The title compoud, C
21H
24N
4O
8, is an important intermediate for the synthesis of more complex glycoluril derivatives. The crystal structure is stabilized mostly by intermolecular C—H
O and C—H
π interactions.
Supporting information
CCDC reference: 633855
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.064
- wR factor = 0.196
- Data-to-parameter ratio = 11.5
checkCIF/PLATON results
No syntax errors found
Alert level B
DIFMX01_ALERT_2_B The maximum difference density is > 0.1*ZMAX*1.00
_refine_diff_density_max given = 0.835
Test value = 0.800
PLAT097_ALERT_2_B Maximum (Positive) Residual Density ............ 0.83 e/A
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.86 Ratio
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.40 Ratio
Alert level C
DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75
The relevant atom site should be identified.
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.83
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13'
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17'
PLAT301_ALERT_3_C Main Residue Disorder ......................... 20.00 Perc.
0 ALERT level A = In general: serious problem
4 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 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
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A
PUBL023_ALERT_1_A There is a mismatched ^ on line 97
2,13-dioxo-16,18-dioxa-1,3,12,14-tetraazapentacyclo[10.7.2.0^3,21^.0^5,\
If you require a ^ then it should be escaped
with a \, i.e. \^
Otherwise there must be a matching closing ~, e.g. ^12^C
PUBL023_ALERT_1_A There is a mismatched ^ on line 98
10^.0^14,20^]undeca-5,7,9-triene-20,21-dicarboxylate
If you require a ^ then it should be escaped
with a \, i.e. \^
Otherwise there must be a matching closing ~, e.g. ^12^C
2 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.
Diethyl 2,13-dioxo-16,18-dioxa-1,3,12,14-
tetraazapentacyclo[10.7.2.0
3,21.0
5,10.0
14,20]undeca-5,7,9-triene-
20,21-dicarboxylate
top
Crystal data top
C21H24N4O8 | F(000) = 968 |
Mr = 460.44 | Dx = 1.388 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3801 reflections |
a = 8.4954 (8) Å | θ = 2.4–25.4° |
b = 15.0557 (13) Å | µ = 0.11 mm−1 |
c = 17.2379 (16) Å | T = 298 K |
β = 91.541 (2)° | Block, colourless |
V = 2204.0 (3) Å3 | 0.30 × 0.20 × 0.20 mm |
Z = 4 | |
Data collection top
Bruker SMART 4K CCD area-detector diffractometer | 3087 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.068 |
Graphite monochromator | θmax = 26.0°, θmin = 1.8° |
φ and ω scans | h = −10→5 |
12355 measured reflections | k = −18→17 |
4325 independent reflections | l = −20→21 |
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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.196 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.1286P)2] where P = (Fo2 + 2Fc2)/3 |
4325 reflections | (Δ/σ)max = 0.001 |
376 parameters | Δρmax = 0.84 e Å−3 |
122 restraints | Δρmin = −0.22 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) |
C1 | 0.0541 (3) | 0.06890 (15) | 1.08561 (14) | 0.0364 (5) | |
C2 | −0.0688 (3) | 0.05135 (19) | 1.13462 (17) | 0.0503 (7) | |
H2 | −0.1629 | 0.0824 | 1.1282 | 0.060* | |
C3 | −0.0543 (4) | −0.0113 (2) | 1.19282 (18) | 0.0635 (9) | |
H3 | −0.1384 | −0.0228 | 1.2248 | 0.076* | |
C4 | 0.0847 (4) | −0.0567 (2) | 1.20335 (18) | 0.0613 (8) | |
H4 | 0.0955 | −0.0982 | 1.2431 | 0.074* | |
C5 | 0.2068 (3) | −0.04089 (17) | 1.15567 (15) | 0.0477 (6) | |
H5 | 0.3000 | −0.0726 | 1.1629 | 0.057* | |
C6 | 0.1952 (3) | 0.02168 (15) | 1.09638 (13) | 0.0358 (5) | |
C7 | 0.3346 (3) | 0.03534 (15) | 1.04531 (15) | 0.0392 (6) | |
H7A | 0.4196 | −0.0031 | 1.0634 | 0.047* | |
H7B | 0.3054 | 0.0173 | 0.9929 | 0.047* | |
C8 | 0.0341 (3) | 0.13723 (16) | 1.02221 (15) | 0.0409 (6) | |
H8A | 0.0414 | 0.1079 | 0.9723 | 0.049* | |
H8B | −0.0704 | 0.1629 | 1.0249 | 0.049* | |
C9 | 0.1241 (3) | 0.28863 (16) | 1.06034 (15) | 0.0428 (6) | |
C10 | 0.4920 (3) | 0.15982 (18) | 1.10016 (16) | 0.0430 (6) | |
C11 | 0.3083 (3) | 0.19595 (14) | 1.00258 (13) | 0.0368 (6) | |
C12 | 0.3130 (3) | 0.18132 (15) | 0.91360 (14) | 0.0448 (6) | |
O3' | 0.363 (3) | 0.1156 (11) | 0.882 (3) | 0.050 (4) | 0.33 (2) |
O4' | 0.2620 (19) | 0.2548 (7) | 0.8790 (8) | 0.042 (3) | 0.33 (2) |
C13' | 0.271 (2) | 0.2511 (12) | 0.7946 (8) | 0.054 (4) | 0.33 (2) |
H13C | 0.2343 | 0.1937 | 0.7760 | 0.065* | 0.33 (2) |
H13D | 0.3800 | 0.2580 | 0.7798 | 0.065* | 0.33 (2) |
C14' | 0.173 (4) | 0.324 (2) | 0.7584 (11) | 0.117 (9) | 0.33 (2) |
H14D | 0.0761 | 0.3290 | 0.7857 | 0.176* | 0.33 (2) |
H14E | 0.1493 | 0.3091 | 0.7050 | 0.176* | 0.33 (2) |
H14F | 0.2292 | 0.3786 | 0.7612 | 0.176* | 0.33 (2) |
O5 | 0.4406 (18) | 0.4005 (5) | 0.9379 (8) | 0.079 (3) | 0.514 (11) |
O6 | 0.6179 (8) | 0.2855 (5) | 0.9560 (4) | 0.074 (2) | 0.514 (11) |
C17 | 0.7530 (12) | 0.3173 (7) | 0.9096 (5) | 0.096 (3) | 0.514 (11) |
H17A | 0.7743 | 0.3792 | 0.9215 | 0.115* | 0.514 (11) |
H17B | 0.8465 | 0.2831 | 0.9233 | 0.115* | 0.514 (11) |
C18 | 0.7162 (15) | 0.3076 (7) | 0.8263 (4) | 0.121 (4) | 0.514 (11) |
H18A | 0.7099 | 0.2457 | 0.8134 | 0.182* | 0.514 (11) |
H18B | 0.7975 | 0.3351 | 0.7971 | 0.182* | 0.514 (11) |
H18C | 0.6171 | 0.3357 | 0.8141 | 0.182* | 0.514 (11) |
C15 | 0.3917 (3) | 0.28388 (15) | 1.03130 (14) | 0.0418 (6) | |
C16 | 0.4850 (4) | 0.33147 (19) | 0.96881 (19) | 0.0678 (10) | |
C19 | 0.2767 (4) | 0.42308 (16) | 1.09315 (17) | 0.0526 (7) | |
H19A | 0.3560 | 0.4570 | 1.0667 | 0.063* | |
H19B | 0.1775 | 0.4545 | 1.0869 | 0.063* | |
C20 | 0.6113 (3) | 0.3055 (2) | 1.1340 (2) | 0.0602 (8) | |
H20A | 0.7013 | 0.2686 | 1.1481 | 0.072* | |
H20B | 0.6476 | 0.3520 | 1.0999 | 0.072* | |
C21 | 0.4786 (4) | 0.4271 (2) | 1.19290 (19) | 0.0599 (8) | |
H21A | 0.5304 | 0.4612 | 1.1532 | 0.072* | |
H21B | 0.4890 | 0.4597 | 1.2413 | 0.072* | |
C13 | 0.2066 (19) | 0.2439 (6) | 0.7938 (5) | 0.074 (3) | 0.67 (2) |
H13A | 0.1041 | 0.2243 | 0.7744 | 0.088* | 0.67 (2) |
H13B | 0.2860 | 0.2055 | 0.7723 | 0.088* | 0.67 (2) |
C14 | 0.2347 (13) | 0.3376 (6) | 0.7702 (5) | 0.083 (3) | 0.67 (2) |
H14A | 0.1549 | 0.3751 | 0.7912 | 0.125* | 0.67 (2) |
H14B | 0.2309 | 0.3418 | 0.7146 | 0.125* | 0.67 (2) |
H14C | 0.3363 | 0.3564 | 0.7895 | 0.125* | 0.67 (2) |
O3 | 0.3929 (18) | 0.1282 (7) | 0.8839 (13) | 0.062 (3) | 0.67 (2) |
O4 | 0.2139 (12) | 0.2392 (5) | 0.8791 (4) | 0.058 (2) | 0.67 (2) |
C17' | 0.6589 (9) | 0.3204 (6) | 0.8669 (5) | 0.073 (3) | 0.486 (11) |
H17C | 0.6182 | 0.3800 | 0.8591 | 0.087* | 0.486 (11) |
H17D | 0.6411 | 0.2873 | 0.8192 | 0.087* | 0.486 (11) |
C18' | 0.8305 (9) | 0.3243 (10) | 0.8860 (8) | 0.138 (6) | 0.486 (11) |
H18D | 0.8469 | 0.3514 | 0.9360 | 0.207* | 0.486 (11) |
H18E | 0.8824 | 0.3588 | 0.8474 | 0.207* | 0.486 (11) |
H18F | 0.8731 | 0.2652 | 0.8869 | 0.207* | 0.486 (11) |
O5' | 0.472 (2) | 0.4130 (5) | 0.9552 (9) | 0.093 (4) | 0.486 (11) |
O6' | 0.5759 (9) | 0.2768 (5) | 0.9309 (5) | 0.069 (2) | 0.486 (11) |
N1 | 0.1500 (2) | 0.20809 (12) | 1.02691 (11) | 0.0375 (5) | |
N2 | 0.3929 (2) | 0.12718 (12) | 1.04331 (11) | 0.0374 (5) | |
N3 | 0.2615 (3) | 0.33674 (13) | 1.05653 (12) | 0.0449 (6) | |
N4 | 0.4963 (3) | 0.25166 (14) | 1.09201 (13) | 0.0475 (6) | |
O1 | 0.0013 (2) | 0.31394 (13) | 1.08677 (14) | 0.0648 (6) | |
O2 | 0.5646 (2) | 0.11707 (13) | 1.14815 (13) | 0.0608 (6) | |
O7 | 0.3180 (2) | 0.41891 (13) | 1.17247 (11) | 0.0566 (5) | |
O8 | 0.5545 (3) | 0.34474 (14) | 1.20144 (12) | 0.0618 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0355 (12) | 0.0315 (12) | 0.0422 (13) | −0.0067 (10) | 0.0018 (10) | −0.0061 (9) |
C2 | 0.0360 (14) | 0.0530 (16) | 0.0624 (17) | −0.0072 (12) | 0.0105 (12) | −0.0092 (13) |
C3 | 0.062 (2) | 0.070 (2) | 0.0591 (18) | −0.0242 (17) | 0.0251 (15) | −0.0011 (15) |
C4 | 0.072 (2) | 0.0566 (18) | 0.0555 (17) | −0.0118 (16) | 0.0055 (15) | 0.0170 (14) |
C5 | 0.0474 (15) | 0.0429 (14) | 0.0525 (15) | −0.0064 (12) | −0.0009 (12) | 0.0112 (11) |
C6 | 0.0365 (12) | 0.0292 (11) | 0.0417 (13) | −0.0044 (9) | 0.0016 (10) | −0.0033 (9) |
C7 | 0.0406 (13) | 0.0275 (11) | 0.0500 (14) | 0.0023 (10) | 0.0075 (11) | 0.0015 (10) |
C8 | 0.0376 (13) | 0.0352 (13) | 0.0497 (14) | 0.0000 (10) | −0.0049 (11) | −0.0029 (10) |
C9 | 0.0482 (15) | 0.0355 (13) | 0.0445 (13) | 0.0068 (11) | 0.0000 (12) | −0.0019 (10) |
C10 | 0.0277 (12) | 0.0464 (14) | 0.0554 (15) | 0.0002 (11) | 0.0096 (12) | −0.0036 (12) |
C11 | 0.0475 (14) | 0.0264 (11) | 0.0371 (12) | −0.0030 (10) | 0.0100 (11) | 0.0013 (9) |
C12 | 0.0659 (18) | 0.0314 (13) | 0.0376 (13) | −0.0028 (13) | 0.0095 (12) | 0.0003 (10) |
O3' | 0.077 (9) | 0.035 (5) | 0.038 (5) | −0.010 (5) | 0.012 (6) | −0.011 (4) |
O4' | 0.062 (6) | 0.031 (4) | 0.032 (3) | 0.001 (4) | 0.006 (4) | 0.006 (3) |
C13' | 0.062 (7) | 0.068 (7) | 0.032 (5) | −0.003 (6) | −0.006 (5) | 0.008 (4) |
C14' | 0.126 (17) | 0.136 (16) | 0.088 (11) | 0.032 (13) | −0.017 (10) | 0.024 (10) |
O5 | 0.149 (7) | 0.033 (3) | 0.057 (6) | −0.034 (4) | 0.032 (5) | −0.006 (3) |
O6 | 0.087 (4) | 0.075 (4) | 0.064 (4) | −0.044 (3) | 0.044 (3) | −0.022 (3) |
C17 | 0.093 (7) | 0.116 (6) | 0.080 (6) | −0.014 (5) | 0.032 (5) | 0.011 (5) |
C18 | 0.138 (10) | 0.144 (8) | 0.083 (6) | −0.059 (7) | 0.026 (7) | −0.022 (6) |
C15 | 0.0516 (15) | 0.0324 (12) | 0.0418 (13) | −0.0073 (11) | 0.0111 (12) | −0.0018 (10) |
C16 | 0.101 (3) | 0.0435 (17) | 0.0611 (19) | −0.0278 (17) | 0.0359 (18) | −0.0115 (15) |
C19 | 0.0693 (19) | 0.0316 (13) | 0.0570 (16) | 0.0024 (13) | 0.0018 (14) | −0.0053 (11) |
C20 | 0.0413 (15) | 0.0573 (17) | 0.082 (2) | −0.0108 (13) | 0.0072 (15) | −0.0167 (15) |
C21 | 0.070 (2) | 0.0495 (17) | 0.0606 (18) | −0.0125 (15) | −0.0006 (15) | −0.0127 (13) |
C13 | 0.112 (7) | 0.070 (4) | 0.040 (3) | 0.006 (5) | 0.007 (4) | 0.010 (3) |
C14 | 0.091 (6) | 0.100 (5) | 0.057 (4) | −0.013 (4) | −0.017 (4) | 0.046 (4) |
O3 | 0.083 (6) | 0.055 (4) | 0.048 (3) | 0.016 (5) | 0.016 (5) | −0.009 (5) |
O4 | 0.094 (5) | 0.040 (3) | 0.040 (2) | 0.000 (3) | 0.011 (3) | 0.0039 (17) |
C17' | 0.065 (5) | 0.099 (5) | 0.056 (5) | −0.003 (4) | 0.031 (4) | 0.016 (4) |
C18' | 0.075 (6) | 0.191 (11) | 0.152 (11) | 0.014 (7) | 0.056 (7) | 0.082 (9) |
O5' | 0.174 (9) | 0.051 (5) | 0.054 (6) | −0.050 (5) | 0.032 (5) | −0.009 (3) |
O6' | 0.079 (4) | 0.067 (4) | 0.062 (4) | −0.029 (3) | 0.034 (3) | −0.017 (3) |
N1 | 0.0430 (11) | 0.0289 (10) | 0.0408 (11) | −0.0006 (8) | 0.0044 (9) | −0.0017 (8) |
N2 | 0.0383 (11) | 0.0321 (10) | 0.0423 (11) | −0.0031 (8) | 0.0080 (9) | 0.0027 (8) |
N3 | 0.0570 (14) | 0.0281 (10) | 0.0499 (12) | −0.0026 (9) | 0.0066 (10) | −0.0057 (9) |
N4 | 0.0425 (12) | 0.0417 (12) | 0.0584 (14) | −0.0080 (10) | 0.0032 (10) | −0.0066 (10) |
O1 | 0.0508 (12) | 0.0512 (12) | 0.0929 (16) | 0.0124 (10) | 0.0103 (11) | −0.0191 (10) |
O2 | 0.0438 (11) | 0.0592 (12) | 0.0787 (14) | 0.0103 (9) | −0.0125 (10) | 0.0047 (11) |
O7 | 0.0639 (13) | 0.0579 (12) | 0.0485 (11) | −0.0026 (10) | 0.0086 (10) | −0.0118 (9) |
O8 | 0.0685 (14) | 0.0560 (12) | 0.0606 (12) | −0.0036 (10) | −0.0033 (11) | −0.0108 (10) |
Geometric parameters (Å, º) top
C1—C2 | 1.386 (4) | O6—C16 | 1.347 (7) |
C1—C6 | 1.402 (3) | O6—C17 | 1.496 (8) |
C1—C8 | 1.507 (3) | C17—C18 | 1.468 (8) |
C2—C3 | 1.381 (4) | C17—H17A | 0.9700 |
C2—H2 | 0.9300 | C17—H17B | 0.9700 |
C3—C4 | 1.372 (5) | C18—H18A | 0.9600 |
C3—H3 | 0.9300 | C18—H18B | 0.9600 |
C4—C5 | 1.362 (4) | C18—H18C | 0.9600 |
C4—H4 | 0.9300 | C15—N4 | 1.439 (4) |
C5—C6 | 1.392 (3) | C15—N3 | 1.439 (3) |
C5—H5 | 0.9300 | C15—C16 | 1.532 (4) |
C6—C7 | 1.509 (3) | C16—O5' | 1.255 (7) |
C7—N2 | 1.470 (3) | C16—O6' | 1.315 (6) |
C7—H7A | 0.9700 | C19—O7 | 1.404 (3) |
C7—H7B | 0.9700 | C19—N3 | 1.449 (3) |
C8—N1 | 1.453 (3) | C19—H19A | 0.9700 |
C8—H8A | 0.9700 | C19—H19B | 0.9700 |
C8—H8B | 0.9700 | C20—O8 | 1.401 (4) |
C9—O1 | 1.212 (3) | C20—N4 | 1.449 (4) |
C9—N1 | 1.363 (3) | C20—H20A | 0.9700 |
C9—N3 | 1.376 (3) | C20—H20B | 0.9700 |
C10—O2 | 1.205 (3) | C21—O8 | 1.404 (4) |
C10—N2 | 1.366 (3) | C21—O7 | 1.405 (4) |
C10—N4 | 1.390 (4) | C21—H21A | 0.9700 |
C11—N1 | 1.432 (3) | C21—H21B | 0.9700 |
C11—N2 | 1.433 (3) | C13—O4 | 1.472 (6) |
C11—C12 | 1.551 (3) | C13—C14 | 1.490 (7) |
C11—C15 | 1.575 (3) | C13—H13A | 0.9700 |
C12—O3 | 1.174 (13) | C13—H13B | 0.9700 |
C12—O3' | 1.21 (2) | C14—H14A | 0.9600 |
C12—O4' | 1.324 (8) | C14—H14B | 0.9600 |
C12—O4 | 1.340 (6) | C14—H14C | 0.9600 |
O4'—C13' | 1.461 (9) | C17'—O6' | 1.479 (8) |
C13'—C14' | 1.502 (9) | C17'—C18' | 1.488 (8) |
C13'—H13C | 0.9700 | C17'—H17C | 0.9700 |
C13'—H13D | 0.9700 | C17'—H17D | 0.9700 |
C14'—H14D | 0.9600 | C18'—H18D | 0.9600 |
C14'—H14E | 0.9600 | C18'—H18E | 0.9600 |
C14'—H14F | 0.9600 | C18'—H18F | 0.9600 |
O5—C16 | 1.223 (7) | | |
| | | |
C2—C1—C6 | 118.6 (2) | O6—C17—H17B | 109.6 |
C2—C1—C8 | 120.0 (2) | H17A—C17—H17B | 108.1 |
C6—C1—C8 | 121.4 (2) | N4—C15—N3 | 115.5 (2) |
C3—C2—C1 | 121.3 (3) | N4—C15—C16 | 110.4 (2) |
C3—C2—H2 | 119.4 | N3—C15—C16 | 111.7 (2) |
C1—C2—H2 | 119.4 | N4—C15—C11 | 102.06 (18) |
C4—C3—C2 | 119.7 (3) | N3—C15—C11 | 102.55 (19) |
C4—C3—H3 | 120.1 | C16—C15—C11 | 114.1 (2) |
C2—C3—H3 | 120.1 | O5—C16—O6' | 119.6 (9) |
C5—C4—C3 | 120.0 (3) | O5'—C16—O6' | 124.8 (8) |
C5—C4—H4 | 120.0 | O5—C16—O6 | 128.0 (7) |
C3—C4—H4 | 120.0 | O5'—C16—O6 | 123.0 (10) |
C4—C5—C6 | 121.4 (3) | O5—C16—C15 | 123.0 (8) |
C4—C5—H5 | 119.3 | O5'—C16—C15 | 122.9 (9) |
C6—C5—H5 | 119.3 | O6'—C16—C15 | 112.3 (4) |
C5—C6—C1 | 119.0 (2) | O6—C16—C15 | 109.1 (4) |
C5—C6—C7 | 118.6 (2) | O7—C19—N3 | 113.6 (2) |
C1—C6—C7 | 122.4 (2) | O7—C19—H19A | 108.8 |
N2—C7—C6 | 114.35 (19) | N3—C19—H19A | 108.8 |
N2—C7—H7A | 108.7 | O7—C19—H19B | 108.8 |
C6—C7—H7A | 108.7 | N3—C19—H19B | 108.8 |
N2—C7—H7B | 108.7 | H19A—C19—H19B | 107.7 |
C6—C7—H7B | 108.7 | O8—C20—N4 | 114.1 (2) |
H7A—C7—H7B | 107.6 | O8—C20—H20A | 108.7 |
N1—C8—C1 | 113.4 (2) | N4—C20—H20A | 108.7 |
N1—C8—H8A | 108.9 | O8—C20—H20B | 108.7 |
C1—C8—H8A | 108.9 | N4—C20—H20B | 108.7 |
N1—C8—H8B | 108.9 | H20A—C20—H20B | 107.6 |
C1—C8—H8B | 108.9 | O8—C21—O7 | 112.8 (2) |
H8A—C8—H8B | 107.7 | O8—C21—H21A | 109.0 |
O1—C9—N1 | 126.1 (3) | O7—C21—H21A | 109.0 |
O1—C9—N3 | 126.3 (2) | O8—C21—H21B | 109.0 |
N1—C9—N3 | 107.6 (2) | O7—C21—H21B | 109.0 |
O2—C10—N2 | 126.5 (2) | H21A—C21—H21B | 107.8 |
O2—C10—N4 | 125.9 (3) | O4—C13—C14 | 108.4 (5) |
N2—C10—N4 | 107.6 (2) | O4—C13—H13A | 110.0 |
N1—C11—N2 | 114.30 (18) | C14—C13—H13A | 110.0 |
N1—C11—C12 | 110.9 (2) | O4—C13—H13B | 110.0 |
N2—C11—C12 | 110.86 (18) | C14—C13—H13B | 110.0 |
N1—C11—C15 | 102.62 (18) | H13A—C13—H13B | 108.4 |
N2—C11—C15 | 103.76 (19) | C12—O4—C13 | 118.9 (7) |
C12—C11—C15 | 114.01 (18) | O6'—C17'—C18' | 109.6 (7) |
O3—C12—O4' | 124.0 (13) | O6'—C17'—H17C | 109.7 |
O3'—C12—O4' | 126.5 (19) | C18'—C17'—H17C | 109.7 |
O3—C12—O4 | 127.8 (11) | O6'—C17'—H17D | 109.7 |
O3'—C12—O4 | 123.8 (19) | C18'—C17'—H17D | 109.7 |
O3—C12—C11 | 123.9 (11) | H17C—C17'—H17D | 108.2 |
O3'—C12—C11 | 125.3 (19) | C17'—C18'—H18D | 109.5 |
O4'—C12—C11 | 108.0 (7) | C17'—C18'—H18E | 109.5 |
O4—C12—C11 | 108.3 (4) | H18D—C18'—H18E | 109.5 |
C12—O4'—C13' | 113.0 (12) | C17'—C18'—H18F | 109.5 |
O4'—C13'—C14' | 110.0 (9) | H18D—C18'—H18F | 109.5 |
O4'—C13'—H13C | 109.7 | H18E—C18'—H18F | 109.5 |
C14'—C13'—H13C | 109.7 | C16—O6'—C17' | 113.0 (6) |
O4'—C13'—H13D | 109.7 | C9—N1—C11 | 113.6 (2) |
C14'—C13'—H13D | 109.7 | C9—N1—C8 | 124.1 (2) |
H13C—C13'—H13D | 108.2 | C11—N1—C8 | 122.06 (18) |
C13'—C14'—H14D | 109.5 | C10—N2—C11 | 112.5 (2) |
C13'—C14'—H14E | 109.5 | C10—N2—C7 | 121.6 (2) |
H14D—C14'—H14E | 109.5 | C11—N2—C7 | 121.8 (2) |
C13'—C14'—H14F | 109.5 | C9—N3—C15 | 112.50 (19) |
H14D—C14'—H14F | 109.5 | C9—N3—C19 | 121.1 (2) |
H14E—C14'—H14F | 109.5 | C15—N3—C19 | 124.6 (2) |
C16—O6—C17 | 125.6 (7) | C10—N4—C15 | 113.0 (2) |
C18—C17—O6 | 110.2 (8) | C10—N4—C20 | 121.7 (2) |
C18—C17—H17A | 109.6 | C15—N4—C20 | 124.8 (2) |
O6—C17—H17A | 109.6 | C19—O7—C21 | 117.1 (2) |
C18—C17—H17B | 109.6 | C20—O8—C21 | 117.0 (2) |
| | | |
C6—C1—C2—C3 | −0.3 (4) | O4'—C12—O4—C13 | 82 (3) |
C8—C1—C2—C3 | 179.5 (2) | C11—C12—O4—C13 | 175.0 (5) |
C1—C2—C3—C4 | 0.8 (4) | C14—C13—O4—C12 | −125.5 (15) |
C2—C3—C4—C5 | −1.1 (5) | O5—C16—O6'—C17' | 20.8 (11) |
C3—C4—C5—C6 | 0.9 (5) | O5'—C16—O6'—C17' | −2.3 (13) |
C4—C5—C6—C1 | −0.3 (4) | O6—C16—O6'—C17' | −96.4 (14) |
C4—C5—C6—C7 | −179.5 (3) | C15—C16—O6'—C17' | 176.2 (5) |
C2—C1—C6—C5 | 0.0 (3) | C18'—C17'—O6'—C16 | 111.6 (10) |
C8—C1—C6—C5 | −179.8 (2) | O1—C9—N1—C11 | −178.6 (3) |
C2—C1—C6—C7 | 179.2 (2) | N3—C9—N1—C11 | 3.1 (3) |
C8—C1—C6—C7 | −0.5 (3) | O1—C9—N1—C8 | −4.0 (4) |
C5—C6—C7—N2 | −123.3 (2) | N3—C9—N1—C8 | 177.7 (2) |
C1—C6—C7—N2 | 57.5 (3) | N2—C11—N1—C9 | 115.2 (2) |
C2—C1—C8—N1 | 122.6 (2) | C12—C11—N1—C9 | −118.6 (2) |
C6—C1—C8—N1 | −57.7 (3) | C15—C11—N1—C9 | 3.5 (3) |
N1—C11—C12—O3 | −137.7 (11) | N2—C11—N1—C8 | −59.6 (3) |
N2—C11—C12—O3 | −9.6 (11) | C12—C11—N1—C8 | 66.7 (3) |
C15—C11—C12—O3 | 107.0 (11) | C15—C11—N1—C8 | −171.2 (2) |
N1—C11—C12—O3' | −119.2 (19) | C1—C8—N1—C9 | −97.1 (3) |
N2—C11—C12—O3' | 8.9 (19) | C1—C8—N1—C11 | 77.0 (3) |
C15—C11—C12—O3' | 125.5 (19) | O2—C10—N2—C11 | 171.9 (2) |
N1—C11—C12—O4' | 64.3 (8) | N4—C10—N2—C11 | −9.1 (3) |
N2—C11—C12—O4' | −167.5 (8) | O2—C10—N2—C7 | 14.5 (4) |
C15—C11—C12—O4' | −50.9 (8) | N4—C10—N2—C7 | −166.44 (19) |
N1—C11—C12—O4 | 42.9 (5) | N1—C11—N2—C10 | −100.4 (2) |
N2—C11—C12—O4 | 171.0 (5) | C12—C11—N2—C10 | 133.3 (2) |
C15—C11—C12—O4 | −72.3 (5) | C15—C11—N2—C10 | 10.5 (2) |
O3—C12—O4'—C13' | 18.1 (16) | N1—C11—N2—C7 | 56.9 (3) |
O3'—C12—O4'—C13' | 0 (2) | C12—C11—N2—C7 | −69.4 (3) |
O4—C12—O4'—C13' | −90 (3) | C15—C11—N2—C7 | 167.85 (19) |
C11—C12—O4'—C13' | 176.0 (9) | C6—C7—N2—C10 | 82.1 (3) |
C12—O4'—C13'—C14' | 164 (3) | C6—C7—N2—C11 | −73.2 (3) |
C16—O6—C17—C18 | −78.9 (11) | O1—C9—N3—C15 | 172.3 (3) |
N1—C11—C15—N4 | 111.6 (2) | N1—C9—N3—C15 | −9.4 (3) |
N2—C11—C15—N4 | −7.7 (2) | O1—C9—N3—C19 | 6.9 (4) |
C12—C11—C15—N4 | −128.4 (2) | N1—C9—N3—C19 | −174.8 (2) |
N1—C11—C15—N3 | −8.4 (2) | N4—C15—N3—C9 | −99.0 (2) |
N2—C11—C15—N3 | −127.63 (19) | C16—C15—N3—C9 | 133.7 (2) |
C12—C11—C15—N3 | 111.7 (2) | C11—C15—N3—C9 | 11.1 (3) |
N1—C11—C15—C16 | −129.4 (2) | N4—C15—N3—C19 | 65.8 (3) |
N2—C11—C15—C16 | 111.4 (3) | C16—C15—N3—C19 | −61.5 (3) |
C12—C11—C15—C16 | −9.3 (3) | C11—C15—N3—C19 | 175.9 (2) |
C17—O6—C16—O5 | 10.4 (12) | O7—C19—N3—C9 | 83.6 (3) |
C17—O6—C16—O5' | −13.8 (12) | O7—C19—N3—C15 | −79.9 (3) |
C17—O6—C16—O6' | 88.9 (14) | O2—C10—N4—C15 | −177.6 (2) |
C17—O6—C16—C15 | −169.1 (6) | N2—C10—N4—C15 | 3.4 (3) |
N4—C15—C16—O5 | −138.8 (8) | O2—C10—N4—C20 | 10.3 (4) |
N3—C15—C16—O5 | −8.8 (8) | N2—C10—N4—C20 | −168.7 (2) |
C11—C15—C16—O5 | 107.0 (8) | N3—C15—N4—C10 | 113.3 (2) |
N4—C15—C16—O5' | −114.6 (10) | C16—C15—N4—C10 | −118.8 (2) |
N3—C15—C16—O5' | 15.4 (10) | C11—C15—N4—C10 | 2.9 (3) |
C11—C15—C16—O5' | 131.1 (9) | N3—C15—N4—C20 | −74.9 (3) |
N4—C15—C16—O6' | 66.9 (5) | C16—C15—N4—C20 | 53.0 (3) |
N3—C15—C16—O6' | −163.1 (5) | C11—C15—N4—C20 | 174.7 (2) |
C11—C15—C16—O6' | −47.3 (6) | O8—C20—N4—C10 | −98.2 (3) |
N4—C15—C16—O6 | 40.7 (5) | O8—C20—N4—C15 | 90.6 (3) |
N3—C15—C16—O6 | 170.7 (4) | N3—C19—O7—C21 | 95.6 (3) |
C11—C15—C16—O6 | −73.5 (5) | O8—C21—O7—C19 | −94.7 (3) |
O3—C12—O4—C13 | −4.3 (13) | N4—C20—O8—C21 | −86.9 (3) |
O3'—C12—O4—C13 | −23 (2) | O7—C21—O8—C20 | 85.3 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O2i | 0.93 | 2.41 | 3.282 (3) | 157 |
C3—H3···O7ii | 0.93 | 2.53 | 3.434 (3) | 165 |
C13—H13B···O7iii | 0.97 | 2.56 | 3.374 (10) | 141 |
C8—H8A···Cgiv | 0.97 | 2.79 | 3.679 (3) | 153 |
Symmetry codes: (i) x−1, y, z; (ii) −x, y−1/2, −z+5/2; (iii) x, −y+1/2, z−1/2; (iv) −x, −y, −z+2. |