In the title molecule, C
12H
12N
4O
4S, the dihedral angle between the thiazole and benzene rings is 40.3 (1)°. In the crystal structure, intermolecular N—H
N [H
N = 2.13 (2) Å] and N—H
O [H
O = 2.17 (2) Å] hydrogen bonds link molecules into a two-dimensional network perpendicular to the
a axis.
Supporting information
CCDC reference: 643076
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.003 Å
- R factor = 0.047
- wR factor = 0.131
- Data-to-parameter ratio = 15.2
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.740 0.974
Tmin(prime) and Tmax expected: 0.945 0.974
RR(prime) = 0.783
Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.78
PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ?
PLAT432_ALERT_2_C Short Inter X...Y Contact O3 .. C2 .. 2.97 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 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
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: COLLECT (Nonius, 2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL/PC (Sheldrick, 2001); molecular graphics: PLATON (Spek, 2003) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL/PC.
N-(4-Methoxybenzyl)-
N'-(5-nitro-1,3-thiazol-2-yl)urea
top
Crystal data top
C12H12N4O4S | F(000) = 640 |
Mr = 308.32 | Dx = 1.545 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9008 reflections |
a = 17.4348 (5) Å | θ = 2.6–27.5° |
b = 8.7877 (4) Å | µ = 0.27 mm−1 |
c = 8.6574 (10) Å | T = 150 K |
β = 92.308 (3)° | Needle, colourless |
V = 1325.34 (17) Å3 | 0.21 × 0.12 × 0.10 mm |
Z = 4 | |
Data collection top
Bruker–Nonius KappaCCD diffractometer | 3017 independent reflections |
Radiation source: fine-focus sealed tube | 2070 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.053 |
Detector resolution: 9 pixels mm-1 | θmax = 27.5°, θmin = 2.6° |
φ scans, and ω scans with κ offsets | h = −21→22 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −11→11 |
Tmin = 0.740, Tmax = 0.974 | l = −11→11 |
9008 measured reflections | |
Refinement top
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.131 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.071P)2 + 0.0564P] where P = (Fo2 + 2Fc2)/3 |
3017 reflections | (Δ/σ)max = 0.001 |
199 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.43 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.54329 (3) | 0.34180 (6) | 0.91166 (6) | 0.02588 (19) | |
O1 | 0.38472 (8) | 0.32768 (15) | 0.87749 (16) | 0.0246 (4) | |
O2 | 0.03054 (9) | 0.52916 (16) | 0.23599 (18) | 0.0329 (4) | |
O3 | 0.67899 (10) | 0.34036 (17) | 1.12152 (18) | 0.0379 (4) | |
O4 | 0.75905 (9) | 0.44473 (19) | 0.96587 (19) | 0.0390 (4) | |
N1 | 0.57442 (10) | 0.46805 (19) | 0.6484 (2) | 0.0248 (4) | |
N2 | 0.44733 (10) | 0.3881 (2) | 0.6587 (2) | 0.0240 (4) | |
N3 | 0.32051 (10) | 0.3274 (2) | 0.6414 (2) | 0.0246 (4) | |
N4 | 0.69477 (11) | 0.3954 (2) | 0.9956 (2) | 0.0290 (4) | |
C1 | 0.51876 (12) | 0.4048 (2) | 0.7270 (2) | 0.0216 (5) | |
C2 | 0.64062 (13) | 0.4669 (2) | 0.7374 (2) | 0.0253 (5) | |
H2A | 0.6874 | 0.5073 | 0.7022 | 0.030* | |
C3 | 0.63519 (12) | 0.4044 (2) | 0.8791 (2) | 0.0244 (5) | |
C4 | 0.38286 (12) | 0.3442 (2) | 0.7359 (2) | 0.0210 (5) | |
C5 | 0.24291 (12) | 0.3141 (2) | 0.6988 (2) | 0.0251 (5) | |
H5A | 0.2389 | 0.3746 | 0.7946 | 0.030* | |
H5B | 0.2320 | 0.2064 | 0.7235 | 0.030* | |
C6 | 0.18545 (12) | 0.3708 (2) | 0.5777 (2) | 0.0237 (5) | |
C7 | 0.19224 (12) | 0.5155 (2) | 0.5112 (3) | 0.0277 (5) | |
H7A | 0.2333 | 0.5802 | 0.5445 | 0.033* | |
C8 | 0.14023 (13) | 0.5651 (2) | 0.3983 (3) | 0.0303 (5) | |
H8A | 0.1463 | 0.6625 | 0.3527 | 0.036* | |
C9 | 0.07869 (12) | 0.4728 (2) | 0.3508 (2) | 0.0261 (5) | |
C10 | 0.07008 (13) | 0.3308 (2) | 0.4177 (2) | 0.0262 (5) | |
H10A | 0.0276 | 0.2681 | 0.3879 | 0.031* | |
C11 | 0.12411 (12) | 0.2813 (2) | 0.5285 (2) | 0.0252 (5) | |
H11A | 0.1187 | 0.1828 | 0.5719 | 0.030* | |
C12 | −0.03608 (13) | 0.4392 (3) | 0.1947 (3) | 0.0336 (6) | |
H12A | −0.0664 | 0.4906 | 0.1124 | 0.050* | |
H12B | −0.0674 | 0.4265 | 0.2853 | 0.050* | |
H12C | −0.0199 | 0.3391 | 0.1582 | 0.050* | |
H2N | 0.4412 (12) | 0.430 (2) | 0.574 (3) | 0.018 (6)* | |
H3N | 0.3279 (14) | 0.303 (2) | 0.551 (3) | 0.028 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0250 (3) | 0.0301 (3) | 0.0223 (3) | −0.0025 (2) | −0.0022 (2) | 0.0044 (2) |
O1 | 0.0248 (8) | 0.0308 (8) | 0.0183 (8) | −0.0011 (6) | 0.0003 (6) | 0.0014 (6) |
O2 | 0.0281 (9) | 0.0307 (8) | 0.0391 (10) | 0.0004 (7) | −0.0083 (7) | 0.0060 (7) |
O3 | 0.0440 (11) | 0.0374 (9) | 0.0314 (10) | −0.0076 (7) | −0.0104 (8) | 0.0115 (7) |
O4 | 0.0239 (9) | 0.0490 (10) | 0.0438 (11) | −0.0041 (8) | −0.0053 (8) | −0.0011 (8) |
N1 | 0.0229 (10) | 0.0274 (9) | 0.0241 (10) | −0.0030 (7) | 0.0003 (8) | 0.0006 (7) |
N2 | 0.0226 (10) | 0.0312 (10) | 0.0180 (10) | −0.0014 (8) | −0.0011 (8) | 0.0042 (8) |
N3 | 0.0218 (10) | 0.0342 (10) | 0.0178 (10) | −0.0008 (8) | 0.0022 (8) | −0.0019 (8) |
N4 | 0.0285 (11) | 0.0253 (10) | 0.0326 (11) | 0.0019 (8) | −0.0045 (8) | 0.0004 (8) |
C1 | 0.0244 (11) | 0.0192 (10) | 0.0212 (11) | 0.0001 (9) | 0.0013 (9) | −0.0018 (8) |
C2 | 0.0230 (12) | 0.0261 (11) | 0.0269 (12) | −0.0028 (9) | 0.0004 (9) | −0.0027 (9) |
C3 | 0.0242 (12) | 0.0220 (10) | 0.0267 (12) | −0.0005 (9) | −0.0015 (9) | −0.0025 (9) |
C4 | 0.0224 (11) | 0.0191 (10) | 0.0214 (11) | 0.0017 (8) | −0.0002 (9) | 0.0011 (8) |
C5 | 0.0181 (11) | 0.0311 (11) | 0.0263 (11) | −0.0004 (9) | 0.0033 (9) | 0.0007 (9) |
C6 | 0.0210 (11) | 0.0291 (11) | 0.0215 (11) | 0.0028 (9) | 0.0042 (9) | −0.0023 (9) |
C7 | 0.0218 (12) | 0.0269 (11) | 0.0342 (13) | −0.0016 (9) | 0.0009 (10) | −0.0047 (9) |
C8 | 0.0303 (13) | 0.0242 (11) | 0.0364 (13) | 0.0012 (10) | 0.0019 (10) | 0.0050 (9) |
C9 | 0.0216 (12) | 0.0295 (11) | 0.0272 (12) | 0.0054 (9) | 0.0008 (9) | −0.0002 (9) |
C10 | 0.0235 (11) | 0.0270 (11) | 0.0281 (12) | −0.0023 (9) | −0.0002 (9) | −0.0009 (9) |
C11 | 0.0259 (12) | 0.0247 (10) | 0.0250 (11) | −0.0006 (9) | 0.0019 (9) | 0.0019 (9) |
C12 | 0.0288 (13) | 0.0352 (13) | 0.0362 (14) | 0.0024 (10) | −0.0065 (10) | 0.0028 (10) |
Geometric parameters (Å, º) top
S1—C3 | 1.728 (2) | C2—H2A | 0.9500 |
S1—C1 | 1.729 (2) | C5—C6 | 1.506 (3) |
O1—C4 | 1.234 (2) | C5—H5A | 0.9900 |
O2—C9 | 1.368 (3) | C5—H5B | 0.9900 |
O2—C12 | 1.438 (3) | C6—C11 | 1.381 (3) |
O3—N4 | 1.234 (2) | C6—C7 | 1.403 (3) |
O4—N4 | 1.238 (2) | C7—C8 | 1.377 (3) |
N1—C1 | 1.329 (3) | C7—H7A | 0.9500 |
N1—C2 | 1.361 (3) | C8—C9 | 1.394 (3) |
N2—C1 | 1.365 (3) | C8—H8A | 0.9500 |
N2—C4 | 1.385 (3) | C9—C10 | 1.386 (3) |
N2—H2N | 0.82 (2) | C10—C11 | 1.387 (3) |
N3—C4 | 1.342 (3) | C10—H10A | 0.9500 |
N3—C5 | 1.465 (3) | C11—H11A | 0.9500 |
N3—H3N | 0.82 (2) | C12—H12A | 0.9800 |
N4—C3 | 1.420 (3) | C12—H12B | 0.9800 |
C2—C3 | 1.351 (3) | C12—H12C | 0.9800 |
| | | |
C3—S1—C1 | 86.77 (10) | N3—C5—H5B | 109.8 |
C9—O2—C12 | 116.58 (17) | C6—C5—H5B | 109.8 |
C1—N1—C2 | 109.12 (18) | H5A—C5—H5B | 108.2 |
C1—N2—C4 | 124.41 (19) | C11—C6—C7 | 117.8 (2) |
C1—N2—H2N | 115.0 (15) | C11—C6—C5 | 120.76 (19) |
C4—N2—H2N | 118.3 (15) | C7—C6—C5 | 121.42 (19) |
C4—N3—C5 | 122.59 (18) | C8—C7—C6 | 121.0 (2) |
C4—N3—H3N | 116.9 (17) | C8—C7—H7A | 119.5 |
C5—N3—H3N | 118.9 (17) | C6—C7—H7A | 119.5 |
O3—N4—O4 | 123.81 (19) | C7—C8—C9 | 120.1 (2) |
O3—N4—C3 | 117.80 (18) | C7—C8—H8A | 119.9 |
O4—N4—C3 | 118.38 (18) | C9—C8—H8A | 119.9 |
N1—C1—N2 | 119.72 (19) | O2—C9—C10 | 123.8 (2) |
N1—C1—S1 | 116.65 (16) | O2—C9—C8 | 116.51 (19) |
N2—C1—S1 | 123.59 (16) | C10—C9—C8 | 119.7 (2) |
C3—C2—N1 | 115.32 (19) | C9—C10—C11 | 119.3 (2) |
C3—C2—H2A | 122.3 | C9—C10—H10A | 120.4 |
N1—C2—H2A | 122.3 | C11—C10—H10A | 120.4 |
C2—C3—N4 | 126.25 (19) | C6—C11—C10 | 122.0 (2) |
C2—C3—S1 | 112.14 (17) | C6—C11—H11A | 119.0 |
N4—C3—S1 | 121.53 (15) | C10—C11—H11A | 119.0 |
O1—C4—N3 | 125.51 (19) | O2—C12—H12A | 109.5 |
O1—C4—N2 | 121.5 (2) | O2—C12—H12B | 109.5 |
N3—C4—N2 | 112.96 (18) | H12A—C12—H12B | 109.5 |
N3—C5—C6 | 109.58 (17) | O2—C12—H12C | 109.5 |
N3—C5—H5A | 109.8 | H12A—C12—H12C | 109.5 |
C6—C5—H5A | 109.8 | H12B—C12—H12C | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···N1i | 0.82 (2) | 2.13 (2) | 2.955 (3) | 179 (2) |
N3—H3N···O1ii | 0.82 (2) | 2.17 (2) | 2.922 (2) | 153 (2) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+1/2, z−1/2. |