[2-(3,5-Dibromo-2-oxidobenzyl­amino)-3-phenyl­propionato-κ³O,N,O′](1,10-phenanthroline-κ²N,N′)manganese(II) dihydrate

In the title compound, [Mn(C₁₆H₁₃Br₂NO₃)(C₁₂H₈N₂)]·2H₂O, the Mn^II atom is coordinated in a slightly distorted square-pyramidal geometry by one N and two O atoms from the tridentate 2-(3,5-dibromo-2-oxidobenzyl­amino)-3-phenyl­propionate ligand and two N atoms from the bidentate 1,10-phenanthroline ligand. The benzyl group is oriented so that an additional axial inter­action with the aromatic ring imparts pseudo-octa­hedral coordination geometry to the Mn^II atom.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.016 Å
• R factor = 0.062
• wR factor = 0.212
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT341_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ...         16
PLAT417_ALERT_2_B Short Inter D-H..H-D       H29    ..  H32     ..       1.74 Ang.

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.247     0.337
            Tmin and Tmax expected:      0.219     0.337
            RR =      1.130
            Please check that your absorption correction is appropriate.
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.118
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.12
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large .......       1.10
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Mn1    -   O1      ..       6.16 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Mn1    -   N1      ..       7.04 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Mn1    -   N2      ..       5.31 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Mn1    -   N3      ..       5.04 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Mn1
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      35.00 A   3 

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  10 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
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

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: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

[2-(3,5-Dibromo-2-oxidobenzylamino)-3-phenylpropionato-κ³O,N,O'](1,10- phenanthroline-κ²N,N')manganese(II) dihydrate

Crystal data

[Mn(C16H13Br2NO3)(C12H8N2)]·2H2O	F(000) = 2792
Mr = 698.27	Dx = 1.622 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3852 reflections
a = 11.199 (3) Å	θ = 2.2–20.8°
b = 18.962 (2) Å	µ = 3.30 mm^−1
c = 26.932 (3) Å	T = 298 K
V = 5719.4 (17) Å^3	Prism, colourless
Z = 8	0.48 × 0.40 × 0.33 mm

Data collection

Bruker SMART CCD diffractometer	5044 independent reflections
Radiation source: fine-focus sealed tube	2646 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.118
φ and ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.247, Tmax = 0.337	k = −12→22
28160 measured reflections	l = −32→31

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.212	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0776P)^2 + 33.98P] where P = (Fo^2 + 2Fc^2)/3
5044 reflections	(Δ/σ)max = 0.001
352 parameters	Δρmax = 1.48 e Å^−3
18 restraints	Δρmin = −0.93 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
Mn1	0.66681 (9)	0.25413 (6)	0.65785 (4)	0.0257 (3)
Br1	0.67674 (10)	0.43454 (7)	0.53345 (4)	0.0675 (4)
Br2	0.24783 (13)	0.53092 (10)	0.62098 (6)	0.1058 (6)
N1	0.5531 (6)	0.2811 (4)	0.7121 (3)	0.0430 (19)
H1	0.4785	0.2644	0.7055	0.052*
N2	0.7798 (7)	0.2070 (4)	0.6107 (3)	0.051 (2)
N3	0.5458 (7)	0.2311 (4)	0.6024 (3)	0.052 (2)
O1	0.7837 (5)	0.2536 (3)	0.7126 (2)	0.0476 (16)
O2	0.7954 (6)	0.2511 (4)	0.7952 (2)	0.062 (2)
O3	0.6994 (5)	0.3590 (3)	0.6332 (2)	0.0510 (17)
O4	0.9449 (8)	0.3738 (5)	0.6334 (4)	0.128 (4)
H29	1.0107	0.3734	0.6491	0.153*
H30	0.8872	0.3716	0.6538	0.153*
O5	0.6512 (12)	0.2862 (8)	0.8800 (5)	0.177 (5)
H31	0.6895	0.2714	0.8549	0.213*
H32	0.6346	0.3291	0.8740	0.213*
C1	0.7369 (8)	0.2524 (5)	0.7562 (4)	0.046 (2)
C2	0.6015 (7)	0.2489 (5)	0.7586 (3)	0.043 (2)
H2	0.5740	0.2766	0.7871	0.052*
C3	0.5607 (8)	0.1723 (5)	0.7652 (3)	0.049 (2)
H3A	0.5877	0.1560	0.7974	0.058*
H3B	0.4741	0.1715	0.7655	0.058*
C4	0.6031 (8)	0.1210 (5)	0.7268 (4)	0.052 (3)
C5	0.5342 (9)	0.1054 (6)	0.6855 (4)	0.064 (3)
H5	0.4586	0.1252	0.6826	0.077*
C6	0.5756 (11)	0.0607 (6)	0.6483 (5)	0.074 (3)
H6	0.5278	0.0502	0.6210	0.089*
C7	0.6899 (12)	0.0317 (7)	0.6524 (6)	0.088 (4)
H7	0.7202	0.0031	0.6273	0.105*
C8	0.7577 (12)	0.0463 (7)	0.6943 (6)	0.088 (4)
H8	0.8329	0.0261	0.6978	0.105*
C9	0.7156 (9)	0.0894 (6)	0.7303 (5)	0.072 (3)
H9	0.7627	0.0983	0.7580	0.086*
C10	0.5514 (9)	0.3599 (5)	0.7176 (4)	0.053 (3)
H10A	0.6297	0.3757	0.7283	0.064*
H10B	0.4946	0.3725	0.7434	0.064*
C11	0.5184 (8)	0.3977 (5)	0.6705 (3)	0.046 (2)
C12	0.6018 (8)	0.3955 (5)	0.6303 (4)	0.051 (3)
C13	0.5693 (8)	0.4360 (5)	0.5877 (3)	0.047 (2)
C14	0.4652 (9)	0.4744 (6)	0.5849 (4)	0.058 (3)
H14	0.4461	0.4990	0.5561	0.069*
C15	0.3890 (9)	0.4759 (6)	0.6254 (4)	0.060 (3)
C16	0.4151 (9)	0.4375 (6)	0.6674 (4)	0.056 (3)
H16	0.3625	0.4384	0.6941	0.067*
C17	0.8951 (9)	0.1978 (6)	0.6156 (4)	0.059 (3)
H17	0.9322	0.2140	0.6443	0.071*
C18	0.9651 (10)	0.1641 (7)	0.5791 (5)	0.077 (4)
H18	1.0470	0.1586	0.5833	0.092*
C19	0.9097 (12)	0.1399 (7)	0.5375 (5)	0.085 (4)
H19	0.9547	0.1179	0.5129	0.102*
C20	0.7861 (11)	0.1475 (6)	0.5310 (4)	0.068 (3)
C21	0.7244 (9)	0.1827 (5)	0.5685 (3)	0.050 (2)
C22	0.5994 (9)	0.1955 (5)	0.5642 (4)	0.052 (3)
C23	0.5382 (10)	0.1723 (6)	0.5222 (4)	0.063 (3)
C24	0.4183 (11)	0.1862 (7)	0.5193 (4)	0.074 (3)
H24	0.3745	0.1715	0.4919	0.089*
C25	0.3627 (10)	0.2225 (7)	0.5578 (5)	0.074 (3)
H25	0.2815	0.2325	0.5562	0.089*
C26	0.4308 (9)	0.2439 (6)	0.5990 (4)	0.066 (3)
H26	0.3932	0.2679	0.6248	0.079*
C27	0.7200 (13)	0.1242 (7)	0.4886 (4)	0.082 (4)
H27	0.7595	0.1000	0.4635	0.098*
C28	0.6045 (14)	0.1363 (7)	0.4843 (5)	0.086 (4)
H28	0.5649	0.1211	0.4560	0.103*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mn1	0.0173 (5)	0.0336 (7)	0.0261 (6)	0.0051 (5)	0.0018 (5)	−0.0042 (5)
Br1	0.0577 (7)	0.0915 (9)	0.0531 (6)	0.0082 (6)	0.0000 (5)	0.0054 (6)
Br2	0.0797 (9)	0.1343 (14)	0.1035 (11)	0.0634 (9)	−0.0100 (8)	−0.0082 (10)
N1	0.031 (4)	0.052 (5)	0.047 (4)	−0.002 (4)	−0.007 (3)	0.003 (4)
N2	0.042 (5)	0.058 (6)	0.053 (5)	0.006 (4)	0.003 (4)	0.004 (4)
N3	0.041 (5)	0.063 (6)	0.053 (5)	0.002 (4)	0.004 (4)	−0.003 (4)
O1	0.035 (3)	0.059 (4)	0.049 (4)	0.003 (3)	0.004 (3)	−0.003 (3)
O2	0.038 (4)	0.102 (6)	0.045 (4)	−0.002 (4)	−0.005 (3)	−0.004 (4)
O3	0.037 (4)	0.055 (4)	0.061 (4)	0.005 (3)	0.007 (3)	0.003 (3)
O4	0.076 (6)	0.120 (7)	0.187 (8)	0.011 (5)	0.018 (6)	0.009 (6)
O5	0.162 (9)	0.215 (9)	0.156 (8)	0.030 (8)	0.001 (7)	−0.011 (8)
C1	0.035 (5)	0.051 (6)	0.052 (6)	0.004 (5)	0.000 (5)	0.000 (5)
C2	0.032 (5)	0.057 (6)	0.040 (5)	0.003 (4)	−0.003 (4)	−0.002 (5)
C3	0.036 (5)	0.057 (7)	0.053 (6)	−0.003 (5)	0.007 (4)	0.001 (5)
C4	0.033 (5)	0.052 (6)	0.069 (7)	−0.006 (4)	0.003 (5)	0.000 (6)
C5	0.043 (6)	0.078 (8)	0.072 (7)	−0.002 (6)	0.005 (6)	−0.008 (7)
C6	0.072 (8)	0.066 (8)	0.084 (8)	−0.012 (6)	0.010 (7)	−0.010 (7)
C7	0.083 (10)	0.063 (8)	0.117 (12)	0.002 (7)	0.029 (9)	−0.018 (8)
C8	0.061 (8)	0.071 (9)	0.131 (12)	0.016 (7)	−0.003 (9)	−0.028 (9)
C9	0.043 (6)	0.073 (8)	0.099 (9)	0.010 (6)	−0.003 (6)	−0.013 (7)
C10	0.049 (6)	0.053 (7)	0.056 (6)	0.004 (5)	0.000 (5)	−0.002 (5)
C11	0.044 (5)	0.046 (6)	0.047 (5)	0.010 (4)	−0.006 (4)	−0.008 (5)
C12	0.032 (5)	0.056 (7)	0.064 (7)	−0.002 (5)	−0.002 (5)	−0.010 (5)
C13	0.040 (5)	0.054 (6)	0.048 (6)	0.004 (5)	−0.011 (4)	−0.005 (5)
C14	0.055 (6)	0.065 (7)	0.054 (6)	0.009 (6)	−0.013 (5)	−0.005 (5)
C15	0.052 (6)	0.066 (7)	0.061 (7)	0.012 (6)	−0.008 (5)	−0.003 (6)
C16	0.046 (6)	0.068 (7)	0.055 (6)	0.007 (5)	0.003 (5)	−0.007 (6)
C17	0.046 (6)	0.080 (8)	0.051 (6)	0.007 (5)	0.002 (5)	0.001 (6)
C18	0.047 (7)	0.104 (10)	0.080 (9)	0.025 (7)	0.022 (6)	−0.005 (8)
C19	0.078 (9)	0.106 (11)	0.072 (8)	0.027 (8)	0.019 (7)	−0.012 (8)
C20	0.076 (8)	0.073 (8)	0.054 (7)	0.008 (7)	0.017 (6)	−0.008 (6)
C21	0.069 (7)	0.043 (6)	0.039 (5)	−0.006 (5)	−0.002 (5)	−0.001 (5)
C22	0.047 (6)	0.058 (7)	0.050 (6)	−0.007 (5)	0.000 (5)	0.004 (5)
C23	0.064 (7)	0.075 (8)	0.051 (6)	−0.006 (6)	−0.005 (6)	−0.008 (6)
C24	0.070 (8)	0.095 (10)	0.057 (7)	−0.014 (7)	−0.014 (6)	−0.011 (7)
C25	0.047 (6)	0.096 (9)	0.080 (8)	−0.013 (6)	−0.014 (6)	0.000 (8)
C26	0.051 (6)	0.094 (9)	0.052 (6)	−0.005 (6)	−0.004 (5)	−0.008 (6)
C27	0.097 (10)	0.094 (10)	0.054 (7)	0.008 (8)	0.010 (7)	−0.032 (7)
C28	0.098 (11)	0.094 (10)	0.066 (8)	−0.004 (9)	−0.010 (8)	−0.027 (7)

Geometric parameters (Å, º)

Mn1—O1	1.972 (6)	C8—C9	1.351 (16)
Mn1—N1	2.004 (7)	C8—H8	0.930
Mn1—N2	2.003 (8)	C9—H9	0.930
Mn1—N3	2.064 (8)	C10—C11	1.504 (12)
Mn1—O3	2.128 (6)	C10—H10A	0.970
Br1—C13	1.892 (9)	C10—H10B	0.970
Br2—C15	1.898 (10)	C11—C16	1.384 (12)
N1—C2	1.497 (10)	C11—C12	1.430 (13)
N1—C10	1.502 (12)	C12—C13	1.429 (13)
N1—H1	0.910	C13—C14	1.376 (13)
N2—C17	1.310 (12)	C14—C15	1.386 (14)
N2—C21	1.374 (12)	C14—H14	0.930
N3—C26	1.314 (12)	C15—C16	1.375 (14)
N3—C22	1.368 (12)	C16—H16	0.930
O1—C1	1.286 (10)	C17—C18	1.411 (14)
O2—C1	1.238 (11)	C17—H17	0.930
O3—C12	1.296 (11)	C18—C19	1.360 (16)
O4—H29	0.850	C18—H18	0.930
O4—H30	0.850	C19—C20	1.403 (16)
O5—H31	0.850	C19—H19	0.930
O5—H32	0.850	C20—C21	1.394 (14)
C1—C2	1.519 (12)	C20—C27	1.430 (16)
C2—C3	1.533 (13)	C21—C22	1.425 (13)
C2—H2	0.980	C22—C23	1.394 (13)
C3—C4	1.497 (13)	C23—C24	1.371 (15)
C3—H3A	0.970	C23—C28	1.433 (16)
C3—H3B	0.970	C24—C25	1.390 (16)
C4—C5	1.385 (13)	C24—H24	0.930
C4—C9	1.399 (13)	C25—C26	1.408 (14)
C5—C6	1.393 (14)	C25—H25	0.930
C5—H5	0.930	C26—H26	0.930
C6—C7	1.397 (17)	C27—C28	1.319 (17)
C6—H6	0.930	C27—H27	0.930
C7—C8	1.389 (18)	C28—H28	0.930
C7—H7	0.930
O1—Mn1—N2	93.0 (3)	N1—C10—H10A	109.0
O1—Mn1—N1	83.0 (3)	C11—C10—H10A	109.0
N2—Mn1—N1	167.8 (3)	N1—C10—H10B	109.0
O1—Mn1—N3	167.5 (3)	C11—C10—H10B	109.0
N2—Mn1—N3	82.0 (3)	H10A—C10—H10B	107.8
N1—Mn1—N3	99.5 (3)	C16—C11—C12	121.0 (9)
O1—Mn1—O3	97.1 (3)	C16—C11—C10	121.1 (9)
N2—Mn1—O3	96.3 (3)	C12—C11—C10	117.7 (8)
N1—Mn1—O3	95.6 (3)	O3—C12—C13	123.4 (9)
N3—Mn1—O3	94.8 (3)	O3—C12—C11	121.4 (9)
C2—N1—C10	109.1 (7)	C13—C12—C11	115.2 (8)
C2—N1—Mn1	106.0 (5)	C14—C13—C12	123.0 (9)
C10—N1—Mn1	109.6 (5)	C14—C13—Br1	120.3 (8)
C2—N1—H1	110.7	C12—C13—Br1	116.7 (7)
C10—N1—H1	110.7	C13—C14—C15	119.3 (10)
Mn1—N1—H1	110.7	C13—C14—H14	120.4
C17—N2—C21	119.0 (9)	C15—C14—H14	120.4
C17—N2—Mn1	128.1 (7)	C16—C15—C14	120.4 (10)
C21—N2—Mn1	112.9 (6)	C16—C15—Br2	121.3 (8)
C26—N3—C22	118.0 (9)	C14—C15—Br2	118.3 (8)
C26—N3—Mn1	130.8 (7)	C15—C16—C11	121.1 (9)
C22—N3—Mn1	111.1 (6)	C15—C16—H16	119.5
C1—O1—Mn1	114.4 (5)	C11—C16—H16	119.5
C12—O3—Mn1	111.9 (6)	N2—C17—C18	122.4 (10)
H29—O4—H30	109.6	N2—C17—H17	118.8
H31—O5—H32	105.9	C18—C17—H17	118.8
O2—C1—O1	124.0 (8)	C19—C18—C17	118.3 (11)
O2—C1—C2	119.4 (8)	C19—C18—H18	120.8
O1—C1—C2	116.5 (8)	C17—C18—H18	120.8
N1—C2—C1	107.9 (7)	C18—C19—C20	121.2 (11)
N1—C2—C3	112.1 (7)	C18—C19—H19	119.4
C1—C2—C3	110.1 (8)	C20—C19—H19	119.4
N1—C2—H2	108.9	C21—C20—C19	116.6 (11)
C1—C2—H2	108.9	C21—C20—C27	118.0 (11)
C3—C2—H2	108.9	C19—C20—C27	125.3 (11)
C4—C3—C2	116.2 (8)	N2—C21—C20	122.4 (10)
C4—C3—H3A	108.2	N2—C21—C22	117.0 (9)
C2—C3—H3A	108.2	C20—C21—C22	120.6 (10)
C4—C3—H3B	108.2	N3—C22—C23	123.4 (9)
C2—C3—H3B	108.2	N3—C22—C21	117.0 (9)
H3A—C3—H3B	107.4	C23—C22—C21	119.6 (10)
C5—C4—C9	117.6 (10)	C24—C23—C22	117.8 (10)
C5—C4—C3	121.2 (9)	C24—C23—C28	124.0 (11)
C9—C4—C3	121.2 (10)	C22—C23—C28	118.2 (11)
C4—C5—C6	121.5 (11)	C23—C24—C25	119.5 (10)
C4—C5—H5	119.2	C23—C24—H24	120.2
C6—C5—H5	119.2	C25—C24—H24	120.2
C5—C6—C7	119.2 (12)	C24—C25—C26	119.2 (11)
C5—C6—H6	120.4	C24—C25—H25	120.4
C7—C6—H6	120.4	C26—C25—H25	120.4
C8—C7—C6	119.1 (12)	N3—C26—C25	122.1 (11)
C8—C7—H7	120.4	N3—C26—H26	118.9
C6—C7—H7	120.4	C25—C26—H26	118.9
C9—C8—C7	120.8 (12)	C28—C27—C20	121.6 (11)
C9—C8—H8	119.6	C28—C27—H27	119.2
C7—C8—H8	119.6	C20—C27—H27	119.2
C8—C9—C4	121.7 (12)	C27—C28—C23	121.9 (12)
C8—C9—H9	119.1	C27—C28—H28	119.0
C4—C9—H9	119.1	C23—C28—H28	119.0
N1—C10—C11	113.1 (8)
O1—Mn1—N1—C2	−28.8 (5)	N1—C10—C11—C12	−68.8 (11)
N2—Mn1—N1—C2	42.9 (17)	Mn1—O3—C12—C13	−130.5 (8)
N3—Mn1—N1—C2	138.8 (6)	Mn1—O3—C12—C11	49.4 (10)
O3—Mn1—N1—C2	−125.4 (5)	C16—C11—C12—O3	179.2 (9)
O1—Mn1—N1—C10	88.7 (6)	C10—C11—C12—O3	3.9 (14)
N2—Mn1—N1—C10	160.4 (13)	C16—C11—C12—C13	−0.9 (13)
N3—Mn1—N1—C10	−103.7 (6)	C10—C11—C12—C13	−176.2 (8)
O3—Mn1—N1—C10	−7.8 (6)	O3—C12—C13—C14	179.7 (9)
O1—Mn1—N2—C17	−13.4 (9)	C11—C12—C13—C14	−0.2 (14)
N1—Mn1—N2—C17	−84.1 (18)	O3—C12—C13—Br1	0.0 (12)
N3—Mn1—N2—C17	178.1 (9)	C11—C12—C13—Br1	−179.8 (7)
O3—Mn1—N2—C17	84.1 (9)	C12—C13—C14—C15	1.8 (15)
O1—Mn1—N2—C21	166.8 (7)	Br1—C13—C14—C15	−178.6 (8)
N1—Mn1—N2—C21	96.1 (15)	C13—C14—C15—C16	−2.2 (16)
N3—Mn1—N2—C21	−1.6 (7)	C13—C14—C15—Br2	178.6 (8)
O3—Mn1—N2—C21	−95.7 (7)	C14—C15—C16—C11	1.2 (16)
O1—Mn1—N3—C26	113.1 (14)	Br2—C15—C16—C11	−179.7 (8)
N2—Mn1—N3—C26	−179.5 (10)	C12—C11—C16—C15	0.5 (15)
N1—Mn1—N3—C26	12.7 (10)	C10—C11—C16—C15	175.6 (10)
O3—Mn1—N3—C26	−83.8 (10)	C21—N2—C17—C18	0.4 (16)
O1—Mn1—N3—C22	−65.6 (16)	Mn1—N2—C17—C18	−179.3 (8)
N2—Mn1—N3—C22	1.7 (7)	N2—C17—C18—C19	−0.7 (18)
N1—Mn1—N3—C22	−166.0 (6)	C17—C18—C19—C20	−1 (2)
O3—Mn1—N3—C22	97.5 (7)	C18—C19—C20—C21	1.9 (19)
N2—Mn1—O1—C1	−152.5 (7)	C18—C19—C20—C27	179.6 (13)
N1—Mn1—O1—C1	15.9 (6)	C17—N2—C21—C20	1.1 (15)
N3—Mn1—O1—C1	−86.3 (14)	Mn1—N2—C21—C20	−179.2 (8)
O3—Mn1—O1—C1	110.7 (6)	C17—N2—C21—C22	−178.5 (9)
O1—Mn1—O3—C12	−127.5 (6)	Mn1—N2—C21—C22	1.3 (11)
N2—Mn1—O3—C12	138.6 (6)	C19—C20—C21—N2	−2.2 (16)
N1—Mn1—O3—C12	−43.9 (6)	C27—C20—C21—N2	179.9 (10)
N3—Mn1—O3—C12	56.1 (6)	C19—C20—C21—C22	177.4 (10)
Mn1—O1—C1—O2	179.1 (8)	C27—C20—C21—C22	−0.5 (16)
Mn1—O1—C1—C2	2.2 (11)	C26—N3—C22—C23	0.0 (15)
C10—N1—C2—C1	−81.8 (9)	Mn1—N3—C22—C23	178.9 (8)
Mn1—N1—C2—C1	36.1 (8)	C26—N3—C22—C21	179.5 (10)
C10—N1—C2—C3	156.7 (7)	Mn1—N3—C22—C21	−1.6 (11)
Mn1—N1—C2—C3	−85.4 (7)	N2—C21—C22—N3	0.2 (13)
O2—C1—C2—N1	156.4 (8)	C20—C21—C22—N3	−179.3 (9)
O1—C1—C2—N1	−26.5 (11)	N2—C21—C22—C23	179.8 (9)
O2—C1—C2—C3	−80.9 (11)	C20—C21—C22—C23	0.2 (15)
O1—C1—C2—C3	96.1 (10)	N3—C22—C23—C24	0.1 (17)
N1—C2—C3—C4	64.0 (10)	C21—C22—C23—C24	−179.5 (11)
C1—C2—C3—C4	−56.2 (11)	N3—C22—C23—C28	179.2 (10)
C2—C3—C4—C5	−93.5 (11)	C21—C22—C23—C28	−0.3 (16)
C2—C3—C4—C9	83.8 (12)	C22—C23—C24—C25	0.1 (18)
C9—C4—C5—C6	−0.9 (16)	C28—C23—C24—C25	−179.0 (12)
C3—C4—C5—C6	176.5 (10)	C23—C24—C25—C26	−0.3 (19)
C4—C5—C6—C7	−0.9 (17)	C22—N3—C26—C25	−0.2 (16)
C5—C6—C7—C8	2.3 (19)	Mn1—N3—C26—C25	−178.9 (8)
C6—C7—C8—C9	−2 (2)	C24—C25—C26—N3	0.4 (18)
C7—C8—C9—C4	0 (2)	C21—C20—C27—C28	1 (2)
C5—C4—C9—C8	1.4 (17)	C19—C20—C27—C28	−176.7 (14)
C3—C4—C9—C8	−176.1 (11)	C20—C27—C28—C23	−1 (2)
C2—N1—C10—C11	172.9 (7)	C24—C23—C28—C27	179.8 (14)
Mn1—N1—C10—C11	57.2 (9)	C22—C23—C28—C27	1 (2)
N1—C10—C11—C16	115.9 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^i	0.91	2.07	2.948 (9)	163
O4—H30···O3	0.85	2.19	2.764 (11)	125
O4—H29···O5^ii	0.85	2.41	2.868 (17)	114
O5—H31···O2	0.85	2.03	2.876 (15)	171
O5—H32···O4^i	0.85	2.30	2.868 (17)	125

Symmetry codes: (i) x−1/2, y, −z+3/2; (ii) x+1/2, y, −z+3/2.