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In the title compound, C
20H
32N
6O
6, the five-membered imidazolone rings adopt envelope conformations. The six-membered rings are in chair conformations. The crystal packing is stabilized by C—H
O hydrogen bonds.
Supporting information
CCDC reference: 622511
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.005 Å
- Disorder in main residue
- R factor = 0.064
- wR factor = 0.197
- Data-to-parameter ratio = 12.0
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C10
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C14
Alert level C
DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75
_refine_diff_density_max given = 0.625
Test value = 0.600
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 .... 2.02
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.62 e/A
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.50 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.79 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C18
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for O6'
PLAT301_ALERT_3_C Main Residue Disorder ......................... 11.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 29.00 Deg.
C11' -C10 -H10B 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 24.10 Deg.
C11 -C10 -H10C 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 24.70 Deg.
H10A -C10 -H10D 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 32.40 Deg.
C10 -C11 -H10C 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 27.50 Deg.
O6 -C13 -O6' 1.555 1.555 1.555
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
15 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
13 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 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, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.
Diethyl 2,6-diisopropyl-4,8-dioxoperhydro-2,3a,4a,6,7a,8a-
hexaazacyclopenta[def]fluorene-8 b,8c-dicarboxylate
top
Crystal data top
C20H32N6O6 | F(000) = 968 |
Mr = 452.52 | Dx = 1.356 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4685 reflections |
a = 11.4577 (15) Å | θ = 2.4–24.8° |
b = 9.2015 (13) Å | µ = 0.10 mm−1 |
c = 21.164 (3) Å | T = 292 K |
β = 96.621 (2)° | Block, colorless |
V = 2216.4 (5) Å3 | 0.30 × 0.20 × 0.10 mm |
Z = 4 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 2920 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.021 |
Graphite monochromator | θmax = 25.0°, θmin = 2.4° |
φ and ω scans | h = −13→13 |
10681 measured reflections | k = −7→10 |
3883 independent reflections | l = −23→25 |
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) = 0.197 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.1136P)2 + 0.6272P] where P = (Fo2 + 2Fc2)/3 |
3883 reflections | (Δ/σ)max = 0.010 |
323 parameters | Δρmax = 0.63 e Å−3 |
6 restraints | Δρmin = −0.31 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 | 0.6073 (3) | 0.8703 (5) | 0.1107 (2) | 0.1155 (13) | |
H1A | 0.6056 | 0.9741 | 0.1152 | 0.173* | |
H1B | 0.6021 | 0.8457 | 0.0663 | 0.173* | |
H1C | 0.6794 | 0.8331 | 0.1322 | 0.173* | |
C2 | 0.3910 (3) | 0.8675 (6) | 0.10168 (18) | 0.1161 (13) | |
H2A | 0.3220 | 0.8195 | 0.1130 | 0.174* | |
H2B | 0.3960 | 0.8544 | 0.0571 | 0.174* | |
H2C | 0.3865 | 0.9694 | 0.1109 | 0.174* | |
C3 | 0.5010 (3) | 0.8019 (4) | 0.14032 (17) | 0.0886 (9) | |
H3 | 0.5013 | 0.6961 | 0.1349 | 0.106* | |
C4 | 0.4031 (2) | 0.8055 (3) | 0.23705 (15) | 0.0736 (7) | |
H4A | 0.3340 | 0.8293 | 0.2080 | 0.088* | |
H4B | 0.4031 | 0.8676 | 0.2741 | 0.088* | |
C5 | 0.6105 (2) | 0.7840 (3) | 0.24423 (16) | 0.0759 (8) | |
H5A | 0.6247 | 0.8433 | 0.2822 | 0.091* | |
H5B | 0.6773 | 0.7957 | 0.2204 | 0.091* | |
C6 | 0.33226 (18) | 0.5467 (3) | 0.22114 (12) | 0.0595 (6) | |
C7 | 0.63975 (18) | 0.5165 (3) | 0.22799 (12) | 0.0606 (6) | |
C8 | 0.49889 (18) | 0.5923 (3) | 0.29224 (12) | 0.0583 (6) | |
C9 | 0.5107 (2) | 0.6420 (3) | 0.36224 (13) | 0.0715 (7) | |
C10 | 0.6286 (4) | 0.6224 (6) | 0.46011 (17) | 0.1132 (13) | |
H10A | 0.5552 | 0.6453 | 0.4766 | 0.136* | 0.579 (7) |
H10B | 0.6818 | 0.7041 | 0.4681 | 0.136* | 0.579 (7) |
H10C | 0.6901 | 0.5620 | 0.4788 | 0.136* | 0.421 (7) |
H10D | 0.5575 | 0.6007 | 0.4786 | 0.136* | 0.421 (7) |
C11 | 0.6809 (12) | 0.4892 (12) | 0.4900 (5) | 0.199 (4) | 0.579 (7) |
H11A | 0.6215 | 0.4349 | 0.5082 | 0.299* | 0.579 (7) |
H11B | 0.7424 | 0.5150 | 0.5228 | 0.299* | 0.579 (7) |
H11C | 0.7128 | 0.4311 | 0.4584 | 0.299* | 0.579 (7) |
C11' | 0.6529 (15) | 0.7776 (12) | 0.4806 (7) | 0.199 (4) | 0.421 (7) |
H11D | 0.7361 | 0.7946 | 0.4855 | 0.299* | 0.421 (7) |
H11E | 0.6226 | 0.7947 | 0.5204 | 0.299* | 0.421 (7) |
H11F | 0.6154 | 0.8423 | 0.4489 | 0.299* | 0.421 (7) |
C12 | 0.48730 (18) | 0.4253 (3) | 0.28070 (11) | 0.0569 (6) | |
C13 | 0.4805 (2) | 0.3345 (3) | 0.34084 (13) | 0.0699 (7) | |
C14 | 0.5209 (7) | 0.1052 (9) | 0.3912 (4) | 0.108 (2) | 0.684 (9) |
H14A | 0.4490 | 0.1257 | 0.4097 | 0.129* | 0.684 (9) |
H14B | 0.5159 | 0.0073 | 0.3740 | 0.129* | 0.684 (9) |
C15 | 0.6199 (8) | 0.1173 (17) | 0.4387 (5) | 0.199 (6) | 0.684 (9) |
H15A | 0.6896 | 0.0872 | 0.4211 | 0.299* | 0.684 (9) |
H15B | 0.6082 | 0.0563 | 0.4742 | 0.299* | 0.684 (9) |
H15C | 0.6284 | 0.2164 | 0.4526 | 0.299* | 0.684 (9) |
O6 | 0.5357 (5) | 0.2084 (5) | 0.3414 (4) | 0.0824 (15) | 0.684 (9) |
C14' | 0.573 (3) | 0.172 (2) | 0.4103 (8) | 0.152 (9) | 0.316 (9) |
H14C | 0.4998 | 0.1939 | 0.4269 | 0.182* | 0.316 (9) |
H14D | 0.6364 | 0.2073 | 0.4409 | 0.182* | 0.316 (9) |
C15' | 0.584 (2) | 0.012 (2) | 0.4049 (12) | 0.199 (6) | 0.316 (9) |
H15D | 0.6256 | −0.0113 | 0.3692 | 0.299* | 0.316 (9) |
H15E | 0.5076 | −0.0313 | 0.3990 | 0.299* | 0.316 (9) |
H15F | 0.6272 | −0.0260 | 0.4431 | 0.299* | 0.316 (9) |
O6' | 0.5765 (9) | 0.2524 (14) | 0.3503 (9) | 0.091 (4) | 0.316 (9) |
C16 | 0.3639 (2) | 0.2820 (3) | 0.19963 (12) | 0.0656 (7) | |
H16A | 0.3600 | 0.1965 | 0.2261 | 0.079* | |
H16B | 0.2908 | 0.2882 | 0.1717 | 0.079* | |
C17 | 0.5701 (2) | 0.2635 (3) | 0.20300 (13) | 0.0673 (7) | |
H17A | 0.6347 | 0.2601 | 0.1772 | 0.081* | |
H17B | 0.5734 | 0.1758 | 0.2286 | 0.081* | |
C18 | 0.4553 (3) | 0.3631 (3) | 0.10532 (13) | 0.0736 (7) | |
H18 | 0.4625 | 0.4640 | 0.1201 | 0.088* | |
C19 | 0.5560 (3) | 0.3291 (5) | 0.06708 (16) | 0.1059 (11) | |
H19A | 0.6291 | 0.3545 | 0.0914 | 0.159* | |
H19B | 0.5469 | 0.3842 | 0.0283 | 0.159* | |
H19C | 0.5558 | 0.2273 | 0.0573 | 0.159* | |
C20 | 0.3403 (3) | 0.3453 (5) | 0.06353 (16) | 0.1051 (11) | |
H20A | 0.3300 | 0.2452 | 0.0514 | 0.158* | |
H20B | 0.3408 | 0.4043 | 0.0262 | 0.158* | |
H20C | 0.2768 | 0.3752 | 0.0865 | 0.158* | |
N1 | 0.50701 (18) | 0.8369 (3) | 0.20629 (12) | 0.0790 (7) | |
N2 | 0.39475 (15) | 0.6520 (2) | 0.25720 (10) | 0.0596 (5) | |
N3 | 0.60335 (15) | 0.6303 (2) | 0.26333 (10) | 0.0614 (5) | |
N4 | 0.37556 (15) | 0.4119 (2) | 0.24068 (9) | 0.0577 (5) | |
N5 | 0.58585 (15) | 0.3908 (2) | 0.24580 (9) | 0.0595 (5) | |
N6 | 0.46019 (18) | 0.2653 (2) | 0.16136 (10) | 0.0651 (6) | |
O1 | 0.24938 (14) | 0.5685 (2) | 0.18158 (9) | 0.0754 (5) | |
O2 | 0.71177 (14) | 0.5239 (2) | 0.19057 (10) | 0.0777 (6) | |
O3 | 0.4415 (2) | 0.7187 (3) | 0.38417 (11) | 0.0983 (7) | |
O4 | 0.60861 (18) | 0.5906 (3) | 0.39258 (9) | 0.0881 (6) | |
O5 | 0.4165 (2) | 0.3683 (3) | 0.37911 (10) | 0.0911 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.091 (2) | 0.154 (4) | 0.106 (3) | −0.002 (2) | 0.032 (2) | 0.010 (3) |
C2 | 0.083 (2) | 0.173 (4) | 0.089 (2) | 0.010 (2) | −0.0016 (18) | −0.005 (2) |
C3 | 0.0761 (18) | 0.082 (2) | 0.109 (2) | 0.0035 (15) | 0.0133 (17) | −0.0172 (18) |
C4 | 0.0525 (14) | 0.0733 (17) | 0.0963 (19) | 0.0087 (12) | 0.0141 (13) | 0.0081 (15) |
C5 | 0.0494 (13) | 0.0752 (18) | 0.104 (2) | −0.0060 (12) | 0.0117 (13) | 0.0076 (15) |
C6 | 0.0364 (11) | 0.0729 (16) | 0.0708 (14) | 0.0020 (10) | 0.0131 (10) | 0.0013 (12) |
C7 | 0.0354 (11) | 0.0724 (16) | 0.0742 (14) | 0.0033 (10) | 0.0076 (10) | 0.0093 (12) |
C8 | 0.0413 (11) | 0.0659 (15) | 0.0682 (14) | 0.0000 (10) | 0.0080 (10) | −0.0010 (11) |
C9 | 0.0605 (15) | 0.0773 (17) | 0.0768 (17) | −0.0068 (13) | 0.0078 (13) | −0.0100 (14) |
C10 | 0.123 (3) | 0.139 (3) | 0.074 (2) | −0.011 (3) | −0.008 (2) | −0.011 (2) |
C11 | 0.195 (9) | 0.265 (12) | 0.133 (6) | 0.012 (9) | −0.002 (6) | −0.033 (8) |
C11' | 0.195 (9) | 0.265 (12) | 0.133 (6) | 0.012 (9) | −0.002 (6) | −0.033 (8) |
C12 | 0.0445 (11) | 0.0662 (15) | 0.0608 (13) | 0.0012 (10) | 0.0101 (10) | −0.0007 (11) |
C13 | 0.0697 (16) | 0.0774 (18) | 0.0634 (15) | −0.0040 (14) | 0.0114 (12) | 0.0032 (13) |
C14 | 0.133 (5) | 0.095 (5) | 0.089 (4) | 0.001 (4) | −0.019 (3) | 0.015 (3) |
C15 | 0.151 (8) | 0.281 (17) | 0.157 (9) | −0.025 (8) | −0.016 (6) | 0.062 (9) |
O6 | 0.092 (3) | 0.072 (3) | 0.082 (2) | 0.006 (2) | 0.007 (3) | 0.022 (2) |
C14' | 0.23 (3) | 0.133 (16) | 0.084 (11) | 0.049 (16) | −0.024 (12) | 0.052 (11) |
C15' | 0.151 (8) | 0.281 (17) | 0.157 (9) | −0.025 (8) | −0.016 (6) | 0.062 (9) |
O6' | 0.100 (8) | 0.070 (6) | 0.107 (8) | 0.017 (6) | 0.028 (7) | 0.029 (6) |
C16 | 0.0595 (14) | 0.0669 (16) | 0.0714 (15) | −0.0112 (11) | 0.0120 (12) | 0.0003 (12) |
C17 | 0.0630 (14) | 0.0660 (16) | 0.0750 (15) | 0.0091 (12) | 0.0173 (12) | −0.0001 (13) |
C18 | 0.0850 (18) | 0.0677 (16) | 0.0699 (15) | −0.0049 (13) | 0.0168 (14) | 0.0013 (13) |
C19 | 0.115 (3) | 0.127 (3) | 0.083 (2) | 0.001 (2) | 0.0387 (19) | 0.010 (2) |
C20 | 0.107 (3) | 0.130 (3) | 0.0764 (19) | −0.010 (2) | 0.0014 (18) | 0.012 (2) |
N1 | 0.0571 (12) | 0.0857 (16) | 0.0953 (17) | 0.0028 (11) | 0.0134 (11) | 0.0140 (13) |
N2 | 0.0404 (9) | 0.0639 (12) | 0.0749 (12) | 0.0039 (8) | 0.0087 (8) | −0.0010 (10) |
N3 | 0.0405 (9) | 0.0667 (13) | 0.0774 (13) | −0.0001 (8) | 0.0090 (9) | 0.0030 (10) |
N4 | 0.0428 (9) | 0.0659 (12) | 0.0651 (11) | −0.0030 (8) | 0.0089 (8) | 0.0004 (9) |
N5 | 0.0436 (9) | 0.0680 (13) | 0.0679 (12) | 0.0055 (8) | 0.0110 (8) | 0.0008 (10) |
N6 | 0.0674 (12) | 0.0627 (13) | 0.0668 (12) | −0.0035 (10) | 0.0151 (10) | −0.0021 (10) |
O1 | 0.0454 (9) | 0.0889 (13) | 0.0899 (12) | 0.0044 (8) | −0.0014 (9) | 0.0017 (10) |
O2 | 0.0498 (9) | 0.0884 (13) | 0.0997 (13) | 0.0076 (8) | 0.0286 (9) | 0.0099 (11) |
O3 | 0.0982 (15) | 0.1089 (17) | 0.0901 (14) | 0.0148 (13) | 0.0204 (12) | −0.0255 (13) |
O4 | 0.0753 (12) | 0.1164 (17) | 0.0695 (11) | 0.0006 (11) | −0.0046 (10) | −0.0079 (11) |
O5 | 0.1038 (15) | 0.0980 (15) | 0.0773 (12) | −0.0060 (12) | 0.0355 (12) | 0.0057 (11) |
Geometric parameters (Å, º) top
C1—C3 | 1.565 (5) | C11'—H11D | 0.9600 |
C1—H1A | 0.9600 | C11'—H11E | 0.9600 |
C1—H1B | 0.9600 | C11'—H11F | 0.9600 |
C1—H1C | 0.9600 | C12—N5 | 1.454 (3) |
C2—C3 | 1.544 (5) | C12—N4 | 1.457 (3) |
C2—H2A | 0.9600 | C12—C13 | 1.532 (4) |
C2—H2B | 0.9600 | C13—O5 | 1.195 (3) |
C2—H2C | 0.9600 | C13—O6 | 1.321 (5) |
C3—N1 | 1.427 (4) | C13—O6' | 1.330 (8) |
C3—H3 | 0.9800 | C14—C15 | 1.431 (7) |
C4—N1 | 1.450 (3) | C14—O6 | 1.444 (10) |
C4—N2 | 1.482 (4) | C14—H14A | 0.9700 |
C4—H4A | 0.9700 | C14—H14B | 0.9700 |
C4—H4B | 0.9700 | C15—H15A | 0.9600 |
C5—N1 | 1.438 (4) | C15—H15B | 0.9600 |
C5—N3 | 1.476 (3) | C15—H15C | 0.9600 |
C5—H5A | 0.9700 | C14'—O6' | 1.47 (2) |
C5—H5B | 0.9700 | C14'—C15' | 1.488 (9) |
C6—O1 | 1.208 (3) | C14'—H14C | 0.9700 |
C6—N2 | 1.381 (3) | C14'—H14D | 0.9700 |
C6—N4 | 1.382 (3) | C15'—H15D | 0.9600 |
C7—O2 | 1.210 (3) | C15'—H15E | 0.9600 |
C7—N3 | 1.379 (3) | C15'—H15F | 0.9600 |
C7—N5 | 1.384 (3) | C16—N6 | 1.450 (3) |
C8—N2 | 1.439 (3) | C16—N4 | 1.474 (3) |
C8—N3 | 1.449 (3) | C16—H16A | 0.9700 |
C8—C9 | 1.541 (4) | C16—H16B | 0.9700 |
C8—C12 | 1.559 (4) | C17—N6 | 1.452 (3) |
C9—O3 | 1.194 (3) | C17—N5 | 1.479 (3) |
C9—O4 | 1.315 (3) | C17—H17A | 0.9700 |
C10—O4 | 1.451 (4) | C17—H17B | 0.9700 |
C10—C11 | 1.474 (8) | C18—N6 | 1.484 (3) |
C10—C11' | 1.509 (9) | C18—C20 | 1.509 (4) |
C10—H10A | 0.9700 | C18—C19 | 1.516 (4) |
C10—H10B | 0.9700 | C18—H18 | 0.9800 |
C10—H10C | 0.9475 | C19—H19A | 0.9600 |
C10—H10D | 0.9643 | C19—H19B | 0.9600 |
C11—H10C | 0.7223 | C19—H19C | 0.9600 |
C11—H11A | 0.9600 | C20—H20A | 0.9600 |
C11—H11B | 0.9600 | C20—H20B | 0.9600 |
C11—H11C | 0.9600 | C20—H20C | 0.9600 |
| | | |
C3—C1—H1A | 109.5 | N5—C12—C13 | 114.8 (2) |
C3—C1—H1B | 109.5 | N4—C12—C13 | 108.15 (19) |
H1A—C1—H1B | 109.5 | N5—C12—C8 | 103.75 (18) |
C3—C1—H1C | 109.5 | N4—C12—C8 | 103.18 (18) |
H1A—C1—H1C | 109.5 | C13—C12—C8 | 114.8 (2) |
H1B—C1—H1C | 109.5 | O5—C13—O6 | 123.6 (4) |
C3—C2—H2A | 109.5 | O5—C13—O6' | 127.4 (8) |
C3—C2—H2B | 109.5 | O6—C13—O6' | 27.5 (6) |
H2A—C2—H2B | 109.5 | O5—C13—C12 | 121.0 (2) |
C3—C2—H2C | 109.5 | O6—C13—C12 | 114.6 (4) |
H2A—C2—H2C | 109.5 | O6'—C13—C12 | 108.4 (7) |
H2B—C2—H2C | 109.5 | C15—C14—O6 | 108.1 (8) |
N1—C3—C2 | 112.0 (3) | C15—C14—H14A | 110.1 |
N1—C3—C1 | 110.5 (3) | O6—C14—H14A | 110.1 |
C2—C3—C1 | 104.8 (3) | C15—C14—H14B | 110.1 |
N1—C3—H3 | 109.8 | O6—C14—H14B | 110.1 |
C2—C3—H3 | 109.8 | H14A—C14—H14B | 108.4 |
C1—C3—H3 | 109.8 | C13—O6—C14 | 119.2 (7) |
N1—C4—N2 | 113.7 (2) | O6'—C14'—C15' | 114.9 (17) |
N1—C4—H4A | 108.8 | O6'—C14'—H14C | 108.6 |
N2—C4—H4A | 108.8 | C15'—C14'—H14C | 108.6 |
N1—C4—H4B | 108.8 | O6'—C14'—H14D | 108.5 |
N2—C4—H4B | 108.8 | C15'—C14'—H14D | 108.5 |
H4A—C4—H4B | 107.7 | H14C—C14'—H14D | 107.5 |
N1—C5—N3 | 114.1 (2) | C14'—C15'—H15D | 109.5 |
N1—C5—H5A | 108.7 | C14'—C15'—H15E | 109.5 |
N3—C5—H5A | 108.7 | H15D—C15'—H15E | 109.5 |
N1—C5—H5B | 108.7 | C14'—C15'—H15F | 109.5 |
N3—C5—H5B | 108.7 | H15D—C15'—H15F | 109.5 |
H5A—C5—H5B | 107.6 | H15E—C15'—H15F | 109.5 |
O1—C6—N2 | 125.6 (2) | C13—O6'—C14' | 108.2 (14) |
O1—C6—N4 | 125.6 (2) | N6—C16—N4 | 113.07 (19) |
N2—C6—N4 | 108.61 (19) | N6—C16—H16A | 109.0 |
O2—C7—N3 | 125.8 (2) | N4—C16—H16A | 109.0 |
O2—C7—N5 | 125.8 (2) | N6—C16—H16B | 109.0 |
N3—C7—N5 | 108.3 (2) | N4—C16—H16B | 109.0 |
N2—C8—N3 | 111.5 (2) | H16A—C16—H16B | 107.8 |
N2—C8—C9 | 111.0 (2) | N6—C17—N5 | 113.48 (19) |
N3—C8—C9 | 110.43 (19) | N6—C17—H17A | 108.9 |
N2—C8—C12 | 104.18 (18) | N5—C17—H17A | 108.9 |
N3—C8—C12 | 103.38 (18) | N6—C17—H17B | 108.9 |
C9—C8—C12 | 116.1 (2) | N5—C17—H17B | 108.9 |
O3—C9—O4 | 126.1 (3) | H17A—C17—H17B | 107.7 |
O3—C9—C8 | 124.1 (3) | N6—C18—C20 | 110.6 (2) |
O4—C9—C8 | 109.8 (2) | N6—C18—C19 | 109.9 (3) |
O4—C10—C11 | 105.4 (6) | C20—C18—C19 | 109.4 (3) |
O4—C10—C11' | 118.5 (7) | N6—C18—H18 | 109.0 |
C11—C10—C11' | 127.7 (8) | C20—C18—H18 | 109.0 |
O4—C10—H10A | 110.7 | C19—C18—H18 | 109.0 |
C11—C10—H10A | 110.7 | C18—C19—H19A | 109.5 |
C11'—C10—H10A | 80.2 | C18—C19—H19B | 109.5 |
O4—C10—H10B | 110.7 | H19A—C19—H19B | 109.5 |
C11—C10—H10B | 110.7 | C18—C19—H19C | 109.5 |
C11'—C10—H10B | 29.0 | H19A—C19—H19C | 109.5 |
H10A—C10—H10B | 108.8 | H19B—C19—H19C | 109.5 |
O4—C10—H10C | 108.5 | C18—C20—H20A | 109.5 |
C11—C10—H10C | 24.1 | C18—C20—H20B | 109.5 |
C11'—C10—H10C | 109.4 | H20A—C20—H20B | 109.5 |
H10A—C10—H10C | 127.7 | C18—C20—H20C | 109.5 |
H10B—C10—H10C | 87.7 | H20A—C20—H20C | 109.5 |
O4—C10—H10D | 108.2 | H20B—C20—H20C | 109.5 |
C11—C10—H10D | 88.5 | C3—N1—C5 | 114.4 (2) |
C11'—C10—H10D | 102.5 | C3—N1—C4 | 116.4 (2) |
H10A—C10—H10D | 24.7 | C5—N1—C4 | 110.4 (2) |
H10B—C10—H10D | 129.2 | C6—N2—C8 | 111.3 (2) |
H10C—C10—H10D | 109.4 | C6—N2—C4 | 123.8 (2) |
C10—C11—H10C | 32.4 | C8—N2—C4 | 115.79 (19) |
C10—C11—H11A | 109.5 | C7—N3—C8 | 111.23 (19) |
H10C—C11—H11A | 138.8 | C7—N3—C5 | 123.3 (2) |
C10—C11—H11B | 109.5 | C8—N3—C5 | 114.95 (19) |
H10C—C11—H11B | 83.4 | C6—N4—C12 | 111.03 (19) |
C10—C11—H11C | 109.5 | C6—N4—C16 | 123.1 (2) |
H10C—C11—H11C | 101.9 | C12—N4—C16 | 115.17 (19) |
C10—C11'—H11D | 109.5 | C7—N5—C12 | 110.67 (19) |
C10—C11'—H11E | 109.5 | C7—N5—C17 | 121.5 (2) |
H11D—C11'—H11E | 109.5 | C12—N5—C17 | 115.92 (18) |
C10—C11'—H11F | 109.5 | C16—N6—C17 | 108.96 (19) |
H11D—C11'—H11F | 109.5 | C16—N6—C18 | 114.9 (2) |
H11E—C11'—H11F | 109.5 | C17—N6—C18 | 116.2 (2) |
N5—C12—N4 | 111.60 (18) | C9—O4—C10 | 115.9 (3) |
| | | |
N2—C8—C9—O3 | 0.7 (4) | N1—C4—N2—C6 | −95.1 (3) |
N3—C8—C9—O3 | 124.8 (3) | N1—C4—N2—C8 | 48.9 (3) |
C12—C8—C9—O3 | −118.0 (3) | O2—C7—N3—C8 | 167.2 (2) |
N2—C8—C9—O4 | −177.6 (2) | N5—C7—N3—C8 | −16.8 (3) |
N3—C8—C9—O4 | −53.5 (3) | O2—C7—N3—C5 | 24.4 (4) |
C12—C8—C9—O4 | 63.8 (3) | N5—C7—N3—C5 | −159.6 (2) |
N2—C8—C12—N5 | 115.78 (18) | N2—C8—N3—C7 | −100.8 (2) |
N3—C8—C12—N5 | −0.9 (2) | C9—C8—N3—C7 | 135.4 (2) |
C9—C8—C12—N5 | −121.9 (2) | C12—C8—N3—C7 | 10.6 (2) |
N2—C8—C12—N4 | −0.7 (2) | N2—C8—N3—C5 | 45.4 (3) |
N3—C8—C12—N4 | −117.39 (18) | C9—C8—N3—C5 | −78.5 (3) |
C9—C8—C12—N4 | 121.6 (2) | C12—C8—N3—C5 | 156.7 (2) |
N2—C8—C12—C13 | −118.2 (2) | N1—C5—N3—C7 | 90.8 (3) |
N3—C8—C12—C13 | 125.2 (2) | N1—C5—N3—C8 | −50.8 (3) |
C9—C8—C12—C13 | 4.1 (3) | O1—C6—N4—C12 | 170.3 (2) |
N5—C12—C13—O5 | 167.1 (2) | N2—C6—N4—C12 | −13.4 (2) |
N4—C12—C13—O5 | −67.5 (3) | O1—C6—N4—C16 | 27.6 (3) |
C8—C12—C13—O5 | 47.0 (3) | N2—C6—N4—C16 | −156.10 (19) |
N5—C12—C13—O6 | −22.7 (4) | N5—C12—N4—C6 | −102.3 (2) |
N4—C12—C13—O6 | 102.6 (4) | C13—C12—N4—C6 | 130.5 (2) |
C8—C12—C13—O6 | −142.8 (4) | C8—C12—N4—C6 | 8.5 (2) |
N5—C12—C13—O6' | 6.1 (8) | N5—C12—N4—C16 | 43.5 (3) |
N4—C12—C13—O6' | 131.5 (8) | C13—C12—N4—C16 | −83.7 (2) |
C8—C12—C13—O6' | −114.0 (8) | C8—C12—N4—C16 | 154.36 (19) |
O5—C13—O6—C14 | −1.2 (8) | N6—C16—N4—C6 | 88.8 (3) |
O6'—C13—O6—C14 | 106 (2) | N6—C16—N4—C12 | −52.5 (3) |
C12—C13—O6—C14 | −171.1 (4) | O2—C7—N5—C12 | −168.0 (2) |
C15—C14—O6—C13 | −98.7 (10) | N3—C7—N5—C12 | 16.0 (3) |
O5—C13—O6'—C14' | 17.1 (18) | O2—C7—N5—C17 | −26.8 (3) |
O6—C13—O6'—C14' | −75 (2) | N3—C7—N5—C17 | 157.2 (2) |
C12—C13—O6'—C14' | 176.5 (13) | N4—C12—N5—C7 | 101.4 (2) |
C15'—C14'—O6'—C13 | 125 (2) | C13—C12—N5—C7 | −135.0 (2) |
C2—C3—N1—C5 | −177.4 (3) | C8—C12—N5—C7 | −9.0 (2) |
C1—C3—N1—C5 | −61.0 (4) | N4—C12—N5—C17 | −42.0 (3) |
C2—C3—N1—C4 | 51.8 (4) | C13—C12—N5—C17 | 81.5 (3) |
C1—C3—N1—C4 | 168.3 (3) | C8—C12—N5—C17 | −152.5 (2) |
N3—C5—N1—C3 | −82.0 (3) | N6—C17—N5—C7 | −90.0 (3) |
N3—C5—N1—C4 | 51.6 (3) | N6—C17—N5—C12 | 49.2 (3) |
N2—C4—N1—C3 | 82.3 (3) | N4—C16—N6—C17 | 55.8 (3) |
N2—C4—N1—C5 | −50.4 (3) | N4—C16—N6—C18 | −76.6 (3) |
O1—C6—N2—C8 | −170.8 (2) | N5—C17—N6—C16 | −54.1 (3) |
N4—C6—N2—C8 | 12.9 (2) | N5—C17—N6—C18 | 77.6 (3) |
O1—C6—N2—C4 | −25.5 (3) | C20—C18—N6—C16 | −55.6 (3) |
N4—C6—N2—C4 | 158.28 (19) | C19—C18—N6—C16 | −176.5 (2) |
N3—C8—N2—C6 | 103.6 (2) | C20—C18—N6—C17 | 175.4 (3) |
C9—C8—N2—C6 | −132.9 (2) | C19—C18—N6—C17 | 54.5 (3) |
C12—C8—N2—C6 | −7.2 (2) | O3—C9—O4—C10 | 4.9 (5) |
N3—C8—N2—C4 | −44.7 (3) | C8—C9—O4—C10 | −176.9 (3) |
C9—C8—N2—C4 | 78.8 (3) | C11—C10—O4—C9 | 141.0 (6) |
C12—C8—N2—C4 | −155.6 (2) | C11'—C10—O4—C9 | −68.5 (9) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17A···O2 | 0.97 | 2.59 | 2.923 (3) | 100 |
C14—H14A···O5 | 0.97 | 2.34 | 2.700 (9) | 101 |
C10—H10A···O3 | 0.97 | 2.32 | 2.677 (5) | 101 |
C5—H5A···O2i | 0.97 | 2.52 | 3.205 (3) | 128 |
Symmetry code: (i) −x+3/2, y+1/2, −z+1/2. |
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