In the title compound, C
26H
24N
4O
5, the salicylaldehyde group makes dihedral angles of 7.06 (10), 75.88 (9) and 37.62 (12)° with the pyrazolone ring, the terminal nitrobenzene ring and the terminal phenyl ring, respectively. The crystal packing is stabilized by π–π interactions and intermolecular C—H
O hydrogen bonds that form centrosymmetric dimers.
Supporting information
CCDC reference: 623968
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.005 Å
- R factor = 0.057
- wR factor = 0.129
- Data-to-parameter ratio = 13.1
checkCIF/PLATON results
No syntax errors found
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.102
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.10
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 48 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); 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.
(
E)-1,5-Dimethyl-4-{2-[2-(2-nitrophenoxy)ethoxy]benzylideneamino}-2-phenyl- 1
H-pyrazol-3(2
H)-one
top
Crystal data top
C26H24N4O5 | F(000) = 992 |
Mr = 472.49 | Dx = 1.318 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2344 reflections |
a = 13.255 (4) Å | θ = 2.7–26.3° |
b = 18.369 (5) Å | µ = 0.09 mm−1 |
c = 10.040 (3) Å | T = 294 K |
β = 103.140 (5)° | Block, yellow |
V = 2380.6 (12) Å3 | 0.22 × 0.14 × 0.08 mm |
Z = 4 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 4173 independent reflections |
Radiation source: fine-focus sealed tube | 1986 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.102 |
φ and ω scans | θmax = 25.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −15→8 |
Tmin = 0.968, Tmax = 0.993 | k = −21→21 |
11202 measured reflections | l = −11→11 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.129 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0418P)2 + 0.3376P] where P = (Fo2 + 2Fc2)/3 |
4173 reflections | (Δ/σ)max = 0.001 |
318 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.3954 (2) | 0.18062 (14) | 1.0379 (3) | 0.0832 (8) | |
O2 | 0.3156 (2) | 0.19113 (14) | 0.8264 (3) | 0.0776 (8) | |
O3 | 0.41896 (18) | 0.09153 (12) | 0.7040 (2) | 0.0662 (7) | |
O4 | 0.54619 (15) | 0.12133 (10) | 0.51040 (19) | 0.0483 (6) | |
O5 | 0.75766 (16) | −0.03508 (11) | 0.7282 (2) | 0.0535 (6) | |
N1 | 0.3581 (2) | 0.15495 (17) | 0.9246 (4) | 0.0572 (8) | |
N2 | 0.8552 (2) | 0.09536 (13) | 0.5989 (2) | 0.0429 (6) | |
N3 | 1.02532 (18) | −0.04255 (15) | 0.7749 (2) | 0.0482 (7) | |
N4 | 0.92898 (19) | −0.07322 (14) | 0.7819 (2) | 0.0461 (7) | |
C1 | 0.3643 (2) | 0.07581 (18) | 0.9094 (3) | 0.0473 (8) | |
C2 | 0.3423 (3) | 0.0340 (2) | 1.0123 (4) | 0.0647 (10) | |
H2 | 0.3256 | 0.0558 | 1.0881 | 0.078* | |
C3 | 0.3452 (3) | −0.0404 (2) | 1.0019 (4) | 0.0761 (12) | |
H3 | 0.3296 | −0.0696 | 1.0702 | 0.091* | |
C4 | 0.3713 (3) | −0.0716 (2) | 0.8900 (5) | 0.0749 (11) | |
H4 | 0.3738 | −0.1221 | 0.8833 | 0.090* | |
C5 | 0.3937 (3) | −0.0292 (2) | 0.7878 (4) | 0.0658 (10) | |
H5 | 0.4111 | −0.0512 | 0.7126 | 0.079* | |
C6 | 0.3906 (2) | 0.04590 (19) | 0.7959 (3) | 0.0506 (9) | |
C7 | 0.3986 (3) | 0.06975 (18) | 0.5655 (3) | 0.0597 (10) | |
H7A | 0.3248 | 0.0624 | 0.5313 | 0.072* | |
H7B | 0.4337 | 0.0242 | 0.5573 | 0.072* | |
C8 | 0.4362 (2) | 0.12742 (18) | 0.4843 (3) | 0.0544 (9) | |
H8A | 0.4060 | 0.1208 | 0.3875 | 0.065* | |
H8B | 0.4166 | 0.1751 | 0.5113 | 0.065* | |
C9 | 0.6004 (2) | 0.17281 (16) | 0.4563 (3) | 0.0392 (8) | |
C10 | 0.5538 (3) | 0.22674 (18) | 0.3679 (3) | 0.0528 (9) | |
H10 | 0.4820 | 0.2294 | 0.3409 | 0.063* | |
C11 | 0.6148 (3) | 0.27705 (18) | 0.3196 (3) | 0.0636 (10) | |
H11 | 0.5837 | 0.3138 | 0.2607 | 0.076* | |
C12 | 0.7209 (3) | 0.27294 (19) | 0.3580 (4) | 0.0664 (11) | |
H12 | 0.7614 | 0.3073 | 0.3263 | 0.080* | |
C13 | 0.7668 (3) | 0.21848 (17) | 0.4425 (3) | 0.0539 (9) | |
H13 | 0.8387 | 0.2159 | 0.4675 | 0.065* | |
C14 | 0.7081 (2) | 0.16638 (16) | 0.4924 (3) | 0.0381 (8) | |
C15 | 0.7570 (2) | 0.10536 (16) | 0.5752 (3) | 0.0407 (8) | |
H15 | 0.7163 | 0.0731 | 0.6116 | 0.049* | |
C16 | 0.8991 (2) | 0.03392 (16) | 0.6707 (3) | 0.0386 (8) | |
C17 | 1.0022 (2) | 0.02004 (18) | 0.6993 (3) | 0.0446 (8) | |
C18 | 0.8493 (2) | −0.02573 (16) | 0.7257 (3) | 0.0394 (8) | |
C19 | 1.0869 (2) | 0.06350 (18) | 0.6607 (3) | 0.0662 (10) | |
H19A | 1.1168 | 0.0359 | 0.5981 | 0.099* | |
H19B | 1.1393 | 0.0743 | 0.7413 | 0.099* | |
H19C | 1.0588 | 0.1081 | 0.6178 | 0.099* | |
C20 | 1.1003 (3) | −0.09503 (19) | 0.7445 (4) | 0.0724 (11) | |
H20A | 1.0735 | −0.1162 | 0.6562 | 0.109* | |
H20B | 1.1121 | −0.1326 | 0.8127 | 0.109* | |
H20C | 1.1644 | −0.0706 | 0.7448 | 0.109* | |
C21 | 0.9250 (3) | −0.12698 (17) | 0.8830 (3) | 0.0432 (8) | |
C22 | 0.8468 (3) | −0.17782 (18) | 0.8560 (3) | 0.0532 (9) | |
H22 | 0.7968 | −0.1762 | 0.7743 | 0.064* | |
C23 | 0.8436 (3) | −0.23127 (19) | 0.9518 (4) | 0.0661 (10) | |
H23 | 0.7907 | −0.2656 | 0.9350 | 0.079* | |
C24 | 0.9182 (4) | −0.2339 (2) | 1.0717 (4) | 0.0759 (12) | |
H24 | 0.9169 | −0.2707 | 1.1349 | 0.091* | |
C25 | 0.9946 (3) | −0.1821 (2) | 1.0980 (4) | 0.0696 (11) | |
H25 | 1.0443 | −0.1836 | 1.1799 | 0.084* | |
C26 | 0.9987 (3) | −0.12811 (18) | 1.0049 (3) | 0.0568 (9) | |
H26 | 1.0503 | −0.0928 | 1.0236 | 0.068* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.092 (2) | 0.079 (2) | 0.079 (2) | −0.0135 (16) | 0.0194 (17) | −0.0274 (17) |
O2 | 0.0748 (19) | 0.0703 (19) | 0.087 (2) | 0.0131 (15) | 0.0174 (16) | 0.0098 (16) |
O3 | 0.0889 (18) | 0.0600 (15) | 0.0568 (16) | −0.0278 (14) | 0.0312 (14) | −0.0182 (13) |
O4 | 0.0359 (12) | 0.0515 (14) | 0.0577 (14) | 0.0029 (11) | 0.0109 (11) | 0.0060 (11) |
O5 | 0.0347 (13) | 0.0669 (15) | 0.0569 (14) | 0.0012 (12) | 0.0064 (11) | 0.0186 (12) |
N1 | 0.0488 (19) | 0.061 (2) | 0.064 (2) | −0.0024 (17) | 0.0193 (18) | −0.008 (2) |
N2 | 0.0370 (16) | 0.0487 (17) | 0.0416 (16) | 0.0016 (14) | 0.0061 (12) | 0.0036 (14) |
N3 | 0.0324 (15) | 0.0592 (18) | 0.0518 (17) | 0.0050 (14) | 0.0069 (13) | 0.0035 (15) |
N4 | 0.0336 (15) | 0.0554 (17) | 0.0472 (17) | 0.0056 (15) | 0.0046 (13) | 0.0112 (14) |
C1 | 0.0382 (19) | 0.050 (2) | 0.052 (2) | −0.0037 (17) | 0.0077 (17) | −0.0056 (19) |
C2 | 0.067 (3) | 0.072 (3) | 0.056 (2) | −0.008 (2) | 0.017 (2) | −0.003 (2) |
C3 | 0.074 (3) | 0.077 (3) | 0.074 (3) | −0.014 (2) | 0.011 (2) | 0.020 (3) |
C4 | 0.068 (3) | 0.051 (2) | 0.101 (3) | −0.007 (2) | 0.010 (3) | 0.000 (3) |
C5 | 0.068 (3) | 0.058 (3) | 0.074 (3) | −0.012 (2) | 0.022 (2) | −0.016 (2) |
C6 | 0.048 (2) | 0.053 (2) | 0.052 (2) | −0.0117 (18) | 0.0123 (18) | −0.011 (2) |
C7 | 0.049 (2) | 0.075 (3) | 0.056 (2) | −0.017 (2) | 0.0145 (18) | −0.017 (2) |
C8 | 0.039 (2) | 0.068 (2) | 0.055 (2) | −0.0010 (18) | 0.0074 (17) | −0.0047 (19) |
C9 | 0.044 (2) | 0.039 (2) | 0.0367 (19) | 0.0027 (17) | 0.0135 (16) | −0.0011 (16) |
C10 | 0.048 (2) | 0.059 (2) | 0.049 (2) | 0.012 (2) | 0.0076 (18) | 0.0060 (19) |
C11 | 0.075 (3) | 0.055 (2) | 0.063 (2) | 0.024 (2) | 0.020 (2) | 0.024 (2) |
C12 | 0.064 (3) | 0.059 (2) | 0.084 (3) | 0.013 (2) | 0.034 (2) | 0.026 (2) |
C13 | 0.048 (2) | 0.049 (2) | 0.069 (2) | 0.0065 (18) | 0.0241 (19) | 0.014 (2) |
C14 | 0.041 (2) | 0.0378 (18) | 0.0360 (19) | 0.0048 (16) | 0.0094 (16) | 0.0004 (15) |
C15 | 0.039 (2) | 0.0411 (19) | 0.043 (2) | −0.0035 (16) | 0.0109 (16) | −0.0020 (16) |
C16 | 0.0324 (18) | 0.046 (2) | 0.0354 (18) | 0.0006 (16) | 0.0036 (15) | 0.0010 (16) |
C17 | 0.037 (2) | 0.055 (2) | 0.041 (2) | −0.0024 (17) | 0.0064 (16) | −0.0017 (17) |
C18 | 0.0353 (19) | 0.050 (2) | 0.0298 (18) | 0.0000 (18) | 0.0005 (16) | 0.0006 (15) |
C19 | 0.043 (2) | 0.079 (3) | 0.077 (3) | −0.006 (2) | 0.0151 (19) | 0.006 (2) |
C20 | 0.050 (2) | 0.081 (3) | 0.090 (3) | 0.023 (2) | 0.024 (2) | 0.008 (2) |
C21 | 0.048 (2) | 0.046 (2) | 0.035 (2) | 0.0096 (18) | 0.0085 (18) | 0.0030 (17) |
C22 | 0.053 (2) | 0.055 (2) | 0.051 (2) | 0.0068 (19) | 0.0106 (18) | 0.0044 (19) |
C23 | 0.066 (3) | 0.057 (2) | 0.080 (3) | 0.009 (2) | 0.026 (2) | 0.013 (2) |
C24 | 0.088 (3) | 0.076 (3) | 0.073 (3) | 0.029 (3) | 0.036 (3) | 0.032 (2) |
C25 | 0.071 (3) | 0.087 (3) | 0.047 (2) | 0.024 (3) | 0.007 (2) | 0.015 (2) |
C26 | 0.063 (2) | 0.061 (2) | 0.043 (2) | 0.008 (2) | 0.003 (2) | 0.002 (2) |
Geometric parameters (Å, º) top
O1—N1 | 1.227 (3) | C9—C14 | 1.395 (4) |
O2—N1 | 1.216 (3) | C10—C11 | 1.387 (4) |
O3—C6 | 1.362 (4) | C10—H10 | 0.9300 |
O3—C7 | 1.412 (3) | C11—C12 | 1.373 (4) |
O4—C9 | 1.372 (3) | C11—H11 | 0.9300 |
O4—C8 | 1.426 (3) | C12—C13 | 1.363 (4) |
O5—C18 | 1.233 (3) | C12—H12 | 0.9300 |
N1—C1 | 1.466 (4) | C13—C14 | 1.397 (4) |
N2—C15 | 1.282 (3) | C13—H13 | 0.9300 |
N2—C16 | 1.393 (3) | C14—C15 | 1.457 (4) |
N3—C17 | 1.373 (4) | C15—H15 | 0.9300 |
N3—N4 | 1.412 (3) | C16—C17 | 1.356 (4) |
N3—C20 | 1.465 (4) | C16—C18 | 1.451 (4) |
N4—C18 | 1.387 (3) | C17—C19 | 1.498 (4) |
N4—C21 | 1.426 (4) | C19—H19A | 0.9600 |
C1—C2 | 1.371 (4) | C19—H19B | 0.9600 |
C1—C6 | 1.379 (4) | C19—H19C | 0.9600 |
C2—C3 | 1.373 (5) | C20—H20A | 0.9600 |
C2—H2 | 0.9300 | C20—H20B | 0.9600 |
C3—C4 | 1.374 (5) | C20—H20C | 0.9600 |
C3—H3 | 0.9300 | C21—C22 | 1.375 (4) |
C4—C5 | 1.373 (5) | C21—C26 | 1.381 (4) |
C4—H4 | 0.9300 | C22—C23 | 1.382 (4) |
C5—C6 | 1.383 (4) | C22—H22 | 0.9300 |
C5—H5 | 0.9300 | C23—C24 | 1.375 (5) |
C7—C8 | 1.490 (4) | C23—H23 | 0.9300 |
C7—H7A | 0.9700 | C24—C25 | 1.370 (5) |
C7—H7B | 0.9700 | C24—H24 | 0.9300 |
C8—H8A | 0.9700 | C25—C26 | 1.373 (4) |
C8—H8B | 0.9700 | C25—H25 | 0.9300 |
C9—C10 | 1.379 (4) | C26—H26 | 0.9300 |
| | | |
C6—O3—C7 | 118.2 (2) | C13—C12—C11 | 119.9 (3) |
C9—O4—C8 | 118.6 (2) | C13—C12—H12 | 120.0 |
O2—N1—O1 | 123.8 (3) | C11—C12—H12 | 120.0 |
O2—N1—C1 | 118.9 (3) | C12—C13—C14 | 121.3 (3) |
O1—N1—C1 | 117.2 (3) | C12—C13—H13 | 119.3 |
C15—N2—C16 | 119.9 (3) | C14—C13—H13 | 119.3 |
C17—N3—N4 | 105.7 (2) | C9—C14—C13 | 118.0 (3) |
C17—N3—C20 | 120.8 (3) | C9—C14—C15 | 120.6 (3) |
N4—N3—C20 | 114.3 (3) | C13—C14—C15 | 121.3 (3) |
C18—N4—N3 | 110.0 (2) | N2—C15—C14 | 121.2 (3) |
C18—N4—C21 | 125.2 (2) | N2—C15—H15 | 119.4 |
N3—N4—C21 | 119.5 (2) | C14—C15—H15 | 119.4 |
C2—C1—C6 | 122.5 (3) | C17—C16—N2 | 123.0 (3) |
C2—C1—N1 | 116.7 (3) | C17—C16—C18 | 107.5 (3) |
C6—C1—N1 | 120.8 (3) | N2—C16—C18 | 129.5 (3) |
C1—C2—C3 | 119.1 (4) | C16—C17—N3 | 111.2 (3) |
C1—C2—H2 | 120.5 | C16—C17—C19 | 128.6 (3) |
C3—C2—H2 | 120.5 | N3—C17—C19 | 120.2 (3) |
C2—C3—C4 | 119.6 (4) | O5—C18—N4 | 124.5 (3) |
C2—C3—H3 | 120.2 | O5—C18—C16 | 130.4 (3) |
C4—C3—H3 | 120.2 | N4—C18—C16 | 105.1 (3) |
C5—C4—C3 | 120.8 (4) | C17—C19—H19A | 109.5 |
C5—C4—H4 | 119.6 | C17—C19—H19B | 109.5 |
C3—C4—H4 | 119.6 | H19A—C19—H19B | 109.5 |
C4—C5—C6 | 120.5 (4) | C17—C19—H19C | 109.5 |
C4—C5—H5 | 119.8 | H19A—C19—H19C | 109.5 |
C6—C5—H5 | 119.8 | H19B—C19—H19C | 109.5 |
O3—C6—C1 | 118.4 (3) | N3—C20—H20A | 109.5 |
O3—C6—C5 | 123.9 (3) | N3—C20—H20B | 109.5 |
C1—C6—C5 | 117.6 (3) | H20A—C20—H20B | 109.5 |
O3—C7—C8 | 108.9 (3) | N3—C20—H20C | 109.5 |
O3—C7—H7A | 109.9 | H20A—C20—H20C | 109.5 |
C8—C7—H7A | 109.9 | H20B—C20—H20C | 109.5 |
O3—C7—H7B | 109.9 | C22—C21—C26 | 121.0 (3) |
C8—C7—H7B | 109.9 | C22—C21—N4 | 118.5 (3) |
H7A—C7—H7B | 108.3 | C26—C21—N4 | 120.5 (3) |
O4—C8—C7 | 107.4 (3) | C21—C22—C23 | 119.1 (3) |
O4—C8—H8A | 110.2 | C21—C22—H22 | 120.5 |
C7—C8—H8A | 110.2 | C23—C22—H22 | 120.5 |
O4—C8—H8B | 110.2 | C24—C23—C22 | 120.3 (4) |
C7—C8—H8B | 110.2 | C24—C23—H23 | 119.9 |
H8A—C8—H8B | 108.5 | C22—C23—H23 | 119.9 |
O4—C9—C10 | 123.5 (3) | C25—C24—C23 | 119.8 (4) |
O4—C9—C14 | 115.8 (3) | C25—C24—H24 | 120.1 |
C10—C9—C14 | 120.7 (3) | C23—C24—H24 | 120.1 |
C9—C10—C11 | 119.5 (3) | C24—C25—C26 | 120.8 (4) |
C9—C10—H10 | 120.3 | C24—C25—H25 | 119.6 |
C11—C10—H10 | 120.3 | C26—C25—H25 | 119.6 |
C12—C11—C10 | 120.5 (3) | C25—C26—C21 | 119.0 (3) |
C12—C11—H11 | 119.8 | C25—C26—H26 | 120.5 |
C10—C11—H11 | 119.8 | C21—C26—H26 | 120.5 |
| | | |
C17—N3—N4—C18 | −7.0 (3) | C12—C13—C14—C9 | −1.8 (4) |
C20—N3—N4—C18 | −142.3 (3) | C12—C13—C14—C15 | 175.8 (3) |
C17—N3—N4—C21 | −162.7 (2) | C16—N2—C15—C14 | −175.7 (2) |
C20—N3—N4—C21 | 62.0 (3) | C9—C14—C15—N2 | 173.8 (3) |
O2—N1—C1—C2 | −135.9 (3) | C13—C14—C15—N2 | −3.8 (4) |
O1—N1—C1—C2 | 43.1 (4) | C15—N2—C16—C17 | −180.0 (3) |
O2—N1—C1—C6 | 43.8 (4) | C15—N2—C16—C18 | 1.1 (4) |
O1—N1—C1—C6 | −137.2 (3) | N2—C16—C17—N3 | 178.0 (2) |
C6—C1—C2—C3 | −0.8 (5) | C18—C16—C17—N3 | −2.9 (3) |
N1—C1—C2—C3 | 178.9 (3) | N2—C16—C17—C19 | −1.4 (5) |
C1—C2—C3—C4 | 0.8 (6) | C18—C16—C17—C19 | 177.8 (3) |
C2—C3—C4—C5 | −0.5 (6) | N4—N3—C17—C16 | 6.1 (3) |
C3—C4—C5—C6 | 0.1 (6) | C20—N3—C17—C16 | 137.8 (3) |
C7—O3—C6—C1 | −150.3 (3) | N4—N3—C17—C19 | −174.5 (3) |
C7—O3—C6—C5 | 34.6 (5) | C20—N3—C17—C19 | −42.8 (4) |
C2—C1—C6—O3 | −175.0 (3) | N3—N4—C18—O5 | −173.5 (3) |
N1—C1—C6—O3 | 5.3 (5) | C21—N4—C18—O5 | −19.5 (5) |
C2—C1—C6—C5 | 0.4 (5) | N3—N4—C18—C16 | 5.3 (3) |
N1—C1—C6—C5 | −179.3 (3) | C21—N4—C18—C16 | 159.2 (3) |
C4—C5—C6—O3 | 175.1 (3) | C17—C16—C18—O5 | 177.1 (3) |
C4—C5—C6—C1 | −0.1 (5) | N2—C16—C18—O5 | −3.8 (5) |
C6—O3—C7—C8 | −179.8 (3) | C17—C16—C18—N4 | −1.5 (3) |
C9—O4—C8—C7 | −174.4 (2) | N2—C16—C18—N4 | 177.5 (3) |
O3—C7—C8—O4 | 76.3 (3) | C18—N4—C21—C22 | 56.2 (4) |
C8—O4—C9—C10 | −5.9 (4) | N3—N4—C21—C22 | −152.0 (3) |
C8—O4—C9—C14 | 176.2 (2) | C18—N4—C21—C26 | −124.3 (3) |
O4—C9—C10—C11 | 179.2 (3) | N3—N4—C21—C26 | 27.4 (4) |
C14—C9—C10—C11 | −3.0 (4) | C26—C21—C22—C23 | −1.0 (4) |
C9—C10—C11—C12 | 0.7 (5) | N4—C21—C22—C23 | 178.4 (3) |
C10—C11—C12—C13 | 1.0 (5) | C21—C22—C23—C24 | −0.7 (5) |
C11—C12—C13—C14 | −0.4 (5) | C22—C23—C24—C25 | 1.7 (5) |
O4—C9—C14—C13 | −178.5 (2) | C23—C24—C25—C26 | −1.0 (5) |
C10—C9—C14—C13 | 3.5 (4) | C24—C25—C26—C21 | −0.7 (5) |
O4—C9—C14—C15 | 3.8 (4) | C22—C21—C26—C25 | 1.7 (4) |
C10—C9—C14—C15 | −174.1 (3) | N4—C21—C26—C25 | −177.7 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O5i | 0.93 | 2.39 | 3.180 (4) | 143 |
Symmetry code: (i) −x+1, −y, −z+2. |