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The cation of the title compound, C
18H
24N
4O
22+·2Br
−·2H
2O, is centrosymmetric. O—H
Br, N—H
Br and C—H
O hydrogen bonds and π–π stacking help to establish the crystal packing.
Supporting information
CCDC reference: 643016
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.032
- wR factor = 0.084
- Data-to-parameter ratio = 17.0
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C1'
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.95
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.24 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.37 Ratio
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.06
PLAT301_ALERT_3_C Main Residue Disorder ......................... 13.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 5
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 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
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
4,4'-Bis(propionylamino)-1,1'-ethylenedipyridinium dibromide dihydrate
top
Crystal data top
C18H24N4O22+·2Br−·2H2O | F(000) = 532 |
Mr = 524.26 | Dx = 1.544 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2439 reflections |
a = 8.7548 (18) Å | θ = 2.6–25.8° |
b = 10.030 (2) Å | µ = 3.62 mm−1 |
c = 12.969 (3) Å | T = 294 K |
β = 97.951 (3)° | Block, colourless |
V = 1127.9 (4) Å3 | 0.18 × 0.16 × 0.14 mm |
Z = 2 | |
Data collection top
Bruker SMART 1000 CCD area-detector diffractometer | 2312 independent reflections |
Radiation source: fine-focus sealed tube | 1706 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
ω scans | θmax = 26.4°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→10 |
Tmin = 0.562, Tmax = 0.631 | k = −11→12 |
6324 measured reflections | l = −15→16 |
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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.084 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0367P)2 + 0.4814P] where P = (Fo2 + 2Fc2)/3 |
2312 reflections | (Δ/σ)max < 0.001 |
136 parameters | Δρmax = 0.52 e Å−3 |
25 restraints | Δρmin = −0.53 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
Br1 | 0.08083 (3) | 0.00596 (3) | 0.30679 (2) | 0.04724 (13) | |
O1 | 0.7223 (2) | 0.2309 (2) | 0.16953 (16) | 0.0508 (6) | |
N1 | 0.5856 (2) | 0.2934 (2) | 0.01473 (16) | 0.0343 (5) | |
H1 | 0.5897 | 0.3441 | −0.0383 | 0.041* | |
N2 | 0.2037 (2) | 0.0476 (2) | −0.01196 (16) | 0.0310 (5) | |
C1 | 0.9749 (9) | 0.3936 (10) | 0.1332 (8) | 0.070 (3) | 0.50 |
H1A | 1.0388 | 0.4687 | 0.1226 | 0.105* | 0.50 |
H1B | 1.0145 | 0.3154 | 0.1034 | 0.105* | 0.50 |
H1C | 0.9748 | 0.3801 | 0.2065 | 0.105* | 0.50 |
C2 | 0.8125 (4) | 0.4195 (3) | 0.0817 (3) | 0.0573 (9) | 0.50 |
H2A | 0.7739 | 0.4998 | 0.1109 | 0.069* | 0.50 |
H2B | 0.8133 | 0.4345 | 0.0079 | 0.069* | 0.50 |
C1' | 0.9401 (13) | 0.4437 (14) | 0.1649 (8) | 0.092 (4) | 0.50 |
H1'A | 0.9984 | 0.5194 | 0.1473 | 0.138* | 0.50 |
H1'B | 1.0057 | 0.3667 | 0.1731 | 0.138* | 0.50 |
H1'C | 0.8999 | 0.4610 | 0.2288 | 0.138* | 0.50 |
C2' | 0.8125 (4) | 0.4195 (3) | 0.0817 (3) | 0.0573 (9) | 0.50 |
H2'A | 0.8557 | 0.4045 | 0.0177 | 0.069* | 0.50 |
H2'B | 0.7510 | 0.5002 | 0.0723 | 0.069* | 0.50 |
C3 | 0.7062 (3) | 0.3053 (3) | 0.0960 (2) | 0.0369 (6) | |
C4 | 0.4611 (3) | 0.2100 (3) | 0.00945 (18) | 0.0284 (6) | |
C5 | 0.3558 (3) | 0.2085 (3) | −0.08244 (19) | 0.0348 (6) | |
H5A | 0.3720 | 0.2633 | −0.1378 | 0.042* | |
C6 | 0.2301 (3) | 0.1275 (3) | −0.09106 (19) | 0.0364 (6) | |
H6A | 0.1614 | 0.1273 | −0.1525 | 0.044* | |
C7 | 0.3033 (3) | 0.0481 (3) | 0.0780 (2) | 0.0350 (6) | |
H7A | 0.2839 | −0.0069 | 0.1324 | 0.042* | |
C8 | 0.4303 (3) | 0.1265 (3) | 0.09044 (19) | 0.0350 (6) | |
H8A | 0.4970 | 0.1249 | 0.1528 | 0.042* | |
C9 | 0.0645 (3) | −0.0377 (3) | −0.0207 (2) | 0.0351 (6) | |
H9A | 0.0873 | −0.1190 | 0.0189 | 0.042* | |
H9B | 0.0330 | −0.0616 | −0.0930 | 0.042* | |
O2 | 0.3423 (3) | 0.2490 (3) | 0.33428 (19) | 0.0858 (9) | |
H2C | 0.2836 | 0.1801 | 0.3215 | 0.103* | |
H2D | 0.3369 | 0.3061 | 0.2830 | 0.103* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0516 (2) | 0.0507 (2) | 0.03969 (19) | −0.00359 (15) | 0.00714 (13) | −0.00971 (14) |
O1 | 0.0420 (12) | 0.0616 (14) | 0.0444 (11) | −0.0126 (11) | −0.0099 (9) | 0.0123 (11) |
N1 | 0.0327 (12) | 0.0402 (13) | 0.0297 (11) | −0.0090 (10) | 0.0028 (9) | 0.0038 (10) |
N2 | 0.0262 (11) | 0.0354 (12) | 0.0309 (11) | −0.0061 (10) | 0.0026 (9) | 0.0000 (10) |
C1 | 0.048 (4) | 0.062 (5) | 0.096 (7) | −0.023 (4) | −0.004 (4) | −0.008 (5) |
C2 | 0.0492 (19) | 0.056 (2) | 0.063 (2) | −0.0218 (17) | −0.0040 (16) | 0.0031 (18) |
C1' | 0.096 (7) | 0.106 (8) | 0.067 (5) | −0.057 (6) | −0.016 (5) | −0.002 (5) |
C2' | 0.0492 (19) | 0.056 (2) | 0.063 (2) | −0.0218 (17) | −0.0040 (16) | 0.0031 (18) |
C3 | 0.0304 (14) | 0.0418 (16) | 0.0380 (15) | −0.0048 (13) | 0.0032 (12) | −0.0025 (13) |
C4 | 0.0253 (13) | 0.0318 (14) | 0.0287 (13) | 0.0005 (10) | 0.0056 (10) | −0.0030 (11) |
C5 | 0.0365 (15) | 0.0407 (16) | 0.0264 (13) | −0.0041 (13) | 0.0023 (11) | 0.0055 (12) |
C6 | 0.0320 (14) | 0.0469 (17) | 0.0290 (13) | −0.0049 (13) | −0.0005 (11) | 0.0028 (13) |
C7 | 0.0333 (15) | 0.0420 (15) | 0.0291 (13) | −0.0049 (12) | 0.0022 (11) | 0.0056 (12) |
C8 | 0.0321 (14) | 0.0464 (17) | 0.0253 (12) | −0.0061 (12) | 0.0001 (11) | 0.0050 (12) |
C9 | 0.0309 (14) | 0.0382 (15) | 0.0355 (14) | −0.0083 (12) | 0.0018 (11) | −0.0027 (12) |
O2 | 0.132 (3) | 0.0671 (17) | 0.0603 (16) | −0.0391 (18) | 0.0193 (16) | −0.0032 (14) |
Geometric parameters (Å, º) top
O1—C3 | 1.204 (3) | C1'—H1'B | 0.9600 |
N1—C4 | 1.368 (3) | C1'—H1'C | 0.9600 |
N1—C3 | 1.390 (3) | C4—C8 | 1.398 (3) |
N1—H1 | 0.8600 | C4—C5 | 1.402 (3) |
N2—C6 | 1.347 (3) | C5—C6 | 1.360 (4) |
N2—C7 | 1.356 (3) | C5—H5A | 0.9300 |
N2—C9 | 1.480 (3) | C6—H6A | 0.9300 |
C1—C2 | 1.508 (7) | C7—C8 | 1.353 (4) |
C1—H1A | 0.9600 | C7—H7A | 0.9300 |
C1—H1B | 0.9600 | C8—H8A | 0.9300 |
C1—H1C | 0.9600 | C9—C9i | 1.518 (6) |
C2—C3 | 1.504 (4) | C9—H9A | 0.9700 |
C2—H2A | 0.9700 | C9—H9B | 0.9700 |
C2—H2B | 0.9700 | O2—H2C | 0.8634 |
C1'—H1'A | 0.9600 | O2—H2D | 0.8738 |
| | | |
C4—N1—C3 | 127.4 (2) | N1—C3—C2 | 113.0 (2) |
C4—N1—H1 | 116.3 | N1—C4—C8 | 124.3 (2) |
C3—N1—H1 | 116.3 | N1—C4—C5 | 118.3 (2) |
C6—N2—C7 | 119.7 (2) | C8—C4—C5 | 117.4 (2) |
C6—N2—C9 | 120.8 (2) | C6—C5—C4 | 120.4 (2) |
C7—N2—C9 | 119.5 (2) | C6—C5—H5A | 119.8 |
C2—C1—H1A | 109.5 | C4—C5—H5A | 119.8 |
C2—C1—H1B | 109.5 | N2—C6—C5 | 121.0 (2) |
H1A—C1—H1B | 109.5 | N2—C6—H6A | 119.5 |
C2—C1—H1C | 109.5 | C5—C6—H6A | 119.5 |
H1A—C1—H1C | 109.5 | C8—C7—N2 | 121.6 (2) |
H1B—C1—H1C | 109.5 | C8—C7—H7A | 119.2 |
C3—C2—C1 | 112.1 (5) | N2—C7—H7A | 119.2 |
C3—C2—H2A | 109.2 | C7—C8—C4 | 119.9 (2) |
C1—C2—H2A | 109.2 | C7—C8—H8A | 120.0 |
C3—C2—H2B | 109.2 | C4—C8—H8A | 120.0 |
C1—C2—H2B | 109.2 | N2—C9—C9i | 109.3 (3) |
H2A—C2—H2B | 107.9 | N2—C9—H9A | 109.8 |
H1'A—C1'—H1'B | 109.5 | C9i—C9—H9A | 109.8 |
H1'A—C1'—H1'C | 109.5 | N2—C9—H9B | 109.8 |
H1'B—C1'—H1'C | 109.5 | C9i—C9—H9B | 109.8 |
O1—C3—N1 | 122.7 (2) | H9A—C9—H9B | 108.3 |
O1—C3—C2 | 124.3 (2) | H2C—O2—H2D | 114.2 |
| | | |
C4—N1—C3—O1 | 7.9 (5) | C9—N2—C6—C5 | 178.3 (3) |
C4—N1—C3—C2 | −172.4 (3) | C4—C5—C6—N2 | 0.2 (4) |
C1—C2—C3—O1 | 28.9 (6) | C6—N2—C7—C8 | −0.5 (4) |
C1—C2—C3—N1 | −150.9 (5) | C9—N2—C7—C8 | −178.5 (3) |
C3—N1—C4—C8 | 4.0 (4) | N2—C7—C8—C4 | 0.2 (4) |
C3—N1—C4—C5 | −176.8 (3) | N1—C4—C8—C7 | 179.6 (3) |
N1—C4—C5—C6 | −179.8 (3) | C5—C4—C8—C7 | 0.3 (4) |
C8—C4—C5—C6 | −0.5 (4) | C6—N2—C9—C9i | −91.4 (3) |
C7—N2—C6—C5 | 0.3 (4) | C7—N2—C9—C9i | 86.7 (4) |
Symmetry code: (i) −x, −y, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2C···Br1 | 0.86 | 2.48 | 3.329 (3) | 168 |
O2—H2D···Br1ii | 0.87 | 2.47 | 3.283 (3) | 154 |
N1—H1···Br1iii | 0.86 | 2.50 | 3.361 (2) | 176 |
C9—H9A···O2iv | 0.97 | 2.33 | 3.247 (4) | 157 |
C9—H9B···Br1i | 0.97 | 2.87 | 3.766 (3) | 154 |
Symmetry codes: (i) −x, −y, −z; (ii) −x+1/2, y+1/2, −z+1/2; (iii) x+1/2, −y+1/2, z−1/2; (iv) −x+1/2, y−1/2, −z+1/2. |
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