Crystal structure, shape analysis and bioactivity of new Li^I, Na^I and Mg^II complexes with 1,10-phen­an­throline and 2-(3,4-di­chloro­phen­yl)acetic acid

Reactions of 1,10-phenanthroline (phen) and 2-(3,4-di­chloro­phen­yl)acetic acid (dcaH) with M_n(CO₃) (M = Li^I, Na^I and Mg^II; n = 1 and 2) in MeOH yield the mononuclear lithium complex aqua­[2-(3,4-di­chloro­phen­yl)acetato-κO](1,10-phenanthroline-κ²N,N′)lithium(I), [Li(C₈H₅Cl₂O₂)(C₁₂H₈N₂)(H₂O)] or [Li(dca)(phen)(H₂O)] (1), the dinuclear sodium complex di-μ-aqua-bis­{[2-(3,4-di­chloro­phen­yl)acetato-κO](1,10-phenanthroline-κ²N,N′)sodium(I)}, [Na₂(C₈H₅Cl₂O₂)₂(C₁₂H₈N₂)₂(H₂O)₂] or [Na₂(dca)₂(phen)₂(H₂O)₂] (2), and the one-dimensional chain magnesium complex catena-poly[[[di­aqua­(1,10-phenanthroline-κ²N,N′)magnesium]-μ-2-(3,4-di­chloro­phen­yl)acetato-κ²O:O′] 2-(3,4-di­chloro­phen­yl)acetate monohydrate], {[Mg(C₈H₅Cl₂O₂)(C₁₂H₈N₂)(H₂O)₂](C₈H₅Cl₂O₂)·H₂O}_n or {[Mg(dca)(phen)(H₂O)₂](dca)·H₂O}_n (3). In these complexes, phen binds via an N,N′-chelate pocket, while the deprotonated dca⁻ ligands coordinate either in a monodentate (in 1 and 2) or bidentate (in 3) fashion. The remaining coordination sites around the metal ions are occupied by water mol­ecules in all three complexes. Complex 1 crystallizes in the triclinic space group P with one mol­ecule in the asymmetric unit. The Li⁺ ion adopts a four-coordinated distorted seesaw geometry comprising an [N₂O₂] donor set. Complex 2 crystallizes in the triclinic space group P with half a mol­ecule in the asymmetric unit, in which the Na⁺ ion adopts a five-coordinated distorted spherical square-pyramidal geometry, with an [N₂O₃] donor set. Complex 3 crystallizes in the ortho­rhom­bic space group P2₁2₁2₁, with one Mg²⁺ ion, one phen ligand, two dca⁻ ligands and three water mol­ecules in the asymmetric unit. Both dcaH ligands are deprotonated, however, one dca⁻ anion is not coordinated, whereas the second dca⁻ anion coordinates in a bidentate fashion bridging two Mg²⁺ ions, resulting in a one-dimensional chain structure for 3. The Mg²⁺ ion adopts a distorted octa­hedral geometry, with an [N₂O₄] donor set. Complexes 1–3 were evaluated against urease and α-glucosidase enzymes for their inhibition potential and were found to be inactive.

Computing details

For all structures, data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Aqua[2-(3,4-dichlorophenyl)acetato-κO](1,10-phenanthroline-κ²N,N')lithium(I) (AN_Li_b_0m_a)

Crystal data

[Li(C8H5Cl2O2)(C12H8N2)(H2O)]	Z = 2
Mr = 409.18	F(000) = 420
Triclinic, P1	Dx = 1.443 Mg m^−3
a = 7.056 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.226 (5) Å	Cell parameters from 8992 reflections
c = 13.451 (5) Å	θ = 3.0–26.4°
α = 87.21 (2)°	µ = 0.37 mm^−1
β = 86.978 (13)°	T = 296 K
γ = 76.42 (2)°	Prism, colorless
V = 941.5 (7) Å^3	0.32 × 0.10 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer	3197 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.033
Absorption correction: multi-scan (SADABS; Bruker, 2010)	θmax = 26.4°, θmin = 3.0°
Tmin = 0.591, Tmax = 0.745	h = −8→8
29466 measured reflections	k = −12→12
3827 independent reflections	l = −16→16

Refinement

Refinement on F^2	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.128	w = 1/[σ^2(Fo^2) + (0.0637P)^2 + 0.5649P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3827 reflections	Δρmax = 0.44 e Å^−3
259 parameters	Δρmin = −0.44 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
Cl1	0.42417 (11)	0.83941 (6)	−0.04450 (4)	0.0642 (2)
Cl2	−0.00534 (10)	0.80394 (8)	0.00756 (5)	0.0734 (2)
O1	0.9135 (2)	0.43625 (15)	0.31886 (11)	0.0480 (4)
O2	0.5988 (2)	0.51587 (16)	0.35839 (10)	0.0492 (4)
O3	1.2490 (3)	0.47075 (17)	0.45196 (12)	0.0525 (4)
H3A	1.277 (4)	0.475 (3)	0.5101 (9)	0.063*
H3B	1.336 (3)	0.493 (3)	0.4178 (18)	0.063*
N1	1.1877 (2)	0.16122 (16)	0.34819 (12)	0.0385 (4)
N2	1.1291 (2)	0.20964 (15)	0.54463 (12)	0.0341 (3)
C1	1.2085 (4)	0.1363 (2)	0.25181 (16)	0.0513 (5)
H1	1.176828	0.208714	0.206344	0.062*
C2	1.2751 (4)	0.0077 (3)	0.21479 (18)	0.0564 (6)
H2	1.285669	−0.004676	0.146514	0.068*
C3	1.3247 (3)	−0.0996 (2)	0.28053 (18)	0.0507 (6)
H3	1.371415	−0.185925	0.257230	0.061*
C4	1.3048 (3)	−0.07914 (19)	0.38359 (16)	0.0373 (4)
C5	1.3533 (3)	−0.18614 (19)	0.45715 (19)	0.0458 (5)
H5	1.401208	−0.273927	0.437027	0.055*
C6	1.3308 (3)	−0.1617 (2)	0.55499 (18)	0.0453 (5)
H6	1.365118	−0.232790	0.601357	0.054*
C7	1.2549 (3)	−0.02819 (19)	0.58897 (15)	0.0351 (4)
C8	1.2275 (3)	0.0026 (2)	0.69018 (16)	0.0481 (5)
H8	1.259113	−0.065244	0.739262	0.058*
C9	1.1543 (3)	0.1327 (3)	0.71580 (16)	0.0518 (5)
H9	1.136576	0.154414	0.782526	0.062*
C10	1.1061 (3)	0.2335 (2)	0.64093 (16)	0.0442 (5)
H10	1.055349	0.321598	0.659800	0.053*
C11	1.2042 (2)	0.08038 (17)	0.51855 (13)	0.0285 (4)
C12	1.2321 (2)	0.05443 (17)	0.41369 (14)	0.0300 (4)
C13	0.7370 (3)	0.46480 (17)	0.29992 (13)	0.0340 (4)
C14	0.6895 (3)	0.4312 (2)	0.19580 (15)	0.0472 (5)
H14A	0.802539	0.430821	0.151473	0.057*
H14B	0.668305	0.340659	0.198980	0.057*
C15	0.5147 (3)	0.52449 (19)	0.15057 (13)	0.0360 (4)
C16	0.3249 (3)	0.5126 (2)	0.17414 (15)	0.0442 (5)
H16	0.304035	0.445914	0.220043	0.053*
C17	0.1666 (3)	0.5981 (2)	0.13063 (16)	0.0479 (5)
H17	0.040880	0.588283	0.147095	0.058*
C18	0.1957 (3)	0.6986 (2)	0.06227 (14)	0.0414 (5)
C19	0.3828 (3)	0.71335 (19)	0.03927 (13)	0.0369 (4)
C20	0.5416 (3)	0.6266 (2)	0.08266 (14)	0.0382 (4)
H20	0.667061	0.636774	0.066162	0.046*
Li1	1.0846 (5)	0.3505 (3)	0.4211 (3)	0.0436 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0972 (5)	0.0556 (4)	0.0443 (3)	−0.0300 (3)	−0.0044 (3)	0.0129 (3)
Cl2	0.0581 (4)	0.0924 (5)	0.0540 (4)	0.0152 (3)	−0.0162 (3)	0.0057 (3)
O1	0.0454 (8)	0.0467 (8)	0.0490 (9)	−0.0027 (6)	−0.0169 (7)	0.0015 (7)
O2	0.0505 (9)	0.0629 (10)	0.0339 (7)	−0.0104 (7)	−0.0034 (6)	−0.0113 (7)
O3	0.0636 (10)	0.0559 (9)	0.0484 (9)	−0.0328 (8)	−0.0240 (8)	0.0125 (7)
N1	0.0474 (9)	0.0325 (8)	0.0382 (9)	−0.0138 (7)	−0.0065 (7)	0.0022 (6)
N2	0.0355 (8)	0.0285 (8)	0.0389 (8)	−0.0086 (6)	−0.0027 (6)	−0.0013 (6)
C1	0.0676 (15)	0.0554 (13)	0.0367 (11)	−0.0260 (11)	−0.0044 (10)	0.0019 (9)
C2	0.0663 (15)	0.0681 (16)	0.0413 (12)	−0.0280 (12)	0.0056 (10)	−0.0142 (11)
C3	0.0467 (12)	0.0476 (12)	0.0610 (14)	−0.0155 (10)	0.0082 (10)	−0.0238 (11)
C4	0.0298 (9)	0.0307 (9)	0.0535 (12)	−0.0102 (7)	−0.0012 (8)	−0.0081 (8)
C5	0.0384 (10)	0.0237 (9)	0.0747 (15)	−0.0046 (8)	−0.0055 (10)	−0.0036 (9)
C6	0.0416 (11)	0.0282 (9)	0.0654 (14)	−0.0075 (8)	−0.0118 (10)	0.0131 (9)
C7	0.0286 (9)	0.0341 (9)	0.0438 (10)	−0.0106 (7)	−0.0069 (7)	0.0094 (8)
C8	0.0490 (12)	0.0528 (13)	0.0426 (11)	−0.0143 (10)	−0.0085 (9)	0.0157 (9)
C9	0.0559 (13)	0.0654 (15)	0.0355 (11)	−0.0173 (11)	−0.0002 (9)	−0.0009 (10)
C10	0.0454 (11)	0.0424 (11)	0.0446 (11)	−0.0095 (9)	0.0007 (9)	−0.0068 (9)
C11	0.0235 (8)	0.0259 (8)	0.0379 (9)	−0.0094 (6)	−0.0038 (7)	0.0023 (7)
C12	0.0261 (8)	0.0266 (8)	0.0393 (9)	−0.0097 (6)	−0.0035 (7)	−0.0009 (7)
C13	0.0451 (10)	0.0247 (8)	0.0326 (9)	−0.0077 (7)	−0.0101 (8)	0.0017 (7)
C14	0.0562 (13)	0.0442 (11)	0.0361 (10)	0.0024 (9)	−0.0129 (9)	−0.0098 (9)
C15	0.0448 (10)	0.0375 (10)	0.0259 (8)	−0.0075 (8)	−0.0078 (7)	−0.0074 (7)
C16	0.0550 (12)	0.0471 (11)	0.0344 (10)	−0.0203 (10)	−0.0028 (9)	0.0041 (8)
C17	0.0419 (11)	0.0651 (14)	0.0390 (11)	−0.0174 (10)	−0.0016 (9)	0.0004 (10)
C18	0.0421 (11)	0.0494 (11)	0.0293 (9)	−0.0020 (9)	−0.0079 (8)	−0.0037 (8)
C19	0.0512 (11)	0.0382 (10)	0.0225 (8)	−0.0120 (8)	−0.0036 (7)	−0.0020 (7)
C20	0.0420 (10)	0.0462 (11)	0.0299 (9)	−0.0156 (8)	−0.0037 (8)	−0.0068 (8)
Li1	0.053 (2)	0.0339 (17)	0.0472 (19)	−0.0144 (14)	−0.0205 (15)	0.0085 (14)

Geometric parameters (Å, º)

Li1—O1	1.918 (4)	C6—C7	1.432 (3)
Li1—O3	1.950 (4)	C6—H6	0.9300
Li1—N1	2.164 (4)	C7—C8	1.405 (3)
Li1—N2	2.132 (4)	C7—C11	1.416 (2)
N1—C1	1.327 (3)	C8—C9	1.364 (3)
N1—C12	1.357 (2)	C8—H8	0.9300
N2—C10	1.324 (3)	C9—C10	1.401 (3)
N2—C11	1.359 (2)	C9—H9	0.9300
Cl1—C19	1.737 (2)	C10—H10	0.9300
Cl2—C18	1.741 (2)	C11—C12	1.443 (3)
O1—C13	1.248 (2)	C13—C14	1.531 (3)
O2—C13	1.250 (2)	C14—C15	1.507 (3)
O3—H3A	0.822 (10)	C14—H14A	0.9700
O3—H3B	0.815 (10)	C14—H14B	0.9700
C1—C2	1.395 (3)	C15—C16	1.392 (3)
C1—H1	0.9300	C15—C20	1.394 (3)
C2—C3	1.367 (4)	C16—C17	1.384 (3)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.407 (3)	C17—C18	1.390 (3)
C3—H3	0.9300	C17—H17	0.9300
C4—C12	1.413 (3)	C18—C19	1.381 (3)
C4—C5	1.431 (3)	C19—C20	1.391 (3)
C5—C6	1.346 (3)	C20—H20	0.9300
C5—H5	0.9300
C13—O1—Li1	140.53 (18)	N2—C11—C7	123.19 (17)
C1—N1—Li1	129.77 (17)	N2—C11—C12	117.59 (15)
C12—N1—Li1	112.75 (15)	C7—C11—C12	119.23 (16)
C10—N2—Li1	128.55 (17)	N1—C12—C4	122.99 (18)
C11—N2—Li1	113.78 (16)	N1—C12—C11	117.75 (16)
C1—N1—C12	117.47 (18)	C4—C12—C11	119.26 (16)
Li1—O3—H3A	119 (2)	O1—C13—O2	125.84 (18)
Li1—O3—H3B	129 (2)	O1—C13—C14	115.85 (18)
H3A—O3—H3B	106 (3)	O2—C13—C14	118.30 (18)
C10—N2—C11	117.48 (17)	C15—C14—C13	115.93 (16)
N1—C1—C2	123.8 (2)	C15—C14—H14A	108.3
N1—C1—H1	118.1	C13—C14—H14A	108.3
C2—C1—H1	118.1	C15—C14—H14B	108.3
C3—C2—C1	118.9 (2)	C13—C14—H14B	108.3
C3—C2—H2	120.6	H14A—C14—H14B	107.4
C1—C2—H2	120.6	C16—C15—C20	118.15 (18)
C2—C3—C4	119.7 (2)	C16—C15—C14	122.23 (19)
C2—C3—H3	120.1	C20—C15—C14	119.62 (19)
C4—C3—H3	120.1	C17—C16—C15	121.32 (19)
C3—C4—C12	117.09 (19)	C17—C16—H16	119.3
C3—C4—C5	123.16 (19)	C15—C16—H16	119.3
C12—C4—C5	119.75 (18)	C16—C17—C18	119.9 (2)
C6—C5—C4	121.04 (18)	C16—C17—H17	120.0
C6—C5—H5	119.5	C18—C17—H17	120.0
C4—C5—H5	119.5	C19—C18—C17	119.57 (19)
C5—C6—C7	121.15 (18)	C19—C18—Cl2	121.32 (17)
C5—C6—H6	119.4	C17—C18—Cl2	119.12 (17)
C7—C6—H6	119.4	C18—C19—C20	120.31 (18)
C8—C7—C11	117.05 (18)	C18—C19—Cl1	120.77 (16)
C8—C7—C6	123.39 (18)	C20—C19—Cl1	118.92 (16)
C11—C7—C6	119.55 (18)	C19—C20—C15	120.74 (18)
C9—C8—C7	119.44 (19)	C19—C20—H20	119.6
C9—C8—H8	120.3	C15—C20—H20	119.6
C7—C8—H8	120.3	O1—Li1—O3	108.37 (17)
C8—C9—C10	119.6 (2)	O1—Li1—N2	146.7 (2)
C8—C9—H9	120.2	O3—Li1—N2	101.65 (16)
C10—C9—H9	120.2	O1—Li1—N1	95.98 (16)
N2—C10—C9	123.3 (2)	O3—Li1—N1	124.7 (2)
N2—C10—H10	118.4	N2—Li1—N1	78.02 (13)
C9—C10—H10	118.4

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2^i	0.82 (2)	2.03 (2)	2.841 (3)	168 (3)
O3—H3B···O2^ii	0.82 (2)	2.04 (2)	2.835 (3)	165 (3)

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

Di-µ-aqua-bis{[2-(3,4-dichlorophenyl)acetato-κO](1,10-phenanthroline-κ²N,N')sodium(I)} (An_Na_b_0m_a)

Crystal data

[Na2(C8H5Cl2O2)2(C12H8N2)2(H2O)2]	Z = 1
Mr = 850.46	F(000) = 436
Triclinic, P1	Dx = 1.476 Mg m^−3
a = 6.9518 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.8369 (16) Å	Cell parameters from 9990 reflections
c = 13.5077 (17) Å	θ = 3.1–26.4°
α = 82.823 (6)°	µ = 0.39 mm^−1
β = 83.700 (6)°	T = 296 K
γ = 71.920 (7)°	Plate, colorless
V = 957.1 (2) Å^3	0.45 × 0.40 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer	3119 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.038
Absorption correction: multi-scan (SADABS; Bruker, 2010)	θmax = 26.5°, θmin = 3.1°
Tmin = 0.669, Tmax = 0.745	h = −8→8
29417 measured reflections	k = −13→13
3931 independent reflections	l = −16→16

Refinement

Refinement on F^2	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.123	w = 1/[σ^2(Fo^2) + (0.0576P)^2 + 0.6986P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
3931 reflections	Δρmax = 0.29 e Å^−3
259 parameters	Δρmin = −0.44 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
Cl1	0.73690 (12)	0.33088 (8)	1.02936 (5)	0.0677 (2)
Cl2	1.19017 (13)	0.32639 (8)	0.96614 (5)	0.0672 (2)
Na1	0.44884 (12)	0.14776 (7)	0.55547 (6)	0.0361 (2)
O1	0.6010 (2)	0.05309 (16)	0.70211 (11)	0.0449 (4)
O2	0.9153 (2)	−0.03743 (15)	0.64207 (11)	0.0413 (4)
O3	0.2655 (2)	0.00151 (14)	0.53343 (11)	0.0346 (3)
H3A	0.207 (3)	0.018 (2)	0.4819 (12)	0.041*
H3B	0.179 (3)	−0.008 (2)	0.5767 (14)	0.041*
N1	0.3257 (3)	0.37406 (16)	0.59860 (12)	0.0330 (4)
N2	0.3647 (2)	0.30471 (16)	0.40809 (12)	0.0317 (4)
C1	0.3072 (4)	0.4094 (3)	0.69022 (18)	0.0484 (6)
H1	0.347749	0.344601	0.742320	0.058*
C2	0.2299 (4)	0.5391 (3)	0.7131 (2)	0.0601 (8)
H2	0.217555	0.559060	0.778982	0.072*
C3	0.1737 (4)	0.6346 (3)	0.6383 (2)	0.0558 (7)
H3	0.122959	0.721198	0.652161	0.067*
C4	0.1920 (3)	0.60284 (19)	0.53966 (19)	0.0410 (5)
C5	0.1372 (4)	0.6986 (2)	0.4573 (3)	0.0569 (7)
H5	0.087498	0.786278	0.468486	0.068*
C6	0.1561 (4)	0.6648 (2)	0.3641 (3)	0.0592 (8)
H6	0.118970	0.729497	0.311598	0.071*
C7	0.2322 (3)	0.5311 (2)	0.34337 (18)	0.0436 (5)
C8	0.2562 (4)	0.4910 (3)	0.2468 (2)	0.0609 (7)
H8	0.219631	0.552553	0.192310	0.073*
C9	0.3325 (4)	0.3629 (3)	0.23263 (19)	0.0596 (7)
H9	0.349448	0.335885	0.168699	0.071*
C10	0.3850 (3)	0.2726 (2)	0.31511 (17)	0.0440 (5)
H10	0.437204	0.184806	0.304577	0.053*
C11	0.2892 (3)	0.43332 (18)	0.42262 (15)	0.0288 (4)
C12	0.2692 (3)	0.46939 (18)	0.52317 (15)	0.0292 (4)
C13	0.7807 (3)	−0.00943 (18)	0.71201 (14)	0.0295 (4)
C14	0.8441 (4)	−0.0577 (2)	0.81847 (15)	0.0398 (5)
H14A	0.727192	−0.065924	0.861954	0.048*
H14B	0.944496	−0.142986	0.818607	0.048*
C15	0.9319 (3)	0.03660 (19)	0.85735 (13)	0.0325 (4)
C16	0.8132 (3)	0.1291 (2)	0.91919 (14)	0.0353 (4)
H16	0.679484	0.131581	0.938336	0.042*
C17	0.8921 (3)	0.2177 (2)	0.95257 (14)	0.0376 (5)
C18	1.0895 (3)	0.2160 (2)	0.92540 (15)	0.0391 (5)
C19	1.2095 (3)	0.1249 (2)	0.86338 (16)	0.0429 (5)
H19	1.342765	0.123290	0.843997	0.051*
C20	1.1304 (3)	0.0360 (2)	0.83028 (15)	0.0399 (5)
H20	1.212240	−0.025365	0.789021	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0699 (5)	0.0735 (5)	0.0584 (4)	−0.0125 (4)	0.0097 (3)	−0.0377 (3)
Cl2	0.0903 (5)	0.0815 (5)	0.0521 (4)	−0.0536 (4)	−0.0108 (3)	−0.0127 (3)
Na1	0.0412 (5)	0.0245 (4)	0.0401 (4)	−0.0048 (3)	−0.0071 (3)	−0.0033 (3)
O1	0.0378 (9)	0.0514 (9)	0.0371 (8)	−0.0009 (7)	−0.0036 (6)	−0.0041 (7)
O2	0.0356 (8)	0.0535 (9)	0.0332 (8)	−0.0106 (7)	0.0011 (6)	−0.0084 (7)
O3	0.0301 (8)	0.0395 (8)	0.0339 (8)	−0.0093 (6)	−0.0027 (6)	−0.0054 (6)
N1	0.0339 (9)	0.0318 (9)	0.0351 (9)	−0.0114 (7)	−0.0005 (7)	−0.0076 (7)
N2	0.0304 (8)	0.0299 (8)	0.0365 (9)	−0.0103 (7)	−0.0012 (7)	−0.0074 (7)
C1	0.0522 (14)	0.0579 (15)	0.0414 (12)	−0.0238 (12)	0.0024 (10)	−0.0151 (11)
C2	0.0543 (15)	0.0766 (19)	0.0635 (17)	−0.0329 (14)	0.0169 (13)	−0.0446 (16)
C3	0.0355 (12)	0.0472 (14)	0.092 (2)	−0.0170 (11)	0.0159 (12)	−0.0423 (15)
C4	0.0203 (9)	0.0266 (10)	0.0772 (16)	−0.0069 (8)	0.0041 (9)	−0.0161 (10)
C5	0.0339 (12)	0.0219 (10)	0.109 (2)	−0.0024 (9)	−0.0054 (13)	−0.0005 (12)
C6	0.0442 (14)	0.0334 (12)	0.092 (2)	−0.0087 (11)	−0.0157 (14)	0.0242 (13)
C7	0.0305 (11)	0.0420 (12)	0.0558 (14)	−0.0132 (9)	−0.0092 (9)	0.0158 (10)
C8	0.0566 (16)	0.082 (2)	0.0448 (14)	−0.0292 (15)	−0.0163 (12)	0.0230 (13)
C9	0.0576 (16)	0.098 (2)	0.0334 (12)	−0.0392 (16)	−0.0029 (11)	−0.0061 (13)
C10	0.0432 (12)	0.0537 (14)	0.0421 (12)	−0.0219 (11)	0.0023 (10)	−0.0163 (10)
C11	0.0200 (9)	0.0265 (9)	0.0396 (10)	−0.0082 (7)	−0.0030 (7)	0.0014 (8)
C12	0.0181 (8)	0.0236 (9)	0.0464 (11)	−0.0071 (7)	0.0022 (8)	−0.0069 (8)
C13	0.0377 (11)	0.0259 (9)	0.0272 (9)	−0.0122 (8)	−0.0037 (8)	−0.0035 (7)
C14	0.0557 (13)	0.0357 (11)	0.0293 (10)	−0.0160 (10)	−0.0103 (9)	0.0040 (8)
C15	0.0410 (11)	0.0344 (10)	0.0210 (9)	−0.0096 (9)	−0.0087 (8)	0.0029 (7)
C16	0.0339 (10)	0.0447 (12)	0.0263 (9)	−0.0100 (9)	−0.0041 (8)	−0.0023 (8)
C17	0.0436 (12)	0.0423 (11)	0.0236 (9)	−0.0068 (9)	−0.0029 (8)	−0.0064 (8)
C18	0.0484 (13)	0.0468 (12)	0.0277 (10)	−0.0211 (10)	−0.0100 (9)	−0.0011 (9)
C19	0.0357 (11)	0.0573 (14)	0.0350 (11)	−0.0143 (10)	−0.0030 (9)	−0.0012 (10)
C20	0.0398 (12)	0.0420 (12)	0.0325 (11)	−0.0040 (9)	−0.0016 (9)	−0.0059 (9)

Geometric parameters (Å, º)

Na1—O1	2.3180 (17)	C5—H5	0.9300
Na1—O3	2.3834 (17)	C6—C7	1.432 (4)
Na1—O3^i	2.4436 (16)	C6—H6	0.9300
Na1—N2	2.4475 (19)	C7—C8	1.403 (4)
Na1—N1	2.4558 (18)	C7—C11	1.406 (3)
Na1—Na1^i	3.5438 (16)	C8—C9	1.353 (4)
Cl1—C17	1.730 (2)	C8—H8	0.9300
Cl2—C18	1.730 (2)	C9—C10	1.389 (4)
O1—C13	1.235 (2)	C9—H9	0.9300
O2—C13	1.250 (2)	C10—H10	0.9300
O3—H3A	0.816 (10)	C11—C12	1.440 (3)
O3—H3B	0.813 (10)	C13—C14	1.531 (3)
N1—C1	1.322 (3)	C14—C15	1.511 (3)
N1—C12	1.354 (3)	C14—H14A	0.9700
N2—C10	1.326 (3)	C14—H14B	0.9700
N2—C11	1.359 (2)	C15—C20	1.387 (3)
C1—C2	1.401 (4)	C15—C16	1.389 (3)
C1—H1	0.9300	C16—C17	1.384 (3)
C2—C3	1.349 (4)	C16—H16	0.9300
C2—H2	0.9300	C17—C18	1.376 (3)
C3—C4	1.400 (4)	C18—C19	1.384 (3)
C3—H3	0.9300	C19—C20	1.386 (3)
C4—C12	1.415 (3)	C19—H19	0.9300
C4—C5	1.421 (4)	C20—H20	0.9300
C5—C6	1.336 (4)
O1—Na1—O3	101.40 (6)	C8—C7—C11	117.1 (2)
O1—Na1—O3^i	87.33 (6)	C8—C7—C6	123.5 (2)
O3—Na1—O3^i	85.54 (6)	C11—C7—C6	119.3 (2)
O1—Na1—N2	157.58 (7)	C9—C8—C7	120.2 (2)
O3—Na1—N2	101.02 (6)	C9—C8—H8	119.9
O3^i—Na1—N2	93.74 (6)	C7—C8—H8	119.9
O1—Na1—N1	97.83 (6)	C8—C9—C10	118.9 (2)
O3—Na1—N1	130.20 (6)	C8—C9—H9	120.5
O3^i—Na1—N1	141.12 (6)	C10—C9—H9	120.5
N2—Na1—N1	67.72 (6)	N2—C10—C9	123.5 (2)
O1—Na1—Na1^i	95.78 (5)	N2—C10—H10	118.2
O3—Na1—Na1^i	43.43 (4)	C9—C10—H10	118.2
O3^i—Na1—Na1^i	42.11 (4)	N2—C11—C7	122.4 (2)
N2—Na1—Na1^i	99.99 (5)	N2—C11—C12	118.20 (17)
N1—Na1—Na1^i	166.14 (6)	C7—C11—C12	119.39 (18)
C13—O1—Na1	128.00 (13)	N1—C12—C4	122.3 (2)
Na1—O3—Na1^i	94.46 (6)	N1—C12—C11	118.66 (16)
Na1—O3—H3A	114.5 (17)	C4—C12—C11	118.99 (19)
Na1^i—O3—H3A	87.9 (17)	O1—C13—O2	125.36 (18)
Na1—O3—H3B	118.6 (18)	O1—C13—C14	117.57 (18)
Na1^i—O3—H3B	134.0 (18)	O2—C13—C14	117.07 (18)
H3A—O3—H3B	104 (2)	C15—C14—C13	110.28 (16)
C1—N1—C12	117.66 (19)	C15—C14—H14A	109.6
C1—N1—Na1	124.80 (16)	C13—C14—H14A	109.6
C12—N1—Na1	117.52 (12)	C15—C14—H14B	109.6
C10—N2—C11	117.77 (19)	C13—C14—H14B	109.6
C10—N2—Na1	124.38 (15)	H14A—C14—H14B	108.1
C11—N2—Na1	117.84 (13)	C20—C15—C16	118.07 (19)
N1—C1—C2	123.6 (3)	C20—C15—C14	121.28 (19)
N1—C1—H1	118.2	C16—C15—C14	120.62 (19)
C2—C1—H1	118.2	C17—C16—C15	120.6 (2)
C3—C2—C1	119.0 (2)	C17—C16—H16	119.7
C3—C2—H2	120.5	C15—C16—H16	119.7
C1—C2—H2	120.5	C18—C17—C16	120.83 (19)
C2—C3—C4	119.8 (2)	C18—C17—Cl1	120.65 (17)
C2—C3—H3	120.1	C16—C17—Cl1	118.52 (17)
C4—C3—H3	120.1	C17—C18—C19	119.3 (2)
C3—C4—C12	117.6 (2)	C17—C18—Cl2	121.41 (17)
C3—C4—C5	122.6 (2)	C19—C18—Cl2	119.25 (18)
C12—C4—C5	119.8 (2)	C18—C19—C20	119.7 (2)
C6—C5—C4	121.1 (2)	C18—C19—H19	120.1
C6—C5—H5	119.5	C20—C19—H19	120.1
C4—C5—H5	119.5	C19—C20—C15	121.4 (2)
C5—C6—C7	121.4 (2)	C19—C20—H20	119.3
C5—C6—H6	119.3	C15—C20—H20	119.3
C7—C6—H6	119.3

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2^i	0.82 (2)	1.92 (2)	2.733 (2)	174 (2)
O3—H3B···O2^ii	0.81 (2)	2.04 (2)	2.821 (2)	160 (2)

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

catena-Poly[[[diaqua(1,10-phenanthroline-κ²N,N')magnesium]-µ-2-(3,4-dichlorophenyl)acetato-κ²O:O'] 2-(3,4-dichlorophenyl)acetate monohydrate] (ANMGB_0m_a)

Crystal data

[Mg(C8H5Cl2O2)(C12H8N2)(H2O)2](C8H5Cl2O2)·H2O	Dx = 1.515 Mg m^−3
Mr = 666.60	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 9986 reflections
a = 8.3889 (4) Å	θ = 3.0–26.4°
b = 11.9459 (6) Å	µ = 0.48 mm^−1
c = 29.1630 (15) Å	T = 296 K
V = 2922.5 (3) Å^3	Plate, colorless
Z = 4	0.45 × 0.21 × 0.10 mm
F(000) = 1368

Data collection

Bruker APEXII CCD diffractometer	5186 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.042
Absorption correction: multi-scan (SADABS; Bruker, 2010)	θmax = 26.4°, θmin = 3.0°
Tmin = 0.516, Tmax = 0.745	h = −10→10
29717 measured reflections	k = −14→12
5875 independent reflections	l = −36→35

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.043	w = 1/[σ^2(Fo^2) + (0.032P)^2 + 1.6964P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.095	(Δ/σ)max = 0.001
S = 1.11	Δρmax = 0.19 e Å^−3
5875 reflections	Δρmin = −0.30 e Å^−3
397 parameters	Absolute structure: Flack x determined using 1954 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
6 restraints	Absolute structure parameter: −0.02 (2)

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	0.74975 (13)	0.61684 (9)	0.47862 (4)	0.0267 (2)
N1	0.9037 (4)	0.6149 (3)	0.41702 (11)	0.0365 (7)
O1	0.9217 (3)	0.6992 (2)	0.51478 (9)	0.0385 (6)
Cl1	1.54405 (14)	0.55375 (12)	0.66319 (5)	0.0633 (3)
C1	1.0494 (5)	0.6545 (4)	0.41426 (18)	0.0530 (12)
H1	1.099013	0.679111	0.440952	0.064*
C2	1.1337 (7)	0.6614 (5)	0.3727 (2)	0.0780 (19)
H2	1.236266	0.690840	0.371965	0.094*
N2	0.6022 (4)	0.5362 (3)	0.42262 (11)	0.0369 (7)
O2	1.1607 (3)	0.7335 (2)	0.54372 (9)	0.0357 (6)
Cl2	1.4063 (2)	0.67185 (14)	0.75186 (5)	0.0790 (5)
Cl3	0.15576 (17)	0.37562 (13)	0.73575 (4)	0.0663 (4)
O3	0.6602 (4)	0.3036 (2)	0.54131 (11)	0.0493 (7)
C3	1.0631 (8)	0.6243 (5)	0.3337 (2)	0.082 (2)
H3	1.117209	0.629134	0.305907	0.099*
Cl4	−0.16156 (14)	0.37371 (13)	0.67738 (5)	0.0699 (4)
O4	0.4435 (3)	0.4096 (2)	0.55004 (10)	0.0419 (6)
C4	0.9097 (7)	0.5789 (4)	0.33488 (16)	0.0610 (14)
C5	0.8254 (11)	0.5346 (5)	0.29550 (17)	0.084 (2)
H5	0.875538	0.534589	0.267065	0.101*
O5	1.1543 (4)	0.4146 (3)	0.49366 (11)	0.0479 (7)
H5A	1.171 (6)	0.351 (2)	0.4841 (16)	0.057*
H5B	1.222 (5)	0.418 (4)	0.5141 (12)	0.057*
C6	0.6766 (11)	0.4933 (5)	0.29891 (18)	0.080 (2)
H6	0.626427	0.465292	0.272900	0.096*
O6	0.5677 (3)	0.6048 (2)	0.52461 (10)	0.0398 (6)
H6A	0.534 (5)	0.547 (2)	0.5358 (14)	0.048*
H6B	0.499 (4)	0.652 (3)	0.5197 (15)	0.048*
C7	0.5954 (7)	0.4920 (4)	0.34131 (15)	0.0577 (14)
O7	0.8298 (3)	0.4614 (2)	0.49807 (10)	0.0392 (6)
H7A	0.9266 (18)	0.452 (4)	0.4979 (15)	0.047*
H7B	0.780 (5)	0.416 (3)	0.5129 (13)	0.047*
C8	0.4402 (8)	0.4523 (4)	0.3470 (2)	0.0694 (16)
H8	0.384505	0.424534	0.321840	0.083*
C9	0.3702 (7)	0.4541 (4)	0.3887 (2)	0.0673 (15)
H9	0.267073	0.427043	0.392538	0.081*
C10	0.4546 (5)	0.4969 (4)	0.42594 (17)	0.0522 (11)
H10	0.405179	0.497982	0.454485	0.063*
C11	0.6733 (5)	0.5346 (3)	0.38090 (13)	0.0367 (9)
C12	0.8325 (6)	0.5775 (3)	0.37770 (13)	0.0402 (9)
C13	1.0286 (4)	0.6864 (3)	0.54477 (12)	0.0290 (7)
C14	0.9945 (5)	0.6065 (4)	0.58447 (13)	0.0408 (9)
H14A	0.883664	0.614531	0.593312	0.049*
H14B	1.009482	0.530295	0.573815	0.049*
C15	1.0973 (4)	0.6245 (3)	0.62627 (12)	0.0336 (8)
C16	1.0394 (5)	0.6754 (4)	0.66536 (14)	0.0457 (10)
H16	0.934188	0.699894	0.666065	0.055*
C17	1.1349 (6)	0.6905 (4)	0.70345 (14)	0.0538 (12)
H17	1.093717	0.725093	0.729441	0.065*
C18	1.2902 (5)	0.6546 (4)	0.70310 (14)	0.0465 (11)
C19	1.3500 (5)	0.6034 (3)	0.66423 (14)	0.0404 (9)
C20	1.2544 (5)	0.5880 (3)	0.62600 (13)	0.0351 (8)
H20	1.295637	0.553031	0.600080	0.042*
C21	0.5252 (5)	0.3253 (3)	0.55813 (13)	0.0352 (8)
C22	0.4613 (5)	0.2369 (3)	0.59174 (16)	0.0479 (11)
H22A	0.448975	0.166578	0.575469	0.057*
H22B	0.539763	0.225382	0.615715	0.057*
C24	0.0211 (5)	0.2985 (4)	0.60812 (14)	0.0434 (10)
H24	−0.072029	0.297885	0.590816	0.052*
C23	0.0185 (5)	0.3335 (3)	0.65342 (14)	0.0386 (9)
C26	0.3042 (4)	0.2669 (3)	0.61370 (14)	0.0351 (9)
C27	0.1555 (5)	0.3334 (3)	0.67863 (13)	0.0386 (9)
C28	0.2987 (5)	0.3005 (3)	0.65896 (14)	0.0379 (9)
H28	0.391555	0.301079	0.676383	0.045*
C25	0.1641 (6)	0.2645 (3)	0.58899 (13)	0.0423 (9)
H25	0.165698	0.239476	0.558795	0.051*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mg1	0.0224 (5)	0.0244 (6)	0.0333 (6)	−0.0004 (5)	0.0015 (5)	0.0023 (5)
N1	0.0324 (16)	0.0279 (16)	0.0491 (19)	0.0050 (14)	0.0122 (14)	0.0064 (14)
O1	0.0354 (14)	0.0318 (14)	0.0483 (15)	−0.0068 (11)	−0.0164 (12)	0.0089 (12)
Cl1	0.0390 (6)	0.0676 (8)	0.0833 (9)	0.0155 (6)	−0.0107 (6)	0.0032 (6)
C1	0.035 (2)	0.040 (2)	0.084 (3)	0.0020 (19)	0.021 (2)	0.006 (2)
C2	0.053 (3)	0.062 (3)	0.119 (5)	0.014 (3)	0.049 (4)	0.029 (3)
N2	0.0324 (17)	0.0345 (17)	0.0437 (18)	0.0013 (14)	−0.0041 (14)	0.0000 (14)
O2	0.0279 (13)	0.0329 (13)	0.0463 (14)	−0.0072 (12)	−0.0067 (12)	0.0130 (11)
Cl2	0.0955 (11)	0.0839 (10)	0.0576 (7)	0.0175 (8)	−0.0370 (7)	−0.0105 (7)
Cl3	0.0697 (8)	0.0861 (9)	0.0433 (6)	−0.0050 (8)	0.0050 (6)	−0.0119 (6)
O3	0.0368 (16)	0.0370 (15)	0.074 (2)	−0.0009 (14)	0.0198 (15)	0.0066 (14)
C3	0.090 (4)	0.080 (4)	0.077 (4)	0.031 (4)	0.052 (4)	0.029 (3)
Cl4	0.0393 (6)	0.0871 (9)	0.0832 (9)	0.0180 (7)	0.0161 (6)	0.0076 (7)
O4	0.0367 (15)	0.0297 (14)	0.0592 (17)	−0.0010 (12)	0.0094 (13)	0.0089 (12)
C4	0.085 (4)	0.050 (3)	0.049 (3)	0.030 (3)	0.027 (3)	0.013 (2)
C5	0.148 (7)	0.074 (4)	0.031 (2)	0.056 (5)	0.015 (4)	0.004 (2)
O5	0.0343 (16)	0.0431 (16)	0.066 (2)	0.0036 (14)	−0.0050 (14)	0.0015 (15)
C6	0.136 (6)	0.062 (4)	0.041 (3)	0.041 (4)	−0.017 (4)	−0.008 (2)
O6	0.0416 (16)	0.0282 (14)	0.0496 (16)	0.0068 (12)	0.0166 (13)	0.0102 (12)
C7	0.093 (4)	0.035 (2)	0.045 (2)	0.027 (3)	−0.022 (2)	−0.0044 (19)
O7	0.0267 (13)	0.0284 (14)	0.0624 (17)	0.0009 (12)	0.0034 (13)	0.0110 (12)
C8	0.084 (4)	0.041 (3)	0.082 (4)	0.006 (3)	−0.049 (3)	−0.007 (3)
C9	0.057 (3)	0.048 (3)	0.097 (4)	−0.004 (2)	−0.033 (3)	−0.001 (3)
C10	0.041 (2)	0.050 (3)	0.066 (3)	−0.004 (2)	−0.009 (2)	0.000 (2)
C11	0.049 (2)	0.0243 (18)	0.037 (2)	0.0141 (18)	−0.0069 (18)	0.0015 (15)
C12	0.058 (3)	0.0239 (18)	0.039 (2)	0.0165 (19)	0.011 (2)	0.0077 (15)
C13	0.0307 (19)	0.0209 (17)	0.0355 (18)	0.0004 (15)	−0.0020 (16)	0.0004 (14)
C14	0.040 (2)	0.039 (2)	0.044 (2)	−0.0130 (18)	−0.0047 (17)	0.0107 (18)
C15	0.0352 (19)	0.0263 (18)	0.0393 (19)	−0.0034 (17)	−0.0025 (15)	0.0086 (16)
C16	0.041 (2)	0.050 (2)	0.045 (2)	0.017 (2)	0.0015 (19)	0.0063 (19)
C17	0.068 (3)	0.054 (3)	0.039 (2)	0.020 (2)	0.003 (2)	−0.003 (2)
C18	0.058 (3)	0.042 (2)	0.040 (2)	0.008 (2)	−0.0133 (19)	0.0016 (18)
C19	0.039 (2)	0.033 (2)	0.050 (2)	0.0084 (18)	−0.0059 (19)	0.0059 (17)
C20	0.039 (2)	0.0276 (18)	0.039 (2)	0.0016 (17)	0.0013 (17)	0.0012 (15)
C21	0.035 (2)	0.028 (2)	0.042 (2)	−0.0031 (17)	0.0055 (17)	0.0000 (16)
C22	0.049 (3)	0.032 (2)	0.063 (3)	0.007 (2)	0.019 (2)	0.012 (2)
C24	0.040 (2)	0.042 (2)	0.048 (2)	−0.0087 (19)	−0.0048 (19)	0.0126 (19)
C23	0.035 (2)	0.034 (2)	0.047 (2)	0.0030 (17)	0.0057 (17)	0.0075 (17)
C26	0.034 (2)	0.0256 (18)	0.046 (2)	−0.0005 (16)	0.0087 (17)	0.0077 (16)
C27	0.043 (2)	0.036 (2)	0.0369 (19)	−0.0023 (18)	0.0060 (18)	0.0029 (16)
C28	0.032 (2)	0.035 (2)	0.046 (2)	0.0009 (16)	−0.0006 (17)	0.0082 (17)
C25	0.052 (2)	0.038 (2)	0.036 (2)	−0.008 (2)	0.008 (2)	0.0029 (17)

Geometric parameters (Å, º)

Mg1—O6	2.037 (3)	C7—C11	1.421 (6)
Mg1—O1	2.040 (3)	O7—H7A	0.820 (14)
Mg1—O2^i	2.044 (3)	O7—H7B	0.815 (14)
Mg1—O7	2.054 (3)	C8—C9	1.352 (8)
Mg1—N1	2.213 (3)	C8—H8	0.9300
Mg1—N2	2.264 (3)	C9—C10	1.394 (7)
N1—C1	1.313 (5)	C9—H9	0.9300
N1—C12	1.368 (5)	C10—H10	0.9300
O1—C13	1.262 (4)	C11—C12	1.434 (6)
Cl1—C19	1.732 (4)	C13—C14	1.528 (5)
C1—C2	1.405 (7)	C14—C15	1.509 (5)
C1—H1	0.9300	C14—H14A	0.9700
C2—C3	1.358 (9)	C14—H14B	0.9700
C2—H2	0.9300	C15—C16	1.380 (6)
N2—C10	1.328 (6)	C15—C20	1.389 (5)
N2—C11	1.355 (5)	C16—C17	1.382 (6)
O2—C13	1.243 (4)	C16—H16	0.9300
Cl2—C18	1.736 (4)	C17—C18	1.371 (7)
Cl3—C27	1.741 (4)	C17—H17	0.9300
O3—C21	1.261 (5)	C18—C19	1.383 (6)
C3—C4	1.397 (9)	C19—C20	1.386 (5)
C3—H3	0.9300	C20—H20	0.9300
Cl4—C23	1.732 (4)	C21—C22	1.537 (5)
O4—C21	1.241 (5)	C22—C26	1.509 (6)
C4—C12	1.407 (6)	C22—H22A	0.9700
C4—C5	1.449 (9)	C22—H22B	0.9700
C5—C6	1.345 (10)	C24—C25	1.384 (6)
C5—H5	0.9300	C24—C23	1.386 (6)
O5—H5A	0.826 (14)	C24—H24	0.9300
O5—H5B	0.822 (14)	C23—C27	1.364 (6)
C6—C7	1.412 (8)	C26—C25	1.379 (6)
C6—H6	0.9300	C26—C28	1.380 (6)
O6—H6A	0.817 (14)	C27—C28	1.388 (6)
O6—H6B	0.817 (13)	C28—H28	0.9300
C7—C8	1.395 (8)	C25—H25	0.9300
O6—Mg1—O1	102.91 (13)	N2—C11—C7	122.2 (4)
O6—Mg1—O2^i	89.87 (11)	N2—C11—C12	117.6 (3)
O1—Mg1—O2^i	90.07 (12)	C7—C11—C12	120.2 (4)
O6—Mg1—O7	89.95 (12)	N1—C12—C4	122.6 (5)
O1—Mg1—O7	93.57 (12)	N1—C12—C11	118.0 (3)
O2^i—Mg1—O7	176.30 (13)	C4—C12—C11	119.4 (4)
O6—Mg1—N1	166.23 (14)	O2—C13—O1	124.2 (3)
O1—Mg1—N1	90.68 (13)	O2—C13—C14	117.9 (3)
O2^i—Mg1—N1	87.92 (11)	O1—C13—C14	117.9 (3)
O7—Mg1—N1	91.38 (12)	C15—C14—C13	114.6 (3)
O6—Mg1—N2	92.01 (13)	C15—C14—H14A	108.6
O1—Mg1—N2	164.72 (13)	C13—C14—H14A	108.6
O2^i—Mg1—N2	86.70 (12)	C15—C14—H14B	108.6
O7—Mg1—N2	89.62 (13)	C13—C14—H14B	108.6
N1—Mg1—N2	74.29 (12)	H14A—C14—H14B	107.6
C1—N1—C12	118.2 (4)	C16—C15—C20	118.5 (4)
C1—N1—Mg1	126.1 (3)	C16—C15—C14	121.9 (4)
C12—N1—Mg1	115.4 (3)	C20—C15—C14	119.5 (4)
C13—O1—Mg1	143.3 (2)	C15—C16—C17	121.1 (4)
N1—C1—C2	122.8 (5)	C15—C16—H16	119.4
N1—C1—H1	118.6	C17—C16—H16	119.4
C2—C1—H1	118.6	C18—C17—C16	120.3 (4)
C3—C2—C1	119.0 (5)	C18—C17—H17	119.9
C3—C2—H2	120.5	C16—C17—H17	119.9
C1—C2—H2	120.5	C17—C18—C19	119.3 (4)
C10—N2—C11	118.1 (4)	C17—C18—Cl2	119.3 (3)
C10—N2—Mg1	127.4 (3)	C19—C18—Cl2	121.3 (3)
C11—N2—Mg1	114.4 (3)	C18—C19—C20	120.5 (4)
C13—O2—Mg1^ii	136.9 (2)	C18—C19—Cl1	120.5 (3)
C2—C3—C4	120.5 (5)	C20—C19—Cl1	119.0 (3)
C2—C3—H3	119.8	C19—C20—C15	120.2 (4)
C4—C3—H3	119.8	C19—C20—H20	119.9
C3—C4—C12	116.8 (5)	C15—C20—H20	119.9
C3—C4—C5	124.8 (6)	O4—C21—O3	126.1 (4)
C12—C4—C5	118.3 (6)	O4—C21—C22	119.1 (3)
C6—C5—C4	121.9 (5)	O3—C21—C22	114.8 (3)
C6—C5—H5	119.1	C26—C22—C21	114.3 (3)
C4—C5—H5	119.1	C26—C22—H22A	108.7
H5A—O5—H5B	100 (5)	C21—C22—H22A	108.7
C5—C6—C7	121.1 (6)	C26—C22—H22B	108.7
C5—C6—H6	119.4	C21—C22—H22B	108.7
C7—C6—H6	119.4	H22A—C22—H22B	107.6
Mg1—O6—H6A	126 (3)	C25—C24—C23	119.1 (4)
Mg1—O6—H6B	112 (3)	C25—C24—H24	120.4
H6A—O6—H6B	114 (5)	C23—C24—H24	120.4
C8—C7—C6	123.9 (6)	C27—C23—C24	120.0 (4)
C8—C7—C11	117.0 (5)	C27—C23—Cl4	121.2 (3)
C6—C7—C11	119.1 (6)	C24—C23—Cl4	118.8 (3)
Mg1—O7—H7A	117 (3)	C25—C26—C28	118.5 (4)
Mg1—O7—H7B	126 (3)	C25—C26—C22	121.2 (4)
H7A—O7—H7B	115 (5)	C28—C26—C22	120.3 (4)
C9—C8—C7	120.4 (5)	C23—C27—C28	120.4 (3)
C9—C8—H8	119.8	C23—C27—Cl3	121.1 (3)
C7—C8—H8	119.8	C28—C27—Cl3	118.4 (3)
C8—C9—C10	119.1 (5)	C26—C28—C27	120.4 (4)
C8—C9—H9	120.4	C26—C28—H28	119.8
C10—C9—H9	120.4	C27—C28—H28	119.8
N2—C10—C9	123.2 (5)	C26—C25—C24	121.5 (4)
N2—C10—H10	118.4	C26—C25—H25	119.3
C9—C10—H10	118.4	C24—C25—H25	119.3

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O3^iii	0.82 (3)	1.99 (3)	2.799 (4)	168 (5)
O5—H5B···O4^iv	0.82 (4)	2.14 (4)	2.931 (4)	162 (4)
O6—H6A···O4	0.81 (3)	1.86 (3)	2.660 (3)	169 (4)
O7—H7B···O5	0.81 (4)	1.87 (4)	2.677 (4)	174 (4)

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