The title compound, C
28H
32N
2O
7, which was obtained by condensation of 4′-acetylbenzo-15-crown-5 and 2-naphthyloxyacetic acid hydrazide, adopts a
syn–
anti conformation, which enables N—H
O intermolecular hydrogen bonds to be formed between centrosymmetrically related molecules. The resulting eight-membered rings join these molecules together as characteristic dimers. The naphthalene ring system is almost perpendicular to the crown ether ring.
Supporting information
CCDC reference: 238825
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.059
- wR factor = 0.149
- Data-to-parameter ratio = 14.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 49 Perc.
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.56 Ratio
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... O3
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... O4
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C9'
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C11'
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C10
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... O3'
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... O4'
PLAT301_ALERT_3_C Main Residue Disorder ......................... 16.00 Perc.
PLAT412_ALERT_2_C Short Intra XH3 .. XHn H3 .. H16B .. 1.86 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
13 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
9 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
Crystal data top
C28H32N2O7 | F(000) = 1080 |
Mr = 508.56 | Dx = 1.313 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.808 (3) Å | Cell parameters from 920 reflections |
b = 24.579 (7) Å | θ = 2.4–25.4° |
c = 11.984 (4) Å | µ = 0.10 mm−1 |
β = 97.248 (6)° | T = 293 K |
V = 2573.6 (13) Å3 | Block, colorless |
Z = 4 | 0.38 × 0.22 × 0.20 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2575 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.051 |
Graphite monochromator | θmax = 26.4°, θmin = 1.9° |
φ and ω scans | h = −11→9 |
14670 measured reflections | k = −30→30 |
5263 independent reflections | l = −14→14 |
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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.149 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0576P)2 + 0.3872P] where P = (Fo2 + 2Fc2)/3 |
5263 reflections | (Δ/σ)max = 0.001 |
368 parameters | Δρmax = 0.19 e Å−3 |
46 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 | Occ. (<1) |
N1 | 0.4595 (2) | 0.87764 (9) | 0.61312 (18) | 0.0513 (6) | |
N2 | 0.5024 (3) | 0.92519 (9) | 0.56379 (19) | 0.0569 (6) | |
H2 | 0.4741 | 0.9563 | 0.5867 | 0.068* | |
O1 | 0.2403 (2) | 0.67657 (7) | 0.87079 (15) | 0.0554 (5) | |
O2 | 0.4118 (2) | 0.68012 (7) | 0.71573 (15) | 0.0563 (5) | |
O5 | 0.0090 (2) | 0.59705 (9) | 0.84484 (18) | 0.0699 (6) | |
O6 | 0.6206 (3) | 0.96288 (8) | 0.42773 (18) | 0.0762 (6) | |
O7 | 0.7447 (2) | 0.84584 (8) | 0.54020 (15) | 0.0575 (5) | |
C1 | 0.2699 (3) | 0.72754 (11) | 0.8346 (2) | 0.0440 (6) | |
C2 | 0.2156 (3) | 0.77513 (12) | 0.8747 (2) | 0.0533 (7) | |
H2A | 0.1543 | 0.7740 | 0.9325 | 0.064* | |
C3 | 0.2511 (3) | 0.82472 (12) | 0.8300 (2) | 0.0535 (7) | |
H3 | 0.2136 | 0.8565 | 0.8584 | 0.064* | |
C4 | 0.3416 (3) | 0.82782 (11) | 0.7436 (2) | 0.0448 (6) | |
C5 | 0.3961 (3) | 0.77870 (11) | 0.7031 (2) | 0.0452 (7) | |
H5 | 0.4562 | 0.7798 | 0.6447 | 0.054* | |
C6 | 0.3628 (3) | 0.72958 (11) | 0.7473 (2) | 0.0429 (6) | |
C7 | 0.4995 (3) | 0.67722 (11) | 0.6235 (2) | 0.0584 (8) | |
H7A | 0.5969 | 0.6956 | 0.6420 | 0.070* | |
H7B | 0.4447 | 0.6943 | 0.5574 | 0.070* | |
O3 | 0.3939 (10) | 0.5915 (3) | 0.5503 (7) | 0.115 (4) | 0.612 (8) |
O4 | 0.1672 (10) | 0.5119 (3) | 0.7134 (8) | 0.116 (3) | 0.612 (8) |
C8 | 0.5241 (4) | 0.61800 (14) | 0.6020 (3) | 0.0758 (10) | 0.612 (8) |
H8A | 0.6052 | 0.6144 | 0.5548 | 0.091* | 0.612 (8) |
H8B | 0.5578 | 0.6002 | 0.6731 | 0.091* | 0.612 (8) |
C9 | 0.3407 (15) | 0.5466 (4) | 0.5997 (9) | 0.109 (2) | 0.612 (8) |
H9A | 0.4237 | 0.5205 | 0.6110 | 0.131* | 0.612 (8) |
H9B | 0.2609 | 0.5306 | 0.5465 | 0.131* | 0.612 (8) |
C10 | 0.2793 (10) | 0.5530 (3) | 0.7068 (6) | 0.0836 (19) | 0.612 (8) |
H10A | 0.3608 | 0.5494 | 0.7689 | 0.100* | 0.612 (8) |
H10B | 0.2335 | 0.5887 | 0.7110 | 0.100* | 0.612 (8) |
C11 | 0.1223 (13) | 0.5080 (5) | 0.8233 (11) | 0.109 (4) | 0.612 (8) |
H11A | 0.2051 | 0.5206 | 0.8783 | 0.130* | 0.612 (8) |
H11B | 0.1022 | 0.4702 | 0.8398 | 0.130* | 0.612 (8) |
C12 | −0.0157 (5) | 0.54054 (16) | 0.8327 (3) | 0.0959 (12) | 0.612 (8) |
H12A | −0.0884 | 0.5343 | 0.7662 | 0.115* | 0.612 (8) |
H12B | −0.0621 | 0.5276 | 0.8970 | 0.115* | 0.612 (8) |
O3' | 0.3702 (10) | 0.5974 (4) | 0.5629 (11) | 0.077 (5) | 0.388 (8) |
O4' | 0.1625 (10) | 0.5331 (4) | 0.6952 (9) | 0.066 (3) | 0.388 (8) |
C8' | 0.5241 (4) | 0.61800 (14) | 0.6020 (3) | 0.0758 (10) | 0.388 (8) |
H8'A | 0.5919 | 0.6131 | 0.5450 | 0.091* | 0.388 (8) |
H8'B | 0.5674 | 0.5996 | 0.6704 | 0.091* | 0.388 (8) |
C9' | 0.354 (2) | 0.5413 (5) | 0.5723 (13) | 0.109 (2) | 0.388 (8) |
H9'A | 0.4475 | 0.5237 | 0.5565 | 0.131* | 0.388 (8) |
H9'B | 0.2718 | 0.5291 | 0.5163 | 0.131* | 0.388 (8) |
C10' | 0.3198 (11) | 0.5240 (6) | 0.6861 (10) | 0.0836 (19) | 0.388 (8) |
H10C | 0.3438 | 0.4857 | 0.6974 | 0.100* | 0.388 (8) |
H10D | 0.3827 | 0.5446 | 0.7435 | 0.100* | 0.388 (8) |
C11' | 0.115 (2) | 0.5111 (7) | 0.7949 (17) | 0.101 (7) | 0.388 (8) |
H11C | 0.2006 | 0.5121 | 0.8544 | 0.121* | 0.388 (8) |
H11D | 0.0867 | 0.4733 | 0.7817 | 0.121* | 0.388 (8) |
C12' | −0.0157 (5) | 0.54054 (16) | 0.8327 (3) | 0.0959 (12) | 0.388 (8) |
H12C | −0.1058 | 0.5344 | 0.7788 | 0.115* | 0.388 (8) |
H12D | −0.0359 | 0.5257 | 0.9044 | 0.115* | 0.388 (8) |
C13 | 0.0872 (3) | 0.61291 (12) | 0.9502 (2) | 0.0627 (8) | |
H13A | 0.1804 | 0.5918 | 0.9671 | 0.075* | |
H13B | 0.0232 | 0.6065 | 1.0091 | 0.075* | |
C14 | 0.1244 (3) | 0.67139 (11) | 0.9446 (2) | 0.0545 (7) | |
H14A | 0.0341 | 0.6920 | 0.9156 | 0.065* | |
H14B | 0.1620 | 0.6850 | 1.0189 | 0.065* | |
C15 | 0.3820 (3) | 0.88045 (11) | 0.6963 (2) | 0.0491 (7) | |
C16 | 0.3321 (5) | 0.93209 (13) | 0.7475 (3) | 0.0909 (12) | |
H16A | 0.4205 | 0.9534 | 0.7746 | 0.136* | |
H16B | 0.2762 | 0.9235 | 0.8090 | 0.136* | |
H16C | 0.2678 | 0.9524 | 0.6917 | 0.136* | |
C17 | 0.5892 (3) | 0.92188 (12) | 0.4796 (2) | 0.0565 (8) | |
C18 | 0.6418 (3) | 0.86648 (11) | 0.4488 (2) | 0.0562 (7) | |
H18A | 0.5546 | 0.8423 | 0.4332 | 0.067* | |
H18B | 0.6928 | 0.8688 | 0.3818 | 0.067* | |
C19 | 0.7862 (3) | 0.79206 (12) | 0.5345 (2) | 0.0474 (7) | |
C20 | 0.8863 (3) | 0.77351 (14) | 0.6275 (2) | 0.0596 (8) | |
H20 | 0.9182 | 0.7971 | 0.6865 | 0.072* | |
C21 | 0.9361 (3) | 0.72145 (15) | 0.6311 (2) | 0.0676 (9) | |
H21 | 1.0010 | 0.7096 | 0.6937 | 0.081* | |
C22 | 0.8928 (3) | 0.68475 (13) | 0.5431 (2) | 0.0576 (8) | |
C23 | 0.9453 (4) | 0.63017 (15) | 0.5432 (3) | 0.0792 (10) | |
H23 | 1.0104 | 0.6171 | 0.6045 | 0.095* | |
C24 | 0.9018 (4) | 0.59705 (15) | 0.4555 (4) | 0.0864 (11) | |
H24 | 0.9384 | 0.5615 | 0.4561 | 0.104* | |
C25 | 0.8027 (4) | 0.61562 (14) | 0.3641 (3) | 0.0772 (10) | |
H25 | 0.7725 | 0.5922 | 0.3044 | 0.093* | |
C26 | 0.7496 (3) | 0.66718 (12) | 0.3608 (2) | 0.0586 (8) | |
H26 | 0.6832 | 0.6788 | 0.2988 | 0.070* | |
C27 | 0.7929 (3) | 0.70370 (12) | 0.4497 (2) | 0.0469 (7) | |
C28 | 0.7397 (3) | 0.75777 (11) | 0.4474 (2) | 0.0471 (7) | |
H28 | 0.6728 | 0.7701 | 0.3864 | 0.057* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0525 (14) | 0.0482 (14) | 0.0541 (14) | −0.0084 (11) | 0.0106 (12) | 0.0005 (11) |
N2 | 0.0649 (16) | 0.0466 (15) | 0.0624 (15) | −0.0056 (12) | 0.0214 (14) | −0.0050 (12) |
O1 | 0.0475 (11) | 0.0638 (13) | 0.0592 (12) | 0.0027 (9) | 0.0237 (10) | 0.0096 (10) |
O2 | 0.0604 (12) | 0.0572 (13) | 0.0571 (12) | 0.0078 (10) | 0.0303 (10) | 0.0082 (9) |
O5 | 0.0665 (14) | 0.0719 (16) | 0.0728 (15) | −0.0080 (11) | 0.0146 (12) | 0.0007 (11) |
O6 | 0.0870 (16) | 0.0596 (14) | 0.0892 (16) | −0.0031 (12) | 0.0388 (13) | 0.0098 (12) |
O7 | 0.0509 (12) | 0.0647 (14) | 0.0553 (12) | −0.0042 (10) | 0.0006 (10) | −0.0084 (10) |
C1 | 0.0326 (14) | 0.0572 (18) | 0.0425 (15) | 0.0020 (13) | 0.0063 (12) | 0.0037 (13) |
C2 | 0.0471 (16) | 0.072 (2) | 0.0440 (16) | −0.0028 (15) | 0.0165 (14) | −0.0019 (15) |
C3 | 0.0516 (17) | 0.060 (2) | 0.0498 (17) | 0.0023 (14) | 0.0100 (15) | −0.0081 (14) |
C4 | 0.0411 (15) | 0.0532 (18) | 0.0397 (15) | −0.0014 (13) | 0.0028 (13) | −0.0039 (13) |
C5 | 0.0385 (15) | 0.0569 (18) | 0.0414 (15) | 0.0013 (13) | 0.0091 (12) | 0.0009 (13) |
C6 | 0.0345 (14) | 0.0531 (18) | 0.0412 (15) | 0.0042 (12) | 0.0051 (12) | 0.0020 (13) |
C7 | 0.0614 (18) | 0.066 (2) | 0.0532 (17) | −0.0029 (15) | 0.0277 (15) | 0.0028 (15) |
O3 | 0.199 (9) | 0.081 (6) | 0.069 (5) | −0.075 (5) | 0.030 (5) | −0.004 (4) |
O4 | 0.173 (7) | 0.067 (5) | 0.126 (6) | −0.040 (4) | 0.088 (5) | −0.015 (4) |
C8 | 0.082 (3) | 0.077 (3) | 0.076 (2) | 0.002 (2) | 0.038 (2) | −0.0052 (19) |
C9 | 0.124 (5) | 0.112 (4) | 0.100 (6) | −0.015 (4) | 0.042 (4) | −0.003 (3) |
C10 | 0.088 (5) | 0.082 (6) | 0.083 (4) | 0.002 (4) | 0.022 (3) | 0.005 (4) |
C11 | 0.130 (10) | 0.103 (9) | 0.102 (8) | −0.024 (8) | 0.046 (6) | 0.006 (6) |
C12 | 0.103 (3) | 0.082 (3) | 0.110 (3) | −0.023 (2) | 0.046 (3) | −0.011 (2) |
O3' | 0.098 (7) | 0.066 (8) | 0.061 (7) | 0.038 (7) | −0.009 (5) | −0.001 (5) |
O4' | 0.061 (5) | 0.054 (6) | 0.088 (5) | −0.013 (4) | 0.026 (4) | 0.012 (4) |
C8' | 0.082 (3) | 0.077 (3) | 0.076 (2) | 0.002 (2) | 0.038 (2) | −0.0052 (19) |
C9' | 0.124 (5) | 0.112 (4) | 0.100 (6) | −0.015 (4) | 0.042 (4) | −0.003 (3) |
C10' | 0.088 (5) | 0.082 (6) | 0.083 (4) | 0.002 (4) | 0.022 (3) | 0.005 (4) |
C11' | 0.158 (17) | 0.074 (10) | 0.090 (11) | 0.048 (10) | 0.088 (11) | 0.028 (8) |
C12' | 0.103 (3) | 0.082 (3) | 0.110 (3) | −0.023 (2) | 0.046 (3) | −0.011 (2) |
C13 | 0.0599 (19) | 0.076 (2) | 0.0560 (19) | −0.0001 (16) | 0.0208 (16) | 0.0126 (16) |
C14 | 0.0474 (16) | 0.076 (2) | 0.0437 (16) | 0.0008 (15) | 0.0187 (14) | 0.0057 (14) |
C15 | 0.0502 (16) | 0.0542 (18) | 0.0422 (15) | −0.0032 (13) | 0.0031 (14) | −0.0056 (13) |
C16 | 0.140 (3) | 0.057 (2) | 0.085 (2) | −0.003 (2) | 0.050 (2) | −0.0057 (18) |
C17 | 0.0567 (19) | 0.055 (2) | 0.0595 (19) | −0.0059 (15) | 0.0127 (16) | −0.0008 (15) |
C18 | 0.0612 (19) | 0.0569 (19) | 0.0514 (17) | −0.0028 (15) | 0.0109 (15) | −0.0003 (14) |
C19 | 0.0382 (15) | 0.0626 (19) | 0.0430 (16) | −0.0028 (14) | 0.0110 (13) | 0.0006 (14) |
C20 | 0.0502 (18) | 0.090 (2) | 0.0380 (16) | −0.0067 (17) | 0.0030 (14) | −0.0065 (16) |
C21 | 0.0547 (19) | 0.100 (3) | 0.0456 (18) | 0.0102 (18) | −0.0017 (15) | 0.0136 (18) |
C22 | 0.0490 (17) | 0.078 (2) | 0.0469 (18) | 0.0073 (16) | 0.0103 (15) | 0.0107 (16) |
C23 | 0.073 (2) | 0.088 (3) | 0.076 (2) | 0.024 (2) | 0.0053 (19) | 0.022 (2) |
C24 | 0.091 (3) | 0.073 (2) | 0.097 (3) | 0.023 (2) | 0.019 (2) | 0.004 (2) |
C25 | 0.084 (3) | 0.073 (2) | 0.077 (2) | 0.008 (2) | 0.017 (2) | −0.0084 (19) |
C26 | 0.0559 (18) | 0.067 (2) | 0.0532 (18) | 0.0080 (16) | 0.0085 (15) | 0.0009 (15) |
C27 | 0.0365 (15) | 0.0636 (19) | 0.0425 (16) | 0.0019 (14) | 0.0123 (13) | 0.0020 (14) |
C28 | 0.0372 (15) | 0.064 (2) | 0.0398 (15) | −0.0014 (13) | 0.0050 (12) | 0.0031 (14) |
Geometric parameters (Å, º) top
N1—C15 | 1.279 (3) | C12—H12B | 0.9700 |
N1—N2 | 1.384 (3) | O3'—C9' | 1.393 (9) |
N2—C17 | 1.343 (3) | O4'—C10' | 1.422 (9) |
N2—H2 | 0.8600 | O4'—C11' | 1.422 (9) |
O1—C1 | 1.362 (3) | C9'—C10' | 1.493 (9) |
O1—C14 | 1.438 (3) | C9'—H9'A | 0.9700 |
O2—C6 | 1.360 (3) | C9'—H9'B | 0.9700 |
O2—C7 | 1.428 (3) | C10'—H10C | 0.9700 |
O5—C12 | 1.411 (4) | C10'—H10D | 0.9700 |
O5—C13 | 1.415 (3) | C11'—H11C | 0.9700 |
O6—C17 | 1.233 (3) | C11'—H11D | 0.9700 |
O7—C19 | 1.376 (3) | C13—C14 | 1.478 (4) |
O7—C18 | 1.424 (3) | C13—H13A | 0.9700 |
C1—C2 | 1.373 (4) | C13—H13B | 0.9700 |
C1—C6 | 1.408 (3) | C14—H14A | 0.9700 |
C2—C3 | 1.383 (4) | C14—H14B | 0.9700 |
C2—H2A | 0.9300 | C15—C16 | 1.499 (4) |
C3—C4 | 1.386 (4) | C16—H16A | 0.9600 |
C3—H3 | 0.9300 | C16—H16B | 0.9600 |
C4—C5 | 1.408 (3) | C16—H16C | 0.9600 |
C4—C15 | 1.474 (4) | C17—C18 | 1.500 (4) |
C5—C6 | 1.366 (3) | C18—H18A | 0.9700 |
C5—H5 | 0.9300 | C18—H18B | 0.9700 |
C7—C8 | 1.498 (4) | C19—C28 | 1.363 (4) |
C7—H7A | 0.9700 | C19—C20 | 1.407 (4) |
C7—H7B | 0.9700 | C20—C21 | 1.352 (4) |
O3—C9 | 1.363 (7) | C20—H20 | 0.9300 |
O3—C8 | 1.394 (7) | C21—C22 | 1.403 (4) |
O4—C10 | 1.421 (7) | C21—H21 | 0.9300 |
O4—C11 | 1.426 (8) | C22—C27 | 1.413 (4) |
C8—H8A | 0.9700 | C22—C23 | 1.419 (4) |
C8—H8B | 0.9700 | C23—C24 | 1.346 (5) |
C9—C10 | 1.463 (7) | C23—H23 | 0.9300 |
C9—H9A | 0.9700 | C24—C25 | 1.389 (5) |
C9—H9B | 0.9700 | C24—H24 | 0.9300 |
C10—H10A | 0.9700 | C25—C26 | 1.350 (4) |
C10—H10B | 0.9700 | C25—H25 | 0.9300 |
C11—C12 | 1.471 (8) | C26—C27 | 1.408 (4) |
C11—H11A | 0.9700 | C26—H26 | 0.9300 |
C11—H11B | 0.9700 | C27—C28 | 1.408 (4) |
C12—H12A | 0.9700 | C28—H28 | 0.9300 |
| | | |
C15—N1—N2 | 119.3 (2) | H9'A—C9'—H9'B | 107.8 |
C17—N2—N1 | 118.8 (2) | O4'—C10'—C9' | 109.6 (9) |
C17—N2—H2 | 120.6 | O4'—C10'—H10C | 109.7 |
N1—N2—H2 | 120.6 | C9'—C10'—H10C | 109.7 |
C1—O1—C14 | 117.2 (2) | O4'—C10'—H10D | 109.7 |
C6—O2—C7 | 118.8 (2) | C9'—C10'—H10D | 109.7 |
C12—O5—C13 | 114.5 (3) | H10C—C10'—H10D | 108.2 |
C19—O7—C18 | 116.8 (2) | O4'—C11'—H11C | 108.9 |
O1—C1—C2 | 125.7 (2) | O4'—C11'—H11D | 108.9 |
O1—C1—C6 | 115.0 (2) | H11C—C11'—H11D | 107.8 |
C2—C1—C6 | 119.4 (2) | O5—C13—C14 | 108.3 (2) |
C1—C2—C3 | 120.6 (2) | O5—C13—H13A | 110.0 |
C1—C2—H2A | 119.7 | C14—C13—H13A | 110.0 |
C3—C2—H2A | 119.7 | O5—C13—H13B | 110.0 |
C2—C3—C4 | 121.1 (3) | C14—C13—H13B | 110.0 |
C2—C3—H3 | 119.4 | H13A—C13—H13B | 108.4 |
C4—C3—H3 | 119.4 | O1—C14—C13 | 107.0 (2) |
C3—C4—C5 | 117.6 (2) | O1—C14—H14A | 110.3 |
C3—C4—C15 | 121.7 (2) | C13—C14—H14A | 110.3 |
C5—C4—C15 | 120.7 (2) | O1—C14—H14B | 110.3 |
C6—C5—C4 | 121.7 (2) | C13—C14—H14B | 110.3 |
C6—C5—H5 | 119.2 | H14A—C14—H14B | 108.6 |
C4—C5—H5 | 119.2 | N1—C15—C4 | 115.5 (2) |
O2—C6—C5 | 126.2 (2) | N1—C15—C16 | 125.3 (3) |
O2—C6—C1 | 114.2 (2) | C4—C15—C16 | 119.2 (2) |
C5—C6—C1 | 119.6 (2) | C15—C16—H16A | 109.5 |
O2—C7—C8 | 106.6 (2) | C15—C16—H16B | 109.5 |
O2—C7—H7A | 110.4 | H16A—C16—H16B | 109.5 |
C8—C7—H7A | 110.4 | C15—C16—H16C | 109.5 |
O2—C7—H7B | 110.4 | H16A—C16—H16C | 109.5 |
C8—C7—H7B | 110.4 | H16B—C16—H16C | 109.5 |
H7A—C7—H7B | 108.6 | O6—C17—N2 | 120.9 (3) |
C9—O3—C8 | 119.6 (8) | O6—C17—C18 | 121.5 (3) |
C10—O4—C11 | 112.1 (8) | N2—C17—C18 | 117.6 (3) |
O3—C8—C7 | 113.6 (5) | O7—C18—C17 | 108.7 (2) |
O3—C8—H8A | 108.8 | O7—C18—H18A | 109.9 |
C7—C8—H8A | 108.8 | C17—C18—H18A | 109.9 |
O3—C8—H8B | 108.8 | O7—C18—H18B | 109.9 |
C7—C8—H8B | 108.8 | C17—C18—H18B | 109.9 |
H8A—C8—H8B | 107.7 | H18A—C18—H18B | 108.3 |
O3—C9—C10 | 118.7 (7) | C28—C19—O7 | 125.2 (3) |
O3—C9—H9A | 107.6 | C28—C19—C20 | 120.2 (3) |
C10—C9—H9A | 107.6 | O7—C19—C20 | 114.6 (3) |
O3—C9—H9B | 107.6 | C21—C20—C19 | 120.0 (3) |
C10—C9—H9B | 107.6 | C21—C20—H20 | 120.0 |
H9A—C9—H9B | 107.1 | C19—C20—H20 | 120.0 |
O4—C10—C9 | 108.0 (6) | C20—C21—C22 | 121.9 (3) |
O4—C10—H10A | 110.1 | C20—C21—H21 | 119.1 |
C9—C10—H10A | 110.1 | C22—C21—H21 | 119.1 |
O4—C10—H10B | 110.1 | C21—C22—C27 | 117.8 (3) |
C9—C10—H10B | 110.1 | C21—C22—C23 | 123.4 (3) |
H10A—C10—H10B | 108.4 | C27—C22—C23 | 118.9 (3) |
O4—C11—C12 | 111.2 (8) | C24—C23—C22 | 120.7 (3) |
O4—C11—H11A | 109.4 | C24—C23—H23 | 119.6 |
C12—C11—H11A | 109.4 | C22—C23—H23 | 119.6 |
O4—C11—H11B | 109.4 | C23—C24—C25 | 120.4 (3) |
C12—C11—H11B | 109.4 | C23—C24—H24 | 119.8 |
H11A—C11—H11B | 108.0 | C25—C24—H24 | 119.8 |
O5—C12—C11 | 115.2 (7) | C26—C25—C24 | 120.8 (3) |
O5—C12—H12A | 108.5 | C26—C25—H25 | 119.6 |
C11—C12—H12A | 108.5 | C24—C25—H25 | 119.6 |
O5—C12—H12B | 108.5 | C25—C26—C27 | 121.1 (3) |
C11—C12—H12B | 108.5 | C25—C26—H26 | 119.4 |
H12A—C12—H12B | 107.5 | C27—C26—H26 | 119.4 |
C10'—O4'—C11' | 113.4 (9) | C28—C27—C26 | 121.9 (3) |
O3'—C9'—C10' | 112.9 (10) | C28—C27—C22 | 119.9 (3) |
O3'—C9'—H9'A | 109.0 | C26—C27—C22 | 118.1 (3) |
C10'—C9'—H9'A | 109.0 | C19—C28—C27 | 120.1 (3) |
O3'—C9'—H9'B | 109.0 | C19—C28—H28 | 119.9 |
C10'—C9'—H9'B | 109.0 | C27—C28—H28 | 119.9 |
| | | |
C15—N1—N2—C17 | 177.2 (2) | N2—N1—C15—C16 | −0.3 (4) |
C14—O1—C1—C2 | 10.0 (4) | C3—C4—C15—N1 | −176.5 (2) |
C14—O1—C1—C6 | −168.9 (2) | C5—C4—C15—N1 | 4.3 (4) |
O1—C1—C2—C3 | −178.8 (2) | C3—C4—C15—C16 | 3.8 (4) |
C6—C1—C2—C3 | 0.1 (4) | C5—C4—C15—C16 | −175.3 (3) |
C1—C2—C3—C4 | 0.2 (4) | N1—N2—C17—O6 | 174.6 (2) |
C2—C3—C4—C5 | 0.0 (4) | N1—N2—C17—C18 | −3.5 (4) |
C2—C3—C4—C15 | −179.2 (2) | C19—O7—C18—C17 | 170.1 (2) |
C3—C4—C5—C6 | −0.6 (4) | O6—C17—C18—O7 | 115.6 (3) |
C15—C4—C5—C6 | 178.6 (2) | N2—C17—C18—O7 | −66.3 (3) |
C7—O2—C6—C5 | −3.9 (4) | C18—O7—C19—C28 | 1.7 (3) |
C7—O2—C6—C1 | 176.5 (2) | C18—O7—C19—C20 | −179.2 (2) |
C4—C5—C6—O2 | −178.7 (2) | C28—C19—C20—C21 | −0.3 (4) |
C4—C5—C6—C1 | 0.9 (4) | O7—C19—C20—C21 | −179.5 (3) |
O1—C1—C6—O2 | −2.0 (3) | C19—C20—C21—C22 | 1.0 (4) |
C2—C1—C6—O2 | 179.0 (2) | C20—C21—C22—C27 | −0.7 (4) |
O1—C1—C6—C5 | 178.3 (2) | C20—C21—C22—C23 | 178.8 (3) |
C2—C1—C6—C5 | −0.7 (4) | C21—C22—C23—C24 | −178.9 (3) |
C6—O2—C7—C8 | −174.9 (2) | C27—C22—C23—C24 | 0.6 (5) |
C9—O3—C8—C7 | −124.3 (9) | C22—C23—C24—C25 | −1.1 (5) |
O2—C7—C8—O3 | 74.0 (5) | C23—C24—C25—C26 | 0.8 (5) |
C8—O3—C9—C10 | 66.6 (15) | C24—C25—C26—C27 | 0.0 (5) |
C11—O4—C10—C9 | 168.5 (8) | C25—C26—C27—C28 | 179.4 (3) |
O3—C9—C10—O4 | 151.1 (11) | C25—C26—C27—C22 | −0.5 (4) |
C10—O4—C11—C12 | 94.5 (12) | C21—C22—C27—C28 | −0.2 (4) |
C13—O5—C12—C11 | −70.7 (7) | C23—C22—C27—C28 | −179.7 (3) |
O4—C11—C12—O5 | −77.4 (11) | C21—C22—C27—C26 | 179.7 (3) |
C11'—O4'—C10'—C9' | 171.9 (13) | C23—C22—C27—C26 | 0.2 (4) |
O3'—C9'—C10'—O4' | 78.8 (18) | O7—C19—C28—C27 | 178.5 (2) |
C12—O5—C13—C14 | 171.9 (2) | C20—C19—C28—C27 | −0.6 (4) |
C1—O1—C14—C13 | 166.8 (2) | C26—C27—C28—C19 | −179.0 (2) |
O5—C13—C14—O1 | −69.8 (3) | C22—C27—C28—C19 | 0.9 (4) |
N2—N1—C15—C4 | −179.9 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O6i | 0.86 | 2.15 | 2.963 (3) | 157 |
Symmetry code: (i) −x+1, −y+2, −z+1. |