Synthesis and characterization of a photochromic magnesium(II) coordination polymer based on a naphthalene di­imide ligand

Naphthalene di­imides, which are planar, chemically robust and redox-active, are an attractive class of electron-deficient dyes, which can undergo a single reversible one-electron reduction to form stable radical anions in the presence of electron donors upon irradiation. This makes them excellent candidates for organic linkers in the construction of photochromic coordination polymers. Such a photochromic one-dimensional linear coordination polymer has been pre­pared using N,N′-bis­(3-carb­oxy­phen­yl)naphthalene-1,8:4,5-tetra­carboximide (H₂BBNDI). Crystallization of H₂BBNDI with magnesium nitrate in an N,N′-di­methyl­formamide (DMF)/ethanol/H₂O mixed-solvent system under solvothermal conditions afforded the one-dimensional coordination polymer catena-poly[[bis­(di­methyl­formamide-κO)magnesium(II)]-bis­[μ-N-(3-carb­oxylato­phen­yl)-N′-(3-carboxyl­phen­yl)naphthalene-1,8:4,5-tetra­carboximide-κ²O:O′]], [Mg(C₂₈H₁₃N₂O₈)₂(C₃H₇NO)₂]_n. The asymmetric unit contains half of a magnesium cation, one HBBNDI⁻ ligand and one DMF mol­ecule. Two partially deprotonated HBBNDI⁻ ligands bridge two magnesium cations to form a one-dimensional chain. Strong inter-chain π–π inter­actions between the naphthalene rings of the HBBNDI⁻ ligand and the imide rings of adjacent chains provide a two-dimensional structure. The supra­molecular three-dimensional framework is stabilized by π–π inter­actions between naphthalene rings of neighbouring two-dimensional supra­molecular networks. The complex exhibits a reversible photochromic behaviour, which may originate from the photoinduced electron-transfer generation of radicals in the HBBNDI⁻ ligand.

Computing details

Data collection: CrystalClear (Rigaku, 2002); cell refinement: CrystalClear (Rigaku, 2002); data reduction: CrystalClear (Rigaku, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: publCIF (Westrip, 2010).

catena-Poly[[bis(dimethylformamide-κO)magnesium(II)]bis[µ-N-(3-carboxyphenyl)-N'-(3-carboxylatophenyl)naphthalene-1,8:4,5-tetracarboximide-κ²O:O']]

Crystal data

[Mg(C28H13N2O8)2(C3H7NO)2]	Z = 1
Mr = 1181.31	F(000) = 610
Triclinic, P1	Dx = 1.446 Mg m^−3
a = 9.2595 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.2711 (3) Å	Cell parameters from 4416 reflections
c = 16.0049 (5) Å	θ = 2.6–30.3°
α = 96.056 (3)°	µ = 0.12 mm^−1
β = 92.679 (3)°	T = 153 K
γ = 115.714 (4)°	Block, yellow
V = 1356.47 (9) Å^3	0.36 × 0.26 × 0.12 mm

Data collection

Rigaku Saturn 724 CCD area-detector diffractometer	3779 reflections with I > 2σ(I)
ω scans	Rint = 0.035
Absorption correction: multi-scan (RAPID-AUTO; Rigaku, 1998)	θmax = 26.4°, θmin = 2.7°
Tmin = 0.755, Tmax = 1.000	h = −10→11
11817 measured reflections	k = −12→12
5346 independent reflections	l = −15→19

Refinement

Refinement on F^2	1 restraint
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.133	w = 1/[σ^2(Fo^2) + (0.0702P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
5346 reflections	Δρmax = 0.28 e Å^−3
399 parameters	Δρmin = −0.36 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	0.5000	0.5000	0.0000	0.0242 (2)
O1	0.66770 (18)	0.67020 (17)	0.08226 (9)	0.0379 (4)
O2	0.8779 (2)	0.83854 (18)	0.02998 (10)	0.0510 (5)
H2A	0.861 (4)	0.782 (3)	−0.0165 (11)	0.076*
O3	0.86387 (16)	0.79463 (18)	0.43684 (9)	0.0358 (4)
O4	0.53270 (16)	0.97666 (16)	0.33614 (9)	0.0305 (3)
O5	0.32634 (17)	0.48081 (17)	0.73603 (9)	0.0347 (4)
O6	−0.04390 (16)	0.58976 (15)	0.60254 (9)	0.0296 (3)
O7	−0.32602 (17)	0.47366 (16)	0.93384 (9)	0.0343 (4)
O8	−0.1435 (2)	0.68347 (17)	0.89849 (10)	0.0459 (4)
O9	0.49130 (18)	0.64797 (17)	−0.07407 (9)	0.0365 (4)
N1	0.69306 (18)	0.87747 (17)	0.38331 (9)	0.0219 (4)
N2	0.14153 (18)	0.53810 (17)	0.67140 (10)	0.0222 (4)
N3	0.4236 (2)	0.8138 (2)	−0.12225 (14)	0.0464 (5)
C1	0.7887 (3)	0.7883 (2)	0.08897 (13)	0.0298 (5)
C2	0.8407 (2)	0.8851 (2)	0.17158 (12)	0.0243 (4)
C3	0.9812 (2)	1.0156 (2)	0.18413 (13)	0.0280 (5)
H3	1.0444	1.0470	0.1387	0.034*
C4	1.0286 (2)	1.0994 (2)	0.26247 (14)	0.0317 (5)
H4	1.1252	1.1879	0.2710	0.038*
C5	0.9357 (2)	1.0550 (2)	0.32891 (13)	0.0279 (5)
H5	0.9687	1.1121	0.3831	0.034*
C6	0.7942 (2)	0.9263 (2)	0.31519 (12)	0.0225 (4)
C7	0.7459 (2)	0.8410 (2)	0.23772 (12)	0.0234 (4)
H7	0.6489	0.7528	0.2293	0.028*
C8	0.5547 (2)	0.9015 (2)	0.38359 (12)	0.0226 (4)
C9	0.7386 (2)	0.8054 (2)	0.44077 (12)	0.0239 (4)
C10	0.6256 (2)	0.7410 (2)	0.50406 (12)	0.0222 (4)
C11	0.4780 (2)	0.7505 (2)	0.50178 (11)	0.0201 (4)
C12	0.4390 (2)	0.8278 (2)	0.44399 (11)	0.0209 (4)
C13	0.2924 (2)	0.8328 (2)	0.44234 (12)	0.0239 (4)
H13	0.2681	0.8873	0.4043	0.029*
C14	0.1790 (2)	0.7579 (2)	0.49646 (12)	0.0228 (4)
H14	0.0767	0.7587	0.4932	0.027*
C15	0.2149 (2)	0.6831 (2)	0.55429 (12)	0.0209 (4)
C16	0.3661 (2)	0.6807 (2)	0.55903 (11)	0.0202 (4)
C17	0.4077 (2)	0.6079 (2)	0.61901 (11)	0.0214 (4)
C18	0.5539 (2)	0.6025 (2)	0.62074 (12)	0.0242 (4)
H18	0.5814	0.5543	0.6617	0.029*
C19	0.6625 (2)	0.6677 (2)	0.56230 (12)	0.0242 (4)
H19	0.7619	0.6612	0.5630	0.029*
C20	0.2931 (2)	0.5372 (2)	0.68052 (12)	0.0239 (4)
C21	0.0923 (2)	0.6016 (2)	0.60953 (12)	0.0216 (4)
C22	0.0234 (2)	0.4614 (2)	0.72746 (12)	0.0228 (4)
C23	−0.0294 (2)	0.3122 (2)	0.72589 (12)	0.0264 (5)
H23	0.0141	0.2613	0.6902	0.032*
C24	−0.1461 (3)	0.2386 (2)	0.77713 (14)	0.0323 (5)
H24	−0.1834	0.1365	0.7764	0.039*
C25	−0.2091 (3)	0.3129 (2)	0.82941 (13)	0.0316 (5)
H25	−0.2912	0.2612	0.8633	0.038*
C26	−0.1523 (2)	0.4632 (2)	0.83249 (12)	0.0267 (5)
C27	−0.0345 (2)	0.5377 (2)	0.78099 (12)	0.0264 (5)
H27	0.0055	0.6403	0.7828	0.032*
C28	−0.2143 (3)	0.5449 (2)	0.89273 (13)	0.0321 (5)
C29	0.3972 (3)	0.7010 (2)	−0.08188 (14)	0.0366 (5)
H29	0.2986	0.6585	−0.0574	0.044*
C30	0.5740 (3)	0.8808 (4)	−0.1608 (2)	0.0744 (10)
H30A	0.6498	0.9692	−0.1239	0.112*
H30B	0.5523	0.9065	−0.2157	0.112*
H30C	0.6209	0.8118	−0.1687	0.112*
C31	0.3168 (4)	0.8826 (3)	−0.1246 (2)	0.0701 (9)
H31A	0.2198	0.8260	−0.0981	0.105*
H31B	0.2865	0.8867	−0.1834	0.105*
H31C	0.3717	0.9819	−0.0939	0.105*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mg1	0.0304 (5)	0.0190 (5)	0.0244 (5)	0.0094 (4)	0.0131 (4)	0.0101 (4)
O1	0.0405 (9)	0.0329 (9)	0.0280 (8)	0.0036 (8)	0.0107 (7)	0.0070 (7)
O2	0.0749 (12)	0.0264 (9)	0.0382 (9)	0.0062 (9)	0.0360 (9)	0.0080 (7)
O3	0.0240 (8)	0.0555 (11)	0.0389 (9)	0.0233 (8)	0.0142 (7)	0.0221 (8)
O4	0.0279 (8)	0.0337 (9)	0.0358 (8)	0.0146 (7)	0.0131 (6)	0.0207 (7)
O5	0.0269 (8)	0.0432 (10)	0.0368 (8)	0.0133 (7)	0.0085 (7)	0.0245 (7)
O6	0.0190 (7)	0.0327 (9)	0.0387 (8)	0.0097 (7)	0.0105 (6)	0.0162 (7)
O7	0.0396 (9)	0.0284 (9)	0.0393 (8)	0.0146 (7)	0.0254 (7)	0.0159 (7)
O8	0.0697 (11)	0.0238 (9)	0.0423 (9)	0.0138 (8)	0.0388 (8)	0.0131 (7)
O9	0.0418 (9)	0.0344 (9)	0.0412 (9)	0.0195 (8)	0.0142 (7)	0.0221 (7)
N1	0.0190 (8)	0.0238 (9)	0.0226 (8)	0.0073 (7)	0.0093 (7)	0.0088 (7)
N2	0.0184 (8)	0.0223 (9)	0.0257 (8)	0.0066 (7)	0.0086 (7)	0.0102 (7)
N3	0.0337 (11)	0.0337 (12)	0.0721 (15)	0.0102 (9)	0.0060 (10)	0.0290 (11)
C1	0.0372 (12)	0.0218 (11)	0.0315 (11)	0.0113 (10)	0.0147 (10)	0.0120 (9)
C2	0.0235 (10)	0.0206 (10)	0.0293 (10)	0.0083 (9)	0.0085 (8)	0.0094 (8)
C3	0.0248 (11)	0.0263 (11)	0.0346 (11)	0.0092 (9)	0.0158 (9)	0.0150 (9)
C4	0.0226 (11)	0.0240 (12)	0.0408 (12)	0.0013 (9)	0.0109 (9)	0.0102 (10)
C5	0.0253 (11)	0.0244 (11)	0.0304 (11)	0.0070 (9)	0.0083 (9)	0.0044 (9)
C6	0.0189 (10)	0.0243 (11)	0.0266 (10)	0.0092 (9)	0.0090 (8)	0.0118 (8)
C7	0.0192 (10)	0.0197 (10)	0.0302 (11)	0.0058 (8)	0.0067 (8)	0.0106 (8)
C8	0.0201 (10)	0.0218 (11)	0.0244 (10)	0.0072 (9)	0.0053 (8)	0.0054 (8)
C9	0.0217 (11)	0.0255 (11)	0.0244 (10)	0.0094 (9)	0.0056 (8)	0.0061 (8)
C10	0.0185 (10)	0.0215 (10)	0.0255 (10)	0.0070 (8)	0.0048 (8)	0.0061 (8)
C11	0.0183 (10)	0.0176 (10)	0.0221 (9)	0.0052 (8)	0.0050 (8)	0.0035 (8)
C12	0.0201 (10)	0.0204 (10)	0.0219 (9)	0.0077 (8)	0.0061 (8)	0.0051 (8)
C13	0.0231 (10)	0.0248 (11)	0.0245 (10)	0.0100 (9)	0.0038 (8)	0.0088 (8)
C14	0.0171 (10)	0.0234 (11)	0.0287 (10)	0.0088 (9)	0.0056 (8)	0.0063 (8)
C15	0.0181 (10)	0.0192 (10)	0.0238 (10)	0.0058 (8)	0.0061 (8)	0.0049 (8)
C16	0.0175 (10)	0.0170 (10)	0.0233 (10)	0.0048 (8)	0.0050 (8)	0.0034 (8)
C17	0.0201 (10)	0.0188 (10)	0.0222 (10)	0.0055 (8)	0.0036 (8)	0.0041 (8)
C18	0.0219 (10)	0.0266 (11)	0.0260 (10)	0.0106 (9)	0.0049 (8)	0.0109 (8)
C19	0.0168 (10)	0.0270 (11)	0.0291 (10)	0.0091 (9)	0.0041 (8)	0.0067 (9)
C20	0.0209 (10)	0.0219 (11)	0.0265 (10)	0.0058 (9)	0.0055 (8)	0.0085 (8)
C21	0.0183 (10)	0.0199 (10)	0.0258 (10)	0.0072 (8)	0.0040 (8)	0.0053 (8)
C22	0.0182 (10)	0.0254 (11)	0.0247 (10)	0.0079 (9)	0.0068 (8)	0.0096 (8)
C23	0.0249 (11)	0.0248 (11)	0.0307 (11)	0.0109 (9)	0.0094 (9)	0.0060 (9)
C24	0.0346 (12)	0.0190 (11)	0.0438 (13)	0.0094 (10)	0.0186 (10)	0.0116 (9)
C25	0.0302 (11)	0.0269 (12)	0.0375 (12)	0.0085 (10)	0.0189 (10)	0.0145 (9)
C26	0.0287 (11)	0.0220 (11)	0.0279 (10)	0.0078 (9)	0.0113 (9)	0.0081 (8)
C27	0.0261 (11)	0.0203 (11)	0.0300 (11)	0.0061 (9)	0.0086 (9)	0.0085 (9)
C28	0.0418 (13)	0.0257 (12)	0.0317 (11)	0.0144 (10)	0.0183 (10)	0.0118 (9)
C29	0.0319 (12)	0.0322 (13)	0.0435 (13)	0.0094 (11)	0.0072 (10)	0.0163 (10)
C30	0.0526 (17)	0.067 (2)	0.106 (2)	0.0151 (16)	0.0201 (17)	0.064 (2)
C31	0.0618 (19)	0.0530 (19)	0.106 (3)	0.0335 (17)	−0.0045 (18)	0.0232 (17)

Geometric parameters (Å, º)

Mg1—O1^i	2.0416 (15)	C8—C12	1.484 (3)
Mg1—O1	2.0417 (15)	C9—C10	1.483 (3)
Mg1—O9^i	2.0491 (14)	C10—C19	1.376 (3)
Mg1—O9	2.0491 (14)	C10—C11	1.411 (3)
Mg1—O7^ii	2.0656 (13)	C11—C12	1.411 (3)
Mg1—O7^iii	2.0656 (13)	C11—C16	1.418 (3)
O1—C1	1.233 (2)	C12—C13	1.379 (3)
O2—C1	1.283 (2)	C13—C14	1.403 (3)
O2—H2A	0.855 (10)	C13—H13	0.9500
O3—C9	1.215 (2)	C14—C15	1.379 (3)
O4—C8	1.208 (2)	C14—H14	0.9500
O5—C20	1.207 (2)	C15—C16	1.410 (3)
O6—C21	1.212 (2)	C15—C21	1.482 (3)
O7—C28	1.244 (2)	C16—C17	1.412 (3)
O7—Mg1^iv	2.0657 (13)	C17—C18	1.379 (3)
O8—C28	1.273 (3)	C17—C20	1.484 (3)
O9—C29	1.219 (3)	C18—C19	1.404 (3)
N1—C9	1.397 (2)	C18—H18	0.9500
N1—C8	1.406 (2)	C19—H19	0.9500
N1—C6	1.456 (2)	C22—C27	1.379 (3)
N2—C21	1.402 (2)	C22—C23	1.389 (3)
N2—C20	1.409 (2)	C23—C24	1.385 (3)
N2—C22	1.454 (2)	C23—H23	0.9500
N3—C29	1.322 (3)	C24—C25	1.385 (3)
N3—C31	1.445 (3)	C24—H24	0.9500
N3—C30	1.460 (3)	C25—C26	1.392 (3)
C1—C2	1.488 (3)	C25—H25	0.9500
C2—C3	1.391 (3)	C26—C27	1.395 (3)
C2—C7	1.392 (3)	C26—C28	1.504 (3)
C3—C4	1.378 (3)	C27—H27	0.9500
C3—H3	0.9500	C29—H29	0.9500
C4—C5	1.387 (3)	C30—H30A	0.9800
C4—H4	0.9500	C30—H30B	0.9800
C5—C6	1.386 (3)	C30—H30C	0.9800
C5—H5	0.9500	C31—H31A	0.9800
C6—C7	1.373 (3)	C31—H31B	0.9800
C7—H7	0.9500	C31—H31C	0.9800
O1^i—Mg1—O1	180.0	C12—C13—C14	120.41 (17)
O1^i—Mg1—O9^i	88.54 (6)	C12—C13—H13	119.8
O1—Mg1—O9^i	91.46 (6)	C14—C13—H13	119.8
O1^i—Mg1—O9	91.46 (6)	C15—C14—C13	120.51 (16)
O1—Mg1—O9	88.54 (6)	C15—C14—H14	119.7
O9^i—Mg1—O9	180.0	C13—C14—H14	119.7
O1^i—Mg1—O7^ii	87.35 (6)	C14—C15—C16	120.01 (17)
O1—Mg1—O7^ii	92.65 (6)	C14—C15—C21	119.79 (16)
O9^i—Mg1—O7^ii	88.16 (6)	C16—C15—C21	120.18 (16)
O9—Mg1—O7^ii	91.84 (6)	C15—C16—C17	121.25 (17)
O1^i—Mg1—O7^iii	92.65 (6)	C15—C16—C11	119.58 (16)
O1—Mg1—O7^iii	87.35 (6)	C17—C16—C11	119.17 (16)
O9^i—Mg1—O7^iii	91.84 (6)	C18—C17—C16	120.37 (17)
O9—Mg1—O7^iii	88.16 (6)	C18—C17—C20	119.93 (16)
O7^ii—Mg1—O7^iii	180.0	C16—C17—C20	119.70 (16)
C1—O1—Mg1	145.30 (14)	C17—C18—C19	120.41 (17)
C1—O2—H2A	118 (2)	C17—C18—H18	119.8
C28—O7—Mg1^iv	139.00 (14)	C19—C18—H18	119.8
C29—O9—Mg1	132.21 (14)	C10—C19—C18	120.22 (16)
C9—N1—C8	125.65 (15)	C10—C19—H19	119.9
C9—N1—C6	116.96 (14)	C18—C19—H19	119.9
C8—N1—C6	117.33 (14)	O5—C20—N2	120.80 (17)
C21—N2—C20	125.00 (15)	O5—C20—C17	122.31 (17)
C21—N2—C22	117.00 (14)	N2—C20—C17	116.89 (16)
C20—N2—C22	117.93 (15)	O6—C21—N2	120.93 (17)
C29—N3—C31	123.3 (2)	O6—C21—C15	122.49 (16)
C29—N3—C30	119.0 (2)	N2—C21—C15	116.58 (15)
C31—N3—C30	117.6 (2)	C27—C22—C23	121.17 (18)
O1—C1—O2	125.8 (2)	C27—C22—N2	119.57 (17)
O1—C1—C2	119.30 (18)	C23—C22—N2	119.26 (17)
O2—C1—C2	114.94 (18)	C24—C23—C22	119.07 (18)
C3—C2—C7	119.92 (18)	C24—C23—H23	120.5
C3—C2—C1	121.77 (18)	C22—C23—H23	120.5
C7—C2—C1	118.30 (17)	C23—C24—C25	120.44 (19)
C4—C3—C2	120.03 (18)	C23—C24—H24	119.8
C4—C3—H3	120.0	C25—C24—H24	119.8
C2—C3—H3	120.0	C24—C25—C26	120.18 (19)
C3—C4—C5	120.29 (19)	C24—C25—H25	119.9
C3—C4—H4	119.9	C26—C25—H25	119.9
C5—C4—H4	119.9	C25—C26—C27	119.51 (18)
C6—C5—C4	119.15 (19)	C25—C26—C28	120.11 (18)
C6—C5—H5	120.4	C27—C26—C28	120.36 (18)
C4—C5—H5	120.4	C22—C27—C26	119.57 (19)
C7—C6—C5	121.30 (18)	C22—C27—H27	120.2
C7—C6—N1	118.16 (17)	C26—C27—H27	120.2
C5—C6—N1	120.54 (17)	O7—C28—O8	125.51 (19)
C6—C7—C2	119.28 (18)	O7—C28—C26	118.36 (19)
C6—C7—H7	120.4	O8—C28—C26	116.10 (18)
C2—C7—H7	120.4	O9—C29—N3	124.2 (2)
O4—C8—N1	120.92 (16)	O9—C29—H29	117.9
O4—C8—C12	123.00 (16)	N3—C29—H29	117.9
N1—C8—C12	116.07 (16)	N3—C30—H30A	109.5
O3—C9—N1	120.55 (17)	N3—C30—H30B	109.5
O3—C9—C10	122.66 (17)	H30A—C30—H30B	109.5
N1—C9—C10	116.77 (15)	N3—C30—H30C	109.5
C19—C10—C11	120.61 (17)	H30A—C30—H30C	109.5
C19—C10—C9	119.83 (16)	H30B—C30—H30C	109.5
C11—C10—C9	119.51 (16)	N3—C31—H31A	109.5
C12—C11—C10	121.68 (17)	N3—C31—H31B	109.5
C12—C11—C16	119.15 (16)	H31A—C31—H31B	109.5
C10—C11—C16	119.17 (16)	N3—C31—H31C	109.5
C13—C12—C11	120.23 (17)	H31A—C31—H31C	109.5
C13—C12—C8	119.90 (16)	H31B—C31—H31C	109.5
C11—C12—C8	119.86 (16)
Mg1—O1—C1—O2	−14.5 (4)	C12—C11—C16—C15	3.3 (3)
Mg1—O1—C1—C2	165.48 (17)	C10—C11—C16—C15	−176.68 (17)
O1—C1—C2—C3	176.29 (18)	C12—C11—C16—C17	−177.63 (17)
O2—C1—C2—C3	−3.8 (3)	C10—C11—C16—C17	2.4 (3)
O1—C1—C2—C7	−2.7 (3)	C15—C16—C17—C18	177.76 (17)
O2—C1—C2—C7	177.24 (18)	C11—C16—C17—C18	−1.3 (3)
C7—C2—C3—C4	1.6 (3)	C15—C16—C17—C20	−2.3 (3)
C1—C2—C3—C4	−177.42 (19)	C11—C16—C17—C20	178.64 (17)
C2—C3—C4—C5	−0.7 (3)	C16—C17—C18—C19	−0.7 (3)
C3—C4—C5—C6	−0.6 (3)	C20—C17—C18—C19	179.34 (18)
C4—C5—C6—C7	1.1 (3)	C11—C10—C19—C18	−0.5 (3)
C4—C5—C6—N1	−179.29 (17)	C9—C10—C19—C18	−178.01 (18)
C9—N1—C6—C7	98.4 (2)	C17—C18—C19—C10	1.7 (3)
C8—N1—C6—C7	−79.0 (2)	C21—N2—C20—O5	179.47 (18)
C9—N1—C6—C5	−81.1 (2)	C22—N2—C20—O5	−3.7 (3)
C8—N1—C6—C5	101.4 (2)	C21—N2—C20—C17	−0.6 (3)
C5—C6—C7—C2	−0.3 (3)	C22—N2—C20—C17	176.13 (16)
N1—C6—C7—C2	−179.90 (15)	C18—C17—C20—O5	4.2 (3)
C3—C2—C7—C6	−1.0 (3)	C16—C17—C20—O5	−175.72 (18)
C1—C2—C7—C6	177.99 (17)	C18—C17—C20—N2	−175.69 (17)
C9—N1—C8—O4	173.12 (18)	C16—C17—C20—N2	4.4 (3)
C6—N1—C8—O4	−9.7 (3)	C20—N2—C21—O6	175.29 (17)
C9—N1—C8—C12	−7.8 (3)	C22—N2—C21—O6	−1.5 (3)
C6—N1—C8—C12	169.41 (16)	C20—N2—C21—C15	−4.9 (3)
C8—N1—C9—O3	−177.42 (18)	C22—N2—C21—C15	178.33 (16)
C6—N1—C9—O3	5.4 (3)	C14—C15—C21—O6	4.9 (3)
C8—N1—C9—C10	4.0 (3)	C16—C15—C21—O6	−173.25 (18)
C6—N1—C9—C10	−173.18 (16)	C14—C15—C21—N2	−174.98 (17)
O3—C9—C10—C19	1.1 (3)	C16—C15—C21—N2	6.9 (3)
N1—C9—C10—C19	179.66 (17)	C21—N2—C22—C27	−63.7 (2)
O3—C9—C10—C11	−176.37 (18)	C20—N2—C22—C27	119.25 (19)
N1—C9—C10—C11	2.2 (3)	C21—N2—C22—C23	116.12 (19)
C19—C10—C11—C12	178.51 (18)	C20—N2—C22—C23	−60.9 (2)
C9—C10—C11—C12	−4.0 (3)	C27—C22—C23—C24	2.2 (3)
C19—C10—C11—C16	−1.5 (3)	N2—C22—C23—C24	−177.67 (17)
C9—C10—C11—C16	176.00 (18)	C22—C23—C24—C25	−0.2 (3)
C10—C11—C12—C13	178.79 (17)	C23—C24—C25—C26	−1.7 (3)
C16—C11—C12—C13	−1.2 (3)	C24—C25—C26—C27	1.6 (3)
C10—C11—C12—C8	0.0 (3)	C24—C25—C26—C28	−176.68 (19)
C16—C11—C12—C8	−179.96 (17)	C23—C22—C27—C26	−2.2 (3)
O4—C8—C12—C13	5.9 (3)	N2—C22—C27—C26	177.60 (16)
N1—C8—C12—C13	−173.19 (17)	C25—C26—C27—C22	0.3 (3)
O4—C8—C12—C11	−175.37 (18)	C28—C26—C27—C22	178.60 (18)
N1—C8—C12—C11	5.6 (3)	Mg1^iv—O7—C28—O8	21.2 (4)
C11—C12—C13—C14	−1.7 (3)	Mg1^iv—O7—C28—C26	−160.65 (15)
C8—C12—C13—C14	177.03 (18)	C25—C26—C28—O7	−6.0 (3)
C12—C13—C14—C15	2.6 (3)	C27—C26—C28—O7	175.76 (19)
C13—C14—C15—C16	−0.4 (3)	C25—C26—C28—O8	172.3 (2)
C13—C14—C15—C21	−178.53 (18)	C27—C26—C28—O8	−5.9 (3)
C14—C15—C16—C17	178.45 (17)	Mg1—O9—C29—N3	168.06 (18)
C21—C15—C16—C17	−3.4 (3)	C31—N3—C29—O9	−174.5 (2)
C14—C15—C16—C11	−2.5 (3)	C30—N3—C29—O9	0.3 (4)
C21—C15—C16—C11	175.58 (17)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O8^ii	0.86 (1)	1.60 (1)	2.447 (2)	171 (3)

Symmetry code: (ii) x+1, y, z−1.