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The structure analyses of racemic 3-chloro-1-(4-morpholino-5-nitroimidazol-1-yl)propan-2-ol, C
10H
15ClN
4O
4, (II), and 3-chloro-1-(5-morpholino-4-nitroimidazol-1-yl)propan-2-ol, C
10H
15ClN
4O
4, (III), have been undertaken in order to determine the position of the morpholine residue in these two isomers. The morpholine residue in (II) is connected at the 4-position, while in (III), it is connected at the 5-position of the imidazole ring. The morpholine mean planes and nitro groups in the two compounds deviate from the imidazole planes to different extents. The nitro groups in (II) and (III) take part in the conjugation system of the imidazole rings. In consequence, the exocyclic C—N bonds are significantly shorter than the normal single C
sp2—NO
2 bond and the nitro groups in (II) and (III) show an extraordinary stability on treatment with morpholine and piperidine [Gzella, Wrzeciono & Pöppel (1999).
Acta Cryst. C
55, 1562–1565]. In the crystal lattice, the molecules of both compounds are linked by O—H
N and C—H
O intermolecular hydrogen bonds.
Supporting information
CCDC references: 150863; 150864
For both compounds, data collection: Kuma KM-4 Software (Kuma Diffraction, 1991); cell refinement: Kuma KM-4 Software; data reduction: Kuma KM-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
(II) 3-Chloro-1-(4-morpholinyl-5-nitroimidazol-1-yl)propan-2-ol
top
Crystal data top
C10H15ClN4O4 | F(000) = 304 |
Mr = 290.71 | Dx = 1.534 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54178 Å |
a = 9.6840 (8) Å | Cell parameters from 55 reflections |
b = 5.2868 (8) Å | θ = 16.8–31.8° |
c = 12.8212 (7) Å | µ = 2.88 mm−1 |
β = 106.470 (6)° | T = 293 K |
V = 629.48 (11) Å3 | Needle, yellow |
Z = 2 | 0.54 × 0.17 × 0.10 mm |
Data collection top
Kuma Diffraction KM-4 diffractometer | 2201 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.032 |
Graphite monochromator | θmax = 70.1°, θmin = 3.6° |
ω/2θ scans | h = −11→11 |
Absorption correction: ψ-scan (North et al., 1968) | k = −6→6 |
Tmin = 0.511, Tmax = 0.750 | l = 0→15 |
2286 measured reflections | 2 standard reflections every 100 reflections |
2245 independent reflections | intensity decay: 0.8% |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.025 | w = 1/[σ2(Fo2) + (0.0482P)2 + 0.0886P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.072 | (Δ/σ)max = 0.010 |
S = 1.04 | Δρmax = 0.17 e Å−3 |
2245 reflections | Δρmin = −0.26 e Å−3 |
178 parameters | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.0246 (15) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983) |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.344 (13) |
Special details top
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 | |
N1 | 0.25344 (13) | 0.2996 (3) | 0.44535 (10) | 0.0324 (3) | |
C2 | 0.35945 (16) | 0.1446 (4) | 0.49604 (12) | 0.0364 (3) | |
H2A | 0.4013 | 0.0288 | 0.4596 | 0.044* | |
N3 | 0.39995 (14) | 0.1702 (3) | 0.60289 (11) | 0.0360 (3) | |
C4 | 0.31146 (15) | 0.3495 (3) | 0.62562 (12) | 0.0316 (3) | |
C5 | 0.22027 (15) | 0.4378 (3) | 0.52711 (12) | 0.0315 (3) | |
C6 | 0.17975 (16) | 0.2867 (3) | 0.32829 (12) | 0.0346 (3) | |
H6A | 0.0845 | 0.3606 | 0.3142 | 0.042* | |
H6B | 0.1685 | 0.1111 | 0.3055 | 0.042* | |
C7 | 0.26426 (16) | 0.4268 (3) | 0.26313 (12) | 0.0341 (3) | |
H7A | 0.2771 | 0.6024 | 0.2885 | 0.041* | |
C8 | 0.1863 (2) | 0.4274 (4) | 0.14286 (13) | 0.0437 (4) | |
H8A | 0.2432 | 0.5202 | 0.1045 | 0.052* | |
H8B | 0.0950 | 0.5146 | 0.1313 | 0.052* | |
Cl9 | 0.15358 (5) | 0.11495 (11) | 0.08745 (3) | 0.05587 (16) | |
O10 | 0.40081 (13) | 0.3153 (3) | 0.28177 (10) | 0.0419 (3) | |
H10A | 0.462 (3) | 0.395 (5) | 0.3097 (19) | 0.049 (7)* | |
N11 | 0.32214 (13) | 0.4247 (3) | 0.72854 (10) | 0.0363 (3) | |
C12 | 0.45195 (17) | 0.3614 (3) | 0.81480 (12) | 0.0362 (3) | |
H12A | 0.5354 | 0.3695 | 0.7873 | 0.043* | |
H12B | 0.4446 | 0.1910 | 0.8408 | 0.043* | |
C13 | 0.46770 (18) | 0.5472 (4) | 0.90583 (13) | 0.0403 (4) | |
H13A | 0.5519 | 0.5035 | 0.9648 | 0.048* | |
H13B | 0.4828 | 0.7148 | 0.8803 | 0.048* | |
O14 | 0.34471 (13) | 0.5516 (3) | 0.94579 (10) | 0.0488 (3) | |
C15 | 0.21984 (19) | 0.6160 (5) | 0.86044 (15) | 0.0494 (4) | |
H15A | 0.2313 | 0.7843 | 0.8340 | 0.059* | |
H15B | 0.1367 | 0.6180 | 0.8884 | 0.059* | |
C16 | 0.19449 (17) | 0.4310 (4) | 0.76809 (13) | 0.0417 (4) | |
H16A | 0.1763 | 0.2640 | 0.7927 | 0.050* | |
H16B | 0.1110 | 0.4818 | 0.7099 | 0.050* | |
N17 | 0.14224 (13) | 0.6623 (3) | 0.50655 (11) | 0.0351 (3) | |
O18 | 0.11854 (15) | 0.7774 (3) | 0.58335 (11) | 0.0509 (3) | |
O19 | 0.10343 (15) | 0.7434 (3) | 0.41192 (11) | 0.0492 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0317 (6) | 0.0353 (7) | 0.0286 (6) | 0.0005 (5) | 0.0060 (5) | −0.0009 (5) |
C2 | 0.0366 (7) | 0.0351 (8) | 0.0369 (8) | 0.0061 (7) | 0.0092 (6) | −0.0013 (7) |
N3 | 0.0350 (6) | 0.0350 (8) | 0.0356 (6) | 0.0068 (6) | 0.0063 (5) | 0.0009 (6) |
C4 | 0.0295 (6) | 0.0318 (8) | 0.0319 (7) | 0.0004 (6) | 0.0062 (5) | 0.0002 (6) |
C5 | 0.0300 (6) | 0.0327 (8) | 0.0309 (7) | 0.0022 (6) | 0.0073 (5) | 0.0011 (6) |
C6 | 0.0325 (7) | 0.0407 (9) | 0.0283 (7) | −0.0067 (7) | 0.0049 (5) | −0.0012 (6) |
C7 | 0.0362 (7) | 0.0340 (8) | 0.0324 (7) | −0.0055 (6) | 0.0103 (6) | −0.0020 (6) |
C8 | 0.0492 (9) | 0.0483 (10) | 0.0333 (8) | −0.0023 (8) | 0.0109 (6) | 0.0045 (7) |
Cl9 | 0.0524 (3) | 0.0688 (3) | 0.0433 (2) | −0.0123 (2) | 0.00850 (17) | −0.0192 (2) |
O10 | 0.0322 (6) | 0.0464 (8) | 0.0471 (7) | −0.0075 (5) | 0.0110 (5) | −0.0112 (6) |
N11 | 0.0309 (6) | 0.0478 (8) | 0.0290 (6) | 0.0055 (6) | 0.0064 (5) | −0.0010 (6) |
C12 | 0.0354 (7) | 0.0393 (9) | 0.0309 (7) | 0.0051 (6) | 0.0046 (6) | 0.0025 (6) |
C13 | 0.0405 (8) | 0.0488 (10) | 0.0316 (7) | −0.0037 (7) | 0.0102 (6) | −0.0026 (7) |
O14 | 0.0475 (7) | 0.0691 (9) | 0.0329 (6) | −0.0036 (6) | 0.0164 (5) | −0.0027 (6) |
C15 | 0.0435 (9) | 0.0637 (12) | 0.0450 (9) | 0.0055 (9) | 0.0190 (7) | −0.0047 (9) |
C16 | 0.0338 (7) | 0.0534 (10) | 0.0389 (8) | −0.0010 (7) | 0.0121 (6) | 0.0008 (8) |
N17 | 0.0314 (6) | 0.0319 (7) | 0.0411 (7) | 0.0037 (6) | 0.0088 (5) | 0.0047 (6) |
O18 | 0.0546 (7) | 0.0446 (8) | 0.0558 (8) | 0.0154 (6) | 0.0193 (6) | −0.0037 (6) |
O19 | 0.0543 (7) | 0.0433 (7) | 0.0473 (7) | 0.0109 (6) | 0.0098 (5) | 0.0170 (6) |
Geometric parameters (Å, º) top
N1—C2 | 1.330 (2) | C8—Cl9 | 1.791 (2) |
N1—C5 | 1.388 (2) | O10—H10A | 0.73 (3) |
N1—C6 | 1.4693 (18) | N11—C12 | 1.4585 (19) |
C2—N3 | 1.321 (2) | N11—C16 | 1.4634 (19) |
N3—C4 | 1.364 (2) | C12—C13 | 1.500 (2) |
C4—N11 | 1.354 (2) | C13—O14 | 1.424 (2) |
C4—C5 | 1.400 (2) | O14—C15 | 1.423 (2) |
C5—N17 | 1.391 (2) | C15—C16 | 1.501 (3) |
C6—C7 | 1.518 (2) | N17—O18 | 1.2331 (18) |
C7—O10 | 1.405 (2) | N17—O19 | 1.2403 (18) |
C7—C8 | 1.512 (2) | | |
| | | |
C2—N1—C5 | 105.48 (12) | C8—C7—C6 | 111.77 (13) |
C2—N1—C6 | 123.67 (14) | C7—C8—Cl9 | 112.55 (13) |
C5—N1—C6 | 130.28 (13) | C7—O10—H10A | 116 (2) |
N3—C2—N1 | 113.89 (14) | C4—N11—C12 | 118.88 (13) |
C2—N3—C4 | 105.83 (13) | C4—N11—C16 | 120.38 (13) |
N11—C4—N3 | 122.24 (14) | C12—N11—C16 | 111.94 (12) |
N11—C4—C5 | 129.48 (15) | N11—C12—C13 | 108.38 (14) |
N3—C4—C5 | 108.23 (13) | O14—C13—C12 | 112.32 (14) |
N1—C5—N17 | 122.36 (13) | C15—O14—C13 | 110.02 (12) |
N1—C5—C4 | 106.50 (13) | O14—C15—C16 | 111.35 (17) |
N17—C5—C4 | 128.68 (14) | N11—C16—C15 | 108.82 (14) |
N1—C6—C7 | 110.98 (12) | O18—N17—O19 | 122.50 (15) |
O10—C7—C8 | 110.39 (13) | O18—N17—C5 | 118.92 (13) |
O10—C7—C6 | 109.28 (14) | O19—N17—C5 | 118.54 (13) |
| | | |
C5—N1—C2—N3 | −0.76 (19) | C6—C7—C8—Cl9 | −59.45 (17) |
C6—N1—C2—N3 | −172.93 (14) | N3—C4—N11—C12 | 15.4 (2) |
N1—C2—N3—C4 | 2.1 (2) | C5—C4—N11—C12 | −161.53 (16) |
C2—N3—C4—N11 | 179.97 (16) | N3—C4—N11—C16 | −129.44 (18) |
C2—N3—C4—C5 | −2.49 (18) | C5—C4—N11—C16 | 53.6 (3) |
C2—N1—C5—N17 | 162.78 (15) | C4—N11—C12—C13 | 156.38 (15) |
C6—N1—C5—N17 | −25.8 (2) | C16—N11—C12—C13 | −55.97 (19) |
C2—N1—C5—C4 | −0.84 (17) | N11—C12—C13—O14 | 56.87 (18) |
C6—N1—C5—C4 | 170.61 (15) | C12—C13—O14—C15 | −58.9 (2) |
N11—C4—C5—N1 | 179.38 (16) | C13—O14—C15—C16 | 58.9 (2) |
N3—C4—C5—N1 | 2.08 (17) | C4—N11—C16—C15 | −156.19 (17) |
N11—C4—C5—N17 | 17.1 (3) | C12—N11—C16—C15 | 56.7 (2) |
N3—C4—C5—N17 | −160.15 (15) | O14—C15—C16—N11 | −57.5 (2) |
C2—N1—C6—C7 | −83.3 (2) | N1—C5—N17—O18 | −178.89 (14) |
C5—N1—C6—C7 | 106.64 (17) | C4—C5—N17—O18 | −19.1 (2) |
N1—C6—C7—O10 | 60.52 (17) | N1—C5—N17—O19 | −1.3 (2) |
N1—C6—C7—C8 | −176.99 (15) | C4—C5—N17—O19 | 158.41 (16) |
O10—C7—C8—Cl9 | 62.41 (16) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O10—H10A···N3i | 0.73 (3) | 2.08 (3) | 2.7948 (19) | 167 (3) |
C6—H6B···O19ii | 0.97 | 2.55 | 3.224 (2) | 126 |
C8—H8A···O14iii | 0.97 | 2.50 | 3.372 (2) | 149 |
C16—H16B···O18 | 0.97 | 2.27 | 2.918 (2) | 124 |
C16—H16B···O19iv | 0.97 | 2.55 | 3.295 (2) | 134 |
Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) x, y−1, z; (iii) x, y, z−1; (iv) −x, y−1/2, −z+1. |
(III) 3-Chloro-1-(5-morpholinyl-4-nitroimidazol-1-yl)propan-2-ol
top
Crystal data top
C10H15ClN4O4 | Z = 2 |
Mr = 290.71 | F(000) = 304 |
Triclinic, P1 | Dx = 1.521 Mg m−3 |
a = 6.5036 (8) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 7.8493 (9) Å | Cell parameters from 43 reflections |
c = 12.9757 (14) Å | θ = 11.3–30.0° |
α = 91.101 (9)° | µ = 2.85 mm−1 |
β = 101.026 (10)° | T = 293 K |
γ = 101.94 (1)° | Plate, yellow |
V = 634.91 (13) Å3 | 0.38 × 0.27 × 0.05 mm |
Data collection top
Kuma Diffraction KM-4 diffractometer | 2036 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.022 |
Graphite monochromator | θmax = 70.0°, θmin = 3.5° |
ω/2θ scans | h = −7→7 |
Absorption correction: ψ-scan (North et al., 1968) | k = −9→9 |
Tmin = 0.440, Tmax = 0.867 | l = 0→15 |
2386 measured reflections | 2 standard reflections every 100 reflections |
2281 independent reflections | intensity decay: 3.8% |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0695P)2 + 0.2622P] where P = (Fo2 + 2Fc2)/3 |
2281 reflections | (Δ/σ)max < 0.001 |
176 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
Special details top
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 | |
N1 | 0.8161 (2) | 0.51309 (19) | 0.14522 (12) | 0.0354 (3) | |
C2 | 0.7643 (3) | 0.5726 (2) | 0.04814 (15) | 0.0379 (4) | |
H2A | 0.7488 | 0.6863 | 0.0368 | 0.046* | |
N3 | 0.7385 (2) | 0.4537 (2) | −0.02739 (12) | 0.0396 (4) | |
C4 | 0.7703 (3) | 0.3077 (2) | 0.02411 (14) | 0.0364 (4) | |
C5 | 0.8218 (3) | 0.3398 (2) | 0.13179 (14) | 0.0338 (4) | |
C6 | 0.8466 (3) | 0.6089 (2) | 0.24612 (15) | 0.0386 (4) | |
H6A | 0.9424 | 0.7213 | 0.2456 | 0.046* | |
H6B | 0.9132 | 0.5448 | 0.3014 | 0.046* | |
C7 | 0.6325 (3) | 0.6369 (2) | 0.26959 (14) | 0.0387 (4) | |
H7A | 0.5964 | 0.7392 | 0.2344 | 0.046* | |
C8 | 0.6605 (4) | 0.6696 (3) | 0.38694 (16) | 0.0502 (5) | |
H8A | 0.7863 | 0.7616 | 0.4119 | 0.060* | |
H8B | 0.6834 | 0.5647 | 0.4216 | 0.060* | |
Cl9 | 0.43074 (12) | 0.73111 (11) | 0.42040 (5) | 0.0762 (3) | |
O10 | 0.4646 (2) | 0.49088 (19) | 0.23518 (12) | 0.0462 (4) | |
H10A | 0.389 (5) | 0.512 (4) | 0.175 (2) | 0.071 (9)* | |
N11 | 0.7442 (3) | 0.1472 (2) | −0.03436 (13) | 0.0439 (4) | |
O12 | 0.7421 (3) | 0.0135 (2) | 0.01360 (14) | 0.0599 (4) | |
O13 | 0.7223 (3) | 0.1494 (2) | −0.13030 (12) | 0.0661 (5) | |
N14 | 0.8900 (3) | 0.2497 (2) | 0.21725 (12) | 0.0368 (4) | |
C15 | 0.7373 (3) | 0.1714 (3) | 0.28089 (16) | 0.0436 (5) | |
H15A | 0.6553 | 0.0594 | 0.2483 | 0.052* | |
H15B | 0.6384 | 0.2465 | 0.2867 | 0.052* | |
C16 | 0.8614 (4) | 0.1479 (3) | 0.38845 (19) | 0.0571 (6) | |
H16A | 0.9332 | 0.2613 | 0.4226 | 0.068* | |
H16B | 0.7629 | 0.0911 | 0.4310 | 0.068* | |
O17 | 1.0168 (3) | 0.0456 (2) | 0.38198 (13) | 0.0600 (5) | |
C18 | 1.1640 (4) | 0.1254 (3) | 0.32027 (18) | 0.0507 (5) | |
H18A | 1.2689 | 0.0547 | 0.3176 | 0.061* | |
H18B | 1.2396 | 0.2391 | 0.3528 | 0.061* | |
C19 | 1.0502 (3) | 0.1458 (3) | 0.21028 (16) | 0.0439 (5) | |
H19A | 1.1520 | 0.2039 | 0.1698 | 0.053* | |
H19B | 0.9809 | 0.0322 | 0.1756 | 0.053* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0401 (8) | 0.0308 (8) | 0.0360 (8) | 0.0085 (7) | 0.0082 (6) | 0.0034 (6) |
C2 | 0.0368 (9) | 0.0372 (10) | 0.0414 (10) | 0.0095 (8) | 0.0093 (7) | 0.0093 (7) |
N3 | 0.0356 (8) | 0.0477 (9) | 0.0373 (8) | 0.0128 (7) | 0.0074 (6) | 0.0066 (7) |
C4 | 0.0336 (9) | 0.0397 (10) | 0.0367 (9) | 0.0095 (8) | 0.0070 (7) | 0.0001 (7) |
C5 | 0.0334 (9) | 0.0326 (9) | 0.0367 (9) | 0.0074 (7) | 0.0095 (7) | 0.0025 (7) |
C6 | 0.0424 (10) | 0.0322 (9) | 0.0390 (9) | 0.0069 (8) | 0.0041 (7) | −0.0013 (7) |
C7 | 0.0452 (11) | 0.0330 (9) | 0.0373 (9) | 0.0101 (8) | 0.0052 (8) | 0.0014 (7) |
C8 | 0.0545 (12) | 0.0578 (13) | 0.0404 (11) | 0.0191 (10) | 0.0073 (9) | −0.0023 (9) |
Cl9 | 0.0755 (5) | 0.1039 (6) | 0.0603 (4) | 0.0367 (4) | 0.0231 (3) | −0.0085 (3) |
O10 | 0.0460 (8) | 0.0439 (8) | 0.0457 (8) | 0.0068 (6) | 0.0050 (6) | 0.0047 (6) |
N11 | 0.0394 (9) | 0.0478 (10) | 0.0444 (9) | 0.0134 (7) | 0.0044 (7) | −0.0064 (7) |
O12 | 0.0669 (11) | 0.0411 (9) | 0.0676 (10) | 0.0133 (8) | 0.0025 (8) | −0.0075 (7) |
O13 | 0.0807 (12) | 0.0767 (12) | 0.0430 (9) | 0.0301 (10) | 0.0046 (8) | −0.0142 (8) |
N14 | 0.0394 (8) | 0.0371 (8) | 0.0384 (8) | 0.0139 (7) | 0.0118 (6) | 0.0088 (6) |
C15 | 0.0424 (11) | 0.0421 (11) | 0.0521 (11) | 0.0132 (9) | 0.0179 (9) | 0.0140 (8) |
C16 | 0.0650 (14) | 0.0686 (15) | 0.0511 (12) | 0.0303 (12) | 0.0255 (11) | 0.0227 (11) |
O17 | 0.0653 (10) | 0.0716 (11) | 0.0591 (9) | 0.0355 (9) | 0.0257 (8) | 0.0334 (8) |
C18 | 0.0454 (11) | 0.0594 (13) | 0.0528 (12) | 0.0207 (10) | 0.0115 (9) | 0.0172 (10) |
C19 | 0.0461 (11) | 0.0478 (11) | 0.0459 (10) | 0.0213 (9) | 0.0161 (8) | 0.0111 (8) |
Geometric parameters (Å, º) top
N1—C2 | 1.358 (2) | C8—Cl9 | 1.787 (2) |
N1—C5 | 1.377 (2) | O10—H10A | 0.88 (3) |
N1—C6 | 1.456 (2) | N11—O13 | 1.227 (2) |
C2—N3 | 1.303 (3) | N11—O12 | 1.229 (2) |
N3—C4 | 1.370 (2) | N14—C15 | 1.458 (2) |
C4—C5 | 1.379 (3) | N14—C19 | 1.463 (2) |
C4—N11 | 1.421 (2) | C15—C16 | 1.508 (3) |
C5—N14 | 1.378 (2) | C16—O17 | 1.427 (3) |
C6—C7 | 1.538 (3) | O17—C18 | 1.419 (3) |
C7—O10 | 1.407 (2) | C18—C19 | 1.505 (3) |
C7—C8 | 1.509 (3) | | |
| | | |
C2—N1—C5 | 107.45 (15) | C8—C7—C6 | 108.05 (16) |
C2—N1—C6 | 127.10 (15) | C7—C8—Cl9 | 111.27 (15) |
C5—N1—C6 | 125.33 (15) | C7—O10—H10A | 108.8 (19) |
N3—C2—N1 | 112.92 (16) | O13—N11—O12 | 123.55 (18) |
C2—N3—C4 | 103.95 (15) | O13—N11—C4 | 118.07 (18) |
N3—C4—C5 | 112.18 (16) | O12—N11—C4 | 118.38 (17) |
N3—C4—N11 | 119.78 (16) | C5—N14—C15 | 119.37 (15) |
C5—C4—N11 | 128.02 (17) | C5—N14—C19 | 118.71 (15) |
N1—C5—N14 | 120.03 (16) | C15—N14—C19 | 112.40 (14) |
N1—C5—C4 | 103.47 (15) | N14—C15—C16 | 108.18 (17) |
N14—C5—C4 | 136.16 (17) | O17—C16—C15 | 111.35 (18) |
N1—C6—C7 | 111.54 (15) | C18—O17—C16 | 110.78 (16) |
O10—C7—C8 | 109.33 (17) | O17—C18—C19 | 111.02 (18) |
O10—C7—C6 | 111.85 (15) | N14—C19—C18 | 108.05 (16) |
| | | |
C5—N1—C2—N3 | −0.9 (2) | C6—C7—C8—Cl9 | 172.58 (14) |
C6—N1—C2—N3 | −177.08 (17) | N3—C4—N11—O13 | 9.8 (3) |
N1—C2—N3—C4 | 1.6 (2) | C5—C4—N11—O13 | −171.78 (19) |
C2—N3—C4—C5 | −1.7 (2) | N3—C4—N11—O12 | −169.34 (17) |
C2—N3—C4—N11 | 176.94 (17) | C5—C4—N11—O12 | 9.1 (3) |
C2—N1—C5—N14 | 174.00 (16) | N1—C5—N14—C15 | 85.0 (2) |
C6—N1—C5—N14 | −9.7 (3) | C4—C5—N14—C15 | −103.1 (3) |
C2—N1—C5—C4 | −0.3 (2) | N1—C5—N14—C19 | −131.23 (19) |
C6—N1—C5—C4 | 176.04 (16) | C4—C5—N14—C19 | 40.7 (3) |
N3—C4—C5—N1 | 1.3 (2) | C5—N14—C15—C16 | −157.27 (18) |
N11—C4—C5—N1 | −177.31 (18) | C19—N14—C15—C16 | 56.8 (2) |
N3—C4—C5—N14 | −171.6 (2) | N14—C15—C16—O17 | −56.5 (2) |
N11—C4—C5—N14 | 9.9 (4) | C15—C16—O17—C18 | 59.1 (3) |
C2—N1—C6—C7 | 71.6 (2) | C16—O17—C18—C19 | −59.8 (3) |
C5—N1—C6—C7 | −103.9 (2) | C5—N14—C19—C18 | 156.31 (18) |
N1—C6—C7—O10 | 37.7 (2) | C15—N14—C19—C18 | −57.5 (2) |
N1—C6—C7—C8 | 158.05 (16) | O17—C18—C19—N14 | 57.9 (2) |
O10—C7—C8—Cl9 | −65.47 (19) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O10—H10A···N3i | 0.88 (3) | 1.98 (3) | 2.850 (2) | 169 (3) |
C7—H7A···O13i | 0.98 | 2.57 | 3.396 (2) | 142 |
C8—H8A···O17ii | 0.97 | 2.50 | 3.364 (3) | 149 |
C15—H15B···O10 | 0.97 | 2.46 | 3.359 (2) | 154 |
C19—H19B···O12 | 0.97 | 2.34 | 2.947 (3) | 120 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x, y+1, z. |
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