Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680703557X/cv2276sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680703557X/cv2276Isup2.hkl |
CCDC reference: 657641
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- R factor = 0.039
- wR factor = 0.097
- Data-to-parameter ratio = 12.8
checkCIF/PLATON results
No syntax errors found Datablock: I
Alert level C PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Mn1 - O3 .. 6.92 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Mn1 - N1 .. 5.30 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Mn1 - N3 .. 5.65 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Mn2 - O7 .. 8.02 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O7 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N5 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N8 PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1 - C2 ... 1.54 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact F5 .. C33 .. 2.91 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H28 .. F1 .. 2.61 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H33 .. F5 .. 2.58 Ang.
Alert level G PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT794_ALERT_5_G Check Predicted Bond Valency for Mn1 (2) 1.98 PLAT794_ALERT_5_G Check Predicted Bond Valency for Mn2 (2) 1.86
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 3 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 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
Fluorobenzene derivatives such as pentafluorobenzoic acid have been analysed based on single-crystal X-ray structure analysis (Benghiat & Leiserowitz, 1972; Bach et al., 2001). C6F5CO2H, C6F4HCO2H or monofluoro benzoic acid derivatives have been used to prepare metal carboxylates (Mitsuhiro et al., 2003; Ribas et al., 1997). For an attractive interaction between the F atom of fluorobenzene and a π system, see: Thalladi et al. (1998).
The title compound was obtained as following: added aqueous solution of manganese(II) nitrate (1 mmol) and phen (3 mmol) slowly to aqueous solution of pentafluorobenzoic acid (1 mmol) and KOH (1 mmol) with stirring, then the resulting mixture was stirred 4 h under refluxing. The solution was filtered. By slow evaporation, yellow block-shape single crystals suitable for X-ray analysis were obtained within several weeks.
All H atoms were geometrically positioned [C—H 0.93 Å], and treated as riding, with Uiso(H) = 1.2Ueq(C).
The title compound contains two types of neutral molecules - Mn(Phen)2(F5C6COO)(NO3) (A) and Mn(Phen)2(NO3)2 (B), respectively, with a 2:1 ratio. The Mn ions in two molecules are coordinated by four N atoms and two O atoms in a distorted octahedral geometry each (Table 2).
In the crystal, significant F···F interactions are favored (F3···F3(1/2 - x,-1/2 - y,1 - z) = 2.813 (2) Å; F3—F4(1/2 - x,-1/2 - y,1 - z) =3.020 (3) Å). The crystal packing exhibits weak intermolecular C—H···O and C—H···F hydrogen bonds (Table 1), and π···π interactions proved by relatively short distances of 3.6775 (14) and 3.8214 (13) Å between the centroids of six-membered rings from the neighbouring molecules (Table 2).
Fluorobenzene derivatives such as pentafluorobenzoic acid have been analysed based on single-crystal X-ray structure analysis (Benghiat & Leiserowitz, 1972; Bach et al., 2001). C6F5CO2H, C6F4HCO2H or monofluoro benzoic acid derivatives have been used to prepare metal carboxylates (Mitsuhiro et al., 2003; Ribas et al., 1997). For an attractive interaction between the F atom of fluorobenzene and a π system, see: Thalladi et al. (1998).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Bruker SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXL97.
Fig. 1. View of (I), showing atomic labels and displacement ellipsoids drawn at the 50% probability level [symmetry code: (A) -x, y, -z + 1/2]. H atoms omitted for clarity. |
[Mn(C7F5O2)(NO3)(C12H8N2)2]2·[Mn(NO3)2(C12H8N2)2] | F(000) = 3876 |
Mr = 1916.22 | Dx = 1.649 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C2yc | Cell parameters from 749 reflections |
a = 45.889 (3) Å | θ = 2.6–22.7° |
b = 10.1112 (6) Å | µ = 0.59 mm−1 |
c = 17.7948 (10) Å | T = 295 K |
β = 110.756 (1)° | Block, yellow |
V = 7720.8 (8) Å3 | 0.15 × 0.12 × 0.10 mm |
Z = 4 |
CCD area-detector diffractometer | 7585 independent reflections |
Radiation source: fine-focus sealed tube | 6126 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
phi and ω scans | θmax = 26.1°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −52→56 |
Tmin = 0.911, Tmax = 0.933 | k = −11→12 |
21136 measured reflections | l = −19→21 |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.097 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0449P)2 + 5.7994P] where P = (Fo2 + 2Fc2)/3 |
7585 reflections | (Δ/σ)max = 0.001 |
591 parameters | Δρmax = 0.48 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
[Mn(C7F5O2)(NO3)(C12H8N2)2]2·[Mn(NO3)2(C12H8N2)2] | V = 7720.8 (8) Å3 |
Mr = 1916.22 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 45.889 (3) Å | µ = 0.59 mm−1 |
b = 10.1112 (6) Å | T = 295 K |
c = 17.7948 (10) Å | 0.15 × 0.12 × 0.10 mm |
β = 110.756 (1)° |
CCD area-detector diffractometer | 7585 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 6126 reflections with I > 2σ(I) |
Tmin = 0.911, Tmax = 0.933 | Rint = 0.027 |
21136 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.097 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.48 e Å−3 |
7585 reflections | Δρmin = −0.25 e Å−3 |
591 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C43 | 0.03336 (6) | 1.1563 (2) | 0.50464 (15) | 0.0444 (6) | |
H43 | 0.0310 | 1.2245 | 0.5371 | 0.053* | |
C42 | 0.00697 (6) | 1.1132 (2) | 0.43748 (13) | 0.0350 (5) | |
Mn1 | 0.148454 (7) | 0.35412 (3) | 0.382044 (19) | 0.02757 (10) | |
N5 | 0.16267 (4) | 0.14679 (19) | 0.50756 (12) | 0.0356 (4) | |
O3 | 0.17706 (4) | 0.20487 (16) | 0.46679 (9) | 0.0402 (4) | |
F1 | 0.20011 (3) | 0.17676 (16) | 0.25519 (10) | 0.0578 (4) | |
F3 | 0.24872 (4) | −0.14013 (16) | 0.45045 (10) | 0.0661 (5) | |
F4 | 0.19236 (4) | −0.21137 (16) | 0.45704 (10) | 0.0672 (5) | |
O5 | 0.17547 (4) | 0.05628 (17) | 0.55339 (10) | 0.0480 (4) | |
O2 | 0.13379 (4) | 0.22998 (16) | 0.28005 (9) | 0.0380 (4) | |
N4 | 0.15013 (4) | 0.48379 (18) | 0.48769 (10) | 0.0311 (4) | |
N1 | 0.19547 (4) | 0.42421 (18) | 0.37690 (11) | 0.0321 (4) | |
F5 | 0.14027 (4) | −0.08701 (17) | 0.36266 (10) | 0.0622 (4) | |
N3 | 0.09923 (4) | 0.37216 (18) | 0.37779 (11) | 0.0330 (4) | |
N2 | 0.13914 (4) | 0.53424 (17) | 0.29593 (10) | 0.0300 (4) | |
C1 | 0.13860 (5) | 0.1196 (2) | 0.25465 (13) | 0.0343 (5) | |
C11 | 0.22118 (5) | 0.5765 (2) | 0.31515 (13) | 0.0351 (5) | |
C2 | 0.16855 (5) | 0.0482 (2) | 0.30657 (13) | 0.0322 (5) | |
C5 | 0.22249 (6) | −0.0790 (2) | 0.40499 (15) | 0.0434 (6) | |
C31 | 0.09537 (5) | 0.4385 (2) | 0.43976 (13) | 0.0314 (5) | |
C4 | 0.22417 (6) | 0.0196 (3) | 0.35357 (16) | 0.0459 (6) | |
C23 | 0.06602 (6) | 0.4514 (2) | 0.44829 (15) | 0.0406 (6) | |
C19 | 0.19443 (5) | 0.5265 (2) | 0.32645 (12) | 0.0302 (5) | |
C14 | 0.16242 (5) | 0.6912 (2) | 0.23027 (13) | 0.0344 (5) | |
C30 | 0.12250 (5) | 0.4971 (2) | 0.49869 (13) | 0.0308 (5) | |
C15 | 0.13288 (6) | 0.7456 (2) | 0.19022 (14) | 0.0422 (6) | |
H15 | 0.1305 | 0.8162 | 0.1551 | 0.051* | |
C3 | 0.19740 (6) | 0.0817 (2) | 0.30517 (14) | 0.0394 (6) | |
C18 | 0.16441 (5) | 0.5852 (2) | 0.28339 (12) | 0.0288 (5) | |
O1 | 0.12288 (5) | 0.06588 (19) | 0.19263 (11) | 0.0615 (6) | |
C17 | 0.11156 (5) | 0.5883 (2) | 0.25586 (13) | 0.0365 (5) | |
H17 | 0.0941 | 0.5534 | 0.2635 | 0.044* | |
C8 | 0.22307 (5) | 0.3704 (2) | 0.41628 (15) | 0.0400 (6) | |
H8 | 0.2239 | 0.3001 | 0.4507 | 0.048* | |
F2 | 0.25214 (3) | 0.05384 (19) | 0.35069 (12) | 0.0786 (6) | |
C7 | 0.16769 (6) | −0.0508 (2) | 0.35868 (14) | 0.0390 (6) | |
C25 | 0.08929 (7) | 0.5742 (3) | 0.57119 (17) | 0.0528 (8) | |
H25 | 0.0872 | 0.6184 | 0.6149 | 0.063* | |
C6 | 0.19429 (6) | −0.1149 (2) | 0.40790 (14) | 0.0427 (6) | |
C13 | 0.19028 (6) | 0.7384 (2) | 0.22008 (14) | 0.0408 (6) | |
H13 | 0.1890 | 0.8077 | 0.1847 | 0.049* | |
C28 | 0.17431 (7) | 0.6064 (3) | 0.60876 (15) | 0.0528 (7) | |
H28 | 0.1924 | 0.6423 | 0.6455 | 0.063* | |
C29 | 0.17518 (6) | 0.5374 (2) | 0.54133 (14) | 0.0402 (6) | |
H29 | 0.1942 | 0.5290 | 0.5340 | 0.048* | |
O4 | 0.13659 (4) | 0.1855 (2) | 0.50111 (15) | 0.0706 (7) | |
C21 | 0.04466 (6) | 0.3249 (3) | 0.32733 (18) | 0.0506 (7) | |
H21 | 0.0278 | 0.2854 | 0.2879 | 0.061* | |
C24 | 0.06391 (7) | 0.5208 (3) | 0.51567 (17) | 0.0512 (7) | |
H24 | 0.0446 | 0.5294 | 0.5215 | 0.061* | |
C10 | 0.24987 (5) | 0.5164 (3) | 0.35839 (15) | 0.0437 (6) | |
H10 | 0.2681 | 0.5466 | 0.3526 | 0.052* | |
C27 | 0.14646 (7) | 0.6202 (2) | 0.61980 (15) | 0.0517 (7) | |
H27 | 0.1455 | 0.6665 | 0.6640 | 0.062* | |
C26 | 0.11950 (6) | 0.5648 (2) | 0.56462 (14) | 0.0407 (6) | |
C22 | 0.04045 (6) | 0.3911 (3) | 0.38896 (18) | 0.0490 (7) | |
H22 | 0.0207 | 0.3968 | 0.3921 | 0.059* | |
C16 | 0.10750 (6) | 0.6942 (2) | 0.20318 (15) | 0.0437 (6) | |
H16 | 0.0878 | 0.7295 | 0.1771 | 0.052* | |
C9 | 0.25084 (5) | 0.4131 (3) | 0.40909 (16) | 0.0464 (6) | |
H9 | 0.2696 | 0.3723 | 0.4381 | 0.056* | |
C12 | 0.21817 (6) | 0.6845 (2) | 0.26066 (15) | 0.0406 (6) | |
H12 | 0.2359 | 0.7178 | 0.2533 | 0.049* | |
C20 | 0.07433 (5) | 0.3166 (3) | 0.32369 (15) | 0.0420 (6) | |
H20 | 0.0769 | 0.2700 | 0.2814 | 0.050* | |
Mn2 | 0.0000 | 0.80281 (5) | 0.2500 | 0.03132 (13) | |
N6 | 0.04381 (4) | 0.85364 (18) | 0.35662 (10) | 0.0313 (4) | |
O7 | 0.03107 (5) | 0.64739 (19) | 0.23530 (11) | 0.0595 (5) | |
N7 | −0.01335 (4) | 0.96512 (17) | 0.32351 (10) | 0.0306 (4) | |
N8 | 0.02222 (5) | 0.5963 (2) | 0.16596 (12) | 0.0380 (5) | |
C36 | 0.04087 (5) | 0.9521 (2) | 0.40558 (12) | 0.0284 (5) | |
O6 | 0.03469 (4) | 0.49363 (19) | 0.15545 (11) | 0.0558 (5) | |
C38 | −0.04137 (5) | 1.0173 (2) | 0.30939 (14) | 0.0377 (5) | |
H38 | −0.0580 | 0.9855 | 0.2659 | 0.045* | |
C41 | 0.01066 (5) | 1.0118 (2) | 0.38751 (12) | 0.0289 (5) | |
O8 | 0.00093 (5) | 0.65110 (19) | 0.11162 (12) | 0.0600 (5) | |
C39 | −0.04727 (6) | 1.1173 (2) | 0.35620 (15) | 0.0429 (6) | |
H39 | −0.0673 | 1.1501 | 0.3443 | 0.051* | |
C35 | 0.06611 (5) | 0.9952 (2) | 0.47287 (13) | 0.0344 (5) | |
C33 | 0.09753 (5) | 0.8308 (2) | 0.44203 (14) | 0.0387 (6) | |
H33 | 0.1164 | 0.7866 | 0.4530 | 0.046* | |
C34 | 0.09500 (5) | 0.9304 (2) | 0.49049 (14) | 0.0397 (6) | |
H34 | 0.1121 | 0.9557 | 0.5348 | 0.048* | |
C40 | −0.02308 (6) | 1.1661 (2) | 0.41972 (15) | 0.0411 (6) | |
H40 | −0.0264 | 1.2339 | 0.4510 | 0.049* | |
C32 | 0.07157 (5) | 0.7955 (2) | 0.37567 (14) | 0.0372 (5) | |
H32 | 0.0737 | 0.7275 | 0.3428 | 0.045* | |
C37 | 0.06136 (6) | 1.0997 (3) | 0.52117 (15) | 0.0454 (6) | |
H37 | 0.0781 | 1.1293 | 0.5652 | 0.055* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C43 | 0.0645 (18) | 0.0331 (13) | 0.0360 (14) | −0.0094 (12) | 0.0181 (13) | −0.0101 (11) |
C42 | 0.0496 (14) | 0.0262 (12) | 0.0315 (12) | −0.0034 (10) | 0.0173 (11) | 0.0023 (9) |
Mn1 | 0.02432 (17) | 0.03202 (19) | 0.02553 (18) | 0.00347 (13) | 0.00780 (14) | −0.00017 (14) |
N5 | 0.0316 (10) | 0.0351 (11) | 0.0360 (11) | −0.0004 (8) | 0.0070 (9) | 0.0012 (9) |
O3 | 0.0455 (10) | 0.0439 (10) | 0.0354 (9) | 0.0075 (8) | 0.0195 (8) | 0.0093 (7) |
F1 | 0.0483 (9) | 0.0644 (10) | 0.0637 (10) | 0.0076 (7) | 0.0233 (8) | 0.0350 (8) |
F3 | 0.0537 (10) | 0.0632 (11) | 0.0679 (11) | 0.0216 (8) | 0.0049 (8) | 0.0263 (9) |
F4 | 0.0812 (12) | 0.0574 (10) | 0.0641 (11) | 0.0053 (9) | 0.0272 (9) | 0.0313 (9) |
O5 | 0.0457 (10) | 0.0475 (11) | 0.0469 (10) | 0.0054 (8) | 0.0116 (8) | 0.0192 (9) |
O2 | 0.0412 (9) | 0.0375 (9) | 0.0308 (8) | 0.0103 (7) | 0.0073 (7) | −0.0034 (7) |
N4 | 0.0330 (10) | 0.0301 (10) | 0.0286 (10) | −0.0011 (8) | 0.0089 (8) | −0.0003 (8) |
N1 | 0.0291 (10) | 0.0373 (11) | 0.0285 (10) | 0.0060 (8) | 0.0085 (8) | 0.0065 (8) |
F5 | 0.0506 (9) | 0.0743 (11) | 0.0693 (11) | −0.0065 (8) | 0.0304 (8) | 0.0169 (9) |
N3 | 0.0292 (10) | 0.0359 (11) | 0.0325 (10) | 0.0018 (8) | 0.0092 (8) | −0.0002 (8) |
N2 | 0.0295 (10) | 0.0309 (10) | 0.0273 (9) | 0.0054 (8) | 0.0072 (8) | −0.0004 (8) |
C1 | 0.0360 (13) | 0.0359 (13) | 0.0301 (12) | 0.0048 (10) | 0.0104 (10) | 0.0006 (10) |
C11 | 0.0359 (12) | 0.0376 (13) | 0.0334 (12) | −0.0011 (10) | 0.0143 (10) | 0.0005 (10) |
C2 | 0.0373 (12) | 0.0313 (12) | 0.0278 (11) | 0.0031 (9) | 0.0112 (10) | −0.0024 (9) |
C5 | 0.0393 (14) | 0.0418 (14) | 0.0439 (14) | 0.0129 (11) | 0.0081 (12) | 0.0099 (12) |
C31 | 0.0337 (12) | 0.0283 (12) | 0.0355 (12) | 0.0085 (9) | 0.0162 (10) | 0.0085 (9) |
C4 | 0.0353 (13) | 0.0489 (16) | 0.0535 (16) | 0.0060 (11) | 0.0156 (12) | 0.0111 (13) |
C23 | 0.0410 (14) | 0.0362 (13) | 0.0537 (16) | 0.0143 (10) | 0.0279 (13) | 0.0191 (11) |
C19 | 0.0317 (11) | 0.0324 (12) | 0.0261 (11) | 0.0021 (9) | 0.0096 (9) | −0.0016 (9) |
C14 | 0.0434 (13) | 0.0289 (12) | 0.0282 (12) | 0.0011 (10) | 0.0096 (10) | −0.0009 (9) |
C30 | 0.0412 (13) | 0.0254 (11) | 0.0288 (11) | 0.0084 (9) | 0.0160 (10) | 0.0064 (9) |
C15 | 0.0524 (15) | 0.0309 (13) | 0.0374 (14) | 0.0069 (11) | 0.0087 (12) | 0.0076 (10) |
C3 | 0.0423 (14) | 0.0368 (13) | 0.0404 (14) | 0.0067 (11) | 0.0160 (11) | 0.0114 (11) |
C18 | 0.0332 (12) | 0.0288 (11) | 0.0231 (11) | 0.0037 (9) | 0.0082 (9) | −0.0021 (9) |
O1 | 0.0604 (12) | 0.0545 (12) | 0.0471 (11) | 0.0161 (9) | −0.0088 (9) | −0.0188 (9) |
C17 | 0.0319 (12) | 0.0378 (13) | 0.0359 (13) | 0.0058 (10) | 0.0074 (10) | 0.0004 (10) |
C8 | 0.0307 (12) | 0.0469 (15) | 0.0404 (14) | 0.0089 (10) | 0.0102 (11) | 0.0133 (11) |
F2 | 0.0366 (9) | 0.0964 (14) | 0.1034 (15) | 0.0115 (9) | 0.0254 (9) | 0.0439 (12) |
C7 | 0.0411 (13) | 0.0395 (14) | 0.0407 (14) | −0.0038 (11) | 0.0197 (11) | 0.0004 (11) |
C25 | 0.084 (2) | 0.0431 (16) | 0.0484 (16) | 0.0265 (15) | 0.0448 (17) | 0.0127 (13) |
C6 | 0.0580 (16) | 0.0335 (13) | 0.0353 (13) | 0.0063 (11) | 0.0147 (12) | 0.0108 (11) |
C13 | 0.0539 (16) | 0.0335 (13) | 0.0343 (13) | −0.0037 (11) | 0.0147 (12) | 0.0042 (10) |
C28 | 0.0695 (19) | 0.0415 (15) | 0.0361 (14) | −0.0066 (13) | 0.0049 (13) | −0.0088 (12) |
C29 | 0.0427 (14) | 0.0392 (14) | 0.0336 (13) | −0.0050 (11) | 0.0072 (11) | −0.0028 (11) |
O4 | 0.0381 (11) | 0.0547 (12) | 0.124 (2) | 0.0078 (9) | 0.0341 (12) | 0.0272 (12) |
C21 | 0.0274 (13) | 0.0558 (17) | 0.0612 (18) | −0.0029 (11) | 0.0064 (13) | 0.0067 (14) |
C24 | 0.0591 (17) | 0.0503 (16) | 0.0605 (18) | 0.0258 (14) | 0.0413 (16) | 0.0223 (14) |
C10 | 0.0313 (13) | 0.0544 (16) | 0.0478 (15) | −0.0014 (11) | 0.0170 (11) | 0.0052 (12) |
C27 | 0.087 (2) | 0.0359 (15) | 0.0313 (14) | 0.0082 (14) | 0.0200 (14) | −0.0031 (11) |
C26 | 0.0638 (17) | 0.0294 (12) | 0.0341 (13) | 0.0143 (11) | 0.0237 (13) | 0.0081 (10) |
C22 | 0.0269 (13) | 0.0486 (16) | 0.075 (2) | 0.0094 (11) | 0.0216 (13) | 0.0240 (14) |
C16 | 0.0406 (14) | 0.0396 (14) | 0.0417 (14) | 0.0113 (11) | 0.0031 (11) | 0.0058 (11) |
C9 | 0.0276 (12) | 0.0595 (17) | 0.0502 (16) | 0.0083 (11) | 0.0113 (11) | 0.0133 (13) |
C12 | 0.0441 (14) | 0.0401 (14) | 0.0416 (14) | −0.0065 (11) | 0.0201 (12) | 0.0003 (11) |
C20 | 0.0304 (12) | 0.0490 (15) | 0.0407 (14) | −0.0030 (11) | 0.0053 (11) | 0.0004 (11) |
Mn2 | 0.0355 (3) | 0.0298 (3) | 0.0232 (2) | 0.000 | 0.0037 (2) | 0.000 |
N6 | 0.0331 (10) | 0.0339 (10) | 0.0242 (9) | 0.0018 (8) | 0.0070 (8) | −0.0002 (8) |
O7 | 0.0690 (13) | 0.0547 (12) | 0.0433 (11) | 0.0116 (10) | 0.0054 (10) | −0.0206 (9) |
N7 | 0.0325 (10) | 0.0291 (10) | 0.0272 (10) | 0.0013 (8) | 0.0069 (8) | 0.0027 (8) |
N8 | 0.0367 (11) | 0.0407 (12) | 0.0383 (12) | −0.0083 (9) | 0.0154 (10) | −0.0039 (10) |
C36 | 0.0342 (12) | 0.0276 (11) | 0.0226 (11) | −0.0038 (9) | 0.0089 (9) | 0.0030 (9) |
O6 | 0.0485 (11) | 0.0610 (12) | 0.0629 (12) | 0.0015 (9) | 0.0261 (10) | −0.0249 (10) |
C38 | 0.0345 (13) | 0.0400 (13) | 0.0352 (13) | 0.0024 (10) | 0.0083 (10) | 0.0050 (11) |
C41 | 0.0356 (12) | 0.0260 (11) | 0.0251 (11) | −0.0035 (9) | 0.0109 (9) | 0.0030 (9) |
O8 | 0.0557 (12) | 0.0597 (13) | 0.0520 (12) | −0.0066 (10) | 0.0036 (10) | 0.0132 (10) |
C39 | 0.0430 (14) | 0.0416 (14) | 0.0473 (15) | 0.0133 (11) | 0.0201 (12) | 0.0102 (12) |
C35 | 0.0387 (13) | 0.0362 (13) | 0.0257 (11) | −0.0110 (10) | 0.0081 (10) | 0.0016 (10) |
C33 | 0.0313 (12) | 0.0459 (15) | 0.0367 (13) | 0.0023 (10) | 0.0096 (11) | 0.0144 (11) |
C34 | 0.0341 (13) | 0.0469 (15) | 0.0306 (12) | −0.0117 (11) | 0.0023 (10) | 0.0060 (11) |
C40 | 0.0584 (16) | 0.0311 (13) | 0.0402 (14) | 0.0072 (11) | 0.0254 (13) | 0.0033 (10) |
C32 | 0.0380 (13) | 0.0415 (14) | 0.0320 (12) | 0.0055 (10) | 0.0121 (11) | 0.0037 (10) |
C37 | 0.0518 (16) | 0.0429 (15) | 0.0338 (13) | −0.0139 (12) | 0.0057 (12) | −0.0099 (11) |
C43—C37 | 1.341 (4) | C8—H8 | 0.9300 |
C43—C42 | 1.435 (3) | C7—C6 | 1.385 (3) |
C43—H43 | 0.9300 | C25—C24 | 1.345 (4) |
C42—C41 | 1.406 (3) | C25—C26 | 1.435 (4) |
C42—C40 | 1.407 (3) | C25—H25 | 0.9300 |
Mn1—O2 | 2.1111 (15) | C13—C12 | 1.342 (3) |
Mn1—O3 | 2.2073 (16) | C13—H13 | 0.9300 |
Mn1—N3 | 2.2405 (18) | C28—C27 | 1.367 (4) |
Mn1—N4 | 2.2708 (18) | C28—C29 | 1.401 (3) |
Mn1—N1 | 2.3034 (18) | C28—H28 | 0.9300 |
Mn1—N2 | 2.3202 (18) | C29—H29 | 0.9300 |
N5—O4 | 1.225 (2) | C21—C22 | 1.356 (4) |
N5—O5 | 1.228 (2) | C21—C20 | 1.388 (3) |
N5—O3 | 1.283 (2) | C21—H21 | 0.9300 |
F1—C3 | 1.345 (3) | C24—H24 | 0.9300 |
F3—C5 | 1.340 (3) | C10—C9 | 1.370 (3) |
F4—C6 | 1.334 (3) | C10—H10 | 0.9300 |
O2—C1 | 1.253 (3) | C27—C26 | 1.396 (4) |
N4—C29 | 1.322 (3) | C27—H27 | 0.9300 |
N4—C30 | 1.357 (3) | C22—H22 | 0.9300 |
N1—C8 | 1.327 (3) | C16—H16 | 0.9300 |
N1—C19 | 1.359 (3) | C9—H9 | 0.9300 |
F5—C7 | 1.337 (3) | C12—H12 | 0.9300 |
N3—C20 | 1.330 (3) | C20—H20 | 0.9300 |
N3—C31 | 1.355 (3) | Mn2—O7i | 2.1988 (19) |
N2—C17 | 1.330 (3) | Mn2—O7 | 2.1988 (19) |
N2—C18 | 1.358 (3) | Mn2—N6 | 2.2808 (18) |
C1—O1 | 1.212 (3) | Mn2—N6i | 2.2808 (18) |
C1—C2 | 1.538 (3) | Mn2—N7 | 2.3124 (18) |
C11—C10 | 1.406 (3) | Mn2—N7i | 2.3124 (18) |
C11—C19 | 1.407 (3) | N6—C32 | 1.333 (3) |
C11—C12 | 1.434 (3) | N6—C36 | 1.361 (3) |
C2—C7 | 1.374 (3) | O7—N8 | 1.264 (3) |
C2—C3 | 1.376 (3) | N7—C38 | 1.329 (3) |
C5—C6 | 1.363 (4) | N7—C41 | 1.358 (3) |
C5—C4 | 1.374 (3) | N8—O6 | 1.231 (3) |
C31—C23 | 1.414 (3) | N8—O8 | 1.236 (3) |
C31—C30 | 1.440 (3) | C36—C35 | 1.408 (3) |
C4—F2 | 1.347 (3) | C36—C41 | 1.440 (3) |
C4—C3 | 1.376 (3) | C38—C39 | 1.396 (3) |
C23—C22 | 1.409 (4) | C38—H38 | 0.9300 |
C23—C24 | 1.422 (4) | C39—C40 | 1.365 (4) |
C19—C18 | 1.445 (3) | C39—H39 | 0.9300 |
C14—C15 | 1.401 (3) | C35—C34 | 1.411 (3) |
C14—C18 | 1.410 (3) | C35—C37 | 1.426 (3) |
C14—C13 | 1.435 (3) | C33—C34 | 1.358 (3) |
C30—C26 | 1.407 (3) | C33—C32 | 1.394 (3) |
C15—C16 | 1.367 (3) | C33—H33 | 0.9300 |
C15—H15 | 0.9300 | C34—H34 | 0.9300 |
C17—C16 | 1.391 (3) | C40—H40 | 0.9300 |
C17—H17 | 0.9300 | C32—H32 | 0.9300 |
C8—C9 | 1.394 (3) | C37—H37 | 0.9300 |
C37—C43—C42 | 120.9 (2) | C12—C13—H13 | 119.4 |
C37—C43—H43 | 119.6 | C14—C13—H13 | 119.4 |
C42—C43—H43 | 119.6 | C27—C28—C29 | 119.1 (2) |
C41—C42—C40 | 117.6 (2) | C27—C28—H28 | 120.5 |
C41—C42—C43 | 119.5 (2) | C29—C28—H28 | 120.5 |
C40—C42—C43 | 122.8 (2) | N4—C29—C28 | 122.7 (2) |
O2—Mn1—O3 | 96.43 (6) | N4—C29—H29 | 118.6 |
O2—Mn1—N3 | 90.51 (6) | C28—C29—H29 | 118.6 |
O3—Mn1—N3 | 115.29 (6) | C22—C21—C20 | 119.4 (2) |
O2—Mn1—N4 | 164.15 (6) | C22—C21—H21 | 120.3 |
O3—Mn1—N4 | 89.52 (6) | C20—C21—H21 | 120.3 |
N3—Mn1—N4 | 73.68 (6) | C25—C24—C23 | 121.2 (2) |
O2—Mn1—N1 | 99.58 (6) | C25—C24—H24 | 119.4 |
O3—Mn1—N1 | 84.19 (6) | C23—C24—H24 | 119.4 |
N3—Mn1—N1 | 157.06 (7) | C9—C10—C11 | 119.7 (2) |
N4—Mn1—N1 | 95.61 (7) | C9—C10—H10 | 120.1 |
O2—Mn1—N2 | 88.34 (6) | C11—C10—H10 | 120.1 |
O3—Mn1—N2 | 156.01 (6) | C28—C27—C26 | 119.9 (2) |
N3—Mn1—N2 | 88.07 (6) | C28—C27—H27 | 120.0 |
N4—Mn1—N2 | 92.17 (6) | C26—C27—H27 | 120.0 |
N1—Mn1—N2 | 71.83 (6) | C27—C26—C30 | 117.3 (2) |
O4—N5—O5 | 121.5 (2) | C27—C26—C25 | 123.8 (2) |
O4—N5—O3 | 118.83 (19) | C30—C26—C25 | 118.9 (2) |
O5—N5—O3 | 119.69 (19) | C21—C22—C23 | 120.0 (2) |
N5—O3—Mn1 | 113.47 (13) | C21—C22—H22 | 120.0 |
C1—O2—Mn1 | 142.82 (15) | C23—C22—H22 | 120.0 |
C29—N4—C30 | 118.25 (19) | C15—C16—C17 | 119.2 (2) |
C29—N4—Mn1 | 126.88 (16) | C15—C16—H16 | 120.4 |
C30—N4—Mn1 | 114.66 (14) | C17—C16—H16 | 120.4 |
C8—N1—C19 | 117.66 (19) | C10—C9—C8 | 118.6 (2) |
C8—N1—Mn1 | 125.80 (15) | C10—C9—H9 | 120.7 |
C19—N1—Mn1 | 116.49 (13) | C8—C9—H9 | 120.7 |
C20—N3—C31 | 118.1 (2) | C13—C12—C11 | 121.2 (2) |
C20—N3—Mn1 | 125.98 (16) | C13—C12—H12 | 119.4 |
C31—N3—Mn1 | 115.71 (14) | C11—C12—H12 | 119.4 |
C17—N2—C18 | 117.50 (19) | N3—C20—C21 | 123.1 (2) |
C17—N2—Mn1 | 126.45 (15) | N3—C20—H20 | 118.4 |
C18—N2—Mn1 | 116.00 (13) | C21—C20—H20 | 118.4 |
O1—C1—O2 | 127.2 (2) | O7i—Mn2—O7 | 88.77 (11) |
O1—C1—C2 | 117.0 (2) | O7i—Mn2—N6 | 118.66 (7) |
O2—C1—C2 | 115.84 (19) | O7—Mn2—N6 | 80.93 (7) |
C10—C11—C19 | 117.5 (2) | O7i—Mn2—N6i | 80.93 (7) |
C10—C11—C12 | 123.1 (2) | O7—Mn2—N6i | 118.66 (7) |
C19—C11—C12 | 119.4 (2) | N6—Mn2—N6i | 153.95 (9) |
C7—C2—C3 | 116.7 (2) | O7i—Mn2—N7 | 97.30 (7) |
C7—C2—C1 | 121.0 (2) | O7—Mn2—N7 | 152.55 (6) |
C3—C2—C1 | 122.3 (2) | N6—Mn2—N7 | 72.64 (6) |
F3—C5—C6 | 121.1 (2) | N6i—Mn2—N7 | 88.77 (6) |
F3—C5—C4 | 119.1 (2) | O7i—Mn2—N7i | 152.55 (6) |
C6—C5—C4 | 119.8 (2) | O7—Mn2—N7i | 97.30 (7) |
N3—C31—C23 | 122.5 (2) | N6—Mn2—N7i | 88.77 (6) |
N3—C31—C30 | 117.86 (19) | N6i—Mn2—N7i | 72.64 (6) |
C23—C31—C30 | 119.6 (2) | N7—Mn2—N7i | 89.58 (9) |
F2—C4—C5 | 119.4 (2) | C32—N6—C36 | 117.54 (19) |
F2—C4—C3 | 120.7 (2) | C32—N6—Mn2 | 126.40 (15) |
C5—C4—C3 | 119.9 (2) | C36—N6—Mn2 | 116.05 (14) |
C22—C23—C31 | 116.9 (2) | N8—O7—Mn2 | 114.23 (15) |
C22—C23—C24 | 123.9 (2) | C38—N7—C41 | 117.61 (19) |
C31—C23—C24 | 119.2 (2) | C38—N7—Mn2 | 127.41 (15) |
N1—C19—C11 | 122.7 (2) | C41—N7—Mn2 | 114.98 (14) |
N1—C19—C18 | 117.82 (19) | O6—N8—O8 | 122.7 (2) |
C11—C19—C18 | 119.5 (2) | O6—N8—O7 | 119.1 (2) |
C15—C14—C18 | 117.4 (2) | O8—N8—O7 | 118.2 (2) |
C15—C14—C13 | 123.4 (2) | N6—C36—C35 | 122.2 (2) |
C18—C14—C13 | 119.2 (2) | N6—C36—C41 | 118.01 (18) |
N4—C30—C26 | 122.8 (2) | C35—C36—C41 | 119.8 (2) |
N4—C30—C31 | 117.73 (19) | N7—C38—C39 | 123.6 (2) |
C26—C30—C31 | 119.5 (2) | N7—C38—H38 | 118.2 |
C16—C15—C14 | 119.5 (2) | C39—C38—H38 | 118.2 |
C16—C15—H15 | 120.2 | N7—C41—C42 | 122.7 (2) |
C14—C15—H15 | 120.2 | N7—C41—C36 | 118.18 (19) |
F1—C3—C2 | 120.2 (2) | C42—C41—C36 | 119.11 (19) |
F1—C3—C4 | 117.9 (2) | C40—C39—C38 | 118.9 (2) |
C2—C3—C4 | 121.9 (2) | C40—C39—H39 | 120.6 |
N2—C18—C14 | 122.8 (2) | C38—C39—H39 | 120.6 |
N2—C18—C19 | 117.76 (19) | C36—C35—C34 | 118.0 (2) |
C14—C18—C19 | 119.4 (2) | C36—C35—C37 | 119.1 (2) |
N2—C17—C16 | 123.5 (2) | C34—C35—C37 | 122.8 (2) |
N2—C17—H17 | 118.2 | C34—C33—C32 | 119.2 (2) |
C16—C17—H17 | 118.2 | C34—C33—H33 | 120.4 |
N1—C8—C9 | 123.9 (2) | C32—C33—H33 | 120.4 |
N1—C8—H8 | 118.1 | C33—C34—C35 | 119.3 (2) |
C9—C8—H8 | 118.1 | C33—C34—H34 | 120.4 |
F5—C7—C2 | 119.2 (2) | C35—C34—H34 | 120.4 |
F5—C7—C6 | 118.3 (2) | C39—C40—C42 | 119.6 (2) |
C2—C7—C6 | 122.5 (2) | C39—C40—H40 | 120.2 |
C24—C25—C26 | 121.6 (2) | C42—C40—H40 | 120.2 |
C24—C25—H25 | 119.2 | N6—C32—C33 | 123.7 (2) |
C26—C25—H25 | 119.2 | N6—C32—H32 | 118.1 |
F4—C6—C5 | 120.3 (2) | C33—C32—H32 | 118.1 |
F4—C6—C7 | 120.6 (2) | C43—C37—C35 | 121.5 (2) |
C5—C6—C7 | 119.2 (2) | C43—C37—H37 | 119.2 |
C12—C13—C14 | 121.3 (2) | C35—C37—H37 | 119.2 |
Symmetry code: (i) −x, y, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9···O3ii | 0.93 | 2.56 | 3.474 (3) | 170 |
C9—H9···O5ii | 0.93 | 2.57 | 3.221 (3) | 127 |
C13—H13···O5iii | 0.93 | 2.59 | 3.485 (3) | 162 |
C24—H24···O6iv | 0.93 | 2.59 | 3.220 (4) | 125 |
C27—H27···O2iv | 0.93 | 2.54 | 3.455 (3) | 170 |
C39—H39···O1v | 0.93 | 2.54 | 3.306 (4) | 139 |
C43—H43···O8vi | 0.93 | 2.56 | 3.412 (3) | 153 |
C28—H28···F1iv | 0.93 | 2.61 | 3.288 (3) | 131 |
C33—H33···F5vii | 0.93 | 2.58 | 2.915 (3) | 101 |
Symmetry codes: (ii) −x+1/2, −y+1/2, −z+1; (iii) x, −y+1, z−1/2; (iv) x, −y+1, z+1/2; (v) −x, y+1, −z+1/2; (vi) x, −y+2, z+1/2; (vii) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | [Mn(C7F5O2)(NO3)(C12H8N2)2]2·[Mn(NO3)2(C12H8N2)2] |
Mr | 1916.22 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 295 |
a, b, c (Å) | 45.889 (3), 10.1112 (6), 17.7948 (10) |
β (°) | 110.756 (1) |
V (Å3) | 7720.8 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.59 |
Crystal size (mm) | 0.15 × 0.12 × 0.10 |
Data collection | |
Diffractometer | CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.911, 0.933 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21136, 7585, 6126 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.618 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.097, 1.03 |
No. of reflections | 7585 |
No. of parameters | 591 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.48, −0.25 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), Bruker SHELXTL (Bruker, 2001), SHELXL97.
Mn1—O2 | 2.1111 (15) | Mn1—N2 | 2.3202 (18) |
Mn1—O3 | 2.2073 (16) | Mn2—O7 | 2.1988 (19) |
Mn1—N3 | 2.2405 (18) | Mn2—N6 | 2.2808 (18) |
Mn1—N4 | 2.2708 (18) | Mn2—N7 | 2.3124 (18) |
Mn1—N1 | 2.3034 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9···O3i | 0.93 | 2.56 | 3.474 (3) | 170 |
C9—H9···O5i | 0.93 | 2.57 | 3.221 (3) | 127 |
C13—H13···O5ii | 0.93 | 2.59 | 3.485 (3) | 162 |
C24—H24···O6iii | 0.93 | 2.59 | 3.220 (4) | 125 |
C27—H27···O2iii | 0.93 | 2.54 | 3.455 (3) | 170 |
C39—H39···O1iv | 0.93 | 2.54 | 3.306 (4) | 139 |
C43—H43···O8v | 0.93 | 2.56 | 3.412 (3) | 153 |
C28—H28···F1iii | 0.93 | 2.61 | 3.288 (3) | 131 |
C33—H33···F5vi | 0.93 | 2.58 | 2.915 (3) | 101 |
Symmetry codes: (i) −x+1/2, −y+1/2, −z+1; (ii) x, −y+1, z−1/2; (iii) x, −y+1, z+1/2; (iv) −x, y+1, −z+1/2; (v) x, −y+2, z+1/2; (vi) x, y+1, z. |
Cg1—Cg2vii | 3.6775 (14) | Cg3—Cg4viii | 3.8214 (13) |
Cg1, Cg2, Cg3 and Cg4 are centroids of the rings N7/C38–C42, C35–C37/C41–C43, C2–C7 and C11–C14/C18/C19, respectively. Symmetry codes: (vii) x, 2-y, -1/2+z; (viii) x, -1+y, z. |
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The title compound contains two types of neutral molecules - Mn(Phen)2(F5C6COO)(NO3) (A) and Mn(Phen)2(NO3)2 (B), respectively, with a 2:1 ratio. The Mn ions in two molecules are coordinated by four N atoms and two O atoms in a distorted octahedral geometry each (Table 2).
In the crystal, significant F···F interactions are favored (F3···F3(1/2 - x,-1/2 - y,1 - z) = 2.813 (2) Å; F3—F4(1/2 - x,-1/2 - y,1 - z) =3.020 (3) Å). The crystal packing exhibits weak intermolecular C—H···O and C—H···F hydrogen bonds (Table 1), and π···π interactions proved by relatively short distances of 3.6775 (14) and 3.8214 (13) Å between the centroids of six-membered rings from the neighbouring molecules (Table 2).