The title compound, 4,7,13,16,21,24-hexaoxa-1-azonia-10-azabicyclo[8.8.8]hexacosane picrate monohydrate, C
18H
37N
2O
6+·C
6H
2N
3O
7−·H
2O, is a salt of [2.2.2]cryptand (4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane) with picric acid (2,4,6-trinitrophenol). The monoprotonated cryptand cation encapsulates a water molecule through N—H
O and O—H
O hydrogen bonds.
Supporting information
CCDC reference: 624969
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.003 Å
- R factor = 0.047
- wR factor = 0.131
- Data-to-parameter ratio = 16.6
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.855 0.984
Tmin(prime) and Tmax expected: 0.980 0.984
RR(prime) = 0.872
Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.87
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 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
1 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
Data collection: PROCESS-AUTO (Rigaku/MSC, 2004); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.
4,7,13,16,21,24-hexaoxa-1-azonia-10-azabicyclo[8.8.8]hexacosane picrate
monohydrate
top
Crystal data top
C18H37N2O6+·C6H2N3O7−·H2O | F(000) = 1328.00 |
Mr = 623.61 | Dx = 1.424 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71075 Å |
Hall symbol: -P 2ybc | Cell parameters from 17071 reflections |
a = 9.2633 (3) Å | θ = 3.1–30.0° |
b = 19.2661 (6) Å | µ = 0.12 mm−1 |
c = 16.3624 (5) Å | T = 150 K |
β = 94.8805 (11)° | Block, light orange |
V = 2909.57 (16) Å3 | 0.17 × 0.16 × 0.14 mm |
Z = 4 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 3809 reflections with I > 2σ(I) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.067 |
ω scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −12→12 |
Tmin = 0.855, Tmax = 0.984 | k = −22→25 |
27944 measured reflections | l = −21→21 |
6652 independent reflections | |
Refinement top
Refinement on F2 | 2 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.047 | w = 1/[σ2(Fo2) + (0.0486P)2 + 0.9805P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.131 | (Δ/σ)max < 0.001 |
S = 1.10 | Δρmax = 0.37 e Å−3 |
6652 reflections | Δρmin = −0.36 e Å−3 |
401 parameters | |
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 | 0.77296 (19) | 0.52106 (10) | 0.83919 (9) | 0.0464 (5) | |
O2 | 0.6582 (2) | 0.44969 (11) | 0.95639 (11) | 0.0607 (6) | |
O3 | 0.6790 (2) | 0.49018 (11) | 1.07753 (11) | 0.0643 (7) | |
O4 | 1.05127 (18) | 0.64775 (9) | 1.16624 (9) | 0.0373 (4) | |
O5 | 1.18712 (17) | 0.69393 (8) | 1.07946 (9) | 0.0346 (4) | |
O6 | 1.0762 (2) | 0.65528 (10) | 0.78939 (10) | 0.0492 (5) | |
O7 | 1.0162 (2) | 0.54904 (10) | 0.76017 (10) | 0.0485 (5) | |
O8 | 0.54308 (16) | 0.25531 (8) | 0.66018 (9) | 0.0291 (4) | |
O9 | 0.35637 (17) | 0.20206 (8) | 0.51844 (8) | 0.0298 (4) | |
O10 | 0.74915 (17) | 0.41107 (7) | 0.52728 (8) | 0.0279 (4) | |
O11 | 0.55384 (16) | 0.38291 (8) | 0.38443 (8) | 0.0278 (4) | |
O12 | 0.30244 (17) | 0.40292 (9) | 0.67876 (9) | 0.0343 (4) | |
O13 | 0.13705 (16) | 0.35294 (8) | 0.54391 (8) | 0.0284 (4) | |
O14 | 0.44094 (19) | 0.39776 (10) | 0.53867 (9) | 0.0344 (4) | |
N1 | 0.7108 (2) | 0.49058 (10) | 1.00681 (11) | 0.0300 (4) | |
N2 | 1.0875 (2) | 0.65521 (9) | 1.09566 (10) | 0.0255 (4) | |
N3 | 1.0239 (2) | 0.59899 (11) | 0.80699 (11) | 0.0342 (5) | |
N4 | 0.5989 (2) | 0.41072 (9) | 0.68611 (10) | 0.0236 (4) | |
N5 | 0.27304 (19) | 0.30947 (9) | 0.38879 (10) | 0.0251 (4) | |
C1 | 0.8487 (2) | 0.54625 (12) | 0.89796 (13) | 0.0276 (5) | |
C2 | 0.8213 (2) | 0.53840 (11) | 0.98380 (13) | 0.0240 (5) | |
C3 | 0.8978 (2) | 0.57320 (11) | 1.04679 (12) | 0.0243 (5) | |
H3 | 0.8757 | 0.5665 | 1.1006 | 0.029* | |
C4 | 1.0079 (2) | 0.61823 (11) | 1.02986 (12) | 0.0227 (5) | |
C5 | 1.0459 (2) | 0.62718 (11) | 0.95026 (12) | 0.0250 (5) | |
H5 | 1.1205 | 0.6573 | 0.9395 | 0.030* | |
C6 | 0.9725 (2) | 0.59117 (11) | 0.88815 (12) | 0.0257 (5) | |
C7 | 0.6165 (3) | 0.35071 (11) | 0.74403 (12) | 0.0280 (5) | |
H7B | 0.5247 | 0.3415 | 0.7664 | 0.034* | |
H7A | 0.6865 | 0.3628 | 0.7893 | 0.034* | |
C8 | 0.6661 (2) | 0.28606 (12) | 0.70310 (14) | 0.0313 (5) | |
H8A | 0.7377 | 0.2976 | 0.6653 | 0.038* | |
H8B | 0.7096 | 0.2541 | 0.7438 | 0.038* | |
C9 | 0.5804 (3) | 0.19835 (12) | 0.61064 (13) | 0.0308 (5) | |
H9B | 0.6413 | 0.1660 | 0.6433 | 0.037* | |
H9A | 0.6339 | 0.2148 | 0.5660 | 0.037* | |
C10 | 0.4439 (3) | 0.16258 (12) | 0.57672 (13) | 0.0315 (5) | |
H10A | 0.4700 | 0.1194 | 0.5512 | 0.038* | |
H10B | 0.3869 | 0.1510 | 0.6219 | 0.038* | |
C11 | 0.4121 (3) | 0.20478 (13) | 0.44022 (13) | 0.0324 (5) | |
H11B | 0.4385 | 0.1585 | 0.4234 | 0.039* | |
H11A | 0.4980 | 0.2337 | 0.4428 | 0.039* | |
C12 | 0.2975 (3) | 0.23436 (11) | 0.37928 (13) | 0.0297 (5) | |
H12A | 0.3252 | 0.2257 | 0.3243 | 0.036* | |
H12B | 0.2070 | 0.2101 | 0.3848 | 0.036* | |
C13 | 0.7463 (2) | 0.43803 (12) | 0.66877 (12) | 0.0270 (5) | |
H13A | 0.7747 | 0.4740 | 0.7084 | 0.032* | |
H13B | 0.8163 | 0.4006 | 0.6766 | 0.032* | |
C14 | 0.7527 (3) | 0.46717 (11) | 0.58383 (12) | 0.0292 (5) | |
H14A | 0.6709 | 0.4978 | 0.5706 | 0.035* | |
H14B | 0.8411 | 0.4937 | 0.5809 | 0.035* | |
C15 | 0.7697 (3) | 0.43410 (12) | 0.44615 (12) | 0.0310 (5) | |
H15B | 0.8722 | 0.4403 | 0.4403 | 0.037* | |
H15A | 0.7217 | 0.4784 | 0.4359 | 0.037* | |
C16 | 0.7082 (3) | 0.38133 (13) | 0.38558 (13) | 0.0318 (5) | |
H16A | 0.7376 | 0.3919 | 0.3314 | 0.038* | |
H16B | 0.7440 | 0.3355 | 0.4012 | 0.038* | |
C17 | 0.4844 (3) | 0.34652 (12) | 0.31610 (12) | 0.0304 (5) | |
H17B | 0.5173 | 0.2987 | 0.3168 | 0.037* | |
H17A | 0.5096 | 0.3677 | 0.2655 | 0.037* | |
C18 | 0.3226 (3) | 0.34849 (12) | 0.31983 (13) | 0.0316 (5) | |
H18A | 0.2921 | 0.3964 | 0.3239 | 0.038* | |
H18B | 0.2764 | 0.3297 | 0.2691 | 0.038* | |
C19 | 0.5107 (3) | 0.46852 (12) | 0.71860 (13) | 0.0299 (5) | |
H19A | 0.5643 | 0.4884 | 0.7665 | 0.036* | |
H19B | 0.4982 | 0.5046 | 0.6773 | 0.036* | |
C20 | 0.3641 (3) | 0.44628 (13) | 0.74158 (13) | 0.0312 (5) | |
H20A | 0.3733 | 0.4214 | 0.7933 | 0.037* | |
H20B | 0.3030 | 0.4866 | 0.7475 | 0.037* | |
C21 | 0.1547 (2) | 0.38701 (14) | 0.68409 (14) | 0.0343 (6) | |
H21B | 0.0952 | 0.4275 | 0.6706 | 0.041* | |
H21A | 0.1387 | 0.3724 | 0.7393 | 0.041* | |
C22 | 0.1161 (3) | 0.32961 (13) | 0.62449 (13) | 0.0347 (6) | |
H22A | 0.1767 | 0.2895 | 0.6379 | 0.042* | |
H22B | 0.0158 | 0.3162 | 0.6276 | 0.042* | |
C23 | 0.0788 (2) | 0.30457 (12) | 0.48371 (13) | 0.0288 (5) | |
H23B | −0.0260 | 0.3037 | 0.4832 | 0.035* | |
H23A | 0.1149 | 0.2584 | 0.4974 | 0.035* | |
C24 | 0.1214 (2) | 0.32502 (12) | 0.40028 (13) | 0.0301 (5) | |
H24A | 0.0598 | 0.3007 | 0.3587 | 0.036* | |
H24B | 0.1050 | 0.3744 | 0.3925 | 0.036* | |
H4N | 0.544 (3) | 0.3974 (14) | 0.6354 (16) | 0.054 (8)* | |
H14C | 0.362 (3) | 0.3763 (16) | 0.5414 (19) | 0.077 (12)* | |
H14D | 0.471 (4) | 0.3842 (17) | 0.4927 (14) | 0.083 (11)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0372 (11) | 0.0700 (13) | 0.0313 (9) | −0.0171 (10) | −0.0019 (7) | −0.0157 (9) |
O2 | 0.0672 (15) | 0.0661 (14) | 0.0487 (11) | −0.0405 (12) | 0.0051 (10) | −0.0131 (10) |
O3 | 0.0701 (15) | 0.0795 (15) | 0.0478 (11) | −0.0419 (12) | 0.0321 (10) | −0.0203 (10) |
O4 | 0.0311 (10) | 0.0569 (11) | 0.0241 (8) | −0.0037 (8) | 0.0034 (7) | −0.0078 (7) |
O5 | 0.0298 (10) | 0.0350 (10) | 0.0381 (9) | −0.0092 (8) | −0.0025 (7) | −0.0008 (7) |
O6 | 0.0533 (13) | 0.0622 (13) | 0.0319 (9) | −0.0237 (10) | 0.0024 (8) | 0.0083 (8) |
O7 | 0.0553 (13) | 0.0575 (13) | 0.0341 (9) | −0.0021 (10) | 0.0123 (8) | −0.0137 (9) |
O8 | 0.0232 (9) | 0.0312 (9) | 0.0324 (8) | 0.0025 (7) | 0.0005 (6) | −0.0016 (7) |
O9 | 0.0282 (9) | 0.0342 (9) | 0.0270 (8) | 0.0049 (7) | 0.0026 (6) | 0.0017 (6) |
O10 | 0.0320 (9) | 0.0279 (8) | 0.0240 (8) | −0.0018 (7) | 0.0040 (6) | −0.0014 (6) |
O11 | 0.0265 (9) | 0.0347 (9) | 0.0225 (7) | −0.0012 (7) | 0.0038 (6) | −0.0049 (6) |
O12 | 0.0231 (9) | 0.0512 (11) | 0.0290 (8) | −0.0048 (8) | 0.0056 (6) | −0.0132 (7) |
O13 | 0.0266 (9) | 0.0311 (9) | 0.0276 (8) | −0.0064 (7) | 0.0027 (6) | −0.0034 (6) |
O14 | 0.0262 (10) | 0.0534 (11) | 0.0237 (9) | −0.0062 (9) | 0.0020 (7) | −0.0053 (7) |
N1 | 0.0253 (11) | 0.0298 (11) | 0.0351 (11) | −0.0019 (9) | 0.0037 (8) | −0.0044 (8) |
N2 | 0.0203 (10) | 0.0287 (10) | 0.0272 (10) | 0.0019 (8) | −0.0002 (7) | −0.0022 (8) |
N3 | 0.0277 (11) | 0.0496 (14) | 0.0250 (10) | −0.0035 (10) | −0.0002 (8) | −0.0006 (9) |
N4 | 0.0214 (10) | 0.0275 (10) | 0.0216 (9) | −0.0014 (8) | −0.0011 (7) | 0.0001 (7) |
N5 | 0.0233 (10) | 0.0261 (10) | 0.0256 (9) | −0.0002 (8) | 0.0003 (7) | −0.0004 (7) |
C1 | 0.0221 (12) | 0.0334 (13) | 0.0269 (12) | 0.0025 (10) | −0.0002 (9) | −0.0040 (9) |
C2 | 0.0157 (11) | 0.0256 (12) | 0.0305 (11) | −0.0004 (9) | 0.0012 (8) | −0.0031 (9) |
C3 | 0.0225 (12) | 0.0255 (12) | 0.0251 (11) | 0.0073 (9) | 0.0027 (9) | −0.0008 (9) |
C4 | 0.0196 (11) | 0.0258 (12) | 0.0222 (10) | 0.0012 (9) | −0.0019 (8) | −0.0034 (8) |
C5 | 0.0219 (12) | 0.0235 (11) | 0.0290 (11) | 0.0030 (9) | −0.0004 (9) | 0.0015 (9) |
C6 | 0.0257 (12) | 0.0314 (12) | 0.0201 (11) | 0.0022 (10) | 0.0019 (9) | 0.0004 (9) |
C7 | 0.0266 (13) | 0.0343 (13) | 0.0230 (11) | 0.0000 (10) | 0.0002 (9) | 0.0064 (9) |
C8 | 0.0232 (12) | 0.0311 (13) | 0.0392 (13) | −0.0015 (10) | 0.0003 (10) | 0.0048 (10) |
C9 | 0.0296 (13) | 0.0314 (13) | 0.0316 (12) | 0.0073 (10) | 0.0045 (10) | 0.0019 (9) |
C10 | 0.0355 (14) | 0.0278 (13) | 0.0308 (12) | 0.0037 (10) | 0.0014 (10) | 0.0054 (9) |
C11 | 0.0310 (14) | 0.0374 (14) | 0.0293 (12) | 0.0057 (11) | 0.0057 (10) | 0.0003 (10) |
C12 | 0.0323 (13) | 0.0284 (12) | 0.0281 (12) | −0.0001 (10) | 0.0020 (9) | −0.0050 (9) |
C13 | 0.0222 (12) | 0.0311 (12) | 0.0272 (11) | −0.0069 (10) | −0.0014 (9) | −0.0023 (9) |
C14 | 0.0312 (13) | 0.0270 (12) | 0.0294 (12) | −0.0072 (10) | 0.0026 (9) | −0.0032 (9) |
C15 | 0.0273 (13) | 0.0387 (14) | 0.0279 (12) | −0.0046 (11) | 0.0079 (9) | 0.0011 (10) |
C16 | 0.0286 (14) | 0.0399 (14) | 0.0282 (11) | 0.0003 (11) | 0.0105 (9) | −0.0016 (10) |
C17 | 0.0375 (14) | 0.0325 (13) | 0.0219 (11) | −0.0060 (11) | 0.0059 (9) | −0.0040 (9) |
C18 | 0.0399 (15) | 0.0317 (13) | 0.0219 (11) | −0.0028 (11) | −0.0040 (9) | −0.0006 (9) |
C19 | 0.0312 (13) | 0.0290 (12) | 0.0280 (12) | 0.0006 (10) | −0.0051 (9) | −0.0054 (9) |
C20 | 0.0304 (14) | 0.0370 (14) | 0.0260 (12) | 0.0027 (11) | 0.0008 (9) | −0.0067 (10) |
C21 | 0.0206 (12) | 0.0520 (16) | 0.0318 (12) | −0.0029 (11) | 0.0111 (9) | −0.0049 (11) |
C22 | 0.0283 (14) | 0.0433 (15) | 0.0336 (13) | −0.0082 (11) | 0.0092 (10) | −0.0011 (11) |
C23 | 0.0198 (12) | 0.0292 (13) | 0.0366 (12) | −0.0035 (10) | −0.0031 (9) | −0.0046 (9) |
C24 | 0.0272 (13) | 0.0291 (12) | 0.0329 (12) | −0.0010 (10) | −0.0043 (9) | −0.0024 (9) |
Geometric parameters (Å, º) top
O1—C1 | 1.240 (3) | C8—H8A | 0.9700 |
O2—N1 | 1.213 (2) | C8—H8B | 0.9700 |
O3—N1 | 1.218 (2) | C9—C10 | 1.504 (3) |
O4—N2 | 1.238 (2) | C9—H9B | 0.9700 |
O5—N2 | 1.233 (2) | C9—H9A | 0.9700 |
O6—N3 | 1.232 (3) | C10—H10A | 0.9700 |
O7—N3 | 1.228 (3) | C10—H10B | 0.9700 |
O8—C8 | 1.416 (3) | C11—C12 | 1.505 (3) |
O8—C9 | 1.424 (3) | C11—H11B | 0.9700 |
O9—C10 | 1.419 (3) | C11—H11A | 0.9700 |
O9—C11 | 1.421 (2) | C12—H12A | 0.9700 |
O10—C14 | 1.422 (2) | C12—H12B | 0.9700 |
O10—C15 | 1.428 (2) | C13—C14 | 1.505 (3) |
O11—C17 | 1.426 (2) | C13—H13A | 0.9700 |
O11—C16 | 1.429 (3) | C13—H13B | 0.9700 |
O12—C20 | 1.407 (3) | C14—H14A | 0.9700 |
O12—C21 | 1.413 (3) | C14—H14B | 0.9700 |
O13—C22 | 1.422 (2) | C15—C16 | 1.498 (3) |
O13—C23 | 1.428 (2) | C15—H15B | 0.9700 |
O14—H14C | 0.844 (18) | C15—H15A | 0.9700 |
O14—H14D | 0.863 (18) | C16—H16A | 0.9700 |
N1—C2 | 1.451 (3) | C16—H16B | 0.9700 |
N2—C4 | 1.441 (3) | C17—C18 | 1.506 (3) |
N3—C6 | 1.456 (3) | C17—H17B | 0.9700 |
N4—C7 | 1.495 (3) | C17—H17A | 0.9700 |
N4—C19 | 1.504 (3) | C18—H18A | 0.9700 |
N4—C13 | 1.513 (3) | C18—H18B | 0.9700 |
N4—H4N | 0.97 (3) | C19—C20 | 1.503 (3) |
N5—C18 | 1.462 (3) | C19—H19A | 0.9700 |
N5—C24 | 1.464 (3) | C19—H19B | 0.9700 |
N5—C12 | 1.475 (3) | C20—H20A | 0.9700 |
C1—C2 | 1.456 (3) | C20—H20B | 0.9700 |
C1—C6 | 1.456 (3) | C21—C22 | 1.497 (3) |
C2—C3 | 1.375 (3) | C21—H21B | 0.9700 |
C3—C4 | 1.385 (3) | C21—H21A | 0.9700 |
C3—H3 | 0.9300 | C22—H22A | 0.9700 |
C4—C5 | 1.389 (3) | C22—H22B | 0.9700 |
C5—C6 | 1.364 (3) | C23—C24 | 1.505 (3) |
C5—H5 | 0.9300 | C23—H23B | 0.9700 |
C7—C8 | 1.505 (3) | C23—H23A | 0.9700 |
C7—H7B | 0.9700 | C24—H24A | 0.9700 |
C7—H7A | 0.9700 | C24—H24B | 0.9700 |
| | | |
C8—O8—C9 | 112.36 (17) | N5—C12—H12B | 108.7 |
C10—O9—C11 | 113.24 (17) | C11—C12—H12B | 108.7 |
C14—O10—C15 | 111.79 (16) | H12A—C12—H12B | 107.6 |
C17—O11—C16 | 112.60 (16) | C14—C13—N4 | 114.22 (18) |
C20—O12—C21 | 114.75 (16) | C14—C13—H13A | 108.7 |
C22—O13—C23 | 111.09 (16) | N4—C13—H13A | 108.7 |
H14C—O14—H14D | 104 (3) | C14—C13—H13B | 108.7 |
O2—N1—O3 | 121.8 (2) | N4—C13—H13B | 108.7 |
O2—N1—C2 | 119.19 (18) | H13A—C13—H13B | 107.6 |
O3—N1—C2 | 118.92 (18) | O10—C14—C13 | 108.47 (17) |
O5—N2—O4 | 122.55 (18) | O10—C14—H14A | 110.0 |
O5—N2—C4 | 118.91 (17) | C13—C14—H14A | 110.0 |
O4—N2—C4 | 118.52 (18) | O10—C14—H14B | 110.0 |
O7—N3—O6 | 123.2 (2) | C13—C14—H14B | 110.0 |
O7—N3—C6 | 118.8 (2) | H14A—C14—H14B | 108.4 |
O6—N3—C6 | 118.02 (19) | O10—C15—C16 | 109.32 (18) |
C7—N4—C19 | 112.43 (16) | O10—C15—H15B | 109.8 |
C7—N4—C13 | 109.66 (17) | C16—C15—H15B | 109.8 |
C19—N4—C13 | 109.55 (17) | O10—C15—H15A | 109.8 |
C7—N4—H4N | 111.0 (16) | C16—C15—H15A | 109.8 |
C19—N4—H4N | 103.8 (16) | H15B—C15—H15A | 108.3 |
C13—N4—H4N | 110.3 (16) | O11—C16—C15 | 108.53 (18) |
C18—N5—C24 | 111.19 (17) | O11—C16—H16A | 110.0 |
C18—N5—C12 | 111.23 (17) | C15—C16—H16A | 110.0 |
C24—N5—C12 | 111.83 (17) | O11—C16—H16B | 110.0 |
O1—C1—C2 | 125.0 (2) | C15—C16—H16B | 110.0 |
O1—C1—C6 | 123.1 (2) | H16A—C16—H16B | 108.4 |
C2—C1—C6 | 111.80 (18) | O11—C17—C18 | 109.89 (17) |
C3—C2—N1 | 116.45 (19) | O11—C17—H17B | 109.7 |
C3—C2—C1 | 123.5 (2) | C18—C17—H17B | 109.7 |
N1—C2—C1 | 120.06 (18) | O11—C17—H17A | 109.7 |
C2—C3—C4 | 119.80 (19) | C18—C17—H17A | 109.7 |
C2—C3—H3 | 120.1 | H17B—C17—H17A | 108.2 |
C4—C3—H3 | 120.1 | N5—C18—C17 | 113.40 (18) |
C3—C4—C5 | 121.02 (19) | N5—C18—H18A | 108.9 |
C3—C4—N2 | 119.95 (18) | C17—C18—H18A | 108.9 |
C5—C4—N2 | 119.01 (19) | N5—C18—H18B | 108.9 |
C6—C5—C4 | 119.0 (2) | C17—C18—H18B | 108.9 |
C6—C5—H5 | 120.5 | H18A—C18—H18B | 107.7 |
C4—C5—H5 | 120.5 | C20—C19—N4 | 114.00 (18) |
C5—C6—N3 | 116.5 (2) | C20—C19—H19A | 108.8 |
C5—C6—C1 | 124.60 (19) | N4—C19—H19A | 108.8 |
N3—C6—C1 | 118.92 (18) | C20—C19—H19B | 108.8 |
N4—C7—C8 | 112.27 (17) | N4—C19—H19B | 108.8 |
N4—C7—H7B | 109.2 | H19A—C19—H19B | 107.6 |
C8—C7—H7B | 109.2 | O12—C20—C19 | 107.80 (17) |
N4—C7—H7A | 109.2 | O12—C20—H20A | 110.1 |
C8—C7—H7A | 109.2 | C19—C20—H20A | 110.1 |
H7B—C7—H7A | 107.9 | O12—C20—H20B | 110.1 |
O8—C8—C7 | 107.67 (18) | C19—C20—H20B | 110.1 |
O8—C8—H8A | 110.2 | H20A—C20—H20B | 108.5 |
C7—C8—H8A | 110.2 | O12—C21—C22 | 107.39 (18) |
O8—C8—H8B | 110.2 | O12—C21—H21B | 110.2 |
C7—C8—H8B | 110.2 | C22—C21—H21B | 110.2 |
H8A—C8—H8B | 108.5 | O12—C21—H21A | 110.2 |
O8—C9—C10 | 109.02 (19) | C22—C21—H21A | 110.2 |
O8—C9—H9B | 109.9 | H21B—C21—H21A | 108.5 |
C10—C9—H9B | 109.9 | O13—C22—C21 | 109.06 (19) |
O8—C9—H9A | 109.9 | O13—C22—H22A | 109.9 |
C10—C9—H9A | 109.9 | C21—C22—H22A | 109.9 |
H9B—C9—H9A | 108.3 | O13—C22—H22B | 109.9 |
O9—C10—C9 | 114.62 (18) | C21—C22—H22B | 109.9 |
O9—C10—H10A | 108.6 | H22A—C22—H22B | 108.3 |
C9—C10—H10A | 108.6 | O13—C23—C24 | 109.97 (18) |
O9—C10—H10B | 108.6 | O13—C23—H23B | 109.7 |
C9—C10—H10B | 108.6 | C24—C23—H23B | 109.7 |
H10A—C10—H10B | 107.6 | O13—C23—H23A | 109.7 |
O9—C11—C12 | 108.73 (18) | C24—C23—H23A | 109.7 |
O9—C11—H11B | 109.9 | H23B—C23—H23A | 108.2 |
C12—C11—H11B | 109.9 | N5—C24—C23 | 113.06 (18) |
O9—C11—H11A | 109.9 | N5—C24—H24A | 109.0 |
C12—C11—H11A | 109.9 | C23—C24—H24A | 109.0 |
H11B—C11—H11A | 108.3 | N5—C24—H24B | 109.0 |
N5—C12—C11 | 114.04 (18) | C23—C24—H24B | 109.0 |
N5—C12—H12A | 108.7 | H24A—C24—H24B | 107.8 |
C11—C12—H12A | 108.7 | | |
| | | |
O2—N1—C2—C3 | −167.0 (2) | N4—C7—C8—O8 | −80.5 (2) |
O3—N1—C2—C3 | 9.2 (3) | C8—O8—C9—C10 | 172.15 (17) |
O2—N1—C2—C1 | 11.6 (3) | C11—O9—C10—C9 | 75.6 (2) |
O3—N1—C2—C1 | −172.3 (2) | O8—C9—C10—O9 | 68.2 (2) |
O1—C1—C2—C3 | −172.6 (2) | C10—O9—C11—C12 | 168.19 (18) |
C6—C1—C2—C3 | 4.1 (3) | C18—N5—C12—C11 | 111.3 (2) |
O1—C1—C2—N1 | 9.0 (3) | C24—N5—C12—C11 | −123.8 (2) |
C6—C1—C2—N1 | −174.36 (18) | O9—C11—C12—N5 | 72.5 (2) |
N1—C2—C3—C4 | 178.16 (19) | C7—N4—C13—C14 | 147.63 (18) |
C1—C2—C3—C4 | −0.3 (3) | C19—N4—C13—C14 | −88.5 (2) |
C2—C3—C4—C5 | −2.2 (3) | C15—O10—C14—C13 | −174.05 (18) |
C2—C3—C4—N2 | 179.49 (19) | N4—C13—C14—O10 | −73.6 (2) |
O5—N2—C4—C3 | 178.48 (19) | C14—O10—C15—C16 | −157.66 (19) |
O4—N2—C4—C3 | −2.8 (3) | C17—O11—C16—C15 | 166.48 (18) |
O5—N2—C4—C5 | 0.2 (3) | O10—C15—C16—O11 | 70.5 (2) |
O4—N2—C4—C5 | 178.85 (19) | C16—O11—C17—C18 | 178.44 (18) |
C3—C4—C5—C6 | 0.4 (3) | C24—N5—C18—C17 | 167.72 (18) |
N2—C4—C5—C6 | 178.75 (19) | C12—N5—C18—C17 | −66.9 (2) |
C4—C5—C6—N3 | −175.83 (19) | O11—C17—C18—N5 | −67.0 (2) |
C4—C5—C6—C1 | 4.0 (3) | C7—N4—C19—C20 | −55.2 (2) |
O7—N3—C6—C5 | 145.6 (2) | C13—N4—C19—C20 | −177.36 (17) |
O6—N3—C6—C5 | −32.8 (3) | C21—O12—C20—C19 | −169.75 (19) |
O7—N3—C6—C1 | −34.2 (3) | N4—C19—C20—O12 | −44.2 (2) |
O6—N3—C6—C1 | 147.4 (2) | C20—O12—C21—C22 | −168.24 (19) |
O1—C1—C6—C5 | 170.7 (2) | C23—O13—C22—C21 | −170.12 (18) |
C2—C1—C6—C5 | −6.0 (3) | O12—C21—C22—O13 | −61.3 (2) |
O1—C1—C6—N3 | −9.4 (3) | C22—O13—C23—C24 | −171.69 (18) |
C2—C1—C6—N3 | 173.85 (19) | C18—N5—C24—C23 | −162.17 (18) |
C19—N4—C7—C8 | 163.72 (18) | C12—N5—C24—C23 | 72.8 (2) |
C13—N4—C7—C8 | −74.2 (2) | O13—C23—C24—N5 | 75.1 (2) |
C9—O8—C8—C7 | 172.63 (17) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4N···O14 | 0.97 (3) | 1.78 (3) | 2.725 (2) | 164 (2) |
O14—H14C···O13 | 0.85 (3) | 2.14 (3) | 2.953 (2) | 163 (3) |
O14—H14D···O11 | 0.86 (3) | 1.99 (3) | 2.827 (2) | 163 (3) |
C7—H7A···O4i | 0.97 | 2.48 | 3.295 (3) | 141 |
C7—H7A···O5i | 0.97 | 2.60 | 3.391 (3) | 139 |
C13—H13A···O1 | 0.97 | 2.33 | 3.206 (3) | 151 |
C19—H19A···O1 | 0.97 | 2.27 | 3.163 (3) | 152 |
C19—H19B···O11ii | 0.97 | 2.42 | 3.350 (3) | 160 |
C21—H21A···O4iii | 0.97 | 2.47 | 3.299 (3) | 143 |
C23—H23A···O9 | 0.97 | 2.48 | 3.254 (3) | 136 |
Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+1, −z+2. |