Solvent dependence of the solid-state structures of salicylaldiminate magnesium amide complexes

There are challenges in using magnesium coordination complexes as reagents owing to their tendency to adopt varying aggregation states in solution and thus impacting the reactivity of the complexes. Many magnesium complexes are prone to ligand redistribution via Schlenk equilibrium due to the ionic character within the metal-ligand inter­actions. The role of the supporting ligand is often crucial for providing stability to the heteroleptic complex. Strategies to minimize ligand redistribution in alkaline earth metal complexes could include using a supporting ligand with tunable sterics and electronics to influence the degree of association to the metal atom. Magnesium bis­(hexa­methyl­disilazide) was reacted with salicylaldimines [¹L = N-(2,6-diiso­propyl­phen­yl)salicylaldimine and ²L = 3,5-di-tert-butyl-N-(2,6-diiso­propyl­phen­yl)salicylaldimine] in either nondonor (toluene) or donor solvents [tetra­hydro­furan (THF) or pyridine]. The structures of the magnesium complexes were studied in the solid state via X-ray diffraction. In the nondonor solvent, i.e. toluene, the heteroleptic complex bis­{[mu]-2-[(2,6-diiso­propyl­phen­yl)imino­meth­yl]phenolato}-[kappa]³N,O:O;[kappa]³O:N,O-bis­[(hexa­methyl­disilazido-[kappa]N)magnesium(II)], [Mg₂(C₁₉H₂₂NO)₂(C₆H₁₈NSi₂)₂] or [¹LMgN(SiMe₃)₂]₂, (1), was favored, while in the donor solvent, i.e. pyridine (pyr), the formation of the homoleptic complex {2,4-di-tert-but­yl-6-[(2,6-diiso­propyl­phen­yl)imino­meth­yl]phenolato-[kappa]²N,O}bis­(pyridine-[kappa]N)magnesium(II) toluene monosolvate, [Mg(C₂₇H₃₈NO)₂(C₅H₅N)₂]·C₅H₅N or [{²L₂Mg₂(pyr)₂}·pyr], (2), predominated. Heteroleptic complex (1) was crystallized from toluene, while homoleptic complexes (2) and the previously reported [¹L₂Mg·THF] [Quinque et al. (2011). Eur. J. Inorg. Chem. pp. 3321-3326] were crystallized from pyridine and THF, respectively. These studies support solvent-dependent ligand redistribution in solution. In-situ ¹H NMR experiments were carried out to further probe the solution behavior of these systems.

Computing details

For both compounds, data collection: APEX2 (Bruker, 2008); cell refinement: APEX2 and SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008) and XPREP (Sheldrick, 2003); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: CrystalMaker (CrystalMaker, 2010).

(Compound1) Bis{µ-2-[(2,6-diisopropylphenyl)iminomethyl]phenolato}-κ³N,O:O;κ³O:N,O-bis[(hexamethyldisilazido-κN)magnesium(II)]

Crystal data

[Mg2(C19H22NO)2(C6H18NSi2)2]	Z = 1
Mr = 930.16	F(000) = 504
Triclinic, P1	Dx = 1.151 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.4898 (11) Å	Cell parameters from 9880 reflections
b = 11.3067 (12) Å	θ = 2.2–28.3°
c = 12.7370 (13) Å	µ = 0.17 mm^−1
α = 76.033 (1)°	T = 120 K
β = 66.454 (1)°	Plate, pale yellow
γ = 81.772 (1)°	0.32 × 0.28 × 0.12 mm
V = 1342.1 (2) Å^3

Data collection

Bruker X8 APEXII CCD diffractometer	5485 independent reflections
Radiation source: fine-focus sealed tube	4900 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 8.33 pixels mm^-1	θmax = 26.4°, θmin = 1.8°
φ and ω scans	h = −13→13
Absorption correction: multi-scan [Blessing (1995) and SADABS (Bruker, 2008; Krause et al., 2015)]	k = −14→14
Tmin = 0.95, Tmax = 0.98	l = −15→15
31120 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.031	H-atom parameters constrained
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.047P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.59	(Δ/σ)max < 0.001
5485 reflections	Δρmax = 0.32 e Å^−3
290 parameters	Δρmin = −0.20 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
Mg1	0.46802 (4)	0.38473 (4)	0.09838 (3)	0.01378 (11)
O1	0.42473 (8)	0.56590 (8)	0.07456 (7)	0.01461 (19)
N1	0.31637 (10)	0.26956 (10)	0.19366 (9)	0.0160 (2)
N2	0.33855 (10)	0.67594 (9)	−0.11961 (9)	0.0143 (2)
Si1	0.27389 (3)	0.18011 (3)	0.12277 (3)	0.01727 (11)
Si2	0.21224 (3)	0.27877 (3)	0.33493 (3)	0.01727 (11)
C1	0.32446 (12)	0.71594 (11)	−0.23202 (10)	0.0161 (3)
C2	0.31568 (12)	0.62781 (12)	−0.28952 (11)	0.0173 (3)
C3	0.29985 (13)	0.66848 (12)	−0.39636 (11)	0.0211 (3)
H3	0.2939	0.6118	−0.4361	0.025*
C4	0.29292 (14)	0.79139 (13)	−0.44410 (12)	0.0247 (3)
H4	0.2808	0.8170	−0.5148	0.030*
C5	0.30400 (14)	0.87639 (13)	−0.38663 (12)	0.0234 (3)
H5	0.2999	0.9590	−0.4197	0.028*
C6	0.32112 (13)	0.84096 (12)	−0.28013 (11)	0.0189 (3)
C7	0.31658 (13)	0.49267 (12)	−0.23475 (11)	0.0207 (3)
H7	0.3734	0.4792	−0.1873	0.025*
C8	0.38043 (18)	0.41085 (14)	−0.32508 (14)	0.0347 (4)
H8A	0.3180	0.4105	−0.3632	0.052*
H8B	0.3958	0.3292	−0.2865	0.052*
H8C	0.4675	0.4415	−0.3821	0.052*
C9	0.16846 (15)	0.45598 (14)	−0.15230 (14)	0.0334 (4)
H9A	0.1336	0.5022	−0.0915	0.050*
H9B	0.1702	0.3705	−0.1182	0.050*
H9C	0.1090	0.4723	−0.1957	0.050*
C10	0.33702 (13)	0.93965 (12)	−0.22322 (11)	0.0209 (3)
H10	0.3688	0.8996	−0.1600	0.025*
C11	0.19795 (16)	1.00935 (15)	−0.17000 (15)	0.0359 (4)
H11A	0.1627	1.0463	−0.2299	0.054*
H11B	0.2117	1.0716	−0.1365	0.054*
H11C	0.1324	0.9538	−0.1102	0.054*
C12	0.44612 (16)	1.02859 (14)	−0.31090 (13)	0.0307 (3)
H12A	0.5329	0.9842	−0.3438	0.046*
H12B	0.4587	1.0861	−0.2718	0.046*
H12C	0.4154	1.0713	−0.3722	0.046*
C13	0.31164 (12)	0.62873 (11)	0.13634 (10)	0.0147 (3)
C14	0.29025 (13)	0.63827 (12)	0.24970 (11)	0.0187 (3)
H14	0.3577	0.6055	0.2803	0.022*
C15	0.16999 (14)	0.69579 (12)	0.31723 (11)	0.0218 (3)
H15	0.1577	0.7010	0.3925	0.026*
C16	0.06764 (14)	0.74577 (12)	0.27368 (12)	0.0236 (3)
H16	−0.0143	0.7819	0.3201	0.028*
C17	0.08938 (13)	0.74096 (12)	0.16070 (11)	0.0211 (3)
H17	0.0215	0.7751	0.1310	0.025*
C18	0.21190 (12)	0.68555 (11)	0.08902 (10)	0.0162 (3)
C19	0.22793 (12)	0.69780 (11)	−0.03196 (11)	0.0167 (3)
H19	0.1485	0.7248	−0.0482	0.020*
C20	0.39633 (14)	0.20342 (14)	−0.03453 (12)	0.0255 (3)
H20A	0.3922	0.2881	−0.0707	0.038*
H20B	0.3700	0.1552	−0.0744	0.038*
H20C	0.4895	0.1790	−0.0390	0.038*
C21	0.09143 (14)	0.21425 (14)	0.12591 (13)	0.0274 (3)
H21A	0.0259	0.1865	0.2038	0.041*
H21B	0.0792	0.1730	0.0732	0.041*
H21C	0.0762	0.3006	0.1024	0.041*
C22	0.28777 (17)	0.01123 (13)	0.17753 (14)	0.0315 (3)
H22A	0.3820	−0.0134	0.1701	0.047*
H22B	0.2617	−0.0304	0.1323	0.047*
H22C	0.2267	−0.0090	0.2582	0.047*
C23	0.13030 (15)	0.13181 (13)	0.42762 (12)	0.0267 (3)
H23A	0.0684	0.1103	0.3972	0.040*
H23B	0.0789	0.1421	0.5066	0.040*
H23C	0.2018	0.0682	0.4263	0.040*
C24	0.31404 (15)	0.32087 (14)	0.41136 (12)	0.0274 (3)
H24A	0.3754	0.2531	0.4259	0.041*
H24B	0.2511	0.3412	0.4843	0.041*
H24C	0.3677	0.3899	0.3630	0.041*
C25	0.06204 (13)	0.39377 (13)	0.34453 (12)	0.0241 (3)
H25A	0.0942	0.4667	0.2870	0.036*
H25B	0.0228	0.4127	0.4211	0.036*
H25C	−0.0076	0.3607	0.3304	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mg1	0.0128 (2)	0.0147 (2)	0.0130 (2)	−0.00133 (16)	−0.00453 (16)	−0.00165 (16)
O1	0.0139 (4)	0.0148 (4)	0.0138 (4)	0.0009 (3)	−0.0046 (3)	−0.0027 (3)
N1	0.0144 (5)	0.0173 (5)	0.0156 (5)	−0.0023 (4)	−0.0053 (4)	−0.0021 (4)
N2	0.0151 (5)	0.0146 (5)	0.0140 (5)	−0.0022 (4)	−0.0066 (4)	−0.0014 (4)
Si1	0.01604 (18)	0.0178 (2)	0.01889 (19)	−0.00296 (14)	−0.00679 (14)	−0.00388 (14)
Si2	0.01577 (18)	0.0193 (2)	0.01506 (19)	−0.00332 (14)	−0.00416 (14)	−0.00213 (14)
C1	0.0110 (5)	0.0223 (7)	0.0145 (6)	−0.0005 (5)	−0.0054 (5)	−0.0025 (5)
C2	0.0137 (6)	0.0214 (7)	0.0167 (6)	−0.0016 (5)	−0.0056 (5)	−0.0036 (5)
C3	0.0212 (6)	0.0270 (7)	0.0181 (6)	−0.0050 (5)	−0.0089 (5)	−0.0050 (5)
C4	0.0273 (7)	0.0314 (8)	0.0180 (7)	−0.0051 (6)	−0.0130 (6)	0.0000 (6)
C5	0.0278 (7)	0.0209 (7)	0.0225 (7)	−0.0033 (5)	−0.0133 (6)	0.0020 (5)
C6	0.0163 (6)	0.0211 (7)	0.0194 (6)	−0.0009 (5)	−0.0075 (5)	−0.0029 (5)
C7	0.0240 (7)	0.0213 (7)	0.0209 (7)	−0.0013 (5)	−0.0127 (6)	−0.0042 (5)
C8	0.0568 (10)	0.0241 (8)	0.0329 (8)	0.0058 (7)	−0.0265 (8)	−0.0116 (6)
C9	0.0308 (8)	0.0271 (8)	0.0399 (9)	−0.0101 (6)	−0.0167 (7)	0.0084 (7)
C10	0.0241 (7)	0.0183 (7)	0.0225 (7)	−0.0015 (5)	−0.0120 (6)	−0.0025 (5)
C11	0.0292 (8)	0.0316 (9)	0.0497 (10)	0.0039 (7)	−0.0131 (7)	−0.0198 (8)
C12	0.0365 (8)	0.0258 (8)	0.0309 (8)	−0.0097 (6)	−0.0135 (7)	−0.0019 (6)
C13	0.0137 (6)	0.0129 (6)	0.0154 (6)	−0.0028 (5)	−0.0027 (5)	−0.0028 (5)
C14	0.0205 (6)	0.0192 (7)	0.0165 (6)	−0.0021 (5)	−0.0074 (5)	−0.0026 (5)
C15	0.0258 (7)	0.0234 (7)	0.0142 (6)	−0.0038 (5)	−0.0037 (5)	−0.0056 (5)
C16	0.0211 (6)	0.0227 (7)	0.0215 (7)	0.0021 (5)	−0.0013 (5)	−0.0082 (6)
C17	0.0178 (6)	0.0210 (7)	0.0224 (7)	0.0022 (5)	−0.0066 (5)	−0.0047 (5)
C18	0.0157 (6)	0.0156 (6)	0.0161 (6)	−0.0019 (5)	−0.0046 (5)	−0.0029 (5)
C19	0.0141 (6)	0.0167 (6)	0.0198 (6)	−0.0005 (5)	−0.0077 (5)	−0.0028 (5)
C20	0.0246 (7)	0.0309 (8)	0.0233 (7)	−0.0064 (6)	−0.0065 (6)	−0.0112 (6)
C21	0.0204 (7)	0.0370 (8)	0.0287 (7)	−0.0047 (6)	−0.0114 (6)	−0.0082 (6)
C22	0.0432 (9)	0.0211 (8)	0.0345 (8)	−0.0041 (6)	−0.0174 (7)	−0.0074 (6)
C23	0.0309 (7)	0.0257 (8)	0.0184 (7)	−0.0070 (6)	−0.0043 (6)	−0.0007 (6)
C24	0.0265 (7)	0.0357 (8)	0.0225 (7)	−0.0031 (6)	−0.0095 (6)	−0.0089 (6)
C25	0.0184 (6)	0.0234 (7)	0.0267 (7)	−0.0022 (5)	−0.0037 (5)	−0.0063 (6)

Geometric parameters (Å, º)

Mg1—N1	1.9967 (11)	C10—C11	1.5321 (19)
Mg1—O1^i	2.0088 (9)	C10—H10	0.9800
Mg1—O1	2.0095 (9)	C11—H11A	0.9600
Mg1—N2^i	2.1474 (11)	C11—H11B	0.9600
Mg1—Mg1^i	3.0869 (8)	C11—H11C	0.9600
O1—C13	1.3469 (14)	C12—H12A	0.9600
O1—Mg1^i	2.0088 (9)	C12—H12B	0.9600
N1—Si1	1.7112 (11)	C12—H12C	0.9600
N1—Si2	1.7115 (11)	C13—C14	1.3986 (17)
N2—C19	1.2923 (15)	C13—C18	1.4126 (17)
N2—C1	1.4539 (15)	C14—C15	1.3865 (17)
N2—Mg1^i	2.1473 (11)	C14—H14	0.9300
Si1—C22	1.8741 (15)	C15—C16	1.3894 (19)
Si1—C20	1.8760 (14)	C15—H15	0.9300
Si1—C21	1.8838 (14)	C16—C17	1.3777 (19)
Si2—C24	1.8746 (14)	C16—H16	0.9300
Si2—C25	1.8773 (13)	C17—C18	1.4093 (17)
Si2—C23	1.8827 (14)	C17—H17	0.9300
C1—C6	1.3999 (18)	C18—C19	1.4555 (17)
C1—C2	1.4037 (17)	C19—H19	0.9300
C2—C3	1.3955 (18)	C20—H20A	0.9600
C2—C7	1.5192 (18)	C20—H20B	0.9600
C3—C4	1.3802 (19)	C20—H20C	0.9600
C3—H3	0.9300	C21—H21A	0.9600
C4—C5	1.3829 (19)	C21—H21B	0.9600
C4—H4	0.9300	C21—H21C	0.9600
C5—C6	1.3944 (18)	C22—H22A	0.9600
C5—H5	0.9300	C22—H22B	0.9600
C6—C10	1.5294 (18)	C22—H22C	0.9600
C7—C8	1.5327 (19)	C23—H23A	0.9600
C7—C9	1.5361 (19)	C23—H23B	0.9600
C7—H7	0.9800	C23—H23C	0.9600
C8—H8A	0.9600	C24—H24A	0.9600
C8—H8B	0.9600	C24—H24B	0.9600
C8—H8C	0.9600	C24—H24C	0.9600
C9—H9A	0.9600	C25—H25A	0.9600
C9—H9B	0.9600	C25—H25B	0.9600
C9—H9C	0.9600	C25—H25C	0.9600
C10—C12	1.5279 (19)
N1—Mg1—O1^i	132.80 (4)	C6—C10—H10	108.0
N1—Mg1—O1	120.34 (4)	C11—C10—H10	108.0
O1^i—Mg1—O1	79.62 (4)	C10—C11—H11A	109.5
N1—Mg1—N2^i	113.39 (4)	C10—C11—H11B	109.5
O1^i—Mg1—N2^i	88.77 (4)	H11A—C11—H11B	109.5
O1—Mg1—N2^i	115.84 (4)	C10—C11—H11C	109.5
N1—Mg1—Mg1^i	140.45 (4)	H11A—C11—H11C	109.5
O1^i—Mg1—Mg1^i	39.82 (3)	H11B—C11—H11C	109.5
O1—Mg1—Mg1^i	39.80 (2)	C10—C12—H12A	109.5
N2^i—Mg1—Mg1^i	105.64 (3)	C10—C12—H12B	109.5
C13—O1—Mg1^i	124.33 (7)	H12A—C12—H12B	109.5
C13—O1—Mg1	128.89 (7)	C10—C12—H12C	109.5
Mg1^i—O1—Mg1	100.38 (4)	H12A—C12—H12C	109.5
Si1—N1—Si2	120.36 (6)	H12B—C12—H12C	109.5
Si1—N1—Mg1	117.71 (6)	O1—C13—C14	120.33 (11)
Si2—N1—Mg1	120.95 (6)	O1—C13—C18	121.11 (11)
C19—N2—C1	113.90 (10)	C14—C13—C18	118.56 (11)
C19—N2—Mg1^i	120.91 (8)	C15—C14—C13	121.01 (12)
C1—N2—Mg1^i	124.34 (7)	C15—C14—H14	119.5
N1—Si1—C22	116.01 (6)	C13—C14—H14	119.5
N1—Si1—C20	109.90 (6)	C14—C15—C16	120.71 (12)
C22—Si1—C20	103.99 (7)	C14—C15—H15	119.6
N1—Si1—C21	113.17 (6)	C16—C15—H15	119.6
C22—Si1—C21	105.46 (7)	C17—C16—C15	118.97 (12)
C20—Si1—C21	107.62 (6)	C17—C16—H16	120.5
N1—Si2—C24	111.01 (6)	C15—C16—H16	120.5
N1—Si2—C25	112.54 (6)	C16—C17—C18	121.63 (12)
C24—Si2—C25	108.11 (7)	C16—C17—H17	119.2
N1—Si2—C23	114.03 (6)	C18—C17—H17	119.2
C24—Si2—C23	105.74 (7)	C17—C18—C13	118.94 (11)
C25—Si2—C23	104.93 (6)	C17—C18—C19	115.92 (11)
C6—C1—C2	121.95 (11)	C13—C18—C19	125.06 (11)
C6—C1—N2	119.12 (11)	N2—C19—C18	128.21 (11)
C2—C1—N2	118.93 (11)	N2—C19—H19	115.9
C3—C2—C1	117.88 (12)	C18—C19—H19	115.9
C3—C2—C7	120.90 (11)	Si1—C20—H20A	109.5
C1—C2—C7	121.16 (11)	Si1—C20—H20B	109.5
C4—C3—C2	121.16 (12)	H20A—C20—H20B	109.5
C4—C3—H3	119.4	Si1—C20—H20C	109.5
C2—C3—H3	119.4	H20A—C20—H20C	109.5
C3—C4—C5	119.86 (12)	H20B—C20—H20C	109.5
C3—C4—H4	120.1	Si1—C21—H21A	109.5
C5—C4—H4	120.1	Si1—C21—H21B	109.5
C4—C5—C6	121.45 (12)	H21A—C21—H21B	109.5
C4—C5—H5	119.3	Si1—C21—H21C	109.5
C6—C5—H5	119.3	H21A—C21—H21C	109.5
C5—C6—C1	117.67 (12)	H21B—C21—H21C	109.5
C5—C6—C10	118.67 (12)	Si1—C22—H22A	109.5
C1—C6—C10	123.66 (11)	Si1—C22—H22B	109.5
C2—C7—C8	113.28 (11)	H22A—C22—H22B	109.5
C2—C7—C9	110.17 (11)	Si1—C22—H22C	109.5
C8—C7—C9	110.47 (12)	H22A—C22—H22C	109.5
C2—C7—H7	107.6	H22B—C22—H22C	109.5
C8—C7—H7	107.6	Si2—C23—H23A	109.5
C9—C7—H7	107.6	Si2—C23—H23B	109.5
C7—C8—H8A	109.5	H23A—C23—H23B	109.5
C7—C8—H8B	109.5	Si2—C23—H23C	109.5
H8A—C8—H8B	109.5	H23A—C23—H23C	109.5
C7—C8—H8C	109.5	H23B—C23—H23C	109.5
H8A—C8—H8C	109.5	Si2—C24—H24A	109.5
H8B—C8—H8C	109.5	Si2—C24—H24B	109.5
C7—C9—H9A	109.5	H24A—C24—H24B	109.5
C7—C9—H9B	109.5	Si2—C24—H24C	109.5
H9A—C9—H9B	109.5	H24A—C24—H24C	109.5
C7—C9—H9C	109.5	H24B—C24—H24C	109.5
H9A—C9—H9C	109.5	Si2—C25—H25A	109.5
H9B—C9—H9C	109.5	Si2—C25—H25B	109.5
C12—C10—C6	111.13 (11)	H25A—C25—H25B	109.5
C12—C10—C11	110.04 (12)	Si2—C25—H25C	109.5
C6—C10—C11	111.44 (11)	H25A—C25—H25C	109.5
C12—C10—H10	108.0	H25B—C25—H25C	109.5

Symmetry code: (i) −x+1, −y+1, −z.

(CompoundII) {2,4-Di-tert-butyl-6-[(2,6-diisopropylphenyl)iminomethyl]phenolato-κ²N,O}bis(pyridine-κN)magnesium(II) toluene monosolvate

Crystal data

[Mg(C27H38NO)2(C5H5N)2]·C5H5N	F(000) = 2272
Mr = 1046.78	Dx = 1.114 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4322 reflections
a = 31.633 (4) Å	θ = 2.3–24.0°
b = 13.4541 (15) Å	µ = 0.08 mm^−1
c = 17.467 (3) Å	T = 120 K
β = 122.934 (3)°	Block, yellow
V = 6239.4 (15) Å^3	0.28 × 0.24 × 0.24 mm
Z = 4

Data collection

Bruker X8 APEXII CCD diffractometer	6388 independent reflections
Radiation source: fine-focus sealed tube	4572 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.072
φ and ω scans	θmax = 26.4°, θmin = 1.5°
Absorption correction: multi-scan [Blessing (1995) and SADABS (Bruker, 2008; Krause et al., 2015)]	h = −39→39
Tmin = 0.946, Tmax = 0.954	k = −16→16
37297 measured reflections	l = −21→21

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.052	H-atom parameters constrained
wR(F^2) = 0.136	w = 1/[σ^2(Fo^2) + (0.0538P)^2 + 7.6033P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
6388 reflections	Δρmax = 0.27 e Å^−3
359 parameters	Δρmin = −0.28 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

The structure contains a pyrdine solvent molecule of crystallization. Two site disorder of the ring was modeled by refining the positions of N1s and C3s at half occupancy.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Mg1	0.2500	0.2500	0.0000	0.0170 (2)
N1	0.23064 (6)	0.13220 (11)	0.07607 (10)	0.0172 (3)
N2	0.29807 (6)	0.33380 (12)	0.13267 (11)	0.0194 (4)
O1	0.31096 (5)	0.18177 (10)	0.02188 (9)	0.0194 (3)
C1	0.34461 (7)	0.19141 (14)	0.00130 (12)	0.0172 (4)
C2	0.34379 (7)	0.27344 (14)	−0.05039 (12)	0.0187 (4)
C3	0.37973 (7)	0.28316 (15)	−0.07409 (13)	0.0199 (4)
H3	0.3778	0.3391	−0.1091	0.024*
C4	0.41740 (7)	0.21485 (15)	−0.04840 (13)	0.0207 (4)
C5	0.41846 (7)	0.13456 (15)	0.00456 (13)	0.0213 (4)
H5	0.4442	0.0863	0.0233	0.026*
C6	0.38501 (7)	0.12049 (14)	0.03137 (13)	0.0187 (4)
C7	0.45650 (7)	0.22414 (16)	−0.07385 (14)	0.0265 (5)
C8	0.45019 (11)	0.3192 (2)	−0.1260 (2)	0.0584 (8)
H8A	0.4170	0.3195	−0.1832	0.088*
H8B	0.4764	0.3228	−0.1396	0.088*
H8C	0.4531	0.3767	−0.0890	0.088*
C9	0.50936 (9)	0.2231 (3)	0.01159 (18)	0.0555 (8)
H9A	0.5136	0.2799	0.0502	0.083*
H9B	0.5341	0.2273	−0.0056	0.083*
H9C	0.5145	0.1612	0.0453	0.083*
C10	0.45090 (10)	0.1369 (2)	−0.13526 (19)	0.0482 (7)
H10A	0.4565	0.0743	−0.1024	0.072*
H10B	0.4757	0.1435	−0.1520	0.072*
H10C	0.4169	0.1373	−0.1906	0.072*
C11	0.39141 (7)	0.03471 (15)	0.09456 (13)	0.0223 (4)
C12	0.39980 (8)	0.07738 (16)	0.18325 (13)	0.0272 (5)
H12A	0.4304	0.1181	0.2136	0.041*
H12B	0.4035	0.0228	0.2236	0.041*
H12C	0.3709	0.1185	0.1692	0.041*
C13	0.34472 (8)	−0.03246 (15)	0.04883 (14)	0.0272 (5)
H13A	0.3486	−0.0839	0.0919	0.041*
H13B	0.3410	−0.0639	−0.0051	0.041*
H13C	0.3147	0.0075	0.0304	0.041*
C14	0.43705 (8)	−0.03091 (16)	0.12043 (15)	0.0301 (5)
H14A	0.4677	0.0095	0.1517	0.045*
H14B	0.4327	−0.0598	0.0651	0.045*
H14C	0.4398	−0.0843	0.1610	0.045*
C15	0.25426 (7)	0.03688 (14)	0.11543 (13)	0.0183 (4)
C16	0.29431 (7)	0.03258 (14)	0.20726 (13)	0.0195 (4)
C17	0.31473 (7)	−0.06030 (15)	0.24485 (13)	0.0225 (4)
H17	0.3417	−0.0647	0.3070	0.027*
C18	0.29640 (7)	−0.14597 (15)	0.19331 (14)	0.0245 (5)
H18	0.3113	−0.2084	0.2195	0.029*
C19	0.25633 (7)	−0.14061 (15)	0.10359 (14)	0.0233 (4)
H19	0.2437	−0.1999	0.0687	0.028*
C20	0.23398 (7)	−0.04993 (14)	0.06315 (13)	0.0210 (4)
C21	0.31199 (7)	0.12473 (15)	0.26669 (13)	0.0234 (4)
H21	0.3080	0.1825	0.2273	0.028*
C22	0.36695 (8)	0.12169 (17)	0.34634 (14)	0.0295 (5)
H22A	0.3715	0.0685	0.3885	0.044*
H22B	0.3761	0.1856	0.3785	0.044*
H22C	0.3886	0.1091	0.3232	0.044*
C23	0.27888 (8)	0.14405 (18)	0.30436 (15)	0.0338 (5)
H23A	0.2442	0.1573	0.2537	0.051*
H23B	0.2919	0.2017	0.3452	0.051*
H23C	0.2794	0.0855	0.3383	0.051*
C24	0.18748 (8)	−0.04935 (15)	−0.03368 (13)	0.0253 (5)
H24	0.1792	0.0215	−0.0537	0.030*
C25	0.19600 (9)	−0.10245 (19)	−0.10049 (16)	0.0397 (6)
H25A	0.2263	−0.0760	−0.0953	0.059*
H25B	0.1669	−0.0920	−0.1627	0.059*
H25C	0.2003	−0.1737	−0.0868	0.059*
C26	0.14239 (9)	−0.0945 (2)	−0.03592 (18)	0.0512 (7)
H26A	0.1499	−0.1636	−0.0149	0.077*
H26B	0.1127	−0.0926	−0.0984	0.077*
H26C	0.1357	−0.0563	0.0041	0.077*
C27	0.19179 (7)	0.14566 (14)	0.08130 (13)	0.0198 (4)
H27	0.1856	0.0933	0.1105	0.024*
C28	0.27874 (8)	0.36972 (14)	0.17890 (14)	0.0230 (4)
H28	0.2432	0.3682	0.1503	0.028*
C29	0.30745 (8)	0.40873 (16)	0.26551 (14)	0.0280 (5)
H29	0.2921	0.4318	0.2962	0.034*
C30	0.35909 (8)	0.41350 (17)	0.30674 (15)	0.0319 (5)
H30	0.3799	0.4403	0.3663	0.038*
C31	0.37989 (8)	0.37867 (16)	0.25988 (14)	0.0291 (5)
H31	0.4152	0.3820	0.2863	0.035*
C32	0.34839 (7)	0.33897 (15)	0.17408 (14)	0.0228 (4)
H32	0.3630	0.3140	0.1426	0.027*
C1S	0.01672 (15)	0.8155 (3)	0.2958 (3)	0.0791 (13)
H1S	0.0291	0.7550	0.3288	0.095*
C2S	0.01538 (12)	0.9886 (2)	0.2923 (2)	0.0796 (12)
H2S	0.0270	1.0502	0.3237	0.095*
N1S	0.03202 (12)	0.9046 (4)	0.3388 (2)	0.0934 (13)	0.5
C3S	0.03202 (12)	0.9046 (4)	0.3388 (2)	0.0934 (13)	0.5
H3S	0.0550	0.9067	0.4031	0.112*	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mg1	0.0153 (4)	0.0210 (5)	0.0167 (5)	0.0037 (4)	0.0101 (4)	0.0009 (4)
N1	0.0160 (8)	0.0198 (8)	0.0155 (8)	0.0033 (6)	0.0082 (7)	−0.0004 (6)
N2	0.0203 (8)	0.0202 (8)	0.0189 (8)	0.0023 (7)	0.0114 (7)	0.0021 (7)
O1	0.0177 (7)	0.0243 (7)	0.0208 (7)	0.0051 (5)	0.0133 (6)	0.0029 (6)
C1	0.0138 (9)	0.0235 (10)	0.0136 (9)	0.0000 (8)	0.0070 (8)	−0.0037 (8)
C2	0.0163 (9)	0.0230 (10)	0.0167 (9)	0.0032 (8)	0.0089 (8)	−0.0006 (8)
C3	0.0191 (10)	0.0233 (10)	0.0200 (10)	0.0004 (8)	0.0123 (8)	0.0006 (8)
C4	0.0160 (9)	0.0274 (10)	0.0193 (10)	0.0004 (8)	0.0100 (8)	−0.0032 (8)
C5	0.0169 (9)	0.0260 (11)	0.0196 (10)	0.0063 (8)	0.0089 (8)	−0.0014 (8)
C6	0.0160 (9)	0.0229 (10)	0.0154 (9)	0.0023 (8)	0.0072 (8)	−0.0021 (8)
C7	0.0199 (10)	0.0359 (12)	0.0305 (11)	0.0028 (9)	0.0181 (9)	0.0017 (9)
C8	0.0574 (18)	0.0598 (18)	0.094 (2)	0.0188 (15)	0.0646 (19)	0.0286 (17)
C9	0.0228 (13)	0.102 (2)	0.0422 (15)	−0.0083 (14)	0.0182 (12)	−0.0063 (16)
C10	0.0428 (15)	0.0616 (18)	0.0614 (18)	−0.0071 (13)	0.0420 (14)	−0.0190 (14)
C11	0.0201 (10)	0.0263 (11)	0.0219 (10)	0.0085 (8)	0.0123 (9)	0.0035 (8)
C12	0.0291 (11)	0.0326 (12)	0.0212 (11)	0.0067 (9)	0.0145 (10)	0.0062 (9)
C13	0.0311 (12)	0.0248 (11)	0.0305 (12)	0.0050 (9)	0.0199 (10)	0.0044 (9)
C14	0.0299 (12)	0.0342 (12)	0.0297 (12)	0.0142 (10)	0.0184 (10)	0.0103 (9)
C15	0.0198 (10)	0.0186 (10)	0.0221 (10)	0.0038 (8)	0.0149 (9)	0.0042 (8)
C16	0.0170 (9)	0.0241 (10)	0.0216 (10)	0.0024 (8)	0.0131 (8)	0.0033 (8)
C17	0.0188 (10)	0.0288 (11)	0.0200 (10)	0.0047 (8)	0.0106 (9)	0.0082 (8)
C18	0.0251 (11)	0.0206 (10)	0.0309 (11)	0.0061 (8)	0.0173 (10)	0.0069 (9)
C19	0.0249 (11)	0.0207 (10)	0.0274 (11)	0.0024 (8)	0.0161 (9)	0.0018 (8)
C20	0.0208 (10)	0.0232 (10)	0.0229 (10)	0.0031 (8)	0.0145 (9)	0.0029 (8)
C21	0.0244 (11)	0.0262 (11)	0.0195 (10)	0.0027 (8)	0.0119 (9)	0.0022 (8)
C22	0.0267 (11)	0.0381 (13)	0.0231 (11)	−0.0011 (10)	0.0132 (10)	−0.0019 (9)
C23	0.0291 (12)	0.0441 (14)	0.0272 (12)	0.0064 (10)	0.0146 (10)	−0.0052 (10)
C24	0.0285 (11)	0.0219 (10)	0.0226 (11)	0.0038 (9)	0.0121 (9)	0.0004 (8)
C25	0.0415 (14)	0.0440 (14)	0.0270 (12)	0.0050 (11)	0.0145 (11)	−0.0062 (11)
C26	0.0243 (13)	0.083 (2)	0.0351 (14)	−0.0032 (13)	0.0085 (11)	0.0031 (14)
C27	0.0211 (10)	0.0216 (10)	0.0177 (10)	0.0025 (8)	0.0111 (8)	0.0008 (8)
C28	0.0242 (10)	0.0232 (10)	0.0255 (11)	−0.0001 (8)	0.0161 (9)	−0.0019 (8)
C29	0.0325 (12)	0.0307 (12)	0.0257 (11)	−0.0002 (9)	0.0189 (10)	−0.0053 (9)
C30	0.0318 (12)	0.0381 (13)	0.0222 (11)	−0.0045 (10)	0.0124 (10)	−0.0081 (10)
C31	0.0214 (11)	0.0366 (12)	0.0255 (11)	−0.0014 (9)	0.0103 (9)	−0.0021 (9)
C32	0.0215 (10)	0.0246 (10)	0.0236 (10)	0.0016 (8)	0.0130 (9)	0.0017 (8)
C1S	0.114 (3)	0.063 (2)	0.118 (3)	0.046 (2)	0.101 (3)	0.046 (2)
C2S	0.047 (2)	0.0495 (18)	0.103 (3)	−0.0019 (15)	0.0151 (18)	−0.0331 (18)
N1S	0.0482 (18)	0.168 (4)	0.0472 (18)	0.028 (2)	0.0154 (15)	−0.008 (2)
C3S	0.0482 (18)	0.168 (4)	0.0472 (18)	0.028 (2)	0.0154 (15)	−0.008 (2)

Geometric parameters (Å, º)

Mg1—O1	1.9764 (12)	C16—C17	1.396 (3)
Mg1—O1^i	1.9764 (12)	C16—C21	1.515 (3)
Mg1—N2	2.2631 (16)	C17—C18	1.381 (3)
Mg1—N2^i	2.2632 (16)	C17—H17	0.9500
Mg1—N1^i	2.3532 (16)	C18—C19	1.381 (3)
Mg1—N1	2.3533 (15)	C18—H18	0.9500
N1—C27	1.294 (2)	C19—C20	1.394 (3)
N1—C15	1.455 (2)	C19—H19	0.9500
N2—C28	1.340 (2)	C20—C24	1.523 (3)
N2—C32	1.345 (2)	C21—C22	1.526 (3)
O1—C1	1.302 (2)	C21—C23	1.532 (3)
C1—C2	1.417 (3)	C21—H21	1.0000
C1—C6	1.445 (3)	C22—H22A	0.9800
C2—C3	1.411 (3)	C22—H22B	0.9800
C2—C27^i	1.443 (3)	C22—H22C	0.9800
C3—C4	1.373 (3)	C23—H23A	0.9800
C3—H3	0.9500	C23—H23B	0.9800
C4—C5	1.411 (3)	C23—H23C	0.9800
C4—C7	1.530 (3)	C24—C25	1.512 (3)
C5—C6	1.383 (3)	C24—C26	1.531 (3)
C5—H5	0.9500	C24—H24	1.0000
C6—C11	1.532 (3)	C25—H25A	0.9800
C7—C8	1.520 (3)	C25—H25B	0.9800
C7—C9	1.520 (3)	C25—H25C	0.9800
C7—C10	1.534 (3)	C26—H26A	0.9800
C8—H8A	0.9800	C26—H26B	0.9800
C8—H8B	0.9800	C26—H26C	0.9800
C8—H8C	0.9800	C27—C2^i	1.443 (3)
C9—H9A	0.9800	C27—H27	0.9500
C9—H9B	0.9800	C28—C29	1.377 (3)
C9—H9C	0.9800	C28—H28	0.9500
C10—H10A	0.9800	C29—C30	1.383 (3)
C10—H10B	0.9800	C29—H29	0.9500
C10—H10C	0.9800	C30—C31	1.381 (3)
C11—C13	1.534 (3)	C30—H30	0.9500
C11—C12	1.534 (3)	C31—C32	1.379 (3)
C11—C14	1.536 (3)	C31—H31	0.9500
C12—H12A	0.9800	C32—H32	0.9500
C12—H12B	0.9800	C1S—C1S^ii	1.355 (8)
C12—H12C	0.9800	C1S—N1S	1.357 (5)
C13—H13A	0.9800	C1S—C3S	1.357 (5)
C13—H13B	0.9800	C1S—H1S	0.9500
C13—H13C	0.9800	C2S—C2S^ii	1.252 (7)
C14—H14A	0.9800	C2S—N1S	1.322 (5)
C14—H14B	0.9800	C2S—C3S	1.322 (5)
C14—H14C	0.9800	C2S—H2S	0.9500
C15—C20	1.404 (3)	C3S—H3S	0.9500
C15—C16	1.404 (3)
O1—Mg1—O1^i	180.00 (4)	H14A—C14—H14C	109.5
O1—Mg1—N2	89.52 (5)	H14B—C14—H14C	109.5
O1^i—Mg1—N2	90.48 (5)	C20—C15—C16	121.20 (17)
O1—Mg1—N2^i	90.48 (5)	C20—C15—N1	119.34 (16)
O1^i—Mg1—N2^i	89.52 (5)	C16—C15—N1	119.25 (16)
N2—Mg1—N2^i	180.0	C17—C16—C15	118.27 (18)
O1—Mg1—N1^i	84.02 (5)	C17—C16—C21	120.41 (17)
O1^i—Mg1—N1^i	95.98 (5)	C15—C16—C21	121.10 (17)
N2—Mg1—N1^i	90.37 (5)	C18—C17—C16	121.17 (18)
N2^i—Mg1—N1^i	89.63 (5)	C18—C17—H17	119.4
O1—Mg1—N1	95.98 (5)	C16—C17—H17	119.4
O1^i—Mg1—N1	84.02 (5)	C19—C18—C17	119.80 (18)
N2—Mg1—N1	89.63 (5)	C19—C18—H18	120.1
N2^i—Mg1—N1	90.37 (5)	C17—C18—H18	120.1
N1^i—Mg1—N1	180.0	C18—C19—C20	121.35 (19)
C27—N1—C15	110.72 (15)	C18—C19—H19	119.3
C27—N1—Mg1	119.63 (13)	C20—C19—H19	119.3
C15—N1—Mg1	129.48 (11)	C19—C20—C15	118.15 (18)
C28—N2—C32	116.83 (17)	C19—C20—C24	118.98 (18)
C28—N2—Mg1	121.60 (13)	C15—C20—C24	122.81 (17)
C32—N2—Mg1	121.07 (13)	C16—C21—C22	114.56 (17)
C1—O1—Mg1	139.34 (12)	C16—C21—C23	110.45 (17)
O1—C1—C2	121.26 (16)	C22—C21—C23	108.60 (17)
O1—C1—C6	121.86 (17)	C16—C21—H21	107.7
C2—C1—C6	116.87 (16)	C22—C21—H21	107.7
C3—C2—C1	121.35 (17)	C23—C21—H21	107.7
C3—C2—C27^i	114.16 (17)	C21—C22—H22A	109.5
C1—C2—C27^i	124.47 (17)	C21—C22—H22B	109.5
C4—C3—C2	122.44 (18)	H22A—C22—H22B	109.5
C4—C3—H3	118.8	C21—C22—H22C	109.5
C2—C3—H3	118.8	H22A—C22—H22C	109.5
C3—C4—C5	115.72 (17)	H22B—C22—H22C	109.5
C3—C4—C7	123.06 (18)	C21—C23—H23A	109.5
C5—C4—C7	121.22 (17)	C21—C23—H23B	109.5
C6—C5—C4	125.23 (18)	H23A—C23—H23B	109.5
C6—C5—H5	117.4	C21—C23—H23C	109.5
C4—C5—H5	117.4	H23A—C23—H23C	109.5
C5—C6—C1	118.32 (17)	H23B—C23—H23C	109.5
C5—C6—C11	121.40 (16)	C25—C24—C20	112.63 (17)
C1—C6—C11	120.23 (16)	C25—C24—C26	110.3 (2)
C8—C7—C9	108.2 (2)	C20—C24—C26	110.51 (17)
C8—C7—C4	112.32 (17)	C25—C24—H24	107.7
C9—C7—C4	110.21 (18)	C20—C24—H24	107.7
C8—C7—C10	107.3 (2)	C26—C24—H24	107.7
C9—C7—C10	109.1 (2)	C24—C25—H25A	109.5
C4—C7—C10	109.66 (17)	C24—C25—H25B	109.5
C7—C8—H8A	109.5	H25A—C25—H25B	109.5
C7—C8—H8B	109.5	C24—C25—H25C	109.5
H8A—C8—H8B	109.5	H25A—C25—H25C	109.5
C7—C8—H8C	109.5	H25B—C25—H25C	109.5
H8A—C8—H8C	109.5	C24—C26—H26A	109.5
H8B—C8—H8C	109.5	C24—C26—H26B	109.5
C7—C9—H9A	109.5	H26A—C26—H26B	109.5
C7—C9—H9B	109.5	C24—C26—H26C	109.5
H9A—C9—H9B	109.5	H26A—C26—H26C	109.5
C7—C9—H9C	109.5	H26B—C26—H26C	109.5
H9A—C9—H9C	109.5	N1—C27—C2^i	131.07 (18)
H9B—C9—H9C	109.5	N1—C27—H27	114.5
C7—C10—H10A	109.5	C2^i—C27—H27	114.5
C7—C10—H10B	109.5	N2—C28—C29	123.72 (19)
H10A—C10—H10B	109.5	N2—C28—H28	118.1
C7—C10—H10C	109.5	C29—C28—H28	118.1
H10A—C10—H10C	109.5	C28—C29—C30	118.5 (2)
H10B—C10—H10C	109.5	C28—C29—H29	120.8
C6—C11—C13	110.84 (16)	C30—C29—H29	120.8
C6—C11—C12	109.16 (16)	C31—C30—C29	118.9 (2)
C13—C11—C12	109.59 (17)	C31—C30—H30	120.5
C6—C11—C14	112.32 (16)	C29—C30—H30	120.5
C13—C11—C14	107.43 (17)	C32—C31—C30	118.7 (2)
C12—C11—C14	107.41 (16)	C32—C31—H31	120.7
C11—C12—H12A	109.5	C30—C31—H31	120.7
C11—C12—H12B	109.5	N2—C32—C31	123.30 (19)
H12A—C12—H12B	109.5	N2—C32—H32	118.3
C11—C12—H12C	109.5	C31—C32—H32	118.3
H12A—C12—H12C	109.5	C1S^ii—C1S—N1S	117.9 (2)
H12B—C12—H12C	109.5	C1S^ii—C1S—C3S	117.9 (2)
C11—C13—H13A	109.5	C1S^ii—C1S—H1S	121.1
C11—C13—H13B	109.5	N1S—C1S—H1S	121.1
H13A—C13—H13B	109.5	C2S^ii—C2S—N1S	121.3 (2)
C11—C13—H13C	109.5	C2S^ii—C2S—C3S	121.3 (2)
H13A—C13—H13C	109.5	C2S^ii—C2S—H2S	119.4
H13B—C13—H13C	109.5	N1S—C2S—H2S	119.4
C11—C14—H14A	109.5	C2S—N1S—C1S	120.8 (3)
C11—C14—H14B	109.5	C2S—C3S—C1S	120.8 (3)
H14A—C14—H14B	109.5	C2S—C3S—H3S	119.6
C11—C14—H14C	109.5	C1S—C3S—H3S	119.6

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