Crystals of the title compound, C
11H
11N
3O
3S
2, were obtained from the sulfonylation reaction of 4-methylthiazole-5-carbohydrazide with benzenesulfonic chloride. The crystal packing is stabilized by intermolecular N—H
O and N—H
N hydrogen bonds.
Supporting information
CCDC reference: 248768
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.034
- wR factor = 0.094
- Data-to-parameter ratio = 12.6
checkCIF/PLATON results
No syntax errors found
Alert level B
ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
Tmin and Tmax reported: 0.430 0.850
Tmin' and Tmax expected: 0.823 0.850
RR' = 0.522
Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.52
PLAT482_ALERT_4_B Small D-H..A Angle Rep for C5 .. O1 .. 85.00 Deg.
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ?
PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ...... C5
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5C .. O1 .. 2.83 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7 .. O2 .. 2.61 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11 .. O3 .. 2.64 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10 .. O2 .. 2.86 Ang.
0 ALERT level A = In general: serious problem
3 ALERT level B = Potentially serious problem
7 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
1 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
7 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
N'-(Benzenesulfonyl)-4-methylthiazole-5-carbohydrazide
top
Crystal data top
C11H11N3O3S2 | F(000) = 616 |
Mr = 297.35 | Dx = 1.532 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.5593 (9) Å | Cell parameters from 3203 reflections |
b = 12.8979 (11) Å | θ = 5.2–56.0° |
c = 10.1875 (9) Å | µ = 0.42 mm−1 |
β = 111.703 (2)° | T = 293 K |
V = 1289.11 (19) Å3 | Prism, colorless |
Z = 4 | 0.45 × 0.42 × 0.39 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2275 independent reflections |
Radiation source: fine-focus sealed tube | 1995 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
φ and ω scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −12→12 |
Tmin = 0.430, Tmax = 0.850 | k = −15→15 |
6372 measured reflections | l = −10→12 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.094 | w = 1/[σ2(Fo2) + (0.0558P)2 + 0.1299P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
2275 reflections | Δρmax = 0.29 e Å−3 |
181 parameters | Δρmin = −0.28 e Å−3 |
2 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.018 (2) |
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 | |
H3 | 0.8162 (19) | 0.2150 (13) | 0.214 (2) | 0.044 (6)* | |
H2 | 0.711 (2) | 0.1542 (16) | −0.024 (2) | 0.053 (7)* | |
S1 | 0.98520 (6) | 0.01366 (4) | 0.31617 (5) | 0.0455 (2) | |
S2 | 0.63695 (5) | 0.14918 (3) | 0.22529 (5) | 0.02977 (18) | |
N1 | 1.06229 (17) | −0.16075 (12) | 0.25524 (18) | 0.0424 (4) | |
N2 | 0.75864 (16) | 0.11877 (12) | 0.05100 (16) | 0.0346 (4) | |
N3 | 0.77553 (16) | 0.15443 (11) | 0.18567 (16) | 0.0311 (4) | |
O1 | 0.78233 (15) | 0.00078 (11) | −0.09669 (15) | 0.0464 (4) | |
O2 | 0.59350 (14) | 0.04366 (10) | 0.21108 (15) | 0.0435 (4) | |
O3 | 0.67817 (15) | 0.19938 (11) | 0.36025 (13) | 0.0426 (4) | |
C1 | 1.0838 (2) | −0.09411 (17) | 0.3570 (2) | 0.0494 (6) | |
H1A | 1.1492 | −0.1050 | 0.4467 | 0.059* | |
C2 | 0.96289 (19) | −0.12569 (14) | 0.1331 (2) | 0.0333 (4) | |
C3 | 0.90819 (18) | −0.03133 (14) | 0.14550 (19) | 0.0294 (4) | |
C4 | 0.81143 (18) | 0.02815 (14) | 0.02579 (19) | 0.0303 (4) | |
C5 | 0.9265 (2) | −0.19291 (16) | 0.0052 (2) | 0.0493 (6) | |
H5A | 0.9816 | −0.2544 | 0.0278 | 0.074* | |
H5B | 0.9426 | −0.1558 | −0.0689 | 0.074* | |
H5C | 0.8320 | −0.2118 | −0.0257 | 0.074* | |
C6 | 0.51290 (17) | 0.22417 (14) | 0.09714 (19) | 0.0298 (4) | |
C7 | 0.43317 (19) | 0.17754 (16) | −0.0288 (2) | 0.0371 (5) | |
H7 | 0.4399 | 0.1067 | −0.0417 | 0.045* | |
C8 | 0.3436 (2) | 0.23751 (18) | −0.1349 (2) | 0.0474 (6) | |
H8 | 0.2909 | 0.2074 | −0.2206 | 0.057* | |
C9 | 0.3321 (2) | 0.34225 (19) | −0.1137 (2) | 0.0526 (6) | |
H9 | 0.2722 | 0.3826 | −0.1855 | 0.063* | |
C10 | 0.4091 (2) | 0.38700 (17) | 0.0134 (3) | 0.0526 (6) | |
H10 | 0.3984 | 0.4571 | 0.0279 | 0.063* | |
C11 | 0.5018 (2) | 0.32934 (15) | 0.1195 (2) | 0.0421 (5) | |
H11 | 0.5558 | 0.3602 | 0.2042 | 0.051* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0527 (4) | 0.0408 (3) | 0.0285 (3) | 0.0140 (2) | −0.0020 (2) | −0.0020 (2) |
S2 | 0.0349 (3) | 0.0258 (3) | 0.0243 (3) | 0.00087 (18) | 0.0059 (2) | 0.00007 (17) |
N1 | 0.0435 (10) | 0.0370 (9) | 0.0454 (11) | 0.0127 (8) | 0.0149 (9) | 0.0092 (8) |
N2 | 0.0396 (9) | 0.0351 (9) | 0.0261 (9) | 0.0099 (7) | 0.0086 (8) | 0.0064 (7) |
N3 | 0.0315 (8) | 0.0253 (8) | 0.0313 (9) | 0.0003 (6) | 0.0055 (7) | −0.0026 (6) |
O1 | 0.0541 (9) | 0.0523 (9) | 0.0265 (8) | 0.0089 (7) | 0.0076 (7) | −0.0036 (6) |
O2 | 0.0529 (9) | 0.0287 (7) | 0.0469 (9) | −0.0060 (6) | 0.0159 (7) | 0.0041 (6) |
O3 | 0.0506 (8) | 0.0439 (8) | 0.0258 (7) | 0.0083 (6) | 0.0054 (6) | −0.0049 (6) |
C1 | 0.0481 (13) | 0.0493 (13) | 0.0387 (12) | 0.0159 (10) | 0.0019 (10) | 0.0087 (10) |
C2 | 0.0329 (10) | 0.0305 (10) | 0.0383 (11) | 0.0011 (8) | 0.0152 (9) | 0.0028 (8) |
C3 | 0.0293 (9) | 0.0297 (10) | 0.0280 (10) | 0.0007 (7) | 0.0092 (8) | 0.0007 (7) |
C4 | 0.0276 (9) | 0.0338 (10) | 0.0285 (10) | −0.0015 (8) | 0.0093 (8) | 0.0015 (8) |
C5 | 0.0606 (14) | 0.0384 (12) | 0.0507 (13) | 0.0063 (10) | 0.0225 (12) | −0.0075 (10) |
C6 | 0.0275 (9) | 0.0330 (10) | 0.0273 (10) | 0.0023 (8) | 0.0084 (8) | 0.0020 (8) |
C7 | 0.0321 (10) | 0.0419 (11) | 0.0342 (11) | −0.0025 (8) | 0.0087 (9) | −0.0021 (9) |
C8 | 0.0332 (11) | 0.0686 (16) | 0.0322 (12) | −0.0008 (10) | 0.0027 (9) | 0.0022 (10) |
C9 | 0.0439 (12) | 0.0665 (16) | 0.0428 (13) | 0.0181 (11) | 0.0107 (11) | 0.0197 (11) |
C10 | 0.0607 (15) | 0.0418 (12) | 0.0550 (15) | 0.0181 (11) | 0.0214 (12) | 0.0119 (11) |
C11 | 0.0498 (13) | 0.0369 (11) | 0.0352 (11) | 0.0051 (9) | 0.0107 (10) | −0.0021 (9) |
Geometric parameters (Å, º) top
S1—C1 | 1.694 (2) | C3—C4 | 1.483 (2) |
S1—C3 | 1.7250 (18) | C5—H5A | 0.9600 |
S2—O2 | 1.4264 (14) | C5—H5B | 0.9600 |
S2—O3 | 1.4340 (13) | C5—H5C | 0.9600 |
S2—N3 | 1.6569 (17) | C6—C7 | 1.385 (3) |
S2—C6 | 1.7582 (18) | C6—C11 | 1.388 (3) |
N1—C1 | 1.301 (3) | C7—C8 | 1.380 (3) |
N1—C2 | 1.374 (2) | C7—H7 | 0.9300 |
N2—C4 | 1.360 (2) | C8—C9 | 1.380 (3) |
N2—N3 | 1.395 (2) | C8—H8 | 0.9300 |
N2—H2 | 0.875 (16) | C9—C10 | 1.375 (3) |
N3—H3 | 0.886 (15) | C9—H9 | 0.9300 |
O1—C4 | 1.222 (2) | C10—C11 | 1.377 (3) |
C1—H1A | 0.9300 | C10—H10 | 0.9300 |
C2—C3 | 1.373 (2) | C11—H11 | 0.9300 |
C2—C5 | 1.493 (3) | | |
| | | |
C1—S1—C3 | 89.40 (10) | N2—C4—C3 | 119.70 (16) |
O2—S2—O3 | 120.02 (9) | C2—C5—H5A | 109.5 |
O2—S2—N3 | 107.11 (8) | C2—C5—H5B | 109.5 |
O3—S2—N3 | 103.46 (8) | H5A—C5—H5B | 109.5 |
O2—S2—C6 | 109.04 (8) | C2—C5—H5C | 109.5 |
O3—S2—C6 | 110.01 (8) | H5A—C5—H5C | 109.5 |
N3—S2—C6 | 106.21 (8) | H5B—C5—H5C | 109.5 |
C1—N1—C2 | 110.73 (16) | C7—C6—C11 | 121.15 (18) |
C4—N2—N3 | 123.86 (15) | C7—C6—S2 | 118.67 (14) |
C4—N2—H2 | 115.0 (15) | C11—C6—S2 | 120.07 (15) |
N3—N2—H2 | 121.1 (15) | C8—C7—C6 | 119.19 (19) |
N2—N3—S2 | 115.03 (12) | C8—C7—H7 | 120.4 |
N2—N3—H3 | 118.4 (14) | C6—C7—H7 | 120.4 |
S2—N3—H3 | 109.0 (14) | C7—C8—C9 | 120.0 (2) |
N1—C1—S1 | 115.86 (16) | C7—C8—H8 | 120.0 |
N1—C1—H1A | 122.1 | C9—C8—H8 | 120.0 |
S1—C1—H1A | 122.1 | C10—C9—C8 | 120.2 (2) |
C3—C2—N1 | 114.53 (17) | C10—C9—H9 | 119.9 |
C3—C2—C5 | 127.88 (18) | C8—C9—H9 | 119.9 |
N1—C2—C5 | 117.59 (17) | C9—C10—C11 | 120.9 (2) |
C2—C3—C4 | 124.66 (17) | C9—C10—H10 | 119.6 |
C2—C3—S1 | 109.46 (13) | C11—C10—H10 | 119.6 |
C4—C3—S1 | 125.42 (14) | C10—C11—C6 | 118.5 (2) |
O1—C4—N2 | 118.39 (17) | C10—C11—H11 | 120.7 |
O1—C4—C3 | 121.81 (17) | C6—C11—H11 | 120.7 |
| | | |
C4—N2—N3—S2 | −108.26 (17) | S1—C3—C4—O1 | 164.72 (16) |
O2—S2—N3—N2 | 58.05 (14) | C2—C3—C4—N2 | 176.96 (17) |
O3—S2—N3—N2 | −174.22 (12) | S1—C3—C4—N2 | −11.6 (3) |
C6—S2—N3—N2 | −58.37 (14) | O2—S2—C6—C7 | −28.71 (17) |
C2—N1—C1—S1 | 1.3 (3) | O3—S2—C6—C7 | −162.25 (14) |
C3—S1—C1—N1 | −1.07 (19) | N3—S2—C6—C7 | 86.41 (16) |
C1—N1—C2—C3 | −0.9 (3) | O2—S2—C6—C11 | 155.18 (16) |
C1—N1—C2—C5 | 179.52 (19) | O3—S2—C6—C11 | 21.64 (19) |
N1—C2—C3—C4 | 172.68 (17) | N3—S2—C6—C11 | −89.70 (17) |
C5—C2—C3—C4 | −7.7 (3) | C11—C6—C7—C8 | 1.5 (3) |
N1—C2—C3—S1 | 0.1 (2) | S2—C6—C7—C8 | −174.53 (15) |
C5—C2—C3—S1 | 179.66 (17) | C6—C7—C8—C9 | −1.4 (3) |
C1—S1—C3—C2 | 0.51 (15) | C7—C8—C9—C10 | −0.5 (3) |
C1—S1—C3—C4 | −172.02 (17) | C8—C9—C10—C11 | 2.2 (4) |
N3—N2—C4—O1 | 174.87 (17) | C9—C10—C11—C6 | −2.0 (3) |
N3—N2—C4—C3 | −8.7 (3) | C7—C6—C11—C10 | 0.2 (3) |
C2—C3—C4—O1 | −6.7 (3) | S2—C6—C11—C10 | 176.16 (17) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5B···O1 | 0.96 | 2.58 | 2.910 (3) | 100 |
C5—H5C···O1 | 0.96 | 2.83 | 2.910 (3) | 85 |
C7—H7···O2 | 0.93 | 2.61 | 2.960 (2) | 103 |
C11—H11···O3 | 0.93 | 2.64 | 2.986 (2) | 103 |
N3—H3···N1i | 0.89 (2) | 2.00 (2) | 2.866 (2) | 164 (2) |
N2—H2···O3ii | 0.88 (2) | 2.18 (2) | 2.963 (2) | 148 (2) |
C1—H1A···O3iii | 0.93 | 2.45 | 3.332 (2) | 158 |
C7—H7···O2iv | 0.93 | 2.53 | 3.359 (2) | 148 |
C9—H9···O1v | 0.93 | 2.58 | 3.422 (3) | 152 |
C10—H10···O2vi | 0.93 | 2.86 | 3.467 (3) | 124 |
Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) x, −y+1/2, z−1/2; (iii) −x+2, −y, −z+1; (iv) −x+1, −y, −z; (v) −x+1, y+1/2, −z−1/2; (vi) −x+1, y+1/2, −z+1/2. |