | −174.0 (2) | N2'—C18—N2—O4 | 6 (3) |
C11—O1—C10—C1 | 66.9 (3) | C19—C18—N2—O5 | −41.4 (7) |
Mn—O1—C10—C1 | −81.6 (2) | C17—C18—N2—O5 | 136.6 (5) |
C11—O1—C10—C9 | −118.8 (2) | N2'—C18—N2—O5 | −174 (4) |
Mn—O1—C10—C9 | 92.7 (2) | C19—C18—N2'—O5' | 12 (4) |
C10—O1—C11—C12 | −139.8 (2) | C17—C18—N2'—O5' | −150 (2) |
Mn—O1—C11—C12 | 10.4 (2) | N2—C18—N2'—O5' | 72 (4) |
Mn—O2—C12—N1 | 170.99 (18) | C19—C18—N2'—O4' | 164 (3) |
Mn—O2—C12—C11 | −9.6 (3) | C17—C18—N2'—O4' | 1 (4) |
C13—N1—C12—O2 | 1.8 (4) | N2—C18—N2'—O4' | −137 (7) |
C15—N1—C12—O2 | −172.2 (3) |
Symmetry code: (i) −x+1, y, −z+3/2. |