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Co-crystallization of meso-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane, C16H36N4, with terephthalic acid (1,4-benzenedicarboxylic acid), C8H6O4, from ethanol yields the tetrahydrate (C16H36N4).(C8H6O4).(H2O)4 (1), meso-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane–terephthalic acid–water (1/1/4), while similar co-crystallization from methanol yields the hexahydrate (C16H36N4).(C8H6O4).(H2O)6 (2), meso-5,5,7,12,12,14-hexa­methyl-1,4,8,11-tetraazacyclotetradecane–terephthalic acid–water (1/­1/6). Both compounds are salts, [C16H38N4]2+.[C8H4O4]2−.4H2O (1) and [C16H38N4]2+.[C8H4O4]2−.6H2O (2): in (2) both ionic components lie across centres of inversion and in both salts there are two protons held within the N4 cavity of the cation. In the structure of (1), the cations and anions are linked into chains by means of paired N—H...O hydrogen bonds, and the water molecules are linked into continuous chains by means of O—H...O hydrogen bonds, in which each of the H atoms is independently disordered over two equally populated sites. The water chains link the ionic chains into a continuous three-dimensional framework by means of further O—H...O hydrogen bonds. In (2) the cations and anions are linked by single N—H...O hydrogen bonds, again into chains: at the same time the anions and the water molecules are linked by multiple O—H...O hydrogen bonds into continuous two-dimensional nets, which are linked by the cations, by means of N—H...O hydrogen bonds into a three-dimensional framework, entirely different from that in (1).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768199011544/bm0023sup1.cif
Contains datablocks global, 1, 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768199011544/bm00231sup2.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768199011544/bm00232sup3.hkl
Contains datablock 2

CCDC references: 141649; 141650

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, 1997b) for (1); SOLVER in NRCVAX96 (Gabe et al., 1989) for (2). Program(s) used to refine structure: NRCVAX96 (Gabe et al., 1989)and SHELXL97 (Sheldrick, 1997a) for (1); NRCVAX96 and SHELXL97 (Sheldrick, 1997b) for (2). For both compounds, molecular graphics: NRCVAX96, ORTEP (Johnson, 1976), PLATON (Spek, 1999); software used to prepare material for publication: NRCVAX96, SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

(1) Meso-5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetra- azacyclotetradecane–terephthalic acid–water (1/1/4). top
Crystal data top
C16H38N4·C8H4O4·4H2OF(000) = 1144
Mr = 522.68Dx = 1.234 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 13.3213 (4) ÅCell parameters from 6427 reflections
b = 14.0499 (4) Åθ = 4.1–27.5°
c = 16.0491 (6) ŵ = 0.09 mm1
β = 110.549 (2)°T = 100 K
V = 2812.67 (16) Å3Block, colourless
Z = 40.35 × 0.30 × 0.10 mm
Data collection top
Kappa-CCD
diffractometer
6427 independent reflections
Radiation source: fine-focus sealed X-ray tube4031 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.082
φ scans and ω scans with κ offsetsθmax = 27.5°, θmin = 4.1°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 017
Tmin = 0.969, Tmax = 0.991k = 018
32836 measured reflectionsl = 2019
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.099 w = 1/[σ2(Fo2) + (0.0512P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.91(Δ/σ)max = 0.002
6427 reflectionsΔρmax = 0.23 e Å3
371 parametersΔρmin = 0.20 e Å3
12 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997a), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0036 (7)
Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] 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:-

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N10.55614 (9)0.41092 (8)0.28573 (8)0.0175 (3)
C20.54253 (11)0.37934 (10)0.36943 (10)0.0199 (3)
C30.57108 (11)0.27535 (10)0.38679 (10)0.0202 (3)
N40.49519 (9)0.21587 (8)0.31778 (8)0.0179 (3)
C50.52038 (11)0.11208 (10)0.32400 (10)0.0198 (3)
C510.53580 (13)0.07242 (11)0.41651 (10)0.0279 (4)
C520.62127 (11)0.09660 (10)0.30045 (11)0.0244 (4)
C60.42294 (11)0.05990 (10)0.25729 (10)0.0218 (3)
C70.39833 (11)0.07637 (10)0.15823 (10)0.0207 (3)
C710.30228 (12)0.01707 (10)0.10253 (11)0.0273 (4)
N80.37573 (9)0.18045 (8)0.13754 (8)0.0183 (3)
C90.38448 (12)0.21265 (10)0.05212 (10)0.0212 (3)
C100.35345 (12)0.31622 (10)0.03572 (10)0.0230 (3)
N110.42840 (9)0.37652 (8)0.10425 (8)0.0203 (3)
C120.39486 (11)0.47798 (10)0.10703 (10)0.0216 (3)
C1210.35486 (13)0.52561 (11)0.01525 (11)0.0290 (4)
C1220.30590 (12)0.48136 (11)0.14643 (11)0.0282 (4)
C130.49530 (11)0.53232 (10)0.16589 (10)0.0217 (3)
C140.53339 (11)0.51514 (9)0.26577 (10)0.0200 (3)
C1410.63364 (12)0.57322 (10)0.31442 (10)0.0231 (3)
O211.26221 (8)0.25406 (8)0.28097 (7)0.0306 (3)
O221.17553 (8)0.21642 (7)0.13845 (7)0.0256 (3)
O230.68658 (8)0.34160 (7)0.17262 (7)0.0266 (3)
O240.76698 (8)0.37946 (7)0.31595 (7)0.0244 (2)
C211.07375 (11)0.27914 (9)0.22109 (10)0.0180 (3)
C220.98667 (11)0.30231 (9)0.14531 (10)0.0188 (3)
C230.88937 (11)0.32757 (9)0.15198 (10)0.0186 (3)
C240.87689 (11)0.33057 (9)0.23473 (10)0.0182 (3)
C250.96450 (11)0.30995 (9)0.31087 (10)0.0198 (3)
C261.06222 (11)0.28429 (10)0.30423 (10)0.0195 (3)
C271.17891 (11)0.24799 (10)0.21385 (10)0.0208 (3)
C280.76858 (11)0.35204 (10)0.24072 (10)0.0200 (3)
O30.99709 (10)0.08941 (8)0.04474 (8)0.0324 (3)
O40.82252 (11)0.20923 (10)0.03716 (9)0.0408 (3)
O50.65694 (10)0.20483 (9)0.03737 (9)0.0370 (3)
O60.59445 (10)0.02185 (9)0.06940 (9)0.0359 (3)
H1A0.62540.39840.28940.021*
H1B0.51100.37590.23920.021*
H2A0.46730.38940.36490.024*
H2B0.58910.41790.41980.024*
H3A0.64470.26450.38720.024*
H3B0.56930.25730.44590.024*
H4A0.42790.22390.32060.021*
H51A0.59690.10410.46080.042*
H51B0.54940.00380.41740.042*
H51C0.47090.08400.43050.042*
H52A0.61320.12970.24470.037*
H52B0.63120.02840.29330.037*
H52C0.68380.12190.34830.037*
H6A0.43370.00930.26860.026*
H6B0.35860.07810.27090.026*
H70.46230.05760.14310.025*
H71A0.23930.03480.11720.041*
H71B0.31800.05060.11540.041*
H71C0.28790.02890.03920.041*
H8A0.30760.19350.13640.022*
H8B0.42270.21550.18300.022*
H9A0.33680.17360.00270.025*
H9B0.45900.20390.05410.025*
H10A0.35370.33520.02360.028*
H10B0.28000.32530.03620.028*
H11A0.49320.37620.09570.024*
H12A0.41090.52220.01110.044*
H12B0.33760.59240.02160.044*
H12C0.29050.49260.02340.044*
H12D0.24000.45440.10380.042*
H12E0.29300.54760.15910.042*
H12F0.32760.44430.20170.042*
H13A0.55500.51620.14520.026*
H13B0.48110.60130.15540.026*
H140.47520.53490.28800.024*
H14A0.65920.55740.37790.035*
H14B0.61650.64120.30670.035*
H14C0.68960.55840.28990.035*
H220.99410.30080.08860.023*
H230.83050.34300.09980.022*
H250.95750.31340.36770.024*
H261.12150.27020.35650.023*
H311.0527 (12)0.1232 (13)0.0723 (13)0.061 (4)*
H320.949 (3)0.127 (3)0.014 (3)0.076 (6)*0.50
H330.999 (4)0.042 (2)0.013 (3)0.076 (6)*0.50
H410.7984 (16)0.2144 (15)0.0937 (8)0.061 (4)*
H420.778 (3)0.197 (3)0.012 (3)0.076 (6)*0.50
H430.864 (3)0.166 (2)0.009 (3)0.076 (6)*0.50
H510.6722 (16)0.2457 (13)0.0791 (11)0.061 (4)*
H520.7144 (19)0.197 (3)0.027 (3)0.076 (6)*0.50
H530.641 (4)0.1498 (14)0.050 (3)0.076 (6)*0.50
H610.6315 (15)0.0212 (12)0.1038 (13)0.061 (4)*
H620.539 (2)0.005 (4)0.028 (2)0.076 (6)*0.50
H630.621 (3)0.0731 (17)0.059 (3)0.076 (6)*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0172 (6)0.0168 (6)0.0192 (7)0.0012 (5)0.0072 (5)0.0020 (5)
C20.0213 (8)0.0208 (7)0.0184 (8)0.0004 (6)0.0081 (6)0.0014 (6)
C30.0203 (8)0.0203 (7)0.0184 (8)0.0007 (6)0.0048 (6)0.0012 (6)
N40.0145 (6)0.0181 (6)0.0216 (7)0.0011 (5)0.0070 (5)0.0012 (5)
C50.0213 (8)0.0175 (7)0.0197 (8)0.0024 (6)0.0063 (7)0.0018 (6)
C510.0349 (9)0.0203 (8)0.0265 (9)0.0015 (7)0.0083 (8)0.0019 (7)
C520.0209 (8)0.0229 (8)0.0270 (9)0.0035 (6)0.0056 (7)0.0024 (6)
C60.0224 (8)0.0169 (7)0.0253 (9)0.0009 (6)0.0075 (7)0.0007 (6)
C70.0195 (7)0.0167 (7)0.0256 (9)0.0019 (6)0.0076 (7)0.0021 (6)
C710.0255 (8)0.0220 (8)0.0304 (9)0.0019 (6)0.0050 (7)0.0022 (7)
N80.0159 (6)0.0184 (6)0.0203 (7)0.0002 (5)0.0060 (5)0.0021 (5)
C90.0218 (8)0.0235 (8)0.0192 (8)0.0004 (6)0.0084 (6)0.0015 (6)
C100.0244 (8)0.0244 (8)0.0181 (8)0.0003 (6)0.0049 (7)0.0000 (6)
N110.0191 (6)0.0198 (6)0.0219 (7)0.0011 (5)0.0072 (5)0.0002 (5)
C120.0223 (8)0.0186 (7)0.0224 (9)0.0033 (6)0.0059 (7)0.0012 (6)
C1210.0350 (9)0.0235 (8)0.0248 (9)0.0044 (7)0.0058 (7)0.0029 (7)
C1220.0209 (8)0.0330 (9)0.0283 (9)0.0028 (7)0.0056 (7)0.0039 (7)
C130.0234 (8)0.0184 (7)0.0240 (9)0.0024 (6)0.0092 (7)0.0027 (6)
C140.0206 (8)0.0157 (7)0.0238 (9)0.0026 (6)0.0080 (7)0.0004 (6)
C1410.0239 (8)0.0177 (7)0.0267 (9)0.0008 (6)0.0077 (7)0.0001 (6)
O210.0164 (6)0.0473 (7)0.0272 (7)0.0033 (5)0.0066 (5)0.0064 (5)
O220.0202 (5)0.0334 (6)0.0245 (6)0.0034 (4)0.0096 (5)0.0058 (5)
O230.0175 (5)0.0331 (6)0.0286 (7)0.0026 (4)0.0072 (5)0.0035 (5)
O240.0205 (6)0.0264 (6)0.0290 (6)0.0012 (4)0.0122 (5)0.0051 (5)
C210.0169 (7)0.0150 (7)0.0230 (8)0.0016 (6)0.0081 (6)0.0018 (6)
C220.0209 (7)0.0156 (7)0.0222 (8)0.0010 (6)0.0104 (6)0.0010 (6)
C230.0178 (7)0.0157 (7)0.0212 (8)0.0004 (6)0.0053 (6)0.0001 (6)
C240.0165 (7)0.0133 (7)0.0258 (9)0.0011 (5)0.0088 (6)0.0018 (6)
C250.0215 (8)0.0187 (7)0.0212 (8)0.0011 (6)0.0099 (7)0.0019 (6)
C260.0169 (7)0.0183 (7)0.0222 (8)0.0005 (6)0.0056 (6)0.0011 (6)
C270.0183 (8)0.0202 (7)0.0256 (9)0.0009 (6)0.0097 (7)0.0009 (6)
C280.0184 (7)0.0166 (7)0.0279 (9)0.0011 (6)0.0119 (7)0.0002 (6)
O30.0397 (7)0.0322 (7)0.0278 (7)0.0073 (6)0.0148 (6)0.0022 (5)
O40.0449 (8)0.0489 (8)0.0232 (7)0.0094 (6)0.0052 (6)0.0003 (6)
O50.0327 (7)0.0341 (7)0.0371 (8)0.0016 (6)0.0036 (6)0.0092 (6)
O60.0336 (7)0.0378 (8)0.0340 (8)0.0074 (6)0.0091 (6)0.0079 (6)
Geometric parameters (Å, º) top
N1—C21.485 (2)C12—C1211.533 (2)
N1—C141.507 (2)C12—C131.542 (2)
C2—C31.511 (2)C13—C141.521 (2)
C3—N41.470 (2)C14—C1411.525 (2)
N4—C51.492 (2)O21—C271.249 (2)
C5—C511.531 (2)O22—C271.275 (2)
C5—C521.534 (2)O23—C281.254 (2)
C5—C61.547 (2)O24—C281.275 (2)
C6—C71.524 (2)C21—C221.393 (2)
C7—N81.506 (2)C21—C261.398 (2)
C7—C711.526 (2)C21—C271.511 (2)
N8—C91.487 (2)C22—C231.384 (2)
C9—C101.510 (2)C23—C241.396 (2)
C10—N111.467 (2)C24—C251.392 (2)
N11—C121.499 (2)C24—C281.510 (2)
C12—C1221.527 (2)C25—C261.391 (2)
C2—N1—C14113.78 (10)C122—C12—C13111.31 (12)
N1—C2—C3110.67 (11)C121—C12—C13107.86 (12)
N4—C3—C2110.42 (11)C14—C13—C12117.62 (12)
C3—N4—C5115.23 (11)N1—C14—C13110.24 (11)
N4—C5—C51111.79 (12)N1—C14—C141109.66 (11)
N4—C5—C52108.55 (11)C13—C14—C141111.27 (12)
C51—C5—C52110.88 (12)C22—C21—C26118.98 (13)
N4—C5—C6107.61 (11)C22—C21—C27120.74 (13)
C51—C5—C6107.05 (11)C26—C21—C27120.28 (13)
C52—C5—C6110.92 (12)C23—C22—C21120.53 (14)
C7—C6—C5118.10 (12)C22—C23—C24120.60 (14)
N8—C7—C6109.30 (11)C25—C24—C23119.07 (13)
N8—C7—C71109.84 (11)C25—C24—C28120.73 (13)
C6—C7—C71110.94 (12)C23—C24—C28120.15 (13)
C9—N8—C7115.12 (11)C26—C25—C24120.37 (14)
N8—C9—C10110.41 (11)C25—C26—C21120.42 (13)
N11—C10—C9110.67 (12)O21—C27—O22124.56 (13)
C10—N11—C12116.09 (11)O21—C27—C21118.75 (13)
N11—C12—C122108.94 (11)O22—C27—C21116.69 (13)
N11—C12—C121113.15 (12)O23—C28—O24124.19 (13)
C122—C12—C121109.01 (12)O23—C28—C24118.75 (13)
N11—C12—C13106.58 (11)O24—C28—C24117.06 (13)
N1—C2—C3—N465.42 (15)C13—C14—N1—C2152.22 (11)
C2—C3—N4—C5175.44 (11)C14—N1—C2—C3177.67 (11)
C3—N4—C5—C5153.07 (16)C2—N1—C14—C14184.95 (14)
C3—N4—C5—C5269.55 (15)C12—C13—C14—C141179.54 (12)
C3—N4—C5—C6170.33 (11)C26—C21—C22—C231.7 (2)
N4—C5—C6—C767.49 (15)C27—C21—C22—C23177.71 (12)
C51—C5—C6—C7172.19 (12)C21—C22—C23—C240.2 (2)
C52—C5—C6—C751.10 (16)C22—C23—C24—C251.49 (19)
C5—C6—C7—N860.57 (16)C22—C23—C24—C28176.07 (12)
C5—C6—C7—C71178.15 (12)C23—C24—C25—C261.7 (2)
C6—C7—N8—C9161.45 (11)C28—C24—C25—C26175.86 (12)
C71—C7—N8—C976.61 (15)C24—C25—C26—C210.2 (2)
C7—N8—C9—C10176.44 (11)C22—C21—C26—C251.5 (2)
N8—C9—C10—N1163.91 (15)C27—C21—C26—C25177.91 (12)
C9—C10—N11—C12167.97 (12)C22—C21—C27—O21159.70 (13)
C10—N11—C12—C12273.79 (16)C26—C21—C27—O2120.9 (2)
C10—N11—C12—C12147.62 (17)C22—C21—C27—O2220.7 (2)
C10—N11—C12—C13166.01 (12)C26—C21—C27—O22158.69 (13)
N11—C12—C13—C1473.27 (15)C25—C24—C28—O23158.41 (13)
C122—C12—C13—C1445.40 (17)C23—C24—C28—O2319.11 (19)
C121—C12—C13—C14164.94 (12)C25—C24—C28—O2421.24 (19)
C12—C13—C14—N157.65 (16)C23—C24—C28—O24161.24 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···N110.922.062.852 (2)144
N1—H1A···O240.921.802.714 (2)170
N4—H4A···O21i0.922.112.997 (2)160
N8—H8A···O22i0.921.802.720 (2)178
N8—H8B···N40.922.042.814 (2)141
N11—H11A···O230.922.483.260 (2)142
O3—H31···O220.862.072.930 (2)174
O3—H32···O40.841.972.797 (2)167
O3—H33···O3ii0.842.072.908 (2)169
O4—H41···O21iii0.851.952.790 (2)169
O4—H42···O50.842.032.855 (2)164
O4—H43···O30.841.992.797 (2)160
O5—H51···O230.851.982.821 (2)172
O5—H52···O40.852.052.855 (2)159
O5—H53···O60.851.962.805 (2)175
O6—H61···O24iv0.852.052.900 (2)175
O6—H62···O6v0.841.952.781 (2)175
O6—H63···O50.841.972.805 (2)168
Symmetry codes: (i) x1, y, z; (ii) x+2, y, z; (iii) x1/2, y+1/2, z1/2; (iv) x+3/2, y1/2, z+1/2; (v) x+1, y, z.
(2) meso-5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetra- azacyclotetradecane–terephthalic acid–water (1/1/6) top
Crystal data top
C16H38N4·C8H4O4·6H2OF(000) = 612
Mr = 558.71Dx = 1.209 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 8.1772 (3) ÅCell parameters from 3512 reflections
b = 12.3974 (4) Åθ = 4.1–27.5°
c = 16.8804 (5) ŵ = 0.09 mm1
β = 116.231 (2)°T = 100 K
V = 1535.04 (9) Å3Block, colourless
Z = 20.40 × 0.32 × 0.24 mm
Data collection top
Kappa-CCD
diffractometer
3512 independent reflections
Radiation source: fine-focus sealed X-ray tube2756 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
φ scans and ω scans with κ offsetsθmax = 27.5°, θmin = 4.1°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 010
Tmin = 0.964, Tmax = 0.978k = 160
16757 measured reflectionsl = 2118
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H-atom parameters constrained
S = 0.98 w = 1/[σ2(Fo2) + (0.0696P)2 + 0.1606P]
where P = (Fo2 + 2Fc2)/3
3512 reflections(Δ/σ)max < 0.001
195 parametersΔρmax = 0.24 e Å3
6 restraintsΔρmin = 0.26 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.43906 (13)0.34031 (7)0.45781 (6)0.0186 (2)
C20.34495 (16)0.37368 (9)0.36312 (7)0.0229 (3)
C30.46504 (17)0.44708 (9)0.33952 (8)0.0218 (3)
N40.48453 (13)0.55262 (7)0.38237 (6)0.0181 (2)
C50.62579 (15)0.62579 (9)0.37848 (7)0.0202 (2)
C510.59812 (18)0.64618 (11)0.28345 (8)0.0277 (3)
C520.81481 (16)0.57641 (10)0.43225 (8)0.0258 (3)
C60.60556 (16)0.73514 (9)0.41699 (8)0.0217 (2)
C70.66696 (16)0.74052 (9)0.51631 (8)0.0219 (3)
C710.64470 (19)0.85370 (10)0.54544 (9)0.0306 (3)
O110.86632 (13)0.20922 (7)0.61269 (6)0.0290 (2)
O120.75750 (11)0.25689 (6)0.47077 (5)0.0236 (2)
C110.92580 (15)0.09386 (9)0.51667 (7)0.0176 (2)
C121.06615 (15)0.03939 (9)0.58550 (7)0.0191 (2)
C131.14005 (15)0.05361 (9)0.56921 (7)0.0186 (2)
C140.84476 (16)0.19463 (9)0.53520 (8)0.0203 (2)
O30.90241 (12)0.36486 (7)0.73534 (6)0.0254 (2)
O41.13898 (14)0.53980 (7)0.77455 (6)0.0309 (2)
O50.87974 (13)0.19899 (7)0.84420 (6)0.0282 (2)
H1A0.54800.31160.46860.022*
H1B0.45960.39930.49200.022*
H2A0.23270.41100.35220.027*
H2B0.31380.31010.32580.027*
H3A0.58420.41440.35850.026*
H3B0.41160.45650.27600.026*
H4A0.37620.58660.35720.022*
H51A0.59720.57850.25560.042*
H51B0.69580.69020.28470.042*
H51C0.48410.68250.25080.042*
H52A0.82530.55280.48850.039*
H52B0.90670.62960.44110.039*
H52C0.83090.51600.40080.039*
H6A0.67400.78860.40200.026*
H6B0.47820.75600.38750.026*
H70.79640.72110.54640.026*
H71A0.52050.87660.51260.046*
H71B0.72380.90250.53470.046*
H71C0.67580.85320.60730.046*
H121.11050.06570.64280.023*
H131.23370.08930.61550.022*
H3C0.901 (2)0.3263 (14)0.6913 (9)0.054 (2)*
H3D0.984 (2)0.4159 (12)0.7468 (12)0.054 (2)*
H4C1.140 (3)0.5793 (13)0.7317 (9)0.054 (2)*
H4D1.136 (2)0.5849 (13)0.8140 (10)0.054 (2)*
H5C0.837 (2)0.2163 (15)0.8821 (10)0.054 (2)*
H5D0.889 (3)0.2556 (11)0.8152 (11)0.054 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0192 (5)0.0160 (4)0.0206 (5)0.0002 (4)0.0087 (4)0.0018 (4)
C20.0244 (6)0.0204 (6)0.0189 (6)0.0010 (5)0.0050 (5)0.0027 (4)
C30.0276 (6)0.0195 (6)0.0181 (6)0.0013 (5)0.0099 (5)0.0009 (4)
N40.0174 (5)0.0169 (5)0.0197 (5)0.0011 (4)0.0078 (4)0.0009 (4)
C50.0190 (5)0.0226 (6)0.0200 (6)0.0004 (4)0.0096 (5)0.0016 (4)
C510.0301 (6)0.0325 (7)0.0224 (6)0.0001 (5)0.0132 (5)0.0039 (5)
C520.0201 (6)0.0308 (6)0.0255 (6)0.0025 (5)0.0091 (5)0.0003 (5)
C60.0221 (6)0.0191 (5)0.0250 (6)0.0013 (4)0.0115 (5)0.0019 (4)
C70.0207 (6)0.0203 (6)0.0262 (6)0.0037 (5)0.0117 (5)0.0019 (4)
C710.0377 (7)0.0203 (6)0.0394 (8)0.0091 (5)0.0222 (6)0.0067 (5)
O110.0462 (5)0.0216 (4)0.0258 (5)0.0051 (4)0.0219 (4)0.0003 (3)
O120.0268 (4)0.0204 (4)0.0284 (5)0.0058 (3)0.0166 (4)0.0056 (3)
C110.0197 (5)0.0155 (5)0.0207 (6)0.0017 (4)0.0117 (5)0.0009 (4)
C120.0213 (5)0.0194 (5)0.0170 (5)0.0020 (4)0.0088 (5)0.0005 (4)
C130.0182 (5)0.0181 (5)0.0183 (5)0.0010 (4)0.0069 (4)0.0033 (4)
C140.0221 (5)0.0174 (5)0.0253 (6)0.0002 (5)0.0140 (5)0.0013 (4)
O30.0298 (5)0.0239 (4)0.0246 (5)0.0012 (4)0.0140 (4)0.0032 (3)
O40.0484 (6)0.0222 (5)0.0290 (5)0.0024 (4)0.0234 (5)0.0007 (4)
O50.0405 (5)0.0237 (4)0.0274 (5)0.0004 (4)0.0214 (4)0.0014 (4)
Geometric parameters (Å, º) top
N1—C21.494 (2)C7—N1i1.5104 (14)
N1—C7i1.510 (2)C7—C711.5241 (16)
C2—C31.5155 (16)O11—C141.254 (2)
C3—N41.469 (2)O12—C141.266 (2)
N4—C51.493 (2)C11—C121.3945 (16)
C5—C521.5321 (16)C11—C13ii1.3965 (16)
C5—C511.5385 (16)C11—C141.5103 (15)
C5—C61.5437 (16)C12—C131.3846 (16)
C6—C71.5243 (16)C13—C11ii1.3965 (16)
C2—N1—C7i113.8 (1)N1i—C7—C71110.60 (9)
N1—C2—C3111.12 (9)N1i—C7—C6109.70 (9)
N4—C3—C2110.32 (9)C71—C7—C6111.52 (10)
C3—N4—C5115.9 (1)C12—C11—C13ii119.32 (10)
N4—C5—C52109.19 (9)C12—C11—C14120.19 (10)
N4—C5—C51112.69 (9)C13ii—C11—C14120.49 (10)
C52—C5—C51109.17 (10)C13—C12—C11120.56 (10)
N4—C5—C6106.62 (9)C12—C13—C11ii120.12 (10)
C52—C5—C6111.66 (10)O11—C14—O12125.1 (2)
C51—C5—C6107.51 (9)O11—C14—C11117.60 (10)
C7—C6—C5117.20 (10)O12—C14—C11117.31 (10)
C7i—N1—C2—C3175.1 (1)C5—C6—C7—N1i58.9 (2)
N1—C2—C3—N470.1 (2)C5—C6—C7—C71178.25 (10)
C2—C3—N4—C5169.2 (1)C13ii—C11—C12—C130.08 (18)
C3—N4—C5—C5265.94 (12)C14—C11—C12—C13179.39 (10)
C3—N4—C5—C5155.55 (13)C11—C12—C13—C11ii0.07 (18)
C3—N4—C5—C6173.3 (1)C12—C11—C14—O1120.59 (16)
N4—C5—C6—C771.7 (2)C13ii—C11—C14—O11158.72 (11)
C52—C5—C6—C747.49 (13)C12—C11—C14—O12160.6 (1)
C51—C5—C6—C7167.21 (10)C13ii—C11—C14—O1220.1 (2)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+2, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O120.901.832.719 (2)170
N1—H1B···N4i0.902.052.818 (2)142
O3—H3C···O110.88 (2)1.90 (2)2.749 (2)161
O3—H3D···O40.88 (2)1.91 (2)2.784 (2)172
N4—H4A···O3i0.902.203.074 (2)163
O4—H4C···O5iii0.88 (2)1.92 (2)2.769 (2)163
O4—H4D···O11iii0.88 (2)1.98 (2)2.848 (2)169
O5—H5C···O12iv0.88 (2)1.91 (2)2.784 (2)175
O5—H5D···O30.88 (2)1.95 (2)2.818 (2)171
C7—H7···O5iii0.982.493.440 (2)165
Symmetry codes: (i) x+1, y+1, z+1; (iii) x+2, y+1/2, z+3/2; (iv) x, y1/2, z1/2.
 

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