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In the centrosymmetric title compound, 2C10H18N+·C2N102-·2H2O, the 5,5'-diazenediylditetra­zolate anions are linked to amantadinium cations and water mol­ecules via hydrogen bonding into a two-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807006034/xu2201sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807006034/xu2201Isup2.hkl
Contains datablock I

CCDC reference: 611506

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.058
  • wR factor = 0.181
  • Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.120 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12 PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.82 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 33.00 A   3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Bis(amantadinium) 5,5'-diazenediylditetrazolate dihydrate top
Crystal data top
2C10H18N+·C2N102·2H2OF(000) = 544
Mr = 504.66Dx = 1.249 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1292 reflections
a = 9.789 (7) Åθ = 2.4–23.2°
b = 12.614 (9) ŵ = 0.09 mm1
c = 10.961 (8) ÅT = 298 K
β = 97.657 (11)°Block, yellow
V = 1341.4 (17) Å30.35 × 0.32 × 0.13 mm
Z = 2
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
1295 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.120
Graphite monochromatorθmax = 25.0°, θmin = 2.4°
φ and ω scansh = 1110
6567 measured reflectionsk = 1514
2349 independent reflectionsl = 713
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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.181H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0765P)2]
where P = (Fo2 + 2Fc2)/3
2349 reflections(Δ/σ)max < 0.001
163 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.23 e Å3
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
N10.1831 (2)0.42391 (17)0.6586 (2)0.0381 (7)
N20.2881 (2)0.4474 (2)0.7464 (2)0.0458 (8)
N30.3116 (2)0.5505 (2)0.7471 (2)0.0439 (7)
N40.2220 (2)0.59699 (19)0.6602 (2)0.0410 (7)
N50.0358 (2)0.54014 (17)0.5161 (2)0.0328 (6)
N60.3958 (2)0.70876 (17)0.0540 (2)0.0329 (6)
H6A0.37820.66170.11460.049*
H6B0.48530.70770.02570.049*
H6C0.37220.77320.08240.049*
O10.17614 (19)0.80233 (16)0.54678 (18)0.0445 (6)
H20.17330.84510.60630.053*
H10.18980.74250.58190.053*
C10.1452 (3)0.5179 (2)0.6105 (3)0.0293 (7)
C20.3142 (3)0.6813 (2)0.0480 (3)0.0309 (7)
C30.3584 (3)0.5709 (2)0.0958 (3)0.0384 (8)
H3A0.34010.51940.02990.046*
H3B0.45650.57050.12440.046*
C40.1609 (3)0.6805 (3)0.0007 (3)0.0488 (9)
H4A0.14250.62970.06730.059*
H4B0.13220.75010.03210.059*
C50.3436 (3)0.7631 (2)0.1504 (3)0.0455 (9)
H5A0.31580.83290.11940.055*
H5B0.44160.76480.17960.055*
C60.2784 (4)0.5413 (3)0.2015 (3)0.0553 (10)
H60.30710.47080.23270.066*
C70.1250 (4)0.5401 (3)0.1533 (4)0.0669 (12)
H7A0.10690.48860.08740.080*
H7B0.07270.51990.21880.080*
C80.0809 (3)0.6500 (3)0.1057 (4)0.0630 (11)
H80.01810.64950.07600.076*
C90.1101 (4)0.7312 (3)0.2095 (4)0.0763 (13)
H9A0.08030.80090.17950.092*
H9B0.05900.71270.27640.092*
C100.2634 (4)0.7332 (3)0.2558 (3)0.0634 (11)
H100.28180.78540.32220.076*
C110.3082 (4)0.6229 (3)0.3047 (3)0.0723 (12)
H11A0.40600.62330.33480.087*
H11B0.25850.60430.37250.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0412 (14)0.0286 (14)0.0387 (16)0.0003 (11)0.0161 (12)0.0020 (12)
N20.0507 (16)0.0347 (15)0.0449 (17)0.0007 (12)0.0204 (13)0.0019 (14)
N30.0474 (15)0.0360 (15)0.0422 (17)0.0013 (12)0.0166 (13)0.0004 (14)
N40.0471 (14)0.0288 (14)0.0402 (16)0.0024 (11)0.0195 (13)0.0007 (13)
N50.0382 (14)0.0286 (14)0.0281 (15)0.0005 (10)0.0084 (12)0.0015 (12)
N60.0366 (13)0.0277 (13)0.0321 (15)0.0023 (11)0.0038 (11)0.0010 (11)
O10.0537 (13)0.0329 (12)0.0430 (14)0.0040 (9)0.0073 (10)0.0012 (10)
C10.0339 (16)0.0256 (16)0.0260 (17)0.0007 (12)0.0050 (13)0.0002 (13)
C20.0331 (15)0.0269 (16)0.0317 (18)0.0051 (12)0.0011 (13)0.0051 (13)
C30.0429 (17)0.0314 (17)0.0393 (19)0.0013 (14)0.0008 (15)0.0017 (15)
C40.0362 (17)0.046 (2)0.062 (2)0.0069 (14)0.0004 (16)0.0022 (18)
C50.060 (2)0.0305 (18)0.047 (2)0.0067 (15)0.0094 (16)0.0072 (16)
C60.071 (2)0.042 (2)0.055 (2)0.0072 (17)0.0144 (19)0.0117 (18)
C70.070 (2)0.055 (2)0.082 (3)0.0247 (19)0.035 (2)0.014 (2)
C80.041 (2)0.069 (3)0.082 (3)0.0065 (18)0.0204 (19)0.013 (2)
C90.080 (3)0.062 (3)0.098 (4)0.003 (2)0.052 (2)0.022 (3)
C100.088 (3)0.054 (3)0.053 (2)0.017 (2)0.028 (2)0.025 (2)
C110.096 (3)0.078 (3)0.046 (2)0.024 (2)0.023 (2)0.002 (2)
Geometric parameters (Å, º) top
N1—C11.330 (3)C4—H4A0.9700
N1—N21.344 (3)C4—H4B0.9700
N2—N31.320 (3)C5—C101.528 (5)
N3—N41.341 (3)C5—H5A0.9700
N4—C11.323 (3)C5—H5B0.9700
N5—N5i1.254 (4)C6—C71.524 (5)
N5—C11.415 (3)C6—C111.528 (5)
N6—C21.498 (4)C6—H60.9800
N6—H6A0.8900C7—C81.523 (5)
N6—H6B0.8900C7—H7A0.9700
N6—H6C0.8900C7—H7B0.9700
O1—H20.8500C8—C91.529 (5)
O1—H10.8500C8—H80.9800
C2—C51.524 (4)C9—C101.520 (5)
C2—C41.525 (4)C9—H9A0.9700
C2—C31.529 (4)C9—H9B0.9700
C3—C61.529 (4)C10—C111.534 (5)
C3—H3A0.9700C10—H100.9800
C3—H3B0.9700C11—H11A0.9700
C4—C81.538 (5)C11—H11B0.9700
C1—N1—N2103.5 (2)H5A—C5—H5B108.3
N3—N2—N1109.7 (2)C7—C6—C11110.2 (3)
N2—N3—N4109.3 (2)C7—C6—C3108.7 (3)
C1—N4—N3104.2 (2)C11—C6—C3109.3 (3)
N5i—N5—C1112.6 (3)C7—C6—H6109.6
C2—N6—H6A109.5C11—C6—H6109.6
C2—N6—H6B109.5C3—C6—H6109.6
H6A—N6—H6B109.5C8—C7—C6109.3 (3)
C2—N6—H6C109.5C8—C7—H7A109.8
H6A—N6—H6C109.5C6—C7—H7A109.8
H6B—N6—H6C109.5C8—C7—H7B109.8
H2—O1—H1103.6C6—C7—H7B109.8
N4—C1—N1113.3 (2)H7A—C7—H7B108.3
N4—C1—N5119.0 (2)C7—C8—C9109.8 (3)
N1—C1—N5127.7 (2)C7—C8—C4109.7 (3)
N6—C2—C5109.0 (2)C9—C8—C4109.4 (3)
N6—C2—C4109.7 (2)C7—C8—H8109.3
C5—C2—C4110.0 (2)C9—C8—H8109.3
N6—C2—C3108.2 (2)C4—C8—H8109.3
C5—C2—C3110.3 (2)C10—C9—C8109.8 (3)
C4—C2—C3109.5 (2)C10—C9—H9A109.7
C6—C3—C2109.4 (2)C8—C9—H9A109.7
C6—C3—H3A109.8C10—C9—H9B109.7
C2—C3—H3A109.8C8—C9—H9B109.7
C6—C3—H3B109.8H9A—C9—H9B108.2
C2—C3—H3B109.8C9—C10—C5109.6 (3)
H3A—C3—H3B108.2C9—C10—C11109.0 (3)
C2—C4—C8108.3 (3)C5—C10—C11109.6 (3)
C2—C4—H4A110.0C9—C10—H10109.5
C8—C4—H4A110.0C5—C10—H10109.5
C2—C4—H4B110.0C11—C10—H10109.5
C8—C4—H4B110.0C6—C11—C10109.6 (3)
H4A—C4—H4B108.4C6—C11—H11A109.8
C2—C5—C10108.9 (3)C10—C11—H11A109.8
C2—C5—H5A109.9C6—C11—H11B109.8
C10—C5—H5A109.9C10—C11—H11B109.8
C2—C5—H5B109.9H11A—C11—H11B108.2
C10—C5—H5B109.9
C1—N1—N2—N31.2 (3)C2—C3—C6—C760.8 (3)
N1—N2—N3—N40.3 (3)C2—C3—C6—C1159.5 (3)
N2—N3—N4—C10.7 (3)C11—C6—C7—C859.0 (4)
N3—N4—C1—N11.6 (3)C3—C6—C7—C860.7 (4)
N3—N4—C1—N5178.2 (2)C6—C7—C8—C959.2 (4)
N2—N1—C1—N41.7 (3)C6—C7—C8—C461.1 (4)
N2—N1—C1—N5178.0 (3)C2—C4—C8—C760.4 (3)
N5i—N5—C1—N4174.5 (3)C2—C4—C8—C960.1 (4)
N5i—N5—C1—N15.3 (5)C7—C8—C9—C1060.5 (4)
N6—C2—C3—C6179.1 (2)C4—C8—C9—C1060.0 (4)
C5—C2—C3—C660.0 (3)C8—C9—C10—C559.7 (4)
C4—C2—C3—C661.3 (3)C8—C9—C10—C1160.2 (4)
N6—C2—C4—C8178.9 (3)C2—C5—C10—C959.9 (4)
C5—C2—C4—C861.1 (3)C2—C5—C10—C1159.7 (4)
C3—C2—C4—C860.3 (3)C7—C6—C11—C1059.4 (4)
N6—C2—C5—C10178.5 (3)C3—C6—C11—C1060.0 (4)
C4—C2—C5—C1061.1 (3)C9—C10—C11—C659.6 (4)
C3—C2—C5—C1059.8 (3)C5—C10—C11—C660.3 (4)
Symmetry code: (i) x, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N6—H6A···N3ii0.892.102.990 (4)173
N6—H6B···O1iii0.891.932.822 (3)175
N6—H6C···N1iv0.892.123.007 (4)177
O1—H1···N40.852.032.882 (4)178
O1—H2···N2v0.852.062.898 (4)168
Symmetry codes: (ii) x, y, z1; (iii) x+1/2, y+3/2, z1/2; (iv) x+1/2, y+1/2, z+1/2; (v) x+1/2, y+1/2, z+3/2.
 

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