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In the crystal structure of the title compound, C16H16N4O22+·2NO3, the cation, which lies on a twofold rotation axis, inter­acts with the nitrate anions, giving rise to a hydrogen-bonded layer structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806037044/bt2176sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806037044/bt2176Isup2.hkl
Contains datablock I

CCDC reference: 624003

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.010 Å
  • R factor = 0.077
  • wR factor = 0.234
  • Data-to-parameter ratio = 6.4

checkCIF/PLATON results

No syntax errors found



Alert level B DIFMX01_ALERT_2_B The maximum difference density is > 0.1*ZMAX*1.00 _refine_diff_density_max given = 1.150 Test value = 0.800 PLAT097_ALERT_2_B Maximum (Positive) Residual Density ............ 1.15 e/A   
Alert level C DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.39 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.19 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N3 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 876 Count of symmetry unique reflns 880 Completeness (_total/calc) 99.55% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1 = . S
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.

2,2'-(1,2-dihydroxyethane-1,2-diyl)bis(benzimidazolylium) dinitrate top
Crystal data top
C16H16N4O22+·2NO3F(000) = 436
Mr = 420.35Dx = 1.504 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2yCell parameters from 1180 reflections
a = 13.120 (2) Åθ = 2.2–25.6°
b = 7.596 (1) ŵ = 0.12 mm1
c = 10.391 (2 ÅT = 295 K
β = 116.357 (3)°Block, yellow
V = 927.9 (2) Å30.35 × 0.18 × 0.12 mm
Z = 2
Data collection top
Bruker SMART area-detector
diffractometer
839 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
Graphite monochromatorθmax = 25.0°, θmin = 3.2°
φ and ω scansh = 1514
2266 measured reflectionsk = 69
876 independent reflectionsl = 1212
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)] = 0.077Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.234H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.1739P)2 + 1.1826P]
where P = (Fo2 + 2Fc2)/3
876 reflections(Δ/σ)max = 0.001
137 parametersΔρmax = 1.15 e Å3
8 restraintsΔρmin = 0.36 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.3946 (4)0.5069 (8)0.4901 (5)0.0551 (13)
H1O0.33230.51900.49580.066*
O20.4794 (4)0.1839 (9)0.7277 (7)0.110 (3)
O30.3325 (5)0.0549 (8)0.5674 (6)0.0815 (19)
O40.3113 (7)0.2603 (11)0.6932 (10)0.155 (5)
N10.5429 (4)0.5446 (7)0.7810 (6)0.0423 (13)
H1N0.52840.43710.75740.051*
N20.5509 (5)0.8270 (7)0.7633 (5)0.0413 (12)
H2N0.54290.92940.72700.050*
N30.3743 (5)0.1667 (5)0.6627 (6)0.093 (3)
C10.4558 (4)0.6654 (10)0.5287 (5)0.0421 (14)
H10.40380.76510.48850.051*
C20.5165 (4)0.6803 (10)0.6906 (5)0.0400 (13)
C30.5984 (5)0.6090 (10)0.9208 (6)0.0415 (15)
C40.6444 (6)0.5239 (12)1.0510 (7)0.0549 (18)
H40.64030.40231.05760.066*
C50.6969 (6)0.6280 (13)1.1713 (7)0.062 (2)
H50.72970.57631.26180.074*
C60.7010 (6)0.8092 (15)1.1586 (7)0.066 (2)
H60.73910.87481.24210.079*
C70.6525 (6)0.8969 (12)1.0310 (8)0.059 (2)
H70.65261.01911.02540.071*
C80.6023 (5)0.7893 (9)0.9082 (6)0.0395 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.048 (2)0.068 (3)0.044 (2)0.016 (2)0.0155 (19)0.012 (2)
O20.076 (4)0.050 (3)0.124 (6)0.018 (4)0.030 (4)0.007 (4)
O30.073 (3)0.086 (5)0.063 (3)0.019 (3)0.009 (3)0.019 (3)
O40.110 (6)0.096 (6)0.157 (9)0.029 (5)0.034 (5)0.068 (6)
N10.043 (3)0.043 (3)0.033 (2)0.005 (2)0.0095 (19)0.005 (2)
N20.054 (3)0.034 (3)0.031 (2)0.005 (2)0.014 (2)0.003 (2)
N30.083 (5)0.035 (3)0.090 (5)0.006 (4)0.025 (4)0.001 (3)
C10.034 (2)0.053 (4)0.030 (2)0.001 (3)0.006 (2)0.003 (3)
C20.036 (3)0.046 (3)0.034 (3)0.001 (3)0.012 (2)0.000 (3)
C30.039 (3)0.053 (3)0.029 (3)0.006 (3)0.012 (2)0.003 (2)
C40.053 (4)0.064 (4)0.040 (3)0.001 (3)0.012 (3)0.012 (3)
C50.056 (4)0.096 (7)0.031 (3)0.008 (4)0.016 (3)0.000 (3)
C60.050 (4)0.106 (7)0.032 (3)0.013 (4)0.012 (3)0.022 (4)
C70.063 (5)0.068 (5)0.050 (4)0.018 (4)0.028 (4)0.025 (4)
C80.040 (3)0.044 (3)0.033 (3)0.002 (2)0.016 (3)0.006 (3)
Geometric parameters (Å, º) top
O1—C11.403 (8)C1—C21.513 (7)
O1—H1O0.8501C1—H10.9800
O2—N31.245 (6)C3—C41.374 (9)
O3—N31.233 (7)C3—C81.379 (9)
O4—N31.234 (7)C4—C51.378 (11)
N1—C21.333 (9)C4—H40.9300
N1—C31.393 (8)C5—C61.386 (15)
N1—H1N0.8500C5—H50.9300
N2—C21.309 (8)C6—C71.363 (12)
N2—C81.379 (7)C6—H60.9300
N2—H2N0.8500C7—C81.409 (9)
C1—C1i1.522 (11)C7—H70.9300
C1—O1—H1O109.5C4—C3—C8122.8 (7)
C2—N1—C3108.4 (6)C4—C3—N1131.3 (7)
C2—N1—H1N125.8C8—C3—N1105.9 (6)
C3—N1—H1N125.8C5—C4—C3116.6 (8)
C2—N2—C8109.2 (5)C5—C4—H4121.7
C2—N2—H2N125.4C3—C4—H4121.7
C8—N2—H2N125.4C4—C5—C6120.6 (7)
O4—N3—O3119.6 (5)C4—C5—H5119.7
O4—N3—O2120.5 (6)C6—C5—H5119.7
O3—N3—O2119.9 (6)C7—C6—C5123.8 (7)
O1—C1—C1i109.1 (3)C7—C6—H6118.1
O1—C1—C2109.5 (5)C5—C6—H6118.1
C1i—C1—C2108.7 (5)C6—C7—C8115.2 (8)
O1—C1—H1109.9C6—C7—H7122.4
C1i—C1—H1109.9C8—C7—H7122.4
C2—C1—H1109.9N2—C8—C3106.8 (5)
N2—C2—N1109.7 (4)N2—C8—C7132.4 (7)
N2—C2—C1125.6 (6)C3—C8—C7120.8 (6)
N1—C2—C1124.7 (6)
C8—N2—C2—N10.1 (6)C3—C4—C5—C60.5 (10)
C8—N2—C2—C1179.9 (5)C4—C5—C6—C71.9 (12)
C3—N1—C2—N20.3 (6)C5—C6—C7—C83.8 (11)
C3—N1—C2—C1179.7 (4)C2—N2—C8—C30.5 (6)
O1—C1—C2—N2157.5 (5)C2—N2—C8—C7179.5 (6)
C1i—C1—C2—N283.4 (5)C4—C3—C8—N2178.6 (5)
O1—C1—C2—N122.5 (7)N1—C3—C8—N20.6 (7)
C1i—C1—C2—N196.6 (5)C4—C3—C8—C71.4 (10)
C2—N1—C3—C4178.5 (6)N1—C3—C8—C7179.4 (5)
C2—N1—C3—C80.6 (7)C6—C7—C8—N2176.5 (6)
C8—C3—C4—C50.6 (10)C6—C7—C8—C33.5 (9)
N1—C3—C4—C5178.3 (6)
Symmetry code: (i) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1o···O3ii0.851.982.790 (7)159
N1—H1n···O20.852.012.845 (9)169
N2—H2n···O2iii0.852.112.839 (9)144
Symmetry codes: (ii) x+1/2, y+1/2, z+1; (iii) x, y+1, z.
 

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