Aqua­(phthalocyaninato)­magnesium

The title compound, [Mg(C₃₂H₁₆N₈)(H₂O)], crystallizes with two MgPc(H₂O) mol­ecules (Pc is phthalocyaninate) in the asymmetric unit. The geometries of the two mol­ecules are very similar, with the Mg atoms each 4+1-coordinated by four iso­indole N atoms at the base and by the O atom of the water mol­ecule. The Mg atoms are displaced by 0.447 (1) and 0.468 (1) Å from the basal coordination planes towards the water O atoms. O—H...N hydrogen bonds form dimers stacked along the b axis in a herring-bone fashion.

S1. Comment

Our interest in magnesium phthalocyaninate, MgPc, and its 4 + 1- and 4 + 2-coordinated complexes (Kubiak et al., 1995; Janczak & Kubiak, 2001, 2002) is due to their optical properties in the solid state, especially the X-phase. The literature data related to this phase are inconsistent (Davidson, 1982; Hor & Loutfy, 1983; Krishankumer & Menon, 1997; Sakakibara et al., 2001). Endo et al. (1999) assigned the MgPc(H₂O)₂ composition to the X-phase. However, until now there is no evidence for the existence of this complex. Quite recently, we have determined the crystal structure of the β-modification of MgPc and, contrary to our expectations, the geometry of MgPc molecule was found to be different from that of other M^IIPc compounds in that it is non-planar. The Mg atom in the crystal of MgPc is displaced by 0.557 (2) Å (at 120 K) from the plane defined by the four isoindole N atoms of the Pc^2- ring due to the interaction with an azamethine N atom of a neighbouring MgPc molecule (Janczak & Kubiak, 2001).

In the asymmetric unit of the triclinic form of aqua(phthalocyaninato)magnesium, (I), there are two crystallographically independent MgPc(H₂O) molecules (Fig. 1). The geometries of these independent molecules are very similar and neither are planar. The central Mg atom in (I) is significantly displaced [0.447 (1) for Mg1 and 0.468 (1) Å for Mg2] from the weighted least-squares plane defined by the four isoindole N atoms towards the water O atom. The displacement of the central Mg atom from the Pc^2- plane is comparable to that observed in the other aqua(phthalocyaninato)magnesium complexes (Mizuguchi, 2002; Mizuguchi & Mochizuhi, 2002; Fischer et al., 1977). In the title crystal, the MgPc(H₂O) molecules form dimers via intermolecular O—H···N_azamethine hydrogen bonds. These dimers are stacked along the b axis in a herring-bone fashion. The Pc···Pc distances between the benzo rings in the dimers are shorter than the distance of 3.4 Å between π-aromatic ring systems (Pauling, 1960) and indicate strong π–π interactions between the Pc rings. The face-to-face orientation of the MgPc(H₂O) molecules in the dimers is similar to the orientation of the MgPc molecules in the crystal, in which, due to intermolecular Mg···N_azamethine interactions, the MgPc molecules also form a dimeric (MgPc)₂ structure (Janczak & Kubiak, 2001).

The geometry of the MgPc(H₂O) molecules in the triclinic crystals is similar to that of the monoclinic modification, although the refinement parameters of the latter are relatively large (R = 10.6% and wR = 20.9%; Mizuguchi, 2002). The difference between these two crystallographic modifications of MgPc(H₂O) can be found only in the arrangements of the molecules in the crystals. In the triclinic crystals, the complex molecules form face-to-face hydrogen-bonded dimers, in contrast with the monoclinic crystals, in which the MgPc(H₂O) molecules form a hydrogen-bonded polymeric structure (Mizuguchi, 2002). The differences in the arrangement of MgPc(H₂O) molecules between these two crystallographic modifications implicate differences in the solid-state optical properties, the study of which is now in progress (Janczak & Idemori, 2002).

S2. Experimental

Crystals of the title compound were obtained from a solution in cyanobenzene–water as described elsewhere (Janczak & Idemori, 2002).

S3. Refinement

The water H atoms wererefined, while the H atoms of the benzene rings of the Pc^2- system were treated as riding.

Computing details

Data collection: COLLECT (Nonius, 1997-2000); cell refinement: COLLECT; data reduction: COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990b); software used to prepare material for publication: SHELXL97.

Figures

Fig. 1. A view of both independent molecules in (I), shown with 50% probability displacement ellipsoids. H atoms are shown as spheres of arbitrary radii.

Aqua(phthalocyaninato)magnesium

Crystal data

[Mg(C32H16MgN8)(H2O)]	Z = 4
Mr = 554.86	F(000) = 1144
Triclinic, P1	Dx = 1.474 Mg m^−3 Dm = 1.47 Mg m^−3 Dm measured by flotation
Hall symbol: -P 1	Melting point: dehydratated K
a = 12.955 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.293 (3) Å	Cell parameters from 4680 reflections
c = 16.202 (3) Å	θ = 3–27°
α = 65.03 (2)°	µ = 0.12 mm^−1
β = 81.91 (2)°	T = 200 K
γ = 83.73 (2)°	Parallelepiped, violet
V = 2500.3 (9) Å^3	0.25 × 0.22 × 0.16 mm

Data collection

Nonius CCD area-detector diffractometer	11221 independent reflections
Radiation source: fine-focus sealed tube	8172 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
Detector resolution: 1024x1024 pixels mm^-1	θmax = 27.4°, θmin = 1.4°
ω scans	h = −16→16
Absorption correction: analytical face-indexed (SHELXTL; Sheldrick, 1990)	k = −17→16
Tmin = 0.966, Tmax = 0.982	l = −20→20
47310 measured reflections

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0301P)^2 + 0.8806P] where P = (Fo^2 + 2Fc^2)/3
11221 reflections	(Δ/σ)max = 0.001
769 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.29 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
Mg1	0.55455 (4)	0.25395 (4)	0.45874 (4)	0.01876 (13)
O1	0.55054 (11)	0.23121 (11)	0.34308 (9)	0.0257 (3)
H1O1	0.5402 (16)	0.1700 (19)	0.3425 (15)	0.038*
H2O1	0.5621 (16)	0.2793 (18)	0.2899 (15)	0.038*
N1	0.68829 (11)	0.33569 (11)	0.42990 (9)	0.0204 (3)
N2	0.61982 (11)	0.52844 (11)	0.36974 (9)	0.0214 (3)
N3	0.47523 (11)	0.40472 (11)	0.43323 (9)	0.0205 (3)
N4	0.29989 (11)	0.34250 (11)	0.48821 (9)	0.0208 (3)
N5	0.42404 (11)	0.18021 (11)	0.53993 (9)	0.0205 (3)
N6	0.49296 (11)	−0.01077 (11)	0.61993 (9)	0.0207 (3)
N7	0.63492 (11)	0.10997 (11)	0.53602 (9)	0.0201 (3)
N8	0.81195 (11)	0.17568 (11)	0.48734 (9)	0.0211 (3)
C1	0.78614 (12)	0.28291 (14)	0.44611 (11)	0.0184 (3)
C2	0.86376 (13)	0.36922 (14)	0.41301 (12)	0.0207 (4)
C3	0.97031 (14)	0.36158 (15)	0.41600 (12)	0.0247 (4)
H3	1.0069	0.2930	0.4401	0.030*
C4	1.02110 (14)	0.46080 (15)	0.38147 (13)	0.0286 (4)
H4	1.0932	0.4583	0.3806	0.034*
C5	0.96585 (15)	0.56336 (16)	0.34825 (14)	0.0323 (4)
H5	1.0020	0.6279	0.3260	0.039*
C6	0.85762 (14)	0.57191 (15)	0.34752 (12)	0.0266 (4)
H6	0.8210	0.6407	0.3268	0.032*
C7	0.80651 (13)	0.47346 (14)	0.37898 (11)	0.0202 (4)
C8	0.69703 (13)	0.44882 (13)	0.39154 (11)	0.0196 (3)
C9	0.51844 (13)	0.50650 (13)	0.39006 (11)	0.0202 (4)
C10	0.43459 (14)	0.59491 (14)	0.37127 (11)	0.0213 (4)
C11	0.43585 (14)	0.71035 (14)	0.33009 (11)	0.0243 (4)
H11	0.4984	0.7458	0.3084	0.029*
C12	0.34051 (15)	0.77079 (15)	0.32246 (12)	0.0263 (4)
H12	0.3392	0.8480	0.2948	0.032*
C13	0.24628 (15)	0.71758 (14)	0.35568 (12)	0.0251 (4)
H13	0.1835	0.7600	0.3489	0.030*
C14	0.24514 (14)	0.60224 (14)	0.39871 (11)	0.0230 (4)
H14	0.1826	0.5672	0.4222	0.028*
C15	0.34062 (13)	0.54055 (14)	0.40565 (12)	0.0212 (4)
C16	0.36951 (13)	0.42047 (14)	0.44562 (11)	0.0204 (4)
C17	0.32611 (13)	0.23327 (13)	0.53226 (11)	0.0190 (3)
C18	0.24783 (13)	0.15059 (14)	0.58105 (11)	0.0209 (4)
C19	0.13917 (13)	0.16190 (15)	0.59202 (12)	0.0232 (4)
H19	0.1040	0.2313	0.5679	0.028*
C20	0.08513 (14)	0.06569 (15)	0.64031 (12)	0.0260 (4)
H20	0.0125	0.0704	0.6473	0.031*
C21	0.13921 (14)	−0.03898 (15)	0.67887 (12)	0.0255 (4)
H21	0.1014	−0.1022	0.7106	0.031*
C22	0.24802 (14)	−0.04970 (15)	0.67043 (12)	0.0243 (4)
H22	0.2830	−0.1187	0.6975	0.029*
C23	0.30294 (13)	0.04619 (14)	0.62010 (11)	0.0217 (4)
C24	0.41423 (13)	0.06828 (13)	0.59362 (11)	0.0192 (3)
C25	0.59505 (13)	0.01017 (13)	0.59352 (11)	0.0201 (4)
C26	0.68085 (13)	−0.07496 (14)	0.62551 (11)	0.0216 (4)
C27	0.68699 (14)	−0.18959 (15)	0.68366 (12)	0.0266 (4)
H27	0.6268	−0.2280	0.7111	0.032*
C28	0.78528 (14)	−0.24350 (15)	0.69878 (12)	0.0280 (4)
H28	0.7907	−0.3191	0.7363	0.034*
C29	0.87633 (14)	−0.18558 (14)	0.65831 (12)	0.0244 (4)
H29	0.9410	−0.2233	0.6710	0.029*
C30	0.87246 (14)	−0.07365 (14)	0.59992 (11)	0.0231 (4)
H30	0.9331	−0.0362	0.5723	0.028*
C31	0.77400 (13)	−0.01922 (14)	0.58418 (11)	0.0212 (4)
C32	0.74198 (13)	0.09735 (13)	0.53001 (11)	0.0191 (3)
Mg2	0.54172 (4)	0.20995 (5)	0.04847 (4)	0.01931 (13)
O2	0.50146 (10)	0.07052 (11)	0.16324 (9)	0.0257 (3)
H1O2	0.4881 (17)	0.0569 (18)	0.2151 (16)	0.039*
H2O2	0.4953 (17)	0.0145 (18)	0.1553 (15)	0.039*
N9	0.45513 (11)	0.33878 (11)	0.06780 (9)	0.0203 (3)
N10	0.57527 (11)	0.39078 (12)	0.14498 (9)	0.0219 (3)
N11	0.66561 (11)	0.26524 (11)	0.08028 (9)	0.0209 (3)
N12	0.80748 (11)	0.16949 (11)	0.02153 (9)	0.0218 (3)
N13	0.64498 (11)	0.14388 (11)	−0.02647 (9)	0.0201 (3)
N14	0.52632 (12)	0.09250 (11)	−0.10507 (9)	0.0203 (3)
N15	0.43582 (12)	0.21533 (11)	−0.03685 (9)	0.0210 (3)
N16	0.29831 (11)	0.33419 (11)	0.00292 (9)	0.0207 (3)
C33	0.35355 (13)	0.36932 (13)	0.04871 (11)	0.0204 (4)
C34	0.31147 (13)	0.44932 (13)	0.08770 (11)	0.0195 (4)
C35	0.21362 (14)	0.50439 (13)	0.08877 (11)	0.0225 (4)
H35	0.1605	0.4953	0.0598	0.027*
C36	0.19838 (15)	0.57419 (14)	0.13525 (12)	0.0270 (4)
H36	0.1335	0.6109	0.1380	0.032*
C37	0.27930 (15)	0.58996 (15)	0.17790 (12)	0.0297 (4)
H37	0.2670	0.6372	0.2077	0.036*
C38	0.37716 (15)	0.53585 (15)	0.17602 (12)	0.0265 (4)
H38	0.4308	0.5464	0.2036	0.032*
C39	0.39197 (14)	0.46435 (14)	0.13076 (11)	0.0222 (4)
C40	0.48213 (13)	0.39454 (14)	0.11602 (11)	0.0217 (4)
C41	0.66034 (13)	0.33556 (14)	0.12325 (11)	0.0212 (4)
C42	0.76513 (13)	0.34830 (14)	0.14035 (11)	0.0217 (4)
C43	0.80216 (15)	0.41365 (15)	0.17820 (12)	0.0262 (4)
H43	0.7567	0.4560	0.2023	0.031*
C44	0.91003 (15)	0.41205 (16)	0.17795 (13)	0.0316 (4)
H44	0.9373	0.4529	0.2035	0.038*
C45	0.97874 (15)	0.34914 (15)	0.13932 (12)	0.0285 (4)
H45	1.0503	0.3496	0.1401	0.034*
C46	0.94137 (14)	0.28625 (15)	0.09999 (12)	0.0253 (4)
H46	0.9869	0.2466	0.0733	0.030*
C47	0.83364 (13)	0.28536 (14)	0.10230 (11)	0.0217 (4)
C48	0.76885 (13)	0.23266 (13)	0.06486 (11)	0.0201 (4)
C49	0.75068 (13)	0.13011 (13)	−0.02086 (11)	0.0197 (4)
C50	0.79811 (13)	0.06508 (14)	−0.07115 (11)	0.0219 (4)
C51	0.90271 (14)	0.03322 (15)	−0.08808 (12)	0.0254 (4)
H51	0.9556	0.0534	−0.0657	0.031*
C52	0.92522 (14)	−0.02945 (15)	−0.13941 (12)	0.0278 (4)
H52	0.9942	−0.0506	−0.1524	0.033*
C53	0.84492 (15)	−0.06118 (15)	−0.17190 (12)	0.0288 (4)
H53	0.8616	−0.1049	−0.2046	0.035*
C54	0.74116 (14)	−0.02865 (14)	−0.15631 (12)	0.0254 (4)
H54	0.6886	−0.0498	−0.1784	0.030*
C55	0.71704 (14)	0.03752 (14)	−0.10610 (12)	0.0215 (4)
C56	0.62139 (14)	0.09160 (13)	−0.07841 (12)	0.0203 (4)
C57	0.44173 (13)	0.15183 (13)	−0.08654 (12)	0.0183 (3)
C58	0.33810 (13)	0.15730 (14)	−0.11797 (12)	0.0217 (4)
C59	0.29750 (14)	0.10739 (15)	−0.16661 (12)	0.0252 (4)
H59	0.3396	0.0613	−0.1891	0.030*
C60	0.19253 (14)	0.12906 (15)	−0.18000 (12)	0.0271 (4)
H60	0.1639	0.0961	−0.2114	0.032*
C61	0.12850 (14)	0.19942 (15)	−0.14739 (12)	0.0271 (4)
H61	0.0584	0.2122	−0.1576	0.033*
C62	0.16820 (13)	0.25098 (14)	−0.09962 (12)	0.0240 (4)
H62	0.1263	0.2984	−0.0785	0.029*
C63	0.27304 (13)	0.22771 (14)	−0.08543 (12)	0.0211 (4)
C64	0.33661 (12)	0.26470 (13)	−0.03595 (12)	0.0183 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mg1	0.0188 (3)	0.0171 (3)	0.0188 (3)	−0.0012 (2)	−0.0020 (2)	−0.0057 (2)
O1	0.0337 (7)	0.0199 (7)	0.0212 (6)	−0.0041 (6)	−0.0033 (5)	−0.0056 (5)
N1	0.0230 (8)	0.0170 (7)	0.0206 (7)	0.0004 (6)	−0.0031 (6)	−0.0074 (6)
N2	0.0225 (8)	0.0201 (7)	0.0215 (7)	−0.0014 (6)	−0.0027 (6)	−0.0082 (6)
N3	0.0221 (8)	0.0185 (7)	0.0200 (7)	−0.0018 (6)	−0.0027 (6)	−0.0067 (6)
N4	0.0218 (8)	0.0200 (7)	0.0213 (7)	−0.0009 (6)	−0.0028 (6)	−0.0092 (6)
N5	0.0204 (7)	0.0185 (7)	0.0215 (7)	0.0001 (6)	−0.0024 (6)	−0.0075 (6)
N6	0.0213 (7)	0.0196 (7)	0.0211 (7)	−0.0019 (6)	−0.0008 (6)	−0.0087 (6)
N7	0.0207 (7)	0.0181 (7)	0.0215 (7)	−0.0001 (6)	−0.0025 (6)	−0.0082 (6)
N8	0.0212 (7)	0.0190 (7)	0.0222 (7)	−0.0010 (6)	−0.0017 (6)	−0.0079 (6)
C1	0.0157 (8)	0.0254 (9)	0.0163 (8)	−0.0003 (7)	−0.0023 (6)	−0.0109 (7)
C2	0.0227 (9)	0.0213 (9)	0.0182 (8)	−0.0011 (7)	−0.0016 (7)	−0.0084 (7)
C3	0.0238 (9)	0.0245 (9)	0.0253 (9)	0.0011 (7)	−0.0042 (7)	−0.0100 (8)
C4	0.0219 (9)	0.0332 (10)	0.0339 (10)	−0.0052 (8)	−0.0039 (8)	−0.0159 (9)
C5	0.0277 (10)	0.0282 (10)	0.0397 (11)	−0.0101 (8)	0.0009 (8)	−0.0123 (9)
C6	0.0266 (10)	0.0254 (9)	0.0242 (9)	−0.0038 (8)	0.0000 (7)	−0.0071 (8)
C7	0.0242 (9)	0.0188 (8)	0.0182 (8)	−0.0013 (7)	−0.0001 (7)	−0.0088 (7)
C8	0.0238 (9)	0.0176 (8)	0.0180 (8)	−0.0002 (7)	−0.0036 (7)	−0.0077 (7)
C9	0.0261 (9)	0.0173 (8)	0.0160 (8)	−0.0027 (7)	−0.0036 (7)	−0.0051 (7)
C10	0.0267 (9)	0.0199 (8)	0.0169 (8)	−0.0007 (7)	−0.0023 (7)	−0.0076 (7)
C11	0.0304 (10)	0.0211 (9)	0.0208 (9)	−0.0001 (7)	−0.0034 (7)	−0.0081 (7)
C12	0.0397 (11)	0.0182 (9)	0.0210 (9)	0.0030 (8)	−0.0079 (8)	−0.0076 (7)
C13	0.0315 (10)	0.0242 (9)	0.0225 (9)	0.0091 (8)	−0.0100 (7)	−0.0126 (7)
C14	0.0247 (9)	0.0266 (9)	0.0214 (9)	0.0019 (7)	−0.0044 (7)	−0.0137 (7)
C15	0.0263 (9)	0.0194 (8)	0.0188 (8)	0.0002 (7)	−0.0052 (7)	−0.0082 (7)
C16	0.0228 (9)	0.0213 (9)	0.0182 (8)	−0.0003 (7)	−0.0020 (7)	−0.0094 (7)
C17	0.0175 (8)	0.0197 (8)	0.0183 (8)	−0.0009 (7)	−0.0029 (6)	−0.0061 (7)
C18	0.0239 (9)	0.0243 (9)	0.0168 (8)	−0.0020 (7)	−0.0033 (7)	−0.0102 (7)
C19	0.0237 (9)	0.0257 (9)	0.0199 (8)	0.0001 (7)	−0.0037 (7)	−0.0091 (7)
C20	0.0205 (9)	0.0323 (10)	0.0245 (9)	−0.0043 (8)	−0.0015 (7)	−0.0107 (8)
C21	0.0268 (10)	0.0267 (9)	0.0244 (9)	−0.0096 (8)	0.0030 (7)	−0.0117 (8)
C22	0.0258 (9)	0.0218 (9)	0.0238 (9)	−0.0036 (7)	−0.0020 (7)	−0.0076 (7)
C23	0.0223 (9)	0.0237 (9)	0.0197 (8)	−0.0018 (7)	0.0006 (7)	−0.0102 (7)
C24	0.0205 (9)	0.0184 (8)	0.0190 (8)	−0.0017 (7)	−0.0040 (6)	−0.0072 (7)
C25	0.0236 (9)	0.0174 (8)	0.0198 (8)	−0.0007 (7)	−0.0024 (7)	−0.0083 (7)
C26	0.0220 (9)	0.0212 (9)	0.0207 (8)	0.0009 (7)	−0.0022 (7)	−0.0084 (7)
C27	0.0260 (10)	0.0231 (9)	0.0250 (9)	−0.0037 (7)	−0.0006 (7)	−0.0046 (8)
C28	0.0299 (10)	0.0219 (9)	0.0260 (9)	0.0040 (8)	−0.0026 (8)	−0.0055 (8)
C29	0.0254 (9)	0.0243 (9)	0.0237 (9)	0.0086 (7)	−0.0073 (7)	−0.0108 (8)
C30	0.0240 (9)	0.0244 (9)	0.0212 (8)	0.0017 (7)	−0.0017 (7)	−0.0107 (7)
C31	0.0246 (9)	0.0183 (8)	0.0210 (8)	−0.0001 (7)	−0.0048 (7)	−0.0079 (7)
C32	0.0194 (8)	0.0194 (8)	0.0195 (8)	−0.0002 (7)	−0.0020 (6)	−0.0094 (7)
Mg2	0.0195 (3)	0.0198 (3)	0.0196 (3)	−0.0009 (2)	−0.0026 (2)	−0.0090 (2)
O2	0.0342 (7)	0.0220 (7)	0.0213 (6)	−0.0039 (6)	−0.0009 (6)	−0.0093 (6)
N9	0.0213 (7)	0.0184 (7)	0.0214 (7)	−0.0008 (6)	−0.0022 (6)	−0.0085 (6)
N10	0.0224 (8)	0.0227 (8)	0.0191 (7)	−0.0005 (6)	−0.0025 (6)	−0.0071 (6)
N11	0.0239 (8)	0.0192 (7)	0.0187 (7)	−0.0013 (6)	−0.0024 (6)	−0.0070 (6)
N12	0.0220 (8)	0.0193 (7)	0.0218 (7)	−0.0018 (6)	−0.0032 (6)	−0.0058 (6)
N13	0.0213 (7)	0.0186 (7)	0.0193 (7)	−0.0006 (6)	−0.0031 (6)	−0.0066 (6)
N14	0.0212 (7)	0.0199 (7)	0.0181 (7)	−0.0031 (6)	−0.0009 (6)	−0.0060 (6)
N15	0.0205 (7)	0.0209 (7)	0.0227 (7)	−0.0008 (6)	−0.0024 (6)	−0.0103 (6)
N16	0.0221 (8)	0.0192 (7)	0.0200 (7)	−0.0022 (6)	−0.0023 (6)	−0.0069 (6)
C33	0.0209 (9)	0.0187 (8)	0.0201 (8)	−0.0017 (7)	−0.0005 (7)	−0.0067 (7)
C34	0.0217 (9)	0.0162 (8)	0.0170 (8)	−0.0034 (7)	0.0012 (6)	−0.0037 (7)
C35	0.0250 (9)	0.0178 (8)	0.0201 (8)	−0.0013 (7)	0.0015 (7)	−0.0044 (7)
C36	0.0297 (10)	0.0205 (9)	0.0235 (9)	0.0043 (7)	0.0019 (7)	−0.0048 (7)
C37	0.0413 (12)	0.0248 (9)	0.0228 (9)	0.0047 (8)	−0.0010 (8)	−0.0120 (8)
C38	0.0360 (11)	0.0255 (9)	0.0198 (9)	−0.0013 (8)	−0.0052 (7)	−0.0103 (7)
C39	0.0270 (9)	0.0185 (8)	0.0183 (8)	−0.0007 (7)	−0.0001 (7)	−0.0058 (7)
C40	0.0254 (9)	0.0199 (9)	0.0186 (8)	−0.0054 (7)	−0.0004 (7)	−0.0064 (7)
C41	0.0235 (9)	0.0202 (9)	0.0181 (8)	−0.0035 (7)	−0.0026 (7)	−0.0056 (7)
C42	0.0264 (9)	0.0187 (8)	0.0159 (8)	−0.0050 (7)	−0.0029 (7)	−0.0021 (7)
C43	0.0322 (10)	0.0255 (9)	0.0212 (9)	−0.0032 (8)	−0.0059 (7)	−0.0085 (7)
C44	0.0358 (11)	0.0342 (11)	0.0263 (10)	−0.0110 (9)	−0.0090 (8)	−0.0100 (8)
C45	0.0274 (10)	0.0261 (10)	0.0271 (9)	−0.0101 (8)	−0.0081 (8)	−0.0026 (8)
C46	0.0238 (9)	0.0231 (9)	0.0239 (9)	−0.0023 (7)	−0.0037 (7)	−0.0044 (7)
C47	0.0231 (9)	0.0210 (9)	0.0188 (8)	−0.0040 (7)	−0.0042 (7)	−0.0049 (7)
C48	0.0186 (8)	0.0180 (8)	0.0187 (8)	−0.0052 (7)	−0.0034 (6)	−0.0012 (7)
C49	0.0187 (8)	0.0169 (8)	0.0209 (8)	0.0002 (7)	−0.0018 (7)	−0.0056 (7)
C50	0.0234 (9)	0.0202 (9)	0.0171 (8)	0.0016 (7)	−0.0022 (7)	−0.0036 (7)
C51	0.0215 (9)	0.0263 (9)	0.0238 (9)	0.0008 (7)	−0.0022 (7)	−0.0063 (8)
C52	0.0262 (10)	0.0286 (10)	0.0249 (9)	0.0040 (8)	0.0028 (7)	−0.0104 (8)
C53	0.0338 (11)	0.0278 (10)	0.0250 (9)	0.0030 (8)	0.0019 (8)	−0.0135 (8)
C54	0.0290 (10)	0.0241 (9)	0.0224 (9)	0.0007 (8)	−0.0040 (7)	−0.0092 (7)
C55	0.0239 (9)	0.0194 (8)	0.0186 (8)	0.0002 (7)	−0.0013 (7)	−0.0061 (7)
C56	0.0231 (9)	0.0175 (8)	0.0174 (8)	−0.0040 (7)	−0.0013 (7)	−0.0038 (7)
C57	0.0202 (8)	0.0147 (8)	0.0180 (8)	−0.0006 (6)	−0.0031 (6)	−0.0046 (6)
C58	0.0236 (9)	0.0207 (9)	0.0192 (8)	−0.0026 (7)	−0.0042 (7)	−0.0056 (7)
C59	0.0281 (10)	0.0238 (9)	0.0237 (9)	−0.0026 (7)	−0.0046 (7)	−0.0088 (8)
C60	0.0297 (10)	0.0283 (10)	0.0237 (9)	−0.0044 (8)	−0.0086 (7)	−0.0088 (8)
C61	0.0217 (9)	0.0284 (10)	0.0293 (10)	−0.0007 (8)	−0.0098 (7)	−0.0080 (8)
C62	0.0227 (9)	0.0242 (9)	0.0227 (9)	−0.0003 (7)	−0.0028 (7)	−0.0073 (7)
C63	0.0236 (9)	0.0186 (8)	0.0193 (8)	−0.0026 (7)	−0.0030 (7)	−0.0056 (7)
C64	0.0164 (8)	0.0169 (8)	0.0205 (8)	0.0001 (6)	−0.0031 (6)	−0.0067 (7)

Geometric parameters (Å, º)

Mg1—O1	2.029 (2)	C29—C30	1.386 (2)
Mg1—N1	2.039 (2)	C29—H29	0.9300
Mg1—N5	2.049 (2)	C30—C31	1.396 (2)
Mg1—N3	2.053 (2)	C30—H30	0.9300
Mg1—N7	2.055 (2)	C31—C32	1.469 (2)
Mg2—O2	2.048 (2)	O2—H1O2	0.78 (2)
Mg2—N9	2.055 (2)	O2—H2O2	0.82 (2)
Mg2—N13	2.055 (2)	N9—C33	1.373 (2)
Mg2—N11	2.048 (2)	N9—C40	1.380 (2)
Mg2—N15	2.056 (2)	N10—C40	1.343 (2)
O1—H1O1	0.84 (2)	N10—C41	1.345 (2)
O1—H2O1	0.83 (2)	N11—C41	1.373 (2)
N1—C8	1.374 (2)	N11—C48	1.382 (2)
N1—C1	1.383 (2)	N12—C48	1.325 (2)
N2—C8	1.341 (2)	N12—C49	1.348 (2)
N2—C9	1.341 (2)	N13—C49	1.372 (2)
N3—C16	1.362 (2)	N13—C56	1.377 (2)
N3—C9	1.375 (2)	N14—C57	1.353 (2)
N4—C16	1.338 (2)	N14—C56	1.359 (2)
N4—C17	1.349 (2)	N15—C64	1.379 (2)
N5—C17	1.378 (2)	N15—C57	1.382 (2)
N5—C24	1.380 (2)	N16—C33	1.340 (2)
N6—C25	1.353 (2)	N16—C64	1.341 (2)
N6—C24	1.355 (2)	C33—C34	1.473 (2)
N7—C25	1.366 (2)	C34—C35	1.395 (2)
N7—C32	1.374 (2)	C34—C39	1.408 (2)
N8—C1	1.321 (2)	C35—C36	1.405 (3)
N8—C32	1.344 (2)	C35—H35	0.9300
C1—C2	1.482 (2)	C36—C37	1.412 (3)
C2—C3	1.379 (2)	C36—H36	0.9300
C2—C7	1.421 (2)	C37—C38	1.391 (3)
C3—C4	1.396 (2)	C37—H37	0.9300
C3—H3	0.9300	C38—C39	1.410 (2)
C4—C5	1.392 (3)	C38—H38	0.9300
C4—H4	0.9300	C39—C40	1.468 (2)
C5—C6	1.396 (3)	C41—C42	1.464 (2)
C5—H5	0.9300	C42—C43	1.409 (2)
C6—C7	1.394 (2)	C42—C47	1.410 (3)
C6—H6	0.9300	C43—C44	1.395 (3)
C7—C8	1.458 (2)	C43—H43	0.9300
C9—C10	1.472 (2)	C44—C45	1.416 (3)
C10—C11	1.392 (2)	C44—H44	0.9300
C10—C15	1.406 (2)	C45—C46	1.402 (3)
C11—C12	1.389 (3)	C45—H45	0.9300
C11—H11	0.9300	C46—C47	1.392 (2)
C12—C13	1.401 (3)	C46—H46	0.9300
C12—H12	0.9300	C47—C48	1.481 (2)
C13—C14	1.392 (2)	C49—C50	1.458 (2)
C13—H13	0.9300	C50—C51	1.400 (2)
C14—C15	1.398 (2)	C50—C55	1.409 (2)
C14—H14	0.9300	C51—C52	1.391 (3)
C15—C16	1.474 (2)	C51—H51	0.9300
C17—C18	1.465 (2)	C52—C53	1.405 (3)
C18—C19	1.393 (2)	C52—H52	0.9300
C18—C23	1.416 (2)	C53—C54	1.388 (3)
C19—C20	1.391 (2)	C53—H53	0.9300
C19—H19	0.9300	C54—C55	1.416 (2)
C20—C21	1.412 (3)	C54—H54	0.9300
C20—H20	0.9300	C55—C56	1.475 (2)
C21—C22	1.394 (2)	C57—C58	1.486 (2)
C21—H21	0.9300	C58—C59	1.404 (2)
C22—C23	1.398 (2)	C58—C63	1.408 (2)
C22—H22	0.9300	C59—C60	1.387 (3)
C23—C24	1.470 (2)	C59—H59	0.9300
C25—C26	1.475 (2)	C60—C61	1.402 (3)
C26—C27	1.414 (2)	C60—H60	0.9300
C26—C31	1.415 (2)	C61—C62	1.404 (3)
C27—C28	1.391 (3)	C61—H61	0.9300
C27—H27	0.9300	C62—C63	1.389 (2)
C28—C29	1.403 (3)	C62—H62	0.9300
C28—H28	0.9300	C63—C64	1.473 (2)
O1—Mg1—N1	102.00 (6)	C28—C29—H29	119.1
O1—Mg1—N5	103.58 (6)	C29—C30—C31	117.5 (2)
N1—Mg1—N5	154.41 (6)	C29—C30—H30	121.3
O1—Mg1—N3	104.09 (6)	C31—C30—H30	121.3
N1—Mg1—N3	86.85 (6)	C30—C31—C26	122.0 (2)
N5—Mg1—N3	87.80 (6)	C30—C31—C32	131.7 (2)
O1—Mg1—N7	100.71 (6)	C26—C31—C32	106.3 (2)
N1—Mg1—N7	88.78 (6)	N8—C32—N7	128.5 (2)
N5—Mg1—N7	85.66 (6)	N8—C32—C31	121.8 (2)
N3—Mg1—N7	155.18 (6)	N7—C32—C31	109.5 (2)
O2—Mg2—N9	105.07 (6)	Mg2—O2—H1O2	135 (2)
O2—Mg2—N13	101.63 (6)	Mg2—O2—H2O2	116 (2)
N13—Mg2—N9	153.24 (6)	H1O2—O2—H2O2	109 (2)
O2—Mg2—N11	104.53 (6)	C33—N9—C40	108.9 (2)
N11—Mg2—N9	86.06 (6)	C33—N9—Mg2	124.5 (2)
N11—Mg2—N13	88.85 (6)	C40—N9—Mg2	125.6 (2)
O2—Mg2—N15	101.42 (6)	C40—N10—C41	122.6 (2)
N9—Mg2—N15	88.22 (6)	C41—N11—C48	109.2 (2)
N13—Mg2—N15	84.94 (6)	C41—N11—Mg2	126.4 (2)
N11—Mg2—N15	154.03 (6)	C48—N11—Mg2	124.4 (2)
Mg1—O1—H1O1	124 (2)	C48—N12—C49	124.6 (2)
Mg1—O1—H2O1	125 (2)	C49—N13—C56	108.3 (2)
H1O1—O1—H2O1	111 (2)	C49—N13—Mg2	123.8 (2)
C8—N1—C1	109.4 (2)	C56—N13—Mg2	127.3 (1)
C8—N1—Mg1	126.8 (1)	C57—N14—C56	122.7 (2)
C1—N1—Mg1	123.8 (1)	C64—N15—C57	109.1 (2)
C8—N2—C9	122.9 (2)	C64—N15—Mg2	123.1 (1)
C16—N3—C9	109.0 (2)	C57—N15—Mg2	126.3 (1)
C16—N3—Mg1	125.0 (1)	C33—N16—C64	124.4 (2)
C9—N3—Mg1	125.5 (2)	N16—C33—N9	127.5 (2)
C16—N4—C17	123.8 (2)	N16—C33—C34	123.7 (2)
C17—N5—C24	108.9 (2)	N9—C33—C34	108.8 (2)
C17—N5—Mg1	122.9 (1)	C35—C34—C39	121.1 (2)
C24—N5—Mg1	126.7 (1)	C35—C34—C33	132.1 (2)
C25—N6—C24	123.5 (2)	C39—C34—C33	106.8 (2)
C25—N7—C32	108.6 (2)	C34—C35—C36	117.4 (2)
C25—N7—Mg1	127.7 (1)	C34—C35—H35	121.3
C32—N7—Mg1	123.4 (1)	C36—C35—H35	121.3
C1—N8—C32	123.7 (2)	C35—C36—C37	121.6 (2)
N8—C1—N1	129.1 (2)	C35—C36—H36	119.2
N8—C1—C2	122.7 (2)	C37—C36—H36	119.2
N1—C1—C2	108.2 (2)	C38—C37—C36	121.0 (2)
C3—C2—C7	121.9 (2)	C38—C37—H37	119.5
C3—C2—C1	131.6 (2)	C36—C37—H37	119.5
C7—C2—C1	106.4 (2)	C37—C38—C39	117.5 (2)
C2—C3—C4	117.4 (2)	C37—C38—H38	121.2
C2—C3—H3	121.3	C39—C38—H38	121.2
C4—C3—H3	121.3	C34—C39—C38	121.5 (2)
C5—C4—C3	121.3 (2)	C34—C39—C40	106.1 (2)
C5—C4—H4	119.4	C38—C39—C40	132.5 (2)
C3—C4—H4	119.4	N10—C40—N9	127.7 (2)
C4—C5—C6	121.8 (2)	N10—C40—C39	123.0 (2)
C4—C5—H5	119.1	N9—C40—C39	109.3 (2)
C6—C5—H5	119.1	N10—C41—N11	127.8 (2)
C7—C6—C5	117.5 (2)	N10—C41—C42	122.2 (2)
C7—C6—H6	121.3	N11—C41—C42	109.9 (2)
C5—C6—H6	121.3	C43—C42—C47	121.8 (2)
C6—C7—C2	120.2 (2)	C43—C42—C41	132.3 (2)
C6—C7—C8	133.4 (2)	C47—C42—C41	105.7 (2)
C2—C7—C8	106.3 (2)	C44—C43—C42	117.1 (2)
N2—C8—N1	127.7 (2)	C44—C43—H43	121.5
N2—C8—C7	122.6 (2)	C42—C43—H43	121.5
N1—C8—C7	109.7 (2)	C43—C44—C45	121.0 (2)
N2—C9—N3	128.3 (2)	C43—C44—H44	119.5
N2—C9—C10	122.4 (2)	C45—C44—H44	119.5
N3—C9—C10	109.3 (2)	C46—C45—C44	121.6 (2)
C11—C10—C15	121.6 (2)	C46—C45—H45	119.2
C11—C10—C9	132.4 (2)	C44—C45—H45	119.2
C15—C10—C9	106.0 (2)	C47—C46—C45	117.5 (2)
C12—C11—C10	117.7 (2)	C47—C46—H46	121.2
C12—C11—H11	121.1	C45—C46—H46	121.2
C10—C11—H11	121.1	C46—C47—C42	121.0 (2)
C11—C12—C13	121.2 (2)	C46—C47—C48	131.7 (2)
C11—C12—H12	119.4	C42—C47—C48	107.2 (2)
C13—C12—H12	119.4	N12—C48—N11	128.1 (2)
C14—C13—C12	121.1 (2)	N12—C48—C47	123.9 (2)
C14—C13—H13	119.5	N11—C48—C47	107.9 (2)
C12—C13—H13	119.5	N12—C49—N13	128.3 (2)
C13—C14—C15	118.2 (2)	N12—C49—C50	122.3 (2)
C13—C14—H14	120.9	N13—C49—C50	109.4 (2)
C15—C14—H14	120.9	C51—C50—C55	121.9 (2)
C14—C15—C10	120.2 (2)	C51—C50—C49	130.8 (2)
C14—C15—C16	133.3 (2)	C55—C50—C49	107.3 (2)
C10—C15—C16	106.5 (2)	C52—C51—C50	118.0 (2)
N4—C16—N3	127.4 (2)	C52—C51—H51	121.0
N4—C16—C15	123.4 (2)	C50—C51—H51	121.0
N3—C16—C15	109.3 (2)	C51—C52—C53	120.8 (2)
N4—C17—N5	128.7 (2)	C51—C52—H52	119.6
N4—C17—C18	122.3 (2)	C53—C52—H52	119.6
N5—C17—C18	109.0 (2)	C54—C53—C52	121.4 (2)
C19—C18—C23	122.1 (2)	C54—C53—H53	119.3
C19—C18—C17	131.1 (2)	C52—C53—H53	119.3
C23—C18—C17	106.9 (2)	C53—C54—C55	118.5 (2)
C20—C19—C18	117.6 (2)	C53—C54—H54	120.7
C20—C19—H19	121.2	C55—C54—H54	120.7
C18—C19—H19	121.2	C50—C55—C54	119.2 (2)
C19—C20—C21	120.8 (2)	C50—C55—C56	105.1 (2)
C19—C20—H20	119.6	C54—C55—C56	135.6 (2)
C21—C20—H20	119.6	N14—C56—N13	126.5 (2)
C22—C21—C20	121.5 (2)	N14—C56—C55	123.7 (2)
C22—C21—H21	119.3	N13—C56—C55	109.8 (2)
C20—C21—H21	119.3	N14—C57—N15	127.2 (2)
C21—C22—C23	118.1 (2)	N14—C57—C58	123.6 (2)
C21—C22—H22	121.0	N15—C57—C58	109.2 (2)
C23—C22—H22	121.0	C59—C58—C63	120.1 (2)
C22—C23—C18	119.9 (2)	C59—C58—C57	134.3 (2)
C22—C23—C24	134.2 (2)	C63—C58—C57	105.6 (2)
C18—C23—C24	105.9 (2)	C60—C59—C58	117.8 (2)
N6—C24—N5	126.7 (2)	C60—C59—H59	121.1
N6—C24—C23	124.0 (2)	C58—C59—H59	121.1
N5—C24—C23	109.3 (2)	C59—C60—C61	121.7 (2)
N6—C25—N7	126.7 (2)	C59—C60—H60	119.2
N6—C25—C26	123.4 (2)	C61—C60—H60	119.2
N7—C25—C26	109.9 (2)	C60—C61—C62	121.2 (2)
C27—C26—C31	119.4 (2)	C60—C61—H61	119.4
C27—C26—C25	135.0 (2)	C62—C61—H61	119.4
C31—C26—C25	105.6 (2)	C63—C62—C61	116.8 (2)
C28—C27—C26	118.4 (2)	C63—C62—H62	121.6
C28—C27—H27	120.8	C61—C62—H62	121.6
C26—C27—H27	120.8	C62—C63—C58	122.5 (2)
C27—C28—C29	121.0 (2)	C62—C63—C64	130.1 (2)
C27—C28—H28	119.5	C58—C63—C64	107.4 (2)
C29—C28—H28	119.5	N16—C64—N15	128.6 (2)
C30—C29—C28	121.7 (2)	N16—C64—C63	122.7 (2)
C30—C29—H29	119.1	N15—C64—C63	108.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N6^i	0.84 (2)	2.02 (2)	2.837 (3)	164 (2)
O2—H2O2···N14^ii	0.82 (2)	1.97 (2)	2.776 (3)	166 (2)

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