Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802015878/ci6158sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802015878/ci6158Isup2.hkl |
CCDC reference: 198335
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.002 Å
- R factor = 0.038
- wR factor = 0.104
- Data-to-parameter ratio = 15.0
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
The title compound was obtained from Key Organics Ltd and crystals were grown from ethanol solution.
All aromatic H atoms were included in the refinement, at calculated positions, as riding models with C—H set to 0.95 Å. All H atoms involved in the hydrogen-bonding network were located on difference syntheses and both positional and thermal parameters 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. Molecular configuration and atom-numbering scheme for the title compound, showing 50% probability ellipsoids. |
C9H11N3·H2O·2Cl | Z = 2 |
Mr = 250.12 | F(000) = 260 |
Triclinic, P1 | Dx = 1.518 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.9716 (14) Å | Cell parameters from 3835 reflections |
b = 8.9866 (18) Å | θ = 2.9–27.5° |
c = 9.986 (2) Å | µ = 0.57 mm−1 |
α = 70.04 (3)° | T = 150 K |
β = 89.20 (3)° | Plate, colourless |
γ = 69.60 (3)° | 0.40 × 0.30 × 0.10 mm |
V = 547.2 (3) Å3 |
Bruker-Nonius KappaCCD area-detector diffractometer | 2465 independent reflections |
Radiation source: Bruker Nonius FR591 rotating-anode | 2168 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.075 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ϕ and ω scans | h = −9→9 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −11→11 |
Tmin = 0.804, Tmax = 0.945 | l = −12→12 |
7519 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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.104 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0551P)2 + 0.1837P] where P = (Fo2 + 2Fc2)/3 |
2465 reflections | (Δ/σ)max < 0.001 |
164 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.60 e Å−3 |
C9H11N3·H2O·2Cl | γ = 69.60 (3)° |
Mr = 250.12 | V = 547.2 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.9716 (14) Å | Mo Kα radiation |
b = 8.9866 (18) Å | µ = 0.57 mm−1 |
c = 9.986 (2) Å | T = 150 K |
α = 70.04 (3)° | 0.40 × 0.30 × 0.10 mm |
β = 89.20 (3)° |
Bruker-Nonius KappaCCD area-detector diffractometer | 2465 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | 2168 reflections with I > 2σ(I) |
Tmin = 0.804, Tmax = 0.945 | Rint = 0.075 |
7519 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.104 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.32 e Å−3 |
2465 reflections | Δρmin = −0.60 e Å−3 |
164 parameters |
x | y | z | Uiso*/Ueq | ||
N1 | 0.1739 (2) | 0.07021 (18) | 0.21676 (16) | 0.0155 (3) | |
H1 | 0.134 (3) | 0.116 (3) | 0.135 (3) | 0.030 (6)* | |
C2 | 0.3176 (3) | −0.0843 (2) | 0.25755 (19) | 0.0191 (4) | |
H2 | 0.3641 | −0.1364 | 0.1888 | 0.024* | |
C3 | 0.4012 (3) | −0.1711 (2) | 0.40145 (19) | 0.0211 (4) | |
H3 | 0.4996 | −0.2840 | 0.4318 | 0.026* | |
C4 | 0.3395 (3) | −0.0915 (2) | 0.49820 (18) | 0.0188 (4) | |
H4 | 0.3994 | −0.1481 | 0.5955 | 0.023* | |
C5 | 0.1176 (3) | 0.1629 (2) | 0.54967 (17) | 0.0185 (4) | |
H5 | 0.1748 | 0.1122 | 0.6476 | 0.023* | |
C6 | −0.0323 (3) | 0.3219 (2) | 0.50005 (18) | 0.0185 (4) | |
H6 | −0.0776 | 0.3813 | 0.5640 | 0.023* | |
C7 | −0.1209 (3) | 0.3991 (2) | 0.35551 (18) | 0.0170 (3) | |
H7 | −0.2248 | 0.5097 | 0.3237 | 0.021* | |
C8 | −0.0597 (2) | 0.31715 (19) | 0.26010 (16) | 0.0129 (3) | |
N81 | −0.1340 (2) | 0.38149 (17) | 0.11329 (14) | 0.0154 (3) | |
H81 | −0.188 (3) | 0.313 (3) | 0.091 (2) | 0.024 (5)* | |
N82 | −0.2880 (2) | 0.54946 (17) | 0.06257 (16) | 0.0153 (3) | |
H82 | −0.405 (4) | 0.551 (3) | 0.105 (2) | 0.026 (5)* | |
H83 | −0.233 (3) | 0.620 (3) | 0.070 (2) | 0.017 (5)* | |
H84 | −0.319 (4) | 0.578 (3) | −0.031 (3) | 0.034 (6)* | |
C9 | 0.1006 (2) | 0.15379 (19) | 0.30938 (16) | 0.0135 (3) | |
C10 | 0.1875 (2) | 0.0741 (2) | 0.45477 (17) | 0.0155 (3) | |
Cl1 | 0.65290 (6) | 0.12401 (5) | 0.09802 (4) | 0.01981 (15) | |
Cl2 | 0.33779 (6) | 0.50675 (5) | 0.23075 (4) | 0.01915 (14) | |
O1W | 0.1078 (2) | 0.22369 (16) | 0.91537 (13) | 0.0191 (3) | |
H1W | 0.159 (4) | 0.134 (4) | 0.896 (3) | 0.051 (8)* | |
H2W | 0.001 (4) | 0.266 (3) | 0.875 (3) | 0.033 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0183 (7) | 0.0164 (7) | 0.0118 (7) | −0.0062 (6) | −0.0005 (5) | −0.0049 (6) |
C2 | 0.0201 (9) | 0.0168 (8) | 0.0209 (9) | −0.0056 (7) | 0.0025 (7) | −0.0084 (7) |
C3 | 0.0182 (8) | 0.0153 (8) | 0.0237 (9) | −0.0037 (7) | −0.0016 (7) | −0.0022 (7) |
C4 | 0.0185 (8) | 0.0199 (8) | 0.0157 (8) | −0.0097 (7) | −0.0028 (6) | −0.0008 (7) |
C5 | 0.0234 (9) | 0.0257 (9) | 0.0102 (7) | −0.0143 (7) | −0.0004 (6) | −0.0055 (7) |
C6 | 0.0247 (9) | 0.0242 (9) | 0.0139 (8) | −0.0139 (7) | 0.0046 (6) | −0.0109 (7) |
C7 | 0.0193 (8) | 0.0168 (8) | 0.0169 (8) | −0.0070 (7) | 0.0013 (6) | −0.0081 (7) |
C8 | 0.0164 (8) | 0.0136 (7) | 0.0102 (7) | −0.0078 (6) | 0.0000 (6) | −0.0038 (6) |
N81 | 0.0203 (7) | 0.0120 (6) | 0.0112 (7) | −0.0016 (5) | −0.0034 (5) | −0.0053 (5) |
N82 | 0.0178 (8) | 0.0126 (7) | 0.0131 (7) | −0.0026 (6) | −0.0018 (6) | −0.0044 (6) |
C9 | 0.0160 (8) | 0.0151 (8) | 0.0116 (7) | −0.0080 (6) | 0.0011 (6) | −0.0052 (6) |
C10 | 0.0180 (8) | 0.0184 (8) | 0.0122 (7) | −0.0111 (6) | −0.0013 (6) | −0.0031 (6) |
Cl1 | 0.0258 (3) | 0.0132 (2) | 0.0176 (2) | −0.00356 (17) | −0.00399 (16) | −0.00546 (17) |
Cl2 | 0.0202 (2) | 0.0218 (2) | 0.0137 (2) | −0.00540 (17) | 0.00096 (16) | −0.00665 (17) |
O1W | 0.0211 (7) | 0.0165 (6) | 0.0183 (6) | −0.0021 (5) | −0.0021 (5) | −0.0091 (5) |
N1—C2 | 1.325 (2) | C6—H6 | 0.95 |
N1—C9 | 1.369 (2) | C7—C8 | 1.371 (2) |
N1—H1 | 0.78 (2) | C7—H7 | 0.95 |
C2—C3 | 1.398 (3) | C8—N81 | 1.409 (2) |
C2—H2 | 0.95 | C8—C9 | 1.423 (2) |
C3—C4 | 1.370 (3) | N81—N82 | 1.432 (2) |
C3—H3 | 0.95 | N81—H81 | 0.91 (2) |
C4—C10 | 1.414 (2) | N82—H82 | 0.91 (2) |
C4—H4 | 0.95 | N82—H83 | 0.87 (2) |
C5—C6 | 1.367 (3) | N82—H84 | 0.89 (3) |
C5—C10 | 1.416 (2) | C9—C10 | 1.414 (2) |
C5—H5 | 0.95 | O1W—H1W | 0.84 (3) |
C6—C7 | 1.410 (2) | O1W—H2W | 0.76 (3) |
C2—N1—C9 | 123.19 (15) | C6—C7—H7 | 119.4 |
C2—N1—H1 | 117.0 (16) | C7—C8—N81 | 126.43 (15) |
C9—N1—H1 | 119.7 (16) | C7—C8—C9 | 118.32 (14) |
N1—C2—C3 | 120.21 (16) | N81—C8—C9 | 115.20 (14) |
N1—C2—H2 | 119.9 | C8—N81—N82 | 115.00 (13) |
C3—C2—H2 | 119.9 | C8—N81—H81 | 111.7 (13) |
C4—C3—C2 | 119.24 (16) | N82—N81—H81 | 106.8 (13) |
C4—C3—H3 | 120.4 | N81—N82—H82 | 111.0 (13) |
C2—C3—H3 | 120.4 | N81—N82—H83 | 108.6 (13) |
C3—C4—C10 | 120.66 (15) | H82—N82—H83 | 116.2 (19) |
C3—C4—H4 | 119.7 | N81—N82—H84 | 107.1 (15) |
C10—C4—H4 | 119.7 | H82—N82—H84 | 108 (2) |
C6—C5—C10 | 119.82 (15) | H83—N82—H84 | 106 (2) |
C6—C5—H5 | 120.1 | N1—C9—C10 | 118.57 (15) |
C10—C5—H5 | 120.1 | N1—C9—C8 | 120.56 (14) |
C5—C6—C7 | 121.10 (15) | C10—C9—C8 | 120.87 (15) |
C5—C6—H6 | 119.4 | C4—C10—C9 | 118.04 (15) |
C7—C6—H6 | 119.4 | C4—C10—C5 | 123.25 (15) |
C8—C7—C6 | 121.11 (16) | C9—C10—C5 | 118.71 (15) |
C8—C7—H7 | 119.4 | H1W—O1W—H2W | 104 (2) |
C9—N1—C2—C3 | 0.6 (2) | N81—C8—C9—N1 | 0.5 (2) |
N1—C2—C3—C4 | −2.9 (3) | C7—C8—C9—C10 | 3.2 (2) |
C2—C3—C4—C10 | 2.3 (2) | N81—C8—C9—C10 | −179.41 (13) |
C10—C5—C6—C7 | 0.6 (2) | C3—C4—C10—C9 | 0.5 (2) |
C5—C6—C7—C8 | 0.1 (2) | C3—C4—C10—C5 | −179.92 (16) |
C6—C7—C8—N81 | −179.04 (15) | N1—C9—C10—C4 | −2.8 (2) |
C6—C7—C8—C9 | −1.9 (2) | C8—C9—C10—C4 | 177.10 (14) |
C7—C8—N81—N82 | 0.2 (2) | N1—C9—C10—C5 | 177.62 (14) |
C9—C8—N81—N82 | −177.01 (13) | C8—C9—C10—C5 | −2.5 (2) |
C2—N1—C9—C10 | 2.3 (2) | C6—C5—C10—C4 | −178.98 (15) |
C2—N1—C9—C8 | −177.57 (14) | C6—C5—C10—C9 | 0.6 (2) |
C7—C8—C9—N1 | −176.98 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1Wi | 0.78 (2) | 2.05 (2) | 2.817 (2) | 165 (2) |
N81—H81···Cl1ii | 0.91 (2) | 2.32 (2) | 3.1983 (16) | 164.5 (18) |
N82—H82···Cl2ii | 0.91 (2) | 2.25 (2) | 3.1476 (18) | 169.8 (18) |
N82—H83···O1Wiii | 0.87 (2) | 1.94 (2) | 2.808 (2) | 178.7 (19) |
N82—H84···Cl2iv | 0.89 (3) | 2.39 (3) | 3.1805 (17) | 149.1 (19) |
O1W—H1W···Cl1v | 0.84 (3) | 2.21 (3) | 3.0348 (17) | 164 (2) |
O1W—H2W···Cl2iii | 0.76 (3) | 2.47 (3) | 3.180 (2) | 158 (2) |
Symmetry codes: (i) x, y, z−1; (ii) x−1, y, z; (iii) −x, −y+1, −z+1; (iv) −x, −y+1, −z; (v) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C9H11N3·H2O·2Cl |
Mr | 250.12 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 150 |
a, b, c (Å) | 6.9716 (14), 8.9866 (18), 9.986 (2) |
α, β, γ (°) | 70.04 (3), 89.20 (3), 69.60 (3) |
V (Å3) | 547.2 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.57 |
Crystal size (mm) | 0.40 × 0.30 × 0.10 |
Data collection | |
Diffractometer | Bruker-Nonius KappaCCD area-detector diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1995) |
Tmin, Tmax | 0.804, 0.945 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7519, 2465, 2168 |
Rint | 0.075 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.104, 1.04 |
No. of reflections | 2465 |
No. of parameters | 164 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.32, −0.60 |
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 |
N1—H1···O1Wi | 0.78 (2) | 2.05 (2) | 2.817 (2) | 165 (2) |
N81—H81···Cl1ii | 0.91 (2) | 2.32 (2) | 3.1983 (16) | 164.5 (18) |
N82—H82···Cl2ii | 0.91 (2) | 2.25 (2) | 3.1476 (18) | 169.8 (18) |
N82—H83···O1Wiii | 0.87 (2) | 1.94 (2) | 2.808 (2) | 178.7 (19) |
N82—H84···Cl2iv | 0.89 (3) | 2.39 (3) | 3.1805 (17) | 149.1 (19) |
O1W—H1W···Cl1v | 0.84 (3) | 2.21 (3) | 3.0348 (17) | 164 (2) |
O1W—H2W···Cl2iii | 0.76 (3) | 2.47 (3) | 3.180 (2) | 158 (2) |
Symmetry codes: (i) x, y, z−1; (ii) x−1, y, z; (iii) −x, −y+1, −z+1; (iv) −x, −y+1, −z; (v) −x+1, −y, −z+1. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
no comment