Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680600239X/bt6804sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680600239X/bt6804Isup2.hkl |
CCDC reference: 298377
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.003 Å
- R factor = 0.046
- wR factor = 0.121
- Data-to-parameter ratio = 12.1
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT222_ALERT_3_A Large Non-Solvent H Ueq(max)/Ueq(min) ... 5.91 Ratio
Author Response: The hydrogens in the tail of molecule do not take part in hydrogen bonds and hence their mobility is higher. |
Alert level B PLAT063_ALERT_3_B Crystal Probably too Large for Beam Size ....... 1.00 mm PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.81 Ratio
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT141_ALERT_4_C su on a - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N9
1 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT and SADABS (Sheldrick, 2002); program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXTL.
C10H19N5O | F(000) = 488 |
Mr = 225.30 | Dx = 1.212 Mg m−3 Dm = 1.202 Mg m−3 Dm measured by flotation in what |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 8192 reflections |
a = 14.2768 (1) Å | θ = 2.8–25.0° |
b = 5.9066 (1) Å | µ = 0.08 mm−1 |
c = 14.6413 (2) Å | T = 173 K |
β = 90.778 (1)° | Plate, colourless |
V = 1234.55 (3) Å3 | 1.00 × 0.20 × 0.04 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 2161 independent reflections |
Radiation source: fine-focus sealed tube | 1866 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
ω scans | θmax = 25.0°, θmin = 2.8° |
Absorption correction: multi scan (SADABS; Sheldrick, 2002) | h = −16→16 |
Tmin = 0.921, Tmax = 0.997 | k = −7→7 |
11862 measured reflections | l = −17→17 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0608P)2 + 0.6313P] where P = (Fo2 + 2Fc2)/3 |
2161 reflections | (Δ/σ)max < 0.001 |
178 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.58092 (9) | 0.0292 (2) | 0.19368 (8) | 0.0294 (3) | |
N1 | 0.65589 (10) | −0.0247 (2) | −0.08315 (9) | 0.0239 (3) | |
C2 | 0.62471 (12) | 0.1887 (3) | −0.10284 (11) | 0.0253 (4) | |
H2 | 0.6272 | 0.2548 | −0.1619 | 0.022 (4)* | |
N3 | 0.59109 (10) | 0.2920 (2) | −0.03133 (9) | 0.0247 (3) | |
C4 | 0.60062 (11) | 0.1367 (3) | 0.04006 (11) | 0.0215 (4) | |
C5 | 0.64087 (11) | −0.0592 (3) | 0.00829 (11) | 0.0225 (4) | |
N4 | 0.66756 (12) | −0.2548 (3) | 0.05283 (12) | 0.0320 (4) | |
H41 | 0.6453 (16) | −0.253 (4) | 0.1090 (16) | 0.043 (6)* | |
H42 | 0.6517 (15) | −0.382 (4) | 0.0221 (15) | 0.040 (6)* | |
C6 | 0.56757 (11) | 0.1742 (3) | 0.13270 (11) | 0.0229 (4) | |
N5 | 0.52470 (11) | 0.3725 (3) | 0.14865 (11) | 0.0285 (4) | |
H51 | 0.4982 (14) | 0.399 (3) | 0.2016 (14) | 0.028 (5)* | |
H52 | 0.5080 (15) | 0.459 (4) | 0.0996 (16) | 0.043 (6)* | |
C7 | 0.70255 (14) | −0.1794 (3) | −0.14585 (13) | 0.0339 (5) | |
H7A | 0.6757 | −0.1597 | −0.2080 | 0.041 (6)* | |
H7B | 0.6909 | −0.3374 | −0.1266 | 0.047 (6)* | |
C8 | 0.80774 (15) | −0.1375 (4) | −0.14820 (15) | 0.0423 (5) | |
H8A | 0.8338 | −0.1480 | −0.0854 | 0.056 (7)* | |
H8B | 0.8375 | −0.2569 | −0.1853 | 0.057 (7)* | |
N9 | 0.83077 (11) | 0.0840 (3) | −0.18629 (11) | 0.0386 (4) | |
C10 | 0.92446 (17) | 0.1584 (5) | −0.15690 (17) | 0.0620 (7) | |
H10A | 0.9458 | 0.2798 | −0.1984 | 0.084 (9)* | |
H10B | 0.9685 | 0.0298 | −0.1624 | 0.091 (10)* | |
C11 | 0.9280 (2) | 0.2443 (6) | −0.0610 (2) | 0.0818 (10) | |
H11A | 0.8836 | 0.3697 | −0.0546 | 0.104 (13)* | |
H11B | 0.9914 | 0.2975 | −0.0464 | 0.124 (13)* | |
H11C | 0.9112 | 0.1219 | −0.0190 | 0.093 (11)* | |
C12 | 0.82316 (18) | 0.0835 (5) | −0.28663 (15) | 0.0588 (7) | |
H12A | 0.8790 | 0.0080 | −0.3119 | 0.058 (7)* | |
H12B | 0.7674 | −0.0058 | −0.3053 | 0.087 (10)* | |
C13 | 0.8152 (2) | 0.3170 (6) | −0.3266 (2) | 0.0737 (9) | |
H13A | 0.7629 | 0.3971 | −0.2984 | 0.130 (15)* | |
H13B | 0.8041 | 0.3060 | −0.3926 | 0.124 (13)* | |
H13C | 0.8735 | 0.4004 | −0.3148 | 0.104 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0375 (7) | 0.0272 (7) | 0.0236 (6) | −0.0007 (5) | 0.0024 (5) | 0.0056 (5) |
N1 | 0.0266 (8) | 0.0208 (8) | 0.0243 (7) | −0.0011 (6) | 0.0026 (6) | −0.0039 (6) |
C2 | 0.0317 (10) | 0.0235 (9) | 0.0207 (8) | −0.0014 (7) | 0.0017 (7) | 0.0024 (7) |
N3 | 0.0311 (8) | 0.0205 (7) | 0.0224 (7) | 0.0009 (6) | 0.0023 (6) | 0.0013 (6) |
C4 | 0.0226 (9) | 0.0199 (8) | 0.0220 (8) | −0.0031 (7) | −0.0004 (7) | 0.0000 (7) |
C5 | 0.0221 (8) | 0.0210 (9) | 0.0244 (8) | −0.0048 (7) | −0.0003 (6) | 0.0005 (7) |
N4 | 0.0423 (10) | 0.0204 (9) | 0.0332 (9) | 0.0026 (7) | 0.0008 (7) | 0.0025 (7) |
C6 | 0.0232 (9) | 0.0234 (9) | 0.0222 (8) | −0.0049 (7) | −0.0007 (7) | 0.0008 (7) |
N5 | 0.0347 (9) | 0.0300 (9) | 0.0210 (8) | 0.0044 (7) | 0.0061 (7) | −0.0008 (7) |
C7 | 0.0418 (11) | 0.0254 (10) | 0.0347 (10) | −0.0015 (8) | 0.0111 (8) | −0.0094 (8) |
C8 | 0.0380 (12) | 0.0414 (12) | 0.0477 (12) | 0.0088 (9) | 0.0093 (9) | −0.0061 (10) |
N9 | 0.0291 (9) | 0.0496 (11) | 0.0373 (9) | −0.0068 (8) | 0.0043 (7) | −0.0019 (8) |
C10 | 0.0387 (13) | 0.091 (2) | 0.0562 (15) | −0.0169 (14) | −0.0021 (11) | 0.0022 (14) |
C11 | 0.089 (2) | 0.091 (2) | 0.0646 (18) | −0.027 (2) | −0.0238 (16) | −0.0043 (17) |
C12 | 0.0509 (15) | 0.086 (2) | 0.0396 (12) | −0.0157 (14) | 0.0065 (10) | −0.0024 (13) |
C13 | 0.0478 (15) | 0.109 (3) | 0.0644 (18) | −0.0125 (16) | −0.0032 (13) | 0.0315 (17) |
O1—C6 | 1.250 (2) | C8—N9 | 1.461 (3) |
N1—C2 | 1.366 (2) | C8—H8A | 0.9900 |
N1—C5 | 1.374 (2) | C8—H8B | 0.9900 |
N1—C7 | 1.462 (2) | N9—C10 | 1.467 (3) |
C2—N3 | 1.309 (2) | N9—C12 | 1.472 (3) |
C2—H2 | 0.9500 | C10—C11 | 1.494 (4) |
N3—C4 | 1.396 (2) | C10—H10A | 0.9900 |
C4—C5 | 1.376 (2) | C10—H10B | 0.9900 |
C4—C6 | 1.459 (2) | C11—H11A | 0.9800 |
C5—N4 | 1.378 (2) | C11—H11B | 0.9800 |
N4—H41 | 0.89 (2) | C11—H11C | 0.9800 |
N4—H42 | 0.90 (2) | C12—C13 | 1.502 (4) |
C6—N5 | 1.343 (2) | C12—H12A | 0.9900 |
N5—H51 | 0.88 (2) | C12—H12B | 0.9900 |
N5—H52 | 0.91 (2) | C13—H13A | 0.9800 |
C7—C8 | 1.523 (3) | C13—H13B | 0.9800 |
C7—H7A | 0.9900 | C13—H13C | 0.9800 |
C7—H7B | 0.9900 | ||
C2—N1—C5 | 106.74 (13) | N9—C8—H8B | 109.1 |
C2—N1—C7 | 126.44 (15) | C7—C8—H8B | 109.1 |
C5—N1—C7 | 126.68 (15) | H8A—C8—H8B | 107.9 |
N3—C2—N1 | 112.53 (15) | C10—N9—C8 | 111.42 (19) |
N3—C2—H2 | 123.7 | C10—N9—C12 | 110.37 (17) |
N1—C2—H2 | 123.7 | C8—N9—C12 | 111.42 (18) |
C2—N3—C4 | 105.07 (14) | N9—C10—C11 | 113.4 (2) |
C5—C4—N3 | 109.66 (14) | N9—C10—H10A | 108.9 |
C5—C4—C6 | 125.69 (15) | C11—C10—H10A | 108.9 |
N3—C4—C6 | 124.56 (15) | N9—C10—H10B | 108.9 |
N1—C5—N4 | 122.67 (16) | C11—C10—H10B | 108.9 |
N1—C5—C4 | 106.01 (14) | H10A—C10—H10B | 107.7 |
N4—C5—C4 | 131.26 (16) | C10—C11—H11A | 109.5 |
C5—N4—H41 | 109.2 (15) | C10—C11—H11B | 109.5 |
C5—N4—H42 | 113.3 (13) | H11A—C11—H11B | 109.5 |
H41—N4—H42 | 112 (2) | C10—C11—H11C | 109.5 |
O1—C6—N5 | 122.58 (16) | H11A—C11—H11C | 109.5 |
O1—C6—C4 | 120.82 (15) | H11B—C11—H11C | 109.5 |
N5—C6—C4 | 116.58 (15) | C13—C12—N9 | 113.0 (2) |
C6—N5—H51 | 120.7 (13) | C13—C12—H12A | 109.0 |
C6—N5—H52 | 118.0 (14) | N9—C12—H12A | 109.0 |
H51—N5—H52 | 118.8 (19) | C13—C12—H12B | 109.0 |
N1—C7—C8 | 111.74 (15) | N9—C12—H12B | 109.0 |
N1—C7—H7A | 109.3 | H12A—C12—H12B | 107.8 |
C8—C7—H7A | 109.3 | C12—C13—H13A | 109.5 |
N1—C7—H7B | 109.3 | C12—C13—H13B | 109.5 |
C8—C7—H7B | 109.3 | H13A—C13—H13B | 109.5 |
H7A—C7—H7B | 107.9 | C12—C13—H13C | 109.5 |
N9—C8—C7 | 112.41 (17) | H13A—C13—H13C | 109.5 |
N9—C8—H8A | 109.1 | H13B—C13—H13C | 109.5 |
C7—C8—H8A | 109.1 | ||
C5—N1—C2—N3 | −0.06 (19) | C5—C4—C6—O1 | 5.7 (3) |
C7—N1—C2—N3 | −175.93 (16) | N3—C4—C6—O1 | −178.09 (15) |
N1—C2—N3—C4 | −0.06 (19) | C5—C4—C6—N5 | −175.77 (16) |
C2—N3—C4—C5 | 0.15 (18) | N3—C4—C6—N5 | 0.4 (2) |
C2—N3—C4—C6 | −176.56 (15) | C2—N1—C7—C8 | 85.7 (2) |
C2—N1—C5—N4 | −177.36 (16) | C5—N1—C7—C8 | −89.4 (2) |
C7—N1—C5—N4 | −1.5 (3) | N1—C7—C8—N9 | −65.6 (2) |
C2—N1—C5—C4 | 0.15 (17) | C7—C8—N9—C10 | 158.08 (18) |
C7—N1—C5—C4 | 176.01 (16) | C7—C8—N9—C12 | −78.2 (2) |
N3—C4—C5—N1 | −0.19 (18) | C8—N9—C10—C11 | −76.8 (3) |
C6—C4—C5—N1 | 176.48 (15) | C12—N9—C10—C11 | 158.8 (3) |
N3—C4—C5—N4 | 177.03 (17) | C10—N9—C12—C13 | −74.3 (3) |
C6—C4—C5—N4 | −6.3 (3) | C8—N9—C12—C13 | 161.33 (19) |
Label | D—H···A | D—H | H···A | D···A | D—H···A |
a | N4—H41···O1 | 0.89 (2) | 2.28 (2) | 2.944 (2) | 132 (2) |
b | N4—H42 N3i | 0.90 (2) | 2.25 (2) | 3.137 (2) | 168 (2) |
c | N5—H51···O1ii | 0.88 (2) | 2.06 (2) | 2.9248 (19) | 165 (2) |
d | N5—H52···N3 | 0.91 (2) | 2.47 (2) | 2.852 (2) | 105 (2) |
e | N5—H52···N3iii | 0.91 (2) | 2.26 (2) | 3.088 (2) | 150 (2) |
f | C2—H2···O1iv | 0.95 | 2.55 | 3.463 (2) | 162 |
Symmetry codes: (i) x, y-1, z; (ii) 1-x, 1/2+y, 1/2-z; (iii) 1-x, 1-y, -z; (iv) x, 1/2-y, z-1/2. |
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