Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806020125/cs2005sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806020125/cs2005Isup2.hkl |
CCDC reference: 613642
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).
C21H18N2O3 | F(000) = 728 |
Mr = 346.37 | Dx = 1.275 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54184 Å |
a = 11.260 (13) Å | Cell parameters from 25 reflections |
b = 12.74 (2) Å | θ = 8–17° |
c = 12.81 (2) Å | µ = 0.7 mm−1 |
β = 100.76 (13)° | T = 293 K |
V = 1805 (5) Å3 | Prism, colourless |
Z = 4 | 0.32 × 0.3 × 0.2 mm |
Enraf–Nonius CAD-4 diffractometer | θmax = 76.5°, θmin = 4.9° |
non–profiled ω/2θ scans | h = −14→14 |
7498 measured reflections | k = 0→16 |
3756 independent reflections | l = −16→16 |
2854 reflections with I > 2σ(I) | 3 standard reflections every 120 min |
Rint = 0.031 | intensity decay: −1% |
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0506P)2 + 0.2871P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.039 | (Δ/σ)max < 0.001 |
wR(F2) = 0.110 | Δρmax = 0.24 e Å−3 |
S = 1.02 | Δρmin = −0.28 e Å−3 |
3756 reflections | Extinction correction: SHELXS97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
296 parameters | Extinction coefficient: 0.0032 (4) |
0 restraints |
Experimental. Spectroscopic analysis: 1H NMR (DMSO-d6, δ, p.p.m.): 1.83 (s, CH3, 3H), 7.16–7.28 (m, BiPhe, 5H, Phe, 3H), 7.36–7.40 (m, BiPhe, 1H, Phe, 2H), 7.50–7.51 (BiPhe, 2H), 9.15 (s, NHCOCH3, 1H), 10.27 (s, NH, 1H); 13C NMR (DMSO-d6, δ, p.p.m.): 23.02 (CH3), 118.40, 121.85, 125.39, 125.77, 127.03, 127.34, 129.20, 129.40, 130.05, 133.59, 134.89, 136.07, 137.73, 150.53, 151.70, 168.57; IR (KBr, ν, cm-1): 3454.26, 3394.47, 3238.24, 3172.67, 3093.59, 3041.52, 2937.37, 2856.37, 2790.79, 2362.63, 2335.62, 2219.90, 1951.82, 1930.60, 1733.88, 1666.37, 1608.51, 1589.23, 1483.15, 1446.51, 1407.93, 1321.14, 1298.00, 1228.57, 1157.20, 1068.49, 1022.20, 1010.63, 916.20, 835.12, 811.97, 796.54, 756.04, 719.40, 663.46, 561.24, 507.24, 466.74, 379.95, 329.80, 287.37. |
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) | |
C1 | 0.31521 (14) | 0.46781 (14) | 0.88579 (13) | 0.0580 (4) | |
C2 | 0.19798 (13) | 0.42740 (11) | 0.82207 (11) | 0.0461 (3) | |
C3 | 0.08911 (12) | 0.38805 (11) | 0.64074 (10) | 0.0439 (3) | |
C4 | −0.02684 (14) | 0.42802 (14) | 0.63844 (13) | 0.0562 (4) | |
C5 | −0.12322 (15) | 0.39400 (16) | 0.56271 (15) | 0.0683 (5) | |
C6 | −0.10448 (16) | 0.32182 (18) | 0.48750 (15) | 0.0728 (5) | |
C7 | 0.01107 (15) | 0.28208 (15) | 0.48943 (13) | 0.0604 (4) | |
C8 | 0.10982 (12) | 0.31247 (11) | 0.56694 (10) | 0.0439 (3) | |
C9 | 0.23102 (12) | 0.26326 (11) | 0.57023 (10) | 0.0420 (3) | |
C10 | 0.27938 (13) | 0.25041 (12) | 0.47827 (11) | 0.0491 (3) | |
C11 | 0.39088 (13) | 0.20179 (13) | 0.48166 (10) | 0.0487 (3) | |
C12 | 0.45839 (12) | 0.16628 (11) | 0.57723 (10) | 0.0429 (3) | |
C13 | 0.41005 (12) | 0.17648 (12) | 0.66959 (10) | 0.0450 (3) | |
C14 | 0.29829 (13) | 0.22417 (11) | 0.66496 (10) | 0.0443 (3) | |
C15 | 0.66316 (13) | 0.11177 (13) | 0.66091 (11) | 0.0487 (3) | |
C16 | 0.86395 (13) | 0.05460 (13) | 0.71359 (11) | 0.0494 (3) | |
C17 | 0.88001 (18) | −0.04234 (16) | 0.76027 (15) | 0.0660 (4) | |
C18 | 0.9781 (2) | −0.0575 (2) | 0.84284 (17) | 0.0798 (6) | |
C19 | 1.05668 (18) | 0.0220 (2) | 0.87639 (15) | 0.0776 (6) | |
C20 | 1.04112 (16) | 0.1173 (2) | 0.82793 (17) | 0.0751 (6) | |
C21 | 0.94430 (16) | 0.13453 (15) | 0.74553 (15) | 0.0618 (4) | |
H1A | 0.3674 | 0.4894 | 0.8384 | 0.087* | 0.5 |
H1B | 0.3538 | 0.4132 | 0.9316 | 0.087* | 0.5 |
H1C | 0.2992 | 0.5266 | 0.928 | 0.087* | 0.5 |
H1D | 0.3128 | 0.4634 | 0.9602 | 0.087* | 0.5 |
H1E | 0.3264 | 0.5396 | 0.8671 | 0.087* | 0.5 |
H1F | 0.381 | 0.4262 | 0.8707 | 0.087* | 0.5 |
H1N | 0.2553 (19) | 0.4464 (15) | 0.6900 (16) | 0.077 (6)* | |
H2N | 0.5943 (17) | 0.1095 (15) | 0.5116 (16) | 0.071 (5)* | |
H4 | −0.0367 (16) | 0.4793 (14) | 0.6935 (15) | 0.065 (5)* | |
H5 | −0.206 (2) | 0.4229 (16) | 0.5595 (17) | 0.085 (6)* | |
H6 | −0.1740 (19) | 0.2979 (16) | 0.4354 (17) | 0.085 (6)* | |
H7 | 0.0244 (17) | 0.2282 (15) | 0.4355 (16) | 0.075 (5)* | |
H10 | 0.2302 (14) | 0.2756 (13) | 0.4099 (14) | 0.056 (4)* | |
H11 | 0.4230 (14) | 0.1945 (13) | 0.4167 (14) | 0.056 (4)* | |
H13 | 0.4549 (14) | 0.1530 (12) | 0.7374 (13) | 0.048 (4)* | |
H14 | 0.2654 (14) | 0.2303 (12) | 0.7326 (13) | 0.054 (4)* | |
H17 | 0.8264 (19) | −0.0942 (19) | 0.7374 (17) | 0.088 (7)* | |
H18 | 0.990 (2) | −0.120 (2) | 0.8746 (19) | 0.102 (8)* | |
H19 | 1.128 (2) | 0.0093 (17) | 0.9387 (18) | 0.088 (6)* | |
H20 | 1.100 (2) | 0.175 (2) | 0.856 (2) | 0.117 (9)* | |
H21 | 0.934 (2) | 0.2006 (19) | 0.7127 (19) | 0.099 (7)* | |
N1 | 0.18901 (11) | 0.42823 (10) | 0.71585 (9) | 0.0472 (3) | |
N2 | 0.57348 (11) | 0.12143 (11) | 0.57576 (9) | 0.0520 (3) | |
O1 | 0.11529 (11) | 0.39476 (12) | 0.86327 (9) | 0.0741 (4) | |
O2 | 0.65950 (10) | 0.13264 (12) | 0.75166 (8) | 0.0693 (4) | |
O3 | 0.76480 (10) | 0.07135 (11) | 0.63069 (8) | 0.0671 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0528 (9) | 0.0687 (10) | 0.0506 (8) | −0.0058 (7) | 0.0047 (7) | 0.0023 (7) |
C2 | 0.0487 (7) | 0.0491 (8) | 0.0416 (7) | −0.0015 (6) | 0.0114 (6) | 0.0019 (6) |
C3 | 0.0443 (7) | 0.0497 (7) | 0.0385 (6) | 0.0003 (6) | 0.0094 (5) | 0.0026 (6) |
C4 | 0.0518 (8) | 0.0631 (10) | 0.0552 (9) | 0.0104 (7) | 0.0134 (7) | −0.0016 (7) |
C5 | 0.0463 (9) | 0.0891 (13) | 0.0663 (10) | 0.0199 (9) | 0.0028 (7) | 0.0008 (9) |
C6 | 0.0496 (9) | 0.1016 (15) | 0.0592 (10) | 0.0129 (9) | −0.0104 (8) | −0.0096 (10) |
C7 | 0.0530 (9) | 0.0765 (11) | 0.0474 (8) | 0.0100 (8) | −0.0021 (7) | −0.0094 (8) |
C8 | 0.0433 (7) | 0.0515 (8) | 0.0360 (6) | 0.0045 (6) | 0.0052 (5) | 0.0021 (6) |
C9 | 0.0424 (7) | 0.0464 (7) | 0.0362 (6) | 0.0019 (6) | 0.0048 (5) | −0.0007 (5) |
C10 | 0.0500 (8) | 0.0642 (9) | 0.0313 (6) | 0.0075 (7) | 0.0032 (6) | 0.0007 (6) |
C11 | 0.0488 (8) | 0.0655 (9) | 0.0323 (6) | 0.0058 (7) | 0.0084 (6) | −0.0027 (6) |
C12 | 0.0416 (7) | 0.0495 (7) | 0.0373 (6) | 0.0022 (6) | 0.0068 (5) | −0.0035 (5) |
C13 | 0.0453 (7) | 0.0559 (8) | 0.0336 (6) | 0.0056 (6) | 0.0073 (5) | 0.0061 (6) |
C14 | 0.0469 (7) | 0.0529 (8) | 0.0342 (6) | 0.0037 (6) | 0.0105 (5) | 0.0029 (6) |
C15 | 0.0416 (7) | 0.0655 (9) | 0.0392 (7) | 0.0039 (6) | 0.0079 (5) | −0.0044 (6) |
C16 | 0.0409 (7) | 0.0684 (10) | 0.0392 (7) | 0.0105 (7) | 0.0081 (5) | −0.0024 (6) |
C17 | 0.0696 (11) | 0.0615 (10) | 0.0682 (11) | 0.0009 (9) | 0.0160 (9) | −0.0041 (8) |
C18 | 0.0925 (15) | 0.0827 (14) | 0.0661 (11) | 0.0375 (12) | 0.0196 (11) | 0.0189 (11) |
C19 | 0.0544 (10) | 0.1231 (19) | 0.0533 (10) | 0.0295 (12) | 0.0049 (8) | −0.0109 (11) |
C20 | 0.0435 (9) | 0.1037 (16) | 0.0787 (12) | −0.0032 (10) | 0.0128 (8) | −0.0250 (12) |
C21 | 0.0550 (9) | 0.0655 (11) | 0.0679 (10) | 0.0015 (8) | 0.0194 (8) | 0.0010 (9) |
N1 | 0.0455 (6) | 0.0575 (7) | 0.0416 (6) | −0.0064 (5) | 0.0157 (5) | −0.0054 (5) |
N2 | 0.0444 (6) | 0.0767 (9) | 0.0346 (6) | 0.0120 (6) | 0.0061 (5) | −0.0055 (6) |
O1 | 0.0676 (7) | 0.1128 (10) | 0.0439 (6) | −0.0328 (7) | 0.0157 (5) | 0.0044 (6) |
O2 | 0.0462 (6) | 0.1212 (11) | 0.0388 (5) | 0.0096 (6) | 0.0040 (4) | −0.0165 (6) |
O3 | 0.0488 (6) | 0.1116 (10) | 0.0397 (5) | 0.0235 (6) | 0.0051 (4) | −0.0081 (6) |
C1—H1A | 0.96 | C14—C13 | 1.389 (2) |
C1—H1B | 0.96 | C14—C9 | 1.396 (3) |
C1—H1C | 0.96 | C14—H14 | 1.006 (16) |
C1—H1D | 0.96 | C15—O2 | 1.200 (3) |
C1—H1E | 0.96 | C15—O3 | 1.375 (2) |
C1—H1F | 0.96 | C16—C17 | 1.369 (3) |
C2—C1 | 1.507 (3) | C16—C21 | 1.373 (3) |
C3—C4 | 1.397 (3) | C17—C18 | 1.393 (4) |
C4—C5 | 1.383 (3) | C17—H17 | 0.91 (2) |
C4—H4 | 0.983 (18) | C18—H18 | 0.90 (3) |
C5—C6 | 1.376 (3) | C19—C20 | 1.360 (4) |
C5—H5 | 0.99 (2) | C19—C18 | 1.360 (4) |
C6—H6 | 0.98 (2) | C19—H19 | 1.03 (2) |
C7—C6 | 1.392 (3) | C20—H20 | 1.01 (3) |
C7—H7 | 1.00 (2) | C21—C20 | 1.386 (4) |
C8—C3 | 1.399 (3) | C21—H21 | 0.94 (2) |
C8—C7 | 1.400 (3) | N1—C2 | 1.345 (3) |
C9—C10 | 1.396 (3) | N1—C3 | 1.431 (3) |
C9—C8 | 1.495 (2) | N1—H1N | 0.90 (2) |
C10—C11 | 1.393 (2) | N2—C15 | 1.346 (3) |
C10—H10 | 0.998 (17) | N2—C12 | 1.420 (2) |
C11—H11 | 0.971 (17) | N2—H2N | 0.91 (2) |
C12—C11 | 1.390 (3) | O1—C2 | 1.225 (2) |
C12—C13 | 1.397 (3) | O3—C16 | 1.406 (3) |
C13—H13 | 0.967 (16) | ||
C2—C1—H1A | 109.5 | C14—C13—H13 | 119.4 (9) |
C2—C1—H1B | 109.5 | C14—C9—C8 | 121.21 (16) |
C2—C1—H1C | 109.5 | C15—N2—C12 | 125.06 (15) |
C2—C1—H1D | 109.5 | C15—N2—H2N | 115.9 (12) |
C2—C1—H1E | 109.5 | C15—O3—C16 | 115.45 (15) |
C2—C1—H1F | 109.5 | C16—C17—C18 | 118.5 (2) |
C2—N1—C3 | 125.31 (16) | C16—C17—H17 | 119.4 (14) |
C2—N1—H1N | 117.5 (13) | C16—C21—C20 | 119.4 (2) |
C3—C4—H4 | 117.3 (11) | C16—C21—H21 | 120.6 (14) |
C3—C8—C7 | 117.31 (15) | C17—C16—C21 | 120.86 (19) |
C3—C8—C9 | 122.41 (15) | C17—C16—O3 | 119.22 (16) |
C3—N1—H1N | 116.5 (13) | C17—C18—H18 | 119.9 (16) |
C4—C3—C8 | 120.66 (16) | C18—C17—H17 | 122.0 (14) |
C4—C3—N1 | 119.87 (16) | C18—C19—H19 | 119.4 (12) |
C4—C5—H5 | 121.2 (12) | C19—C18—C17 | 120.9 (2) |
C5—C4—C3 | 120.56 (18) | C19—C18—H18 | 119.2 (16) |
C5—C4—H4 | 122.2 (11) | C19—C20—C21 | 120.3 (2) |
C5—C6—C7 | 119.71 (19) | C19—C20—H20 | 117.7 (15) |
C5—C6—H6 | 118.5 (12) | C20—C19—C18 | 120.0 (2) |
C6—C5—C4 | 119.83 (17) | C20—C19—H19 | 120.6 (12) |
C6—C5—H5 | 119.0 (12) | C20—C21—H21 | 120.0 (15) |
C6—C7—C8 | 121.87 (18) | C21—C16—O3 | 119.91 (17) |
C6—C7—H7 | 119.7 (11) | C21—C20—H20 | 122.0 (15) |
C7—C6—H6 | 121.7 (12) | H1A—C1—H1B | 109.5 |
C7—C8—C9 | 120.26 (16) | H1A—C1—H1C | 109.5 |
C8—C3—N1 | 119.40 (14) | H1A—C1—H1D | 141.1 |
C8—C7—H7 | 118.4 (11) | H1A—C1—H1E | 56.3 |
C9—C10—H10 | 117.6 (9) | H1A—C1—H1F | 56.3 |
C9—C14—H14 | 119.5 (9) | H1B—C1—H1C | 109.5 |
C10—C11—H11 | 119.5 (10) | H1B—C1—H1D | 56.3 |
C10—C9—C14 | 117.20 (16) | H1B—C1—H1E | 141.1 |
C10—C9—C8 | 121.54 (16) | H1B—C1—H1F | 56.3 |
C11—C10—C9 | 121.13 (16) | H1C—C1—H1D | 56.3 |
C11—C10—H10 | 121.3 (9) | H1C—C1—H1E | 56.3 |
C11—C12—C13 | 118.66 (16) | H1C—C1—H1F | 141.1 |
C11—C12—N2 | 118.01 (16) | H1D—C1—H1E | 109.5 |
C12—C11—C10 | 120.89 (16) | H1D—C1—H1F | 109.5 |
C12—C11—H11 | 119.5 (10) | H1E—C1—H1F | 109.5 |
C12—C13—H13 | 120.7 (9) | N1—C2—C1 | 115.96 (17) |
C12—N2—H2N | 118.0 (12) | N2—C15—O3 | 110.12 (16) |
C13—C12—N2 | 123.33 (16) | O1—C2—C1 | 122.82 (16) |
C13—C14—C9 | 122.24 (16) | O1—C2—N1 | 121.22 (17) |
C13—C14—H14 | 118.2 (9) | O2—C15—N2 | 127.43 (17) |
C14—C13—C12 | 119.84 (16) | O2—C15—O3 | 122.44 (17) |
C2—N1—C3—C4 | 58.4 (2) | C13—C14—C9—C10 | 1.5 (2) |
C2—N1—C3—C8 | −124.6 (2) | C13—C14—C9—C8 | 178.8 (1) |
C3—C4—C5—C6 | −1.4 (3) | C14—C9—C10—C11 | −0.8 (2) |
C3—C8—C7—C6 | −2.4 (3) | C14—C9—C8—C3 | 47.6 (2) |
C3—N1—C2—C1 | 176.2 (1) | C14—C9—C8—C7 | −131.2 (2) |
C3—N1—C2—O1 | −3.3 (2) | C15—N2—C12—C11 | 159.5 (2) |
C4—C5—C6—C7 | 1.2 (3) | C15—N2—C12—C13 | −20.4 (2) |
C7—C8—C3—C4 | 2.2 (2) | C15—O3—C16—C17 | 93.9 (2) |
C7—C8—C3—N1 | −174.7 (1) | C15—O3—C16—C21 | −87.1 (2) |
C8—C3—C4—C5 | −0.4 (2) | C16—C17—C18—C19 | −0.2 (3) |
C8—C7—C6—C5 | 0.8 (3) | C16—C21—C20—C19 | 0.3 (3) |
C8—C9—C10—C11 | −178.2 (1) | C17—C16—C21—C20 | −1.6 (2) |
C9—C10—C11—C12 | −1.2 (2) | C18—C19—C20—C21 | 1.1 (3) |
C9—C14—C13—C12 | −0.1 (2) | C20—C19—C18—C17 | −1.1 (3) |
C9—C8—C3—C4 | −176.5 (1) | C21—C16—C17—C18 | 1.6 (3) |
C9—C8—C3—N1 | 6.5 (2) | N1—C3—C4—C5 | 176.6 (1) |
C9—C8—C7—C6 | 176.3 (2) | N2—C12—C11—C10 | −177.4 (1) |
C10—C9—C8—C3 | −135.2 (2) | N2—C12—C13—C14 | 178.0 (1) |
C10—C9—C8—C7 | 46.1 (2) | N2—C15—O3—C16 | −178.2 (1) |
C11—C12—C13—C14 | −1.9 (2) | O2—C15—O3—C16 | 0.9 (2) |
C12—N2—C15—O2 | 4.9 (3) | O3—C16—C17—C18 | −179.5 (1) |
C12—N2—C15—O3 | −176.1 (1) | O3—C16—C21—C20 | 179.5 (1) |
C13—C12—C11—C10 | 2.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···O1i | 0.91 (2) | 1.96 (2) | 2.855 (5) | 169 (2) |
C1—H1D···O3ii | 0.96 | 2.39 | 3.328 (6) | 166 |
C4—H4···O2iii | 0.98 (2) | 2.57 (2) | 3.434 (6) | 147 (1) |
C10—H10···O2iv | 0.99 (2) | 2.35 (2) | 3.318 (6) | 164 (1) |
C11—H11···O1i | 0.97 (2) | 2.65 (2) | 3.410 (6) | 136 (1) |
Symmetry codes: (i) x+1/2, −y+1/2, z−1/2; (ii) x−1/2, −y+1/2, z+1/2; (iii) −x+1/2, y+1/2, −z+3/2; (iv) x−1/2, −y+1/2, z−1/2. |