1. Chemical context
Thiosemicarbazones are potent intermediates for the synthesis of pharmaceutical and bioactive materials and they are used extensively in the field of medicinal chemistry. The biological activity of these ligands is related to their ability to coordinate to metal centres in enzymes (Seena et al., 2006
). These derivatives possess an additional functional group that is not coordinated to their `primary' metal ion, thereby suggesting that the biological activity may also depend on the non-coordinating groups (Venkatesh et al., 2016
). Thiosemicarbazones in their neutral or deprotonated form behave as N,N,S-thiodentate chelates towards metal ions. They display antiproliferative activity on different tumors cell lines and have been a common feature of all compounds with carcinogenic potency. A strong correlation has been found between tumor growth rate and the ribonucleoside diphosphate reductase (RDR) enzyme (Arora et al., 2014
).
Thiosemicarbazone derivatives have found applications in drug development for the treatment of central nervous system disorders and bacterial infection as well as being analgesic and anti-allergic agents. They are inhibitors of DNA replication and also of many proteases. This inhibitory activity explains the level of interest given to them in the fight against microbial and parasitic diseases (Mani et al., 2015
). Thiosemicarbazones have many biological activities such as antiviral, antibacterial, antitumor, anti African trypanosome (Fatondji et al., 2013
), antimicrobial, sodium channel blocker, anticancer, antitubercular, antiviral (Venkatesh et al., 2016
), antifungal, locomotor activity (Singh et al., 2011
), antimalarial, anticancer and they are used as a cure for leprosy, rheumatism and trypanosomiasis (Parul et al., 2012
). As part of our studies in this area, we now describe the syntheses and structures of the title compounds (I
) and (II
).
2. Structural commentary
The molecular structure of compounds (I)
and (II)
are shown in Figs. 1
and 2
, respectively. Compound (I)
crystallizes with two independent molecules in the asymmetric unit. In both the compounds, there is a short N—H⋯N contact, forming an S(5) ring motif (Figs. 1
and 2
, and Tables 1
and 2
). In both compounds, the thiosemicarbazone group adopts an extended conformation, as can be seen from the torsion angle S1—C11—N2—N1 [−173.1 (1)° in molecule A and −174.9 (1)° in molecule B of compound (I)] and S1—C16—N2—N1 [172.2 (1)° in compound (II)]. In compound (I)
, the acetate group adopts an extended conformation, which is evidenced by the torsion angle C1—C2—O2—C3 [−173.2 (2) and 179.9 (2)° in molecules A and B, respectively]. The bond lengths C11A—S1A [1.692 (2) Å] and C11B—S1B [1.680 (2) Å] in (I)
and C16—S1 [1.679 (1) Å] in (II)
are comparable with the values reported in the literature (CSD; Groom et al., 2016
). In compound (II)
, the benzoate and acetophenone thiosemicarbozone groups lie in a plane [C6—C7—O2—C8 = 175.9 (1)°]. The carbonyl group is oriented syn-periplanar to C5 [C5—C6—C7—O1 = −15.8 (2) °] and anti-periplanar to C1 [C1—C6—C7—O1 = 160.7 (1) °]. The dihedral angle between the benzene rings in compound (II)
is 46.70 (7)°.
D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A | N3A—H3A1⋯N1A | 0.86 | 2.26 | 2.617 (2) | 105 | N3B—H3B1⋯N1B | 0.86 | 2.28 | 2.633 (2) | 105 | N2A—H2A⋯S1B | 0.86 | 2.63 | 3.4724 (15) | 167 | N2B—H2B⋯S1A | 0.86 | 2.71 | 3.4228 (16) | 141 | N3A—H3A1⋯O1Bi | 0.86 | 2.44 | 3.164 (2) | 142 | N3B—H3B2⋯S1Aii | 0.86 | 2.57 | 3.4262 (17) | 176 | N3A—H3A2⋯Cg2iii | 0.86 | 2.62 | 3.4763 (19) | 130 | C1B—H1B3⋯Cg1iv | 0.96 | 2.73 | 3.691 (3) | 154 | Symmetry codes: (i) -x, -y+1, -z+1; (ii) x+1, y, z; (iii) -x, -y+1, -z; (iv) -x+1, -y+1, -z. | |
D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A | N3—H3A⋯N1 | 0.86 | 2.24 | 2.5953 (18) | 105 | N2—H2A⋯S1i | 0.86 | 2.68 | 3.4697 (12) | 153 | N3—H3A⋯O1ii | 0.86 | 2.27 | 3.0653 (15) | 153 | C15—H15B⋯O1iii | 0.96 | 2.55 | 3.454 (2) | 156 | N3—H3B⋯Cg2ii | 0.86 | 2.47 | 3.3385 (15) | 122 | Symmetry codes: (i) -x+1, -y, -z+2; (ii) x+1, y, z; (iii) -x, -y, -z+1. | |
| Figure 1 The molecular structure of the compound (I) , showing the atom labelling and displacement ellipsoids drawn at the 30% probability level. The short intramolecular N—H⋯N contact is shown as a dashed line (see Table 1 ). |
| Figure 2 The molecular structure of the compound (II) , showing the atom labelling and displacement ellipsoids drawn at the 40% probability level. The short intramolecular N—H⋯N contact is shown as a dashed line (see Table 2 ). |
6. Refinement
Crystal data, data collection and structure refinement details are summarized in Table 3
. Hydrogen atoms were placed in calculated positions and refined as riding atoms: C—H = 0.93–0.96 Å and N—H = 0.86 Å, with Uiso(H) = 1.5Ueq(C-methyl) and 1.2Ueq(C,N) for other H atoms.
| (I) | (II) | Crystal data | Chemical formula | C11H13N3O2S | C16H15N3O2S | Mr | 251.30 | 313.37 | Crystal system, space group | Triclinic, P![[\overline{1}]](teximages/su5323fi3.gif) | Triclinic, P![[\overline{1}]](teximages/su5323fi3.gif) | Temperature (K) | 293 | 293 | a, b, c (Å) | 7.8783 (2), 8.9254 (3), 18.7372 (5) | 7.8145 (4), 9.7538 (5), 10.9050 (7) | α, β, γ (°) | 77.243 (2), 82.423 (2), 78.856 (2) | 78.855 (4), 69.031 (2), 84.200 (3) | V (Å3) | 1255.30 (6) | 761.05 (8) | Z | 4 | 2 | Radiation type | Mo Kα | Mo Kα | μ (mm−1) | 0.25 | 0.22 | Crystal size (mm) | 0.20 × 0.15 × 0.10 | 0.25 × 0.18 × 0.14 | | Data collection | Diffractometer | Bruker SMART APEXII area-detector | Bruker SMART APEXII area-detector | Absorption correction | Multi-scan (SADABS; Bruker, 2008 ) | Multi-scan (SADABS; Bruker, 2008 ) | Tmin, Tmax | 0.785, 0.854 | 0.745, 0.865 | No. of measured, independent and observed [I > 2σ(I)] reflections | 18970, 5128, 4104 | 11596, 3154, 2857 | Rint | 0.023 | 0.027 | (sin θ/λ)max (Å−1) | 0.625 | 0.628 | | Refinement | R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.109, 1.03 | 0.034, 0.099, 1.05 | No. of reflections | 5128 | 3154 | No. of parameters | 311 | 201 | H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | Δρmax, Δρmin (e Å−3) | 0.25, −0.31 | 0.26, −0.29 | Computer programs: APEX2 and SAINT (Bruker, 2008 ), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ), Mercury (Macrae et al., 2008 ) and PLATON (Spek, 2009 ). | |
Supporting information
For both compounds, data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008). Software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009) for (I); SHELXL2014 (Sheldrick, 2008) and PLATON (Spek, 2009) for (II).
(I) (
E)-4-[1-(2-Carbamothioylhydrazinylidene)ethyl]phenyl acetate
top Crystal data top C11H13N3O2S | Z = 4 |
Mr = 251.30 | F(000) = 528 |
Triclinic, P1 | Dx = 1.330 Mg m−3 |
a = 7.8783 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.9254 (3) Å | Cell parameters from 5128 reflections |
c = 18.7372 (5) Å | θ = 1.1–26.4° |
α = 77.243 (2)° | µ = 0.25 mm−1 |
β = 82.423 (2)° | T = 293 K |
γ = 78.856 (2)° | Block, yellow |
V = 1255.30 (6) Å3 | 0.20 × 0.15 × 0.10 mm |
Data collection top Bruker SMART APEXII area-detector diffractometer | 4104 reflections with I > 2σ(I) |
ω and φ scans | Rint = 0.023 |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | θmax = 26.4°, θmin = 1.1° |
Tmin = 0.785, Tmax = 0.854 | h = −9→9 |
18970 measured reflections | k = −11→11 |
5128 independent reflections | l = −23→23 |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.109 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0498P)2 + 0.3822P] where P = (Fo2 + 2Fc2)/3 |
5128 reflections | (Δ/σ)max = 0.001 |
311 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
Special details top Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C10B | 0.2271 (3) | 0.1728 (3) | 0.52308 (11) | 0.0616 (5) | |
H10A | 0.1335 | 0.2449 | 0.5001 | 0.092* | |
H10B | 0.2263 | 0.1858 | 0.5726 | 0.092* | |
H10C | 0.2129 | 0.0681 | 0.5235 | 0.092* | |
C1A | 0.0183 (3) | 0.8835 (3) | 1.22191 (11) | 0.0706 (6) | |
H1A1 | 0.0436 | 0.9807 | 1.2279 | 0.106* | |
H1A2 | 0.0630 | 0.8015 | 1.2607 | 0.106* | |
H1A3 | −0.1051 | 0.8899 | 1.2236 | 0.106* | |
C1B | 0.5549 (3) | 0.0841 (3) | 0.07427 (10) | 0.0632 (5) | |
H1B1 | 0.4721 | 0.1283 | 0.0388 | 0.095* | |
H1B2 | 0.5685 | −0.0275 | 0.0835 | 0.095* | |
H1B3 | 0.6646 | 0.1158 | 0.0556 | 0.095* | |
C2A | 0.1010 (3) | 0.8500 (2) | 1.15003 (10) | 0.0506 (4) | |
C2B | 0.4920 (3) | 0.1395 (2) | 0.14379 (9) | 0.0515 (4) | |
C3A | 0.0618 (2) | 0.7263 (2) | 1.05471 (9) | 0.0438 (4) | |
C3B | 0.5256 (3) | 0.0862 (2) | 0.27010 (9) | 0.0501 (4) | |
C4A | −0.0202 (2) | 0.7922 (2) | 0.99205 (10) | 0.0497 (4) | |
H4A | −0.1086 | 0.8781 | 0.9916 | 0.060* | |
C4B | 0.6282 (3) | 0.1679 (2) | 0.29458 (10) | 0.0564 (5) | |
H4B | 0.7253 | 0.1982 | 0.2652 | 0.068* | |
C5A | 0.0297 (2) | 0.7298 (2) | 0.92993 (9) | 0.0476 (4) | |
H5A | −0.0266 | 0.7738 | 0.8877 | 0.057* | |
C5B | 0.5867 (3) | 0.2050 (2) | 0.36322 (9) | 0.0533 (5) | |
H5B | 0.6566 | 0.2603 | 0.3800 | 0.064* | |
C6A | 0.1629 (2) | 0.60209 (19) | 0.92929 (8) | 0.0396 (4) | |
C6B | 0.4412 (2) | 0.16043 (19) | 0.40777 (9) | 0.0438 (4) | |
C7A | 0.2445 (2) | 0.5402 (2) | 0.99344 (9) | 0.0459 (4) | |
H7A | 0.3351 | 0.4559 | 0.9942 | 0.055* | |
C7B | 0.3427 (3) | 0.0750 (2) | 0.38147 (10) | 0.0548 (5) | |
H7B | 0.2464 | 0.0423 | 0.4106 | 0.066* | |
C8A | 0.1934 (2) | 0.6015 (2) | 1.05617 (9) | 0.0481 (4) | |
H8A | 0.2482 | 0.5581 | 1.0988 | 0.058* | |
C8B | 0.3850 (3) | 0.0372 (2) | 0.31264 (10) | 0.0588 (5) | |
H8B | 0.3182 | −0.0207 | 0.2958 | 0.071* | |
C9A | 0.2116 (2) | 0.5324 (2) | 0.86296 (8) | 0.0412 (4) | |
C9B | 0.3961 (2) | 0.20310 (19) | 0.48111 (9) | 0.0427 (4) | |
C10A | 0.3766 (3) | 0.4199 (3) | 0.85640 (11) | 0.0705 (6) | |
H10D | 0.4646 | 0.4736 | 0.8273 | 0.106* | |
H10E | 0.3581 | 0.3395 | 0.8332 | 0.106* | |
H10F | 0.4132 | 0.3743 | 0.9045 | 0.106* | |
C11A | 0.0194 (2) | 0.5408 (2) | 0.70414 (9) | 0.0428 (4) | |
C11B | 0.6013 (2) | 0.3524 (2) | 0.59815 (9) | 0.0448 (4) | |
N1A | 0.10302 (18) | 0.57512 (17) | 0.81405 (7) | 0.0423 (3) | |
N1B | 0.50947 (19) | 0.26330 (17) | 0.50292 (7) | 0.0460 (3) | |
N2A | 0.14402 (18) | 0.52010 (17) | 0.74940 (7) | 0.0444 (3) | |
H2A | 0.2473 | 0.4736 | 0.7384 | 0.053* | |
N2B | 0.47614 (19) | 0.30636 (18) | 0.57038 (7) | 0.0483 (4) | |
H2B | 0.3756 | 0.3037 | 0.5945 | 0.058* | |
N3A | −0.1399 (2) | 0.5972 (2) | 0.72772 (8) | 0.0602 (4) | |
H3A1 | −0.1609 | 0.6193 | 0.7708 | 0.072* | |
H3A2 | −0.2229 | 0.6120 | 0.7001 | 0.072* | |
N3B | 0.7503 (2) | 0.3608 (2) | 0.55723 (9) | 0.0641 (5) | |
H3B1 | 0.7642 | 0.3371 | 0.5145 | 0.077* | |
H3B2 | 0.8335 | 0.3898 | 0.5733 | 0.077* | |
O1A | 0.2381 (2) | 0.8767 (2) | 1.12093 (9) | 0.0800 (5) | |
O1B | 0.3862 (2) | 0.2510 (2) | 0.15026 (8) | 0.0863 (5) | |
O2A | −0.00302 (17) | 0.78178 (16) | 1.11913 (7) | 0.0555 (3) | |
O2B | 0.57246 (19) | 0.04701 (15) | 0.20057 (7) | 0.0607 (4) | |
S1A | 0.07063 (6) | 0.49355 (7) | 0.62043 (2) | 0.05713 (16) | |
S1B | 0.56754 (6) | 0.39051 (7) | 0.68325 (2) | 0.05582 (15) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C10B | 0.0553 (12) | 0.0813 (14) | 0.0553 (11) | −0.0165 (11) | 0.0010 (9) | −0.0283 (10) |
C1A | 0.0818 (15) | 0.0834 (15) | 0.0541 (11) | −0.0020 (12) | −0.0163 (11) | −0.0344 (11) |
C1B | 0.0750 (14) | 0.0799 (14) | 0.0428 (10) | −0.0222 (11) | 0.0034 (9) | −0.0265 (9) |
C2A | 0.0566 (12) | 0.0518 (10) | 0.0477 (10) | −0.0062 (9) | −0.0142 (9) | −0.0161 (8) |
C2B | 0.0558 (11) | 0.0610 (11) | 0.0406 (9) | −0.0078 (10) | −0.0053 (8) | −0.0179 (8) |
C3A | 0.0435 (9) | 0.0564 (10) | 0.0378 (8) | −0.0175 (8) | 0.0009 (7) | −0.0177 (7) |
C3B | 0.0664 (12) | 0.0445 (9) | 0.0384 (9) | 0.0034 (9) | −0.0108 (8) | −0.0140 (7) |
C4A | 0.0490 (10) | 0.0543 (10) | 0.0488 (10) | −0.0039 (8) | −0.0074 (8) | −0.0192 (8) |
C4B | 0.0699 (13) | 0.0590 (11) | 0.0427 (9) | −0.0163 (10) | 0.0035 (9) | −0.0158 (8) |
C5A | 0.0514 (10) | 0.0539 (10) | 0.0396 (9) | −0.0061 (8) | −0.0110 (7) | −0.0126 (7) |
C5B | 0.0665 (12) | 0.0565 (10) | 0.0428 (9) | −0.0181 (9) | −0.0010 (8) | −0.0181 (8) |
C6A | 0.0379 (9) | 0.0493 (9) | 0.0352 (8) | −0.0144 (7) | −0.0021 (6) | −0.0106 (7) |
C6B | 0.0530 (10) | 0.0417 (9) | 0.0364 (8) | −0.0031 (8) | −0.0094 (7) | −0.0086 (7) |
C7A | 0.0440 (10) | 0.0544 (10) | 0.0394 (8) | −0.0043 (8) | −0.0064 (7) | −0.0118 (7) |
C7B | 0.0580 (12) | 0.0644 (11) | 0.0464 (10) | −0.0153 (9) | −0.0054 (8) | −0.0157 (8) |
C8A | 0.0500 (10) | 0.0623 (11) | 0.0340 (8) | −0.0116 (9) | −0.0081 (7) | −0.0095 (7) |
C8B | 0.0694 (13) | 0.0628 (12) | 0.0530 (11) | −0.0124 (10) | −0.0154 (10) | −0.0235 (9) |
C9A | 0.0368 (9) | 0.0536 (10) | 0.0352 (8) | −0.0112 (7) | −0.0013 (7) | −0.0113 (7) |
C9B | 0.0452 (9) | 0.0456 (9) | 0.0365 (8) | −0.0022 (7) | −0.0078 (7) | −0.0093 (7) |
C10A | 0.0578 (13) | 0.1042 (17) | 0.0488 (11) | 0.0159 (12) | −0.0143 (9) | −0.0341 (11) |
C11A | 0.0387 (9) | 0.0554 (10) | 0.0362 (8) | −0.0082 (8) | −0.0039 (7) | −0.0130 (7) |
C11B | 0.0403 (9) | 0.0559 (10) | 0.0388 (8) | −0.0021 (8) | −0.0052 (7) | −0.0153 (7) |
N1A | 0.0410 (8) | 0.0560 (8) | 0.0335 (7) | −0.0104 (6) | −0.0013 (6) | −0.0158 (6) |
N1B | 0.0477 (8) | 0.0579 (9) | 0.0338 (7) | −0.0041 (7) | −0.0047 (6) | −0.0156 (6) |
N2A | 0.0355 (7) | 0.0657 (9) | 0.0349 (7) | −0.0049 (7) | −0.0024 (6) | −0.0202 (6) |
N2B | 0.0397 (8) | 0.0720 (10) | 0.0371 (7) | −0.0072 (7) | −0.0011 (6) | −0.0228 (7) |
N3A | 0.0410 (9) | 0.0971 (13) | 0.0450 (8) | 0.0060 (8) | −0.0084 (7) | −0.0322 (8) |
N3B | 0.0451 (9) | 0.1090 (14) | 0.0489 (9) | −0.0192 (9) | 0.0046 (7) | −0.0384 (9) |
O1A | 0.0727 (11) | 0.1024 (12) | 0.0834 (11) | −0.0401 (10) | 0.0012 (8) | −0.0408 (9) |
O1B | 0.1032 (13) | 0.0907 (11) | 0.0507 (8) | 0.0349 (10) | −0.0177 (8) | −0.0223 (8) |
O2A | 0.0525 (8) | 0.0791 (9) | 0.0448 (7) | −0.0190 (7) | 0.0029 (6) | −0.0311 (6) |
O2B | 0.0776 (9) | 0.0599 (8) | 0.0442 (7) | 0.0098 (7) | −0.0114 (6) | −0.0246 (6) |
S1A | 0.0422 (3) | 0.0971 (4) | 0.0381 (2) | −0.0090 (2) | −0.00201 (18) | −0.0298 (2) |
S1B | 0.0444 (3) | 0.0874 (4) | 0.0418 (2) | −0.0056 (2) | −0.00359 (19) | −0.0310 (2) |
Geometric parameters (Å, º) top C10B—C9B | 1.494 (3) | C6A—C7A | 1.392 (2) |
C10B—H10A | 0.9600 | C6A—C9A | 1.484 (2) |
C10B—H10B | 0.9600 | C6B—C7B | 1.387 (2) |
C10B—H10C | 0.9600 | C6B—C9B | 1.487 (2) |
C1A—C2A | 1.483 (3) | C7A—C8A | 1.385 (2) |
C1A—H1A1 | 0.9600 | C7A—H7A | 0.9300 |
C1A—H1A2 | 0.9600 | C7B—C8B | 1.387 (2) |
C1A—H1A3 | 0.9600 | C7B—H7B | 0.9300 |
C1B—C2B | 1.485 (2) | C8A—H8A | 0.9300 |
C1B—H1B1 | 0.9600 | C8B—H8B | 0.9300 |
C1B—H1B2 | 0.9600 | C9A—N1A | 1.282 (2) |
C1B—H1B3 | 0.9600 | C9A—C10A | 1.490 (3) |
C2A—O1A | 1.186 (2) | C9B—N1B | 1.278 (2) |
C2A—O2A | 1.361 (2) | C10A—H10D | 0.9600 |
C2B—O1B | 1.186 (2) | C10A—H10E | 0.9600 |
C2B—O2B | 1.343 (2) | C10A—H10F | 0.9600 |
C3A—C8A | 1.366 (3) | C11A—N3A | 1.315 (2) |
C3A—C4A | 1.375 (2) | C11A—N2A | 1.341 (2) |
C3A—O2A | 1.4023 (19) | C11A—S1A | 1.6915 (16) |
C3B—C8B | 1.361 (3) | C11B—N3B | 1.320 (2) |
C3B—C4B | 1.367 (3) | C11B—N2B | 1.341 (2) |
C3B—O2B | 1.4074 (19) | C11B—S1B | 1.6799 (16) |
C4A—C5A | 1.379 (2) | N1A—N2A | 1.3825 (17) |
C4A—H4A | 0.9300 | N1B—N2B | 1.3792 (18) |
C4B—C5B | 1.381 (2) | N2A—H2A | 0.8600 |
C4B—H4B | 0.9300 | N2B—H2B | 0.8600 |
C5A—C6A | 1.394 (2) | N3A—H3A1 | 0.8600 |
C5A—H5A | 0.9300 | N3A—H3A2 | 0.8600 |
C5B—C6B | 1.395 (3) | N3B—H3B1 | 0.8600 |
C5B—H5B | 0.9300 | N3B—H3B2 | 0.8600 |
| | | |
C9B—C10B—H10A | 109.5 | C5B—C6B—C9B | 120.40 (15) |
C9B—C10B—H10B | 109.5 | C8A—C7A—C6A | 121.27 (17) |
H10A—C10B—H10B | 109.5 | C8A—C7A—H7A | 119.4 |
C9B—C10B—H10C | 109.5 | C6A—C7A—H7A | 119.4 |
H10A—C10B—H10C | 109.5 | C8B—C7B—C6B | 121.33 (18) |
H10B—C10B—H10C | 109.5 | C8B—C7B—H7B | 119.3 |
C2A—C1A—H1A1 | 109.5 | C6B—C7B—H7B | 119.3 |
C2A—C1A—H1A2 | 109.5 | C3A—C8A—C7A | 119.29 (16) |
H1A1—C1A—H1A2 | 109.5 | C3A—C8A—H8A | 120.4 |
C2A—C1A—H1A3 | 109.5 | C7A—C8A—H8A | 120.4 |
H1A1—C1A—H1A3 | 109.5 | C3B—C8B—C7B | 119.06 (17) |
H1A2—C1A—H1A3 | 109.5 | C3B—C8B—H8B | 120.5 |
C2B—C1B—H1B1 | 109.5 | C7B—C8B—H8B | 120.5 |
C2B—C1B—H1B2 | 109.5 | N1A—C9A—C6A | 115.51 (15) |
H1B1—C1B—H1B2 | 109.5 | N1A—C9A—C10A | 124.10 (15) |
C2B—C1B—H1B3 | 109.5 | C6A—C9A—C10A | 120.39 (14) |
H1B1—C1B—H1B3 | 109.5 | N1B—C9B—C6B | 115.48 (15) |
H1B2—C1B—H1B3 | 109.5 | N1B—C9B—C10B | 125.51 (15) |
O1A—C2A—O2A | 122.19 (17) | C6B—C9B—C10B | 119.01 (15) |
O1A—C2A—C1A | 127.08 (18) | C9A—C10A—H10D | 109.5 |
O2A—C2A—C1A | 110.72 (17) | C9A—C10A—H10E | 109.5 |
O1B—C2B—O2B | 122.74 (16) | H10D—C10A—H10E | 109.5 |
O1B—C2B—C1B | 126.04 (18) | C9A—C10A—H10F | 109.5 |
O2B—C2B—C1B | 111.22 (17) | H10D—C10A—H10F | 109.5 |
C8A—C3A—C4A | 121.15 (15) | H10E—C10A—H10F | 109.5 |
C8A—C3A—O2A | 120.42 (15) | N3A—C11A—N2A | 117.60 (14) |
C4A—C3A—O2A | 118.20 (16) | N3A—C11A—S1A | 122.72 (13) |
C8B—C3B—C4B | 121.45 (16) | N2A—C11A—S1A | 119.68 (12) |
C8B—C3B—O2B | 119.99 (17) | N3B—C11B—N2B | 117.47 (15) |
C4B—C3B—O2B | 118.50 (17) | N3B—C11B—S1B | 122.55 (13) |
C3A—C4A—C5A | 119.40 (17) | N2B—C11B—S1B | 119.94 (13) |
C3A—C4A—H4A | 120.3 | C9A—N1A—N2A | 118.53 (14) |
C5A—C4A—H4A | 120.3 | C9B—N1B—N2B | 118.72 (14) |
C3B—C4B—C5B | 119.52 (18) | C11A—N2A—N1A | 118.60 (13) |
C3B—C4B—H4B | 120.2 | C11A—N2A—H2A | 120.7 |
C5B—C4B—H4B | 120.2 | N1A—N2A—H2A | 120.7 |
C4A—C5A—C6A | 121.19 (16) | C11B—N2B—N1B | 119.63 (14) |
C4A—C5A—H5A | 119.4 | C11B—N2B—H2B | 120.2 |
C6A—C5A—H5A | 119.4 | N1B—N2B—H2B | 120.2 |
C4B—C5B—C6B | 120.83 (17) | C11A—N3A—H3A1 | 120.0 |
C4B—C5B—H5B | 119.6 | C11A—N3A—H3A2 | 120.0 |
C6B—C5B—H5B | 119.6 | H3A1—N3A—H3A2 | 120.0 |
C7A—C6A—C5A | 117.68 (15) | C11B—N3B—H3B1 | 120.0 |
C7A—C6A—C9A | 121.51 (15) | C11B—N3B—H3B2 | 120.0 |
C5A—C6A—C9A | 120.79 (14) | H3B1—N3B—H3B2 | 120.0 |
C7B—C6B—C5B | 117.77 (16) | C2A—O2A—C3A | 118.74 (14) |
C7B—C6B—C9B | 121.82 (16) | C2B—O2B—C3B | 117.30 (14) |
| | | |
C8A—C3A—C4A—C5A | 0.9 (3) | C5A—C6A—C9A—C10A | 166.64 (18) |
O2A—C3A—C4A—C5A | −173.63 (15) | C7B—C6B—C9B—N1B | 170.96 (17) |
C8B—C3B—C4B—C5B | −1.6 (3) | C5B—C6B—C9B—N1B | −8.5 (2) |
O2B—C3B—C4B—C5B | −178.73 (17) | C7B—C6B—C9B—C10B | −8.7 (3) |
C3A—C4A—C5A—C6A | −0.6 (3) | C5B—C6B—C9B—C10B | 171.80 (17) |
C3B—C4B—C5B—C6B | −0.1 (3) | C6A—C9A—N1A—N2A | 177.13 (13) |
C4A—C5A—C6A—C7A | −0.3 (3) | C10A—C9A—N1A—N2A | −3.3 (3) |
C4A—C5A—C6A—C9A | 177.89 (16) | C6B—C9B—N1B—N2B | 179.76 (14) |
C4B—C5B—C6B—C7B | 1.4 (3) | C10B—C9B—N1B—N2B | −0.6 (3) |
C4B—C5B—C6B—C9B | −179.04 (17) | N3A—C11A—N2A—N1A | −7.3 (2) |
C5A—C6A—C7A—C8A | 1.0 (2) | S1A—C11A—N2A—N1A | 173.06 (12) |
C9A—C6A—C7A—C8A | −177.17 (15) | C9A—N1A—N2A—C11A | 168.09 (16) |
C5B—C6B—C7B—C8B | −1.2 (3) | N3B—C11B—N2B—N1B | 3.0 (3) |
C9B—C6B—C7B—C8B | 179.30 (17) | S1B—C11B—N2B—N1B | −174.85 (12) |
C4A—C3A—C8A—C7A | −0.2 (3) | C9B—N1B—N2B—C11B | 172.12 (16) |
O2A—C3A—C8A—C7A | 174.20 (15) | O1A—C2A—O2A—C3A | 7.0 (3) |
C6A—C7A—C8A—C3A | −0.8 (3) | C1A—C2A—O2A—C3A | −173.17 (16) |
C4B—C3B—C8B—C7B | 1.8 (3) | C8A—C3A—O2A—C2A | 67.9 (2) |
O2B—C3B—C8B—C7B | 178.94 (17) | C4A—C3A—O2A—C2A | −117.52 (19) |
C6B—C7B—C8B—C3B | −0.4 (3) | O1B—C2B—O2B—C3B | 0.6 (3) |
C7A—C6A—C9A—N1A | 164.41 (16) | C1B—C2B—O2B—C3B | 179.85 (16) |
C5A—C6A—C9A—N1A | −13.8 (2) | C8B—C3B—O2B—C2B | 84.9 (2) |
C7A—C6A—C9A—C10A | −15.2 (3) | C4B—C3B—O2B—C2B | −97.9 (2) |
Hydrogen-bond geometry (Å, º) topCg1 and Cg2 are the centroids of the C3A–C8A and C3B–C8B rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3A—H3A1···N1A | 0.86 | 2.26 | 2.617 (2) | 105 |
N3B—H3B1···N1B | 0.86 | 2.28 | 2.633 (2) | 105 |
N2A—H2A···S1B | 0.86 | 2.63 | 3.4724 (15) | 167 |
N2B—H2B···S1A | 0.86 | 2.71 | 3.4228 (16) | 141 |
N3A—H3A1···O1Bi | 0.86 | 2.44 | 3.164 (2) | 142 |
N3B—H3B2···S1Aii | 0.86 | 2.57 | 3.4262 (17) | 176 |
N3A—H3A2···Cg2iii | 0.86 | 2.62 | 3.4763 (19) | 130 |
C1B—H1B3···Cg1iv | 0.96 | 2.73 | 3.691 (3) | 154 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x+1, y, z; (iii) −x, −y+1, −z; (iv) −x+1, −y+1, −z. |
(II) (
E)-4-[1-(2-Carbamothioylhydrazinylidene)ethyl]phenyl benzoate
top Crystal data top C16H15N3O2S | Z = 2 |
Mr = 313.37 | F(000) = 328 |
Triclinic, P1 | Dx = 1.367 Mg m−3 |
a = 7.8145 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.7538 (5) Å | Cell parameters from 3154 reflections |
c = 10.9050 (7) Å | θ = 2.0–26.5° |
α = 78.855 (4)° | µ = 0.22 mm−1 |
β = 69.031 (2)° | T = 293 K |
γ = 84.200 (3)° | Block, pale-yellow |
V = 761.05 (8) Å3 | 0.25 × 0.18 × 0.14 mm |
Data collection top Bruker SMART APEXII area-detector diffractometer | 2857 reflections with I > 2σ(I) |
ω and φ scans | Rint = 0.027 |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | θmax = 26.5°, θmin = 2.0° |
Tmin = 0.745, Tmax = 0.865 | h = −8→9 |
11596 measured reflections | k = −12→12 |
3154 independent reflections | l = −13→13 |
Refinement top Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.034 | w = 1/[σ2(Fo2) + (0.0512P)2 + 0.1914P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.099 | (Δ/σ)max = 0.001 |
S = 1.05 | Δρmax = 0.26 e Å−3 |
3154 reflections | Δρmin = −0.29 e Å−3 |
201 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.080 (6) |
Special details top Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | −0.0574 (2) | 0.60395 (15) | 0.12357 (14) | 0.0461 (3) | |
H1 | 0.0581 | 0.6165 | 0.1252 | 0.055* | |
C2 | −0.1286 (2) | 0.69706 (17) | 0.03984 (16) | 0.0562 (4) | |
H2 | −0.0616 | 0.7736 | −0.0138 | 0.067* | |
C3 | −0.2978 (3) | 0.67730 (18) | 0.03519 (16) | 0.0596 (4) | |
H3 | −0.3439 | 0.7398 | −0.0223 | 0.072* | |
C4 | −0.3993 (2) | 0.56519 (19) | 0.11541 (17) | 0.0579 (4) | |
H4 | −0.5134 | 0.5519 | 0.1117 | 0.069* | |
C5 | −0.3315 (2) | 0.47264 (16) | 0.20141 (15) | 0.0483 (3) | |
H5 | −0.4005 | 0.3977 | 0.2567 | 0.058* | |
C6 | −0.15975 (18) | 0.49176 (14) | 0.20510 (12) | 0.0384 (3) | |
C7 | −0.09783 (18) | 0.39381 (14) | 0.30353 (12) | 0.0392 (3) | |
C8 | 0.15463 (18) | 0.31751 (15) | 0.37198 (13) | 0.0400 (3) | |
C9 | 0.15816 (19) | 0.17391 (15) | 0.39018 (14) | 0.0442 (3) | |
H9 | 0.1159 | 0.1286 | 0.3395 | 0.053* | |
C10 | 0.22566 (19) | 0.09777 (14) | 0.48531 (14) | 0.0412 (3) | |
H10 | 0.2247 | 0.0006 | 0.5004 | 0.049* | |
C11 | 0.29489 (16) | 0.16457 (13) | 0.55862 (12) | 0.0346 (3) | |
C12 | 0.29666 (19) | 0.31025 (14) | 0.53336 (14) | 0.0406 (3) | |
H12 | 0.3466 | 0.3565 | 0.5790 | 0.049* | |
C13 | 0.22498 (19) | 0.38662 (14) | 0.44118 (14) | 0.0433 (3) | |
H13 | 0.2243 | 0.4838 | 0.4260 | 0.052* | |
C14 | 0.36348 (17) | 0.08555 (13) | 0.66391 (12) | 0.0353 (3) | |
C15 | 0.2849 (2) | −0.05203 (16) | 0.73732 (16) | 0.0549 (4) | |
H15A | 0.3642 | −0.1019 | 0.7820 | 0.082* | |
H15B | 0.2737 | −0.1056 | 0.6755 | 0.082* | |
H15C | 0.1661 | −0.0373 | 0.8018 | 0.082* | |
C16 | 0.70223 (17) | 0.13075 (13) | 0.78932 (12) | 0.0358 (3) | |
N1 | 0.48733 (14) | 0.14652 (11) | 0.68311 (10) | 0.0361 (2) | |
N2 | 0.54777 (15) | 0.08471 (11) | 0.78611 (11) | 0.0374 (2) | |
H2A | 0.4883 | 0.0188 | 0.8464 | 0.045* | |
N3 | 0.79854 (16) | 0.21798 (13) | 0.68277 (11) | 0.0467 (3) | |
H3A | 0.7611 | 0.2423 | 0.6162 | 0.056* | |
H3B | 0.8984 | 0.2502 | 0.6803 | 0.056* | |
O1 | −0.19599 (15) | 0.31803 (12) | 0.39711 (10) | 0.0550 (3) | |
O2 | 0.08423 (13) | 0.40017 (11) | 0.27880 (9) | 0.0477 (3) | |
S1 | 0.77088 (5) | 0.07598 (4) | 0.92056 (4) | 0.05405 (15) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0487 (8) | 0.0491 (8) | 0.0399 (7) | −0.0026 (6) | −0.0165 (6) | −0.0032 (6) |
C2 | 0.0671 (10) | 0.0487 (8) | 0.0458 (8) | 0.0029 (7) | −0.0183 (7) | 0.0033 (6) |
C3 | 0.0728 (11) | 0.0613 (10) | 0.0465 (8) | 0.0207 (8) | −0.0300 (8) | −0.0070 (7) |
C4 | 0.0528 (9) | 0.0721 (10) | 0.0583 (9) | 0.0112 (8) | −0.0323 (8) | −0.0149 (8) |
C5 | 0.0451 (8) | 0.0555 (8) | 0.0467 (8) | −0.0013 (6) | −0.0206 (6) | −0.0055 (6) |
C6 | 0.0423 (7) | 0.0432 (7) | 0.0315 (6) | 0.0014 (5) | −0.0157 (5) | −0.0067 (5) |
C7 | 0.0409 (7) | 0.0454 (7) | 0.0333 (6) | −0.0030 (5) | −0.0159 (5) | −0.0048 (5) |
C8 | 0.0341 (6) | 0.0523 (7) | 0.0320 (6) | −0.0008 (5) | −0.0134 (5) | 0.0004 (5) |
C9 | 0.0457 (7) | 0.0526 (8) | 0.0419 (7) | 0.0009 (6) | −0.0224 (6) | −0.0131 (6) |
C10 | 0.0426 (7) | 0.0409 (7) | 0.0447 (7) | 0.0023 (5) | −0.0196 (6) | −0.0112 (5) |
C11 | 0.0308 (6) | 0.0398 (6) | 0.0328 (6) | 0.0008 (5) | −0.0115 (5) | −0.0055 (5) |
C12 | 0.0425 (7) | 0.0419 (7) | 0.0429 (7) | −0.0020 (5) | −0.0211 (6) | −0.0073 (5) |
C13 | 0.0451 (7) | 0.0394 (7) | 0.0473 (7) | −0.0026 (5) | −0.0214 (6) | −0.0006 (5) |
C14 | 0.0332 (6) | 0.0384 (6) | 0.0345 (6) | 0.0000 (5) | −0.0128 (5) | −0.0054 (5) |
C15 | 0.0616 (10) | 0.0520 (8) | 0.0568 (9) | −0.0181 (7) | −0.0328 (8) | 0.0094 (7) |
C16 | 0.0333 (6) | 0.0364 (6) | 0.0365 (6) | −0.0022 (5) | −0.0130 (5) | −0.0010 (5) |
N1 | 0.0360 (5) | 0.0396 (5) | 0.0339 (5) | −0.0005 (4) | −0.0162 (4) | −0.0013 (4) |
N2 | 0.0365 (6) | 0.0404 (6) | 0.0354 (5) | −0.0073 (4) | −0.0166 (4) | 0.0047 (4) |
N3 | 0.0427 (6) | 0.0574 (7) | 0.0394 (6) | −0.0168 (5) | −0.0187 (5) | 0.0098 (5) |
O1 | 0.0480 (6) | 0.0675 (7) | 0.0456 (6) | −0.0137 (5) | −0.0208 (5) | 0.0146 (5) |
O2 | 0.0404 (5) | 0.0622 (6) | 0.0387 (5) | −0.0055 (4) | −0.0193 (4) | 0.0083 (4) |
S1 | 0.0454 (2) | 0.0720 (3) | 0.0464 (2) | −0.01842 (18) | −0.02749 (17) | 0.01713 (18) |
Geometric parameters (Å, º) top C1—C2 | 1.381 (2) | C10—C11 | 1.3923 (18) |
C1—C6 | 1.3853 (19) | C10—H10 | 0.9300 |
C1—H1 | 0.9300 | C11—C12 | 1.3947 (18) |
C2—C3 | 1.375 (3) | C11—C14 | 1.4881 (17) |
C2—H2 | 0.9300 | C12—C13 | 1.3815 (18) |
C3—C4 | 1.378 (3) | C12—H12 | 0.9300 |
C3—H3 | 0.9300 | C13—H13 | 0.9300 |
C4—C5 | 1.381 (2) | C14—N1 | 1.2820 (16) |
C4—H4 | 0.9300 | C14—C15 | 1.4894 (18) |
C5—C6 | 1.389 (2) | C15—H15A | 0.9600 |
C5—H5 | 0.9300 | C15—H15B | 0.9600 |
C6—C7 | 1.4767 (17) | C15—H15C | 0.9600 |
C7—O1 | 1.1995 (16) | C16—N3 | 1.3273 (16) |
C7—O2 | 1.3555 (16) | C16—N2 | 1.3437 (16) |
C8—C9 | 1.375 (2) | C16—S1 | 1.6785 (13) |
C8—C13 | 1.376 (2) | N1—N2 | 1.3816 (14) |
C8—O2 | 1.4067 (15) | N2—H2A | 0.8600 |
C9—C10 | 1.3858 (19) | N3—H3A | 0.8600 |
C9—H9 | 0.9300 | N3—H3B | 0.8600 |
| | | |
C2—C1—C6 | 119.40 (14) | C10—C11—C12 | 118.52 (12) |
C2—C1—H1 | 120.3 | C10—C11—C14 | 122.07 (11) |
C6—C1—H1 | 120.3 | C12—C11—C14 | 119.40 (11) |
C3—C2—C1 | 120.47 (15) | C13—C12—C11 | 120.66 (12) |
C3—C2—H2 | 119.8 | C13—C12—H12 | 119.7 |
C1—C2—H2 | 119.8 | C11—C12—H12 | 119.7 |
C2—C3—C4 | 120.27 (14) | C8—C13—C12 | 119.37 (13) |
C2—C3—H3 | 119.9 | C8—C13—H13 | 120.3 |
C4—C3—H3 | 119.9 | C12—C13—H13 | 120.3 |
C3—C4—C5 | 119.92 (16) | N1—C14—C11 | 114.67 (11) |
C3—C4—H4 | 120.0 | N1—C14—C15 | 126.07 (12) |
C5—C4—H4 | 120.0 | C11—C14—C15 | 119.26 (11) |
C4—C5—C6 | 119.80 (14) | C14—C15—H15A | 109.5 |
C4—C5—H5 | 120.1 | C14—C15—H15B | 109.5 |
C6—C5—H5 | 120.1 | H15A—C15—H15B | 109.5 |
C1—C6—C5 | 120.12 (13) | C14—C15—H15C | 109.5 |
C1—C6—C7 | 122.27 (12) | H15A—C15—H15C | 109.5 |
C5—C6—C7 | 117.51 (12) | H15B—C15—H15C | 109.5 |
O1—C7—O2 | 122.72 (12) | N3—C16—N2 | 116.66 (11) |
O1—C7—C6 | 124.71 (12) | N3—C16—S1 | 122.30 (10) |
O2—C7—C6 | 112.56 (11) | N2—C16—S1 | 121.02 (9) |
C9—C8—C13 | 121.44 (12) | C14—N1—N2 | 118.03 (10) |
C9—C8—O2 | 121.45 (12) | C16—N2—N1 | 117.98 (10) |
C13—C8—O2 | 117.08 (12) | C16—N2—H2A | 121.0 |
C8—C9—C10 | 118.95 (12) | N1—N2—H2A | 121.0 |
C8—C9—H9 | 120.5 | C16—N3—H3A | 120.0 |
C10—C9—H9 | 120.5 | C16—N3—H3B | 120.0 |
C9—C10—C11 | 120.96 (12) | H3A—N3—H3B | 120.0 |
C9—C10—H10 | 119.5 | C7—O2—C8 | 116.96 (10) |
C11—C10—H10 | 119.5 | | |
| | | |
C6—C1—C2—C3 | −1.3 (2) | C14—C11—C12—C13 | −176.57 (12) |
C1—C2—C3—C4 | 0.8 (3) | C9—C8—C13—C12 | −1.6 (2) |
C2—C3—C4—C5 | 0.4 (3) | O2—C8—C13—C12 | −179.67 (12) |
C3—C4—C5—C6 | −1.0 (2) | C11—C12—C13—C8 | −1.3 (2) |
C2—C1—C6—C5 | 0.7 (2) | C10—C11—C14—N1 | 152.10 (12) |
C2—C1—C6—C7 | −175.72 (13) | C12—C11—C14—N1 | −28.98 (17) |
C4—C5—C6—C1 | 0.5 (2) | C10—C11—C14—C15 | −28.60 (19) |
C4—C5—C6—C7 | 177.06 (13) | C12—C11—C14—C15 | 150.32 (14) |
C1—C6—C7—O1 | 160.66 (14) | C11—C14—N1—N2 | 175.16 (10) |
C5—C6—C7—O1 | −15.8 (2) | C15—C14—N1—N2 | −4.1 (2) |
C1—C6—C7—O2 | −18.01 (18) | N3—C16—N2—N1 | −9.43 (18) |
C5—C6—C7—O2 | 165.53 (12) | S1—C16—N2—N1 | 172.24 (9) |
C13—C8—C9—C10 | 3.3 (2) | C14—N1—N2—C16 | 166.17 (12) |
O2—C8—C9—C10 | −178.70 (12) | O1—C7—O2—C8 | −2.8 (2) |
C8—C9—C10—C11 | −2.2 (2) | C6—C7—O2—C8 | 175.91 (11) |
C9—C10—C11—C12 | −0.6 (2) | C9—C8—O2—C7 | 66.31 (17) |
C9—C10—C11—C14 | 178.29 (12) | C13—C8—O2—C7 | −115.64 (14) |
C10—C11—C12—C13 | 2.4 (2) | | |
Hydrogen-bond geometry (Å, º) topCg2 is the centroid of the C8–C13 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···N1 | 0.86 | 2.24 | 2.5953 (18) | 105 |
N2—H2A···S1i | 0.86 | 2.68 | 3.4697 (12) | 153 |
N3—H3A···O1ii | 0.86 | 2.27 | 3.0653 (15) | 153 |
C15—H15B···O1iii | 0.96 | 2.55 | 3.454 (2) | 156 |
N3—H3B···Cg2ii | 0.86 | 2.47 | 3.3385 (15) | 122 |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) x+1, y, z; (iii) −x, −y, −z+1. |
Acknowledgements
The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. VV thanks the DBT, Government of India, for a fellowship.
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