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Three new crystalline phases are reported for the drug niclosamide [5-chloro-
N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide], C
13H
8Cl
2N
2O
4. 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, C
13H
8Cl
2N
2O
4·C
3H
6O, 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, C
13H
8Cl
2N
2O
4·CH
3CN, 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, C
13H
8Cl
2N
2O
4·H
2O, 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. C
70, 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.
Supporting information
CCDC references: 1055611; 1055612; 1055613; 1055614
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.
(niclosamide_FormII) 5-chloro-
N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide
top
Crystal data top
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) Å3 | Block, yellow |
Z = 16 | 0.50 × 0.30 × 0.10 mm |
Data collection top
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 top
Refinement on F2 | 8 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.031 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.076 | w = 1/[σ2(Fo2) + (0.0444P)2] where P = (Fo2 + 2Fc2)/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 |
Crystal data top
C13H8Cl2N2O4 | V = 5277.7 (3) Å3 |
Mr = 327.11 | Z = 16 |
Monoclinic, P2/n | Mo Kα radiation |
a = 15.3040 (5) Å | µ = 0.51 mm−1 |
b = 12.9458 (4) Å | T = 298 K |
c = 26.6596 (9) Å | 0.50 × 0.30 × 0.10 mm |
β = 92.282 (2)° | |
Data collection top
Bruker Nonius X8 APEXII CCD area-detector diffractometer | 6416 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | 4482 reflections with I > 2σ(I) |
Tmin = 0.839, Tmax = 0.951 | Rint = 0.036 |
27935 measured reflections | θmax = 22.0° |
Refinement top
R[F2 > 2σ(F2)] = 0.031 | 8 restraints |
wR(F2) = 0.076 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.92 | Δρmax = 0.42 e Å−3 |
6416 reflections | Δρmin = −0.44 e Å−3 |
789 parameters | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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···O3Ai | 0.84 (1) | 1.84 (1) | 2.682 (2) | 178 (3) |
O4D—H4D···O3Bi | 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)
top
Crystal data top
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) Å3 | 0.15 × 0.05 × 0.02 mm |
Data collection top
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 top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.053 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.095 | w = 1/[σ2(Fo2) + (0.0225P)2] where P = (Fo2 + 2Fc2)/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 |
Crystal data top
C13H8Cl2N2O4·C3H6O | γ = 93.071 (6)° |
Mr = 385.19 | V = 1646.1 (6) Å3 |
Triclinic, P1 | Z = 4 |
a = 7.3426 (12) Å | Mo Kα radiation |
b = 13.165 (3) Å | µ = 0.43 mm−1 |
c = 17.457 (4) Å | T = 120 K |
α = 97.432 (5)° | 0.15 × 0.05 × 0.02 mm |
β = 99.390 (7)° | |
Data collection top
Bruker Nonius X8 APEXII CCD area-detector diffractometer | 3509 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | 1825 reflections with I > 2σ(I) |
Tmin = 0.543, Tmax = 0.992 | Rint = 0.078 |
7324 measured reflections | θmax = 22.0° |
Refinement top
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.095 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.92 | Δρmax = 0.26 e Å−3 |
3509 reflections | Δρmin = −0.36 e Å−3 |
463 parameters | |
Special details top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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)
top
Crystal data top
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) Å3 | 0.10 × 0.02 × 0.02 mm |
Data collection top
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 top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.082 | H-atom parameters constrained |
wR(F2) = 0.228 | w = 1/[σ2(Fo2) + (0.1444P)2] where P = (Fo2 + 2Fc2)/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 |
Crystal data top
C13H8Cl2N2O4·C2H3N | γ = 84.077 (3)° |
Mr = 368.17 | V = 754.20 (6) Å3 |
Triclinic, P1 | Z = 2 |
a = 3.8301 (2) Å | Cu Kα radiation |
b = 11.7321 (5) Å | µ = 4.13 mm−1 |
c = 16.9034 (7) Å | T = 120 K |
α = 87.976 (2)° | 0.10 × 0.02 × 0.02 mm |
β = 87.124 (2)° | |
Data collection top
Bruker D8 QUEST PHOTON-100 diffractometer | 2571 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | 1690 reflections with I > 2σ(I) |
Tmin = 0.532, Tmax = 0.867 | Rint = 0.152 |
5506 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.082 | 0 restraints |
wR(F2) = 0.228 | H-atom parameters constrained |
S = 1.00 | Δρmax = 1.18 e Å−3 |
2571 reflections | Δρmin = −0.71 e Å−3 |
218 parameters | |
Special details top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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
top
Crystal data top
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) Å3 | cylinder, 3.0 × 0.1 mm |
Z = 4 | Specimen preparation: Prepared at 298 K |
Data collection top
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 top
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 |
χ2 = 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) |
Crystal data top
C13H8Cl2N2O4·H2O | V = 1418.08 (11) Å3 |
Mr = 345.13 | Z = 4 |
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 | cylinder, 3.0 × 0.1 mm |
β = 92.874 (2)° | |
Data collection top
PANalytical X'Pert Pro diffractometer | Scan method: continuous |
Specimen mounting: borosilicate capillary | 2θmin = 5.001°, 2θmax = 37.475°, 2θstep = 0.026° |
Data collection mode: transmission | |
Refinement top
Rp = 0.023 | 1249 data points |
Rwp = 0.032 | 148 parameters |
Rexp = 0.023 | 80 restraints |
R(F) = 0.014 | H-atom parameters not refined |
χ2 = 2.016 | |
Special details top
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 (Å2) top | 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) top
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 | | |
Experimental details
| (niclosamide_FormII) | (niclosamide_acetone) | (niclosamide_acetonitrile) | (niclosamide_HA) |
Crystal data |
Chemical formula | C13H8Cl2N2O4 | C13H8Cl2N2O4·C3H6O | C13H8Cl2N2O4·C2H3N | C13H8Cl2N2O4·H2O |
Mr | 327.11 | 385.19 | 368.17 | 345.13 |
Crystal system, space group | Monoclinic, P2/n | Triclinic, P1 | Triclinic, P1 | Monoclinic, P21/c |
Temperature (K) | 298 | 120 | 120 | 298 |
a, b, c (Å) | 15.3040 (5), 12.9458 (4), 26.6596 (9) | 7.3426 (12), 13.165 (3), 17.457 (4) | 3.8301 (2), 11.7321 (5), 16.9034 (7) | 3.81342 (19), 16.1428 (7), 23.0650 (11) |
α, β, γ (°) | 90, 92.282 (2), 90 | 97.432 (5), 99.390 (7), 93.071 (6) | 87.976 (2), 87.124 (2), 84.077 (3) | 90, 92.874 (2), 90 |
V (Å3) | 5277.7 (3) | 1646.1 (6) | 754.20 (6) | 1418.08 (11) |
Z | 16 | 4 | 2 | 4 |
Radiation type | Mo Kα | Mo Kα | Cu Kα | Cu Kα, λ = 1.5418 Å |
µ (mm−1) | 0.51 | 0.43 | 4.13 | 4.38 |
Specimen shape, size (mm) | 0.50 × 0.30 × 0.10 | 0.15 × 0.05 × 0.02 | 0.10 × 0.02 × 0.02 | Cylinder, 3.0 × 0.1 |
|
Data collection |
Diffractometer | Bruker Nonius X8 APEXII CCD area-detector diffractometer | Bruker Nonius X8 APEXII CCD area-detector diffractometer | Bruker D8 QUEST PHOTON-100 diffractometer | PANalytical X'Pert Pro diffractometer |
Specimen mounting | – | – | – | Borosilicate capillary |
Data collection mode | – | – | – | Transmission |
Data collection method | ω and ϕ scans | ω and ϕ scans | ω and ϕ scans | Continuous |
Absorption correction | Multi-scan (SADABS; Bruker, 2012) | Multi-scan (SADABS; Bruker, 2012) | Multi-scan (SADABS; Bruker, 2012) | – |
Tmin, Tmax | 0.839, 0.951 | 0.543, 0.992 | 0.532, 0.867 | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 27935, 6416, 4482 | 7324, 3509, 1825 | 5506, 2571, 1690 | – |
Rint | 0.036 | 0.078 | 0.152 | – |
θ values (°) | θmax = 22.0, θmin = 3.5 | θmax = 22.0, θmin = 3.6 | θmax = 66.5, θmin = 7.9 | 2θmin = 5.001 2θmax = 37.475 2θstep = 0.026 |
(sin θ/λ)max (Å−1) | 0.526 | 0.526 | 0.595 | – |
|
Refinement |
R factors and goodness of fit | R[F2 > 2σ(F2)] = 0.031, wR(F2) = 0.076, S = 0.92 | R[F2 > 2σ(F2)] = 0.053, wR(F2) = 0.095, S = 0.92 | R[F2 > 2σ(F2)] = 0.082, wR(F2) = 0.228, S = 1.00 | Rp = 0.023, Rwp = 0.032, Rexp = 0.023, R(F) = 0.014, χ2 = 2.016 |
No. of reflections/data points | 6416 | 3509 | 2571 | 1249 |
No. of parameters | 789 | 463 | 218 | 148 |
No. of restraints | 8 | 0 | 0 | 80 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H-atom parameters constrained | H-atom parameters not refined |
Δρmax, Δρmin (e Å−3) | 0.42, −0.44 | 0.26, −0.36 | 1.18, −0.71 | – |
Hydrogen-bond geometry (Å, º) for (niclosamide_FormII) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H2A···O4A | 0.878 (10) | 1.838 (18) | 2.610 (3) | 146 (3) |
N2B—H2B···O4B | 0.878 (10) | 1.835 (15) | 2.613 (3) | 147 (2) |
N2C—H2C···O4C | 0.869 (10) | 1.938 (16) | 2.655 (3) | 138.9 (19) |
N2D—H2D···O4D | 0.874 (10) | 1.865 (15) | 2.618 (3) | 143 (2) |
O4A—H4A···O3C | 0.853 (10) | 1.770 (12) | 2.609 (2) | 168 (3) |
O4B—H4B···O3D | 0.846 (10) | 1.833 (13) | 2.646 (2) | 161 (3) |
O4C—H4C···O3Ai | 0.844 (10) | 1.839 (10) | 2.682 (2) | 178 (3) |
O4D—H4D···O3Bi | 0.849 (10) | 1.811 (10) | 2.659 (2) | 176 (2) |
Symmetry code: (i) x, y+1, z. |
Hydrogen-bond geometry (Å, º) for (niclosamide_acetone) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H2A···O4A | 0.88 | 1.94 | 2.671 (7) | 139.3 |
N2B—H2B···O4B | 0.88 | 1.96 | 2.690 (7) | 139.2 |
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) |
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