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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, C14H26N42+·2Cl-·H2O, (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, C14H27N43+·2.826Cl-·0.174NO3-, (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 NO3- ion in a disordered structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100006065/qb0201sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100006065/qb0201Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100006065/qb0201IIsup3.hkl
Contains datablock II

CCDC references: 146092; 146093

Computing details top

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·H2OF(000) = 728
Mr = 339.30Dx = 1.246 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
a = 16.7683 (3) ÅCell parameters from 6095 reflections
b = 9.7089 (2) Åθ = 3–56.6°
c = 11.116 (2) ŵ = 0.36 mm1
β = 90.9963 (11)°T = 293 K
V = 1809.4 (3) Å3Needle, colourless
Z = 40.70 × 0.20 × 0.15 mm
Data collection top
Siemens CCD SMART
diffractometer
2812 independent reflections
Radiation source: fine-focus sealed tube2656 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
ω scansθmax = 28.2°, θmin = 2.4°
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
h = 1622
Tmin = 0.785, Tmax = 0.948k = 1212
6531 measured reflectionsl = 1214
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)] = 0.035H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.112Calculated w = 1/[σ2(Fo2) + (0.0749P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.002
2812 reflectionsΔρmax = 0.29 e Å3
208 parametersΔρmin = 0.29 e Å3
3 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute 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
xyzUiso*/Ueq
Cl10.81700 (4)0.83287 (6)0.55323 (5)0.04561 (17)
Cl20.58601 (5)0.52347 (8)0.53363 (7)0.0614 (2)
O1W0.9975 (2)0.7336 (4)0.5626 (5)0.1050 (15)
N10.82743 (13)0.7522 (2)0.26247 (18)0.0346 (4)
N20.68646 (15)0.6942 (2)0.3611 (2)0.0401 (5)
N30.69080 (15)1.0765 (3)0.36737 (19)0.0433 (5)
N40.85779 (13)1.0194 (2)0.2967 (2)0.0361 (4)
C10.89915 (14)0.7910 (2)0.2247 (2)0.0336 (4)
C20.94779 (18)0.7064 (3)0.1559 (2)0.0445 (6)
H20.99710.73660.12940.053*
C30.9195 (2)0.5747 (3)0.1285 (3)0.0534 (7)
H30.95020.51520.08280.064*
C40.8464 (2)0.5330 (3)0.1689 (3)0.0497 (7)
H40.82710.44540.15120.060*
C50.80172 (17)0.6244 (2)0.2370 (2)0.0392 (5)
C60.7240 (2)0.5816 (3)0.2905 (3)0.0526 (7)
H6A0.68760.55340.22640.063*
H6B0.73300.50280.34270.063*
C90.6358 (2)0.9925 (3)0.4388 (3)0.0557 (8)
H9A0.59871.05340.47860.067*
H9B0.66630.94450.50080.067*
C70.6371 (2)0.7908 (4)0.2872 (3)0.0518 (7)
H7A0.60140.73840.23500.062*
H7B0.67170.84520.23670.062*
C80.5882 (2)0.8868 (4)0.3654 (4)0.0607 (8)
H8A0.55760.83110.42040.073*
H8B0.55060.93580.31390.073*
C100.7361 (2)1.1692 (3)0.4486 (3)0.0524 (7)
H10A0.75431.11740.51850.063*
H10B0.70091.24130.47640.063*
C110.8075 (2)1.2348 (3)0.3895 (3)0.0545 (8)
H11A0.82421.31350.43740.065*
H11B0.79081.26890.31100.065*
C120.8792 (2)1.1403 (3)0.3736 (3)0.0481 (6)
H12A0.92211.19130.33680.058*
H12B0.89791.10830.45180.058*
C130.92735 (16)0.9309 (3)0.2662 (2)0.0402 (5)
H13A0.96200.92070.33650.048*
H13B0.95770.97430.20320.048*
C140.6459 (2)1.1588 (4)0.2769 (3)0.0607 (8)
H14A0.68241.21300.23120.091*
H14B0.60921.21850.31690.091*
H14C0.61681.09810.22380.091*
H2NA0.722 (3)0.745 (5)0.398 (4)0.073*
H2NB0.661 (3)0.662 (5)0.410 (5)0.073*
H4NA0.825 (3)0.979 (5)0.339 (4)0.073*
H4NB0.832 (3)1.051 (5)0.221 (4)0.073*
H1W0.963 (3)0.771 (5)0.601 (4)0.073*
H2W1.025 (3)0.794 (4)0.532 (4)0.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0499 (3)0.0495 (3)0.0371 (3)0.0023 (3)0.0053 (2)0.0016 (2)
Cl20.0585 (4)0.0587 (4)0.0678 (5)0.0034 (4)0.0199 (3)0.0161 (3)
O1W0.0577 (18)0.0572 (17)0.200 (5)0.0060 (13)0.001 (2)0.025 (2)
N10.0407 (10)0.0295 (9)0.0339 (9)0.0016 (8)0.0055 (8)0.0019 (7)
N20.0406 (11)0.0393 (11)0.0407 (11)0.0079 (9)0.0088 (9)0.0005 (8)
N30.0471 (12)0.0491 (12)0.0337 (10)0.0141 (10)0.0020 (9)0.0024 (8)
N40.0406 (11)0.0300 (9)0.0378 (10)0.0032 (8)0.0008 (9)0.0037 (7)
C10.0353 (11)0.0347 (10)0.0308 (10)0.0049 (9)0.0002 (9)0.0041 (8)
C20.0447 (14)0.0459 (13)0.0431 (14)0.0132 (11)0.0074 (11)0.0046 (10)
C30.0712 (19)0.0399 (13)0.0495 (15)0.0197 (14)0.0164 (14)0.0007 (11)
C40.075 (2)0.0271 (11)0.0475 (14)0.0054 (12)0.0116 (14)0.0021 (9)
C50.0519 (14)0.0292 (10)0.0366 (12)0.0010 (10)0.0040 (10)0.0009 (8)
C60.0627 (18)0.0345 (12)0.0610 (17)0.0113 (12)0.0145 (14)0.0092 (11)
C90.0576 (18)0.0638 (18)0.0461 (15)0.0245 (15)0.0178 (13)0.0089 (12)
C70.0486 (15)0.0597 (17)0.0469 (15)0.0011 (13)0.0046 (12)0.0035 (12)
C80.0416 (15)0.068 (2)0.072 (2)0.0109 (14)0.0078 (14)0.0152 (16)
C100.071 (2)0.0489 (15)0.0374 (14)0.0199 (14)0.0006 (13)0.0081 (10)
C110.081 (2)0.0313 (12)0.0504 (15)0.0045 (13)0.0126 (15)0.0110 (10)
C120.0581 (17)0.0387 (12)0.0471 (14)0.0054 (12)0.0091 (12)0.0105 (10)
C130.0361 (12)0.0421 (12)0.0426 (13)0.0017 (10)0.0023 (10)0.0017 (9)
C140.062 (2)0.072 (2)0.0484 (16)0.0170 (16)0.0030 (14)0.0131 (13)
Geometric parameters (Å, º) top
N1—C11.335 (3)C1—C131.508 (4)
N1—C51.342 (3)C2—C31.395 (4)
N2—C71.489 (4)C3—C41.375 (5)
N2—C61.491 (4)C4—C51.394 (4)
N3—C91.474 (4)C5—C61.501 (4)
N3—C101.477 (4)C9—C81.527 (6)
N3—C141.481 (4)C7—C81.523 (5)
N4—C121.492 (3)C10—C111.516 (5)
N4—C131.492 (3)C11—C121.525 (5)
C1—C21.395 (4)
C1—N1—C5118.8 (2)N1—C5—C4122.0 (3)
C7—N2—C6114.0 (3)N1—C5—C6116.8 (2)
C9—N3—C10109.1 (2)C4—C5—C6121.2 (2)
C9—N3—C14110.4 (3)N2—C6—C5112.5 (2)
C10—N3—C14109.7 (3)N3—C9—C8114.2 (2)
C12—N4—C13113.7 (2)N2—C7—C8111.7 (3)
N1—C1—C2123.1 (2)C7—C8—C9115.8 (3)
N1—C1—C13115.9 (2)N3—C10—C11113.1 (2)
C2—C1—C13121.0 (2)C10—C11—C12115.3 (2)
C1—C2—C3117.4 (3)N4—C12—C11111.0 (3)
C4—C3—C2120.0 (2)N4—C13—C1110.2 (2)
C3—C4—C5118.8 (2)
C5—N1—C1—C22.4 (4)C10—N3—C9—C8177.1 (2)
C5—N1—C1—C13174.5 (2)C14—N3—C9—C862.2 (3)
N1—C1—C2—C31.3 (4)C6—N2—C7—C8169.4 (3)
C13—C1—C2—C3175.5 (2)N2—C7—C8—C968.0 (4)
C1—C2—C3—C40.0 (4)N3—C9—C8—C752.9 (4)
C2—C3—C4—C50.1 (4)C9—N3—C10—C11166.2 (2)
C1—N1—C5—C42.3 (4)C14—N3—C10—C1172.7 (3)
C1—N1—C5—C6174.8 (2)N3—C10—C11—C1275.6 (3)
C3—C4—C5—N11.1 (4)C13—N4—C12—C11173.6 (2)
C3—C4—C5—C6175.9 (3)C10—C11—C12—N460.3 (3)
C7—N2—C6—C585.2 (3)C12—N4—C13—C1161.7 (2)
N1—C5—C6—N22.2 (4)N1—C1—C13—N423.8 (3)
C4—C5—C6—N2179.3 (3)C2—C1—C13—N4159.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4NA···Cl10.83 (5)2.77 (5)3.456 (2)140 (4)
N2—H2NA···Cl10.87 (5)2.48 (5)3.317 (3)162 (4)
N2—H2NB···Cl20.77 (5)2.31 (5)3.062 (2)168 (5)
N4—H4NA···N30.83 (5)2.46 (5)2.973 (3)121 (4)
N4—H4NB···Cl1i0.99 (5)2.19 (5)3.128 (2)158 (4)
O1W—H1W···Cl10.81 (3)2.57 (5)3.177 (3)133 (5)
O1W—H2W···Cl2ii0.82 (3)2.45 (4)3.200 (4)152 (4)
Symmetry codes: (i) x, y+2, z1/2; (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·0.174NO3F(000) = 770
Mr = 362.37Dx = 1.329 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.7592 (3) ÅCell parameters from 4178 reflections
b = 10.8825 (3) Åθ = 3–56.6°
c = 15.4988 (3) ŵ = 0.48 mm1
β = 93.9033 (13)°T = 293 K
V = 1810.50 (8) Å3Irregular, colourless
Z = 40.30 × 0.15 × 0.10 mm
Data collection top
Siemens CCD SMART
diffractometer
4252 independent reflections
Radiation source: fine-focus sealed tube2388 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
ω scansθmax = 28.3°, θmin = 2.2°
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
h = 1113
Tmin = 0.868, Tmax = 0.953k = 145
9674 measured reflectionsl = 2020
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H atoms treated by a mixture of independent and constrained refinement
S = 0.98Calculated w = 1/[σ2(Fo2) + (0.0457P)2]
where P = (Fo2 + 2Fc2)/3
4252 reflections(Δ/σ)max = 0.053
224 parametersΔρmax = 0.33 e Å3
6 restraintsΔρmin = 0.25 e Å3
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
xyzUiso*/UeqOcc. (<1)
Cl10.76168 (7)0.91368 (6)0.08908 (4)0.0433 (2)
Cl20.71122 (7)0.96745 (7)0.40628 (4)0.0471 (2)
Cl30.71992 (11)0.98723 (15)0.76760 (8)0.0465 (5)0.826 (4)
N50.717 (2)0.973 (4)0.7695 (17)0.099 (4)0.174 (4)
O10.7333 (14)0.9219 (16)0.7047 (10)0.099 (4)0.174 (4)
O20.8004 (15)0.9904 (15)0.8194 (11)0.099 (4)0.174 (4)
O30.6269 (16)1.0291 (16)0.7770 (10)0.099 (4)0.174 (4)
N10.5643 (2)0.1747 (2)0.08888 (14)0.0414 (6)
N20.7029 (2)0.1116 (2)0.23680 (15)0.0412 (6)
N30.9915 (2)0.2649 (2)0.09213 (15)0.0373 (6)
N40.6914 (2)0.1191 (2)0.05944 (16)0.0417 (6)
C10.5224 (3)0.2226 (3)0.01315 (19)0.0424 (7)
C20.4484 (3)0.3264 (3)0.0066 (2)0.0497 (8)
H20.42100.35780.04720.060*
C30.4162 (3)0.3824 (3)0.0817 (2)0.0534 (9)
H30.36620.45210.07910.064*
C40.4584 (3)0.3347 (3)0.1601 (2)0.0494 (8)
H40.43750.37110.21150.059*
C50.5328 (3)0.2310 (3)0.16112 (18)0.0403 (7)
C60.5798 (3)0.1710 (3)0.24411 (18)0.0500 (8)
H6A0.58680.23230.28960.060*
H6B0.52010.10970.26020.060*
C70.8040 (3)0.2022 (3)0.22812 (18)0.0424 (7)
H7A0.80780.25690.27770.051*
H7B0.78520.25140.17670.051*
C80.9294 (3)0.1415 (3)0.22205 (18)0.0424 (7)
H8A0.91890.06820.18670.051*
H8B0.96090.11610.27950.051*
C91.0251 (3)0.2244 (3)0.18372 (18)0.0471 (8)
H9A1.03650.29690.21990.056*
H9B1.10420.18140.18530.056*
C100.9667 (3)0.1594 (3)0.03129 (18)0.0428 (7)
H10A0.91030.10270.05700.051*
H10B1.04440.11620.02480.051*
C110.9112 (3)0.1955 (3)0.05761 (18)0.0503 (8)
H11A0.92390.12800.09690.060*
H11B0.95740.26540.07740.060*
C120.7736 (3)0.2282 (3)0.06457 (19)0.0474 (8)
H12A0.75680.28470.01840.057*
H12B0.75390.27000.11910.057*
C130.5572 (3)0.1510 (3)0.06484 (18)0.0497 (8)
H13A0.50820.07610.06950.060*
H13B0.53760.19930.11660.060*
C141.0954 (3)0.3446 (3)0.0638 (2)0.0641 (10)
H14A1.10810.41220.10320.096*
H14B1.07390.37540.00670.096*
H14C1.17050.29700.06350.096*
H2NA0.719 (3)0.064 (3)0.289 (2)0.077*
H2NB0.700 (3)0.060 (3)0.186 (2)0.077*
H3N0.923 (3)0.315 (3)0.097 (2)0.077*
H4NA0.705 (3)0.061 (3)0.111 (2)0.077*
H4NB0.714 (3)0.078 (3)0.008 (2)0.077*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0421 (5)0.0365 (4)0.0523 (4)0.0002 (3)0.0098 (3)0.0019 (3)
Cl20.0627 (6)0.0369 (4)0.0423 (4)0.0108 (4)0.0081 (3)0.0011 (3)
Cl30.0474 (9)0.0487 (7)0.0441 (6)0.0019 (5)0.0085 (5)0.0043 (5)
N50.110 (10)0.092 (8)0.094 (8)0.021 (6)0.002 (6)0.035 (6)
O10.110 (10)0.092 (8)0.094 (8)0.021 (6)0.002 (6)0.035 (6)
O20.110 (10)0.092 (8)0.094 (8)0.021 (6)0.002 (6)0.035 (6)
O30.110 (10)0.092 (8)0.094 (8)0.021 (6)0.002 (6)0.035 (6)
N10.0369 (15)0.0451 (15)0.0429 (13)0.0059 (12)0.0072 (11)0.0002 (11)
N20.0467 (17)0.0404 (15)0.0374 (13)0.0034 (13)0.0095 (12)0.0044 (11)
N30.0327 (15)0.0346 (13)0.0458 (13)0.0031 (11)0.0114 (11)0.0026 (11)
N40.0377 (17)0.0477 (16)0.0401 (13)0.0038 (13)0.0048 (11)0.0016 (12)
C10.0293 (18)0.0470 (18)0.0509 (18)0.0041 (14)0.0021 (14)0.0005 (14)
C20.039 (2)0.0478 (19)0.062 (2)0.0056 (16)0.0025 (15)0.0057 (16)
C30.038 (2)0.0385 (18)0.083 (3)0.0084 (15)0.0039 (17)0.0028 (17)
C40.0371 (19)0.0482 (19)0.065 (2)0.0018 (16)0.0171 (16)0.0122 (16)
C50.0297 (18)0.0422 (17)0.0501 (17)0.0028 (14)0.0110 (14)0.0041 (14)
C60.049 (2)0.057 (2)0.0463 (17)0.0003 (17)0.0225 (15)0.0001 (15)
C70.051 (2)0.0334 (16)0.0445 (16)0.0022 (15)0.0126 (14)0.0006 (13)
C80.043 (2)0.0398 (16)0.0435 (16)0.0005 (15)0.0014 (14)0.0029 (13)
C90.0381 (19)0.0493 (19)0.0532 (18)0.0016 (15)0.0018 (15)0.0003 (15)
C100.0385 (19)0.0349 (16)0.0564 (18)0.0006 (14)0.0134 (14)0.0064 (14)
C110.048 (2)0.058 (2)0.0464 (17)0.0024 (17)0.0161 (15)0.0050 (15)
C120.052 (2)0.0457 (18)0.0440 (16)0.0042 (17)0.0033 (15)0.0009 (14)
C130.039 (2)0.064 (2)0.0446 (17)0.0060 (17)0.0035 (14)0.0027 (15)
C140.055 (2)0.061 (2)0.079 (2)0.0228 (19)0.0219 (18)0.0026 (19)
Geometric parameters (Å, º) top
N5—O21.155 (16)N4—C121.486 (4)
N5—O31.160 (16)C1—C21.381 (4)
N5—O11.172 (16)C1—C131.507 (4)
N1—C11.335 (3)C2—C31.379 (4)
N1—C51.340 (3)C3—C41.370 (4)
N2—C71.481 (4)C4—C51.383 (4)
N2—C61.485 (4)C5—C61.499 (4)
N3—C101.498 (3)C7—C81.511 (4)
N3—C141.503 (4)C8—C91.520 (4)
N3—C91.507 (3)C10—C111.516 (4)
N4—C131.482 (4)C11—C121.519 (4)
O2—N5—O3117.6 (16)C4—C3—C2119.7 (3)
O2—N5—O1120.0 (16)C3—C4—C5118.4 (3)
O3—N5—O1120.5 (16)N1—C5—C4122.9 (3)
C1—N1—C5117.8 (3)N1—C5—C6115.3 (3)
C7—N2—C6112.4 (2)C4—C5—C6121.7 (3)
C10—N3—C14111.3 (2)N2—C6—C5112.0 (2)
C10—N3—C9113.0 (2)N2—C7—C8112.3 (2)
C14—N3—C9107.9 (2)C7—C8—C9113.3 (2)
C13—N4—C12113.0 (2)N3—C9—C8114.6 (2)
N1—C1—C2122.9 (3)N3—C10—C11114.6 (2)
N1—C1—C13114.6 (3)C10—C11—C12116.5 (2)
C2—C1—C13122.5 (3)N4—C12—C11112.9 (3)
C3—C2—C1118.4 (3)N4—C13—C1111.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4NB···Cl1i0.92 (3)2.38 (4)3.260 (3)160 (3)
N2—H2NB···Cl1i0.96 (3)2.32 (3)3.237 (3)159 (3)
N2—H2NA···Cl2i0.96 (3)2.11 (3)3.056 (2)167 (3)
N4—H4NA···Cl3ii1.03 (3)2.07 (3)3.074 (3)164 (3)
N4—H4NA···O2ii1.03 (3)1.72 (4)2.676 (14)152 (3)
N4—H4NA···O3ii1.03 (3)1.91 (3)2.761 (14)137 (3)
N3—H3N···Cl2iii0.93 (3)2.20 (3)3.102 (3)166 (3)
Symmetry codes: (i) x, y1, z; (ii) x, y1, z1; (iii) x+3/2, y1/2, z+1/2.
 

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