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The adduct (1) formed between the hexaaza macrocycle 3,6,9,16,19,22-hexaazatricyclo[22.2.2.211,14]triconta-1(26),11(29),12,14(30),24,27-hexaene, C24H38N6, and 4,4′-sulfonyldiphenol, O2S(C6H4OH)2, is a salt [(C24H40N6)2+]·2[(HOC6H4SO2­C6H4O)], and the adduct (2) formed by the same macrocyclic amine with 4,4′-biphenol is an aquated salt which also contains neutral biphenol molecules, [(C24H40N6)2+]·2[(HOC6H4C6H4O)]·(HOC6H4C6H4OH).2H2O. In both compounds the cations lie across centres of inversion: there are two crystallographically distinct cation sites in (1) and the conformations of the cations occupying them are quite different. In (2) the single type of cation site is occupied by a conformationally disordered cation: the major and minor components represent two further distinct conformers. In (1) the anions are linked by O—H...O hydrogen bonds into chains, and each cation is linked by a total of six N—H...O hydrogen bonds to anions in four different chains, so linking the chains into continuous sheets. In (2) the anions and the water molecules are linked into sheets, which are further linked into a continuous three-dimensional framework by both the cations and the neutral biphenol units.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768199014032/na0100sup1.cif
Contains datablocks global, 9891k, 9911

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768199014032/na01001sup2.fcf
Contains datablock 1

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768199014032/na01002sup3.fcf
Contains datablock 2

CCDC references: 144372; 144373

Computing details top

For both compounds, data collection: Kappa-CCD server software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: NRCVAX96 and SHELXL97 (Sheldrick, 1997b); molecular graphics: NRCVAX96, ORTEP (Johnson, 1976), PLATON (Spek, 1999); software used to prepare material for publication: NRCVAX96, SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

(9891k) 3,6,9,16,19,22-Hexa-azatricyclo[22.2.2.211,14]triconta-1(26),11 (29), 12,14 (30),24,27-hexaene – 4,4'-Sulfonyldiphenol (1/2) top
Crystal data top
C24H40N6·2(C12H9O4S)F(000) = 1936
Mr = 911.12Dx = 1.309 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 18.0527 (5) ÅCell parameters from 9421 reflections
b = 13.1074 (2) Åθ = 4.1–26.3°
c = 20.5723 (5) ŵ = 0.18 mm1
β = 108.2524 (11)°T = 100 K
V = 4622.97 (18) Å3Block, colourless
Z = 40.35 × 0.34 × 0.31 mm
Data collection top
Kappa-CCD
diffractometer
9421 independent reflections
Radiation source: fine-focus sealed X-ray tube6549 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.059
φ scans and ω scans with κ offsetsθmax = 26.3°, θmin = 4.1°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 022
Tmin = 0.957, Tmax = 0.966k = 016
40273 measured reflectionsl = 2524
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0642P)2 + 1.8417P]
where P = (Fo2 + 2Fc2)/3
9421 reflections(Δ/σ)max = 0.016
626 parametersΔρmax = 0.40 e Å3
40 restraintsΔρmin = 0.56 e Å3
Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Geometry. Mean-plane data from the final SHELXL97 refinement run:- Least-squares planes(x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

4.1891(0.0200) x - 9.1458(0.0125) y + 11.7454(0.0250) z = 1.2187(0.0151)

* 0.0000(0.0000) S1 * 0.0000(0.0000) C11 * 0.0000(0.0000) C21

Rms deviation of fitted atoms = 0.0000

16.0347(0.0073) x - 4.2793(0.0107) y - 12.0383(0.0147) z = 7.5514(0.0081)

Angle to previous plane(with approximate e.s.d.) = 77.6 (1)

* -0.0110(0.0015) C11 * 0.0056(0.0015) C12 * 0.0073(0.0015) C13 * -0.0149(0.0015) C14 * 0.0097(0.0015) C15 * 0.0033(0.0015) C16 - 0.0447(0.0029) S1 - 0.0422(0.0030) O14

Rms deviation of fitted atoms = 0.0094

4.1891(0.0200) x - 9.1458(0.0125) y + 11.7454(0.0250) z = 1.2187(0.0151)

Angle to previous plane(with approximate e.s.d.) = 77.6 (1)

* 0.0000(0.0000) S1 * 0.0000(0.0000) C11 * 0.0000(0.0000) C21

Rms deviation of fitted atoms = 0.0000

5.3838(0.0152) x + 5.7878(0.0113) y + 14.6111(0.0131) z = 10.1268(0.0120)

Angle to previous plane(with approximate e.s.d.) = 70.5 (1)

* -0.0027(0.0015) C21 * -0.0024(0.0015) C22 * 0.0071(0.0016) C23 * -0.0067(0.0016) C24 * 0.0018(0.0017) C25 * 0.0028(0.0016) C26 - 0.0890(0.0029) S1 - 0.0713(0.0031) O24

Rms deviation of fitted atoms = 0.0045

4.1891(0.0200) x - 9.1458(0.0125) y + 11.7454(0.0250) z = 1.2187(0.0151)

Angle to previous plane(with approximate e.s.d.) = 70.5 (1)

* 0.0000(0.0000) S1 * 0.0000(0.0000) C11 * 0.0000(0.0000) C21

Rms deviation of fitted atoms = 0.0000

15.7188(0.0137) x + 5.9495(0.0144) y - 1.9126(0.0299) z = 14.4307(0.0023)

Angle to previous plane(with approximate e.s.d.) = 89.2 (1)

* 0.0000(0.0000) S1 * 0.0000(0.0000) O11 * 0.0000(0.0000) O12

Rms deviation of fitted atoms = 0.0000

4.4528(0.0219) x + 7.9551(0.0151) y + 13.1715(0.0255) z = 3.6478(0.0038)

Angle to previous plane(with approximate e.s.d.) = 50.7 (1)

* 0.0000(0.0000) S2 * 0.0000(0.0000) C31 * 0.0000(0.0000) C41

Rms deviation of fitted atoms = 0.0000

15.6735(0.0081) x + 5.3770(0.0107) y - 11.0482(0.0159) z = 2.0879(0.0031)

Angle to previous plane(with approximate e.s.d.) = 75.4 (1)

* -0.0124(0.0016) C31 * 0.0054(0.0016) C32 * 0.0079(0.0016) C33 * -0.0141(0.0016) C34 * 0.0070(0.0015) C35 * 0.0062(0.0015) C36 - 0.0951(0.0030) S2 - 0.0651(0.0032) O34

Rms deviation of fitted atoms = 0.0094

4.4528(0.0219) x + 7.9551(0.0151) y + 13.1715(0.0255) z = 3.6478(0.0038)

Angle to previous plane(with approximate e.s.d.) = 75.4 (1)

* 0.0000(0.0000) S2 * 0.0000(0.0000) C31 * 0.0000(0.0000) C41

Rms deviation of fitted atoms = 0.0000

4.4832(0.0159) x - 7.2906(0.0101) y + 13.8941(0.0140) z = 3.5506(0.0054)

Angle to previous plane(with approximate e.s.d.) = 71.2 (1)

* 0.0052(0.0016) C41 * 0.0018(0.0016) C42 * -0.0069(0.0016) C43 * 0.0049(0.0015) C44 * 0.0021(0.0016) C45 * -0.0072(0.0016) C46 0.0350(0.0031) S2 - 0.0166(0.0030) O44

Rms deviation of fitted atoms = 0.0051

4.4528(0.0219) x + 7.9551(0.0151) y + 13.1715(0.0255) z = 3.6478(0.0038)

Angle to previous plane(with approximate e.s.d.) = 71.2 (1)

* 0.0000(0.0000) S2 * 0.0000(0.0000) C31 * 0.0000(0.0000) C41

Rms deviation of fitted atoms = 0.0000

15.7817(0.0144) x - 6.2114(0.0170) y - 3.5645(0.0290) z = 3.2409(0.0037)

Angle to previous plane(with approximate e.s.d.) = 89.5 (1)

* 0.0000(0.0000) S2 * 0.0000(0.0000) O21 * 0.0000(0.0000) O22

Rms deviation of fitted atoms = 0.0000

6.0417(0.0198) x + 7.0687(0.0115) y + 12.9412(0.0179) z = 1.0607(0.0037)

Angle to previous plane(with approximate e.s.d.) = 83.2 (1)

* 0.0020(0.0017) C51 * -0.0066(0.0018) C52 * 0.0027(0.0018) C53 * 0.0057(0.0017) C54 * -0.0104(0.0018) C55 * 0.0065(0.0018) C56 0.1026(0.0040) C57 0.0055(0.0042) C512_$1 [$1 is at -x, -y, -z]

Rms deviation of fitted atoms = 0.0063

3.7650(0.2664) x + 8.8609(0.0647) y + 12.4642(0.2241) z = 1.4867(0.0516)

Angle to previous plane(with approximate e.s.d.) = 11 (1)

* 0.0000(0.0002) C71 [Atoms C71—C77, C712_$1 were constrained to be 'flat'] * 0.0000(0.0001) C72 * 0.0000(0.0003) C73 * 0.0000(0.0004) C74 * 0.0000(0.0004) C75 * 0.0000(0.0004) C76 0.0000(0.0009) C77 0.0000(0.0008) C712_$1 [$1 is at -x, -y, -z]

Rms deviation of fitted atoms = 0.0000

- 4.1804(0.0171) x + 9.0707(0.0088) y - 11.8660(0.0166) z = 3.8371(0.0127)

Angle to previous plane(with approximate e.s.d.) = 86.4 (5)

* -0.0148(0.0017) C61 * -0.0008(0.0018) C62 * 0.0147(0.0018) C63 * -0.0128(0.0016) C64 * -0.0029(0.0016) C65 * 0.0167(0.0016) C66 - 0.0108(0.0036) C67 - 0.1343(0.0040) C612_$2 [$2 is at 1 - x, 1 - y, -z]

Rms deviation of fitted atoms = 0.0122

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.75903 (3)0.48883 (4)0.21368 (3)0.02350 (14)
O110.78096 (9)0.45337 (11)0.28355 (8)0.0277 (4)
O120.72018 (9)0.58632 (11)0.19760 (8)0.0296 (4)
O140.54836 (9)0.18282 (11)0.04164 (8)0.0273 (4)
O241.02947 (9)0.49234 (11)0.11385 (9)0.0330 (4)
C110.69785 (12)0.39527 (15)0.16265 (11)0.0229 (5)
C120.69281 (13)0.29866 (16)0.18889 (11)0.0244 (5)
C130.64358 (13)0.22581 (16)0.14907 (11)0.0252 (5)
C140.59840 (12)0.25016 (16)0.08208 (11)0.0231 (5)
C150.60543 (13)0.34645 (16)0.05519 (11)0.0253 (5)
C160.65429 (13)0.41866 (16)0.09512 (11)0.0244 (5)
C210.84200 (12)0.49302 (15)0.18736 (11)0.0225 (5)
C220.89350 (13)0.41076 (15)0.20098 (11)0.0241 (5)
C230.95697 (13)0.41220 (16)0.17768 (11)0.0262 (5)
C240.97091 (13)0.49436 (16)0.13905 (12)0.0269 (5)
C250.91813 (14)0.57735 (17)0.12621 (13)0.0310 (5)
C260.85486 (14)0.57631 (16)0.15000 (12)0.0298 (5)
S20.25208 (3)0.01329 (4)0.18370 (3)0.03033 (16)
O210.20992 (10)0.07990 (12)0.15944 (10)0.0423 (5)
O220.27674 (10)0.03464 (12)0.25570 (9)0.0361 (4)
O340.04209 (9)0.34211 (12)0.04311 (8)0.0329 (4)
O440.52878 (9)0.01555 (11)0.09189 (8)0.0286 (4)
C310.19312 (12)0.11512 (16)0.14213 (12)0.0263 (5)
C320.14907 (14)0.10532 (17)0.07326 (13)0.0315 (5)
C330.09977 (14)0.18277 (18)0.04079 (12)0.0314 (5)
C340.09371 (13)0.27026 (17)0.07676 (12)0.0262 (5)
C350.13909 (13)0.28190 (16)0.14490 (11)0.0265 (5)
C360.18863 (13)0.20409 (16)0.17738 (12)0.0260 (5)
C410.33383 (13)0.01407 (16)0.15559 (12)0.0271 (5)
C420.34412 (13)0.06182 (16)0.11220 (12)0.0282 (5)
C430.40931 (13)0.06129 (16)0.09082 (12)0.0277 (5)
C440.46686 (13)0.01470 (15)0.11297 (11)0.0243 (5)
C450.45501 (13)0.09150 (17)0.15689 (12)0.0278 (5)
C460.38945 (13)0.09123 (17)0.17724 (12)0.0298 (5)
N510.05031 (12)0.18651 (17)0.13235 (10)0.0278 (5)0.920 (3)
N520.10277 (14)0.36563 (19)0.06923 (12)0.0245 (6)0.920 (3)
N530.14937 (13)0.27976 (16)0.03495 (12)0.0295 (6)0.920 (3)
C510.14282 (15)0.11121 (18)0.08805 (13)0.0258 (6)0.920 (3)
C520.07745 (16)0.08864 (19)0.06919 (13)0.0302 (6)0.920 (3)
C530.03198 (15)0.00389 (18)0.09498 (13)0.0292 (6)0.920 (3)
C540.05066 (15)0.06228 (17)0.14007 (13)0.0265 (6)0.920 (3)
C550.11731 (15)0.04066 (19)0.15813 (14)0.0299 (6)0.920 (3)
C560.16200 (16)0.0453 (2)0.13334 (15)0.0294 (6)0.920 (3)
C570.00087 (15)0.15156 (18)0.17227 (13)0.0294 (6)0.920 (3)
C580.10597 (15)0.26329 (17)0.16995 (12)0.0273 (6)0.920 (3)
C590.15338 (16)0.30464 (18)0.12682 (13)0.0277 (6)0.920 (3)
C5100.14472 (16)0.4291 (2)0.03200 (14)0.0306 (7)0.920 (3)
C5110.19490 (16)0.3649 (2)0.00105 (15)0.0337 (7)0.920 (3)
C5120.19244 (16)0.20398 (19)0.06081 (14)0.0299 (6)0.920 (3)
N610.43281 (11)0.31397 (13)0.20955 (9)0.0262 (4)
N620.40386 (10)0.15458 (13)0.06891 (9)0.0231 (4)
N630.34363 (11)0.25746 (14)0.02518 (10)0.0299 (4)
C610.64295 (14)0.58929 (17)0.09817 (12)0.0294 (5)
C620.57006 (14)0.56489 (18)0.09232 (13)0.0351 (6)
C630.52341 (14)0.49053 (17)0.13403 (13)0.0337 (6)
C640.54806 (13)0.43687 (16)0.18142 (11)0.0259 (5)
C650.61988 (14)0.46260 (17)0.18789 (12)0.0288 (5)
C660.66614 (14)0.53851 (17)0.14781 (12)0.0287 (5)
C670.49920 (13)0.35449 (16)0.22735 (12)0.0266 (5)
C680.45527 (13)0.25561 (17)0.14638 (12)0.0286 (5)
C690.38395 (14)0.22882 (16)0.12611 (11)0.0281 (5)
C6100.33612 (13)0.11221 (16)0.05163 (12)0.0275 (5)
C6110.29077 (14)0.19370 (17)0.02772 (12)0.0302 (5)
C6120.30250 (15)0.33621 (18)0.05036 (13)0.0352 (6)
N710.0735 (8)0.1903 (13)0.2048 (8)0.031 (3)*0.080 (3)
N720.0948 (13)0.353 (2)0.0625 (13)0.031 (3)*0.080 (3)
N730.1472 (11)0.2484 (18)0.0272 (16)0.031 (3)*0.080 (3)
C710.1343 (8)0.0863 (10)0.0985 (10)0.031 (3)*0.080 (3)
C720.0614 (9)0.0638 (13)0.0925 (10)0.031 (3)*0.080 (3)
C730.0156 (8)0.0122 (13)0.1327 (9)0.031 (3)*0.080 (3)
C740.0417 (8)0.0666 (9)0.1792 (7)0.031 (3)*0.080 (3)
C750.1147 (10)0.0440 (14)0.1852 (11)0.031 (3)*0.080 (3)
C760.1606 (10)0.0319 (15)0.1451 (12)0.031 (3)*0.080 (3)
C770.0077 (10)0.1498 (11)0.2234 (8)0.031 (3)*0.080 (3)
C780.0486 (10)0.247 (2)0.1407 (12)0.031 (3)*0.080 (3)
C790.1191 (11)0.282 (2)0.1217 (14)0.031 (3)*0.080 (3)
C7100.1595 (16)0.4008 (12)0.0438 (13)0.031 (3)*0.080 (3)
C7110.2013 (12)0.3259 (18)0.0112 (16)0.031 (3)*0.080 (3)
C7120.1850 (9)0.1689 (14)0.0551 (13)0.031 (3)*0.080 (3)
H140.55010.12770.06290.041*
H120.72330.28250.23440.029*
H130.64050.15980.16710.030*
H150.57640.36200.00920.030*
H160.65840.48420.07690.029*
H220.88470.35390.22630.029*
H230.99230.35640.18790.031*
H250.92650.63440.10090.037*
H260.81980.63250.14100.036*
H340.04260.39100.06960.049*
H320.15310.04520.04880.038*
H330.07000.17630.00610.038*
H350.13600.34290.16890.032*
H360.21960.21150.22390.031*
H420.30620.11420.09720.034*
H430.41550.11310.06060.033*
H450.49280.14390.17250.033*
H460.38190.14390.20620.036*
H51A0.07690.13190.12250.033*0.920 (3)
H52A0.06990.32190.03850.029*0.920 (3)
H52B0.07230.40790.08600.029*0.920 (3)
H53A0.10950.30470.07130.035*0.920 (3)
H520.06350.13220.03800.036*0.920 (3)
H530.01290.00920.08150.035*0.920 (3)
H550.13240.08560.18800.036*0.920 (3)
H560.20630.05940.14750.035*0.920 (3)
H57A0.03450.13160.21850.035*0.920 (3)
H57B0.03250.20890.17760.035*0.920 (3)
H58A0.07750.31990.18330.033*0.920 (3)
H58B0.14140.23250.21220.033*0.920 (3)
H59A0.17680.24740.10870.033*0.920 (3)
H59B0.19620.34790.15540.033*0.920 (3)
H51C0.10620.46740.00480.037*0.920 (3)
H51D0.17810.47920.06410.037*0.920 (3)
H51E0.24120.33970.03760.040*0.920 (3)
H51F0.21310.40670.03100.040*0.920 (3)
H51G0.20940.23460.09780.036*0.920 (3)
H51H0.23960.18310.02350.036*0.920 (3)
H61A0.40150.36730.20540.031*
H62A0.43650.18590.03060.028*
H62B0.43100.10140.07990.028*
H63A0.37090.21680.06120.036*
H620.55200.59940.05950.042*
H630.47350.47630.12980.040*
H650.63800.42760.22040.035*
H660.71430.55590.15450.034*
H67A0.47950.38230.27440.032*
H67B0.53410.29680.22850.032*
H68A0.49190.29610.10950.034*
H68B0.48220.19230.15270.034*
H69A0.36240.29150.11210.034*
H69B0.34350.19930.16590.034*
H61B0.35480.06040.01510.033*
H61C0.30080.07770.09240.033*
H61D0.26200.23680.06700.036*
H61E0.25220.16090.00920.036*
H61F0.26940.30330.07470.042*
H61G0.26780.37410.01090.042*
H71A0.10510.13730.20080.037*0.080 (3)
H72B0.06460.40340.07230.037*0.080 (3)
H72A0.06390.31740.02520.037*0.080 (3)
H73A0.10960.27940.06260.037*0.080 (3)
H720.04290.10040.06080.037*0.080 (3)
H730.03410.02710.12830.037*0.080 (3)
H750.13320.08060.21680.037*0.080 (3)
H760.21030.04690.14950.037*0.080 (3)
H77A0.02810.12310.27070.037*0.080 (3)
H77B0.02720.20750.22440.037*0.080 (3)
H78A0.01520.20310.10390.037*0.080 (3)
H78B0.01750.30710.14560.037*0.080 (3)
H79A0.14570.22190.10980.037*0.080 (3)
H79B0.15640.31660.16120.037*0.080 (3)
H71C0.13860.45750.01150.037*0.080 (3)
H71D0.19740.42990.08540.037*0.080 (3)
H71E0.24430.29280.04730.037*0.080 (3)
H71F0.22420.36290.01990.037*0.080 (3)
H71G0.21360.20250.08310.037*0.080 (3)
H71H0.22440.13540.01620.037*0.080 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0226 (3)0.0227 (3)0.0263 (3)0.0020 (2)0.0092 (2)0.0022 (2)
O110.0291 (9)0.0318 (8)0.0231 (8)0.0004 (7)0.0094 (7)0.0037 (6)
O120.0275 (9)0.0236 (8)0.0388 (10)0.0052 (6)0.0118 (7)0.0021 (7)
O140.0264 (9)0.0291 (8)0.0245 (8)0.0029 (7)0.0055 (7)0.0015 (6)
O240.0290 (9)0.0293 (8)0.0474 (11)0.0010 (7)0.0216 (8)0.0048 (7)
C110.0198 (11)0.0243 (10)0.0260 (12)0.0008 (9)0.0094 (9)0.0015 (8)
C120.0217 (11)0.0297 (11)0.0215 (11)0.0024 (9)0.0063 (9)0.0027 (9)
C130.0240 (12)0.0263 (11)0.0267 (12)0.0005 (9)0.0099 (10)0.0027 (9)
C140.0186 (11)0.0293 (11)0.0239 (12)0.0024 (9)0.0100 (9)0.0032 (9)
C150.0231 (12)0.0300 (11)0.0223 (11)0.0043 (9)0.0064 (9)0.0031 (9)
C160.0243 (12)0.0245 (11)0.0260 (12)0.0028 (9)0.0103 (10)0.0023 (9)
C210.0204 (11)0.0230 (10)0.0243 (11)0.0000 (8)0.0071 (9)0.0023 (8)
C220.0244 (12)0.0216 (10)0.0264 (12)0.0002 (9)0.0080 (10)0.0022 (9)
C230.0239 (12)0.0247 (11)0.0296 (13)0.0044 (9)0.0077 (10)0.0026 (9)
C240.0234 (12)0.0244 (11)0.0334 (13)0.0033 (9)0.0095 (10)0.0000 (9)
C250.0316 (13)0.0229 (11)0.0422 (14)0.0006 (9)0.0168 (11)0.0059 (10)
C260.0295 (13)0.0211 (10)0.0382 (14)0.0036 (9)0.0096 (11)0.0029 (9)
S20.0269 (3)0.0256 (3)0.0439 (4)0.0009 (2)0.0189 (3)0.0000 (2)
O210.0355 (10)0.0259 (8)0.0725 (14)0.0058 (7)0.0271 (10)0.0043 (8)
O220.0330 (10)0.0359 (9)0.0460 (11)0.0073 (7)0.0219 (8)0.0104 (8)
O340.0284 (9)0.0381 (9)0.0310 (9)0.0040 (7)0.0076 (7)0.0005 (7)
O440.0254 (9)0.0272 (8)0.0364 (9)0.0022 (6)0.0143 (7)0.0023 (7)
C310.0174 (11)0.0281 (11)0.0358 (13)0.0024 (9)0.0118 (10)0.0027 (9)
C320.0290 (13)0.0313 (12)0.0380 (14)0.0051 (10)0.0159 (11)0.0117 (10)
C330.0245 (12)0.0425 (14)0.0289 (13)0.0053 (10)0.0107 (10)0.0076 (10)
C340.0187 (11)0.0328 (12)0.0301 (13)0.0017 (9)0.0119 (10)0.0003 (9)
C350.0252 (12)0.0273 (11)0.0300 (13)0.0010 (9)0.0131 (10)0.0052 (9)
C360.0207 (12)0.0321 (12)0.0277 (12)0.0019 (9)0.0111 (10)0.0035 (9)
C410.0238 (12)0.0248 (11)0.0364 (13)0.0020 (9)0.0147 (10)0.0006 (9)
C420.0254 (12)0.0230 (11)0.0355 (14)0.0022 (9)0.0087 (10)0.0015 (9)
C430.0308 (13)0.0217 (11)0.0310 (13)0.0044 (9)0.0102 (10)0.0037 (9)
C440.0231 (12)0.0249 (11)0.0256 (12)0.0032 (9)0.0087 (9)0.0028 (9)
C450.0239 (12)0.0270 (11)0.0330 (13)0.0035 (9)0.0095 (10)0.0042 (9)
C460.0298 (13)0.0278 (11)0.0339 (13)0.0025 (10)0.0132 (11)0.0075 (9)
N510.0263 (12)0.0309 (12)0.0285 (12)0.0023 (9)0.0119 (9)0.0019 (9)
N520.0222 (11)0.0264 (12)0.0255 (12)0.0015 (9)0.0081 (9)0.0048 (9)
N530.0313 (12)0.0313 (12)0.0272 (13)0.0051 (10)0.0110 (10)0.0002 (10)
C510.0289 (14)0.0247 (12)0.0257 (14)0.0057 (10)0.0110 (11)0.0052 (10)
C520.0376 (16)0.0296 (13)0.0294 (15)0.0034 (11)0.0193 (13)0.0002 (11)
C530.0293 (14)0.0328 (13)0.0315 (15)0.0029 (11)0.0181 (12)0.0018 (11)
C540.0325 (14)0.0244 (12)0.0246 (14)0.0068 (10)0.0121 (11)0.0069 (10)
C550.0332 (15)0.0310 (13)0.0304 (15)0.0089 (11)0.0170 (13)0.0012 (11)
C560.0280 (14)0.0330 (14)0.0324 (16)0.0072 (11)0.0169 (12)0.0027 (11)
C570.0356 (15)0.0269 (12)0.0292 (14)0.0051 (11)0.0153 (12)0.0018 (10)
C580.0292 (14)0.0279 (12)0.0238 (13)0.0035 (10)0.0067 (11)0.0027 (10)
C590.0258 (14)0.0276 (13)0.0270 (14)0.0037 (10)0.0045 (11)0.0005 (10)
C5100.0325 (16)0.0275 (13)0.0361 (16)0.0023 (11)0.0167 (13)0.0015 (11)
C5110.0354 (16)0.0295 (13)0.0422 (17)0.0017 (12)0.0211 (13)0.0009 (12)
C5120.0354 (15)0.0311 (13)0.0296 (14)0.0032 (12)0.0194 (12)0.0023 (11)
N610.0282 (11)0.0239 (9)0.0279 (10)0.0007 (8)0.0106 (8)0.0008 (7)
N620.0242 (10)0.0231 (9)0.0221 (10)0.0023 (7)0.0075 (8)0.0010 (7)
N630.0315 (11)0.0321 (10)0.0262 (10)0.0027 (8)0.0092 (9)0.0060 (8)
C610.0276 (13)0.0302 (12)0.0333 (13)0.0016 (10)0.0140 (11)0.0020 (10)
C620.0334 (14)0.0360 (13)0.0427 (15)0.0001 (11)0.0216 (12)0.0118 (11)
C630.0299 (13)0.0336 (13)0.0442 (15)0.0052 (10)0.0211 (12)0.0074 (11)
C640.0292 (12)0.0224 (10)0.0276 (12)0.0033 (9)0.0109 (10)0.0029 (9)
C650.0296 (13)0.0300 (12)0.0306 (13)0.0033 (10)0.0150 (11)0.0026 (9)
C660.0245 (12)0.0341 (12)0.0306 (13)0.0003 (10)0.0133 (10)0.0009 (10)
C670.0295 (12)0.0252 (11)0.0274 (12)0.0024 (9)0.0120 (10)0.0009 (9)
C680.0281 (13)0.0275 (11)0.0312 (13)0.0022 (9)0.0105 (10)0.0007 (9)
C690.0313 (13)0.0270 (11)0.0258 (12)0.0025 (10)0.0084 (10)0.0026 (9)
C6100.0302 (13)0.0286 (11)0.0263 (12)0.0049 (10)0.0127 (10)0.0000 (9)
C6110.0298 (13)0.0352 (12)0.0281 (13)0.0045 (10)0.0129 (11)0.0057 (10)
C6120.0303 (13)0.0393 (13)0.0403 (15)0.0016 (11)0.0174 (11)0.0099 (11)
Geometric parameters (Å, º) top
S1—O111.443 (2)C51—C521.385 (4)
S1—O121.445 (2)C51—C561.391 (3)
S1—C211.746 (2)C52—C531.384 (3)
S1—C111.761 (2)C53—C541.386 (3)
O14—C141.348 (3)C54—C551.395 (4)
O24—C241.315 (3)C54—C571.512 (3)
C11—C121.391 (3)C55—C561.387 (4)
C11—C161.399 (3)C58—C591.513 (4)
C12—C131.384 (3)C510—C5111.515 (4)
C13—C141.401 (3)N61—C681.452 (3)
C14—C151.400 (3)N61—C671.459 (3)
C15—C161.376 (3)N62—C691.482 (3)
C21—C221.394 (3)N62—C6101.484 (3)
C21—C261.396 (3)N63—C6121.458 (3)
C22—C231.374 (3)N63—C6111.464 (3)
C23—C241.407 (3)C61—C661.389 (3)
C24—C251.415 (3)C61—C621.395 (3)
C25—C261.377 (3)C61—C612ii1.511 (3)
S2—O221.434 (2)C62—C631.394 (3)
S2—O211.443 (2)C63—C641.384 (3)
S2—C411.746 (2)C64—C651.386 (3)
S2—C311.754 (2)C64—C671.521 (3)
O34—C341.353 (3)C65—C661.391 (3)
O44—C441.320 (3)C68—C691.514 (3)
C31—C361.389 (3)C610—C6111.518 (3)
C31—C321.397 (3)C612—C61ii1.511 (3)
C32—C331.377 (3)N71—C771.457 (4)
C33—C341.387 (3)N71—C781.458 (4)
C34—C351.393 (3)N72—C7101.482 (4)
C35—C361.383 (3)N72—C791.484 (4)
C41—C421.387 (3)N73—C7121.457 (4)
C41—C461.396 (3)N73—C7111.458 (4)
C42—C431.379 (3)C71—C712i1.517 (12)
C43—C441.408 (3)C71—C761.391 (4)
C44—C451.413 (3)C71—C721.392 (4)
C45—C461.373 (3)C72—C731.390 (4)
N51—C581.461 (3)C73—C741.390 (4)
N51—C571.463 (3)C74—C751.392 (4)
N52—C591.483 (3)C74—C771.517 (4)
N52—C5101.488 (3)C75—C761.389 (4)
N53—C5111.445 (3)C78—C791.514 (4)
N53—C5121.461 (3)C710—C7111.516 (4)
C51—C512i1.510 (3)
O11—S1—O12118.4 (1)C59—N52—C510115.3 (2)
O11—S1—C21108.96 (10)C511—N53—C512115.5 (2)
O12—S1—C21107.65 (10)C52—C51—C56117.9 (2)
O11—S1—C11107.14 (10)C53—C52—C51121.3 (2)
O12—S1—C11108.09 (10)C52—C53—C54121.3 (2)
C21—S1—C11106.0 (1)C53—C54—C55117.5 (2)
C12—C11—C16120.0 (2)C53—C54—C57122.1 (2)
C12—C11—S1120.53 (17)C55—C54—C57120.3 (2)
C16—C11—S1119.47 (16)C56—C55—C54121.2 (2)
C13—C12—C11120.4 (2)C55—C56—C51120.8 (2)
C12—C13—C14119.5 (2)N51—C57—C54113.3 (2)
O14—C14—C15118.2 (2)N51—C58—C59111.0 (2)
O14—C14—C13122.0 (2)N52—C59—C58110.0 (2)
C15—C14—C13119.8 (2)N52—C510—C511112.0 (2)
C16—C15—C14120.3 (2)N53—C511—C510109.0 (2)
C15—C16—C11119.8 (2)N53—C512—C51i111.19 (19)
C22—C21—C26120.0 (2)C68—N61—C67113.29 (18)
C22—C21—S1119.76 (16)C69—N62—C610115.02 (17)
C26—C21—S1120.15 (16)C612—N63—C611112.47 (18)
C23—C22—C21119.7 (2)C66—C61—C62117.6 (2)
C22—C23—C24121.6 (2)C66—C61—C612ii120.2 (2)
O24—C24—C23121.0 (2)C62—C61—C612ii122.1 (2)
O24—C24—C25121.3 (2)C63—C62—C61120.8 (2)
C23—C24—C25117.7 (2)C64—C63—C62121.6 (2)
C26—C25—C24120.7 (2)C63—C64—C65117.5 (2)
C25—C26—C21120.2 (2)C63—C64—C67123.1 (2)
O22—S2—O21118.8 (1)C65—C64—C67119.4 (2)
O22—S2—C41108.65 (11)C64—C65—C66121.5 (2)
O21—S2—C41107.42 (10)C61—C66—C65121.0 (2)
O22—S2—C31107.44 (10)N61—C67—C64117.69 (18)
O21—S2—C31107.56 (11)N61—C68—C69110.22 (18)
C41—S2—C31106.3 (1)N62—C69—C68110.82 (18)
C36—C31—C32119.9 (2)N62—C610—C611112.51 (17)
C36—C31—S2120.68 (18)N63—C611—C610110.51 (19)
C32—C31—S2119.37 (17)N63—C612—C61ii112.8 (2)
C33—C32—C31120.0 (2)C77—N71—C78112.2 (7)
C32—C33—C34119.8 (2)C710—N72—C79115.1 (8)
O34—C34—C33117.3 (2)C712—N73—C711113.2 (7)
O34—C34—C35122.2 (2)C76—C71—C72119.3 (5)
C33—C34—C35120.5 (2)C73—C72—C71120.1 (6)
C36—C35—C34119.5 (2)C72—C73—C74120.7 (6)
C35—C36—C31120.1 (2)C73—C74—C75119.0 (5)
C42—C41—C46119.8 (2)C73—C74—C77121.3 (6)
C42—C41—S2120.42 (17)C75—C74—C77119.7 (6)
C46—C41—S2119.79 (17)C76—C75—C74120.4 (6)
C43—C42—C41120.1 (2)C75—C76—C71120.4 (6)
C42—C43—C44121.1 (2)N71—C77—C74118.6 (7)
O44—C44—C43121.0 (2)N71—C78—C79110.0 (7)
O44—C44—C45121.2 (2)N72—C79—C78110.1 (7)
C43—C44—C45117.8 (2)N72—C710—C711112.4 (8)
C46—C45—C44120.7 (2)N73—C711—C710110.5 (7)
C45—C46—C41120.5 (2)N73—C712—C71i118.1 (9)
C58—N51—C57110.98 (19)
O11—S1—C11—C1214.0 (2)C43—C44—C45—C460.2 (3)
O12—S1—C11—C12142.55 (18)C44—C45—C46—C410.9 (3)
C21—S1—C11—C12102.26 (19)C42—C41—C46—C451.2 (4)
O11—S1—C11—C16166.21 (17)S2—C41—C46—C45178.42 (18)
O12—S1—C11—C1637.6 (2)C56—C51—C52—C530.6 (4)
C21—S1—C11—C1677.54 (19)C51—C52—C53—C540.7 (4)
C16—C11—C12—C131.4 (3)C52—C53—C54—C550.4 (4)
S1—C11—C12—C13178.80 (17)C52—C53—C54—C57176.1 (2)
C11—C12—C13—C140.3 (3)C53—C54—C55—C561.7 (4)
C12—C13—C14—O14178.6 (2)C57—C54—C55—C56174.9 (2)
C12—C13—C14—C152.3 (3)C54—C55—C56—C511.8 (4)
O14—C14—C15—C16178.33 (19)C52—C51—C56—C550.6 (4)
C13—C14—C15—C162.5 (3)C58—N51—C57—C54172.4 (2)
C14—C15—C16—C110.8 (3)C53—C54—C57—N5124.2 (3)
C12—C11—C16—C151.2 (3)C55—C54—C57—N51159.4 (2)
S1—C11—C16—C15179.04 (17)C57—N51—C58—C59176.14 (19)
O11—S1—C21—C2246.2 (2)C510—N52—C59—C58167.1 (2)
O12—S1—C21—C22175.70 (17)N51—C58—C59—N5268.4 (3)
C11—S1—C21—C2268.82 (19)C59—N52—C510—C51159.7 (3)
O11—S1—C21—C26136.80 (18)C512—N53—C511—C510173.0 (2)
O12—S1—C21—C267.3 (2)N52—C510—C511—N5347.8 (3)
C11—S1—C21—C26108.19 (19)C511—N53—C512—C51i171.56 (19)
C26—C21—C22—C230.2 (3)C66—C61—C62—C631.4 (4)
S1—C21—C22—C23177.19 (17)C612ii—C61—C62—C63175.4 (2)
C21—C22—C23—C241.1 (3)C61—C62—C63—C641.4 (4)
C22—C23—C24—O24176.2 (2)C62—C63—C64—C652.5 (4)
C22—C23—C24—C251.5 (3)C62—C63—C64—C67179.4 (2)
O24—C24—C25—C26176.8 (2)C63—C64—C65—C660.8 (3)
C23—C24—C25—C261.0 (3)C67—C64—C65—C66179.0 (2)
C24—C25—C26—C210.1 (4)C62—C61—C66—C653.1 (3)
C22—C21—C26—C250.3 (3)C612ii—C61—C66—C65173.8 (2)
S1—C21—C26—C25176.67 (18)C64—C65—C66—C612.0 (4)
O22—S2—C31—C3610.8 (2)C68—N61—C67—C6467.5 (2)
O21—S2—C31—C36139.84 (18)C63—C64—C67—N6114.9 (3)
C41—S2—C31—C36105.34 (19)C65—C64—C67—N61166.99 (19)
O22—S2—C31—C32167.76 (18)C67—N61—C68—C69172.08 (17)
O21—S2—C31—C3238.8 (2)C610—N62—C69—C68171.77 (17)
C41—S2—C31—C3276.1 (2)N61—C68—C69—N62170.13 (17)
C36—C31—C32—C331.6 (3)C69—N62—C610—C61162.4 (2)
S2—C31—C32—C33177.01 (18)C612—N63—C611—C610179.30 (19)
C31—C32—C33—C340.3 (4)N62—C610—C611—N6349.3 (2)
C32—C33—C34—O34177.4 (2)C611—N63—C612—C61ii172.6 (2)
C32—C33—C34—C352.2 (3)C76—C71—C72—C730.00 (3)
O34—C34—C35—C36177.5 (2)C71—C72—C73—C740.00 (3)
C33—C34—C35—C362.1 (3)C72—C73—C74—C750.00 (7)
C34—C35—C36—C310.1 (3)C72—C73—C74—C77180.00 (4)
C32—C31—C36—C351.7 (3)C73—C74—C75—C760.00 (9)
S2—C31—C36—C35176.90 (17)C77—C74—C75—C76180.00 (6)
O22—S2—C41—C42135.38 (19)C74—C75—C76—C710.00 (9)
O21—S2—C41—C425.7 (2)C72—C71—C76—C750.00 (7)
C31—S2—C41—C42109.2 (2)C78—N71—C77—C7467 (2)
O22—S2—C41—C4644.2 (2)C73—C74—C77—N7116 (2)
O21—S2—C41—C46173.94 (19)C75—C74—C77—N71164.4 (13)
C31—S2—C41—C4671.1 (2)C77—N71—C78—C79177 (2)
C46—C41—C42—C430.3 (3)C710—N72—C79—C78174 (3)
S2—C41—C42—C43179.29 (18)N71—C78—C79—N72171 (3)
C41—C42—C43—C440.8 (3)C79—N72—C710—C71172 (4)
C42—C43—C44—O44179.3 (2)C712—N73—C711—C710175 (3)
C42—C43—C44—C451.1 (3)N72—C710—C711—N7332 (4)
O44—C44—C45—C46178.5 (2)C711—N73—C712—C71i178 (2)
Symmetry codes: (i) x, y, z; (ii) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O14—H14···O440.841.682.496 (2)165
O34—H34···O24iii0.841.672.501 (2)171
N51—H51A···O210.922.383.092 (3)134
N52—H52A···O34i0.922.202.914 (3)134
N52—H52B···O24iv0.921.712.612 (3)167
N61—H61A···O12ii0.922.333.134 (3)145
N62—H62A···O140.922.102.898 (2)144
N62—H62B···O44v0.921.752.652 (2)168
C12—H12···O110.952.542.915 (3)104
C22—H22···N61vi0.952.573.428 (3)150
C26—H26···O120.952.502.895 (3)105
C36—H36···O220.952.542.908 (3)103
C42—H42···O210.952.502.889 (3)104
C43—H43···O14v0.952.563.443 (3)155
C59—H59B···O22vii0.992.323.156 (3)141
C610—H61C···O11viii0.992.503.334 (3)142
C69—H69B···O11viii0.992.373.232 (3)145
Symmetry codes: (i) x, y, z; (ii) x+1, y+1, z; (iii) x1, y, z; (iv) x1, y1, z; (v) x+1, y, z; (vi) x+1/2, y+1/2, z+1/2; (vii) x+1/2, y1/2, z+1/2; (viii) x1/2, y+1/2, z1/2.
(9911) 3,6,9,16,19,22-Hexa-azatricyclo[22.2.2.211,14]triconta-1(26),11 (29), 12,14 (30),24,27-hexaene – 4,4'-Biphenol –Water (1/3/2) top
Crystal data top
C24H40N6·C12H10O2·2(C12H9O2)·2(H2O)F(000) = 1076
Mr = 1005.23Dx = 1.295 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.3442 (4) ÅCell parameters from 4832 reflections
b = 7.6496 (3) Åθ = 4.2–25.6°
c = 29.1745 (9) ŵ = 0.09 mm1
β = 110.686 (2)°T = 100 K
V = 2577.29 (15) Å3Plate, colourless
Z = 20.25 × 0.20 × 0.04 mm
Data collection top
Kappa-CCD
diffractometer
4832 independent reflections
Radiation source: fine-focus sealed X-ray tube2686 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.070
φ scans and ω scans with κ offsetsθmax = 25.6°, θmin = 4.2°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 015
Tmin = 0.979, Tmax = 0.997k = 90
19716 measured reflectionsl = 3532
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H-atom parameters constrained
S = 0.84 w = 1/[σ2(Fo2) + (0.0568P)2]
where P = (Fo2 + 2Fc2)/3
4832 reflections(Δ/σ)max = 0.001
362 parametersΔρmax = 0.16 e Å3
14 restraintsΔρmin = 0.24 e Å3
Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Geometry. Mean-plane data from the final SHELXL97 refinement run:- Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

5.1270(0.0088) x + 6.7225(0.0031) y - 10.6934(0.0235) z = 3.9351(0.0129)

* 0.0007(0.0014) C11 * -0.0050(0.0015) C12 * 0.0032(0.0015) C13 * 0.0028(0.0014) C14 * -0.0070(0.0014) C15 * 0.0053(0.0014) C16 0.0074(0.0026) O14

Rms deviation of fitted atoms = 0.0045

0.8345(0.0087) x + 7.1053(0.0023) y - 10.6384(0.0219) z = 3.2175(0.0105)

Angle to previous plane (with approximate e.s.d.) = 21.6 (1)

* 0.0181(0.0013) C21 * -0.0097(0.0013) C22 * -0.0118(0.0013) C23 * 0.0248(0.0013) C24 * -0.0163(0.0013) C25 * -0.0052(0.0013) C26 0.0851(0.0024) O24 0.3285(0.0051) O34 0.1078(0.0027) C31 - 0.2371(0.0033) C32 - 0.1467(0.0041) C33 0.2891(0.0044) C34 0.6581(0.0040) C35 0.5710(0.0033) C36

Rms deviation of fitted atoms = 0.0156

- 2.7414(0.0085) x - 5.7392(0.0037) y + 19.2852(0.0160) z = 1.5525(0.0110)

Angle to previous plane (with approximate e.s.d.) = 20.2 (1)

* 0.0068(0.0012) C31 * -0.0012(0.0013) C32 * -0.0065(0.0013) C33 * 0.0086(0.0012) C34 * -0.0029(0.0012) C35 * -0.0048(0.0012) C36 - 0.3132(0.0052) O24 0.0396(0.0024) O34 0.0035(0.0027) C21 0.3856(0.0033) C22 0.3068(0.0042) C23 - 0.1759(0.0044) C24 - 0.4971(0.0041) C25 - 0.4222(0.0033) C26

Rms deviation of fitted atoms = 0.0057

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O140.09460 (11)1.20777 (17)0.43595 (5)0.0351 (4)
C110.43918 (16)1.0304 (2)0.49026 (7)0.0299 (5)
C120.36874 (18)1.0057 (3)0.44150 (7)0.0462 (6)
C130.25550 (17)1.0636 (3)0.42285 (7)0.0422 (6)
C140.20649 (17)1.1483 (2)0.45265 (7)0.0295 (5)
C150.27387 (18)1.1728 (3)0.50129 (7)0.0371 (5)
C160.38776 (18)1.1166 (2)0.51939 (7)0.0364 (5)
O240.01767 (10)1.00887 (16)0.36198 (4)0.0281 (3)
O340.87232 (10)0.97300 (17)0.24811 (4)0.0300 (3)
C210.38049 (15)0.9738 (2)0.31639 (6)0.0227 (4)
C220.31278 (16)1.0319 (2)0.36311 (7)0.0299 (5)
C230.19401 (16)1.0407 (2)0.37855 (7)0.0304 (5)
C240.13431 (16)0.9927 (2)0.34771 (7)0.0239 (4)
C250.19980 (16)0.9260 (2)0.30190 (7)0.0284 (5)
C260.31943 (16)0.9188 (2)0.28662 (7)0.0271 (5)
C310.50877 (15)0.9749 (2)0.29867 (6)0.0219 (4)
C320.57601 (16)0.8747 (2)0.25886 (7)0.0274 (5)
C330.69556 (16)0.8763 (2)0.24208 (7)0.0263 (5)
C340.75307 (15)0.9792 (2)0.26530 (6)0.0230 (4)
C350.68938 (16)1.0822 (2)0.30442 (6)0.0252 (5)
C360.56949 (16)1.0804 (2)0.32083 (6)0.0250 (5)
N510.17838 (13)0.74399 (19)0.50313 (5)0.0262 (4)
N520.06850 (13)0.70099 (19)0.40025 (5)0.0277 (4)
N530.24003 (17)0.5531 (3)0.36793 (7)0.0284 (7)0.789 (4)
C510.5503 (2)0.4668 (3)0.62177 (9)0.0249 (6)0.789 (4)
C520.5220 (3)0.5401 (3)0.57540 (10)0.0286 (7)0.789 (4)
C530.4085 (3)0.5892 (4)0.54881 (11)0.0283 (8)0.789 (4)
C540.3209 (2)0.5672 (5)0.56779 (15)0.0241 (8)0.789 (4)
C550.3504 (3)0.4962 (5)0.61469 (16)0.0315 (7)0.789 (4)
C560.4622 (2)0.4466 (4)0.64074 (10)0.0296 (7)0.789 (4)
C570.1954 (3)0.6093 (4)0.54035 (13)0.0249 (9)0.789 (4)
C580.05573 (16)0.7831 (2)0.47860 (7)0.0286 (5)
C590.00593 (16)0.6660 (2)0.43432 (7)0.0292 (5)
C5100.0369 (4)0.5743 (6)0.35862 (15)0.0286 (8)0.789 (4)
C5110.1253 (2)0.5974 (4)0.33378 (10)0.0290 (7)0.789 (4)
C5120.3295 (2)0.5920 (4)0.34708 (9)0.0296 (7)0.789 (4)
O60.03642 (12)1.19090 (17)0.29510 (5)0.0328 (4)*
C610.5693 (6)0.5261 (8)0.6167 (3)0.0258 (14)*0.211 (4)
C620.5313 (10)0.5915 (12)0.5692 (3)0.0258 (14)*0.211 (4)
C630.4135 (11)0.6110 (14)0.5433 (4)0.0258 (14)*0.211 (4)
C640.3336 (7)0.5651 (16)0.5650 (6)0.0258 (14)*0.211 (4)
C650.3716 (8)0.4997 (18)0.6125 (6)0.0258 (14)*0.211 (4)
C660.4894 (9)0.4802 (14)0.6384 (4)0.0258 (14)*0.211 (4)
C670.2077 (11)0.5890 (17)0.5353 (6)0.0258 (14)*0.211 (4)
C6100.0590 (18)0.599 (2)0.3557 (6)0.0258 (14)*0.211 (4)
C6110.1323 (8)0.6726 (15)0.3286 (4)0.0258 (14)*0.211 (4)
N630.2545 (6)0.6636 (10)0.3590 (3)0.0258 (14)*0.211 (4)
C6120.3036 (7)0.4950 (11)0.3553 (3)0.0258 (14)*0.211 (4)
H140.05581.15180.41070.053*
H120.39980.94670.42020.055*
H130.21091.04510.38930.051*
H150.24171.22900.52260.044*
H160.43241.13760.55290.044*
H340.89751.04330.26410.045*
H220.35021.06660.38510.036*
H230.15171.08030.41080.036*
H250.16180.88490.28080.034*
H260.36160.87490.25480.033*
H320.53810.80250.24270.033*
H330.73840.80700.21460.032*
H350.72811.15480.32020.030*
H360.52731.15240.34780.030*
H51A0.21680.84400.51760.031*
H52A0.14690.69490.41720.033*
H52B0.05160.81250.38800.033*
H53A0.24240.43610.37550.034*0.789 (4)
H520.58060.55670.56170.034*0.789 (4)
H530.39060.63860.51710.034*0.789 (4)
H550.29230.48200.62880.038*0.789 (4)
H560.47980.39740.67240.035*0.789 (4)
H57A0.15500.50150.52440.030*0.789 (4)
H57B0.15950.64850.56400.030*0.789 (4)
H58A0.04610.90710.46820.034*
H58B0.01380.76410.50150.034*
H59A0.01520.54180.44450.035*
H59B0.07770.69010.41790.035*
H51C0.04210.59860.33530.034*0.789 (4)
H51D0.03910.45310.37080.034*0.789 (4)
H51E0.10530.52080.30460.035*0.789 (4)
H51F0.12450.72000.32280.035*0.789 (4)
H51G0.33090.71970.34190.035*0.789 (4)
H51H0.30790.53490.31460.035*0.789 (4)
H610.017 (2)1.133 (3)0.3162 (7)0.086 (6)*
H620.0156 (18)1.267 (3)0.2811 (8)0.086 (6)*
H62A0.58590.62280.55440.031*0.211 (4)
H630.38750.65570.51090.031*0.211 (4)
H650.31700.46840.62720.031*0.211 (4)
H660.51540.43550.67080.031*0.211 (4)
H67A0.18020.48360.51480.031*0.211 (4)
H67B0.16450.59600.55810.031*0.211 (4)
H61A0.02300.59730.33350.031*0.211 (4)
H61B0.08290.47690.36530.031*0.211 (4)
H61C0.11850.60530.29810.031*0.211 (4)
H61D0.11020.79570.31950.031*0.211 (4)
H63A0.29430.74940.34950.031*0.1054 (18)
H63B0.26270.68410.39120.031*0.1054 (18)
H61E0.28930.47150.32030.031*0.211 (4)
H61F0.26160.40470.36680.031*0.211 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O140.0293 (9)0.0320 (8)0.0356 (9)0.0003 (7)0.0009 (7)0.0001 (6)
C110.0231 (11)0.0361 (12)0.0269 (11)0.0074 (10)0.0046 (10)0.0047 (10)
C120.0220 (13)0.0916 (19)0.0254 (12)0.0050 (12)0.0090 (10)0.0005 (12)
C130.0220 (13)0.0781 (17)0.0241 (12)0.0095 (11)0.0053 (10)0.0021 (11)
C140.0229 (12)0.0266 (11)0.0337 (13)0.0057 (9)0.0034 (10)0.0055 (9)
C150.0361 (14)0.0293 (12)0.0359 (13)0.0047 (10)0.0006 (11)0.0103 (10)
C160.0369 (14)0.0288 (12)0.0311 (12)0.0009 (10)0.0032 (11)0.0063 (10)
O240.0178 (8)0.0344 (8)0.0289 (8)0.0010 (6)0.0045 (6)0.0018 (6)
O340.0198 (8)0.0370 (8)0.0314 (8)0.0007 (6)0.0069 (6)0.0035 (6)
C210.0203 (11)0.0197 (10)0.0257 (11)0.0001 (8)0.0049 (9)0.0013 (9)
C220.0234 (12)0.0383 (12)0.0271 (12)0.0041 (9)0.0080 (10)0.0052 (9)
C230.0238 (12)0.0376 (12)0.0249 (11)0.0021 (9)0.0024 (9)0.0072 (10)
C240.0188 (11)0.0229 (11)0.0269 (11)0.0011 (8)0.0041 (9)0.0025 (9)
C250.0239 (12)0.0336 (12)0.0280 (11)0.0042 (9)0.0095 (10)0.0033 (9)
C260.0244 (12)0.0289 (11)0.0240 (11)0.0001 (9)0.0036 (9)0.0037 (9)
C310.0205 (11)0.0200 (10)0.0238 (11)0.0003 (8)0.0061 (9)0.0019 (9)
C320.0240 (12)0.0268 (11)0.0301 (12)0.0021 (9)0.0079 (9)0.0039 (9)
C330.0244 (12)0.0261 (11)0.0241 (11)0.0031 (9)0.0033 (9)0.0040 (9)
C340.0179 (11)0.0258 (11)0.0237 (11)0.0000 (8)0.0054 (9)0.0058 (9)
C350.0235 (12)0.0302 (11)0.0234 (11)0.0000 (9)0.0100 (9)0.0005 (9)
C360.0231 (12)0.0281 (11)0.0209 (10)0.0040 (9)0.0041 (9)0.0028 (9)
N510.0239 (10)0.0229 (9)0.0293 (10)0.0016 (7)0.0065 (8)0.0010 (7)
N520.0229 (9)0.0294 (9)0.0274 (9)0.0043 (7)0.0048 (8)0.0013 (8)
N530.0277 (13)0.0262 (14)0.0300 (12)0.0030 (10)0.0084 (10)0.0046 (10)
C510.0299 (16)0.0191 (14)0.0244 (14)0.0014 (12)0.0080 (13)0.0018 (12)
C520.0311 (17)0.0253 (17)0.0327 (18)0.0000 (14)0.0156 (14)0.0001 (13)
C530.0328 (18)0.0289 (17)0.0222 (15)0.0039 (13)0.0086 (14)0.0030 (12)
C540.0241 (16)0.0189 (13)0.0295 (16)0.0018 (11)0.0098 (13)0.0031 (11)
C550.0302 (19)0.0310 (15)0.0347 (17)0.0032 (14)0.0134 (15)0.0009 (13)
C560.034 (2)0.0279 (18)0.0257 (15)0.0006 (13)0.0085 (14)0.0046 (12)
C570.0286 (17)0.0213 (16)0.0299 (17)0.0007 (12)0.0166 (13)0.0015 (13)
C580.0306 (12)0.0269 (11)0.0302 (12)0.0040 (9)0.0132 (10)0.0022 (9)
C590.0260 (12)0.0288 (11)0.0346 (12)0.0002 (9)0.0128 (10)0.0035 (9)
C5100.025 (3)0.033 (2)0.0255 (16)0.0017 (13)0.0059 (14)0.0041 (15)
C5110.0258 (16)0.0294 (17)0.0285 (16)0.0006 (13)0.0055 (13)0.0010 (14)
C5120.0320 (17)0.0332 (17)0.0250 (15)0.0020 (13)0.0120 (13)0.0014 (12)
Geometric parameters (Å, º) top
O14—C141.370 (2)N52—C5101.494 (3)
C11—C121.393 (3)N53—C5111.455 (3)
C11—C161.393 (3)N53—C5121.467 (3)
C11—C11i1.480 (4)C51—C521.390 (3)
C12—C131.382 (3)C51—C561.392 (3)
C13—C141.383 (3)C52—C531.393 (3)
C14—C151.381 (3)C53—C541.388 (3)
C15—C161.384 (3)C54—C551.395 (3)
O24—C241.356 (2)C54—C571.506 (4)
O34—C341.378 (2)C55—C561.373 (4)
C21—C221.396 (2)C58—C591.513 (2)
C21—C261.401 (2)C510—C5111.518 (4)
C21—C311.482 (2)C512—C51ii1.510 (2)
C22—C231.375 (3)C61—C621.3900
C23—C241.399 (2)C61—C661.3900
C24—C251.392 (2)C62—C631.3900
C25—C261.385 (2)C63—C641.3900
C31—C321.395 (2)C64—C651.3900
C31—C361.405 (2)C64—C671.499 (10)
C32—C331.381 (2)C65—C661.3900
C33—C341.386 (2)C610—C6111.506 (9)
C34—C351.381 (2)C611—N631.457 (8)
C35—C361.385 (2)N63—C6121.446 (8)
N51—C571.457 (3)C612—C61ii1.499 (8)
N51—C581.459 (2)O6—H610.86 (2)
N52—C591.483 (2)O6—H620.86 (2)
C12—C11—C16115.62 (18)C57—N51—C58111.21 (18)
C12—C11—C11i122.1 (2)C59—N52—C510112.30 (16)
C16—C11—C11i122.2 (2)C511—N53—C512111.22 (19)
C13—C12—C11122.6 (2)C52—C51—C56118.0 (2)
C14—C13—C12120.60 (19)C51—C52—C53120.5 (2)
O14—C14—C15119.1 (2)C54—C53—C52121.2 (2)
O14—C14—C13122.8 (2)C53—C54—C55117.9 (2)
C15—C14—C13118.10 (19)C53—C54—C57124.2 (3)
C14—C15—C16120.79 (19)C55—C54—C57117.9 (3)
C15—C16—C11122.31 (19)C56—C55—C54120.9 (2)
C22—C21—C26115.68 (17)C55—C56—C51121.5 (2)
C22—C21—C31122.41 (16)N51—C57—C54113.4 (3)
C26—C21—C31121.89 (16)N51—C58—C59109.62 (15)
C23—C22—C21122.47 (17)N52—C59—C58108.34 (15)
C22—C23—C24121.30 (18)N52—C510—C511106.7 (2)
O24—C24—C25121.5 (2)N53—C511—C510109.6 (3)
O24—C24—C23121.5 (2)N53—C512—C51ii114.47 (19)
C25—C24—C23117.04 (17)C62—C61—C66120.0
C26—C25—C24121.05 (17)C63—C62—C61120.0
C25—C26—C21122.31 (17)C64—C63—C62120.0
C32—C31—C36116.22 (16)C63—C64—C65120.0
C32—C31—C21122.37 (16)C63—C64—C67117.7 (12)
C36—C31—C21121.40 (16)C65—C64—C67122.3 (12)
C33—C32—C31122.50 (17)C66—C65—C64120.0
C32—C33—C34119.97 (17)C65—C66—C61120.0
O34—C34—C35122.9 (2)N63—C611—C610110.3 (12)
O34—C34—C33117.9 (2)C612—N63—C611111.6 (8)
C35—C34—C33119.16 (17)N63—C612—C61ii116.2 (6)
C34—C35—C36120.46 (17)H61—O6—H62110 (2)
C35—C36—C31121.67 (17)
C16—C11—C12—C130.5 (3)C34—C35—C36—C310.1 (3)
C11i—C11—C12—C13179.3 (2)C32—C31—C36—C351.0 (3)
C11—C12—C13—C140.7 (3)C21—C31—C36—C35179.95 (16)
C12—C13—C14—O14179.84 (18)C56—C51—C52—C530.8 (3)
C12—C13—C14—C150.1 (3)C51—C52—C53—C540.3 (4)
O14—C14—C15—C16179.17 (17)C52—C53—C54—C550.8 (3)
C13—C14—C15—C161.0 (3)C52—C53—C54—C57177.0 (2)
C14—C15—C16—C111.3 (3)C53—C54—C55—C561.3 (4)
C12—C11—C16—C150.6 (3)C57—C54—C55—C56176.7 (2)
C11i—C11—C16—C15179.7 (2)C54—C55—C56—C510.7 (4)
C26—C21—C22—C232.2 (3)C52—C51—C56—C550.3 (4)
C31—C21—C22—C23175.99 (17)C58—N51—C57—C54178.46 (18)
C21—C22—C23—C240.5 (3)C53—C54—C57—N5126.6 (3)
C22—C23—C24—O24176.91 (16)C55—C54—C57—N51155.6 (3)
C22—C23—C24—C253.7 (3)C57—N51—C58—C5990.3 (2)
O24—C24—C25—C26176.49 (16)C510—N52—C59—C58172.0 (3)
C23—C24—C25—C264.1 (3)N51—C58—C59—N5260.84 (19)
C24—C25—C26—C211.4 (3)C59—N52—C510—C511167.2 (2)
C22—C21—C26—C251.8 (3)C512—N53—C511—C510173.8 (3)
C31—C21—C26—C25176.45 (16)N52—C510—C511—N5362.7 (4)
C22—C21—C31—C32161.47 (17)C511—N53—C512—C51ii174.25 (19)
C26—C21—C31—C3220.4 (3)C66—C61—C62—C630.0
C22—C21—C31—C3619.6 (3)C61—C62—C63—C640.0
C26—C21—C31—C36158.48 (17)C62—C63—C64—C650.0
C36—C31—C32—C330.6 (3)C62—C63—C64—C67180.0
C21—C31—C32—C33179.59 (17)C63—C64—C65—C660.0
C31—C32—C33—C340.6 (3)C67—C64—C65—C66180.0
C32—C33—C34—O34178.26 (16)C64—C65—C66—C610.0
C32—C33—C34—C351.5 (3)C62—C61—C66—C650.0
O34—C34—C35—C36178.59 (16)C610—C611—N63—C61285.1 (12)
C33—C34—C35—C361.2 (3)C611—N63—C612—C61ii177.1 (7)
Symmetry codes: (i) x+1, y+2, z+1; (ii) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O14—H14···O240.841.772.604 (2)172
O34—H34···O6iii0.841.812.649 (2)175
N52—H52B···O240.921.762.662 (2)165
O6—H61···O240.86 (2)1.81 (2)2.667 (2)178 (2)
O6—H62···O34iv0.86 (2)2.07 (2)2.923 (2)173 (2)
Symmetry codes: (iii) x1, y, z; (iv) x1, y+1/2, z+1/2.
 

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