


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536800019589/ob6014sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536800019589/ob6014Isup2.hkl |
CCDC reference: 155885
The title compound, (I), was prepared by Spa Contract Synthesis. Crystals of (I) were grown from a dimethylformamide/water (1:25) solution.
All H atoms were included in the refinement at calculated positions as riding models with C—H set to 0.95 (Ar—H) and 0.99 Å (CH2), except for the H atoms involved in the hydrogen-bonding associations, which were located on difference syntheses and for which both positional and displacement parameters were refined.
Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.
![]() | Fig. 1. The molecular configuration and atom-numbering scheme for (I), showing 30% probability displacement ellipsoids. |
C10H15ClN5O·0.5H2O | Dx = 1.505 Mg m−3 |
Mr = 264.72 | Melting point: 479-481 K K |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 15.559 (3) Å | Cell parameters from 5223 reflections |
b = 9.3139 (19) Å | θ = 2.9–27.5° |
c = 16.493 (3) Å | µ = 0.33 mm−1 |
β = 102.08 (3)° | T = 150 K |
V = 2337.2 (8) Å3 | Block, colourless |
Z = 8 | 0.26 × 0.14 × 0.14 mm |
F(000) = 1112 |
Enraf Nonius KappaCCD area-detector diffractometer | 2672 independent reflections |
Radiation source: Enraf Nonius FR591 rotating anode | 2113 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.0° |
ϕ and ω scans | h = −20→19 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −12→12 |
Tmin = 0.920, Tmax = 0.956 | l = −21→21 |
10159 measured reflections |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.116 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0659P)2 + 0.5619P] where P = (Fo2 + 2Fc2)/3 |
2672 reflections | (Δ/σ)max < 0.001 |
183 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.41 e Å−3 |
C10H15ClN5O·0.5H2O | V = 2337.2 (8) Å3 |
Mr = 264.72 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 15.559 (3) Å | µ = 0.33 mm−1 |
b = 9.3139 (19) Å | T = 150 K |
c = 16.493 (3) Å | 0.26 × 0.14 × 0.14 mm |
β = 102.08 (3)° |
Enraf Nonius KappaCCD area-detector diffractometer | 2672 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | 2113 reflections with I > 2σ(I) |
Tmin = 0.920, Tmax = 0.956 | Rint = 0.047 |
10159 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.116 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.24 e Å−3 |
2672 reflections | Δρmin = −0.41 e Å−3 |
183 parameters |
Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.00203 (8) | 0.37886 (15) | 0.59398 (7) | 0.0250 (3) | |
C2 | −0.04182 (10) | 0.27801 (18) | 0.54389 (9) | 0.0249 (4) | |
N21 | −0.12341 (9) | 0.24368 (18) | 0.55424 (9) | 0.0296 (3) | |
H21 | −0.1456 (13) | 0.301 (3) | 0.5787 (13) | 0.046 (6)* | |
H22 | −0.1510 (13) | 0.186 (2) | 0.5205 (12) | 0.035 (5)* | |
N3 | −0.01179 (8) | 0.20299 (15) | 0.48564 (8) | 0.0261 (3) | |
C4 | 0.06786 (10) | 0.24364 (18) | 0.47735 (9) | 0.0257 (4) | |
Cl4 | 0.10767 (3) | 0.14798 (5) | 0.40232 (3) | 0.03639 (17) | |
C5 | 0.11831 (10) | 0.34908 (17) | 0.51986 (9) | 0.0262 (4) | |
H5 | 0.1743 | 0.3740 | 0.5096 | 0.033* | |
C6 | 0.08140 (10) | 0.41912 (17) | 0.58057 (9) | 0.0238 (3) | |
N61 | 0.12211 (8) | 0.52898 (15) | 0.62697 (8) | 0.0268 (3) | |
C62 | 0.21122 (10) | 0.57591 (18) | 0.62698 (9) | 0.0277 (4) | |
H621 | 0.2128 | 0.6820 | 0.6243 | 0.035* | |
H622 | 0.2297 | 0.5374 | 0.5774 | 0.035* | |
C63 | 0.27461 (10) | 0.52464 (18) | 0.70472 (9) | 0.0252 (3) | |
H631 | 0.3334 | 0.5665 | 0.7061 | 0.032* | |
H632 | 0.2801 | 0.4189 | 0.7027 | 0.032* | |
C64 | 0.24399 (10) | 0.56704 (18) | 0.78406 (9) | 0.0239 (3) | |
H641 | 0.2505 (11) | 0.671 (2) | 0.7900 (11) | 0.030 (5)* | |
C65 | 0.14788 (10) | 0.52713 (19) | 0.77775 (9) | 0.0273 (4) | |
H651 | 0.1274 | 0.5666 | 0.8261 | 0.034* | |
H652 | 0.1422 | 0.4213 | 0.7789 | 0.034* | |
C66 | 0.09035 (10) | 0.5856 (2) | 0.69799 (9) | 0.0295 (4) | |
H661 | 0.0285 | 0.5563 | 0.6944 | 0.037* | |
H662 | 0.0929 | 0.6918 | 0.6980 | 0.037* | |
C67 | 0.30207 (10) | 0.50032 (17) | 0.86049 (9) | 0.0256 (4) | |
O67 | 0.26969 (7) | 0.44034 (13) | 0.91439 (7) | 0.0330 (3) | |
N67 | 0.38837 (9) | 0.50667 (17) | 0.86607 (9) | 0.0309 (4) | |
H671 | 0.4097 (11) | 0.548 (2) | 0.8278 (11) | 0.034 (5)* | |
H672 | 0.4210 (12) | 0.462 (2) | 0.9058 (11) | 0.036 (5)* | |
O1W | 0.0000 | 0.8089 (3) | 0.2500 | 0.0459 (5) | |
H1W | 0.0084 (16) | 0.752 (3) | 0.2890 (15) | 0.077 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0209 (7) | 0.0322 (8) | 0.0218 (6) | 0.0004 (6) | 0.0046 (5) | 0.0001 (6) |
C2 | 0.0222 (8) | 0.0292 (9) | 0.0228 (7) | 0.0020 (7) | 0.0039 (6) | 0.0048 (6) |
N21 | 0.0231 (8) | 0.0367 (9) | 0.0305 (8) | −0.0039 (7) | 0.0092 (6) | −0.0070 (7) |
N3 | 0.0240 (7) | 0.0296 (8) | 0.0252 (7) | 0.0008 (6) | 0.0062 (5) | −0.0015 (6) |
C4 | 0.0253 (8) | 0.0286 (9) | 0.0243 (7) | 0.0047 (7) | 0.0075 (6) | 0.0022 (6) |
Cl4 | 0.0337 (3) | 0.0403 (3) | 0.0387 (3) | 0.00087 (18) | 0.01579 (19) | −0.01113 (18) |
C5 | 0.0230 (8) | 0.0307 (9) | 0.0263 (8) | 0.0008 (7) | 0.0081 (6) | 0.0025 (6) |
C6 | 0.0221 (8) | 0.0273 (9) | 0.0209 (7) | 0.0021 (6) | 0.0021 (6) | 0.0035 (6) |
N61 | 0.0222 (7) | 0.0322 (8) | 0.0264 (6) | −0.0020 (6) | 0.0063 (5) | −0.0028 (6) |
C62 | 0.0259 (8) | 0.0297 (9) | 0.0281 (8) | −0.0042 (7) | 0.0073 (6) | 0.0010 (7) |
C63 | 0.0214 (8) | 0.0272 (9) | 0.0276 (8) | −0.0022 (7) | 0.0064 (6) | −0.0002 (7) |
C64 | 0.0225 (8) | 0.0214 (9) | 0.0275 (8) | 0.0004 (6) | 0.0046 (6) | −0.0012 (6) |
C65 | 0.0237 (8) | 0.0331 (9) | 0.0264 (8) | 0.0016 (7) | 0.0081 (6) | −0.0042 (7) |
C66 | 0.0233 (8) | 0.0359 (10) | 0.0286 (8) | 0.0024 (7) | 0.0040 (6) | −0.0068 (7) |
C67 | 0.0255 (8) | 0.0242 (9) | 0.0274 (8) | 0.0012 (6) | 0.0060 (6) | −0.0031 (6) |
O67 | 0.0288 (6) | 0.0401 (7) | 0.0314 (6) | 0.0026 (5) | 0.0092 (5) | 0.0083 (5) |
N67 | 0.0231 (8) | 0.0391 (9) | 0.0295 (7) | 0.0012 (6) | 0.0031 (6) | 0.0073 (6) |
O1W | 0.0504 (13) | 0.0568 (14) | 0.0289 (10) | 0.000 | 0.0046 (8) | 0.000 |
N1—C2 | 1.340 (2) | C63—C64 | 1.535 (2) |
N1—C6 | 1.3523 (19) | C63—H631 | 0.99 |
C2—N3 | 1.348 (2) | C63—H632 | 0.99 |
C2—N21 | 1.354 (2) | C64—C67 | 1.521 (2) |
N21—H21 | 0.79 (2) | C64—C65 | 1.523 (2) |
N21—H22 | 0.83 (2) | C64—H641 | 0.979 (19) |
N3—C4 | 1.3299 (19) | C65—C66 | 1.528 (2) |
C4—C5 | 1.357 (2) | C65—H651 | 0.99 |
C4—Cl4 | 1.7407 (16) | C65—H652 | 0.99 |
C5—C6 | 1.414 (2) | C66—H661 | 0.99 |
C5—H5 | 0.95 | C66—H662 | 0.99 |
C6—N61 | 1.353 (2) | C67—O67 | 1.2425 (18) |
N61—C62 | 1.4536 (19) | C67—N67 | 1.328 (2) |
N61—C66 | 1.4617 (19) | N67—H671 | 0.862 (18) |
C62—C63 | 1.522 (2) | N67—H672 | 0.85 (2) |
C62—H621 | 0.99 | O1W—H1W | 0.82 (2) |
C62—H622 | 0.99 | ||
C2—N1—C6 | 117.27 (13) | C64—C63—H631 | 109.2 |
N1—C2—N3 | 126.53 (14) | C62—C63—H632 | 109.2 |
N1—C2—N21 | 117.24 (14) | C64—C63—H632 | 109.2 |
N3—C2—N21 | 116.19 (15) | H631—C63—H632 | 107.9 |
C2—N21—H21 | 115.2 (16) | C67—C64—C65 | 111.18 (13) |
C2—N21—H22 | 116.0 (13) | C67—C64—C63 | 111.39 (13) |
H21—N21—H22 | 124 (2) | C65—C64—C63 | 110.76 (13) |
C4—N3—C2 | 113.28 (13) | C67—C64—H641 | 107.0 (11) |
N3—C4—C5 | 127.12 (15) | C65—C64—H641 | 109.1 (10) |
N3—C4—Cl4 | 113.91 (12) | C63—C64—H641 | 107.2 (10) |
C5—C4—Cl4 | 118.97 (12) | C64—C65—C66 | 111.20 (13) |
C4—C5—C6 | 115.03 (14) | C64—C65—H651 | 109.4 |
C4—C5—H5 | 122.5 | C66—C65—H651 | 109.4 |
C6—C5—H5 | 122.5 | C64—C65—H652 | 109.4 |
N1—C6—N61 | 116.91 (13) | C66—C65—H652 | 109.4 |
N1—C6—C5 | 120.54 (14) | H651—C65—H652 | 108.0 |
N61—C6—C5 | 122.55 (14) | N61—C66—C65 | 109.03 (13) |
C6—N61—C62 | 124.13 (13) | N61—C66—H661 | 109.9 |
C6—N61—C66 | 121.95 (13) | C65—C66—H661 | 109.9 |
C62—N61—C66 | 111.96 (13) | N61—C66—H662 | 109.9 |
N61—C62—C63 | 110.83 (12) | C65—C66—H662 | 109.9 |
N61—C62—H621 | 109.5 | H661—C66—H662 | 108.3 |
C63—C62—H621 | 109.5 | O67—C67—N67 | 121.74 (14) |
N61—C62—H622 | 109.5 | O67—C67—C64 | 121.13 (14) |
C63—C62—H622 | 109.5 | N67—C67—C64 | 117.12 (14) |
H621—C62—H622 | 108.1 | C67—N67—H671 | 120.5 (12) |
C62—C63—C64 | 112.06 (13) | C67—N67—H672 | 117.7 (12) |
C62—C63—H631 | 109.2 | H671—N67—H672 | 121.6 (17) |
C6—N1—C2—N3 | 6.2 (2) | C5—C6—N61—C66 | −170.24 (14) |
C6—N1—C2—N21 | −176.29 (14) | C6—N61—C62—C63 | −103.75 (17) |
N1—C2—N3—C4 | −3.7 (2) | C66—N61—C62—C63 | 60.50 (18) |
N21—C2—N3—C4 | 178.74 (14) | N61—C62—C63—C64 | −52.92 (18) |
C2—N3—C4—C5 | −0.5 (2) | C62—C63—C64—C67 | 173.35 (13) |
C2—N3—C4—Cl4 | −179.95 (11) | C62—C63—C64—C65 | 49.05 (18) |
N3—C4—C5—C6 | 1.7 (2) | C67—C64—C65—C66 | −176.14 (13) |
Cl4—C4—C5—C6 | −178.88 (11) | C63—C64—C65—C66 | −51.73 (18) |
C2—N1—C6—N61 | 174.85 (14) | C6—N61—C66—C65 | 101.90 (17) |
C2—N1—C6—C5 | −4.5 (2) | C62—N61—C66—C65 | −62.74 (18) |
C4—C5—C6—N1 | 0.9 (2) | C64—C65—C66—N61 | 58.02 (18) |
C4—C5—C6—N61 | −178.32 (14) | C65—C64—C67—O67 | −9.6 (2) |
N1—C6—N61—C62 | 173.21 (13) | C63—C64—C67—O67 | −133.68 (15) |
C5—C6—N61—C62 | −7.5 (2) | C65—C64—C67—N67 | 169.11 (13) |
N1—C6—N61—C66 | 10.5 (2) | C63—C64—C67—N67 | 45.05 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21···O67i | 0.79 (2) | 2.35 (2) | 3.049 (2) | 148 (2) |
N21—H22···O67ii | 0.83 (2) | 2.25 (2) | 3.069 (2) | 170.6 (19) |
N67—H671···O1Wiii | 0.862 (18) | 2.481 (19) | 3.320 (2) | 164.6 (16) |
N67—H672···N3iv | 0.85 (2) | 2.15 (2) | 2.972 (2) | 163.7 (18) |
O1W—H1W···N1v | 0.82 (2) | 2.32 (2) | 3.1171 (19) | 164 (2) |
Symmetry codes: (i) −x, y, −z+3/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+1/2, −y+3/2, −z+1; (iv) x+1/2, −y+1/2, z+1/2; (v) −x, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C10H15ClN5O·0.5H2O |
Mr | 264.72 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 150 |
a, b, c (Å) | 15.559 (3), 9.3139 (19), 16.493 (3) |
β (°) | 102.08 (3) |
V (Å3) | 2337.2 (8) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.33 |
Crystal size (mm) | 0.26 × 0.14 × 0.14 |
Data collection | |
Diffractometer | Enraf Nonius KappaCCD area-detector diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1995) |
Tmin, Tmax | 0.920, 0.956 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10159, 2672, 2113 |
Rint | 0.047 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.116, 1.02 |
No. of reflections | 2672 |
No. of parameters | 183 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.24, −0.41 |
Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21···O67i | 0.79 (2) | 2.35 (2) | 3.049 (2) | 148 (2) |
N21—H22···O67ii | 0.83 (2) | 2.25 (2) | 3.069 (2) | 170.6 (19) |
N67—H671···O1Wiii | 0.862 (18) | 2.481 (19) | 3.320 (2) | 164.6 (16) |
N67—H672···N3iv | 0.85 (2) | 2.15 (2) | 2.972 (2) | 163.7 (18) |
O1W—H1W···N1v | 0.82 (2) | 2.32 (2) | 3.1171 (19) | 164 (2) |
Symmetry codes: (i) −x, y, −z+3/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+1/2, −y+3/2, −z+1; (iv) x+1/2, −y+1/2, z+1/2; (v) −x, −y+1, −z+1. |
NO COMMENT