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Acta Cryst. (2008). E64, m1621    [ doi:10.1107/S1600536808037859 ]

Nitrato[N,N,N',N'-tetrakis(1H-benzimidazol-2-ylmethyl)ethane-1,2-diamine]calcium(II) nitrate methanol trisolvate

B. Huang, Y. Pei and L. Wang

Abstract top

In the title compound, [Ca(NO3)(C34H32N10)]NO3·3CH4O, the CaII ion is coordinated by six N atoms of the EDTB ligand {EDTB is N,N,N',N'-tetrakis[(2-benzimidazolyl)methyl]-1,2-ethanediamine} and two O atoms from the nitrate ligand, to form a distorted dodecahedral geometry. The crystal packing is stabilized by intermolecular N-H...O, N-H...N and O-H...O hydrogen bonds, which link the constituent units into a three-dimensional network. The uncoordinated nitrate anion is disordered over two sites, with fixed occupancies of 0.77 and 0.23.

Comment top

Benzimidazole containing ligands and their metal complexes have been reported (Chen et al., 2004; Liao et al., 2001; Pei et al., 2007). In continuation of our work on these types of ligands, we report here the crystal structure of the title compound, [Ca(EDTB)(NO3)]+.NO3-.3CH3OH (EDTB is N,N,N',N'-Tetrakis-[(2-benzimidazolyl)methyl] -1,2-ethanediamine).

The asymmetric unit consists of one [Ca(EDTB)(NO3)]+ cationic unit, one uncoordinated nitrate anion and three methanol solvent molecules (Fig. 1). The structure of the monocation shows an eight-coordinated geometry with CaII ion at the centre of a distorted dodecahedral environment (Table 1). The CaII ion is coordinated by four benzimidazole (bzim) N atoms (N3,N5,N7 and N9) and two amine N atoms (N1 and N2) from the EDTB ligand, and two O atoms (O1/O2) from the coordinated nitrate ion.

The coordination cations, uncoordinated nitrate anions and free methanol molecules are interlinked into a three-dimensional network by a combination of six N—H···O, two O—H···O and three C—H···O hydrogen bonds (Table 2 and Fig. 2).

Related literature top

For general background, see: Chen et al. (2004); Liao et al. (2001); Pei et al. (2007). For the synthesis of the EDTB ligand, see: Hendriks et al. (1982).

Experimental top

N,N,N',N'-Tetrakis-[(2-benzimidazolyl)methyl] -1,2-ethanediamine (EDTB) ligand was synthesized according to the literature method (Hendriks et al., 1982). EDTB (0.58 g, 1.0 mmol) in hot methanol (20 ml) was added slowly to a solution of Ca(NO3)2.4H2O (0.236 g, 1.0 mmol) in methanol (10 ml) and the mixture was stirred for 1 h. After filtration, the solution was allowed to stand at room temperature. Block-shaped pale red crystals suitable for X-ray analysis were obtained after several days in 45% yield.

Refinement top

The nitrate anion is disordered over two sites. The site occupancies were initially refined to 0.77 (1) and 0.23 (1) for the major and minor components, respectively, and later fixed. In both disorder components, the N—O distances were restrained to 1.38 (1) Å and the O···O distances were restrained to be equal. C-bound H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and were refined as riding with Uiso(H) = 1.2–1.5Ueq(C). O– and N-bound H atoms were first located in a difference map and then constrained to be at their ideal positions (O—H = 0.82 Å and N—H = 0.86 Å) with Uiso values set at 1.2Ueq(N) and 1.5Ueq(O).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Only the major component of the disordered nitrate ion is shown.
[Figure 2] Fig. 2. The crystal structure of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines.
Nitrato[N,N,N',N'-tetrakis(1H-benzimidazol- 1-ylmethyl)ethane-1,2-diamine]calcium(II) nitrate methanol trisolvate top
Crystal data top
[Ca(NO3)(C34H32N10)]NO3·3CH4OF(000) = 1768
Mr = 840.92Dx = 1.336 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6962 reflections
a = 9.5945 (4) Åθ = 2.2–21.4°
b = 25.3531 (11) ŵ = 0.22 mm−1
c = 17.8402 (7) ÅT = 294 K
β = 105.599 (1)°Block, pale-red
V = 4179.8 (3) Å30.20 × 0.20 × 0.10 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		8189 independent reflections
Radiation source: fine-focus sealed tube4825 reflections with I > 2σ(I)
graphiteRint = 0.146
φ and ω scansθmax = 26.0°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)		h = −11→11
Tmin = 0.948, Tmax = 0.979k = −31→31
43547 measured reflectionsl = −22→22
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171H-atom parameters constrained
S = 0.90 w = 1/[σ2(Fo2) + (0.0978P)2]
where P = (Fo2 + 2Fc2)/3
8189 reflections(Δ/σ)max = 0.001
575 parametersΔρmax = 0.47 e Å−3
23 restraintsΔρmin = −0.37 e Å−3
Crystal data top
[Ca(NO3)(C34H32N10)]NO3·3CH4OV = 4179.8 (3) Å3
Mr = 840.92Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.5945 (4) ŵ = 0.22 mm−1
b = 25.3531 (11) ÅT = 294 K
c = 17.8402 (7) Å0.20 × 0.20 × 0.10 mm
β = 105.599 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		8189 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)		4825 reflections with I > 2σ(I)
Tmin = 0.948, Tmax = 0.979Rint = 0.146
43547 measured reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.065H-atom parameters constrained
wR(F2) = 0.171Δρmax = 0.47 e Å−3
S = 0.90Δρmin = −0.37 e Å−3
8189 reflectionsAbsolute structure: ?
575 parametersFlack parameter: ?
23 restraintsRogers parameter: ?
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
Ca10.93863 (6)0.24863 (2)0.58359 (3)0.03938 (18)
C10.7836 (3)0.14868 (11)0.65167 (19)0.0572 (8)
H1A0.70700.12770.66280.069*
H1B0.86780.14670.69620.069*
C20.8201 (3)0.12762 (11)0.58169 (19)0.0540 (8)
C30.8889 (3)0.12150 (12)0.47646 (19)0.0588 (8)
C40.9379 (4)0.12879 (15)0.4103 (2)0.0768 (11)
H40.96890.16180.39860.092*
C50.9393 (5)0.08604 (18)0.3627 (3)0.1052 (15)
H50.97360.09000.31900.126*
C60.8897 (7)0.03698 (19)0.3796 (3)0.136 (2)
H60.89070.00880.34640.163*
C70.8402 (7)0.02916 (18)0.4427 (3)0.138 (2)
H70.8071−0.00370.45340.165*
C80.8404 (5)0.07194 (13)0.4911 (2)0.0808 (11)
C90.5963 (3)0.20632 (12)0.57942 (19)0.0571 (8)
H9A0.51910.20420.60490.069*
H9B0.58730.17650.54440.069*
C100.5819 (3)0.25616 (11)0.53395 (17)0.0459 (7)
C110.6306 (3)0.32351 (11)0.47183 (16)0.0460 (7)
C120.6945 (4)0.36285 (12)0.43761 (19)0.0595 (8)
H120.79450.36640.44950.071*
C130.6052 (4)0.39592 (12)0.38618 (19)0.0643 (9)
H130.64570.42230.36260.077*
C140.4564 (4)0.39146 (12)0.3680 (2)0.0650 (9)
H140.39890.41480.33260.078*
C150.3923 (3)0.35281 (12)0.40159 (19)0.0594 (8)
H150.29220.34980.39020.071*
C160.4812 (3)0.31902 (11)0.45229 (17)0.0475 (7)
C170.7243 (3)0.23028 (13)0.71045 (18)0.0564 (8)
H17A0.66630.26200.69680.068*
H17B0.67430.20690.73760.068*
C180.8664 (3)0.24460 (12)0.76340 (18)0.0558 (8)
H18A0.85080.26200.80890.067*
H18B0.92080.21260.78080.067*
C190.8988 (3)0.33411 (11)0.72146 (19)0.0562 (8)
H19A0.92110.35000.77280.067*
H19B0.79450.33430.70000.067*
C200.9683 (3)0.36492 (11)0.67018 (17)0.0490 (7)
C211.0657 (3)0.38720 (11)0.57887 (18)0.0492 (7)
C221.1232 (4)0.39029 (12)0.5158 (2)0.0658 (9)
H221.12400.36080.48480.079*
C231.1795 (4)0.43753 (13)0.4995 (2)0.0844 (12)
H231.21770.44040.45690.101*
C241.1788 (5)0.48114 (14)0.5472 (3)0.0960 (14)
H241.21770.51270.53550.115*
C251.1242 (5)0.47959 (14)0.6094 (3)0.0881 (12)
H251.12570.50910.64060.106*
C261.0661 (3)0.43219 (11)0.6248 (2)0.0599 (8)
C271.1042 (3)0.27818 (12)0.77325 (17)0.0532 (8)
H27A1.10900.27740.82820.064*
H27B1.15360.30970.76320.064*
C281.1768 (3)0.23033 (11)0.75227 (16)0.0471 (7)
C291.2351 (3)0.16532 (11)0.68917 (17)0.0499 (7)
C301.2468 (4)0.12775 (13)0.6351 (2)0.0702 (10)
H301.18190.12670.58590.084*
C311.3574 (4)0.09212 (15)0.6566 (2)0.0813 (11)
H311.36820.06660.62120.098*
C321.4533 (4)0.09323 (14)0.7297 (2)0.0750 (10)
H321.52600.06790.74280.090*
C331.4440 (4)0.13041 (14)0.7828 (2)0.0664 (9)
H331.50940.13140.83190.080*
C341.3342 (3)0.16646 (11)0.76108 (17)0.0494 (7)
C350.3284 (6)0.1315 (2)0.4261 (3)0.1300 (19)
H35A0.31480.10530.46230.195*
H35B0.26910.12320.37500.195*
H35C0.30150.16550.44150.195*
C360.4021 (5)0.3258 (2)0.6834 (4)0.136 (2)
H36A0.38230.32400.73340.204*
H36B0.38680.29170.65910.204*
H36C0.33850.35100.65130.204*
C370.6019 (7)0.4540 (3)0.5955 (4)0.147 (2)
H37A0.55680.48790.58340.220*
H37B0.55120.42850.55840.220*
H37C0.70080.45610.59360.220*
N10.7361 (2)0.20398 (9)0.63783 (14)0.0480 (6)
N20.9530 (2)0.27953 (9)0.72732 (13)0.0463 (6)
N30.8747 (3)0.15622 (9)0.53404 (14)0.0510 (6)
N40.7990 (4)0.07761 (10)0.55867 (19)0.0832 (9)
H4A0.76530.05300.58210.100*
N50.6927 (2)0.28340 (9)0.52322 (14)0.0488 (6)
N60.4545 (2)0.27564 (10)0.49387 (15)0.0530 (6)
H6A0.37080.26350.49380.064*
N71.0047 (2)0.34531 (9)0.60981 (14)0.0480 (6)
N81.0045 (3)0.41587 (10)0.68268 (16)0.0637 (7)
H80.99170.43500.72010.076*
N91.1344 (2)0.20637 (9)0.68459 (13)0.0507 (6)
N101.2934 (3)0.20879 (10)0.79974 (14)0.0539 (6)
H101.33610.21920.84610.065*
N111.0825 (3)0.25741 (8)0.45680 (15)0.0452 (6)
O10.9506 (2)0.26521 (8)0.45075 (11)0.0521 (5)
O21.1601 (2)0.24507 (8)0.52220 (12)0.0590 (6)
O31.1313 (2)0.26311 (10)0.40031 (13)0.0689 (6)
N120.8396 (12)0.4913 (3)0.8304 (5)0.109 (5)0.77
O40.9043 (11)0.4561 (3)0.8003 (5)0.205 (5)0.77
O50.7299 (9)0.5142 (3)0.7906 (5)0.155 (4)0.77
O60.8972 (10)0.5031 (4)0.9014 (5)0.142 (4)0.77
O70.4716 (5)0.13242 (19)0.4254 (3)0.1470 (14)
H7A0.48950.10630.40250.220*
O80.5364 (4)0.34029 (15)0.6924 (4)0.177 (2)
H8A0.53860.37130.67950.265*
O90.5977 (8)0.4396 (2)0.6665 (3)0.208 (2)
H90.65310.45820.69880.312*
O5'0.7826 (15)0.5023 (8)0.7646 (13)0.128 (10)0.23
O6'0.9780 (19)0.4577 (8)0.8264 (11)0.101 (6)0.23
N12'0.877 (2)0.4910 (9)0.8299 (11)0.13 (2)0.23
O4'0.834 (3)0.4922 (11)0.8925 (13)0.118 (9)0.23
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ca10.0386 (3)0.0402 (3)0.0392 (3)−0.0034 (2)0.0104 (2)0.0009 (2)
C10.065 (2)0.0470 (17)0.065 (2)−0.0038 (14)0.0252 (16)0.0093 (15)
C20.0602 (19)0.0429 (16)0.0598 (19)−0.0062 (14)0.0177 (16)0.0041 (14)
C30.069 (2)0.0490 (18)0.059 (2)−0.0120 (15)0.0190 (17)−0.0078 (15)
C40.102 (3)0.065 (2)0.072 (2)−0.0244 (19)0.038 (2)−0.0197 (18)
C50.152 (4)0.090 (3)0.092 (3)−0.031 (3)0.064 (3)−0.033 (3)
C60.223 (6)0.078 (3)0.131 (4)−0.047 (4)0.092 (5)−0.048 (3)
C70.236 (7)0.066 (3)0.147 (5)−0.056 (3)0.113 (5)−0.039 (3)
C80.120 (3)0.049 (2)0.085 (3)−0.0203 (19)0.050 (2)−0.0139 (18)
C90.0488 (18)0.0552 (18)0.070 (2)−0.0111 (14)0.0204 (16)0.0041 (16)
C100.0356 (15)0.0493 (17)0.0527 (17)−0.0026 (13)0.0117 (13)−0.0022 (13)
C110.0450 (17)0.0437 (16)0.0505 (17)0.0017 (12)0.0150 (13)−0.0027 (13)
C120.0568 (19)0.0535 (18)0.071 (2)−0.0020 (15)0.0220 (17)0.0052 (16)
C130.078 (2)0.0466 (18)0.068 (2)−0.0015 (16)0.0188 (19)0.0037 (15)
C140.074 (2)0.0493 (19)0.065 (2)0.0160 (17)0.0062 (18)−0.0016 (16)
C150.0529 (18)0.0546 (19)0.066 (2)0.0103 (15)0.0071 (16)−0.0084 (16)
C160.0443 (17)0.0490 (17)0.0481 (17)0.0025 (13)0.0107 (14)−0.0079 (13)
C170.060 (2)0.0584 (18)0.060 (2)−0.0037 (15)0.0324 (17)0.0069 (15)
C180.071 (2)0.0562 (18)0.0481 (17)−0.0032 (15)0.0288 (16)0.0014 (14)
C190.064 (2)0.0507 (18)0.062 (2)0.0030 (14)0.0301 (16)−0.0033 (14)
C200.0485 (17)0.0427 (16)0.0580 (19)0.0012 (13)0.0182 (15)−0.0043 (14)
C210.0526 (18)0.0419 (16)0.0576 (19)−0.0071 (13)0.0222 (15)−0.0049 (13)
C220.085 (2)0.0462 (18)0.076 (2)−0.0164 (16)0.038 (2)−0.0129 (16)
C230.118 (3)0.056 (2)0.102 (3)−0.025 (2)0.067 (3)−0.010 (2)
C240.137 (4)0.052 (2)0.124 (4)−0.034 (2)0.078 (3)−0.014 (2)
C250.126 (3)0.046 (2)0.109 (3)−0.021 (2)0.061 (3)−0.021 (2)
C260.071 (2)0.0416 (17)0.076 (2)−0.0046 (14)0.0355 (18)−0.0061 (15)
C270.0584 (19)0.0545 (18)0.0450 (17)−0.0018 (14)0.0113 (15)−0.0084 (14)
C280.0476 (17)0.0537 (16)0.0385 (16)−0.0039 (13)0.0089 (14)−0.0003 (13)
C290.0502 (17)0.0471 (16)0.0515 (18)0.0021 (13)0.0122 (14)0.0004 (13)
C300.067 (2)0.067 (2)0.068 (2)0.0117 (17)0.0033 (18)−0.0148 (18)
C310.084 (3)0.062 (2)0.098 (3)0.0080 (19)0.024 (2)−0.019 (2)
C320.061 (2)0.064 (2)0.096 (3)0.0147 (17)0.015 (2)0.004 (2)
C330.059 (2)0.069 (2)0.066 (2)0.0101 (17)0.0093 (17)0.0084 (18)
C340.0456 (17)0.0530 (17)0.0482 (17)−0.0010 (14)0.0102 (14)0.0057 (14)
C350.120 (5)0.140 (5)0.141 (5)−0.007 (4)0.054 (4)−0.030 (4)
C360.079 (3)0.154 (5)0.186 (6)−0.009 (3)0.054 (4)−0.033 (4)
C370.193 (6)0.135 (5)0.122 (5)−0.006 (4)0.059 (5)0.003 (4)
N10.0480 (14)0.0466 (14)0.0518 (14)−0.0044 (10)0.0176 (12)0.0054 (11)
N20.0498 (14)0.0475 (14)0.0441 (14)0.0013 (11)0.0172 (11)0.0011 (10)
N30.0591 (15)0.0444 (13)0.0510 (15)−0.0113 (11)0.0176 (12)−0.0040 (11)
N40.126 (3)0.0428 (16)0.097 (2)−0.0225 (16)0.057 (2)0.0000 (15)
N50.0382 (13)0.0489 (14)0.0597 (15)−0.0036 (10)0.0138 (12)0.0055 (11)
N60.0340 (13)0.0583 (15)0.0665 (17)−0.0058 (11)0.0134 (12)−0.0002 (13)
N70.0517 (14)0.0411 (13)0.0555 (15)−0.0048 (11)0.0219 (12)−0.0065 (11)
N80.0808 (19)0.0448 (14)0.0768 (19)−0.0018 (13)0.0407 (16)−0.0149 (13)
N90.0536 (15)0.0523 (14)0.0424 (14)0.0042 (11)0.0063 (11)−0.0014 (11)
N100.0521 (15)0.0625 (16)0.0404 (14)0.0001 (12)0.0009 (12)−0.0049 (12)
N110.0423 (14)0.0449 (13)0.0499 (15)−0.0071 (10)0.0152 (12)0.0003 (11)
O10.0349 (11)0.0757 (14)0.0457 (12)−0.0008 (9)0.0107 (9)0.0087 (10)
O20.0432 (11)0.0752 (15)0.0525 (13)0.0030 (10)0.0025 (10)0.0073 (11)
O30.0608 (14)0.0940 (17)0.0617 (15)−0.0026 (12)0.0334 (12)0.0064 (12)
N120.169 (9)0.063 (6)0.134 (12)−0.034 (5)0.107 (10)−0.030 (6)
O40.319 (12)0.123 (6)0.252 (11)0.008 (7)0.214 (10)−0.065 (6)
O50.243 (10)0.101 (4)0.126 (5)−0.001 (5)0.058 (6)−0.003 (4)
O60.150 (7)0.116 (6)0.179 (8)−0.010 (5)0.077 (6)−0.051 (5)
O70.128 (3)0.170 (4)0.132 (3)−0.008 (3)0.018 (2)−0.053 (3)
O80.096 (3)0.113 (3)0.342 (7)0.029 (2)0.096 (3)0.051 (4)
O90.299 (7)0.161 (4)0.176 (5)−0.108 (4)0.086 (5)−0.012 (4)
O5'0.037 (7)0.111 (15)0.19 (2)−0.029 (8)−0.048 (11)0.074 (15)
O6'0.157 (16)0.079 (11)0.068 (8)−0.031 (10)0.031 (10)0.001 (7)
N12'0.14 (3)0.12 (3)0.14 (4)−0.03 (2)0.05 (3)0.00 (3)
O4'0.13 (2)0.090 (15)0.130 (18)0.016 (14)0.034 (12)−0.066 (12)
Geometric parameters (Å, °) top
Ca1—O12.440 (2)C21—N71.396 (4)
Ca1—N92.470 (2)C21—C261.404 (4)
Ca1—N52.477 (2)C22—C231.377 (4)
Ca1—N32.521 (2)C22—H220.93
Ca1—N72.543 (2)C23—C241.396 (5)
Ca1—O22.641 (2)C23—H230.93
Ca1—N12.647 (2)C24—C251.349 (5)
Ca1—N22.649 (2)C24—H240.93
C1—N11.474 (4)C25—C261.383 (5)
C1—C21.484 (4)C25—H250.93
C1—H1A0.97C26—N81.384 (4)
C1—H1B0.97C27—N21.462 (3)
C2—N31.328 (4)C27—C281.496 (4)
C2—N41.331 (4)C27—H27A0.97
C3—N31.387 (4)C27—H27B0.97
C3—C81.389 (4)C28—N91.315 (3)
C3—C41.394 (5)C28—N101.326 (3)
C4—C51.380 (5)C29—C341.376 (4)
C4—H40.93C29—C301.382 (4)
C5—C61.394 (6)C29—N91.407 (3)
C5—H50.93C30—C311.368 (5)
C6—C71.348 (6)C30—H300.93
C6—H60.93C31—C321.379 (5)
C7—C81.385 (5)C31—H310.93
C7—H70.93C32—C331.357 (5)
C8—N41.375 (4)C32—H320.93
C9—N11.462 (4)C33—C341.370 (4)
C9—C101.488 (4)C33—H330.93
C9—H9A0.97C34—N101.388 (4)
C9—H9B0.97C35—O71.377 (6)
C10—N51.324 (3)C35—H35A0.96
C10—N61.334 (3)C35—H35B0.96
C11—C161.386 (4)C35—H35C0.96
C11—N51.391 (3)C36—O81.308 (5)
C11—C121.395 (4)C36—H36A0.96
C12—C131.362 (4)C36—H36B0.96
C12—H120.93C36—H36C0.96
C13—C141.381 (4)C37—O91.328 (6)
C13—H130.93C37—H37A0.96
C14—C151.377 (5)C37—H37B0.96
C14—H140.93C37—H37C0.96
C15—C161.366 (4)N4—H4A0.86
C15—H150.93N6—H6A0.86
C16—N61.388 (4)N8—H80.86
C17—C181.480 (4)N10—H100.86
C17—N11.488 (4)N11—O31.229 (3)
C17—H17A0.97N11—O21.244 (3)
C17—H17B0.97N11—O11.257 (3)
C18—N21.476 (4)N12—O51.245 (8)
C18—H18A0.97N12—O61.275 (7)
C18—H18B0.97N12—O41.283 (8)
C19—N21.472 (4)O7—H7A0.82
C19—C201.490 (4)O8—H8A0.82
C19—H19A0.97O9—H90.82
C19—H19B0.97O5'—N12'1.301 (10)
C20—N71.316 (3)O6'—N12'1.297 (10)
C20—N81.340 (4)N12'—O4'1.292 (10)
C21—C221.382 (4)
O1—Ca1—N9123.93 (8)C21—C22—H22120.4
O1—Ca1—N578.72 (7)C22—C23—C24119.6 (3)
N9—Ca1—N5156.91 (8)C22—C23—H23120.2
O1—Ca1—N383.69 (8)C24—C23—H23120.2
N9—Ca1—N385.31 (8)C25—C24—C23123.0 (3)
N5—Ca1—N393.72 (8)C25—C24—H24118.5
O1—Ca1—N786.46 (8)C23—C24—H24118.5
N9—Ca1—N7100.42 (8)C24—C25—C26117.1 (3)
N5—Ca1—N784.15 (8)C24—C25—H25121.4
N3—Ca1—N7170.14 (8)C26—C25—H25121.4
O1—Ca1—O249.45 (6)C25—C26—N8133.2 (3)
N9—Ca1—O275.46 (7)C25—C26—C21121.8 (3)
N5—Ca1—O2127.61 (7)N8—C26—C21105.0 (2)
N3—Ca1—O288.27 (7)N2—C27—C28109.7 (2)
N7—Ca1—O285.46 (7)N2—C27—H27A109.7
O1—Ca1—N1131.28 (7)C28—C27—H27A109.7
N9—Ca1—N192.11 (8)N2—C27—H27B109.7
N5—Ca1—N166.68 (7)C28—C27—H27B109.7
N3—Ca1—N166.25 (8)H27A—C27—H27B108.2
N7—Ca1—N1121.07 (8)N9—C28—N10113.3 (3)
O2—Ca1—N1152.71 (7)N9—C28—C27123.7 (2)
O1—Ca1—N2152.31 (7)N10—C28—C27123.0 (2)
N9—Ca1—N265.84 (7)C34—C29—C30120.0 (3)
N5—Ca1—N296.39 (8)C34—C29—N9109.3 (3)
N3—Ca1—N2123.96 (8)C30—C29—N9130.7 (3)
N7—Ca1—N265.88 (7)C31—C30—C29117.5 (3)
O2—Ca1—N2124.98 (7)C31—C30—H30121.2
N1—Ca1—N267.97 (7)C29—C30—H30121.2
N1—C1—C2109.5 (2)C30—C31—C32121.5 (3)
N1—C1—H1A109.8C30—C31—H31119.3
C2—C1—H1A109.8C32—C31—H31119.3
N1—C1—H1B109.8C33—C32—C31121.5 (3)
C2—C1—H1B109.8C33—C32—H32119.2
H1A—C1—H1B108.2C31—C32—H32119.2
N3—C2—N4112.1 (3)C32—C33—C34117.1 (3)
N3—C2—C1124.4 (3)C32—C33—H33121.4
N4—C2—C1123.5 (3)C34—C33—H33121.4
N3—C3—C8109.3 (3)C33—C34—C29122.4 (3)
N3—C3—C4131.7 (3)C33—C34—N10132.3 (3)
C8—C3—C4119.0 (3)C29—C34—N10105.3 (2)
C5—C4—C3118.6 (4)O7—C35—H35A109.5
C5—C4—H4120.7O7—C35—H35B109.5
C3—C4—H4120.7H35A—C35—H35B109.5
C4—C5—C6120.5 (4)O7—C35—H35C109.5
C4—C5—H5119.8H35A—C35—H35C109.5
C6—C5—H5119.8H35B—C35—H35C109.5
C7—C6—C5122.0 (4)O8—C36—H36A109.5
C7—C6—H6119.0O8—C36—H36B109.5
C5—C6—H6119.0H36A—C36—H36B109.5
C6—C7—C8117.6 (4)O8—C36—H36C109.5
C6—C7—H7121.2H36A—C36—H36C109.5
C8—C7—H7121.2H36B—C36—H36C109.5
N4—C8—C7132.5 (4)O9—C37—H37A109.5
N4—C8—C3105.1 (3)O9—C37—H37B109.5
C7—C8—C3122.4 (4)H37A—C37—H37B109.5
N1—C9—C10110.9 (2)O9—C37—H37C109.5
N1—C9—H9A109.5H37A—C37—H37C109.5
C10—C9—H9A109.5H37B—C37—H37C109.5
N1—C9—H9B109.5C9—N1—C1110.0 (2)
C10—C9—H9B109.5C9—N1—C17109.4 (2)
H9A—C9—H9B108.1C1—N1—C17111.9 (2)
N5—C10—N6112.7 (3)C9—N1—Ca1110.18 (16)
N5—C10—C9124.1 (2)C1—N1—Ca1104.11 (17)
N6—C10—C9123.0 (2)C17—N1—Ca1111.23 (16)
C16—C11—N5109.7 (2)C27—N2—C19109.9 (2)
C16—C11—C12119.7 (3)C27—N2—C18109.4 (2)
N5—C11—C12130.6 (3)C19—N2—C18111.4 (2)
C13—C12—C11117.7 (3)C27—N2—Ca1108.73 (16)
C13—C12—H12121.2C19—N2—Ca1106.49 (17)
C11—C12—H12121.2C18—N2—Ca1110.85 (17)
C12—C13—C14122.1 (3)C2—N3—C3105.2 (2)
C12—C13—H13119.0C2—N3—Ca1112.57 (19)
C14—C13—H13119.0C3—N3—Ca1141.8 (2)
C15—C14—C13120.7 (3)C2—N4—C8108.3 (3)
C15—C14—H14119.7C2—N4—H4A125.8
C13—C14—H14119.7C8—N4—H4A125.8
C16—C15—C14117.5 (3)C10—N5—C11104.9 (2)
C16—C15—H15121.2C10—N5—Ca1117.35 (18)
C14—C15—H15121.2C11—N5—Ca1137.37 (18)
C15—C16—C11122.3 (3)C10—N6—C16107.8 (2)
C15—C16—N6132.8 (3)C10—N6—H6A126.1
C11—C16—N6104.9 (2)C16—N6—H6A126.1
C18—C17—N1113.1 (2)C20—N7—C21105.6 (2)
C18—C17—H17A109.0C20—N7—Ca1114.01 (18)
N1—C17—H17A109.0C21—N7—Ca1140.40 (19)
C18—C17—H17B109.0C20—N8—C26107.9 (2)
N1—C17—H17B109.0C20—N8—H8126.0
H17A—C17—H17B107.8C26—N8—H8126.0
N2—C18—C17113.5 (2)C28—N9—C29104.5 (2)
N2—C18—H18A108.9C28—N9—Ca1117.15 (19)
C17—C18—H18A108.9C29—N9—Ca1137.61 (18)
N2—C18—H18B108.9C28—N10—C34107.7 (2)
C17—C18—H18B108.9C28—N10—H10126.2
H18A—C18—H18B107.7C34—N10—H10126.2
N2—C19—C20109.2 (2)O3—N11—O2122.4 (2)
N2—C19—H19A109.8O3—N11—O1120.5 (2)
C20—C19—H19A109.8O2—N11—O1117.1 (2)
N2—C19—H19B109.8N11—O1—Ca1101.47 (15)
C20—C19—H19B109.8N11—O2—Ca192.01 (15)
H19A—C19—H19B108.3O5—N12—O6122.0 (7)
N7—C20—N8112.7 (3)O5—N12—O4121.1 (7)
N7—C20—C19124.4 (3)O6—N12—O4116.8 (8)
N8—C20—C19122.8 (3)C35—O7—H7A109.5
C22—C21—N7131.8 (3)C36—O8—H8A109.5
C22—C21—C26119.4 (3)C37—O9—H9109.5
N7—C21—C26108.8 (3)O4'—N12'—O6'118.1 (10)
C23—C22—C21119.1 (3)O4'—N12'—O5'117.4 (10)
C23—C22—H22120.4O6'—N12'—O5'116.7 (9)
N1—C1—C2—N332.3 (4)C1—C2—N3—Ca16.9 (4)
N1—C1—C2—N4−146.5 (3)C8—C3—N3—C20.4 (4)
N3—C3—C4—C5−179.8 (4)C4—C3—N3—C2178.9 (4)
C8—C3—C4—C5−1.5 (6)C8—C3—N3—Ca1172.0 (3)
C3—C4—C5—C61.4 (7)C4—C3—N3—Ca1−9.6 (6)
C4—C5—C6—C7−0.6 (9)O1—Ca1—N3—C2−165.3 (2)
C5—C6—C7—C8−0.1 (10)N9—Ca1—N3—C269.7 (2)
C6—C7—C8—N4−179.7 (5)N5—Ca1—N3—C2−87.1 (2)
C6—C7—C8—C30.1 (9)O2—Ca1—N3—C2145.3 (2)
N3—C3—C8—N4−0.8 (4)N1—Ca1—N3—C2−24.65 (19)
C4—C3—C8—N4−179.4 (3)N2—Ca1—N3—C213.1 (2)
N3—C3—C8—C7179.4 (4)O1—Ca1—N3—C323.5 (3)
C4—C3—C8—C70.7 (7)N9—Ca1—N3—C3−101.5 (3)
N1—C9—C10—N526.2 (4)N5—Ca1—N3—C3101.7 (3)
N1—C9—C10—N6−159.9 (3)O2—Ca1—N3—C3−25.9 (3)
C16—C11—C12—C130.6 (4)N1—Ca1—N3—C3164.2 (3)
N5—C11—C12—C13177.2 (3)N2—Ca1—N3—C3−158.1 (3)
C11—C12—C13—C140.2 (5)N3—C2—N4—C8−0.6 (4)
C12—C13—C14—C15−0.1 (5)C1—C2—N4—C8178.3 (3)
C13—C14—C15—C16−0.9 (5)C7—C8—N4—C2−179.3 (5)
C14—C15—C16—C111.8 (4)C3—C8—N4—C20.8 (4)
C14—C15—C16—N6−177.8 (3)N6—C10—N5—C11−0.2 (3)
N5—C11—C16—C15−178.9 (3)C9—C10—N5—C11174.3 (3)
C12—C11—C16—C15−1.7 (4)N6—C10—N5—Ca1−174.70 (18)
N5—C11—C16—N60.7 (3)C9—C10—N5—Ca1−0.2 (4)
C12—C11—C16—N6178.0 (3)C16—C11—N5—C10−0.4 (3)
N1—C17—C18—N257.6 (3)C12—C11—N5—C10−177.2 (3)
N2—C19—C20—N733.5 (4)C16—C11—N5—Ca1172.5 (2)
N2—C19—C20—N8−144.3 (3)C12—C11—N5—Ca1−4.4 (5)
N7—C21—C22—C23−178.7 (3)O1—Ca1—N5—C10130.8 (2)
C26—C21—C22—C23−0.1 (5)N9—Ca1—N5—C10−38.7 (3)
C21—C22—C23—C240.7 (6)N3—Ca1—N5—C1048.0 (2)
C22—C23—C24—C25−0.4 (7)N7—Ca1—N5—C10−141.6 (2)
C23—C24—C25—C26−0.5 (7)O2—Ca1—N5—C10138.70 (19)
C24—C25—C26—N8178.7 (4)N1—Ca1—N5—C10−14.1 (2)
C24—C25—C26—C211.1 (6)N2—Ca1—N5—C10−76.8 (2)
C22—C21—C26—C25−0.8 (5)O1—Ca1—N5—C11−41.4 (3)
N7—C21—C26—C25178.1 (3)N9—Ca1—N5—C11149.1 (2)
C22—C21—C26—N8−179.0 (3)N3—Ca1—N5—C11−124.2 (3)
N7—C21—C26—N80.0 (3)N7—Ca1—N5—C1146.2 (3)
N2—C27—C28—N925.6 (4)O2—Ca1—N5—C11−33.5 (3)
N2—C27—C28—N10−156.4 (3)N1—Ca1—N5—C11173.7 (3)
C34—C29—C30—C311.1 (5)N2—Ca1—N5—C11111.0 (3)
N9—C29—C30—C31−179.7 (3)N5—C10—N6—C160.6 (3)
C29—C30—C31—C320.5 (6)C9—C10—N6—C16−173.9 (3)
C30—C31—C32—C33−1.5 (6)C15—C16—N6—C10178.8 (3)
C31—C32—C33—C340.7 (6)C11—C16—N6—C10−0.8 (3)
C32—C33—C34—C290.9 (5)N8—C20—N7—C21−1.9 (3)
C32—C33—C34—N10179.9 (3)C19—C20—N7—C21−179.9 (3)
C30—C29—C34—C33−1.9 (5)N8—C20—N7—Ca1179.92 (19)
N9—C29—C34—C33178.8 (3)C19—C20—N7—Ca11.9 (3)
C30—C29—C34—N10178.9 (3)C22—C21—N7—C20179.9 (3)
N9—C29—C34—N10−0.5 (3)C26—C21—N7—C201.1 (3)
C10—C9—N1—C1−149.5 (3)C22—C21—N7—Ca1−2.7 (5)
C10—C9—N1—C1787.3 (3)C26—C21—N7—Ca1178.5 (2)
C10—C9—N1—Ca1−35.3 (3)O1—Ca1—N7—C20158.32 (19)
C2—C1—N1—C968.8 (3)N9—Ca1—N7—C20−77.8 (2)
C2—C1—N1—C17−169.4 (2)N5—Ca1—N7—C2079.3 (2)
C2—C1—N1—Ca1−49.2 (3)O2—Ca1—N7—C20−152.1 (2)
C18—C17—N1—C9−162.2 (2)N1—Ca1—N7—C2021.1 (2)
C18—C17—N1—C175.7 (3)N2—Ca1—N7—C20−20.38 (18)
C18—C17—N1—Ca1−40.2 (3)O1—Ca1—N7—C21−18.9 (3)
O1—Ca1—N1—C9−22.1 (2)N9—Ca1—N7—C21104.9 (3)
N9—Ca1—N1—C9−162.98 (19)N5—Ca1—N7—C21−98.0 (3)
N5—Ca1—N1—C926.43 (18)O2—Ca1—N7—C2130.6 (3)
N3—Ca1—N1—C9−79.05 (19)N1—Ca1—N7—C21−156.2 (3)
N7—Ca1—N1—C993.51 (19)N2—Ca1—N7—C21162.4 (3)
O2—Ca1—N1—C9−101.5 (2)N7—C20—N8—C261.9 (3)
N2—Ca1—N1—C9134.2 (2)C19—C20—N8—C26−180.0 (3)
O1—Ca1—N1—C195.72 (18)C25—C26—N8—C20−178.9 (4)
N9—Ca1—N1—C1−45.13 (18)C21—C26—N8—C20−1.1 (3)
N5—Ca1—N1—C1144.28 (19)N10—C28—N9—C29−0.3 (3)
N3—Ca1—N1—C138.81 (17)C27—C28—N9—C29177.8 (3)
N7—Ca1—N1—C1−148.63 (17)N10—C28—N9—Ca1−172.16 (19)
O2—Ca1—N1—C116.4 (3)C27—C28—N9—Ca16.0 (4)
N2—Ca1—N1—C1−107.96 (18)C34—C29—N9—C280.5 (3)
O1—Ca1—N1—C17−143.63 (17)C30—C29—N9—C28−178.7 (3)
N9—Ca1—N1—C1775.53 (18)C34—C29—N9—Ca1169.7 (2)
N5—Ca1—N1—C17−95.06 (19)C30—C29—N9—Ca1−9.6 (5)
N3—Ca1—N1—C17159.5 (2)O1—Ca1—N9—C28130.0 (2)
N7—Ca1—N1—C17−28.0 (2)N5—Ca1—N9—C28−62.4 (3)
O2—Ca1—N1—C17137.05 (19)N3—Ca1—N9—C28−150.9 (2)
N2—Ca1—N1—C1712.70 (17)N7—Ca1—N9—C2837.2 (2)
C28—C27—N2—C19−156.1 (2)O2—Ca1—N9—C28119.7 (2)
C28—C27—N2—C1881.3 (3)N1—Ca1—N9—C28−84.9 (2)
C28—C27—N2—Ca1−39.9 (3)N2—Ca1—N9—C28−20.3 (2)
C20—C19—N2—C2770.5 (3)O1—Ca1—N9—C29−38.3 (3)
C20—C19—N2—C18−168.0 (2)N5—Ca1—N9—C29129.4 (3)
C20—C19—N2—Ca1−47.1 (3)N3—Ca1—N9—C2940.9 (3)
C17—C18—N2—C27−162.4 (2)N7—Ca1—N9—C29−131.0 (3)
C17—C18—N2—C1975.9 (3)O2—Ca1—N9—C29−48.5 (3)
C17—C18—N2—Ca1−42.5 (3)N1—Ca1—N9—C29106.8 (3)
O1—Ca1—N2—C27−85.5 (2)N2—Ca1—N9—C29171.5 (3)
N9—Ca1—N2—C2732.01 (17)N9—C28—N10—C340.0 (3)
N5—Ca1—N2—C27−163.35 (17)C27—C28—N10—C34−178.1 (3)
N3—Ca1—N2—C2797.79 (18)C33—C34—N10—C28−178.9 (3)
N7—Ca1—N2—C27−82.70 (17)C29—C34—N10—C280.3 (3)
O2—Ca1—N2—C27−17.5 (2)O3—N11—O1—Ca1−178.7 (2)
N1—Ca1—N2—C27135.01 (18)O2—N11—O1—Ca1−0.3 (2)
O1—Ca1—N2—C1932.9 (2)N9—Ca1—O1—N11−12.96 (18)
N9—Ca1—N2—C19150.38 (19)N5—Ca1—O1—N11171.96 (16)
N5—Ca1—N2—C19−44.97 (17)N3—Ca1—O1—N11−92.96 (16)
N3—Ca1—N2—C19−143.84 (17)N7—Ca1—O1—N1187.23 (16)
N7—Ca1—N2—C1935.67 (17)O2—Ca1—O1—N110.18 (13)
O2—Ca1—N2—C19100.90 (17)N1—Ca1—O1—N11−143.45 (14)
N1—Ca1—N2—C19−106.62 (18)N2—Ca1—O1—N1189.8 (2)
O1—Ca1—N2—C18154.23 (18)O3—N11—O2—Ca1178.6 (2)
N9—Ca1—N2—C18−88.26 (18)O1—N11—O2—Ca10.3 (2)
N5—Ca1—N2—C1876.38 (18)O1—Ca1—O2—N11−0.18 (13)
N3—Ca1—N2—C18−22.5 (2)N9—Ca1—O2—N11168.59 (16)
N7—Ca1—N2—C18157.03 (19)N5—Ca1—O2—N11−10.37 (18)
O2—Ca1—N2—C18−137.75 (17)N3—Ca1—O2—N1182.99 (15)
N1—Ca1—N2—C1814.73 (17)N7—Ca1—O2—N11−89.40 (15)
N4—C2—N3—C30.1 (4)N1—Ca1—O2—N11103.43 (19)
C1—C2—N3—C3−178.8 (3)N2—Ca1—O2—N11−145.63 (14)
N4—C2—N3—Ca1−174.3 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···O5i0.862.463.208 (8)145
N4—H4A···O6i0.862.092.888 (10)154
N6—H6A···O2ii0.862.263.099 (3)165
N6—H6A···O3ii0.862.453.118 (3)135
N10—H10···O1iii0.861.942.789 (3)172
O7—H7A···O4iv0.822.393.109 (11)147
N8—H8···O40.861.922.730 (7)157
O8—H8A···O90.821.862.655 (6)164
O9—H9···O50.822.142.929 (9)160
C9—H9B···O70.972.393.274 (5)151
C17—H17A···O80.972.333.290 (5)168
C19—H19B···O80.972.453.378 (5)160
Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) x−1, y, z; (iii) x+1/2, −y+1/2, z+1/2; (iv) x−1/2, −y+1/2, z−1/2.
Table 1
Selected geometric parameters (Å) top
Ca1—O12.440 (2)Ca1—N72.543 (2)
Ca1—N92.470 (2)Ca1—O22.641 (2)
Ca1—N52.477 (2)Ca1—N12.647 (2)
Ca1—N32.521 (2)Ca1—N22.649 (2)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···O5i0.862.463.208 (8)145
N4—H4A···O6i0.862.092.888 (10)154
N6—H6A···O2ii0.862.263.099 (3)165
N6—H6A···O3ii0.862.453.118 (3)135
N10—H10···O1iii0.861.942.789 (3)172
O7—H7A···O4iv0.822.393.109 (11)147
N8—H8···O40.861.922.730 (7)157
O8—H8A···O90.821.862.655 (6)164
O9—H9···O50.822.142.929 (9)160
C9—H9B···O70.972.393.274 (5)151
C17—H17A···O80.972.333.290 (5)168
C19—H19B···O80.972.453.378 (5)160
Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) x−1, y, z; (iii) x+1/2, −y+1/2, z+1/2; (iv) x−1/2, −y+1/2, z−1/2.
references
References top

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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.