Expanding the structural landscape of niclosamide: a high Z′ polymorph, two new solvates and monohydrate H_A

Three new crystalline phases are reported for the drug niclosamide [5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide], C₁₃H₈Cl₂N₂O₄. A new high-Z′ polymorph (denoted Form II) is described, with four molecules in the asymmetric unit in the space group P2/n. The structure exhibits pseudosymmetry, including local translations and screw-type operations. The niclosamide molecules are linked by O—H...O hydrogen bonds into chains, and the chains are packed so that the molecules form face-to-face (stacking) and end-to-end interactions within layers perpendicular to the chains. There are two different layer arrangements, giving a structure that is relatively complex. In the acetone and acetonitrile solvates, the incorporated solvent molecules accept hydrogen bonds from the OH groups of niclosamide, and the niclosamide molecules are stacked in a face-to-face manner. In the acetone solvate, C₁₃H₈Cl₂N₂O₄·C₃H₆O, V-shaped arrangements are formed in which the nitrobenzene ends of the niclosamide molecules are brought into face-to-face contact. In the acetonitrile solvate, C₁₃H₈Cl₂N₂O₄·CH₃CN, stacking occurs by translation along a short axis (ca 3.8 Å) and the crystals are frequently observed to be twinned by twofold rotation around that axis. The acetonitrile molecules occupy channels in the structure. A complete structure is provided for niclosamide monohydrate, C₁₃H₈Cl₂N₂O₄·H₂O, polymorph H_A, obtained by Rietveld refinement against laboratory powder X-ray diffraction data. It has been suggested that this compound is related to the methanol solvate of niclosamide [Harriss, Wilson & Radosevljevic Evans (2014). Acta Cryst. C70, 758–763], but it is found that the two are not fully isostructural: they contain isostructural two-dimensional layers, but the layers are arranged differently in the two structures. This suggests that H_A may have the potential for polytypism, and features in the Rietveld difference curve indicate that a polytype fully isostructural with the methanol solvate might be present.

Computing details

Data collection: APEX2 (Bruker, 2012) for niclosamide_FormII, niclosamide_acetone, niclosamide_acetonitrile; Data Collector (PANalytical, 2010) for niclosamide_HA. Cell refinement: SAINT (Bruker, 2012) for niclosamide_FormII, niclosamide_acetone, niclosamide_acetonitrile; TOPAS Academic (Coelho, 2007) for niclosamide_HA. Data reduction: SAINT (Bruker, 2012) for niclosamide_FormII, niclosamide_acetone, niclosamide_acetonitrile. Program(s) used to solve structure: SHELXT (Sheldrick, 2015a) for niclosamide_FormII, niclosamide_acetone, niclosamide_acetonitrile; DASH (David et al., 2006) for niclosamide_HA. Program(s) used to refine structure: SHELXL (Sheldrick, 2015b) for niclosamide_FormII, niclosamide_acetone, niclosamide_acetonitrile; TOPAS Academic (Coelho, 2007) for niclosamide_HA. For all compounds, molecular graphics: Mercury (Macrae et al., 2008). Software used to prepare material for publication: SHELXL (Sheldrick, 2015b) for niclosamide_FormII, niclosamide_acetone, niclosamide_acetonitrile.

Figures

(niclosamide_FormII) 5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide

Crystal data

C13H8Cl2N2O4	F(000) = 2656
Mr = 327.11	Dx = 1.647 Mg m^−3
Monoclinic, P2/n	Mo Kα radiation, λ = 0.71073 Å
a = 15.3040 (5) Å	Cell parameters from 8327 reflections
b = 12.9458 (4) Å	θ = 2.7–25.6°
c = 26.6596 (9) Å	µ = 0.51 mm^−1
β = 92.282 (2)°	T = 298 K
V = 5277.7 (3) Å^3	Block, yellow
Z = 16	0.50 × 0.30 × 0.10 mm

Data collection

Bruker Nonius X8 APEXII CCD area-detector diffractometer	6416 independent reflections
Radiation source: fine-focus sealed tube	4482 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
ω and ϕ scans	θmax = 22.0°, θmin = 3.5°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −16→16
Tmin = 0.839, Tmax = 0.951	k = −13→13
27935 measured reflections	l = −28→28

Refinement

Refinement on F^2	8 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.076	w = 1/[σ^2(Fo^2) + (0.0444P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.92	(Δ/σ)max = 0.001
6416 reflections	Δρmax = 0.42 e Å^−3
789 parameters	Δρmin = −0.44 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.

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

	x	y	z	Uiso*/Ueq
Cl1A	0.48648 (5)	0.21278 (5)	0.30791 (3)	0.0763 (3)
Cl2A	0.96903 (5)	−0.16350 (6)	0.32901 (3)	0.0741 (3)
O1A	0.18401 (13)	−0.10670 (17)	0.31084 (8)	0.0723 (6)
O2A	0.17279 (13)	0.05881 (17)	0.31201 (7)	0.0719 (6)
O3A	0.62956 (10)	−0.14930 (11)	0.31123 (6)	0.0473 (5)
O4A	0.70212 (13)	0.15952 (14)	0.31130 (8)	0.0600 (6)
H4A	0.7229 (17)	0.2171 (13)	0.3218 (10)	0.089 (11)*
N1A	0.21579 (16)	−0.0202 (2)	0.31162 (8)	0.0532 (6)
N2A	0.58220 (15)	0.01606 (15)	0.30928 (8)	0.0387 (5)
H2A	0.6030 (17)	0.0792 (11)	0.3086 (10)	0.080 (10)*
C1A	0.49195 (17)	0.00271 (17)	0.30909 (8)	0.0368 (6)
C2A	0.43852 (19)	0.09122 (17)	0.30864 (9)	0.0436 (7)
C3A	0.34929 (19)	0.0837 (2)	0.30957 (9)	0.0486 (7)
H3A	0.3149	0.1429	0.3091	0.058*
C4A	0.31157 (18)	−0.0117 (2)	0.31118 (9)	0.0420 (7)
C5A	0.36114 (19)	−0.09985 (19)	0.31190 (9)	0.0464 (7)
H5A	0.3344	−0.1642	0.3133	0.056*
C6A	0.45054 (17)	−0.09257 (18)	0.31052 (9)	0.0423 (7)
H6A	0.4839	−0.1526	0.3105	0.051*
C7A	0.64677 (17)	−0.05666 (18)	0.31127 (8)	0.0345 (6)
C8A	0.73798 (16)	−0.01853 (17)	0.31405 (8)	0.0341 (6)
C9A	0.80419 (17)	−0.09354 (18)	0.31787 (9)	0.0402 (7)
H9A	0.7888	−0.1630	0.3173	0.048*
C10A	0.89031 (18)	−0.06736 (19)	0.32234 (9)	0.0448 (7)
C11A	0.91554 (19)	0.0350 (2)	0.32217 (10)	0.0528 (8)
H11A	0.9744	0.0528	0.3244	0.063*
C12A	0.8523 (2)	0.1101 (2)	0.31858 (10)	0.0539 (8)
H12A	0.8687	0.1793	0.3186	0.065*
C13A	0.76440 (19)	0.08458 (18)	0.31499 (9)	0.0417 (7)
Cl1B	0.49972 (5)	0.20294 (4)	0.57158 (3)	0.0572 (2)
Cl2B	0.96521 (5)	−0.19967 (6)	0.56736 (4)	0.0947 (3)
O1B	0.18366 (13)	−0.09915 (18)	0.55684 (8)	0.0725 (6)
O2B	0.17865 (13)	0.06649 (17)	0.56005 (7)	0.0712 (6)
O3B	0.62734 (10)	−0.16401 (12)	0.56198 (7)	0.0495 (5)
O4B	0.71280 (12)	0.13981 (13)	0.56594 (7)	0.0571 (5)
H4B	0.7349 (16)	0.1968 (12)	0.5753 (10)	0.075 (10)*
N1B	0.21904 (16)	−0.0147 (2)	0.55912 (8)	0.0539 (6)
N2B	0.58672 (14)	0.00354 (14)	0.56368 (7)	0.0355 (5)
H2B	0.6111 (13)	0.0648 (10)	0.5663 (8)	0.044 (8)*
C1B	0.49610 (17)	−0.00547 (17)	0.56305 (8)	0.0345 (6)
C2B	0.44614 (17)	0.08558 (16)	0.56573 (8)	0.0365 (7)
C3B	0.35678 (18)	0.08329 (19)	0.56425 (9)	0.0428 (7)
H3B	0.3247	0.1442	0.5656	0.051*
C4B	0.31523 (17)	−0.0108 (2)	0.56074 (9)	0.0409 (7)
C5B	0.36110 (18)	−0.10119 (18)	0.55862 (9)	0.0431 (7)
H5B	0.3318	−0.1641	0.5566	0.052*
C6B	0.45089 (17)	−0.09808 (17)	0.55955 (9)	0.0411 (7)
H6B	0.4820	−0.1596	0.5578	0.049*
C7B	0.64836 (16)	−0.07221 (18)	0.56325 (8)	0.0341 (6)
C8B	0.74140 (16)	−0.03960 (17)	0.56431 (9)	0.0349 (6)
C9B	0.80383 (17)	−0.11873 (18)	0.56400 (9)	0.0452 (7)
H9B	0.7853	−0.1871	0.5625	0.054*
C10B	0.89067 (19)	−0.0978 (2)	0.56586 (10)	0.0521 (8)
C11B	0.92088 (19)	0.0025 (2)	0.56776 (10)	0.0557 (8)
H11B	0.9806	0.0162	0.5687	0.067*
C12B	0.8614 (2)	0.0817 (2)	0.56819 (10)	0.0506 (8)
H12B	0.8811	0.1496	0.5697	0.061*
C13B	0.77286 (19)	0.06178 (18)	0.56638 (9)	0.0410 (7)
Cl1C	0.81456 (5)	0.68313 (5)	0.43923 (3)	0.0576 (2)
Cl2C	0.54517 (4)	0.36784 (5)	0.18020 (3)	0.0526 (2)
O1C	0.95800 (14)	0.32486 (17)	0.57316 (8)	0.0819 (7)
O2C	0.96096 (14)	0.48707 (16)	0.58939 (8)	0.0752 (6)
O3C	0.74200 (10)	0.34472 (11)	0.34327 (6)	0.0444 (5)
O4C	0.69289 (12)	0.66005 (13)	0.32798 (7)	0.0505 (5)
H4C	0.6731 (15)	0.7199 (11)	0.3221 (9)	0.064 (9)*
N1C	0.94147 (14)	0.4144 (2)	0.56257 (9)	0.0535 (6)
N2C	0.76087 (13)	0.50131 (15)	0.37911 (8)	0.0364 (5)
H2C	0.7500 (13)	0.5669 (8)	0.3758 (8)	0.042 (7)*
C1C	0.80771 (15)	0.47616 (17)	0.42329 (9)	0.0339 (6)
C2C	0.83484 (16)	0.55585 (17)	0.45583 (10)	0.0386 (7)
C3C	0.87824 (15)	0.53632 (18)	0.50091 (9)	0.0417 (7)
H3C	0.8951	0.5902	0.5222	0.050*
C4C	0.89630 (15)	0.4358 (2)	0.51393 (10)	0.0403 (6)
C5C	0.87210 (16)	0.35520 (19)	0.48275 (10)	0.0430 (7)
H5C	0.8853	0.2876	0.4921	0.052*
C6C	0.82831 (16)	0.37490 (18)	0.43759 (9)	0.0412 (7)
H6C	0.8123	0.3204	0.4165	0.049*
C7C	0.72819 (15)	0.43797 (18)	0.34249 (9)	0.0323 (6)
C8C	0.67613 (15)	0.48634 (16)	0.30013 (9)	0.0310 (6)
C9C	0.63963 (15)	0.41888 (17)	0.26421 (9)	0.0359 (6)
H9C	0.6470	0.3481	0.2685	0.043*
C10C	0.59333 (15)	0.45457 (18)	0.22286 (9)	0.0357 (6)
C11C	0.58260 (15)	0.55897 (19)	0.21520 (10)	0.0428 (7)
H11C	0.5525	0.5831	0.1866	0.051*
C12C	0.61650 (16)	0.62674 (18)	0.25002 (10)	0.0421 (7)
H12C	0.6092	0.6973	0.2449	0.051*
C13C	0.66179 (15)	0.59198 (17)	0.29292 (10)	0.0365 (6)
Cl1D	0.80809 (5)	0.67803 (5)	0.68478 (3)	0.0648 (2)
Cl2D	0.56957 (5)	0.35710 (5)	0.42128 (3)	0.0559 (2)
O1D	0.94384 (16)	0.33596 (16)	0.82967 (8)	0.0915 (8)
O2D	0.95526 (15)	0.49831 (15)	0.83900 (8)	0.0819 (7)
O3D	0.74445 (12)	0.33296 (12)	0.59360 (7)	0.0569 (5)
O4D	0.68447 (12)	0.64489 (13)	0.57942 (7)	0.0595 (6)
H4D	0.6667 (15)	0.7056 (10)	0.5726 (9)	0.061 (9)*
N1D	0.93300 (14)	0.4235 (2)	0.81470 (9)	0.0523 (6)
N2D	0.75909 (13)	0.49085 (15)	0.62818 (8)	0.0425 (6)
H2D	0.7459 (13)	0.5557 (9)	0.6230 (8)	0.049 (8)*
C1D	0.80614 (15)	0.46965 (17)	0.67275 (10)	0.0364 (6)
C2D	0.83060 (16)	0.55262 (17)	0.70383 (10)	0.0401 (7)
C3D	0.87255 (16)	0.53780 (18)	0.74955 (10)	0.0413 (7)
H3D	0.8883	0.5939	0.7697	0.050*
C4D	0.89105 (15)	0.43928 (19)	0.76511 (9)	0.0380 (6)
C5D	0.87014 (16)	0.35546 (18)	0.73520 (10)	0.0431 (7)
H5D	0.8843	0.2890	0.7460	0.052*
C6D	0.82826 (16)	0.37079 (17)	0.68928 (10)	0.0438 (7)
H6D	0.8145	0.3143	0.6689	0.053*
C7D	0.72830 (15)	0.42551 (18)	0.59194 (9)	0.0371 (6)
C8D	0.67738 (15)	0.47227 (16)	0.54873 (9)	0.0346 (6)
C9D	0.64856 (15)	0.40549 (17)	0.51084 (10)	0.0387 (7)
H9D	0.6596	0.3351	0.5141	0.046*
C10D	0.60405 (16)	0.44147 (17)	0.46863 (10)	0.0383 (6)
C11D	0.58593 (15)	0.54477 (17)	0.46310 (10)	0.0422 (7)
H11D	0.5562	0.5691	0.4344	0.051*
C12D	0.61245 (16)	0.61140 (17)	0.50067 (10)	0.0463 (7)
H12D	0.5995	0.6813	0.4974	0.056*
C13D	0.65781 (16)	0.57698 (18)	0.54306 (10)	0.0411 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1A	0.0747 (6)	0.0294 (4)	0.1247 (8)	0.0067 (4)	0.0010 (5)	0.0112 (4)
Cl2A	0.0472 (5)	0.0653 (5)	0.1083 (7)	0.0058 (4)	−0.0148 (5)	−0.0251 (5)
O1A	0.0569 (15)	0.0781 (16)	0.0816 (17)	−0.0121 (12)	−0.0008 (12)	−0.0101 (13)
O2A	0.0592 (15)	0.0826 (15)	0.0734 (16)	0.0265 (13)	−0.0032 (12)	0.0009 (12)
O3A	0.0474 (12)	0.0210 (10)	0.0730 (13)	−0.0005 (8)	−0.0026 (10)	−0.0032 (9)
O4A	0.0670 (15)	0.0254 (11)	0.0864 (16)	−0.0044 (11)	−0.0137 (12)	−0.0033 (10)
N1A	0.0495 (19)	0.0741 (19)	0.0357 (15)	0.0079 (16)	−0.0036 (13)	−0.0047 (14)
N2A	0.0458 (17)	0.0235 (13)	0.0464 (14)	0.0006 (12)	−0.0025 (11)	−0.0004 (11)
C1A	0.049 (2)	0.0318 (16)	0.0292 (16)	0.0034 (14)	−0.0057 (13)	−0.0007 (11)
C2A	0.057 (2)	0.0295 (15)	0.0439 (18)	0.0068 (14)	0.0008 (15)	0.0030 (12)
C3A	0.055 (2)	0.0467 (18)	0.0437 (18)	0.0175 (15)	−0.0038 (16)	0.0010 (14)
C4A	0.044 (2)	0.0496 (18)	0.0321 (16)	0.0060 (15)	−0.0030 (14)	−0.0019 (13)
C5A	0.057 (2)	0.0405 (16)	0.0417 (18)	−0.0019 (15)	−0.0023 (15)	−0.0074 (13)
C6A	0.049 (2)	0.0308 (15)	0.0467 (18)	0.0034 (13)	−0.0036 (15)	−0.0062 (12)
C7A	0.0473 (19)	0.0266 (15)	0.0294 (16)	0.0016 (14)	−0.0029 (13)	−0.0020 (12)
C8A	0.0448 (18)	0.0282 (14)	0.0290 (15)	−0.0032 (13)	−0.0007 (13)	−0.0032 (11)
C9A	0.0467 (19)	0.0341 (15)	0.0397 (17)	−0.0057 (14)	−0.0013 (14)	−0.0057 (12)
C10A	0.046 (2)	0.0465 (17)	0.0418 (18)	−0.0021 (14)	−0.0020 (14)	−0.0103 (13)
C11A	0.049 (2)	0.0564 (19)	0.0528 (19)	−0.0168 (17)	−0.0011 (15)	−0.0059 (15)
C12A	0.066 (2)	0.0357 (16)	0.060 (2)	−0.0167 (16)	−0.0020 (17)	0.0009 (14)
C13A	0.058 (2)	0.0290 (16)	0.0374 (17)	−0.0045 (15)	−0.0044 (15)	−0.0014 (12)
Cl1B	0.0686 (5)	0.0269 (4)	0.0743 (5)	0.0073 (3)	−0.0185 (4)	−0.0043 (3)
Cl2B	0.0510 (6)	0.0755 (6)	0.1569 (9)	0.0160 (4)	−0.0031 (6)	−0.0285 (6)
O1B	0.0555 (15)	0.0802 (16)	0.0817 (17)	−0.0111 (12)	0.0006 (12)	−0.0001 (13)
O2B	0.0575 (15)	0.0830 (15)	0.0730 (16)	0.0261 (12)	0.0018 (12)	0.0001 (12)
O3B	0.0489 (12)	0.0204 (10)	0.0786 (14)	0.0017 (8)	−0.0058 (10)	−0.0031 (9)
O4B	0.0620 (14)	0.0276 (11)	0.0803 (15)	−0.0053 (11)	−0.0132 (11)	−0.0022 (10)
N1B	0.054 (2)	0.0706 (19)	0.0366 (15)	0.0057 (16)	−0.0007 (13)	−0.0002 (13)
N2B	0.0450 (16)	0.0207 (12)	0.0404 (14)	−0.0004 (12)	−0.0052 (11)	−0.0027 (10)
C1B	0.0447 (19)	0.0319 (15)	0.0265 (15)	0.0027 (13)	−0.0043 (13)	0.0008 (11)
C2B	0.050 (2)	0.0283 (14)	0.0303 (16)	0.0062 (13)	−0.0075 (14)	−0.0023 (11)
C3B	0.052 (2)	0.0432 (17)	0.0330 (17)	0.0150 (15)	−0.0039 (14)	−0.0011 (13)
C4B	0.0376 (19)	0.0514 (18)	0.0334 (16)	0.0044 (15)	−0.0019 (13)	0.0002 (13)
C5B	0.051 (2)	0.0388 (16)	0.0391 (17)	−0.0016 (14)	0.0012 (14)	−0.0016 (12)
C6B	0.046 (2)	0.0291 (15)	0.0479 (18)	0.0037 (13)	−0.0012 (14)	−0.0017 (12)
C7B	0.0431 (18)	0.0289 (15)	0.0298 (16)	0.0048 (14)	−0.0039 (13)	−0.0015 (12)
C8B	0.0455 (19)	0.0282 (14)	0.0305 (15)	−0.0008 (13)	−0.0035 (13)	−0.0044 (11)
C9B	0.048 (2)	0.0346 (15)	0.0523 (19)	−0.0009 (14)	−0.0008 (15)	−0.0075 (13)
C10B	0.042 (2)	0.0526 (19)	0.062 (2)	0.0002 (15)	−0.0021 (16)	−0.0103 (15)
C11B	0.046 (2)	0.063 (2)	0.057 (2)	−0.0126 (17)	−0.0039 (16)	−0.0056 (16)
C12B	0.058 (2)	0.0457 (17)	0.0470 (19)	−0.0168 (16)	−0.0088 (16)	0.0021 (14)
C13B	0.051 (2)	0.0351 (16)	0.0361 (17)	0.0012 (15)	−0.0073 (14)	−0.0009 (12)
Cl1C	0.0687 (5)	0.0317 (4)	0.0713 (5)	−0.0009 (3)	−0.0092 (4)	−0.0040 (3)
Cl2C	0.0534 (5)	0.0480 (4)	0.0552 (5)	0.0077 (3)	−0.0131 (4)	−0.0104 (3)
O1C	0.0929 (18)	0.0722 (15)	0.0776 (16)	0.0010 (13)	−0.0343 (13)	0.0207 (13)
O2C	0.0852 (17)	0.0857 (16)	0.0529 (14)	−0.0031 (13)	−0.0187 (12)	−0.0139 (12)
O3C	0.0569 (12)	0.0234 (10)	0.0519 (12)	0.0049 (8)	−0.0109 (9)	−0.0006 (8)
O4C	0.0615 (13)	0.0244 (10)	0.0639 (13)	0.0067 (10)	−0.0184 (10)	−0.0025 (10)
N1C	0.0410 (16)	0.0715 (19)	0.0480 (18)	−0.0051 (14)	−0.0002 (13)	0.0047 (15)
N2C	0.0448 (14)	0.0211 (12)	0.0432 (15)	0.0032 (11)	−0.0006 (12)	0.0009 (11)
C1C	0.0324 (16)	0.0338 (15)	0.0358 (16)	0.0037 (12)	0.0032 (13)	0.0042 (13)
C2C	0.0368 (17)	0.0304 (14)	0.0488 (18)	−0.0020 (12)	0.0056 (15)	−0.0058 (13)
C3C	0.0372 (18)	0.0441 (17)	0.0438 (19)	−0.0030 (13)	0.0010 (14)	−0.0091 (14)
C4C	0.0292 (16)	0.0540 (18)	0.0373 (17)	0.0004 (13)	−0.0022 (13)	0.0021 (15)
C5C	0.0403 (17)	0.0375 (15)	0.0513 (19)	0.0060 (13)	0.0030 (15)	0.0072 (14)
C6C	0.0447 (18)	0.0360 (16)	0.0425 (18)	0.0030 (13)	−0.0031 (14)	−0.0017 (13)
C7C	0.0318 (16)	0.0292 (15)	0.0362 (17)	−0.0001 (12)	0.0056 (13)	0.0000 (13)
C8C	0.0294 (15)	0.0254 (14)	0.0385 (16)	0.0024 (11)	0.0052 (13)	0.0012 (12)
C9C	0.0353 (16)	0.0280 (13)	0.0445 (17)	0.0048 (12)	0.0041 (14)	0.0000 (13)
C10C	0.0303 (16)	0.0368 (16)	0.0399 (17)	0.0031 (12)	0.0013 (13)	−0.0048 (13)
C11C	0.0380 (17)	0.0443 (17)	0.0460 (18)	0.0078 (13)	0.0004 (14)	0.0058 (14)
C12C	0.0438 (18)	0.0288 (14)	0.0536 (19)	0.0053 (13)	−0.0012 (15)	0.0060 (14)
C13C	0.0329 (16)	0.0313 (15)	0.0455 (18)	0.0011 (12)	0.0018 (14)	0.0001 (13)
Cl1D	0.0798 (6)	0.0273 (4)	0.0853 (6)	0.0088 (3)	−0.0220 (5)	−0.0025 (4)
Cl2D	0.0758 (6)	0.0402 (4)	0.0512 (5)	0.0000 (4)	−0.0045 (4)	−0.0044 (3)
O1D	0.153 (2)	0.0511 (14)	0.0678 (16)	0.0050 (14)	−0.0280 (15)	0.0161 (12)
O2D	0.115 (2)	0.0617 (14)	0.0663 (16)	0.0001 (13)	−0.0275 (14)	−0.0120 (12)
O3D	0.0824 (15)	0.0242 (10)	0.0626 (13)	0.0078 (9)	−0.0176 (10)	0.0003 (9)
O4D	0.0742 (15)	0.0241 (10)	0.0778 (14)	0.0102 (10)	−0.0303 (11)	−0.0047 (11)
N1D	0.0569 (17)	0.0521 (16)	0.0478 (17)	0.0018 (13)	0.0022 (13)	0.0005 (14)
N2D	0.0456 (15)	0.0234 (13)	0.0576 (17)	0.0055 (11)	−0.0071 (12)	0.0034 (12)
C1D	0.0323 (17)	0.0279 (15)	0.0490 (18)	0.0010 (12)	0.0039 (14)	0.0038 (13)
C2D	0.0353 (17)	0.0248 (14)	0.060 (2)	0.0034 (12)	0.0016 (15)	−0.0008 (14)
C3D	0.0388 (18)	0.0341 (16)	0.0508 (19)	0.0010 (12)	0.0009 (15)	−0.0076 (13)
C4D	0.0317 (16)	0.0408 (16)	0.0418 (18)	0.0009 (12)	0.0036 (14)	0.0031 (14)
C5D	0.0498 (18)	0.0301 (15)	0.0494 (19)	0.0022 (13)	0.0046 (15)	0.0077 (14)
C6D	0.0492 (18)	0.0292 (15)	0.0528 (19)	0.0006 (13)	0.0006 (15)	−0.0005 (13)
C7D	0.0368 (17)	0.0267 (15)	0.0481 (19)	0.0002 (13)	0.0047 (14)	−0.0007 (14)
C8D	0.0308 (16)	0.0245 (14)	0.0485 (18)	0.0023 (12)	0.0020 (13)	0.0028 (13)
C9D	0.0374 (17)	0.0258 (13)	0.0536 (19)	0.0015 (12)	0.0087 (15)	0.0012 (14)
C10D	0.0380 (17)	0.0320 (15)	0.0449 (18)	−0.0003 (12)	0.0038 (14)	0.0004 (13)
C11D	0.0407 (18)	0.0373 (16)	0.0485 (18)	0.0045 (13)	−0.0011 (14)	0.0057 (14)
C12D	0.0476 (19)	0.0264 (14)	0.064 (2)	0.0080 (13)	−0.0061 (16)	0.0027 (14)
C13D	0.0362 (17)	0.0297 (15)	0.057 (2)	0.0027 (12)	−0.0031 (15)	−0.0004 (14)

Geometric parameters (Å, º)

Cl1A—C2A	1.737 (2)	Cl1C—C2C	1.731 (2)
Cl2A—C10A	1.736 (3)	Cl2C—C10C	1.741 (2)
O1A—N1A	1.220 (3)	O1C—N1C	1.218 (3)
O2A—N1A	1.217 (3)	O2C—N1C	1.211 (3)
O3A—C7A	1.228 (2)	O3C—C7C	1.226 (2)
O4A—C13A	1.361 (3)	O4C—C13C	1.357 (3)
O4A—H4A	0.853 (10)	O4C—H4C	0.844 (10)
N1A—C4A	1.470 (3)	N1C—C4C	1.471 (3)
N2A—C7A	1.364 (3)	N2C—C7C	1.355 (3)
N2A—C1A	1.392 (3)	N2C—C1C	1.393 (3)
N2A—H2A	0.878 (10)	N2C—H2C	0.869 (10)
C1A—C6A	1.388 (3)	C1C—C6C	1.398 (3)
C1A—C2A	1.407 (3)	C1C—C2C	1.400 (3)
C2A—C3A	1.370 (3)	C2C—C3C	1.373 (3)
C3A—C4A	1.365 (3)	C3C—C4C	1.372 (3)
C3A—H3A	0.9300	C3C—H3C	0.9300
C4A—C5A	1.370 (3)	C4C—C5C	1.375 (3)
C5A—C6A	1.373 (3)	C5C—C6C	1.378 (3)
C5A—H5A	0.9300	C5C—H5C	0.9300
C6A—H6A	0.9300	C6C—H6C	0.9300
C7A—C8A	1.480 (3)	C7C—C8C	1.494 (3)
C8A—C13A	1.395 (3)	C8C—C9C	1.396 (3)
C8A—C9A	1.404 (3)	C8C—C13C	1.397 (3)
C9A—C10A	1.362 (3)	C9C—C10C	1.367 (3)
C9A—H9A	0.9300	C9C—H9C	0.9300
C10A—C11A	1.380 (3)	C10C—C11C	1.376 (3)
C11A—C12A	1.373 (3)	C11C—C12C	1.365 (3)
C11A—H11A	0.9300	C11C—H11C	0.9300
C12A—C13A	1.384 (3)	C12C—C13C	1.389 (3)
C12A—H12A	0.9300	C12C—H12C	0.9300
Cl1B—C2B	1.731 (2)	Cl1D—C2D	1.732 (2)
Cl2B—C10B	1.743 (3)	Cl2D—C10D	1.736 (2)
O1B—N1B	1.220 (3)	O1D—N1D	1.211 (3)
O2B—N1B	1.220 (3)	O2D—N1D	1.207 (3)
O3B—C7B	1.231 (3)	O3D—C7D	1.224 (3)
O4B—C13B	1.365 (3)	O4D—C13D	1.359 (3)
O4B—H4B	0.846 (10)	O4D—H4D	0.849 (10)
N1B—C4B	1.472 (3)	N1D—C4D	1.461 (3)
N2B—C7B	1.361 (3)	N2D—C7D	1.355 (3)
N2B—C1B	1.391 (3)	N2D—C1D	1.392 (3)
N2B—H2B	0.878 (10)	N2D—H2D	0.874 (10)
C1B—C6B	1.386 (3)	C1D—C6D	1.391 (3)
C1B—C2B	1.408 (3)	C1D—C2D	1.398 (3)
C2B—C3B	1.367 (3)	C2D—C3D	1.368 (3)
C3B—C4B	1.375 (3)	C3D—C4D	1.367 (3)
C3B—H3B	0.9300	C3D—H3D	0.9300
C4B—C5B	1.367 (3)	C4D—C5D	1.377 (3)
C5B—C6B	1.374 (3)	C5D—C6D	1.374 (3)
C5B—H5B	0.9300	C5D—H5D	0.9300
C6B—H6B	0.9300	C6D—H6D	0.9300
C7B—C8B	1.484 (3)	C7D—C8D	1.493 (3)
C8B—C13B	1.398 (3)	C8D—C9D	1.388 (3)
C8B—C9B	1.401 (3)	C8D—C13D	1.395 (3)
C9B—C10B	1.355 (3)	C9D—C10D	1.373 (3)
C9B—H9B	0.9300	C9D—H9D	0.9300
C10B—C11B	1.379 (3)	C10D—C11D	1.373 (3)
C11B—C12B	1.371 (3)	C11D—C12D	1.371 (3)
C11B—H11B	0.9300	C11D—H11D	0.9300
C12B—C13B	1.379 (3)	C12D—C13D	1.377 (3)
C12B—H12B	0.9300	C12D—H12D	0.9300
C13A—O4A—H4A	110 (2)	C13C—O4C—H4C	110.8 (18)
O2A—N1A—O1A	123.8 (3)	O2C—N1C—O1C	123.9 (3)
O2A—N1A—C4A	118.5 (3)	O2C—N1C—C4C	118.1 (2)
O1A—N1A—C4A	117.7 (2)	O1C—N1C—C4C	118.0 (2)
C7A—N2A—C1A	129.2 (2)	C7C—N2C—C1C	129.1 (2)
C7A—N2A—H2A	112.4 (18)	C7C—N2C—H2C	117.1 (14)
C1A—N2A—H2A	118.4 (18)	C1C—N2C—H2C	113.8 (14)
C6A—C1A—N2A	124.4 (2)	N2C—C1C—C6C	123.6 (2)
C6A—C1A—C2A	117.3 (2)	N2C—C1C—C2C	118.8 (2)
N2A—C1A—C2A	118.4 (2)	C6C—C1C—C2C	117.6 (2)
C3A—C2A—C1A	121.4 (2)	C3C—C2C—C1C	121.9 (2)
C3A—C2A—Cl1A	119.09 (19)	C3C—C2C—Cl1C	118.33 (19)
C1A—C2A—Cl1A	119.5 (2)	C1C—C2C—Cl1C	119.8 (2)
C4A—C3A—C2A	119.2 (2)	C4C—C3C—C2C	118.8 (2)
C4A—C3A—H3A	120.4	C4C—C3C—H3C	120.6
C2A—C3A—H3A	120.4	C2C—C3C—H3C	120.6
C3A—C4A—C5A	121.3 (3)	C3C—C4C—C5C	121.3 (2)
C3A—C4A—N1A	119.4 (2)	C3C—C4C—N1C	118.9 (2)
C5A—C4A—N1A	119.3 (2)	C5C—C4C—N1C	119.7 (2)
C4A—C5A—C6A	119.6 (2)	C4C—C5C—C6C	119.8 (2)
C4A—C5A—H5A	120.2	C4C—C5C—H5C	120.1
C6A—C5A—H5A	120.2	C6C—C5C—H5C	120.1
C5A—C6A—C1A	121.2 (2)	C5C—C6C—C1C	120.6 (2)
C5A—C6A—H6A	119.4	C5C—C6C—H6C	119.7
C1A—C6A—H6A	119.4	C1C—C6C—H6C	119.7
O3A—C7A—N2A	121.3 (2)	O3C—C7C—N2C	121.7 (2)
O3A—C7A—C8A	121.9 (2)	O3C—C7C—C8C	120.8 (2)
N2A—C7A—C8A	116.9 (2)	N2C—C7C—C8C	117.5 (2)
C13A—C8A—C9A	116.9 (2)	C9C—C8C—C13C	117.5 (2)
C13A—C8A—C7A	126.3 (2)	C9C—C8C—C7C	116.3 (2)
C9A—C8A—C7A	116.7 (2)	C13C—C8C—C7C	126.2 (2)
C10A—C9A—C8A	121.8 (2)	C10C—C9C—C8C	121.5 (2)
C10A—C9A—H9A	119.1	C10C—C9C—H9C	119.3
C8A—C9A—H9A	119.1	C8C—C9C—H9C	119.3
C9A—C10A—C11A	120.6 (2)	C9C—C10C—C11C	120.4 (2)
C9A—C10A—Cl2A	119.7 (2)	C9C—C10C—Cl2C	120.08 (18)
C11A—C10A—Cl2A	119.7 (2)	C11C—C10C—Cl2C	119.5 (2)
C12A—C11A—C10A	118.9 (3)	C12C—C11C—C10C	119.4 (2)
C12A—C11A—H11A	120.5	C12C—C11C—H11C	120.3
C10A—C11A—H11A	120.5	C10C—C11C—H11C	120.3
C11A—C12A—C13A	121.1 (2)	C11C—C12C—C13C	121.0 (2)
C11A—C12A—H12A	119.5	C11C—C12C—H12C	119.5
C13A—C12A—H12A	119.5	C13C—C12C—H12C	119.5
O4A—C13A—C12A	120.7 (2)	O4C—C13C—C12C	120.4 (2)
O4A—C13A—C8A	118.6 (2)	O4C—C13C—C8C	119.5 (2)
C12A—C13A—C8A	120.7 (2)	C12C—C13C—C8C	120.1 (2)
C13B—O4B—H4B	112.4 (19)	C13D—O4D—H4D	111.1 (17)
O1B—N1B—O2B	123.3 (3)	O2D—N1D—O1D	122.8 (2)
O1B—N1B—C4B	118.3 (2)	O2D—N1D—C4D	118.6 (2)
O2B—N1B—C4B	118.4 (2)	O1D—N1D—C4D	118.6 (2)
C7B—N2B—C1B	129.1 (2)	C7D—N2D—C1D	129.7 (2)
C7B—N2B—H2B	111.0 (15)	C7D—N2D—H2D	114.6 (15)
C1B—N2B—H2B	119.8 (15)	C1D—N2D—H2D	115.6 (15)
C6B—C1B—N2B	124.6 (2)	C6D—C1D—N2D	124.3 (2)
C6B—C1B—C2B	117.2 (2)	C6D—C1D—C2D	117.6 (2)
N2B—C1B—C2B	118.2 (2)	N2D—C1D—C2D	118.1 (2)
C3B—C2B—C1B	121.7 (2)	C3D—C2D—C1D	121.7 (2)
C3B—C2B—Cl1B	119.44 (18)	C3D—C2D—Cl1D	118.25 (19)
C1B—C2B—Cl1B	118.9 (2)	C1D—C2D—Cl1D	120.1 (2)
C2B—C3B—C4B	118.7 (2)	C4D—C3D—C2D	119.0 (2)
C2B—C3B—H3B	120.6	C4D—C3D—H3D	120.5
C4B—C3B—H3B	120.6	C2D—C3D—H3D	120.5
C5B—C4B—C3B	121.6 (3)	C3D—C4D—C5D	121.3 (2)
C5B—C4B—N1B	118.9 (2)	C3D—C4D—N1D	118.9 (2)
C3B—C4B—N1B	119.5 (2)	C5D—C4D—N1D	119.8 (2)
C4B—C5B—C6B	119.3 (2)	C6D—C5D—C4D	119.5 (2)
C4B—C5B—H5B	120.4	C6D—C5D—H5D	120.3
C6B—C5B—H5B	120.4	C4D—C5D—H5D	120.3
C5B—C6B—C1B	121.5 (2)	C5D—C6D—C1D	121.0 (2)
C5B—C6B—H6B	119.2	C5D—C6D—H6D	119.5
C1B—C6B—H6B	119.2	C1D—C6D—H6D	119.5
O3B—C7B—N2B	121.0 (2)	O3D—C7D—N2D	121.4 (2)
O3B—C7B—C8B	121.6 (2)	O3D—C7D—C8D	121.6 (2)
N2B—C7B—C8B	117.4 (2)	N2D—C7D—C8D	116.9 (2)
C13B—C8B—C9B	116.9 (2)	C9D—C8D—C13D	117.8 (2)
C13B—C8B—C7B	126.6 (2)	C9D—C8D—C7D	116.7 (2)
C9B—C8B—C7B	116.5 (2)	C13D—C8D—C7D	125.5 (2)
C10B—C9B—C8B	121.4 (2)	C10D—C9D—C8D	121.2 (2)
C10B—C9B—H9B	119.3	C10D—C9D—H9D	119.4
C8B—C9B—H9B	119.3	C8D—C9D—H9D	119.4
C9B—C10B—C11B	121.1 (3)	C11D—C10D—C9D	120.7 (2)
C9B—C10B—Cl2B	119.3 (2)	C11D—C10D—Cl2D	118.7 (2)
C11B—C10B—Cl2B	119.6 (2)	C9D—C10D—Cl2D	120.61 (18)
C12B—C11B—C10B	118.9 (3)	C12D—C11D—C10D	118.8 (2)
C12B—C11B—H11B	120.6	C12D—C11D—H11D	120.6
C10B—C11B—H11B	120.6	C10D—C11D—H11D	120.6
C11B—C12B—C13B	120.8 (2)	C11D—C12D—C13D	121.4 (2)
C11B—C12B—H12B	119.6	C11D—C12D—H12D	119.3
C13B—C12B—H12B	119.6	C13D—C12D—H12D	119.3
O4B—C13B—C12B	121.5 (2)	O4D—C13D—C12D	120.2 (2)
O4B—C13B—C8B	117.6 (2)	O4D—C13D—C8D	119.6 (2)
C12B—C13B—C8B	120.9 (2)	C12D—C13D—C8D	120.2 (2)
C7A—N2A—C1A—C6A	−0.7 (4)	C7C—N2C—C1C—C6C	−0.9 (4)
C7A—N2A—C1A—C2A	177.7 (2)	C7C—N2C—C1C—C2C	−179.9 (2)
C6A—C1A—C2A—C3A	0.0 (4)	N2C—C1C—C2C—C3C	177.4 (2)
N2A—C1A—C2A—C3A	−178.5 (2)	C6C—C1C—C2C—C3C	−1.6 (4)
C6A—C1A—C2A—Cl1A	178.95 (18)	N2C—C1C—C2C—Cl1C	−3.2 (3)
N2A—C1A—C2A—Cl1A	0.4 (3)	C6C—C1C—C2C—Cl1C	177.81 (17)
C1A—C2A—C3A—C4A	0.3 (4)	C1C—C2C—C3C—C4C	0.8 (4)
Cl1A—C2A—C3A—C4A	−178.68 (19)	Cl1C—C2C—C3C—C4C	−178.61 (18)
C2A—C3A—C4A—C5A	0.0 (4)	C2C—C3C—C4C—C5C	0.2 (4)
C2A—C3A—C4A—N1A	−179.3 (2)	C2C—C3C—C4C—N1C	−179.0 (2)
O2A—N1A—C4A—C3A	−2.1 (4)	O2C—N1C—C4C—C3C	0.1 (4)
O1A—N1A—C4A—C3A	176.9 (2)	O1C—N1C—C4C—C3C	−179.0 (2)
O2A—N1A—C4A—C5A	178.5 (2)	O2C—N1C—C4C—C5C	−179.1 (2)
O1A—N1A—C4A—C5A	−2.5 (4)	O1C—N1C—C4C—C5C	1.8 (4)
C3A—C4A—C5A—C6A	−0.6 (4)	C3C—C4C—C5C—C6C	−0.4 (4)
N1A—C4A—C5A—C6A	178.8 (2)	N1C—C4C—C5C—C6C	178.8 (2)
C4A—C5A—C6A—C1A	0.9 (4)	C4C—C5C—C6C—C1C	−0.4 (4)
N2A—C1A—C6A—C5A	177.8 (2)	N2C—C1C—C6C—C5C	−177.6 (2)
C2A—C1A—C6A—C5A	−0.6 (4)	C2C—C1C—C6C—C5C	1.4 (4)
C1A—N2A—C7A—O3A	3.0 (4)	C1C—N2C—C7C—O3C	−4.6 (4)
C1A—N2A—C7A—C8A	−176.4 (2)	C1C—N2C—C7C—C8C	176.9 (2)
O3A—C7A—C8A—C13A	−179.1 (2)	O3C—C7C—C8C—C9C	4.5 (3)
N2A—C7A—C8A—C13A	0.2 (4)	N2C—C7C—C8C—C9C	−177.0 (2)
O3A—C7A—C8A—C9A	−1.5 (3)	O3C—C7C—C8C—C13C	−174.6 (2)
N2A—C7A—C8A—C9A	177.8 (2)	N2C—C7C—C8C—C13C	3.9 (3)
C13A—C8A—C9A—C10A	0.1 (4)	C13C—C8C—C9C—C10C	1.5 (3)
C7A—C8A—C9A—C10A	−177.8 (2)	C7C—C8C—C9C—C10C	−177.6 (2)
C8A—C9A—C10A—C11A	−1.4 (4)	C8C—C9C—C10C—C11C	1.0 (4)
C8A—C9A—C10A—Cl2A	177.87 (18)	C8C—C9C—C10C—Cl2C	−177.46 (17)
C9A—C10A—C11A—C12A	1.5 (4)	C9C—C10C—C11C—C12C	−1.9 (4)
Cl2A—C10A—C11A—C12A	−177.8 (2)	Cl2C—C10C—C11C—C12C	176.59 (19)
C10A—C11A—C12A—C13A	−0.2 (4)	C10C—C11C—C12C—C13C	0.2 (4)
C11A—C12A—C13A—O4A	−179.8 (2)	C11C—C12C—C13C—O4C	−178.0 (2)
C11A—C12A—C13A—C8A	−1.1 (4)	C11C—C12C—C13C—C8C	2.4 (4)
C9A—C8A—C13A—O4A	179.9 (2)	C9C—C8C—C13C—O4C	177.2 (2)
C7A—C8A—C13A—O4A	−2.5 (4)	C7C—C8C—C13C—O4C	−3.7 (4)
C9A—C8A—C13A—C12A	1.2 (4)	C9C—C8C—C13C—C12C	−3.2 (3)
C7A—C8A—C13A—C12A	178.8 (2)	C7C—C8C—C13C—C12C	175.9 (2)
C7B—N2B—C1B—C6B	−3.1 (4)	C7D—N2D—C1D—C6D	−2.4 (4)
C7B—N2B—C1B—C2B	177.5 (2)	C7D—N2D—C1D—C2D	179.7 (2)
C6B—C1B—C2B—C3B	−0.9 (4)	C6D—C1D—C2D—C3D	−1.8 (4)
N2B—C1B—C2B—C3B	178.6 (2)	N2D—C1D—C2D—C3D	176.2 (2)
C6B—C1B—C2B—Cl1B	178.55 (18)	C6D—C1D—C2D—Cl1D	178.08 (18)
N2B—C1B—C2B—Cl1B	−2.0 (3)	N2D—C1D—C2D—Cl1D	−3.9 (3)
C1B—C2B—C3B—C4B	0.9 (4)	C1D—C2D—C3D—C4D	0.1 (4)
Cl1B—C2B—C3B—C4B	−178.53 (18)	Cl1D—C2D—C3D—C4D	−179.82 (18)
C2B—C3B—C4B—C5B	−0.1 (4)	C2D—C3D—C4D—C5D	1.6 (4)
C2B—C3B—C4B—N1B	180.0 (2)	C2D—C3D—C4D—N1D	−177.8 (2)
O1B—N1B—C4B—C5B	1.3 (4)	O2D—N1D—C4D—C3D	−4.9 (4)
O2B—N1B—C4B—C5B	−178.6 (2)	O1D—N1D—C4D—C3D	175.1 (2)
O1B—N1B—C4B—C3B	−178.8 (2)	O2D—N1D—C4D—C5D	175.8 (2)
O2B—N1B—C4B—C3B	1.3 (3)	O1D—N1D—C4D—C5D	−4.3 (4)
C3B—C4B—C5B—C6B	−0.6 (4)	C3D—C4D—C5D—C6D	−1.4 (4)
N1B—C4B—C5B—C6B	179.3 (2)	N1D—C4D—C5D—C6D	178.0 (2)
C4B—C5B—C6B—C1B	0.6 (4)	C4D—C5D—C6D—C1D	−0.5 (4)
N2B—C1B—C6B—C5B	−179.3 (2)	N2D—C1D—C6D—C5D	−175.9 (2)
C2B—C1B—C6B—C5B	0.1 (4)	C2D—C1D—C6D—C5D	2.0 (4)
C1B—N2B—C7B—O3B	0.3 (4)	C1D—N2D—C7D—O3D	−4.5 (4)
C1B—N2B—C7B—C8B	−179.8 (2)	C1D—N2D—C7D—C8D	178.3 (2)
O3B—C7B—C8B—C13B	−179.2 (2)	O3D—C7D—C8D—C9D	0.6 (3)
N2B—C7B—C8B—C13B	0.9 (4)	N2D—C7D—C8D—C9D	177.8 (2)
O3B—C7B—C8B—C9B	−0.3 (3)	O3D—C7D—C8D—C13D	−178.3 (2)
N2B—C7B—C8B—C9B	179.8 (2)	N2D—C7D—C8D—C13D	−1.1 (4)
C13B—C8B—C9B—C10B	0.3 (4)	C13D—C8D—C9D—C10D	1.5 (4)
C7B—C8B—C9B—C10B	−178.7 (2)	C7D—C8D—C9D—C10D	−177.5 (2)
C8B—C9B—C10B—C11B	−0.5 (4)	C8D—C9D—C10D—C11D	−0.8 (4)
C8B—C9B—C10B—Cl2B	177.99 (19)	C8D—C9D—C10D—Cl2D	179.25 (18)
C9B—C10B—C11B—C12B	0.6 (4)	C9D—C10D—C11D—C12D	−0.5 (4)
Cl2B—C10B—C11B—C12B	−177.9 (2)	Cl2D—C10D—C11D—C12D	179.43 (19)
C10B—C11B—C12B—C13B	−0.5 (4)	C10D—C11D—C12D—C13D	1.1 (4)
C11B—C12B—C13B—O4B	−178.9 (2)	C11D—C12D—C13D—O4D	179.0 (2)
C11B—C12B—C13B—C8B	0.3 (4)	C11D—C12D—C13D—C8D	−0.4 (4)
C9B—C8B—C13B—O4B	179.0 (2)	C9D—C8D—C13D—O4D	179.7 (2)
C7B—C8B—C13B—O4B	−2.1 (4)	C7D—C8D—C13D—O4D	−1.4 (4)
C9B—C8B—C13B—C12B	−0.2 (4)	C9D—C8D—C13D—C12D	−0.9 (4)
C7B—C8B—C13B—C12B	178.7 (2)	C7D—C8D—C13D—C12D	178.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2A···O4A	0.88 (1)	1.84 (2)	2.610 (3)	146 (3)
N2B—H2B···O4B	0.88 (1)	1.84 (2)	2.613 (3)	147 (2)
N2C—H2C···O4C	0.87 (1)	1.94 (2)	2.655 (3)	139 (2)
N2D—H2D···O4D	0.87 (1)	1.87 (2)	2.618 (3)	143 (2)
O4A—H4A···O3C	0.85 (1)	1.77 (1)	2.609 (2)	168 (3)
O4B—H4B···O3D	0.85 (1)	1.83 (1)	2.646 (2)	161 (3)
O4C—H4C···O3A^i	0.84 (1)	1.84 (1)	2.682 (2)	178 (3)
O4D—H4D···O3B^i	0.85 (1)	1.81 (1)	2.659 (2)	176 (2)

Symmetry code: (i) x, y+1, z.

(niclosamide_acetone) 5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide–acetone (1/1)

Crystal data

C13H8Cl2N2O4·C3H6O	Z = 4
Mr = 385.19	F(000) = 792
Triclinic, P1	Dx = 1.554 Mg m^−3
a = 7.3426 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.165 (3) Å	Cell parameters from 549 reflections
c = 17.457 (4) Å	θ = 3.2–21.1°
α = 97.432 (5)°	µ = 0.43 mm^−1
β = 99.390 (7)°	T = 120 K
γ = 93.071 (6)°	Plate, colourless
V = 1646.1 (6) Å^3	0.15 × 0.05 × 0.02 mm

Data collection

Bruker Nonius X8 APEXII CCD area-detector diffractometer	3509 independent reflections
Radiation source: fine-focus sealed tube	1825 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.078
ω and ϕ scans	θmax = 22.0°, θmin = 3.6°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −6→7
Tmin = 0.543, Tmax = 0.992	k = −13→13
7324 measured reflections	l = −17→18

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.095	w = 1/[σ^2(Fo^2) + (0.0225P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.92	(Δ/σ)max < 0.001
3509 reflections	Δρmax = 0.26 e Å^−3
463 parameters	Δρmin = −0.36 e Å^−3

Special details

Experimental. Relatively small crystal and weak scatterer. Data are truncated at 0.95 Å resolution (q max ca 22°) with ca 50% observed at the 2σ(I) level to this resolution. Diffraction at room temperature was too weak to collect usable data.

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.

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

	x	y	z	Uiso*/Ueq
Cl1A	0.2548 (2)	0.38078 (11)	0.39333 (9)	0.0298 (5)
Cl2A	−0.0485 (2)	−0.21813 (12)	0.08249 (10)	0.0417 (6)
O1A	0.6673 (6)	0.2522 (3)	0.7017 (2)	0.0382 (14)
O2A	0.6363 (6)	0.4059 (3)	0.6715 (2)	0.0351 (13)
O3A	0.2478 (6)	−0.0164 (3)	0.3517 (3)	0.0371 (14)
O4A	0.0276 (6)	0.2125 (4)	0.2275 (3)	0.0317 (14)
H4A	−0.051 (8)	0.247 (4)	0.200 (3)	0.04 (2)*
N1A	0.6061 (7)	0.3118 (5)	0.6571 (3)	0.0270 (15)
N2A	0.2122 (6)	0.1547 (4)	0.3577 (3)	0.0249 (15)
H2A	0.1642	0.2018	0.3308	0.030*
C1A	0.3057 (8)	0.1900 (5)	0.4337 (4)	0.0205 (17)
C2A	0.3356 (8)	0.2969 (5)	0.4572 (4)	0.0212 (17)
C3A	0.4269 (8)	0.3368 (5)	0.5305 (4)	0.0218 (17)
H3A	0.4416	0.4090	0.5464	0.026*
C4A	0.4978 (8)	0.2702 (5)	0.5812 (4)	0.0231 (17)
C5A	0.4683 (8)	0.1649 (5)	0.5599 (4)	0.0251 (18)
H5A	0.5131	0.1200	0.5960	0.030*
C6A	0.3740 (8)	0.1255 (4)	0.4865 (4)	0.0203 (17)
H6A	0.3556	0.0532	0.4718	0.024*
C7A	0.1860 (9)	0.0555 (5)	0.3199 (4)	0.0235 (18)
C8A	0.0847 (8)	0.0388 (5)	0.2378 (4)	0.0212 (17)
C9A	0.0644 (8)	−0.0639 (5)	0.2012 (4)	0.0251 (18)
H9A	0.1128	−0.1165	0.2293	0.030*
C10A	−0.0236 (9)	−0.0877 (5)	0.1265 (4)	0.0275 (18)
C11A	−0.0994 (8)	−0.0155 (5)	0.0819 (4)	0.0298 (19)
H11A	−0.1634	−0.0344	0.0297	0.036*
C12A	−0.0769 (8)	0.0856 (5)	0.1175 (4)	0.0279 (18)
H12A	−0.1229	0.1380	0.0886	0.033*
C13A	0.0110 (9)	0.1118 (5)	0.1942 (4)	0.0253 (18)
O5A	−0.0998 (6)	0.3326 (3)	0.1233 (3)	0.0393 (14)
C14A	−0.0643 (9)	0.4265 (6)	0.1431 (4)	0.0321 (19)
C15A	−0.1171 (8)	0.5005 (5)	0.0873 (4)	0.038 (2)
H15A	−0.1920	0.4637	0.0391	0.057*
H15B	−0.0051	0.5339	0.0748	0.057*
H15C	−0.1891	0.5527	0.1111	0.057*
C16A	0.0326 (9)	0.4687 (4)	0.2221 (3)	0.036 (2)
H16A	0.0113	0.4208	0.2589	0.054*
H16B	−0.0144	0.5348	0.2386	0.054*
H16C	0.1656	0.4785	0.2216	0.054*
Cl1B	0.2364 (2)	0.92845 (11)	0.61030 (9)	0.0304 (5)
Cl2B	0.5719 (2)	0.42423 (12)	0.88875 (10)	0.0386 (6)
O1B	−0.1591 (6)	0.6874 (3)	0.2919 (3)	0.0451 (14)
O2B	−0.1418 (6)	0.8507 (3)	0.3286 (2)	0.0363 (13)
O3B	0.2638 (6)	0.5411 (3)	0.6325 (2)	0.0336 (13)
O4B	0.4806 (6)	0.8188 (3)	0.7697 (3)	0.0287 (13)
H4B	0.498 (7)	0.866 (4)	0.810 (3)	0.014 (19)*
O5B	0.5732 (5)	0.9741 (3)	0.8882 (2)	0.0299 (12)
N1B	−0.1067 (7)	0.7633 (5)	0.3403 (3)	0.0254 (15)
N2B	0.2868 (6)	0.7136 (4)	0.6364 (3)	0.0213 (14)
H2B	0.3315	0.7716	0.6661	0.026*
C1B	0.1909 (8)	0.7221 (4)	0.5621 (4)	0.0165 (17)
C2B	0.1581 (8)	0.8205 (4)	0.5420 (4)	0.0211 (17)
C3B	0.0647 (8)	0.8350 (4)	0.4700 (4)	0.0235 (17)
H3B	0.0443	0.9022	0.4579	0.028*
C4B	0.0007 (8)	0.7491 (5)	0.4153 (4)	0.0186 (17)
C5B	0.0289 (8)	0.6528 (5)	0.4328 (4)	0.0222 (17)
H5B	−0.0189	0.5950	0.3951	0.027*
C6B	0.1263 (9)	0.6379 (4)	0.5046 (4)	0.0243 (18)
H6B	0.1495	0.5703	0.5150	0.029*
C7B	0.3195 (9)	0.6258 (5)	0.6685 (4)	0.0275 (18)
C8B	0.4250 (8)	0.6378 (5)	0.7503 (4)	0.0215 (17)
C9B	0.4470 (8)	0.5451 (5)	0.7809 (4)	0.0239 (18)
H9B	0.3925	0.4828	0.7500	0.029*
C10B	0.5446 (9)	0.5422 (4)	0.8536 (4)	0.0258 (18)
C11B	0.6184 (8)	0.6319 (5)	0.9024 (4)	0.0261 (18)
H11B	0.6813	0.6298	0.9542	0.031*
C12B	0.5975 (8)	0.7235 (5)	0.8734 (4)	0.0266 (18)
H12B	0.6502	0.7855	0.9051	0.032*
C13B	0.5017 (8)	0.7272 (5)	0.7992 (4)	0.0247 (18)
C14B	0.5372 (8)	1.0625 (5)	0.8784 (4)	0.0286 (19)
C15B	0.5571 (8)	1.1444 (4)	0.9481 (4)	0.034 (2)
H15D	0.5657	1.1123	0.9961	0.051*
H15E	0.4492	1.1853	0.9433	0.051*
H15F	0.6696	1.1891	0.9505	0.051*
C16B	0.4677 (8)	1.0901 (5)	0.7996 (4)	0.039 (2)
H16D	0.4814	1.0332	0.7593	0.058*
H16E	0.5391	1.1518	0.7918	0.058*
H16F	0.3367	1.1035	0.7957	0.058*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1A	0.0360 (12)	0.0226 (10)	0.0297 (11)	−0.0015 (8)	0.0009 (9)	0.0071 (8)
Cl2A	0.0427 (13)	0.0293 (11)	0.0469 (13)	−0.0099 (9)	0.0049 (11)	−0.0090 (9)
O1A	0.055 (4)	0.030 (3)	0.027 (3)	0.001 (3)	−0.008 (3)	0.012 (2)
O2A	0.043 (3)	0.022 (3)	0.036 (3)	−0.004 (2)	0.000 (2)	−0.002 (2)
O3A	0.041 (3)	0.023 (3)	0.039 (3)	0.006 (2)	−0.014 (3)	−0.002 (2)
O4A	0.036 (4)	0.026 (3)	0.027 (3)	0.005 (3)	−0.008 (3)	0.000 (3)
N1A	0.020 (4)	0.033 (4)	0.025 (4)	−0.008 (3)	0.004 (3)	−0.005 (3)
N2A	0.030 (4)	0.017 (3)	0.026 (4)	−0.005 (3)	0.004 (3)	0.000 (3)
C1A	0.014 (4)	0.032 (5)	0.014 (4)	−0.003 (3)	−0.001 (3)	0.000 (4)
C2A	0.024 (5)	0.028 (4)	0.013 (4)	0.007 (3)	0.002 (4)	0.006 (4)
C3A	0.017 (4)	0.025 (4)	0.024 (5)	0.000 (3)	0.004 (4)	0.002 (4)
C4A	0.016 (4)	0.025 (4)	0.027 (5)	−0.004 (3)	0.007 (4)	−0.002 (4)
C5A	0.025 (5)	0.023 (4)	0.029 (5)	−0.004 (3)	0.014 (4)	0.000 (4)
C6A	0.025 (4)	0.012 (4)	0.022 (4)	−0.004 (3)	−0.001 (4)	0.001 (4)
C7A	0.022 (5)	0.024 (5)	0.026 (5)	−0.007 (4)	0.006 (4)	0.008 (4)
C8A	0.024 (5)	0.015 (4)	0.025 (5)	−0.001 (3)	0.006 (4)	0.005 (4)
C9A	0.018 (5)	0.030 (5)	0.026 (5)	−0.003 (3)	0.007 (4)	−0.001 (4)
C10A	0.023 (5)	0.025 (4)	0.031 (5)	−0.012 (4)	0.012 (4)	−0.011 (4)
C11A	0.023 (5)	0.047 (5)	0.016 (4)	−0.002 (4)	−0.009 (4)	0.011 (4)
C12A	0.024 (5)	0.028 (5)	0.032 (5)	−0.002 (4)	0.008 (4)	0.003 (4)
C13A	0.027 (5)	0.018 (5)	0.024 (5)	−0.011 (4)	0.000 (4)	−0.008 (4)
O5A	0.043 (3)	0.034 (3)	0.038 (3)	0.003 (3)	0.000 (3)	0.004 (3)
C14A	0.021 (5)	0.038 (5)	0.038 (5)	0.001 (4)	0.009 (4)	0.002 (5)
C15A	0.034 (5)	0.042 (5)	0.036 (5)	−0.007 (4)	−0.002 (4)	0.017 (4)
C16A	0.042 (5)	0.030 (4)	0.029 (5)	−0.008 (4)	−0.006 (4)	−0.003 (4)
Cl1B	0.0410 (12)	0.0194 (10)	0.0285 (12)	−0.0063 (8)	0.0044 (9)	0.0002 (8)
Cl2B	0.0454 (13)	0.0278 (11)	0.0399 (13)	−0.0002 (9)	−0.0037 (10)	0.0101 (9)
O1B	0.062 (4)	0.030 (3)	0.033 (3)	−0.013 (3)	−0.012 (3)	−0.002 (3)
O2B	0.049 (3)	0.026 (3)	0.032 (3)	0.006 (3)	−0.001 (3)	0.006 (3)
O3B	0.042 (3)	0.019 (3)	0.030 (3)	−0.013 (2)	−0.013 (3)	0.000 (2)
O4B	0.044 (3)	0.013 (3)	0.024 (3)	−0.005 (2)	0.001 (3)	−0.008 (3)
O5B	0.036 (3)	0.024 (3)	0.029 (3)	−0.011 (2)	0.004 (2)	0.007 (2)
N1B	0.021 (4)	0.029 (4)	0.027 (4)	0.001 (3)	0.006 (3)	0.003 (4)
N2B	0.020 (4)	0.016 (3)	0.024 (4)	−0.002 (3)	−0.004 (3)	0.003 (3)
C1B	0.016 (4)	0.008 (4)	0.023 (5)	−0.005 (3)	−0.004 (4)	0.008 (4)
C2B	0.014 (4)	0.021 (4)	0.024 (5)	−0.009 (3)	0.002 (4)	−0.007 (3)
C3B	0.030 (5)	0.015 (4)	0.026 (5)	−0.003 (3)	0.006 (4)	0.002 (4)
C4B	0.008 (4)	0.027 (5)	0.024 (5)	0.006 (3)	0.006 (4)	0.010 (4)
C5B	0.025 (5)	0.021 (4)	0.019 (5)	−0.006 (3)	0.006 (4)	−0.002 (3)
C6B	0.032 (5)	0.017 (4)	0.025 (5)	0.000 (3)	0.009 (4)	0.005 (4)
C7B	0.029 (5)	0.028 (5)	0.027 (5)	0.003 (4)	0.003 (4)	0.009 (4)
C8B	0.018 (4)	0.021 (4)	0.025 (5)	−0.003 (3)	0.002 (4)	0.007 (4)
C9B	0.011 (4)	0.028 (4)	0.030 (5)	−0.007 (3)	0.002 (4)	0.001 (4)
C10B	0.024 (5)	0.025 (4)	0.027 (5)	0.001 (3)	0.000 (4)	0.007 (4)
C11B	0.026 (5)	0.027 (4)	0.021 (4)	−0.005 (4)	−0.003 (4)	0.000 (4)
C12B	0.030 (5)	0.026 (5)	0.019 (5)	−0.012 (3)	−0.004 (4)	0.000 (4)
C13B	0.021 (5)	0.016 (4)	0.035 (5)	−0.012 (3)	0.004 (4)	0.003 (4)
C14B	0.015 (4)	0.029 (5)	0.043 (6)	−0.012 (4)	0.009 (4)	0.012 (4)
C15B	0.034 (5)	0.029 (4)	0.035 (5)	−0.004 (4)	−0.002 (4)	0.001 (4)
C16B	0.028 (5)	0.049 (5)	0.038 (5)	0.003 (4)	−0.004 (4)	0.013 (4)

Geometric parameters (Å, º)

Cl1A—C2A	1.729 (6)	Cl1B—C2B	1.738 (6)
Cl2A—C10A	1.775 (6)	Cl2B—C10B	1.752 (6)
O1A—N1A	1.227 (5)	O1B—N1B	1.224 (6)
O2A—N1A	1.233 (5)	O2B—N1B	1.228 (5)
O3A—C7A	1.228 (6)	O3B—C7B	1.221 (7)
O4A—C13A	1.368 (7)	O4B—C13B	1.378 (7)
O4A—H4A	0.87 (5)	O4B—H4B	0.87 (5)
N1A—C4A	1.453 (7)	O5B—C14B	1.234 (6)
N2A—C7A	1.374 (7)	N1B—C4B	1.453 (7)
N2A—C1A	1.399 (7)	N2B—C7B	1.364 (7)
N2A—H2A	0.88	N2B—C1B	1.392 (6)
C1A—C6A	1.385 (7)	N2B—H2B	0.88
C1A—C2A	1.410 (7)	C1B—C6B	1.400 (7)
C2A—C3A	1.367 (7)	C1B—C2B	1.408 (7)
C3A—C4A	1.386 (7)	C2B—C3B	1.372 (7)
C3A—H3A	0.95	C3B—C4B	1.389 (7)
C4A—C5A	1.384 (7)	C3B—H3B	0.95
C5A—C6A	1.375 (7)	C4B—C5B	1.361 (7)
C5A—H5A	0.95	C5B—C6B	1.381 (7)
C6A—H6A	0.95	C5B—H5B	0.95
C7A—C8A	1.486 (8)	C6B—H6B	0.95
C8A—C13A	1.380 (7)	C7B—C8B	1.494 (8)
C8A—C9A	1.407 (7)	C8B—C13B	1.394 (8)
C9A—C10A	1.348 (8)	C8B—C9B	1.400 (7)
C9A—H9A	0.95	C9B—C10B	1.358 (7)
C10A—C11A	1.388 (8)	C9B—H9B	0.95
C11A—C12A	1.383 (8)	C10B—C11B	1.391 (8)
C11A—H11A	0.95	C11B—C12B	1.374 (7)
C12A—C13A	1.379 (8)	C11B—H11B	0.9500
C12A—H12A	0.95	C12B—C13B	1.376 (7)
O5A—C14A	1.242 (7)	C12B—H12B	0.95
C14A—C16A	1.467 (8)	C14B—C16B	1.484 (8)
C14A—C15A	1.488 (7)	C14B—C15B	1.501 (8)
C15A—H15A	0.98	C15B—H15D	0.98
C15A—H15B	0.98	C15B—H15E	0.98
C15A—H15C	0.98	C15B—H15F	0.98
C16A—H16A	0.98	C16B—H16D	0.98
C16A—H16B	0.98	C16B—H16E	0.98
C16A—H16C	0.98	C16B—H16F	0.98
C13A—O4A—H4A	110 (4)	C13B—O4B—H4B	106 (3)
O1A—N1A—O2A	123.8 (5)	O1B—N1B—O2B	122.9 (5)
O1A—N1A—C4A	119.0 (5)	O1B—N1B—C4B	118.4 (5)
O2A—N1A—C4A	117.2 (6)	O2B—N1B—C4B	118.7 (5)
C7A—N2A—C1A	128.0 (6)	C7B—N2B—C1B	127.5 (5)
C7A—N2A—H2A	116.0	C7B—N2B—H2B	116.2
C1A—N2A—H2A	116.0	C1B—N2B—H2B	116.2
C6A—C1A—N2A	123.5 (6)	N2B—C1B—C6B	123.9 (5)
C6A—C1A—C2A	118.2 (6)	N2B—C1B—C2B	119.0 (5)
N2A—C1A—C2A	118.2 (5)	C6B—C1B—C2B	117.1 (5)
C3A—C2A—C1A	121.4 (5)	C3B—C2B—C1B	122.4 (5)
C3A—C2A—Cl1A	118.5 (5)	C3B—C2B—Cl1B	118.0 (5)
C1A—C2A—Cl1A	120.1 (5)	C1B—C2B—Cl1B	119.6 (5)
C2A—C3A—C4A	118.9 (6)	C2B—C3B—C4B	118.4 (6)
C2A—C3A—H3A	120.5	C2B—C3B—H3B	120.8
C4A—C3A—H3A	120.5	C4B—C3B—H3B	120.8
C5A—C4A—C3A	120.8 (6)	C5B—C4B—C3B	120.8 (6)
C5A—C4A—N1A	119.7 (6)	C5B—C4B—N1B	120.2 (6)
C3A—C4A—N1A	119.4 (6)	C3B—C4B—N1B	118.9 (6)
C6A—C5A—C4A	119.8 (6)	C4B—C5B—C6B	120.9 (6)
C6A—C5A—H5A	120.1	C4B—C5B—H5B	119.5
C4A—C5A—H5A	120.1	C6B—C5B—H5B	119.5
C5A—C6A—C1A	120.8 (5)	C5B—C6B—C1B	120.3 (6)
C5A—C6A—H6A	119.6	C5B—C6B—H6B	119.9
C1A—C6A—H6A	119.6	C1B—C6B—H6B	119.9
O3A—C7A—N2A	121.5 (6)	O3B—C7B—N2B	121.7 (6)
O3A—C7A—C8A	121.2 (6)	O3B—C7B—C8B	121.3 (6)
N2A—C7A—C8A	117.3 (6)	N2B—C7B—C8B	117.0 (6)
C13A—C8A—C9A	117.4 (6)	C13B—C8B—C9B	116.8 (6)
C13A—C8A—C7A	127.6 (6)	C13B—C8B—C7B	129.1 (6)
C9A—C8A—C7A	115.0 (6)	C9B—C8B—C7B	114.0 (6)
C10A—C9A—C8A	120.0 (6)	C10B—C9B—C8B	121.5 (6)
C10A—C9A—H9A	120.0	C10B—C9B—H9B	119.2
C8A—C9A—H9A	120.0	C8B—C9B—H9B	119.2
C9A—C10A—C11A	123.4 (6)	C9B—C10B—C11B	121.2 (6)
C9A—C10A—Cl2A	118.9 (5)	C9B—C10B—Cl2B	120.0 (5)
C11A—C10A—Cl2A	117.8 (5)	C11B—C10B—Cl2B	118.8 (5)
C12A—C11A—C10A	116.5 (6)	C12B—C11B—C10B	117.9 (6)
C12A—C11A—H11A	121.8	C12B—C11B—H11B	121.1
C10A—C11A—H11A	121.8	C10B—C11B—H11B	121.1
C13A—C12A—C11A	121.2 (6)	C11B—C12B—C13B	121.3 (6)
C13A—C12A—H12A	119.4	C11B—C12B—H12B	119.3
C11A—C12A—H12A	119.4	C13B—C12B—H12B	119.3
O4A—C13A—C12A	119.3 (6)	C12B—C13B—O4B	121.6 (6)
O4A—C13A—C8A	119.2 (6)	C12B—C13B—C8B	121.1 (6)
C12A—C13A—C8A	121.5 (6)	O4B—C13B—C8B	117.3 (6)
O5A—C14A—C16A	121.4 (6)	O5B—C14B—C16B	122.0 (6)
O5A—C14A—C15A	121.1 (6)	O5B—C14B—C15B	119.5 (6)
C16A—C14A—C15A	117.5 (6)	C16B—C14B—C15B	118.5 (6)
C14A—C15A—H15A	109.5	C14B—C15B—H15D	109.5
C14A—C15A—H15B	109.5	C14B—C15B—H15E	109.5
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
C14A—C15A—H15C	109.5	C14B—C15B—H15F	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5
C14A—C16A—H16A	109.5	C14B—C16B—H16D	109.5
C14A—C16A—H16B	109.5	C14B—C16B—H16E	109.5
H16A—C16A—H16B	109.5	H16D—C16B—H16E	109.5
C14A—C16A—H16C	109.5	C14B—C16B—H16F	109.5
H16A—C16A—H16C	109.5	H16D—C16B—H16F	109.5
H16B—C16A—H16C	109.5	H16E—C16B—H16F	109.5
C7A—N2A—C1A—C6A	−6.3 (10)	C7B—N2B—C1B—C6B	−6.4 (9)
C7A—N2A—C1A—C2A	172.2 (6)	C7B—N2B—C1B—C2B	174.7 (6)
C6A—C1A—C2A—C3A	−1.1 (10)	N2B—C1B—C2B—C3B	−180.0 (6)
N2A—C1A—C2A—C3A	−179.6 (5)	C6B—C1B—C2B—C3B	1.0 (9)
C6A—C1A—C2A—Cl1A	179.5 (5)	N2B—C1B—C2B—Cl1B	−0.4 (8)
N2A—C1A—C2A—Cl1A	0.9 (8)	C6B—C1B—C2B—Cl1B	−179.4 (5)
C1A—C2A—C3A—C4A	2.7 (9)	C1B—C2B—C3B—C4B	0.0 (9)
Cl1A—C2A—C3A—C4A	−177.8 (5)	Cl1B—C2B—C3B—C4B	−179.6 (5)
C2A—C3A—C4A—C5A	−3.5 (9)	C2B—C3B—C4B—C5B	0.4 (9)
C2A—C3A—C4A—N1A	175.7 (5)	C2B—C3B—C4B—N1B	176.9 (5)
O1A—N1A—C4A—C5A	−1.2 (8)	O1B—N1B—C4B—C5B	−5.0 (8)
O2A—N1A—C4A—C5A	176.4 (5)	O2B—N1B—C4B—C5B	174.6 (5)
O1A—N1A—C4A—C3A	179.6 (6)	O1B—N1B—C4B—C3B	178.5 (6)
O2A—N1A—C4A—C3A	−2.9 (8)	O2B—N1B—C4B—C3B	−2.0 (8)
C3A—C4A—C5A—C6A	2.6 (9)	C3B—C4B—C5B—C6B	−1.7 (9)
N1A—C4A—C5A—C6A	−176.6 (5)	N1B—C4B—C5B—C6B	−178.2 (5)
C4A—C5A—C6A—C1A	−0.9 (9)	C4B—C5B—C6B—C1B	2.8 (9)
N2A—C1A—C6A—C5A	178.6 (6)	N2B—C1B—C6B—C5B	178.7 (5)
C2A—C1A—C6A—C5A	0.1 (9)	C2B—C1B—C6B—C5B	−2.3 (9)
C1A—N2A—C7A—O3A	−0.3 (10)	C1B—N2B—C7B—O3B	0.0 (10)
C1A—N2A—C7A—C8A	−178.5 (5)	C1B—N2B—C7B—C8B	−179.3 (5)
O3A—C7A—C8A—C13A	−178.7 (6)	O3B—C7B—C8B—C13B	178.5 (7)
N2A—C7A—C8A—C13A	−0.5 (10)	N2B—C7B—C8B—C13B	−2.1 (10)
O3A—C7A—C8A—C9A	0.7 (9)	O3B—C7B—C8B—C9B	−1.9 (9)
N2A—C7A—C8A—C9A	179.0 (5)	N2B—C7B—C8B—C9B	177.5 (5)
C13A—C8A—C9A—C10A	0.2 (9)	C13B—C8B—C9B—C10B	−2.4 (9)
C7A—C8A—C9A—C10A	−179.3 (6)	C7B—C8B—C9B—C10B	177.9 (6)
C8A—C9A—C10A—C11A	−0.6 (10)	C8B—C9B—C10B—C11B	3.5 (10)
C8A—C9A—C10A—Cl2A	−179.4 (5)	C8B—C9B—C10B—Cl2B	−178.9 (5)
C9A—C10A—C11A—C12A	1.5 (10)	C9B—C10B—C11B—C12B	−3.1 (10)
Cl2A—C10A—C11A—C12A	−179.6 (5)	Cl2B—C10B—C11B—C12B	179.2 (5)
C10A—C11A—C12A—C13A	−2.1 (9)	C10B—C11B—C12B—C13B	2.0 (9)
C11A—C12A—C13A—O4A	−178.9 (6)	C11B—C12B—C13B—O4B	−179.9 (6)
C11A—C12A—C13A—C8A	1.9 (10)	C11B—C12B—C13B—C8B	−1.1 (10)
C9A—C8A—C13A—O4A	180.0 (5)	C9B—C8B—C13B—C12B	1.3 (9)
C7A—C8A—C13A—O4A	−0.6 (10)	C7B—C8B—C13B—C12B	−179.1 (6)
C9A—C8A—C13A—C12A	−0.9 (10)	C9B—C8B—C13B—O4B	−179.9 (5)
C7A—C8A—C13A—C12A	178.6 (6)	C7B—C8B—C13B—O4B	−0.3 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2A···O4A	0.88	1.94	2.671 (7)	139
N2B—H2B···O4B	0.88	1.96	2.690 (7)	139
O4A—H4A···O5A	0.87 (5)	1.87 (6)	2.652 (6)	149 (6)
O4B—H4B···O5B	0.87 (5)	1.83 (5)	2.685 (6)	169 (5)

(niclosamide_acetonitrile) 5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide–acetonitrile (1/1)

Crystal data

C13H8Cl2N2O4·C2H3N	Z = 2
Mr = 368.17	F(000) = 376
Triclinic, P1	Dx = 1.621 Mg m^−3
a = 3.8301 (2) Å	Cu Kα radiation, λ = 1.54178 Å
b = 11.7321 (5) Å	Cell parameters from 2967 reflections
c = 16.9034 (7) Å	θ = 3.7–47.3°
α = 87.976 (2)°	µ = 4.13 mm^−1
β = 87.124 (2)°	T = 120 K
γ = 84.077 (3)°	Needle, colourless
V = 754.20 (6) Å^3	0.10 × 0.02 × 0.02 mm

Data collection

Bruker D8 QUEST PHOTON-100 diffractometer	1690 reflections with I > 2σ(I)
Radiation source: Incoatec IµS Cu microsource	Rint = 0.152
ω and ϕ scans	θmax = 66.5°, θmin = 7.9°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −4→4
Tmin = 0.532, Tmax = 0.867	k = −13→13
5506 measured reflections	l = −15→20
2571 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.082	H-atom parameters constrained
wR(F^2) = 0.228	w = 1/[σ^2(Fo^2) + (0.1444P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
2571 reflections	Δρmax = 1.18 e Å^−3
218 parameters	Δρmin = −0.71 e Å^−3

Special details

Experimental. Crystal was a non-merohedral twin with major components related by 2-fold rotation around the a axis. Possible further components. The best result was obtained by integrating the major domain as a single component in the standard way.

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.

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

	x	y	z	Uiso*/Ueq
Cl1	0.9370 (3)	0.51883 (10)	0.36251 (8)	0.0252 (4)
Cl2	0.1868 (3)	0.89028 (11)	−0.07123 (7)	0.0248 (4)
O1	1.4085 (9)	0.8952 (3)	0.5719 (2)	0.0298 (9)
O2	1.4458 (10)	0.7119 (3)	0.5968 (2)	0.0369 (10)
O3	0.6687 (9)	0.9074 (3)	0.2094 (2)	0.0240 (8)
O4	0.5055 (9)	0.5633 (3)	0.1920 (2)	0.0277 (9)
H4	0.4500	0.4984	0.1810	0.042*
N1	1.3681 (10)	0.7955 (4)	0.5541 (3)	0.0234 (10)
N2	0.7713 (9)	0.7267 (3)	0.2650 (2)	0.0184 (9)
H2	0.7503	0.6542	0.2568	0.022*
N3	0.2786 (12)	0.3458 (4)	0.1893 (3)	0.0325 (11)
C1	0.9231 (11)	0.7494 (4)	0.3349 (3)	0.0189 (11)
C2	1.0128 (12)	0.6561 (4)	0.3871 (3)	0.0191 (11)
C3	1.1606 (12)	0.6705 (5)	0.4585 (3)	0.0222 (11)
H3	1.2229	0.6069	0.4931	0.027*
C4	1.2149 (11)	0.7811 (4)	0.4779 (3)	0.0192 (11)
C5	1.1364 (11)	0.8739 (4)	0.4287 (3)	0.0219 (11)
H5	1.1819	0.9482	0.4433	0.026*
C6	0.9886 (12)	0.8584 (4)	0.3567 (3)	0.0204 (11)
H6	0.9321	0.9226	0.3222	0.024*
C7	0.6496 (11)	0.8037 (4)	0.2068 (3)	0.0194 (11)
C8	0.4947 (11)	0.7535 (4)	0.1380 (3)	0.0175 (10)
C9	0.4175 (11)	0.8300 (4)	0.0741 (3)	0.0193 (11)
H9	0.4605	0.9080	0.0772	0.023*
C10	0.2797 (11)	0.7930 (4)	0.0070 (3)	0.0194 (11)
C11	0.2128 (11)	0.6800 (4)	0.0008 (3)	0.0208 (11)
H11	0.1180	0.6554	−0.0458	0.025*
C12	0.2857 (12)	0.6034 (4)	0.0633 (3)	0.0228 (12)
H12	0.2371	0.5260	0.0599	0.027*
C13	0.4293 (11)	0.6387 (4)	0.1311 (3)	0.0202 (11)
C14	0.2185 (13)	0.2599 (5)	0.2168 (3)	0.0248 (12)
C15	0.1485 (13)	0.1492 (5)	0.2519 (3)	0.0277 (12)
H15A	0.2752	0.0880	0.2206	0.042*
H15B	−0.1043	0.1421	0.2525	0.042*
H15C	0.2275	0.1429	0.3063	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0346 (7)	0.0122 (7)	0.0288 (7)	−0.0010 (5)	−0.0038 (5)	−0.0014 (5)
Cl2	0.0291 (6)	0.0208 (7)	0.0244 (8)	−0.0002 (5)	−0.0042 (5)	0.0006 (5)
O1	0.043 (2)	0.018 (2)	0.030 (2)	−0.0030 (16)	−0.0060 (17)	−0.0059 (16)
O2	0.059 (3)	0.022 (2)	0.030 (2)	0.0001 (19)	−0.0173 (19)	0.0045 (18)
O3	0.0343 (19)	0.0107 (19)	0.027 (2)	0.0020 (15)	−0.0075 (15)	−0.0018 (15)
O4	0.043 (2)	0.014 (2)	0.027 (2)	−0.0073 (16)	−0.0063 (16)	0.0028 (15)
N1	0.022 (2)	0.023 (3)	0.026 (2)	−0.0025 (18)	−0.0020 (17)	−0.0016 (19)
N2	0.022 (2)	0.008 (2)	0.024 (2)	0.0056 (16)	−0.0003 (17)	−0.0040 (16)
N3	0.038 (3)	0.023 (3)	0.036 (3)	−0.001 (2)	−0.001 (2)	0.001 (2)
C1	0.015 (2)	0.016 (3)	0.024 (3)	0.0024 (19)	−0.0001 (19)	0.000 (2)
C2	0.017 (2)	0.015 (3)	0.026 (3)	0.0008 (19)	0.0021 (19)	−0.005 (2)
C3	0.023 (2)	0.019 (3)	0.023 (3)	0.002 (2)	0.001 (2)	0.002 (2)
C4	0.018 (2)	0.019 (3)	0.020 (3)	0.0016 (19)	0.0003 (19)	−0.002 (2)
C5	0.018 (2)	0.014 (3)	0.034 (3)	0.0027 (19)	0.002 (2)	−0.005 (2)
C6	0.022 (2)	0.014 (3)	0.024 (3)	0.002 (2)	0.005 (2)	0.000 (2)
C7	0.017 (2)	0.016 (3)	0.024 (3)	0.0047 (19)	0.0009 (19)	0.003 (2)
C8	0.016 (2)	0.011 (3)	0.023 (3)	0.0040 (18)	0.0013 (18)	−0.001 (2)
C9	0.019 (2)	0.013 (3)	0.025 (3)	0.0012 (19)	0.0008 (19)	0.001 (2)
C10	0.016 (2)	0.017 (3)	0.024 (3)	0.0029 (19)	0.0013 (18)	0.000 (2)
C11	0.017 (2)	0.021 (3)	0.024 (3)	0.000 (2)	−0.0013 (19)	−0.005 (2)
C12	0.026 (3)	0.015 (3)	0.028 (3)	−0.003 (2)	0.001 (2)	−0.008 (2)
C13	0.018 (2)	0.016 (3)	0.026 (3)	0.0002 (19)	0.002 (2)	0.001 (2)
C14	0.026 (2)	0.020 (3)	0.027 (3)	0.006 (2)	−0.001 (2)	−0.008 (2)
C15	0.027 (3)	0.022 (3)	0.034 (3)	−0.001 (2)	−0.003 (2)	0.000 (2)

Geometric parameters (Å, º)

Cl1—C2	1.734 (5)	C5—C6	1.392 (7)
Cl2—C10	1.742 (5)	C5—H5	0.9500
O1—N1	1.246 (5)	C6—H6	0.9500
O2—N1	1.217 (5)	C7—C8	1.498 (7)
O3—C7	1.228 (6)	C8—C9	1.402 (7)
O4—C13	1.357 (6)	C8—C13	1.405 (6)
O4—H4	0.8400	C9—C10	1.378 (7)
N1—C4	1.465 (6)	C9—H9	0.9500
N2—C7	1.376 (6)	C10—C11	1.384 (7)
N2—C1	1.389 (6)	C11—C12	1.383 (7)
N2—H2	0.8800	C11—H11	0.9500
N3—C14	1.135 (7)	C12—C13	1.390 (7)
C1—C6	1.393 (7)	C12—H12	0.9500
C1—C2	1.407 (7)	C14—C15	1.454 (7)
C2—C3	1.381 (7)	C15—H15A	0.9800
C3—C4	1.388 (7)	C15—H15B	0.9800
C3—H3	0.9500	C15—H15C	0.9800
C4—C5	1.364 (7)
C13—O4—H4	109.5	N2—C7—C8	115.9 (4)
O2—N1—O1	123.4 (4)	C9—C8—C13	118.1 (4)
O2—N1—C4	119.8 (4)	C9—C8—C7	115.4 (4)
O1—N1—C4	116.8 (4)	C13—C8—C7	126.4 (5)
C7—N2—C1	128.1 (4)	C10—C9—C8	120.6 (5)
C7—N2—H2	116.0	C10—C9—H9	119.7
C1—N2—H2	116.0	C8—C9—H9	119.7
N2—C1—C6	124.2 (5)	C9—C10—C11	121.1 (5)
N2—C1—C2	117.5 (5)	C9—C10—Cl2	119.3 (4)
C6—C1—C2	118.3 (5)	C11—C10—Cl2	119.6 (4)
C3—C2—C1	121.6 (5)	C12—C11—C10	119.2 (5)
C3—C2—Cl1	118.4 (4)	C12—C11—H11	120.4
C1—C2—Cl1	120.0 (4)	C10—C11—H11	120.4
C2—C3—C4	117.7 (5)	C11—C12—C13	120.6 (5)
C2—C3—H3	121.1	C11—C12—H12	119.7
C4—C3—H3	121.1	C13—C12—H12	119.7
C5—C4—C3	122.6 (5)	O4—C13—C12	120.6 (5)
C5—C4—N1	120.1 (5)	O4—C13—C8	118.9 (4)
C3—C4—N1	117.2 (5)	C12—C13—C8	120.4 (5)
C4—C5—C6	119.2 (5)	N3—C14—C15	178.9 (6)
C4—C5—H5	120.4	C14—C15—H15A	109.5
C6—C5—H5	120.4	C14—C15—H15B	109.5
C5—C6—C1	120.5 (5)	H15A—C15—H15B	109.5
C5—C6—H6	119.7	C14—C15—H15C	109.5
C1—C6—H6	119.7	H15A—C15—H15C	109.5
O3—C7—N2	123.1 (4)	H15B—C15—H15C	109.5
O3—C7—C8	121.0 (4)

(niclosamide_HA) 5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide monohydrate

Crystal data

C13H8Cl2N2O4·H2O	F(000) = 704
Mr = 345.13	Dx = 1.617 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.5418 Å
a = 3.81342 (19) Å	µ = 4.38 mm^−1
b = 16.1428 (7) Å	T = 298 K
c = 23.0650 (11) Å	Particle morphology: powder
β = 92.874 (2)°	white
V = 1418.08 (11) Å^3	cylinder, 3.0 × 0.1 mm
Z = 4	Specimen preparation: Prepared at 298 K

Data collection

PANalytical X'Pert Pro diffractometer	Data collection mode: transmission
None monochromator	Scan method: continuous
Specimen mounting: borosilicate capillary	2θmin = 5.001°, 2θmax = 37.475°, 2θstep = 0.026°

Refinement

Least-squares matrix: full with fixed elements per cycle	148 parameters
Rp = 0.023	80 restraints
Rwp = 0.032	0 constraints
Rexp = 0.023	H-atom parameters not refined
R(F) = 0.014	Weighting scheme based on measured s.u.'s
χ^2 = 2.016	(Δ/σ)max = 0.001
1249 data points	Background function: Chebyshev function with 20 terms
Excluded region(s): none	Preferred orientation correction: March (1932) Direction: [1 0 0] (corresponds to needle axis) Scale factor: 0.942 (3)

Special details

Geometry. All bond distances and angles are restrained to values taken from a DFT-D minimized structure in CASTEP, using the PBE functional and a dispersion correction according to Grimme (2006). The H atom positions are obtained using a final CASTEP optimization, where the non-H atoms were fixed to the positions obtained from the Rietveld refinement.

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

	x	y	z	Uiso*/Ueq
CL1	−0.0615 (10)	0.7759 (2)	0.29885 (15)	0.048 (3)
CL2	0.7616 (11)	0.3943 (2)	0.06746 (15)	0.048 (3)
O1	−0.343 (3)	0.5946 (4)	0.5304 (2)	0.048 (3)
O2	−0.482 (2)	0.7234 (3)	0.5052 (3)	0.048 (3)
O3	0.283 (2)	0.4644 (3)	0.2704 (3)	0.048 (3)
O4	0.3496 (16)	0.6957 (3)	0.18573 (18)	0.048 (3)
N1	−0.3828 (17)	0.6516 (2)	0.49257 (15)	0.048 (3)
N2	0.1497 (15)	0.6027 (2)	0.27318 (14)	0.048 (3)
C1	0.0208 (12)	0.6116 (2)	0.32708 (13)	0.048 (3)
C2	−0.0914 (15)	0.6917 (2)	0.34455 (16)	0.048 (3)
C3	−0.2278 (15)	0.7038 (2)	0.39850 (15)	0.048 (3)
C4	−0.2520 (16)	0.6370 (2)	0.43623 (15)	0.048 (3)
C5	−0.1460 (15)	0.5574 (2)	0.42043 (15)	0.048 (3)
C6	−0.0103 (13)	0.5456 (2)	0.36647 (15)	0.048 (3)
C7	0.2824 (15)	0.5339 (2)	0.24699 (16)	0.048 (3)
C8	0.4149 (15)	0.5484 (2)	0.18837 (15)	0.048 (3)
C9	0.5197 (14)	0.4775 (2)	0.15847 (15)	0.048 (3)
C10	0.6454 (15)	0.4832 (2)	0.10376 (16)	0.048 (3)
C11	0.6670 (14)	0.5597 (2)	0.07633 (15)	0.048 (3)
C12	0.5632 (14)	0.6295 (2)	0.10464 (15)	0.048 (3)
C13	0.4392 (14)	0.6260 (2)	0.15971 (15)	0.048 (3)
H2	0.17088	0.65695	0.24914	0.058
H3	−0.31272	0.76515	0.41136	0.058
H4	0.41554	0.75044	0.16678	0.058
H5	−0.17290	0.50556	0.44992	0.058
H6	0.06269	0.48397	0.35309	0.058
H9	0.49949	0.41774	0.17991	0.058
H11	0.76197	0.56404	0.03266	0.058
H12	0.57692	0.68960	0.08338	0.058
O1W	0.4905 (11)	0.8479 (5)	0.14960 (17)	0.048 (3)
H1W	0.56546	0.86438	0.11104	0.058
H2W	0.58308	0.88856	0.17851	0.058

Geometric parameters (Å, º)

CL1—C2	1.728 (5)	C4—C5	1.401 (5)
CL2—C10	1.730 (5)	C5—C6	1.385 (6)
O1—N1	1.272 (7)	C5—H5	1.09
O2—N1	1.258 (7)	C6—H6	1.08
O3—C7	1.245 (6)	C7—C8	1.486 (6)
O4—C13	1.328 (6)	C8—C9	1.404 (5)
O4—H4	1.02	C8—C13	1.421 (5)
N1—C4	1.435 (6)	C9—C10	1.375 (6)
N2—C1	1.367 (5)	C9—H9	1.09
N2—C7	1.373 (5)	C10—C11	1.391 (5)
N2—H2	1.04	C11—C12	1.371 (5)
C1—C2	1.425 (5)	C11—H11	1.09
C1—C6	1.410 (5)	C12—C13	1.379 (5)
C2—C3	1.387 (6)	C12—H12	1.09
C3—C4	1.392 (5)	O1W—H1W	0.98
C3—H3	1.09	O1W—H2W	0.99
C13—O4—H4	117.7	C1—C6—H6	118.7
O2—N1—O1	122.4 (5)	N2—C7—O3	122.1 (5)
O2—N1—C4	118.9 (4)	N2—C7—C8	115.0 (3)
O1—N1—C4	117.8 (5)	O3—C7—C8	122.9 (4)
C1—N2—C7	130.0 (3)	C7—C8—C9	115.9 (3)
C1—N2—H2	115.9	C7—C8—C13	126.5 (3)
C7—N2—H2	113.9	C9—C8—C13	117.6 (3)
N2—C1—C2	118.6 (3)	C8—C9—C10	121.1 (3)
N2—C1—C6	123.5 (3)	C8—C9—H9	118.1
C2—C1—C6	117.8 (3)	C10—C9—H9	120.8
C1—C2—CL1	120.7 (3)	C9—C10—CL2	119.8 (3)
C1—C2—C3	120.9 (3)	C9—C10—C11	120.6 (4)
CL1—C2—C3	118.3 (3)	CL2—C10—C11	119.5 (3)
C2—C3—C4	119.4 (3)	C10—C11—C12	119.2 (4)
C2—C3—H3	120.2	C10—C11—H11	120.5
C4—C3—H3	120.3	C12—C11—H11	120.3
C3—C4—N1	118.4 (3)	C11—C12—C13	121.7 (3)
C3—C4—C5	121.3 (4)	C11—C12—H12	119.7
N1—C4—C5	120.3 (3)	C13—C12—H12	118.5
C4—C5—C6	119.0 (3)	C12—C13—C8	119.9 (3)
C4—C5—H5	120.4	C12—C13—O4	119.3 (3)
C6—C5—H5	120.5	C8—C13—O4	120.8 (4)
C5—C6—C1	121.5 (3)	H1W—O1W—H2W	108.7
C5—C6—H6	119.7