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The
meso and racemic forms of 5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane, C
16H
36N
4 (tet-a and tet-b, respectively), form adducts with trigonally trisubstituted benzene carboxylic acids; tet-a–3,5-dinitrobenzoic acid (1/2) (1), tet-a–5-hydroxyisophthalic acid–water (1/1/1) (3) and tet-b–5-hydroxyisophthalic acid–water (1/1/1) (4) are all salts, [C
16H
38N
4]
2+·2[C
7H
3N
2O
6]
− (1) and [C
16H
38N
4]
2+·[C
8H
4O
5]
2−·H
2O (3) and (4). The conformations of the [(tet-a)H
2]
2+ and [(tet-b)H
2]
2+ cations are entirely different: [(tet-a)H
2]
2+ is precisely centrosymmetric in (1) and approximately so in (3), while [(tet-b)H
2]
2+ has approximate
C2 symmetry in (4). In each salt the cation forms two intramolecular N—H
N and four intermolecular N—H
O hydrogen bonds. In (1) the supramolecular structure is one-dimensional, a
C22(13)[
R24(16)] chain of rings. Compounds (3) and (4) crystallize in space groups
P2
12
12
1 and
P2
1/
c, respectively, but the supramolecular structures are very similar: in each, the anions and the water molecules form a
C(7)[
R33(13)] chain of rings, generated in (3) by a 2
1 axis and in (4) by a glide plane. These chains are linked, in both (3) and (4), by cations to form sheets. Adjacent
meso cations in (3) are related by a 2
1 axis and adjacent chiral cations in (4) are related by a glide plane.
Supporting information
CCDC references: 156706; 156707; 156708
For all 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, 2000); 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-tetraazacyclotetradecane–3,5- dinitrobenzoic acid(1/2)
top
Crystal data top
C16H38N4·2(C7H3N2O6) | Z = 1 |
Mr = 708.73 | F(000) = 376 |
Triclinic, P1 | Dx = 1.356 Mg m−3 |
a = 8.7336 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.9388 (3) Å | Cell parameters from 12749 reflections |
c = 11.0284 (3) Å | θ = 3.0–30.0° |
α = 114.5800 (17)° | µ = 0.11 mm−1 |
β = 91.9660 (18)° | T = 150 K |
γ = 111.6740 (18)° | Block, colourless |
V = 868.09 (4) Å3 | 0.26 × 0.16 × 0.14 mm |
Data collection top
Kappa-CCD diffractometer | 5013 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 3651 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ϕ scans and ω scans with κ offsets | θmax = 30.0°, θmin = 3.0° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = 0→12 |
Tmin = 0.973, Tmax = 0.985 | k = −15→14 |
12749 measured reflections | l = −15→15 |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0542P)2 + 0.1566P] where P = (Fo2 + 2Fc2)/3 |
5013 reflections | (Δ/σ)max = 0.001 |
229 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
Crystal data top
C16H38N4·2(C7H3N2O6) | γ = 111.6740 (18)° |
Mr = 708.73 | V = 868.09 (4) Å3 |
Triclinic, P1 | Z = 1 |
a = 8.7336 (3) Å | Mo Kα radiation |
b = 10.9388 (3) Å | µ = 0.11 mm−1 |
c = 11.0284 (3) Å | T = 150 K |
α = 114.5800 (17)° | 0.26 × 0.16 × 0.14 mm |
β = 91.9660 (18)° | |
Data collection top
Kappa-CCD diffractometer | 5013 independent reflections |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | 3651 reflections with I > 2σ(I) |
Tmin = 0.973, Tmax = 0.985 | Rint = 0.023 |
12749 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.24 e Å−3 |
5013 reflections | Δρmin = −0.27 e Å−3 |
229 parameters | |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.38165 (12) | 0.63318 (10) | 0.55172 (10) | 0.0214 (2) | |
C2 | 0.23199 (16) | 0.54780 (13) | 0.58511 (13) | 0.0252 (3) | |
C3 | 0.27683 (16) | 0.47571 (13) | 0.66386 (12) | 0.0259 (3) | |
N4 | 0.35154 (13) | 0.37403 (10) | 0.58203 (10) | 0.0214 (2) | |
C5 | 0.39028 (16) | 0.28369 (13) | 0.64208 (12) | 0.0242 (3) | |
C51 | 0.22302 (19) | 0.17058 (15) | 0.64215 (15) | 0.0351 (3) | |
C52 | 0.4994 (2) | 0.38603 (16) | 0.78661 (13) | 0.0356 (3) | |
C6 | 0.48122 (16) | 0.20053 (13) | 0.54566 (13) | 0.0254 (3) | |
C7 | 0.64938 (16) | 0.28992 (13) | 0.52269 (12) | 0.0238 (3) | |
C71 | 0.73192 (18) | 0.18624 (15) | 0.44979 (15) | 0.0344 (3) | |
O1 | 0.12100 (13) | 0.17636 (11) | 0.34034 (9) | 0.0387 (3) | |
O2 | 0.30300 (12) | 0.31943 (12) | 0.26448 (10) | 0.0399 (3) | |
O3 | 0.06891 (16) | 0.39464 (13) | −0.09511 (12) | 0.0507 (3) | |
O4 | −0.18082 (19) | 0.24172 (18) | −0.22159 (14) | 0.0710 (4) | |
O5 | −0.52769 (12) | −0.15405 (11) | −0.12954 (10) | 0.0399 (3) | |
O6 | −0.42798 (15) | −0.18797 (13) | 0.02998 (12) | 0.0545 (3) | |
N3 | −0.06477 (18) | 0.28683 (16) | −0.12643 (13) | 0.0422 (3) | |
N5 | −0.41460 (15) | −0.12071 (13) | −0.03649 (11) | 0.0353 (3) | |
C11 | 0.01922 (16) | 0.17937 (14) | 0.14061 (12) | 0.0256 (3) | |
C12 | 0.04189 (17) | 0.25421 (15) | 0.06233 (13) | 0.0289 (3) | |
C13 | −0.08773 (18) | 0.20456 (15) | −0.04618 (13) | 0.0305 (3) | |
C14 | −0.23778 (17) | 0.08107 (15) | −0.08256 (12) | 0.0310 (3) | |
C15 | −0.25553 (16) | 0.00957 (14) | −0.00260 (12) | 0.0275 (3) | |
C16 | −0.13147 (16) | 0.05700 (14) | 0.10921 (12) | 0.0261 (3) | |
C17 | 0.16098 (16) | 0.23011 (14) | 0.25890 (12) | 0.0286 (3) | |
H1 | 0.4610 | 0.7026 | 0.6316 | 0.026* | |
H2A | 0.1470 | 0.4702 | 0.4997 | 0.030* | |
H2B | 0.1816 | 0.6141 | 0.6407 | 0.030* | |
H3A | 0.3587 | 0.5534 | 0.7509 | 0.031* | |
H3B | 0.1739 | 0.4192 | 0.6860 | 0.031* | |
H4A | 0.4503 | 0.4297 | 0.5672 | 0.026* | |
H4B | 0.2785 | 0.3092 | 0.4980 | 0.026* | |
H51A | 0.1631 | 0.2226 | 0.7016 | 0.053* | |
H51B | 0.2452 | 0.1076 | 0.6761 | 0.053* | |
H51C | 0.1534 | 0.1089 | 0.5488 | 0.053* | |
H52A | 0.5929 | 0.4706 | 0.7871 | 0.053* | |
H52B | 0.5447 | 0.3314 | 0.8171 | 0.053* | |
H52C | 0.4306 | 0.4219 | 0.8485 | 0.053* | |
H6A | 0.5014 | 0.1367 | 0.5808 | 0.030* | |
H6B | 0.4021 | 0.1338 | 0.4552 | 0.030* | |
H7 | 0.7255 | 0.3666 | 0.6141 | 0.029* | |
H71A | 0.6581 | 0.1090 | 0.3606 | 0.052* | |
H71B | 0.7496 | 0.1401 | 0.5053 | 0.052* | |
H71C | 0.8410 | 0.2431 | 0.4368 | 0.052* | |
H12 | 0.1446 | 0.3380 | 0.0829 | 0.035* | |
H14 | −0.3243 | 0.0471 | −0.1587 | 0.037* | |
H16 | −0.1494 | 0.0066 | 0.1634 | 0.031* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0207 (5) | 0.0216 (5) | 0.0230 (5) | 0.0078 (4) | 0.0038 (4) | 0.0124 (4) |
C2 | 0.0226 (6) | 0.0272 (6) | 0.0323 (6) | 0.0121 (5) | 0.0097 (5) | 0.0176 (5) |
C3 | 0.0303 (7) | 0.0279 (6) | 0.0275 (6) | 0.0154 (5) | 0.0131 (5) | 0.0166 (5) |
N4 | 0.0228 (5) | 0.0227 (5) | 0.0215 (5) | 0.0094 (4) | 0.0058 (4) | 0.0127 (4) |
C5 | 0.0289 (6) | 0.0236 (5) | 0.0250 (6) | 0.0109 (5) | 0.0063 (5) | 0.0156 (5) |
C51 | 0.0390 (8) | 0.0300 (6) | 0.0463 (8) | 0.0146 (6) | 0.0210 (6) | 0.0254 (6) |
C52 | 0.0455 (8) | 0.0400 (7) | 0.0255 (6) | 0.0200 (6) | 0.0041 (6) | 0.0173 (6) |
C6 | 0.0288 (6) | 0.0214 (5) | 0.0290 (6) | 0.0104 (5) | 0.0065 (5) | 0.0144 (5) |
C7 | 0.0261 (6) | 0.0239 (5) | 0.0258 (6) | 0.0119 (5) | 0.0046 (5) | 0.0142 (5) |
C71 | 0.0365 (8) | 0.0348 (7) | 0.0475 (8) | 0.0225 (6) | 0.0164 (6) | 0.0257 (6) |
O1 | 0.0394 (6) | 0.0444 (6) | 0.0269 (5) | 0.0124 (5) | −0.0022 (4) | 0.0169 (4) |
O2 | 0.0255 (5) | 0.0521 (6) | 0.0335 (5) | 0.0097 (4) | 0.0007 (4) | 0.0184 (5) |
O3 | 0.0584 (8) | 0.0582 (7) | 0.0545 (7) | 0.0272 (6) | 0.0268 (6) | 0.0394 (6) |
O4 | 0.0688 (9) | 0.1056 (11) | 0.0595 (8) | 0.0336 (8) | 0.0036 (7) | 0.0601 (8) |
O5 | 0.0273 (5) | 0.0414 (5) | 0.0315 (5) | 0.0130 (4) | −0.0015 (4) | 0.0017 (4) |
O6 | 0.0455 (7) | 0.0526 (7) | 0.0528 (7) | 0.0008 (5) | 0.0040 (5) | 0.0310 (6) |
N3 | 0.0486 (8) | 0.0600 (8) | 0.0368 (7) | 0.0304 (7) | 0.0171 (6) | 0.0318 (6) |
N5 | 0.0286 (6) | 0.0367 (6) | 0.0283 (6) | 0.0100 (5) | 0.0050 (5) | 0.0074 (5) |
C11 | 0.0247 (6) | 0.0316 (6) | 0.0196 (5) | 0.0144 (5) | 0.0045 (4) | 0.0089 (5) |
C12 | 0.0270 (6) | 0.0334 (6) | 0.0256 (6) | 0.0135 (5) | 0.0070 (5) | 0.0123 (5) |
C13 | 0.0334 (7) | 0.0426 (7) | 0.0256 (6) | 0.0213 (6) | 0.0112 (5) | 0.0198 (6) |
C14 | 0.0280 (7) | 0.0448 (7) | 0.0207 (6) | 0.0192 (6) | 0.0043 (5) | 0.0122 (6) |
C15 | 0.0221 (6) | 0.0314 (6) | 0.0235 (6) | 0.0107 (5) | 0.0049 (5) | 0.0083 (5) |
C16 | 0.0287 (7) | 0.0303 (6) | 0.0199 (5) | 0.0150 (5) | 0.0068 (5) | 0.0099 (5) |
C17 | 0.0266 (7) | 0.0335 (6) | 0.0218 (6) | 0.0152 (5) | 0.0017 (5) | 0.0075 (5) |
Geometric parameters (Å, º) top
N1—C2 | 1.461 (2) | C7—C71 | 1.5288 (18) |
N1—C7i | 1.477 (2) | C7—H7 | 1.00 |
N1—H1 | 0.92 | C71—H71A | 0.98 |
C2—C3 | 1.5179 (17) | C71—H71B | 0.98 |
C2—H2A | 0.99 | C71—H71C | 0.98 |
C2—H2B | 0.99 | O1—C17 | 1.258 (2) |
C3—N4 | 1.490 (2) | O2—C17 | 1.244 (2) |
C3—H3A | 0.99 | O3—N3 | 1.2204 (18) |
C3—H3B | 0.99 | O4—N3 | 1.2244 (18) |
N4—C5 | 1.518 (2) | O5—N5 | 1.2307 (15) |
N4—H4A | 0.92 | O6—N5 | 1.2179 (17) |
N4—H4B | 0.92 | N3—C13 | 1.4747 (18) |
C5—C52 | 1.5248 (17) | N5—C15 | 1.4696 (17) |
C5—C51 | 1.5267 (18) | C11—C12 | 1.3910 (18) |
C5—C6 | 1.5415 (17) | C11—C16 | 1.3876 (18) |
C51—H51A | 0.98 | C11—C17 | 1.5238 (17) |
C51—H51B | 0.98 | C12—C13 | 1.3859 (18) |
C51—H51C | 0.98 | C12—H12 | 0.95 |
C52—H52A | 0.98 | C13—C14 | 1.382 (2) |
C52—H52B | 0.98 | C14—C15 | 1.3809 (19) |
C52—H52C | 0.98 | C14—H14 | 0.95 |
C6—C7 | 1.5324 (17) | C15—C16 | 1.3873 (17) |
C6—H6A | 0.99 | C16—H16 | 0.95 |
C6—H6B | 0.99 | | |
| | | |
C2—N1—C7i | 114.71 (9) | C7—C6—H6B | 107.5 |
C2—N1—H1 | 108.6 | C5—C6—H6B | 107.5 |
C7i—N1—H1 | 108.6 | H6A—C6—H6B | 107.0 |
N1—C2—C3 | 110.90 (10) | N1i—C7—C71 | 114.04 (10) |
N1—C2—H2A | 109.5 | N1i—C7—C6 | 108.96 (10) |
C3—C2—H2A | 109.5 | C71—C7—C6 | 108.99 (10) |
N1—C2—H2B | 109.5 | N1i—C7—H7 | 108.2 |
C3—C2—H2B | 109.5 | C71—C7—H7 | 108.2 |
H2A—C2—H2B | 108.0 | C6—C7—H7 | 108.2 |
N4—C3—C2 | 110.67 (10) | C7—C71—H71A | 109.5 |
N4—C3—H3A | 109.5 | C7—C71—H71B | 109.5 |
C2—C3—H3A | 109.5 | H71A—C71—H71B | 109.5 |
N4—C3—H3B | 109.5 | C7—C71—H71C | 109.5 |
C2—C3—H3B | 109.5 | H71A—C71—H71C | 109.5 |
H3A—C3—H3B | 108.1 | H71B—C71—H71C | 109.5 |
C3—N4—C5 | 117.10 (9) | O3—N3—O4 | 123.91 (14) |
C3—N4—H4A | 108.0 | O3—N3—C13 | 118.27 (12) |
C5—N4—H4A | 108.0 | O4—N3—C13 | 117.82 (14) |
C3—N4—H4B | 108.0 | O6—N5—O5 | 123.84 (12) |
C5—N4—H4B | 108.0 | O6—N5—C15 | 118.41 (11) |
H4A—N4—H4B | 107.3 | O5—N5—C15 | 117.74 (12) |
N4—C5—C52 | 109.85 (10) | C16—C11—C12 | 119.86 (11) |
N4—C5—C51 | 108.22 (10) | C16—C11—C17 | 120.16 (12) |
C52—C5—C51 | 111.06 (11) | C12—C11—C17 | 119.97 (12) |
N4—C5—C6 | 106.76 (9) | C13—C12—C11 | 118.96 (12) |
C52—C5—C6 | 111.86 (11) | C13—C12—H12 | 120.5 |
C51—C5—C6 | 108.93 (10) | C11—C12—H12 | 120.5 |
C5—C51—H51A | 109.5 | C14—C13—C12 | 122.80 (12) |
C5—C51—H51B | 109.5 | C14—C13—N3 | 118.49 (12) |
H51A—C51—H51B | 109.5 | C12—C13—N3 | 118.70 (13) |
C5—C51—H51C | 109.5 | C15—C14—C13 | 116.54 (11) |
H51A—C51—H51C | 109.5 | C15—C14—H14 | 121.7 |
H51B—C51—H51C | 109.5 | C13—C14—H14 | 121.7 |
C5—C52—H52A | 109.5 | C14—C15—C16 | 122.91 (12) |
C5—C52—H52B | 109.5 | C14—C15—N5 | 118.19 (11) |
H52A—C52—H52B | 109.5 | C16—C15—N5 | 118.88 (12) |
C5—C52—H52C | 109.5 | C15—C16—C11 | 118.88 (12) |
H52A—C52—H52C | 109.5 | C15—C16—H16 | 120.6 |
H52B—C52—H52C | 109.5 | C11—C16—H16 | 120.6 |
C7—C6—C5 | 119.13 (10) | O2—C17—O1 | 127.1 (2) |
C7—C6—H6A | 107.5 | O2—C17—C11 | 116.81 (12) |
C5—C6—H6A | 107.5 | O1—C17—C11 | 116.07 (12) |
| | | |
C7i—N1—C2—C3 | −178.79 (9) | O3—N3—C13—C12 | 0.97 (19) |
N1—C2—C3—N4 | −59.6 (2) | O4—N3—C13—C12 | −179.73 (14) |
C2—C3—N4—C5 | −175.2 (2) | C12—C13—C14—C15 | 1.6 (2) |
C3—N4—C5—C52 | −53.2 (2) | N3—C13—C14—C15 | −178.45 (11) |
C3—N4—C5—C51 | 68.2 (2) | C13—C14—C15—C16 | 0.15 (19) |
C3—N4—C5—C6 | −174.6 (2) | C13—C14—C15—N5 | 178.92 (11) |
N4—C5—C6—C7 | 60.7 (2) | O6—N5—C15—C14 | 176.83 (13) |
C52—C5—C6—C7 | −59.54 (14) | O5—N5—C15—C14 | −4.22 (18) |
C51—C5—C6—C7 | 177.29 (11) | O6—N5—C15—C16 | −4.36 (19) |
C5—C6—C7—N1i | −67.1 (2) | O5—N5—C15—C16 | 174.60 (11) |
C6—C7—N1i—C2i | −177.8 (2) | C14—C15—C16—C11 | −1.71 (19) |
C5—C6—C7—C71 | 167.88 (11) | N5—C15—C16—C11 | 179.53 (11) |
C16—C11—C12—C13 | 0.06 (18) | C12—C11—C16—C15 | 1.57 (18) |
C17—C11—C12—C13 | 178.93 (11) | C17—C11—C16—C15 | −177.30 (11) |
C11—C12—C13—C14 | −1.7 (2) | C16—C11—C17—O2 | 165.61 (12) |
C11—C12—C13—N3 | 178.33 (11) | C12—C11—C17—O2 | −13.25 (18) |
O3—N3—C13—C14 | −178.99 (13) | C16—C11—C17—O1 | −14.25 (18) |
O4—N3—C13—C14 | 0.3 (2) | C12—C11—C17—O1 | 166.88 (11) |
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—H1···O5ii | 0.92 | 2.42 | 3.169 (2) | 139 |
N1—H1···O2i | 0.92 | 2.46 | 3.107 (2) | 127 |
N4—H4A···N1i | 0.92 | 2.12 | 2.808 (2) | 131 |
N4—H4B···O1 | 0.92 | 1.81 | 2.730 (2) | 175 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y+1, z+1. |
(3)
meso-5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetraazacyclotetradecane–5- hydroxyisophthalic acid–water (1/1/1)
top
Crystal data top
C16H38N4·C8H4O5·H2O | Dx = 1.235 Mg m−3 |
Mr = 484.63 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 4203 reflections |
a = 11.8760 (5) Å | θ = 2.6–30.0° |
b = 13.8395 (6) Å | µ = 0.09 mm−1 |
c = 15.8571 (7) Å | T = 100 K |
V = 2606.2 (2) Å3 | Block, colourless |
Z = 4 | 0.24 × 0.24 × 0.16 mm |
F(000) = 1056 | |
Data collection top
Kappa-CCD diffractometer | 4203 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 3479 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ϕ scans and ω scans with κ offsets | θmax = 30.0°, θmin = 2.6° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = 0→16 |
Tmin = 0.979, Tmax = 0.986 | k = 0→19 |
30326 measured reflections | l = 0→22 |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.048P)2 + 0.8417P] where P = (Fo2 + 2Fc2)/3 |
4203 reflections | (Δ/σ)max = 0.008 |
323 parameters | Δρmax = 0.30 e Å−3 |
4 restraints | Δρmin = −0.27 e Å−3 |
Crystal data top
C16H38N4·C8H4O5·H2O | V = 2606.2 (2) Å3 |
Mr = 484.63 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 11.8760 (5) Å | µ = 0.09 mm−1 |
b = 13.8395 (6) Å | T = 100 K |
c = 15.8571 (7) Å | 0.24 × 0.24 × 0.16 mm |
Data collection top
Kappa-CCD diffractometer | 4203 independent reflections |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | 3479 reflections with I > 2σ(I) |
Tmin = 0.979, Tmax = 0.986 | Rint = 0.033 |
30326 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.058 | 4 restraints |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.30 e Å−3 |
4203 reflections | Δρmin = −0.27 e Å−3 |
323 parameters | |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
N1 | 0.34185 (16) | 0.59626 (15) | 0.40203 (12) | 0.0254 (4) | |
C2 | 0.4132 (2) | 0.5455 (2) | 0.33948 (16) | 0.0336 (6) | |
C3 | 0.3886 (2) | 0.43810 (19) | 0.34068 (15) | 0.0334 (6) | |
N4 | 0.42921 (16) | 0.39450 (14) | 0.41955 (12) | 0.0260 (4) | |
C5 | 0.4173 (2) | 0.28717 (19) | 0.42516 (16) | 0.0337 (6) | |
C51 | 0.2922 (3) | 0.2597 (3) | 0.4211 (2) | 0.0473 (9) | 0.853 (3) |
C52 | 0.4820 (4) | 0.2351 (3) | 0.3553 (2) | 0.0593 (10) | |
C6 | 0.4705 (2) | 0.2565 (2) | 0.51002 (17) | 0.0344 (6) | |
C7 | 0.4090 (2) | 0.28755 (18) | 0.58984 (17) | 0.0324 (6) | |
C71' | 0.2824 (5) | 0.2699 (16) | 0.5801 (15) | 0.049 (5)* | 0.147 (3) |
C71 | 0.4670 (3) | 0.2496 (2) | 0.66905 (18) | 0.0440 (7) | |
N8 | 0.40503 (17) | 0.39646 (14) | 0.59278 (12) | 0.0257 (4) | |
C10 | 0.3226 (2) | 0.5429 (2) | 0.65570 (15) | 0.0386 (7) | |
C9 | 0.3136 (2) | 0.4351 (2) | 0.64702 (16) | 0.0347 (6) | |
N11 | 0.30714 (17) | 0.59140 (15) | 0.57453 (12) | 0.0271 (4) | |
C12 | 0.3310 (3) | 0.6962 (2) | 0.57481 (18) | 0.0385 (7) | |
C121 | 0.4609 (3) | 0.7076 (3) | 0.5890 (3) | 0.0475 (9) | 0.853 (3) |
C122 | 0.2638 (4) | 0.7483 (2) | 0.6430 (2) | 0.0634 (11) | |
C13 | 0.2956 (3) | 0.73753 (19) | 0.48878 (18) | 0.0373 (6) | |
C14 | 0.3596 (2) | 0.70319 (19) | 0.41085 (18) | 0.0344 (6) | |
C14' | 0.4828 (7) | 0.7282 (17) | 0.4288 (15) | 0.054 (6)* | 0.147 (3) |
C141 | 0.3172 (3) | 0.7541 (2) | 0.3324 (2) | 0.0532 (9) | |
O21 | 0.08937 (16) | 0.5272 (2) | 0.47951 (11) | 0.0544 (6) | |
O22 | 0.13527 (15) | 0.56795 (16) | 0.34915 (11) | 0.0409 (5) | |
O23 | −0.12615 (14) | 0.53861 (14) | 0.11341 (10) | 0.0305 (4) | |
O24 | −0.30472 (15) | 0.50267 (15) | 0.13734 (11) | 0.0379 (5) | |
O25 | −0.33493 (15) | 0.45280 (17) | 0.44872 (11) | 0.0418 (5) | |
C21 | −0.05301 (18) | 0.52055 (17) | 0.37323 (14) | 0.0222 (5) | |
C22 | −0.07526 (19) | 0.52725 (16) | 0.28719 (14) | 0.0223 (4) | |
C23 | −0.18219 (19) | 0.50781 (16) | 0.25599 (13) | 0.0206 (4) | |
C24 | −0.26708 (19) | 0.48109 (17) | 0.31173 (14) | 0.0253 (5) | |
C25 | −0.24583 (19) | 0.47660 (18) | 0.39838 (14) | 0.0258 (5) | |
C26 | −0.13844 (19) | 0.49559 (16) | 0.42937 (14) | 0.0234 (5) | |
C27 | 0.06621 (19) | 0.53952 (19) | 0.40395 (14) | 0.0276 (5) | |
C28 | −0.2070 (2) | 0.51642 (17) | 0.16184 (14) | 0.0240 (5) | |
O1 | 0.03353 (15) | 0.5312 (3) | 0.64583 (11) | 0.0798 (10) | |
H1A | 0.3537 | 0.5682 | 0.4539 | 0.030* | |
H1B | 0.2677 | 0.5859 | 0.3880 | 0.030* | |
H2A | 0.4936 | 0.5566 | 0.3528 | 0.040* | |
H2B | 0.3982 | 0.5717 | 0.2825 | 0.040* | |
H3A | 0.3064 | 0.4275 | 0.3354 | 0.040* | |
H3B | 0.4260 | 0.4067 | 0.2921 | 0.040* | |
H4A | 0.5040 | 0.4100 | 0.4260 | 0.031* | |
H51A | 0.2493 | 0.3011 | 0.4596 | 0.071* | 0.853 (3) |
H51B | 0.2830 | 0.1920 | 0.4377 | 0.071* | 0.853 (3) |
H51C | 0.2645 | 0.2686 | 0.3634 | 0.071* | 0.853 (3) |
H52A | 0.4499 | 0.2524 | 0.3004 | 0.089* | |
H52B | 0.4763 | 0.1651 | 0.3636 | 0.089* | |
H52C | 0.5614 | 0.2545 | 0.3571 | 0.089* | |
H6A | 0.4768 | 0.1852 | 0.5105 | 0.041* | |
H6B | 0.5480 | 0.2829 | 0.5123 | 0.041* | |
H71X | 0.2472 | 0.2677 | 0.6360 | 0.073* | 0.147 (3) |
H71Y | 0.2700 | 0.2084 | 0.5510 | 0.073* | 0.147 (3) |
H71Z | 0.2490 | 0.3225 | 0.5471 | 0.073* | 0.147 (3) |
H71A | 0.5456 | 0.2710 | 0.6696 | 0.066* | |
H71B | 0.4643 | 0.1788 | 0.6693 | 0.066* | |
H71C | 0.4282 | 0.2745 | 0.7191 | 0.066* | |
H8A | 0.4730 | 0.4191 | 0.6124 | 0.031* | |
H8B | 0.3955 | 0.4196 | 0.5389 | 0.031* | |
H10A | 0.2648 | 0.5661 | 0.6959 | 0.046* | |
H10B | 0.3975 | 0.5597 | 0.6788 | 0.046* | |
H9A | 0.3181 | 0.4049 | 0.7035 | 0.042* | |
H9B | 0.2397 | 0.4183 | 0.6221 | 0.042* | |
H11A | 0.2340 | 0.5822 | 0.5572 | 0.032* | |
H12A | 0.4801 | 0.6873 | 0.6464 | 0.071* | 0.853 (3) |
H12B | 0.4823 | 0.7754 | 0.5811 | 0.071* | 0.853 (3) |
H12C | 0.5015 | 0.6673 | 0.5483 | 0.071* | 0.853 (3) |
H12D | 0.1835 | 0.7338 | 0.6361 | 0.095* | |
H12E | 0.2758 | 0.8181 | 0.6381 | 0.095* | |
H12F | 0.2889 | 0.7264 | 0.6987 | 0.095* | |
H13A | 0.2149 | 0.7225 | 0.4803 | 0.045* | |
H13B | 0.3025 | 0.8087 | 0.4917 | 0.045* | |
H14X | 0.5093 | 0.6904 | 0.4772 | 0.081* | 0.147 (3) |
H14Y | 0.4892 | 0.7972 | 0.4416 | 0.081* | 0.147 (3) |
H14Z | 0.5287 | 0.7128 | 0.3793 | 0.081* | 0.147 (3) |
H14A | 0.3586 | 0.7303 | 0.2831 | 0.080* | |
H14B | 0.3290 | 0.8238 | 0.3382 | 0.080* | |
H14C | 0.2367 | 0.7409 | 0.3252 | 0.080* | |
H25 | −0.3192 | 0.4656 | 0.4991 | 0.063* | |
H22 | −0.0168 | 0.5453 | 0.2495 | 0.027* | |
H24 | −0.3399 | 0.4658 | 0.2908 | 0.030* | |
H26 | −0.1236 | 0.4916 | 0.4881 | 0.028* | |
H41 | 0.0383 | 0.5276 | 0.5930 | 0.040* | |
H42 | −0.0371 | 0.5330 | 0.6507 | 0.040* | |
H35 | 0.3360 | 0.2685 | 0.4236 | 0.040* | 0.147 (3) |
H37 | 0.3303 | 0.2620 | 0.5880 | 0.039* | 0.853 (3) |
H312 | 0.4133 | 0.7073 | 0.5839 | 0.046* | 0.147 (3) |
H314 | 0.4417 | 0.7167 | 0.4182 | 0.041* | 0.853 (3) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0179 (9) | 0.0360 (11) | 0.0222 (9) | −0.0037 (8) | 0.0000 (7) | 0.0032 (9) |
C2 | 0.0315 (13) | 0.0451 (14) | 0.0241 (12) | −0.0020 (12) | 0.0044 (10) | 0.0021 (11) |
C3 | 0.0359 (14) | 0.0436 (15) | 0.0208 (11) | −0.0008 (12) | −0.0028 (10) | −0.0013 (11) |
N4 | 0.0205 (9) | 0.0341 (10) | 0.0234 (10) | −0.0056 (8) | −0.0010 (8) | −0.0027 (8) |
C5 | 0.0385 (14) | 0.0329 (13) | 0.0297 (13) | −0.0034 (11) | 0.0008 (11) | −0.0072 (11) |
C51 | 0.046 (2) | 0.053 (2) | 0.043 (2) | −0.0258 (17) | −0.0080 (16) | 0.0007 (17) |
C52 | 0.084 (3) | 0.054 (2) | 0.0400 (17) | 0.013 (2) | 0.0132 (18) | −0.0091 (16) |
C6 | 0.0371 (14) | 0.0312 (12) | 0.0350 (14) | −0.0015 (11) | −0.0005 (11) | −0.0005 (11) |
C7 | 0.0357 (13) | 0.0324 (13) | 0.0290 (13) | −0.0069 (11) | −0.0028 (11) | 0.0008 (11) |
C71 | 0.064 (2) | 0.0316 (14) | 0.0364 (15) | 0.0003 (14) | −0.0077 (14) | 0.0073 (12) |
N8 | 0.0248 (9) | 0.0332 (10) | 0.0189 (9) | −0.0024 (8) | −0.0019 (8) | 0.0021 (8) |
C10 | 0.0419 (15) | 0.0559 (17) | 0.0181 (11) | 0.0188 (14) | 0.0003 (11) | −0.0039 (12) |
C9 | 0.0275 (12) | 0.0506 (15) | 0.0260 (12) | 0.0046 (12) | 0.0054 (10) | 0.0072 (12) |
N11 | 0.0197 (9) | 0.0373 (11) | 0.0242 (10) | −0.0033 (8) | −0.0032 (8) | −0.0012 (8) |
C12 | 0.0445 (16) | 0.0380 (14) | 0.0331 (15) | −0.0131 (12) | 0.0031 (12) | −0.0087 (12) |
C121 | 0.0389 (18) | 0.054 (2) | 0.049 (2) | −0.0217 (16) | −0.0056 (17) | −0.0082 (18) |
C122 | 0.102 (3) | 0.0410 (17) | 0.0471 (19) | −0.0081 (19) | 0.024 (2) | −0.0160 (15) |
C13 | 0.0428 (16) | 0.0300 (12) | 0.0389 (15) | −0.0051 (12) | 0.0059 (12) | −0.0016 (12) |
C14 | 0.0324 (13) | 0.0360 (13) | 0.0348 (14) | −0.0073 (11) | 0.0048 (12) | 0.0047 (12) |
C141 | 0.075 (2) | 0.0423 (16) | 0.0424 (17) | 0.0013 (17) | 0.0045 (17) | 0.0116 (14) |
O21 | 0.0247 (9) | 0.1147 (19) | 0.0238 (9) | −0.0193 (12) | −0.0066 (7) | 0.0121 (11) |
O22 | 0.0203 (8) | 0.0765 (14) | 0.0260 (9) | −0.0126 (9) | 0.0001 (7) | 0.0068 (9) |
O23 | 0.0262 (8) | 0.0482 (10) | 0.0172 (7) | −0.0037 (8) | 0.0005 (6) | 0.0021 (7) |
O24 | 0.0265 (9) | 0.0639 (13) | 0.0234 (8) | −0.0096 (9) | −0.0068 (7) | 0.0043 (9) |
O25 | 0.0241 (9) | 0.0830 (15) | 0.0182 (8) | −0.0216 (10) | 0.0018 (7) | −0.0009 (9) |
C21 | 0.0179 (10) | 0.0282 (12) | 0.0204 (10) | −0.0017 (9) | −0.0015 (8) | −0.0002 (9) |
C22 | 0.0199 (10) | 0.0282 (11) | 0.0190 (10) | −0.0018 (9) | 0.0007 (8) | 0.0011 (9) |
C23 | 0.0208 (10) | 0.0245 (10) | 0.0165 (9) | 0.0012 (9) | −0.0006 (8) | −0.0005 (8) |
C24 | 0.0181 (10) | 0.0367 (13) | 0.0211 (10) | −0.0062 (10) | −0.0003 (8) | −0.0042 (10) |
C25 | 0.0199 (10) | 0.0374 (13) | 0.0202 (11) | −0.0061 (10) | 0.0021 (8) | −0.0014 (10) |
C26 | 0.0219 (10) | 0.0294 (12) | 0.0189 (10) | −0.0009 (9) | −0.0004 (8) | −0.0005 (9) |
C27 | 0.0207 (11) | 0.0424 (13) | 0.0197 (11) | −0.0042 (10) | −0.0007 (9) | 0.0004 (11) |
C28 | 0.0241 (11) | 0.0289 (11) | 0.0188 (10) | −0.0014 (9) | −0.0014 (8) | −0.0005 (9) |
O1 | 0.0356 (12) | 0.173 (3) | 0.0305 (11) | −0.0270 (17) | −0.0003 (9) | −0.0124 (16) |
Geometric parameters (Å, º) top
N1—C2 | 1.481 (3) | N11—C12 | 1.478 (3) |
N1—C14 | 1.501 (3) | N11—H11A | 0.9200 |
N1—H1A | 0.9200 | C12—C122 | 1.525 (4) |
N1—H1B | 0.9200 | C12—C13 | 1.538 (4) |
C2—C3 | 1.515 (4) | C12—C121 | 1.567 (5) |
C2—H2A | 0.9900 | C121—H12A | 0.9800 |
C2—H2B | 0.9900 | C121—H12B | 0.9800 |
C3—N4 | 1.470 (3) | C121—H12C | 0.9800 |
C3—H3A | 0.9900 | C122—H12D | 0.9800 |
C3—H3B | 0.9900 | C122—H12E | 0.9800 |
N4—C5 | 1.495 (3) | C122—H12F | 0.9800 |
N4—H4A | 0.9200 | C13—C14 | 1.526 (4) |
C5—C52 | 1.529 (4) | C13—H13A | 0.9900 |
C5—C51 | 1.534 (4) | C13—H13B | 0.9900 |
C5—C6 | 1.546 (4) | C14—C141 | 1.515 (4) |
C51—H51A | 0.9800 | C14—C14' | 1.530 (3) |
C51—H51B | 0.9800 | C14'—H14X | 0.9800 |
C51—H51C | 0.9800 | C14'—H14Y | 0.9800 |
C52—H52A | 0.9800 | C14'—H14Z | 0.9800 |
C52—H52B | 0.9800 | C141—H14A | 0.9800 |
C52—H52C | 0.9800 | C141—H14B | 0.9800 |
C6—C7 | 1.523 (4) | C141—H14C | 0.9800 |
C6—H6A | 0.9900 | O21—C27 | 1.241 (3) |
C6—H6B | 0.9900 | O22—C27 | 1.258 (3) |
C7—N8 | 1.509 (3) | O23—C28 | 1.267 (3) |
C7—C71 | 1.526 (4) | O24—C28 | 1.238 (3) |
C7—C71' | 1.531 (3) | O25—C25 | 1.366 (3) |
C71'—H71X | 0.9800 | O25—H25 | 0.8400 |
C71'—H71Y | 0.9800 | C21—C22 | 1.393 (3) |
C71'—H71Z | 0.9800 | C21—C26 | 1.393 (3) |
C71—H71A | 0.9800 | C21—C27 | 1.520 (3) |
C71—H71B | 0.9800 | C22—C23 | 1.389 (3) |
C71—H71C | 0.9800 | C22—H22 | 0.9500 |
N8—C9 | 1.485 (3) | C23—C24 | 1.391 (3) |
N8—H8A | 0.9200 | C23—C28 | 1.526 (3) |
N8—H8B | 0.9200 | C24—C25 | 1.398 (3) |
C10—N11 | 1.463 (3) | C24—H24 | 0.9500 |
C10—C9 | 1.502 (4) | C25—C26 | 1.392 (3) |
C10—H10A | 0.9900 | C26—H26 | 0.9500 |
C10—H10B | 0.9900 | O1—H41 | 0.8412 |
C9—H9A | 0.9900 | O1—H42 | 0.8427 |
C9—H9B | 0.9900 | | |
| | | |
C2—N1—C14 | 116.7 (2) | N8—C9—H9A | 109.4 |
C2—N1—H1A | 108.1 | C10—C9—H9A | 109.4 |
C14—N1—H1A | 108.1 | N8—C9—H9B | 109.4 |
C2—N1—H1B | 108.1 | C10—C9—H9B | 109.4 |
C14—N1—H1B | 108.1 | H9A—C9—H9B | 108.0 |
H1A—N1—H1B | 107.3 | C10—N11—C12 | 115.0 (2) |
N1—C2—C3 | 110.3 (2) | C10—N11—H11A | 108.5 |
N1—C2—H2A | 109.6 | C12—N11—H11A | 108.5 |
C3—C2—H2A | 109.6 | N11—C12—C122 | 111.4 (2) |
N1—C2—H2B | 109.6 | N11—C12—C13 | 108.0 (2) |
C3—C2—H2B | 109.6 | C122—C12—C13 | 108.1 (3) |
H2A—C2—H2B | 108.1 | N11—C12—C121 | 106.7 (3) |
N4—C3—C2 | 110.5 (2) | C122—C12—C121 | 111.5 (3) |
N4—C3—H3A | 109.6 | C13—C12—C121 | 111.0 (3) |
C2—C3—H3A | 109.6 | C14—C13—C12 | 117.8 (2) |
N4—C3—H3B | 109.6 | C14—C13—H13A | 107.9 |
C2—C3—H3B | 109.6 | C12—C13—H13A | 107.9 |
H3A—C3—H3B | 108.1 | C14—C13—H13B | 107.9 |
C3—N4—C5 | 115.3 (2) | C12—C13—H13B | 107.9 |
C3—N4—H4A | 108.5 | H13A—C13—H13B | 107.2 |
C5—N4—H4A | 108.5 | N1—C14—C141 | 109.6 (2) |
N4—C5—C52 | 112.2 (2) | N1—C14—C13 | 108.2 (2) |
N4—C5—C51 | 109.6 (2) | C141—C14—C13 | 110.8 (2) |
C52—C5—C51 | 109.9 (3) | N1—C14—C14' | 112.0 (9) |
N4—C5—C6 | 106.6 (2) | C141—C14—C14' | 111.4 (9) |
C52—C5—C6 | 107.2 (2) | C13—C14—C14' | 104.7 (9) |
C51—C5—C6 | 111.4 (2) | C14—C14'—H14X | 109.5 |
C7—C6—C5 | 116.7 (2) | C14—C14'—H14Y | 109.5 |
C7—C6—H6A | 108.1 | H14X—C14'—H14Y | 109.5 |
C5—C6—H6A | 108.1 | C14—C14'—H14Z | 109.5 |
C7—C6—H6B | 108.1 | H14X—C14'—H14Z | 109.5 |
C5—C6—H6B | 108.1 | C25—O25—H25 | 109.5 |
H6A—C6—H6B | 107.3 | C22—C21—C26 | 120.3 (2) |
N8—C7—C6 | 108.8 (2) | C22—C21—C27 | 118.63 (19) |
N8—C7—C71 | 109.5 (2) | C26—C21—C27 | 121.09 (19) |
C6—C7—C71 | 111.8 (2) | C23—C22—C21 | 120.6 (2) |
N8—C7—C71' | 97.5 (9) | C23—C22—H22 | 119.7 |
C6—C7—C71' | 110.0 (9) | C21—C22—H22 | 119.7 |
C71—C7—C71' | 118.1 (9) | C22—C23—C24 | 119.20 (19) |
C7—C71'—H71X | 109.5 | C22—C23—C28 | 120.64 (19) |
C7—C71'—H71Y | 109.5 | C24—C23—C28 | 120.2 (2) |
H71X—C71'—H71Y | 109.5 | C23—C24—C25 | 120.4 (2) |
C7—C71'—H71Z | 109.5 | C23—C24—H24 | 119.8 |
H71X—C71'—H71Z | 109.5 | C25—C24—H24 | 119.8 |
H71Y—C71'—H71Z | 109.5 | O25—C25—C26 | 123.3 (2) |
C9—N8—C7 | 113.6 (2) | O25—C25—C24 | 116.4 (2) |
C9—N8—H8A | 108.8 | C26—C25—C24 | 120.3 (2) |
C7—N8—H8A | 108.8 | C25—C26—C21 | 119.2 (2) |
C9—N8—H8B | 108.8 | C25—C26—H26 | 120.4 |
C7—N8—H8B | 108.8 | C21—C26—H26 | 120.4 |
H8A—N8—H8B | 107.7 | O21—C27—O22 | 124.4 (2) |
N11—C10—C9 | 111.5 (2) | O21—C27—C21 | 119.5 (2) |
N11—C10—H10A | 109.3 | O22—C27—C21 | 116.1 (2) |
C9—C10—H10A | 109.3 | O23—C28—O24 | 123.9 (2) |
N11—C10—H10B | 109.3 | O24—C28—C23 | 118.4 (2) |
C9—C10—H10B | 109.3 | O23—C28—C23 | 117.7 (2) |
H10A—C10—H10B | 108.0 | H41—O1—H42 | 99 |
N8—C9—C10 | 111.0 (2) | | |
| | | |
C14—N1—C2—C3 | 177.7 (2) | C2—N1—C14—C14' | −54.3 (10) |
N1—C2—C3—N4 | −69.4 (3) | C12—C13—C14—N1 | 62.2 (3) |
C2—C3—N4—C5 | −175.6 (2) | C12—C13—C14—C141 | −177.6 (2) |
C3—N4—C5—C52 | 59.9 (3) | C12—C13—C14—C14' | −57.3 (10) |
C3—N4—C5—C51 | −62.4 (3) | C13—C14—N1—C2 | −169.3 (2) |
C3—N4—C5—C6 | 177.0 (2) | C26—C21—C22—C23 | −1.0 (4) |
N4—C5—C6—C7 | 68.5 (3) | C27—C21—C22—C23 | 178.1 (2) |
C52—C5—C6—C7 | −171.2 (3) | C21—C22—C23—C24 | −0.3 (3) |
C51—C5—C6—C7 | −51.0 (3) | C21—C22—C23—C28 | 179.2 (2) |
C5—C6—C7—N8 | −61.4 (3) | C22—C23—C24—C25 | 1.9 (4) |
C5—C6—C7—C71 | 177.6 (2) | C28—C23—C24—C25 | −177.6 (2) |
C5—C6—C7—C71' | 44.4 (10) | C23—C24—C25—O25 | 177.9 (2) |
C6—C7—N8—C9 | 158.0 (2) | C23—C24—C25—C26 | −2.2 (4) |
C71—C7—N8—C9 | −79.6 (3) | O25—C25—C26—C21 | −179.2 (2) |
C71'—C7—N8—C9 | 43.8 (9) | C24—C25—C26—C21 | 1.0 (4) |
C7—N8—C9—C10 | 173.2 (2) | C22—C21—C26—C25 | 0.6 (3) |
N8—C9—C10—N11 | 63.8 (3) | C27—C21—C26—C25 | −178.5 (2) |
C9—C10—N11—C12 | −171.5 (2) | C22—C21—C27—O21 | −174.9 (3) |
C10—N11—C12—C122 | −54.0 (3) | C26—C21—C27—O21 | 4.2 (4) |
C10—N11—C12—C13 | −172.5 (2) | C22—C21—C27—O22 | 5.6 (4) |
C10—N11—C12—C121 | 68.0 (3) | C26—C21—C27—O22 | −175.3 (2) |
N11—C12—C13—C14 | −64.9 (3) | C22—C23—C28—O24 | −176.8 (2) |
C122—C12—C13—C14 | 174.4 (3) | C24—C23—C28—O24 | 2.7 (3) |
C121—C12—C13—C14 | 51.9 (3) | C22—C23—C28—O23 | 2.3 (3) |
C2—N1—C14—C141 | 69.8 (3) | C24—C23—C28—O23 | −178.3 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···N11 | 0.92 | 2.02 | 2.767 (3) | 138 |
N8—H8B···N4 | 0.92 | 1.97 | 2.762 (3) | 144 |
N1—H1B···O22 | 0.92 | 1.71 | 2.622 (3) | 173 |
N4—H4A···O25i | 0.92 | 2.03 | 2.952 (3) | 175 |
N8—H8A···O23ii | 0.92 | 1.91 | 2.795 (3) | 160 |
N11—H11A···O21 | 0.92 | 2.25 | 3.122 (3) | 159 |
O1—H41···O21 | 0.84 | 1.90 | 2.720 (2) | 165 |
O1—H42···O24iii | 0.84 | 1.95 | 2.761 (3) | 160 |
O25—H25···O23iii | 0.84 | 1.93 | 2.655 (2) | 144 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1/2, −y+1, z+1/2; (iii) −x−1/2, −y+1, z+1/2. |
(4) racemic-5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetraazacyclotetradecane–5- hydroxyisophthalic acid–water (1/1/1)
top
Crystal data top
C16H38N4·C8H4O5·H2O | F(000) = 1056 |
Mr = 484.63 | Dx = 1.245 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 16.0262 (4) Å | Cell parameters from 5899 reflections |
b = 11.6461 (3) Å | θ = 2.6–27.5° |
c = 15.7907 (3) Å | µ = 0.09 mm−1 |
β = 118.6520 (12)° | T = 100 K |
V = 2586.33 (10) Å3 | Block, colourless |
Z = 4 | 0.32 × 0.26 × 0.20 mm |
Data collection top
Kappa-CCD diffractometer | 5899 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 4676 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
ϕ scans and ω scans with κ offsets | θmax = 27.5°, θmin = 2.6° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = −20→18 |
Tmin = 0.972, Tmax = 0.982 | k = −15→0 |
23221 measured reflections | l = 0→20 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.126 | w = 1/[σ2(Fo2) + (0.0515P)2 + 1.3466P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
5899 reflections | Δρmax = 0.28 e Å−3 |
321 parameters | Δρmin = −0.24 e Å−3 |
2 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0051 (10) |
Crystal data top
C16H38N4·C8H4O5·H2O | V = 2586.33 (10) Å3 |
Mr = 484.63 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.0262 (4) Å | µ = 0.09 mm−1 |
b = 11.6461 (3) Å | T = 100 K |
c = 15.7907 (3) Å | 0.32 × 0.26 × 0.20 mm |
β = 118.6520 (12)° | |
Data collection top
Kappa-CCD diffractometer | 5899 independent reflections |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | 4676 reflections with I > 2σ(I) |
Tmin = 0.972, Tmax = 0.982 | Rint = 0.035 |
23221 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.049 | 2 restraints |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.28 e Å−3 |
5899 reflections | Δρmin = −0.24 e Å−3 |
321 parameters | |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.35926 (9) | 0.84725 (11) | 0.35845 (9) | 0.0200 (3) | |
C2 | 0.31516 (11) | 0.91385 (13) | 0.40710 (11) | 0.0230 (3) | |
C3 | 0.20995 (11) | 0.88704 (14) | 0.36339 (11) | 0.0233 (3) | |
N4 | 0.15907 (9) | 0.92016 (11) | 0.26131 (9) | 0.0200 (3) | |
C5 | 0.05475 (11) | 0.89519 (14) | 0.20911 (11) | 0.0238 (3) | |
C51 | 0.01036 (13) | 0.98121 (16) | 0.12642 (13) | 0.0355 (4) | |
C52 | 0.00739 (13) | 0.90913 (17) | 0.27324 (14) | 0.0363 (4) | |
C6 | 0.04043 (11) | 0.77038 (14) | 0.17185 (12) | 0.0262 (3) | |
C7 | 0.06873 (11) | 0.74529 (14) | 0.09403 (11) | 0.0253 (3) | |
C71 | 0.04701 (14) | 0.62234 (16) | 0.05796 (14) | 0.0384 (4) | |
N8 | 0.17377 (9) | 0.76942 (11) | 0.13576 (9) | 0.0198 (3) | |
C9 | 0.20578 (11) | 0.79709 (14) | 0.06392 (11) | 0.0239 (3) | |
C10 | 0.31246 (11) | 0.81417 (13) | 0.11267 (11) | 0.0233 (3) | |
N11 | 0.34067 (9) | 0.90996 (11) | 0.18152 (9) | 0.0217 (3) | |
C12 | 0.44486 (11) | 0.93542 (14) | 0.23666 (12) | 0.0269 (3) | |
C121 | 0.45304 (14) | 1.05967 (15) | 0.27200 (14) | 0.0380 (4) | |
C122 | 0.49412 (14) | 0.9260 (2) | 0.17389 (15) | 0.0449 (5) | |
C13 | 0.49262 (12) | 0.85147 (15) | 0.32156 (12) | 0.0298 (4) | |
C14 | 0.46520 (11) | 0.86210 (14) | 0.40126 (11) | 0.0261 (3) | |
C141 | 0.51695 (13) | 0.77857 (19) | 0.48305 (13) | 0.0415 (5) | |
O21 | 0.28021 (9) | 0.58533 (9) | 0.24440 (8) | 0.0281 (3) | |
O22 | 0.31083 (10) | 0.63637 (10) | 0.39172 (9) | 0.0378 (3) | |
O23 | 0.23050 (10) | 0.37353 (10) | 0.58891 (8) | 0.0349 (3) | |
O24 | 0.19062 (10) | 0.19354 (10) | 0.54074 (9) | 0.0353 (3) | |
O25 | 0.21227 (11) | 0.15342 (9) | 0.24045 (9) | 0.0362 (3) | |
C21 | 0.26545 (10) | 0.44329 (12) | 0.34551 (10) | 0.0183 (3) | |
C22 | 0.25704 (10) | 0.42315 (12) | 0.42832 (10) | 0.0189 (3) | |
C23 | 0.23106 (10) | 0.31493 (12) | 0.44489 (10) | 0.0181 (3) | |
C24 | 0.21613 (11) | 0.22665 (12) | 0.38011 (10) | 0.0199 (3) | |
C25 | 0.22660 (11) | 0.24538 (12) | 0.29835 (10) | 0.0215 (3) | |
C26 | 0.25003 (11) | 0.35447 (12) | 0.28028 (10) | 0.0198 (3) | |
C27 | 0.28762 (11) | 0.56353 (12) | 0.32615 (11) | 0.0216 (3) | |
C28 | 0.21697 (11) | 0.29156 (13) | 0.53189 (10) | 0.0213 (3) | |
O1 | 0.28442 (11) | 0.51328 (12) | 0.08053 (9) | 0.0404 (3) | |
H1A | 0.3309 | 0.8687 | 0.2946 | 0.024* | |
H1B | 0.3465 | 0.7706 | 0.3605 | 0.024* | |
H2A | 0.3237 | 0.9970 | 0.4006 | 0.028* | |
H2B | 0.3474 | 0.8948 | 0.4767 | 0.028* | |
H3A | 0.2014 | 0.8038 | 0.3694 | 0.028* | |
H3B | 0.1830 | 0.9290 | 0.3992 | 0.028* | |
H4A | 0.1674 | 0.9977 | 0.2572 | 0.024* | |
H51A | 0.0084 | 1.0572 | 0.1521 | 0.053* | |
H51B | −0.0544 | 0.9567 | 0.0808 | 0.053* | |
H51C | 0.0486 | 0.9850 | 0.0932 | 0.053* | |
H52A | 0.0298 | 0.8484 | 0.3222 | 0.054* | |
H52B | −0.0618 | 0.9036 | 0.2334 | 0.054* | |
H52C | 0.0240 | 0.9843 | 0.3050 | 0.054* | |
H6A | 0.0776 | 0.7191 | 0.2274 | 0.031* | |
H6B | −0.0275 | 0.7503 | 0.1459 | 0.031* | |
H7 | 0.0328 | 0.7983 | 0.0384 | 0.030* | |
H71A | 0.0706 | 0.6084 | 0.0120 | 0.058* | |
H71B | −0.0219 | 0.6097 | 0.0260 | 0.058* | |
H71C | 0.0783 | 0.5695 | 0.1126 | 0.058* | |
H8A | 0.1893 | 0.8299 | 0.1781 | 0.024* | |
H8B | 0.2070 | 0.7062 | 0.1706 | 0.024* | |
H9A | 0.1736 | 0.8679 | 0.0287 | 0.029* | |
H9B | 0.1876 | 0.7338 | 0.0165 | 0.029* | |
H10A | 0.3448 | 0.7430 | 0.1471 | 0.028* | |
H10B | 0.3323 | 0.8305 | 0.0634 | 0.028* | |
H11A | 0.3098 | 0.9751 | 0.1482 | 0.026* | |
H12A | 0.4308 | 1.1121 | 0.2169 | 0.057* | |
H12B | 0.5196 | 1.0768 | 0.3178 | 0.057* | |
H12C | 0.4140 | 1.0695 | 0.3039 | 0.057* | |
H12D | 0.4959 | 0.8454 | 0.1571 | 0.067* | |
H12E | 0.5592 | 0.9557 | 0.2098 | 0.067* | |
H12F | 0.4587 | 0.9710 | 0.1148 | 0.067* | |
H13A | 0.4778 | 0.7724 | 0.2956 | 0.036* | |
H13B | 0.5623 | 0.8616 | 0.3509 | 0.036* | |
H14 | 0.4816 | 0.9416 | 0.4283 | 0.031* | |
H14A | 0.4962 | 0.7895 | 0.5317 | 0.062* | |
H14B | 0.5856 | 0.7921 | 0.5124 | 0.062* | |
H14C | 0.5027 | 0.6999 | 0.4582 | 0.062* | |
H25 | 0.2206 | 0.1728 | 0.1938 | 0.054* | |
H22 | 0.2691 | 0.4834 | 0.4733 | 0.023* | |
H24 | 0.1986 | 0.1527 | 0.3915 | 0.024* | |
H26 | 0.2555 | 0.3684 | 0.2239 | 0.024* | |
H41 | 0.2841 (18) | 0.529 (2) | 0.1323 (10) | 0.060* | |
H42 | 0.2555 (16) | 0.4503 (11) | 0.0629 (17) | 0.060* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0218 (6) | 0.0196 (6) | 0.0177 (6) | −0.0010 (5) | 0.0088 (5) | −0.0007 (5) |
C2 | 0.0245 (8) | 0.0247 (7) | 0.0207 (7) | −0.0016 (6) | 0.0115 (6) | −0.0042 (6) |
C3 | 0.0245 (8) | 0.0273 (8) | 0.0204 (7) | −0.0024 (6) | 0.0126 (6) | −0.0013 (6) |
N4 | 0.0209 (6) | 0.0183 (6) | 0.0209 (6) | −0.0019 (5) | 0.0100 (5) | −0.0005 (5) |
C5 | 0.0201 (7) | 0.0266 (8) | 0.0245 (7) | −0.0013 (6) | 0.0106 (6) | −0.0039 (6) |
C51 | 0.0315 (9) | 0.0322 (9) | 0.0326 (9) | 0.0031 (7) | 0.0072 (7) | −0.0007 (7) |
C52 | 0.0291 (9) | 0.0466 (10) | 0.0384 (10) | −0.0034 (8) | 0.0202 (8) | −0.0119 (8) |
C6 | 0.0236 (8) | 0.0279 (8) | 0.0277 (8) | −0.0063 (6) | 0.0125 (6) | −0.0047 (7) |
C7 | 0.0223 (8) | 0.0265 (8) | 0.0252 (8) | −0.0053 (6) | 0.0099 (6) | −0.0059 (6) |
C71 | 0.0369 (10) | 0.0354 (10) | 0.0458 (11) | −0.0146 (8) | 0.0222 (9) | −0.0193 (8) |
N8 | 0.0226 (6) | 0.0179 (6) | 0.0197 (6) | −0.0022 (5) | 0.0109 (5) | −0.0012 (5) |
C9 | 0.0316 (8) | 0.0246 (7) | 0.0180 (7) | −0.0039 (6) | 0.0139 (6) | −0.0016 (6) |
C10 | 0.0284 (8) | 0.0229 (7) | 0.0236 (7) | −0.0013 (6) | 0.0165 (7) | −0.0004 (6) |
N11 | 0.0234 (6) | 0.0200 (6) | 0.0240 (6) | −0.0023 (5) | 0.0133 (5) | 0.0001 (5) |
C12 | 0.0245 (8) | 0.0313 (8) | 0.0293 (8) | −0.0067 (7) | 0.0164 (7) | −0.0033 (7) |
C121 | 0.0386 (10) | 0.0304 (9) | 0.0416 (10) | −0.0129 (8) | 0.0164 (8) | −0.0019 (8) |
C122 | 0.0358 (10) | 0.0669 (14) | 0.0433 (11) | −0.0119 (10) | 0.0280 (9) | −0.0037 (10) |
C13 | 0.0241 (8) | 0.0328 (9) | 0.0334 (9) | 0.0003 (7) | 0.0145 (7) | −0.0038 (7) |
C14 | 0.0200 (8) | 0.0303 (8) | 0.0251 (8) | −0.0017 (6) | 0.0086 (6) | −0.0031 (7) |
C141 | 0.0303 (9) | 0.0524 (12) | 0.0328 (10) | 0.0082 (9) | 0.0079 (8) | 0.0088 (9) |
O21 | 0.0460 (7) | 0.0196 (5) | 0.0257 (6) | 0.0012 (5) | 0.0228 (5) | 0.0043 (4) |
O22 | 0.0695 (9) | 0.0204 (6) | 0.0314 (6) | −0.0122 (6) | 0.0306 (7) | −0.0062 (5) |
O23 | 0.0593 (8) | 0.0301 (6) | 0.0270 (6) | −0.0119 (6) | 0.0302 (6) | −0.0079 (5) |
O24 | 0.0600 (9) | 0.0264 (6) | 0.0314 (6) | −0.0063 (6) | 0.0315 (6) | 0.0014 (5) |
O25 | 0.0751 (10) | 0.0191 (5) | 0.0323 (6) | −0.0134 (6) | 0.0402 (7) | −0.0089 (5) |
C21 | 0.0223 (7) | 0.0159 (7) | 0.0174 (7) | 0.0003 (5) | 0.0102 (6) | 0.0011 (5) |
C22 | 0.0232 (7) | 0.0182 (7) | 0.0164 (7) | 0.0005 (6) | 0.0104 (6) | −0.0018 (5) |
C23 | 0.0200 (7) | 0.0200 (7) | 0.0152 (6) | 0.0016 (5) | 0.0093 (6) | 0.0022 (5) |
C24 | 0.0258 (7) | 0.0165 (7) | 0.0207 (7) | −0.0008 (6) | 0.0136 (6) | 0.0014 (6) |
C25 | 0.0299 (8) | 0.0180 (7) | 0.0196 (7) | −0.0009 (6) | 0.0141 (6) | −0.0033 (6) |
C26 | 0.0253 (7) | 0.0203 (7) | 0.0174 (7) | 0.0000 (6) | 0.0131 (6) | 0.0001 (6) |
C27 | 0.0264 (8) | 0.0177 (7) | 0.0240 (7) | −0.0001 (6) | 0.0147 (6) | 0.0004 (6) |
C28 | 0.0257 (8) | 0.0226 (7) | 0.0178 (7) | 0.0007 (6) | 0.0121 (6) | 0.0014 (6) |
O1 | 0.0604 (9) | 0.0388 (7) | 0.0308 (7) | −0.0065 (6) | 0.0291 (7) | −0.0008 (6) |
Geometric parameters (Å, º) top
N1—C2 | 1.487 (2) | N11—C12 | 1.497 (2) |
N1—C14 | 1.506 (2) | N11—H11A | 0.9200 |
N1—H1A | 0.9200 | C12—C121 | 1.534 (2) |
N1—H1B | 0.9200 | C12—C13 | 1.535 (2) |
C2—C3 | 1.517 (2) | C12—C122 | 1.539 (2) |
C2—H2A | 0.9900 | C121—H12A | 0.9800 |
C2—H2B | 0.9900 | C121—H12B | 0.9800 |
C3—N4 | 1.467 (2) | C121—H12C | 0.9800 |
C3—H3A | 0.9900 | C122—H12D | 0.9800 |
C3—H3B | 0.9900 | C122—H12E | 0.9800 |
N4—C5 | 1.496 (2) | C122—H12F | 0.9800 |
N4—H4A | 0.9200 | C13—C14 | 1.524 (2) |
C5—C51 | 1.524 (2) | C13—H13A | 0.9900 |
C5—C52 | 1.538 (2) | C13—H13B | 0.9900 |
C5—C6 | 1.543 (2) | C14—C141 | 1.508 (2) |
C51—H51A | 0.9800 | C14—H14 | 1.0000 |
C51—H51B | 0.9800 | C141—H14A | 0.9800 |
C51—H51C | 0.9800 | C141—H14B | 0.9800 |
C52—H52A | 0.9800 | C141—H14C | 0.9800 |
C52—H52B | 0.9800 | O21—C27 | 1.264 (2) |
C52—H52C | 0.9800 | O22—C27 | 1.249 (2) |
C6—C7 | 1.528 (2) | O23—C28 | 1.258 (2) |
C6—H6A | 0.9900 | O24—C28 | 1.248 (2) |
C6—H6B | 0.9900 | O25—C25 | 1.3544 (18) |
C7—N8 | 1.511 (2) | O25—H25 | 0.8400 |
C7—C71 | 1.518 (2) | C21—C26 | 1.396 (2) |
C7—H7 | 1.0000 | C21—C22 | 1.3971 (19) |
C71—H71A | 0.9800 | C21—C27 | 1.511 (2) |
C71—H71B | 0.9800 | C22—C23 | 1.391 (2) |
C71—H71C | 0.9800 | C22—H22 | 0.9500 |
N8—C9 | 1.487 (2) | C23—C24 | 1.388 (2) |
N8—H8A | 0.9200 | C23—C28 | 1.5198 (19) |
N8—H8B | 0.9200 | C24—C25 | 1.396 (2) |
C9—C10 | 1.514 (2) | C24—H24 | 0.9500 |
C9—H9A | 0.9900 | C25—C26 | 1.393 (2) |
C9—H9B | 0.9900 | C26—H26 | 0.9500 |
C10—N11 | 1.470 (12) | O1—H41 | 0.841 |
C10—H10A | 0.9900 | O1—H42 | 0.841 |
C10—H10B | 0.9900 | | |
| | | |
C2—N1—C14 | 114.9 (2) | N11—C10—H10A | 109.6 |
C2—N1—H1A | 108.5 | C9—C10—H10A | 109.6 |
C14—N1—H1A | 108.5 | N11—C10—H10B | 109.6 |
C2—N1—H1B | 108.5 | C9—C10—H10B | 109.6 |
C14—N1—H1B | 108.5 | H10A—C10—H10B | 108.1 |
H1A—N1—H1B | 107.5 | C10—N11—C12 | 116.3 (2) |
N1—C2—C3 | 110.94 (12) | C10—N11—H11A | 108.2 |
N1—C2—H2A | 109.5 | C12—N11—H11A | 108.2 |
C3—C2—H2A | 109.5 | N11—C12—C121 | 106.00 (13) |
N1—C2—H2B | 109.5 | N11—C12—C13 | 109.39 (13) |
C3—C2—H2B | 109.5 | C121—C12—C13 | 111.31 (14) |
H2A—C2—H2B | 108.0 | N11—C12—C122 | 112.64 (14) |
N4—C3—C2 | 110.91 (12) | C121—C12—C122 | 108.70 (15) |
N4—C3—H3A | 109.5 | C13—C12—C122 | 108.80 (15) |
C2—C3—H3A | 109.5 | C12—C121—H12A | 109.5 |
N4—C3—H3B | 109.5 | C12—C121—H12B | 109.5 |
C2—C3—H3B | 109.5 | H12A—C121—H12B | 109.5 |
H3A—C3—H3B | 108.0 | C12—C121—H12C | 109.5 |
C3—N4—C5 | 116.1 (2) | H12A—C121—H12C | 109.5 |
C3—N4—H4A | 108.3 | H12B—C121—H12C | 109.5 |
C5—N4—H4A | 108.3 | C12—C122—H12D | 109.5 |
N4—C5—C51 | 106.46 (13) | C12—C122—H12E | 109.5 |
N4—C5—C52 | 112.99 (13) | H12D—C122—H12E | 109.5 |
C51—C5—C52 | 108.65 (14) | C12—C122—H12F | 109.5 |
N4—C5—C6 | 108.41 (12) | H12D—C122—H12F | 109.5 |
C51—C5—C6 | 111.68 (13) | H12E—C122—H12F | 109.5 |
C52—C5—C6 | 108.69 (14) | C14—C13—C12 | 116.69 (14) |
C5—C51—H51A | 109.5 | C14—C13—H13A | 108.1 |
C5—C51—H51B | 109.5 | C12—C13—H13A | 108.1 |
H51A—C51—H51B | 109.5 | C14—C13—H13B | 108.1 |
C5—C51—H51C | 109.5 | C12—C13—H13B | 108.1 |
H51A—C51—H51C | 109.5 | H13A—C13—H13B | 107.3 |
H51B—C51—H51C | 109.5 | N1—C14—C141 | 110.42 (14) |
C5—C52—H52A | 109.5 | N1—C14—C13 | 109.23 (12) |
C5—C52—H52B | 109.5 | C141—C14—C13 | 113.38 (15) |
H52A—C52—H52B | 109.5 | N1—C14—H14 | 107.9 |
C5—C52—H52C | 109.5 | C141—C14—H14 | 107.9 |
H52A—C52—H52C | 109.5 | C13—C14—H14 | 107.9 |
H52B—C52—H52C | 109.5 | C14—C141—H14A | 109.5 |
C7—C6—C5 | 116.07 (13) | C14—C141—H14B | 109.5 |
C7—C6—H6A | 108.3 | H14A—C141—H14B | 109.5 |
C5—C6—H6A | 108.3 | C14—C141—H14C | 109.5 |
C7—C6—H6B | 108.3 | H14A—C141—H14C | 109.5 |
C5—C6—H6B | 108.3 | H14B—C141—H14C | 109.5 |
H6A—C6—H6B | 107.4 | C25—O25—H25 | 109.5 |
N8—C7—C71 | 110.24 (13) | C26—C21—C22 | 120.26 (13) |
N8—C7—C6 | 108.17 (12) | C26—C21—C27 | 120.86 (12) |
C71—C7—C6 | 112.27 (14) | C22—C21—C27 | 118.84 (13) |
N8—C7—H7 | 108.7 | C23—C22—C21 | 120.01 (13) |
C71—C7—H7 | 108.7 | C23—C22—H22 | 120.0 |
C6—C7—H7 | 108.7 | C21—C22—H22 | 120.0 |
C7—C71—H71A | 109.5 | C24—C23—C22 | 119.60 (13) |
C7—C71—H71B | 109.5 | C24—C23—C28 | 119.07 (13) |
H71A—C71—H71B | 109.5 | C22—C23—C28 | 121.33 (13) |
C7—C71—H71C | 109.5 | C23—C24—C25 | 120.74 (13) |
H71A—C71—H71C | 109.5 | C23—C24—H24 | 119.6 |
H71B—C71—H71C | 109.5 | C25—C24—H24 | 119.6 |
C9—N8—C7 | 115.3 (2) | O25—C25—C26 | 123.93 (13) |
C9—N8—H8A | 108.4 | O25—C25—C24 | 116.36 (13) |
C7—N8—H8A | 108.4 | C26—C25—C24 | 119.71 (13) |
C9—N8—H8B | 108.4 | C25—C26—C21 | 119.65 (13) |
C7—N8—H8B | 108.4 | C25—C26—H26 | 120.2 |
H8A—N8—H8B | 107.5 | C21—C26—H26 | 120.2 |
N8—C9—C10 | 111.04 (12) | O22—C27—O21 | 123.7 (2) |
N8—C9—H9A | 109.4 | O22—C27—C21 | 117.83 (13) |
C10—C9—H9A | 109.4 | O21—C27—C21 | 118.47 (13) |
N8—C9—H9B | 109.4 | O24—C28—O23 | 124.4 (2) |
C10—C9—H9B | 109.4 | O24—C28—C23 | 118.02 (13) |
H9A—C9—H9B | 108.0 | O23—C28—C23 | 117.51 (13) |
N11—C10—C9 | 110.35 (12) | H41—O1—H42 | 105 |
| | | |
C14—N1—C2—C3 | −176.1 (2) | C2—N1—C14—C13 | −148.1 (2) |
N1—C2—C3—N4 | −62.2 (2) | C12—C13—C14—N1 | 57.8 (2) |
C2—C3—N4—C5 | 178.5 (2) | C12—C13—C14—C141 | −178.60 (15) |
C3—N4—C5—C51 | 154.09 (13) | C26—C21—C22—C23 | −1.5 (2) |
C3—N4—C5—C52 | 34.91 (19) | C27—C21—C22—C23 | 176.13 (13) |
C3—N4—C5—C6 | −85.6 (2) | C21—C22—C23—C24 | 1.7 (2) |
N4—C5—C6—C7 | −66.3 (2) | C21—C22—C23—C28 | −177.23 (13) |
C51—C5—C6—C7 | 50.68 (19) | C22—C23—C24—C25 | −0.2 (2) |
C52—C5—C6—C7 | 170.53 (14) | C28—C23—C24—C25 | 178.78 (14) |
C5—C6—C7—N8 | 61.3 (2) | C23—C24—C25—O25 | 178.80 (14) |
C5—C6—C7—C71 | −176.79 (14) | C23—C24—C25—C26 | −1.6 (2) |
C71—C7—N8—C9 | 81.27 (17) | O25—C25—C26—C21 | −178.59 (15) |
C6—C7—N8—C9 | −155.6 (2) | C24—C25—C26—C21 | 1.8 (2) |
C7—N8—C9—C10 | −177.3 (2) | C22—C21—C26—C25 | −0.3 (2) |
N8—C9—C10—N11 | −60.7 (2) | C27—C21—C26—C25 | −177.87 (14) |
C9—C10—N11—C12 | 178.9 (2) | C26—C21—C27—O22 | −172.39 (15) |
C10—N11—C12—C121 | 159.18 (13) | C22—C21—C27—O22 | 10.0 (2) |
C10—N11—C12—C13 | −80.7 (2) | C26—C21—C27—O21 | 8.7 (2) |
C10—N11—C12—C122 | 40.43 (19) | C22—C21—C27—O21 | −168.87 (14) |
N11—C12—C13—C14 | −66.5 (2) | C24—C23—C28—O24 | −1.3 (2) |
C121—C12—C13—C14 | 50.26 (19) | C22—C23—C28—O24 | 177.68 (15) |
C122—C12—C13—C14 | 170.03 (15) | C24—C23—C28—O23 | −179.58 (14) |
C2—N1—C14—C141 | 86.60 (17) | C22—C23—C28—O23 | −0.6 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···N11 | 0.92 | 1.93 | 2.762 (2) | 150 |
N8—H8A···N4 | 0.92 | 1.92 | 2.742 (2) | 148 |
N1—H1B···O22 | 0.92 | 1.81 | 2.702 (2) | 162 |
N4—H4A···O25i | 0.92 | 2.01 | 2.913 (2) | 165 |
N8—H8B···O21 | 0.92 | 1.85 | 2.765 (2) | 176 |
N11—H11A···O23ii | 0.92 | 2.11 | 3.023 (2) | 170 |
O1—H41···O21 | 0.84 | 1.92 (2) | 2.752 (2) | 172 (2) |
O1—H42···O24iii | 0.84 | 1.91 (2) | 2.748 (2) | 172 (2) |
O25—H25···O23iii | 0.84 | 1.82 | 2.565 (2) | 147 |
Symmetry codes: (i) x, y+1, z; (ii) x, −y+3/2, z−1/2; (iii) x, −y+1/2, z−1/2. |
Experimental details
| (1) | (3) | (4) |
Crystal data |
Chemical formula | C16H38N4·2(C7H3N2O6) | C16H38N4·C8H4O5·H2O | C16H38N4·C8H4O5·H2O |
Mr | 708.73 | 484.63 | 484.63 |
Crystal system, space group | Triclinic, P1 | Orthorhombic, P212121 | Monoclinic, P21/c |
Temperature (K) | 150 | 100 | 100 |
a, b, c (Å) | 8.7336 (3), 10.9388 (3), 11.0284 (3) | 11.8760 (5), 13.8395 (6), 15.8571 (7) | 16.0262 (4), 11.6461 (3), 15.7907 (3) |
α, β, γ (°) | 114.5800 (17), 91.9660 (18), 111.6740 (18) | 90, 90, 90 | 90, 118.6520 (12), 90 |
V (Å3) | 868.09 (4) | 2606.2 (2) | 2586.33 (10) |
Z | 1 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.11 | 0.09 | 0.09 |
Crystal size (mm) | 0.26 × 0.16 × 0.14 | 0.24 × 0.24 × 0.16 | 0.32 × 0.26 × 0.20 |
|
Data collection |
Diffractometer | Kappa-CCD diffractometer | Kappa-CCD diffractometer | Kappa-CCD diffractometer |
Absorption correction | Multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | Multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | Multi-scan DENZO-SMN (Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.973, 0.985 | 0.979, 0.986 | 0.972, 0.982 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12749, 5013, 3651 | 30326, 4203, 3479 | 23221, 5899, 4676 |
Rint | 0.023 | 0.033 | 0.035 |
(sin θ/λ)max (Å−1) | 0.703 | 0.704 | 0.649 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.133, 1.07 | 0.058, 0.124, 1.04 | 0.049, 0.126, 1.02 |
No. of reflections | 5013 | 4203 | 5899 |
No. of parameters | 229 | 323 | 321 |
No. of restraints | 0 | 4 | 2 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.27 | 0.30, −0.27 | 0.28, −0.24 |
Hydrogen-bond geometry (Å, º) for (1) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O5i | 0.92 | 2.42 | 3.169 (2) | 139 |
N1—H1···O2ii | 0.92 | 2.46 | 3.107 (2) | 127 |
N4—H4A···N1ii | 0.92 | 2.12 | 2.808 (2) | 131 |
N4—H4B···O1 | 0.92 | 1.81 | 2.730 (2) | 175 |
Symmetry codes: (i) x+1, y+1, z+1; (ii) −x+1, −y+1, −z+1. |
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