Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807001341/at2204sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807001341/at2204Isup2.hkl |
CCDC reference: 636121
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
C15H14N2O4 | Z = 4 |
Mr = 286.28 | F(000) = 600 |
Triclinic, P1 | Dx = 1.379 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.821 (2) Å | Cell parameters from 2372 reflections |
b = 8.960 (3) Å | θ = 2.3–24.5° |
c = 26.909 (3) Å | µ = 0.10 mm−1 |
α = 96.397 (3)° | T = 298 K |
β = 92.116 (3)° | Block, yellow |
γ = 98.070 (3)° | 0.48 × 0.46 × 0.19 mm |
V = 1379.0 (7) Å3 |
Bruker SMART CCD area-detector diffractometer | 5596 independent reflections |
Radiation source: fine-focus sealed tube | 2885 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
φ and ω scans | θmax = 26.5°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −7→7 |
Tmin = 0.953, Tmax = 0.981 | k = −11→10 |
8165 measured reflections | l = −22→33 |
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)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.130 | w = 1/[σ2(Fo2) + (0.0511P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max < 0.001 |
5596 reflections | Δρmax = 0.16 e Å−3 |
380 parameters | Δρmin = −0.16 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0164 (16) |
Experimental. IR data (KBr pellet, cm-1): 3331 (s), 3082 (m), 3028 (m), 2932 (m), 2937 (m), 1649 (s), 1593 (s), 1540 (s), 1493 (s), 1350 (s), 1268 (s), 1255 (s), 1172 (s), 1111 (s), 848 (s), 744 (s), 695 (m). 1H NMR (200 MHz, CDCl3, TMS internal reference): δ 8.38–8.41 (t, 1H, NH), 8.17–8.22 (m, 2H, p-NO2–C6H4), 7.00–7.32 (m, 7H, p-NO2–C6H4 and –C6H5), 4.95 (s, 2H, O–CH2–CO), 4.61–4.62 (d, 2H, N–CH2–Ar). Elemental analysis: found: C 62.83, H 4.88, N 9.92%; calculated: C 62.93, H 4.93, N 9.79%. |
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.4420 (3) | 0.16512 (17) | 0.25666 (6) | 0.0607 (5) | |
O2 | 0.5887 (3) | 0.44600 (17) | 0.17662 (6) | 0.0580 (5) | |
O3 | 0.5393 (4) | 0.7992 (3) | −0.00817 (7) | 0.0970 (7) | |
O4 | 0.1953 (4) | 0.6789 (2) | −0.01445 (8) | 0.0984 (7) | |
O5 | 0.0881 (3) | 0.60285 (18) | 0.23664 (7) | 0.0757 (6) | |
O6 | 0.5682 (3) | 0.83668 (18) | 0.30762 (6) | 0.0595 (5) | |
O7 | 0.5059 (4) | 1.2628 (3) | 0.50351 (8) | 0.1147 (9) | |
O8 | 0.1608 (5) | 1.1455 (3) | 0.49740 (9) | 0.1167 (9) | |
N1 | 0.7641 (3) | 0.33481 (19) | 0.25186 (6) | 0.0471 (5) | |
H1 | 0.8233 | 0.4134 | 0.2385 | 0.057* | |
N2 | 0.3885 (5) | 0.7093 (2) | 0.00606 (8) | 0.0628 (6) | |
N3 | 0.1875 (3) | 0.8564 (2) | 0.24511 (7) | 0.0501 (5) | |
H3 | 0.2945 | 0.9310 | 0.2554 | 0.060* | |
N4 | 0.3558 (5) | 1.1666 (3) | 0.48283 (9) | 0.0745 (7) | |
C1 | 0.5497 (4) | 0.2709 (2) | 0.23749 (8) | 0.0438 (6) | |
C2 | 0.4319 (4) | 0.3317 (2) | 0.19511 (8) | 0.0485 (6) | |
H2A | 0.3813 | 0.2501 | 0.1685 | 0.058* | |
H2B | 0.2960 | 0.3738 | 0.2067 | 0.058* | |
C3 | 0.5256 (4) | 0.5045 (2) | 0.13427 (8) | 0.0452 (6) | |
C4 | 0.3091 (4) | 0.4720 (3) | 0.11031 (9) | 0.0522 (6) | |
H4 | 0.1932 | 0.4055 | 0.1225 | 0.063* | |
C5 | 0.2659 (4) | 0.5392 (3) | 0.06799 (9) | 0.0551 (6) | |
H5 | 0.1202 | 0.5182 | 0.0513 | 0.066* | |
C6 | 0.4383 (4) | 0.6371 (2) | 0.05063 (8) | 0.0474 (6) | |
C7 | 0.6552 (4) | 0.6713 (3) | 0.07424 (9) | 0.0535 (6) | |
H7 | 0.7700 | 0.7388 | 0.0621 | 0.064* | |
C8 | 0.6990 (4) | 0.6031 (2) | 0.11628 (9) | 0.0524 (6) | |
H8 | 0.8455 | 0.6234 | 0.1326 | 0.063* | |
C9 | 0.9033 (4) | 0.2774 (2) | 0.28921 (8) | 0.0524 (6) | |
H9A | 1.0517 | 0.2632 | 0.2756 | 0.063* | |
H9B | 0.8259 | 0.1786 | 0.2954 | 0.063* | |
C10 | 0.9478 (4) | 0.3771 (2) | 0.33854 (8) | 0.0460 (6) | |
C11 | 1.1432 (4) | 0.3710 (3) | 0.36829 (10) | 0.0622 (7) | |
H11 | 1.2508 | 0.3092 | 0.3570 | 0.075* | |
C12 | 1.1807 (5) | 0.4558 (3) | 0.41473 (11) | 0.0788 (9) | |
H12 | 1.3124 | 0.4497 | 0.4346 | 0.095* | |
C13 | 1.0262 (6) | 0.5483 (3) | 0.43159 (10) | 0.0750 (8) | |
H13 | 1.0529 | 0.6060 | 0.4627 | 0.090* | |
C14 | 0.8323 (5) | 0.5557 (3) | 0.40251 (11) | 0.0773 (8) | |
H14 | 0.7257 | 0.6181 | 0.4139 | 0.093* | |
C15 | 0.7940 (4) | 0.4706 (3) | 0.35620 (9) | 0.0633 (7) | |
H15 | 0.6615 | 0.4767 | 0.3366 | 0.076* | |
C16 | 0.2190 (4) | 0.7182 (3) | 0.25354 (8) | 0.0514 (6) | |
C17 | 0.4291 (4) | 0.7004 (3) | 0.28526 (9) | 0.0614 (7) | |
H17A | 0.3776 | 0.6407 | 0.3118 | 0.074* | |
H17B | 0.5267 | 0.6425 | 0.2647 | 0.074* | |
C18 | 0.5048 (4) | 0.9079 (3) | 0.35164 (9) | 0.0492 (6) | |
C19 | 0.6704 (4) | 1.0218 (3) | 0.37482 (9) | 0.0586 (7) | |
H19 | 0.8145 | 1.0416 | 0.3612 | 0.070* | |
C20 | 0.6227 (5) | 1.1060 (3) | 0.41794 (10) | 0.0644 (7) | |
H20 | 0.7334 | 1.1835 | 0.4336 | 0.077* | |
C21 | 0.4104 (5) | 1.0746 (3) | 0.43764 (9) | 0.0557 (6) | |
C22 | 0.2469 (4) | 0.9583 (3) | 0.41602 (9) | 0.0598 (7) | |
H22 | 0.1054 | 0.9363 | 0.4305 | 0.072* | |
C23 | 0.2947 (4) | 0.8733 (3) | 0.37211 (9) | 0.0587 (7) | |
H23 | 0.1856 | 0.7941 | 0.3569 | 0.070* | |
C24 | −0.0198 (4) | 0.8876 (3) | 0.21925 (8) | 0.0540 (6) | |
H24A | −0.0919 | 0.9586 | 0.2413 | 0.065* | |
H24B | −0.1281 | 0.7940 | 0.2131 | 0.065* | |
C25 | 0.0165 (4) | 0.9513 (2) | 0.17036 (8) | 0.0428 (5) | |
C26 | 0.1980 (4) | 0.9251 (2) | 0.14061 (8) | 0.0484 (6) | |
H26 | 0.3076 | 0.8676 | 0.1512 | 0.058* | |
C27 | 0.2186 (4) | 0.9833 (3) | 0.09516 (9) | 0.0573 (7) | |
H27 | 0.3428 | 0.9661 | 0.0756 | 0.069* | |
C28 | 0.0560 (5) | 1.0664 (3) | 0.07896 (9) | 0.0619 (7) | |
H28 | 0.0689 | 1.1042 | 0.0482 | 0.074* | |
C29 | −0.1246 (5) | 1.0936 (3) | 0.10784 (10) | 0.0637 (7) | |
H29 | −0.2344 | 1.1504 | 0.0970 | 0.076* | |
C30 | −0.1436 (4) | 1.0367 (3) | 0.15312 (9) | 0.0555 (6) | |
H30 | −0.2670 | 1.0560 | 0.1727 | 0.067* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0651 (11) | 0.0480 (10) | 0.0664 (11) | −0.0073 (8) | 0.0028 (9) | 0.0153 (8) |
O2 | 0.0573 (11) | 0.0598 (10) | 0.0525 (10) | −0.0134 (8) | −0.0093 (8) | 0.0187 (8) |
O3 | 0.0958 (16) | 0.1193 (17) | 0.0843 (15) | 0.0057 (13) | 0.0176 (12) | 0.0572 (14) |
O4 | 0.1057 (17) | 0.0964 (15) | 0.0894 (16) | −0.0056 (13) | −0.0405 (14) | 0.0353 (12) |
O5 | 0.0906 (14) | 0.0428 (10) | 0.0844 (14) | −0.0170 (9) | 0.0022 (11) | 0.0011 (9) |
O6 | 0.0596 (11) | 0.0675 (11) | 0.0499 (10) | 0.0029 (9) | 0.0070 (8) | 0.0065 (9) |
O7 | 0.1152 (19) | 0.1178 (18) | 0.0934 (17) | 0.0059 (15) | −0.0204 (14) | −0.0424 (15) |
O8 | 0.126 (2) | 0.1133 (18) | 0.1027 (19) | 0.0052 (16) | 0.0488 (17) | −0.0212 (14) |
N1 | 0.0526 (12) | 0.0417 (10) | 0.0446 (11) | −0.0038 (9) | 0.0000 (9) | 0.0091 (9) |
N2 | 0.0803 (18) | 0.0578 (14) | 0.0516 (14) | 0.0135 (13) | 0.0012 (13) | 0.0080 (11) |
N3 | 0.0601 (13) | 0.0393 (11) | 0.0464 (12) | −0.0058 (9) | −0.0037 (10) | 0.0039 (9) |
N4 | 0.092 (2) | 0.0706 (16) | 0.0600 (16) | 0.0168 (15) | 0.0000 (15) | 0.0004 (13) |
C1 | 0.0524 (15) | 0.0337 (12) | 0.0424 (14) | 0.0008 (11) | 0.0059 (11) | −0.0024 (10) |
C2 | 0.0509 (15) | 0.0411 (13) | 0.0496 (14) | −0.0042 (11) | 0.0012 (12) | 0.0021 (11) |
C3 | 0.0523 (15) | 0.0406 (13) | 0.0400 (13) | −0.0008 (11) | −0.0002 (11) | 0.0036 (11) |
C4 | 0.0473 (15) | 0.0528 (14) | 0.0533 (15) | −0.0074 (11) | −0.0010 (12) | 0.0118 (12) |
C5 | 0.0492 (15) | 0.0574 (15) | 0.0556 (16) | −0.0009 (12) | −0.0087 (12) | 0.0072 (13) |
C6 | 0.0572 (16) | 0.0465 (13) | 0.0388 (13) | 0.0103 (12) | 0.0016 (12) | 0.0034 (11) |
C7 | 0.0573 (16) | 0.0514 (14) | 0.0509 (15) | −0.0011 (12) | 0.0090 (13) | 0.0111 (12) |
C8 | 0.0486 (15) | 0.0535 (14) | 0.0515 (15) | −0.0042 (12) | −0.0011 (12) | 0.0064 (12) |
C9 | 0.0561 (15) | 0.0522 (14) | 0.0500 (15) | 0.0106 (12) | 0.0043 (12) | 0.0078 (12) |
C10 | 0.0432 (14) | 0.0459 (13) | 0.0493 (14) | 0.0021 (11) | 0.0022 (11) | 0.0133 (11) |
C11 | 0.0545 (17) | 0.0624 (16) | 0.0687 (18) | 0.0060 (13) | −0.0092 (14) | 0.0110 (14) |
C12 | 0.080 (2) | 0.0760 (19) | 0.075 (2) | −0.0046 (17) | −0.0296 (17) | 0.0134 (17) |
C13 | 0.097 (2) | 0.0702 (19) | 0.0508 (17) | −0.0057 (18) | −0.0043 (17) | 0.0017 (14) |
C14 | 0.082 (2) | 0.082 (2) | 0.066 (2) | 0.0182 (17) | 0.0077 (17) | −0.0085 (16) |
C15 | 0.0574 (17) | 0.0757 (18) | 0.0563 (17) | 0.0171 (14) | −0.0053 (13) | −0.0012 (14) |
C16 | 0.0666 (17) | 0.0390 (14) | 0.0463 (14) | −0.0023 (12) | 0.0111 (12) | 0.0047 (11) |
C17 | 0.0772 (19) | 0.0480 (15) | 0.0605 (17) | 0.0109 (14) | 0.0113 (15) | 0.0073 (13) |
C18 | 0.0498 (15) | 0.0570 (15) | 0.0424 (14) | 0.0059 (12) | 0.0022 (12) | 0.0153 (12) |
C19 | 0.0501 (15) | 0.0710 (17) | 0.0524 (16) | −0.0049 (13) | −0.0017 (12) | 0.0163 (14) |
C20 | 0.0649 (19) | 0.0660 (17) | 0.0578 (18) | −0.0049 (14) | −0.0140 (15) | 0.0108 (14) |
C21 | 0.0643 (18) | 0.0581 (15) | 0.0447 (15) | 0.0107 (14) | −0.0027 (13) | 0.0053 (12) |
C22 | 0.0536 (16) | 0.0715 (17) | 0.0542 (16) | 0.0036 (14) | 0.0084 (13) | 0.0124 (14) |
C23 | 0.0554 (16) | 0.0625 (16) | 0.0531 (16) | −0.0058 (13) | 0.0030 (13) | 0.0027 (13) |
C24 | 0.0552 (16) | 0.0547 (15) | 0.0505 (15) | 0.0030 (12) | 0.0097 (12) | 0.0034 (12) |
C25 | 0.0428 (13) | 0.0404 (12) | 0.0431 (13) | 0.0014 (10) | 0.0035 (11) | 0.0009 (10) |
C26 | 0.0492 (15) | 0.0445 (13) | 0.0511 (15) | 0.0085 (11) | 0.0033 (12) | 0.0019 (11) |
C27 | 0.0573 (16) | 0.0605 (16) | 0.0517 (16) | 0.0002 (13) | 0.0153 (13) | 0.0022 (13) |
C28 | 0.0726 (19) | 0.0584 (16) | 0.0519 (16) | −0.0029 (14) | −0.0049 (15) | 0.0121 (13) |
C29 | 0.0604 (18) | 0.0668 (17) | 0.0669 (19) | 0.0156 (14) | −0.0034 (15) | 0.0155 (14) |
C30 | 0.0484 (15) | 0.0569 (15) | 0.0625 (17) | 0.0125 (12) | 0.0082 (13) | 0.0048 (13) |
O1—C1 | 1.234 (2) | C11—C12 | 1.381 (4) |
O2—C3 | 1.366 (2) | C11—H11 | 0.9300 |
O2—C2 | 1.419 (2) | C12—C13 | 1.363 (4) |
O3—N2 | 1.209 (3) | C12—H12 | 0.9300 |
O4—N2 | 1.216 (3) | C13—C14 | 1.363 (4) |
O5—C16 | 1.226 (2) | C13—H13 | 0.9300 |
O6—C18 | 1.370 (3) | C14—C15 | 1.380 (3) |
O6—C17 | 1.425 (3) | C14—H14 | 0.9300 |
O7—N4 | 1.209 (3) | C15—H15 | 0.9300 |
O8—N4 | 1.211 (3) | C16—C17 | 1.502 (3) |
N1—C1 | 1.323 (3) | C17—H17A | 0.9700 |
N1—C9 | 1.450 (3) | C17—H17B | 0.9700 |
N1—H1 | 0.8600 | C18—C23 | 1.370 (3) |
N2—C6 | 1.463 (3) | C18—C19 | 1.377 (3) |
N3—C16 | 1.320 (3) | C19—C20 | 1.371 (3) |
N3—C24 | 1.447 (3) | C19—H19 | 0.9300 |
N3—H3 | 0.8600 | C20—C21 | 1.368 (3) |
N4—C21 | 1.462 (3) | C20—H20 | 0.9300 |
C1—C2 | 1.501 (3) | C21—C22 | 1.370 (3) |
C2—H2A | 0.9700 | C22—C23 | 1.391 (3) |
C2—H2B | 0.9700 | C22—H22 | 0.9300 |
C3—C4 | 1.373 (3) | C23—H23 | 0.9300 |
C3—C8 | 1.384 (3) | C24—C25 | 1.502 (3) |
C4—C5 | 1.377 (3) | C24—H24A | 0.9700 |
C4—H4 | 0.9300 | C24—H24B | 0.9700 |
C5—C6 | 1.369 (3) | C25—C26 | 1.380 (3) |
C5—H5 | 0.9300 | C25—C30 | 1.384 (3) |
C6—C7 | 1.371 (3) | C26—C27 | 1.385 (3) |
C7—C8 | 1.376 (3) | C26—H26 | 0.9300 |
C7—H7 | 0.9300 | C27—C28 | 1.371 (3) |
C8—H8 | 0.9300 | C27—H27 | 0.9300 |
C9—C10 | 1.507 (3) | C28—C29 | 1.363 (4) |
C9—H9A | 0.9700 | C28—H28 | 0.9300 |
C9—H9B | 0.9700 | C29—C30 | 1.375 (3) |
C10—C15 | 1.372 (3) | C29—H29 | 0.9300 |
C10—C11 | 1.377 (3) | C30—H30 | 0.9300 |
C3—O2—C2 | 119.19 (16) | C14—C13—H13 | 120.2 |
C18—O6—C17 | 119.20 (19) | C13—C14—C15 | 120.0 (3) |
C1—N1—C9 | 122.49 (18) | C13—C14—H14 | 120.0 |
C1—N1—H1 | 118.8 | C15—C14—H14 | 120.0 |
C9—N1—H1 | 118.8 | C10—C15—C14 | 121.2 (2) |
O3—N2—O4 | 122.7 (2) | C10—C15—H15 | 119.4 |
O3—N2—C6 | 118.7 (2) | C14—C15—H15 | 119.4 |
O4—N2—C6 | 118.5 (2) | O5—C16—N3 | 124.0 (2) |
C16—N3—C24 | 122.62 (19) | O5—C16—C17 | 117.8 (2) |
C16—N3—H3 | 118.7 | N3—C16—C17 | 118.2 (2) |
C24—N3—H3 | 118.7 | O6—C17—C16 | 116.64 (19) |
O7—N4—O8 | 122.7 (3) | O6—C17—H17A | 108.1 |
O7—N4—C21 | 118.6 (3) | C16—C17—H17A | 108.1 |
O8—N4—C21 | 118.7 (3) | O6—C17—H17B | 108.1 |
O1—C1—N1 | 124.1 (2) | C16—C17—H17B | 108.1 |
O1—C1—C2 | 118.5 (2) | H17A—C17—H17B | 107.3 |
N1—C1—C2 | 117.40 (19) | C23—C18—O6 | 124.5 (2) |
O2—C2—C1 | 109.58 (17) | C23—C18—C19 | 120.8 (2) |
O2—C2—H2A | 109.8 | O6—C18—C19 | 114.7 (2) |
C1—C2—H2A | 109.8 | C20—C19—C18 | 120.0 (2) |
O2—C2—H2B | 109.8 | C20—C19—H19 | 120.0 |
C1—C2—H2B | 109.8 | C18—C19—H19 | 120.0 |
H2A—C2—H2B | 108.2 | C21—C20—C19 | 119.3 (2) |
O2—C3—C4 | 124.5 (2) | C21—C20—H20 | 120.4 |
O2—C3—C8 | 114.8 (2) | C19—C20—H20 | 120.4 |
C4—C3—C8 | 120.7 (2) | C20—C21—C22 | 121.5 (2) |
C3—C4—C5 | 119.1 (2) | C20—C21—N4 | 119.6 (2) |
C3—C4—H4 | 120.4 | C22—C21—N4 | 119.0 (3) |
C5—C4—H4 | 120.4 | C21—C22—C23 | 119.3 (2) |
C6—C5—C4 | 119.7 (2) | C21—C22—H22 | 120.4 |
C6—C5—H5 | 120.2 | C23—C22—H22 | 120.4 |
C4—C5—H5 | 120.2 | C18—C23—C22 | 119.1 (2) |
C5—C6—C7 | 121.9 (2) | C18—C23—H23 | 120.4 |
C5—C6—N2 | 119.0 (2) | C22—C23—H23 | 120.4 |
C7—C6—N2 | 119.1 (2) | N3—C24—C25 | 115.64 (19) |
C6—C7—C8 | 118.4 (2) | N3—C24—H24A | 108.4 |
C6—C7—H7 | 120.8 | C25—C24—H24A | 108.4 |
C8—C7—H7 | 120.8 | N3—C24—H24B | 108.4 |
C7—C8—C3 | 120.2 (2) | C25—C24—H24B | 108.4 |
C7—C8—H8 | 119.9 | H24A—C24—H24B | 107.4 |
C3—C8—H8 | 119.9 | C26—C25—C30 | 117.8 (2) |
N1—C9—C10 | 115.17 (18) | C26—C25—C24 | 123.3 (2) |
N1—C9—H9A | 108.5 | C30—C25—C24 | 118.8 (2) |
C10—C9—H9A | 108.5 | C25—C26—C27 | 120.7 (2) |
N1—C9—H9B | 108.5 | C25—C26—H26 | 119.7 |
C10—C9—H9B | 108.5 | C27—C26—H26 | 119.7 |
H9A—C9—H9B | 107.5 | C28—C27—C26 | 120.1 (2) |
C15—C10—C11 | 118.1 (2) | C28—C27—H27 | 120.0 |
C15—C10—C9 | 122.0 (2) | C26—C27—H27 | 120.0 |
C11—C10—C9 | 119.8 (2) | C29—C28—C27 | 120.1 (2) |
C10—C11—C12 | 120.6 (3) | C29—C28—H28 | 119.9 |
C10—C11—H11 | 119.7 | C27—C28—H28 | 119.9 |
C12—C11—H11 | 119.7 | C28—C29—C30 | 119.7 (2) |
C13—C12—C11 | 120.5 (3) | C28—C29—H29 | 120.2 |
C13—C12—H12 | 119.8 | C30—C29—H29 | 120.2 |
C11—C12—H12 | 119.8 | C29—C30—C25 | 121.6 (2) |
C12—C13—C14 | 119.6 (3) | C29—C30—H30 | 119.2 |
C12—C13—H13 | 120.2 | C25—C30—H30 | 119.2 |
C9—N1—C1—O1 | 5.6 (3) | C24—N3—C16—O5 | 6.9 (4) |
C9—N1—C1—C2 | −174.34 (19) | C24—N3—C16—C17 | −173.8 (2) |
C3—O2—C2—C1 | 172.61 (18) | C18—O6—C17—C16 | 83.1 (3) |
O1—C1—C2—O2 | −176.67 (19) | O5—C16—C17—O6 | −175.2 (2) |
N1—C1—C2—O2 | 3.2 (3) | N3—C16—C17—O6 | 5.4 (3) |
C2—O2—C3—C4 | 6.9 (3) | C17—O6—C18—C23 | −11.8 (3) |
C2—O2—C3—C8 | −173.41 (19) | C17—O6—C18—C19 | 168.8 (2) |
O2—C3—C4—C5 | 179.5 (2) | C23—C18—C19—C20 | −2.5 (4) |
C8—C3—C4—C5 | −0.1 (3) | O6—C18—C19—C20 | 177.0 (2) |
C3—C4—C5—C6 | −0.2 (4) | C18—C19—C20—C21 | 0.5 (4) |
C4—C5—C6—C7 | −0.1 (4) | C19—C20—C21—C22 | 1.9 (4) |
C4—C5—C6—N2 | −179.1 (2) | C19—C20—C21—N4 | −178.3 (2) |
O3—N2—C6—C5 | 177.7 (2) | O7—N4—C21—C20 | −4.5 (4) |
O4—N2—C6—C5 | −0.6 (3) | O8—N4—C21—C20 | 174.0 (3) |
O3—N2—C6—C7 | −1.3 (3) | O7—N4—C21—C22 | 175.4 (2) |
O4—N2—C6—C7 | −179.6 (2) | O8—N4—C21—C22 | −6.1 (4) |
C5—C6—C7—C8 | 0.6 (3) | C20—C21—C22—C23 | −2.2 (4) |
N2—C6—C7—C8 | 179.6 (2) | N4—C21—C22—C23 | 178.0 (2) |
C6—C7—C8—C3 | −0.9 (3) | O6—C18—C23—C22 | −177.3 (2) |
O2—C3—C8—C7 | −179.0 (2) | C19—C18—C23—C22 | 2.1 (4) |
C4—C3—C8—C7 | 0.7 (3) | C21—C22—C23—C18 | 0.2 (4) |
C1—N1—C9—C10 | −110.3 (2) | C16—N3—C24—C25 | −116.5 (2) |
N1—C9—C10—C15 | 29.1 (3) | N3—C24—C25—C26 | 26.9 (3) |
N1—C9—C10—C11 | −153.7 (2) | N3—C24—C25—C30 | −155.37 (19) |
C15—C10—C11—C12 | 0.6 (3) | C30—C25—C26—C27 | 0.3 (3) |
C9—C10—C11—C12 | −176.7 (2) | C24—C25—C26—C27 | 178.1 (2) |
C10—C11—C12—C13 | −0.8 (4) | C25—C26—C27—C28 | −0.9 (3) |
C11—C12—C13—C14 | 0.6 (4) | C26—C27—C28—C29 | 0.9 (3) |
C12—C13—C14—C15 | −0.4 (4) | C27—C28—C29—C30 | −0.4 (4) |
C11—C10—C15—C14 | −0.4 (4) | C28—C29—C30—C25 | −0.2 (4) |
C9—C10—C15—C14 | 176.9 (2) | C26—C25—C30—C29 | 0.2 (3) |
C13—C14—C15—C10 | 0.2 (4) | C24—C25—C30—C29 | −177.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O1i | 0.86 | 2.15 | 2.927 (2) | 150 |
N1—H1···O5ii | 0.86 | 2.13 | 2.915 (3) | 151 |
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z. |