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organic compounds
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
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806037044/bt2176sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806037044/bt2176Isup2.hkl |
CCDC reference: 624003
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (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+·2NO3− | F(000) = 436 |
Mr = 420.35 | Dx = 1.504 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2y | Cell parameters from 1180 reflections |
a = 13.120 (2) Å | θ = 2.2–25.6° |
b = 7.596 (1) Å | µ = 0.12 mm−1 |
c = 10.391 (2 Å | T = 295 K |
β = 116.357 (3)° | Block, yellow |
V = 927.9 (2) Å3 | 0.35 × 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 tube | Rint = 0.032 |
Graphite monochromator | θmax = 25.0°, θmin = 3.2° |
φ and ω scans | h = −15→14 |
2266 measured reflections | k = −6→9 |
876 independent reflections | l = −12→12 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.077 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.234 | H-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 parameters | Δρmax = 1.15 e Å−3 |
8 restraints | Δρmin = −0.36 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.3946 (4) | 0.5069 (8) | 0.4901 (5) | 0.0551 (13) | |
H1O | 0.3323 | 0.5190 | 0.4958 | 0.066* | |
O2 | 0.4794 (4) | 0.1839 (9) | 0.7277 (7) | 0.110 (3) | |
O3 | 0.3325 (5) | 0.0549 (8) | 0.5674 (6) | 0.0815 (19) | |
O4 | 0.3113 (7) | 0.2603 (11) | 0.6932 (10) | 0.155 (5) | |
N1 | 0.5429 (4) | 0.5446 (7) | 0.7810 (6) | 0.0423 (13) | |
H1N | 0.5284 | 0.4371 | 0.7574 | 0.051* | |
N2 | 0.5509 (5) | 0.8270 (7) | 0.7633 (5) | 0.0413 (12) | |
H2N | 0.5429 | 0.9294 | 0.7270 | 0.050* | |
N3 | 0.3743 (5) | 0.1667 (5) | 0.6627 (6) | 0.093 (3) | |
C1 | 0.4558 (4) | 0.6654 (10) | 0.5287 (5) | 0.0421 (14) | |
H1 | 0.4038 | 0.7651 | 0.4885 | 0.051* | |
C2 | 0.5165 (4) | 0.6803 (10) | 0.6906 (5) | 0.0400 (13) | |
C3 | 0.5984 (5) | 0.6090 (10) | 0.9208 (6) | 0.0415 (15) | |
C4 | 0.6444 (6) | 0.5239 (12) | 1.0510 (7) | 0.0549 (18) | |
H4 | 0.6403 | 0.4023 | 1.0576 | 0.066* | |
C5 | 0.6969 (6) | 0.6280 (13) | 1.1713 (7) | 0.062 (2) | |
H5 | 0.7297 | 0.5763 | 1.2618 | 0.074* | |
C6 | 0.7010 (6) | 0.8092 (15) | 1.1586 (7) | 0.066 (2) | |
H6 | 0.7391 | 0.8748 | 1.2421 | 0.079* | |
C7 | 0.6525 (6) | 0.8969 (12) | 1.0310 (8) | 0.059 (2) | |
H7 | 0.6526 | 1.0191 | 1.0254 | 0.071* | |
C8 | 0.6023 (5) | 0.7893 (9) | 0.9082 (6) | 0.0395 (14) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.048 (2) | 0.068 (3) | 0.044 (2) | −0.016 (2) | 0.0155 (19) | −0.012 (2) |
O2 | 0.076 (4) | 0.050 (3) | 0.124 (6) | −0.018 (4) | −0.030 (4) | 0.007 (4) |
O3 | 0.073 (3) | 0.086 (5) | 0.063 (3) | −0.019 (3) | 0.009 (3) | −0.019 (3) |
O4 | 0.110 (6) | 0.096 (6) | 0.157 (9) | 0.029 (5) | −0.034 (5) | −0.068 (6) |
N1 | 0.043 (3) | 0.043 (3) | 0.033 (2) | −0.005 (2) | 0.0095 (19) | −0.005 (2) |
N2 | 0.054 (3) | 0.034 (3) | 0.031 (2) | −0.005 (2) | 0.014 (2) | −0.003 (2) |
N3 | 0.083 (5) | 0.035 (3) | 0.090 (5) | −0.006 (4) | −0.025 (4) | 0.001 (3) |
C1 | 0.034 (2) | 0.053 (4) | 0.030 (2) | −0.001 (3) | 0.006 (2) | −0.003 (3) |
C2 | 0.036 (3) | 0.046 (3) | 0.034 (3) | −0.001 (3) | 0.012 (2) | 0.000 (3) |
C3 | 0.039 (3) | 0.053 (3) | 0.029 (3) | −0.006 (3) | 0.012 (2) | −0.003 (2) |
C4 | 0.053 (4) | 0.064 (4) | 0.040 (3) | 0.001 (3) | 0.012 (3) | 0.012 (3) |
C5 | 0.056 (4) | 0.096 (7) | 0.031 (3) | −0.008 (4) | 0.016 (3) | 0.000 (3) |
C6 | 0.050 (4) | 0.106 (7) | 0.032 (3) | −0.013 (4) | 0.012 (3) | −0.022 (4) |
C7 | 0.063 (5) | 0.068 (5) | 0.050 (4) | −0.018 (4) | 0.028 (4) | −0.025 (4) |
C8 | 0.040 (3) | 0.044 (3) | 0.033 (3) | −0.002 (2) | 0.016 (3) | −0.006 (3) |
Geometric parameters (Å, º) top
O1—C1 | 1.403 (8) | C1—C2 | 1.513 (7) |
O1—H1O | 0.8501 | C1—H1 | 0.9800 |
O2—N3 | 1.245 (6) | C3—C4 | 1.374 (9) |
O3—N3 | 1.233 (7) | C3—C8 | 1.379 (9) |
O4—N3 | 1.234 (7) | C4—C5 | 1.378 (11) |
N1—C2 | 1.333 (9) | C4—H4 | 0.9300 |
N1—C3 | 1.393 (8) | C5—C6 | 1.386 (15) |
N1—H1N | 0.8500 | C5—H5 | 0.9300 |
N2—C2 | 1.309 (8) | C6—C7 | 1.363 (12) |
N2—C8 | 1.379 (7) | C6—H6 | 0.9300 |
N2—H2N | 0.8500 | C7—C8 | 1.409 (9) |
C1—C1i | 1.522 (11) | C7—H7 | 0.9300 |
C1—O1—H1O | 109.5 | C4—C3—C8 | 122.8 (7) |
C2—N1—C3 | 108.4 (6) | C4—C3—N1 | 131.3 (7) |
C2—N1—H1N | 125.8 | C8—C3—N1 | 105.9 (6) |
C3—N1—H1N | 125.8 | C5—C4—C3 | 116.6 (8) |
C2—N2—C8 | 109.2 (5) | C5—C4—H4 | 121.7 |
C2—N2—H2N | 125.4 | C3—C4—H4 | 121.7 |
C8—N2—H2N | 125.4 | C4—C5—C6 | 120.6 (7) |
O4—N3—O3 | 119.6 (5) | C4—C5—H5 | 119.7 |
O4—N3—O2 | 120.5 (6) | C6—C5—H5 | 119.7 |
O3—N3—O2 | 119.9 (6) | C7—C6—C5 | 123.8 (7) |
O1—C1—C1i | 109.1 (3) | C7—C6—H6 | 118.1 |
O1—C1—C2 | 109.5 (5) | C5—C6—H6 | 118.1 |
C1i—C1—C2 | 108.7 (5) | C6—C7—C8 | 115.2 (8) |
O1—C1—H1 | 109.9 | C6—C7—H7 | 122.4 |
C1i—C1—H1 | 109.9 | C8—C7—H7 | 122.4 |
C2—C1—H1 | 109.9 | N2—C8—C3 | 106.8 (5) |
N2—C2—N1 | 109.7 (4) | N2—C8—C7 | 132.4 (7) |
N2—C2—C1 | 125.6 (6) | C3—C8—C7 | 120.8 (6) |
N1—C2—C1 | 124.7 (6) | ||
C8—N2—C2—N1 | −0.1 (6) | C3—C4—C5—C6 | 0.5 (10) |
C8—N2—C2—C1 | 179.9 (5) | C4—C5—C6—C7 | 1.9 (12) |
C3—N1—C2—N2 | −0.3 (6) | C5—C6—C7—C8 | −3.8 (11) |
C3—N1—C2—C1 | 179.7 (4) | C2—N2—C8—C3 | 0.5 (6) |
O1—C1—C2—N2 | −157.5 (5) | C2—N2—C8—C7 | −179.5 (6) |
C1i—C1—C2—N2 | 83.4 (5) | C4—C3—C8—N2 | 178.6 (5) |
O1—C1—C2—N1 | 22.5 (7) | N1—C3—C8—N2 | −0.6 (7) |
C1i—C1—C2—N1 | −96.6 (5) | C4—C3—C8—C7 | −1.4 (10) |
C2—N1—C3—C4 | −178.5 (6) | N1—C3—C8—C7 | 179.4 (5) |
C2—N1—C3—C8 | 0.6 (7) | C6—C7—C8—N2 | −176.5 (6) |
C8—C3—C4—C5 | −0.6 (10) | C6—C7—C8—C3 | 3.5 (9) |
N1—C3—C4—C5 | 178.3 (6) |
Symmetry code: (i) −x+1, y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1o···O3ii | 0.85 | 1.98 | 2.790 (7) | 159 |
N1—H1n···O2 | 0.85 | 2.01 | 2.845 (9) | 169 |
N2—H2n···O2iii | 0.85 | 2.11 | 2.839 (9) | 144 |
Symmetry codes: (ii) −x+1/2, y+1/2, −z+1; (iii) x, y+1, z. |
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