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Acta Crystallogr Sect E Struct Rep Online. 2010 March 1; 66(Pt 3): m305.
Published online 2010 February 17. doi:  10.1107/S1600536810005684
PMCID: PMC2983537

Diaqua­bis(5-carb­oxy-2-propyl-1H-imidazole-4-carboxyl­ato-κ2 N 3,O 4)magnesium(II) 3.5-hydrate

Abstract

In the title complex, [Mg(C8H9N2O4)2(H2O)2]·3.5H2O, the MgII atom is six-coordinated by two N,O-bidentate 5-carb­oxy-2-propyl-1H-imidazole-4-carboxyl­ate ligands and two water mol­ecules, forming a distorted octa­hedral environment. The complex mol­ecules are linked into a three-dimensional network by N—H(...)O and O—H(...)O hydrogen-bonding inter­actions. The propyl groups are disordered over two sites, with site occupancies of 0.755 (7):0.245 (7) and 0.556 (13):0.444 (13).

Related literature

For related structures, see: Sengupta et al. (2001 [triangle]); Song et al. (2010 [triangle]); Wang et al. (2004 [triangle]); Yan et al. (2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m305-scheme1.jpg

Experimental

Crystal data

  • [Mg(C8H9N2O4)2(H2O)2]·3.5H2O
  • M r = 517.74
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m305-efi1.jpg
  • a = 10.516 (1) Å
  • b = 10.5332 (11) Å
  • c = 11.3989 (13) Å
  • α = 83.288 (1)°
  • β = 81.783 (1)°
  • γ = 86.458 (2)°
  • V = 1239.8 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.14 mm−1
  • T = 298 K
  • 0.48 × 0.38 × 0.35 mm

Data collection

  • Bruker SMART 1000 CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.935, T max = 0.952
  • 6478 measured reflections
  • 4321 independent reflections
  • 2780 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.058
  • wR(F 2) = 0.178
  • S = 1.00
  • 4321 reflections
  • 378 parameters
  • H-atom parameters constrained
  • Δρmax = 0.58 e Å−3
  • Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]) and DIAMOND (Brandenburg, 1999 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, 1R. DOI: 10.1107/S1600536810005684/hy2281sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005684/hy2281Isup2.hkl

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

Acknowledgments

The authors thank Henan University of Urban Construction.

supplementary crystallographic information

Comment

Imidazole-4,5-dicarboxylate ligands with efficient N,O-donors have been been widely used to obtain new complexes with excellent properties (Sengupta et al., 2001; Song et al.,2010; Wang et al., 2004; Yan et al., 2010). Bearing this in mind, we introduced Mg(CH3CO2)2 and 2-propyl-1H-imidazole-4,5-dicarboxylic acid into reaction so as to obtain a new MgII complex.

As illustrated in Fig. 1, the title complex molecule contains one MgII ion, two mono-deprotonated 2-propyl-1H-imidazole-4,5-dicarboxylate ligands, two coordinated water molecules and three and half uncoordinated water molecules. The Mg II atom is six-coordinated by two N,O-bidentate ligands and two water molecules in a slightly distorted octahedral environment. Both ligands coordinate through N atoms and carboxylate O atoms in a bidentate chelate fashion, forming two five-membered Mg, O, C, C, N rings. Uncoordinated solvent water molecules are located in cavities of the three-dimensional network, participating in N—H···O and O—H···O hydrogen bonds, which contribute to the stability of the network. The two propyl residues are disordered over two sites, with site occupancies of 0.755 (7):0.245 (7) and 0.556 (13):0.444 (13).

Experimental

The title compound was prepared by the hydrothermal reaction of Mg(CH3CO2)2 (0.5 mmol, 0.07 g) and 2-propyl-1H-imidazole-4,5-dicarboxylic acid (0.5 mmol, 0.99 g) in 15 ml of H2O solution. The reaction was performed in a Teflon-lined autoclave (20 ml), which was heated at 433 K for 2 d. Crystals of the title compound were obtained by slow evaporation of the solvent at room temperature.

Refinement

C- and N-bound H atoms were placed at calculated positions and were treated as riding atoms, with C—H = 0.97 (CH2) and 0.96 (CH3) Å and N—H = 0.86 Å and with Uiso(H) = 1.2(1.5 for methyl)Ueq(C,N). The water H atoms were located in a difference map and refined as riding, with O—H = 0.85 Å and Uiso(H) = 1.2Ueq(O). H atoms of carboxyl groups were located in a difference map and refined as riding, with O—H = 0.82 Å and Uiso(H) = 1.5Ueq(O).

Figures

Fig. 1.
Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms are omitted for clarity.
Fig. 2.
A view of the three-dimensional network constructed by N—H···O and O—H···O hydrogen bonding interactions (dashed lines).

Crystal data

[Mg(C8H9N2O4)2(H2O)2]·3.5H2OZ = 2
Mr = 517.74F(000) = 546
Triclinic, P1Dx = 1.387 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.516 (1) ÅCell parameters from 2051 reflections
b = 10.5332 (11) Åθ = 2.5–23.9°
c = 11.3989 (13) ŵ = 0.14 mm1
α = 83.288 (1)°T = 298 K
β = 81.783 (1)°Block, colorless
γ = 86.458 (2)°0.48 × 0.38 × 0.35 mm
V = 1239.8 (2) Å3

Data collection

Bruker SMART 1000 CCD diffractometer4321 independent reflections
Radiation source: fine-focus sealed tube2780 reflections with I > 2σ(I)
graphiteRint = 0.028
[var phi] and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→12
Tmin = 0.935, Tmax = 0.952k = −7→12
6478 measured reflectionsl = −12→13

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0865P)2 + 0.6255P] where P = (Fo2 + 2Fc2)/3
4321 reflections(Δ/σ)max = 0.001
378 parametersΔρmax = 0.58 e Å3
0 restraintsΔρmin = −0.31 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
Mg10.20602 (10)0.14342 (10)0.81297 (9)0.0417 (3)
N10.2821 (2)0.1678 (3)0.6227 (2)0.0429 (6)
N20.3556 (3)0.1891 (3)0.4316 (2)0.0518 (7)
H20.35650.20230.35560.062*
N30.2165 (2)0.3506 (2)0.8307 (2)0.0406 (6)
N40.2228 (2)0.5498 (3)0.8701 (2)0.0455 (7)
H40.25250.61920.88590.055*
O10.4034 (2)0.1060 (2)0.81403 (18)0.0481 (6)
O20.5972 (2)0.1009 (3)0.7049 (2)0.0601 (7)
O30.6855 (2)0.1268 (3)0.4872 (2)0.0639 (7)
H30.65630.11200.55780.096*
O40.6100 (2)0.1666 (2)0.3161 (2)0.0652 (7)
O50.0167 (2)0.2175 (2)0.7964 (2)0.0483 (6)
O6−0.1219 (2)0.3840 (2)0.8141 (2)0.0602 (7)
O7−0.1173 (2)0.6067 (2)0.8584 (2)0.0588 (7)
H7−0.11780.53040.85040.088*
O80.0222 (2)0.7397 (2)0.8968 (2)0.0580 (7)
O90.1655 (3)0.1075 (2)0.9919 (2)0.0653 (8)
H9C0.10710.15291.02900.078*
H9D0.18320.04181.03850.078*
O100.1704 (3)−0.0415 (2)0.7915 (2)0.0674 (8)
H10C0.2394−0.07440.75690.081*
H10D0.1228−0.10180.82410.081*
O110.2291 (3)0.8974 (3)0.1314 (3)0.0858 (10)
H11C0.27620.89400.18640.103*
H11D0.15920.86190.15970.103*
O120.3299 (3)0.2189 (4)0.1936 (3)0.1094 (13)
H12C0.27050.26760.16710.131*
H12D0.37290.18390.13590.131*
O130.3434 (3)0.7359 (3)0.9551 (3)0.1053 (12)
H13C0.41030.77950.94190.126*
H13D0.29140.76841.00880.126*
O140.5130 (5)0.9089 (5)0.9622 (4)0.0584 (13)0.50
H14G0.48160.97840.92980.070*0.50
H14H0.53330.92201.02920.070*0.50
C10.4763 (3)0.1168 (3)0.7168 (3)0.0438 (8)
C20.4130 (3)0.1509 (3)0.6087 (3)0.0382 (7)
C30.4614 (3)0.1646 (3)0.4896 (3)0.0430 (8)
C40.5913 (3)0.1533 (3)0.4242 (3)0.0482 (8)
C50.2496 (3)0.1891 (4)0.5137 (3)0.0563 (10)
C60.1138 (11)0.1962 (10)0.4864 (9)0.064 (2)0.755 (7)
H6A0.05980.14920.55110.077*0.755 (7)
H6B0.11080.15660.41420.077*0.755 (7)
C70.0631 (7)0.3333 (8)0.4701 (6)0.082 (2)0.755 (7)
H7A0.11030.37780.39950.099*0.755 (7)
H7B0.07530.37600.53830.099*0.755 (7)
C8−0.0804 (6)0.3375 (8)0.4573 (7)0.111 (3)0.755 (7)
H8A−0.09270.29050.39290.166*0.755 (7)
H8B−0.11060.42480.44100.166*0.755 (7)
H8C−0.12780.29990.53010.166*0.755 (7)
C6'0.129 (3)0.259 (3)0.478 (3)0.061 (7)0.245 (7)
H6'10.14630.31220.40290.073*0.245 (7)
H6'20.08750.31020.53890.073*0.245 (7)
C7'0.047 (2)0.145 (2)0.4661 (19)0.081 (6)0.245 (7)
H7'10.04510.08720.53890.097*0.245 (7)
H7'2−0.04010.17810.46060.097*0.245 (7)
C8'0.091 (2)0.069 (2)0.361 (2)0.106 (8)0.245 (7)
H8'10.06650.11520.28990.158*0.245 (7)
H8'20.0511−0.01220.37550.158*0.245 (7)
H8'30.18270.05490.35260.158*0.245 (7)
C9−0.0087 (3)0.3316 (3)0.8131 (3)0.0440 (8)
C100.0964 (3)0.4090 (3)0.8322 (3)0.0394 (7)
C110.0983 (3)0.5332 (3)0.8570 (3)0.0414 (7)
C12−0.0035 (3)0.6349 (3)0.8720 (3)0.0458 (8)
C130.2919 (3)0.4388 (3)0.8542 (3)0.0461 (8)
C140.4291 (18)0.4147 (17)0.8779 (12)0.053 (3)0.556 (13)
H14A0.45490.32550.87140.064*0.556 (13)
H14B0.43590.43240.95840.064*0.556 (13)
C150.5185 (8)0.5000 (8)0.7884 (11)0.072 (3)0.556 (13)
H15A0.49070.58890.79430.086*0.556 (13)
H15B0.60500.48830.80940.086*0.556 (13)
C160.5214 (18)0.472 (2)0.6607 (18)0.099 (7)0.556 (13)
H16A0.53810.38170.65610.149*0.556 (13)
H16B0.58790.51840.61040.149*0.556 (13)
H16C0.43980.49730.63460.149*0.556 (13)
C14'0.434 (2)0.435 (2)0.8282 (14)0.055 (4)0.444 (13)
H14C0.46710.34810.84670.066*0.444 (13)
H14D0.46740.48820.87990.066*0.444 (13)
C15'0.484 (2)0.481 (2)0.6993 (19)0.073 (6)0.444 (13)
H15C0.44400.43480.64670.087*0.444 (13)
H15D0.46140.57110.68310.087*0.444 (13)
C16'0.6296 (14)0.4600 (12)0.6737 (12)0.097 (5)0.444 (13)
H16D0.66940.49890.73040.146*0.444 (13)
H16E0.65940.49790.59460.146*0.444 (13)
H16F0.65170.36990.67990.146*0.444 (13)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Mg10.0463 (6)0.0375 (6)0.0393 (6)0.0013 (5)0.0014 (5)−0.0057 (5)
N10.0440 (16)0.0449 (16)0.0392 (15)0.0004 (13)−0.0037 (12)−0.0055 (12)
N20.0598 (18)0.0601 (19)0.0335 (14)0.0063 (15)−0.0045 (13)−0.0041 (13)
N30.0397 (15)0.0359 (15)0.0455 (15)0.0011 (12)−0.0020 (11)−0.0077 (12)
N40.0455 (16)0.0369 (15)0.0544 (17)−0.0044 (13)0.0001 (12)−0.0136 (13)
O10.0561 (14)0.0522 (14)0.0338 (12)0.0090 (11)−0.0037 (10)−0.0042 (10)
O20.0467 (15)0.0847 (19)0.0490 (14)0.0051 (13)−0.0072 (11)−0.0112 (13)
O30.0505 (15)0.081 (2)0.0572 (15)−0.0037 (14)0.0082 (12)−0.0142 (15)
O40.0756 (18)0.0645 (17)0.0461 (15)0.0060 (14)0.0160 (12)−0.0019 (12)
O50.0453 (13)0.0449 (14)0.0563 (14)−0.0062 (11)−0.0051 (10)−0.0118 (11)
O60.0408 (14)0.0581 (16)0.0834 (18)0.0030 (12)−0.0140 (12)−0.0103 (14)
O70.0511 (15)0.0474 (15)0.0758 (17)0.0120 (12)−0.0069 (12)−0.0071 (14)
O80.0629 (16)0.0412 (14)0.0641 (16)0.0011 (12)0.0120 (12)−0.0083 (12)
O90.0830 (18)0.0568 (16)0.0445 (14)0.0250 (14)0.0133 (12)0.0008 (12)
O100.0755 (18)0.0428 (15)0.0765 (17)−0.0136 (13)0.0259 (14)−0.0151 (13)
O110.087 (2)0.078 (2)0.098 (2)−0.0325 (17)−0.0461 (17)0.0259 (17)
O120.131 (3)0.138 (3)0.0634 (19)0.048 (2)−0.0415 (19)−0.021 (2)
O130.113 (3)0.090 (3)0.129 (3)0.003 (2)−0.041 (2)−0.056 (2)
O140.072 (3)0.060 (3)0.045 (3)0.006 (3)−0.017 (2)−0.006 (2)
C10.047 (2)0.0414 (19)0.0438 (19)0.0021 (15)−0.0063 (15)−0.0119 (15)
C20.0417 (18)0.0346 (17)0.0378 (17)0.0005 (14)−0.0015 (13)−0.0072 (13)
C30.0495 (19)0.0372 (18)0.0415 (18)−0.0001 (15)−0.0029 (15)−0.0064 (14)
C40.056 (2)0.0393 (19)0.046 (2)−0.0010 (16)0.0065 (17)−0.0071 (15)
C50.055 (2)0.071 (3)0.044 (2)0.0056 (19)−0.0095 (17)−0.0099 (18)
C60.063 (5)0.076 (7)0.058 (4)−0.007 (6)−0.018 (3)−0.006 (5)
C70.072 (4)0.091 (5)0.083 (4)0.003 (4)−0.017 (3)0.003 (4)
C80.068 (4)0.132 (7)0.126 (6)0.010 (4)−0.023 (4)0.013 (5)
C6'0.060 (15)0.064 (18)0.057 (12)0.005 (18)−0.014 (10)−0.002 (14)
C7'0.072 (14)0.095 (17)0.075 (13)−0.001 (12)−0.015 (11)−0.001 (12)
C8'0.092 (15)0.117 (19)0.108 (17)−0.004 (14)−0.025 (13)0.001 (15)
C90.0417 (19)0.045 (2)0.0439 (18)−0.0009 (16)−0.0028 (14)−0.0023 (15)
C100.0393 (17)0.0366 (18)0.0393 (17)0.0017 (14)0.0013 (13)−0.0020 (14)
C110.0438 (18)0.0407 (19)0.0368 (17)0.0000 (15)0.0004 (13)−0.0009 (14)
C120.055 (2)0.041 (2)0.0374 (18)0.0005 (16)0.0043 (15)0.0007 (15)
C130.0423 (18)0.0410 (19)0.055 (2)−0.0019 (15)0.0004 (15)−0.0118 (16)
C140.045 (5)0.055 (7)0.062 (8)−0.005 (4)−0.010 (7)−0.015 (7)
C150.050 (5)0.064 (5)0.099 (8)−0.012 (4)0.002 (5)−0.015 (5)
C160.091 (19)0.097 (10)0.098 (13)−0.009 (10)0.031 (9)−0.015 (8)
C14'0.048 (6)0.049 (8)0.068 (11)−0.004 (6)0.000 (10)−0.016 (9)
C15'0.051 (10)0.070 (8)0.089 (17)0.006 (7)0.017 (10)−0.015 (10)
C16'0.060 (9)0.090 (9)0.133 (11)0.005 (6)0.003 (7)0.003 (7)

Geometric parameters (Å, °)

Mg1—O92.019 (2)C5—C6'1.51 (3)
Mg1—O102.055 (3)C6—C71.508 (11)
Mg1—O12.090 (2)C6—H6A0.9700
Mg1—O52.118 (2)C6—H6B0.9700
Mg1—N12.193 (3)C7—C81.535 (9)
Mg1—N32.226 (3)C7—H7A0.9700
N1—C51.325 (4)C7—H7B0.9700
N1—C21.365 (4)C8—H8A0.9600
N2—C51.349 (4)C8—H8B0.9600
N2—C31.370 (4)C8—H8C0.9600
N2—H20.8600C6'—C7'1.54 (3)
N3—C131.332 (4)C6'—H6'10.9700
N3—C101.369 (4)C6'—H6'20.9700
N4—C131.354 (4)C7'—C8'1.52 (3)
N4—C111.363 (4)C7'—H7'10.9700
N4—H40.8600C7'—H7'20.9700
O1—C11.252 (4)C8'—H8'10.9600
O2—C11.262 (4)C8'—H8'20.9600
O3—C41.303 (4)C8'—H8'30.9600
O3—H30.8200C9—C101.467 (5)
O4—C41.213 (4)C10—C111.372 (4)
O5—C91.246 (4)C11—C121.474 (5)
O6—C91.280 (4)C13—C14'1.48 (2)
O7—C121.285 (4)C13—C141.506 (19)
O7—H70.8200C14—C151.533 (17)
O8—C121.227 (4)C14—H14A0.9700
O9—H9C0.8500C14—H14B0.9700
O9—H9D0.8500C15—C161.52 (2)
O10—H10C0.8500C15—H15A0.9700
O10—H10D0.8500C15—H15B0.9700
O11—H11C0.8501C16—H16A0.9600
O11—H11D0.8500C16—H16B0.9600
O12—H12C0.8499C16—H16C0.9600
O12—H12D0.8499C14'—C15'1.52 (2)
O13—H13C0.8500C14'—H14C0.9700
O13—H13D0.8499C14'—H14D0.9700
O14—H14G0.8500C15'—C16'1.52 (2)
O14—H14H0.8500C15'—H15C0.9700
C1—C21.481 (4)C15'—H15D0.9700
C2—C31.374 (4)C16'—H16D0.9600
C3—C41.465 (5)C16'—H16E0.9600
C5—C61.500 (11)C16'—H16F0.9600
O9—Mg1—O1091.24 (11)C8—C7—H7B109.7
O9—Mg1—O193.24 (10)H7A—C7—H7B108.2
O10—Mg1—O194.26 (11)C5—C6'—C7'101.1 (19)
O9—Mg1—O592.42 (10)C5—C6'—H6'1111.6
O10—Mg1—O595.35 (11)C7'—C6'—H6'1111.6
O1—Mg1—O5168.73 (10)C5—C6'—H6'2111.6
O9—Mg1—N1170.33 (11)C7'—C6'—H6'2111.6
O10—Mg1—N187.42 (10)H6'1—C6'—H6'2109.4
O1—Mg1—N177.33 (9)C8'—C7'—C6'117 (2)
O5—Mg1—N197.24 (10)C8'—C7'—H7'1108.1
O9—Mg1—N389.86 (10)C6'—C7'—H7'1108.1
O10—Mg1—N3171.92 (12)C8'—C7'—H7'2108.1
O1—Mg1—N393.67 (10)C6'—C7'—H7'2108.1
O5—Mg1—N376.60 (9)H7'1—C7'—H7'2107.3
N1—Mg1—N392.82 (10)C7'—C8'—H8'1109.5
C5—N1—C2106.2 (3)C7'—C8'—H8'2109.5
C5—N1—Mg1144.1 (2)H8'1—C8'—H8'2109.5
C2—N1—Mg1109.73 (19)C7'—C8'—H8'3109.5
C5—N2—C3108.5 (3)H8'1—C8'—H8'3109.5
C5—N2—H2125.7H8'2—C8'—H8'3109.5
C3—N2—H2125.7O5—C9—O6123.0 (3)
C13—N3—C10105.7 (3)O5—C9—C10118.2 (3)
C13—N3—Mg1144.0 (2)O6—C9—C10118.8 (3)
C10—N3—Mg1109.6 (2)N3—C10—C11110.4 (3)
C13—N4—C11108.7 (3)N3—C10—C9117.6 (3)
C13—N4—H4125.6C11—C10—C9131.9 (3)
C11—N4—H4125.6N4—C11—C10105.0 (3)
C1—O1—Mg1118.6 (2)N4—C11—C12122.6 (3)
C4—O3—H3109.5C10—C11—C12132.3 (3)
C9—O5—Mg1117.5 (2)O8—C12—O7123.4 (3)
C12—O7—H7109.5O8—C12—C11120.1 (3)
Mg1—O9—H9C119.2O7—C12—C11116.5 (3)
Mg1—O9—H9D130.5N3—C13—N4110.1 (3)
H9C—O9—H9D108.5N3—C13—C14'125.5 (9)
Mg1—O10—H10C107.2N4—C13—C14'121.5 (9)
Mg1—O10—H10D140.1N3—C13—C14125.3 (7)
H10C—O10—H10D108.2N4—C13—C14124.0 (7)
H11C—O11—H11D108.6C13—C14—C15110.3 (9)
H12C—O12—H12D108.7C13—C14—H14A109.6
H13C—O13—H13D107.8C15—C14—H14A109.6
H14G—O14—H14H108.8C13—C14—H14B109.6
O1—C1—O2125.2 (3)C15—C14—H14B109.6
O1—C1—C2116.1 (3)H14A—C14—H14B108.1
O2—C1—C2118.6 (3)C16—C15—C14113.1 (11)
N1—C2—C3110.1 (3)C16—C15—H15A109.0
N1—C2—C1118.1 (3)C14—C15—H15A109.0
C3—C2—C1131.7 (3)C16—C15—H15B109.0
N2—C3—C2104.8 (3)C14—C15—H15B109.0
N2—C3—C4121.6 (3)H15A—C15—H15B107.8
C2—C3—C4133.5 (3)C13—C14'—C15'113.6 (16)
O4—C4—O3121.5 (3)C13—C14'—H14C108.9
O4—C4—C3121.4 (3)C15'—C14'—H14C108.9
O3—C4—C3117.1 (3)C13—C14'—H14D108.9
N1—C5—N2110.3 (3)C15'—C14'—H14D108.9
N1—C5—C6124.3 (5)H14C—C14'—H14D107.7
N2—C5—C6125.0 (5)C16'—C15'—C14'111 (2)
N1—C5—C6'126.9 (12)C16'—C15'—H15C109.3
N2—C5—C6'118.1 (12)C14'—C15'—H15C109.3
C5—C6—C7110.8 (7)C16'—C15'—H15D109.3
C5—C6—H6A109.5C14'—C15'—H15D109.3
C7—C6—H6A109.5H15C—C15'—H15D108.0
C5—C6—H6B109.5C15'—C16'—H16D109.5
C7—C6—H6B109.5C15'—C16'—H16E109.5
H6A—C6—H6B108.1H16D—C16'—H16E109.5
C6—C7—C8109.9 (6)C15'—C16'—H16F109.5
C6—C7—H7A109.7H16D—C16'—H16F109.5
C8—C7—H7A109.7H16E—C16'—H16F109.5
C6—C7—H7B109.7
O10—Mg1—N1—C579.7 (4)C2—N1—C5—C6'−156.2 (14)
O1—Mg1—N1—C5174.6 (4)Mg1—N1—C5—C6'26.8 (15)
O5—Mg1—N1—C5−15.4 (4)C3—N2—C5—N11.0 (4)
N3—Mg1—N1—C5−92.2 (4)C3—N2—C5—C6−172.1 (6)
O10—Mg1—N1—C2−97.2 (2)C3—N2—C5—C6'158.3 (13)
O1—Mg1—N1—C2−2.28 (19)N1—C5—C6—C797.0 (7)
O5—Mg1—N1—C2167.7 (2)N2—C5—C6—C7−90.8 (8)
N3—Mg1—N1—C290.9 (2)C6'—C5—C6—C7−8(3)
O9—Mg1—N3—C1381.6 (4)C5—C6—C7—C8−173.2 (6)
O1—Mg1—N3—C13−11.7 (4)N1—C5—C6'—C7'−100.8 (18)
O5—Mg1—N3—C13174.1 (4)N2—C5—C6'—C7'106.1 (17)
N1—Mg1—N3—C13−89.1 (4)C6—C5—C6'—C7'−6.8 (19)
O9—Mg1—N3—C10−87.2 (2)C5—C6'—C7'—C8'−70 (2)
O1—Mg1—N3—C10179.55 (19)Mg1—O5—C9—O6−174.7 (2)
O5—Mg1—N3—C105.30 (19)Mg1—O5—C9—C105.3 (4)
N1—Mg1—N3—C10102.1 (2)C13—N3—C10—C11−0.2 (3)
O9—Mg1—O1—C1−179.6 (2)Mg1—N3—C10—C11173.0 (2)
O10—Mg1—O1—C188.9 (2)C13—N3—C10—C9−177.8 (3)
O5—Mg1—O1—C1−59.6 (6)Mg1—N3—C10—C9−4.6 (3)
N1—Mg1—O1—C12.5 (2)O5—C9—C10—N3−0.1 (4)
N3—Mg1—O1—C1−89.5 (2)O6—C9—C10—N3180.0 (3)
O9—Mg1—O5—C983.4 (2)O5—C9—C10—C11−177.1 (3)
O10—Mg1—O5—C9174.8 (2)O6—C9—C10—C112.9 (5)
O1—Mg1—O5—C9−36.7 (6)C13—N4—C11—C10−0.3 (3)
N1—Mg1—O5—C9−97.1 (2)C13—N4—C11—C12178.3 (3)
N3—Mg1—O5—C9−5.9 (2)N3—C10—C11—N40.3 (3)
Mg1—O1—C1—O2177.7 (3)C9—C10—C11—N4177.5 (3)
Mg1—O1—C1—C2−2.2 (4)N3—C10—C11—C12−178.1 (3)
C5—N1—C2—C31.2 (4)C9—C10—C11—C12−0.9 (6)
Mg1—N1—C2—C3179.3 (2)N4—C11—C12—O80.3 (5)
C5—N1—C2—C1−176.1 (3)C10—C11—C12—O8178.4 (3)
Mg1—N1—C2—C12.0 (3)N4—C11—C12—O7−179.3 (3)
O1—C1—C2—N10.0 (4)C10—C11—C12—O7−1.1 (5)
O2—C1—C2—N1180.0 (3)C10—N3—C13—N40.0 (4)
O1—C1—C2—C3−176.7 (3)Mg1—N3—C13—N4−169.0 (3)
O2—C1—C2—C33.4 (5)C10—N3—C13—C14'−161.0 (8)
C5—N2—C3—C2−0.2 (4)Mg1—N3—C13—C14'29.9 (9)
C5—N2—C3—C4177.5 (3)C10—N3—C13—C14171.5 (7)
N1—C2—C3—N2−0.6 (3)Mg1—N3—C13—C142.5 (8)
C1—C2—C3—N2176.2 (3)C11—N4—C13—N30.2 (4)
N1—C2—C3—C4−178.0 (3)C11—N4—C13—C14'162.1 (8)
C1—C2—C3—C4−1.1 (6)C11—N4—C13—C14−171.5 (7)
N2—C3—C4—O40.9 (5)N3—C13—C14—C15122.3 (10)
C2—C3—C4—O4177.9 (3)N4—C13—C14—C15−67.3 (11)
N2—C3—C4—O3−178.4 (3)C14'—C13—C14—C1524 (3)
C2—C3—C4—O3−1.4 (6)C13—C14—C15—C16−63.5 (15)
C2—N1—C5—N2−1.4 (4)N3—C13—C14'—C15'81.0 (19)
Mg1—N1—C5—N2−178.4 (3)N4—C13—C14'—C15'−78.0 (18)
C2—N1—C5—C6171.8 (6)C14—C13—C14'—C15'179 (5)
Mg1—N1—C5—C6−5.2 (8)C13—C14'—C15'—C16'−173.1 (15)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···O120.861.892.745 (4)170
N4—H4···O130.861.912.737 (4)162
O3—H3···O20.821.702.511 (3)173
O7—H7···O60.821.652.461 (3)172
O9—H9C···O8i0.851.882.732 (3)177
O9—H9D···O11ii0.851.832.678 (4)176
O10—H10C···O4iii0.851.942.787 (3)174
O10—H10D···O8iv0.852.062.905 (3)174
O11—H11C···O2v0.851.952.794 (3)172
O11—H11D···O5vi0.852.052.893 (3)172
O12—H12C···O7vi0.852.052.888 (4)167
O12—H12D···O14v0.851.842.672 (6)167
O13—H13C···O140.851.852.643 (6)156
O13—H13D···O11vii0.852.072.869 (5)156
O14—H14G···O1viii0.852.002.816 (5)162
O14—H14H···O1ix0.851.982.799 (5)162

Symmetry codes: (i) −x, −y+1, −z+2; (ii) x, y−1, z+1; (iii) −x+1, −y, −z+1; (iv) x, y−1, z; (v) −x+1, −y+1, −z+1; (vi) −x, −y+1, −z+1; (vii) x, y, z+1; (viii) x, y+1, z; (ix) −x+1, −y+1, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2281).

References

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