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In the title compound, C
14H
12N
2O
2S, the benzoyl and 3-hydroxyphenyl fragments adopt
trans–
cis positions with respect to the S atom across their C—N bonds. The dihedral angle between the 3-hydroxyphenyl and N
2CS thiourea groups is 72.09 (8)°. The crystal structure is stabilized by O—H
S and N—H
S hydrogen bonds, forming a polymeric chain along the
c axis.
Supporting information
CCDC reference: 646710
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.039
- wR factor = 0.102
- Data-to-parameter ratio = 13.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 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
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 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: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
N-Benzoyl-
N'-(3-hydroxyphenyl)thiourea
top
Crystal data top
C14H12N2O2S | F(000) = 568 |
Mr = 272.32 | Dx = 1.392 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 813 reflections |
a = 12.209 (3) Å | θ = 1.8–25.0° |
b = 7.3126 (17) Å | µ = 0.25 mm−1 |
c = 15.710 (4) Å | T = 298 K |
β = 112.133 (4)° | Block, colourless |
V = 1299.2 (5) Å3 | 0.50 × 0.40 × 0.30 mm |
Z = 4 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 2289 independent reflections |
Radiation source: fine-focus sealed tube | 1997 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
Detector resolution: 83.66 pixels mm-1 | θmax = 25.0°, θmin = 1.8° |
ω scans | h = −14→14 |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | k = −6→8 |
Tmin = 0.886, Tmax = 0.929 | l = −18→18 |
6357 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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.102 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0546P)2 + 0.361P] where P = (Fo2 + 2Fc2)/3 |
2289 reflections | (Δ/σ)max < 0.001 |
173 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.14187 (5) | 1.25114 (7) | 0.07193 (3) | 0.05609 (19) | |
O1 | 0.33387 (14) | 0.72948 (17) | 0.05556 (9) | 0.0590 (4) | |
O2 | 0.26079 (12) | 1.12409 (17) | 0.43127 (8) | 0.0495 (3) | |
H2 | 0.2343 | 1.1097 | 0.4717 | 0.074* | |
N1 | 0.25159 (12) | 1.0082 (2) | 0.00724 (9) | 0.0411 (3) | |
H1 | 0.2401 | 1.0890 | −0.0350 | 0.049* | |
N2 | 0.21006 (14) | 0.9144 (2) | 0.13100 (10) | 0.0451 (4) | |
H2A | 0.2420 | 0.8135 | 0.1242 | 0.054* | |
C1 | 0.31501 (17) | 0.9631 (3) | −0.15128 (12) | 0.0474 (4) | |
H1A | 0.2506 | 1.0386 | −0.1592 | 0.057* | |
C2 | 0.36227 (19) | 0.9539 (3) | −0.21865 (13) | 0.0561 (5) | |
H2B | 0.3291 | 1.0226 | −0.2721 | 0.067* | |
C3 | 0.45786 (18) | 0.8435 (3) | −0.20688 (14) | 0.0594 (5) | |
H3 | 0.4897 | 0.8383 | −0.2521 | 0.071* | |
C4 | 0.50653 (17) | 0.7407 (3) | −0.12841 (14) | 0.0568 (5) | |
H4 | 0.5712 | 0.6660 | −0.1207 | 0.068* | |
C5 | 0.45979 (16) | 0.7479 (3) | −0.06100 (13) | 0.0473 (4) | |
H5 | 0.4926 | 0.6775 | −0.0081 | 0.057* | |
C6 | 0.36393 (14) | 0.8600 (2) | −0.07219 (11) | 0.0386 (4) | |
C7 | 0.31602 (15) | 0.8569 (2) | 0.00222 (11) | 0.0404 (4) | |
C8 | 0.20290 (14) | 1.0463 (2) | 0.07212 (11) | 0.0394 (4) | |
C9 | 0.16954 (15) | 0.9238 (2) | 0.20543 (11) | 0.0389 (4) | |
C10 | 0.23177 (14) | 1.0250 (2) | 0.28212 (11) | 0.0367 (4) | |
H10 | 0.2964 | 1.0947 | 0.2842 | 0.044* | |
C11 | 0.19688 (14) | 1.0218 (2) | 0.35637 (10) | 0.0351 (4) | |
C12 | 0.10204 (15) | 0.9162 (2) | 0.35381 (11) | 0.0401 (4) | |
H12 | 0.0798 | 0.9125 | 0.4043 | 0.048* | |
C13 | 0.04073 (16) | 0.8168 (3) | 0.27635 (12) | 0.0507 (5) | |
H13 | −0.0236 | 0.7464 | 0.2744 | 0.061* | |
C14 | 0.07343 (17) | 0.8200 (3) | 0.20115 (12) | 0.0509 (5) | |
H14 | 0.0313 | 0.7532 | 0.1486 | 0.061* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0738 (4) | 0.0563 (3) | 0.0551 (3) | 0.0229 (2) | 0.0436 (3) | 0.0126 (2) |
O1 | 0.0941 (11) | 0.0466 (8) | 0.0511 (8) | 0.0179 (7) | 0.0443 (8) | 0.0095 (6) |
O2 | 0.0652 (8) | 0.0501 (7) | 0.0372 (6) | −0.0169 (6) | 0.0236 (6) | −0.0080 (6) |
N1 | 0.0536 (8) | 0.0411 (8) | 0.0364 (7) | 0.0047 (6) | 0.0260 (7) | 0.0030 (6) |
N2 | 0.0644 (9) | 0.0400 (8) | 0.0417 (8) | 0.0035 (7) | 0.0322 (7) | 0.0001 (6) |
C1 | 0.0595 (11) | 0.0448 (10) | 0.0450 (10) | 0.0039 (8) | 0.0278 (9) | −0.0013 (8) |
C2 | 0.0731 (13) | 0.0593 (12) | 0.0454 (10) | −0.0021 (10) | 0.0331 (10) | 0.0013 (9) |
C3 | 0.0606 (12) | 0.0778 (14) | 0.0545 (11) | −0.0123 (11) | 0.0386 (10) | −0.0141 (11) |
C4 | 0.0421 (10) | 0.0763 (14) | 0.0560 (12) | 0.0018 (9) | 0.0231 (9) | −0.0150 (10) |
C5 | 0.0450 (10) | 0.0540 (11) | 0.0425 (10) | 0.0011 (8) | 0.0161 (8) | −0.0075 (8) |
C6 | 0.0439 (9) | 0.0387 (9) | 0.0368 (8) | −0.0043 (7) | 0.0192 (7) | −0.0077 (7) |
C7 | 0.0497 (10) | 0.0390 (9) | 0.0354 (8) | −0.0019 (8) | 0.0193 (7) | −0.0048 (7) |
C8 | 0.0406 (9) | 0.0462 (10) | 0.0344 (8) | −0.0018 (7) | 0.0175 (7) | −0.0025 (7) |
C9 | 0.0467 (9) | 0.0410 (9) | 0.0348 (8) | 0.0021 (7) | 0.0218 (7) | 0.0015 (7) |
C10 | 0.0375 (8) | 0.0358 (9) | 0.0408 (9) | −0.0012 (7) | 0.0194 (7) | 0.0024 (7) |
C11 | 0.0402 (8) | 0.0319 (8) | 0.0330 (8) | 0.0012 (7) | 0.0135 (7) | 0.0013 (6) |
C12 | 0.0425 (9) | 0.0461 (10) | 0.0380 (9) | −0.0006 (7) | 0.0224 (7) | 0.0022 (7) |
C13 | 0.0459 (10) | 0.0618 (12) | 0.0489 (10) | −0.0167 (9) | 0.0229 (8) | −0.0065 (9) |
C14 | 0.0547 (11) | 0.0603 (12) | 0.0395 (9) | −0.0150 (9) | 0.0200 (8) | −0.0103 (9) |
Geometric parameters (Å, º) top
S1—C8 | 1.6725 (18) | C3—H3 | 0.9300 |
O1—C7 | 1.217 (2) | C4—C5 | 1.380 (3) |
O2—C11 | 1.3644 (19) | C4—H4 | 0.9300 |
O2—H2 | 0.8200 | C5—C6 | 1.385 (2) |
N1—C7 | 1.377 (2) | C5—H5 | 0.9300 |
N1—C8 | 1.388 (2) | C6—C7 | 1.492 (2) |
N1—H1 | 0.8600 | C9—C10 | 1.373 (2) |
N2—C8 | 1.316 (2) | C9—C14 | 1.378 (2) |
N2—C9 | 1.433 (2) | C10—C11 | 1.384 (2) |
N2—H2A | 0.8600 | C10—H10 | 0.9300 |
C1—C6 | 1.382 (2) | C11—C12 | 1.379 (2) |
C1—C2 | 1.385 (2) | C12—C13 | 1.372 (2) |
C1—H1A | 0.9300 | C12—H12 | 0.9300 |
C2—C3 | 1.373 (3) | C13—C14 | 1.382 (2) |
C2—H2B | 0.9300 | C13—H13 | 0.9300 |
C3—C4 | 1.373 (3) | C14—H14 | 0.9300 |
| | | |
C11—O2—H2 | 109.5 | O1—C7—N1 | 122.27 (15) |
C7—N1—C8 | 127.97 (14) | O1—C7—C6 | 122.01 (15) |
C7—N1—H1 | 116.0 | N1—C7—C6 | 115.71 (14) |
C8—N1—H1 | 116.0 | N2—C8—N1 | 115.83 (15) |
C8—N2—C9 | 125.91 (15) | N2—C8—S1 | 124.68 (13) |
C8—N2—H2A | 117.0 | N1—C8—S1 | 119.48 (12) |
C9—N2—H2A | 117.0 | C10—C9—C14 | 121.27 (15) |
C6—C1—C2 | 119.80 (18) | C10—C9—N2 | 119.66 (15) |
C6—C1—H1A | 120.1 | C14—C9—N2 | 118.90 (15) |
C2—C1—H1A | 120.1 | C9—C10—C11 | 119.07 (15) |
C3—C2—C1 | 120.25 (19) | C9—C10—H10 | 120.5 |
C3—C2—H2B | 119.9 | C11—C10—H10 | 120.5 |
C1—C2—H2B | 119.9 | O2—C11—C12 | 122.20 (14) |
C2—C3—C4 | 120.07 (17) | O2—C11—C10 | 117.37 (14) |
C2—C3—H3 | 120.0 | C12—C11—C10 | 120.42 (14) |
C4—C3—H3 | 120.0 | C13—C12—C11 | 119.58 (15) |
C3—C4—C5 | 120.26 (18) | C13—C12—H12 | 120.2 |
C3—C4—H4 | 119.9 | C11—C12—H12 | 120.2 |
C5—C4—H4 | 119.9 | C12—C13—C14 | 120.81 (16) |
C4—C5—C6 | 119.93 (18) | C12—C13—H13 | 119.6 |
C4—C5—H5 | 120.0 | C14—C13—H13 | 119.6 |
C6—C5—H5 | 120.0 | C9—C14—C13 | 118.84 (16) |
C1—C6—C5 | 119.70 (16) | C9—C14—H14 | 120.6 |
C1—C6—C7 | 123.28 (16) | C13—C14—H14 | 120.6 |
C5—C6—C7 | 116.98 (15) | | |
| | | |
C6—C1—C2—C3 | −0.4 (3) | C9—N2—C8—S1 | −1.3 (3) |
C1—C2—C3—C4 | 0.5 (3) | C7—N1—C8—N2 | −6.7 (2) |
C2—C3—C4—C5 | −0.1 (3) | C7—N1—C8—S1 | 172.59 (14) |
C3—C4—C5—C6 | −0.4 (3) | C8—N2—C9—C10 | −73.5 (2) |
C2—C1—C6—C5 | −0.1 (3) | C8—N2—C9—C14 | 111.2 (2) |
C2—C1—C6—C7 | −177.81 (17) | C14—C9—C10—C11 | 0.1 (3) |
C4—C5—C6—C1 | 0.5 (3) | N2—C9—C10—C11 | −175.13 (15) |
C4—C5—C6—C7 | 178.35 (16) | C9—C10—C11—O2 | −179.94 (14) |
C8—N1—C7—O1 | 3.3 (3) | C9—C10—C11—C12 | 1.0 (2) |
C8—N1—C7—C6 | −176.03 (15) | O2—C11—C12—C13 | 179.70 (16) |
C1—C6—C7—O1 | 156.65 (18) | C10—C11—C12—C13 | −1.2 (3) |
C5—C6—C7—O1 | −21.1 (2) | C11—C12—C13—C14 | 0.5 (3) |
C1—C6—C7—N1 | −24.1 (2) | C10—C9—C14—C13 | −0.8 (3) |
C5—C6—C7—N1 | 158.17 (15) | N2—C9—C14—C13 | 174.43 (17) |
C9—N2—C8—N1 | 178.00 (15) | C12—C13—C14—C9 | 0.5 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1 | 0.86 | 1.93 | 2.621 (2) | 137 |
N1—H1···O2i | 0.86 | 2.20 | 2.961 (2) | 147 |
O2—H2···S1ii | 0.82 | 2.48 | 3.2002 (17) | 148 |
Symmetry codes: (i) x, −y+5/2, z−1/2; (ii) x, −y+5/2, z+1/2. |
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