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Acta Cryst. (2011). E67, o87-o88    [ doi:10.1107/S160053681005110X ]

Bis(2,9-dimethyl-1,10-phenanthrolin-1-ium) hydrogen (S,S)-tartrate nonahydrate

Z. Derikvand and M. M. Olmstead

Abstract top

The asymmetric unit of the title compound, 2C14H13N2+·2C4H5O6-·9H2O, contains two cations and two anions in addition to nine molecules of water. Each of the hydrogen tartrate anions is hydrogen bonded to itself by translation along [100] in a head-to-tail fashion via a short hydrogen bond with donor-acceptor distances of 2.473 (4) and 2.496 (4) Å. A large number of intermolecular O-H...O, N-H...O and C-H...O hydrogen-bonding interactions, as well as [pi]-[pi] stacking [centroid-centroid distances in the range 3.642 (3) to 3.866 (3) Å], play an important role in the crystal structure.

Comment top

We recently reported the structure of the trihydrate of a salt formed by proton transfer from D-tartaric acid to phenanthroline (Derikvand & Olmstead, 2010). An interesting feature of this structure was the existence of a short hydrogen bond between adjacent tartrate anions. There are many other proton transfer structures of tartaric acid, for example, (Paixão et al., 1999; Ryttersgaard & Larsen, 2003; Bai et al., 2005; Zhang et al., 2006; Smith, et al., 2006; Suresh et al., 2006; Wang et al., 2008; Su et al., 2009), some of which feature similar short hydrogen bonds. The title structure contains two protonated cations of 2,9-dimethyl-1,10-phenanthroline (neocuproine), two anions of mono-deprotonated D-tartaric acid and nine water molecules. As shown in Fig. 1, one of the protons of the tartaric acid carboxylic groups has been transferred to one of the nitrogen atoms of the 2,9-dimethyl-1,10-phenanthroline molecule. The structure reveals a pattern similar to that seen in the previous structure of (phen)(D-tartrate).3H2O. In particular, the carboxylic acid group at one end of the tartrate anion is hydrogen bonded to the deprotonated carboxylic acid group of an adjacent tartrate anion in a linear, head-to-tail fashion. Each of the two tartrate anions in the asymmetric unit displays this kind of hydrogen bond (Fig. 2). These hydrogen bonds are short (O···O distances of 2.473 (4) Å and 2.496 (4) Å), and are propagated by unit translations of the anions along the a-direction. In addition, the O—H distance is longer, the H···O distance is shorter and the O—H···O angle is more linear than other O—H···O interactions in the structure. A large number of additional hydrogen bonding interactions are also present. It is notable that crystal growth along the a-direction is clearly preferred. In the crystal used for data collection, the longest dimension, 0.53 mm, corresponds to the [100] direction. The two shorter dimensions, 0.05 mm and 0.06 mm, correspond to [010] and [001], respectively. Details of the O–H···O, N–H···O and C–H···O hydrogen bonds are given in Table 1. As was seen in the structure containing phen, the cationic dmpH+ units are stacked together via π–π interactions. The centroid-centroid distances fall in the range 3.642 (3) Å to 3.866 (3) Å. The overall packing of the structure is depicted in Fig. 3.

Related literature top

For proton-transfer structures of tartaric acid, see: Bai et al. (2005); Derikvand & Olmstead (2010); Paixão et al. (1999); Ryttersgaard & Larsen (2003); Smith et al. (2006); Su et al. (2009); Suresh et al. (2006); Wang et al. (2008); Zhang et al. (2006).

Experimental top

To an aqueous solution of D-tartaric acid (75 mg, 1 mmol) in water (10 ml) was added a solution of 2,9-dimethyl-1,10-phenanthroline (100 mg, 1 mmol) in methanol (10 ml) in a 1:1 molar ratio. The solution was stirred for 1 h. By slow evaporation of the solvent at room temperature, colorless needles were obtained after 1 week.

Refinement top

Hydrogen atoms H1 and H7 were allowed to freely refine with isotropic thermal parameters tied to 1.2 times the equivalent isotropic values of their parent O atoms. Water hydrogen atoms were located in a difference Fourier map and subsequently refined with restraints of 0.87 (2) for O—H distances and 1.34 (4) for O···O distances. N—H distances were restrained to 0.88 Å, hydroxyl O—H to 0.84 Å, and C—H to 0.98 Å using a riding model and U(iso) = 1.2 U(eq). The carbon atoms C29 to C36 were restrained to ISOR 0.004. In addition, the positional parameters of H2D were fixed due to disorder involving O2W and O8W that could not be resolved. In the absence of significant anomalous dispersion, Friedel opposites were merged in the final cycles of refinement.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A drawing of the asymmetric unit of the title compound. Thermal ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The hydrogen bonding interactions that support the strong hydrogen bonding between tartrate anions (symmetry code: i = x - 1, y, z).
[Figure 3] Fig. 3. Crystal packing diagram as viewed down c.
Bis(2,9-dimethyl-1,10-phenanthrolin-1-ium) hydrogen (S,S)-tartrate nonahydrate top
Crystal data top
2C14H13N2+·2C4H5O6−·9H2ODx = 1.411 Mg m−3
Mr = 878.83Melting point: 523 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 7481 reflections
a = 7.0927 (5) Åθ = 3.0–30.5°
b = 23.3998 (15) ŵ = 0.12 mm−1
c = 24.9335 (16) ÅT = 90 K
V = 4138.2 (5) Å3Needle, colorless
Z = 40.53 × 0.06 × 0.05 mm
F(000) = 1864
Data collection top
Bruker APEXII
diffractometer		7023 independent reflections
Radiation source: fine-focus sealed tube6177 reflections with I > 2σ(I)
graphiteRint = 0.097
Detector resolution: 8.3 pixels mm-1θmax = 30.5°, θmin = 2.6°
ω scansh = −10→10
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		k = −32→33
Tmin = 0.975, Tmax = 0.994l = −35→35
49446 measured reflections
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)] = 0.090Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173H atoms treated by a mixture of independent and constrained refinement
S = 1.25 w = 1/[σ2(Fo2) + (0.0387P)2 + 8.4022P]
where P = (Fo2 + 2Fc2)/3
7023 reflections(Δ/σ)max = 0.001
611 parametersΔρmax = 0.47 e Å−3
111 restraintsΔρmin = −0.46 e Å−3
Crystal data top
2C14H13N2+·2C4H5O6−·9H2OV = 4138.2 (5) Å3
Mr = 878.83Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.0927 (5) ŵ = 0.12 mm−1
b = 23.3998 (15) ÅT = 90 K
c = 24.9335 (16) Å0.53 × 0.06 × 0.05 mm
Data collection top
Bruker APEXII
diffractometer		7023 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		6177 reflections with I > 2σ(I)
Tmin = 0.975, Tmax = 0.994Rint = 0.097
49446 measured reflectionsθmax = 30.5°
Refinement top
R[F2 > 2σ(F2)] = 0.090H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.173Δρmax = 0.47 e Å−3
S = 1.25Δρmin = −0.46 e Å−3
7023 reflectionsAbsolute structure: ?
611 parametersFlack parameter: ?
111 restraintsRogers parameter: ?
Special details top

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*/Ueq
N10.0327 (5)0.46527 (16)0.33329 (14)0.0095 (7)
N20.0442 (6)0.56743 (15)0.38606 (15)0.0099 (7)
H2A0.01540.56480.35180.012*
C10.0288 (7)0.41562 (18)0.30782 (18)0.0117 (8)
C20.0453 (7)0.36264 (18)0.33514 (18)0.0113 (8)
H20.03730.32790.31560.014*
C30.0728 (7)0.36145 (19)0.38948 (18)0.0123 (9)
H30.08350.32620.40800.015*
C40.0850 (7)0.41442 (18)0.41757 (18)0.0109 (8)
C50.1207 (7)0.4176 (2)0.47412 (18)0.0134 (9)
H50.13050.38340.49460.016*
C60.1406 (7)0.4690 (2)0.49855 (19)0.0163 (9)
H60.17090.47050.53560.020*
C70.1163 (7)0.52117 (19)0.46895 (18)0.0117 (8)
C80.1368 (8)0.5760 (2)0.49209 (19)0.0172 (10)
H80.17220.57950.52870.021*
C90.1059 (7)0.62418 (19)0.46203 (19)0.0154 (9)
H90.11730.66080.47810.018*
C100.0575 (6)0.61955 (18)0.40778 (18)0.0105 (8)
C110.0611 (7)0.46398 (18)0.38698 (17)0.0101 (8)
C120.0728 (6)0.51851 (18)0.41399 (17)0.0098 (8)
C130.0119 (7)0.4179 (2)0.24814 (18)0.0138 (9)
H13A−0.04640.45420.23760.021*
H13B−0.06640.38610.23570.021*
H13C0.13760.41500.23200.021*
C140.0211 (7)0.67108 (18)0.37334 (19)0.0125 (9)
H14A0.05760.66270.33630.019*
H14B0.09530.70340.38670.019*
H14C−0.11320.68070.37460.019*
N30.5130 (5)0.01878 (15)0.17341 (15)0.0100 (7)
N40.4445 (6)−0.07881 (15)0.11789 (14)0.0092 (7)
H4C0.4710−0.07840.15240.011*
C150.5497 (7)0.06682 (19)0.20033 (19)0.0124 (9)
C160.5333 (7)0.12188 (18)0.1758 (2)0.0143 (9)
H160.55850.15530.19620.017*
C170.4817 (7)0.1269 (2)0.1230 (2)0.0151 (9)
H170.47150.16330.10650.018*
C180.4442 (7)0.07635 (19)0.09370 (19)0.0135 (9)
C190.3935 (7)0.0763 (2)0.0377 (2)0.0168 (10)
H190.38160.11170.01930.020*
C200.3627 (8)0.0273 (2)0.0110 (2)0.0195 (10)
H200.33060.0286−0.02600.023*
C210.3776 (7)−0.0270 (2)0.03751 (19)0.0155 (9)
C220.3541 (7)−0.0806 (2)0.01155 (18)0.0150 (9)
H220.3215−0.0817−0.02540.018*
C230.3776 (7)−0.13030 (19)0.03872 (18)0.0125 (9)
H230.3621−0.16580.02070.015*
C240.4246 (7)−0.12946 (19)0.09344 (18)0.0115 (8)
C250.4603 (7)0.02428 (19)0.12140 (18)0.0120 (8)
C260.4256 (7)−0.02800 (19)0.09198 (18)0.0115 (8)
C270.6064 (8)0.0606 (2)0.25742 (19)0.0164 (10)
H27A0.63250.02040.26520.025*
H27B0.50420.07410.28060.025*
H27C0.72010.08340.26410.025*
C280.4518 (7)−0.18329 (17)0.12542 (18)0.0116 (8)
H28A0.5132−0.17410.15960.017*
H28B0.5311−0.20990.10510.017*
H28C0.3290−0.20090.13240.017*
O10.0522 (5)0.35066 (13)0.12922 (12)0.0088 (6)
H1−0.088 (8)0.353 (2)0.129 (2)0.011*
O20.0346 (4)0.28017 (13)0.18981 (13)0.0101 (6)
O30.4033 (5)0.25951 (12)0.18514 (12)0.0094 (6)
H3B0.50200.26710.20230.011*
O40.3405 (5)0.26187 (13)0.07110 (13)0.0101 (6)
H40.25050.27190.05130.012*
O50.7038 (4)0.35075 (13)0.12500 (13)0.0096 (6)
O60.7107 (5)0.27534 (13)0.07009 (13)0.0110 (6)
C290.1247 (6)0.31162 (17)0.16055 (16)0.0068 (8)
C300.3399 (6)0.30930 (18)0.15785 (16)0.0059 (7)
H300.39180.34360.17660.007*
C310.4082 (6)0.30995 (18)0.09990 (16)0.0068 (8)
H310.35970.34540.08220.008*
C320.6237 (6)0.31068 (17)0.09741 (16)0.0062 (7)
O7−0.4298 (4)0.13513 (13)0.38098 (13)0.0088 (6)
H7−0.557 (9)0.132 (2)0.377 (2)0.011*
O8−0.4525 (5)0.19870 (13)0.31384 (13)0.0102 (6)
O9−0.0879 (5)0.22177 (13)0.31636 (12)0.0101 (6)
H9C0.00580.21260.29760.012*
O10−0.1366 (5)0.22847 (13)0.43072 (13)0.0096 (6)
H10A−0.23980.22190.44600.012*
O110.2185 (4)0.13303 (13)0.38332 (12)0.0077 (6)
O120.2307 (5)0.21666 (13)0.42670 (13)0.0112 (6)
C33−0.3603 (6)0.17098 (17)0.34588 (17)0.0073 (8)
C34−0.1458 (6)0.17432 (17)0.34727 (17)0.0061 (7)
H34−0.09370.13890.33050.007*
C35−0.0721 (6)0.17825 (17)0.40533 (17)0.0059 (7)
H35−0.11890.14440.42590.007*
C360.1436 (6)0.17735 (18)0.40528 (16)0.0066 (8)
O1W−0.0728 (6)0.58367 (14)0.27904 (14)0.0177 (7)
H1A−0.076 (9)0.5612 (18)0.2511 (15)0.021*
H1B−0.132 (8)0.6140 (15)0.268 (2)0.021*
O2W0.1114 (5)0.03182 (14)0.33319 (14)0.0173 (7)
H2C0.153 (8)0.0565 (14)0.3558 (16)0.021*
H2D0.10890.00030.35210.021*
O3W0.5757 (5)0.45505 (14)0.16602 (14)0.0161 (7)
H3C0.599 (8)0.4224 (14)0.151 (2)0.019*
H3D0.466 (5)0.464 (2)0.153 (2)0.019*
O4W−0.4478 (5)0.21368 (13)0.48609 (12)0.0100 (6)
H4A−0.479 (7)0.2357 (18)0.5126 (14)0.012*
H4B−0.550 (5)0.215 (2)0.4667 (17)0.012*
O5W0.2110 (5)0.18871 (13)0.25895 (12)0.0090 (6)
H5A0.229 (7)0.2143 (17)0.2344 (14)0.011*
H5B0.307 (5)0.195 (2)0.2797 (17)0.011*
O6W0.0447 (5)0.29367 (14)0.01471 (13)0.0112 (6)
H6A0.035 (8)0.2697 (17)−0.0118 (14)0.013*
H6B−0.064 (4)0.293 (2)0.0301 (19)0.013*
O7W0.4713 (5)−0.10319 (14)0.22815 (13)0.0143 (7)
H7A0.453 (8)−0.0775 (16)0.2527 (17)0.017*
H7B0.407 (7)−0.1320 (15)0.240 (2)0.017*
O8W−0.2016 (5)−0.03301 (14)0.37713 (14)0.0153 (7)
H8A−0.146 (7)−0.0662 (12)0.378 (2)0.018*
H8B−0.108 (5)−0.0129 (18)0.365 (2)0.018*
O9W−0.3015 (5)0.28971 (14)0.24357 (12)0.0105 (6)
H9A−0.200 (5)0.286 (2)0.2251 (18)0.013*
H9B−0.283 (8)0.2656 (18)0.2694 (14)0.013*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0071 (16)0.0114 (17)0.0099 (16)−0.0012 (14)−0.0031 (14)−0.0001 (13)
N20.0111 (17)0.0084 (17)0.0102 (16)−0.0026 (14)−0.0035 (15)−0.0004 (13)
C10.012 (2)0.009 (2)0.015 (2)0.0000 (17)0.0034 (17)−0.0036 (16)
C20.014 (2)0.0051 (18)0.015 (2)0.0008 (16)−0.0018 (18)−0.0039 (15)
C30.013 (2)0.011 (2)0.0127 (19)−0.0005 (17)−0.0035 (18)0.0029 (16)
C40.010 (2)0.011 (2)0.0119 (19)0.0030 (17)0.0004 (16)0.0020 (15)
C50.015 (2)0.014 (2)0.012 (2)0.0048 (18)−0.0010 (18)0.0074 (16)
C60.018 (2)0.019 (2)0.012 (2)0.001 (2)−0.0013 (19)0.0028 (18)
C70.010 (2)0.013 (2)0.0119 (19)−0.0019 (17)−0.0003 (17)0.0003 (16)
C80.019 (2)0.019 (2)0.013 (2)−0.001 (2)−0.0055 (19)−0.0060 (18)
C90.019 (2)0.010 (2)0.017 (2)0.0022 (18)−0.005 (2)−0.0097 (17)
C100.0056 (19)0.011 (2)0.015 (2)−0.0015 (16)−0.0013 (17)0.0000 (16)
C110.012 (2)0.0079 (19)0.0100 (19)0.0017 (16)0.0003 (17)−0.0007 (15)
C120.007 (2)0.010 (2)0.0118 (19)−0.0013 (16)0.0012 (16)−0.0010 (15)
C130.021 (2)0.011 (2)0.0097 (18)0.0004 (18)0.0034 (17)−0.0036 (16)
C140.008 (2)0.0073 (19)0.022 (2)−0.0009 (16)−0.0018 (18)−0.0030 (17)
N30.0077 (17)0.0094 (17)0.0130 (17)0.0006 (13)−0.0016 (14)−0.0025 (14)
N40.0122 (18)0.0065 (16)0.0089 (16)−0.0011 (14)−0.0017 (15)−0.0023 (13)
C150.010 (2)0.011 (2)0.017 (2)−0.0013 (17)0.0069 (18)−0.0055 (16)
C160.015 (2)0.0040 (19)0.024 (2)0.0016 (16)0.011 (2)−0.0054 (16)
C170.009 (2)0.009 (2)0.027 (2)0.0023 (16)0.0029 (19)−0.0036 (18)
C180.011 (2)0.009 (2)0.021 (2)0.0006 (17)0.0056 (19)0.0014 (17)
C190.011 (2)0.017 (2)0.023 (2)0.0020 (18)−0.0004 (19)0.0108 (19)
C200.018 (2)0.024 (3)0.017 (2)−0.004 (2)−0.004 (2)0.009 (2)
C210.017 (2)0.016 (2)0.014 (2)−0.0025 (19)−0.0036 (19)0.0015 (18)
C220.013 (2)0.024 (3)0.0084 (19)−0.002 (2)−0.0013 (17)−0.0025 (18)
C230.010 (2)0.013 (2)0.014 (2)−0.0029 (17)−0.0014 (18)−0.0018 (17)
C240.009 (2)0.012 (2)0.014 (2)0.0035 (16)0.0032 (17)−0.0014 (16)
C250.0072 (19)0.012 (2)0.016 (2)0.0006 (16)0.0023 (18)−0.0046 (17)
C260.013 (2)0.0080 (19)0.0137 (19)−0.0034 (17)−0.0007 (17)0.0005 (16)
C270.021 (2)0.014 (2)0.014 (2)−0.0050 (19)0.002 (2)−0.0065 (17)
C280.013 (2)0.0046 (19)0.017 (2)0.0021 (16)0.0002 (19)−0.0015 (16)
O10.0051 (14)0.0118 (15)0.0094 (14)0.0019 (12)0.0024 (12)−0.0015 (11)
O20.0050 (14)0.0105 (15)0.0149 (15)−0.0010 (12)0.0052 (12)0.0019 (12)
O30.0074 (15)0.0087 (14)0.0120 (14)0.0004 (11)−0.0032 (12)0.0046 (11)
O40.0066 (15)0.0113 (15)0.0125 (15)−0.0018 (12)0.0003 (12)−0.0040 (12)
O50.0037 (14)0.0078 (14)0.0173 (16)0.0010 (11)−0.0014 (13)−0.0021 (12)
O60.0075 (14)0.0103 (15)0.0151 (15)0.0015 (12)0.0024 (13)−0.0031 (12)
C290.0080 (17)0.0044 (16)0.0079 (17)−0.0027 (14)−0.0010 (14)−0.0048 (13)
C300.0039 (16)0.0064 (17)0.0072 (16)−0.0001 (14)−0.0003 (14)−0.0013 (13)
C310.0041 (16)0.0086 (17)0.0075 (16)0.0002 (14)0.0020 (14)0.0008 (13)
C320.0060 (16)0.0057 (16)0.0071 (16)0.0006 (14)−0.0001 (14)0.0038 (13)
O70.0047 (13)0.0089 (13)0.0129 (14)−0.0003 (11)−0.0039 (12)0.0004 (11)
O80.0078 (14)0.0091 (14)0.0136 (14)0.0020 (11)−0.0024 (12)0.0010 (11)
O90.0076 (14)0.0114 (14)0.0114 (13)−0.0010 (11)0.0040 (12)0.0047 (11)
O100.0055 (13)0.0105 (14)0.0128 (14)0.0017 (11)0.0027 (12)−0.0062 (11)
O110.0048 (13)0.0066 (13)0.0118 (14)0.0012 (11)−0.0025 (11)−0.0006 (11)
O120.0101 (14)0.0095 (14)0.0138 (14)−0.0018 (12)−0.0016 (12)−0.0045 (12)
C330.0086 (17)0.0043 (16)0.0091 (16)0.0023 (14)−0.0018 (15)−0.0036 (14)
C340.0046 (16)0.0068 (17)0.0070 (16)−0.0008 (13)0.0014 (14)−0.0018 (14)
C350.0009 (15)0.0065 (17)0.0102 (16)0.0008 (13)−0.0017 (14)0.0008 (13)
C360.0070 (17)0.0081 (17)0.0047 (15)−0.0004 (14)−0.0023 (14)0.0004 (13)
O1W0.0233 (19)0.0127 (16)0.0170 (16)0.0060 (15)−0.0065 (15)−0.0027 (13)
O2W0.0172 (17)0.0093 (15)0.0255 (18)−0.0048 (14)−0.0002 (15)−0.0022 (13)
O3W0.0138 (17)0.0119 (16)0.0227 (17)0.0042 (13)−0.0016 (15)−0.0046 (13)
O4W0.0082 (15)0.0123 (15)0.0095 (14)0.0018 (13)−0.0012 (12)−0.0019 (11)
O5W0.0075 (14)0.0099 (14)0.0098 (14)−0.0026 (12)−0.0003 (12)0.0039 (11)
O6W0.0089 (15)0.0136 (16)0.0113 (14)−0.0029 (13)−0.0001 (13)−0.0055 (12)
O7W0.0187 (18)0.0106 (15)0.0137 (15)−0.0071 (14)0.0046 (14)−0.0016 (12)
O8W0.0131 (16)0.0117 (16)0.0211 (17)0.0013 (13)0.0070 (14)0.0005 (14)
O9W0.0070 (15)0.0163 (16)0.0082 (14)0.0030 (12)0.0024 (12)0.0041 (12)
Geometric parameters (Å, °) top
N1—C11.324 (5)C24—C281.503 (6)
N1—C111.354 (5)C25—C261.447 (6)
N2—C101.338 (6)C27—H27A0.9800
N2—C121.355 (5)C27—H27B0.9800
N2—H2A0.8800C27—H27C0.9800
C1—C21.419 (6)C28—H28A0.9800
C1—C131.494 (6)C28—H28B0.9800
C2—C31.369 (6)C28—H28C0.9800
C2—H20.9500O1—C291.307 (5)
C3—C41.426 (6)O1—H10.99 (6)
C3—H30.9500O2—C291.217 (5)
C4—C111.398 (6)O3—C301.422 (5)
C4—C51.434 (6)O3—H3B0.8400
C5—C61.355 (7)O4—C311.418 (5)
C5—H50.9500O4—H40.8400
C6—C71.438 (6)O5—C321.294 (5)
C6—H60.9500O6—C321.236 (5)
C7—C121.406 (6)C29—C301.529 (6)
C7—C81.415 (6)C30—C311.524 (6)
C8—C91.371 (7)C30—H301.0000
C8—H80.9500C31—C321.530 (6)
C9—C101.399 (6)C31—H311.0000
C9—H90.9500O7—C331.309 (5)
C10—C141.503 (6)O7—H70.91 (6)
C11—C121.445 (6)O8—C331.219 (5)
C13—H13A0.9800O9—C341.412 (5)
C13—H13B0.9800O9—H9C0.8400
C13—H13C0.9800O10—C351.411 (5)
C14—H14A0.9800O10—H10A0.8400
C14—H14B0.9800O11—C361.287 (5)
C14—H14C0.9800O12—C361.230 (5)
N3—C151.335 (6)C33—C341.524 (6)
N3—C251.356 (6)C34—C351.542 (6)
N4—C241.340 (5)C34—H341.0000
N4—C261.360 (6)C35—C361.530 (6)
N4—H4C0.8800C35—H351.0000
C15—C161.431 (6)O1W—H1A0.87 (4)
C15—C271.486 (7)O1W—H1B0.87 (4)
C16—C171.371 (7)O2W—H2C0.86 (4)
C16—H160.9500O2W—H2D0.88
C17—C181.414 (6)O3W—H3C0.87 (4)
C17—H170.9500O3W—H3D0.87 (4)
C18—C251.405 (6)O4W—H4A0.87 (4)
C18—C191.442 (7)O4W—H4B0.87 (4)
C19—C201.344 (7)O5W—H5A0.87 (4)
C19—H190.9500O5W—H5B0.87 (4)
C20—C211.436 (7)O6W—H6A0.87 (4)
C20—H200.9500O6W—H6B0.86 (3)
C21—C261.400 (6)O7W—H7A0.87 (4)
C21—C221.421 (7)O7W—H7B0.87 (4)
C22—C231.356 (7)O8W—H8A0.87 (4)
C22—H220.9500O8W—H8B0.87 (2)
C23—C241.405 (6)O9W—H9A0.86 (4)
C23—H230.9500O9W—H9B0.87 (4)
C1—N1—C11117.2 (4)C23—C22—H22119.5
C10—N2—C12123.5 (4)C21—C22—H22119.5
C10—N2—H2A118.3C22—C23—C24120.2 (4)
C12—N2—H2A118.3C22—C23—H23119.9
N1—C1—C2122.3 (4)C24—C23—H23119.9
N1—C1—C13116.6 (4)N4—C24—C23118.6 (4)
C2—C1—C13121.1 (4)N4—C24—C28119.1 (4)
C3—C2—C1120.3 (4)C23—C24—C28122.3 (4)
C3—C2—H2119.9N3—C25—C18125.1 (4)
C1—C2—H2119.9N3—C25—C26116.8 (4)
C2—C3—C4118.5 (4)C18—C25—C26118.0 (4)
C2—C3—H3120.8N4—C26—C21119.9 (4)
C4—C3—H3120.8N4—C26—C25118.8 (4)
C11—C4—C3116.5 (4)C21—C26—C25121.3 (4)
C11—C4—C5121.0 (4)C15—C27—H27A109.5
C3—C4—C5122.6 (4)C15—C27—H27B109.5
C6—C5—C4120.4 (4)H27A—C27—H27B109.5
C6—C5—H5119.8C15—C27—H27C109.5
C4—C5—H5119.8H27A—C27—H27C109.5
C5—C6—C7120.7 (4)H27B—C27—H27C109.5
C5—C6—H6119.6C24—C28—H28A109.5
C7—C6—H6119.6C24—C28—H28B109.5
C12—C7—C8117.4 (4)H28A—C28—H28B109.5
C12—C7—C6119.3 (4)C24—C28—H28C109.5
C8—C7—C6123.3 (4)H28A—C28—H28C109.5
C9—C8—C7120.4 (4)H28B—C28—H28C109.5
C9—C8—H8119.8C29—O1—H1116 (3)
C7—C8—H8119.8C30—O3—H3B109.5
C8—C9—C10120.3 (4)C31—O4—H4109.5
C8—C9—H9119.9O2—C29—O1125.0 (4)
C10—C9—H9119.9O2—C29—C30121.9 (4)
N2—C10—C9118.6 (4)O1—C29—C30113.0 (4)
N2—C10—C14119.2 (4)O3—C30—C31111.2 (3)
C9—C10—C14122.2 (4)O3—C30—C29108.9 (3)
N1—C11—C4125.1 (4)C31—C30—C29111.0 (4)
N1—C11—C12116.7 (4)O3—C30—H30108.6
C4—C11—C12118.1 (4)C31—C30—H30108.6
N2—C12—C7119.8 (4)C29—C30—H30108.6
N2—C12—C11119.8 (4)O4—C31—C30111.4 (3)
C7—C12—C11120.4 (4)O4—C31—C32109.1 (3)
C1—C13—H13A109.5C30—C31—C32110.9 (4)
C1—C13—H13B109.5O4—C31—H31108.5
H13A—C13—H13B109.5C30—C31—H31108.5
C1—C13—H13C109.5C32—C31—H31108.5
H13A—C13—H13C109.5O6—C32—O5124.0 (4)
H13B—C13—H13C109.5O6—C32—C31120.9 (4)
C10—C14—H14A109.5O5—C32—C31115.1 (4)
C10—C14—H14B109.5C33—O7—H7111 (3)
H14A—C14—H14B109.5C34—O9—H9C109.5
C10—C14—H14C109.5C35—O10—H10A109.5
H14A—C14—H14C109.5O8—C33—O7125.2 (4)
H14B—C14—H14C109.5O8—C33—C34121.6 (4)
C15—N3—C25117.1 (4)O7—C33—C34113.2 (4)
C24—N4—C26123.2 (4)O9—C34—C33108.6 (4)
C24—N4—H4C118.4O9—C34—C35111.5 (3)
C26—N4—H4C118.4C33—C34—C35111.3 (4)
N3—C15—C16121.8 (4)O9—C34—H34108.5
N3—C15—C27116.9 (4)C33—C34—H34108.5
C16—C15—C27121.3 (4)C35—C34—H34108.5
C17—C16—C15120.6 (4)O10—C35—C36109.6 (4)
C17—C16—H16119.7O10—C35—C34111.2 (3)
C15—C16—H16119.7C36—C35—C34109.7 (4)
C16—C17—C18118.3 (4)O10—C35—H35108.8
C16—C17—H17120.8C36—C35—H35108.8
C18—C17—H17120.8C34—C35—H35108.8
C25—C18—C17117.1 (4)O12—C36—O11125.4 (4)
C25—C18—C19119.7 (4)O12—C36—C35119.4 (4)
C17—C18—C19123.2 (4)O11—C36—C35115.1 (4)
C20—C19—C18121.4 (4)H1A—O1W—H1B103 (4)
C20—C19—H19119.3H2C—O2W—H2D103
C18—C19—H19119.3H3C—O3W—H3D102 (4)
C19—C20—C21121.0 (5)H4A—O4W—H4B101 (4)
C19—C20—H20119.5H5A—O5W—H5B101 (3)
C21—C20—H20119.5H6A—O6W—H6B105 (4)
C26—C21—C22117.1 (4)H7A—O7W—H7B102 (4)
C26—C21—C20118.6 (4)H8A—O8W—H8B98 (4)
C22—C21—C20124.2 (4)H9A—O9W—H9B102 (4)
C23—C22—C21121.0 (4)
C11—N1—C1—C22.7 (7)C26—C21—C22—C230.0 (7)
C11—N1—C1—C13−175.5 (4)C20—C21—C22—C23177.4 (5)
N1—C1—C2—C3−2.3 (8)C21—C22—C23—C240.4 (7)
C13—C1—C2—C3175.8 (5)C26—N4—C24—C23−1.6 (7)
C1—C2—C3—C4−0.2 (7)C26—N4—C24—C28178.9 (4)
C2—C3—C4—C112.1 (7)C22—C23—C24—N40.4 (7)
C2—C3—C4—C5−177.6 (5)C22—C23—C24—C28179.9 (5)
C11—C4—C5—C6−3.0 (7)C15—N3—C25—C181.0 (7)
C3—C4—C5—C6176.6 (5)C15—N3—C25—C26178.4 (4)
C4—C5—C6—C73.3 (7)C17—C18—C25—N3−1.6 (7)
C5—C6—C7—C12−0.5 (7)C19—C18—C25—N3177.7 (4)
C5—C6—C7—C8−179.4 (5)C17—C18—C25—C26−179.0 (4)
C12—C7—C8—C93.1 (7)C19—C18—C25—C260.3 (7)
C6—C7—C8—C9−177.9 (5)C24—N4—C26—C212.0 (7)
C7—C8—C9—C10−1.4 (8)C24—N4—C26—C25−176.6 (4)
C12—N2—C10—C90.9 (7)C22—C21—C26—N4−1.1 (7)
C12—N2—C10—C14−179.4 (4)C20—C21—C26—N4−178.7 (5)
C8—C9—C10—N2−0.7 (7)C22—C21—C26—C25177.4 (5)
C8—C9—C10—C14179.6 (5)C20—C21—C26—C25−0.1 (7)
C1—N1—C11—C4−0.6 (7)N3—C25—C26—N41.1 (6)
C1—N1—C11—C12177.5 (4)C18—C25—C26—N4178.7 (4)
C3—C4—C11—N1−1.8 (7)N3—C25—C26—C21−177.5 (4)
C5—C4—C11—N1177.9 (5)C18—C25—C26—C210.1 (7)
C3—C4—C11—C12−179.9 (4)O2—C29—C30—O311.4 (6)
C5—C4—C11—C12−0.2 (7)O1—C29—C30—O3−169.4 (3)
C10—N2—C12—C71.0 (7)O2—C29—C30—C31134.1 (4)
C10—N2—C12—C11−178.2 (4)O1—C29—C30—C31−46.7 (5)
C8—C7—C12—N2−2.9 (7)O3—C30—C31—O460.1 (4)
C6—C7—C12—N2178.1 (4)C29—C30—C31—O4−61.2 (5)
C8—C7—C12—C11176.2 (4)O3—C30—C31—C32−61.5 (5)
C6—C7—C12—C11−2.8 (7)C29—C30—C31—C32177.1 (3)
N1—C11—C12—N24.0 (6)O4—C31—C32—O64.8 (6)
C4—C11—C12—N2−177.8 (4)C30—C31—C32—O6127.8 (4)
N1—C11—C12—C7−175.2 (4)O4—C31—C32—O5−176.0 (3)
C4—C11—C12—C73.0 (7)C30—C31—C32—O5−53.1 (5)
C25—N3—C15—C160.3 (6)O8—C33—C34—O913.3 (6)
C25—N3—C15—C27179.7 (4)O7—C33—C34—O9−168.2 (3)
N3—C15—C16—C17−1.0 (7)O8—C33—C34—C35136.4 (4)
C27—C15—C16—C17179.7 (5)O7—C33—C34—C35−45.1 (5)
C15—C16—C17—C180.4 (7)O9—C34—C35—O1058.9 (4)
C16—C17—C18—C250.8 (7)C33—C34—C35—O10−62.5 (5)
C16—C17—C18—C19−178.4 (5)O9—C34—C35—C36−62.5 (5)
C25—C18—C19—C20−0.6 (7)C33—C34—C35—C36176.1 (3)
C17—C18—C19—C20178.6 (5)O10—C35—C36—O121.5 (6)
C18—C19—C20—C210.5 (8)C34—C35—C36—O12123.8 (4)
C19—C20—C21—C26−0.2 (8)O10—C35—C36—O11179.6 (3)
C19—C20—C21—C22−177.5 (5)C34—C35—C36—O11−58.1 (5)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O1W0.881.972.820 (5)162
N4—H4C···O7W0.881.982.814 (5)159
O4—H4···O6W0.841.802.633 (5)175
O9—H9C···O5W0.841.832.673 (4)177
O10—H10A···O4W0.841.792.627 (5)172
O2W—H2C···O110.86 (4)1.97 (2)2.783 (4)157 (4)
O3W—H3C···O50.87 (4)1.95 (2)2.798 (5)168 (5)
O2W—H2D···O8W0.882.422.903 (5)115
O5W—H5A···O30.87 (4)2.04 (3)2.827 (4)151 (5)
O5W—H5A···O20.87 (4)2.35 (4)3.020 (4)135 (5)
O8W—H8B···O2W0.87 (2)2.03 (2)2.903 (5)178 (5)
O9W—H9A···O20.86 (4)1.89 (2)2.744 (4)175 (5)
O9W—H9B···O90.87 (4)2.08 (4)2.849 (4)147 (5)
O9W—H9B···O80.87 (4)2.26 (4)2.958 (4)137 (5)
O1—H1···O5i0.99 (6)1.49 (6)2.473 (4)172 (5)
O7—H7···O11i0.91 (6)1.60 (6)2.496 (4)167 (5)
O4W—H4B···O12i0.87 (2)1.85 (2)2.720 (5)178 (6)
O6W—H6B···O6i0.86 (3)1.93 (2)2.776 (5)167 (5)
O3—H3B···O9Wii0.841.812.647 (5)173
O5W—H5B···O8ii0.87 (4)1.91 (2)2.761 (4)168 (5)
O1W—H1A···O2Wiii0.87 (4)2.22 (3)3.062 (5)161 (5)
O1W—H1B···O5Wiii0.87 (4)1.96 (2)2.811 (5)168 (6)
O3W—H3D···O8Wiii0.87 (4)2.02 (2)2.876 (5)168 (5)
O4W—H4A···O10iv0.87 (4)1.99 (3)2.815 (4)160 (5)
O4W—H4A···O12iv0.87 (4)2.40 (4)2.998 (4)127 (4)
O6W—H6A···O4v0.87 (4)2.15 (4)2.892 (4)143 (5)
O6W—H6A···O6v0.87 (4)2.19 (4)2.909 (5)140 (5)
O7W—H7A···O3Wvi0.87 (4)2.17 (3)2.988 (5)156 (5)
O7W—H7B···O9Wvii0.87 (4)2.02 (2)2.869 (5)165 (5)
O8W—H8A···O1vii0.87 (4)2.06 (2)2.926 (5)170 (5)
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x, y+1/2, −z+1/2; (iv) x−1/2, −y+1/2, −z+1; (v) x−1/2, −y+1/2, −z; (vi) −x+1, y−1/2, −z+1/2; (vii) −x, y−1/2, −z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O1W0.881.972.820 (5)162
N4—H4C···O7W0.881.982.814 (5)159
O4—H4···O6W0.841.802.633 (5)175
O9—H9C···O5W0.841.832.673 (4)177
O10—H10A···O4W0.841.792.627 (5)172
O2W—H2C···O110.86 (4)1.97 (2)2.783 (4)157 (4)
O3W—H3C···O50.87 (4)1.95 (2)2.798 (5)168 (5)
O2W—H2D···O8W0.882.422.903 (5)115
O5W—H5A···O30.87 (4)2.04 (3)2.827 (4)151 (5)
O5W—H5A···O20.87 (4)2.35 (4)3.020 (4)135 (5)
O8W—H8B···O2W0.87 (2)2.03 (2)2.903 (5)178 (5)
O9W—H9A···O20.86 (4)1.89 (2)2.744 (4)175 (5)
O9W—H9B···O90.87 (4)2.08 (4)2.849 (4)147 (5)
O9W—H9B···O80.87 (4)2.26 (4)2.958 (4)137 (5)
O1—H1···O5i0.99 (6)1.49 (6)2.473 (4)172 (5)
O7—H7···O11i0.91 (6)1.60 (6)2.496 (4)167 (5)
O4W—H4B···O12i0.87 (2)1.85 (2)2.720 (5)178 (6)
O6W—H6B···O6i0.86 (3)1.93 (2)2.776 (5)167 (5)
O3—H3B···O9Wii0.841.812.647 (5)173
O5W—H5B···O8ii0.87 (4)1.91 (2)2.761 (4)168 (5)
O1W—H1A···O2Wiii0.87 (4)2.22 (3)3.062 (5)161 (5)
O1W—H1B···O5Wiii0.87 (4)1.96 (2)2.811 (5)168 (6)
O3W—H3D···O8Wiii0.87 (4)2.02 (2)2.876 (5)168 (5)
O4W—H4A···O10iv0.87 (4)1.99 (3)2.815 (4)160 (5)
O4W—H4A···O12iv0.87 (4)2.40 (4)2.998 (4)127 (4)
O6W—H6A···O4v0.87 (4)2.15 (4)2.892 (4)143 (5)
O6W—H6A···O6v0.87 (4)2.19 (4)2.909 (5)140 (5)
O7W—H7A···O3Wvi0.87 (4)2.17 (3)2.988 (5)156 (5)
O7W—H7B···O9Wvii0.87 (4)2.02 (2)2.869 (5)165 (5)
O8W—H8A···O1vii0.87 (4)2.06 (2)2.926 (5)170 (5)
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x, y+1/2, −z+1/2; (iv) x−1/2, −y+1/2, −z+1; (v) x−1/2, −y+1/2, −z; (vi) −x+1, y−1/2, −z+1/2; (vii) −x, y−1/2, −z+1/2.
references
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