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In the title compound, C
18H
13N
5O
3S, both the five- and six-membered rings are planar. The phenyl ring attached to the sydnone ring is nearly perpendicular to both the sydnone ring [78.2 (1)°] and the thiazole ring [80.1 (1)°]. The dihedral angle between the sydnone and thiazole rings is 20.5 (1)°. The molecular packing in the crystal is stabilized by intermolecular N—H
O hydrogen bonds and C—H
O interactions.
Supporting information
CCDC reference: 189913
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.043
- wR factor = 0.129
- Data-to-parameter ratio = 12.7
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
REFLT_03
From the CIF: _diffrn_reflns_theta_max 69.92
From the CIF: _reflns_number_total 3105
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 3310
Completeness (_total/calc) 93.81%
Alert C: < 95% complete
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: SDP (Frenz, 1978); data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: PARST97 (Nardelli, 1995).
4–2(2'-Benzoylhydrazino-4'-thiazolyl)-3-phenylsydnone
top
Crystal data top
C18H13N5O3S | Z = 2 |
Mr = 379.39 | F(000) = 392 |
Triclinic, P1 | Dx = 1.441 Mg m−3 |
a = 8.290 (2) Å | Cu Kα radiation, λ = 1.5418 Å |
b = 9.646 (3) Å | Cell parameters from 25 reflections |
c = 11.715 (3) Å | θ = 14–30° |
α = 81.54 (2)° | µ = 1.92 mm−1 |
β = 81.74 (2)° | T = 293 K |
γ = 71.59 (2)° | Needle, yellow |
V = 874.4 (4) Å3 | 0.3 × 0.3 × 0.2 mm |
Data collection top
Enraf-Nonius CAD-4 diffractometer | 2709 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.012 |
Graphite monochromator | θmax = 69.9°, θmin = 3.8° |
ω–2θ scans | h = −9→10 |
Absorption correction: ψ scan (North et al., 1968) | k = −3→11 |
Tmin = 0.637, Tmax = 0.682 | l = −14→14 |
3306 measured reflections | 3 standard reflections every 120min min |
3105 independent reflections | intensity decay: <1% |
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)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.129 | w = 1/[σ2(Fo2) + (0.0778P)2 + 0.1813P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
3105 reflections | Δρmax = 0.22 e Å−3 |
245 parameters | Δρmin = −0.34 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0056 (9) |
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' | 0.77553 (6) | 0.40163 (6) | 0.25273 (5) | 0.0627 (2) | |
C2' | 0.5537 (2) | 0.4777 (2) | 0.26516 (18) | 0.0506 (4) | |
N3' | 0.49125 (19) | 0.56841 (19) | 0.17799 (15) | 0.0528 (4) | |
C4' | 0.6231 (2) | 0.5833 (2) | 0.09467 (18) | 0.0529 (5) | |
C5' | 0.7828 (3) | 0.5035 (3) | 0.1203 (2) | 0.0630 (6) | |
H5' | 0.8826 | 0.5040 | 0.0727 | 0.076* | |
O1 | 0.5838 (2) | 0.7779 (2) | −0.19526 (14) | 0.0747 (5) | |
N2 | 0.4277 (3) | 0.8478 (2) | −0.13855 (16) | 0.0722 (5) | |
N3 | 0.4372 (2) | 0.7827 (2) | −0.03141 (15) | 0.0572 (4) | |
C4 | 0.5842 (3) | 0.6765 (2) | −0.01223 (18) | 0.0558 (5) | |
C5 | 0.6856 (3) | 0.6701 (3) | −0.1213 (2) | 0.0642 (6) | |
O5 | 0.8269 (2) | 0.5972 (2) | −0.15687 (16) | 0.0799 (5) | |
N6 | 0.4578 (2) | 0.4348 (2) | 0.36025 (16) | 0.0603 (5) | |
H6 | 0.5035 | 0.3653 | 0.4115 | 0.072* | |
N7 | 0.2838 (2) | 0.5076 (2) | 0.37084 (15) | 0.0566 (4) | |
H7 | 0.2153 | 0.4734 | 0.3431 | 0.068* | |
C8 | 0.2208 (2) | 0.6310 (2) | 0.42400 (16) | 0.0518 (4) | |
O8 | 0.3130 (2) | 0.68021 (19) | 0.46809 (15) | 0.0731 (5) | |
C9 | 0.0320 (2) | 0.7012 (2) | 0.42925 (17) | 0.0528 (5) | |
C10 | −0.0378 (3) | 0.8164 (3) | 0.4954 (3) | 0.0889 (9) | |
H10 | 0.0317 | 0.8467 | 0.5357 | 0.107* | |
C11 | −0.2118 (4) | 0.8871 (4) | 0.5020 (3) | 0.1177 (14) | |
H11 | −0.2589 | 0.9634 | 0.5484 | 0.141* | |
C12 | −0.3153 (3) | 0.8463 (4) | 0.4413 (3) | 0.0946 (9) | |
H12 | −0.4318 | 0.8957 | 0.4454 | 0.114* | |
C13 | −0.2470 (3) | 0.7328 (3) | 0.3748 (3) | 0.0772 (7) | |
H13 | −0.3164 | 0.7050 | 0.3327 | 0.093* | |
C14 | −0.0735 (3) | 0.6592 (3) | 0.3702 (2) | 0.0640 (6) | |
H14 | −0.0277 | 0.5801 | 0.3264 | 0.077* | |
C15 | 0.2898 (3) | 0.8422 (2) | 0.05030 (18) | 0.0576 (5) | |
C16 | 0.3010 (4) | 0.9384 (3) | 0.1211 (2) | 0.0812 (7) | |
H16 | 0.4020 | 0.9613 | 0.1205 | 0.097* | |
C17 | 0.1566 (4) | 1.0009 (3) | 0.1939 (3) | 0.0927 (9) | |
H17 | 0.1605 | 1.0665 | 0.2435 | 0.111* | |
C18 | 0.0090 (3) | 0.9668 (3) | 0.1934 (2) | 0.0794 (8) | |
H18 | −0.0877 | 1.0107 | 0.2415 | 0.095* | |
C19 | 0.0029 (3) | 0.8693 (3) | 0.1232 (2) | 0.0775 (7) | |
H19 | −0.0976 | 0.8452 | 0.1247 | 0.093* | |
C20 | 0.1438 (3) | 0.8053 (3) | 0.0494 (2) | 0.0679 (6) | |
H20 | 0.1396 | 0.7391 | 0.0005 | 0.082* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1' | 0.0363 (3) | 0.0725 (4) | 0.0713 (4) | −0.0018 (2) | −0.0026 (2) | −0.0183 (3) |
C2' | 0.0370 (9) | 0.0571 (11) | 0.0573 (11) | −0.0085 (8) | −0.0032 (8) | −0.0193 (9) |
N3' | 0.0359 (7) | 0.0644 (10) | 0.0556 (9) | −0.0107 (7) | 0.0010 (7) | −0.0144 (8) |
C4' | 0.0414 (9) | 0.0612 (11) | 0.0568 (11) | −0.0139 (8) | 0.0043 (8) | −0.0208 (9) |
C5' | 0.0392 (10) | 0.0761 (14) | 0.0702 (14) | −0.0119 (9) | 0.0080 (9) | −0.0220 (11) |
O1 | 0.0670 (10) | 0.1021 (13) | 0.0544 (9) | −0.0268 (9) | 0.0088 (7) | −0.0180 (8) |
N2 | 0.0642 (11) | 0.0935 (14) | 0.0528 (10) | −0.0181 (10) | 0.0014 (8) | −0.0090 (10) |
N3 | 0.0509 (9) | 0.0692 (11) | 0.0506 (9) | −0.0164 (8) | 0.0013 (7) | −0.0134 (8) |
C4 | 0.0468 (10) | 0.0642 (12) | 0.0585 (12) | −0.0182 (9) | 0.0052 (8) | −0.0202 (9) |
C5 | 0.0539 (12) | 0.0820 (15) | 0.0613 (13) | −0.0261 (11) | 0.0087 (10) | −0.0238 (11) |
O5 | 0.0568 (9) | 0.1063 (13) | 0.0751 (11) | −0.0240 (9) | 0.0192 (8) | −0.0315 (10) |
N6 | 0.0390 (8) | 0.0742 (11) | 0.0576 (10) | −0.0054 (8) | −0.0017 (7) | −0.0043 (8) |
N7 | 0.0363 (8) | 0.0709 (11) | 0.0599 (10) | −0.0112 (7) | 0.0002 (7) | −0.0152 (8) |
C8 | 0.0470 (10) | 0.0623 (11) | 0.0423 (9) | −0.0135 (9) | −0.0044 (8) | −0.0013 (8) |
O8 | 0.0591 (9) | 0.0845 (11) | 0.0788 (11) | −0.0152 (8) | −0.0218 (8) | −0.0188 (9) |
C9 | 0.0465 (10) | 0.0598 (11) | 0.0446 (10) | −0.0083 (8) | 0.0003 (8) | −0.0041 (8) |
C10 | 0.0654 (15) | 0.109 (2) | 0.0853 (18) | 0.0053 (14) | −0.0182 (13) | −0.0501 (16) |
C11 | 0.0710 (18) | 0.145 (3) | 0.121 (3) | 0.0252 (18) | −0.0170 (17) | −0.084 (2) |
C12 | 0.0480 (13) | 0.110 (2) | 0.109 (2) | 0.0087 (13) | −0.0027 (13) | −0.0384 (18) |
C13 | 0.0467 (12) | 0.0781 (16) | 0.106 (2) | −0.0118 (11) | −0.0083 (12) | −0.0218 (14) |
C14 | 0.0438 (10) | 0.0636 (12) | 0.0825 (15) | −0.0102 (9) | −0.0030 (10) | −0.0179 (11) |
C15 | 0.0505 (11) | 0.0617 (12) | 0.0525 (11) | −0.0082 (9) | 0.0018 (8) | −0.0070 (9) |
C16 | 0.0699 (15) | 0.0990 (19) | 0.0783 (17) | −0.0272 (14) | 0.0099 (12) | −0.0343 (14) |
C17 | 0.098 (2) | 0.098 (2) | 0.0741 (17) | −0.0163 (17) | 0.0130 (15) | −0.0350 (16) |
C18 | 0.0654 (15) | 0.0834 (17) | 0.0643 (14) | 0.0005 (12) | 0.0123 (11) | 0.0015 (13) |
C19 | 0.0540 (13) | 0.0892 (18) | 0.0765 (16) | −0.0138 (12) | 0.0036 (11) | 0.0042 (14) |
C20 | 0.0590 (12) | 0.0720 (14) | 0.0681 (14) | −0.0162 (11) | −0.0003 (10) | −0.0069 (11) |
Geometric parameters (Å, º) top
S1'—C5' | 1.714 (3) | C9—C14 | 1.375 (3) |
S1'—C2' | 1.7446 (19) | C10—C11 | 1.383 (4) |
C2'—N3' | 1.296 (3) | C10—H10 | 0.93 |
C2'—N6 | 1.365 (3) | C11—C12 | 1.367 (4) |
N3'—C4' | 1.385 (2) | C11—H11 | 0.93 |
C4'—C5' | 1.356 (3) | C12—C13 | 1.364 (4) |
C4'—C4 | 1.443 (3) | C12—H12 | 0.93 |
C5'—H5' | 0.93 | C13—C14 | 1.385 (3) |
O1—N2 | 1.380 (2) | C13—H13 | 0.93 |
O1—C5 | 1.391 (3) | C14—H14 | 0.93 |
N2—N3 | 1.319 (3) | C15—C16 | 1.363 (3) |
N3—C4 | 1.344 (3) | C15—C20 | 1.367 (3) |
N3—C15 | 1.457 (3) | C16—C17 | 1.388 (4) |
C4—C5 | 1.423 (3) | C16—H16 | 0.93 |
C5—O5 | 1.210 (3) | C17—C18 | 1.365 (4) |
N6—N7 | 1.387 (2) | C17—H17 | 0.93 |
N6—H6 | 0.86 | C18—C19 | 1.354 (4) |
N7—C8 | 1.345 (3) | C18—H18 | 0.93 |
N7—H7 | 0.86 | C19—C20 | 1.380 (3) |
C8—O8 | 1.221 (2) | C19—H19 | 0.93 |
C8—C9 | 1.492 (3) | C20—H20 | 0.93 |
C9—C10 | 1.374 (3) | | |
| | | |
C5'—S1'—C2' | 88.23 (10) | C9—C10—C11 | 119.8 (3) |
N3'—C2'—N6 | 124.48 (17) | C9—C10—H10 | 120.1 |
N3'—C2'—S1' | 115.83 (15) | C11—C10—H10 | 120.1 |
N6—C2'—S1' | 119.61 (16) | C12—C11—C10 | 120.9 (3) |
C2'—N3'—C4' | 109.53 (16) | C12—C11—H11 | 119.6 |
C5'—C4'—N3' | 115.7 (2) | C10—C11—H11 | 119.6 |
C5'—C4'—C4 | 124.61 (19) | C13—C12—C11 | 119.7 (2) |
N3'—C4'—C4 | 119.62 (18) | C13—C12—H12 | 120.2 |
C4'—C5'—S1' | 110.64 (16) | C11—C12—H12 | 120.2 |
C4'—C5'—H5' | 124.7 | C12—C13—C14 | 119.7 (2) |
S1'—C5'—H5' | 124.7 | C12—C13—H13 | 120.2 |
N2—O1—C5 | 111.69 (16) | C14—C13—H13 | 120.2 |
N3—N2—O1 | 103.30 (17) | C9—C14—C13 | 121.0 (2) |
N2—N3—C4 | 115.62 (17) | C9—C14—H14 | 119.5 |
N2—N3—C15 | 114.90 (17) | C13—C14—H14 | 119.5 |
C4—N3—C15 | 129.40 (18) | C16—C15—C20 | 122.7 (2) |
N3—C4—C5 | 105.1 (2) | C16—C15—N3 | 118.2 (2) |
N3—C4—C4' | 126.59 (18) | C20—C15—N3 | 119.1 (2) |
C5—C4—C4' | 128.2 (2) | C15—C16—C17 | 117.7 (3) |
O5—C5—O1 | 120.5 (2) | C15—C16—H16 | 121.1 |
O5—C5—C4 | 135.2 (2) | C17—C16—H16 | 121.1 |
O1—C5—C4 | 104.28 (19) | C18—C17—C16 | 120.5 (3) |
C2'—N6—N7 | 117.30 (17) | C18—C17—H17 | 119.7 |
C2'—N6—H6 | 121.3 | C16—C17—H17 | 119.7 |
N7—N6—H6 | 121.3 | C19—C18—C17 | 120.2 (2) |
C8—N7—N6 | 120.84 (17) | C19—C18—H18 | 119.9 |
C8—N7—H7 | 119.6 | C17—C18—H18 | 119.9 |
N6—N7—H7 | 119.6 | C18—C19—C20 | 120.8 (3) |
O8—C8—N7 | 121.57 (19) | C18—C19—H19 | 119.6 |
O8—C8—C9 | 122.09 (19) | C20—C19—H19 | 119.6 |
N7—C8—C9 | 116.31 (18) | C15—C20—C19 | 118.0 (2) |
C10—C9—C14 | 118.9 (2) | C15—C20—H20 | 121.0 |
C10—C9—C8 | 117.3 (2) | C19—C20—H20 | 121.0 |
C14—C9—C8 | 123.78 (18) | | |
| | | |
C5'—S1'—C2'—N3' | 1.04 (16) | C2'—N6—N7—C8 | −88.2 (2) |
C5'—S1'—C2'—N6 | 177.97 (18) | N6—N7—C8—O8 | −2.6 (3) |
N6—C2'—N3'—C4' | −177.57 (18) | N6—N7—C8—C9 | 179.31 (17) |
S1'—C2'—N3'—C4' | −0.8 (2) | O8—C8—C9—C10 | −6.0 (3) |
C2'—N3'—C4'—C5' | 0.0 (2) | N7—C8—C9—C10 | 172.1 (2) |
C2'—N3'—C4'—C4 | 178.47 (17) | O8—C8—C9—C14 | 172.6 (2) |
N3'—C4'—C5'—S1' | 0.7 (2) | N7—C8—C9—C14 | −9.3 (3) |
C4—C4'—C5'—S1' | −177.61 (16) | C14—C9—C10—C11 | 0.4 (5) |
C2'—S1'—C5'—C4' | −0.93 (17) | C8—C9—C10—C11 | 179.0 (3) |
C5—O1—N2—N3 | 0.4 (2) | C9—C10—C11—C12 | −1.6 (6) |
O1—N2—N3—C4 | −0.2 (2) | C10—C11—C12—C13 | 1.1 (6) |
O1—N2—N3—C15 | 176.71 (18) | C11—C12—C13—C14 | 0.6 (5) |
N2—N3—C4—C5 | −0.1 (2) | C10—C9—C14—C13 | 1.3 (4) |
C15—N3—C4—C5 | −176.5 (2) | C8—C9—C14—C13 | −177.3 (2) |
N2—N3—C4—C4' | −176.17 (19) | C12—C13—C14—C9 | −1.8 (4) |
C15—N3—C4—C4' | 7.5 (3) | N2—N3—C15—C16 | −99.3 (3) |
C5'—C4'—C4—N3 | −163.0 (2) | C4—N3—C15—C16 | 77.1 (3) |
N3'—C4'—C4—N3 | 18.7 (3) | N2—N3—C15—C20 | 77.6 (3) |
C5'—C4'—C4—C5 | 21.8 (3) | C4—N3—C15—C20 | −106.0 (3) |
N3'—C4'—C4—C5 | −156.5 (2) | C20—C15—C16—C17 | −0.4 (4) |
N2—O1—C5—O5 | 179.7 (2) | N3—C15—C16—C17 | 176.4 (2) |
N2—O1—C5—C4 | −0.5 (2) | C15—C16—C17—C18 | −0.3 (5) |
N3—C4—C5—O5 | −179.9 (3) | C16—C17—C18—C19 | 1.2 (5) |
C4'—C4—C5—O5 | −3.9 (4) | C17—C18—C19—C20 | −1.4 (4) |
N3—C4—C5—O1 | 0.3 (2) | C16—C15—C20—C19 | 0.3 (4) |
C4'—C4—C5—O1 | 176.33 (19) | N3—C15—C20—C19 | −176.5 (2) |
N3'—C2'—N6—N7 | −8.8 (3) | C18—C19—C20—C15 | 0.7 (4) |
S1'—C2'—N6—N7 | 174.58 (14) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N6—H6···O8i | 0.86 | 2.12 | 2.827 (2) | 139 |
N7—H7···O5ii | 0.86 | 2.48 | 3.185 (3) | 140 |
C5′—H5′···O5iii | 0.93 | 2.58 | 3.144 (3) | 120 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z; (iii) −x+2, −y+1, −z. |
Comparison of the bond lengths (Å) in the sydnone ring of the
title compound with the corresponding average values found in
3,4-disubstituted sydnone compounds topBond | O1–C5 | O1–N2 | N2–N3 | N3–C4 | C4–C5 | C5–O5 |
| | | | | | |
Title | 1.391 (3) | 1.380 (3) | 1.319 (3) | 1.344 (3) | 1.423 (3) | 1.210 (3) |
compound | | | | | | |
| | | | | | |
Average | 1.407 (4) | 1.379 (3) | 1.310 (3) | 1.351 (3) | 1.413 (3) | 1.206 (3) |
value | | | | | | |
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