organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Low-temperature redetermination of 4-chloro-2-[tris­­(hy­droxy­meth­yl)methyl­imino­meth­yl]phenol as zwitterionic 4-chloro-2-[tris­­(hy­droxy­meth­yl)methyl­iminiometh­yl]phenolate

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 15 November 2008; accepted 19 November 2008; online 26 November 2008)

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[Chumakov, Yu. M., Antosyak, B. Ya., Mazus, M. D., Tsapkov, V. I. & Samus', N. M. (2000). Crystallogr. Rep. 45, 945-950.]). The unsubstituted parent Schiff base is also a zwitterion; its structure has been determined several times, see: Asgedom et al. (1996[Asgedom, G., Sreedhara, A., Kivikoski, J., Valkonen, J., Kolehmainen, E. & Rao, C. P. (1996). Inorg. Chem. 35, 5674-5683.]); Odabas˛ogˇlu et al. (2003[Odabas˛oǧlu, M., Albayrak, Ç., Büyükgüngör, O. & Lönnecke, P. (2003). Acta Cryst. C59, o616-o619.]); Tatar et al. (2005[Tatar, L., Nazir, H., Gümüser, M., Kate, C. & Atakol, O. (2005). Z. Kristallogr. 220, 639-642.]); Zhang et al. (2000[Zhang, C. G., Zu, P. Z., Wu, D. & Yu, K. B. (2000). J. Chem. Res. pp. 402-403.]).

[Scheme 1]

Experimental

Crystal data
  • C11H14ClNO4

  • Mr = 259.68

  • Triclinic, [P \overline 1]

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.908, Tmax = 0.984

  • 11241 measured reflections

  • 5361 independent reflections

  • 4771 reflections with I > 2σ(I)

  • Rint = 0.018

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 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[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2008[Westrip, S. P. (2008). publCIF. In preparation.]).

Supporting information


Comment top

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.

Related literature top

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 top

The compound was synthesized from the reaction of 5-chlorosalicylaldehyde and tris(hydroxymethyl)aminomethane (Chumakov et al., 2000), and was recrystallized from ethanol.

Refinement top

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.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: pubCIF (Westrip, 2008).

Figures top
[Figure 1] 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.
4-chloro-2-[tris(hydroxymethyl)methyliminiomethyl]phenolate top
Crystal data top
C11H14ClNO4Z = 4
Mr = 259.68F(000) = 544
Triclinic, P1Dx = 1.471 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.0174 (1) ÅCell parameters from 6864 reflections
b = 10.1935 (1) Åθ = 2.2–28.3°
c = 16.7234 (2) ŵ = 0.33 mm1
α = 79.520 (1)°T = 100 K
β = 89.031 (1)°Prism, yellow
γ = 85.258 (1)°0.30 × 0.20 × 0.05 mm
V = 1172.27 (2) Å3
Data collection top
Bruker SMART APEX
diffractometer
5361 independent reflections
Radiation source: fine-focus sealed tube4771 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
ω scansθmax = 27.5°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.908, Tmax = 0.984k = 1313
11241 measured reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0573P)2 + 1.0948P]
where P = (Fo2 + 2Fc2)/3
5361 reflections(Δ/σ)max = 0.001
360 parametersΔρmax = 0.41 e Å3
47 restraintsΔρmin = 0.74 e Å3
Crystal data top
C11H14ClNO4γ = 85.258 (1)°
Mr = 259.68V = 1172.27 (2) Å3
Triclinic, P1Z = 4
a = 7.0174 (1) ÅMo Kα radiation
b = 10.1935 (1) ŵ = 0.33 mm1
c = 16.7234 (2) ÅT = 100 K
α = 79.520 (1)°0.30 × 0.20 × 0.05 mm
β = 89.031 (1)°
Data collection top
Bruker SMART APEX
diffractometer
5361 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4771 reflections with I > 2σ(I)
Tmin = 0.908, Tmax = 0.984Rint = 0.018
11241 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04247 restraints
wR(F2) = 0.117H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.41 e Å3
5361 reflectionsΔρmin = 0.74 e Å3
360 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.74259 (7)0.67565 (5)0.56473 (3)0.03176 (13)
Cl20.23984 (7)0.77985 (6)0.56151 (3)0.03809 (15)
O10.54240 (19)0.73990 (13)0.21969 (8)0.0239 (3)
O50.03446 (18)0.95420 (12)0.21807 (8)0.0246 (3)
O20.1961 (3)1.1785 (2)0.17629 (14)0.0204 (4)0.535 (2)
H20.14711.10630.19390.031*0.535 (2)
O2'0.2372 (5)1.0814 (4)0.0932 (2)0.0204 (4)0.328 (3)
H2'0.16881.03970.12920.031*0.328 (3)
O2"0.3318 (13)1.2743 (9)0.0813 (5)0.0204 (4)0.137 (3)
H2"0.40771.31890.10150.031*0.137 (3)
O30.6388 (3)0.98149 (19)0.05581 (12)0.0256 (4)0.650 (3)
H30.74450.94110.04760.038*0.650 (3)
O3'0.8488 (9)1.1295 (10)0.0883 (6)0.0256 (4)0.183 (6)
H3'0.89681.08560.13170.038*0.183 (6)
O3"0.8481 (9)1.0984 (11)0.0690 (7)0.0256 (4)0.166 (6)
H3"0.89951.02270.08940.038*0.166 (6)
O40.6047 (3)1.35087 (18)0.13329 (12)0.0254 (5)0.660 (5)
H40.53751.41320.14920.038*0.660 (5)
O4'0.5213 (6)1.2777 (4)0.2551 (2)0.0254 (5)0.34
H4'0.46311.35310.23940.038*0.340 (5)
O60.3862 (2)0.54296 (15)0.17552 (10)0.0241 (5)0.835 (6)
H60.44030.60310.19250.036*0.835 (6)
O6'0.2819 (11)0.5226 (7)0.0539 (5)0.0241 (5)0.16
H6'0.17800.49130.04620.036*0.165 (6)
O70.0249 (2)0.40172 (15)0.12281 (10)0.0251 (5)0.831 (6)
H70.01710.32260.14120.038*0.831 (6)
O7'0.1139 (11)0.3978 (7)0.2403 (4)0.0251 (5)0.17
H7'0.22640.41540.22760.038*0.169 (6)
O80.0449 (2)0.81865 (13)0.05073 (8)0.0336 (3)
H80.00690.83060.00230.050*
N10.5472 (2)0.99524 (14)0.21010 (9)0.0194 (3)
H1N0.537 (4)0.9209 (17)0.1907 (15)0.043 (7)*
N20.0469 (2)0.70644 (14)0.20403 (9)0.0174 (3)
H2N0.029 (3)0.7936 (11)0.1854 (14)0.033 (6)*
C10.5840 (2)0.72652 (17)0.29646 (11)0.0192 (3)
C20.6121 (3)0.59874 (18)0.34689 (12)0.0271 (4)
H2A0.59900.52090.32430.032*
C30.6579 (3)0.58514 (18)0.42746 (12)0.0268 (4)
H3A0.67600.49830.45980.032*
C40.6782 (2)0.69780 (18)0.46259 (11)0.0232 (4)
C50.6502 (2)0.82333 (18)0.41675 (11)0.0224 (3)
H50.66190.89960.44110.027*
C60.6041 (2)0.84008 (16)0.33387 (11)0.0188 (3)
C70.5840 (2)0.97254 (17)0.28681 (11)0.0216 (3)
H7A0.59841.04630.31310.026*
C80.5387 (2)1.12384 (17)0.15371 (10)0.0203 (3)
C90.3328 (3)1.1578 (2)0.12391 (13)0.0329 (4)
H9A0.33161.23920.08130.039*0.535 (2)
H9B0.29781.08420.09720.039*0.535 (2)
H9C0.25771.18040.17090.039*0.328 (3)
H9D0.33351.24170.08340.039*0.328 (3)
H9E0.29571.09290.09080.039*0.137 (3)
H9F0.24331.15690.17040.039*0.137 (3)
C100.6699 (3)1.1019 (2)0.08285 (13)0.0338 (5)
H10A0.64711.17820.03730.041*0.650 (3)
H10B0.80481.09870.10000.041*0.650 (3)
H10C0.66971.00700.07690.041*0.183 (6)
H10D0.61461.15730.03250.041*0.183 (6)
H10E0.63521.01500.07120.041*0.166 (6)
H10F0.61631.16980.03710.041*0.166 (6)
C110.6064 (3)1.23560 (18)0.19279 (12)0.0289 (4)
H11A0.52041.25140.23820.035*0.660 (5)
H11B0.73721.21060.21460.035*0.660 (5)
H11C0.74081.20830.20920.035*0.340 (5)
H11D0.60951.31500.14890.035*0.340 (5)
C120.0782 (2)0.91510 (17)0.29366 (12)0.0216 (3)
C130.1062 (3)1.00731 (19)0.34634 (14)0.0292 (4)
H130.09161.10060.32530.035*
C140.1531 (3)0.9650 (2)0.42592 (15)0.0335 (5)
H140.17141.02910.45930.040*
C150.1751 (3)0.8282 (2)0.45953 (12)0.0271 (4)
C160.1489 (2)0.73448 (18)0.41255 (11)0.0219 (3)
H160.16190.64190.43570.026*
C170.1027 (2)0.77585 (16)0.32963 (11)0.0187 (3)
C180.0882 (2)0.67582 (16)0.28079 (10)0.0175 (3)
H180.10950.58420.30530.021*
C190.0507 (2)0.61584 (16)0.14497 (10)0.0172 (3)
C200.2570 (2)0.60202 (17)0.11302 (11)0.0213 (3)
H20A0.26210.54650.07010.026*0.835 (6)
H20B0.29590.69170.08840.026*0.835 (6)
H20C0.29630.69240.09020.026*0.165 (6)
H20D0.34250.56360.15930.026*0.165 (6)
C210.0160 (2)0.47961 (16)0.18370 (10)0.0197 (3)
H21A0.07470.43440.22670.024*0.831 (6)
H21B0.14360.49140.20880.024*0.831 (6)
H21C0.13890.49440.21190.024*0.169 (6)
H21D0.04070.42990.13980.024*0.169 (6)
C220.0847 (3)0.68282 (17)0.07586 (11)0.0229 (3)
H22A0.06760.63500.02940.027*
H22B0.21890.67840.09470.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0346 (3)0.0301 (2)0.0279 (2)0.00246 (19)0.01100 (18)0.00271 (18)
Cl20.0343 (3)0.0474 (3)0.0384 (3)0.0139 (2)0.0164 (2)0.0295 (2)
O10.0282 (7)0.0225 (6)0.0243 (6)0.0092 (5)0.0037 (5)0.0100 (5)
O50.0241 (6)0.0153 (6)0.0333 (7)0.0013 (5)0.0054 (5)0.0018 (5)
O20.0200 (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)
O30.0374 (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)
O40.0304 (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)
O60.0191 (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)
O70.0273 (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)
O80.0575 (10)0.0221 (7)0.0194 (6)0.0016 (6)0.0017 (6)0.0000 (5)
N10.0198 (7)0.0167 (7)0.0231 (7)0.0006 (5)0.0021 (5)0.0075 (5)
N20.0191 (7)0.0132 (6)0.0200 (7)0.0008 (5)0.0024 (5)0.0042 (5)
C10.0150 (7)0.0201 (8)0.0246 (8)0.0050 (6)0.0038 (6)0.0082 (6)
C20.0326 (10)0.0189 (8)0.0318 (10)0.0069 (7)0.0093 (8)0.0088 (7)
C30.0286 (9)0.0187 (8)0.0315 (10)0.0017 (7)0.0052 (7)0.0014 (7)
C40.0185 (8)0.0250 (9)0.0250 (9)0.0013 (6)0.0032 (6)0.0020 (7)
C50.0199 (8)0.0210 (8)0.0275 (9)0.0013 (6)0.0078 (7)0.0068 (7)
C60.0145 (7)0.0181 (8)0.0244 (8)0.0002 (6)0.0039 (6)0.0059 (6)
C70.0211 (8)0.0192 (8)0.0262 (9)0.0016 (6)0.0069 (6)0.0094 (7)
C80.0208 (8)0.0198 (8)0.0203 (8)0.0005 (6)0.0008 (6)0.0044 (6)
C90.0230 (9)0.0364 (11)0.0336 (10)0.0047 (8)0.0029 (8)0.0098 (8)
C100.0383 (11)0.0307 (10)0.0367 (11)0.0115 (8)0.0183 (9)0.0150 (8)
C110.0396 (11)0.0174 (8)0.0301 (10)0.0014 (7)0.0068 (8)0.0066 (7)
C120.0132 (7)0.0175 (8)0.0360 (10)0.0019 (6)0.0056 (6)0.0101 (7)
C130.0212 (9)0.0185 (8)0.0515 (12)0.0012 (7)0.0006 (8)0.0161 (8)
C140.0225 (9)0.0308 (10)0.0549 (13)0.0016 (7)0.0065 (8)0.0292 (9)
C150.0175 (8)0.0338 (10)0.0344 (10)0.0042 (7)0.0049 (7)0.0202 (8)
C160.0174 (8)0.0230 (8)0.0273 (9)0.0019 (6)0.0009 (6)0.0114 (7)
C170.0136 (7)0.0185 (8)0.0261 (8)0.0013 (6)0.0024 (6)0.0096 (6)
C180.0161 (7)0.0150 (7)0.0219 (8)0.0011 (6)0.0022 (6)0.0052 (6)
C190.0191 (8)0.0158 (7)0.0176 (7)0.0014 (6)0.0016 (6)0.0056 (6)
C200.0204 (8)0.0213 (8)0.0236 (8)0.0034 (6)0.0042 (6)0.0076 (6)
C210.0211 (8)0.0167 (7)0.0225 (8)0.0037 (6)0.0018 (6)0.0054 (6)
C220.0251 (9)0.0214 (8)0.0215 (8)0.0007 (7)0.0012 (7)0.0036 (6)
Geometric parameters (Å, º) top
Cl1—C41.7442 (19)C6—C71.431 (2)
Cl2—C151.744 (2)C7—H7A0.9500
O1—C11.302 (2)C8—C111.524 (2)
O5—C121.289 (2)C8—C101.526 (2)
O2—C91.318 (3)C8—C91.528 (3)
O2—H20.8400C9—H9A0.9900
O2'—C91.251 (4)C9—H9B0.9900
O2'—H2'0.8400C9—H9C0.9900
O2"—C91.268 (9)C9—H9D0.9900
O2"—H2"0.8400C9—H9E0.9900
O3—C101.417 (3)C9—H9F0.9900
O3—H30.8400C10—H10A0.9900
O3'—C101.318 (6)C10—H10B0.9900
O3'—H3'0.8400C10—H10C0.9900
O3"—C101.266 (6)C10—H10D0.9900
O3"—H3"0.8400C10—H10E0.9900
O4—C111.394 (3)C10—H10F0.9900
O4—H40.8400C11—H11A0.9900
O4'—C111.313 (4)C11—H11B0.9900
O4'—H4'0.8400C11—H11C0.9900
O6—C201.411 (2)C11—H11D0.9900
O6—H60.8400C12—C131.427 (2)
O6'—C201.389 (6)C12—C171.435 (2)
O6'—H6'0.8400C13—C141.360 (3)
O7—C211.405 (2)C13—H130.9500
O7—H70.8400C14—C151.402 (3)
O7'—C211.428 (6)C14—H140.9500
O7'—H7'0.8400C15—C161.368 (2)
O8—C221.421 (2)C16—C171.409 (2)
O8—H80.8400C16—H160.9500
N1—C71.288 (2)C17—C181.428 (2)
N1—C81.467 (2)C18—H180.9500
N1—H1N0.885 (10)C19—C211.529 (2)
N2—C181.297 (2)C19—C221.532 (2)
N2—C191.468 (2)C19—C201.539 (2)
N2—H2N0.886 (10)C20—H20A0.9900
C1—C21.418 (2)C20—H20B0.9900
C1—C61.430 (2)C20—H20C0.9900
C2—C31.370 (3)C20—H20D0.9900
C2—H2A0.9500C21—H21A0.9900
C3—C41.400 (3)C21—H21B0.9900
C3—H3A0.9500C21—H21C0.9900
C4—C51.368 (2)C21—H21D0.9900
C5—C61.405 (2)C22—H22A0.9900
C5—H50.9500C22—H22B0.9900
C9—O2—H2109.5H10E—C10—H10F105.1
C9—O2'—H2'109.5O4'—C11—O4103.6 (2)
C9—O2"—H2"109.5O4'—C11—C8123.9 (2)
C10—O3—H3109.5O4—C11—C8107.90 (16)
C10—O3'—H3'109.5O4—C11—H11A110.1
C10—O3"—H3"109.5C8—C11—H11A110.1
C11—O4—H4109.5O4'—C11—H11B100.6
C11—O4'—H4'109.5O4—C11—H11B110.1
C20—O6—H6109.5C8—C11—H11B110.1
C20—O6'—H6'109.5H11A—C11—H11B108.4
C21—O7—H7109.5O4'—C11—H11C106.4
C21—O7'—H7'109.5O4—C11—H11C108.0
C22—O8—H8109.5C8—C11—H11C106.4
C7—N1—C8127.86 (14)O4'—C11—H11D106.4
C7—N1—H1N112.8 (18)C8—C11—H11D106.4
C8—N1—H1N119.1 (18)H11B—C11—H11D108.8
C18—N2—C19127.48 (14)H11C—C11—H11D106.4
C18—N2—H2N114.0 (16)O5—C12—C13122.12 (16)
C19—N2—H2N118.0 (16)O5—C12—C17121.79 (15)
O1—C1—C2121.63 (15)C13—C12—C17116.09 (17)
O1—C1—C6121.54 (15)C14—C13—C12121.68 (18)
C2—C1—C6116.83 (16)C14—C13—H13119.2
C3—C2—C1121.40 (16)C12—C13—H13119.2
C3—C2—H2A119.3C13—C14—C15120.98 (17)
C1—C2—H2A119.3C13—C14—H14119.5
C2—C3—C4120.73 (17)C15—C14—H14119.5
C2—C3—H3A119.6C16—C15—C14120.36 (19)
C4—C3—H3A119.6C16—C15—Cl2120.69 (16)
C5—C4—C3120.11 (17)C14—C15—Cl2118.94 (14)
C5—C4—Cl1120.71 (14)C15—C16—C17119.69 (17)
C3—C4—Cl1119.18 (14)C15—C16—H16120.2
C4—C5—C6120.31 (16)C17—C16—H16120.2
C4—C5—H5119.8C16—C17—C18118.51 (15)
C6—C5—H5119.8C16—C17—C12121.20 (15)
C5—C6—C1120.61 (15)C18—C17—C12120.24 (16)
C5—C6—C7118.89 (15)N2—C18—C17121.93 (15)
C1—C6—C7120.46 (15)N2—C18—H18119.0
N1—C7—C6122.31 (15)C17—C18—H18119.0
N1—C7—H7A118.8N2—C19—C21111.20 (13)
C6—C7—H7A118.8N2—C19—C22106.69 (13)
N1—C8—C11112.26 (14)C21—C19—C22109.93 (14)
N1—C8—C10105.88 (15)N2—C19—C20107.43 (13)
C11—C8—C10109.77 (15)C21—C19—C20111.18 (14)
N1—C8—C9108.14 (14)C22—C19—C20110.29 (14)
C11—C8—C9110.66 (16)O6'—C20—O6105.2 (4)
C10—C8—C9110.00 (16)O6'—C20—C19114.2 (3)
O2'—C9—C8124.6 (2)O6—C20—C19111.78 (14)
O2"—C9—C8104.9 (4)O6—C20—H20A109.3
O2—C9—C8119.54 (19)C19—C20—H20A109.3
O2'—C9—H9A103.4O6'—C20—H20B106.9
O2—C9—H9A107.4O6—C20—H20B109.3
C8—C9—H9A107.4C19—C20—H20B109.3
O2"—C9—H9B118.1H20A—C20—H20B107.9
O2—C9—H9B107.4O6'—C20—H20C108.7
C8—C9—H9B107.4O6—C20—H20C108.0
H9A—C9—H9B107.0C19—C20—H20C108.7
O2'—C9—H9C106.2H20A—C20—H20C109.8
C8—C9—H9C106.2O6'—C20—H20D108.7
H9A—C9—H9C108.2C19—C20—H20D108.7
H9B—C9—H9C120.1H20A—C20—H20D112.6
O2'—C9—H9D106.2H20B—C20—H20D109.0
O2—C9—H9D106.2H20C—C20—H20D107.6
C8—C9—H9D106.2O7—C21—O7'101.9 (3)
H9B—C9—H9D109.8O7—C21—C19108.48 (14)
O2"—C9—H9E110.8O7'—C21—C19115.5 (3)
O2—C9—H9E110.1O7—C21—H21A110.0
C8—C9—H9E110.8C19—C21—H21A110.0
O2"—C9—H9F110.8O7—C21—H21B110.0
C8—C9—H9F110.8O7'—C21—H21B110.7
H9E—C9—H9F108.8C19—C21—H21B110.0
O3'—C10—C8116.5 (5)H21A—C21—H21B108.4
O3—C10—C8111.74 (16)O7—C21—H21C114.3
O3—C10—H10A109.3O7'—C21—H21C108.4
C8—C10—H10A109.3C19—C21—H21C108.4
O3—C10—H10B109.3H21A—C21—H21C105.6
C8—C10—H10B109.3O7'—C21—H21D108.4
H10A—C10—H10B107.9C19—C21—H21D108.4
O3'—C10—H10C108.2H21A—C21—H21D116.7
C8—C10—H10C108.2H21B—C21—H21D103.1
O3'—C10—H10D108.2H21C—C21—H21D107.5
C8—C10—H10D108.2O8—C22—C19109.62 (14)
H10C—C10—H10D107.3O8—C22—H22A109.7
C8—C10—H10E103.1C19—C22—H22A109.7
O3"—C10—H10F103.1O8—C22—H22B109.7
O3'—C10—H10F104.6C19—C22—H22B109.7
O3—C10—H10F101.4H22A—C22—H22B108.2
C8—C10—H10F103.1
O1—C1—C2—C3179.32 (17)C9—C8—C11—O4'58.1 (3)
C6—C1—C2—C30.5 (3)N1—C8—C11—O4176.23 (16)
C1—C2—C3—C40.0 (3)C10—C8—C11—O458.8 (2)
C2—C3—C4—C50.8 (3)C9—C8—C11—O462.8 (2)
C2—C3—C4—Cl1178.35 (15)O5—C12—C13—C14179.70 (17)
C3—C4—C5—C61.1 (3)C17—C12—C13—C140.0 (3)
Cl1—C4—C5—C6178.02 (13)C12—C13—C14—C150.3 (3)
C4—C5—C6—C10.6 (3)C13—C14—C15—C160.2 (3)
C4—C5—C6—C7177.26 (16)C13—C14—C15—Cl2178.80 (15)
O1—C1—C6—C5179.64 (15)C14—C15—C16—C171.0 (3)
C2—C1—C6—C50.2 (2)Cl2—C15—C16—C17177.95 (13)
O1—C1—C6—C71.8 (2)C15—C16—C17—C18176.05 (16)
C2—C1—C6—C7178.03 (16)C15—C16—C17—C121.4 (3)
C8—N1—C7—C6174.53 (16)O5—C12—C17—C16179.45 (15)
C5—C6—C7—N1178.05 (16)C13—C12—C17—C160.9 (2)
C1—C6—C7—N10.2 (3)O5—C12—C17—C183.2 (2)
C7—N1—C8—C117.8 (2)C13—C12—C17—C18176.51 (15)
C7—N1—C8—C10127.59 (19)C19—N2—C18—C17171.78 (15)
C7—N1—C8—C9114.5 (2)C16—C17—C18—N2179.76 (15)
N1—C8—C9—O2'52.8 (3)C12—C17—C18—N22.3 (2)
C11—C8—C9—O2'176.2 (3)C18—N2—C19—C2136.7 (2)
C10—C8—C9—O2'62.4 (3)C18—N2—C19—C22156.57 (16)
N1—C8—C9—O2"174.6 (5)C18—N2—C19—C2085.16 (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—O263.7 (2)C22—C19—C20—O6'61.8 (4)
C11—C8—C9—O259.6 (2)N2—C19—C20—O662.94 (17)
C10—C8—C9—O2178.90 (19)C21—C19—C20—O658.93 (18)
N1—C8—C10—O3"80.6 (7)C22—C19—C20—O6178.86 (14)
C11—C8—C10—O3"40.8 (7)N2—C19—C21—O7175.00 (14)
C9—C8—C10—O3"162.8 (7)C22—C19—C21—O757.08 (18)
N1—C8—C10—O3'92.1 (5)C20—C19—C21—O765.33 (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—O346.0 (2)C20—C19—C21—O7'48.2 (4)
C11—C8—C10—O3167.35 (18)N2—C19—C22—O848.05 (18)
C9—C8—C10—O370.7 (2)C21—C19—C22—O8168.73 (14)
N1—C8—C11—O4'62.9 (3)C20—C19—C22—O868.33 (18)
C10—C8—C11—O4'179.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1n···O10.87 (1)1.82 (2)2.582 (2)143 (2)
N2—H2n···O50.87 (1)1.82 (2)2.573 (2)141 (2)

Experimental details

Crystal data
Chemical formulaC11H14ClNO4
Mr259.68
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)7.0174 (1), 10.1935 (1), 16.7234 (2)
α, β, γ (°)79.520 (1), 89.031 (1), 85.258 (1)
V3)1172.27 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.33
Crystal size (mm)0.30 × 0.20 × 0.05
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.908, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections
11241, 5361, 4771
Rint0.018
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.117, 1.01
No. of reflections5361
No. of parameters360
No. of restraints47
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.41, 0.74

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), pubCIF (Westrip, 2008).

 

Acknowledgements

I thank the University of Malaya for supporting this study.

References

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First citationTatar, L., Nazir, H., Gümüser, M., Kate, C. & Atakol, O. (2005). Z. Kristallogr. 220, 639–642.  Web of Science CSD CrossRef CAS Google Scholar
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