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The inclusion complex, C6H10N22+·2I-·C36H36N24O12.10H2O, displays a large ellipsoidal deformation of the cucurbit[6]uril skeleton upon complex formation. The cucurbit[6]uril molecule and the phenylenediammonium dication are each disposed about a center of inversion.
Supporting information
CCDC reference: 636820
Key indicators
- Single-crystal X-ray study
- T = 223 K
- Mean (C-C) = 0.004 Å
- R factor = 0.035
- wR factor = 0.085
- Data-to-parameter ratio = 14.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT731_ALERT_1_C Bond Calc 0.84(4), Rep 0.841(10) ...... 4.00 su-Ra
O1W -H11W 1.555 1.555
PLAT731_ALERT_1_C Bond Calc 0.83(3), Rep 0.829(10) ...... 3.00 su-Ra
O1W -H12W 1.555 1.555
PLAT731_ALERT_1_C Bond Calc 0.85(4), Rep 0.844(10) ...... 4.00 su-Ra
O2W -H21W 1.555 1.555
PLAT731_ALERT_1_C Bond Calc 0.84(4), Rep 0.844(10) ...... 4.00 su-Ra
O2W -H22W 1.555 1.555
PLAT731_ALERT_1_C Bond Calc 0.83(3), Rep 0.826(10) ...... 3.00 su-Ra
O3W -H32W 1.555 1.555
PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.849(10) ...... 3.00 su-Ra
O4W -H41W 1.555 1.555
PLAT731_ALERT_1_C Bond Calc 0.84(3), Rep 0.842(10) ...... 3.00 su-Ra
O4W -H42W 1.555 1.555
PLAT731_ALERT_1_C Bond Calc 0.83(4), Rep 0.832(10) ...... 4.00 su-Ra
O5W -H51W 1.555 1.555
PLAT731_ALERT_1_C Bond Calc 0.84(4), Rep 0.834(10) ...... 4.00 su-Ra
O5W -H52W 1.555 1.555
PLAT732_ALERT_1_C Angle Calc 102(5), Rep 102(2) ...... 2.50 su-Ra
H21W -O2W -H22W 1.555 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.84(4), Rep 0.841(10) ...... 4.00 su-Ra
O1W -H11W 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.83(3), Rep 0.829(10) ...... 3.00 su-Ra
O1W -H12W 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.83(3), Rep 0.829(10) ...... 3.00 su-Ra
O1W -H12W 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.85(4), Rep 0.844(10) ...... 4.00 su-Ra
O2W -H21W 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.84(4), Rep 0.844(10) ...... 4.00 su-Ra
O2W -H22W 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.83(3), Rep 0.826(10) ...... 3.00 su-Ra
O3W -H32W 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.849(10) ...... 3.00 su-Ra
O4W -H41W 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.84(3), Rep 0.842(10) ...... 3.00 su-Ra
O4W -H42W 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.83(4), Rep 0.832(10) ...... 4.00 su-Ra
O5W -H51W 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.84(4), Rep 0.834(10) ...... 4.00 su-Ra
O5W -H52W 1.555 1.555
PLAT736_ALERT_1_C H...A Calc 1.93(4), Rep 1.923(19) ...... 2.11 su-Ra
H22W -O33 1.555 1.655
PLAT736_ALERT_1_C H...A Calc 2.77(4), Rep 2.769(15) ...... 2.67 su-Ra
H51W -I1 1.555 1.555
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
25 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
25 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
0 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, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XSHELL (Bruker, 1999); software used to prepare material for publication: SHELXL97.
Cucurbit[6]uril
p-phenylenediammonium diiodide decahydrate
top
Crystal data top
C6H10N22+·2I−·C36H36N24O12·10H2O | F(000) = 1564 |
Mr = 1541.01 | Dx = 1.828 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 6948 reflections |
a = 11.854 (3) Å | θ = 2.1–28.3° |
b = 15.460 (4) Å | µ = 1.23 mm−1 |
c = 15.279 (4) Å | T = 223 K |
β = 90.447 (4)° | Prism, yellow |
V = 2800.1 (11) Å3 | 0.32 × 0.23 × 0.21 mm |
Z = 2 | |
Data collection top
Three-circle diffractometer | 6417 independent reflections |
Radiation source: fine-focus sealed tube | 5677 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
Detector resolution: 8.33 pixels mm-1 | θmax = 27.5°, θmin = 2.5° |
ω and φ scans | h = −15→15 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −20→19 |
Tmin = 0.720, Tmax = 0.773 | l = −19→19 |
31829 measured reflections | |
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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.085 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.02P)2 + 9.444P], P = (max(Fo2,0) + 2Fc2)/3 |
6417 reflections | (Δ/σ)max < 0.001 |
446 parameters | Δρmax = 0.83 e Å−3 |
18 restraints | Δρmin = −0.94 e Å−3 |
Special details top
Experimental. 3 omega runs of 606 frames at phi=60,180,300 and 1 phi run of 847 frames. Step
size =-0.3 deg; exposure 23 sec. |
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 | |
I1 | 0.228768 (18) | 0.501545 (13) | 0.000747 (13) | 0.03403 (7) | |
N1 | 0.7229 (2) | 0.54985 (17) | 0.45318 (17) | 0.0317 (5) | |
H1A | 0.7585 | 0.5723 | 0.5002 | 0.048* | |
H1B | 0.7193 | 0.5899 | 0.4105 | 0.048* | |
H1C | 0.7611 | 0.5034 | 0.4340 | 0.048* | |
C1 | 0.6081 (2) | 0.52380 (18) | 0.47751 (19) | 0.0260 (5) | |
C2 | 0.5707 (3) | 0.5390 (2) | 0.5604 (2) | 0.0385 (7) | |
H2 | 0.6186 | 0.5652 | 0.6020 | 0.046* | |
C3 | 0.4618 (3) | 0.5155 (3) | 0.5830 (2) | 0.0436 (8) | |
H3 | 0.4356 | 0.5265 | 0.6398 | 0.052* | |
N10 | 0.43844 (19) | 0.38962 (15) | 0.18776 (16) | 0.0269 (5) | |
C11 | 0.5250 (2) | 0.44380 (17) | 0.15035 (18) | 0.0240 (5) | |
H11 | 0.5408 | 0.4278 | 0.0889 | 0.029* | |
N12 | 0.62852 (18) | 0.45090 (14) | 0.20237 (15) | 0.0227 (4) | |
C13 | 0.3508 (2) | 0.43690 (18) | 0.22087 (17) | 0.0248 (5) | |
O13 | 0.26468 (16) | 0.40702 (13) | 0.25198 (14) | 0.0312 (4) | |
C14 | 0.6547 (2) | 0.53503 (18) | 0.22118 (17) | 0.0243 (5) | |
O14 | 0.74200 (16) | 0.56062 (14) | 0.25574 (14) | 0.0313 (4) | |
N15 | 0.37653 (18) | 0.52329 (15) | 0.21319 (15) | 0.0236 (4) | |
C16 | 0.4742 (2) | 0.53624 (17) | 0.15719 (18) | 0.0236 (5) | |
H16 | 0.4522 | 0.5594 | 0.0991 | 0.028* | |
N17 | 0.56535 (18) | 0.58571 (15) | 0.19654 (16) | 0.0257 (5) | |
C18 | 0.2893 (2) | 0.58831 (18) | 0.22567 (19) | 0.0266 (5) | |
H18A | 0.2829 | 0.6233 | 0.1724 | 0.032* | |
H18B | 0.2169 | 0.5591 | 0.2344 | 0.032* | |
C19 | 0.5619 (2) | 0.67727 (18) | 0.21462 (19) | 0.0273 (6) | |
H19A | 0.5261 | 0.7066 | 0.1648 | 0.033* | |
H19B | 0.6395 | 0.6987 | 0.2195 | 0.033* | |
N20 | 0.31094 (19) | 0.64486 (15) | 0.29920 (15) | 0.0254 (5) | |
C21 | 0.3830 (2) | 0.72033 (17) | 0.29345 (17) | 0.0232 (5) | |
H21 | 0.3613 | 0.7580 | 0.2437 | 0.028* | |
N22 | 0.50201 (18) | 0.70065 (15) | 0.29340 (16) | 0.0259 (5) | |
C23 | 0.2517 (2) | 0.64159 (18) | 0.37562 (18) | 0.0251 (5) | |
O23 | 0.18261 (17) | 0.58696 (14) | 0.39595 (14) | 0.0338 (5) | |
C24 | 0.5557 (2) | 0.72665 (16) | 0.36901 (19) | 0.0251 (5) | |
O24 | 0.65678 (16) | 0.72046 (13) | 0.38415 (14) | 0.0313 (4) | |
N25 | 0.28132 (19) | 0.71299 (15) | 0.42437 (15) | 0.0253 (5) | |
C26 | 0.3654 (2) | 0.76587 (17) | 0.38254 (17) | 0.0231 (5) | |
H26 | 0.3400 | 0.8259 | 0.3738 | 0.028* | |
N27 | 0.47668 (19) | 0.76124 (15) | 0.42382 (15) | 0.0257 (5) | |
C28 | 0.2190 (2) | 0.7404 (2) | 0.50036 (17) | 0.0270 (6) | |
H28A | 0.1471 | 0.7091 | 0.5015 | 0.032* | |
H28B | 0.2020 | 0.8021 | 0.4947 | 0.032* | |
C29 | 0.5059 (2) | 0.81238 (18) | 0.50042 (18) | 0.0267 (5) | |
H29A | 0.5877 | 0.8216 | 0.5012 | 0.032* | |
H29B | 0.4698 | 0.8692 | 0.4950 | 0.032* | |
N30 | 0.27749 (19) | 0.72627 (16) | 0.58276 (15) | 0.0266 (5) | |
C31 | 0.3614 (2) | 0.78389 (17) | 0.62051 (18) | 0.0250 (5) | |
H31 | 0.3360 | 0.8449 | 0.6200 | 0.030* | |
N32 | 0.47334 (19) | 0.77415 (16) | 0.58318 (16) | 0.0273 (5) | |
C33 | 0.2493 (2) | 0.66074 (18) | 0.63801 (17) | 0.0246 (5) | |
O33 | 0.18299 (16) | 0.60210 (14) | 0.62093 (13) | 0.0305 (4) | |
C34 | 0.5516 (2) | 0.75020 (17) | 0.64527 (19) | 0.0264 (5) | |
O34 | 0.65351 (16) | 0.74796 (14) | 0.63445 (15) | 0.0336 (5) | |
N35 | 0.30454 (19) | 0.67265 (15) | 0.71586 (15) | 0.0253 (5) | |
C36 | 0.3766 (2) | 0.74857 (17) | 0.71570 (18) | 0.0252 (5) | |
H36 | 0.3534 | 0.7915 | 0.7602 | 0.030* | |
N37 | 0.49631 (19) | 0.72989 (16) | 0.72072 (16) | 0.0270 (5) | |
C38 | 0.2883 (2) | 0.61760 (18) | 0.79139 (17) | 0.0251 (5) | |
H38A | 0.2128 | 0.5918 | 0.7882 | 0.030* | |
H38B | 0.2921 | 0.6530 | 0.8445 | 0.030* | |
C39 | 0.5539 (2) | 0.70307 (18) | 0.80061 (19) | 0.0284 (6) | |
H39A | 0.6303 | 0.7272 | 0.8006 | 0.034* | |
H39B | 0.5141 | 0.7277 | 0.8508 | 0.034* | |
O1W | 0.1706 (2) | 0.3561 (2) | 0.41969 (18) | 0.0523 (7) | |
H11W | 0.117 (3) | 0.387 (3) | 0.401 (3) | 0.078* | |
H12W | 0.215 (3) | 0.350 (3) | 0.3784 (19) | 0.078* | |
O2W | 0.9822 (3) | 0.6077 (2) | 0.7085 (3) | 0.0659 (8) | |
H21W | 0.974 (5) | 0.563 (2) | 0.740 (3) | 0.099* | |
H22W | 1.040 (3) | 0.595 (3) | 0.680 (3) | 0.099* | |
O3W | 0.9051 (3) | 0.7979 (2) | 0.5053 (2) | 0.0649 (8) | |
H31W | 0.889 (4) | 0.7463 (11) | 0.513 (4) | 0.097* | |
H32W | 0.845 (2) | 0.825 (3) | 0.510 (4) | 0.097* | |
O4W | 0.9412 (3) | 0.5969 (2) | 0.3665 (3) | 0.0714 (9) | |
H41W | 0.938 (3) | 0.577 (4) | 0.3149 (17) | 0.107* | |
H42W | 1.004 (2) | 0.578 (3) | 0.383 (3) | 0.107* | |
O5W | 0.0048 (3) | 0.5178 (3) | 0.1569 (2) | 0.0763 (10) | |
H51W | 0.062 (3) | 0.513 (4) | 0.126 (3) | 0.114* | |
H52W | −0.047 (3) | 0.501 (4) | 0.123 (3) | 0.114* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.03898 (12) | 0.03138 (11) | 0.03170 (11) | −0.00423 (8) | −0.00214 (8) | −0.00152 (8) |
N1 | 0.0281 (12) | 0.0362 (14) | 0.0310 (13) | −0.0045 (10) | 0.0022 (10) | −0.0022 (11) |
C1 | 0.0228 (12) | 0.0241 (13) | 0.0313 (14) | −0.0007 (10) | 0.0009 (10) | 0.0026 (11) |
C2 | 0.0353 (16) | 0.052 (2) | 0.0285 (15) | −0.0137 (14) | −0.0035 (12) | −0.0086 (14) |
C3 | 0.0395 (18) | 0.067 (2) | 0.0244 (14) | −0.0121 (16) | 0.0057 (13) | −0.0117 (15) |
N10 | 0.0233 (11) | 0.0217 (11) | 0.0357 (13) | 0.0000 (9) | −0.0039 (9) | 0.0018 (9) |
C11 | 0.0236 (12) | 0.0247 (13) | 0.0237 (12) | 0.0018 (10) | −0.0041 (10) | −0.0011 (10) |
N12 | 0.0203 (10) | 0.0227 (11) | 0.0252 (11) | 0.0028 (8) | −0.0018 (8) | −0.0009 (9) |
C13 | 0.0238 (12) | 0.0255 (13) | 0.0250 (13) | −0.0010 (10) | −0.0070 (10) | 0.0013 (10) |
O13 | 0.0242 (10) | 0.0303 (11) | 0.0391 (11) | −0.0048 (8) | −0.0024 (8) | 0.0043 (9) |
C14 | 0.0221 (12) | 0.0264 (13) | 0.0246 (13) | −0.0006 (10) | 0.0038 (10) | −0.0006 (10) |
O14 | 0.0223 (9) | 0.0318 (11) | 0.0398 (11) | −0.0024 (8) | −0.0034 (8) | −0.0033 (9) |
N15 | 0.0198 (10) | 0.0236 (11) | 0.0276 (11) | 0.0008 (8) | −0.0002 (8) | 0.0005 (9) |
C16 | 0.0221 (12) | 0.0236 (13) | 0.0250 (13) | 0.0011 (10) | −0.0013 (10) | 0.0021 (10) |
N17 | 0.0204 (10) | 0.0222 (11) | 0.0345 (12) | 0.0000 (8) | 0.0001 (9) | −0.0020 (9) |
C18 | 0.0214 (12) | 0.0270 (13) | 0.0314 (14) | 0.0017 (10) | −0.0045 (10) | −0.0037 (11) |
C19 | 0.0265 (13) | 0.0225 (13) | 0.0331 (14) | −0.0030 (10) | 0.0066 (11) | 0.0020 (11) |
N20 | 0.0252 (11) | 0.0240 (11) | 0.0268 (11) | −0.0034 (9) | 0.0016 (9) | −0.0029 (9) |
C21 | 0.0231 (12) | 0.0215 (12) | 0.0251 (13) | 0.0016 (10) | −0.0002 (10) | 0.0022 (10) |
N22 | 0.0203 (10) | 0.0264 (11) | 0.0309 (12) | 0.0009 (9) | 0.0020 (9) | −0.0016 (9) |
C23 | 0.0209 (12) | 0.0266 (13) | 0.0278 (13) | 0.0034 (10) | −0.0025 (10) | 0.0022 (11) |
O23 | 0.0280 (10) | 0.0343 (11) | 0.0390 (12) | −0.0075 (9) | 0.0048 (9) | 0.0006 (9) |
C24 | 0.0246 (13) | 0.0164 (11) | 0.0345 (14) | −0.0020 (9) | 0.0010 (10) | 0.0034 (10) |
O24 | 0.0206 (9) | 0.0299 (10) | 0.0435 (12) | −0.0017 (8) | −0.0013 (8) | −0.0002 (9) |
N25 | 0.0227 (11) | 0.0295 (12) | 0.0236 (11) | −0.0022 (9) | 0.0023 (8) | −0.0014 (9) |
C26 | 0.0225 (12) | 0.0203 (12) | 0.0264 (13) | 0.0024 (9) | −0.0016 (10) | 0.0017 (10) |
N27 | 0.0208 (10) | 0.0267 (12) | 0.0296 (12) | 0.0011 (9) | −0.0035 (9) | −0.0019 (9) |
C28 | 0.0221 (12) | 0.0354 (15) | 0.0234 (13) | 0.0043 (11) | −0.0019 (10) | 0.0007 (11) |
C29 | 0.0259 (13) | 0.0228 (13) | 0.0314 (14) | −0.0037 (10) | −0.0018 (11) | 0.0006 (11) |
N30 | 0.0241 (11) | 0.0321 (12) | 0.0235 (11) | −0.0016 (9) | −0.0036 (9) | 0.0031 (9) |
C31 | 0.0235 (12) | 0.0221 (12) | 0.0294 (13) | 0.0025 (10) | −0.0030 (10) | 0.0010 (10) |
N32 | 0.0208 (11) | 0.0311 (12) | 0.0298 (12) | −0.0006 (9) | −0.0028 (9) | 0.0047 (10) |
C33 | 0.0216 (12) | 0.0279 (13) | 0.0242 (13) | 0.0043 (10) | 0.0008 (10) | 0.0005 (10) |
O33 | 0.0256 (10) | 0.0347 (11) | 0.0312 (10) | −0.0058 (8) | −0.0014 (8) | −0.0009 (9) |
C34 | 0.0258 (13) | 0.0183 (12) | 0.0351 (15) | −0.0009 (10) | −0.0065 (11) | −0.0001 (11) |
O34 | 0.0214 (9) | 0.0331 (11) | 0.0463 (12) | −0.0022 (8) | −0.0050 (8) | 0.0062 (9) |
N35 | 0.0271 (11) | 0.0256 (11) | 0.0231 (11) | −0.0011 (9) | −0.0032 (9) | 0.0021 (9) |
C36 | 0.0256 (13) | 0.0216 (12) | 0.0283 (13) | 0.0040 (10) | −0.0033 (10) | −0.0011 (10) |
N37 | 0.0233 (11) | 0.0292 (12) | 0.0285 (12) | 0.0021 (9) | −0.0062 (9) | 0.0029 (10) |
C38 | 0.0236 (12) | 0.0273 (13) | 0.0245 (13) | 0.0058 (10) | 0.0021 (10) | 0.0022 (10) |
C39 | 0.0318 (14) | 0.0215 (13) | 0.0318 (14) | −0.0015 (11) | −0.0114 (11) | −0.0027 (11) |
O1W | 0.0501 (15) | 0.0591 (17) | 0.0479 (15) | −0.0156 (13) | 0.0070 (12) | −0.0083 (13) |
O2W | 0.0457 (16) | 0.063 (2) | 0.089 (2) | 0.0026 (14) | 0.0166 (15) | 0.0045 (17) |
O3W | 0.069 (2) | 0.0525 (17) | 0.074 (2) | −0.0078 (15) | 0.0012 (17) | 0.0040 (16) |
O4W | 0.0493 (17) | 0.074 (2) | 0.091 (2) | −0.0027 (16) | −0.0110 (16) | 0.0022 (19) |
O5W | 0.0505 (18) | 0.114 (3) | 0.064 (2) | −0.001 (2) | −0.0051 (15) | 0.018 (2) |
Geometric parameters (Å, º) top
N1—C1 | 1.470 (3) | N25—C26 | 1.442 (3) |
N1—H1A | 0.9000 | N25—C28 | 1.444 (3) |
N1—H1B | 0.9000 | C26—N27 | 1.460 (3) |
N1—H1C | 0.9000 | C26—H26 | 0.9848 |
C1—C2 | 1.365 (4) | N27—C29 | 1.452 (4) |
C1—C3i | 1.378 (4) | C28—N30 | 1.449 (3) |
C2—C3 | 1.387 (5) | C28—H28A | 0.9800 |
C2—H2 | 0.9400 | C28—H28B | 0.9800 |
C3—C1i | 1.378 (4) | C29—N32 | 1.451 (4) |
C3—H3 | 0.9400 | C29—H29A | 0.9800 |
N10—C13 | 1.370 (4) | C29—H29B | 0.9800 |
N10—C11 | 1.446 (3) | N30—C33 | 1.362 (4) |
N10—C39i | 1.447 (3) | N30—C31 | 1.451 (3) |
C11—N12 | 1.461 (3) | C31—N32 | 1.456 (3) |
C11—C16 | 1.555 (4) | C31—C36 | 1.563 (4) |
C11—H11 | 0.9900 | C31—H31 | 0.9900 |
N12—C14 | 1.367 (4) | N32—C34 | 1.372 (3) |
N12—C38i | 1.450 (3) | C33—O33 | 1.227 (3) |
C13—O13 | 1.220 (3) | C33—N35 | 1.366 (3) |
C13—N15 | 1.375 (3) | C34—O34 | 1.221 (3) |
C14—O14 | 1.224 (3) | C34—N37 | 1.367 (4) |
C14—N17 | 1.368 (3) | N35—C38 | 1.448 (3) |
N15—C18 | 1.455 (3) | N35—C36 | 1.452 (3) |
N15—C16 | 1.459 (3) | C36—N37 | 1.450 (3) |
C16—N17 | 1.451 (3) | C36—H36 | 0.9900 |
C16—H16 | 0.9900 | N37—C39 | 1.454 (3) |
N17—C19 | 1.443 (3) | C38—N12i | 1.450 (3) |
C18—N20 | 1.445 (3) | C38—H38A | 0.9800 |
C18—H18A | 0.9800 | C38—H38B | 0.9800 |
C18—H18B | 0.9800 | C39—N10i | 1.447 (3) |
C19—N22 | 1.448 (4) | C39—H39A | 0.9800 |
C19—H19A | 0.9800 | C39—H39B | 0.9800 |
C19—H19B | 0.9800 | O1W—H11W | 0.841 (10) |
N20—C23 | 1.368 (4) | O1W—H12W | 0.829 (10) |
N20—C21 | 1.449 (3) | O2W—H21W | 0.844 (10) |
C21—N22 | 1.444 (3) | O2W—H22W | 0.844 (10) |
C21—C26 | 1.548 (4) | O3W—H31W | 0.830 (10) |
C21—H21 | 0.9900 | O3W—H32W | 0.826 (10) |
N22—C24 | 1.375 (4) | O4W—H41W | 0.849 (10) |
C23—O23 | 1.218 (3) | O4W—H42W | 0.842 (10) |
C23—N25 | 1.376 (4) | O5W—H51W | 0.832 (10) |
C24—O24 | 1.223 (3) | O5W—H52W | 0.834 (10) |
C24—N27 | 1.370 (4) | | |
| | | |
C1—N1—H1A | 109.5 | O24—C24—N22 | 125.6 (3) |
C1—N1—H1B | 109.5 | N27—C24—N22 | 108.3 (2) |
H1A—N1—H1B | 109.5 | C23—N25—C26 | 112.9 (2) |
C1—N1—H1C | 109.5 | C23—N25—C28 | 122.7 (2) |
H1A—N1—H1C | 109.5 | C26—N25—C28 | 123.3 (2) |
H1B—N1—H1C | 109.5 | N25—C26—N27 | 114.0 (2) |
C2—C1—C3i | 120.0 (3) | N25—C26—C21 | 103.3 (2) |
C2—C1—N1 | 119.7 (3) | N27—C26—C21 | 103.3 (2) |
C3i—C1—N1 | 120.3 (3) | N25—C26—H26 | 112.5 |
C1—C2—C3 | 119.7 (3) | N27—C26—H26 | 112.3 |
C1—C2—H2 | 120.2 | C21—C26—H26 | 110.6 |
C3—C2—H2 | 120.2 | C24—N27—C29 | 123.0 (2) |
C1i—C3—C2 | 120.3 (3) | C24—N27—C26 | 112.0 (2) |
C1i—C3—H3 | 119.8 | C29—N27—C26 | 122.1 (2) |
C2—C3—H3 | 119.8 | N25—C28—N30 | 114.2 (2) |
C13—N10—C11 | 112.3 (2) | N25—C28—H28A | 108.7 |
C13—N10—C39i | 122.0 (2) | N30—C28—H28A | 108.7 |
C11—N10—C39i | 125.3 (2) | N25—C28—H28B | 108.7 |
N10—C11—N12 | 115.1 (2) | N30—C28—H28B | 108.7 |
N10—C11—C16 | 103.3 (2) | H28A—C28—H28B | 107.6 |
N12—C11—C16 | 102.6 (2) | N32—C29—N27 | 114.6 (2) |
N10—C11—H11 | 111.7 | N32—C29—H29A | 108.6 |
N12—C11—H11 | 111.7 | N27—C29—H29A | 108.6 |
C16—C11—H11 | 111.7 | N32—C29—H29B | 108.6 |
C14—N12—C38i | 121.9 (2) | N27—C29—H29B | 108.6 |
C14—N12—C11 | 112.0 (2) | H29A—C29—H29B | 107.6 |
C38i—N12—C11 | 123.3 (2) | C33—N30—C28 | 122.2 (2) |
O13—C13—N10 | 125.5 (3) | C33—N30—C31 | 112.4 (2) |
O13—C13—N15 | 126.0 (3) | C28—N30—C31 | 125.1 (2) |
N10—C13—N15 | 108.5 (2) | N30—C31—N32 | 113.9 (2) |
O14—C14—N12 | 126.0 (3) | N30—C31—C36 | 103.2 (2) |
O14—C14—N17 | 125.7 (3) | N32—C31—C36 | 103.3 (2) |
N12—C14—N17 | 108.2 (2) | N30—C31—H31 | 111.9 |
C13—N15—C18 | 120.1 (2) | N32—C31—H31 | 111.9 |
C13—N15—C16 | 111.2 (2) | C36—C31—H31 | 111.9 |
C18—N15—C16 | 123.3 (2) | C34—N32—C29 | 121.9 (2) |
N17—C16—N15 | 114.9 (2) | C34—N32—C31 | 111.7 (2) |
N17—C16—C11 | 103.0 (2) | C29—N32—C31 | 123.3 (2) |
N15—C16—C11 | 102.9 (2) | O33—C33—N30 | 125.3 (3) |
N17—C16—H16 | 111.8 | O33—C33—N35 | 125.9 (3) |
N15—C16—H16 | 111.8 | N30—C33—N35 | 108.8 (2) |
C11—C16—H16 | 111.8 | O34—C34—N37 | 126.1 (3) |
C14—N17—C19 | 122.2 (2) | O34—C34—N32 | 125.3 (3) |
C14—N17—C16 | 112.6 (2) | N37—C34—N32 | 108.6 (2) |
C19—N17—C16 | 125.1 (2) | C33—N35—C38 | 123.3 (2) |
N20—C18—N15 | 113.5 (2) | C33—N35—C36 | 112.7 (2) |
N20—C18—H18A | 108.9 | C38—N35—C36 | 124.0 (2) |
N15—C18—H18A | 108.9 | N37—C36—N35 | 114.5 (2) |
N20—C18—H18B | 108.9 | N37—C36—C31 | 103.0 (2) |
N15—C18—H18B | 108.9 | N35—C36—C31 | 102.7 (2) |
H18A—C18—H18B | 107.7 | N37—C36—H36 | 112.0 |
N17—C19—N22 | 114.8 (2) | N35—C36—H36 | 112.0 |
N17—C19—H19A | 108.6 | C31—C36—H36 | 112.0 |
N22—C19—H19A | 108.6 | C34—N37—C36 | 112.7 (2) |
N17—C19—H19B | 108.6 | C34—N37—C39 | 123.3 (2) |
N22—C19—H19B | 108.6 | C36—N37—C39 | 123.6 (2) |
H19A—C19—H19B | 107.6 | N35—C38—N12i | 112.8 (2) |
C23—N20—C18 | 123.5 (2) | N35—C38—H38A | 109.0 |
C23—N20—C21 | 112.8 (2) | N12i—C38—H38A | 109.0 |
C18—N20—C21 | 122.8 (2) | N35—C38—H38B | 109.0 |
N22—C21—N20 | 114.0 (2) | N12i—C38—H38B | 109.0 |
N22—C21—C26 | 103.6 (2) | H38A—C38—H38B | 107.8 |
N20—C21—C26 | 103.3 (2) | N10i—C39—N37 | 114.5 (2) |
N22—C21—H21 | 111.8 | N10i—C39—H39A | 108.6 |
N20—C21—H21 | 111.8 | N37—C39—H39A | 108.6 |
C26—C21—H21 | 111.8 | N10i—C39—H39B | 108.6 |
C24—N22—C21 | 112.6 (2) | N37—C39—H39B | 108.6 |
C24—N22—C19 | 123.0 (2) | H39A—C39—H39B | 107.6 |
C21—N22—C19 | 122.6 (2) | H11W—O1W—H12W | 106 (2) |
O23—C23—N20 | 126.4 (3) | H21W—O2W—H22W | 102 (2) |
O23—C23—N25 | 126.0 (3) | H31W—O3W—H32W | 105 (2) |
N20—C23—N25 | 107.6 (2) | H41W—O4W—H42W | 101 (2) |
O24—C24—N27 | 126.1 (3) | H51W—O5W—H52W | 103 (2) |
| | | |
C3i—C1—C2—C3 | −0.7 (6) | N20—C23—N25—C28 | 166.9 (2) |
N1—C1—C2—C3 | 179.1 (3) | C23—N25—C26—N27 | −108.2 (3) |
C1—C2—C3—C1i | 0.7 (6) | C28—N25—C26—N27 | 83.2 (3) |
C13—N10—C11—N12 | 106.3 (3) | C23—N25—C26—C21 | 3.2 (3) |
C39i—N10—C11—N12 | −66.9 (3) | C28—N25—C26—C21 | −165.4 (2) |
C13—N10—C11—C16 | −4.8 (3) | N22—C21—C26—N25 | −122.3 (2) |
C39i—N10—C11—C16 | −177.9 (2) | N20—C21—C26—N25 | −3.2 (3) |
N10—C11—N12—C14 | −124.0 (2) | N22—C21—C26—N27 | −3.3 (3) |
C16—C11—N12—C14 | −12.6 (3) | N20—C21—C26—N27 | 115.8 (2) |
N10—C11—N12—C38i | 74.9 (3) | O24—C24—N27—C29 | 13.7 (4) |
C16—C11—N12—C38i | −173.7 (2) | N22—C24—N27—C29 | −165.8 (2) |
C11—N10—C13—O13 | 176.1 (3) | O24—C24—N27—C26 | 174.8 (3) |
C39i—N10—C13—O13 | −10.4 (4) | N22—C24—N27—C26 | −4.7 (3) |
C11—N10—C13—N15 | −4.0 (3) | N25—C26—N27—C24 | 116.3 (3) |
C39i—N10—C13—N15 | 169.4 (2) | C21—C26—N27—C24 | 5.0 (3) |
C38i—N12—C14—O14 | −10.6 (4) | N25—C26—N27—C29 | −82.4 (3) |
C11—N12—C14—O14 | −172.0 (3) | C21—C26—N27—C29 | 166.3 (2) |
C38i—N12—C14—N17 | 170.7 (2) | C23—N25—C28—N30 | 108.7 (3) |
C11—N12—C14—N17 | 9.3 (3) | C26—N25—C28—N30 | −83.8 (3) |
O13—C13—N15—C18 | −13.3 (4) | C24—N27—C29—N32 | −116.0 (3) |
N10—C13—N15—C18 | 166.8 (2) | C26—N27—C29—N32 | 84.7 (3) |
O13—C13—N15—C16 | −168.2 (3) | N25—C28—N30—C33 | −104.3 (3) |
N10—C13—N15—C16 | 12.0 (3) | N25—C28—N30—C31 | 83.1 (3) |
C13—N15—C16—N17 | −125.4 (2) | C33—N30—C31—N32 | 106.5 (3) |
C18—N15—C16—N17 | 80.7 (3) | C28—N30—C31—N32 | −80.3 (3) |
C13—N15—C16—C11 | −14.3 (3) | C33—N30—C31—C36 | −4.7 (3) |
C18—N15—C16—C11 | −168.2 (2) | C28—N30—C31—C36 | 168.5 (2) |
N10—C11—C16—N17 | 130.7 (2) | N27—C29—N32—C34 | 116.6 (3) |
N12—C11—C16—N17 | 10.8 (3) | N27—C29—N32—C31 | −84.8 (3) |
N10—C11—C16—N15 | 11.0 (2) | N30—C31—N32—C34 | −119.4 (3) |
N12—C11—C16—N15 | −109.0 (2) | C36—C31—N32—C34 | −8.2 (3) |
O14—C14—N17—C19 | −4.2 (4) | N30—C31—N32—C29 | 80.1 (3) |
N12—C14—N17—C19 | 174.4 (2) | C36—C31—N32—C29 | −168.7 (2) |
O14—C14—N17—C16 | 180.0 (3) | C28—N30—C33—O33 | 8.7 (4) |
N12—C14—N17—C16 | −1.4 (3) | C31—N30—C33—O33 | −177.8 (3) |
N15—C16—N17—C14 | 104.8 (3) | C28—N30—C33—N35 | −169.5 (2) |
C11—C16—N17—C14 | −6.2 (3) | C31—N30—C33—N35 | 3.9 (3) |
N15—C16—N17—C19 | −70.8 (3) | C29—N32—C34—O34 | −9.6 (4) |
C11—C16—N17—C19 | 178.1 (2) | C31—N32—C34—O34 | −170.4 (3) |
C13—N15—C18—N20 | 117.0 (3) | C29—N32—C34—N37 | 170.2 (2) |
C16—N15—C18—N20 | −91.3 (3) | C31—N32—C34—N37 | 9.3 (3) |
C14—N17—C19—N22 | −95.6 (3) | O33—C33—N35—C38 | −2.3 (4) |
C16—N17—C19—N22 | 79.7 (3) | N30—C33—N35—C38 | 176.0 (2) |
N15—C18—N20—C23 | −108.0 (3) | O33—C33—N35—C36 | −179.5 (3) |
N15—C18—N20—C21 | 83.6 (3) | N30—C33—N35—C36 | −1.2 (3) |
C23—N20—C21—N22 | 114.0 (3) | C33—N35—C36—N37 | −112.5 (3) |
C18—N20—C21—N22 | −76.4 (3) | C38—N35—C36—N37 | 70.3 (3) |
C23—N20—C21—C26 | 2.4 (3) | C33—N35—C36—C31 | −1.7 (3) |
C18—N20—C21—C26 | 172.0 (2) | C38—N35—C36—C31 | −178.9 (2) |
N20—C21—N22—C24 | −110.6 (3) | N30—C31—C36—N37 | 122.9 (2) |
C26—C21—N22—C24 | 0.8 (3) | N32—C31—C36—N37 | 4.0 (3) |
N20—C21—N22—C19 | 84.3 (3) | N30—C31—C36—N35 | 3.6 (3) |
C26—C21—N22—C19 | −164.3 (2) | N32—C31—C36—N35 | −115.2 (2) |
N17—C19—N22—C24 | 105.7 (3) | O34—C34—N37—C36 | 173.3 (3) |
N17—C19—N22—C21 | −90.8 (3) | N32—C34—N37—C36 | −6.4 (3) |
C18—N20—C23—O23 | 7.9 (4) | O34—C34—N37—C39 | 0.7 (4) |
C21—N20—C23—O23 | 177.4 (3) | N32—C34—N37—C39 | −179.0 (2) |
C18—N20—C23—N25 | −170.0 (2) | N35—C36—N37—C34 | 111.9 (3) |
C21—N20—C23—N25 | −0.5 (3) | C31—C36—N37—C34 | 1.2 (3) |
C21—N22—C24—O24 | −177.2 (3) | N35—C36—N37—C39 | −75.5 (3) |
C19—N22—C24—O24 | −12.2 (4) | C31—C36—N37—C39 | 173.8 (2) |
C21—N22—C24—N27 | 2.3 (3) | C33—N35—C38—N12i | 95.0 (3) |
C19—N22—C24—N27 | 167.3 (2) | C36—N35—C38—N12i | −88.1 (3) |
O23—C23—N25—C26 | −179.8 (3) | C34—N37—C39—N10i | −95.6 (3) |
N20—C23—N25—C26 | −1.8 (3) | C36—N37—C39—N10i | 92.6 (3) |
O23—C23—N25—C28 | −11.1 (4) | | |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1Wi | 0.90 | 1.85 | 2.728 (4) | 165 |
N1—H1B···O24 | 0.90 | 2.19 | 2.945 (3) | 141 |
N1—H1C···O33i | 0.90 | 1.95 | 2.840 (3) | 169 |
O1W—H11W···O2Wi | 0.84 (1) | 2.04 (3) | 2.716 (5) | 137 (4) |
O1W—H12W···O34i | 0.83 (1) | 2.19 (3) | 2.765 (4) | 127 (3) |
O1W—H12W···O13 | 0.83 (1) | 2.21 (3) | 2.911 (3) | 143 (4) |
O2W—H21W···O5Wi | 0.84 (1) | 2.03 (3) | 2.831 (5) | 158 (6) |
O2W—H22W···O33ii | 0.84 (1) | 1.92 (2) | 2.741 (4) | 163 (5) |
O3W—H31W···O1Wi | 0.83 (1) | 2.02 (3) | 2.793 (4) | 156 (6) |
O3W—H32W···I1iii | 0.83 (1) | 3.03 (3) | 3.740 (4) | 146 (4) |
O4W—H41W···O14 | 0.85 (1) | 2.49 (4) | 2.948 (4) | 114 (3) |
O4W—H42W···O23ii | 0.84 (1) | 2.13 (3) | 2.898 (4) | 152 (5) |
O5W—H51W···I1 | 0.83 (1) | 2.77 (2) | 3.592 (4) | 171 (5) |
O5W—H52W···I1iv | 0.83 (1) | 2.86 (2) | 3.668 (3) | 163 (6) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z; (iii) x+1/2, −y+3/2, z+1/2; (iv) −x, −y+1, −z. |
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