Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229621004940/ef3014sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229621004940/ef3014I_shelxsup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229621004940/ef3014II_shelxsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229621004940/ef3014III_shelxsup4.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229621004940/ef3014I_shelxsup5.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229621004940/ef3014II_shelxsup6.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229621004940/ef3014III_shelxsup7.cml |
CCDC references: 1828486; 1828014; 1828286
For all structures, data collection: APEX2 (Bruker, 2008); cell refinement: APEX2 and SAINT (Bruker, 2008); data reduction: SAINT and XPREP (Bruker, 2008); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEP-3 (Farrugia, 2012) and PLATON (Spek, 2020); software used to prepare material for publication: publCIF (Westrip, 2010).
C17H17NO3 | F(000) = 600 |
Mr = 283.31 | Dx = 1.322 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.6750 (7) Å | Cell parameters from 2006 reflections |
b = 8.6138 (5) Å | θ = 2.9–25.0° |
c = 14.1504 (8) Å | µ = 0.09 mm−1 |
β = 90.075 (2)° | T = 296 K |
V = 1423.05 (14) Å3 | Block, colourless |
Z = 4 | 0.30 × 0.25 × 0.20 mm |
Bruker Kappa APEXII CCD diffractometer | 2006 reflections with I > 2σ(I) |
ω and φ scan | Rint = 0.038 |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | θmax = 25.0°, θmin = 2.9° |
Tmin = 0.547, Tmax = 0.746 | h = −13→13 |
25650 measured reflections | k = −10→10 |
2492 independent reflections | l = −16→16 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.051 | H-atom parameters constrained |
wR(F2) = 0.135 | w = 1/[σ2(Fo2) + (0.0497P)2 + 1.0412P] where P = (Fo2 + 2Fc2)/3 |
S = 1.13 | (Δ/σ)max < 0.001 |
2492 reflections | Δρmax = 0.34 e Å−3 |
200 parameters | Δρmin = −0.35 e Å−3 |
0 restraints |
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. |
Refinement. IS1 Alert level G PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ············.. 1 Report The H atom on the O2 hydroxy group was fixed at the calculated position and refined using a riding model with respect to its parent atom, with Uiso(H) = 1.5Ueq(O). The terminal carbon atom (C17)of the allyl group was disordered over two positions with an occupancy ratio of 77:23. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C17 | 0.4443 (3) | 0.3678 (5) | 0.1214 (3) | 0.0569 (13) | 0.774 (9) |
H17A | 0.383299 | 0.336357 | 0.158963 | 0.068* | 0.774 (9) |
H17B | 0.458960 | 0.317257 | 0.064566 | 0.068* | 0.774 (9) |
C17' | 0.5389 (15) | 0.3786 (16) | 0.0988 (11) | 0.073 (5) | 0.226 (9) |
H17C | 0.599696 | 0.316962 | 0.118723 | 0.088* | 0.226 (9) |
H17D | 0.505572 | 0.361613 | 0.039953 | 0.088* | 0.226 (9) |
O2 | 0.29807 (13) | 0.57697 (18) | 0.50335 (10) | 0.0396 (4) | |
H2 | 0.333707 | 0.528897 | 0.543855 | 0.059* | |
O1 | 0.25038 (14) | 0.24387 (19) | 0.28918 (10) | 0.0433 (4) | |
O3 | 0.48480 (12) | 0.39949 (18) | 0.40727 (11) | 0.0410 (4) | |
N1 | 0.40062 (15) | 0.5493 (2) | 0.29226 (12) | 0.0350 (4) | |
C8 | 0.21765 (18) | 0.5725 (2) | 0.34877 (14) | 0.0324 (5) | |
C7 | 0.28373 (17) | 0.4819 (2) | 0.42217 (13) | 0.0295 (4) | |
C1 | 0.21858 (17) | 0.2127 (2) | 0.36904 (14) | 0.0316 (5) | |
C6 | 0.23232 (16) | 0.3253 (2) | 0.44683 (13) | 0.0300 (5) | |
C14 | 0.40240 (17) | 0.4671 (2) | 0.37351 (14) | 0.0308 (5) | |
C13 | 0.29131 (19) | 0.6134 (2) | 0.27556 (15) | 0.0349 (5) | |
C5 | 0.19747 (19) | 0.2887 (3) | 0.53363 (15) | 0.0398 (5) | |
H5 | 0.204474 | 0.363648 | 0.580599 | 0.048* | |
C2 | 0.1618 (2) | 0.0607 (3) | 0.39103 (16) | 0.0464 (6) | |
H2A | 0.191153 | −0.018213 | 0.348555 | 0.056* | |
H2B | 0.080123 | 0.070244 | 0.379731 | 0.056* | |
C3 | 0.1811 (2) | 0.0089 (3) | 0.49190 (16) | 0.0461 (6) | |
H3A | 0.135971 | −0.083448 | 0.504365 | 0.055* | |
H3B | 0.261189 | −0.017272 | 0.500783 | 0.055* | |
C9 | 0.1052 (2) | 0.6184 (3) | 0.34597 (17) | 0.0425 (6) | |
H9 | 0.054779 | 0.590429 | 0.393823 | 0.051* | |
C11 | 0.1425 (3) | 0.7494 (3) | 0.19900 (18) | 0.0556 (7) | |
H11 | 0.116018 | 0.810111 | 0.149202 | 0.067* | |
C4 | 0.1478 (2) | 0.1349 (3) | 0.56037 (17) | 0.0470 (6) | |
H4A | 0.064995 | 0.143126 | 0.562300 | 0.056* | |
H4B | 0.174163 | 0.106951 | 0.623154 | 0.056* | |
C12 | 0.2561 (2) | 0.7025 (3) | 0.20011 (16) | 0.0473 (6) | |
H12 | 0.306286 | 0.730021 | 0.151986 | 0.057* | |
C10 | 0.0683 (2) | 0.7082 (3) | 0.26962 (19) | 0.0530 (7) | |
H10 | −0.007651 | 0.740487 | 0.266694 | 0.064* | |
C15 | 0.5000 (2) | 0.5719 (3) | 0.23170 (18) | 0.0519 (7) | |
H15A | 0.568364 | 0.552388 | 0.268897 | 0.062* | |
H15B | 0.502013 | 0.679859 | 0.212372 | 0.062* | |
C16 | 0.5051 (3) | 0.4749 (4) | 0.1465 (2) | 0.0753 (9) | |
H16 | 0.564230 | 0.499286 | 0.105136 | 0.090* | 0.774 (9) |
H16' | 0.446238 | 0.516368 | 0.110073 | 0.090* | 0.226 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C17 | 0.052 (3) | 0.070 (3) | 0.049 (2) | 0.0023 (19) | 0.0018 (17) | −0.0017 (18) |
C17' | 0.089 (13) | 0.060 (9) | 0.071 (9) | −0.001 (7) | 0.040 (8) | −0.012 (7) |
O2 | 0.0435 (9) | 0.0422 (9) | 0.0332 (8) | 0.0048 (7) | −0.0038 (6) | −0.0122 (6) |
O1 | 0.0539 (10) | 0.0439 (9) | 0.0323 (8) | −0.0099 (7) | 0.0047 (7) | −0.0038 (7) |
O3 | 0.0318 (8) | 0.0457 (9) | 0.0456 (9) | 0.0038 (7) | −0.0053 (7) | −0.0086 (7) |
N1 | 0.0324 (10) | 0.0364 (10) | 0.0363 (9) | −0.0081 (8) | 0.0043 (7) | −0.0011 (8) |
C8 | 0.0362 (11) | 0.0270 (10) | 0.0340 (11) | −0.0015 (9) | −0.0025 (9) | −0.0062 (8) |
C7 | 0.0308 (10) | 0.0298 (10) | 0.0278 (10) | −0.0005 (8) | −0.0006 (8) | −0.0056 (8) |
C1 | 0.0279 (11) | 0.0351 (11) | 0.0318 (11) | −0.0024 (8) | −0.0022 (8) | 0.0003 (9) |
C6 | 0.0246 (10) | 0.0347 (11) | 0.0306 (10) | 0.0018 (8) | 0.0003 (8) | 0.0004 (8) |
C14 | 0.0306 (11) | 0.0294 (10) | 0.0324 (10) | −0.0046 (8) | −0.0031 (8) | −0.0090 (8) |
C13 | 0.0413 (12) | 0.0265 (10) | 0.0368 (11) | −0.0044 (9) | −0.0046 (9) | −0.0034 (9) |
C5 | 0.0409 (13) | 0.0444 (13) | 0.0341 (11) | 0.0010 (10) | 0.0053 (9) | −0.0015 (10) |
C2 | 0.0543 (15) | 0.0410 (13) | 0.0440 (13) | −0.0158 (11) | −0.0064 (11) | 0.0028 (10) |
C3 | 0.0512 (14) | 0.0400 (13) | 0.0471 (13) | −0.0094 (11) | −0.0014 (11) | 0.0092 (11) |
C9 | 0.0378 (12) | 0.0436 (13) | 0.0460 (13) | 0.0064 (10) | −0.0054 (10) | −0.0104 (10) |
C11 | 0.086 (2) | 0.0381 (13) | 0.0432 (13) | 0.0128 (13) | −0.0223 (14) | −0.0030 (11) |
C4 | 0.0470 (14) | 0.0533 (15) | 0.0407 (12) | −0.0036 (11) | 0.0091 (10) | 0.0093 (11) |
C12 | 0.0692 (17) | 0.0344 (12) | 0.0383 (12) | −0.0035 (11) | −0.0054 (11) | 0.0024 (10) |
C10 | 0.0520 (15) | 0.0499 (15) | 0.0571 (15) | 0.0181 (12) | −0.0228 (12) | −0.0150 (12) |
C15 | 0.0468 (14) | 0.0571 (16) | 0.0519 (15) | −0.0126 (12) | 0.0172 (11) | 0.0011 (12) |
C16 | 0.089 (2) | 0.084 (2) | 0.0539 (17) | 0.001 (2) | 0.0196 (16) | −0.0069 (17) |
C17—C16 | 1.217 (5) | C5—C4 | 1.495 (3) |
C17—H17A | 0.9300 | C5—H5 | 0.9300 |
C17—H17B | 0.9300 | C2—C3 | 1.512 (3) |
C17'—C16 | 1.141 (13) | C2—H2A | 0.9700 |
C17'—H17C | 0.9300 | C2—H2B | 0.9700 |
C17'—H17D | 0.9300 | C3—C4 | 1.506 (3) |
O2—C7 | 1.420 (2) | C3—H3A | 0.9700 |
O2—H2 | 0.8200 | C3—H3B | 0.9700 |
O1—C1 | 1.220 (2) | C9—C10 | 1.397 (3) |
O3—C14 | 1.221 (3) | C9—H9 | 0.9300 |
N1—C14 | 1.350 (3) | C11—C10 | 1.370 (4) |
N1—C13 | 1.410 (3) | C11—C12 | 1.387 (4) |
N1—C15 | 1.456 (3) | C11—H11 | 0.9300 |
C8—C9 | 1.371 (3) | C4—H4A | 0.9700 |
C8—C13 | 1.392 (3) | C4—H4B | 0.9700 |
C8—C7 | 1.510 (3) | C12—H12 | 0.9300 |
C7—C6 | 1.517 (3) | C10—H10 | 0.9300 |
C7—C14 | 1.553 (3) | C15—C16 | 1.467 (4) |
C1—C6 | 1.476 (3) | C15—H15A | 0.9700 |
C1—C2 | 1.501 (3) | C15—H15B | 0.9700 |
C6—C5 | 1.332 (3) | C16—H16 | 0.9300 |
C13—C12 | 1.378 (3) | C16—H16' | 0.9300 |
C16—C17—H17A | 120.0 | C3—C2—H2B | 109.0 |
C16—C17—H17B | 120.0 | H2A—C2—H2B | 107.8 |
H17A—C17—H17B | 120.0 | C4—C3—C2 | 110.9 (2) |
C16—C17'—H17C | 120.0 | C4—C3—H3A | 109.5 |
C16—C17'—H17D | 120.0 | C2—C3—H3A | 109.5 |
H17C—C17'—H17D | 120.0 | C4—C3—H3B | 109.5 |
C7—O2—H2 | 109.5 | C2—C3—H3B | 109.5 |
C14—N1—C13 | 111.15 (17) | H3A—C3—H3B | 108.1 |
C14—N1—C15 | 124.0 (2) | C8—C9—C10 | 118.5 (2) |
C13—N1—C15 | 124.81 (19) | C8—C9—H9 | 120.8 |
C9—C8—C13 | 119.8 (2) | C10—C9—H9 | 120.8 |
C9—C8—C7 | 131.1 (2) | C10—C11—C12 | 121.5 (2) |
C13—C8—C7 | 109.08 (18) | C10—C11—H11 | 119.3 |
O2—C7—C8 | 108.55 (16) | C12—C11—H11 | 119.3 |
O2—C7—C6 | 111.89 (16) | C5—C4—C3 | 112.05 (18) |
C8—C7—C6 | 114.55 (16) | C5—C4—H4A | 109.2 |
O2—C7—C14 | 107.55 (15) | C3—C4—H4A | 109.2 |
C8—C7—C14 | 101.10 (16) | C5—C4—H4B | 109.2 |
C6—C7—C14 | 112.49 (16) | C3—C4—H4B | 109.2 |
O1—C1—C6 | 120.88 (19) | H4A—C4—H4B | 107.9 |
O1—C1—C2 | 121.29 (19) | C13—C12—C11 | 117.1 (2) |
C6—C1—C2 | 117.81 (18) | C13—C12—H12 | 121.4 |
C5—C6—C1 | 119.9 (2) | C11—C12—H12 | 121.4 |
C5—C6—C7 | 122.94 (19) | C11—C10—C9 | 120.8 (2) |
C1—C6—C7 | 117.10 (16) | C11—C10—H10 | 119.6 |
O3—C14—N1 | 126.47 (19) | C9—C10—H10 | 119.6 |
O3—C14—C7 | 124.63 (18) | N1—C15—C16 | 116.1 (2) |
N1—C14—C7 | 108.77 (17) | N1—C15—H15A | 108.3 |
C12—C13—C8 | 122.2 (2) | C16—C15—H15A | 108.3 |
C12—C13—N1 | 128.1 (2) | N1—C15—H15B | 108.3 |
C8—C13—N1 | 109.64 (18) | C16—C15—H15B | 108.3 |
C6—C5—C4 | 124.2 (2) | H15A—C15—H15B | 107.4 |
C6—C5—H5 | 117.9 | C17'—C16—C15 | 156.2 (10) |
C4—C5—H5 | 117.9 | C17—C16—C15 | 130.4 (3) |
C1—C2—C3 | 112.82 (18) | C17—C16—H16 | 114.8 |
C1—C2—H2A | 109.0 | C15—C16—H16 | 114.8 |
C3—C2—H2A | 109.0 | C17'—C16—H16' | 101.9 |
C1—C2—H2B | 109.0 | C15—C16—H16' | 101.9 |
C9—C8—C7—O2 | −70.4 (3) | C9—C8—C13—C12 | 1.5 (3) |
C13—C8—C7—O2 | 108.18 (18) | C7—C8—C13—C12 | −177.25 (19) |
C9—C8—C7—C6 | 55.5 (3) | C9—C8—C13—N1 | −178.09 (18) |
C13—C8—C7—C6 | −125.98 (18) | C7—C8—C13—N1 | 3.2 (2) |
C9—C8—C7—C14 | 176.7 (2) | C14—N1—C13—C12 | −179.4 (2) |
C13—C8—C7—C14 | −4.8 (2) | C15—N1—C13—C12 | 2.3 (3) |
O1—C1—C6—C5 | −179.7 (2) | C14—N1—C13—C8 | 0.2 (2) |
C2—C1—C6—C5 | 1.7 (3) | C15—N1—C13—C8 | −178.17 (19) |
O1—C1—C6—C7 | 1.9 (3) | C1—C6—C5—C4 | 2.5 (3) |
C2—C1—C6—C7 | −176.61 (18) | C7—C6—C5—C4 | −179.2 (2) |
O2—C7—C6—C5 | 4.7 (3) | O1—C1—C2—C3 | 151.6 (2) |
C8—C7—C6—C5 | −119.3 (2) | C6—C1—C2—C3 | −29.9 (3) |
C14—C7—C6—C5 | 125.9 (2) | C1—C2—C3—C4 | 52.9 (3) |
O2—C7—C6—C1 | −176.97 (16) | C13—C8—C9—C10 | −1.1 (3) |
C8—C7—C6—C1 | 58.9 (2) | C7—C8—C9—C10 | 177.3 (2) |
C14—C7—C6—C1 | −55.8 (2) | C6—C5—C4—C3 | 21.6 (3) |
C13—N1—C14—O3 | −179.25 (19) | C2—C3—C4—C5 | −48.2 (3) |
C15—N1—C14—O3 | −0.9 (3) | C8—C13—C12—C11 | −0.7 (3) |
C13—N1—C14—C7 | −3.4 (2) | N1—C13—C12—C11 | 178.7 (2) |
C15—N1—C14—C7 | 175.00 (19) | C10—C11—C12—C13 | −0.3 (4) |
O2—C7—C14—O3 | 67.2 (2) | C12—C11—C10—C9 | 0.6 (4) |
C8—C7—C14—O3 | −179.13 (19) | C8—C9—C10—C11 | 0.1 (4) |
C6—C7—C14—O3 | −56.5 (3) | C14—N1—C15—C16 | 101.9 (3) |
O2—C7—C14—N1 | −108.81 (18) | C13—N1—C15—C16 | −79.9 (3) |
C8—C7—C14—N1 | 4.9 (2) | N1—C15—C16—C17' | −110.1 (19) |
C6—C7—C14—N1 | 127.54 (17) | N1—C15—C16—C17 | −7.2 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O3i | 0.82 | 2.31 | 2.839 (2) | 123 |
C15—H15B···O3ii | 0.97 | 2.54 | 3.444 (3) | 155 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, y+1/2, −z+1/2. |
C16H17NO3 | F(000) = 576 |
Mr = 271.30 | Dx = 1.248 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.9227 (6) Å | Cell parameters from 1892 reflections |
b = 12.8741 (6) Å | θ = 2.3–26.3° |
c = 12.5994 (8) Å | µ = 0.09 mm−1 |
β = 93.897 (3)° | T = 296 K |
V = 1443.97 (15) Å3 | Block, colourless |
Z = 4 | 0.35 × 0.30 × 0.25 mm |
Bruker Kappa APEXII CCD diffractometer | 1892 reflections with I > 2σ(I) |
ω and φ scan | Rint = 0.036 |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | θmax = 26.0°, θmin = 2.3° |
Tmin = 0.716, Tmax = 0.746 | h = −11→9 |
19991 measured reflections | k = −15→15 |
2837 independent reflections | l = −15→15 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.118 | w = 1/[σ2(Fo2) + (0.0455P)2 + 0.4767P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
2837 reflections | Δρmax = 0.16 e Å−3 |
210 parameters | Δρmin = −0.15 e Å−3 |
77 restraints |
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. |
Refinement. IS2 Alert level G 1. PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 8 Note Atoms C2, C3, C4 of cyclohexenone moiety are disordered over two positions. The disordered positions were located from difference electron density peaks and refined with a target C-C distance of 1.52 Å using DFIX instruction. 2. PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ··· 6 Report The thermal parameters of atoms in the disordered group are restrained with an effective standard deviation of 0.02 Å2 to have the same Uij components. 3. PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ············.. 1 Report The hydrogen on hydroxy group was fixed at calculated position and refined as a riding model with respect to its parent atom with Uiso(H) = 1.5Ueq(O). 4. PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 2 Report The atoms C2, C3, C4 of cyclohexenone moiety is disordered over two positions. The disordered positions were located from difference electron density peaks and refined with a target C—C distance of 1.52 Å using DFIX instruction. 5. PLAT177_ALERT_4_G The CIF-Embedded .res File Contains DELU Records 2 Report The components of the anisotropic displacement parameters in the direction of the bond of disordered atoms are restrained to be equal within an effective standard deviation of 0.01 using DELU instruction. 6. PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records 1 Report The atoms (C2, C3, C4) in the disordered group are restrained with an effective standard deviation of 0.02 Å2 to have the same Uij components using the SIMU instruction. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.7567 (2) | 0.33711 (16) | 0.19077 (15) | 0.0503 (5) | |
C2 | 0.9239 (5) | 0.3497 (6) | 0.2123 (7) | 0.083 (2) | 0.720 (9) |
H2A | 0.9745 | 0.2880 | 0.1886 | 0.100* | 0.720 (9) |
H2B | 0.9474 | 0.3571 | 0.2882 | 0.100* | 0.720 (9) |
C3 | 0.9802 (5) | 0.4439 (3) | 0.1552 (6) | 0.0914 (16) | 0.720 (9) |
H3A | 0.9587 | 0.4363 | 0.0790 | 0.110* | 0.720 (9) |
H3B | 1.0881 | 0.4503 | 0.1690 | 0.110* | 0.720 (9) |
C4 | 0.9024 (6) | 0.5410 (6) | 0.1944 (10) | 0.088 (2) | 0.720 (9) |
H4A | 0.9390 | 0.5559 | 0.2671 | 0.105* | 0.720 (9) |
H4B | 0.9256 | 0.5999 | 0.1505 | 0.105* | 0.720 (9) |
C2' | 0.9248 (12) | 0.3438 (17) | 0.181 (2) | 0.084 (4) | 0.280 (9) |
H2'1 | 0.9731 | 0.2830 | 0.2128 | 0.101* | 0.280 (9) |
H2'2 | 0.9448 | 0.3446 | 0.1058 | 0.101* | 0.280 (9) |
C3' | 0.9899 (11) | 0.4406 (8) | 0.2338 (15) | 0.086 (3) | 0.280 (9) |
H3'1 | 1.0962 | 0.4459 | 0.2230 | 0.103* | 0.280 (9) |
H3'2 | 0.9776 | 0.4382 | 0.3097 | 0.103* | 0.280 (9) |
C4' | 0.9059 (10) | 0.5334 (16) | 0.184 (2) | 0.079 (4) | 0.280 (9) |
H4'1 | 0.9408 | 0.5962 | 0.2205 | 0.094* | 0.280 (9) |
H4'2 | 0.9290 | 0.5394 | 0.1102 | 0.094* | 0.280 (9) |
C5 | 0.7371 (2) | 0.52491 (16) | 0.18965 (16) | 0.0573 (5) | |
H5 | 0.6767 | 0.5838 | 0.1886 | 0.069* | |
C6 | 0.66896 (19) | 0.43340 (13) | 0.18680 (13) | 0.0389 (4) | |
C7 | 0.49995 (19) | 0.42239 (12) | 0.17933 (13) | 0.0373 (4) | |
C8 | 0.43427 (19) | 0.37039 (13) | 0.27260 (14) | 0.0413 (4) | |
C9 | 0.4432 (2) | 0.39694 (16) | 0.37818 (16) | 0.0556 (5) | |
H9 | 0.5006 | 0.4534 | 0.4027 | 0.067* | |
C10 | 0.3646 (3) | 0.33750 (19) | 0.44785 (18) | 0.0682 (6) | |
H10 | 0.3679 | 0.3547 | 0.5197 | 0.082* | |
C11 | 0.2823 (3) | 0.25373 (19) | 0.41093 (19) | 0.0698 (7) | |
H11 | 0.2312 | 0.2144 | 0.4588 | 0.084* | |
C12 | 0.2727 (2) | 0.22584 (16) | 0.30507 (18) | 0.0594 (6) | |
H12 | 0.2171 | 0.1684 | 0.2809 | 0.071* | |
C13 | 0.3485 (2) | 0.28613 (14) | 0.23678 (15) | 0.0445 (5) | |
C14 | 0.4437 (2) | 0.34990 (13) | 0.08747 (15) | 0.0416 (4) | |
C15 | 0.2720 (3) | 0.20116 (17) | 0.05734 (19) | 0.0673 (6) | |
H15A | 0.2440 | 0.2333 | −0.0108 | 0.081* | |
H15B | 0.1802 | 0.1817 | 0.0894 | 0.081* | |
C16 | 0.3601 (4) | 0.1063 (2) | 0.0393 (3) | 0.1041 (10) | |
H16A | 0.3013 | 0.0596 | −0.0060 | 0.156* | |
H16B | 0.4501 | 0.1246 | 0.0060 | 0.156* | |
H16C | 0.3862 | 0.0730 | 0.1062 | 0.156* | |
N1 | 0.35269 (17) | 0.27687 (11) | 0.12560 (13) | 0.0478 (4) | |
O1 | 0.69642 (17) | 0.25271 (11) | 0.18388 (13) | 0.0672 (4) | |
O2 | 0.42546 (14) | 0.51902 (9) | 0.16291 (10) | 0.0500 (4) | |
H2 | 0.4545 | 0.5470 | 0.1095 | 0.075* | |
O3 | 0.46968 (16) | 0.35971 (10) | −0.00586 (10) | 0.0545 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0423 (12) | 0.0531 (12) | 0.0557 (12) | 0.0060 (10) | 0.0062 (9) | −0.0013 (9) |
C2 | 0.042 (3) | 0.092 (4) | 0.114 (5) | 0.018 (3) | −0.004 (2) | −0.020 (3) |
C3 | 0.0365 (19) | 0.119 (3) | 0.120 (4) | −0.015 (2) | 0.014 (2) | −0.021 (3) |
C4 | 0.056 (4) | 0.083 (4) | 0.124 (5) | −0.019 (3) | 0.006 (4) | −0.020 (4) |
C2' | 0.041 (6) | 0.095 (7) | 0.115 (10) | 0.010 (6) | −0.002 (6) | −0.046 (7) |
C3' | 0.038 (4) | 0.095 (6) | 0.122 (7) | −0.001 (4) | −0.007 (5) | −0.026 (6) |
C4' | 0.040 (8) | 0.090 (7) | 0.105 (9) | −0.032 (7) | −0.001 (7) | −0.006 (8) |
C5 | 0.0492 (13) | 0.0518 (12) | 0.0709 (14) | −0.0060 (10) | 0.0031 (10) | −0.0075 (10) |
C6 | 0.0371 (10) | 0.0406 (10) | 0.0397 (9) | 0.0001 (8) | 0.0069 (7) | −0.0012 (7) |
C7 | 0.0355 (10) | 0.0321 (9) | 0.0453 (10) | 0.0043 (7) | 0.0089 (7) | 0.0051 (7) |
C8 | 0.0355 (10) | 0.0419 (10) | 0.0477 (11) | 0.0061 (8) | 0.0112 (8) | 0.0071 (8) |
C9 | 0.0560 (13) | 0.0595 (12) | 0.0525 (12) | 0.0012 (10) | 0.0129 (10) | 0.0027 (9) |
C10 | 0.0683 (16) | 0.0865 (17) | 0.0523 (12) | 0.0039 (14) | 0.0222 (11) | 0.0136 (12) |
C11 | 0.0559 (14) | 0.0845 (17) | 0.0720 (16) | −0.0013 (13) | 0.0255 (12) | 0.0310 (13) |
C12 | 0.0425 (12) | 0.0590 (13) | 0.0779 (16) | −0.0075 (10) | 0.0119 (10) | 0.0185 (11) |
C13 | 0.0311 (10) | 0.0468 (11) | 0.0563 (12) | 0.0021 (8) | 0.0080 (8) | 0.0106 (9) |
C14 | 0.0362 (10) | 0.0399 (10) | 0.0490 (11) | 0.0050 (8) | 0.0044 (8) | 0.0067 (8) |
C15 | 0.0561 (14) | 0.0667 (14) | 0.0781 (15) | −0.0177 (11) | −0.0031 (11) | −0.0031 (12) |
C16 | 0.111 (2) | 0.0780 (18) | 0.120 (2) | −0.0010 (17) | −0.0182 (19) | −0.0309 (17) |
N1 | 0.0410 (9) | 0.0469 (9) | 0.0556 (10) | −0.0095 (7) | 0.0028 (7) | 0.0026 (7) |
O1 | 0.0585 (10) | 0.0445 (8) | 0.0994 (12) | 0.0102 (7) | 0.0112 (8) | 0.0072 (7) |
O2 | 0.0493 (8) | 0.0395 (7) | 0.0630 (9) | 0.0117 (6) | 0.0170 (6) | 0.0098 (6) |
O3 | 0.0646 (9) | 0.0544 (8) | 0.0447 (8) | −0.0034 (7) | 0.0062 (7) | 0.0047 (6) |
C1—O1 | 1.213 (2) | C7—O2 | 1.4190 (19) |
C1—C6 | 1.465 (3) | C7—C8 | 1.505 (2) |
C1—C2 | 1.507 (5) | C7—C14 | 1.544 (2) |
C1—C2' | 1.516 (10) | C8—C9 | 1.370 (3) |
C2—C3 | 1.514 (7) | C8—C13 | 1.385 (3) |
C2—H2A | 0.9700 | C9—C10 | 1.390 (3) |
C2—H2B | 0.9700 | C9—H9 | 0.9300 |
C3—C4 | 1.528 (8) | C10—C11 | 1.368 (3) |
C3—H3A | 0.9700 | C10—H10 | 0.9300 |
C3—H3B | 0.9700 | C11—C12 | 1.378 (3) |
C4—C5 | 1.486 (6) | C11—H11 | 0.9300 |
C4—H4A | 0.9700 | C12—C13 | 1.371 (3) |
C4—H4B | 0.9700 | C12—H12 | 0.9300 |
C2'—C3' | 1.512 (10) | C13—N1 | 1.409 (2) |
C2'—H2'1 | 0.9700 | C14—O3 | 1.220 (2) |
C2'—H2'2 | 0.9700 | C14—N1 | 1.352 (2) |
C3'—C4' | 1.523 (10) | C15—N1 | 1.457 (3) |
C3'—H3'1 | 0.9700 | C15—C16 | 1.478 (3) |
C3'—H3'2 | 0.9700 | C15—H15A | 0.9700 |
C4'—C5 | 1.516 (9) | C15—H15B | 0.9700 |
C4'—H4'1 | 0.9700 | C16—H16A | 0.9600 |
C4'—H4'2 | 0.9700 | C16—H16B | 0.9600 |
C5—C6 | 1.325 (3) | C16—H16C | 0.9600 |
C5—H5 | 0.9300 | O2—H2 | 0.8200 |
C6—C7 | 1.511 (2) | ||
O1—C1—C6 | 121.48 (17) | C5—C6—C7 | 122.64 (16) |
O1—C1—C2 | 122.5 (4) | C1—C6—C7 | 116.83 (15) |
C6—C1—C2 | 115.8 (3) | O2—C7—C8 | 107.48 (13) |
O1—C1—C2' | 118.8 (8) | O2—C7—C6 | 112.48 (13) |
C6—C1—C2' | 118.5 (9) | C8—C7—C6 | 115.65 (14) |
C1—C2—C3 | 110.9 (5) | O2—C7—C14 | 107.18 (13) |
C1—C2—H2A | 109.5 | C8—C7—C14 | 101.09 (14) |
C3—C2—H2A | 109.5 | C6—C7—C14 | 112.06 (13) |
C1—C2—H2B | 109.5 | C9—C8—C13 | 120.38 (17) |
C3—C2—H2B | 109.5 | C9—C8—C7 | 130.30 (17) |
H2A—C2—H2B | 108.0 | C13—C8—C7 | 109.25 (15) |
C2—C3—C4 | 109.2 (7) | C8—C9—C10 | 118.5 (2) |
C2—C3—H3A | 109.8 | C8—C9—H9 | 120.7 |
C4—C3—H3A | 109.8 | C10—C9—H9 | 120.7 |
C2—C3—H3B | 109.8 | C11—C10—C9 | 120.1 (2) |
C4—C3—H3B | 109.8 | C11—C10—H10 | 119.9 |
H3A—C3—H3B | 108.3 | C9—C10—H10 | 119.9 |
C5—C4—C3 | 110.2 (5) | C10—C11—C12 | 122.05 (19) |
C5—C4—H4A | 109.6 | C10—C11—H11 | 119.0 |
C3—C4—H4A | 109.6 | C12—C11—H11 | 119.0 |
C5—C4—H4B | 109.6 | C13—C12—C11 | 117.3 (2) |
C3—C4—H4B | 109.6 | C13—C12—H12 | 121.3 |
H4A—C4—H4B | 108.1 | C11—C12—H12 | 121.3 |
C3'—C2'—C1 | 111.2 (10) | C12—C13—C8 | 121.61 (19) |
C3'—C2'—H2'1 | 109.4 | C12—C13—N1 | 128.59 (18) |
C1—C2'—H2'1 | 109.4 | C8—C13—N1 | 109.79 (15) |
C3'—C2'—H2'2 | 109.4 | O3—C14—N1 | 124.92 (17) |
C1—C2'—H2'2 | 109.4 | O3—C14—C7 | 125.90 (16) |
H2'1—C2'—H2'2 | 108.0 | N1—C14—C7 | 109.06 (15) |
C2'—C3'—C4' | 107.5 (19) | N1—C15—C16 | 113.4 (2) |
C2'—C3'—H3'1 | 110.2 | N1—C15—H15A | 108.9 |
C4'—C3'—H3'1 | 110.2 | C16—C15—H15A | 108.9 |
C2'—C3'—H3'2 | 110.2 | N1—C15—H15B | 108.9 |
C4'—C3'—H3'2 | 110.2 | C16—C15—H15B | 108.9 |
H3'1—C3'—H3'2 | 108.5 | H15A—C15—H15B | 107.7 |
C5—C4'—C3' | 112.7 (10) | C15—C16—H16A | 109.5 |
C5—C4'—H4'1 | 109.0 | C15—C16—H16B | 109.5 |
C3'—C4'—H4'1 | 109.0 | H16A—C16—H16B | 109.5 |
C5—C4'—H4'2 | 109.0 | C15—C16—H16C | 109.5 |
C3'—C4'—H4'2 | 109.0 | H16A—C16—H16C | 109.5 |
H4'1—C4'—H4'2 | 107.8 | H16B—C16—H16C | 109.5 |
C6—C5—C4 | 125.3 (3) | C14—N1—C13 | 110.60 (15) |
C6—C5—C4' | 121.2 (8) | C14—N1—C15 | 122.69 (17) |
C6—C5—H5 | 117.4 | C13—N1—C15 | 126.72 (16) |
C4—C5—H5 | 117.4 | C7—O2—H2 | 109.5 |
C5—C6—C1 | 120.52 (17) | ||
O1—C1—C2—C3 | 145.9 (5) | C6—C7—C8—C13 | −124.16 (16) |
C6—C1—C2—C3 | −38.7 (7) | C14—C7—C8—C13 | −2.91 (17) |
C1—C2—C3—C4 | 60.3 (9) | C13—C8—C9—C10 | 0.0 (3) |
C2—C3—C4—C5 | −50.3 (10) | C7—C8—C9—C10 | 176.75 (18) |
O1—C1—C2'—C3' | −156.7 (15) | C8—C9—C10—C11 | 0.9 (3) |
C6—C1—C2'—C3' | 36 (2) | C9—C10—C11—C12 | −0.7 (4) |
C1—C2'—C3'—C4' | −57 (3) | C10—C11—C12—C13 | −0.5 (3) |
C2'—C3'—C4'—C5 | 55 (3) | C11—C12—C13—C8 | 1.5 (3) |
C3—C4—C5—C6 | 20.8 (10) | C11—C12—C13—N1 | −177.50 (19) |
C3'—C4'—C5—C6 | −31 (3) | C9—C8—C13—C12 | −1.2 (3) |
C4—C5—C6—C1 | 1.4 (6) | C7—C8—C13—C12 | −178.59 (16) |
C4'—C5—C6—C1 | 7.2 (13) | C9—C8—C13—N1 | 177.89 (17) |
C4—C5—C6—C7 | −178.5 (6) | C7—C8—C13—N1 | 0.55 (19) |
C4'—C5—C6—C7 | −172.7 (13) | O2—C7—C14—O3 | 68.3 (2) |
O1—C1—C6—C5 | −176.95 (19) | C8—C7—C14—O3 | −179.34 (17) |
C2—C1—C6—C5 | 7.6 (4) | C6—C7—C14—O3 | −55.6 (2) |
C2'—C1—C6—C5 | −9.6 (11) | O2—C7—C14—N1 | −107.96 (15) |
O1—C1—C6—C7 | 3.0 (3) | C8—C7—C14—N1 | 4.44 (17) |
C2—C1—C6—C7 | −172.5 (4) | C6—C7—C14—N1 | 128.19 (15) |
C2'—C1—C6—C7 | 170.4 (10) | O3—C14—N1—C13 | 179.29 (17) |
C5—C6—C7—O2 | 7.2 (2) | C7—C14—N1—C13 | −4.45 (19) |
C1—C6—C7—O2 | −172.80 (14) | O3—C14—N1—C15 | −1.0 (3) |
C5—C6—C7—C8 | −116.86 (19) | C7—C14—N1—C15 | 175.25 (16) |
C1—C6—C7—C8 | 63.2 (2) | C12—C13—N1—C14 | −178.41 (18) |
C5—C6—C7—C14 | 127.99 (18) | C8—C13—N1—C14 | 2.5 (2) |
C1—C6—C7—C14 | −52.0 (2) | C12—C13—N1—C15 | 1.9 (3) |
O2—C7—C8—C9 | −67.7 (2) | C8—C13—N1—C15 | −177.15 (18) |
C6—C7—C8—C9 | 58.8 (2) | C16—C15—N1—C14 | 87.6 (3) |
C14—C7—C8—C9 | −179.91 (19) | C16—C15—N1—C13 | −92.8 (3) |
O2—C7—C8—C13 | 109.26 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O3i | 0.82 | 1.93 | 2.7350 (18) | 167 |
C11—H11···O3ii | 0.93 | 2.59 | 3.378 (3) | 143 |
C12—H12···O2iii | 0.93 | 2.44 | 3.237 (2) | 144 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1/2, −y+1/2, z+1/2; (iii) −x+1/2, y−1/2, −z+1/2. |
C15H14BrNO3 | Dx = 1.580 Mg m−3 |
Mr = 336.18 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pna21 | Cell parameters from 2203 reflections |
a = 7.8960 (3) Å | θ = 3.3–25.0° |
b = 19.6458 (8) Å | µ = 2.92 mm−1 |
c = 9.1088 (3) Å | T = 296 K |
V = 1412.99 (9) Å3 | Block, colourless |
Z = 4 | 0.20 × 0.20 × 0.15 mm |
F(000) = 680 |
Bruker Kappa APEXII CCD diffractometer | 2203 reflections with I > 2σ(I) |
ω and φ scan | Rint = 0.035 |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | θmax = 25.0°, θmin = 3.3° |
Tmin = 0.550, Tmax = 0.746 | h = −9→9 |
25065 measured reflections | k = −23→23 |
2365 independent reflections | l = −10→10 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.033 | w = 1/[σ2(Fo2) + (0.0653P)2 + 0.434P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.101 | (Δ/σ)max < 0.001 |
S = 1.13 | Δρmax = 0.31 e Å−3 |
2365 reflections | Δρmin = −0.78 e Å−3 |
182 parameters | Absolute structure: Flack x determined using 952 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
1 restraint | Absolute structure parameter: 0.027 (4) |
Primary atom site location: structure-invariant direct methods |
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. |
Refinement. IS3 Alert level C 1. PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) . 1 Check This low-angle reflection is affected by the beam stop. Hence its I(obs) is much smaller than I(calc) 2. PLAT934_ALERT_3_C Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers .. 1 Check This low angle reflection is affected by the beam stop. Hence its I(obs) is much smaller than I(calc) Alert level G 3. PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ············.. 1 Report The hydroxy H atom was fixed at the calculated position and refined using a riding model with respect to its parent atom, with Uiso(H) = 1.5Ueq(O) |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.31672 (8) | 0.32391 (3) | 0.11497 (10) | 0.0624 (3) | |
O1 | 0.2107 (6) | 0.3645 (2) | 0.7638 (7) | 0.0660 (13) | |
O3 | 0.6023 (4) | 0.43342 (18) | 0.8846 (4) | 0.0376 (7) | |
O2 | 0.5834 (3) | 0.49520 (14) | 0.5940 (4) | 0.0314 (7) | |
H2 | 0.549453 | 0.511227 | 0.516215 | 0.047* | |
N1 | 0.6094 (5) | 0.3447 (2) | 0.7237 (5) | 0.0364 (9) | |
C3 | 0.0437 (9) | 0.5236 (5) | 0.8846 (10) | 0.083 (3) | |
H3A | 0.111623 | 0.520576 | 0.973126 | 0.100* | |
H3B | −0.066127 | 0.541767 | 0.911606 | 0.100* | |
C4 | 0.1279 (8) | 0.5717 (4) | 0.7790 (8) | 0.0615 (18) | |
H4A | 0.046656 | 0.585447 | 0.704834 | 0.074* | |
H4B | 0.163772 | 0.612134 | 0.831452 | 0.074* | |
C5 | 0.2784 (6) | 0.5400 (3) | 0.7055 (6) | 0.0365 (11) | |
H5 | 0.357328 | 0.568568 | 0.661499 | 0.044* | |
C6 | 0.3050 (5) | 0.4732 (2) | 0.6997 (5) | 0.0256 (9) | |
C7 | 0.4709 (5) | 0.44369 (18) | 0.6413 (4) | 0.0231 (9) | |
C8 | 0.4589 (5) | 0.3868 (2) | 0.5291 (5) | 0.0278 (9) | |
C9 | 0.3891 (6) | 0.3861 (2) | 0.3893 (5) | 0.0316 (9) | |
H9 | 0.331908 | 0.423582 | 0.351670 | 0.038* | |
C10 | 0.4086 (7) | 0.3264 (3) | 0.3078 (6) | 0.0397 (12) | |
C11 | 0.4935 (8) | 0.2698 (3) | 0.3627 (7) | 0.0498 (14) | |
H11 | 0.503246 | 0.230694 | 0.305729 | 0.060* | |
C2 | 0.0215 (9) | 0.4557 (5) | 0.8241 (10) | 0.079 (2) | |
H2A | −0.063138 | 0.457560 | 0.747037 | 0.095* | |
H2B | −0.020963 | 0.425903 | 0.900592 | 0.095* | |
C1 | 0.1816 (6) | 0.4257 (3) | 0.7623 (7) | 0.0423 (12) | |
C14 | 0.5661 (5) | 0.4075 (2) | 0.7672 (5) | 0.0291 (9) | |
C13 | 0.5457 (6) | 0.3304 (2) | 0.5830 (6) | 0.0340 (12) | |
C12 | 0.5632 (7) | 0.2715 (2) | 0.5013 (7) | 0.0460 (13) | |
H12 | 0.620511 | 0.233994 | 0.538961 | 0.055* | |
C15 | 0.7016 (8) | 0.2968 (3) | 0.8157 (9) | 0.0565 (16) | |
H15A | 0.741654 | 0.319712 | 0.902075 | 0.085* | |
H15B | 0.796180 | 0.278850 | 0.762007 | 0.085* | |
H15C | 0.627731 | 0.260216 | 0.843754 | 0.085* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0783 (4) | 0.0760 (4) | 0.0329 (4) | −0.0279 (3) | 0.0028 (3) | −0.0196 (3) |
O1 | 0.069 (3) | 0.047 (2) | 0.081 (4) | −0.0148 (19) | 0.030 (2) | 0.005 (2) |
O3 | 0.0407 (17) | 0.0458 (18) | 0.0261 (18) | 0.0064 (15) | −0.0042 (14) | −0.0053 (15) |
O2 | 0.0303 (13) | 0.0297 (13) | 0.034 (2) | −0.0053 (11) | 0.0053 (14) | 0.0026 (14) |
N1 | 0.044 (2) | 0.0304 (18) | 0.035 (2) | 0.0091 (18) | −0.0023 (19) | 0.0006 (19) |
C3 | 0.059 (4) | 0.127 (7) | 0.063 (5) | 0.037 (4) | 0.020 (4) | −0.015 (5) |
C4 | 0.053 (3) | 0.072 (4) | 0.060 (4) | 0.034 (3) | −0.002 (3) | −0.019 (3) |
C5 | 0.037 (2) | 0.037 (2) | 0.035 (3) | 0.0113 (19) | 0.000 (2) | −0.003 (2) |
C6 | 0.0235 (18) | 0.030 (2) | 0.023 (2) | 0.0021 (15) | 0.0022 (15) | −0.0045 (18) |
C7 | 0.0256 (17) | 0.0225 (17) | 0.021 (2) | 0.0011 (14) | 0.0039 (15) | −0.0038 (15) |
C8 | 0.030 (2) | 0.028 (2) | 0.024 (2) | −0.0008 (16) | 0.0084 (17) | −0.0049 (18) |
C9 | 0.032 (2) | 0.035 (2) | 0.028 (2) | −0.0068 (18) | 0.0033 (18) | −0.0074 (19) |
C10 | 0.046 (3) | 0.041 (3) | 0.032 (3) | −0.016 (2) | 0.007 (2) | −0.013 (2) |
C11 | 0.056 (3) | 0.037 (3) | 0.057 (4) | −0.006 (2) | 0.011 (3) | −0.025 (2) |
C2 | 0.045 (3) | 0.120 (7) | 0.072 (5) | 0.000 (4) | 0.026 (3) | 0.008 (5) |
C1 | 0.033 (2) | 0.053 (3) | 0.041 (3) | −0.007 (2) | 0.005 (2) | 0.000 (3) |
C14 | 0.0254 (19) | 0.032 (2) | 0.030 (2) | 0.0037 (16) | 0.0052 (17) | −0.0012 (18) |
C13 | 0.040 (2) | 0.026 (2) | 0.036 (4) | 0.0070 (16) | 0.004 (2) | −0.0038 (17) |
C12 | 0.057 (3) | 0.026 (2) | 0.055 (4) | 0.009 (2) | 0.005 (3) | −0.011 (2) |
C15 | 0.069 (4) | 0.039 (3) | 0.061 (4) | 0.019 (3) | −0.017 (3) | 0.008 (3) |
Br1—C10 | 1.902 (6) | C6—C7 | 1.528 (5) |
O1—C1 | 1.226 (8) | C7—C8 | 1.518 (5) |
O3—C14 | 1.219 (6) | C7—C14 | 1.544 (6) |
O2—C7 | 1.414 (5) | C8—C9 | 1.388 (7) |
O2—H2 | 0.8200 | C8—C13 | 1.392 (6) |
N1—C14 | 1.340 (6) | C9—C10 | 1.395 (7) |
N1—C13 | 1.406 (7) | C9—H9 | 0.9300 |
N1—C15 | 1.456 (7) | C10—C11 | 1.392 (9) |
C3—C2 | 1.453 (12) | C11—C12 | 1.377 (9) |
C3—C4 | 1.503 (12) | C11—H11 | 0.9300 |
C3—H3A | 0.9700 | C2—C1 | 1.504 (9) |
C3—H3B | 0.9700 | C2—H2A | 0.9700 |
C4—C5 | 1.499 (7) | C2—H2B | 0.9700 |
C4—H4A | 0.9700 | C13—C12 | 1.382 (7) |
C4—H4B | 0.9700 | C12—H12 | 0.9300 |
C5—C6 | 1.330 (7) | C15—H15A | 0.9600 |
C5—H5 | 0.9300 | C15—H15B | 0.9600 |
C6—C1 | 1.464 (7) | C15—H15C | 0.9600 |
C7—O2—H2 | 109.5 | C8—C9—H9 | 121.5 |
C14—N1—C13 | 111.3 (4) | C10—C9—H9 | 121.5 |
C14—N1—C15 | 123.6 (5) | C11—C10—C9 | 122.2 (5) |
C13—N1—C15 | 125.1 (5) | C11—C10—Br1 | 119.6 (4) |
C2—C3—C4 | 112.8 (6) | C9—C10—Br1 | 118.1 (4) |
C2—C3—H3A | 109.0 | C12—C11—C10 | 120.1 (4) |
C4—C3—H3A | 109.0 | C12—C11—H11 | 119.9 |
C2—C3—H3B | 109.0 | C10—C11—H11 | 119.9 |
C4—C3—H3B | 109.0 | C3—C2—C1 | 113.6 (6) |
H3A—C3—H3B | 107.8 | C3—C2—H2A | 108.9 |
C5—C4—C3 | 112.0 (5) | C1—C2—H2A | 108.9 |
C5—C4—H4A | 109.2 | C3—C2—H2B | 108.9 |
C3—C4—H4A | 109.2 | C1—C2—H2B | 108.9 |
C5—C4—H4B | 109.2 | H2A—C2—H2B | 107.7 |
C3—C4—H4B | 109.2 | O1—C1—C6 | 120.4 (5) |
H4A—C4—H4B | 107.9 | O1—C1—C2 | 122.5 (6) |
C6—C5—C4 | 123.6 (5) | C6—C1—C2 | 117.1 (5) |
C6—C5—H5 | 118.2 | O3—C14—N1 | 125.7 (4) |
C4—C5—H5 | 118.2 | O3—C14—C7 | 125.0 (4) |
C5—C6—C1 | 120.5 (4) | N1—C14—C7 | 109.2 (4) |
C5—C6—C7 | 121.6 (4) | C12—C13—C8 | 121.7 (5) |
C1—C6—C7 | 117.7 (4) | C12—C13—N1 | 128.5 (4) |
O2—C7—C8 | 111.2 (3) | C8—C13—N1 | 109.7 (4) |
O2—C7—C6 | 111.9 (3) | C11—C12—C13 | 118.3 (5) |
C8—C7—C6 | 117.4 (3) | C11—C12—H12 | 120.9 |
O2—C7—C14 | 104.5 (3) | C13—C12—H12 | 120.9 |
C8—C7—C14 | 101.0 (3) | N1—C15—H15A | 109.5 |
C6—C7—C14 | 109.5 (3) | N1—C15—H15B | 109.5 |
C9—C8—C13 | 120.7 (4) | H15A—C15—H15B | 109.5 |
C9—C8—C7 | 130.5 (4) | N1—C15—H15C | 109.5 |
C13—C8—C7 | 108.6 (4) | H15A—C15—H15C | 109.5 |
C8—C9—C10 | 116.9 (5) | H15B—C15—H15C | 109.5 |
C2—C3—C4—C5 | −45.4 (9) | C5—C6—C1—C2 | 3.5 (8) |
C3—C4—C5—C6 | 18.6 (9) | C7—C6—C1—C2 | 177.9 (6) |
C4—C5—C6—C1 | 2.3 (8) | C3—C2—C1—O1 | 148.5 (8) |
C4—C5—C6—C7 | −171.9 (5) | C3—C2—C1—C6 | −31.0 (10) |
C5—C6—C7—O2 | −1.3 (6) | C13—N1—C14—O3 | 179.3 (4) |
C1—C6—C7—O2 | −175.7 (4) | C15—N1—C14—O3 | 2.8 (8) |
C5—C6—C7—C8 | −131.6 (5) | C13—N1—C14—C7 | −3.8 (5) |
C1—C6—C7—C8 | 54.0 (6) | C15—N1—C14—C7 | 179.7 (5) |
C5—C6—C7—C14 | 114.1 (5) | O2—C7—C14—O3 | 66.0 (5) |
C1—C6—C7—C14 | −60.3 (5) | C8—C7—C14—O3 | −178.5 (4) |
O2—C7—C8—C9 | −68.7 (5) | C6—C7—C14—O3 | −54.0 (5) |
C6—C7—C8—C9 | 62.0 (6) | O2—C7—C14—N1 | −110.9 (4) |
C14—C7—C8—C9 | −179.1 (4) | C8—C7—C14—N1 | 4.6 (4) |
O2—C7—C8—C13 | 106.6 (4) | C6—C7—C14—N1 | 129.1 (4) |
C6—C7—C8—C13 | −122.7 (4) | C9—C8—C13—C12 | −1.1 (7) |
C14—C7—C8—C13 | −3.8 (4) | C7—C8—C13—C12 | −177.0 (4) |
C13—C8—C9—C10 | 0.7 (6) | C9—C8—C13—N1 | 177.7 (4) |
C7—C8—C9—C10 | 175.5 (4) | C7—C8—C13—N1 | 1.9 (5) |
C8—C9—C10—C11 | 0.1 (7) | C14—N1—C13—C12 | −180.0 (5) |
C8—C9—C10—Br1 | −179.3 (3) | C15—N1—C13—C12 | −3.5 (8) |
C9—C10—C11—C12 | −0.6 (8) | C14—N1—C13—C8 | 1.3 (5) |
Br1—C10—C11—C12 | 178.9 (4) | C15—N1—C13—C8 | 177.7 (5) |
C4—C3—C2—C1 | 52.1 (10) | C10—C11—C12—C13 | 0.2 (8) |
C5—C6—C1—O1 | −176.1 (6) | C8—C13—C12—C11 | 0.6 (8) |
C7—C6—C1—O1 | −1.6 (8) | N1—C13—C12—C11 | −178.0 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O3i | 0.93 | 2.54 | 3.115 (7) | 120 |
O2—H2···O3i | 0.82 | 2.01 | 2.785 (5) | 156 |
Symmetry code: (i) −x+1, −y+1, z−1/2. |
Parameters | Optimized | Experimental |
C17—C16 | 1.240 | 1.217 (5) |
O1—C1 | 1.218 | 1.220 (2) |
O3—C14 | 1.231 | 1.221 (3) |
O2—C7 | 1.394 | 1.420 (2) |
N1—C14 | 1.344 | 1.350 (3) |
N1—C13 | 1.383 | 1.410 (3) |
N1—C15 | 1.421 | 1.456 (3) |
C8—C7 | 1.506 | 1.510 (3) |
C8—C13 | 1.349 | 1.392 (3) |
C8—C9 | 1.378 | 1.371 (3) |
C7—C6 | 1.516 | 1.517 (3) |
C7—C14 | 1.520 | 1.553 (3) |
C1—C6 | 1.446 | 1.476 (3) |
C6—C5 | 1.337 | 1.332 (3) |
C13—C12 | 1.375 | 1.378 (3) |
C5—C4 | 1.471 | 1.495 (3) |
C2—C3 | 1.482 | 1.512 (3) |
C3—C4 | 1.468 | 1.506 (3) |
C9—C10 | 1.372 | 1.397 (3) |
C11—C12 | 1.367 | 1.387 (4) |
C11—C10 | 1.357 | 1.370 (4) |
C15—C16 | 1.359 | 1.467 (4) |
Parameters | Optimized | Experimental |
C1—O1 | 1.229 | 1.213 (2) |
C1—C2 | 1.515 | 1.507 (5) |
C1—C6 | 1.499 | 1.465 (3) |
C2—C3 | 1.518 | 1.514 (7) |
C3—C4 | 1.521 | 1.528 (8) |
C4—C5 | 1.499 | 1.486 (6) |
C5—C6 | 1.351 | 1.325 (3) |
C6—C7 | 1.511 | 1.511 (2) |
C7—C8 | 1.506 | 1.505 (2) |
C7—C14 | 1.567 | 1.544 (2) |
C7—O2 | 1.437 | 1.4190 (19) |
C8—C9 | 1.388 | 1.370 (3) |
C8—C13 | 1.401 | 1.385 (3) |
C9—C10 | 1.395 | 1.390 (3) |
C10—C11 | 1.405 | 1.368 (3) |
C11—C12 | 1.399 | 1.378 (3) |
C12—C13 | 1.383 | 1.371 (3) |
C13—N1 | 1.403 | 1.409 (2) |
C14—N1 | 1.400 | 1.352 (2) |
C14—O3 | 1.226 | 1.220 (2) |
C15—C16 | 1.519 | 1.478 (3) |
C15—N1 | 1.443 | 1.457 (3) |
Parameters | Optimized | Experimental |
Br1—C10 | 1.893 | 1.902 (6) |
O1—C1 | 1.228 | 1.226 (8) |
O3—C14 | 1.231 | 1.219 (6) |
O2—C7 | 1.434 | 1.414 (5) |
N1—C14 | 1.392 | 1.340 (6) |
N1—C13 | 1.395 | 1.406 (7) |
N1—C15 | 1.434 | 1.456 (7) |
C3—C4 | 1.521 | 1.503 (12) |
C3—C2 | 1.515 | 1.453 (12) |
C4—C5 | 1.490 | 1.499 (7) |
C5—C6 | 1.349 | 1.330 (7) |
C6—C7 | 1.505 | 1.528 (5) |
C6—C1 | 1.494 | 1.464 (7) |
C7—C8 | 1.510 | 1.518 (5) |
C7—C14 | 1.550 | 1.544 (6) |
C8—C9 | 1.388 | 1.388 (7) |
C8—C13 | 1.403 | 1.392 (6) |
C9—C10 | 1.399 | 1.395 (7) |
C10—C11 | 1.405 | 1.392 (9) |
C2—C1 | 1.513 | 1.504 (9) |
C11—C12 | 1.382 | 1.377 (9) |
C13—C12 | 1.381 | 1.382 (7) |
Parameters | Optimized | Experimental |
O2—C7—C6 | 114.98 | 111.89 (16) |
O2—C7—C14 | 109.32 | 107.55 (15) |
O1—C1—C6 | 120.84 | 120.88 (19) |
O3—C14—N1 | 124.02 | 126.47 (19) |
C14—N1—C15 | 125.01 | 124.0 (2) |
N1—C13—C12 | 128.41 | 128.1 (2) |
C7—C8—C13 | 110.24 | 109.08 (18) |
C8—C7—C6 | 113.58 | 114.55 (16) |
C8—C7—C14 | 98.94 | 101.10 (16) |
C13—C8—C9 | 119.77 | 119.8 (2) |
C12—C11—C10 | 120.42 | 121.5 (2) |
O2—C7—C8 | 106.07 | 108.55 (16) |
O1—C1—C2 | 120.67 | 121.29 (19) |
O3—C14—C7 | 125.14 | 124.63 (18) |
C8—C13—C12 | 121.03 | 122.2 (2) |
C9—C10—C11 | 120.33 | 120.8 (2) |
Parameters | Optimized | Experimental |
C6—C1—O1 | 121.10 | 121.48 (17) |
C7—C8—C13 | 109.68 | 109.25 (15) |
C7—C14—O3 | 125.22 | 125.90 (16) |
C8—C9—C10 | 118.21 | 118.5 (2) |
C8—C13—C12 | 121.20 | 121.61 (19) |
C9—C10—C11 | 120.62 | 120.1 (2) |
C11—C12—C13 | 118.04 | 117.3 (2) |
C12—C13—N1 | 128.74 | 128.59 (18) |
C13—N1—C14 | 111.04 | 110.60 (15) |
C13—N1—C15 | 125.44 | 126.72 (16) |
C16—C15—N1 | 112.50 | 113.4 (2) |
C14—N1—C15 | 123.51 | 122.69 (17) |
N1—C14—O3 | 127.35 | 124.92 (17) |
Parameters | Optimized | Experimental |
O1—C1—C6 | 120.97 | 120.4 (5) |
Br1—C10—C9 | 121.81 | 118.1 (4) |
O3—C14—C7 | 127.76 | 125.0 (4) |
O2—C7—C6 | 112 | 111.9 (3) |
N1—C13—C12 | 128.48 | 128.5 (4) |
C7—C8—C9 | 132.04 | 130.5 (4) |
C8—C7—C14 | 103.09 | 101.0 (3) |
C8—C9—C10 | 121.49 | 116.9 (5) |
C8—C13—C12 | 120.89 | 121.7 (5) |
C9—C10—C11 | 117.34 | 122.2 (5) |
C10—C11—C12 | 121.62 | 120.1 (4) |
N1—C14—C7 | 105.49 | 109.2 (4) |
C11—C12—C13 | 119.35 | 118.3 (5) |
Br1—C10—C11 | 119.05 | 119.6 (4) |
O3—C14—N1 | 126.55 | 125.7 (4) |
No | Atom | Charge | No | Atom | Charge |
1 | C17 | -0.3745 | 12 | C11 | -0.1224 |
2 | O2 | -0.5446 | 13 | C4 | -0.3959 |
3 | O1 | -0.4810 | 14 | C12 | -0.2986 |
4 | O3 | -0.4976 | 15 | C10 | -0.2727 |
5 | N1 | -0.6113 | 16 | C15 | -0.1100 |
6 | C8 | -0.1583 | 17 | C16 | -0.2432 |
7 | C6 | -0.2569 | 18 | C1 | 0.5185 |
8 | C5 | -0.0593 | 19 | C14 | 0.6083 |
9 | C2 | -0.4697 | 20 | C13 | 0.2769 |
10 | C3 | -0.3351 | 21 | C7 | 0.2383 |
11 | C9 | -0.0997 |
No | Atom | Charge | No | Atom | Charge |
1 | C2 | -0.4717 | 11 | C15 | -0.0829 |
2 | C3 | -0.3333 | 12 | C16 | -0.6165 |
3 | C4 | -0.3952 | 13 | N1 | -0.6074 |
4 | C5 | -0.0600 | 14 | O1 | -0.4818 |
5 | C6 | -0.2601 | 15 | O2 | -0.5427 |
6 | C8 | -0.1619 | 16 | O3 | -0.4887 |
7 | C9 | -0.1000 | 17 | C1 | 0.5162 |
8 | C10 | -0.2737 | 18 | C7 | 0.2314 |
9 | C11 | -0.1223 | 19 | C13 | 0.2721 |
10 | C12 | -0.3013 | 20 | C14 | 0.6103 |
No | Atom | Charge | No | Atom | Charge |
1 | C2 | -0.4712 | 12 | C16 | -0.6165 |
2 | C3 | -0.3334 | 13 | N1 | -0.6063 |
3 | C4 | -0.4010 | 14 | O1 | -0.4820 |
4 | C5 | -0.0307 | 15 | O2 | -0.5471 |
5 | C6 | -0.2515 | 16 | O3 | -0.4462 |
6 | C8 | -0.2184 | 17 | C1 | 0.5151 |
7 | C9 | -0.1340 | 18 | C7 | 0.2608 |
8 | C10 | -0.5168 | 19 | C13 | 0.2896 |
9 | C11 | -0.1509 | 20 | C14 | 0.5952 |
10 | C12 | -0.2977 | 21 | Br | 0.4344 |
11 | C15 | -0.3149 |
Parameters | Units | IS1 | IS2 | IS3 |
EHOMO | eV | -8.661 | -8.584 | -8.706 |
ELUMO | eV | -0.355 | -0.324 | -0.463 |
Energy gap (ELUMO – EHOMO) | eV | 8.306 | 8.260 | 8.243 |
Electronic energy | eV | -25238.3454 | -24210.9893 | -23758.9724 |
Chemical potential (µ) | eV | -4.508 | -4.454 | -4.585 |
Global hardness (η) | eV | 4.153 | 4.130 | 4.121 |
Global softness (S) | eV-1 | 0.1118 | 0.121 | 0.121 |
Electrophilicity index (ω) | eV | 2.252 | 2.402 | 2.550 |
Electronegativity (χ) | eV | 4.508 | 4.454 | 4.584 |
Dipole (µ) | Debye | 4.303 | 3.771 | 1.450 |
Static second-order hyperpolarizability (γ) | 10–35 esu | 1.8889 | 0.9213 | 1.2904 |
Compounds | log P | TPSA | MW | Volume | nON | nOH-NH | nrotb | No. violations |
IS1 | 1.99 | 57.61 | 283.33 | 259.99 | 4 | 1 | 3 | 0 |
IS2 | 1.72 | 57.61 | 271.32 | 248.82 | 4 | 1 | 2 | 0 |
IS3 | 2.13 | 57.61 | 336.19 | 249.90 | 1 | 1 | 1 | 0 |
Compounds | GPCR | ICM | KI | NR | PI | EI |
IS1 | -0.29 | -0.52 | -1.04 | -0.22 | -0.59 | -0.31 |
IS2 | -0.29 | -0.60 | -1.02 | -0.24 | -0.63 | -0.30 |
IS3 | -0.46 | -0.64 | -1.05 | -0.40 | -0.69 | -0.33 |
Compounds | E. coli | P. vulgaris | S. flexneri | S. aureus | M. luteus |
IS1 | 10 | 10 | 10 | 12 | 13 |
IS2 | 13 | 11 | 12 | 13 | 14 |
IS3 | 14 | 13 | 14 | 15 | 15 |
Compound | Aspergillus niger | Compound | Aspergillus niger |
IS1 | 16 | IS3 | 18 |
IS2 | 17 |
Inhibitor | Binding energy (K cal mol-1) | Distance (Å) | Inhibition constant (µM) | Binding site of protein | Binding site of ligand |
IS1 | -6.11 | 2.94,2.84 | 33.27 | OH (Thr600), COOH (Glu447) | Aliphatic CHC═O |
IS2 | -7.37 | 2.43,2.79,2.69,2.85 | 3.95 | COOH (Glu447), COOH (Gln521), NH2 (Gln521), NH2(Gln521) | OH, C═O, C═O, α,β-unsaturated ketone |
IS3 | -7.23 | 2.86,3.24,2.89,3.09,3.35 | 14.69 | NH2 (Ser400), COOH (Thr399), COOH (Glu602), NH2 (Lys604), NH2 (Asn632) | OH, Ar-CH, N-CH3, N-CH3, Br |
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