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The X-ray structure determinations of the two title compounds, namely 7-methyl-7,17-diaza-3,11-diazoniabicyclo[11.3.1]heptadeca-1(17),13,15-triene dichloride monohydrate, C
14H
26N
42+·2Cl
-·H
2O, (I), and 7-methyl-17-aza-3,7,11-triazoniabicyclo[11.3.1]heptadeca-1(17),13,15-triene 2.826-chloride 0.174-nitrate, C
14H
27N
43+·2.826Cl
-·0.174NO
3-, (II), are reported. Protonation occurs at the secondary amine N atoms in (I) and at all three amine N atoms in (II) to which the Cl
- ions are linked
via N-H
Cl hydrogen bonds. The macrocyclic hole is quite different in both structures, as is observed by comparing particularly the N3
N4 distances [2.976 (4) and 4.175 (4) Å for (I) and (II), respectively]. In (II), a Cl
- ion alternates with an NO
3- ion in a disordered structure.
Supporting information
CCDC references: 146092; 146093
For both compounds, data collection: SMART (Siemens, 1994); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.
(I) 7-Methyl-3,7,11,17-tetraazabicyclo[11.3.1]-heptadeca-1(17),13,15-triene
dihydrochloride monohydrate
top
Crystal data top
C14H26N42+·2Cl−·H2O | F(000) = 728 |
Mr = 339.30 | Dx = 1.246 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
a = 16.7683 (3) Å | Cell parameters from 6095 reflections |
b = 9.7089 (2) Å | θ = 3–56.6° |
c = 11.116 (2) Å | µ = 0.36 mm−1 |
β = 90.9963 (11)° | T = 293 K |
V = 1809.4 (3) Å3 | Needle, colourless |
Z = 4 | 0.70 × 0.20 × 0.15 mm |
Data collection top
Siemens CCD SMART diffractometer | 2812 independent reflections |
Radiation source: fine-focus sealed tube | 2656 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
ω scans | θmax = 28.2°, θmin = 2.4° |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | h = −16→22 |
Tmin = 0.785, Tmax = 0.948 | k = −12→12 |
6531 measured reflections | l = −12→14 |
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)] = 0.035 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.112 | Calculated w = 1/[σ2(Fo2) + (0.0749P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max = 0.002 |
2812 reflections | Δρmax = 0.29 e Å−3 |
208 parameters | Δρmin = −0.29 e Å−3 |
3 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.02 (6) |
Special details top
Experimental. Colourless crystals of C14H26N4·H2O. 2 Cl (I) and
C14H27N4.2.826Cl.0.174NO3 (II) crystallized from ethanol were used for
structure determination. The reason for using such a large crystal (0.70 mm)
for the structure determination of (I) was that we had few crystals and all
attemps to cut them before mounting in the diffractometer leds to the breaking
in the longitudinal direction of the needles. The chosen crystals were mounted
on a glass fiber using an epoxy resin. Data were collected using a Siemens
SMART CCD area detector single-crystal diffractometer with graphite
monochromated Mo Kα radiation (λ = 0.71073 Å). Preliminary unit
cell constants were determined with a set of 45 narrow frames (0.3 in ω
scans. A total of 1420 frames of intensity data were collected with a frame
width of 0.3° per frame in ω (and counting time of 10 and 20 s/frame for (I)
and (II) respectively at a crystal to detector distance of 4.5 cm. Both series
of data were corrected for absorption (Sheldrick, 1996). The structures were
solved by direct methods. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | 0.81700 (4) | 0.83287 (6) | 0.55323 (5) | 0.04561 (17) | |
Cl2 | 0.58601 (5) | 0.52347 (8) | 0.53363 (7) | 0.0614 (2) | |
O1W | 0.9975 (2) | 0.7336 (4) | 0.5626 (5) | 0.1050 (15) | |
N1 | 0.82743 (13) | 0.7522 (2) | 0.26247 (18) | 0.0346 (4) | |
N2 | 0.68646 (15) | 0.6942 (2) | 0.3611 (2) | 0.0401 (5) | |
N3 | 0.69080 (15) | 1.0765 (3) | 0.36737 (19) | 0.0433 (5) | |
N4 | 0.85779 (13) | 1.0194 (2) | 0.2967 (2) | 0.0361 (4) | |
C1 | 0.89915 (14) | 0.7910 (2) | 0.2247 (2) | 0.0336 (4) | |
C2 | 0.94779 (18) | 0.7064 (3) | 0.1559 (2) | 0.0445 (6) | |
H2 | 0.9971 | 0.7366 | 0.1294 | 0.053* | |
C3 | 0.9195 (2) | 0.5747 (3) | 0.1285 (3) | 0.0534 (7) | |
H3 | 0.9502 | 0.5152 | 0.0828 | 0.064* | |
C4 | 0.8464 (2) | 0.5330 (3) | 0.1689 (3) | 0.0497 (7) | |
H4 | 0.8271 | 0.4454 | 0.1512 | 0.060* | |
C5 | 0.80172 (17) | 0.6244 (2) | 0.2370 (2) | 0.0392 (5) | |
C6 | 0.7240 (2) | 0.5816 (3) | 0.2905 (3) | 0.0526 (7) | |
H6A | 0.6876 | 0.5534 | 0.2264 | 0.063* | |
H6B | 0.7330 | 0.5028 | 0.3427 | 0.063* | |
C9 | 0.6358 (2) | 0.9925 (3) | 0.4388 (3) | 0.0557 (8) | |
H9A | 0.5987 | 1.0534 | 0.4786 | 0.067* | |
H9B | 0.6663 | 0.9445 | 0.5008 | 0.067* | |
C7 | 0.6371 (2) | 0.7908 (4) | 0.2872 (3) | 0.0518 (7) | |
H7A | 0.6014 | 0.7384 | 0.2350 | 0.062* | |
H7B | 0.6717 | 0.8452 | 0.2367 | 0.062* | |
C8 | 0.5882 (2) | 0.8868 (4) | 0.3654 (4) | 0.0607 (8) | |
H8A | 0.5576 | 0.8311 | 0.4204 | 0.073* | |
H8B | 0.5506 | 0.9358 | 0.3139 | 0.073* | |
C10 | 0.7361 (2) | 1.1692 (3) | 0.4486 (3) | 0.0524 (7) | |
H10A | 0.7543 | 1.1174 | 0.5185 | 0.063* | |
H10B | 0.7009 | 1.2413 | 0.4764 | 0.063* | |
C11 | 0.8075 (2) | 1.2348 (3) | 0.3895 (3) | 0.0545 (8) | |
H11A | 0.8242 | 1.3135 | 0.4374 | 0.065* | |
H11B | 0.7908 | 1.2689 | 0.3110 | 0.065* | |
C12 | 0.8792 (2) | 1.1403 (3) | 0.3736 (3) | 0.0481 (6) | |
H12A | 0.9221 | 1.1913 | 0.3368 | 0.058* | |
H12B | 0.8979 | 1.1083 | 0.4518 | 0.058* | |
C13 | 0.92735 (16) | 0.9309 (3) | 0.2662 (2) | 0.0402 (5) | |
H13A | 0.9620 | 0.9207 | 0.3365 | 0.048* | |
H13B | 0.9577 | 0.9743 | 0.2032 | 0.048* | |
C14 | 0.6459 (2) | 1.1588 (4) | 0.2769 (3) | 0.0607 (8) | |
H14A | 0.6824 | 1.2130 | 0.2312 | 0.091* | |
H14B | 0.6092 | 1.2185 | 0.3169 | 0.091* | |
H14C | 0.6168 | 1.0981 | 0.2238 | 0.091* | |
H2NA | 0.722 (3) | 0.745 (5) | 0.398 (4) | 0.073* | |
H2NB | 0.661 (3) | 0.662 (5) | 0.410 (5) | 0.073* | |
H4NA | 0.825 (3) | 0.979 (5) | 0.339 (4) | 0.073* | |
H4NB | 0.832 (3) | 1.051 (5) | 0.221 (4) | 0.073* | |
H1W | 0.963 (3) | 0.771 (5) | 0.601 (4) | 0.073* | |
H2W | 1.025 (3) | 0.794 (4) | 0.532 (4) | 0.073* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0499 (3) | 0.0495 (3) | 0.0371 (3) | 0.0023 (3) | −0.0053 (2) | 0.0016 (2) |
Cl2 | 0.0585 (4) | 0.0587 (4) | 0.0678 (5) | −0.0034 (4) | 0.0199 (3) | 0.0161 (3) |
O1W | 0.0577 (18) | 0.0572 (17) | 0.200 (5) | 0.0060 (13) | −0.001 (2) | 0.025 (2) |
N1 | 0.0407 (10) | 0.0295 (9) | 0.0339 (9) | 0.0016 (8) | 0.0055 (8) | −0.0019 (7) |
N2 | 0.0406 (11) | 0.0393 (11) | 0.0407 (11) | −0.0079 (9) | 0.0088 (9) | −0.0005 (8) |
N3 | 0.0471 (12) | 0.0491 (12) | 0.0337 (10) | 0.0141 (10) | 0.0020 (9) | 0.0024 (8) |
N4 | 0.0406 (11) | 0.0300 (9) | 0.0378 (10) | −0.0032 (8) | −0.0008 (9) | −0.0037 (7) |
C1 | 0.0353 (11) | 0.0347 (10) | 0.0308 (10) | 0.0049 (9) | 0.0002 (9) | 0.0041 (8) |
C2 | 0.0447 (14) | 0.0459 (13) | 0.0431 (14) | 0.0132 (11) | 0.0074 (11) | 0.0046 (10) |
C3 | 0.0712 (19) | 0.0399 (13) | 0.0495 (15) | 0.0197 (14) | 0.0164 (14) | −0.0007 (11) |
C4 | 0.075 (2) | 0.0271 (11) | 0.0475 (14) | 0.0054 (12) | 0.0116 (14) | −0.0021 (9) |
C5 | 0.0519 (14) | 0.0292 (10) | 0.0366 (12) | −0.0010 (10) | 0.0040 (10) | 0.0009 (8) |
C6 | 0.0627 (18) | 0.0345 (12) | 0.0610 (17) | −0.0113 (12) | 0.0145 (14) | −0.0092 (11) |
C9 | 0.0576 (18) | 0.0638 (18) | 0.0461 (15) | 0.0245 (15) | 0.0178 (13) | 0.0089 (12) |
C7 | 0.0486 (15) | 0.0597 (17) | 0.0469 (15) | −0.0011 (13) | −0.0046 (12) | 0.0035 (12) |
C8 | 0.0416 (15) | 0.068 (2) | 0.072 (2) | 0.0109 (14) | 0.0078 (14) | 0.0152 (16) |
C10 | 0.071 (2) | 0.0489 (15) | 0.0374 (14) | 0.0199 (14) | −0.0006 (13) | −0.0081 (10) |
C11 | 0.081 (2) | 0.0313 (12) | 0.0504 (15) | 0.0045 (13) | −0.0126 (15) | −0.0110 (10) |
C12 | 0.0581 (17) | 0.0387 (12) | 0.0471 (14) | −0.0054 (12) | −0.0091 (12) | −0.0105 (10) |
C13 | 0.0361 (12) | 0.0421 (12) | 0.0426 (13) | −0.0017 (10) | 0.0023 (10) | −0.0017 (9) |
C14 | 0.062 (2) | 0.072 (2) | 0.0484 (16) | 0.0170 (16) | −0.0030 (14) | 0.0131 (13) |
Geometric parameters (Å, º) top
N1—C1 | 1.335 (3) | C1—C13 | 1.508 (4) |
N1—C5 | 1.342 (3) | C2—C3 | 1.395 (4) |
N2—C7 | 1.489 (4) | C3—C4 | 1.375 (5) |
N2—C6 | 1.491 (4) | C4—C5 | 1.394 (4) |
N3—C9 | 1.474 (4) | C5—C6 | 1.501 (4) |
N3—C10 | 1.477 (4) | C9—C8 | 1.527 (6) |
N3—C14 | 1.481 (4) | C7—C8 | 1.523 (5) |
N4—C12 | 1.492 (3) | C10—C11 | 1.516 (5) |
N4—C13 | 1.492 (3) | C11—C12 | 1.525 (5) |
C1—C2 | 1.395 (4) | | |
| | | |
C1—N1—C5 | 118.8 (2) | N1—C5—C4 | 122.0 (3) |
C7—N2—C6 | 114.0 (3) | N1—C5—C6 | 116.8 (2) |
C9—N3—C10 | 109.1 (2) | C4—C5—C6 | 121.2 (2) |
C9—N3—C14 | 110.4 (3) | N2—C6—C5 | 112.5 (2) |
C10—N3—C14 | 109.7 (3) | N3—C9—C8 | 114.2 (2) |
C12—N4—C13 | 113.7 (2) | N2—C7—C8 | 111.7 (3) |
N1—C1—C2 | 123.1 (2) | C7—C8—C9 | 115.8 (3) |
N1—C1—C13 | 115.9 (2) | N3—C10—C11 | 113.1 (2) |
C2—C1—C13 | 121.0 (2) | C10—C11—C12 | 115.3 (2) |
C1—C2—C3 | 117.4 (3) | N4—C12—C11 | 111.0 (3) |
C4—C3—C2 | 120.0 (2) | N4—C13—C1 | 110.2 (2) |
C3—C4—C5 | 118.8 (2) | | |
| | | |
C5—N1—C1—C2 | 2.4 (4) | C10—N3—C9—C8 | −177.1 (2) |
C5—N1—C1—C13 | −174.5 (2) | C14—N3—C9—C8 | 62.2 (3) |
N1—C1—C2—C3 | −1.3 (4) | C6—N2—C7—C8 | 169.4 (3) |
C13—C1—C2—C3 | 175.5 (2) | N2—C7—C8—C9 | 68.0 (4) |
C1—C2—C3—C4 | 0.0 (4) | N3—C9—C8—C7 | 52.9 (4) |
C2—C3—C4—C5 | 0.1 (4) | C9—N3—C10—C11 | 166.2 (2) |
C1—N1—C5—C4 | −2.3 (4) | C14—N3—C10—C11 | −72.7 (3) |
C1—N1—C5—C6 | 174.8 (2) | N3—C10—C11—C12 | −75.6 (3) |
C3—C4—C5—N1 | 1.1 (4) | C13—N4—C12—C11 | 173.6 (2) |
C3—C4—C5—C6 | −175.9 (3) | C10—C11—C12—N4 | 60.3 (3) |
C7—N2—C6—C5 | 85.2 (3) | C12—N4—C13—C1 | 161.7 (2) |
N1—C5—C6—N2 | 2.2 (4) | N1—C1—C13—N4 | −23.8 (3) |
C4—C5—C6—N2 | 179.3 (3) | C2—C1—C13—N4 | 159.2 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4NA···Cl1 | 0.83 (5) | 2.77 (5) | 3.456 (2) | 140 (4) |
N2—H2NA···Cl1 | 0.87 (5) | 2.48 (5) | 3.317 (3) | 162 (4) |
N2—H2NB···Cl2 | 0.77 (5) | 2.31 (5) | 3.062 (2) | 168 (5) |
N4—H4NA···N3 | 0.83 (5) | 2.46 (5) | 2.973 (3) | 121 (4) |
N4—H4NB···Cl1i | 0.99 (5) | 2.19 (5) | 3.128 (2) | 158 (4) |
O1W—H1W···Cl1 | 0.81 (3) | 2.57 (5) | 3.177 (3) | 133 (5) |
O1W—H2W···Cl2ii | 0.82 (3) | 2.45 (4) | 3.200 (4) | 152 (4) |
Symmetry codes: (i) x, −y+2, z−1/2; (ii) x+1/2, y+1/2, z. |
(II) 7-Methyl-3,7,11,17-tetraazabicyclo[11.3.1]-heptadeca-1(17),13,15-triene
trihydrochloride
top
Crystal data top
C14H27N43+·2.826Cl−·0.174NO3− | F(000) = 770 |
Mr = 362.37 | Dx = 1.329 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.7592 (3) Å | Cell parameters from 4178 reflections |
b = 10.8825 (3) Å | θ = 3–56.6° |
c = 15.4988 (3) Å | µ = 0.48 mm−1 |
β = 93.9033 (13)° | T = 293 K |
V = 1810.50 (8) Å3 | Irregular, colourless |
Z = 4 | 0.30 × 0.15 × 0.10 mm |
Data collection top
Siemens CCD SMART diffractometer | 4252 independent reflections |
Radiation source: fine-focus sealed tube | 2388 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.056 |
ω scans | θmax = 28.3°, θmin = 2.2° |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | h = −11→13 |
Tmin = 0.868, Tmax = 0.953 | k = −14→5 |
9674 measured reflections | l = −20→20 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.98 | Calculated w = 1/[σ2(Fo2) + (0.0457P)2] where P = (Fo2 + 2Fc2)/3 |
4252 reflections | (Δ/σ)max = 0.053 |
224 parameters | Δρmax = 0.33 e Å−3 |
6 restraints | Δρmin = −0.25 e Å−3 |
Special details top
Experimental. Colourless crystals of C14H26N4·H2O. 2 Cl (I) and
C14H27N4.2.826Cl.0.174NO3 (II) crystallized from ethanol were used for
structure determination. The reason for using such a large crystal (0.70 mm)
for the structure determination of (I) was that we had few crystals and all
attemps to cut them before mounting in the diffractometer leds to the breaking
in the longitudinal direction of the needles. The chosen crystals were mounted
on a glass fiber using an epoxy resin. Data were collected using a Siemens
SMART CCD area detector single-crystal diffractometer with graphite
monochromated Mo Kα radiation (λ = 0.71073 Å). Preliminary unit
cell constants were determined with a set of 45 narrow frames (0.3 in ω
scans. A total of 1420 frames of intensity data were collected with a frame
width of 0.3° per frame in ω (and counting time of 10 and 20 s/frame for (I)
and (II) respectively at a crystal to detector distance of 4.5 cm. Both series
of data were corrected for absorption (Sheldrick, 1996). The structures were
solved by direct methods. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Cl1 | 0.76168 (7) | 0.91368 (6) | 0.08908 (4) | 0.0433 (2) | |
Cl2 | 0.71122 (7) | 0.96745 (7) | 0.40628 (4) | 0.0471 (2) | |
Cl3 | 0.71992 (11) | 0.98723 (15) | 0.76760 (8) | 0.0465 (5) | 0.826 (4) |
N5 | 0.717 (2) | 0.973 (4) | 0.7695 (17) | 0.099 (4) | 0.174 (4) |
O1 | 0.7333 (14) | 0.9219 (16) | 0.7047 (10) | 0.099 (4) | 0.174 (4) |
O2 | 0.8004 (15) | 0.9904 (15) | 0.8194 (11) | 0.099 (4) | 0.174 (4) |
O3 | 0.6269 (16) | 1.0291 (16) | 0.7770 (10) | 0.099 (4) | 0.174 (4) |
N1 | 0.5643 (2) | 0.1747 (2) | 0.08888 (14) | 0.0414 (6) | |
N2 | 0.7029 (2) | 0.1116 (2) | 0.23680 (15) | 0.0412 (6) | |
N3 | 0.9915 (2) | 0.2649 (2) | 0.09213 (15) | 0.0373 (6) | |
N4 | 0.6914 (2) | 0.1191 (2) | −0.05944 (16) | 0.0417 (6) | |
C1 | 0.5224 (3) | 0.2226 (3) | 0.01315 (19) | 0.0424 (7) | |
C2 | 0.4484 (3) | 0.3264 (3) | 0.0066 (2) | 0.0497 (8) | |
H2 | 0.4210 | 0.3578 | −0.0472 | 0.060* | |
C3 | 0.4162 (3) | 0.3824 (3) | 0.0817 (2) | 0.0534 (9) | |
H3 | 0.3662 | 0.4521 | 0.0791 | 0.064* | |
C4 | 0.4584 (3) | 0.3347 (3) | 0.1601 (2) | 0.0494 (8) | |
H4 | 0.4375 | 0.3711 | 0.2115 | 0.059* | |
C5 | 0.5328 (3) | 0.2310 (3) | 0.16112 (18) | 0.0403 (7) | |
C6 | 0.5798 (3) | 0.1710 (3) | 0.24411 (18) | 0.0500 (8) | |
H6A | 0.5868 | 0.2323 | 0.2896 | 0.060* | |
H6B | 0.5201 | 0.1097 | 0.2602 | 0.060* | |
C7 | 0.8040 (3) | 0.2022 (3) | 0.22812 (18) | 0.0424 (7) | |
H7A | 0.8078 | 0.2569 | 0.2777 | 0.051* | |
H7B | 0.7852 | 0.2514 | 0.1767 | 0.051* | |
C8 | 0.9294 (3) | 0.1415 (3) | 0.22205 (18) | 0.0424 (7) | |
H8A | 0.9189 | 0.0682 | 0.1867 | 0.051* | |
H8B | 0.9609 | 0.1161 | 0.2795 | 0.051* | |
C9 | 1.0251 (3) | 0.2244 (3) | 0.18372 (18) | 0.0471 (8) | |
H9A | 1.0365 | 0.2969 | 0.2199 | 0.056* | |
H9B | 1.1042 | 0.1814 | 0.1853 | 0.056* | |
C10 | 0.9667 (3) | 0.1594 (3) | 0.03129 (18) | 0.0428 (7) | |
H10A | 0.9103 | 0.1027 | 0.0570 | 0.051* | |
H10B | 1.0444 | 0.1162 | 0.0248 | 0.051* | |
C11 | 0.9112 (3) | 0.1955 (3) | −0.05761 (18) | 0.0503 (8) | |
H11A | 0.9239 | 0.1280 | −0.0969 | 0.060* | |
H11B | 0.9574 | 0.2654 | −0.0774 | 0.060* | |
C12 | 0.7736 (3) | 0.2282 (3) | −0.06457 (19) | 0.0474 (8) | |
H12A | 0.7568 | 0.2847 | −0.0184 | 0.057* | |
H12B | 0.7539 | 0.2700 | −0.1191 | 0.057* | |
C13 | 0.5572 (3) | 0.1510 (3) | −0.06484 (18) | 0.0497 (8) | |
H13A | 0.5082 | 0.0761 | −0.0695 | 0.060* | |
H13B | 0.5376 | 0.1993 | −0.1166 | 0.060* | |
C14 | 1.0954 (3) | 0.3446 (3) | 0.0638 (2) | 0.0641 (10) | |
H14A | 1.1081 | 0.4122 | 0.1032 | 0.096* | |
H14B | 1.0739 | 0.3754 | 0.0067 | 0.096* | |
H14C | 1.1705 | 0.2970 | 0.0635 | 0.096* | |
H2NA | 0.719 (3) | 0.064 (3) | 0.289 (2) | 0.077* | |
H2NB | 0.700 (3) | 0.060 (3) | 0.186 (2) | 0.077* | |
H3N | 0.923 (3) | 0.315 (3) | 0.097 (2) | 0.077* | |
H4NA | 0.705 (3) | 0.061 (3) | −0.111 (2) | 0.077* | |
H4NB | 0.714 (3) | 0.078 (3) | −0.008 (2) | 0.077* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0421 (5) | 0.0365 (4) | 0.0523 (4) | −0.0002 (3) | 0.0098 (3) | −0.0019 (3) |
Cl2 | 0.0627 (6) | 0.0369 (4) | 0.0423 (4) | −0.0108 (4) | 0.0081 (3) | 0.0011 (3) |
Cl3 | 0.0474 (9) | 0.0487 (7) | 0.0441 (6) | 0.0019 (5) | 0.0085 (5) | −0.0043 (5) |
N5 | 0.110 (10) | 0.092 (8) | 0.094 (8) | 0.021 (6) | 0.002 (6) | −0.035 (6) |
O1 | 0.110 (10) | 0.092 (8) | 0.094 (8) | 0.021 (6) | 0.002 (6) | −0.035 (6) |
O2 | 0.110 (10) | 0.092 (8) | 0.094 (8) | 0.021 (6) | 0.002 (6) | −0.035 (6) |
O3 | 0.110 (10) | 0.092 (8) | 0.094 (8) | 0.021 (6) | 0.002 (6) | −0.035 (6) |
N1 | 0.0369 (15) | 0.0451 (15) | 0.0429 (13) | 0.0059 (12) | 0.0072 (11) | 0.0002 (11) |
N2 | 0.0467 (17) | 0.0404 (15) | 0.0374 (13) | −0.0034 (13) | 0.0095 (12) | 0.0044 (11) |
N3 | 0.0327 (15) | 0.0346 (13) | 0.0458 (13) | −0.0031 (11) | 0.0114 (11) | −0.0026 (11) |
N4 | 0.0377 (17) | 0.0477 (16) | 0.0401 (13) | 0.0038 (13) | 0.0048 (11) | −0.0016 (12) |
C1 | 0.0293 (18) | 0.0470 (18) | 0.0509 (18) | 0.0041 (14) | 0.0021 (14) | −0.0005 (14) |
C2 | 0.039 (2) | 0.0478 (19) | 0.062 (2) | 0.0056 (16) | −0.0025 (15) | 0.0057 (16) |
C3 | 0.038 (2) | 0.0385 (18) | 0.083 (3) | 0.0084 (15) | 0.0039 (17) | −0.0028 (17) |
C4 | 0.0371 (19) | 0.0482 (19) | 0.065 (2) | 0.0018 (16) | 0.0171 (16) | −0.0122 (16) |
C5 | 0.0297 (18) | 0.0422 (17) | 0.0501 (17) | −0.0028 (14) | 0.0110 (14) | −0.0041 (14) |
C6 | 0.049 (2) | 0.057 (2) | 0.0463 (17) | 0.0003 (17) | 0.0225 (15) | −0.0001 (15) |
C7 | 0.051 (2) | 0.0334 (16) | 0.0445 (16) | −0.0022 (15) | 0.0126 (14) | 0.0006 (13) |
C8 | 0.043 (2) | 0.0398 (16) | 0.0435 (16) | −0.0005 (15) | −0.0014 (14) | 0.0029 (13) |
C9 | 0.0381 (19) | 0.0493 (19) | 0.0532 (18) | 0.0016 (15) | −0.0018 (15) | 0.0003 (15) |
C10 | 0.0385 (19) | 0.0349 (16) | 0.0564 (18) | −0.0006 (14) | 0.0134 (14) | −0.0064 (14) |
C11 | 0.048 (2) | 0.058 (2) | 0.0464 (17) | −0.0024 (17) | 0.0161 (15) | −0.0050 (15) |
C12 | 0.052 (2) | 0.0457 (18) | 0.0440 (16) | 0.0042 (17) | 0.0033 (15) | 0.0009 (14) |
C13 | 0.039 (2) | 0.064 (2) | 0.0446 (17) | 0.0060 (17) | −0.0035 (14) | −0.0027 (15) |
C14 | 0.055 (2) | 0.061 (2) | 0.079 (2) | −0.0228 (19) | 0.0219 (18) | −0.0026 (19) |
Geometric parameters (Å, º) top
N5—O2 | 1.155 (16) | N4—C12 | 1.486 (4) |
N5—O3 | 1.160 (16) | C1—C2 | 1.381 (4) |
N5—O1 | 1.172 (16) | C1—C13 | 1.507 (4) |
N1—C1 | 1.335 (3) | C2—C3 | 1.379 (4) |
N1—C5 | 1.340 (3) | C3—C4 | 1.370 (4) |
N2—C7 | 1.481 (4) | C4—C5 | 1.383 (4) |
N2—C6 | 1.485 (4) | C5—C6 | 1.499 (4) |
N3—C10 | 1.498 (3) | C7—C8 | 1.511 (4) |
N3—C14 | 1.503 (4) | C8—C9 | 1.520 (4) |
N3—C9 | 1.507 (3) | C10—C11 | 1.516 (4) |
N4—C13 | 1.482 (4) | C11—C12 | 1.519 (4) |
| | | |
O2—N5—O3 | 117.6 (16) | C4—C3—C2 | 119.7 (3) |
O2—N5—O1 | 120.0 (16) | C3—C4—C5 | 118.4 (3) |
O3—N5—O1 | 120.5 (16) | N1—C5—C4 | 122.9 (3) |
C1—N1—C5 | 117.8 (3) | N1—C5—C6 | 115.3 (3) |
C7—N2—C6 | 112.4 (2) | C4—C5—C6 | 121.7 (3) |
C10—N3—C14 | 111.3 (2) | N2—C6—C5 | 112.0 (2) |
C10—N3—C9 | 113.0 (2) | N2—C7—C8 | 112.3 (2) |
C14—N3—C9 | 107.9 (2) | C7—C8—C9 | 113.3 (2) |
C13—N4—C12 | 113.0 (2) | N3—C9—C8 | 114.6 (2) |
N1—C1—C2 | 122.9 (3) | N3—C10—C11 | 114.6 (2) |
N1—C1—C13 | 114.6 (3) | C10—C11—C12 | 116.5 (2) |
C2—C1—C13 | 122.5 (3) | N4—C12—C11 | 112.9 (3) |
C3—C2—C1 | 118.4 (3) | N4—C13—C1 | 111.7 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4NB···Cl1i | 0.92 (3) | 2.38 (4) | 3.260 (3) | 160 (3) |
N2—H2NB···Cl1i | 0.96 (3) | 2.32 (3) | 3.237 (3) | 159 (3) |
N2—H2NA···Cl2i | 0.96 (3) | 2.11 (3) | 3.056 (2) | 167 (3) |
N4—H4NA···Cl3ii | 1.03 (3) | 2.07 (3) | 3.074 (3) | 164 (3) |
N4—H4NA···O2ii | 1.03 (3) | 1.72 (4) | 2.676 (14) | 152 (3) |
N4—H4NA···O3ii | 1.03 (3) | 1.91 (3) | 2.761 (14) | 137 (3) |
N3—H3N···Cl2iii | 0.93 (3) | 2.20 (3) | 3.102 (3) | 166 (3) |
Symmetry codes: (i) x, y−1, z; (ii) x, y−1, z−1; (iii) −x+3/2, y−1/2, −z+1/2. |
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