Structural comparison of group 7 tricarbonyl complexes of 2-{[2-(1H-imidazol-4-yl)eth­yl]imino­meth­yl}-5-methyl­phenolate

Two tricarbonyl complexes of rhenium(I) and manganese(I) coordinated by the ligand 2-{[2-(1H-imidazol-4-yl)eth­yl]imino­meth­yl}-5-methyl­phenolate are re­ported, viz. fac-tricarbon­yl(2-{[2-(1H-imidazol-4-yl-κN³)eth­yl]imino­methyl-κN}-5-methyl­phenolato-κO)rhenium(I) methanol monosolvate, [Re(C₁₆H₁₄N₃O₄)(CO)₃]·CH₃OH, (I), and fac-tricarbon­yl(2-{[2-(1H-imidazol-4-yl-κN³)eth­yl]imino­methyl-κN}-5-methyl­phenolato-κO)manganese(I), fac-[Mn(C₁₆H₁₄N₃O₄)(CO)₃], (II), display facial coordination in a distorted octa­hedral environ­ment. The crystal structure of (I) is stabilized by O—H...O, N—H...O and C—H...O hydrogen-bond inter­actions, while that of (II) is stabilized by N—H...O hydrogen-bond inter­actions only. These inter­actions result in two-dimensional networks and π–π stacking for both structures.

Computing details

For both compounds, data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2004); software used to prepare material for publication: WinGX (Farrugia, 2012).

(I) fac-Tricarbonyl(2-{[2-(1H-imidazol-4-yl-κN³)ethyl]iminomethyl}-5-methylphenolato-κO)rhenium(I) methanol monosolvate

Crystal data

[Re(C13H14N3O)(CO)3]·CH4O	F(000) = 2048
Mr = 530.54	Dx = 1.908 Mg m^−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 9887 reflections
a = 28.400 (6) Å	θ = 2.8–27.7°
b = 9.0380 (18) Å	µ = 6.61 mm^−1
c = 14.390 (3) Å	T = 100 K
V = 3693.6 (13) Å^3	Plate, yellow
Z = 8	0.31 × 0.31 × 0.16 mm

Data collection

Bruker X8 APEXII 4K KappaCCD diffractometer	4450 independent reflections
Radiation source: sealed tube	3497 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.095
Detector resolution: 512 pixels mm^-1	θmax = 28.0°, θmin = 3.1°
ω and φ scans	h = −37→37
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −11→11
Tmin = 0.234, Tmax = 0.418	l = −19→18
69947 measured reflections

Refinement

Refinement on F^2	0 constraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.068	w = 1/[σ^2(Fo^2) + (0.0237P)^2 + 6.9735P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.005
4450 reflections	Δρmax = 1.06 e Å^−3
242 parameters	Δρmin = −0.86 e Å^−3
1 restraint

Special details

Experimental. The intensity data was collected on a Bruker X8 Apex II 4 K Kappa CCD diffractometer using an exposure time of 30 s/frame. A total of 1938 frames were collected with a frame width of 0.5° covering up to θ = 28.0° with 99.8% completeness accomplished

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Re1	0.61225 (2)	0.66513 (2)	0.79099 (2)	0.02398 (6)
O41	0.53458 (13)	0.8937 (4)	0.8267 (3)	0.0565 (10)
O1	0.63942 (9)	0.6769 (3)	0.92923 (18)	0.0256 (6)
O42	0.57825 (13)	0.6416 (4)	0.5896 (2)	0.0535 (10)
O43	0.67439 (13)	0.9209 (4)	0.7231 (2)	0.0476 (9)
O5	0.57715 (12)	0.2316 (4)	0.5542 (3)	0.0446 (8)
H5	0.5989	0.2599	0.5188	0.067*
N1	0.66422 (11)	0.4915 (4)	0.7816 (2)	0.0254 (7)
N32	0.56903 (11)	0.4803 (3)	0.8391 (2)	0.0262 (7)
N34	0.50537 (13)	0.3633 (4)	0.8854 (3)	0.0366 (9)
C1	0.70382 (13)	0.4915 (4)	0.8246 (3)	0.0242 (8)
H1	0.7252	0.4135	0.8112	0.029*
C41	0.56374 (17)	0.8090 (5)	0.8124 (3)	0.0358 (11)
C42	0.59057 (16)	0.6480 (5)	0.6669 (3)	0.0340 (10)
C2	0.65135 (15)	0.3573 (5)	0.7301 (3)	0.0319 (10)
H2A	0.6801	0.3023	0.7123	0.038*
H2B	0.6343	0.3844	0.6726	0.038*
C43	0.65167 (16)	0.8242 (5)	0.7498 (3)	0.0309 (9)
C3	0.62036 (15)	0.2608 (5)	0.7908 (3)	0.0332 (10)
H3A	0.6119	0.171	0.7551	0.04*
H3B	0.6391	0.2284	0.8451	0.04*
C5	0.57604 (19)	0.0748 (6)	0.5561 (4)	0.0512 (13)
H5A	0.5737	0.0369	0.4925	0.077*
H5B	0.5487	0.0417	0.5921	0.077*
H5C	0.6049	0.0376	0.5851	0.077*
C11	0.71850 (14)	0.6013 (4)	0.8919 (3)	0.0237 (8)
C12	0.68576 (14)	0.6855 (4)	0.9436 (3)	0.0232 (8)
C13	0.70319 (14)	0.7782 (4)	1.0141 (3)	0.0249 (8)
H13	0.6816	0.836	1.0491	0.03*
C14	0.75045 (15)	0.7881 (4)	1.0343 (3)	0.0266 (9)
C15	0.78284 (15)	0.7030 (4)	0.9832 (3)	0.0281 (9)
H15	0.8156	0.7091	0.9963	0.034*
C16	0.76661 (15)	0.6105 (5)	0.9139 (3)	0.0277 (9)
H16	0.7885	0.5516	0.8804	0.033*
C31	0.57568 (15)	0.3301 (4)	0.8260 (3)	0.0282 (9)
C33	0.52601 (14)	0.4943 (5)	0.8750 (3)	0.0321 (9)
H33	0.5119	0.586	0.8912	0.038*
C35	0.53635 (16)	0.2587 (5)	0.8538 (3)	0.0354 (10)
H35	0.5311	0.1549	0.8518	0.043*
C141	0.76777 (16)	0.8881 (5)	1.1103 (3)	0.0346 (10)
H14A	0.7518	0.984	1.1058	0.052*
H14B	0.8018	0.9025	1.1038	0.052*
H14C	0.761	0.8432	1.1708	0.052*
H34	0.4775 (9)	0.353 (5)	0.906 (3)	0.038 (14)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Re1	0.02367 (9)	0.02276 (9)	0.02550 (10)	−0.00083 (6)	−0.00229 (6)	−0.00093 (6)
O41	0.053 (2)	0.044 (2)	0.073 (3)	0.0243 (19)	−0.015 (2)	−0.0127 (19)
O1	0.0230 (14)	0.0291 (15)	0.0248 (14)	0.0012 (12)	−0.0015 (11)	−0.0053 (12)
O42	0.055 (2)	0.074 (3)	0.0311 (19)	−0.012 (2)	−0.0132 (16)	0.0027 (17)
O43	0.055 (2)	0.0357 (18)	0.052 (2)	−0.0166 (17)	0.0041 (17)	0.0035 (15)
O5	0.039 (2)	0.0409 (18)	0.054 (2)	−0.0010 (15)	0.0171 (16)	0.0034 (16)
N1	0.0245 (16)	0.0279 (17)	0.0239 (17)	−0.0011 (15)	0.0066 (13)	−0.0043 (14)
N32	0.0250 (17)	0.0238 (17)	0.0300 (18)	−0.0036 (14)	−0.0005 (14)	−0.0009 (14)
N34	0.027 (2)	0.040 (2)	0.043 (2)	−0.0066 (17)	0.0085 (18)	−0.0003 (17)
C1	0.024 (2)	0.027 (2)	0.0215 (18)	−0.0017 (17)	0.0064 (15)	−0.0005 (17)
C41	0.038 (3)	0.029 (2)	0.040 (3)	0.000 (2)	−0.012 (2)	0.0001 (19)
C42	0.031 (2)	0.037 (2)	0.033 (2)	−0.007 (2)	0.001 (2)	0.008 (2)
C2	0.029 (2)	0.032 (2)	0.035 (2)	−0.0026 (18)	0.0031 (18)	−0.0129 (18)
C43	0.034 (2)	0.029 (2)	0.030 (2)	0.0034 (19)	−0.0026 (19)	−0.0043 (19)
C3	0.031 (2)	0.023 (2)	0.046 (3)	0.0004 (17)	−0.0008 (19)	−0.0082 (19)
C5	0.050 (3)	0.047 (3)	0.056 (3)	−0.005 (3)	0.004 (3)	0.007 (3)
C11	0.027 (2)	0.0218 (18)	0.022 (2)	−0.0018 (16)	0.0012 (16)	0.0008 (16)
C12	0.025 (2)	0.0204 (19)	0.024 (2)	0.0015 (15)	0.0012 (16)	0.0030 (15)
C13	0.031 (2)	0.0208 (18)	0.023 (2)	0.0041 (16)	−0.0006 (16)	0.0003 (16)
C14	0.032 (2)	0.0238 (19)	0.024 (2)	−0.0007 (17)	−0.0056 (18)	0.0037 (16)
C15	0.025 (2)	0.032 (2)	0.028 (2)	−0.0014 (17)	−0.0038 (17)	0.0062 (17)
C16	0.029 (2)	0.028 (2)	0.027 (2)	0.0020 (17)	0.0028 (17)	0.0016 (17)
C31	0.028 (2)	0.027 (2)	0.031 (2)	−0.0015 (18)	−0.0017 (17)	−0.0015 (18)
C33	0.028 (2)	0.031 (2)	0.037 (2)	−0.0036 (19)	0.0037 (19)	−0.0041 (19)
C35	0.034 (2)	0.025 (2)	0.047 (3)	−0.0033 (19)	0.001 (2)	0.001 (2)
C141	0.039 (3)	0.036 (2)	0.029 (2)	−0.002 (2)	−0.0094 (19)	−0.0026 (19)

Geometric parameters (Å, º)

Re1—C42	1.896 (5)	C2—H2B	0.99
Re1—C43	1.916 (5)	C3—C31	1.503 (6)
Re1—C41	1.919 (5)	C3—H3A	0.99
Re1—O1	2.136 (3)	C3—H3B	0.99
Re1—N1	2.159 (3)	C5—H5A	0.98
Re1—N32	2.185 (3)	C5—H5B	0.98
O41—C41	1.146 (5)	C5—H5C	0.98
O1—C12	1.334 (5)	C11—C16	1.405 (6)
O42—C42	1.167 (5)	C11—C12	1.413 (5)
O43—C43	1.153 (5)	C12—C13	1.406 (5)
O5—C5	1.417 (6)	C13—C14	1.376 (6)
O5—H5	0.84	C13—H13	0.95
N1—C1	1.283 (5)	C14—C15	1.406 (6)
N1—C2	1.467 (5)	C14—C141	1.502 (5)
N32—C33	1.333 (5)	C15—C16	1.380 (6)
N32—C31	1.383 (5)	C15—H15	0.95
N34—C33	1.329 (5)	C16—H16	0.95
N34—C35	1.369 (6)	C31—C35	1.351 (6)
N34—H34	0.851 (19)	C33—H33	0.95
C1—C11	1.448 (5)	C35—H35	0.95
C1—H1	0.95	C141—H14A	0.98
C2—C3	1.516 (6)	C141—H14B	0.98
C2—H2A	0.99	C141—H14C	0.98
C42—Re1—C43	87.69 (18)	C2—C3—H3B	108.2
C42—Re1—C41	88.5 (2)	H3A—C3—H3B	107.3
C43—Re1—C41	87.74 (19)	O5—C5—H5A	109.5
C42—Re1—O1	177.16 (16)	O5—C5—H5B	109.5
C43—Re1—O1	92.26 (15)	H5A—C5—H5B	109.5
C41—Re1—O1	94.35 (15)	O5—C5—H5C	109.5
C42—Re1—N1	95.96 (16)	H5A—C5—H5C	109.5
C43—Re1—N1	97.28 (16)	H5B—C5—H5C	109.5
C41—Re1—N1	173.41 (16)	C16—C11—C12	119.3 (4)
O1—Re1—N1	81.23 (11)	C16—C11—C1	118.1 (4)
C42—Re1—N32	93.07 (16)	C12—C11—C1	122.1 (4)
C43—Re1—N32	178.42 (15)	O1—C12—C13	119.6 (3)
C41—Re1—N32	93.66 (17)	O1—C12—C11	122.4 (3)
O1—Re1—N32	86.91 (11)	C13—C12—C11	118.0 (4)
N1—Re1—N32	81.26 (13)	C14—C13—C12	122.3 (4)
C12—O1—Re1	120.2 (2)	C14—C13—H13	118.9
C5—O5—H5	109.5	C12—C13—H13	118.9
C1—N1—C2	117.5 (4)	C13—C14—C15	119.5 (4)
C1—N1—Re1	124.6 (3)	C13—C14—C141	120.8 (4)
C2—N1—Re1	117.5 (3)	C15—C14—C141	119.7 (4)
C33—N32—C31	105.7 (3)	C16—C15—C14	119.3 (4)
C33—N32—Re1	124.5 (3)	C16—C15—H15	120.3
C31—N32—Re1	129.1 (3)	C14—C15—H15	120.3
C33—N34—C35	107.1 (4)	C15—C16—C11	121.6 (4)
C33—N34—H34	123 (3)	C15—C16—H16	119.2
C35—N34—H34	130 (3)	C11—C16—H16	119.2
N1—C1—C11	125.1 (4)	C35—C31—N32	108.4 (4)
N1—C1—H1	117.4	C35—C31—C3	126.8 (4)
C11—C1—H1	117.4	N32—C31—C3	124.8 (4)
O41—C41—Re1	178.7 (5)	N34—C33—N32	111.3 (4)
O42—C42—Re1	177.6 (4)	N34—C33—H33	124.3
N1—C2—C3	109.2 (3)	N32—C33—H33	124.3
N1—C2—H2A	109.8	C31—C35—N34	107.5 (4)
C3—C2—H2A	109.8	C31—C35—H35	126.3
N1—C2—H2B	109.8	N34—C35—H35	126.3
C3—C2—H2B	109.8	C14—C141—H14A	109.5
H2A—C2—H2B	108.3	C14—C141—H14B	109.5
O43—C43—Re1	178.0 (4)	H14A—C141—H14B	109.5
C31—C3—C2	116.4 (4)	C14—C141—H14C	109.5
C31—C3—H3A	108.2	H14A—C141—H14C	109.5
C2—C3—H3A	108.2	H14B—C141—H14C	109.5
C31—C3—H3B	108.2
C2—N1—C1—C11	−168.2 (4)	C13—C14—C15—C16	−0.2 (6)
Re1—N1—C1—C11	5.3 (5)	C141—C14—C15—C16	179.5 (4)
C1—N1—C2—C3	95.4 (4)	C14—C15—C16—C11	1.2 (6)
Re1—N1—C2—C3	−78.5 (4)	C12—C11—C16—C15	−1.8 (6)
N1—C2—C3—C31	57.8 (5)	C1—C11—C16—C15	−174.2 (4)
N1—C1—C11—C16	−162.9 (4)	C33—N32—C31—C35	0.5 (5)
N1—C1—C11—C12	24.9 (6)	Re1—N32—C31—C35	−169.6 (3)
Re1—O1—C12—C13	140.6 (3)	C33—N32—C31—C3	−177.0 (4)
Re1—O1—C12—C11	−41.2 (5)	Re1—N32—C31—C3	13.0 (6)
C16—C11—C12—O1	−176.8 (3)	C2—C3—C31—C35	156.8 (4)
C1—C11—C12—O1	−4.8 (6)	C2—C3—C31—N32	−26.2 (6)
C16—C11—C12—C13	1.4 (5)	C35—N34—C33—N32	−0.6 (5)
C1—C11—C12—C13	173.5 (4)	C31—N32—C33—N34	0.1 (5)
O1—C12—C13—C14	177.8 (3)	Re1—N32—C33—N34	170.7 (3)
C11—C12—C13—C14	−0.5 (6)	N32—C31—C35—N34	−0.8 (5)
C12—C13—C14—C15	−0.1 (6)	C3—C31—C35—N34	176.6 (4)
C12—C13—C14—C141	−179.9 (4)	C33—N34—C35—C31	0.9 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O1^i	0.84	1.82	2.654 (4)	172
N34—H34···O5^ii	0.851 (19)	1.98 (3)	2.769 (5)	153 (4)
C35—H35···O41^iii	0.95	2.39	3.322 (6)	167

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

(II) fac-Tricarbonyl(2-{[2-(1H-imidazol-4-yl-κN³)ethyl]iminomethyl}-5-methylphenolato-κO)manganese(I)

Crystal data

[Mn(C13H14N3O)(CO)3]	Z = 2
Mr = 367.24	F(000) = 376
Triclinic, P1	Dx = 1.533 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4262 (11) Å	Cell parameters from 9881 reflections
b = 9.0038 (12) Å	θ = 2.4–28.4°
c = 13.0780 (18) Å	µ = 0.86 mm^−1
α = 108.494 (4)°	T = 100 K
β = 104.058 (5)°	Cuboid, yellow
γ = 93.363 (4)°	0.45 × 0.4 × 0.35 mm
V = 795.65 (19) Å^3

Data collection

Bruker X8 ApexII 4K Kappa CCD diffractometer	3840 independent reflections
Radiation source: sealed tube	3465 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
Detector resolution: 512 pixels mm^-1	θmax = 28.0°, θmin = 2.9°
ω and φ scans	h = −9→9
Absorption correction: multi-scan SADABS (Bruker, 2004)	k = −11→11
Tmin = 0.700, Tmax = 0.754	l = −17→17
23065 measured reflections

Refinement

Refinement on F^2	0 constraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.076	w = 1/[σ^2(Fo^2) + (0.0331P)^2 + 0.2774P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
3840 reflections	Δρmax = 0.30 e Å^−3
222 parameters	Δρmin = −0.25 e Å^−3
0 restraints

Special details

Experimental. The intensity data was collected on a Bruker X8 Apex II 4 K Kappa CCD diffractometer using an exposure time of 30 s/frame. A total of 1938 frames were collected with a frame width of 0.5° covering up to θ = 28.0° with 99.9% completeness accomplished

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Mn1	0.33044 (3)	0.28915 (2)	0.20671 (2)	0.02042 (8)
N1	0.49591 (17)	0.27765 (14)	0.35149 (9)	0.0213 (2)
N32	0.36595 (17)	0.05560 (14)	0.13724 (9)	0.0227 (2)
N34	0.35498 (19)	−0.17573 (16)	0.00903 (11)	0.0294 (3)
O41	0.1128 (2)	0.3236 (2)	−0.00342 (11)	0.0554 (4)
O1	0.57914 (14)	0.35750 (12)	0.18199 (8)	0.0238 (2)
O42	−0.03464 (16)	0.19609 (14)	0.23735 (10)	0.0350 (3)
O43	0.29572 (18)	0.62397 (14)	0.31472 (10)	0.0375 (3)
C1	0.6465 (2)	0.37608 (17)	0.41049 (11)	0.0239 (3)
H1	0.7102	0.3678	0.4804	0.029*
C41	0.1990 (2)	0.3054 (2)	0.07546 (13)	0.0306 (3)
C42	0.1103 (2)	0.22980 (17)	0.22737 (11)	0.0245 (3)
C2	0.4559 (2)	0.14201 (18)	0.38527 (11)	0.0261 (3)
H2A	0.3191	0.118	0.3739	0.031*
H2B	0.5198	0.1665	0.4658	0.031*
C43	0.3104 (2)	0.49447 (18)	0.27341 (12)	0.0246 (3)
C3	0.5257 (2)	−0.00027 (19)	0.31443 (13)	0.0310 (3)
H3A	0.6639	0.0233	0.3315	0.037*
H3B	0.4976	−0.0922	0.337	0.037*
C141	0.9950 (3)	0.8520 (2)	0.28463 (16)	0.0393 (4)
H14A	1.0777	0.8052	0.2389	0.059*
H14B	1.0689	0.9376	0.3524	0.059*
H14C	0.898	0.8947	0.2413	0.059*
C11	0.7243 (2)	0.49784 (17)	0.37729 (11)	0.0229 (3)
C12	0.69326 (19)	0.47922 (16)	0.26234 (11)	0.0215 (3)
C13	0.7893 (2)	0.59395 (18)	0.23528 (12)	0.0258 (3)
H13	0.7756	0.5803	0.1586	0.031*
C14	0.9038 (2)	0.72695 (18)	0.31738 (13)	0.0280 (3)
C15	0.9313 (2)	0.74383 (18)	0.43009 (13)	0.0306 (3)
H15	1.0084	0.8347	0.4869	0.037*
C16	0.8473 (2)	0.62951 (18)	0.45900 (12)	0.0284 (3)
H16	0.8726	0.6394	0.5358	0.034*
C31	0.4431 (2)	−0.04588 (18)	0.19044 (12)	0.0261 (3)
C33	0.3148 (2)	−0.02888 (18)	0.02809 (12)	0.0260 (3)
H33	0.2568	0.0107	−0.0291	0.031*
C35	0.4371 (2)	−0.18877 (19)	0.11063 (13)	0.0315 (3)
H35	0.4816	−0.2799	0.1234	0.038*
H34	0.354 (3)	−0.236 (3)	−0.0497 (19)	0.048 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mn1	0.02184 (12)	0.02117 (13)	0.01545 (11)	0.00187 (8)	0.00444 (8)	0.00328 (8)
N1	0.0248 (6)	0.0215 (6)	0.0166 (5)	0.0039 (5)	0.0071 (4)	0.0043 (4)
N32	0.0249 (6)	0.0219 (6)	0.0183 (5)	−0.0004 (5)	0.0070 (4)	0.0025 (4)
N34	0.0336 (7)	0.0251 (7)	0.0236 (6)	−0.0016 (5)	0.0134 (5)	−0.0025 (5)
O41	0.0596 (9)	0.0752 (11)	0.0313 (7)	0.0122 (8)	0.0001 (6)	0.0271 (7)
O1	0.0258 (5)	0.0239 (5)	0.0165 (4)	−0.0017 (4)	0.0068 (4)	0.0004 (4)
O42	0.0255 (6)	0.0401 (7)	0.0393 (6)	0.0009 (5)	0.0102 (5)	0.0133 (5)
O43	0.0412 (7)	0.0272 (6)	0.0422 (7)	0.0105 (5)	0.0139 (5)	0.0065 (5)
C1	0.0262 (7)	0.0266 (7)	0.0157 (6)	0.0043 (6)	0.0049 (5)	0.0035 (5)
C41	0.0327 (8)	0.0337 (9)	0.0233 (7)	0.0019 (7)	0.0075 (6)	0.0075 (6)
C42	0.0286 (7)	0.0224 (7)	0.0190 (6)	0.0044 (6)	0.0031 (5)	0.0047 (5)
C2	0.0323 (8)	0.0266 (7)	0.0185 (6)	0.0019 (6)	0.0066 (6)	0.0072 (5)
C43	0.0227 (7)	0.0293 (8)	0.0221 (6)	0.0041 (6)	0.0065 (5)	0.0089 (6)
C3	0.0407 (9)	0.0258 (8)	0.0248 (7)	0.0070 (7)	0.0063 (6)	0.0078 (6)
C141	0.0396 (10)	0.0275 (9)	0.0485 (10)	−0.0041 (7)	0.0145 (8)	0.0097 (7)
C11	0.0222 (7)	0.0232 (7)	0.0189 (6)	0.0024 (5)	0.0040 (5)	0.0026 (5)
C12	0.0206 (6)	0.0205 (7)	0.0205 (6)	0.0043 (5)	0.0064 (5)	0.0025 (5)
C13	0.0257 (7)	0.0260 (7)	0.0249 (7)	0.0025 (6)	0.0088 (6)	0.0065 (6)
C14	0.0240 (7)	0.0225 (7)	0.0360 (8)	0.0035 (6)	0.0107 (6)	0.0063 (6)
C15	0.0255 (7)	0.0234 (7)	0.0313 (8)	−0.0020 (6)	0.0034 (6)	−0.0017 (6)
C16	0.0283 (8)	0.0276 (8)	0.0205 (7)	0.0019 (6)	0.0026 (6)	0.0001 (6)
C31	0.0282 (7)	0.0236 (7)	0.0251 (7)	0.0030 (6)	0.0096 (6)	0.0051 (6)
C33	0.0280 (7)	0.0250 (7)	0.0201 (6)	−0.0033 (6)	0.0078 (5)	0.0016 (5)
C35	0.0369 (9)	0.0245 (8)	0.0320 (8)	0.0055 (6)	0.0133 (7)	0.0052 (6)

Geometric parameters (Å, º)

Mn1—C42	1.7988 (16)	C2—H2B	0.99
Mn1—C43	1.8090 (16)	C3—C31	1.496 (2)
Mn1—C41	1.8119 (16)	C3—H3A	0.99
Mn1—N1	2.0285 (12)	C3—H3B	0.99
Mn1—O1	2.0438 (10)	C141—C14	1.506 (2)
Mn1—N32	2.0704 (12)	C141—H14A	0.98
N1—C1	1.2890 (18)	C141—H14B	0.98
N1—C2	1.4624 (19)	C141—H14C	0.98
N32—C33	1.3321 (17)	C11—C16	1.4058 (19)
N32—C31	1.385 (2)	C11—C12	1.4172 (19)
N34—C33	1.331 (2)	C12—C13	1.403 (2)
N34—C35	1.366 (2)	C13—C14	1.390 (2)
N34—H34	0.79 (2)	C13—H13	0.95
O41—C41	1.140 (2)	C14—C15	1.395 (2)
O1—C12	1.3234 (16)	C15—C16	1.370 (2)
O42—C42	1.1498 (19)	C15—H15	0.95
O43—C43	1.1434 (19)	C16—H16	0.95
C1—C11	1.440 (2)	C31—C35	1.366 (2)
C1—H1	0.95	C33—H33	0.95
C2—C3	1.526 (2)	C35—H35	0.95
C2—H2A	0.99
C42—Mn1—C43	89.84 (7)	C31—C3—H3A	108.5
C42—Mn1—C41	87.95 (7)	C2—C3—H3A	108.5
C43—Mn1—C41	87.61 (7)	C31—C3—H3B	108.5
C42—Mn1—N1	96.49 (6)	C2—C3—H3B	108.5
C43—Mn1—N1	92.03 (6)	H3A—C3—H3B	107.5
C41—Mn1—N1	175.55 (6)	C14—C141—H14A	109.5
C42—Mn1—O1	179.40 (6)	C14—C141—H14B	109.5
C43—Mn1—O1	89.96 (5)	H14A—C141—H14B	109.5
C41—Mn1—O1	91.48 (6)	C14—C141—H14C	109.5
N1—Mn1—O1	84.08 (5)	H14A—C141—H14C	109.5
C42—Mn1—N32	91.51 (6)	H14B—C141—H14C	109.5
C43—Mn1—N32	176.96 (6)	C16—C11—C12	119.31 (14)
C41—Mn1—N32	95.16 (6)	C16—C11—C1	119.69 (13)
N1—Mn1—N32	85.11 (5)	C12—C11—C1	120.72 (12)
O1—Mn1—N32	88.72 (4)	O1—C12—C13	120.30 (13)
C1—N1—C2	117.42 (12)	O1—C12—C11	121.82 (13)
C1—N1—Mn1	123.27 (10)	C13—C12—C11	117.88 (13)
C2—N1—Mn1	118.97 (9)	C14—C13—C12	121.93 (14)
C33—N32—C31	105.52 (12)	C14—C13—H13	119
C33—N32—Mn1	125.39 (11)	C12—C13—H13	119
C31—N32—Mn1	129.09 (9)	C13—C14—C15	119.25 (14)
C33—N34—C35	107.41 (13)	C13—C14—C141	120.17 (15)
C33—N34—H34	125.6 (17)	C15—C14—C141	120.58 (14)
C35—N34—H34	125.6 (17)	C16—C15—C14	120.12 (13)
C12—O1—Mn1	117.60 (8)	C16—C15—H15	119.9
N1—C1—C11	124.24 (13)	C14—C15—H15	119.9
N1—C1—H1	117.9	C15—C16—C11	121.36 (14)
C11—C1—H1	117.9	C15—C16—H16	119.3
O41—C41—Mn1	175.88 (16)	C11—C16—H16	119.3
O42—C42—Mn1	176.58 (14)	C35—C31—N32	108.45 (13)
N1—C2—C3	108.66 (12)	C35—C31—C3	127.01 (15)
N1—C2—H2A	110	N32—C31—C3	124.49 (13)
C3—C2—H2A	110	N34—C33—N32	111.62 (14)
N1—C2—H2B	110	N34—C33—H33	124.2
C3—C2—H2B	110	N32—C33—H33	124.2
H2A—C2—H2B	108.3	N34—C35—C31	106.99 (15)
O43—C43—Mn1	179.18 (15)	N34—C35—H35	126.5
C31—C3—C2	114.95 (13)	C31—C35—H35	126.5
C2—N1—C1—C11	167.97 (13)	C13—C14—C15—C16	0.5 (2)
Mn1—N1—C1—C11	−5.2 (2)	C141—C14—C15—C16	179.85 (15)
C1—N1—C2—C3	−96.77 (15)	C14—C15—C16—C11	−3.5 (2)
Mn1—N1—C2—C3	76.68 (14)	C12—C11—C16—C15	2.9 (2)
N1—C2—C3—C31	−57.83 (17)	C1—C11—C16—C15	176.77 (14)
N1—C1—C11—C16	158.87 (14)	C33—N32—C31—C35	0.51 (17)
N1—C1—C11—C12	−27.4 (2)	Mn1—N32—C31—C35	179.96 (10)
Mn1—O1—C12—C13	−138.71 (11)	C33—N32—C31—C3	178.05 (14)
Mn1—O1—C12—C11	41.89 (17)	Mn1—N32—C31—C3	−2.5 (2)
C16—C11—C12—O1	179.94 (13)	C2—C3—C31—C35	−160.03 (16)
C1—C11—C12—O1	6.2 (2)	C2—C3—C31—N32	22.9 (2)
C16—C11—C12—C13	0.5 (2)	C35—N34—C33—N32	−0.12 (17)
C1—C11—C12—C13	−173.25 (13)	C31—N32—C33—N34	−0.24 (17)
O1—C12—C13—C14	177.11 (14)	Mn1—N32—C33—N34	−179.72 (9)
C11—C12—C13—C14	−3.5 (2)	C33—N34—C35—C31	0.44 (17)
C12—C13—C14—C15	3.0 (2)	N32—C31—C35—N34	−0.59 (18)
C12—C13—C14—C141	−176.33 (14)	C3—C31—C35—N34	−178.05 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N34—H34···O1^i	0.79 (2)	1.93 (2)	2.6931 (16)	164 (2)

Symmetry code: (i) −x+1, −y, −z.