Diaqua-(5,10,15,20-tetra-phenyl-porphyrinato-κ(4)N)magnesium-18-crown-6 (1/1).

In the title compound, [Mg(C(44)H(28)N(4))(H(2)O)(2)]·C(12)H(24)O(6), the Mg(II) cation lies on an inversion center and is octa-hedrally coordinated by the four N atoms of the deprotonated tetra-phenyl-porphyrin (TPP) ligand and by two water mol-ecules. The asymmetric unit contains one half of the [Mg(TPP)(H(2)O)(2)] complex and one half of an 18-crown-6 mol-ecule. The average equatorial magnesium-pyrrole N atom distance (Mg-N(p)) is 2.071 (1) Å and the axial Mg-O(H(2)O) bond length is 2.213 (1) Å. The crystal packing is stabilized by two O-H⋯O hydrogen bonds between coordinating water mol-ecules and adjacent 18-crown-6 mol-ecules, and exhibits a one-dimensional supramolecular structure along the a axis. The supramolecular architecture is futher stabilized by weak C-H⋯π inter-actions. The 18-crown-6 mol-ecule is disordered over two sets of sites with an occupancy ratio of 0.8:0.2.

Related literature

For general background to magnesium porphyrin species and their applications, see: Ghosh et al. (2010 ▶). For related structures, see: Belghith et al. (2012 ▶); McArdle (1995 ▶); McKee et al. (1984 ▶); Choon et al. (1986 ▶); McKee & Rodley (1988 ▶); Gryz et al. (2007 ▶); Imaz et al. (2005 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

[Mg(C44H28N4)(H2O)2]·C12H24O6

M = 937.36

Triclinic,

a = 8.1440 (3) Å

b = 12.3080 (4) Å

c = 12.4170 (4) Å

α = 86.894 (3)°

β = 75.163 (3)°

γ = 79.529 (3)°

V = 1183.06 (7) Å3

Z = 1

Mo Kα radiation

μ = 0.10 mm−1

T = 180 K

0.56 × 0.51 × 0.19 mm

Data collection

Oxford Diffraction Xcalibur (Sapphire1) diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.946, T max = 0.981

23613 measured reflections

4650 independent reflections

4013 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.118

S = 1.04

4650 reflections

400 parameters

119 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813001219/xu5669sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813001219/xu5669Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Mg(C44H28N4)(H2O)2]·C12H24O6	Z = 1
Mr = 937.36	F(000) = 496
Triclinic, P1	Dx = 1.316 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1440 (3) Å	Cell parameters from 14229 reflections
b = 12.3080 (4) Å	θ = 2.9–28.4°
c = 12.4170 (4) Å	µ = 0.10 mm−1
α = 86.894 (3)°	T = 180 K
β = 75.163 (3)°	Prism, purple
γ = 79.529 (3)°	0.56 × 0.51 × 0.19 mm
V = 1183.06 (7) Å3

Oxford Diffraction Xcalibur (Sapphire1) diffractometer	4650 independent reflections
Radiation source: fine-focus sealed tube	4013 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 8.2632 pixels mm-1	θmax = 26.0°, θmin = 2.9°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −15→15
Tmin = 0.946, Tmax = 0.981	l = −15→15
23613 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0568P)2 + 0.6503P] where P = (Fo2 + 2Fc2)/3
4650 reflections	(Δ/σ)max < 0.001
400 parameters	Δρmax = 0.46 e Å−3
119 restraints	Δρmin = −0.28 e Å−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Mg1	0.0000	0.0000	0.5000	0.01893 (17)
O1	0.27384 (14)	−0.00267 (10)	0.49625 (10)	0.0273 (3)
H1O1	0.323 (3)	−0.0256 (18)	0.5592 (13)	0.050*
H2O1	0.360 (2)	−0.0260 (18)	0.4278 (12)	0.050*
N1	−0.05837 (16)	−0.03608 (10)	0.66901 (10)	0.0189 (3)
N2	−0.06769 (16)	0.16696 (10)	0.53555 (10)	0.0185 (3)
C1	−0.04664 (19)	−0.13929 (12)	0.71606 (12)	0.0197 (3)
C2	−0.1086 (2)	−0.12941 (13)	0.83554 (13)	0.0253 (3)
H2	−0.1120	−0.1871	0.8872	0.030*
C3	−0.1607 (2)	−0.02077 (13)	0.85834 (13)	0.0256 (3)
H3	−0.2093	0.0103	0.9284	0.031*
C4	−0.12687 (19)	0.03831 (12)	0.75337 (12)	0.0203 (3)
C5	−0.15851 (19)	0.15423 (12)	0.74036 (12)	0.0202 (3)
C6	−0.12549 (19)	0.21291 (12)	0.63867 (12)	0.0198 (3)
C7	−0.1471 (2)	0.33201 (13)	0.62737 (13)	0.0239 (3)
H7	−0.1822	0.3827	0.6851	0.029*
C8	−0.1069 (2)	0.35562 (12)	0.51726 (13)	0.0234 (3)
H8	−0.1091	0.4256	0.4848	0.028*
C9	−0.05984 (19)	0.25119 (12)	0.45940 (12)	0.0193 (3)
C10	0.01238 (19)	−0.23950 (12)	0.65711 (12)	0.0198 (3)
C11	0.0337 (2)	−0.34328 (12)	0.72424 (12)	0.0215 (3)
C12	0.1988 (2)	−0.40022 (13)	0.71999 (14)	0.0277 (4)
H12	0.2936	−0.3734	0.6755	0.033*
C13	0.2240 (3)	−0.49656 (14)	0.78129 (15)	0.0346 (4)
H13	0.3353	−0.5339	0.7777	0.042*
C14	0.0846 (3)	−0.53712 (14)	0.84755 (15)	0.0355 (4)
H14	0.1015	−0.6014	0.8892	0.043*
C15	−0.0798 (3)	−0.48205 (15)	0.85186 (15)	0.0373 (4)
H15	−0.1743	−0.5097	0.8958	0.045*
C16	−0.1050 (2)	−0.38552 (14)	0.79099 (14)	0.0311 (4)
H16	−0.2166	−0.3485	0.7950	0.037*
C17	−0.2409 (2)	0.22080 (12)	0.84322 (12)	0.0214 (3)
C18	−0.1582 (2)	0.22428 (13)	0.92774 (13)	0.0262 (3)
H18	−0.0482	0.1834	0.9210	0.031*
C19	−0.2371 (2)	0.28757 (14)	1.02156 (13)	0.0295 (4)
H19	−0.1797	0.2894	1.0771	0.035*
C20	−0.4005 (2)	0.34789 (14)	1.03309 (13)	0.0296 (4)
H20	−0.4535	0.3906	1.0961	0.036*
C21	−0.4850 (2)	0.34448 (14)	0.95063 (14)	0.0319 (4)
H21	−0.5958	0.3844	0.9585	0.038*
C22	−0.4054 (2)	0.28192 (14)	0.85624 (14)	0.0275 (4)
H22	−0.4631	0.2808	0.8007	0.033*
C23A	0.5253 (4)	−0.1823 (3)	0.7059 (2)	0.0620 (12)	0.80
H23A	0.6378	−0.1605	0.6826	0.074*	0.80
H23B	0.5341	−0.2468	0.7539	0.074*	0.80
O4A	0.4741 (2)	−0.20837 (18)	0.61214 (18)	0.0495 (5)	0.80
C24A	0.3972 (4)	−0.0906 (3)	0.7682 (2)	0.0682 (10)	0.80
H24A	0.2828	−0.1097	0.7866	0.082*	0.80
H24B	0.4258	−0.0775	0.8370	0.082*	0.80
O2A	0.4010 (3)	0.0049 (2)	0.70026 (15)	0.0583 (5)	0.80
C25A	0.3047 (6)	0.1004 (4)	0.7585 (5)	0.0708 (16)	0.80
H25A	0.3639	0.1206	0.8110	0.085*	0.80
H25B	0.1925	0.0859	0.8001	0.085*	0.80
C26A	0.2830 (3)	0.1925 (3)	0.6784 (3)	0.0665 (10)	0.80
H26A	0.2331	0.1705	0.6218	0.080*	0.80
H26B	0.2067	0.2563	0.7168	0.080*	0.80
C27A	0.4410 (6)	0.3090 (3)	0.5543 (3)	0.0657 (11)	0.80
H27A	0.5529	0.3318	0.5349	0.079*	0.80
H27B	0.3573	0.3703	0.5919	0.079*	0.80
C28A	0.3963 (4)	0.2866 (3)	0.4501 (2)	0.0658 (9)	0.80
H28A	0.2878	0.2595	0.4680	0.079*	0.80
H28B	0.3831	0.3543	0.4071	0.079*	0.80
O3A	0.4463 (2)	0.2189 (2)	0.62918 (17)	0.0605 (6)	0.80
C23B	0.485 (2)	−0.1672 (8)	0.7359 (12)	0.0502 (12)	0.20
H23C	0.3729	−0.1875	0.7676	0.060*	0.20
H23D	0.5497	−0.1783	0.7925	0.060*	0.20
C24B	0.3936 (16)	0.0228 (9)	0.7901 (8)	0.0497 (11)	0.20
H24C	0.4858	0.0447	0.8157	0.060*	0.20
H24D	0.3206	−0.0108	0.8523	0.060*	0.20
C25B	0.290 (2)	0.1223 (19)	0.750 (2)	0.0485 (11)	0.20
H25C	0.2036	0.1007	0.7179	0.058*	0.20
H25D	0.2324	0.1728	0.8103	0.058*	0.20
C26B	0.3267 (13)	0.2581 (8)	0.6048 (9)	0.0466 (11)	0.20
H26C	0.2533	0.3143	0.6558	0.056*	0.20
H26D	0.2538	0.2265	0.5689	0.056*	0.20
C27B	0.453 (2)	0.3115 (11)	0.5178 (11)	0.0464 (12)	0.20
H27C	0.3923	0.3764	0.4874	0.056*	0.20
H27D	0.5364	0.3346	0.5508	0.056*	0.20
C28B	0.5792 (17)	−0.2380 (10)	0.6372 (11)	0.0500 (13)	0.20
H28C	0.6817	−0.2096	0.5971	0.060*	0.20
H28D	0.6139	−0.3131	0.6611	0.060*	0.20
O2B	0.4649 (11)	−0.0550 (7)	0.7021 (7)	0.0507 (11)	0.20
O3B	0.4086 (12)	0.1731 (7)	0.6670 (7)	0.0473 (10)	0.20
O4B	0.5366 (12)	0.2356 (7)	0.4328 (7)	0.0463 (12)	0.20

	U11	U22	U33	U12	U13	U23
Mg1	0.0259 (4)	0.0142 (3)	0.0152 (3)	−0.0009 (3)	−0.0041 (3)	−0.0010 (3)
O1	0.0240 (6)	0.0324 (6)	0.0247 (6)	−0.0030 (5)	−0.0060 (5)	−0.0011 (5)
N1	0.0217 (6)	0.0157 (6)	0.0181 (6)	0.0000 (5)	−0.0050 (5)	−0.0011 (5)
N2	0.0218 (6)	0.0166 (6)	0.0162 (6)	−0.0011 (5)	−0.0047 (5)	−0.0009 (5)
C1	0.0203 (7)	0.0195 (7)	0.0189 (7)	−0.0011 (6)	−0.0060 (6)	0.0010 (6)
C2	0.0327 (9)	0.0228 (8)	0.0183 (8)	−0.0021 (6)	−0.0050 (6)	0.0026 (6)
C3	0.0340 (9)	0.0235 (8)	0.0163 (7)	−0.0016 (7)	−0.0030 (6)	−0.0012 (6)
C4	0.0222 (7)	0.0205 (7)	0.0171 (7)	−0.0005 (6)	−0.0045 (6)	−0.0022 (6)
C5	0.0221 (7)	0.0193 (7)	0.0185 (7)	−0.0002 (6)	−0.0057 (6)	−0.0034 (6)
C6	0.0212 (7)	0.0184 (7)	0.0195 (7)	−0.0007 (6)	−0.0061 (6)	−0.0030 (6)
C7	0.0309 (8)	0.0180 (7)	0.0224 (8)	−0.0007 (6)	−0.0075 (6)	−0.0043 (6)
C8	0.0315 (8)	0.0154 (7)	0.0237 (8)	−0.0029 (6)	−0.0084 (6)	−0.0010 (6)
C9	0.0202 (7)	0.0169 (7)	0.0206 (7)	−0.0015 (5)	−0.0061 (6)	−0.0003 (6)
C10	0.0201 (7)	0.0182 (7)	0.0208 (7)	−0.0020 (6)	−0.0058 (6)	0.0015 (6)
C11	0.0315 (8)	0.0163 (7)	0.0170 (7)	−0.0025 (6)	−0.0074 (6)	−0.0017 (6)
C12	0.0316 (9)	0.0249 (8)	0.0265 (8)	−0.0020 (7)	−0.0092 (7)	0.0017 (7)
C13	0.0434 (10)	0.0252 (9)	0.0355 (10)	0.0053 (7)	−0.0183 (8)	0.0001 (7)
C14	0.0617 (12)	0.0185 (8)	0.0255 (9)	−0.0017 (8)	−0.0139 (8)	0.0036 (7)
C15	0.0500 (11)	0.0271 (9)	0.0297 (9)	−0.0097 (8)	−0.0001 (8)	0.0056 (7)
C16	0.0330 (9)	0.0263 (8)	0.0300 (9)	−0.0026 (7)	−0.0030 (7)	0.0038 (7)
C17	0.0282 (8)	0.0164 (7)	0.0178 (7)	−0.0024 (6)	−0.0034 (6)	−0.0006 (6)
C18	0.0286 (8)	0.0265 (8)	0.0220 (8)	0.0001 (6)	−0.0067 (6)	−0.0022 (6)
C19	0.0400 (10)	0.0301 (9)	0.0192 (8)	−0.0059 (7)	−0.0085 (7)	−0.0024 (6)
C20	0.0414 (10)	0.0233 (8)	0.0187 (8)	−0.0019 (7)	0.0007 (7)	−0.0047 (6)
C21	0.0314 (9)	0.0286 (9)	0.0290 (9)	0.0063 (7)	−0.0027 (7)	−0.0054 (7)
C22	0.0308 (9)	0.0269 (8)	0.0235 (8)	0.0010 (7)	−0.0083 (7)	−0.0039 (6)
C23A	0.042 (2)	0.091 (3)	0.054 (3)	−0.0160 (18)	−0.0204 (18)	0.040 (2)
O4A	0.0354 (10)	0.0570 (13)	0.0543 (13)	−0.0082 (9)	−0.0101 (9)	0.0096 (10)
C24A	0.060 (2)	0.115 (3)	0.0319 (14)	−0.032 (2)	−0.0086 (13)	0.0206 (17)
O2A	0.0538 (13)	0.0805 (16)	0.0346 (10)	−0.0104 (11)	−0.0002 (9)	−0.0045 (10)
C25A	0.047 (2)	0.106 (5)	0.053 (3)	−0.029 (3)	0.0190 (19)	−0.045 (3)
C26A	0.0301 (15)	0.077 (2)	0.089 (3)	−0.0051 (14)	−0.0012 (15)	−0.050 (2)
C27A	0.056 (2)	0.068 (2)	0.078 (3)	−0.0151 (16)	−0.020 (2)	−0.008 (2)
C28A	0.0435 (17)	0.076 (2)	0.076 (2)	−0.0041 (15)	−0.0145 (16)	−0.0034 (18)
O3A	0.0388 (11)	0.0919 (18)	0.0554 (13)	−0.0145 (11)	−0.0143 (10)	−0.0184 (13)
C23B	0.0502 (13)	0.0501 (13)	0.0497 (13)	−0.0081 (7)	−0.0120 (7)	0.0002 (7)
C24B	0.0495 (12)	0.0499 (12)	0.0491 (12)	−0.0080 (7)	−0.0117 (7)	0.0003 (7)
C25B	0.0482 (12)	0.0488 (12)	0.0483 (12)	−0.0084 (7)	−0.0120 (7)	−0.0004 (7)
C26B	0.0461 (12)	0.0469 (12)	0.0472 (12)	−0.0086 (7)	−0.0120 (7)	−0.0007 (7)
C27B	0.0459 (13)	0.0468 (13)	0.0471 (13)	−0.0086 (7)	−0.0125 (7)	0.0001 (7)
C28B	0.0501 (14)	0.0499 (14)	0.0498 (14)	−0.0082 (8)	−0.0125 (8)	−0.0002 (8)
O2B	0.0504 (12)	0.0504 (12)	0.0499 (12)	−0.0074 (7)	−0.0112 (7)	0.0010 (7)
O3B	0.0470 (12)	0.0478 (12)	0.0474 (12)	−0.0088 (7)	−0.0117 (7)	−0.0008 (7)
O4B	0.0457 (14)	0.0465 (14)	0.0471 (14)	−0.0084 (8)	−0.0127 (8)	0.0009 (8)

Mg1—N2	2.0697 (12)	C21—C22	1.383 (2)
Mg1—N2i	2.0697 (12)	C21—H21	0.9300
Mg1—N1	2.0717 (12)	C22—H22	0.9300
Mg1—N1i	2.0717 (12)	C23A—O4A	1.404 (3)
Mg1—O1	2.2130 (11)	C23A—C24A	1.488 (4)
Mg1—O1i	2.2130 (11)	C23A—H23A	0.9700
O1—H1O1	0.972 (10)	C23A—H23B	0.9700
O1—H2O1	0.972 (10)	O4A—C28Aii	1.389 (4)
N1—C4	1.3659 (19)	C24A—O2A	1.410 (3)
N1—C1	1.3669 (18)	C24A—H24A	0.9700
N2—C6	1.3615 (19)	C24A—H24B	0.9700
N2—C9	1.3638 (19)	O2A—C25A	1.410 (5)
C1—C10	1.411 (2)	C25A—C26A	1.484 (3)
C1—C2	1.444 (2)	C25A—H25A	0.9700
C2—C3	1.350 (2)	C25A—H25B	0.9700
C2—H2	0.9300	C26A—O3A	1.402 (3)
C3—C4	1.446 (2)	C26A—H26A	0.9700
C3—H3	0.9300	C26A—H26B	0.9700
C4—C5	1.411 (2)	C27A—O3A	1.409 (3)
C5—C6	1.409 (2)	C27A—C28A	1.483 (3)
C5—C17	1.493 (2)	C27A—H27A	0.9700
C6—C7	1.448 (2)	C27A—H27B	0.9700
C7—C8	1.350 (2)	C28A—O4Aii	1.389 (4)
C7—H7	0.9300	C28A—H28A	0.9700
C8—C9	1.447 (2)	C28A—H28B	0.9700
C8—H8	0.9300	C23B—O2B	1.413 (6)
C9—C10i	1.407 (2)	C23B—C28B	1.497 (6)
C10—C9i	1.407 (2)	C23B—H23C	0.9700
C10—C11	1.495 (2)	C23B—H23D	0.9700
C11—C16	1.386 (2)	C24B—O2B	1.427 (6)
C11—C12	1.388 (2)	C24B—C25B	1.497 (6)
C12—C13	1.386 (2)	C24B—H24C	0.9700
C12—H12	0.9300	C24B—H24D	0.9700
C13—C14	1.378 (3)	C25B—O3B	1.420 (6)
C13—H13	0.9300	C25B—H25C	0.9700
C14—C15	1.375 (3)	C25B—H25D	0.9700
C14—H14	0.9300	C26B—O3B	1.435 (6)
C15—C16	1.385 (2)	C26B—C27B	1.500 (6)
C15—H15	0.9300	C26B—H26C	0.9700
C16—H16	0.9300	C26B—H26D	0.9700
C17—C22	1.387 (2)	C27B—O4B	1.400 (6)
C17—C18	1.391 (2)	C27B—H27C	0.9700
C18—C19	1.382 (2)	C27B—H27D	0.9700
C18—H18	0.9300	C28B—O4Bii	1.433 (15)
C19—C20	1.377 (2)	C28B—H28C	0.9700
C19—H19	0.9300	C28B—H28D	0.9700
C20—C21	1.378 (3)	O4B—C28Bii	1.433 (15)
C20—H20	0.9300
N2—Mg1—N2i	180.0	C20—C21—C22	120.24 (16)
N2—Mg1—N1	89.79 (5)	C20—C21—H21	119.9
N2i—Mg1—N1	90.21 (5)	C22—C21—H21	119.9
N2—Mg1—N1i	90.21 (5)	C21—C22—C17	120.94 (15)
N2i—Mg1—N1i	89.79 (5)	C21—C22—H22	119.5
N1—Mg1—N1i	180.0	C17—C22—H22	119.5
N2—Mg1—O1	92.86 (5)	O4A—C23A—C24A	109.8 (3)
N2i—Mg1—O1	87.14 (5)	O4A—C23A—H23A	109.7
N1—Mg1—O1	91.48 (4)	C24A—C23A—H23A	109.7
N1i—Mg1—O1	88.52 (4)	O4A—C23A—H23B	109.7
N2—Mg1—O1i	87.14 (5)	C24A—C23A—H23B	109.7
N2i—Mg1—O1i	92.86 (5)	H23A—C23A—H23B	108.2
N1—Mg1—O1i	88.52 (4)	C28Aii—O4A—C23A	108.6 (2)
N1i—Mg1—O1i	91.48 (4)	O2A—C24A—C23A	108.2 (2)
O1—Mg1—O1i	180.0	O2A—C24A—H24A	110.1
Mg1—O1—H1O1	123.5 (14)	C23A—C24A—H24A	110.1
Mg1—O1—H2O1	117.8 (14)	O2A—C24A—H24B	110.1
H1O1—O1—H2O1	108.9 (19)	C23A—C24A—H24B	110.1
C4—N1—C1	107.47 (12)	H24A—C24A—H24B	108.4
C4—N1—Mg1	126.28 (10)	C24A—O2A—C25A	112.3 (3)
C1—N1—Mg1	126.10 (10)	O2A—C25A—C26A	109.6 (4)
C6—N2—C9	107.51 (12)	O2A—C25A—H25A	109.8
C6—N2—Mg1	126.51 (10)	C26A—C25A—H25A	109.8
C9—N2—Mg1	125.97 (10)	O2A—C25A—H25B	109.8
N1—C1—C10	125.43 (13)	C26A—C25A—H25B	109.8
N1—C1—C2	109.09 (13)	H25A—C25A—H25B	108.2
C10—C1—C2	125.46 (14)	O3A—C26A—C25A	107.9 (3)
C3—C2—C1	107.21 (13)	O3A—C26A—H26A	110.1
C3—C2—H2	126.4	C25A—C26A—H26A	110.1
C1—C2—H2	126.4	O3A—C26A—H26B	110.1
C2—C3—C4	107.15 (14)	C25A—C26A—H26B	110.1
C2—C3—H3	126.4	H26A—C26A—H26B	108.4
C4—C3—H3	126.4	O3A—C27A—C28A	114.9 (3)
N1—C4—C5	125.54 (13)	O3A—C27A—H27A	108.5
N1—C4—C3	109.05 (13)	C28A—C27A—H27A	108.5
C5—C4—C3	125.41 (14)	O3A—C27A—H27B	108.5
C6—C5—C4	126.02 (14)	C28A—C27A—H27B	108.5
C6—C5—C17	116.87 (13)	H27A—C27A—H27B	107.5
C4—C5—C17	117.07 (13)	O4Aii—C28A—C27A	109.7 (3)
N2—C6—C5	125.61 (13)	O4Aii—C28A—H28A	109.7
N2—C6—C7	109.11 (13)	C27A—C28A—H28A	109.7
C5—C6—C7	125.28 (14)	O4Aii—C28A—H28B	109.7
C8—C7—C6	107.17 (14)	C27A—C28A—H28B	109.7
C8—C7—H7	126.4	H28A—C28A—H28B	108.2
C6—C7—H7	126.4	C26A—O3A—C27A	113.0 (3)
C7—C8—C9	106.88 (13)	O2B—C23B—C28B	109.3 (10)
C7—C8—H8	126.6	O2B—C23B—H23C	109.8
C9—C8—H8	126.6	C28B—C23B—H23C	109.8
N2—C9—C10i	125.84 (13)	O2B—C23B—H23D	109.8
N2—C9—C8	109.24 (13)	C28B—C23B—H23D	109.8
C10i—C9—C8	124.92 (14)	H23C—C23B—H23D	108.3
C9i—C10—C1	126.30 (14)	O2B—C24B—C25B	109.7 (16)
C9i—C10—C11	116.47 (13)	O2B—C24B—H24C	109.7
C1—C10—C11	117.18 (13)	C25B—C24B—H24C	109.7
C16—C11—C12	118.25 (14)	O2B—C24B—H24D	109.7
C16—C11—C10	122.71 (14)	C25B—C24B—H24D	109.7
C12—C11—C10	119.04 (14)	H24C—C24B—H24D	108.2
C13—C12—C11	120.79 (16)	O3B—C25B—C24B	106.3 (10)
C13—C12—H12	119.6	O3B—C25B—H25C	110.5
C11—C12—H12	119.6	C24B—C25B—H25C	110.5
C14—C13—C12	120.16 (17)	O3B—C25B—H25D	110.5
C14—C13—H13	119.9	C24B—C25B—H25D	110.5
C12—C13—H13	119.9	H25C—C25B—H25D	108.7
C15—C14—C13	119.68 (16)	O3B—C26B—C27B	113.2 (12)
C15—C14—H14	120.2	O3B—C26B—H26C	108.9
C13—C14—H14	120.2	C27B—C26B—H26C	108.9
C14—C15—C16	120.15 (17)	O3B—C26B—H26D	108.9
C14—C15—H15	119.9	C27B—C26B—H26D	108.9
C16—C15—H15	119.9	H26C—C26B—H26D	107.8
C15—C16—C11	120.96 (17)	O4B—C27B—C26B	109.0 (10)
C15—C16—H16	119.5	O4B—C27B—H27C	109.9
C11—C16—H16	119.5	C26B—C27B—H27C	109.9
C22—C17—C18	118.08 (14)	O4B—C27B—H27D	109.9
C22—C17—C5	119.67 (14)	C26B—C27B—H27D	109.9
C18—C17—C5	122.25 (14)	H27C—C27B—H27D	108.3
C19—C18—C17	120.96 (15)	O4Bii—C28B—C23B	107.2 (13)
C19—C18—H18	119.5	O4Bii—C28B—H28C	110.3
C17—C18—H18	119.5	C23B—C28B—H28C	110.3
C20—C19—C18	120.19 (16)	O4Bii—C28B—H28D	110.3
C20—C19—H19	119.9	C23B—C28B—H28D	110.3
C18—C19—H19	119.9	H28C—C28B—H28D	108.5
C19—C20—C21	119.59 (15)	C23B—O2B—C24B	115.3 (10)
C19—C20—H20	120.2	C25B—O3B—C26B	113.4 (10)
C21—C20—H20	120.2	C27B—O4B—C28Bii	106.0 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2A	0.97 (2)	2.08 (2)	2.984 (2)	153 (2)
O1—H2O1···O2Aii	0.97 (2)	2.22 (2)	3.105 (2)	150 (2)
O1—H1O1···O2B	0.97 (2)	2.33 (2)	3.297 (10)	170 (2)
O1—H2O1···O2Bii	0.97 (2)	2.19 (2)	2.962 (8)	135 (1)
C15—H15···Cg4iii	0.93	2.96	3.730 (2)	141
C27A—H27A···Cg2iv	0.97	2.86	3.671 (5)	142
C26B—H26D···Cg2	0.97	2.89	3.678 (11)	139
C27B—H27D···Cg2iv	0.97	2.94	3.715 (17)	139

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg4 are the centroids of the N2/C6–C9 and C17–C22 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2A	0.97 (2)	2.08 (2)	2.984 (2)	153 (2)
O1—H2O1⋯O2A i	0.97 (2)	2.22 (2)	3.105 (2)	150 (2)
O1—H1O1⋯O2B	0.97 (2)	2.33 (2)	3.297 (10)	170 (2)
O1—H2O1⋯O2B i	0.97 (2)	2.19 (2)	2.962 (8)	135 (1)
C15—H15⋯Cg4ii	0.93	2.96	3.730 (2)	141
C27A—H27A⋯Cg2iii	0.97	2.86	3.671 (5)	142
C26B—H26D⋯Cg2	0.97	2.89	3.678 (11)	139
C27B—H27D⋯Cg2iii	0.97	2.94	3.715 (17)	139

Symmetry codes: (i) ; (ii) ; (iii) .