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In the crystal structure of the title compound, [CdBr
2(C
4H
5N
3O)
2], two N atoms at the 3-position of the cytosine ligands and the two bromide ions complete the distorted tetrahedral geometry around the Cd
II atom. The cytosine ligands of one type are paired through N—H
O hydrogen bonds while the cytosine ligands of another type are chained through N—H
O hydrogen bonds.
Supporting information
CCDC reference: 177174
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.011 Å
- R factor = 0.061
- wR factor = 0.158
- Data-to-parameter ratio = 18.9
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
PLAT_420 Alert C D-H Without Acceptor N(4) - H(4A) ?
PLAT_420 Alert C D-H Without Acceptor N(4) - H(4B) ?
General Notes
ABSTM_02 When printed, the submitted absorption T values will be replaced
by the scaled T values. Since the ratio of scaled T's is
identical to the ratio of reported T values, the scaling does
not imply a change to the absorption corrections used in the
study.
Ratio of Tmax expected/reported 1.121
Tmax scaled 0.241 Tmin scaled 0.121
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check
Data collection: MolEN (Fair, 1990); cell refinement: MolEN; data reduction: MolEN; program(s) used to solve structure: SHELXS86 (Sheldrick, 1986); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: PLATON (Spek, 1997); software used to prepare material for publication: PLATON.
Bis-(4-amino-2(1
H)-pyridinone)dibromocadmium(II)
top
Crystal data top
[Cd(C4H5N3O)2Br2] | Z = 2 |
Mr = 494.43 | F(000) = 468 |
Triclinic, P1 | Dx = 2.417 Mg m−3 |
a = 7.874 (2) Å | Mo Kα radiation, λ = 0.71075 Å |
b = 12.624 (3) Å | Cell parameters from 25 reflections |
c = 7.117 (3) Å | θ = 3.0–27.7° |
α = 105.87 (4)° | µ = 7.49 mm−1 |
β = 92.67 (3)° | T = 293 K |
γ = 87.93 (3)° | Thin plate, colourless |
V = 679.5 (4) Å3 | 0.28 × 0.23 × 0.19 mm |
Data collection top
Enraf Nonius CAD-4 diffractometer | 2427 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.0 |
Graphite monochromator | θmax = 27.7°, θmin = 3.0° |
ω–2θ scans | h = −10→9 |
Absorption correction: ψ scan (North et al., 1968) | k = −16→16 |
Tmin = 0.108, Tmax = 0.215 | l = −9→4 |
3301 measured reflections | 1 standard reflections every 100 reflections |
3301 independent reflections | intensity decay: none |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.061 | w = 1/[σ2(Fo2) + (0.1171P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.158 | (Δ/σ)max < 0.001 |
S = 0.96 | Δρmax = 1.66 e Å−3 |
3301 reflections | Δρmin = −2.87 e Å−3 |
175 parameters | |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All e.s.d.'s are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cd1 | 0.14906 (7) | 0.25317 (5) | 0.11992 (8) | 0.0329 (2) | |
Br2 | −0.06966 (10) | 0.31915 (7) | 0.39137 (11) | 0.0384 (3) | |
Br3 | −0.02797 (10) | 0.14175 (7) | −0.17849 (11) | 0.0420 (3) | |
O2 | 0.3696 (8) | 0.3964 (5) | 0.3755 (8) | 0.0454 (17) | |
O2' | 0.4443 (7) | 0.1657 (5) | −0.0839 (8) | 0.0393 (17) | |
N1 | 0.4122 (8) | 0.5564 (5) | 0.2996 (8) | 0.0323 (17) | |
N1' | 0.6424 (8) | 0.1086 (6) | 0.1097 (10) | 0.040 (2) | |
N3 | 0.2482 (7) | 0.4160 (5) | 0.0941 (8) | 0.0283 (17) | |
N3' | 0.3648 (7) | 0.1549 (5) | 0.2110 (8) | 0.0280 (17) | |
N4 | 0.1366 (10) | 0.4348 (6) | −0.1946 (10) | 0.044 (2) | |
N4' | 0.2958 (9) | 0.1562 (6) | 0.5187 (10) | 0.044 (3) | |
C2 | 0.3437 (9) | 0.4545 (6) | 0.2632 (10) | 0.0295 (19) | |
C2' | 0.4838 (8) | 0.1431 (5) | 0.0714 (10) | 0.0277 (17) | |
C4 | 0.2237 (9) | 0.4779 (6) | −0.0293 (10) | 0.0320 (19) | |
C4' | 0.4109 (9) | 0.1398 (6) | 0.3855 (10) | 0.0293 (17) | |
C5 | 0.2944 (10) | 0.5827 (6) | 0.0101 (12) | 0.037 (2) | |
C5' | 0.5802 (10) | 0.1067 (6) | 0.4277 (11) | 0.033 (2) | |
C6 | 0.3857 (9) | 0.6200 (6) | 0.1757 (11) | 0.036 (2) | |
C6' | 0.6899 (9) | 0.0917 (7) | 0.2854 (12) | 0.037 (2) | |
H1 | 0.4740 | 0.5807 | 0.4045 | 0.0390* | |
H1' | 0.7158 | 0.0968 | 0.0201 | 0.0480* | |
H4A | 0.0985 | 0.3693 | −0.2185 | 0.0530* | |
H4B | 0.1181 | 0.4723 | −0.2781 | 0.0530* | |
H5 | 0.2776 | 0.6251 | −0.0777 | 0.0450* | |
H5' | 0.6124 | 0.0961 | 0.5488 | 0.0400* | |
H6 | 0.4314 | 0.6898 | 0.2062 | 0.0430* | |
H6' | 0.8012 | 0.0692 | 0.3066 | 0.0440* | |
H41' | 0.1938 | 0.1762 | 0.4928 | 0.0530* | |
H42' | 0.3224 | 0.1471 | 0.6319 | 0.0530* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cd1 | 0.0223 (3) | 0.0413 (3) | 0.0357 (3) | −0.0018 (2) | −0.0012 (2) | 0.0119 (2) |
Br2 | 0.0279 (4) | 0.0539 (5) | 0.0307 (4) | −0.0010 (3) | 0.0014 (3) | 0.0070 (3) |
Br3 | 0.0235 (4) | 0.0640 (5) | 0.0333 (4) | −0.0060 (3) | 0.0028 (3) | 0.0038 (3) |
O2 | 0.045 (3) | 0.050 (3) | 0.044 (3) | −0.019 (3) | −0.020 (3) | 0.019 (3) |
O2' | 0.030 (3) | 0.061 (3) | 0.029 (3) | −0.004 (2) | 0.003 (2) | 0.015 (2) |
N1 | 0.028 (3) | 0.043 (3) | 0.025 (3) | −0.007 (3) | −0.004 (2) | 0.008 (3) |
N1' | 0.018 (3) | 0.054 (4) | 0.048 (4) | −0.001 (3) | 0.010 (3) | 0.014 (3) |
N3 | 0.019 (3) | 0.038 (3) | 0.027 (3) | −0.004 (2) | 0.000 (2) | 0.007 (2) |
N3' | 0.022 (3) | 0.038 (3) | 0.026 (3) | 0.002 (2) | 0.004 (2) | 0.012 (2) |
N4 | 0.048 (4) | 0.051 (4) | 0.031 (3) | −0.001 (3) | −0.009 (3) | 0.011 (3) |
N4' | 0.037 (4) | 0.065 (5) | 0.037 (4) | 0.014 (3) | 0.013 (3) | 0.024 (3) |
C2 | 0.019 (3) | 0.039 (4) | 0.030 (3) | −0.005 (3) | −0.004 (3) | 0.009 (3) |
C2' | 0.019 (3) | 0.030 (3) | 0.033 (3) | 0.000 (2) | 0.005 (3) | 0.006 (3) |
C4 | 0.021 (3) | 0.048 (4) | 0.026 (3) | 0.006 (3) | 0.001 (3) | 0.009 (3) |
C4' | 0.026 (3) | 0.033 (3) | 0.026 (3) | 0.000 (3) | 0.001 (3) | 0.003 (3) |
C5 | 0.033 (4) | 0.042 (4) | 0.040 (4) | 0.001 (3) | −0.004 (3) | 0.018 (3) |
C5' | 0.031 (4) | 0.039 (4) | 0.033 (4) | −0.003 (3) | −0.001 (3) | 0.015 (3) |
C6 | 0.026 (4) | 0.040 (4) | 0.043 (4) | −0.003 (3) | 0.001 (3) | 0.014 (3) |
C6' | 0.014 (3) | 0.048 (4) | 0.049 (5) | −0.004 (3) | −0.002 (3) | 0.015 (4) |
Geometric parameters (Å, º) top
Cd1—Br2 | 2.5920 (14) | N4'—C4' | 1.312 (10) |
Cd1—Br3 | 2.5815 (15) | C4—C5 | 1.405 (11) |
Cd1—N3 | 2.281 (6) | C4'—C5' | 1.426 (11) |
Cd1—N3' | 2.243 (6) | C5—C6 | 1.330 (11) |
O2—C2 | 1.230 (10) | C5'—C6' | 1.331 (11) |
O2'—C2' | 1.238 (9) | N1—H1 | 0.860 (8) |
N1—C2 | 1.367 (10) | N1'—H1' | 0.860 (9) |
N1—C6 | 1.350 (10) | N4—H4A | 0.860 (11) |
N1'—C2' | 1.348 (9) | N4—H4B | 0.860 (10) |
N1'—C6' | 1.359 (11) | N4'—H41' | 0.860 (10) |
N3—C2 | 1.368 (9) | N4'—H42' | 0.860 (10) |
N3—C4 | 1.330 (10) | C5—H5 | 0.930 (11) |
N3'—C2' | 1.372 (9) | C5'—H5' | 0.930 (11) |
N3'—C4' | 1.339 (9) | C6—H6 | 0.930 (11) |
N4—C4 | 1.324 (10) | C6'—H6' | 0.930 (11) |
| | | |
Cd1···C5i | 4.191 (8) | Cd1···H5i | 3.677 (8) |
Br2···N1ii | 3.597 (6) | Br2···H41' | 2.895 (8) |
Br2···N4iii | 3.290 (7) | Br2···H6'iv | 3.238 (9) |
Br2···C6'iv | 3.387 (9) | Br2···H4Biii | 2.975 (7) |
Br3···N1'iv | 3.487 (7) | Br2···H4Aiii | 2.936 (7) |
Br3···N4'v | 3.455 (7) | Br2···H4Bi | 2.964 (8) |
O2···C4' | 3.264 (10) | Br2···H5i | 2.932 (8) |
O2···N1vi | 2.758 (8) | Br3···H4A | 3.163 (8) |
O2···N3' | 2.953 (9) | Br3···H41'v | 3.115 (7) |
O2'···C6'vii | 3.360 (11) | Br3···H1'iv | 2.679 (7) |
O2'···N4'v | 2.983 (9) | Br3···H6'vii | 3.097 (9) |
O2'···C6viii | 3.294 (10) | Br3···H42'v | 3.138 (7) |
N1···C5viii | 3.368 (10) | O2···H1vi | 1.911 (8) |
N1···O2vi | 2.758 (8) | O2'···H42'v | 2.155 (9) |
N1···Br2ii | 3.597 (6) | O2'···H6viii | 2.474 (10) |
N1'···C2'vii | 3.258 (10) | O2'···H5'v | 2.888 (9) |
N1'···Br3ix | 3.487 (7) | C2···H1vi | 2.840 (9) |
N3'···O2 | 2.953 (9) | C5'···H5'x | 3.069 (11) |
N4···Br2v | 3.290 (7) | H1···O2vi | 1.911 (8) |
N4···C4i | 3.322 (11) | H1···C2vi | 2.840 (9) |
N4'···O2'iii | 2.983 (9) | H1'···Br3ix | 2.679 (7) |
N4'···Br3iii | 3.455 (7) | H4A···Cd1 | 3.148 (7) |
C2···C5viii | 3.470 (11) | H4A···Br2v | 2.936 (7) |
C2'···N1'vii | 3.258 (10) | H4A···Br3 | 3.163 (8) |
C2'···C2'vii | 3.479 (9) | H4B···Br2v | 2.975 (7) |
C2'···C6'vii | 3.600 (11) | H4B···H5 | 2.416 (11) |
C4···C6viii | 3.375 (10) | H4B···Br2i | 2.964 (8) |
C4···C4i | 3.573 (10) | H5···H4B | 2.416 (11) |
C4···N4i | 3.322 (11) | H5···Cd1i | 3.677 (8) |
C4'···O2 | 3.264 (10) | H5···Br2i | 2.932 (8) |
C5···N1viii | 3.368 (10) | H5'···O2'iii | 2.888 (9) |
C5···C2viii | 3.470 (11) | H5'···H42' | 2.406 (11) |
C5···Cd1i | 4.191 (8) | H5'···C5'x | 3.069 (11) |
C5···C6viii | 3.555 (11) | H6···O2'viii | 2.474 (10) |
C5'···C5'x | 3.434 (11) | H6'···Br2ix | 3.238 (9) |
C6···C4viii | 3.375 (10) | H6'···Br3vii | 3.097 (9) |
C6···O2'viii | 3.294 (10) | H41'···Cd1 | 3.067 (7) |
C6···C5viii | 3.555 (11) | H41'···Br2 | 2.895 (8) |
C6'···O2'vii | 3.360 (11) | H41'···Br3iii | 3.115 (7) |
C6'···C2'vii | 3.600 (11) | H42'···Cd1iii | 3.672 (7) |
C6'···Br2ix | 3.387 (9) | H42'···Br3iii | 3.138 (7) |
Cd1···H42'v | 3.672 (7) | H42'···O2'iii | 2.155 (9) |
Cd1···H41' | 3.067 (7) | H42'···H5' | 2.406 (11) |
Cd1···H4A | 3.148 (7) | | |
| | | |
Br2—Cd1—Br3 | 104.24 (5) | N3'—C4'—C5' | 121.5 (6) |
Br2—Cd1—N3 | 101.91 (15) | N4'—C4'—C5' | 120.2 (7) |
Br2—Cd1—N3' | 111.93 (15) | C4—C5—C6 | 118.6 (7) |
Br3—Cd1—N3 | 115.59 (15) | C4'—C5'—C6' | 116.8 (7) |
Br3—Cd1—N3' | 113.24 (16) | N1—C6—C5 | 120.0 (7) |
N3—Cd1—N3' | 109.3 (2) | N1'—C6'—C5' | 121.3 (7) |
C2—N1—C6 | 121.9 (6) | C2—N1—H1 | 119.0 (8) |
C2'—N1'—C6' | 122.1 (6) | C6—N1—H1 | 119.1 (8) |
Cd1—N3—C2 | 103.8 (5) | C2'—N1'—H1' | 119.0 (9) |
Cd1—N3—C4 | 136.2 (5) | C6'—N1'—H1' | 118.9 (8) |
C2—N3—C4 | 119.8 (6) | C4—N4—H4A | 120.0 (9) |
Cd1—N3'—C2' | 105.5 (4) | C4—N4—H4B | 120.0 (10) |
Cd1—N3'—C4' | 131.1 (5) | H4A—N4—H4B | 120.0 (11) |
C2'—N3'—C4' | 119.8 (6) | C4'—N4'—H41' | 120.0 (9) |
O2—C2—N1 | 121.7 (7) | C4'—N4'—H42' | 120.0 (9) |
O2—C2—N3 | 119.9 (7) | H41'—N4'—H42' | 120.0 (10) |
N1—C2—N3 | 118.4 (6) | C4—C5—H5 | 120.7 (9) |
O2'—C2'—N1' | 121.8 (6) | C6—C5—H5 | 120.7 (9) |
O2'—C2'—N3' | 119.7 (6) | C4'—C5'—H5' | 121.6 (9) |
N1'—C2'—N3' | 118.5 (6) | C6'—C5'—H5' | 121.6 (9) |
N3—C4—N4 | 117.3 (7) | N1—C6—H6 | 119.9 (9) |
N3—C4—C5 | 121.3 (7) | C5—C6—H6 | 120.1 (9) |
N4—C4—C5 | 121.4 (7) | N1'—C6'—H6' | 119.3 (9) |
N3'—C4'—N4' | 118.3 (7) | C5'—C6'—H6' | 119.4 (10) |
| | | |
Br2—Cd1—N3—C2 | 70.9 (4) | C4—N3—C2—O2 | −178.4 (7) |
Br2—Cd1—N3—C4 | −102.9 (7) | C4—N3—C2—N1 | −0.3 (10) |
Br3—Cd1—N3—C2 | −176.7 (4) | Cd1—N3—C4—N4 | −9.8 (11) |
Br3—Cd1—N3—C4 | 9.4 (7) | Cd1—N3—C4—C5 | 173.2 (5) |
N3'—Cd1—N3—C2 | −47.6 (5) | C2—N3—C4—N4 | 177.1 (7) |
N3'—Cd1—N3—C4 | 138.6 (7) | C2—N3—C4—C5 | 0.1 (12) |
Br2—Cd1—N3'—C2' | −169.3 (4) | Cd1—N3'—C2'—O2' | −13.3 (8) |
Br2—Cd1—N3'—C4' | −11.5 (7) | Cd1—N3'—C2'—N1' | 165.6 (6) |
Br3—Cd1—N3'—C2' | 73.2 (4) | C4'—N3'—C2'—O2' | −174.2 (7) |
Br3—Cd1—N3'—C4' | −128.9 (6) | C4'—N3'—C2'—N1' | 4.7 (10) |
N3—Cd1—N3'—C2' | −57.2 (5) | Cd1—N3'—C4'—N4' | 21.9 (11) |
N3—Cd1—N3'—C4' | 100.7 (7) | Cd1—N3'—C4'—C5' | −158.1 (6) |
C6—N1—C2—O2 | 179.3 (7) | C2'—N3'—C4'—N4' | 177.2 (7) |
C6—N1—C2—N3 | 1.2 (10) | C2'—N3'—C4'—C5' | −2.9 (11) |
C2—N1—C6—C5 | −1.8 (11) | N3—C4—C5—C6 | −0.8 (11) |
C6'—N1'—C2'—O2' | 174.9 (8) | N4—C4—C5—C6 | −177.7 (7) |
C6'—N1'—C2'—N3' | −4.0 (11) | N3'—C4'—C5'—C6' | 0.1 (12) |
C2'—N1'—C6'—C5' | 1.2 (13) | N4'—C4'—C5'—C6' | −180.0 (13) |
Cd1—N3—C2—O2 | 6.5 (8) | C4—C5—C6—N1 | 1.6 (11) |
Cd1—N3—C2—N1 | −175.4 (5) | C4'—C5'—C6'—N1' | 0.8 (12) |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x, −y+1, −z+1; (iii) x, y, z+1; (iv) x−1, y, z; (v) x, y, z−1; (vi) −x+1, −y+1, −z+1; (vii) −x+1, −y, −z; (viii) −x+1, −y+1, −z; (ix) x+1, y, z; (x) −x+1, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2vi | 0.86 | 1.91 | 2.758 (8) | 168 |
N1′—H1′···Br3ix | 0.86 | 2.68 | 3.487 (7) | 157 |
N4′—H41′···Br2 | 0.86 | 2.90 | 3.699 (8) | 156 |
N4′—H42′···O2′iii | 0.86 | 2.16 | 2.983 (9) | 162 |
C6—H6···O2′viii | 0.93 | 2.47 | 3.294 (10) | 147 |
Symmetry codes: (iii) x, y, z+1; (vi) −x+1, −y+1, −z+1; (viii) −x+1, −y+1, −z; (ix) x+1, y, z. |
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