Abstract
The title Schiff base, C11H14ClNO4, originally refined as a neutral molecule [Chumakov, Antosyak, Mazus, Tsapkov & Samus (2000), Crystallogr. Rep. 45, 945–950], is interpreted as a zwitterionic compound. There are two independent zwitterions in the asymmetric unit. Five of the six hydroxy groups of the –CH2OH fragments are disordered. In one zwitterion, two are disordered over three sites [0.53 (1):0.33 (1):0.14 (1) and 0.65 (1):0.18 (1):0.17 (1)] and the third over two sites [0.66 (1):0.34 (1)]. In the second zwitterion, two are disordered over two sites [0.84 (1):0.16 (1) and 0.83 (1):0.17 (1)] and the third hydroxy group is ordered.
Related literature
The room-temperature crystal structure was interpreted as a neutral molecule; the disordered structure (the disorder confined to the hydroxy part of one of the six –CH2OH groups) refined to 0.072, see: Chumakov et al. (2000 ▶). The unsubstituted parent Schiff base is also a zwitterion; its structure has been determined several times, see: Asgedom et al. (1996 ▶); Odabas˛ogˇlu et al. (2003 ▶); Tatar et al. (2005 ▶); Zhang et al. (2000 ▶).
Experimental
Crystal data
C11H14ClNO4
M r = 259.68
Triclinic,
a = 7.0174 (1) Å
b = 10.1935 (1) Å
c = 16.7234 (2) Å
α = 79.520 (1)°
β = 89.031 (1)°
γ = 85.258 (1)°
V = 1172.27 (2) Å3
Z = 4
Mo Kα radiation
μ = 0.33 mm−1
T = 100 (2) K
0.30 × 0.20 × 0.05 mm
Data collection
Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.908, T max = 0.984
11241 measured reflections
5361 independent reflections
4771 reflections with I > 2σ(I)
R int = 0.018
Refinement
R[F 2 > 2σ(F 2)] = 0.042
wR(F 2) = 0.117
S = 1.01
5361 reflections
360 parameters
47 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρmax = 0.41 e Å−3
Δρmin = −0.74 e Å−3
Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).
Supplementary Material
Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680803866X/tk2330sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S160053680803866X/tk2330Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Acknowledgments
I thank the University of Malaya for supporting this study.
supplementary crystallographic information
Comment
A reevaluation of the title compound, originally reported as a neutral molecule (Chumakov et al., 2000), shows a zwitterionic compound, at low temperature, Fig. 1.
Experimental
The compound was synthesized from the reaction of 5-chlorosalicylaldehyde and tris(hydroxymethyl)aminomethane (Chumakov et al., 2000), and was recrystallized from ethanol.
Refinement
Five of the six hydroxy groups of the –CH2OH fragments are disordered. In one zwitterion, two are disordered over three sites [0.53 (1): 0.33: 0.14] and the third over two sites [0.65 (1): 0.18: 0.17]. In the second zwitterion, two are disordered over two sites [0.84 (1): 0.16 and 0.83 (1): 0.17] and the third is ordered. For each disordered –CH2OH fragment, the C–O distances (of the unprimed and primed atoms) were restrained to within 0.01 Å. The temperature factors of the primed atom(s) were restrained to those of the unprimed ones.
Carbon- and oxygen-bound hydrogen atoms were placed at calculated positions (C–H 0.95–0.99, O–H 0.84 Å) and were treated as riding on their parent atoms, with U(H) set to 1.2–1.5 times Ueq(C,O). The iminium hydrogen atoms were located in a difference Fourier map, and were refined with a distance restraint of N–H 0.88±0.01 Å; their temperature factors were freely refined.
Owing to the disorder, hydrogen bonding interactions involving the hydroxyl groups were not computed.
Figures
Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C22H28Cl2N2O8 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. The minor disorder components are not shown for clarity.
Crystal data
| C11H14ClNO4 | Z = 4 |
| Mr = 259.68 | F000 = 544 |
| Triclinic, P1 | Dx = 1.471 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation λ = 0.71073 Å |
| a = 7.0174 (1) Å | Cell parameters from 6864 reflections |
| b = 10.1935 (1) Å | θ = 2.2–28.3º |
| c = 16.7234 (2) Å | µ = 0.33 mm−1 |
| α = 79.520 (1)º | T = 100 (2) K |
| β = 89.031 (1)º | Prism, yellow |
| γ = 85.258 (1)º | 0.30 × 0.20 × 0.05 mm |
| V = 1172.27 (2) Å3 |
Data collection
| Bruker SMART APEX diffractometer | 5361 independent reflections |
| Radiation source: fine-focus sealed tube | 4771 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.018 |
| T = 100(2) K | θmax = 27.5º |
| ω scans | θmin = 1.2º |
| Absorption correction: Multi-scan(SADABS; Sheldrick, 1996) | h = −9→9 |
| Tmin = 0.908, Tmax = 0.984 | k = −13→13 |
| 11241 measured reflections | l = −21→21 |
Refinement
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.117 | w = 1/[σ2(Fo2) + (0.0573P)2 + 1.0948P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.01 | (Δ/σ)max = 0.001 |
| 5361 reflections | Δρmax = 0.41 e Å−3 |
| 360 parameters | Δρmin = −0.74 e Å−3 |
| 47 restraints | Extinction correction: none |
| Primary atom site location: structure-invariant direct methods |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | Occ. (<1) | |
| Cl1 | 0.74259 (7) | 0.67565 (5) | 0.56473 (3) | 0.03176 (13) | |
| Cl2 | 0.23984 (7) | 0.77985 (6) | 0.56151 (3) | 0.03809 (15) | |
| O1 | 0.54240 (19) | 0.73990 (13) | 0.21969 (8) | 0.0239 (3) | |
| O5 | 0.03446 (18) | 0.95420 (12) | 0.21807 (8) | 0.0246 (3) | |
| O2 | 0.1961 (3) | 1.1785 (2) | 0.17629 (14) | 0.0204 (4) | 0.535 (2) |
| H2 | 0.1471 | 1.1063 | 0.1939 | 0.031* | 0.535 (2) |
| O2' | 0.2372 (5) | 1.0814 (4) | 0.0932 (2) | 0.0204 (4) | 0.328 (3) |
| H2' | 0.1688 | 1.0397 | 0.1292 | 0.031* | 0.328 (3) |
| O2" | 0.3318 (13) | 1.2743 (9) | 0.0813 (5) | 0.0204 (4) | 0.137 (3) |
| H2" | 0.4077 | 1.3189 | 0.1015 | 0.031* | 0.137 (3) |
| O3 | 0.6388 (3) | 0.98149 (19) | 0.05581 (12) | 0.0256 (4) | 0.650 (3) |
| H3 | 0.7445 | 0.9411 | 0.0476 | 0.038* | 0.650 (3) |
| O3' | 0.8488 (9) | 1.1295 (10) | 0.0883 (6) | 0.0256 (4) | 0.183 (6) |
| H3' | 0.8968 | 1.0856 | 0.1317 | 0.038* | 0.183 (6) |
| O3" | 0.8481 (9) | 1.0984 (11) | 0.0690 (7) | 0.0256 (4) | 0.166 (6) |
| H3" | 0.8995 | 1.0227 | 0.0894 | 0.038* | 0.166 (6) |
| O4 | 0.6047 (3) | 1.35087 (18) | 0.13329 (12) | 0.0254 (5) | 0.660 (5) |
| H4 | 0.5375 | 1.4132 | 0.1492 | 0.038* | 0.660 (5) |
| O4' | 0.5213 (6) | 1.2777 (4) | 0.2551 (2) | 0.0254 (5) | 0.34 |
| H4' | 0.4631 | 1.3531 | 0.2394 | 0.038* | 0.340 (5) |
| O6 | 0.3862 (2) | 0.54296 (15) | 0.17552 (10) | 0.0241 (5) | 0.835 (6) |
| H6 | 0.4403 | 0.6031 | 0.1925 | 0.036* | 0.835 (6) |
| O6' | 0.2819 (11) | 0.5226 (7) | 0.0539 (5) | 0.0241 (5) | 0.16 |
| H6' | 0.1780 | 0.4913 | 0.0462 | 0.036* | 0.165 (6) |
| O7 | −0.0249 (2) | 0.40172 (15) | 0.12281 (10) | 0.0251 (5) | 0.831 (6) |
| H7 | 0.0171 | 0.3226 | 0.1412 | 0.038* | 0.831 (6) |
| O7' | 0.1139 (11) | 0.3978 (7) | 0.2403 (4) | 0.0251 (5) | 0.17 |
| H7' | 0.2264 | 0.4154 | 0.2276 | 0.038* | 0.169 (6) |
| O8 | −0.0449 (2) | 0.81865 (13) | 0.05073 (8) | 0.0336 (3) | |
| H8 | −0.0069 | 0.8306 | 0.0023 | 0.050* | |
| N1 | 0.5472 (2) | 0.99524 (14) | 0.21010 (9) | 0.0194 (3) | |
| H1N | 0.537 (4) | 0.9209 (17) | 0.1907 (15) | 0.043 (7)* | |
| N2 | 0.0469 (2) | 0.70644 (14) | 0.20403 (9) | 0.0174 (3) | |
| H2N | 0.029 (3) | 0.7936 (11) | 0.1854 (14) | 0.033 (6)* | |
| C1 | 0.5840 (2) | 0.72652 (17) | 0.29646 (11) | 0.0192 (3) | |
| C2 | 0.6121 (3) | 0.59874 (18) | 0.34689 (12) | 0.0271 (4) | |
| H2A | 0.5990 | 0.5209 | 0.3243 | 0.032* | |
| C3 | 0.6579 (3) | 0.58514 (18) | 0.42746 (12) | 0.0268 (4) | |
| H3A | 0.6760 | 0.4983 | 0.4598 | 0.032* | |
| C4 | 0.6782 (2) | 0.69780 (18) | 0.46259 (11) | 0.0232 (4) | |
| C5 | 0.6502 (2) | 0.82333 (18) | 0.41675 (11) | 0.0224 (3) | |
| H5 | 0.6619 | 0.8996 | 0.4411 | 0.027* | |
| C6 | 0.6041 (2) | 0.84008 (16) | 0.33387 (11) | 0.0188 (3) | |
| C7 | 0.5840 (2) | 0.97254 (17) | 0.28681 (11) | 0.0216 (3) | |
| H7A | 0.5984 | 1.0463 | 0.3131 | 0.026* | |
| C8 | 0.5387 (2) | 1.12384 (17) | 0.15371 (10) | 0.0203 (3) | |
| C9 | 0.3328 (3) | 1.1578 (2) | 0.12391 (13) | 0.0329 (4) | |
| H9A | 0.3316 | 1.2392 | 0.0813 | 0.039* | 0.535 (2) |
| H9B | 0.2978 | 1.0842 | 0.0972 | 0.039* | 0.535 (2) |
| H9C | 0.2577 | 1.1804 | 0.1709 | 0.039* | 0.328 (3) |
| H9D | 0.3335 | 1.2417 | 0.0834 | 0.039* | 0.328 (3) |
| H9E | 0.2957 | 1.0929 | 0.0908 | 0.039* | 0.137 (3) |
| H9F | 0.2433 | 1.1569 | 0.1704 | 0.039* | 0.137 (3) |
| C10 | 0.6699 (3) | 1.1019 (2) | 0.08285 (13) | 0.0338 (5) | |
| H10A | 0.6471 | 1.1782 | 0.0373 | 0.041* | 0.650 (3) |
| H10B | 0.8048 | 1.0987 | 0.1000 | 0.041* | 0.650 (3) |
| H10C | 0.6697 | 1.0070 | 0.0769 | 0.041* | 0.183 (6) |
| H10D | 0.6146 | 1.1573 | 0.0325 | 0.041* | 0.183 (6) |
| H10E | 0.6352 | 1.0150 | 0.0712 | 0.041* | 0.166 (6) |
| H10F | 0.6163 | 1.1698 | 0.0371 | 0.041* | 0.166 (6) |
| C11 | 0.6064 (3) | 1.23560 (18) | 0.19279 (12) | 0.0289 (4) | |
| H11A | 0.5204 | 1.2514 | 0.2382 | 0.035* | 0.660 (5) |
| H11B | 0.7372 | 1.2106 | 0.2146 | 0.035* | 0.660 (5) |
| H11C | 0.7408 | 1.2083 | 0.2092 | 0.035* | 0.340 (5) |
| H11D | 0.6095 | 1.3150 | 0.1489 | 0.035* | 0.340 (5) |
| C12 | 0.0782 (2) | 0.91510 (17) | 0.29366 (12) | 0.0216 (3) | |
| C13 | 0.1062 (3) | 1.00731 (19) | 0.34634 (14) | 0.0292 (4) | |
| H13 | 0.0916 | 1.1006 | 0.3253 | 0.035* | |
| C14 | 0.1531 (3) | 0.9650 (2) | 0.42592 (15) | 0.0335 (5) | |
| H14 | 0.1714 | 1.0291 | 0.4593 | 0.040* | |
| C15 | 0.1751 (3) | 0.8282 (2) | 0.45953 (12) | 0.0271 (4) | |
| C16 | 0.1489 (2) | 0.73448 (18) | 0.41255 (11) | 0.0219 (3) | |
| H16 | 0.1619 | 0.6419 | 0.4357 | 0.026* | |
| C17 | 0.1027 (2) | 0.77585 (16) | 0.32963 (11) | 0.0187 (3) | |
| C18 | 0.0882 (2) | 0.67582 (16) | 0.28079 (10) | 0.0175 (3) | |
| H18 | 0.1095 | 0.5842 | 0.3053 | 0.021* | |
| C19 | 0.0507 (2) | 0.61584 (16) | 0.14497 (10) | 0.0172 (3) | |
| C20 | 0.2570 (2) | 0.60202 (17) | 0.11302 (11) | 0.0213 (3) | |
| H20A | 0.2621 | 0.5465 | 0.0701 | 0.026* | 0.835 (6) |
| H20B | 0.2959 | 0.6917 | 0.0884 | 0.026* | 0.835 (6) |
| H20C | 0.2963 | 0.6924 | 0.0902 | 0.026* | 0.165 (6) |
| H20D | 0.3425 | 0.5636 | 0.1593 | 0.026* | 0.165 (6) |
| C21 | −0.0160 (2) | 0.47961 (16) | 0.18370 (10) | 0.0197 (3) | |
| H21A | 0.0747 | 0.4344 | 0.2267 | 0.024* | 0.831 (6) |
| H21B | −0.1436 | 0.4914 | 0.2088 | 0.024* | 0.831 (6) |
| H21C | −0.1389 | 0.4944 | 0.2119 | 0.024* | 0.169 (6) |
| H21D | −0.0407 | 0.4299 | 0.1398 | 0.024* | 0.169 (6) |
| C22 | −0.0847 (3) | 0.68282 (17) | 0.07586 (11) | 0.0229 (3) | |
| H22A | −0.0676 | 0.6350 | 0.0294 | 0.027* | |
| H22B | −0.2189 | 0.6784 | 0.0947 | 0.027* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0346 (3) | 0.0301 (2) | 0.0279 (2) | −0.00246 (19) | −0.01100 (18) | 0.00271 (18) |
| Cl2 | 0.0343 (3) | 0.0474 (3) | 0.0384 (3) | 0.0139 (2) | −0.0164 (2) | −0.0295 (2) |
| O1 | 0.0282 (7) | 0.0225 (6) | 0.0243 (6) | −0.0092 (5) | 0.0037 (5) | −0.0100 (5) |
| O5 | 0.0241 (6) | 0.0153 (6) | 0.0333 (7) | −0.0013 (5) | 0.0054 (5) | −0.0018 (5) |
| O2 | 0.0200 (9) | 0.0169 (9) | 0.0237 (9) | −0.0017 (7) | −0.0014 (7) | −0.0023 (7) |
| O2' | 0.0200 (9) | 0.0169 (9) | 0.0237 (9) | −0.0017 (7) | −0.0014 (7) | −0.0023 (7) |
| O2" | 0.0200 (9) | 0.0169 (9) | 0.0237 (9) | −0.0017 (7) | −0.0014 (7) | −0.0023 (7) |
| O3 | 0.0374 (10) | 0.0208 (9) | 0.0184 (9) | 0.0056 (7) | 0.0022 (7) | −0.0069 (7) |
| O3' | 0.0374 (10) | 0.0208 (9) | 0.0184 (9) | 0.0056 (7) | 0.0022 (7) | −0.0069 (7) |
| O3" | 0.0374 (10) | 0.0208 (9) | 0.0184 (9) | 0.0056 (7) | 0.0022 (7) | −0.0069 (7) |
| O4 | 0.0304 (10) | 0.0163 (8) | 0.0289 (10) | 0.0014 (7) | −0.0012 (7) | −0.0035 (7) |
| O4' | 0.0304 (10) | 0.0163 (8) | 0.0289 (10) | 0.0014 (7) | −0.0012 (7) | −0.0035 (7) |
| O6 | 0.0191 (8) | 0.0217 (8) | 0.0350 (9) | −0.0028 (6) | −0.0028 (6) | −0.0135 (6) |
| O6' | 0.0191 (8) | 0.0217 (8) | 0.0350 (9) | −0.0028 (6) | −0.0028 (6) | −0.0135 (6) |
| O7 | 0.0273 (9) | 0.0185 (8) | 0.0326 (9) | −0.0019 (6) | 0.0009 (6) | −0.0125 (6) |
| O7' | 0.0273 (9) | 0.0185 (8) | 0.0326 (9) | −0.0019 (6) | 0.0009 (6) | −0.0125 (6) |
| O8 | 0.0575 (10) | 0.0221 (7) | 0.0194 (6) | −0.0016 (6) | −0.0017 (6) | 0.0000 (5) |
| N1 | 0.0198 (7) | 0.0167 (7) | 0.0231 (7) | −0.0006 (5) | −0.0021 (5) | −0.0075 (5) |
| N2 | 0.0191 (7) | 0.0132 (6) | 0.0200 (7) | −0.0008 (5) | 0.0024 (5) | −0.0042 (5) |
| C1 | 0.0150 (7) | 0.0201 (8) | 0.0246 (8) | −0.0050 (6) | 0.0038 (6) | −0.0082 (6) |
| C2 | 0.0326 (10) | 0.0189 (8) | 0.0318 (10) | −0.0069 (7) | 0.0093 (8) | −0.0088 (7) |
| C3 | 0.0286 (9) | 0.0187 (8) | 0.0315 (10) | −0.0017 (7) | 0.0052 (7) | −0.0014 (7) |
| C4 | 0.0185 (8) | 0.0250 (9) | 0.0250 (9) | −0.0013 (6) | −0.0032 (6) | −0.0020 (7) |
| C5 | 0.0199 (8) | 0.0210 (8) | 0.0275 (9) | −0.0013 (6) | −0.0078 (7) | −0.0068 (7) |
| C6 | 0.0145 (7) | 0.0181 (8) | 0.0244 (8) | −0.0002 (6) | −0.0039 (6) | −0.0059 (6) |
| C7 | 0.0211 (8) | 0.0192 (8) | 0.0262 (9) | 0.0016 (6) | −0.0069 (6) | −0.0094 (7) |
| C8 | 0.0208 (8) | 0.0198 (8) | 0.0203 (8) | −0.0005 (6) | 0.0008 (6) | −0.0044 (6) |
| C9 | 0.0230 (9) | 0.0364 (11) | 0.0336 (10) | −0.0047 (8) | −0.0029 (8) | 0.0098 (8) |
| C10 | 0.0383 (11) | 0.0307 (10) | 0.0367 (11) | −0.0115 (8) | 0.0183 (9) | −0.0150 (8) |
| C11 | 0.0396 (11) | 0.0174 (8) | 0.0301 (10) | 0.0014 (7) | −0.0068 (8) | −0.0066 (7) |
| C12 | 0.0132 (7) | 0.0175 (8) | 0.0360 (10) | −0.0019 (6) | 0.0056 (6) | −0.0101 (7) |
| C13 | 0.0212 (9) | 0.0185 (8) | 0.0515 (12) | −0.0012 (7) | −0.0006 (8) | −0.0161 (8) |
| C14 | 0.0225 (9) | 0.0308 (10) | 0.0549 (13) | 0.0016 (7) | −0.0065 (8) | −0.0292 (9) |
| C15 | 0.0175 (8) | 0.0338 (10) | 0.0344 (10) | 0.0042 (7) | −0.0049 (7) | −0.0202 (8) |
| C16 | 0.0174 (8) | 0.0230 (8) | 0.0273 (9) | 0.0019 (6) | −0.0009 (6) | −0.0114 (7) |
| C17 | 0.0136 (7) | 0.0185 (8) | 0.0261 (8) | −0.0013 (6) | 0.0024 (6) | −0.0096 (6) |
| C18 | 0.0161 (7) | 0.0150 (7) | 0.0219 (8) | −0.0011 (6) | 0.0022 (6) | −0.0052 (6) |
| C19 | 0.0191 (8) | 0.0158 (7) | 0.0176 (7) | −0.0014 (6) | 0.0016 (6) | −0.0056 (6) |
| C20 | 0.0204 (8) | 0.0213 (8) | 0.0236 (8) | −0.0034 (6) | 0.0042 (6) | −0.0076 (6) |
| C21 | 0.0211 (8) | 0.0167 (7) | 0.0225 (8) | −0.0037 (6) | 0.0018 (6) | −0.0054 (6) |
| C22 | 0.0251 (9) | 0.0214 (8) | 0.0215 (8) | 0.0007 (7) | −0.0012 (7) | −0.0036 (6) |
Geometric parameters (Å, °)
| Cl1—C4 | 1.7442 (19) | C6—C7 | 1.431 (2) |
| Cl2—C15 | 1.744 (2) | C7—H7A | 0.9500 |
| O1—C1 | 1.302 (2) | C8—C11 | 1.524 (2) |
| O5—C12 | 1.289 (2) | C8—C10 | 1.526 (2) |
| O2—C9 | 1.318 (3) | C8—C9 | 1.528 (3) |
| O2—H2 | 0.8400 | C9—H9A | 0.9900 |
| O2'—C9 | 1.251 (4) | C9—H9B | 0.9900 |
| O2'—H2' | 0.8400 | C9—H9C | 0.9900 |
| O2"—C9 | 1.268 (9) | C9—H9D | 0.9900 |
| O2"—H2" | 0.8400 | C9—H9E | 0.9900 |
| O3—C10 | 1.417 (3) | C9—H9F | 0.9900 |
| O3—H3 | 0.8400 | C10—H10A | 0.9900 |
| O3'—C10 | 1.318 (6) | C10—H10B | 0.9900 |
| O3'—H3' | 0.8400 | C10—H10C | 0.9900 |
| O3"—C10 | 1.266 (6) | C10—H10D | 0.9900 |
| O3"—H3" | 0.8400 | C10—H10E | 0.9900 |
| O4—C11 | 1.394 (3) | C10—H10F | 0.9900 |
| O4—H4 | 0.8400 | C11—H11A | 0.9900 |
| O4'—C11 | 1.313 (4) | C11—H11B | 0.9900 |
| O4'—H4' | 0.8400 | C11—H11C | 0.9900 |
| O6—C20 | 1.411 (2) | C11—H11D | 0.9900 |
| O6—H6 | 0.8400 | C12—C13 | 1.427 (2) |
| O6'—C20 | 1.389 (6) | C12—C17 | 1.435 (2) |
| O6'—H6' | 0.8400 | C13—C14 | 1.360 (3) |
| O7—C21 | 1.405 (2) | C13—H13 | 0.9500 |
| O7—H7 | 0.8400 | C14—C15 | 1.402 (3) |
| O7'—C21 | 1.428 (6) | C14—H14 | 0.9500 |
| O7'—H7' | 0.8400 | C15—C16 | 1.368 (2) |
| O8—C22 | 1.421 (2) | C16—C17 | 1.409 (2) |
| O8—H8 | 0.8400 | C16—H16 | 0.9500 |
| N1—C7 | 1.288 (2) | C17—C18 | 1.428 (2) |
| N1—C8 | 1.467 (2) | C18—H18 | 0.9500 |
| N1—H1N | 0.885 (10) | C19—C21 | 1.529 (2) |
| N2—C18 | 1.297 (2) | C19—C22 | 1.532 (2) |
| N2—C19 | 1.468 (2) | C19—C20 | 1.539 (2) |
| N2—H2N | 0.886 (10) | C20—H20A | 0.9900 |
| C1—C2 | 1.418 (2) | C20—H20B | 0.9900 |
| C1—C6 | 1.430 (2) | C20—H20C | 0.9900 |
| C2—C3 | 1.370 (3) | C20—H20D | 0.9900 |
| C2—H2A | 0.9500 | C21—H21A | 0.9900 |
| C3—C4 | 1.400 (3) | C21—H21B | 0.9900 |
| C3—H3A | 0.9500 | C21—H21C | 0.9900 |
| C4—C5 | 1.368 (2) | C21—H21D | 0.9900 |
| C5—C6 | 1.405 (2) | C22—H22A | 0.9900 |
| C5—H5 | 0.9500 | C22—H22B | 0.9900 |
| C9—O2—H2 | 109.5 | H10E—C10—H10F | 105.1 |
| C9—O2'—H2' | 109.5 | O4'—C11—O4 | 103.6 (2) |
| C9—O2"—H2" | 109.5 | O4'—C11—C8 | 123.9 (2) |
| C10—O3—H3 | 109.5 | O4—C11—C8 | 107.90 (16) |
| C10—O3'—H3' | 109.5 | O4—C11—H11A | 110.1 |
| C10—O3"—H3" | 109.5 | C8—C11—H11A | 110.1 |
| C11—O4—H4 | 109.5 | O4'—C11—H11B | 100.6 |
| C11—O4'—H4' | 109.5 | O4—C11—H11B | 110.1 |
| C20—O6—H6 | 109.5 | C8—C11—H11B | 110.1 |
| C20—O6'—H6' | 109.5 | H11A—C11—H11B | 108.4 |
| C21—O7—H7 | 109.5 | O4'—C11—H11C | 106.4 |
| C21—O7'—H7' | 109.5 | O4—C11—H11C | 108.0 |
| C22—O8—H8 | 109.5 | C8—C11—H11C | 106.4 |
| C7—N1—C8 | 127.86 (14) | O4'—C11—H11D | 106.4 |
| C7—N1—H1N | 112.8 (18) | C8—C11—H11D | 106.4 |
| C8—N1—H1N | 119.1 (18) | H11B—C11—H11D | 108.8 |
| C18—N2—C19 | 127.48 (14) | H11C—C11—H11D | 106.4 |
| C18—N2—H2N | 114.0 (16) | O5—C12—C13 | 122.12 (16) |
| C19—N2—H2N | 118.0 (16) | O5—C12—C17 | 121.79 (15) |
| O1—C1—C2 | 121.63 (15) | C13—C12—C17 | 116.09 (17) |
| O1—C1—C6 | 121.54 (15) | C14—C13—C12 | 121.68 (18) |
| C2—C1—C6 | 116.83 (16) | C14—C13—H13 | 119.2 |
| C3—C2—C1 | 121.40 (16) | C12—C13—H13 | 119.2 |
| C3—C2—H2A | 119.3 | C13—C14—C15 | 120.98 (17) |
| C1—C2—H2A | 119.3 | C13—C14—H14 | 119.5 |
| C2—C3—C4 | 120.73 (17) | C15—C14—H14 | 119.5 |
| C2—C3—H3A | 119.6 | C16—C15—C14 | 120.36 (19) |
| C4—C3—H3A | 119.6 | C16—C15—Cl2 | 120.69 (16) |
| C5—C4—C3 | 120.11 (17) | C14—C15—Cl2 | 118.94 (14) |
| C5—C4—Cl1 | 120.71 (14) | C15—C16—C17 | 119.69 (17) |
| C3—C4—Cl1 | 119.18 (14) | C15—C16—H16 | 120.2 |
| C4—C5—C6 | 120.31 (16) | C17—C16—H16 | 120.2 |
| C4—C5—H5 | 119.8 | C16—C17—C18 | 118.51 (15) |
| C6—C5—H5 | 119.8 | C16—C17—C12 | 121.20 (15) |
| C5—C6—C1 | 120.61 (15) | C18—C17—C12 | 120.24 (16) |
| C5—C6—C7 | 118.89 (15) | N2—C18—C17 | 121.93 (15) |
| C1—C6—C7 | 120.46 (15) | N2—C18—H18 | 119.0 |
| N1—C7—C6 | 122.31 (15) | C17—C18—H18 | 119.0 |
| N1—C7—H7A | 118.8 | N2—C19—C21 | 111.20 (13) |
| C6—C7—H7A | 118.8 | N2—C19—C22 | 106.69 (13) |
| N1—C8—C11 | 112.26 (14) | C21—C19—C22 | 109.93 (14) |
| N1—C8—C10 | 105.88 (15) | N2—C19—C20 | 107.43 (13) |
| C11—C8—C10 | 109.77 (15) | C21—C19—C20 | 111.18 (14) |
| N1—C8—C9 | 108.14 (14) | C22—C19—C20 | 110.29 (14) |
| C11—C8—C9 | 110.66 (16) | O6'—C20—O6 | 105.2 (4) |
| C10—C8—C9 | 110.00 (16) | O6'—C20—C19 | 114.2 (3) |
| O2'—C9—C8 | 124.6 (2) | O6—C20—C19 | 111.78 (14) |
| O2"—C9—C8 | 104.9 (4) | O6—C20—H20A | 109.3 |
| O2—C9—C8 | 119.54 (19) | C19—C20—H20A | 109.3 |
| O2'—C9—H9A | 103.4 | O6'—C20—H20B | 106.9 |
| O2—C9—H9A | 107.4 | O6—C20—H20B | 109.3 |
| C8—C9—H9A | 107.4 | C19—C20—H20B | 109.3 |
| O2"—C9—H9B | 118.1 | H20A—C20—H20B | 107.9 |
| O2—C9—H9B | 107.4 | O6'—C20—H20C | 108.7 |
| C8—C9—H9B | 107.4 | O6—C20—H20C | 108.0 |
| H9A—C9—H9B | 107.0 | C19—C20—H20C | 108.7 |
| O2'—C9—H9C | 106.2 | H20A—C20—H20C | 109.8 |
| C8—C9—H9C | 106.2 | O6'—C20—H20D | 108.7 |
| H9A—C9—H9C | 108.2 | C19—C20—H20D | 108.7 |
| H9B—C9—H9C | 120.1 | H20A—C20—H20D | 112.6 |
| O2'—C9—H9D | 106.2 | H20B—C20—H20D | 109.0 |
| O2—C9—H9D | 106.2 | H20C—C20—H20D | 107.6 |
| C8—C9—H9D | 106.2 | O7—C21—O7' | 101.9 (3) |
| H9B—C9—H9D | 109.8 | O7—C21—C19 | 108.48 (14) |
| O2"—C9—H9E | 110.8 | O7'—C21—C19 | 115.5 (3) |
| O2—C9—H9E | 110.1 | O7—C21—H21A | 110.0 |
| C8—C9—H9E | 110.8 | C19—C21—H21A | 110.0 |
| O2"—C9—H9F | 110.8 | O7—C21—H21B | 110.0 |
| C8—C9—H9F | 110.8 | O7'—C21—H21B | 110.7 |
| H9E—C9—H9F | 108.8 | C19—C21—H21B | 110.0 |
| O3'—C10—C8 | 116.5 (5) | H21A—C21—H21B | 108.4 |
| O3—C10—C8 | 111.74 (16) | O7—C21—H21C | 114.3 |
| O3—C10—H10A | 109.3 | O7'—C21—H21C | 108.4 |
| C8—C10—H10A | 109.3 | C19—C21—H21C | 108.4 |
| O3—C10—H10B | 109.3 | H21A—C21—H21C | 105.6 |
| C8—C10—H10B | 109.3 | O7'—C21—H21D | 108.4 |
| H10A—C10—H10B | 107.9 | C19—C21—H21D | 108.4 |
| O3'—C10—H10C | 108.2 | H21A—C21—H21D | 116.7 |
| C8—C10—H10C | 108.2 | H21B—C21—H21D | 103.1 |
| O3'—C10—H10D | 108.2 | H21C—C21—H21D | 107.5 |
| C8—C10—H10D | 108.2 | O8—C22—C19 | 109.62 (14) |
| H10C—C10—H10D | 107.3 | O8—C22—H22A | 109.7 |
| C8—C10—H10E | 103.1 | C19—C22—H22A | 109.7 |
| O3"—C10—H10F | 103.1 | O8—C22—H22B | 109.7 |
| O3'—C10—H10F | 104.6 | C19—C22—H22B | 109.7 |
| O3—C10—H10F | 101.4 | H22A—C22—H22B | 108.2 |
| C8—C10—H10F | 103.1 | ||
| O1—C1—C2—C3 | 179.32 (17) | C9—C8—C11—O4' | 58.1 (3) |
| C6—C1—C2—C3 | −0.5 (3) | N1—C8—C11—O4 | 176.23 (16) |
| C1—C2—C3—C4 | 0.0 (3) | C10—C8—C11—O4 | 58.8 (2) |
| C2—C3—C4—C5 | 0.8 (3) | C9—C8—C11—O4 | −62.8 (2) |
| C2—C3—C4—Cl1 | −178.35 (15) | O5—C12—C13—C14 | −179.70 (17) |
| C3—C4—C5—C6 | −1.1 (3) | C17—C12—C13—C14 | 0.0 (3) |
| Cl1—C4—C5—C6 | 178.02 (13) | C12—C13—C14—C15 | −0.3 (3) |
| C4—C5—C6—C1 | 0.6 (3) | C13—C14—C15—C16 | −0.2 (3) |
| C4—C5—C6—C7 | −177.26 (16) | C13—C14—C15—Cl2 | 178.80 (15) |
| O1—C1—C6—C5 | −179.64 (15) | C14—C15—C16—C17 | 1.0 (3) |
| C2—C1—C6—C5 | 0.2 (2) | Cl2—C15—C16—C17 | −177.95 (13) |
| O1—C1—C6—C7 | −1.8 (2) | C15—C16—C17—C18 | 176.05 (16) |
| C2—C1—C6—C7 | 178.03 (16) | C15—C16—C17—C12 | −1.4 (3) |
| C8—N1—C7—C6 | −174.53 (16) | O5—C12—C17—C16 | −179.45 (15) |
| C5—C6—C7—N1 | 178.05 (16) | C13—C12—C17—C16 | 0.9 (2) |
| C1—C6—C7—N1 | 0.2 (3) | O5—C12—C17—C18 | 3.2 (2) |
| C7—N1—C8—C11 | 7.8 (2) | C13—C12—C17—C18 | −176.51 (15) |
| C7—N1—C8—C10 | 127.59 (19) | C19—N2—C18—C17 | 171.78 (15) |
| C7—N1—C8—C9 | −114.5 (2) | C16—C17—C18—N2 | −179.76 (15) |
| N1—C8—C9—O2' | −52.8 (3) | C12—C17—C18—N2 | −2.3 (2) |
| C11—C8—C9—O2' | −176.2 (3) | C18—N2—C19—C21 | 36.7 (2) |
| C10—C8—C9—O2' | 62.4 (3) | C18—N2—C19—C22 | 156.57 (16) |
| N1—C8—C9—O2" | 174.6 (5) | C18—N2—C19—C20 | −85.16 (19) |
| C11—C8—C9—O2" | 51.2 (5) | N2—C19—C20—O6' | −177.7 (4) |
| C10—C8—C9—O2" | −70.2 (5) | C21—C19—C20—O6' | 60.4 (4) |
| N1—C8—C9—O2 | 63.7 (2) | C22—C19—C20—O6' | −61.8 (4) |
| C11—C8—C9—O2 | −59.6 (2) | N2—C19—C20—O6 | 62.94 (17) |
| C10—C8—C9—O2 | 178.90 (19) | C21—C19—C20—O6 | −58.93 (18) |
| N1—C8—C10—O3" | −80.6 (7) | C22—C19—C20—O6 | 178.86 (14) |
| C11—C8—C10—O3" | 40.8 (7) | N2—C19—C21—O7 | 175.00 (14) |
| C9—C8—C10—O3" | 162.8 (7) | C22—C19—C21—O7 | 57.08 (18) |
| N1—C8—C10—O3' | −92.1 (5) | C20—C19—C21—O7 | −65.33 (18) |
| C11—C8—C10—O3' | 29.3 (5) | N2—C19—C21—O7' | −71.5 (4) |
| C9—C8—C10—O3' | 151.3 (4) | C22—C19—C21—O7' | 170.6 (4) |
| N1—C8—C10—O3 | 46.0 (2) | C20—C19—C21—O7' | 48.2 (4) |
| C11—C8—C10—O3 | 167.35 (18) | N2—C19—C22—O8 | 48.05 (18) |
| C9—C8—C10—O3 | −70.7 (2) | C21—C19—C22—O8 | 168.73 (14) |
| N1—C8—C11—O4' | −62.9 (3) | C20—C19—C22—O8 | −68.33 (18) |
| C10—C8—C11—O4' | 179.7 (3) |
Hydrogen-bond geometry (Å, °)
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1n···O1 | 0.87 (1) | 1.82 (2) | 2.582 (2) | 143 (2) |
| N2—H2n···O5 | 0.87 (1) | 1.82 (2) | 2.573 (2) | 141 (2) |
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2330).
References
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680803866X/tk2330sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S160053680803866X/tk2330Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report