Azole. 44. Über Morpholino­nitro­imidazolderivate

The structure analyses of racemic 3-chloro-1-(4-morpholino-5-nitro­imidazol-1-yl)­propan-2-ol, C₁₀H₁₅ClN₄O₄, (II), and 3-chloro-1-(5-morpholino-4-nitro­imidazol-1-yl)­propan-2-ol, C₁₀H₁₅ClN₄O₄, (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 Csp²—NO₂ 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. C55, 1562–1565]. In the crystal lattice, the mol­ecules of both compounds are linked by O—H...N and C—H...O intermolecular hydrogen bonds.

Computing details

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

Crystal data

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) Å^3	Needle, yellow
Z = 2	0.54 × 0.17 × 0.10 mm

Data collection

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

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.025	w = 1/[σ^2(Fo^2) + (0.0482P)^2 + 0.0886P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 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+0.001xFc^2λ^3/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
O10—H10A···N3^i	0.73 (3)	2.08 (3)	2.7948 (19)	167 (3)
C6—H6B···O19^ii	0.97	2.55	3.224 (2)	126
C8—H8A···O14^iii	0.97	2.50	3.372 (2)	149
C16—H16B···O18	0.97	2.27	2.918 (2)	124
C16—H16B···O19^iv	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

Crystal data

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) Å^3	0.38 × 0.27 × 0.05 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0695P)^2 + 0.2622P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
O10—H10A···N3^i	0.88 (3)	1.98 (3)	2.850 (2)	169 (3)
C7—H7A···O13^i	0.98	2.57	3.396 (2)	142
C8—H8A···O17^ii	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.