The title compound, C8H9N3OS, crystallizes in a triclinic unit cell, with two crystallographically independent molecules in the asymmetric unit. It has a two-dimensional layer structure with intermolecular hydrogen bonding.
Supporting information
CCDC reference: 269358
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.042
- wR factor = 0.124
- Data-to-parameter ratio = 12.8
checkCIF/PLATON results
No syntax errors found
Alert level A
ABSTM02_ALERT_3_A Test not performed as the _exptl_absorpt_correction_type
has not been identified. See test ABSTY_01.
ABSTY01_ALERT_1_A The absorption correction should be one of the following
* none
* analytical
* integration
* numerical
* gaussian
* empirical
* psi-scan
* multi-scan
* refdelf
* sphere
* cylinder
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.58 Ratio
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.18 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.74 Ratio
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C12
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.13
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.03
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C9 -C14 1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
PLAT420_ALERT_2_C D-H Without Acceptor N4 - H4 ... ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4 .. S1 .. 2.99 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4 .. S2 .. 2.90 Ang.
2 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
14 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
8 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
N-Benzoylthiosemicarbazide
top
Crystal data top
C8H9N3OS | Z = 4 |
Mr = 195.24 | F(000) = 408 |
Triclinic, P1 | Dx = 1.331 Mg m−3 |
a = 8.237 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.438 (3) Å | Cell parameters from 905 reflections |
c = 14.590 (6) Å | θ = 2.6–26.1° |
α = 83.554 (7)° | µ = 0.30 mm−1 |
β = 75.631 (7)° | T = 293 K |
γ = 84.998 (7)° | Block, colorless |
V = 974.3 (7) Å3 | 0.20 × 0.16 × 0.14 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3408 independent reflections |
Radiation source: fine-focus sealed tube | 2413 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
φ and ω scans | θmax = 25.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −9→9 |
Tmin = 0.927, Tmax = 0.959 | k = −10→8 |
5064 measured reflections | l = −17→11 |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | w = 1/[σ2(Fo2) + (0.066P)2] where P = (Fo2 + 2Fc2)/3 |
3408 reflections | (Δ/σ)max = 0.001 |
267 parameters | Δρmax = 0.33 e Å−3 |
8 restraints | Δρmin = −0.29 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 | 0.20558 (8) | 0.44361 (8) | 0.96438 (5) | 0.0403 (2) | |
S2 | 1.32622 (9) | 0.95077 (8) | −0.07452 (5) | 0.0478 (2) | |
O1 | 0.5848 (3) | 0.7382 (4) | 0.70866 (17) | 0.0863 (9) | |
O2 | 1.1635 (3) | 0.7167 (3) | 0.24999 (15) | 0.0663 (6) | |
N1 | 0.6476 (3) | 0.6042 (3) | 0.83852 (17) | 0.0404 (6) | |
H1 | 0.707 (3) | 0.599 (3) | 0.8799 (14) | 0.037 (8)* | |
N2 | 0.4791 (3) | 0.5889 (3) | 0.88217 (17) | 0.0431 (6) | |
H2 | 0.422 (3) | 0.675 (2) | 0.899 (2) | 0.069 (11)* | |
N3 | 0.5057 (3) | 0.3180 (3) | 0.87782 (19) | 0.0465 (6) | |
H3A | 0.6077 (17) | 0.323 (3) | 0.8447 (18) | 0.051 (9)* | |
H3B | 0.463 (3) | 0.228 (2) | 0.899 (2) | 0.057 (9)* | |
N4 | 0.9933 (3) | 0.7925 (3) | 0.15231 (17) | 0.0477 (6) | |
H4 | 0.897 (2) | 0.801 (4) | 0.140 (3) | 0.083 (12)* | |
N5 | 1.1247 (3) | 0.8012 (3) | 0.07203 (17) | 0.0447 (6) | |
H5 | 1.150 (3) | 0.720 (2) | 0.0404 (16) | 0.039 (8)* | |
N6 | 1.1315 (4) | 1.0684 (3) | 0.0787 (2) | 0.0564 (7) | |
H6A | 1.050 (3) | 1.055 (4) | 0.1284 (15) | 0.074 (12)* | |
H6B | 1.165 (4) | 1.158 (2) | 0.047 (2) | 0.073 (11)* | |
C1 | 0.9941 (3) | 0.6650 (3) | 0.7617 (2) | 0.0450 (7) | |
H1A | 0.9693 | 0.5860 | 0.8121 | 0.054* | |
C2 | 1.1558 (3) | 0.7113 (4) | 0.7282 (2) | 0.0583 (8) | |
H2A | 1.2403 | 0.6620 | 0.7555 | 0.070* | |
C3 | 1.1938 (4) | 0.8289 (4) | 0.6553 (3) | 0.0682 (10) | |
H3 | 1.3034 | 0.8599 | 0.6333 | 0.082* | |
C4 | 1.0709 (5) | 0.9005 (5) | 0.6151 (3) | 0.0855 (13) | |
H4A | 1.0969 | 0.9810 | 0.5657 | 0.103* | |
C5 | 0.9074 (4) | 0.8550 (5) | 0.6467 (3) | 0.0723 (10) | |
H5A | 0.8243 | 0.9045 | 0.6185 | 0.087* | |
C6 | 0.8679 (3) | 0.7357 (3) | 0.72037 (19) | 0.0423 (7) | |
C7 | 0.6889 (3) | 0.6944 (4) | 0.7533 (2) | 0.0454 (7) | |
C8 | 0.4128 (3) | 0.4473 (3) | 0.90322 (18) | 0.0332 (6) | |
C9 | 0.8911 (5) | 0.6543 (5) | 0.4042 (3) | 0.0815 (11) | |
H9 | 0.9985 | 0.6221 | 0.4114 | 0.098* | |
C10 | 0.7542 (7) | 0.6333 (6) | 0.4809 (3) | 0.1065 (16) | |
H10 | 0.7701 | 0.5862 | 0.5390 | 0.128* | |
C11 | 0.5989 (7) | 0.6804 (6) | 0.4717 (4) | 0.1105 (17) | |
H11 | 0.5075 | 0.6670 | 0.5236 | 0.133* | |
C12 | 0.5750 (5) | 0.7477 (7) | 0.3869 (4) | 0.1216 (19) | |
H12 | 0.4671 | 0.7795 | 0.3806 | 0.146* | |
C13 | 0.7110 (4) | 0.7692 (5) | 0.3093 (3) | 0.0863 (13) | |
H13 | 0.6938 | 0.8158 | 0.2514 | 0.104* | |
C14 | 0.8695 (4) | 0.7223 (3) | 0.3178 (2) | 0.0511 (8) | |
C15 | 1.0215 (4) | 0.7418 (3) | 0.2391 (2) | 0.0439 (7) | |
C16 | 1.1862 (3) | 0.9415 (3) | 0.03145 (19) | 0.0384 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0275 (3) | 0.0386 (4) | 0.0503 (5) | −0.0041 (3) | −0.0012 (3) | −0.0019 (3) |
S2 | 0.0476 (4) | 0.0360 (4) | 0.0510 (5) | −0.0051 (3) | 0.0040 (3) | −0.0014 (3) |
O1 | 0.0432 (13) | 0.154 (3) | 0.0584 (16) | −0.0189 (14) | −0.0172 (11) | 0.0246 (16) |
O2 | 0.0440 (12) | 0.0970 (18) | 0.0524 (14) | 0.0131 (11) | −0.0074 (10) | −0.0069 (12) |
N1 | 0.0287 (12) | 0.0451 (13) | 0.0445 (15) | −0.0096 (10) | −0.0033 (11) | 0.0022 (11) |
N2 | 0.0287 (11) | 0.0376 (14) | 0.0552 (16) | −0.0056 (10) | 0.0052 (10) | −0.0035 (11) |
N3 | 0.0312 (13) | 0.0359 (14) | 0.0663 (18) | −0.0037 (11) | 0.0002 (12) | −0.0049 (12) |
N4 | 0.0391 (14) | 0.0592 (16) | 0.0414 (15) | −0.0061 (12) | −0.0041 (12) | −0.0008 (12) |
N5 | 0.0481 (14) | 0.0385 (14) | 0.0418 (14) | −0.0067 (11) | 0.0019 (11) | −0.0058 (11) |
N6 | 0.0650 (18) | 0.0398 (16) | 0.0557 (18) | −0.0048 (14) | 0.0034 (15) | −0.0073 (14) |
C1 | 0.0376 (15) | 0.0468 (17) | 0.0461 (17) | −0.0058 (12) | −0.0008 (13) | −0.0040 (13) |
C2 | 0.0366 (16) | 0.068 (2) | 0.069 (2) | −0.0091 (15) | −0.0091 (15) | −0.0061 (18) |
C3 | 0.0442 (18) | 0.079 (2) | 0.076 (3) | −0.0215 (17) | 0.0023 (17) | −0.008 (2) |
C4 | 0.068 (2) | 0.093 (3) | 0.083 (3) | −0.031 (2) | −0.004 (2) | 0.035 (2) |
C5 | 0.0515 (19) | 0.096 (3) | 0.062 (2) | −0.0153 (18) | −0.0112 (17) | 0.027 (2) |
C6 | 0.0363 (15) | 0.0519 (17) | 0.0369 (16) | −0.0095 (13) | −0.0038 (12) | −0.0029 (13) |
C7 | 0.0356 (15) | 0.0607 (18) | 0.0384 (17) | −0.0063 (13) | −0.0055 (13) | −0.0032 (14) |
C8 | 0.0282 (13) | 0.0381 (15) | 0.0334 (14) | −0.0037 (11) | −0.0070 (11) | −0.0030 (11) |
C9 | 0.081 (3) | 0.103 (3) | 0.050 (2) | 0.006 (2) | −0.0025 (19) | 0.000 (2) |
C10 | 0.125 (4) | 0.124 (4) | 0.050 (3) | −0.004 (3) | 0.012 (3) | 0.002 (2) |
C11 | 0.105 (4) | 0.118 (4) | 0.077 (3) | −0.014 (3) | 0.040 (3) | −0.007 (3) |
C12 | 0.057 (3) | 0.172 (5) | 0.112 (4) | −0.007 (3) | 0.016 (3) | 0.009 (4) |
C13 | 0.049 (2) | 0.127 (4) | 0.067 (3) | 0.001 (2) | 0.0050 (18) | 0.010 (2) |
C14 | 0.0511 (18) | 0.0513 (18) | 0.0453 (18) | −0.0045 (14) | 0.0000 (14) | −0.0059 (14) |
C15 | 0.0474 (17) | 0.0383 (16) | 0.0436 (18) | −0.0016 (13) | −0.0047 (13) | −0.0087 (13) |
C16 | 0.0371 (14) | 0.0343 (15) | 0.0438 (16) | −0.0021 (11) | −0.0105 (12) | −0.0022 (12) |
Geometric parameters (Å, º) top
S1—C8 | 1.720 (2) | C1—H1A | 0.9300 |
S2—C16 | 1.682 (3) | C2—C3 | 1.366 (4) |
O1—C7 | 1.210 (3) | C2—H2A | 0.9300 |
O2—C15 | 1.216 (3) | C3—C4 | 1.357 (5) |
N1—C7 | 1.365 (4) | C3—H3 | 0.9300 |
N1—N2 | 1.387 (3) | C4—C5 | 1.384 (4) |
N1—H1 | 0.860 (10) | C4—H4A | 0.9300 |
N2—C8 | 1.329 (3) | C5—C6 | 1.384 (4) |
N2—H2 | 0.858 (10) | C5—H5A | 0.9300 |
N3—C8 | 1.311 (3) | C6—C7 | 1.493 (4) |
N3—H3A | 0.861 (10) | C9—C14 | 1.371 (5) |
N3—H3B | 0.855 (10) | C9—C10 | 1.385 (5) |
N4—C15 | 1.359 (4) | C9—H9 | 0.9300 |
N4—N5 | 1.384 (3) | C10—C11 | 1.341 (7) |
N4—H4 | 0.854 (10) | C10—H10 | 0.9300 |
N5—C16 | 1.344 (3) | C11—C12 | 1.355 (7) |
N5—H5 | 0.851 (10) | C11—H11 | 0.9300 |
N6—C16 | 1.324 (4) | C12—C13 | 1.389 (5) |
N6—H6A | 0.861 (10) | C12—H12 | 0.9300 |
N6—H6B | 0.866 (10) | C13—C14 | 1.363 (4) |
C1—C2 | 1.376 (4) | C13—H13 | 0.9300 |
C1—C6 | 1.386 (4) | C14—C15 | 1.481 (4) |
| | | |
C7—N1—N2 | 118.5 (2) | C5—C6—C1 | 118.8 (3) |
C7—N1—H1 | 122.3 (17) | C5—C6—C7 | 117.7 (3) |
N2—N1—H1 | 111.1 (17) | C1—C6—C7 | 123.5 (3) |
C8—N2—N1 | 122.0 (2) | O1—C7—N1 | 121.2 (3) |
C8—N2—H2 | 122 (2) | O1—C7—C6 | 123.0 (3) |
N1—N2—H2 | 116 (2) | N1—C7—C6 | 115.8 (2) |
C8—N3—H3A | 121.1 (19) | N3—C8—N2 | 119.8 (2) |
C8—N3—H3B | 117 (2) | N3—C8—S1 | 122.9 (2) |
H3A—N3—H3B | 122 (3) | N2—C8—S1 | 117.36 (19) |
C15—N4—N5 | 120.8 (2) | C14—C9—C10 | 120.6 (4) |
C15—N4—H4 | 124 (2) | C14—C9—H9 | 119.7 |
N5—N4—H4 | 114 (2) | C10—C9—H9 | 119.7 |
C16—N5—N4 | 121.7 (2) | C11—C10—C9 | 120.3 (5) |
C16—N5—H5 | 118.5 (18) | C11—C10—H10 | 119.8 |
N4—N5—H5 | 118.1 (17) | C9—C10—H10 | 119.8 |
C16—N6—H6A | 116 (2) | C10—C11—C12 | 120.0 (4) |
C16—N6—H6B | 114 (2) | C10—C11—H11 | 120.0 |
H6A—N6—H6B | 128 (3) | C12—C11—H11 | 120.0 |
C2—C1—C6 | 120.1 (3) | C11—C12—C13 | 120.3 (4) |
C2—C1—H1A | 120.0 | C11—C12—H12 | 119.8 |
C6—C1—H1A | 120.0 | C13—C12—H12 | 119.8 |
C3—C2—C1 | 120.7 (3) | C14—C13—C12 | 120.3 (4) |
C3—C2—H2A | 119.6 | C14—C13—H13 | 119.9 |
C1—C2—H2A | 119.6 | C12—C13—H13 | 119.9 |
C4—C3—C2 | 119.7 (3) | C13—C14—C9 | 118.6 (3) |
C4—C3—H3 | 120.1 | C13—C14—C15 | 123.8 (3) |
C2—C3—H3 | 120.1 | C9—C14—C15 | 117.6 (3) |
C3—C4—C5 | 120.8 (3) | O2—C15—N4 | 121.2 (3) |
C3—C4—H4A | 119.6 | O2—C15—C14 | 123.2 (3) |
C5—C4—H4A | 119.6 | N4—C15—C14 | 115.7 (3) |
C6—C5—C4 | 119.9 (3) | N6—C16—N5 | 116.9 (3) |
C6—C5—H5A | 120.0 | N6—C16—S2 | 122.8 (2) |
C4—C5—H5A | 120.0 | N5—C16—S2 | 120.3 (2) |
| | | |
C7—N1—N2—C8 | 121.3 (3) | N1—N2—C8—S1 | 175.8 (2) |
C15—N4—N5—C16 | −103.9 (3) | C14—C9—C10—C11 | −0.6 (7) |
C6—C1—C2—C3 | 1.1 (5) | C9—C10—C11—C12 | 0.6 (8) |
C1—C2—C3—C4 | −0.3 (5) | C10—C11—C12—C13 | −0.5 (9) |
C2—C3—C4—C5 | −0.4 (6) | C11—C12—C13—C14 | 0.3 (8) |
C3—C4—C5—C6 | 0.2 (6) | C12—C13—C14—C9 | −0.2 (6) |
C4—C5—C6—C1 | 0.5 (5) | C12—C13—C14—C15 | −179.5 (4) |
C4—C5—C6—C7 | 178.4 (3) | C10—C9—C14—C13 | 0.4 (6) |
C2—C1—C6—C5 | −1.2 (4) | C10—C9—C14—C15 | 179.7 (4) |
C2—C1—C6—C7 | −179.0 (3) | N5—N4—C15—O2 | 6.8 (4) |
N2—N1—C7—O1 | −12.3 (4) | N5—N4—C15—C14 | −174.1 (2) |
N2—N1—C7—C6 | 167.2 (2) | C13—C14—C15—O2 | 171.2 (3) |
C5—C6—C7—O1 | 13.7 (5) | C9—C14—C15—O2 | −8.1 (5) |
C1—C6—C7—O1 | −168.5 (3) | C13—C14—C15—N4 | −7.8 (5) |
C5—C6—C7—N1 | −165.7 (3) | C9—C14—C15—N4 | 172.8 (3) |
C1—C6—C7—N1 | 12.1 (4) | N4—N5—C16—N6 | 9.0 (4) |
N1—N2—C8—N3 | −3.8 (4) | N4—N5—C16—S2 | −171.1 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N6—H6B···S1i | 0.87 (1) | 2.58 (1) | 3.439 (3) | 169 (3) |
N5—H5···S1ii | 0.85 (1) | 2.65 (1) | 3.495 (3) | 172 (2) |
N4—H4···S1iii | 0.85 (1) | 2.99 (3) | 3.503 (3) | 120 (3) |
N4—H4···S2iv | 0.85 (1) | 2.90 (2) | 3.584 (3) | 138 (3) |
N3—H3B···S2v | 0.85 (1) | 2.64 (1) | 3.475 (3) | 167 (3) |
N3—H3A···O2vi | 0.86 (1) | 2.07 (1) | 2.907 (3) | 164 (3) |
N2—H2···S2vii | 0.86 (1) | 2.43 (1) | 3.268 (3) | 165 (3) |
N1—H1···S1viii | 0.86 (1) | 2.53 (1) | 3.358 (3) | 162 (2) |
Symmetry codes: (i) x+1, y+1, z−1; (ii) x+1, y, z−1; (iii) −x+1, −y+1, −z+1; (iv) −x+2, −y+2, −z; (v) x−1, y−1, z+1; (vi) −x+2, −y+1, −z+1; (vii) x−1, y, z+1; (viii) −x+1, −y+1, −z+2. |