Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807019952/cf2102sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807019952/cf2102Isup2.hkl |
CCDC reference: 601659
Key indicators
- Single-crystal X-ray study
- T = 297 K
- Mean (C-C) = 0.003 Å
- R factor = 0.061
- wR factor = 0.156
- Data-to-parameter ratio = 14.0
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT430_ALERT_2_B Short Inter D...A Contact O15 .. N1 .. 2.86 Ang.
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.06 PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.13 Ratio
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Compound (I) [m.p. >573 K] was prepared according to a known procedure (Cunha et al., 2007). Single crystals of I were obtained by slow evaporation of a solution in CHCl3 at room temperature.
All H atoms were positioned in idealized coordinates with distances 0.93–0.97 and 0.82 Å for the C atoms and O atoms, respectively. H atoms were refined isotropicaly and allowed to ride on their parent atoms with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(methyl C,O).
In continuation of our structural studies of bioactive thioxopyrimidine (Sabino et al., 2007), we present the analysis of the 4-thioxopyrimidine derivative I, which exhibited some level of trypanocidal activity. This derivative differs from 1-[1-(2-hydroxyethyl)-6-methyl-2-phenyl-4-thioxo-1,4-dihydro-5-pyrimidinyl]-1-ethanone by a substituent on the ring atom C5, where (I) has a carboxylate group instead of an acetyl group.
The molecular structure of (I) is depicted in Fig. 1. The conformation of I is defined by steric effects. The angle between the pyrimidine mean plane (r.m.s. 0.017 Å) and the mean plane through the phenyl ring is 87.71 (8)°. The torsion angle C20—C19—N1—C6 is -89.1 (2)° and C4—C5—C14—O15 is 91.1 (3)°. Bond lengths are within the expected ranges with the exception of the C2–C7 and C5–C14 bonds which present the same elongation of 0.03 Å from the formal single bond distance.
The crystal packing (Fig. 2) is mediated by a hydrogen bond of type O21–H21···N3ii and a non-classical hydrogen bond of type C13–H13B···Sii [Symmetry code: (ii) 1 - x, -y, 1 - z], which connect neighboring molecules in a linear chain along [100]. Intermolecular contacts of type C14═ O15i···π-ring [Symmetry code: (i)1 - x, -y, 1 - z] mediate the packing via the sp2 ring atoms C6, N1 and C2, building a dimer about an inversion center. The distance N1···O15i is 2.858 (2) Å, 0.21 Å shorter than the sum of van der Waals radii of the atoms involved.
For the synthesis, see: Cunha et al. (2007). The corresponding compound with an acetyl group on C5 is described by Sabino et al. (2007). Despite the different chemical nature of these substituent groups, both compounds pack in a similar manner.
Data collection: CAD-4-PC (Enraf–Nonius, 1993); cell refinement: CAD-4-PC; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).
C16H18N2O3S | Z = 2 |
Mr = 318.39 | F(000) = 336 |
Triclinic, P1 | Dx = 1.291 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.5418 Å |
a = 8.2262 (15) Å | Cell parameters from 25 reflections |
b = 11.0683 (18) Å | θ = 16.4–50.6° |
c = 11.112 (2) Å | µ = 1.88 mm−1 |
α = 60.317 (15)° | T = 297 K |
β = 74.555 (16)° | Prism, yellow |
γ = 69.765 (16)° | 0.35 × 0.3 × 0.2 mm |
V = 819.1 (3) Å3 |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.025 |
non–profiled ω/2θ scans | θmax = 67.1°, θmin = 4.6° |
Absorption correction: ψ scan (North et al., 1968) | h = −9→9 |
Tmin = 0.597, Tmax = 0.686 | k = −11→13 |
2997 measured reflections | l = 0→13 |
2837 independent reflections | 2 standard reflections every 120 min |
2630 reflections with I > 2σ(I) | intensity decay: 1% |
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0886P)2 + 0.1677P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.061 | (Δ/σ)max < 0.001 |
wR(F2) = 0.156 | Δρmax = 0.33 e Å−3 |
S = 1.18 | Δρmin = −0.38 e Å−3 |
2837 reflections | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
203 parameters | Extinction coefficient: 0.181 (8) |
0 restraints |
C16H18N2O3S | γ = 69.765 (16)° |
Mr = 318.39 | V = 819.1 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.2262 (15) Å | Cu Kα radiation |
b = 11.0683 (18) Å | µ = 1.88 mm−1 |
c = 11.112 (2) Å | T = 297 K |
α = 60.317 (15)° | 0.35 × 0.3 × 0.2 mm |
β = 74.555 (16)° |
Enraf–Nonius CAD-4 diffractometer | 2630 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.025 |
Tmin = 0.597, Tmax = 0.686 | 2 standard reflections every 120 min |
2997 measured reflections | intensity decay: 1% |
2837 independent reflections |
R[F2 > 2σ(F2)] = 0.061 | 0 restraints |
wR(F2) = 0.156 | H-atom parameters constrained |
S = 1.18 | Δρmax = 0.33 e Å−3 |
2837 reflections | Δρmin = −0.38 e Å−3 |
203 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S | 0.87159 (7) | 0.12970 (7) | 0.20413 (8) | 0.0745 (3) | |
N1 | 0.30304 (19) | 0.27798 (15) | 0.30438 (15) | 0.0430 (4) | |
C2 | 0.4169 (2) | 0.35827 (18) | 0.27024 (18) | 0.0430 (4) | |
N3 | 0.5847 (2) | 0.31579 (16) | 0.24112 (17) | 0.0495 (4) | |
C4 | 0.6574 (3) | 0.1819 (2) | 0.2448 (2) | 0.0488 (5) | |
C5 | 0.5435 (2) | 0.09323 (18) | 0.28549 (18) | 0.0456 (5) | |
C6 | 0.3693 (2) | 0.13928 (18) | 0.31766 (18) | 0.0449 (4) | |
C7 | 0.3467 (2) | 0.50303 (18) | 0.2683 (2) | 0.0468 (5) | |
C8 | 0.3321 (3) | 0.5140 (2) | 0.3891 (2) | 0.0645 (6) | |
H8 | 0.3674 | 0.4323 | 0.4703 | 0.077* | |
C9 | 0.2646 (4) | 0.6472 (3) | 0.3889 (3) | 0.0757 (7) | |
H9 | 0.2532 | 0.6551 | 0.4705 | 0.091* | |
C10 | 0.2147 (4) | 0.7674 (3) | 0.2692 (3) | 0.0799 (8) | |
H10 | 0.1683 | 0.8566 | 0.2698 | 0.096* | |
C11 | 0.2326 (4) | 0.7569 (2) | 0.1498 (3) | 0.0876 (9) | |
H11 | 0.1994 | 0.8392 | 0.0685 | 0.105* | |
C12 | 0.2999 (4) | 0.6243 (2) | 0.1476 (2) | 0.0686 (6) | |
H12 | 0.3132 | 0.6177 | 0.0652 | 0.082* | |
C13 | 0.2481 (3) | 0.0445 (2) | 0.3715 (3) | 0.0632 (6) | |
H13A | 0.3096 | −0.0439 | 0.3656 | 0.095* | |
H13B | 0.1524 | 0.0924 | 0.3165 | 0.095* | |
H13C | 0.2045 | 0.0243 | 0.4669 | 0.095* | |
C14 | 0.6211 (3) | −0.0571 (2) | 0.2998 (2) | 0.0520 (5) | |
O15 | 0.6649 (3) | −0.15931 (16) | 0.40618 (18) | 0.0888 (7) | |
O16 | 0.63106 (19) | −0.06239 (13) | 0.18248 (14) | 0.0546 (4) | |
C17 | 0.7073 (3) | −0.2034 (2) | 0.1833 (2) | 0.0651 (6) | |
H17A | 0.6387 | −0.2702 | 0.2507 | 0.078* | |
H17B | 0.8254 | −0.2418 | 0.208 | 0.078* | |
C18 | 0.7075 (4) | −0.1824 (3) | 0.0412 (3) | 0.0876 (9) | |
H18A | 0.7589 | −0.2726 | 0.037 | 0.131* | |
H18B | 0.7738 | −0.1147 | −0.0246 | 0.131* | |
H18C | 0.5897 | −0.1462 | 0.0188 | 0.131* | |
C19 | 0.1130 (2) | 0.3349 (2) | 0.3320 (2) | 0.0515 (5) | |
H19A | 0.0928 | 0.4045 | 0.3667 | 0.062* | |
H19B | 0.0628 | 0.2568 | 0.4035 | 0.062* | |
C20 | 0.0236 (3) | 0.4058 (2) | 0.2020 (3) | 0.0636 (6) | |
H20A | 0.0689 | 0.487 | 0.1312 | 0.076* | |
H20B | 0.0452 | 0.3377 | 0.1651 | 0.076* | |
O21 | −0.1572 (2) | 0.45270 (19) | 0.2374 (3) | 0.0871 (6) | |
H21 | −0.21 | 0.4136 | 0.2198 | 0.131* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S | 0.0453 (4) | 0.0706 (4) | 0.1179 (6) | 0.0022 (3) | −0.0192 (3) | −0.0558 (4) |
N1 | 0.0458 (8) | 0.0357 (8) | 0.0484 (8) | −0.0048 (6) | −0.0136 (6) | −0.0191 (6) |
C2 | 0.0487 (10) | 0.0354 (9) | 0.0458 (9) | −0.0077 (7) | −0.0110 (7) | −0.0181 (8) |
N3 | 0.0491 (9) | 0.0390 (8) | 0.0632 (10) | −0.0073 (6) | −0.0104 (7) | −0.0255 (7) |
C4 | 0.0513 (10) | 0.0429 (10) | 0.0552 (10) | −0.0033 (8) | −0.0176 (8) | −0.0242 (8) |
C5 | 0.0572 (11) | 0.0347 (9) | 0.0467 (10) | −0.0034 (7) | −0.0190 (7) | −0.0185 (8) |
C6 | 0.0565 (10) | 0.0351 (9) | 0.0466 (9) | −0.0073 (7) | −0.0192 (7) | −0.0172 (8) |
C7 | 0.0478 (10) | 0.0353 (9) | 0.0580 (11) | −0.0076 (7) | −0.0078 (8) | −0.0226 (8) |
C8 | 0.0837 (15) | 0.0487 (11) | 0.0625 (13) | −0.0103 (10) | −0.0110 (10) | −0.0287 (10) |
C9 | 0.0861 (17) | 0.0671 (15) | 0.0901 (17) | −0.0139 (12) | −0.0023 (13) | −0.0545 (14) |
C10 | 0.0803 (16) | 0.0480 (13) | 0.124 (2) | 0.0007 (11) | −0.0272 (15) | −0.0513 (15) |
C11 | 0.120 (2) | 0.0358 (11) | 0.105 (2) | −0.0075 (12) | −0.0478 (17) | −0.0210 (12) |
C12 | 0.0980 (18) | 0.0420 (11) | 0.0653 (13) | −0.0137 (11) | −0.0219 (12) | −0.0202 (10) |
C13 | 0.0647 (13) | 0.0467 (11) | 0.0855 (15) | −0.0147 (9) | −0.0221 (11) | −0.0281 (11) |
C14 | 0.0648 (12) | 0.0380 (10) | 0.0541 (11) | −0.0025 (8) | −0.0212 (8) | −0.0211 (9) |
O15 | 0.1527 (19) | 0.0406 (8) | 0.0626 (10) | 0.0108 (9) | −0.0489 (10) | −0.0206 (8) |
O16 | 0.0703 (9) | 0.0381 (7) | 0.0556 (8) | 0.0038 (6) | −0.0226 (6) | −0.0250 (6) |
C17 | 0.0788 (15) | 0.0417 (11) | 0.0746 (14) | 0.0060 (9) | −0.0219 (11) | −0.0334 (10) |
C18 | 0.119 (2) | 0.0667 (15) | 0.0732 (15) | 0.0008 (15) | −0.0080 (14) | −0.0458 (13) |
C19 | 0.0454 (10) | 0.0467 (10) | 0.0645 (12) | −0.0078 (8) | −0.0085 (8) | −0.0278 (9) |
C20 | 0.0557 (12) | 0.0510 (11) | 0.0833 (15) | −0.0028 (9) | −0.0277 (10) | −0.0268 (11) |
O21 | 0.0531 (9) | 0.0676 (10) | 0.1593 (18) | 0.0065 (7) | −0.0400 (10) | −0.0650 (12) |
S—C4 | 1.665 (2) | O16—C17 | 1.463 (2) |
N1—C2 | 1.365 (2) | C17—C18 | 1.478 (3) |
N1—C6 | 1.384 (2) | C19—C20 | 1.512 (3) |
N1—C19 | 1.480 (2) | C20—O21 | 1.412 (3) |
N1—O15i | 2.858 (2) | O21—H21 | 0.82 |
C2—O15i | 3.182 (3) | C8—H8 | 0.93 |
C6—O15i | 3.117 (2) | C9—H9 | 0.93 |
C2—N3 | 1.302 (2) | C10—H10 | 0.93 |
C2—C7 | 1.494 (2) | C11—H11 | 0.93 |
N3—C4 | 1.377 (2) | C12—H12 | 0.93 |
C4—C5 | 1.420 (3) | C13—H13A | 0.96 |
C5—C6 | 1.358 (3) | C13—H13B | 0.96 |
C5—C14 | 1.503 (2) | C13—H13C | 0.96 |
C6—C13 | 1.496 (3) | C17—H17A | 0.97 |
C7—C12 | 1.372 (3) | C17—H17B | 0.97 |
C7—C8 | 1.377 (3) | C18—H18A | 0.96 |
C8—C9 | 1.384 (3) | C18—H18B | 0.96 |
C9—C10 | 1.367 (4) | C18—H18C | 0.96 |
C10—C11 | 1.354 (4) | C19—H19A | 0.97 |
C11—C12 | 1.388 (3) | C19—H19B | 0.97 |
C14—O15 | 1.195 (3) | C20—H20A | 0.97 |
C14—O16 | 1.313 (2) | C20—H20B | 0.97 |
C2—N1—C6 | 118.59 (15) | C6—C13—H13B | 109.5 |
C2—N1—C19 | 121.19 (14) | H13A—C13—H13B | 109.5 |
C6—N1—C19 | 120.19 (15) | C6—C13—H13C | 109.5 |
N3—C2—N1 | 124.07 (15) | H13A—C13—H13C | 109.5 |
N3—C2—C7 | 117.36 (15) | H13B—C13—H13C | 109.5 |
N1—C2—C7 | 118.55 (15) | O15—C14—O16 | 124.43 (17) |
C2—N3—C4 | 119.96 (16) | O15—C14—C5 | 123.69 (18) |
N3—C4—C5 | 117.43 (17) | O16—C14—C5 | 111.86 (15) |
N3—C4—S | 119.70 (15) | C14—O16—C17 | 116.71 (15) |
C5—C4—S | 122.87 (15) | O16—C17—C18 | 106.96 (17) |
C6—C5—C4 | 121.37 (16) | O16—C17—H17A | 110.3 |
C6—C5—C14 | 120.09 (17) | C18—C17—H17A | 110.3 |
C4—C5—C14 | 118.46 (17) | O16—C17—H17B | 110.3 |
C5—C6—N1 | 118.38 (16) | C18—C17—H17B | 110.3 |
C5—C6—C13 | 122.62 (17) | H17A—C17—H17B | 108.6 |
N1—C6—C13 | 118.97 (17) | C17—C18—H18A | 109.5 |
C12—C7—C8 | 120.04 (18) | C17—C18—H18B | 109.5 |
C12—C7—C2 | 120.84 (17) | H18A—C18—H18B | 109.5 |
C8—C7—C2 | 119.11 (17) | C17—C18—H18C | 109.5 |
C7—C8—C9 | 119.5 (2) | H18A—C18—H18C | 109.5 |
C7—C8—H8 | 120.2 | H18B—C18—H18C | 109.5 |
C9—C8—H8 | 120.2 | N1—C19—C20 | 111.69 (17) |
C10—C9—C8 | 120.2 (2) | N1—C19—H19A | 109.3 |
C10—C9—H9 | 119.9 | C20—C19—H19A | 109.3 |
C8—C9—H9 | 119.9 | N1—C19—H19B | 109.3 |
C11—C10—C9 | 120.2 (2) | C20—C19—H19B | 109.3 |
C11—C10—H10 | 119.9 | H19A—C19—H19B | 107.9 |
C9—C10—H10 | 119.9 | O21—C20—C19 | 108.4 (2) |
C10—C11—C12 | 120.6 (2) | O21—C20—H20A | 110 |
C10—C11—H11 | 119.7 | C19—C20—H20A | 110 |
C12—C11—H11 | 119.7 | O21—C20—H20B | 110 |
C7—C12—C11 | 119.4 (2) | C19—C20—H20B | 110 |
C7—C12—H12 | 120.3 | H20A—C20—H20B | 108.4 |
C11—C12—H12 | 120.3 | C20—O21—H21 | 109.5 |
C6—C13—H13A | 109.5 | ||
C6—N1—C2—N3 | 4.2 (3) | N1—C2—C7—C12 | −92.5 (2) |
C19—N1—C2—N3 | −178.05 (16) | N3—C2—C7—C8 | −90.3 (2) |
C6—N1—C2—C7 | −174.66 (15) | N1—C2—C7—C8 | 88.7 (2) |
C19—N1—C2—C7 | 3.1 (2) | C12—C7—C8—C9 | 2.2 (3) |
N1—C2—N3—C4 | −0.5 (3) | C2—C7—C8—C9 | −179.0 (2) |
C7—C2—N3—C4 | 178.33 (15) | C7—C8—C9—C10 | −0.8 (4) |
C2—N3—C4—C5 | −2.0 (3) | C8—C9—C10—C11 | −0.7 (4) |
C2—N3—C4—S | 178.69 (14) | C9—C10—C11—C12 | 0.7 (5) |
N3—C4—C5—C6 | 0.9 (3) | C8—C7—C12—C11 | −2.1 (4) |
S—C4—C5—C6 | −179.84 (13) | C2—C7—C12—C11 | 179.0 (2) |
N3—C4—C5—C14 | −175.92 (15) | C10—C11—C12—C7 | 0.7 (4) |
S—C4—C5—C14 | 3.4 (2) | C6—C5—C14—O15 | −85.8 (3) |
C4—C5—C6—N1 | 2.7 (3) | C4—C5—C14—O15 | 91.1 (3) |
C14—C5—C6—N1 | 179.42 (15) | C6—C5—C14—O16 | 92.9 (2) |
C4—C5—C6—C13 | −175.09 (17) | C4—C5—C14—O16 | −90.3 (2) |
C14—C5—C6—C13 | 1.7 (3) | O15—C14—O16—C17 | −2.3 (3) |
C2—N1—C6—C5 | −5.1 (2) | C5—C14—O16—C17 | 179.06 (17) |
C19—N1—C6—C5 | 177.14 (15) | C14—O16—C17—C18 | −179.1 (2) |
C2—N1—C6—C13 | 172.76 (16) | C2—N1—C19—C20 | 93.1 (2) |
C19—N1—C6—C13 | −5.0 (2) | C6—N1—C19—C20 | −89.1 (2) |
N3—C2—C7—C12 | 88.6 (2) | N1—C19—C20—O21 | 177.98 (15) |
Symmetry code: (i) −x+1, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O21—H21···N3ii | 0.82 | 2.21 | 2.986 (2) | 159 |
C13—H13B···Sii | 0.96 | 2.73 | 3.640 (2) | 160 |
Symmetry code: (ii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C16H18N2O3S |
Mr | 318.39 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 297 |
a, b, c (Å) | 8.2262 (15), 11.0683 (18), 11.112 (2) |
α, β, γ (°) | 60.317 (15), 74.555 (16), 69.765 (16) |
V (Å3) | 819.1 (3) |
Z | 2 |
Radiation type | Cu Kα |
µ (mm−1) | 1.88 |
Crystal size (mm) | 0.35 × 0.3 × 0.2 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.597, 0.686 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2997, 2837, 2630 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.061, 0.156, 1.18 |
No. of reflections | 2837 |
No. of parameters | 203 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.33, −0.38 |
Computer programs: CAD-4-PC (Enraf–Nonius, 1993), CAD-4-PC, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
O21—H21···N3i | 0.82 | 2.21 | 2.986 (2) | 158.5 |
C13—H13B···Si | 0.96 | 2.73 | 3.640 (2) | 159.5 |
Symmetry code: (i) x−1, y, z. |
In continuation of our structural studies of bioactive thioxopyrimidine (Sabino et al., 2007), we present the analysis of the 4-thioxopyrimidine derivative I, which exhibited some level of trypanocidal activity. This derivative differs from 1-[1-(2-hydroxyethyl)-6-methyl-2-phenyl-4-thioxo-1,4-dihydro-5-pyrimidinyl]-1-ethanone by a substituent on the ring atom C5, where (I) has a carboxylate group instead of an acetyl group.
The molecular structure of (I) is depicted in Fig. 1. The conformation of I is defined by steric effects. The angle between the pyrimidine mean plane (r.m.s. 0.017 Å) and the mean plane through the phenyl ring is 87.71 (8)°. The torsion angle C20—C19—N1—C6 is -89.1 (2)° and C4—C5—C14—O15 is 91.1 (3)°. Bond lengths are within the expected ranges with the exception of the C2–C7 and C5–C14 bonds which present the same elongation of 0.03 Å from the formal single bond distance.
The crystal packing (Fig. 2) is mediated by a hydrogen bond of type O21–H21···N3ii and a non-classical hydrogen bond of type C13–H13B···Sii [Symmetry code: (ii) 1 - x, -y, 1 - z], which connect neighboring molecules in a linear chain along [100]. Intermolecular contacts of type C14═ O15i···π-ring [Symmetry code: (i)1 - x, -y, 1 - z] mediate the packing via the sp2 ring atoms C6, N1 and C2, building a dimer about an inversion center. The distance N1···O15i is 2.858 (2) Å, 0.21 Å shorter than the sum of van der Waals radii of the atoms involved.