Synthesis and crystallographic studies of two new 1,3,5-tri­azines

The synthesis and characterization of two new 1,3,5-tri­azines containing 2-(amino­meth­yl)-1H-benzimidazole hydro­chloride as a substituent are reported, namely, 2-{[(4,6-di­chloro-1,3,5-triazin-2-yl)amino]­meth­yl}-1H-benzimidazol-3-ium chloride, C₁₁H₉Cl₂N₆⁺·Cl⁻ (1), and bis­(2,2′-{[(6-chloro-1,3,5-tri­azine-2,4-di­yl)bis­(aza­nedi­yl)]bis­(methyl­ene)}bis­(1H-benzimidazol-3-ium)) tetra­chloride hepta­hydrate, 2C₁₉H₁₈ClN₉²⁺·4Cl⁻·7H₂O (2). Both salts were characterized using single-crystal X-ray diffraction analysis and IR spectroscopy. Moreover, the NMR (¹H and ¹³C) spectra of 1 were obtained. Salts 1 and 2 have triclinic symmetry (space group P) and their supra­molecular structures are stabilized by hydrogen bonding and offset π–π inter­actions. In hydrated salt 2, the non­covalent inter­actions yield pseudo-nanotubes filled with chloride anions and water mol­ecules, which were modelled in the refinement with substitutional and positional disorder.

Computing details

For both structures, data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015b); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015a); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

2-{[(4,6-Dichloro-1,3,5-triazin-2-yl)amino]methyl}-1H-benzimidazol-3-ium chloride (pr109_grande2_05072018)

Crystal data

C11H9Cl2N6^+·Cl^−	Z = 2
Mr = 331.59	F(000) = 336
Triclinic, P1	Dx = 1.570 Mg m^−3
a = 8.1958 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.4184 (5) Å	Cell parameters from 5550 reflections
c = 10.5965 (6) Å	θ = 3.6–25.6°
α = 97.006 (5)°	µ = 0.65 mm^−1
β = 104.543 (5)°	T = 293 K
γ = 91.138 (5)°	Plate, clear light white
V = 701.43 (7) Å^3	0.17 × 0.15 × 0.13 mm

Data collection

Agilent Xcalibur Atlas Gemini diffractometer	1929 reflections with I > 2σ(I)
Detector resolution: 10.3659 pixels mm^-1	Rint = 0.046
ω scans	θmax = 25.0°, θmin = 3.4°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −9→9
Tmin = 0.653, Tmax = 1.000	k = −10→10
21243 measured reflections	l = −12→12
2455 independent reflections

Refinement

Refinement on F^2	3 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.087	w = 1/[σ^2(Fo^2) + (0.0347P)^2 + 0.2894P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
2455 reflections	Δρmax = 0.18 e Å^−3
190 parameters	Δρmin = −0.29 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. X-ray diffraction studies were carried out with an Xcalibur Atlas, Gemini diffractometer with a CCD area detector and graphite monochromator (λ_Moκα = 0.71073 Å). Structures 1 and 2 were solved with the OLEX2 structure solution program (Dolomanov, et al., 2009) using SHELXS (Sheldrick, 2008) and SHELXT (Sheldrick, 2015b) respectively. Moreover, said structures were refined with the SHELXL (Sheldrick, 2015a) refinement package. The non-hydrogen atoms were anisotropically refined.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.92626 (8)	0.86334 (9)	0.60517 (7)	0.0664 (2)
Cl2	0.50433 (10)	1.01755 (10)	0.19354 (8)	0.0726 (2)
N1	0.2585 (2)	0.4649 (2)	0.21225 (19)	0.0429 (5)
H1	0.3646 (14)	0.489 (3)	0.242 (2)	0.051*
N2	−0.0069 (2)	0.4535 (2)	0.2056 (2)	0.0447 (5)
H2	−0.099 (2)	0.473 (3)	0.227 (2)	0.054*
N3	0.3423 (3)	0.6550 (3)	0.4718 (2)	0.0491 (5)
H3	0.362 (3)	0.607 (3)	0.5406 (17)	0.059*
N4	0.6145 (2)	0.7595 (2)	0.53597 (18)	0.0445 (5)
N5	0.7038 (2)	0.9319 (2)	0.4012 (2)	0.0497 (5)
N6	0.4191 (2)	0.8293 (2)	0.34349 (18)	0.0440 (5)
C1	0.1427 (3)	0.5194 (3)	0.2723 (2)	0.0416 (5)
C2	0.1812 (3)	0.3584 (3)	0.1020 (2)	0.0398 (5)
C3	0.2423 (3)	0.2714 (3)	0.0060 (3)	0.0523 (6)
H3A	0.356052	0.277898	0.007056	0.063*
C4	0.1273 (3)	0.1751 (3)	−0.0906 (3)	0.0588 (7)
H4	0.164334	0.114890	−0.156678	0.071*
C5	−0.0434 (3)	0.1645 (3)	−0.0930 (3)	0.0582 (7)
H5	−0.116985	0.096430	−0.159677	0.070*
C6	−0.1053 (3)	0.2522 (3)	0.0007 (3)	0.0534 (6)
H6	−0.219287	0.246255	−0.001128	0.064*
C7	0.0105 (3)	0.3504 (3)	0.0984 (2)	0.0420 (5)
C8	0.1701 (3)	0.6391 (3)	0.3925 (3)	0.0519 (6)
H8A	0.137268	0.742690	0.366177	0.062*
H8B	0.097204	0.608363	0.445683	0.062*
C9	0.4601 (3)	0.7505 (3)	0.4494 (2)	0.0412 (5)
C10	0.7243 (3)	0.8490 (3)	0.5031 (2)	0.0460 (6)
C11	0.5462 (3)	0.9138 (3)	0.3278 (2)	0.0456 (6)
Cl3	0.65237 (7)	0.50305 (8)	0.26932 (6)	0.05188 (19)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0505 (4)	0.0743 (5)	0.0650 (5)	−0.0059 (3)	0.0003 (3)	0.0043 (4)
Cl2	0.0727 (5)	0.0822 (5)	0.0730 (5)	0.0120 (4)	0.0241 (4)	0.0374 (4)
N1	0.0249 (9)	0.0558 (12)	0.0501 (12)	0.0039 (9)	0.0121 (9)	0.0098 (10)
N2	0.0252 (10)	0.0538 (12)	0.0599 (13)	0.0035 (9)	0.0167 (9)	0.0134 (10)
N3	0.0490 (12)	0.0544 (13)	0.0469 (12)	−0.0008 (10)	0.0162 (10)	0.0100 (10)
N4	0.0477 (12)	0.0434 (11)	0.0410 (11)	0.0020 (9)	0.0104 (9)	0.0014 (9)
N5	0.0469 (12)	0.0478 (12)	0.0561 (13)	−0.0025 (9)	0.0165 (10)	0.0070 (10)
N6	0.0407 (11)	0.0469 (11)	0.0474 (12)	0.0054 (9)	0.0150 (9)	0.0089 (9)
C1	0.0324 (12)	0.0481 (14)	0.0493 (14)	0.0046 (10)	0.0163 (11)	0.0137 (11)
C2	0.0302 (11)	0.0459 (13)	0.0458 (13)	0.0063 (10)	0.0101 (10)	0.0142 (11)
C3	0.0388 (13)	0.0673 (17)	0.0567 (16)	0.0158 (12)	0.0176 (12)	0.0171 (13)
C4	0.0617 (17)	0.0674 (18)	0.0469 (15)	0.0131 (14)	0.0135 (13)	0.0058 (13)
C5	0.0516 (16)	0.0638 (17)	0.0530 (16)	0.0013 (13)	0.0029 (13)	0.0058 (13)
C6	0.0343 (13)	0.0631 (17)	0.0610 (16)	0.0018 (12)	0.0050 (12)	0.0162 (14)
C7	0.0347 (12)	0.0465 (13)	0.0480 (14)	0.0070 (10)	0.0126 (11)	0.0141 (11)
C8	0.0408 (13)	0.0573 (16)	0.0634 (16)	0.0007 (11)	0.0250 (12)	0.0056 (13)
C9	0.0438 (13)	0.0382 (13)	0.0439 (13)	0.0026 (10)	0.0174 (11)	0.0014 (10)
C10	0.0452 (14)	0.0423 (14)	0.0478 (14)	−0.0002 (11)	0.0113 (11)	−0.0033 (11)
C11	0.0497 (15)	0.0426 (13)	0.0469 (14)	0.0074 (11)	0.0163 (12)	0.0061 (11)
Cl3	0.0337 (3)	0.0692 (4)	0.0594 (4)	0.0048 (3)	0.0231 (3)	0.0104 (3)

Geometric parameters (Å, º)

Cl1—C10	1.728 (2)	N6—C9	1.347 (3)
Cl2—C11	1.724 (2)	N6—C11	1.306 (3)
N1—H1	0.859 (10)	C1—C8	1.491 (3)
N1—C1	1.328 (3)	C2—C3	1.382 (3)
N1—C2	1.386 (3)	C2—C7	1.389 (3)
N2—H2	0.852 (10)	C3—H3A	0.9300
N2—C1	1.324 (3)	C3—C4	1.370 (4)
N2—C7	1.382 (3)	C4—H4	0.9300
N3—H3	0.856 (10)	C4—C5	1.394 (4)
N3—C8	1.444 (3)	C5—H5	0.9300
N3—C9	1.329 (3)	C5—C6	1.370 (4)
N4—C9	1.358 (3)	C6—H6	0.9300
N4—C10	1.301 (3)	C6—C7	1.386 (3)
N5—C10	1.334 (3)	C8—H8A	0.9700
N5—C11	1.325 (3)	C8—H8B	0.9700
C1—N1—H1	123.4 (16)	C4—C5—H5	119.3
C1—N1—C2	109.27 (18)	C6—C5—C4	121.5 (3)
C2—N1—H1	127.2 (16)	C6—C5—H5	119.3
C1—N2—H2	123.9 (17)	C5—C6—H6	121.7
C1—N2—C7	109.57 (18)	C5—C6—C7	116.7 (2)
C7—N2—H2	126.5 (17)	C7—C6—H6	121.7
C8—N3—H3	115.6 (19)	N2—C7—C2	106.1 (2)
C9—N3—H3	121.0 (19)	N2—C7—C6	132.1 (2)
C9—N3—C8	123.1 (2)	C6—C7—C2	121.7 (2)
C10—N4—C9	112.6 (2)	N3—C8—C1	113.84 (19)
C11—N5—C10	110.9 (2)	N3—C8—H8A	108.8
C11—N6—C9	113.1 (2)	N3—C8—H8B	108.8
N1—C1—C8	127.1 (2)	C1—C8—H8A	108.8
N2—C1—N1	108.9 (2)	C1—C8—H8B	108.8
N2—C1—C8	123.94 (19)	H8A—C8—H8B	107.7
N1—C2—C7	106.1 (2)	N3—C9—N4	116.6 (2)
C3—C2—N1	132.6 (2)	N3—C9—N6	118.3 (2)
C3—C2—C7	121.3 (2)	N6—C9—N4	125.1 (2)
C2—C3—H3A	121.6	N4—C10—Cl1	115.95 (19)
C4—C3—C2	116.8 (2)	N4—C10—N5	129.3 (2)
C4—C3—H3A	121.6	N5—C10—Cl1	114.76 (18)
C3—C4—H4	119.0	N5—C11—Cl2	115.05 (18)
C3—C4—C5	122.0 (2)	N6—C11—Cl2	115.98 (18)
C5—C4—H4	119.0	N6—C11—N5	129.0 (2)
N1—C1—C8—N3	−21.4 (3)	C7—N2—C1—N1	0.7 (3)
N1—C2—C3—C4	179.7 (2)	C7—N2—C1—C8	178.8 (2)
N1—C2—C7—N2	0.6 (2)	C7—C2—C3—C4	−1.2 (3)
N1—C2—C7—C6	−179.2 (2)	C8—N3—C9—N4	176.8 (2)
N2—C1—C8—N3	160.9 (2)	C8—N3—C9—N6	−3.8 (3)
C1—N1—C2—C3	178.9 (2)	C9—N3—C8—C1	85.3 (3)
C1—N1—C2—C7	−0.2 (2)	C9—N4—C10—Cl1	−178.34 (15)
C1—N2—C7—C2	−0.8 (2)	C9—N4—C10—N5	1.5 (4)
C1—N2—C7—C6	178.9 (2)	C9—N6—C11—Cl2	179.65 (16)
C2—N1—C1—N2	−0.3 (3)	C9—N6—C11—N5	−0.7 (4)
C2—N1—C1—C8	−178.3 (2)	C10—N4—C9—N3	176.7 (2)
C2—C3—C4—C5	0.0 (4)	C10—N4—C9—N6	−2.6 (3)
C3—C2—C7—N2	−178.6 (2)	C10—N5—C11—Cl2	179.39 (16)
C3—C2—C7—C6	1.6 (3)	C10—N5—C11—N6	−0.3 (4)
C3—C4—C5—C6	1.0 (4)	C11—N5—C10—Cl1	179.67 (16)
C4—C5—C6—C7	−0.7 (4)	C11—N5—C10—N4	−0.2 (4)
C5—C6—C7—N2	179.7 (2)	C11—N6—C9—N3	−177.1 (2)
C5—C6—C7—C2	−0.6 (4)	C11—N6—C9—N4	2.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl3	0.86 (2)	2.30 (1)	3.1338 (18)	163 (2)
N2—H2···Cl3^i	0.85 (2)	2.21 (2)	3.0582 (18)	175 (2)
N3—H3···Cl3^ii	0.86 (2)	2.35 (2)	3.183 (2)	165 (2)

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+1.

Bis(2,2'-{[(6-chloro-1,3,5-triazine-2,4-diyl)bis(azanediyl)]bis(methylene)}bis(1H-benzimidazol-3-ium)) tetrachloride heptahydrate (pr109_solucion2_16082018)

Crystal data

2C19H18ClN9^2+·4Cl^−·7H2O	Z = 2
Mr = 1095.75	F(000) = 1132
Triclinic, P1	Dx = 1.393 Mg m^−3
a = 12.8675 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.1487 (5) Å	Cell parameters from 16385 reflections
c = 16.5184 (6) Å	θ = 3.3–25.8°
α = 75.570 (3)°	µ = 0.40 mm^−1
β = 78.737 (3)°	T = 293 K
γ = 64.330 (3)°	Plate, clear light white
V = 2611.82 (17) Å^3	0.17 × 0.14 × 0.12 mm

Data collection

Agilent Xcalibur Atlas Gemini diffractometer	7312 reflections with I > 2σ(I)
Detector resolution: 10.3659 pixels mm^-1	Rint = 0.045
ω scans	θmax = 26.5°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −16→16
Tmin = 0.723, Tmax = 1.000	k = −17→17
87453 measured reflections	l = −20→20
10807 independent reflections

Refinement

Refinement on F^2	64 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.179	w = 1/[σ^2(Fo^2) + (0.0828P)^2 + 1.7651P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.007
10807 reflections	Δρmax = 0.57 e Å^−3
769 parameters	Δρmin = −0.33 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. X-ray diffraction studies were carried out with an Xcalibur Atlas, Gemini diffractometer with a CCD area detector and graphite monochromator (λ_Moκα = 0.71073 Å). Structures 1 and 2 were solved with the OLEX2 structure solution program (Dolomanov, et al., 2009) using SHELXS (Sheldrick, 2008) and SHELXT (Sheldrick, 2015b) respectively. Moreover, said structures were refined with the SHELXL (Sheldrick, 2015a) refinement package. The non-hydrogen atoms were anisotropically refined.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl2	0.74836 (8)	0.33683 (6)	0.67378 (4)	0.0686 (2)
N10	1.0189 (2)	0.3570 (2)	0.18021 (15)	0.0652 (7)
H10	1.005 (3)	0.329 (3)	0.1451 (19)	0.078*
N11	1.0216 (2)	0.3959 (2)	0.29817 (15)	0.0549 (6)
H11	1.018 (3)	0.392 (3)	0.3514 (7)	0.066*
N12	0.9195 (2)	0.25422 (18)	0.39583 (14)	0.0511 (5)
H12	0.969 (2)	0.1984 (16)	0.4234 (17)	0.061*
N13	0.83551 (19)	0.29399 (17)	0.52587 (13)	0.0472 (5)
N14	0.67267 (18)	0.45751 (16)	0.53481 (13)	0.0430 (5)
N15	0.76184 (17)	0.41351 (16)	0.40009 (12)	0.0414 (5)
N16	0.60070 (19)	0.56775 (18)	0.41281 (14)	0.0481 (5)
H16	0.551 (2)	0.6116 (19)	0.4432 (16)	0.058*
N17	0.7395 (2)	0.65612 (18)	0.20959 (14)	0.0498 (5)
H17	0.712 (2)	0.647 (2)	0.1700 (14)	0.060*
N18	0.7463 (2)	0.67462 (19)	0.33419 (14)	0.0529 (6)
H18	0.728 (3)	0.672 (3)	0.3873 (7)	0.063*
C20	0.9880 (2)	0.3410 (2)	0.26239 (17)	0.0533 (7)
C21	1.0764 (3)	0.4240 (3)	0.1620 (2)	0.0667 (9)
C22	1.1287 (3)	0.4634 (4)	0.0870 (2)	0.0906 (13)
H22	1.127603	0.447569	0.035900	0.109*
C23	1.1816 (4)	0.5267 (4)	0.0933 (3)	0.0969 (15)
H23	1.217301	0.554589	0.044770	0.116*
C24	1.1838 (3)	0.5505 (3)	0.1682 (3)	0.0879 (12)
H24	1.221400	0.593477	0.168929	0.106*
C25	1.1321 (3)	0.5127 (3)	0.2427 (2)	0.0730 (9)
H25	1.133277	0.529162	0.293499	0.088*
C26	1.0787 (2)	0.4492 (2)	0.23700 (19)	0.0598 (8)
C27	0.9258 (3)	0.2720 (2)	0.30583 (17)	0.0541 (7)
H27A	0.847796	0.304849	0.289078	0.065*
H27B	0.964901	0.203650	0.287753	0.065*
C28	0.8366 (2)	0.32276 (19)	0.44119 (15)	0.0409 (5)
C29	0.7532 (2)	0.3662 (2)	0.56570 (16)	0.0438 (6)
C30	0.6807 (2)	0.47670 (19)	0.44950 (15)	0.0397 (5)
C31	0.6063 (2)	0.5995 (2)	0.32276 (17)	0.0502 (6)
H31A	0.531724	0.654090	0.307002	0.060*
H31B	0.622922	0.538630	0.297789	0.060*
C32	0.6978 (2)	0.6418 (2)	0.28926 (16)	0.0452 (6)
C33	0.8169 (2)	0.7031 (2)	0.20115 (18)	0.0522 (7)
C34	0.8803 (3)	0.7375 (3)	0.1315 (2)	0.0668 (8)
H34	0.877602	0.729498	0.077825	0.080*
C35	0.9469 (3)	0.7837 (3)	0.1460 (3)	0.0773 (10)
H35	0.989965	0.808470	0.100734	0.093*
C36	0.9524 (3)	0.7949 (3)	0.2254 (3)	0.0762 (10)
H36	0.999139	0.827068	0.231764	0.091*
C37	0.8910 (3)	0.7602 (3)	0.2958 (2)	0.0664 (8)
H37	0.895572	0.767113	0.349439	0.080*
C38	0.8221 (2)	0.7143 (2)	0.28095 (18)	0.0525 (7)
Cl1	0.34034 (6)	0.84063 (6)	0.38362 (4)	0.0585 (2)
N1	0.3308 (2)	0.98744 (18)	0.73235 (14)	0.0499 (5)
H1	0.339 (3)	0.997 (2)	0.6785 (7)	0.060*
N2	0.2653 (2)	0.9471 (2)	0.86085 (14)	0.0554 (6)
H2	0.227 (2)	0.922 (2)	0.9018 (14)	0.066*
N3	0.1912 (2)	0.92246 (18)	0.66432 (14)	0.0509 (5)
H3	0.138 (2)	0.9780 (16)	0.6394 (18)	0.061*
N4	0.26194 (18)	0.88149 (17)	0.53280 (13)	0.0468 (5)
N5	0.42493 (17)	0.71779 (17)	0.52059 (13)	0.0433 (5)
N6	0.35358 (17)	0.76924 (16)	0.65518 (13)	0.0426 (5)
N7	0.50763 (19)	0.61101 (18)	0.64051 (13)	0.0486 (5)
H7	0.557 (2)	0.5677 (19)	0.6097 (16)	0.058*
N8	0.6241 (2)	0.7136 (2)	0.69179 (14)	0.0524 (6)
H8	0.637 (3)	0.712 (2)	0.6389 (8)	0.063*
N9	0.5625 (2)	0.68288 (19)	0.82273 (14)	0.0512 (6)
H9	0.528 (2)	0.658 (2)	0.8670 (13)	0.061*
C1	0.2620 (2)	0.9444 (2)	0.78189 (16)	0.0457 (6)
C2	0.3786 (2)	1.0226 (2)	0.78107 (18)	0.0510 (6)
C3	0.4517 (3)	1.0752 (2)	0.7592 (2)	0.0632 (8)
H3A	0.481049	1.090813	0.703790	0.076*
C4	0.4787 (3)	1.1030 (3)	0.8234 (3)	0.0744 (10)
H4	0.527785	1.138450	0.811623	0.089*
C5	0.4344 (3)	1.0795 (3)	0.9057 (3)	0.0797 (11)
H5	0.453586	1.101210	0.947393	0.096*
C6	0.3633 (3)	1.0254 (3)	0.9284 (2)	0.0737 (9)
H6	0.335479	1.008711	0.984023	0.088*
C7	0.3356 (3)	0.9973 (2)	0.86327 (18)	0.0546 (7)
C8	0.1892 (2)	0.9027 (2)	0.75425 (17)	0.0503 (6)
H8A	0.216641	0.826474	0.775332	0.060*
H8B	0.109928	0.935969	0.778484	0.060*
C9	0.2714 (2)	0.8555 (2)	0.61656 (16)	0.0427 (6)
C10	0.3428 (2)	0.8096 (2)	0.49153 (15)	0.0422 (6)
C11	0.4261 (2)	0.7015 (2)	0.60511 (15)	0.0411 (5)
C12	0.5213 (2)	0.5914 (2)	0.72884 (16)	0.0504 (6)
H12A	0.573614	0.517579	0.745908	0.060*
H12B	0.446849	0.602469	0.761268	0.060*
C13	0.5678 (2)	0.6626 (2)	0.74751 (15)	0.0465 (6)
C14	0.6578 (2)	0.7697 (2)	0.73262 (18)	0.0537 (7)
C15	0.7189 (3)	0.8339 (3)	0.7031 (2)	0.0674 (8)
H15	0.743634	0.848697	0.646483	0.081*
C16	0.7406 (3)	0.8741 (3)	0.7619 (3)	0.0773 (10)
H16A	0.781691	0.917127	0.744854	0.093*
C17	0.7031 (3)	0.8523 (3)	0.8464 (3)	0.0769 (10)
H17A	0.719962	0.881302	0.884328	0.092*
C18	0.6417 (3)	0.7894 (3)	0.8761 (2)	0.0680 (9)
H18A	0.616835	0.774987	0.932747	0.082*
C19	0.6193 (2)	0.7488 (2)	0.81608 (18)	0.0532 (7)
Cl4	0.73950 (9)	0.38118 (10)	0.13485 (7)	0.0830 (5)	0.858 (4)
O3	0.6431 (4)	0.6260 (3)	0.0919 (2)	0.1086 (10)
H3B	0.575 (2)	0.638 (4)	0.117 (4)	0.163*
H3C	0.679 (4)	0.5580 (12)	0.108 (4)	0.163*
Cl5	0.9384 (4)	0.9506 (3)	0.9281 (2)	0.148 (2)	0.379 (5)
Cl3	0.03845 (17)	0.39357 (17)	0.47261 (11)	0.1166 (9)	0.739 (4)
O1	0.4460 (3)	0.6079 (3)	0.96348 (17)	0.0973 (9)
H1A	0.429 (4)	0.643 (4)	1.002 (3)	0.146*
H1B	0.381 (2)	0.625 (4)	0.945 (3)	0.146*
O5	0.0851 (3)	0.0538 (2)	0.4337 (3)	0.1043 (11)	0.876 (3)
H5A	0.142 (4)	0.015 (4)	0.463 (4)	0.156*	0.876 (3)
H5B	0.065 (5)	0.008 (4)	0.423 (4)	0.156*	0.876 (3)
Cl5A	0.1261 (10)	0.1083 (8)	0.4767 (8)	0.121 (3)	0.124 (3)
Cl6	0.7129 (5)	0.7248 (5)	0.5061 (3)	0.0929 (15)	0.539 (9)
O6	0.6969 (16)	0.6973 (14)	0.5172 (9)	0.086 (3)	0.461 (9)
Cl7	0.6211 (4)	0.9358 (4)	0.4565 (2)	0.1184 (15)	0.533 (10)
O7	0.6033 (12)	0.9805 (11)	0.4309 (8)	0.124 (3)	0.467 (10)
O8A	1.0106 (7)	0.2004 (9)	0.0900 (4)	0.094 (2)	0.542 (10)
O8	0.9966 (8)	0.2728 (10)	0.0670 (5)	0.100 (2)	0.458 (10)
Cl9	0.6213 (7)	0.2970 (6)	0.8753 (4)	0.1097 (18)	0.429 (10)
O9	0.6212 (14)	0.2614 (11)	0.8942 (9)	0.119 (3)	0.571 (10)
Cl10	0.1383 (5)	0.9650 (4)	0.1677 (3)	0.1483 (19)	0.437 (5)
O10	0.1962 (9)	0.9048 (8)	0.2149 (5)	0.151 (2)	0.563 (5)
O2	0.9641 (2)	0.0855 (2)	0.63765 (18)	0.0881 (8)
H2A	0.932 (4)	0.142 (2)	0.603 (2)	0.132*
H2B	0.914 (3)	0.087 (4)	0.6799 (18)	0.132*
O4	0.1657 (5)	0.8569 (5)	−0.0004 (3)	0.180 (2)
H4A	0.198 (7)	0.863 (7)	0.037 (5)	0.271*
H4B	0.106 (5)	0.917 (4)	−0.008 (6)	0.271*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl2	0.0924 (6)	0.0611 (4)	0.0379 (4)	−0.0183 (4)	−0.0047 (3)	−0.0101 (3)
N10	0.0633 (16)	0.0742 (18)	0.0410 (14)	−0.0145 (14)	0.0034 (11)	−0.0131 (12)
N11	0.0529 (13)	0.0573 (14)	0.0433 (13)	−0.0162 (11)	0.0042 (11)	−0.0087 (11)
N12	0.0526 (13)	0.0470 (13)	0.0429 (12)	−0.0112 (10)	0.0017 (10)	−0.0116 (10)
N13	0.0537 (13)	0.0422 (11)	0.0400 (12)	−0.0161 (10)	−0.0012 (9)	−0.0066 (9)
N14	0.0454 (11)	0.0429 (11)	0.0391 (11)	−0.0183 (10)	0.0034 (9)	−0.0100 (9)
N15	0.0418 (11)	0.0445 (11)	0.0375 (11)	−0.0189 (9)	0.0019 (9)	−0.0091 (9)
N16	0.0456 (12)	0.0482 (13)	0.0407 (12)	−0.0113 (10)	−0.0004 (9)	−0.0087 (9)
N17	0.0547 (13)	0.0532 (13)	0.0400 (12)	−0.0193 (11)	−0.0044 (10)	−0.0114 (10)
N18	0.0616 (14)	0.0583 (14)	0.0404 (12)	−0.0250 (12)	−0.0057 (11)	−0.0101 (11)
C20	0.0469 (15)	0.0551 (16)	0.0415 (14)	−0.0061 (13)	0.0036 (11)	−0.0142 (12)
C21	0.0493 (16)	0.0669 (19)	0.0516 (18)	−0.0054 (15)	0.0053 (13)	0.0022 (14)
C22	0.076 (2)	0.101 (3)	0.055 (2)	−0.016 (2)	0.0086 (17)	0.0061 (19)
C23	0.073 (2)	0.087 (3)	0.084 (3)	−0.020 (2)	0.012 (2)	0.025 (2)
C24	0.062 (2)	0.075 (2)	0.098 (3)	−0.0222 (18)	0.002 (2)	0.016 (2)
C25	0.0550 (18)	0.0623 (19)	0.081 (2)	−0.0169 (16)	0.0006 (16)	0.0038 (17)
C26	0.0453 (15)	0.0554 (17)	0.0550 (18)	−0.0086 (13)	0.0044 (13)	0.0011 (13)
C27	0.0555 (16)	0.0555 (16)	0.0441 (15)	−0.0147 (13)	0.0045 (12)	−0.0190 (12)
C28	0.0442 (13)	0.0417 (13)	0.0393 (13)	−0.0216 (11)	0.0030 (10)	−0.0095 (10)
C29	0.0530 (15)	0.0427 (13)	0.0386 (13)	−0.0233 (12)	−0.0011 (11)	−0.0077 (11)
C30	0.0416 (13)	0.0433 (13)	0.0385 (13)	−0.0227 (11)	0.0021 (10)	−0.0094 (10)
C31	0.0508 (15)	0.0528 (15)	0.0434 (14)	−0.0171 (13)	−0.0082 (11)	−0.0072 (12)
C32	0.0494 (14)	0.0399 (13)	0.0405 (14)	−0.0116 (11)	−0.0072 (11)	−0.0076 (10)
C33	0.0489 (15)	0.0483 (15)	0.0512 (16)	−0.0132 (12)	−0.0040 (12)	−0.0080 (12)
C34	0.0632 (19)	0.070 (2)	0.0585 (19)	−0.0253 (17)	0.0012 (15)	−0.0055 (15)
C35	0.062 (2)	0.073 (2)	0.085 (3)	−0.0296 (18)	0.0019 (18)	0.0023 (19)
C36	0.061 (2)	0.0586 (19)	0.110 (3)	−0.0263 (16)	−0.0123 (19)	−0.0101 (19)
C37	0.0647 (19)	0.0589 (18)	0.079 (2)	−0.0245 (16)	−0.0138 (17)	−0.0147 (16)
C38	0.0528 (15)	0.0453 (14)	0.0552 (17)	−0.0151 (13)	−0.0083 (13)	−0.0088 (12)
Cl1	0.0644 (4)	0.0726 (5)	0.0367 (3)	−0.0278 (4)	−0.0075 (3)	−0.0052 (3)
N1	0.0559 (13)	0.0502 (13)	0.0412 (12)	−0.0195 (11)	−0.0002 (10)	−0.0116 (10)
N2	0.0630 (15)	0.0639 (15)	0.0402 (13)	−0.0290 (12)	0.0016 (10)	−0.0104 (11)
N3	0.0500 (13)	0.0465 (12)	0.0476 (13)	−0.0081 (10)	−0.0077 (10)	−0.0134 (10)
N4	0.0477 (12)	0.0483 (12)	0.0431 (12)	−0.0158 (10)	−0.0109 (9)	−0.0082 (10)
N5	0.0425 (11)	0.0503 (12)	0.0381 (11)	−0.0179 (10)	−0.0027 (9)	−0.0129 (9)
N6	0.0436 (11)	0.0448 (11)	0.0374 (11)	−0.0143 (9)	−0.0042 (9)	−0.0108 (9)
N7	0.0487 (13)	0.0483 (13)	0.0385 (12)	−0.0072 (10)	−0.0048 (9)	−0.0135 (9)
N8	0.0477 (12)	0.0651 (15)	0.0361 (12)	−0.0165 (11)	−0.0037 (10)	−0.0077 (11)
N9	0.0558 (14)	0.0535 (13)	0.0359 (12)	−0.0151 (11)	−0.0023 (10)	−0.0087 (10)
C1	0.0488 (14)	0.0404 (13)	0.0415 (14)	−0.0132 (11)	0.0002 (11)	−0.0092 (11)
C2	0.0488 (15)	0.0434 (14)	0.0551 (16)	−0.0123 (12)	−0.0055 (12)	−0.0111 (12)
C3	0.0573 (17)	0.0529 (17)	0.076 (2)	−0.0199 (14)	−0.0083 (15)	−0.0102 (15)
C4	0.063 (2)	0.0575 (19)	0.105 (3)	−0.0224 (16)	−0.0225 (19)	−0.0122 (19)
C5	0.080 (2)	0.072 (2)	0.093 (3)	−0.0197 (19)	−0.036 (2)	−0.025 (2)
C6	0.084 (2)	0.080 (2)	0.058 (2)	−0.027 (2)	−0.0186 (17)	−0.0176 (17)
C7	0.0568 (16)	0.0517 (16)	0.0513 (16)	−0.0162 (13)	−0.0094 (13)	−0.0101 (12)
C8	0.0516 (15)	0.0469 (14)	0.0487 (15)	−0.0165 (12)	0.0046 (12)	−0.0164 (12)
C9	0.0434 (13)	0.0436 (13)	0.0449 (14)	−0.0187 (11)	−0.0055 (11)	−0.0116 (11)
C10	0.0442 (13)	0.0510 (14)	0.0369 (13)	−0.0240 (12)	−0.0065 (10)	−0.0068 (11)
C11	0.0405 (13)	0.0449 (13)	0.0394 (13)	−0.0172 (11)	−0.0027 (10)	−0.0118 (10)
C12	0.0525 (15)	0.0501 (15)	0.0384 (14)	−0.0115 (12)	−0.0064 (11)	−0.0067 (11)
C13	0.0421 (13)	0.0485 (14)	0.0350 (13)	−0.0070 (11)	−0.0053 (10)	−0.0039 (11)
C14	0.0441 (14)	0.0546 (16)	0.0521 (16)	−0.0105 (13)	−0.0074 (12)	−0.0079 (13)
C15	0.0564 (18)	0.066 (2)	0.072 (2)	−0.0219 (16)	−0.0056 (15)	−0.0059 (16)
C16	0.063 (2)	0.061 (2)	0.106 (3)	−0.0227 (17)	−0.015 (2)	−0.012 (2)
C17	0.070 (2)	0.064 (2)	0.098 (3)	−0.0170 (18)	−0.021 (2)	−0.0280 (19)
C18	0.073 (2)	0.0653 (19)	0.0606 (19)	−0.0149 (17)	−0.0124 (16)	−0.0217 (15)
C19	0.0518 (15)	0.0488 (15)	0.0502 (16)	−0.0096 (13)	−0.0093 (12)	−0.0110 (12)
Cl4	0.0713 (7)	0.1053 (9)	0.0624 (7)	−0.0393 (6)	−0.0106 (5)	0.0107 (5)
O3	0.147 (3)	0.132 (3)	0.0769 (19)	−0.074 (2)	−0.0199 (19)	−0.0312 (18)
Cl5	0.187 (5)	0.099 (3)	0.099 (3)	−0.009 (2)	−0.017 (2)	−0.0065 (19)
Cl3	0.1299 (15)	0.1631 (18)	0.0857 (11)	−0.0798 (13)	−0.0021 (9)	−0.0413 (11)
O1	0.110 (2)	0.138 (3)	0.0630 (17)	−0.077 (2)	−0.0056 (15)	−0.0044 (16)
O5	0.106 (3)	0.0685 (19)	0.114 (3)	−0.0011 (17)	−0.034 (2)	−0.0192 (18)
Cl5A	0.113 (5)	0.084 (4)	0.126 (5)	−0.004 (4)	−0.024 (4)	−0.008 (4)
Cl6	0.115 (2)	0.130 (3)	0.0419 (14)	−0.0598 (17)	0.0091 (11)	−0.0246 (16)
O6	0.106 (5)	0.117 (6)	0.054 (4)	−0.067 (4)	0.006 (3)	−0.020 (4)
Cl7	0.171 (3)	0.098 (3)	0.065 (2)	−0.055 (2)	0.0237 (17)	−0.0066 (15)
O7	0.173 (5)	0.105 (5)	0.072 (5)	−0.057 (5)	0.016 (4)	0.003 (4)
O8A	0.097 (3)	0.164 (7)	0.055 (3)	−0.079 (5)	0.002 (3)	−0.034 (4)
O8	0.097 (3)	0.161 (7)	0.057 (4)	−0.054 (6)	0.000 (3)	−0.045 (4)
Cl9	0.130 (2)	0.130 (4)	0.069 (2)	−0.068 (3)	0.0128 (19)	−0.008 (2)
O9	0.142 (4)	0.140 (7)	0.086 (5)	−0.067 (5)	−0.017 (4)	−0.018 (4)
Cl10	0.209 (4)	0.191 (4)	0.109 (3)	−0.153 (4)	−0.017 (2)	−0.003 (2)
O10	0.218 (6)	0.178 (5)	0.106 (4)	−0.136 (5)	−0.019 (3)	−0.004 (3)
O2	0.0716 (16)	0.0784 (17)	0.0848 (18)	0.0011 (13)	−0.0210 (13)	−0.0129 (14)
O4	0.189 (4)	0.282 (6)	0.104 (3)	−0.164 (5)	0.011 (3)	0.016 (3)

Geometric parameters (Å, º)

Cl2—C29	1.724 (3)	N3—H3	0.859 (10)
N10—H10	0.858 (10)	N3—C8	1.439 (3)
N10—C20	1.329 (4)	N3—C9	1.339 (3)
N10—C21	1.384 (5)	N4—C9	1.356 (3)
N11—H11	0.861 (10)	N4—C10	1.316 (3)
N11—C20	1.326 (4)	N5—C10	1.317 (3)
N11—C26	1.392 (4)	N5—C11	1.359 (3)
N12—H12	0.859 (10)	N6—C9	1.331 (3)
N12—C27	1.437 (4)	N6—C11	1.339 (3)
N12—C28	1.339 (3)	N7—H7	0.856 (10)
N13—C28	1.355 (3)	N7—C11	1.336 (3)
N13—C29	1.313 (3)	N7—C12	1.447 (3)
N14—C29	1.312 (3)	N8—H8	0.861 (10)
N14—C30	1.359 (3)	N8—C13	1.324 (4)
N15—C28	1.336 (3)	N8—C14	1.398 (4)
N15—C30	1.333 (3)	N9—H9	0.861 (10)
N16—H16	0.856 (10)	N9—C13	1.326 (3)
N16—C30	1.339 (3)	N9—C19	1.388 (4)
N16—C31	1.440 (3)	C1—C8	1.488 (4)
N17—H17	0.856 (10)	C2—C3	1.383 (4)
N17—C32	1.322 (3)	C2—C7	1.383 (4)
N17—C33	1.387 (4)	C3—H3A	0.9300
N18—H18	0.859 (10)	C3—C4	1.369 (5)
N18—C32	1.326 (3)	C4—H4	0.9300
N18—C38	1.391 (4)	C4—C5	1.385 (5)
C20—C27	1.487 (4)	C5—H5	0.9300
C21—C22	1.397 (5)	C5—C6	1.376 (5)
C21—C26	1.380 (5)	C6—H6	0.9300
C22—H22	0.9300	C6—C7	1.389 (4)
C22—C23	1.371 (7)	C8—H8A	0.9700
C23—H23	0.9300	C8—H8B	0.9700
C23—C24	1.370 (6)	C12—H12A	0.9700
C24—H24	0.9300	C12—H12B	0.9700
C24—C25	1.379 (5)	C12—C13	1.490 (4)
C25—H25	0.9300	C14—C15	1.388 (4)
C25—C26	1.376 (5)	C14—C19	1.375 (4)
C27—H27A	0.9700	C15—H15	0.9300
C27—H27B	0.9700	C15—C16	1.364 (5)
C31—H31A	0.9700	C16—H16A	0.9300
C31—H31B	0.9700	C16—C17	1.389 (5)
C31—C32	1.497 (4)	C17—H17A	0.9300
C33—C34	1.388 (4)	C17—C18	1.377 (5)
C33—C38	1.384 (4)	C18—H18A	0.9300
C34—H34	0.9300	C18—C19	1.391 (4)
C34—C35	1.364 (5)	O3—H3B	0.858 (10)
C35—H35	0.9300	O3—H3C	0.864 (10)
C35—C36	1.379 (5)	Cl5—O8A^i	2.028 (11)
C36—H36	0.9300	Cl5—Cl10^ii	1.886 (6)
C36—C37	1.382 (5)	O1—H1A	0.844 (10)
C37—H37	0.9300	O1—H1B	0.854 (10)
C37—C38	1.391 (4)	O5—H5A	0.857 (10)
Cl1—C10	1.729 (2)	O5—H5B	0.856 (10)
N1—H1	0.858 (10)	Cl10—O10	1.110 (9)
N1—C1	1.326 (3)	O2—H2A	0.848 (10)
N1—C2	1.389 (4)	O2—H2B	0.850 (10)
N2—H2	0.855 (10)	O4—H4A	0.853 (10)
N2—C1	1.324 (3)	O4—H4B	0.862 (10)
N2—C7	1.381 (4)
C20—N10—H10	124 (3)	C1—N2—C7	109.4 (2)
C20—N10—C21	108.9 (3)	C7—N2—H2	128 (2)
C21—N10—H10	127 (3)	C8—N3—H3	120 (2)
C20—N11—H11	125 (2)	C9—N3—H3	117 (2)
C20—N11—C26	109.3 (3)	C9—N3—C8	122.7 (2)
C26—N11—H11	125 (2)	C10—N4—C9	112.6 (2)
C27—N12—H12	121 (2)	C10—N5—C11	112.4 (2)
C28—N12—H12	116 (2)	C9—N6—C11	114.6 (2)
C28—N12—C27	122.4 (2)	C11—N7—H7	120 (2)
C29—N13—C28	113.1 (2)	C11—N7—C12	120.6 (2)
C29—N14—C30	112.6 (2)	C12—N7—H7	119 (2)
C30—N15—C28	114.5 (2)	C13—N8—H8	124 (2)
C30—N16—H16	119 (2)	C13—N8—C14	109.2 (2)
C30—N16—C31	120.9 (2)	C14—N8—H8	126 (2)
C31—N16—H16	119 (2)	C13—N9—H9	123 (2)
C32—N17—H17	123 (2)	C13—N9—C19	109.2 (2)
C32—N17—C33	109.0 (2)	C19—N9—H9	128 (2)
C33—N17—H17	127 (2)	N1—C1—C8	126.2 (2)
C32—N18—H18	122 (2)	N2—C1—N1	109.0 (2)
C32—N18—C38	109.0 (2)	N2—C1—C8	124.7 (2)
C38—N18—H18	129 (2)	C3—C2—N1	131.3 (3)
N10—C20—C27	124.6 (3)	C3—C2—C7	122.5 (3)
N11—C20—N10	109.1 (3)	C7—C2—N1	106.1 (2)
N11—C20—C27	126.3 (2)	C2—C3—H3A	121.8
N10—C21—C22	132.3 (4)	C4—C3—C2	116.4 (3)
C26—C21—N10	106.9 (3)	C4—C3—H3A	121.8
C26—C21—C22	120.8 (4)	C3—C4—H4	119.3
C21—C22—H22	122.0	C3—C4—C5	121.3 (3)
C23—C22—C21	116.1 (4)	C5—C4—H4	119.3
C23—C22—H22	122.0	C4—C5—H5	118.6
C22—C23—H23	118.7	C6—C5—C4	122.7 (3)
C24—C23—C22	122.5 (4)	C6—C5—H5	118.6
C24—C23—H23	118.7	C5—C6—H6	122.0
C23—C24—H24	118.9	C5—C6—C7	116.0 (3)
C23—C24—C25	122.1 (4)	C7—C6—H6	122.0
C25—C24—H24	118.9	N2—C7—C2	106.3 (2)
C24—C25—H25	122.1	N2—C7—C6	132.7 (3)
C26—C25—C24	115.8 (4)	C2—C7—C6	120.9 (3)
C26—C25—H25	122.1	N3—C8—C1	112.7 (2)
C21—C26—N11	105.8 (3)	N3—C8—H8A	109.1
C25—C26—N11	131.4 (3)	N3—C8—H8B	109.1
C25—C26—C21	122.7 (3)	C1—C8—H8A	109.1
N12—C27—C20	113.4 (2)	C1—C8—H8B	109.1
N12—C27—H27A	108.9	H8A—C8—H8B	107.8
N12—C27—H27B	108.9	N3—C9—N4	117.1 (2)
C20—C27—H27A	108.9	N6—C9—N3	117.4 (2)
C20—C27—H27B	108.9	N6—C9—N4	125.5 (2)
H27A—C27—H27B	107.7	N4—C10—Cl1	115.13 (19)
N12—C28—N13	116.8 (2)	N4—C10—N5	129.3 (2)
N15—C28—N12	118.1 (2)	N5—C10—Cl1	115.55 (19)
N15—C28—N13	125.1 (2)	N6—C11—N5	125.4 (2)
N13—C29—Cl2	115.86 (19)	N7—C11—N5	117.0 (2)
N14—C29—Cl2	115.11 (19)	N7—C11—N6	117.7 (2)
N14—C29—N13	129.0 (2)	N7—C12—H12A	109.2
N15—C30—N14	125.5 (2)	N7—C12—H12B	109.2
N15—C30—N16	118.0 (2)	N7—C12—C13	112.0 (2)
N16—C30—N14	116.5 (2)	H12A—C12—H12B	107.9
N16—C31—H31A	109.3	C13—C12—H12A	109.2
N16—C31—H31B	109.3	C13—C12—H12B	109.2
N16—C31—C32	111.5 (2)	N8—C13—N9	109.0 (3)
H31A—C31—H31B	108.0	N8—C13—C12	125.3 (2)
C32—C31—H31A	109.3	N9—C13—C12	125.6 (2)
C32—C31—H31B	109.3	C15—C14—N8	131.8 (3)
N17—C32—N18	109.4 (2)	C19—C14—N8	106.0 (3)
N17—C32—C31	125.1 (2)	C19—C14—C15	122.2 (3)
N18—C32—C31	125.4 (2)	C14—C15—H15	121.8
N17—C33—C34	132.0 (3)	C16—C15—C14	116.3 (3)
C38—C33—N17	106.5 (2)	C16—C15—H15	121.8
C38—C33—C34	121.5 (3)	C15—C16—H16A	119.1
C33—C34—H34	121.8	C15—C16—C17	121.8 (4)
C35—C34—C33	116.4 (3)	C17—C16—H16A	119.1
C35—C34—H34	121.8	C16—C17—H17A	118.9
C34—C35—H35	118.9	C18—C17—C16	122.3 (3)
C34—C35—C36	122.3 (3)	C18—C17—H17A	118.9
C36—C35—H35	118.9	C17—C18—H18A	122.1
C35—C36—H36	118.8	C17—C18—C19	115.9 (3)
C35—C36—C37	122.4 (3)	C19—C18—H18A	122.0
C37—C36—H36	118.8	N9—C19—C18	131.8 (3)
C36—C37—H37	122.3	C14—C19—N9	106.7 (3)
C36—C37—C38	115.3 (3)	C14—C19—C18	121.5 (3)
C38—C37—H37	122.3	H3B—O3—H3C	102.1 (16)
N18—C38—C37	131.9 (3)	Cl10^ii—Cl5—O8A^i	103.1 (3)
C33—C38—N18	106.0 (2)	H1A—O1—H1B	104.6 (16)
C33—C38—C37	122.1 (3)	H5A—O5—H5B	103.2 (16)
C1—N1—H1	125 (2)	O10—Cl10—Cl5^ii	168.2 (7)
C1—N1—C2	109.1 (2)	H2A—O2—H2B	105.4 (16)
C2—N1—H1	126 (2)	H4A—O4—H4B	103.2 (16)
C1—N2—H2	122 (2)
N10—C20—C27—N12	170.3 (3)	N1—C1—C8—N3	−5.6 (4)
N10—C21—C22—C23	−178.1 (3)	N1—C2—C3—C4	177.1 (3)
N10—C21—C26—N11	−0.1 (3)	N1—C2—C7—N2	0.7 (3)
N10—C21—C26—C25	178.3 (3)	N1—C2—C7—C6	−177.6 (3)
N11—C20—C27—N12	−9.5 (4)	N2—C1—C8—N3	172.3 (2)
N16—C31—C32—N17	165.2 (2)	N7—C12—C13—N8	−20.1 (4)
N16—C31—C32—N18	−17.6 (4)	N7—C12—C13—N9	162.0 (2)
N17—C33—C34—C35	178.2 (3)	N8—C14—C15—C16	−177.7 (3)
N17—C33—C38—N18	−0.7 (3)	N8—C14—C19—N9	−0.9 (3)
N17—C33—C38—C37	−179.2 (3)	N8—C14—C19—C18	177.7 (3)
C20—N10—C21—C22	178.2 (3)	C1—N1—C2—C3	−177.7 (3)
C20—N10—C21—C26	−0.4 (3)	C1—N1—C2—C7	0.6 (3)
C20—N11—C26—C21	0.6 (3)	C1—N2—C7—C2	−1.8 (3)
C20—N11—C26—C25	−177.6 (3)	C1—N2—C7—C6	176.2 (3)
C21—N10—C20—N11	0.8 (3)	C2—N1—C1—N2	−1.8 (3)
C21—N10—C20—C27	−179.1 (3)	C2—N1—C1—C8	176.3 (2)
C21—C22—C23—C24	0.1 (6)	C2—C3—C4—C5	−0.1 (5)
C22—C21—C26—N11	−178.9 (3)	C3—C2—C7—N2	179.2 (3)
C22—C21—C26—C25	−0.5 (5)	C3—C2—C7—C6	0.8 (4)
C22—C23—C24—C25	−0.4 (6)	C3—C4—C5—C6	1.4 (5)
C23—C24—C25—C26	0.3 (5)	C4—C5—C6—C7	−1.5 (5)
C24—C25—C26—N11	178.1 (3)	C5—C6—C7—N2	−177.5 (3)
C24—C25—C26—C21	0.1 (4)	C5—C6—C7—C2	0.4 (5)
C26—N11—C20—N10	−0.9 (3)	C7—N2—C1—N1	2.3 (3)
C26—N11—C20—C27	179.0 (3)	C7—N2—C1—C8	−175.9 (2)
C26—C21—C22—C23	0.4 (5)	C7—C2—C3—C4	−1.0 (4)
C27—N12—C28—N13	176.0 (2)	C8—N3—C9—N4	178.2 (2)
C27—N12—C28—N15	−4.0 (4)	C8—N3—C9—N6	−1.9 (4)
C28—N12—C27—C20	84.8 (3)	C9—N3—C8—C1	87.6 (3)
C28—N13—C29—Cl2	−178.46 (18)	C9—N4—C10—Cl1	−177.05 (18)
C28—N13—C29—N14	2.5 (4)	C9—N4—C10—N5	3.0 (4)
C28—N15—C30—N14	2.8 (4)	C9—N6—C11—N5	3.9 (4)
C28—N15—C30—N16	−178.2 (2)	C9—N6—C11—N7	−177.2 (2)
C29—N13—C28—N12	178.8 (2)	C10—N4—C9—N3	−178.4 (2)
C29—N13—C28—N15	−1.3 (4)	C10—N4—C9—N6	1.7 (4)
C29—N14—C30—N15	−1.8 (4)	C10—N5—C11—N6	−0.1 (4)
C29—N14—C30—N16	179.2 (2)	C10—N5—C11—N7	−179.0 (2)
C30—N14—C29—Cl2	179.86 (17)	C11—N5—C10—Cl1	176.34 (18)
C30—N14—C29—N13	−1.1 (4)	C11—N5—C10—N4	−3.7 (4)
C30—N15—C28—N12	178.9 (2)	C11—N6—C9—N3	175.3 (2)
C30—N15—C28—N13	−1.1 (4)	C11—N6—C9—N4	−4.8 (4)
C30—N16—C31—C32	−75.9 (3)	C11—N7—C12—C13	−69.6 (3)
C31—N16—C30—N14	175.4 (2)	C12—N7—C11—N5	174.8 (2)
C31—N16—C30—N15	−3.7 (4)	C12—N7—C11—N6	−4.2 (4)
C32—N17—C33—C34	−177.5 (3)	C13—N8—C14—C15	179.4 (3)
C32—N17—C33—C38	1.4 (3)	C13—N8—C14—C19	0.4 (3)
C32—N18—C38—C33	−0.3 (3)	C13—N9—C19—C14	1.1 (3)
C32—N18—C38—C37	178.1 (3)	C13—N9—C19—C18	−177.3 (3)
C33—N17—C32—N18	−1.6 (3)	C14—N8—C13—N9	0.3 (3)
C33—N17—C32—C31	176.0 (2)	C14—N8—C13—C12	−178.0 (2)
C33—C34—C35—C36	0.7 (5)	C14—C15—C16—C17	−0.4 (5)
C34—C33—C38—N18	178.4 (3)	C15—C14—C19—N9	180.0 (3)
C34—C33—C38—C37	−0.2 (4)	C15—C14—C19—C18	−1.4 (4)
C34—C35—C36—C37	0.0 (5)	C15—C16—C17—C18	−0.1 (5)
C35—C36—C37—C38	−0.8 (5)	C16—C17—C18—C19	−0.1 (5)
C36—C37—C38—N18	−177.3 (3)	C17—C18—C19—N9	179.1 (3)
C36—C37—C38—C33	0.9 (4)	C17—C18—C19—C14	0.8 (4)
C38—N18—C32—N17	1.1 (3)	C19—N9—C13—N8	−0.9 (3)
C38—N18—C32—C31	−176.4 (2)	C19—N9—C13—C12	177.4 (2)
C38—C33—C34—C35	−0.6 (4)	C19—C14—C15—C16	1.1 (4)

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl7^ii	0.86 (1)	2.25 (2)	3.071 (4)	160 (3)
O1—H1A···O9^iii	0.84 (5)	2.27 (5)	3.112 (15)	179 (6)
O1—H1B···Cl4^iv	0.86 (4)	2.26 (4)	3.071 (4)	156 (5)
N2—H2···O4^v	0.85 (2)	1.86 (2)	2.709 (6)	171 (3)
O2—H2A···N13	0.85 (3)	2.18 (3)	3.016 (3)	174 (4)
O2—H2B···O10^iv	0.85 (4)	2.49 (3)	3.256 (6)	151 (4)
N3—H3···O2^vi	0.86 (2)	2.09 (3)	2.866 (4)	150 (3)
O3—H3B···O9^iv	0.86 (5)	2.32 (5)	3.056 (19)	145 (5)
O3—H3C···Cl4	0.86 (3)	2.23 (2)	3.072 (4)	166 (6)
O4—H4A···O9^iv	0.85 (10)	2.51 (10)	3.136 (19)	132 (7)
O5—H5A···N4^vii	0.85 (6)	2.09 (6)	2.909 (4)	161 (5)
O5—H5B···O2^viii	0.86 (6)	2.03 (6)	2.864 (5)	163 (6)
N7—H7···N14	0.85 (3)	2.10 (3)	2.953 (3)	177 (3)
N8—H8···Cl6	0.86 (1)	2.22 (2)	3.047 (5)	162 (4)
N9—H9···O1	0.86 (2)	1.89 (2)	2.751 (4)	178 (2)
N10—H10···O8A	0.86 (4)	2.20 (4)	3.009 (11)	157 (3)
N11—H11···Cl3^ix	0.86 (1)	2.08 (2)	2.923 (3)	168 (4)
N12—H12···O5^ix	0.86 (2)	1.93 (2)	2.716 (4)	152 (2)
N16—H16···N5	0.86 (3)	2.14 (3)	2.990 (3)	178 (3)
N17—H17···O3	0.86 (3)	1.85 (3)	2.704 (5)	175 (3)
N18—H18···Cl6	0.86 (1)	2.21 (2)	3.003 (6)	153 (3)
C8—H8A···Cl4^iv	0.97	2.81	3.759 (3)	168
C12—H12B···Cl4^iv	0.97	2.62	3.583 (3)	173

Symmetry codes: (ii) −x+1, −y+2, −z+1; (iii) −x+1, −y+1, −z+2; (iv) −x+1, −y+1, −z+1; (v) x, y, z+1; (vi) x−1, y+1, z; (vii) x, y−1, z; (viii) −x+1, −y, −z+1; (ix) x+1, y, z.