Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768106017393/lc5044sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768106017393/lc50442-thiouracilsup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768106017393/lc5044cytosinesup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768106017393/lc5044salicylicacidsup4.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S0108768106017393/lc5044sup5.pdf |
CCDC references: 276206; 276207; 276208
For all compounds, data collection: SMART (Bruker, 2004); cell refinement: SMART; data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: Koritsanszky et al., (2003); molecular graphics: Koritsanszky et al., (2003); software used to prepare material for publication: Koritsanszky et al., (2003).
C4H4N2OS | Z = 2 |
Mr = 128.16 | F(000) = 132 |
Triclinic, P1 | Dx = 1.661 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 4.2427 (4) Å | Cell parameters from 4983 reflections |
b = 5.9648 (5) Å | θ = 3.6–51.6° |
c = 10.5801 (10) Å | µ = 0.51 mm−1 |
α = 105.736 (5)° | T = 90 K |
β = 94.912 (5)° | Block, colorless |
γ = 91.927 (4)° | 0.39 × 0.19 × 0.12 mm |
V = 256.32 (4) Å3 |
Bruker SMART APEX CCD area detector diffractometer | 4983 independent reflections |
Radiation source: fine-focus sealed tube | 4697 reflections with > 3σ(I) |
Graphite monochromator | Rint = 0.031 |
ϕ & ω scans | θmax = 51.6°, θmin = 3.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = 0→9 |
Tmin = 0.831, Tmax = 0.943 | k = −13→13 |
4983 measured reflections | l = −23→22 |
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)] = 0.014 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.017 | H-atom parameters not refined |
S = 1.93 | w2 = 1/[s2(Fo2)] |
4697 reflections | (Δ/σ)max < 0.001 |
229 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C4H4N2OS | γ = 91.927 (4)° |
Mr = 128.16 | V = 256.32 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 4.2427 (4) Å | Mo Kα radiation |
b = 5.9648 (5) Å | µ = 0.51 mm−1 |
c = 10.5801 (10) Å | T = 90 K |
α = 105.736 (5)° | 0.39 × 0.19 × 0.12 mm |
β = 94.912 (5)° |
Bruker SMART APEX CCD area detector diffractometer | 4983 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4697 reflections with > 3σ(I) |
Tmin = 0.831, Tmax = 0.943 | Rint = 0.031 |
4983 measured reflections |
R[F2 > 2σ(F2)] = 0.014 | 0 restraints |
wR(F2) = 0.017 | H-atom parameters not refined |
S = 1.93 | Δρmax = 0.32 e Å−3 |
4697 reflections | Δρmin = −0.20 e Å−3 |
229 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S(2) | 0.45628 (1) | 0.64884 (1) | 0.37117 (1) | 0.012 | |
O(4) | −0.24292 (6) | 0.72104 (4) | −0.01050 (2) | 0.016 | |
N(1) | 0.14216 (4) | 1.02089 (3) | 0.35761 (2) | 0.011 | |
N(3) | 0.08327 (4) | 0.71272 (3) | 0.16998 (2) | 0.011 | |
C(2) | 0.21656 (4) | 0.80251 (3) | 0.29574 (2) | 0.010 | |
C(4) | −0.13325 (4) | 0.82225 (3) | 0.10352 (2) | 0.012 | |
C(6) | −0.06598 (4) | 1.14382 (3) | 0.30023 (2) | 0.012 | |
C(5) | −0.21041 (5) | 1.05168 (3) | 0.17684 (2) | 0.013 | |
H(6) | −0.08610 | 1.31703 | 0.36384 | 0.025 (2) | |
H(5) | −0.37972 | 1.15188 | 0.13684 | 0.030 (3) | |
H(1) | 0.25733 | 1.10703 | 0.44842 | 0.016 (2) | |
H(3) | 0.13712 | 0.54835 | 0.11787 | 0.019 (2) | |
DUM0 | 0.00000 | 0.00000 | 0.00000 | 0.000 | 0.0000 |
U11 | U22 | U33 | U12 | U13 | U23 | |
S(2) | 0.01332 (2) | 0.01045 (2) | 0.01132 (2) | 0.00233 (1) | −0.00329 (1) | 0.00216 (1) |
O(4) | 0.01966 (9) | 0.01683 (8) | 0.00980 (7) | 0.00640 (6) | −0.00425 (6) | 0.00035 (6) |
N(1) | 0.01189 (6) | 0.00996 (5) | 0.00984 (5) | 0.00190 (4) | −0.00153 (4) | 0.00093 (4) |
N(3) | 0.01240 (6) | 0.01115 (5) | 0.00867 (5) | 0.00316 (4) | −0.00155 (4) | 0.00109 (4) |
C(2) | 0.01018 (6) | 0.01001 (5) | 0.00891 (5) | 0.00149 (4) | −0.00099 (4) | 0.00187 (4) |
C(4) | 0.01273 (6) | 0.01243 (6) | 0.00877 (5) | 0.00309 (4) | −0.00129 (4) | 0.00196 (5) |
C(6) | 0.01278 (6) | 0.01019 (5) | 0.01167 (6) | 0.00238 (4) | −0.00070 (4) | 0.00180 (5) |
C(5) | 0.01354 (7) | 0.01200 (6) | 0.01143 (6) | 0.00349 (4) | −0.00124 (4) | 0.00297 (5) |
S(2)—C(2) | 1.6828 (2) | N(3)—C(4) | 1.3942 (2) |
O(4)—C(4) | 1.2354 (3) | N(3)—H(3) | 1.0300 (2) |
N(1)—C(2) | 1.3511 (2) | C(4)—C(5) | 1.4420 (3) |
N(1)—C(6) | 1.3709 (2) | C(6)—C(5) | 1.3538 (3) |
N(1)—H(1) | 1.0300 (2) | C(6)—H(6) | 1.0800 (2) |
N(3)—C(2) | 1.3570 (2) | C(5)—H(5) | 1.0800 (2) |
C(2)—N(1)—C(6) | 122.692 (16) | O(4)—C(4)—N(3) | 119.512 (19) |
C(2)—N(1)—H(1) | 120.009 (16) | O(4)—C(4)—C(5) | 125.049 (18) |
C(6)—N(1)—H(1) | 117.100 (15) | N(3)—C(4)—C(5) | 115.439 (16) |
C(2)—N(3)—C(4) | 125.400 (16) | N(1)—C(6)—C(5) | 121.437 (16) |
C(2)—N(3)—H(3) | 119.129 (15) | N(1)—C(6)—H(6) | 111.386 (16) |
C(4)—N(3)—H(3) | 115.445 (15) | C(5)—C(6)—H(6) | 127.130 (17) |
S(2)—C(2)—N(1) | 121.904 (13) | C(4)—C(5)—C(6) | 118.709 (16) |
S(2)—C(2)—N(3) | 121.868 (13) | C(4)—C(5)—H(5) | 122.272 (17) |
N(1)—C(2)—N(3) | 116.222 (15) | C(6)—C(5)—H(5) | 119.018 (17) |
C(6)—N(1)—C(2)—S(2) | −176.4 (1) | H(3)—N(3)—C(2)—S(2) | −2.5 (1) |
C(6)—N(1)—C(2)—N(3) | 2.7 (1) | H(3)—N(3)—C(2)—N(1) | 178.5 (1) |
C(2)—N(1)—C(6)—C(5) | 0.1 (1) | H(3)—N(3)—C(4)—O(4) | −0.6 (1) |
C(2)—N(1)—C(6)—H(6) | −177.6 (1) | H(3)—N(3)—C(4)—C(5) | 179.6 (1) |
H(1)—N(1)—C(2)—S(2) | 8.9 (1) | O(4)—C(4)—C(5)—C(6) | −178.4 (1) |
H(1)—N(1)—C(2)—N(3) | −172.1 (1) | O(4)—C(4)—C(5)—H(5) | 1.8 (1) |
H(1)—N(1)—C(6)—C(5) | 174.9 (1) | N(3)—C(4)—C(5)—C(6) | 1.4 (1) |
H(1)—N(1)—C(6)—H(6) | −2.7 (1) | N(3)—C(4)—C(5)—H(5) | −178.3 (1) |
C(4)—N(3)—C(2)—S(2) | 175.6 (1) | N(1)—C(6)—C(5)—C(4) | −2.2 (1) |
C(2)—N(3)—C(4)—O(4) | −178.7 (1) | N(1)—C(6)—C(5)—H(5) | 177.6 (1) |
C(4)—N(3)—C(2)—N(1) | −3.4 (1) | H(6)—C(6)—C(5)—C(4) | 175.1 (1) |
C(2)—N(3)—C(4)—C(5) | 1.4 (1) | H(6)—C(6)—C(5)—H(5) | −5.1 (1) |
C4H5N3O·H2O | F(000) = 272 |
Mr = 129.13 | Dx = 1.530 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5948 reflections |
a = 7.7161 (8) Å | θ = 2.7–50.3° |
b = 9.8337 (10) Å | µ = 0.12 mm−1 |
c = 7.5131 (8) Å | T = 90 K |
β = 100.523 (5)° | Block, colorless |
V = 560.49 (10) Å3 | 0.32 × 0.22 × 0.03 mm |
Z = 4 |
Bruker SMART APEX CCD area detector diffractometer | 5948 independent reflections |
Radiation source: fine-focus sealed tube | 4792 reflections with > 3σ(I) |
Graphite monochromator | Rint = 0.040 |
ϕ & ω scans | θmax = 50.3°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −16→16 |
Tmin = 0.961, Tmax = 0.996 | k = 0→21 |
5948 measured reflections | l = 0→16 |
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)] = 0.017 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.015 | H-atom parameters not refined |
S = 1.96 | w2 = 1/[s2(Fo2)] |
4792 reflections | (Δ/σ)max < 0.001 |
337 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C4H5N3O·H2O | V = 560.49 (10) Å3 |
Mr = 129.13 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.7161 (8) Å | µ = 0.12 mm−1 |
b = 9.8337 (10) Å | T = 90 K |
c = 7.5131 (8) Å | 0.32 × 0.22 × 0.03 mm |
β = 100.523 (5)° |
Bruker SMART APEX CCD area detector diffractometer | 5948 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4792 reflections with > 3σ(I) |
Tmin = 0.961, Tmax = 0.996 | Rint = 0.040 |
5948 measured reflections |
R[F2 > 2σ(F2)] = 0.017 | 0 restraints |
wR(F2) = 0.015 | H-atom parameters not refined |
S = 1.96 | Δρmax = 0.27 e Å−3 |
4792 reflections | Δρmin = −0.17 e Å−3 |
337 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O(1) | 0.35423 (3) | 0.20877 (2) | 0.47471 (3) | 0.014 | |
O(2) | 0.14835 (3) | 0.12075 (2) | 0.71691 (3) | 0.012 | |
N(1) | −0.08534 (2) | 0.00432 (2) | 0.78140 (2) | 0.010 | |
N(3) | −0.07914 (2) | 0.24444 (2) | 0.78909 (3) | 0.010 | |
N(4) | −0.31101 (3) | 0.36205 (2) | 0.86904 (3) | 0.013 | |
C(2) | −0.00196 (2) | 0.12502 (2) | 0.76001 (2) | 0.009 | |
C(4) | −0.23597 (2) | 0.24325 (2) | 0.84319 (2) | 0.009 | |
C(5) | −0.32210 (2) | 0.11871 (2) | 0.87386 (3) | 0.011 | |
C(6) | −0.24197 (2) | 0.00145 (2) | 0.83951 (2) | 0.011 | |
H(1) | −0.01911 | −0.08184 | 0.75113 | 0.012 (2) | |
H(1A) | 0.27966 | 0.25771 | 0.37788 | 0.019 (2) | |
H(1B) | 0.27054 | 0.17438 | 0.54462 | 0.022 (2) | |
H(4A) | −0.25000 | 0.44671 | 0.83268 | 0.018 (2) | |
H(4B) | −0.43057 | 0.35719 | 0.90660 | 0.016 (2) | |
H(5) | −0.44472 | 0.12010 | 0.92387 | 0.025 (2) | |
H(6) | −0.29795 | −0.09781 | 0.85832 | 0.024 (2) | |
DUM0 | 0.00000 | 0.00000 | 0.00000 | 0.000 | 0.0000 |
U11 | U22 | U33 | U12 | U13 | U23 | |
O(1) | 0.01137 (6) | 0.01433 (7) | 0.01657 (8) | 0.00056 (5) | 0.00552 (6) | 0.00132 (5) |
O(2) | 0.01007 (6) | 0.01026 (7) | 0.01724 (8) | −0.00009 (5) | 0.00674 (6) | −0.00016 (5) |
N(1) | 0.01008 (6) | 0.00669 (6) | 0.01390 (7) | −0.00033 (4) | 0.00441 (5) | −0.00016 (4) |
N(3) | 0.00906 (6) | 0.00691 (6) | 0.01323 (7) | −0.00036 (4) | 0.00434 (5) | −0.00018 (4) |
N(4) | 0.01145 (6) | 0.00802 (6) | 0.01874 (8) | 0.00080 (5) | 0.00641 (5) | −0.00044 (5) |
C(2) | 0.00850 (6) | 0.00734 (6) | 0.01150 (7) | −0.00026 (4) | 0.00377 (4) | 0.00002 (4) |
C(4) | 0.00899 (6) | 0.00715 (6) | 0.01200 (7) | −0.00006 (4) | 0.00374 (5) | −0.00009 (4) |
C(5) | 0.01042 (6) | 0.00832 (6) | 0.01573 (7) | −0.00063 (5) | 0.00599 (5) | 0.00022 (5) |
C(6) | 0.01081 (7) | 0.00741 (6) | 0.01419 (8) | −0.00109 (5) | 0.00476 (5) | 0.00035 (4) |
O(1)—H(1A) | 0.9690 (2) | N(4)—C(4) | 1.3337 (2) |
O(1)—H(1B) | 0.9650 (2) | N(4)—H(4A) | 1.0180 (2) |
O(2)—C(2) | 1.2605 (2) | N(4)—H(4B) | 1.0140 (2) |
N(1)—C(2) | 1.3734 (2) | C(4)—C(5) | 1.4320 (2) |
N(1)—C(6) | 1.3583 (2) | C(5)—C(6) | 1.3553 (2) |
N(1)—H(1) | 1.0360 (2) | C(5)—H(5) | 1.0800 (2) |
N(3)—C(2) | 1.3524 (2) | C(6)—H(6) | 1.0870 (2) |
N(3)—C(4) | 1.3451 (2) | ||
H(1A)—O(1)—H(1B) | 102.595 (19) | N(1)—C(2)—N(3) | 120.129 (16) |
C(2)—N(1)—C(6) | 121.263 (16) | N(3)—C(4)—N(4) | 118.349 (17) |
C(2)—N(1)—H(1) | 114.880 (16) | N(3)—C(4)—C(5) | 121.711 (16) |
C(6)—N(1)—H(1) | 123.854 (16) | N(4)—C(4)—C(5) | 119.939 (17) |
C(2)—N(3)—C(4) | 119.229 (16) | C(4)—C(5)—C(6) | 117.113 (16) |
C(4)—N(4)—H(4A) | 116.292 (17) | C(4)—C(5)—H(5) | 120.463 (16) |
C(4)—N(4)—H(4B) | 116.138 (17) | C(6)—C(5)—H(5) | 122.420 (17) |
H(4A)—N(4)—H(4B) | 127.015 (18) | N(1)—C(6)—C(5) | 120.473 (17) |
O(2)—C(2)—N(1) | 118.290 (17) | N(1)—C(6)—H(6) | 117.292 (16) |
O(2)—C(2)—N(3) | 121.563 (17) | C(5)—C(6)—H(6) | 122.231 (17) |
C(6)—N(1)—C(2)—O(2) | 175.5 (1) | H(4A)—N(4)—C(4)—N(3) | 6.4 (1) |
C(6)—N(1)—C(2)—N(3) | −3.0 (1) | H(4A)—N(4)—C(4)—C(5) | −173.9 (1) |
C(2)—N(1)—C(6)—C(5) | 1.6 (1) | H(4B)—N(4)—C(4)—N(3) | 178.5 (1) |
C(2)—N(1)—C(6)—H(6) | −177.7 (1) | H(4B)—N(4)—C(4)—C(5) | −1.8 (1) |
H(1)—N(1)—C(2)—O(2) | −4.0 (1) | N(3)—C(4)—C(5)—C(6) | −2.4 (1) |
H(1)—N(1)—C(2)—N(3) | 177.6 (1) | N(3)—C(4)—C(5)—H(5) | 176.8 (1) |
H(1)—N(1)—C(6)—C(5) | −179.0 (1) | N(4)—C(4)—C(5)—C(6) | 177.9 (1) |
H(1)—N(1)—C(6)—H(6) | 1.7 (1) | N(4)—C(4)—C(5)—H(5) | −2.9 (1) |
C(4)—N(3)—C(2)—O(2) | −176.9 (1) | C(4)—C(5)—C(6)—N(1) | 1.0 (1) |
C(4)—N(3)—C(2)—N(1) | 1.6 (1) | C(4)—C(5)—C(6)—H(6) | −179.7 (1) |
C(2)—N(3)—C(4)—N(4) | −179.2 (1) | H(5)—C(5)—C(6)—N(1) | −178.2 (1) |
C(2)—N(3)—C(4)—C(5) | 1.1 (1) | H(5)—C(5)—C(6)—H(6) | 1.0 (1) |
C7H6O3 | F(000) = 288 |
Mr = 138.12 | Dx = 1.495 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 31354 reflections |
a = 4.8818 (2) Å | θ = 2.6–50.3° |
b = 11.2009 (5) Å | µ = 0.12 mm−1 |
c = 11.2335 (5) Å | T = 90 K |
β = 92.621 (2)° | Prism, colorless |
V = 613.61 (5) Å3 | 0.25 × 0.22 × 0.2 mm |
Z = 4 |
Bruker SMART APEX CCD area detector diffractometer | 6440 independent reflections |
Radiation source: fine-focus sealed tube | 5439 reflections with > 3σ(I) |
Graphite monochromator | Rint = 0.029 |
ϕ & ω scans | θmax = 50.3°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→10 |
Tmin = 0.886, Tmax = 0.977 | k = −23→24 |
31354 measured reflections | l = −24→24 |
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)] = 0.020 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.020 | H-atom parameters not refined |
S = 1.96 | w2 = q/[s2(Fo2) + (0.00 P)2 + 0.00 P + 0.00 + 0.00 sin(th)]
where P = (0.3333 Fo2 + 0.6667 Fc2) q = 1.0 |
5439 reflections | (Δ/σ)max < 0.001 |
276 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
C7H6O3 | V = 613.61 (5) Å3 |
Mr = 138.12 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 4.8818 (2) Å | µ = 0.12 mm−1 |
b = 11.2009 (5) Å | T = 90 K |
c = 11.2335 (5) Å | 0.25 × 0.22 × 0.2 mm |
β = 92.621 (2)° |
Bruker SMART APEX CCD area detector diffractometer | 6440 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 5439 reflections with > 3σ(I) |
Tmin = 0.886, Tmax = 0.977 | Rint = 0.029 |
31354 measured reflections |
R[F2 > 2σ(F2)] = 0.020 | 0 restraints |
wR(F2) = 0.020 | H-atom parameters not refined |
S = 1.96 | Δρmax = 0.27 e Å−3 |
5439 reflections | Δρmin = −0.26 e Å−3 |
276 parameters |
Experimental. Crystal to Detector distance was 6.03 cm, ω range is 0.3 ° and exposure time was 20 s, 40 s and 80 s in three batches respectively. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O(1) | 0.83999 (4) | 0.13928 (2) | −0.05215 (2) | 0.014 | |
O(3) | 0.39275 (5) | 0.06756 (2) | 0.24999 (2) | 0.016 | |
O(2) | 0.76762 (4) | 0.01483 (2) | 0.09897 (2) | 0.013 | |
C(1) | 0.50516 (3) | 0.19284 (2) | 0.08238 (2) | 0.010 | |
C(3) | 0.15873 (4) | 0.24924 (2) | 0.22021 (2) | 0.014 | |
C(6) | 0.45370 (4) | 0.29928 (2) | 0.01908 (2) | 0.013 | |
C(2) | 0.35609 (4) | 0.16777 (2) | 0.18410 (2) | 0.012 | |
C(5) | 0.25886 (4) | 0.37961 (2) | 0.05541 (2) | 0.015 | |
C(4) | 0.11104 (4) | 0.35399 (2) | 0.15648 (2) | 0.015 | |
C(7) | 0.71398 (3) | 0.10908 (2) | 0.04397 (2) | 0.010 | |
H(6) | 0.57311 | 0.31697 | −0.05713 | 0.027 (2) | |
H(3) | 0.04064 | 0.22880 | 0.29617 | 0.030 (2) | |
H(5) | 0.21541 | 0.45737 | 0.00156 | 0.036 (2) | |
H(4) | −0.04312 | 0.41534 | 0.18430 | 0.036 (2) | |
H(2) | 0.54071 | 0.02176 | 0.21898 | 0.017 (2) | |
H(1) | 0.98372 | 0.07598 | −0.07049 | 0.013 (2) | |
DUM0 | 0.00000 | 0.00000 | 0.00000 | 0.000 | 0.0000 |
U11 | U22 | U33 | U12 | U13 | U23 | |
O(1) | 0.01430 (7) | 0.01378 (6) | 0.01421 (6) | 0.00347 (6) | 0.00571 (5) | 0.00264 (6) |
O(3) | 0.01832 (8) | 0.01545 (7) | 0.01425 (7) | 0.00385 (6) | 0.00600 (6) | 0.00245 (6) |
O(2) | 0.01341 (6) | 0.01152 (5) | 0.01396 (6) | 0.00309 (5) | 0.00397 (5) | 0.00218 (5) |
C(1) | 0.00986 (5) | 0.01006 (5) | 0.01145 (6) | 0.00119 (5) | 0.00128 (4) | −0.00038 (5) |
C(3) | 0.01351 (7) | 0.01583 (7) | 0.01403 (6) | 0.00326 (6) | 0.00273 (5) | −0.00293 (6) |
C(6) | 0.01237 (6) | 0.01147 (6) | 0.01546 (6) | 0.00205 (5) | 0.00152 (5) | 0.00136 (5) |
C(2) | 0.01145 (6) | 0.01200 (6) | 0.01141 (6) | 0.00152 (5) | 0.00202 (5) | −0.00112 (5) |
C(5) | 0.01407 (7) | 0.01204 (6) | 0.01979 (8) | 0.00347 (5) | 0.00050 (6) | −0.00003 (6) |
C(4) | 0.01348 (7) | 0.01417 (7) | 0.01786 (7) | 0.00388 (6) | 0.00044 (6) | −0.00383 (6) |
C(7) | 0.01001 (5) | 0.01005 (5) | 0.01117 (5) | 0.00092 (5) | 0.00191 (4) | 0.00023 (5) |
O(1)—C(7) | 1.3113 (2) | C(3)—C(2) | 1.4005 (3) |
O(1)—H(1) | 1.0250 (2) | C(3)—C(4) | 1.3886 (3) |
O(3)—C(2) | 1.3519 (3) | C(3)—H(3) | 1.0760 (2) |
O(3)—H(2) | 0.9640 (2) | C(6)—C(5) | 1.3843 (3) |
O(2)—C(7) | 1.2450 (2) | C(6)—H(6) | 1.0760 (2) |
C(1)—C(6) | 1.4049 (3) | C(5)—C(4) | 1.4025 (3) |
C(1)—C(2) | 1.4107 (2) | C(5)—H(5) | 1.0760 (2) |
C(1)—C(7) | 1.4648 (2) | C(4)—H(4) | 1.0760 (2) |
C(7)—O(1)—H(1) | 109.777 (18) | O(3)—C(2)—C(3) | 117.254 (18) |
C(2)—O(3)—H(2) | 109.061 (18) | C(1)—C(2)—C(3) | 119.484 (18) |
C(6)—C(1)—C(2) | 119.465 (16) | C(6)—C(5)—C(4) | 119.444 (19) |
C(6)—C(1)—C(7) | 120.344 (16) | C(6)—C(5)—H(5) | 118.74 (2) |
C(2)—C(1)—C(7) | 120.187 (16) | C(4)—C(5)—H(5) | 121.682 (19) |
C(2)—C(3)—C(4) | 120.166 (18) | C(3)—C(4)—C(5) | 120.659 (18) |
C(2)—C(3)—H(3) | 119.45 (2) | C(3)—C(4)—H(4) | 119.52 (2) |
C(4)—C(3)—H(3) | 120.356 (18) | C(5)—C(4)—H(4) | 119.81 (2) |
C(1)—C(6)—C(5) | 120.781 (18) | O(1)—C(7)—O(2) | 122.100 (17) |
C(1)—C(6)—H(6) | 117.917 (17) | O(1)—C(7)—C(1) | 115.871 (17) |
C(5)—C(6)—H(6) | 121.291 (18) | O(2)—C(7)—C(1) | 122.028 (16) |
O(3)—C(2)—C(1) | 123.262 (17) | ||
H(1)—O(1)—C(7)—O(2) | −1.3 (1) | C(4)—C(3)—C(2)—O(3) | 180.0 (1) |
H(1)—O(1)—C(7)—C(1) | 178.9 (1) | C(4)—C(3)—C(2)—C(1) | −0.2 (1) |
H(2)—O(3)—C(2)—C(1) | 3.7 (1) | C(2)—C(3)—C(4)—C(5) | 0.1 (1) |
H(2)—O(3)—C(2)—C(3) | −176.5 (1) | C(2)—C(3)—C(4)—H(4) | 179.1 (1) |
C(6)—C(1)—C(2)—O(3) | 180.0 (1) | H(3)—C(3)—C(2)—O(3) | −1.8 (1) |
C(6)—C(1)—C(2)—C(3) | 0.1 (1) | H(3)—C(3)—C(2)—C(1) | 178.1 (1) |
C(2)—C(1)—C(6)—C(5) | 0.0 (1) | H(3)—C(3)—C(4)—C(5) | −178.2 (1) |
C(2)—C(1)—C(6)—H(6) | 178.8 (1) | H(3)—C(3)—C(4)—H(4) | 0.9 (1) |
C(6)—C(1)—C(7)—O(1) | −1.3 (1) | C(1)—C(6)—C(5)—C(4) | −0.2 (1) |
C(6)—C(1)—C(7)—O(2) | 178.9 (1) | C(1)—C(6)—C(5)—H(5) | −176.0 (1) |
C(7)—C(1)—C(6)—C(5) | −179.3 (1) | H(6)—C(6)—C(5)—C(4) | −178.9 (1) |
C(7)—C(1)—C(6)—H(6) | −0.5 (1) | H(6)—C(6)—C(5)—H(5) | 5.2 (1) |
C(2)—C(1)—C(7)—O(1) | 179.3 (1) | C(6)—C(5)—C(4)—C(3) | 0.1 (1) |
C(7)—C(1)—C(2)—O(3) | −0.7 (1) | C(6)—C(5)—C(4)—H(4) | −178.9 (1) |
C(2)—C(1)—C(7)—O(2) | −0.4 (1) | H(5)—C(5)—C(4)—C(3) | 175.8 (1) |
C(7)—C(1)—C(2)—C(3) | 179.5 (1) | H(5)—C(5)—C(4)—H(4) | −3.2 (1) |
Experimental details
(2-thiouracil) | (cytosine) | (salicylicacid) | |
Crystal data | |||
Chemical formula | C4H4N2OS | C4H5N3O·H2O | C7H6O3 |
Mr | 128.16 | 129.13 | 138.12 |
Crystal system, space group | Triclinic, P1 | Monoclinic, P21/c | Monoclinic, P21/c |
Temperature (K) | 90 | 90 | 90 |
a, b, c (Å) | 4.2427 (4), 5.9648 (5), 10.5801 (10) | 7.7161 (8), 9.8337 (10), 7.5131 (8) | 4.8818 (2), 11.2009 (5), 11.2335 (5) |
α, β, γ (°) | 105.736 (5), 94.912 (5), 91.927 (4) | 90, 100.523 (5), 90 | 90, 92.621 (2), 90 |
V (Å3) | 256.32 (4) | 560.49 (10) | 613.61 (5) |
Z | 2 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.51 | 0.12 | 0.12 |
Crystal size (mm) | 0.39 × 0.19 × 0.12 | 0.32 × 0.22 × 0.03 | 0.25 × 0.22 × 0.2 |
Data collection | |||
Diffractometer | Bruker SMART APEX CCD area detector diffractometer | Bruker SMART APEX CCD area detector diffractometer | Bruker SMART APEX CCD area detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) | Multi-scan (SADABS; Sheldrick, 1996) | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.831, 0.943 | 0.961, 0.996 | 0.886, 0.977 |
No. of measured, independent and observed [ > 3σ(I)] reflections | 4983, 4983, 4697 | 5948, 5948, 4792 | 31354, 6440, 5439 |
Rint | 0.031 | 0.040 | 0.029 |
(sin θ/λ)max (Å−1) | 1.103 | 1.082 | 1.083 |
Refinement | |||
R[F2 > 2σ(F2)], wR(F2), S | 0.014, 0.017, 1.93 | 0.017, 0.015, 1.96 | 0.020, 0.020, 1.96 |
No. of reflections | 4697 | 4792 | 5439 |
No. of parameters | 229 | 337 | 276 |
H-atom treatment | H-atom parameters not refined | H-atom parameters not refined | H-atom parameters not refined |
Δρmax, Δρmin (e Å−3) | 0.32, −0.20 | 0.27, −0.17 | 0.27, −0.26 |
Computer programs: SMART (Bruker, 2004), SMART, SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 1997), Koritsanszky et al., (2003).
S(2)—C(2) | 1.6828 (2) | N(3)—C(4) | 1.3942 (2) |
O(4)—C(4) | 1.2354 (3) | N(3)—H(3) | 1.0300 (2) |
N(1)—C(2) | 1.3511 (2) | C(4)—C(5) | 1.4420 (3) |
N(1)—C(6) | 1.3709 (2) | C(6)—C(5) | 1.3538 (3) |
N(1)—H(1) | 1.0300 (2) | C(6)—H(6) | 1.0800 (2) |
N(3)—C(2) | 1.3570 (2) | C(5)—H(5) | 1.0800 (2) |
C(2)—N(1)—C(6) | 122.692 (16) | O(4)—C(4)—N(3) | 119.512 (19) |
C(2)—N(1)—H(1) | 120.009 (16) | O(4)—C(4)—C(5) | 125.049 (18) |
C(6)—N(1)—H(1) | 117.100 (15) | N(3)—C(4)—C(5) | 115.439 (16) |
C(2)—N(3)—C(4) | 125.400 (16) | N(1)—C(6)—C(5) | 121.437 (16) |
C(2)—N(3)—H(3) | 119.129 (15) | N(1)—C(6)—H(6) | 111.386 (16) |
C(4)—N(3)—H(3) | 115.445 (15) | C(5)—C(6)—H(6) | 127.130 (17) |
S(2)—C(2)—N(1) | 121.904 (13) | C(4)—C(5)—C(6) | 118.709 (16) |
S(2)—C(2)—N(3) | 121.868 (13) | C(4)—C(5)—H(5) | 122.272 (17) |
N(1)—C(2)—N(3) | 116.222 (15) | C(6)—C(5)—H(5) | 119.018 (17) |
C(6)—N(1)—C(2)—S(2) | −176.4 (1) | H(3)—N(3)—C(2)—S(2) | −2.5 (1) |
C(6)—N(1)—C(2)—N(3) | 2.7 (1) | H(3)—N(3)—C(2)—N(1) | 178.5 (1) |
C(2)—N(1)—C(6)—C(5) | 0.1 (1) | H(3)—N(3)—C(4)—O(4) | −0.6 (1) |
C(2)—N(1)—C(6)—H(6) | −177.6 (1) | H(3)—N(3)—C(4)—C(5) | 179.6 (1) |
H(1)—N(1)—C(2)—S(2) | 8.9 (1) | O(4)—C(4)—C(5)—C(6) | −178.4 (1) |
H(1)—N(1)—C(2)—N(3) | −172.1 (1) | O(4)—C(4)—C(5)—H(5) | 1.8 (1) |
H(1)—N(1)—C(6)—C(5) | 174.9 (1) | N(3)—C(4)—C(5)—C(6) | 1.4 (1) |
H(1)—N(1)—C(6)—H(6) | −2.7 (1) | N(3)—C(4)—C(5)—H(5) | −178.3 (1) |
C(4)—N(3)—C(2)—S(2) | 175.6 (1) | N(1)—C(6)—C(5)—C(4) | −2.2 (1) |
C(2)—N(3)—C(4)—O(4) | −178.7 (1) | N(1)—C(6)—C(5)—H(5) | 177.6 (1) |
C(4)—N(3)—C(2)—N(1) | −3.4 (1) | H(6)—C(6)—C(5)—C(4) | 175.1 (1) |
C(2)—N(3)—C(4)—C(5) | 1.4 (1) | H(6)—C(6)—C(5)—H(5) | −5.1 (1) |
O(1)—H(1A) | 0.9690 (2) | N(4)—C(4) | 1.3337 (2) |
O(1)—H(1B) | 0.9650 (2) | N(4)—H(4A) | 1.0180 (2) |
O(2)—C(2) | 1.2605 (2) | N(4)—H(4B) | 1.0140 (2) |
N(1)—C(2) | 1.3734 (2) | C(4)—C(5) | 1.4320 (2) |
N(1)—C(6) | 1.3583 (2) | C(5)—C(6) | 1.3553 (2) |
N(1)—H(1) | 1.0360 (2) | C(5)—H(5) | 1.0800 (2) |
N(3)—C(2) | 1.3524 (2) | C(6)—H(6) | 1.0870 (2) |
N(3)—C(4) | 1.3451 (2) | ||
H(1A)—O(1)—H(1B) | 102.595 (19) | N(1)—C(2)—N(3) | 120.129 (16) |
C(2)—N(1)—C(6) | 121.263 (16) | N(3)—C(4)—N(4) | 118.349 (17) |
C(2)—N(1)—H(1) | 114.880 (16) | N(3)—C(4)—C(5) | 121.711 (16) |
C(6)—N(1)—H(1) | 123.854 (16) | N(4)—C(4)—C(5) | 119.939 (17) |
C(2)—N(3)—C(4) | 119.229 (16) | C(4)—C(5)—C(6) | 117.113 (16) |
C(4)—N(4)—H(4A) | 116.292 (17) | C(4)—C(5)—H(5) | 120.463 (16) |
C(4)—N(4)—H(4B) | 116.138 (17) | C(6)—C(5)—H(5) | 122.420 (17) |
H(4A)—N(4)—H(4B) | 127.015 (18) | N(1)—C(6)—C(5) | 120.473 (17) |
O(2)—C(2)—N(1) | 118.290 (17) | N(1)—C(6)—H(6) | 117.292 (16) |
O(2)—C(2)—N(3) | 121.563 (17) | C(5)—C(6)—H(6) | 122.231 (17) |
C(6)—N(1)—C(2)—O(2) | 175.5 (1) | H(4A)—N(4)—C(4)—N(3) | 6.4 (1) |
C(6)—N(1)—C(2)—N(3) | −3.0 (1) | H(4A)—N(4)—C(4)—C(5) | −173.9 (1) |
C(2)—N(1)—C(6)—C(5) | 1.6 (1) | H(4B)—N(4)—C(4)—N(3) | 178.5 (1) |
C(2)—N(1)—C(6)—H(6) | −177.7 (1) | H(4B)—N(4)—C(4)—C(5) | −1.8 (1) |
H(1)—N(1)—C(2)—O(2) | −4.0 (1) | N(3)—C(4)—C(5)—C(6) | −2.4 (1) |
H(1)—N(1)—C(2)—N(3) | 177.6 (1) | N(3)—C(4)—C(5)—H(5) | 176.8 (1) |
H(1)—N(1)—C(6)—C(5) | −179.0 (1) | N(4)—C(4)—C(5)—C(6) | 177.9 (1) |
H(1)—N(1)—C(6)—H(6) | 1.7 (1) | N(4)—C(4)—C(5)—H(5) | −2.9 (1) |
C(4)—N(3)—C(2)—O(2) | −176.9 (1) | C(4)—C(5)—C(6)—N(1) | 1.0 (1) |
C(4)—N(3)—C(2)—N(1) | 1.6 (1) | C(4)—C(5)—C(6)—H(6) | −179.7 (1) |
C(2)—N(3)—C(4)—N(4) | −179.2 (1) | H(5)—C(5)—C(6)—N(1) | −178.2 (1) |
C(2)—N(3)—C(4)—C(5) | 1.1 (1) | H(5)—C(5)—C(6)—H(6) | 1.0 (1) |
O(1)—C(7) | 1.3113 (2) | C(3)—C(2) | 1.4005 (3) |
O(1)—H(1) | 1.0250 (2) | C(3)—C(4) | 1.3886 (3) |
O(3)—C(2) | 1.3519 (3) | C(3)—H(3) | 1.0760 (2) |
O(3)—H(2) | 0.9640 (2) | C(6)—C(5) | 1.3843 (3) |
O(2)—C(7) | 1.2450 (2) | C(6)—H(6) | 1.0760 (2) |
C(1)—C(6) | 1.4049 (3) | C(5)—C(4) | 1.4025 (3) |
C(1)—C(2) | 1.4107 (2) | C(5)—H(5) | 1.0760 (2) |
C(1)—C(7) | 1.4648 (2) | C(4)—H(4) | 1.0760 (2) |
C(7)—O(1)—H(1) | 109.777 (18) | O(3)—C(2)—C(3) | 117.254 (18) |
C(2)—O(3)—H(2) | 109.061 (18) | C(1)—C(2)—C(3) | 119.484 (18) |
C(6)—C(1)—C(2) | 119.465 (16) | C(6)—C(5)—C(4) | 119.444 (19) |
C(6)—C(1)—C(7) | 120.344 (16) | C(6)—C(5)—H(5) | 118.74 (2) |
C(2)—C(1)—C(7) | 120.187 (16) | C(4)—C(5)—H(5) | 121.682 (19) |
C(2)—C(3)—C(4) | 120.166 (18) | C(3)—C(4)—C(5) | 120.659 (18) |
C(2)—C(3)—H(3) | 119.45 (2) | C(3)—C(4)—H(4) | 119.52 (2) |
C(4)—C(3)—H(3) | 120.356 (18) | C(5)—C(4)—H(4) | 119.81 (2) |
C(1)—C(6)—C(5) | 120.781 (18) | O(1)—C(7)—O(2) | 122.100 (17) |
C(1)—C(6)—H(6) | 117.917 (17) | O(1)—C(7)—C(1) | 115.871 (17) |
C(5)—C(6)—H(6) | 121.291 (18) | O(2)—C(7)—C(1) | 122.028 (16) |
O(3)—C(2)—C(1) | 123.262 (17) | ||
H(1)—O(1)—C(7)—O(2) | −1.3 (1) | C(4)—C(3)—C(2)—O(3) | 180.0 (1) |
H(1)—O(1)—C(7)—C(1) | 178.9 (1) | C(4)—C(3)—C(2)—C(1) | −0.2 (1) |
H(2)—O(3)—C(2)—C(1) | 3.7 (1) | C(2)—C(3)—C(4)—C(5) | 0.1 (1) |
H(2)—O(3)—C(2)—C(3) | −176.5 (1) | C(2)—C(3)—C(4)—H(4) | 179.1 (1) |
C(6)—C(1)—C(2)—O(3) | 180.0 (1) | H(3)—C(3)—C(2)—O(3) | −1.8 (1) |
C(6)—C(1)—C(2)—C(3) | 0.1 (1) | H(3)—C(3)—C(2)—C(1) | 178.1 (1) |
C(2)—C(1)—C(6)—C(5) | 0.0 (1) | H(3)—C(3)—C(4)—C(5) | −178.2 (1) |
C(2)—C(1)—C(6)—H(6) | 178.8 (1) | H(3)—C(3)—C(4)—H(4) | 0.9 (1) |
C(6)—C(1)—C(7)—O(1) | −1.3 (1) | C(1)—C(6)—C(5)—C(4) | −0.2 (1) |
C(6)—C(1)—C(7)—O(2) | 178.9 (1) | C(1)—C(6)—C(5)—H(5) | −176.0 (1) |
C(7)—C(1)—C(6)—C(5) | −179.3 (1) | H(6)—C(6)—C(5)—C(4) | −178.9 (1) |
C(7)—C(1)—C(6)—H(6) | −0.5 (1) | H(6)—C(6)—C(5)—H(5) | 5.2 (1) |
C(2)—C(1)—C(7)—O(1) | 179.3 (1) | C(6)—C(5)—C(4)—C(3) | 0.1 (1) |
C(7)—C(1)—C(2)—O(3) | −0.7 (1) | C(6)—C(5)—C(4)—H(4) | −178.9 (1) |
C(2)—C(1)—C(7)—O(2) | −0.4 (1) | H(5)—C(5)—C(4)—C(3) | 175.8 (1) |
C(7)—C(1)—C(2)—C(3) | 179.5 (1) | H(5)—C(5)—C(4)—H(4) | −3.2 (1) |