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N,N-Dimethylbiguanidinium bis(hydrogensquarate) features an impressive range of hydrogen bonds within the same crystal structure: neighbouring anions aggregate to a dianionic pair through two strong O—H...O interactions; one of these can be classified among the shortest hydrogen bonds ever studied. Cations and anions in this organic salt further interact via conventional N—H...O and nonclassical C—H...O contacts to an extended structure. As all these interactions occur in the same sample, the title compound is particularly suitable to monitor even subtle trends in hydrogen bonds. Neutron and high-resolution X-ray diffraction experiments have enabled us to determine the electron density precisely and to address its properties with an emphasis on the nature of the X—H...O interactions. Sensitive criteria such as the Laplacian of the electron density and energy densities in the bond-critical points reveal the incipient covalent character of the shortest O—H...O bond. These findings are in agreement with the precise geometry from neutron diffraction: the shortest hydrogen bond is also significantly more symmetric than the longer interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768111043138/so5054sup1.cif
Contains datablocks global, iam

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768111043138/so5054iamsup2.hkl
Contains datablock iam

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768111043138/so5054neutronsup3.hkl
Contains datablock neutron

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768111043138/so5054multipolesup4.hkl
Contains datablock multipole

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768111043138/so5054sup5.pdf
Extra figures and tables

CCDC references: 811599; 811600; 811601

Computing details top

Data collection: Bruker SMART for iam, multipole; PRON2010 for neutron. Cell refinement: Bruker SMART for iam, multipole. Data reduction: Bruker SAINT for iam, multipole. Program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a) for iam, multipole; SHELXS97 (Sheldrick, 1990) for neutron. Program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b) for iam; Volkov et al., (2006) for multipole; SHELXL97 (Sheldrick, 1997) for neutron. Molecular graphics: PLATON (Spek, 2003) for iam; Volkov et al., (2006) for multipole. Software used to prepare material for publication: SHELXL97 (Sheldrick, 1997b) for iam; Volkov et al., (2006) for multipole.

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
(iam) top
Crystal data top
C4H13N5·2(C4HO4)Z = 2
Mr = 357.29F(000) = 372
Triclinic, P1Dx = 1.596 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.0689 (2) ÅCell parameters from 8412 reflections
b = 8.5538 (2) Åθ = 2.4–50.7°
c = 13.0736 (3) ŵ = 0.14 mm1
α = 90.4259 (9)°T = 100 K
β = 105.1185 (9)°Block, colorless
γ = 102.4251 (10)°0.38 × 0.21 × 0.13 mm
V = 743.58 (3) Å3
Data collection top
CCD area detector
diffractometer
9502 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.046
Graphite monochromatorθmax = 52.2°, θmin = 2.4°
ω scansh = 1515
38327 measured reflectionsk = 1818
15808 independent reflectionsl = 2828
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.025P)2]
where P = (Fo2 + 2Fc2)/3
15808 reflections(Δ/σ)max = 0.001
286 parametersΔρmax = 0.82 e Å3
0 restraintsΔρmin = 0.44 e Å3
Crystal data top
C4H13N5·2(C4HO4)γ = 102.4251 (10)°
Mr = 357.29V = 743.58 (3) Å3
Triclinic, P1Z = 2
a = 7.0689 (2) ÅMo Kα radiation
b = 8.5538 (2) ŵ = 0.14 mm1
c = 13.0736 (3) ÅT = 100 K
α = 90.4259 (9)°0.38 × 0.21 × 0.13 mm
β = 105.1185 (9)°
Data collection top
CCD area detector
diffractometer
9502 reflections with I > 2σ(I)
38327 measured reflectionsRint = 0.046
15808 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.106H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.82 e Å3
15808 reflectionsΔρmin = 0.44 e Å3
286 parameters
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*/Ueq
O11.02728 (7)0.82013 (6)0.61291 (3)0.01380 (8)
H10.9664 (17)0.7536 (14)0.5513 (9)0.052 (3)*
O20.75953 (7)0.48456 (5)0.67218 (3)0.01204 (8)
O30.90716 (7)0.62233 (5)0.91952 (3)0.01256 (8)
O41.18711 (7)0.93588 (6)0.85855 (3)0.01435 (8)
C10.99404 (8)0.75549 (7)0.69774 (4)0.00932 (9)
C20.87282 (8)0.60914 (7)0.72196 (4)0.00887 (8)
C30.94112 (8)0.66909 (7)0.83570 (4)0.00911 (9)
C41.06825 (8)0.81400 (7)0.80734 (4)0.00950 (9)
O50.60656 (7)0.35580 (6)0.48209 (3)0.01331 (8)
H50.6708 (17)0.4186 (14)0.5423 (9)0.051 (3)*
O60.91444 (7)0.67924 (6)0.43705 (4)0.01821 (10)
O70.76472 (7)0.57743 (6)0.18786 (3)0.01252 (8)
O80.46746 (7)0.25345 (6)0.23237 (3)0.01397 (8)
C50.65640 (8)0.42058 (7)0.40000 (4)0.00989 (9)
C60.79065 (9)0.56210 (7)0.38264 (4)0.01082 (9)
C70.72452 (8)0.51730 (7)0.26748 (4)0.00974 (9)
C80.58712 (8)0.36880 (7)0.28791 (4)0.01003 (9)
N10.63044 (7)0.12212 (6)0.72119 (4)0.00965 (8)
N20.52866 (8)0.16658 (6)0.87015 (4)0.01028 (8)
H20.4262 (13)0.0901 (11)0.8482 (7)0.018 (2)*
N30.39972 (8)0.18275 (7)1.01241 (4)0.01187 (9)
H3A0.4056 (13)0.2263 (12)1.0734 (7)0.025 (2)*
H3B0.3178 (13)0.0959 (11)0.9852 (7)0.023 (2)*
N40.87102 (8)0.24052 (7)0.87271 (4)0.01209 (9)
H4A0.9082 (14)0.2667 (12)0.9410 (8)0.029 (3)*
H4B0.9620 (13)0.2700 (10)0.8380 (7)0.014 (2)*
N50.65777 (8)0.38725 (6)0.99499 (4)0.01082 (8)
H5A0.6627 (14)0.4359 (12)1.0556 (8)0.027 (3)*
H5B0.7293 (14)0.4329 (12)0.9578 (7)0.026 (3)*
C90.78222 (10)0.09007 (9)0.67128 (5)0.01460 (11)
H9A0.8304 (13)0.1804 (12)0.6341 (7)0.024 (2)*
H9B0.7220 (14)0.0065 (11)0.6255 (7)0.026 (2)*
H9C0.8943 (14)0.0679 (11)0.7230 (7)0.023 (2)*
C100.42488 (10)0.08860 (9)0.65249 (5)0.01488 (11)
H10A0.3661 (14)0.0235 (12)0.6383 (7)0.030 (3)*
H10B0.4293 (14)0.1421 (11)0.5864 (7)0.025 (2)*
H10C0.3366 (13)0.1299 (11)0.6835 (7)0.019 (2)*
C110.68078 (8)0.17996 (7)0.82051 (4)0.00891 (8)
C120.53214 (8)0.24935 (7)0.96159 (4)0.00903 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0183 (2)0.01233 (19)0.00824 (17)0.00355 (16)0.00494 (15)0.00034 (14)
O20.01403 (18)0.00950 (17)0.00948 (17)0.00224 (15)0.00182 (14)0.00152 (13)
O30.01373 (18)0.01367 (19)0.00851 (17)0.00120 (15)0.00337 (14)0.00108 (14)
O40.01462 (19)0.01294 (19)0.01184 (18)0.00490 (16)0.00388 (14)0.00372 (14)
C10.0098 (2)0.0088 (2)0.0086 (2)0.00002 (17)0.00285 (16)0.00054 (16)
C20.0088 (2)0.0090 (2)0.0082 (2)0.00081 (17)0.00199 (15)0.00018 (16)
C30.0083 (2)0.0092 (2)0.0088 (2)0.00031 (17)0.00184 (15)0.00058 (16)
C40.0095 (2)0.0096 (2)0.0085 (2)0.00020 (18)0.00285 (16)0.00071 (16)
O50.0164 (2)0.01345 (19)0.00788 (17)0.00186 (16)0.00377 (14)0.00036 (14)
O60.0211 (2)0.0183 (2)0.00984 (18)0.00826 (18)0.00526 (16)0.00417 (15)
O70.01484 (19)0.01390 (19)0.00844 (17)0.00120 (16)0.00416 (14)0.00077 (14)
O80.01384 (19)0.0144 (2)0.01071 (18)0.00174 (16)0.00232 (14)0.00279 (14)
C50.0098 (2)0.0112 (2)0.0083 (2)0.00126 (18)0.00262 (16)0.00018 (16)
C60.0112 (2)0.0124 (2)0.0081 (2)0.00053 (19)0.00310 (16)0.00033 (17)
C70.0098 (2)0.0112 (2)0.0079 (2)0.00201 (18)0.00213 (16)0.00052 (16)
C80.0096 (2)0.0118 (2)0.0085 (2)0.00213 (18)0.00241 (16)0.00004 (17)
N10.01006 (19)0.01043 (19)0.00796 (18)0.00028 (16)0.00323 (14)0.00100 (14)
N20.00995 (19)0.0106 (2)0.00914 (18)0.00241 (16)0.00445 (14)0.00294 (15)
N30.0120 (2)0.0124 (2)0.0099 (2)0.00268 (17)0.00514 (15)0.00251 (16)
N40.00968 (19)0.0159 (2)0.00938 (19)0.00037 (17)0.00296 (15)0.00190 (16)
N50.0114 (2)0.0102 (2)0.00981 (19)0.00160 (16)0.00430 (15)0.00213 (15)
C90.0162 (3)0.0170 (3)0.0130 (2)0.0041 (2)0.0078 (2)0.0007 (2)
C100.0124 (2)0.0189 (3)0.0101 (2)0.0010 (2)0.00124 (18)0.0008 (2)
C110.0099 (2)0.0079 (2)0.0089 (2)0.00091 (17)0.00346 (16)0.00040 (15)
C120.0092 (2)0.0096 (2)0.0079 (2)0.00137 (17)0.00221 (15)0.00060 (16)
Geometric parameters (Å, º) top
O1—C11.2962 (7)N1—C91.4633 (8)
O1—H10.930 (12)N2—C121.3768 (7)
O2—C21.2453 (7)N2—C111.3794 (7)
O3—C31.2332 (7)N2—H20.848 (9)
O4—C41.2492 (7)N3—C121.3201 (7)
C1—C41.4364 (8)N3—H3A0.865 (9)
C1—C21.4448 (8)N3—H3B0.847 (9)
C2—C31.4883 (7)N4—C111.3261 (7)
C3—C41.4774 (8)N4—H4A0.875 (10)
O5—C51.3058 (7)N4—H4B0.876 (8)
O5—H50.904 (12)N5—C121.3077 (7)
O6—C61.2502 (7)N5—H5A0.881 (10)
O7—C71.2362 (7)N5—H5B0.832 (10)
O8—C81.2354 (7)C9—H9A0.963 (10)
C5—C61.4282 (8)C9—H9B0.964 (9)
C5—C81.4512 (8)C9—H9C0.953 (9)
C6—C71.4762 (8)C10—H10A0.955 (10)
C7—C81.4958 (8)C10—H10B0.985 (9)
N1—C111.3156 (7)C10—H10C0.951 (9)
N1—C101.4617 (8)
C1—O1—H1113.5 (7)C12—N2—H2114.0 (6)
O1—C1—C4130.73 (5)C11—N2—H2117.7 (6)
O1—C1—C2136.50 (5)C12—N3—H3A118.7 (6)
C4—C1—C292.75 (4)C12—N3—H3B117.9 (6)
O2—C2—C1137.15 (5)H3A—N3—H3B123.3 (9)
O2—C2—C3134.32 (5)C11—N4—H4A122.3 (6)
C1—C2—C388.53 (4)C11—N4—H4B120.3 (5)
O3—C3—C4134.09 (5)H4A—N4—H4B116.7 (8)
O3—C3—C2136.53 (5)C12—N5—H5A120.4 (6)
C4—C3—C289.38 (4)C12—N5—H5B120.6 (7)
O4—C4—C1136.17 (5)H5A—N5—H5B118.9 (9)
O4—C4—C3134.54 (5)N1—C9—H9A111.2 (6)
C1—C4—C389.28 (4)N1—C9—H9B107.1 (6)
C5—O5—H5111.2 (7)H9A—C9—H9B112.9 (8)
O5—C5—C6135.97 (5)N1—C9—H9C110.9 (5)
O5—C5—C8131.14 (5)H9A—C9—H9C108.2 (8)
C6—C5—C892.88 (5)H9B—C9—H9C106.4 (8)
O6—C6—C5137.70 (5)N1—C10—H10A113.0 (6)
O6—C6—C7132.52 (5)N1—C10—H10B107.2 (5)
C5—C6—C789.78 (4)H10A—C10—H10B111.3 (8)
O7—C7—C6135.42 (5)N1—C10—H10C112.1 (5)
O7—C7—C8135.39 (5)H10A—C10—H10C105.0 (8)
C6—C7—C889.19 (4)H10B—C10—H10C108.2 (8)
O8—C8—C5136.55 (6)N1—C11—N4121.51 (5)
O8—C8—C7135.31 (5)N1—C11—N2117.19 (5)
C5—C8—C788.14 (4)N4—C11—N2121.20 (5)
C11—N1—C10123.70 (5)N5—C12—N3122.13 (5)
C11—N1—C9121.02 (5)N5—C12—N2121.66 (5)
C10—N1—C9115.27 (5)N3—C12—N2116.21 (5)
C12—N2—C11127.70 (5)
(multipole) top
Crystal data top
?Z = 2
Mr = ?F(000) = 372
?, ?Dx = 1.596 Mg m3
a = 7.0689 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.5538 (2) ÅCell parameters from 8412 reflections
c = 13.0736 (3) Åθ = 2.4–50.7°
α = 90.4260 (9)°µ = 0.14 mm1
β = 105.1180 (9)°T = 100 K
γ = 102.425 (1)°Block, colorless
V = 743.58 (3) Å30.38 × 0.21 × 0.13 mm
Data collection top
CCD area detector
diffractometer
9502 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.046
Graphite monochromatorθmax = 52.2°, θmin = 2.4°
ω scansh = 1515
38327 measured reflectionsk = 1818
15808 independent reflectionsl = 2828
Refinement top
Refinement on F2950 parameters
Least-squares matrix: full0 restraints
R[F2 > 2σ(F2)] = 0.034 w1 = 1/[s2(Fo)]
wR(F2) = 0.047(Δ/σ)max < 0.001
S = 1.05Δρmax = 0.13 e Å3
15808 reflectionsΔρmin = 0.12 e Å3
Crystal data top
?γ = 102.425 (1)°
Mr = ?V = 743.58 (3) Å3
?, ?Z = 2
a = 7.0689 (2) ÅMo Kα radiation
b = 8.5538 (2) ŵ = 0.14 mm1
c = 13.0736 (3) ÅT = 100 K
α = 90.4260 (9)°0.38 × 0.21 × 0.13 mm
β = 105.1180 (9)°
Data collection top
CCD area detector
diffractometer
9502 reflections with I > 2σ(I)
38327 measured reflectionsRint = 0.046
15808 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.034950 parameters
wR(F2) = 0.0470 restraints
S = 1.05Δρmax = 0.13 e Å3
15808 reflectionsΔρmin = 0.12 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O(1)1.02713 (9)0.82004 (6)0.61293 (4)0.013
O(2)0.75979 (8)0.48450 (6)0.67228 (4)0.011
O(3)0.90715 (8)0.62250 (6)0.91944 (4)0.012
O(4)1.18689 (8)0.93559 (6)0.85841 (4)0.014
O(5)0.60656 (8)0.35590 (6)0.48207 (4)0.013
O(6)0.91444 (10)0.67914 (8)0.43696 (4)0.018
O(7)0.76498 (8)0.57744 (7)0.18799 (4)0.012
O(8)0.46732 (8)0.25368 (7)0.23242 (4)0.013
N(1)0.63034 (7)0.12207 (6)0.72110 (4)0.009
N(2)0.52868 (7)0.16648 (6)0.87014 (4)0.01
N(3)0.39946 (7)0.18258 (6)1.01252 (4)0.011
N(4)0.87139 (7)0.24075 (6)0.87279 (4)0.011
N(5)0.65814 (7)0.38762 (6)0.99499 (4)0.01
C(1)0.99400 (6)0.75564 (5)0.69753 (3)0.009
C(2)0.87259 (6)0.60900 (5)0.72191 (3)0.009
C(3)0.94121 (6)0.66909 (5)0.83581 (3)0.009
C(4)1.06835 (6)0.81401 (5)0.80726 (3)0.009
C(5)0.65613 (6)0.42036 (5)0.40015 (3)0.01
C(6)0.79090 (7)0.56219 (6)0.38274 (3)0.01
C(7)0.72436 (6)0.51738 (5)0.26745 (3)0.009
C(8)0.58700 (6)0.36876 (5)0.28786 (3)0.01
C(9)0.78181 (7)0.08988 (6)0.67125 (4)0.014
C(10)0.42517 (7)0.08865 (6)0.65247 (3)0.015
C(11)0.68065 (6)0.18009 (5)0.82055 (3)0.008
C(12)0.53207 (6)0.24928 (5)0.96156 (3)0.009
H(1)0.9628330.747250.5422670.022
H(5)0.6810410.4202740.5524660.022
H(2)0.4066650.0706040.8446380.021
H(3A)0.4090380.2277011.0861020.021
H(3B)0.3038890.0763920.9813550.023
H(4A)0.9195650.2687850.9522870.023
H(4B)0.9748040.2799870.8325110.023
H(5A)0.6673860.4436321.0661110.021
H(5B)0.7467590.449510.9516620.021
H(9A)0.8337690.1881740.6280720.044
H(9B)0.7141630.0174830.6182060.043
H(9C)0.9083120.0676980.731820.034
H(10A)0.3680410.0388690.6372650.04
H(10B)0.4262760.1440670.578950.038
H(10C)0.3267070.1391190.6881360.034
DUM000000
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O(1)0.0175 (2)0.01192 (17)0.00764 (16)0.00344 (16)0.00442 (14)0.00051 (14)
O(2)0.01345 (17)0.00900 (15)0.00856 (16)0.00220 (15)0.00179 (13)0.00158 (12)
O(3)0.01292 (17)0.01275 (18)0.00773 (16)0.00217 (15)0.00314 (13)0.00080 (13)
O(4)0.01433 (18)0.01230 (17)0.01080 (18)0.00519 (16)0.00411 (14)0.00367 (14)
O(5)0.01505 (18)0.01302 (18)0.00731 (16)0.00179 (16)0.00331 (14)0.00040 (14)
O(6)0.0207 (2)0.0180 (2)0.00875 (18)0.0083 (2)0.00523 (16)0.00438 (16)
O(7)0.01405 (18)0.01324 (18)0.00739 (16)0.00044 (16)0.00372 (13)0.00033 (13)
O(8)0.01353 (18)0.01360 (18)0.00970 (17)0.00204 (16)0.00227 (13)0.00254 (14)
N(1)0.00968 (15)0.01035 (15)0.00744 (15)0.00041 (13)0.00318 (12)0.00130 (12)
N(2)0.00935 (15)0.01025 (16)0.00912 (16)0.00205 (14)0.00440 (12)0.00300 (12)
N(3)0.01138 (16)0.01185 (17)0.00950 (16)0.00246 (14)0.00531 (13)0.00231 (13)
N(4)0.00860 (15)0.01567 (18)0.00872 (16)0.00003 (15)0.00235 (12)0.00209 (14)
N(5)0.01074 (16)0.00925 (15)0.00971 (16)0.00180 (14)0.00424 (12)0.00234 (12)
C(1)0.01035 (15)0.00858 (15)0.00716 (15)0.00052 (13)0.00277 (11)0.00046 (12)
C(2)0.00903 (14)0.00787 (14)0.00743 (14)0.00047 (12)0.00177 (11)0.00039 (11)
C(3)0.00875 (14)0.00922 (15)0.00713 (15)0.00045 (12)0.00205 (11)0.00015 (11)
C(4)0.00949 (15)0.00878 (15)0.00797 (15)0.00152 (13)0.00245 (11)0.00124 (12)
C(5)0.00999 (15)0.01082 (16)0.00719 (15)0.00040 (13)0.00253 (11)0.00003 (12)
C(6)0.01115 (16)0.01157 (16)0.00713 (15)0.00090 (14)0.00259 (12)0.00118 (12)
C(7)0.01027 (15)0.01099 (16)0.00663 (15)0.00128 (13)0.00249 (11)0.00014 (12)
C(8)0.00936 (15)0.01090 (16)0.00765 (15)0.00067 (13)0.00183 (11)0.00085 (12)
C(9)0.01559 (17)0.01629 (19)0.01268 (16)0.00399 (15)0.00730 (14)0.00043 (14)
C(10)0.01233 (16)0.0184 (2)0.00973 (16)0.00108 (15)0.00145 (12)0.00091 (13)
C(11)0.00868 (14)0.00858 (14)0.00778 (14)0.00044 (12)0.00289 (11)0.00059 (11)
C(12)0.00871 (14)0.00878 (14)0.00789 (14)0.00007 (12)0.00307 (11)0.00134 (11)
H(1)0.0248740.0227930.015380.0007690.0034810.004255
H(5)0.0234030.0203120.0168390.0025390.0031840.000907
H(2)0.0229520.0163280.0189630.0042430.0049350.004547
H(3A)0.0260830.0256560.0052770.0047240.002870.00294
H(3B)0.0230820.0204730.0192460.0075970.0062560.000597
H(4A)0.021270.0264840.0164510.0006970.0004160.002639
H(4B)0.0169250.0324980.0171940.0019090.0074590.001808
H(5A)0.0220190.0196240.0155250.0012420.0004480.003383
H(5B)0.0198570.0182560.0208450.0053550.006480.000694
H(9A)0.0515410.0443590.0507650.0142410.037050.02668
H(9B)0.0322710.0448180.047060.0006850.0094730.026902
H(9C)0.030670.0509230.0229490.0167620.0056320.001197
H(10A)0.0338530.0278460.0409110.0090790.0055910.004303
H(10B)0.0274670.0617470.0176570.0052870.0001460.011619
H(10C)0.0231370.0605880.0191990.012840.0024490.009426
Geometric parameters (Å, º) top
O(1)—C(1)1.2925 (6)N(4)—H(4A)1.0150 (5)
O(1)—H(1)1.0480 (5)N(4)—H(4B)1.0110 (5)
O(2)—C(2)1.2431 (6)N(5)—C(12)1.3118 (6)
O(3)—C(3)1.2307 (6)N(5)—H(5A)1.0230 (5)
O(4)—C(4)1.2464 (6)N(5)—H(5B)1.0200 (5)
O(5)—C(5)1.3019 (6)C(1)—C(2)1.4480 (6)
O(5)—H(5)1.0210 (5)C(1)—C(4)1.4376 (6)
O(6)—C(6)1.2476 (6)C(2)—C(3)1.4905 (5)
O(7)—C(7)1.2351 (6)C(3)—C(4)1.4785 (6)
O(8)—C(8)1.2334 (6)C(5)—C(6)1.4322 (6)
N(1)—C(9)1.4613 (6)C(5)—C(8)1.4534 (6)
N(1)—C(10)1.4592 (6)C(6)—C(7)1.4779 (6)
N(1)—C(11)1.3177 (6)C(7)—C(8)1.4964 (6)
N(2)—C(11)1.3779 (6)C(9)—H(9A)1.0690 (5)
N(2)—C(12)1.3768 (6)C(9)—H(9B)1.0870 (5)
N(2)—H(2)1.0340 (5)C(9)—H(9C)1.0810 (5)
N(3)—C(12)1.3227 (6)C(10)—H(10A)1.0760 (5)
N(3)—H(3A)1.0140 (5)C(10)—H(10B)1.0760 (5)
N(3)—H(3B)1.0170 (5)C(10)—H(10C)1.0880 (5)
N(4)—C(11)1.3293 (6)
C(1)—O(1)—H(1)115.43 (5)O(5)—C(5)—C(8)131.31 (5)
C(5)—O(5)—H(5)113.87 (5)C(6)—C(5)—C(8)92.77 (4)
C(9)—N(1)—C(10)115.23 (4)O(6)—C(6)—C(5)137.74 (5)
C(9)—N(1)—C(11)121.08 (5)O(6)—C(6)—C(7)132.51 (5)
C(10)—N(1)—C(11)123.68 (4)C(5)—C(6)—C(7)89.75 (3)
C(11)—N(2)—C(12)127.67 (4)O(7)—C(7)—C(6)135.31 (5)
C(11)—N(2)—H(2)117.18 (4)O(7)—C(7)—C(8)135.45 (5)
C(12)—N(2)—H(2)114.24 (4)C(6)—C(7)—C(8)89.24 (3)
C(12)—N(3)—H(3A)119.92 (5)O(8)—C(8)—C(5)136.43 (5)
C(12)—N(3)—H(3B)118.14 (5)O(8)—C(8)—C(7)135.34 (5)
H(3A)—N(3)—H(3B)121.22 (5)C(5)—C(8)—C(7)88.23 (3)
C(11)—N(4)—H(4A)124.00 (5)N(1)—C(9)—H(9A)111.82 (4)
C(11)—N(4)—H(4B)120.22 (5)N(1)—C(9)—H(9B)107.69 (4)
H(4A)—N(4)—H(4B)114.97 (5)N(1)—C(9)—H(9C)109.29 (4)
C(12)—N(5)—H(5A)120.93 (5)H(9A)—C(9)—H(9B)110.17 (4)
C(12)—N(5)—H(5B)123.56 (5)H(9A)—C(9)—H(9C)108.93 (4)
H(5A)—N(5)—H(5B)115.43 (5)H(9B)—C(9)—H(9C)108.89 (4)
O(1)—C(1)—C(2)136.53 (4)N(1)—C(10)—H(10A)109.86 (4)
O(1)—C(1)—C(4)130.79 (5)N(1)—C(10)—H(10B)108.70 (4)
C(2)—C(1)—C(4)92.66 (3)N(1)—C(10)—H(10C)111.31 (4)
O(2)—C(2)—C(1)137.12 (4)H(10A)—C(10)—H(10B)109.89 (4)
O(2)—C(2)—C(3)134.34 (5)H(10A)—C(10)—H(10C)109.51 (4)
C(1)—C(2)—C(3)88.54 (3)H(10B)—C(10)—H(10C)107.53 (5)
O(3)—C(3)—C(2)136.48 (5)N(1)—C(11)—N(2)117.19 (4)
O(3)—C(3)—C(4)134.18 (4)N(1)—C(11)—N(4)121.42 (4)
C(2)—C(3)—C(4)89.33 (3)N(2)—C(11)—N(4)121.27 (4)
O(4)—C(4)—C(1)136.17 (5)N(2)—C(12)—N(3)116.24 (4)
O(4)—C(4)—C(3)134.42 (5)N(2)—C(12)—N(5)121.61 (4)
C(1)—C(4)—C(3)89.40 (3)N(3)—C(12)—N(5)122.15 (4)
O(5)—C(5)—C(6)135.92 (4)
(neutron) top
Crystal data top
C4H13N5·C8H2O8V = 743.58 (3) Å3
Mr = 357.28Z = 2
Triclinic, P1F(000) = 23
Hall symbol: -P 1Dx = 1.596 Mg m3
a = 7.0689 (2) ÅNeutron radiation, λ = 0.86800 Å
b = 8.5538 (2) ŵ = 0.15 mm1
c = 13.0736 (3) ÅT = 100 K
α = 90.4260 (9)°Plate, colorless
β = 105.1180 (9)°3.5 × 3.5 × 3 mm
γ = 102.425 (1)°
Data collection top
Closed Eulerian cradle HEiDi
diffractometer
4116 reflections with I > 2σ(I)
Radiation source: FRM IIRint = 0.073
Graphite monochromatorθmax = 45.4°, θmin = 3.5°
rocking scanh = 1110
7815 measured reflectionsk = 1313
5560 independent reflectionsl = 1817
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.061All H-atom parameters refined
wR(F2) = 0.156 w = 1/[σ2(Fo2) + (0.0563P)2 + 0.0635P]
where P = (Fo2 + 2Fc2)/3
S = 1.14(Δ/σ)max = 0.001
5560 reflectionsΔρmax = 0.10 e Å3
362 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 1.67 (15)
Crystal data top
C4H13N5·C8H2O8γ = 102.425 (1)°
Mr = 357.28V = 743.58 (3) Å3
Triclinic, P1Z = 2
a = 7.0689 (2) ÅNeutron radiation, λ = 0.86800 Å
b = 8.5538 (2) ŵ = 0.15 mm1
c = 13.0736 (3) ÅT = 100 K
α = 90.4260 (9)°3.5 × 3.5 × 3 mm
β = 105.1180 (9)°
Data collection top
Closed Eulerian cradle HEiDi
diffractometer
4116 reflections with I > 2σ(I)
7815 measured reflectionsRint = 0.073
5560 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0610 restraints
wR(F2) = 0.156All H-atom parameters refined
S = 1.14Δρmax = 0.10 e Å3
5560 reflectionsΔρmin = 0.17 e Å3
362 parameters
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*/Ueq
O11.0273 (3)0.8197 (2)0.61322 (17)0.0205 (3)
H10.9630 (6)0.7471 (4)0.5425 (3)0.0298 (6)
O20.7594 (3)0.48481 (18)0.67219 (16)0.0179 (3)
O30.9069 (3)0.62245 (19)0.91923 (16)0.0186 (3)
O41.1864 (3)0.9356 (2)0.85841 (16)0.0196 (3)
C10.9940 (2)0.75569 (15)0.69745 (13)0.0153 (2)
C20.87228 (19)0.60890 (15)0.72189 (12)0.0145 (2)
C30.9411 (2)0.66886 (15)0.83606 (13)0.0153 (2)
C41.0685 (2)0.81410 (15)0.80731 (13)0.0156 (2)
O50.6064 (3)0.3562 (2)0.48223 (16)0.0194 (3)
H50.6819 (5)0.4211 (4)0.5524 (3)0.0297 (7)
O60.9143 (3)0.6790 (2)0.43688 (18)0.0242 (4)
O70.7644 (3)0.5772 (2)0.18796 (16)0.0188 (3)
O80.4680 (3)0.2535 (2)0.23228 (17)0.0199 (3)
C50.6560 (2)0.42020 (16)0.40033 (13)0.0163 (3)
C60.7908 (2)0.56227 (16)0.38259 (13)0.0168 (3)
C70.7247 (2)0.51746 (16)0.26726 (13)0.0159 (2)
C80.5869 (2)0.36876 (16)0.28797 (13)0.0162 (2)
N10.63032 (15)0.12227 (11)0.72094 (9)0.01618 (19)
N20.52882 (15)0.16629 (12)0.87032 (10)0.01702 (19)
H20.4059 (5)0.0713 (4)0.8443 (3)0.0290 (6)
N30.39937 (16)0.18272 (12)1.01253 (10)0.01786 (19)
H3A0.4083 (6)0.2284 (4)1.0859 (3)0.0303 (7)
H3B0.3032 (6)0.0767 (4)0.9817 (3)0.0322 (7)
N40.87128 (15)0.24078 (13)0.87288 (10)0.0185 (2)
H4A0.9178 (6)0.2694 (5)0.9523 (3)0.0321 (7)
H4B0.9744 (5)0.2791 (5)0.8324 (4)0.0323 (7)
N50.65845 (15)0.38779 (11)0.99528 (10)0.01688 (19)
H5A0.6660 (6)0.4443 (4)1.0659 (3)0.0297 (6)
H5B0.7462 (6)0.4493 (4)0.9515 (3)0.0302 (7)
C90.7821 (2)0.09005 (19)0.67127 (15)0.0204 (3)
H9A0.8338 (9)0.1900 (7)0.6292 (6)0.0537 (14)
H9B0.7154 (8)0.0186 (7)0.6194 (5)0.0527 (14)
H9C0.9094 (7)0.0663 (6)0.7307 (5)0.0434 (10)
C100.4254 (2)0.08860 (19)0.65261 (15)0.0208 (3)
H10A0.3663 (8)0.0387 (5)0.6376 (5)0.0501 (13)
H10B0.4263 (7)0.1434 (7)0.5789 (4)0.0477 (12)
H10C0.3253 (6)0.1382 (7)0.6875 (4)0.0445 (11)
C110.6816 (2)0.18013 (15)0.82042 (13)0.0151 (2)
C120.5324 (2)0.24947 (15)0.96148 (13)0.0149 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0235 (7)0.0176 (6)0.0165 (9)0.0026 (5)0.0045 (6)0.0014 (5)
H10.0323 (14)0.0285 (13)0.0255 (19)0.0005 (11)0.0082 (12)0.0009 (11)
O20.0192 (6)0.0144 (5)0.0155 (9)0.0027 (4)0.0022 (5)0.0010 (5)
O30.0181 (6)0.0173 (6)0.0171 (9)0.0016 (5)0.0039 (5)0.0012 (5)
O40.0191 (6)0.0169 (6)0.0183 (9)0.0047 (5)0.0043 (5)0.0036 (5)
C10.0142 (5)0.0144 (5)0.0153 (7)0.0005 (4)0.0025 (4)0.0006 (4)
C20.0134 (4)0.0134 (4)0.0143 (7)0.0004 (3)0.0017 (4)0.0005 (4)
C30.0138 (4)0.0140 (5)0.0167 (7)0.0006 (4)0.0036 (4)0.0010 (4)
C40.0136 (5)0.0142 (5)0.0160 (7)0.0012 (4)0.0025 (4)0.0001 (4)
O50.0196 (6)0.0188 (6)0.0167 (9)0.0004 (5)0.0034 (5)0.0016 (5)
H50.0304 (14)0.0301 (13)0.0231 (18)0.0022 (11)0.0049 (11)0.0004 (11)
O60.0247 (7)0.0235 (7)0.0176 (10)0.0074 (6)0.0047 (6)0.0042 (6)
O70.0191 (6)0.0183 (6)0.0169 (9)0.0002 (5)0.0045 (5)0.0018 (5)
O80.0190 (6)0.0195 (6)0.0170 (9)0.0016 (5)0.0025 (5)0.0028 (5)
C50.0152 (5)0.0161 (5)0.0156 (7)0.0013 (4)0.0023 (4)0.0010 (4)
C60.0162 (5)0.0158 (5)0.0152 (7)0.0003 (4)0.0023 (4)0.0011 (4)
C70.0143 (5)0.0168 (5)0.0149 (7)0.0018 (4)0.0022 (4)0.0013 (4)
C80.0150 (5)0.0163 (5)0.0145 (7)0.0013 (4)0.0007 (4)0.0005 (4)
N10.0161 (4)0.0154 (3)0.0151 (5)0.0008 (3)0.0031 (3)0.0008 (3)
N20.0157 (4)0.0155 (3)0.0177 (5)0.0010 (3)0.0046 (3)0.0021 (3)
H20.0251 (12)0.0285 (13)0.0289 (19)0.0025 (10)0.0068 (11)0.0060 (11)
N30.0174 (4)0.0176 (4)0.0170 (6)0.0010 (3)0.0059 (3)0.0006 (3)
H3A0.0319 (14)0.0332 (14)0.0228 (19)0.0020 (11)0.0096 (12)0.0015 (11)
H3B0.0313 (14)0.0285 (14)0.031 (2)0.0092 (11)0.0111 (13)0.0013 (12)
N40.0150 (4)0.0205 (4)0.0177 (6)0.0010 (3)0.0032 (3)0.0009 (3)
H4A0.0299 (14)0.0368 (16)0.026 (2)0.0048 (12)0.0037 (12)0.0014 (12)
H4B0.0213 (12)0.0409 (17)0.033 (2)0.0006 (11)0.0089 (12)0.0007 (13)
N50.0152 (3)0.0146 (3)0.0183 (6)0.0009 (3)0.0037 (3)0.0018 (3)
H5A0.0318 (14)0.0285 (13)0.0254 (19)0.0003 (11)0.0075 (12)0.0039 (11)
H5B0.0297 (14)0.0292 (13)0.030 (2)0.0016 (11)0.0113 (12)0.0003 (11)
C90.0213 (6)0.0219 (6)0.0192 (9)0.0052 (5)0.0071 (5)0.0005 (5)
H9A0.062 (3)0.051 (2)0.068 (4)0.019 (2)0.044 (3)0.028 (3)
H9B0.045 (2)0.055 (3)0.053 (3)0.005 (2)0.012 (2)0.030 (2)
H9C0.0350 (18)0.056 (2)0.042 (3)0.0225 (18)0.0048 (16)0.0018 (19)
C100.0180 (5)0.0237 (6)0.0174 (8)0.0007 (4)0.0037 (5)0.0002 (5)
H10A0.041 (2)0.0348 (18)0.057 (3)0.0065 (16)0.005 (2)0.0066 (18)
H10B0.0346 (18)0.073 (3)0.025 (3)0.0020 (19)0.0016 (15)0.012 (2)
H10C0.0275 (16)0.070 (3)0.036 (3)0.0156 (17)0.0045 (15)0.006 (2)
C110.0144 (5)0.0140 (4)0.0153 (7)0.0008 (4)0.0034 (4)0.0006 (4)
C120.0140 (5)0.0128 (4)0.0165 (7)0.0012 (4)0.0031 (4)0.0008 (4)
Geometric parameters (Å, º) top
O1—C11.287 (3)N1—C111.317 (2)
O1—H11.048 (4)N1—C101.4564 (19)
O2—C21.2412 (19)N1—C91.462 (2)
O3—C31.225 (3)N2—C121.375 (2)
O4—C41.244 (2)N2—C111.385 (2)
C1—C41.439 (2)N2—H21.034 (3)
C1—C21.4503 (19)N3—C121.3258 (19)
C1—C32.057 (2)N3—H3A1.015 (4)
C2—C31.493 (2)N3—H3B1.016 (3)
C2—C42.0898 (19)N4—C111.3243 (16)
C3—C41.4827 (19)N4—H4A1.015 (4)
O5—C51.300 (3)N4—H4B1.010 (4)
O5—H51.021 (4)N5—C121.3124 (16)
O6—C61.247 (2)N5—H5A1.022 (4)
O7—C71.230 (2)N5—H5B1.019 (4)
O8—C81.234 (2)C9—H9A1.069 (5)
C5—C61.435 (2)C9—H9B1.087 (5)
C5—C81.454 (2)C9—H9C1.082 (5)
C5—C72.060 (2)C10—H10A1.076 (5)
C6—C71.478 (2)C10—H10B1.076 (6)
C6—C82.088 (2)C10—H10C1.088 (5)
C7—C81.500 (2)
C1—O1—H1115.5 (2)O7—C7—C5179.11 (15)
O1—C1—C4130.78 (13)C6—C7—C544.17 (8)
O1—C1—C2136.55 (15)C8—C7—C544.88 (9)
C4—C1—C292.65 (13)O8—C8—C5136.58 (17)
O1—C1—C3176.07 (14)O8—C8—C7135.00 (18)
C4—C1—C346.13 (8)C5—C8—C788.42 (11)
C2—C1—C346.55 (9)O8—C8—C6179.32 (15)
O2—C2—C1137.02 (17)C5—C8—C643.37 (8)
O2—C2—C3134.36 (16)C7—C8—C645.06 (9)
C1—C2—C388.62 (11)C11—N1—C10123.92 (13)
O2—C2—C4178.37 (14)C11—N1—C9120.69 (12)
C1—C2—C443.47 (9)C10—N1—C9115.38 (13)
C3—C2—C445.19 (8)C12—N2—C11127.54 (11)
O3—C3—C4134.30 (15)C12—N2—H2114.4 (3)
O3—C3—C2136.47 (13)C11—N2—H2117.3 (3)
C4—C3—C289.21 (12)C12—N3—H3A120.0 (2)
O3—C3—C1177.46 (14)C12—N3—H3B118.5 (3)
C4—C3—C144.41 (8)H3A—N3—H3B120.9 (3)
C2—C3—C144.83 (8)C11—N4—H4A123.7 (3)
O4—C4—C1136.24 (16)C11—N4—H4B119.7 (3)
O4—C4—C3134.28 (17)H4A—N4—H4B115.7 (3)
C1—C4—C389.46 (11)C12—N5—H5A121.0 (2)
O4—C4—C2179.54 (15)C12—N5—H5B123.0 (2)
C1—C4—C243.89 (8)H5A—N5—H5B115.9 (3)
C3—C4—C245.60 (8)N1—C9—H9A110.9 (3)
C5—O5—H5113.5 (3)N1—C9—H9B107.7 (3)
C6—O6—H1136.6 (2)H9A—C9—H9B112.0 (6)
O5—C5—C6135.95 (15)N1—C9—H9C110.5 (4)
O5—C5—C8131.48 (14)H9A—C9—H9C108.7 (5)
C6—C5—C892.57 (13)H9B—C9—H9C107.0 (5)
O5—C5—C7177.97 (13)N1—C10—H10A110.5 (3)
C6—C5—C745.86 (9)N1—C10—H10B108.7 (3)
C8—C5—C746.71 (8)H10A—C10—H10B109.8 (5)
O6—C6—C5137.51 (19)N1—C10—H10C112.1 (3)
O6—C6—C7132.53 (17)H10A—C10—H10C108.2 (5)
C5—C6—C789.96 (11)H10B—C10—H10C107.5 (5)
O6—C6—C8178.40 (17)N1—C11—N4121.99 (14)
C5—C6—C844.07 (9)N1—C11—N2116.93 (12)
C7—C6—C845.90 (8)N4—C11—N2120.98 (14)
O7—C7—C6135.51 (14)N5—C12—N3121.93 (14)
O7—C7—C8135.44 (15)N5—C12—N2121.96 (13)
C6—C7—C889.05 (12)N3—C12—N2116.10 (11)

Experimental details

(iam)(multipole)(neutron)
Crystal data
Chemical formulaC4H13N5·2(C4HO4)?C4H13N5·C8H2O8
Mr357.29?357.28
Crystal system, space groupTriclinic, P1?, ?Triclinic, P1
Temperature (K)100100100
a, b, c (Å)7.0689 (2), 8.5538 (2), 13.0736 (3)7.0689 (2), 8.5538 (2), 13.0736 (3)7.0689 (2), 8.5538 (2), 13.0736 (3)
α, β, γ (°)90.4259 (9), 105.1185 (9), 102.4251 (10)90.4260 (9), 105.1180 (9), 102.425 (1)90.4260 (9), 105.1180 (9), 102.425 (1)
V3)743.58 (3)743.58 (3)743.58 (3)
Z222
Radiation typeMo KαMo KαNeutron, λ = 0.86800 Å
µ (mm1)0.140.140.15
Crystal size (mm)0.38 × 0.21 × 0.130.38 × 0.21 × 0.133.5 × 3.5 × 3
Data collection
DiffractometerCCD area detector
diffractometer
CCD area detector
diffractometer
Closed Eulerian cradle HEiDi
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
38327, 15808, 9502 38327, 15808, 9502 7815, 5560, 4116
Rint0.0460.0460.073
(sin θ/λ)max1)1.1121.1120.821
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.106, 1.07 0.034, 0.047, 1.05 0.061, 0.156, 1.14
No. of reflections15808158085560
No. of parameters286950362
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.82, 0.440.13, 0.120.10, 0.17

Computer programs: Bruker SMART, PRON2010, Bruker SAINT, SHELXS97 (Sheldrick, 1997a), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997b), Volkov et al., (2006), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).

Selected geometric parameters (Å, º) for (multipole) top
O(1)—C(1)1.2925 (6)N(4)—H(4A)1.0150 (5)
O(1)—H(1)1.0480 (5)N(4)—H(4B)1.0110 (5)
O(2)—C(2)1.2431 (6)N(5)—C(12)1.3118 (6)
O(3)—C(3)1.2307 (6)N(5)—H(5A)1.0230 (5)
O(4)—C(4)1.2464 (6)N(5)—H(5B)1.0200 (5)
O(5)—C(5)1.3019 (6)C(1)—C(2)1.4480 (6)
O(5)—H(5)1.0210 (5)C(1)—C(4)1.4376 (6)
O(6)—C(6)1.2476 (6)C(2)—C(3)1.4905 (5)
O(7)—C(7)1.2351 (6)C(3)—C(4)1.4785 (6)
O(8)—C(8)1.2334 (6)C(5)—C(6)1.4322 (6)
N(1)—C(9)1.4613 (6)C(5)—C(8)1.4534 (6)
N(1)—C(10)1.4592 (6)C(6)—C(7)1.4779 (6)
N(1)—C(11)1.3177 (6)C(7)—C(8)1.4964 (6)
N(2)—C(11)1.3779 (6)C(9)—H(9A)1.0690 (5)
N(2)—C(12)1.3768 (6)C(9)—H(9B)1.0870 (5)
N(2)—H(2)1.0340 (5)C(9)—H(9C)1.0810 (5)
N(3)—C(12)1.3227 (6)C(10)—H(10A)1.0760 (5)
N(3)—H(3A)1.0140 (5)C(10)—H(10B)1.0760 (5)
N(3)—H(3B)1.0170 (5)C(10)—H(10C)1.0880 (5)
N(4)—C(11)1.3293 (6)
C(1)—O(1)—H(1)115.43 (5)O(5)—C(5)—C(8)131.31 (5)
C(5)—O(5)—H(5)113.87 (5)C(6)—C(5)—C(8)92.77 (4)
C(9)—N(1)—C(10)115.23 (4)O(6)—C(6)—C(5)137.74 (5)
C(9)—N(1)—C(11)121.08 (5)O(6)—C(6)—C(7)132.51 (5)
C(10)—N(1)—C(11)123.68 (4)C(5)—C(6)—C(7)89.75 (3)
C(11)—N(2)—C(12)127.67 (4)O(7)—C(7)—C(6)135.31 (5)
C(11)—N(2)—H(2)117.18 (4)O(7)—C(7)—C(8)135.45 (5)
C(12)—N(2)—H(2)114.24 (4)C(6)—C(7)—C(8)89.24 (3)
C(12)—N(3)—H(3A)119.92 (5)O(8)—C(8)—C(5)136.43 (5)
C(12)—N(3)—H(3B)118.14 (5)O(8)—C(8)—C(7)135.34 (5)
H(3A)—N(3)—H(3B)121.22 (5)C(5)—C(8)—C(7)88.23 (3)
C(11)—N(4)—H(4A)124.00 (5)N(1)—C(9)—H(9A)111.82 (4)
C(11)—N(4)—H(4B)120.22 (5)N(1)—C(9)—H(9B)107.69 (4)
H(4A)—N(4)—H(4B)114.97 (5)N(1)—C(9)—H(9C)109.29 (4)
C(12)—N(5)—H(5A)120.93 (5)H(9A)—C(9)—H(9B)110.17 (4)
C(12)—N(5)—H(5B)123.56 (5)H(9A)—C(9)—H(9C)108.93 (4)
H(5A)—N(5)—H(5B)115.43 (5)H(9B)—C(9)—H(9C)108.89 (4)
O(1)—C(1)—C(2)136.53 (4)N(1)—C(10)—H(10A)109.86 (4)
O(1)—C(1)—C(4)130.79 (5)N(1)—C(10)—H(10B)108.70 (4)
C(2)—C(1)—C(4)92.66 (3)N(1)—C(10)—H(10C)111.31 (4)
O(2)—C(2)—C(1)137.12 (4)H(10A)—C(10)—H(10B)109.89 (4)
O(2)—C(2)—C(3)134.34 (5)H(10A)—C(10)—H(10C)109.51 (4)
C(1)—C(2)—C(3)88.54 (3)H(10B)—C(10)—H(10C)107.53 (5)
O(3)—C(3)—C(2)136.48 (5)N(1)—C(11)—N(2)117.19 (4)
O(3)—C(3)—C(4)134.18 (4)N(1)—C(11)—N(4)121.42 (4)
C(2)—C(3)—C(4)89.33 (3)N(2)—C(11)—N(4)121.27 (4)
O(4)—C(4)—C(1)136.17 (5)N(2)—C(12)—N(3)116.24 (4)
O(4)—C(4)—C(3)134.42 (5)N(2)—C(12)—N(5)121.61 (4)
C(1)—C(4)—C(3)89.40 (3)N(3)—C(12)—N(5)122.15 (4)
O(5)—C(5)—C(6)135.92 (4)
 

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