Diaqua­bis(1,10-phenanthroline-κ²N,N′)manganese(II) penta­fluorooxoniobate(V)

In the title compound, [Mn(C₁₂H₈N₂)₂(H₂O)₂][NbOF₅], each of the Mn^II and Nb^V atoms has a distorted octa­hedral coordination. In the [NbOF₅]²⁻ anion, a characteristic short terminal Nb=O bond and a longer Nb—F bond are observed, which result in the out-of-center distortion of the octa­hedron, a manifestation of the second-order Jahn–Teller effect.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.033
• wR factor = 0.092
• Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



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 .....          ?
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Nb1
PLAT432_ALERT_2_C Short Inter X...Y Contact  F4     ..  C22     ..       2.93 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O3     ..  C10     ..       2.97 Ang.

   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

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SMART; data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXTL.

Diaquabis(1,10-phenanthroline-κ²N,N')manganese(II) pentafluorooxoniobate

Crystal data

[Mn(C12H8N2)2(H2O)2][NbF5O]	Z = 2
Mr = 655.29	F(000) = 654
Triclinic, P1	Dx = 1.702 Mg m^−3
a = 9.6242 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.3971 (5) Å	Cell parameters from 2712 reflections
c = 13.0605 (5) Å	θ = 1.7–25.1°
α = 72.341 (2)°	µ = 1.01 mm^−1
β = 70.054 (3)°	T = 273 K
γ = 79.686 (3)°	Block, yellow
V = 1278.62 (9) Å^3	0.31 × 0.20 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer	4530 independent reflections
Radiation source: fine-focus sealed tube	3265 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 25.1°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −11→11
Tmin = 0.746, Tmax = 0.937	k = −13→13
12791 measured reflections	l = −15→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0507P)^2] where P = (Fo^2 + 2Fc^2)/3
4530 reflections	(Δ/σ)max = 0.001
360 parameters	Δρmax = 0.46 e Å^−3
4 restraints	Δρmin = −0.53 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Nb1	0.88497 (4)	0.23500 (3)	0.18405 (3)	0.04906 (14)
Mn1	0.20835 (6)	0.27630 (4)	0.77626 (4)	0.04110 (15)
F1	0.9318 (4)	0.1226 (2)	0.3103 (2)	0.1177 (12)
F2	0.6788 (3)	0.2382 (3)	0.2574 (3)	0.1104 (10)
F3	0.8380 (3)	0.32686 (18)	0.04452 (18)	0.0724 (6)
F4	1.0861 (3)	0.2096 (3)	0.0912 (3)	0.1061 (9)
F5	0.8680 (3)	0.08464 (19)	0.1351 (2)	0.0955 (9)
N1	0.1467 (3)	0.2509 (2)	0.6331 (2)	0.0498 (7)
N2	0.2837 (3)	0.4425 (2)	0.6269 (2)	0.0491 (7)
N3	0.4117 (3)	0.1365 (2)	0.7558 (2)	0.0467 (7)
N4	0.3401 (3)	0.3066 (2)	0.8772 (2)	0.0461 (7)
O1	0.0231 (3)	0.4002 (2)	0.8372 (2)	0.0497 (6)
O2	0.0813 (3)	0.1308 (2)	0.8975 (2)	0.0557 (6)
O3	0.9179 (3)	0.36735 (19)	0.2116 (2)	0.0621 (7)
C1	0.0795 (5)	0.1572 (3)	0.6357 (4)	0.0690 (11)
H1A	0.0609	0.0919	0.7005	0.083*
C2	0.0358 (5)	0.1522 (4)	0.5462 (4)	0.0800 (13)
H2A	−0.0099	0.0845	0.5510	0.096*
C3	0.0606 (5)	0.2471 (5)	0.4522 (4)	0.0833 (14)
H3	0.0314	0.2449	0.3919	0.100*
C4	0.1295 (5)	0.3482 (4)	0.4445 (3)	0.0674 (11)
C5	0.1571 (6)	0.4538 (5)	0.3491 (4)	0.0895 (15)
H5	0.1322	0.4553	0.2859	0.107*
C6	0.2180 (6)	0.5505 (5)	0.3492 (4)	0.0922 (16)
H6	0.2317	0.6188	0.2869	0.111*
C7	0.2619 (4)	0.5512 (4)	0.4417 (3)	0.0666 (11)
C8	0.3248 (5)	0.6505 (4)	0.4469 (4)	0.0861 (15)
H8	0.3371	0.7218	0.3875	0.103*
C9	0.3677 (5)	0.6439 (4)	0.5366 (4)	0.0783 (14)
H9	0.4115	0.7092	0.5386	0.094*
C10	0.3454 (4)	0.5374 (3)	0.6266 (3)	0.0600 (10)
H10	0.3751	0.5332	0.6885	0.072*
C11	0.2418 (4)	0.4486 (3)	0.5360 (3)	0.0497 (9)
C12	0.1724 (4)	0.3459 (3)	0.5382 (3)	0.0500 (9)
C13	0.4458 (5)	0.0517 (3)	0.6990 (3)	0.0667 (11)
H13	0.3858	0.0506	0.6566	0.080*
C14	0.5660 (5)	−0.0354 (4)	0.6992 (4)	0.0814 (13)
H14	0.5857	−0.0930	0.6576	0.098*
C15	0.6556 (5)	−0.0360 (4)	0.7613 (4)	0.0771 (12)
H15	0.7375	−0.0933	0.7613	0.092*
C16	0.6230 (4)	0.0500 (3)	0.8245 (3)	0.0579 (10)
C17	0.7071 (5)	0.0532 (4)	0.8949 (4)	0.0761 (12)
H17	0.7892	−0.0033	0.8981	0.091*
C18	0.6710 (5)	0.1353 (4)	0.9564 (4)	0.0740 (12)
H18	0.7285	0.1358	1.0007	0.089*
C19	0.5445 (4)	0.2222 (3)	0.9542 (3)	0.0548 (9)
C20	0.4998 (5)	0.3084 (4)	1.0192 (4)	0.0691 (11)
H20	0.5520	0.3097	1.0671	0.083*
C21	0.3797 (5)	0.3900 (4)	1.0114 (4)	0.0684 (11)
H21	0.3491	0.4476	1.0537	0.082*
C22	0.3030 (4)	0.3865 (3)	0.9398 (3)	0.0585 (10)
H22	0.2213	0.4432	0.9354	0.070*
C23	0.4600 (4)	0.2241 (3)	0.8851 (3)	0.0449 (8)
C24	0.4994 (4)	0.1347 (3)	0.8194 (3)	0.0450 (8)
H2C	0.091 (4)	0.0578 (19)	0.892 (3)	0.055 (10)*
H2D	0.039 (5)	0.131 (5)	0.964 (2)	0.12 (2)*
H1C	−0.036 (4)	0.380 (3)	0.904 (2)	0.066 (13)*
H1D	0.036 (5)	0.474 (2)	0.822 (4)	0.102 (17)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Nb1	0.0656 (3)	0.03648 (17)	0.0506 (2)	0.00268 (14)	−0.02357 (17)	−0.01656 (13)
Mn1	0.0532 (3)	0.0317 (2)	0.0459 (3)	−0.0003 (2)	−0.0256 (3)	−0.0109 (2)
F1	0.243 (4)	0.0507 (13)	0.0962 (19)	−0.0231 (18)	−0.109 (2)	0.0000 (13)
F2	0.0776 (19)	0.144 (2)	0.117 (2)	−0.0470 (17)	0.0095 (16)	−0.067 (2)
F3	0.0922 (18)	0.0596 (12)	0.0628 (14)	0.0076 (12)	−0.0342 (13)	−0.0084 (10)
F4	0.0708 (18)	0.109 (2)	0.129 (2)	0.0265 (15)	−0.0189 (16)	−0.0502 (18)
F5	0.168 (3)	0.0451 (11)	0.113 (2)	0.0069 (14)	−0.089 (2)	−0.0342 (12)
N1	0.066 (2)	0.0424 (15)	0.0525 (18)	0.0012 (14)	−0.0314 (15)	−0.0170 (13)
N2	0.0573 (19)	0.0364 (14)	0.0507 (18)	0.0035 (13)	−0.0146 (15)	−0.0138 (12)
N3	0.0508 (18)	0.0378 (14)	0.0562 (18)	0.0020 (12)	−0.0208 (15)	−0.0172 (13)
N4	0.0523 (18)	0.0375 (14)	0.0556 (18)	−0.0011 (13)	−0.0257 (14)	−0.0134 (12)
O1	0.0583 (17)	0.0351 (13)	0.0536 (17)	0.0034 (12)	−0.0200 (14)	−0.0095 (11)
O2	0.0773 (19)	0.0344 (13)	0.0560 (18)	−0.0093 (12)	−0.0154 (14)	−0.0159 (12)
O3	0.0744 (18)	0.0383 (12)	0.0869 (19)	−0.0045 (12)	−0.0325 (15)	−0.0263 (12)
C1	0.098 (3)	0.051 (2)	0.079 (3)	−0.004 (2)	−0.048 (3)	−0.0254 (19)
C2	0.102 (4)	0.077 (3)	0.098 (4)	0.004 (3)	−0.064 (3)	−0.044 (3)
C3	0.083 (3)	0.117 (4)	0.081 (3)	0.023 (3)	−0.055 (3)	−0.055 (3)
C4	0.065 (3)	0.091 (3)	0.051 (2)	0.018 (2)	−0.031 (2)	−0.025 (2)
C5	0.084 (4)	0.130 (4)	0.045 (3)	0.015 (3)	−0.035 (2)	−0.008 (3)
C6	0.084 (4)	0.105 (4)	0.050 (3)	0.013 (3)	−0.016 (3)	0.014 (3)
C7	0.053 (3)	0.069 (3)	0.051 (2)	0.008 (2)	−0.0052 (19)	0.0015 (19)
C8	0.076 (3)	0.063 (3)	0.076 (3)	0.000 (2)	0.006 (3)	0.008 (2)
C9	0.071 (3)	0.048 (2)	0.088 (3)	−0.012 (2)	0.011 (3)	−0.014 (2)
C10	0.058 (2)	0.0466 (19)	0.066 (3)	−0.0060 (17)	−0.0009 (19)	−0.0216 (18)
C11	0.042 (2)	0.0495 (19)	0.045 (2)	0.0111 (16)	−0.0080 (16)	−0.0094 (15)
C12	0.050 (2)	0.056 (2)	0.044 (2)	0.0163 (17)	−0.0213 (17)	−0.0168 (16)
C13	0.069 (3)	0.063 (2)	0.077 (3)	0.003 (2)	−0.026 (2)	−0.032 (2)
C14	0.080 (3)	0.062 (2)	0.104 (4)	0.017 (2)	−0.022 (3)	−0.045 (2)
C15	0.056 (3)	0.066 (3)	0.107 (4)	0.017 (2)	−0.028 (3)	−0.029 (2)
C16	0.051 (2)	0.0470 (19)	0.072 (3)	0.0052 (17)	−0.023 (2)	−0.0117 (18)
C17	0.060 (3)	0.070 (3)	0.097 (4)	0.017 (2)	−0.041 (3)	−0.014 (2)
C18	0.062 (3)	0.076 (3)	0.095 (3)	0.007 (2)	−0.049 (3)	−0.017 (2)
C19	0.053 (2)	0.0534 (19)	0.063 (2)	−0.0038 (17)	−0.031 (2)	−0.0066 (17)
C20	0.081 (3)	0.070 (3)	0.079 (3)	−0.012 (2)	−0.052 (2)	−0.018 (2)
C21	0.084 (3)	0.063 (2)	0.084 (3)	−0.005 (2)	−0.043 (3)	−0.036 (2)
C22	0.065 (3)	0.0469 (19)	0.079 (3)	0.0014 (17)	−0.042 (2)	−0.0203 (18)
C23	0.048 (2)	0.0355 (16)	0.051 (2)	−0.0082 (15)	−0.0218 (17)	−0.0019 (14)
C24	0.042 (2)	0.0366 (16)	0.051 (2)	−0.0052 (15)	−0.0157 (16)	−0.0007 (14)

Geometric parameters (Å, º)

Nb1—O3	1.756 (2)	C5—C6	1.337 (6)
Nb1—F2	1.885 (3)	C5—H5	0.9300
Nb1—F1	1.892 (2)	C6—C7	1.413 (7)
Nb1—F4	1.927 (3)	C6—H6	0.9300
Nb1—F3	1.964 (2)	C7—C11	1.401 (5)
Nb1—F5	2.0516 (19)	C7—C8	1.404 (6)
Mn1—O2	2.137 (3)	C8—C9	1.347 (6)
Mn1—O1	2.149 (2)	C8—H8	0.9300
Mn1—N4	2.245 (3)	C9—C10	1.399 (5)
Mn1—N1	2.254 (3)	C9—H9	0.9300
Mn1—N2	2.281 (3)	C10—H10	0.9300
Mn1—N3	2.286 (3)	C11—C12	1.437 (5)
N1—C1	1.330 (4)	C13—C14	1.384 (6)
N1—C12	1.357 (4)	C13—H13	0.9300
N2—C10	1.322 (4)	C14—C15	1.367 (6)
N2—C11	1.358 (4)	C14—H14	0.9300
N3—C13	1.321 (4)	C15—C16	1.395 (6)
N3—C24	1.366 (4)	C15—H15	0.9300
N4—C22	1.327 (4)	C16—C24	1.398 (5)
N4—C23	1.364 (4)	C16—C17	1.429 (6)
O1—H1C	0.849 (18)	C17—C18	1.338 (6)
O1—H1D	0.826 (19)	C17—H17	0.9300
O2—H2C	0.841 (18)	C18—C19	1.428 (5)
O2—H2D	0.825 (19)	C18—H18	0.9300
C1—C2	1.390 (5)	C19—C23	1.399 (5)
C1—H1A	0.9300	C19—C20	1.407 (5)
C2—C3	1.350 (6)	C20—C21	1.360 (6)
C2—H2A	0.9300	C20—H20	0.9300
C3—C4	1.391 (6)	C21—C22	1.387 (5)
C3—H3	0.9300	C21—H21	0.9300
C4—C12	1.410 (5)	C22—H22	0.9300
C4—C5	1.432 (6)	C23—C24	1.445 (5)
O3—Nb1—F2	98.01 (12)	C6—C5—C4	121.3 (4)
O3—Nb1—F1	95.18 (11)	C6—C5—H5	119.4
F2—Nb1—F1	93.64 (16)	C4—C5—H5	119.4
O3—Nb1—F4	93.98 (12)	C5—C6—C7	121.5 (4)
F2—Nb1—F4	167.12 (12)	C5—C6—H6	119.2
F1—Nb1—F4	89.93 (14)	C7—C6—H6	119.2
O3—Nb1—F3	94.22 (11)	C11—C7—C8	116.4 (4)
F2—Nb1—F3	87.14 (13)	C11—C7—C6	119.7 (4)
F1—Nb1—F3	170.37 (9)	C8—C7—C6	123.9 (4)
F4—Nb1—F3	87.32 (12)	C9—C8—C7	120.9 (4)
O3—Nb1—F5	173.18 (12)	C9—C8—H8	119.6
F2—Nb1—F5	88.04 (12)	C7—C8—H8	119.6
F1—Nb1—F5	87.53 (9)	C8—C9—C10	119.1 (4)
F4—Nb1—F5	79.74 (12)	C8—C9—H9	120.5
F3—Nb1—F5	82.91 (9)	C10—C9—H9	120.5
O2—Mn1—O1	86.23 (10)	N2—C10—C9	122.3 (4)
O2—Mn1—N4	100.20 (10)	N2—C10—H10	118.8
O1—Mn1—N4	93.83 (10)	C9—C10—H10	118.8
O2—Mn1—N1	93.04 (10)	N2—C11—C7	122.7 (4)
O1—Mn1—N1	99.39 (10)	N2—C11—C12	118.1 (3)
N4—Mn1—N1	161.86 (11)	C7—C11—C12	119.2 (4)
O2—Mn1—N2	162.58 (11)	N1—C12—C4	122.3 (3)
O1—Mn1—N2	85.17 (10)	N1—C12—C11	118.0 (3)
N4—Mn1—N2	95.46 (10)	C4—C12—C11	119.7 (3)
N1—Mn1—N2	73.51 (10)	N3—C13—C14	123.4 (4)
O2—Mn1—N3	88.46 (10)	N3—C13—H13	118.3
O1—Mn1—N3	165.41 (10)	C14—C13—H13	118.3
N4—Mn1—N3	73.74 (10)	C15—C14—C13	119.4 (4)
N1—Mn1—N3	94.45 (10)	C15—C14—H14	120.3
N2—Mn1—N3	103.30 (10)	C13—C14—H14	120.3
C1—N1—C12	117.8 (3)	C14—C15—C16	119.5 (4)
C1—N1—Mn1	126.5 (2)	C14—C15—H15	120.3
C12—N1—Mn1	115.5 (2)	C16—C15—H15	120.3
C10—N2—C11	118.6 (3)	C15—C16—C24	117.3 (4)
C10—N2—Mn1	126.4 (3)	C15—C16—C17	123.3 (4)
C11—N2—Mn1	114.4 (2)	C24—C16—C17	119.4 (4)
C13—N3—C24	117.3 (3)	C18—C17—C16	121.8 (4)
C13—N3—Mn1	128.0 (3)	C18—C17—H17	119.1
C24—N3—Mn1	114.5 (2)	C16—C17—H17	119.1
C22—N4—C23	117.4 (3)	C17—C18—C19	120.3 (4)
C22—N4—Mn1	126.4 (2)	C17—C18—H18	119.8
C23—N4—Mn1	115.7 (2)	C19—C18—H18	119.8
Mn1—O1—H1C	121 (3)	C23—C19—C20	117.5 (3)
Mn1—O1—H1D	118 (3)	C23—C19—C18	120.0 (4)
H1C—O1—H1D	108 (4)	C20—C19—C18	122.5 (4)
Mn1—O2—H2C	125 (2)	C21—C20—C19	119.3 (4)
Mn1—O2—H2D	124 (4)	C21—C20—H20	120.3
H2C—O2—H2D	109 (4)	C19—C20—H20	120.3
N1—C1—C2	123.2 (4)	C20—C21—C22	119.6 (4)
N1—C1—H1A	118.4	C20—C21—H21	120.2
C2—C1—H1A	118.4	C22—C21—H21	120.2
C3—C2—C1	118.9 (4)	N4—C22—C21	123.4 (4)
C3—C2—H2A	120.5	N4—C22—H22	118.3
C1—C2—H2A	120.5	C21—C22—H22	118.3
C2—C3—C4	120.7 (4)	N4—C23—C19	122.8 (3)
C2—C3—H3	119.7	N4—C23—C24	117.9 (3)
C4—C3—H3	119.7	C19—C23—C24	119.3 (3)
C3—C4—C12	117.1 (4)	N3—C24—C16	123.0 (3)
C3—C4—C5	124.3 (4)	N3—C24—C23	117.7 (3)
C12—C4—C5	118.6 (4)	C16—C24—C23	119.2 (3)
O2—Mn1—N1—C1	−11.3 (3)	C10—N2—C11—C7	0.3 (5)
O1—Mn1—N1—C1	−97.9 (3)	Mn1—N2—C11—C7	172.1 (3)
N4—Mn1—N1—C1	125.8 (4)	C10—N2—C11—C12	−178.9 (3)
N2—Mn1—N1—C1	180.0 (3)	Mn1—N2—C11—C12	−7.1 (4)
N3—Mn1—N1—C1	77.4 (3)	C8—C7—C11—N2	−1.7 (5)
O2—Mn1—N1—C12	163.9 (2)	C6—C7—C11—N2	178.9 (4)
O1—Mn1—N1—C12	77.2 (2)	C8—C7—C11—C12	177.5 (3)
N4—Mn1—N1—C12	−59.0 (4)	C6—C7—C11—C12	−1.9 (5)
N2—Mn1—N1—C12	−4.8 (2)	C1—N1—C12—C4	0.6 (5)
N3—Mn1—N1—C12	−107.4 (2)	Mn1—N1—C12—C4	−175.0 (3)
O2—Mn1—N2—C10	136.7 (4)	C1—N1—C12—C11	178.6 (3)
O1—Mn1—N2—C10	76.0 (3)	Mn1—N1—C12—C11	2.9 (4)
N4—Mn1—N2—C10	−17.4 (3)	C3—C4—C12—N1	−1.0 (6)
N1—Mn1—N2—C10	177.3 (3)	C5—C4—C12—N1	178.2 (4)
N3—Mn1—N2—C10	−91.9 (3)	C3—C4—C12—C11	−178.9 (3)
O2—Mn1—N2—C11	−34.4 (5)	C5—C4—C12—C11	0.2 (5)
O1—Mn1—N2—C11	−95.0 (2)	N2—C11—C12—N1	2.9 (5)
N4—Mn1—N2—C11	171.6 (2)	C7—C11—C12—N1	−176.3 (3)
N1—Mn1—N2—C11	6.3 (2)	N2—C11—C12—C4	−179.0 (3)
N3—Mn1—N2—C11	97.0 (2)	C7—C11—C12—C4	1.8 (5)
O2—Mn1—N3—C13	77.3 (3)	C24—N3—C13—C14	−1.4 (6)
O1—Mn1—N3—C13	145.9 (4)	Mn1—N3—C13—C14	−174.6 (3)
N4—Mn1—N3—C13	178.4 (3)	N3—C13—C14—C15	0.3 (7)
N1—Mn1—N3—C13	−15.6 (3)	C13—C14—C15—C16	0.9 (7)
N2—Mn1—N3—C13	−89.7 (3)	C14—C15—C16—C24	−0.9 (6)
O2—Mn1—N3—C24	−96.0 (2)	C14—C15—C16—C17	177.6 (4)
O1—Mn1—N3—C24	−27.4 (5)	C15—C16—C17—C18	−178.5 (4)
N4—Mn1—N3—C24	5.1 (2)	C24—C16—C17—C18	−0.1 (6)
N1—Mn1—N3—C24	171.0 (2)	C16—C17—C18—C19	0.8 (7)
N2—Mn1—N3—C24	96.9 (2)	C17—C18—C19—C23	−1.8 (6)
O2—Mn1—N4—C22	−92.1 (3)	C17—C18—C19—C20	178.5 (4)
O1—Mn1—N4—C22	−5.2 (3)	C23—C19—C20—C21	−0.9 (6)
N1—Mn1—N4—C22	131.6 (3)	C18—C19—C20—C21	178.8 (4)
N2—Mn1—N4—C22	80.3 (3)	C19—C20—C21—C22	0.2 (6)
N3—Mn1—N4—C22	−177.5 (3)	C23—N4—C22—C21	0.2 (5)
O2—Mn1—N4—C23	79.4 (2)	Mn1—N4—C22—C21	171.5 (3)
O1—Mn1—N4—C23	166.2 (2)	C20—C21—C22—N4	0.2 (6)
N1—Mn1—N4—C23	−56.9 (4)	C22—N4—C23—C19	−1.0 (5)
N2—Mn1—N4—C23	−108.3 (2)	Mn1—N4—C23—C19	−173.3 (3)
N3—Mn1—N4—C23	−6.0 (2)	C22—N4—C23—C24	178.6 (3)
C12—N1—C1—C2	0.3 (6)	Mn1—N4—C23—C24	6.3 (4)
Mn1—N1—C1—C2	175.4 (3)	C20—C19—C23—N4	1.3 (5)
N1—C1—C2—C3	−0.8 (7)	C18—C19—C23—N4	−178.4 (3)
C1—C2—C3—C4	0.3 (7)	C20—C19—C23—C24	−178.2 (3)
C2—C3—C4—C12	0.5 (6)	C18—C19—C23—C24	2.0 (5)
C2—C3—C4—C5	−178.6 (4)	C13—N3—C24—C16	1.4 (5)
C3—C4—C5—C6	177.0 (5)	Mn1—N3—C24—C16	175.5 (3)
C12—C4—C5—C6	−2.1 (7)	C13—N3—C24—C23	−177.8 (3)
C4—C5—C6—C7	1.9 (8)	Mn1—N3—C24—C23	−3.7 (4)
C5—C6—C7—C11	0.1 (7)	C15—C16—C24—N3	−0.3 (5)
C5—C6—C7—C8	−179.3 (5)	C17—C16—C24—N3	−178.8 (3)
C11—C7—C8—C9	2.3 (6)	C15—C16—C24—C23	178.9 (3)
C6—C7—C8—C9	−178.3 (4)	C17—C16—C24—C23	0.4 (5)
C7—C8—C9—C10	−1.6 (7)	N4—C23—C24—N3	−1.7 (4)
C11—N2—C10—C9	0.6 (5)	C19—C23—C24—N3	177.9 (3)
Mn1—N2—C10—C9	−170.1 (3)	N4—C23—C24—C16	179.1 (3)
C8—C9—C10—N2	0.1 (6)	C19—C23—C24—C16	−1.4 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1C···F3^i	0.85 (3)	1.81 (3)	2.660 (3)	176 (4)
O1—H1D···O3^ii	0.83 (3)	1.83 (3)	2.649 (3)	175 (5)
O2—H2C···F5^iii	0.84 (2)	1.72 (2)	2.552 (3)	172 (3)
O2—H2D···F4^i	0.82 (3)	2.31 (4)	2.947 (4)	135 (4)
O2—H2D···F5^i	0.82 (3)	2.25 (3)	3.028 (3)	157 (5)
C1—H1A···F1^iii	0.93	2.48	3.064 (4)	121
C3—H3···F1^iv	0.93	2.46	3.283 (6)	147
C5—H5···O1^v	0.93	2.59	3.330 (6)	137
C17—H17···F4^vi	0.93	2.43	3.278 (6)	152
C18—H18···F5^vii	0.93	2.44	3.344 (6)	166

Symmetry codes: (i) x−1, y, z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y, −z+1; (iv) x−1, y, z; (v) −x, −y+1, −z+1; (vi) −x+2, −y, −z+1; (vii) x, y, z+1.