The title compound, C10H9N2+·Br-·H2O, crystallizes in the orthorhombic crystal system. The structure consists of separate bipyridinium cations stacked along the a axis. The pyridine and pyridinium rings deviate from coplanarity by 29.6 (4)° about the C-C bridging bond. The Br- ions and the water molecules are situated between the stacks.
Supporting information
CCDC reference: 193736
Key indicators
- Single-crystal X-ray study
- T = 90 K
- Mean (C-C) = 0.004 Å
- R factor = 0.025
- wR factor = 0.052
- Data-to-parameter ratio = 16.9
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
General Notes
REFLT_03
From the CIF: _diffrn_reflns_theta_max 27.46
From the CIF: _reflns_number_total 2315
Count of symmetry unique reflns 1391
Completeness (_total/calc) 166.43%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 924
Fraction of Friedel pairs measured 0.664
Are heavy atom types Z>Si present yes
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.
Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO–SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1994); software used to prepare material for publication: SHELXL97.
1-Hydro-4,4'-bipyridinium bromide monohydrate
top
Crystal data top
C10H9N2+·Br−·H2O | Dx = 1.634 Mg m−3 |
Mr = 255.12 | Melting point: >350° K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 3777 reflections |
a = 7.0273 (14) Å | θ = 1.0–27.5° |
b = 9.6840 (19) Å | µ = 3.93 mm−1 |
c = 15.240 (3) Å | T = 90 K |
V = 1037.1 (4) Å3 | Skewed hexagonal column, colourless |
Z = 4 | 0.25 × 0.22 × 0.20 mm |
F(000) = 512 | |
Data collection top
Nonius KappaCCD diffractometer | 2315 independent reflections |
Radiation source: fine-focus sealed tube | 2141 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
Detector resolution: 18 pixels mm-1 | θmax = 27.5°, θmin = 2.5° |
ω scans at fixed χ = 55° | h = −9→8 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −12→8 |
Tmin = 0.395, Tmax = 0.455 | l = −19→18 |
6291 measured reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.025 | w = 1/[σ2(Fo2) + 0.1011P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.052 | (Δ/σ)max = 0.001 |
S = 1.07 | Δρmax = 0.37 e Å−3 |
2315 reflections | Δρmin = −0.36 e Å−3 |
137 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0058 (6) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 924 Friedel pairs [Check] |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.025 (11) |
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 | |
C1 | 0.4915 (4) | 0.3872 (2) | 0.03279 (18) | 0.0112 (5) | |
C2 | 0.4397 (4) | 0.4585 (2) | 0.10858 (18) | 0.0121 (5) | |
H2 | 0.4039 | 0.4092 | 0.1599 | 0.015* | |
C3 | 0.4408 (3) | 0.6009 (2) | 0.10863 (19) | 0.0140 (6) | |
H3 | 0.4070 | 0.6499 | 0.1603 | 0.017* | |
N4 | 0.4894 (3) | 0.67024 (19) | 0.03606 (15) | 0.0125 (5) | |
H4 | 0.4906 | 0.7611 | 0.0373 | 0.015* | |
C5 | 0.5362 (4) | 0.6053 (3) | −0.03852 (18) | 0.0154 (6) | |
H5 | 0.5688 | 0.6576 | −0.0891 | 0.018* | |
C6 | 0.5373 (4) | 0.4627 (2) | −0.04224 (18) | 0.0130 (6) | |
H6 | 0.5689 | 0.4166 | −0.0953 | 0.016* | |
C1' | 0.5015 (3) | 0.2332 (2) | 0.03195 (17) | 0.0108 (5) | |
C2' | 0.5467 (4) | 0.1612 (2) | 0.10857 (18) | 0.0123 (6) | |
H2' | 0.5713 | 0.2088 | 0.1619 | 0.015* | |
C3' | 0.5547 (3) | 0.0177 (2) | 0.10472 (19) | 0.0135 (6) | |
H3' | 0.5865 | −0.0316 | 0.1566 | 0.016* | |
N4' | 0.5197 (3) | −0.05393 (19) | 0.03154 (15) | 0.0127 (5) | |
C5' | 0.4786 (3) | 0.0165 (2) | −0.04263 (18) | 0.0142 (6) | |
H5' | 0.4549 | −0.0338 | −0.0950 | 0.017* | |
C6' | 0.4698 (4) | 0.1593 (2) | −0.04497 (18) | 0.0127 (6) | |
H6' | 0.4426 | 0.2062 | −0.0983 | 0.015* | |
Br1 | 0.16873 (4) | 0.21181 (2) | 0.267035 (18) | 0.01674 (9) | |
O | 0.2505 (3) | −0.1344 (2) | 0.23561 (16) | 0.0213 (4) | |
H1W | 0.138 (4) | −0.173 (3) | 0.241 (2) | 0.035 (9)* | |
H2W | 0.238 (5) | −0.057 (3) | 0.239 (2) | 0.039 (11)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0093 (12) | 0.0081 (12) | 0.0161 (14) | 0.0004 (10) | −0.0031 (12) | 0.0019 (10) |
C2 | 0.0146 (13) | 0.0117 (12) | 0.0101 (14) | −0.0018 (10) | −0.0017 (12) | −0.0004 (11) |
C3 | 0.0146 (14) | 0.0124 (12) | 0.0149 (15) | 0.0013 (10) | −0.0017 (12) | −0.0010 (11) |
N4 | 0.0151 (12) | 0.0055 (9) | 0.0169 (13) | 0.0016 (9) | −0.0041 (11) | 0.0007 (8) |
C5 | 0.0177 (15) | 0.0144 (13) | 0.0142 (15) | 0.0007 (11) | −0.0016 (12) | 0.0015 (11) |
C6 | 0.0153 (14) | 0.0103 (12) | 0.0135 (15) | 0.0005 (10) | 0.0002 (12) | −0.0011 (11) |
C1' | 0.0075 (12) | 0.0084 (11) | 0.0164 (14) | −0.0025 (10) | 0.0026 (11) | −0.0012 (10) |
C2' | 0.0172 (14) | 0.0098 (11) | 0.0100 (14) | 0.0007 (10) | −0.0001 (12) | −0.0018 (10) |
C3' | 0.0126 (13) | 0.0132 (12) | 0.0149 (15) | 0.0000 (10) | 0.0033 (12) | 0.0023 (11) |
N4' | 0.0143 (12) | 0.0069 (10) | 0.0168 (13) | 0.0008 (9) | 0.0028 (11) | −0.0003 (9) |
C5' | 0.0134 (13) | 0.0128 (13) | 0.0164 (15) | 0.0000 (11) | 0.0003 (13) | −0.0042 (11) |
C6' | 0.0141 (14) | 0.0123 (12) | 0.0116 (15) | −0.0009 (10) | −0.0003 (12) | 0.0012 (10) |
Br1 | 0.01925 (13) | 0.01667 (12) | 0.01430 (14) | 0.00265 (11) | 0.00205 (13) | 0.00218 (10) |
O | 0.0202 (10) | 0.0182 (10) | 0.0256 (11) | −0.0007 (8) | −0.0015 (10) | 0.0011 (10) |
Geometric parameters (Å, º) top
C1—C2 | 1.393 (4) | C1'—C6' | 1.391 (4) |
C1—C6 | 1.395 (4) | C1'—C2' | 1.397 (4) |
C1—C1' | 1.494 (3) | C2'—C3' | 1.391 (3) |
C2—C3 | 1.380 (3) | C2'—H2' | 0.9500 |
C2—H2 | 0.95 | C3'—N4' | 1.336 (3) |
C3—N4 | 1.338 (3) | C3'—H3' | 0.9500 |
C3—H3 | 0.95 | N4'—C5' | 1.351 (3) |
N4—C5 | 1.340 (3) | C5'—C6' | 1.385 (3) |
N4—H4 | 0.88 | C5'—H5' | 0.9500 |
C5—C6 | 1.383 (3) | C6'—H6' | 0.9500 |
C5—H5 | 0.95 | O—H1W | 0.88 (3) |
C6—H6 | 0.95 | O—H2W | 0.76 (3) |
| | | |
C2—C1—C6 | 118.7 (2) | C6'—C1'—C2' | 119.0 (2) |
C2—C1—C1' | 120.9 (2) | C6'—C1'—C1 | 120.9 (2) |
C6—C1—C1' | 120.3 (2) | C2'—C1'—C1 | 120.1 (2) |
C3—C2—C1 | 119.6 (3) | C3'—C2'—C1' | 118.2 (3) |
C3—C2—H2 | 120.2 | C3'—C2'—H2' | 120.9 |
C1—C2—H2 | 120.2 | C1'—C2'—H2' | 120.9 |
N4—C3—C2 | 120.2 (3) | N4'—C3'—C2' | 123.1 (3) |
N4—C3—H3 | 119.9 | N4'—C3'—H3' | 118.4 |
C2—C3—H3 | 119.9 | C2'—C3'—H3' | 118.4 |
C3—N4—C5 | 121.9 (2) | C3'—N4'—C5' | 118.4 (2) |
C3—N4—H4 | 119.0 | N4'—C5'—C6' | 122.3 (2) |
C5—N4—H4 | 119.0 | N4'—C5'—H5' | 118.8 |
N4—C5—C6 | 120.3 (3) | C6'—C5'—H5' | 118.8 |
N4—C5—H5 | 119.8 | C5'—C6'—C1' | 119.0 (3) |
C6—C5—H5 | 119.8 | C5'—C6'—H6' | 120.5 |
C5—C6—C1 | 119.2 (3) | C1'—C6'—H6' | 120.5 |
C5—C6—H6 | 120.4 | H1W—O—H2W | 108 (3) |
C1—C6—H6 | 120.4 | | |
| | | |
C6—C1—C2—C3 | −2.0 (4) | C2—C1—C1'—C2' | −29.6 (4) |
C1'—C1—C2—C3 | 176.8 (2) | C6—C1—C1'—C2' | 149.2 (3) |
C1—C2—C3—N4 | 0.7 (4) | C6'—C1'—C2'—C3' | −1.1 (4) |
C2—C3—N4—C5 | 0.7 (4) | C1—C1'—C2'—C3' | −179.9 (2) |
C3—N4—C5—C6 | −0.6 (4) | C1'—C2'—C3'—N4' | −0.6 (4) |
N4—C5—C6—C1 | −0.8 (4) | C2'—C3'—N4'—C5' | 1.5 (4) |
C2—C1—C6—C5 | 2.1 (4) | C3'—N4'—C5'—C6' | −0.6 (4) |
C1'—C1—C6—C5 | −176.7 (2) | N4'—C5'—C6'—C1' | −1.0 (4) |
C2—C1—C1'—C6' | 151.5 (3) | C2'—C1'—C6'—C5' | 1.8 (4) |
C6—C1—C1'—C6' | −29.6 (4) | C1—C1'—C6'—C5' | −179.3 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···N4′i | 0.88 | 1.81 | 2.681 (3) | 173 |
O—H1W···Br1ii | 0.88 (3) | 2.43 (3) | 3.301 (2) | 172 (3) |
O—H2W···Br1 | 0.76 (3) | 2.68 (3) | 3.436 (2) | 174 (3) |
Symmetry codes: (i) x, y+1, z; (ii) −x, y−1/2, −z+1/2. |