Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229622009202/qf3056sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229622009202/qf30562sup2.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229622009202/qf30562sup5.cml | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229622009202/qf30563sup3.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229622009202/qf30563sup6.cml | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229622009202/qf30564sup4.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229622009202/qf30564sup7.cml | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229622009202/qf3056sup8.pdf |
CCDC references: 2207705; 2207704; 2207703
Data collection: CrysAlis PRO (Rigaku OD, 2020) for (2), (3); CrysAlis PRO (Rigaku OD, 2015) for (4). Cell refinement: CrysAlis PRO (Rigaku OD, 2020) for (2), (3); CrysAlis PRO (Rigaku OD, 2015) for (4). Data reduction: CrysAlis PRO (Rigaku OD, 2020) for (2), (3); CrysAlis PRO (Rigaku OD, 2015) for (4). For all structures, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg & Putz, 2014); software used to prepare material for publication: PLATON (Spek, 2020).
C14H11N3O2·C3H7NO | Z = 2 |
Mr = 326.35 | F(000) = 344 |
Triclinic, P1 | Dx = 1.400 Mg m−3 |
a = 6.8722 (2) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 11.0502 (3) Å | Cell parameters from 7662 reflections |
c = 11.2090 (3) Å | θ = 4.3–75.4° |
α = 65.618 (3)° | µ = 0.81 mm−1 |
β = 89.798 (2)° | T = 100 K |
γ = 87.085 (2)° | Needle, colourless |
V = 774.14 (4) Å3 | 0.18 × 0.15 × 0.09 mm |
Rigaku XtaLAB Synergy DW system with a HyPix-Arc 150 detector diffractometer | 3149 independent reflections |
Radiation source: Rotating-anode X-ray tube, Rigaku (Cu) X-ray Source | 2827 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.018 |
Detector resolution: 10.0000 pixels mm-1 | θmax = 75.8°, θmin = 4.3° |
ω scans | h = −8→8 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2020) | k = −13→13 |
Tmin = 0.644, Tmax = 1.000 | l = −11→13 |
10869 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.125 | w = 1/[σ2(Fo2) + (0.068P)2 + 0.2445P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
3149 reflections | Δρmax = 0.26 e Å−3 |
237 parameters | Δρmin = −0.53 e Å−3 |
0 restraints | Extinction correction: SHELXL2018 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0035 (8) |
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 | Occ. (<1) | |
O1 | 0.56251 (15) | 0.57479 (10) | 0.64199 (9) | 0.0336 (3) | |
H1 | 0.623980 | 0.537400 | 0.713697 | 0.050* | |
C1 | 0.6242 (2) | 0.69751 (14) | 0.57667 (12) | 0.0270 (3) | |
N2 | 0.78400 (17) | 0.73073 (12) | 0.61302 (11) | 0.0290 (3) | |
N3 | 0.83698 (16) | 0.85878 (11) | 0.54111 (10) | 0.0267 (3) | |
H3 | 0.943753 | 0.881584 | 0.567844 | 0.032* | |
O4 | 0.81259 (13) | 1.06599 (9) | 0.38091 (9) | 0.0291 (2) | |
C4 | 0.74557 (18) | 0.95407 (13) | 0.43446 (12) | 0.0239 (3) | |
C5 | 0.45536 (18) | 0.99695 (12) | 0.27933 (12) | 0.0227 (3) | |
C51 | 0.51416 (19) | 1.13221 (13) | 0.18729 (13) | 0.0279 (3) | |
H51 | 0.430899 | 1.165143 | 0.108287 | 0.042* | |
H52 | 0.650440 | 1.126537 | 0.163166 | 0.042* | |
H53 | 0.499590 | 1.193383 | 0.230255 | 0.042* | |
N6 | 0.29158 (15) | 0.95746 (10) | 0.24670 (10) | 0.0232 (2) | |
C7 | 0.22803 (18) | 0.83520 (12) | 0.32149 (12) | 0.0219 (3) | |
C71 | 0.04117 (18) | 0.80255 (12) | 0.27739 (12) | 0.0222 (3) | |
C72 | −0.05964 (19) | 0.89735 (13) | 0.16785 (12) | 0.0238 (3) | |
H72 | −0.007941 | 0.982098 | 0.122002 | 0.029* | |
C73 | −0.23431 (19) | 0.86939 (13) | 0.12510 (12) | 0.0258 (3) | |
H73 | −0.300666 | 0.934803 | 0.050269 | 0.031* | |
C74 | −0.31231 (19) | 0.74614 (14) | 0.19136 (13) | 0.0266 (3) | |
H74 | −0.431782 | 0.726916 | 0.162254 | 0.032* | |
C75 | −0.2141 (2) | 0.65153 (14) | 0.30034 (13) | 0.0298 (3) | |
H75 | −0.266948 | 0.567204 | 0.346295 | 0.036* | |
C76 | −0.0388 (2) | 0.67903 (13) | 0.34298 (13) | 0.0282 (3) | |
H76 | 0.027368 | 0.613064 | 0.417545 | 0.034* | |
C8 | 0.33272 (19) | 0.74615 (13) | 0.43018 (12) | 0.0246 (3) | |
H8 | 0.288564 | 0.659736 | 0.479633 | 0.030* | |
C9 | 0.50491 (18) | 0.78613 (13) | 0.46566 (12) | 0.0236 (3) | |
C10 | 0.56726 (18) | 0.91398 (12) | 0.39235 (12) | 0.0222 (3) | |
O1N | 0.6684 (3) | 0.4638 (2) | 0.88789 (17) | 0.0376 (7) | 0.611 (5) |
C1N | 0.8086 (4) | 0.3886 (2) | 0.9393 (2) | 0.0291 (7) | 0.611 (5) |
H1N | 0.890 (4) | 0.338 (3) | 0.891 (3) | 0.035* | 0.611 (5) |
O1N' | 0.7370 (4) | 0.4178 (3) | 0.8593 (3) | 0.0302 (9)* | 0.389 (5) |
C1N' | 0.7224 (5) | 0.4373 (3) | 0.9639 (4) | 0.0230 (10)* | 0.389 (5) |
H1N' | 0.630 (6) | 0.495 (4) | 0.978 (4) | 0.028* | 0.389 (5) |
N1N | 0.86445 (19) | 0.36515 (12) | 1.06150 (11) | 0.0355 (3) | |
C2N | 1.0296 (3) | 0.27128 (17) | 1.0960 (2) | 0.0557 (5) | |
H21N | 1.060941 | 0.248621 | 1.022055 | 0.083* | |
H22N | 0.998795 | 0.190547 | 1.172305 | 0.083* | |
H23N | 1.141804 | 0.310677 | 1.117131 | 0.083* | |
C3N | 0.8029 (2) | 0.40981 (16) | 1.15938 (19) | 0.0472 (4) | |
H31N | 0.699026 | 0.479858 | 1.123019 | 0.071* | |
H32N | 0.913547 | 0.445116 | 1.187269 | 0.071* | |
H33N | 0.754060 | 0.335043 | 1.234874 | 0.071* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0351 (5) | 0.0328 (5) | 0.0236 (5) | −0.0133 (4) | −0.0083 (4) | −0.0009 (4) |
C1 | 0.0288 (6) | 0.0305 (7) | 0.0202 (6) | −0.0082 (5) | −0.0013 (5) | −0.0082 (5) |
N2 | 0.0305 (6) | 0.0308 (6) | 0.0226 (5) | −0.0089 (5) | −0.0041 (4) | −0.0071 (5) |
N3 | 0.0261 (5) | 0.0294 (6) | 0.0244 (5) | −0.0088 (4) | −0.0043 (4) | −0.0102 (4) |
O4 | 0.0282 (5) | 0.0268 (5) | 0.0324 (5) | −0.0079 (4) | −0.0054 (4) | −0.0115 (4) |
C4 | 0.0239 (6) | 0.0273 (6) | 0.0237 (6) | −0.0046 (5) | −0.0002 (5) | −0.0132 (5) |
C5 | 0.0226 (6) | 0.0224 (6) | 0.0258 (6) | −0.0030 (5) | −0.0002 (5) | −0.0123 (5) |
C51 | 0.0272 (6) | 0.0218 (6) | 0.0330 (7) | −0.0047 (5) | −0.0051 (5) | −0.0090 (5) |
N6 | 0.0223 (5) | 0.0214 (5) | 0.0262 (5) | −0.0036 (4) | −0.0014 (4) | −0.0100 (4) |
C7 | 0.0221 (6) | 0.0232 (6) | 0.0224 (6) | −0.0044 (5) | 0.0011 (5) | −0.0110 (5) |
C71 | 0.0225 (6) | 0.0239 (6) | 0.0224 (6) | −0.0047 (5) | 0.0008 (5) | −0.0114 (5) |
C72 | 0.0265 (6) | 0.0228 (6) | 0.0235 (6) | −0.0051 (5) | 0.0009 (5) | −0.0105 (5) |
C73 | 0.0258 (6) | 0.0285 (7) | 0.0244 (6) | −0.0021 (5) | −0.0030 (5) | −0.0121 (5) |
C74 | 0.0230 (6) | 0.0337 (7) | 0.0283 (6) | −0.0075 (5) | 0.0008 (5) | −0.0173 (6) |
C75 | 0.0304 (7) | 0.0282 (7) | 0.0297 (7) | −0.0117 (5) | 0.0007 (5) | −0.0098 (5) |
C76 | 0.0278 (7) | 0.0262 (7) | 0.0270 (6) | −0.0067 (5) | −0.0039 (5) | −0.0070 (5) |
C8 | 0.0261 (6) | 0.0251 (6) | 0.0218 (6) | −0.0082 (5) | 0.0000 (5) | −0.0083 (5) |
C9 | 0.0244 (6) | 0.0275 (6) | 0.0204 (6) | −0.0049 (5) | 0.0001 (5) | −0.0110 (5) |
C10 | 0.0219 (6) | 0.0253 (6) | 0.0228 (6) | −0.0040 (5) | 0.0005 (5) | −0.0129 (5) |
O1N | 0.0315 (10) | 0.0425 (11) | 0.0261 (10) | −0.0040 (8) | −0.0073 (7) | −0.0011 (8) |
C1N | 0.0314 (13) | 0.0293 (12) | 0.0226 (12) | −0.0112 (10) | −0.0027 (9) | −0.0055 (9) |
N1N | 0.0434 (7) | 0.0327 (6) | 0.0237 (6) | −0.0175 (5) | −0.0084 (5) | −0.0031 (5) |
C2N | 0.0631 (11) | 0.0355 (8) | 0.0799 (13) | −0.0145 (8) | 0.0387 (10) | −0.0345 (9) |
C3N | 0.0382 (8) | 0.0305 (8) | 0.0738 (12) | −0.0038 (6) | 0.0176 (8) | −0.0223 (8) |
O1—C1 | 1.3383 (16) | C73—H73 | 0.9500 |
O1—H1 | 0.8400 | C74—C75 | 1.3859 (19) |
C1—N2 | 1.2942 (17) | C74—H74 | 0.9500 |
C1—C9 | 1.4485 (18) | C75—C76 | 1.3905 (18) |
N2—N3 | 1.3759 (15) | C75—H75 | 0.9500 |
N3—C4 | 1.3532 (17) | C76—H76 | 0.9500 |
N3—H3 | 0.8800 | C8—C9 | 1.3982 (17) |
O4—C4 | 1.2430 (15) | C8—H8 | 0.9500 |
C4—C10 | 1.4671 (16) | C9—C10 | 1.3984 (17) |
C5—N6 | 1.3325 (16) | O1N—C1N | 1.215 (4) |
C5—C10 | 1.4188 (17) | C1N—N1N | 1.339 (2) |
C5—C51 | 1.4990 (17) | C1N—H1N | 1.06 (3) |
C51—H51 | 0.9800 | O1N'—C1N' | 1.279 (6) |
C51—H52 | 0.9800 | C1N'—N1N | 1.412 (4) |
C51—H53 | 0.9800 | C1N'—H1N' | 0.94 (4) |
N6—C7 | 1.3569 (16) | N1N—C3N | 1.431 (2) |
C7—C8 | 1.3837 (18) | N1N—C2N | 1.437 (2) |
C7—C71 | 1.4908 (17) | C2N—H21N | 0.9800 |
C71—C76 | 1.3965 (17) | C2N—H22N | 0.9800 |
C71—C72 | 1.3983 (18) | C2N—H23N | 0.9800 |
C72—C73 | 1.3892 (18) | C3N—H31N | 0.9800 |
C72—H72 | 0.9500 | C3N—H32N | 0.9800 |
C73—C74 | 1.3893 (18) | C3N—H33N | 0.9800 |
C1—O1—H1 | 109.5 | C74—C75—H75 | 119.7 |
N2—C1—O1 | 119.90 (12) | C76—C75—H75 | 119.7 |
N2—C1—C9 | 123.63 (12) | C75—C76—C71 | 120.73 (12) |
O1—C1—C9 | 116.47 (11) | C75—C76—H76 | 119.6 |
C1—N2—N3 | 116.34 (11) | C71—C76—H76 | 119.6 |
C4—N3—N2 | 128.17 (10) | C7—C8—C9 | 118.56 (12) |
C4—N3—H3 | 115.9 | C7—C8—H8 | 120.7 |
N2—N3—H3 | 115.9 | C9—C8—H8 | 120.7 |
O4—C4—N3 | 120.11 (11) | C8—C9—C10 | 120.02 (12) |
O4—C4—C10 | 124.99 (11) | C8—C9—C1 | 121.69 (12) |
N3—C4—C10 | 114.89 (11) | C10—C9—C1 | 118.28 (11) |
N6—C5—C10 | 121.55 (11) | C9—C10—C5 | 117.69 (11) |
N6—C5—C51 | 115.52 (11) | C9—C10—C4 | 118.63 (11) |
C10—C5—C51 | 122.91 (11) | C5—C10—C4 | 123.67 (11) |
C5—C51—H51 | 109.5 | O1N—C1N—N1N | 120.2 (2) |
C5—C51—H52 | 109.5 | O1N—C1N—H1N | 122.6 (15) |
H51—C51—H52 | 109.5 | N1N—C1N—H1N | 117.2 (15) |
C5—C51—H53 | 109.5 | O1N'—C1N'—N1N | 114.3 (3) |
H51—C51—H53 | 109.5 | O1N'—C1N'—H1N' | 126 (3) |
H52—C51—H53 | 109.5 | N1N—C1N'—H1N' | 120 (2) |
C5—N6—C7 | 120.28 (11) | C1N—N1N—C3N | 136.48 (18) |
N6—C7—C8 | 121.79 (11) | C1N'—N1N—C3N | 98.5 (2) |
N6—C7—C71 | 115.72 (11) | C1N—N1N—C2N | 107.44 (18) |
C8—C7—C71 | 122.48 (11) | C1N'—N1N—C2N | 145.4 (2) |
C76—C71—C72 | 118.20 (11) | C3N—N1N—C2N | 116.07 (14) |
C76—C71—C7 | 121.91 (11) | N1N—C2N—H21N | 109.5 |
C72—C71—C7 | 119.89 (11) | N1N—C2N—H22N | 109.5 |
C73—C72—C71 | 120.95 (12) | H21N—C2N—H22N | 109.5 |
C73—C72—H72 | 119.5 | N1N—C2N—H23N | 109.5 |
C71—C72—H72 | 119.5 | H21N—C2N—H23N | 109.5 |
C72—C73—C74 | 120.25 (12) | H22N—C2N—H23N | 109.5 |
C72—C73—H73 | 119.9 | N1N—C3N—H31N | 109.5 |
C74—C73—H73 | 119.9 | N1N—C3N—H32N | 109.5 |
C75—C74—C73 | 119.33 (12) | H31N—C3N—H32N | 109.5 |
C75—C74—H74 | 120.3 | N1N—C3N—H33N | 109.5 |
C73—C74—H74 | 120.3 | H31N—C3N—H33N | 109.5 |
C74—C75—C76 | 120.54 (12) | H32N—C3N—H33N | 109.5 |
O1—C1—N2—N3 | −179.77 (11) | C7—C8—C9—C10 | 0.42 (19) |
C9—C1—N2—N3 | 1.1 (2) | C7—C8—C9—C1 | −178.78 (11) |
C1—N2—N3—C4 | −1.9 (2) | N2—C1—C9—C8 | −179.75 (12) |
N2—N3—C4—O4 | 179.58 (12) | O1—C1—C9—C8 | 1.09 (19) |
N2—N3—C4—C10 | 0.41 (19) | N2—C1—C9—C10 | 1.0 (2) |
C10—C5—N6—C7 | −0.34 (19) | O1—C1—C9—C10 | −178.11 (11) |
C51—C5—N6—C7 | 178.26 (11) | C8—C9—C10—C5 | −2.92 (18) |
C5—N6—C7—C8 | −2.37 (19) | C1—C9—C10—C5 | 176.30 (11) |
C5—N6—C7—C71 | 178.79 (10) | C8—C9—C10—C4 | 178.26 (11) |
N6—C7—C71—C76 | 178.28 (11) | C1—C9—C10—C4 | −2.52 (18) |
C8—C7—C71—C76 | −0.6 (2) | N6—C5—C10—C9 | 2.95 (18) |
N6—C7—C71—C72 | −2.10 (17) | C51—C5—C10—C9 | −175.54 (11) |
C8—C7—C71—C72 | 179.06 (12) | N6—C5—C10—C4 | −178.30 (11) |
C76—C71—C72—C73 | −0.19 (19) | C51—C5—C10—C4 | 3.21 (19) |
C7—C71—C72—C73 | −179.82 (11) | O4—C4—C10—C9 | −177.28 (12) |
C71—C72—C73—C74 | 0.3 (2) | N3—C4—C10—C9 | 1.84 (17) |
C72—C73—C74—C75 | 0.0 (2) | O4—C4—C10—C5 | 4.0 (2) |
C73—C74—C75—C76 | −0.3 (2) | N3—C4—C10—C5 | −176.90 (11) |
C74—C75—C76—C71 | 0.3 (2) | O1N—C1N—N1N—C3N | −1.8 (3) |
C72—C71—C76—C75 | −0.1 (2) | O1N—C1N—N1N—C2N | 178.81 (19) |
C7—C71—C76—C75 | 179.50 (12) | O1N'—C1N'—N1N—C3N | −179.6 (2) |
N6—C7—C8—C9 | 2.31 (19) | O1N'—C1N'—N1N—C2N | −0.9 (5) |
C71—C7—C8—C9 | −178.93 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O1N | 0.84 | 1.80 | 2.6006 (19) | 159 |
O1—H1···O1N′ | 0.84 | 1.77 | 2.588 (3) | 164 |
N3—H3···O4i | 0.88 | 1.96 | 2.8413 (14) | 177 |
C75—H75···O1ii | 0.95 | 2.60 | 3.4161 (16) | 144 |
C2N—H22N···O4iii | 0.98 | 2.55 | 3.450 (2) | 153 |
C3N—H31N···O1Niv | 0.98 | 2.56 | 3.415 (3) | 146 |
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x, −y+1, −z+1; (iii) x, y−1, z+1; (iv) −x+1, −y+1, −z+2. |
C18H17N3O4 | F(000) = 712 |
Mr = 339.34 | Dx = 1.409 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 17.4344 (3) Å | Cell parameters from 1548 reflections |
b = 13.0800 (3) Å | θ = 2.5–69.8° |
c = 7.0192 (1) Å | µ = 0.84 mm−1 |
β = 92.315 (1)° | T = 100 K |
V = 1599.37 (5) Å3 | Plate, colourless |
Z = 4 | 0.17 × 0.03 × 0.03 mm |
Rigaku XtaLAB Synergy DW system with a HyPix-Arc 150 detector diffractometer | 3274 independent reflections |
Radiation source: Rotating-anode X-ray tube, Rigaku (Cu) X-ray Source | 2878 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.035 |
Detector resolution: 10.0000 pixels mm-1 | θmax = 75.7°, θmin = 2.5° |
φ scans | h = −21→21 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2020) | k = −15→16 |
Tmin = 0.736, Tmax = 1.000 | l = −8→8 |
15272 measured reflections |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0533P)2 + 0.7835P] where P = (Fo2 + 2Fc2)/3 |
3274 reflections | (Δ/σ)max < 0.001 |
228 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
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 | ||
C1 | 0.20407 (9) | 0.60829 (14) | 0.3354 (2) | 0.0230 (4) | |
O1 | 0.27974 (7) | 0.59919 (9) | 0.30055 (17) | 0.0251 (3) | |
C11 | 0.30819 (10) | 0.49653 (14) | 0.3152 (2) | 0.0242 (4) | |
H111 | 0.280079 | 0.451875 | 0.222334 | 0.029* | |
H112 | 0.301025 | 0.469441 | 0.444930 | 0.029* | |
C12 | 0.39222 (10) | 0.49888 (13) | 0.2738 (2) | 0.0239 (4) | |
O12 | 0.42679 (7) | 0.56808 (10) | 0.20456 (18) | 0.0296 (3) | |
O13 | 0.42359 (7) | 0.40925 (9) | 0.32548 (18) | 0.0279 (3) | |
C13 | 0.50480 (10) | 0.39724 (15) | 0.2903 (3) | 0.0289 (4) | |
H131 | 0.534376 | 0.455913 | 0.343799 | 0.035* | |
H132 | 0.512733 | 0.393650 | 0.151615 | 0.035* | |
C14 | 0.53061 (12) | 0.29977 (16) | 0.3857 (3) | 0.0378 (5) | |
H141 | 0.500106 | 0.242594 | 0.333566 | 0.057* | |
H142 | 0.523598 | 0.304973 | 0.523192 | 0.057* | |
H143 | 0.584979 | 0.288096 | 0.362658 | 0.057* | |
N2 | 0.16413 (8) | 0.52742 (11) | 0.3611 (2) | 0.0243 (3) | |
N3 | 0.08860 (8) | 0.54126 (11) | 0.4001 (2) | 0.0247 (3) | |
H3 | 0.061443 | 0.485415 | 0.415974 | 0.030* | |
C4 | 0.05078 (10) | 0.63117 (13) | 0.4170 (2) | 0.0229 (4) | |
O4 | −0.01768 (7) | 0.63137 (10) | 0.46053 (18) | 0.0272 (3) | |
C5 | 0.06606 (9) | 0.82347 (13) | 0.3958 (2) | 0.0219 (4) | |
C51 | −0.01659 (9) | 0.84556 (14) | 0.4338 (3) | 0.0261 (4) | |
H511 | −0.029101 | 0.816888 | 0.557765 | 0.039* | |
H512 | −0.049690 | 0.814526 | 0.333548 | 0.039* | |
H513 | −0.024832 | 0.919671 | 0.434967 | 0.039* | |
N6 | 0.11052 (8) | 0.90527 (11) | 0.37439 (19) | 0.0231 (3) | |
C7 | 0.18631 (9) | 0.89387 (13) | 0.3400 (2) | 0.0215 (3) | |
C71 | 0.23023 (10) | 0.99101 (14) | 0.3237 (2) | 0.0233 (4) | |
C72 | 0.19108 (11) | 1.08301 (14) | 0.2915 (3) | 0.0304 (4) | |
H72 | 0.136623 | 1.083014 | 0.279027 | 0.036* | |
C73 | 0.23094 (11) | 1.17437 (16) | 0.2777 (3) | 0.0368 (5) | |
H73 | 0.203789 | 1.236386 | 0.254404 | 0.044* | |
C74 | 0.31059 (11) | 1.17518 (15) | 0.2979 (3) | 0.0326 (4) | |
H74 | 0.337833 | 1.237841 | 0.290086 | 0.039* | |
C75 | 0.35012 (10) | 1.08475 (14) | 0.3293 (3) | 0.0278 (4) | |
H75 | 0.404570 | 1.085344 | 0.342154 | 0.033* | |
C76 | 0.31046 (10) | 0.99282 (14) | 0.3420 (2) | 0.0250 (4) | |
H76 | 0.338009 | 0.930930 | 0.363338 | 0.030* | |
C8 | 0.21977 (10) | 0.79844 (13) | 0.3214 (2) | 0.0230 (4) | |
H8 | 0.272420 | 0.792202 | 0.293389 | 0.028* | |
C9 | 0.17444 (9) | 0.71166 (13) | 0.3448 (2) | 0.0217 (3) | |
C10 | 0.09629 (9) | 0.72315 (13) | 0.3834 (2) | 0.0213 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0225 (9) | 0.0251 (9) | 0.0215 (8) | −0.0003 (7) | 0.0032 (6) | −0.0002 (7) |
O1 | 0.0230 (6) | 0.0202 (6) | 0.0326 (7) | 0.0016 (5) | 0.0061 (5) | 0.0010 (5) |
C11 | 0.0275 (9) | 0.0201 (9) | 0.0253 (8) | 0.0020 (7) | 0.0050 (6) | 0.0017 (7) |
C12 | 0.0276 (9) | 0.0209 (8) | 0.0235 (8) | −0.0005 (7) | 0.0036 (6) | −0.0029 (7) |
O12 | 0.0272 (7) | 0.0242 (7) | 0.0380 (7) | −0.0034 (5) | 0.0065 (5) | 0.0023 (5) |
O13 | 0.0260 (7) | 0.0225 (7) | 0.0359 (7) | 0.0023 (5) | 0.0080 (5) | 0.0033 (5) |
C13 | 0.0238 (9) | 0.0273 (10) | 0.0358 (10) | 0.0027 (7) | 0.0062 (7) | −0.0001 (8) |
C14 | 0.0372 (11) | 0.0323 (11) | 0.0442 (11) | 0.0073 (9) | 0.0057 (8) | 0.0005 (9) |
N2 | 0.0241 (7) | 0.0234 (8) | 0.0257 (7) | 0.0004 (6) | 0.0045 (5) | −0.0003 (6) |
N3 | 0.0237 (8) | 0.0202 (7) | 0.0308 (8) | −0.0035 (6) | 0.0067 (6) | −0.0005 (6) |
C4 | 0.0252 (9) | 0.0221 (9) | 0.0214 (8) | −0.0003 (7) | 0.0018 (6) | 0.0001 (6) |
O4 | 0.0235 (6) | 0.0242 (6) | 0.0343 (7) | −0.0015 (5) | 0.0066 (5) | 0.0017 (5) |
C5 | 0.0224 (8) | 0.0232 (9) | 0.0203 (8) | −0.0021 (7) | 0.0025 (6) | −0.0012 (6) |
C51 | 0.0238 (9) | 0.0233 (9) | 0.0315 (9) | 0.0005 (7) | 0.0054 (7) | −0.0006 (7) |
N6 | 0.0246 (7) | 0.0215 (7) | 0.0236 (7) | −0.0007 (6) | 0.0037 (5) | −0.0008 (6) |
C7 | 0.0232 (8) | 0.0226 (9) | 0.0187 (8) | −0.0022 (7) | 0.0016 (6) | −0.0002 (6) |
C71 | 0.0256 (9) | 0.0240 (9) | 0.0206 (8) | −0.0022 (7) | 0.0038 (6) | −0.0012 (7) |
C72 | 0.0256 (9) | 0.0257 (10) | 0.0402 (10) | −0.0009 (7) | 0.0052 (7) | −0.0001 (8) |
C73 | 0.0329 (11) | 0.0230 (10) | 0.0546 (13) | 0.0006 (8) | 0.0042 (9) | 0.0016 (9) |
C74 | 0.0326 (10) | 0.0239 (10) | 0.0415 (11) | −0.0085 (7) | 0.0049 (8) | −0.0012 (8) |
C75 | 0.0242 (9) | 0.0305 (10) | 0.0289 (9) | −0.0038 (7) | 0.0042 (7) | −0.0009 (7) |
C76 | 0.0254 (9) | 0.0254 (9) | 0.0244 (8) | −0.0010 (7) | 0.0025 (6) | −0.0011 (7) |
C8 | 0.0204 (8) | 0.0252 (9) | 0.0235 (8) | −0.0007 (7) | 0.0034 (6) | 0.0000 (7) |
C9 | 0.0241 (8) | 0.0215 (9) | 0.0197 (7) | −0.0002 (7) | 0.0018 (6) | −0.0007 (6) |
C10 | 0.0236 (8) | 0.0219 (9) | 0.0186 (7) | −0.0017 (7) | 0.0017 (6) | 0.0003 (6) |
C1—N2 | 1.283 (2) | C5—C10 | 1.418 (2) |
C1—O1 | 1.3565 (19) | C5—C51 | 1.504 (2) |
C1—C9 | 1.450 (2) | C51—H511 | 0.9800 |
O1—C11 | 1.434 (2) | C51—H512 | 0.9800 |
C11—C12 | 1.505 (2) | C51—H513 | 0.9800 |
C11—H111 | 0.9900 | N6—C7 | 1.361 (2) |
C11—H112 | 0.9900 | C7—C8 | 1.386 (2) |
C12—O12 | 1.201 (2) | C7—C71 | 1.490 (2) |
C12—O13 | 1.338 (2) | C71—C72 | 1.397 (2) |
O13—C13 | 1.456 (2) | C71—C76 | 1.400 (2) |
C13—C14 | 1.501 (3) | C72—C73 | 1.388 (3) |
C13—H131 | 0.9900 | C72—H72 | 0.9500 |
C13—H132 | 0.9900 | C73—C74 | 1.390 (3) |
C14—H141 | 0.9800 | C73—H73 | 0.9500 |
C14—H142 | 0.9800 | C74—C75 | 1.382 (3) |
C14—H143 | 0.9800 | C74—H74 | 0.9500 |
N2—N3 | 1.368 (2) | C75—C76 | 1.392 (2) |
N3—C4 | 1.356 (2) | C75—H75 | 0.9500 |
N3—H3 | 0.8800 | C76—H76 | 0.9500 |
C4—O4 | 1.244 (2) | C8—C9 | 1.397 (2) |
C4—C10 | 1.465 (2) | C8—H8 | 0.9500 |
C5—N6 | 1.333 (2) | C9—C10 | 1.408 (2) |
N2—C1—O1 | 119.35 (16) | C5—C51—H512 | 109.5 |
N2—C1—C9 | 124.47 (15) | H511—C51—H512 | 109.5 |
O1—C1—C9 | 116.16 (15) | C5—C51—H513 | 109.5 |
C1—O1—C11 | 113.92 (13) | H511—C51—H513 | 109.5 |
O1—C11—C12 | 107.68 (14) | H512—C51—H513 | 109.5 |
O1—C11—H111 | 110.2 | C5—N6—C7 | 120.34 (15) |
C12—C11—H111 | 110.2 | N6—C7—C8 | 122.05 (15) |
O1—C11—H112 | 110.2 | N6—C7—C71 | 115.20 (15) |
C12—C11—H112 | 110.2 | C8—C7—C71 | 122.75 (15) |
H111—C11—H112 | 108.5 | C72—C71—C76 | 118.69 (16) |
O12—C12—O13 | 124.33 (16) | C72—C71—C7 | 119.84 (15) |
O12—C12—C11 | 126.99 (16) | C76—C71—C7 | 121.47 (16) |
O13—C12—C11 | 108.68 (14) | C73—C72—C71 | 120.68 (17) |
C12—O13—C13 | 116.01 (13) | C73—C72—H72 | 119.7 |
O13—C13—C14 | 106.99 (15) | C71—C72—H72 | 119.7 |
O13—C13—H131 | 110.3 | C72—C73—C74 | 120.02 (18) |
C14—C13—H131 | 110.3 | C72—C73—H73 | 120.0 |
O13—C13—H132 | 110.3 | C74—C73—H73 | 120.0 |
C14—C13—H132 | 110.3 | C75—C74—C73 | 119.96 (17) |
H131—C13—H132 | 108.6 | C75—C74—H74 | 120.0 |
C13—C14—H141 | 109.5 | C73—C74—H74 | 120.0 |
C13—C14—H142 | 109.5 | C74—C75—C76 | 120.26 (17) |
H141—C14—H142 | 109.5 | C74—C75—H75 | 119.9 |
C13—C14—H143 | 109.5 | C76—C75—H75 | 119.9 |
H141—C14—H143 | 109.5 | C75—C76—C71 | 120.39 (17) |
H142—C14—H143 | 109.5 | C75—C76—H76 | 119.8 |
C1—N2—N3 | 116.83 (15) | C71—C76—H76 | 119.8 |
C4—N3—N2 | 127.43 (14) | C7—C8—C9 | 118.59 (15) |
C4—N3—H3 | 116.3 | C7—C8—H8 | 120.7 |
N2—N3—H3 | 116.3 | C9—C8—H8 | 120.7 |
O4—C4—N3 | 119.87 (16) | C8—C9—C10 | 119.50 (16) |
O4—C4—C10 | 124.68 (16) | C8—C9—C1 | 123.25 (15) |
N3—C4—C10 | 115.45 (15) | C10—C9—C1 | 117.24 (15) |
N6—C5—C10 | 121.09 (15) | C9—C10—C5 | 118.40 (15) |
N6—C5—C51 | 115.55 (15) | C9—C10—C4 | 118.54 (15) |
C10—C5—C51 | 123.36 (15) | C5—C10—C4 | 123.01 (15) |
C5—C51—H511 | 109.5 | ||
N2—C1—O1—C11 | −5.8 (2) | C73—C74—C75—C76 | −0.4 (3) |
C9—C1—O1—C11 | 172.95 (14) | C74—C75—C76—C71 | −0.2 (3) |
C1—O1—C11—C12 | −179.80 (13) | C72—C71—C76—C75 | 0.3 (2) |
O1—C11—C12—O12 | −13.6 (2) | C7—C71—C76—C75 | −178.98 (15) |
O1—C11—C12—O13 | 167.01 (13) | N6—C7—C8—C9 | −2.0 (2) |
O12—C12—O13—C13 | −1.0 (2) | C71—C7—C8—C9 | 178.07 (15) |
C11—C12—O13—C13 | 178.39 (13) | C7—C8—C9—C10 | 1.0 (2) |
C12—O13—C13—C14 | 171.25 (15) | C7—C8—C9—C1 | −177.68 (15) |
O1—C1—N2—N3 | 178.51 (13) | N2—C1—C9—C8 | 178.16 (16) |
C9—C1—N2—N3 | −0.1 (2) | O1—C1—C9—C8 | −0.5 (2) |
C1—N2—N3—C4 | −0.8 (2) | N2—C1—C9—C10 | −0.5 (2) |
N2—N3—C4—O4 | −177.17 (15) | O1—C1—C9—C10 | −179.14 (13) |
N2—N3—C4—C10 | 2.1 (2) | C8—C9—C10—C5 | 0.5 (2) |
C10—C5—N6—C7 | 0.0 (2) | C1—C9—C10—C5 | 179.22 (14) |
C51—C5—N6—C7 | 179.79 (14) | C8—C9—C10—C4 | −176.93 (14) |
C5—N6—C7—C8 | 1.6 (2) | C1—C9—C10—C4 | 1.8 (2) |
C5—N6—C7—C71 | −178.54 (14) | N6—C5—C10—C9 | −1.0 (2) |
N6—C7—C71—C72 | −17.4 (2) | C51—C5—C10—C9 | 179.22 (14) |
C8—C7—C71—C72 | 162.49 (16) | N6—C5—C10—C4 | 176.29 (15) |
N6—C7—C71—C76 | 161.87 (15) | C51—C5—C10—C4 | −3.5 (2) |
C8—C7—C71—C76 | −18.2 (2) | O4—C4—C10—C9 | 176.72 (15) |
C76—C71—C72—C73 | 0.1 (3) | N3—C4—C10—C9 | −2.5 (2) |
C7—C71—C72—C73 | 179.41 (17) | O4—C4—C10—C5 | −0.6 (3) |
C71—C72—C73—C74 | −0.7 (3) | N3—C4—C10—C5 | −179.77 (15) |
C72—C73—C74—C75 | 0.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O4i | 0.88 | 1.93 | 2.7717 (19) | 160 |
C14—H141···O12ii | 0.98 | 2.63 | 3.190 (2) | 116 |
C14—H142···O12iii | 0.98 | 2.65 | 3.411 (3) | 135 |
C13—H132···O12iv | 0.99 | 2.80 | 3.746 (2) | 161 |
C51—H512···O4v | 0.98 | 2.79 | 3.335 (2) | 116 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y+1, −z; (v) x, −y+3/2, z−1/2. |
C22H23N3O6 | Z = 2 |
Mr = 425.43 | F(000) = 448 |
Triclinic, P1 | Dx = 1.371 Mg m−3 |
a = 8.679 (2) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 8.751 (2) Å | Cell parameters from 1514 reflections |
c = 15.137 (4) Å | θ = 3.1–72.4° |
α = 92.24 (2)° | µ = 0.84 mm−1 |
β = 106.06 (3)° | T = 100 K |
γ = 109.46 (3)° | Needle, colourless |
V = 1030.7 (5) Å3 | 0.09 × 0.03 × 0.02 mm |
Rigaku Xcalibur Onyx diffractometer | 4142 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source | 2089 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.068 |
Detector resolution: 8.1956 pixels mm-1 | θmax = 77.3°, θmin = 3.1° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −8→10 |
Tmin = 0.840, Tmax = 1.000 | l = −17→19 |
7128 measured reflections |
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)] = 0.063 | H-atom parameters constrained |
wR(F2) = 0.165 | w = 1/[σ2(Fo2) + (0.063P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max < 0.001 |
4142 reflections | Δρmax = 0.35 e Å−3 |
284 parameters | Δρmin = −0.38 e Å−3 |
0 restraints | Extinction correction: SHELXL2018 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0037 (6) |
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 | ||
C1 | 0.2620 (4) | 0.4605 (4) | 0.3410 (2) | 0.0254 (7) | |
O1 | 0.1154 (3) | 0.4540 (3) | 0.35841 (16) | 0.0280 (5) | |
C11 | −0.0362 (4) | 0.3256 (4) | 0.3014 (2) | 0.0278 (7) | |
H111 | −0.131455 | 0.312960 | 0.327715 | 0.033* | |
H112 | −0.015212 | 0.221076 | 0.301129 | 0.033* | |
C12 | −0.0874 (4) | 0.3619 (4) | 0.2024 (2) | 0.0271 (7) | |
O12 | −0.0317 (3) | 0.4891 (3) | 0.17669 (17) | 0.0319 (6) | |
C13 | −0.2667 (5) | 0.2383 (5) | 0.0501 (3) | 0.0419 (10) | |
H131 | −0.284006 | 0.343818 | 0.042431 | 0.050* | |
H132 | −0.377843 | 0.148709 | 0.019592 | 0.050* | |
O13 | −0.2094 (3) | 0.2259 (3) | 0.14844 (17) | 0.0335 (6) | |
C14 | −0.1360 (6) | 0.2276 (6) | 0.0046 (3) | 0.0553 (12) | |
H141 | −0.025470 | 0.315251 | 0.035544 | 0.083* | |
H142 | −0.174650 | 0.239485 | −0.061125 | 0.083* | |
H143 | −0.122656 | 0.121111 | 0.009848 | 0.083* | |
N2 | 0.2563 (3) | 0.3601 (3) | 0.27490 (19) | 0.0255 (6) | |
N3 | 0.4096 (3) | 0.3724 (3) | 0.26150 (19) | 0.0250 (6) | |
C31 | 0.3876 (5) | 0.2649 (4) | 0.1803 (2) | 0.0291 (7) | |
H311 | 0.294619 | 0.158906 | 0.175297 | 0.035* | |
H312 | 0.494912 | 0.243630 | 0.186311 | 0.035* | |
C32 | 0.3434 (4) | 0.3423 (4) | 0.0937 (2) | 0.0259 (7) | |
O32 | 0.3488 (3) | 0.4824 (3) | 0.09355 (17) | 0.0342 (6) | |
C33 | 0.2566 (5) | 0.2991 (4) | −0.0702 (2) | 0.0340 (8) | |
H331 | 0.355936 | 0.394237 | −0.072688 | 0.041* | |
H332 | 0.157605 | 0.334695 | −0.076461 | 0.041* | |
O33 | 0.2984 (3) | 0.2349 (3) | 0.01799 (16) | 0.0303 (6) | |
C34 | 0.2136 (7) | 0.1640 (6) | −0.1464 (3) | 0.0586 (13) | |
H341 | 0.190424 | 0.204147 | −0.206420 | 0.088* | |
H342 | 0.111686 | 0.072779 | −0.145100 | 0.088* | |
H343 | 0.310542 | 0.126304 | −0.137717 | 0.088* | |
C4 | 0.5693 (4) | 0.4836 (4) | 0.3110 (2) | 0.0267 (7) | |
O4 | 0.6969 (3) | 0.4861 (3) | 0.28866 (18) | 0.0376 (6) | |
C5 | 0.7260 (4) | 0.7091 (4) | 0.4497 (2) | 0.0294 (8) | |
C51 | 0.9019 (4) | 0.7287 (5) | 0.4444 (3) | 0.0377 (9) | |
H511 | 0.909036 | 0.754376 | 0.382928 | 0.057* | |
H512 | 0.922899 | 0.626558 | 0.454786 | 0.057* | |
H513 | 0.988388 | 0.817905 | 0.492179 | 0.057* | |
N6 | 0.7226 (3) | 0.8078 (3) | 0.51761 (19) | 0.0277 (6) | |
C7 | 0.5707 (4) | 0.8014 (4) | 0.5292 (2) | 0.0257 (7) | |
C71 | 0.5809 (4) | 0.9194 (4) | 0.6049 (2) | 0.0248 (7) | |
C72 | 0.7405 (4) | 1.0315 (4) | 0.6607 (2) | 0.0289 (8) | |
H72 | 0.843074 | 1.028627 | 0.650965 | 0.035* | |
C73 | 0.7501 (5) | 1.1461 (4) | 0.7300 (2) | 0.0345 (8) | |
H73 | 0.858905 | 1.221882 | 0.766524 | 0.041* | |
C74 | 0.6019 (5) | 1.1506 (4) | 0.7460 (2) | 0.0338 (8) | |
H74 | 0.608836 | 1.229495 | 0.793324 | 0.041* | |
C75 | 0.4441 (5) | 1.0397 (4) | 0.6929 (2) | 0.0337 (8) | |
H75 | 0.342569 | 1.041059 | 0.704692 | 0.040* | |
C76 | 0.4330 (5) | 0.9267 (4) | 0.6228 (2) | 0.0302 (8) | |
H76 | 0.323325 | 0.852674 | 0.586150 | 0.036* | |
C8 | 0.4162 (4) | 0.6887 (4) | 0.4729 (2) | 0.0257 (7) | |
H8 | 0.310806 | 0.683071 | 0.482375 | 0.031* | |
C9 | 0.4185 (4) | 0.5840 (4) | 0.4022 (2) | 0.0232 (7) | |
C10 | 0.5727 (4) | 0.5921 (4) | 0.3879 (2) | 0.0261 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0263 (17) | 0.0302 (18) | 0.0248 (17) | 0.0126 (14) | 0.0118 (14) | 0.0075 (14) |
O1 | 0.0188 (11) | 0.0366 (13) | 0.0285 (13) | 0.0093 (10) | 0.0085 (10) | 0.0013 (10) |
C11 | 0.0184 (16) | 0.0282 (17) | 0.0296 (18) | 0.0040 (13) | 0.0024 (14) | −0.0013 (14) |
C12 | 0.0145 (15) | 0.0309 (18) | 0.0331 (19) | 0.0079 (13) | 0.0044 (14) | −0.0007 (15) |
O12 | 0.0307 (13) | 0.0221 (12) | 0.0394 (15) | 0.0068 (10) | 0.0083 (11) | 0.0056 (10) |
C13 | 0.035 (2) | 0.047 (2) | 0.035 (2) | 0.0129 (18) | 0.0019 (17) | −0.0007 (18) |
O13 | 0.0305 (13) | 0.0299 (13) | 0.0324 (14) | 0.0041 (10) | 0.0071 (11) | −0.0015 (11) |
C14 | 0.052 (3) | 0.073 (3) | 0.036 (2) | 0.020 (2) | 0.011 (2) | −0.002 (2) |
N2 | 0.0244 (14) | 0.0324 (15) | 0.0254 (14) | 0.0150 (12) | 0.0104 (12) | 0.0070 (12) |
N3 | 0.0229 (14) | 0.0295 (15) | 0.0250 (15) | 0.0111 (11) | 0.0091 (12) | 0.0034 (12) |
C31 | 0.0325 (18) | 0.0296 (17) | 0.0302 (19) | 0.0150 (14) | 0.0125 (16) | 0.0064 (15) |
C32 | 0.0257 (17) | 0.0241 (16) | 0.0266 (18) | 0.0072 (13) | 0.0084 (14) | 0.0021 (14) |
O32 | 0.0399 (15) | 0.0307 (13) | 0.0326 (14) | 0.0139 (11) | 0.0104 (11) | 0.0057 (11) |
C33 | 0.039 (2) | 0.037 (2) | 0.0289 (19) | 0.0167 (16) | 0.0106 (16) | 0.0064 (16) |
O33 | 0.0381 (14) | 0.0281 (12) | 0.0272 (13) | 0.0155 (10) | 0.0094 (11) | 0.0022 (10) |
C34 | 0.089 (4) | 0.067 (3) | 0.030 (2) | 0.048 (3) | 0.010 (2) | 0.007 (2) |
C4 | 0.0220 (16) | 0.0311 (17) | 0.0247 (17) | 0.0099 (13) | 0.0027 (14) | 0.0058 (14) |
O4 | 0.0255 (13) | 0.0459 (15) | 0.0457 (16) | 0.0141 (11) | 0.0167 (12) | 0.0000 (12) |
C5 | 0.0295 (18) | 0.0333 (18) | 0.0277 (18) | 0.0122 (15) | 0.0108 (15) | 0.0102 (15) |
C51 | 0.0249 (19) | 0.049 (2) | 0.038 (2) | 0.0105 (16) | 0.0107 (16) | 0.0020 (18) |
N6 | 0.0233 (14) | 0.0339 (15) | 0.0252 (15) | 0.0096 (12) | 0.0070 (12) | 0.0050 (12) |
C7 | 0.0256 (17) | 0.0289 (17) | 0.0241 (17) | 0.0108 (14) | 0.0082 (14) | 0.0094 (14) |
C71 | 0.0256 (16) | 0.0275 (16) | 0.0210 (16) | 0.0095 (13) | 0.0063 (14) | 0.0076 (13) |
C72 | 0.0231 (17) | 0.0320 (18) | 0.0270 (18) | 0.0089 (14) | 0.0017 (14) | 0.0044 (15) |
C73 | 0.036 (2) | 0.0266 (18) | 0.0299 (19) | 0.0030 (15) | 0.0042 (16) | 0.0026 (15) |
C74 | 0.053 (2) | 0.0227 (17) | 0.0270 (19) | 0.0155 (16) | 0.0112 (18) | 0.0040 (14) |
C75 | 0.046 (2) | 0.0274 (18) | 0.0304 (19) | 0.0134 (16) | 0.0156 (17) | 0.0039 (15) |
C76 | 0.0330 (19) | 0.0269 (17) | 0.0320 (19) | 0.0107 (14) | 0.0116 (16) | 0.0069 (15) |
C8 | 0.0231 (16) | 0.0293 (17) | 0.0250 (17) | 0.0099 (13) | 0.0071 (14) | 0.0065 (14) |
C9 | 0.0192 (15) | 0.0253 (16) | 0.0197 (16) | 0.0040 (12) | 0.0021 (13) | 0.0045 (13) |
C10 | 0.0248 (17) | 0.0274 (17) | 0.0254 (17) | 0.0094 (14) | 0.0067 (14) | 0.0045 (14) |
C1—N2 | 1.285 (4) | C34—H341 | 0.9800 |
C1—O1 | 1.353 (4) | C34—H342 | 0.9800 |
C1—C9 | 1.456 (4) | C34—H343 | 0.9800 |
O1—C11 | 1.432 (4) | C4—O4 | 1.238 (4) |
C11—C12 | 1.519 (5) | C4—C10 | 1.461 (5) |
C11—H111 | 0.9900 | C5—N6 | 1.329 (4) |
C11—H112 | 0.9900 | C5—C10 | 1.422 (5) |
C12—O12 | 1.185 (4) | C5—C51 | 1.504 (5) |
C12—O13 | 1.345 (4) | C51—H511 | 0.9800 |
C13—O13 | 1.454 (4) | C51—H512 | 0.9800 |
C13—C14 | 1.506 (6) | C51—H513 | 0.9800 |
C13—H131 | 0.9900 | N6—C7 | 1.361 (4) |
C13—H132 | 0.9900 | C7—C8 | 1.385 (5) |
C14—H141 | 0.9800 | C7—C71 | 1.475 (5) |
C14—H142 | 0.9800 | C71—C76 | 1.405 (5) |
C14—H143 | 0.9800 | C71—C72 | 1.406 (5) |
N2—N3 | 1.371 (4) | C72—C73 | 1.387 (5) |
N3—C4 | 1.378 (4) | C72—H72 | 0.9500 |
N3—C31 | 1.447 (4) | C73—C74 | 1.387 (5) |
C31—C32 | 1.512 (5) | C73—H73 | 0.9500 |
C31—H311 | 0.9900 | C74—C75 | 1.381 (5) |
C31—H312 | 0.9900 | C74—H74 | 0.9500 |
C32—O32 | 1.211 (4) | C75—C76 | 1.382 (5) |
C32—O33 | 1.331 (4) | C75—H75 | 0.9500 |
C33—O33 | 1.468 (4) | C76—H76 | 0.9500 |
C33—C34 | 1.493 (5) | C8—C9 | 1.390 (4) |
C33—H331 | 0.9900 | C8—H8 | 0.9500 |
C33—H332 | 0.9900 | C9—C10 | 1.393 (4) |
N2—C1—O1 | 119.9 (3) | H341—C34—H342 | 109.5 |
N2—C1—C9 | 124.7 (3) | C33—C34—H343 | 109.5 |
O1—C1—C9 | 115.4 (3) | H341—C34—H343 | 109.5 |
C1—O1—C11 | 114.7 (2) | H342—C34—H343 | 109.5 |
O1—C11—C12 | 111.2 (3) | O4—C4—N3 | 119.8 (3) |
O1—C11—H111 | 109.4 | O4—C4—C10 | 124.8 (3) |
C12—C11—H111 | 109.4 | N3—C4—C10 | 115.4 (3) |
O1—C11—H112 | 109.4 | N6—C5—C10 | 121.6 (3) |
C12—C11—H112 | 109.4 | N6—C5—C51 | 115.3 (3) |
H111—C11—H112 | 108.0 | C10—C5—C51 | 123.0 (3) |
O12—C12—O13 | 125.3 (3) | C5—C51—H511 | 109.5 |
O12—C12—C11 | 126.0 (3) | C5—C51—H512 | 109.5 |
O13—C12—C11 | 108.6 (3) | H511—C51—H512 | 109.5 |
O13—C13—C14 | 110.4 (3) | C5—C51—H513 | 109.5 |
O13—C13—H131 | 109.6 | H511—C51—H513 | 109.5 |
C14—C13—H131 | 109.6 | H512—C51—H513 | 109.5 |
O13—C13—H132 | 109.6 | C5—N6—C7 | 120.7 (3) |
C14—C13—H132 | 109.6 | N6—C7—C8 | 121.1 (3) |
H131—C13—H132 | 108.1 | N6—C7—C71 | 116.3 (3) |
C12—O13—C13 | 115.4 (3) | C8—C7—C71 | 122.6 (3) |
C13—C14—H141 | 109.5 | C76—C71—C72 | 117.5 (3) |
C13—C14—H142 | 109.5 | C76—C71—C7 | 121.7 (3) |
H141—C14—H142 | 109.5 | C72—C71—C7 | 120.8 (3) |
C13—C14—H143 | 109.5 | C73—C72—C71 | 120.9 (3) |
H141—C14—H143 | 109.5 | C73—C72—H72 | 119.6 |
H142—C14—H143 | 109.5 | C71—C72—H72 | 119.6 |
C1—N2—N3 | 116.9 (3) | C74—C73—C72 | 120.4 (3) |
N2—N3—C4 | 126.5 (3) | C74—C73—H73 | 119.8 |
N2—N3—C31 | 112.5 (3) | C72—C73—H73 | 119.8 |
C4—N3—C31 | 120.7 (3) | C75—C74—C73 | 119.6 (3) |
N3—C31—C32 | 110.2 (3) | C75—C74—H74 | 120.2 |
N3—C31—H311 | 109.6 | C73—C74—H74 | 120.2 |
C32—C31—H311 | 109.6 | C74—C75—C76 | 120.5 (4) |
N3—C31—H312 | 109.6 | C74—C75—H75 | 119.8 |
C32—C31—H312 | 109.6 | C76—C75—H75 | 119.8 |
H311—C31—H312 | 108.1 | C75—C76—C71 | 121.2 (3) |
O32—C32—O33 | 125.0 (3) | C75—C76—H76 | 119.4 |
O32—C32—C31 | 124.6 (3) | C71—C76—H76 | 119.4 |
O33—C32—C31 | 110.4 (3) | C7—C8—C9 | 118.6 (3) |
O33—C33—C34 | 107.2 (3) | C7—C8—H8 | 120.7 |
O33—C33—H331 | 110.3 | C9—C8—H8 | 120.7 |
C34—C33—H331 | 110.3 | C8—C9—C10 | 120.9 (3) |
O33—C33—H332 | 110.3 | C8—C9—C1 | 122.0 (3) |
C34—C33—H332 | 110.3 | C10—C9—C1 | 117.1 (3) |
H331—C33—H332 | 108.5 | C9—C10—C5 | 117.1 (3) |
C32—O33—C33 | 114.8 (3) | C9—C10—C4 | 119.2 (3) |
C33—C34—H341 | 109.5 | C5—C10—C4 | 123.7 (3) |
C33—C34—H342 | 109.5 | ||
N2—C1—O1—C11 | 2.7 (4) | C8—C7—C71—C72 | 179.7 (3) |
C9—C1—O1—C11 | −176.4 (3) | C76—C71—C72—C73 | −0.9 (5) |
C1—O1—C11—C12 | −72.1 (3) | C7—C71—C72—C73 | 177.9 (3) |
O1—C11—C12—O12 | −12.4 (5) | C71—C72—C73—C74 | 0.9 (5) |
O1—C11—C12—O13 | 168.7 (3) | C72—C73—C74—C75 | 0.3 (5) |
O12—C12—O13—C13 | 3.9 (5) | C73—C74—C75—C76 | −1.3 (5) |
C11—C12—O13—C13 | −177.2 (3) | C74—C75—C76—C71 | 1.2 (5) |
C14—C13—O13—C12 | 76.7 (4) | C72—C71—C76—C75 | −0.1 (5) |
O1—C1—N2—N3 | −179.5 (3) | C7—C71—C76—C75 | −178.9 (3) |
C9—C1—N2—N3 | −0.5 (5) | N6—C7—C8—C9 | −1.6 (5) |
C1—N2—N3—C4 | −1.1 (5) | C71—C7—C8—C9 | 178.9 (3) |
C1—N2—N3—C31 | −174.5 (3) | C7—C8—C9—C10 | −0.1 (5) |
N2—N3—C31—C32 | 81.7 (3) | C7—C8—C9—C1 | 179.0 (3) |
C4—N3—C31—C32 | −92.2 (4) | N2—C1—C9—C8 | −179.7 (3) |
N3—C31—C32—O32 | 9.4 (5) | O1—C1—C9—C8 | −0.6 (5) |
N3—C31—C32—O33 | −170.9 (3) | N2—C1—C9—C10 | −0.5 (5) |
O32—C32—O33—C33 | 1.1 (5) | O1—C1—C9—C10 | 178.5 (3) |
C31—C32—O33—C33 | −178.6 (3) | C8—C9—C10—C5 | 1.2 (5) |
C34—C33—O33—C32 | 178.7 (3) | C1—C9—C10—C5 | −178.0 (3) |
N2—N3—C4—O4 | −176.6 (3) | C8—C9—C10—C4 | −178.0 (3) |
C31—N3—C4—O4 | −3.7 (5) | C1—C9—C10—C4 | 2.8 (4) |
N2—N3—C4—C10 | 3.3 (5) | N6—C5—C10—C9 | −0.6 (5) |
C31—N3—C4—C10 | 176.2 (3) | C51—C5—C10—C9 | 178.3 (3) |
C10—C5—N6—C7 | −1.0 (5) | N6—C5—C10—C4 | 178.5 (3) |
C51—C5—N6—C7 | 179.9 (3) | C51—C5—C10—C4 | −2.5 (6) |
C5—N6—C7—C8 | 2.2 (5) | O4—C4—C10—C9 | 175.9 (3) |
C5—N6—C7—C71 | −178.2 (3) | N3—C4—C10—C9 | −4.1 (5) |
N6—C7—C71—C76 | 179.0 (3) | O4—C4—C10—C5 | −3.3 (6) |
C8—C7—C71—C76 | −1.5 (5) | N3—C4—C10—C5 | 176.8 (3) |
N6—C7—C71—C72 | 0.2 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H111···O4i | 0.99 | 2.44 | 3.053 (4) | 120 |
C13—H131···O32ii | 0.99 | 2.65 | 3.454 (5) | 138 |
C14—H141···O12 | 0.98 | 2.60 | 3.113 (5) | 113 |
C33—H331···O32iii | 0.99 | 2.54 | 3.445 (5) | 152 |
C33—H332···O12ii | 0.99 | 2.50 | 3.278 (4) | 135 |
C73—H73···O12iv | 0.95 | 2.44 | 3.271 (4) | 145 |
Symmetry codes: (i) x−1, y, z; (ii) −x, −y+1, −z; (iii) −x+1, −y+1, −z; (iv) −x+1, −y+2, −z+1. |
Compound | MW | LogP | Hydrogen-bond donors | Hydrogen-bond acceptors | RotB | PSA |
2 | 253.26 | 1.65 | 2 | 5 | 1 | 78.62 |
3 | 425.44 | 2.92 | 0 | 9 | 10 | 109.63 |
4 | 339.35 | 2.62 | 1 | 7 | 6 | 94.19 |
2 | 3 | 4 | |
Bond distances | |||
C1—O1 | 1.3383 (16) | 1.3565 (19) | 1.353 (4) |
C1—N2 | 1.2942 (17) | 1.283 (2) | 1.285 (4) |
N2—N3 | 1.3759 (15) | 1.368 (2) | 1.371 (4) |
C4—N3 | 1.3532 (17) | 1.356 (2) | 1.378 (4) |
C4—O4 | 1.2430 (15) | 1.244 (2) | 1.238 (4) |
C4—C10 | 1.4671 (16) | 1.465 (2) | 1.461 (5) |
C5—C10 | 1.4671 (16) | 1.418 (2) | 1.422 (5) |
C5—C51 | 1.4990 (17) | 1.504 (2) | 1.504 (5) |
C5—N6 | 1.3325 (16) | 1.333 (2) | 1.329 (4) |
C7—N6 | 1.3569 (16) | 1.361 (2) | 1.361 (4) |
C7—C71 | 1.4908 (17) | 1.490 (2) | 1.475 (5) |
C7—C8 | 1.3837 (18) | 1.386 (2) | 1.385 (5) |
C8—C9 | 1.3982 (17) | 1.397 (2) | 1.390 (4) |
C9—C10 | 1.3984 (17) | 1.408 (2) | 1.393 (4) |
Bond angles | |||
O1—C1—N2 | 119.90 (12) | 119.35 (16) | 119.9 (3) |
O1—C1—C9 | 116.47 (11) | 116.16 (15) | 115.4 (3) |
C1—N2—N3 | 116.34 (11) | 116.83 (15) | 116.9 (3) |
N2—N3—C4 | 128.17 (10) | 127.43 (14) | 126.5 (3) |
N2—C1—C9 | 123.63 (12) | 124.47 (15) | 124.7 (3) |
N3—C4—O4 | 120.11 (11) | 119.87 (16) | 119.8 (3) |
O4—C4—C10 | 124.99 (11) | 124.68 (16) | 124.8 (3) |
N3—C4—C10 | 114.89 (11) | 115.45 (15) | 115.4 (3) |
C5—N6—C7 | 120.28 (11) | 120.34 (15) | 120.7 (3) |
N6—C5—C10 | 121.55 (11) | 121.09 (15) | 121.6 (3) |
N6—C5—C51 | 115.52 (11) | 115.55 (15) | 115.3 (3) |
Torsion angles | |||
O1—C1—N2—N3 | -179.77 (11) | 178.51 (13) | -179.5 (3) |
O1—C1—C9—C8 | 1.09 (19) | -0.5 (2) | -0.6 (5) |
C1—N2—N3—C4 | -1.9 (2) | -0.8 (2) | -1.1 (5) |
N2—N3—C4—O4 | 179.58 (12) | -177.17 (15) | -176.6 (3) |
O4—C4—C10—C5 | 4.0 (2) | -0.6 (3) | -3.3 (6) |
C4—C10—C5—C51 | 3.21 (19) | -3.5 (2) | -2.5 (6) |
C4—C10—C5—N6 | -178.30 (11) | 176.29 (15) | 178.5 (3) |
C51—C5—N6—C7 | 178.26 (11) | 179.79 (14) | 179.9 (3) |
C5—N6—C7—C71 | 178.79 (10) | -178.54 (14) | -178.2 (3) |
N6—C7—C71—C72 | -2.10 (17) | -17.4 (2) | 0.2 (5) |
24 h | 72 h | |
HACAT | 3.24 | 1.17 |
A549 | 1.20 | 1.10 |
DU145 | 4.60 | 0.73 |
SKOV-3 | 0.90 | 0.37 |
MDA-MB-231 | 0.36 | 0.27 |
Note: (*) compound concentration that reduces cell proliferation by 50%, as was estimated by the MTT assay. The results are presented in millimolar concentration. The data correspond to mean values (±SD) for n ≥ 3. |
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