(E)-N′-[2-(4-Chloro-3-nitro­phenyl­sulfon­yloxy)-3-methoxy­benzyl­idene]isonicotinohydrazide acetic acid tetra­solvate

Zhen, X.-L.; Li, X.-L.

doi:10.1107/S1600536808034089

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2170

doi:10.1107/S1600536808034089

Open

access

(E)-N′-[2-(4-Chloro-3-nitrophenylsulfonyloxy)-3-methoxybenzylidene]isonicotinohydrazide acetic acid tetrasolvate

Xiao-Li Zhen ^a,^b and Xiao-Liu Li ^a ^*

^aCollege of Chemistry & Environmental Science, Hebei University, Baoding 071002, People's Republic of China, and ^bCollege of Sciences, Hebei University of Science & Technology, Shijiazhuang 050018, People's Republic of China
^*Correspondence e-mail: li_xiaoliu99@163.com

(Received 7 October 2008; accepted 18 October 2008; online 22 October 2008)

In the title compound, C₂₀H₁₅ClN₄O₇S·4CH₃COOH, the central o-vanillin group makes dihedral angles of 9.50 (11) and 42.86 (7)°, respectively, with its attached pyridine and nitrobenzene rings. The crystal packing is stabilized by N—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds and C—H⋯O interactions, leading to an infinite three-dimensional network. A short intramolecular C—H⋯O contact is also seen.

Related literature

For general background, see: Allen et al. (1987 ); Jones et al. (1979 ); Larson & Pecoraro, (1991 ); Santos et al. (2001 ).

Experimental

Crystal data

C₂₀H₁₅ClN₄O₇S·4C₂H₄O₂
M_r = 731.09
Triclinic, $[P \overline 1]$
a = 8.0565 (16) Å
b = 13.876 (3) Å
c = 16.097 (3) Å
α = 79.01 (3)°
β = 76.01 (3)°
γ = 75.44 (3)°
V = 1673.8 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 294 (2) K
0.23 × 0.18 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.913, T_max = 0.970
9794 measured reflections
5882 independent reflections
4448 reflections with I > 2σ(I)
R_int = 0.081

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.146
S = 1.01
5882 reflections
451 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O71—H71⋯N11ⁱ	0.82	1.84	2.661 (3)	176
C35—H35⋯O17ⁱⁱ	0.93	2.51	3.360 (3)	152
O41—H41⋯O17ⁱⁱⁱ	0.82	1.96	2.698 (3)	150
O41—H41⋯N27ⁱⁱⁱ	0.82	2.59	3.211 (3)	134
N17—H17⋯O42^iv	0.86	2.10	2.875 (3)	150
C27—H27⋯O42^iv	0.93	2.43	3.206 (4)	140
O51—H51⋯O52ⁱⁱⁱ	0.82	1.87	2.672 (3)	167
C24—H24⋯O62ⁱⁱⁱ	0.93	2.54	3.461 (3)	170
O61—H61⋯O62^v	0.82	1.83	2.648 (3)	178
C12—H12⋯O72ⁱ	0.93	2.59	3.255 (3)	129
C32—H32⋯O72	0.93	2.37	3.122 (4)	137
Symmetry codes: (i) -x+2, -y+1, -z+2; (ii) x-1, y+1, z; (iii) -x+1, -y+1, -z+1; (iv) x, y, z+1; (v) -x+2, -y, -z+1.

Data collection: SMART (Bruker, 1999 ); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808034089/at2646sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808034089/at2646Isup2.hkl

checkCIF report

Comment top

There has been a steady growth of interest in the synthesis, structure, and reactivity of Schiff bases due to their potential applications in areas such as biological modelling, catalysis, and molecular magnets (Jones et al., 1979; Larson & Pecoraro, 1991). One of the aims of investigating the structural chemistry of Schiff bases is to develop protein and enzyme mimics (Santos et al., 2001). As part of an investigation of the coordination properties of Schiff bases functioning as ligands, we report the synthesis and structure of the title compound (I).

In the title molecule (Fig. 1), bond lengths and angles are within normal ranges (Allen et al., 1987). The o-vanillin group (C21–C27/O22/O23) is essentially planar, with an r.m.s. deviation for fitted atoms of 0.0236 Å. This group makes dihedral angles of 9.50 (11)° and 42.86 (7)°, respectively, with the pyridine ring (C12—C16/N11) and the benzene ring (C31—C36). Furthermore, the dihedral angle between the pyridine ring (C12—C16/N11) and the benzene ring (C31—C36) is 50.43 (8)°.

The crystal packing is stabilized by N—H···O, O—H···O, O—H···N hydrogen bonds and C—H···O interactions (Table 1, Fig. 2), leading to an infinite network.

Related literature top

For general background, see: Allen et al. (1987); Jones et al. (1979); Larson & Pecoraro, (1991); Santos et al. (2001).

Experimental top

An anhydrous ethanol solution (50 ml) of 2-formyl-6-methoxyphenyl 4-chloro-3-nitrobenzenesulfonate (3.72 g, 10 mmol) was added to an anhydrous ethanol solution (50 ml) of isonicotinohydrazide (1.37 g, 10 mmol) and the mixture stirred at 350 K for 5 h under nitrogen, giving a yellow precipitate. The product was isolated, recrystallized from ethanol and then dried in a vacuum to give the pure compound in 78% yield. Yellow single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an acetic acid solution.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of (I) with displacement ellipsoids for non-H atoms drawn at the 30% probability level.
	Fig. 2. A stereoview of part of the crystal structure of compound (I), showing the formation of a complex network. For the sake of clarity, H atoms not involved in the hydrogen bonds shown have been omitted.

(E)-N'-[2-(4-Chloro-3-nitrophenylsulfonyloxy)-3- methoxybenzylidene]isonicotinohydrazide acetic acid tetrasolvate top

Crystal data top

C₂₀H₁₅ClN₄O₇S·4C₂H₄O₂	Z = 2
M_r = 731.09	F(000) = 760
Triclinic, P1	D_x = 1.451 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0565 (16) Å	Cell parameters from 4854 reflections
b = 13.876 (3) Å	θ = 2.2–28.0°
c = 16.097 (3) Å	µ = 0.25 mm⁻¹
α = 79.01 (3)°	T = 294 K
β = 76.01 (3)°	Block, yellow
γ = 75.44 (3)°	0.23 × 0.18 × 0.12 mm
V = 1673.8 (7) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5882 independent reflections
Radiation source: fine-focus sealed tube	4448 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.081
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→9
T_min = 0.913, T_max = 0.970	k = −16→13
9794 measured reflections	l = −19→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0627P)²] where P = (F_o² + 2F_c²)/3
5882 reflections	(Δ/σ)_max = 0.001
451 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₂₀H₁₅ClN₄O₇S·4C₂H₄O₂	γ = 75.44 (3)°
M_r = 731.09	V = 1673.8 (7) Å³
Triclinic, P1	Z = 2
a = 8.0565 (16) Å	Mo Kα radiation
b = 13.876 (3) Å	µ = 0.25 mm⁻¹
c = 16.097 (3) Å	T = 294 K
α = 79.01 (3)°	0.23 × 0.18 × 0.12 mm
β = 76.01 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5882 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4448 reflections with I > 2σ(I)
T_min = 0.913, T_max = 0.970	R_int = 0.081
9794 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.146	H-atom parameters constrained
S = 1.01	Δρ_max = 0.30 e Å⁻³
5882 reflections	Δρ_min = −0.44 e Å⁻³
451 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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.36674 (7)	0.89584 (4)	0.99002 (5)	0.01955 (19)
O1	0.2825 (2)	0.90760 (14)	1.07606 (14)	0.0286 (5)
O2	0.5507 (2)	0.85500 (13)	0.96749 (14)	0.0244 (5)
N11	1.0675 (2)	0.32110 (15)	1.23406 (16)	0.0208 (5)
C12	1.1069 (3)	0.27264 (19)	1.1657 (2)	0.0207 (6)
H12	1.1880	0.2117	1.1662	0.025*
C13	1.0324 (3)	0.30910 (18)	1.0941 (2)	0.0201 (6)
H13	1.0630	0.2731	1.0475	0.024*
C14	0.9115 (3)	0.40008 (17)	1.09249 (18)	0.0169 (6)
C15	0.8746 (3)	0.45215 (19)	1.1617 (2)	0.0226 (6)
H15	0.7976	0.5146	1.1618	0.027*
C16	0.9547 (3)	0.4098 (2)	1.2318 (2)	0.0247 (6)
H16	0.9284	0.4448	1.2788	0.030*
C17	0.8325 (3)	0.43673 (18)	1.01316 (19)	0.0178 (6)
N17	0.7134 (2)	0.52433 (14)	1.01405 (16)	0.0181 (5)
H17	0.6802	0.5543	1.0593	0.022*
O17	0.8782 (2)	0.38954 (13)	0.95161 (13)	0.0238 (5)
C21	0.4519 (3)	0.70078 (17)	0.87464 (18)	0.0164 (6)
C22	0.3222 (3)	0.78844 (18)	0.88440 (18)	0.0155 (5)
O22	0.26276 (19)	0.82421 (12)	0.96469 (12)	0.0177 (4)
C23	0.2359 (3)	0.83875 (17)	0.81745 (19)	0.0189 (6)
O23	0.1050 (2)	0.91963 (12)	0.83710 (13)	0.0214 (4)
C23A	0.0280 (3)	0.9805 (2)	0.7665 (2)	0.0268 (7)
H23A	−0.0291	0.9413	0.7440	0.040*
H23B	0.1183	1.0029	0.7216	0.040*
H23C	−0.0561	1.0378	0.7871	0.040*
C24	0.2833 (3)	0.80131 (18)	0.73985 (19)	0.0189 (6)
H24	0.2276	0.8335	0.6946	0.023*
C25	0.4150 (3)	0.71516 (18)	0.72938 (19)	0.0200 (6)
H25	0.4475	0.6907	0.6765	0.024*
C26	0.4983 (3)	0.66517 (18)	0.7960 (2)	0.0206 (6)
H26	0.5857	0.6075	0.7878	0.025*
C27	0.5316 (3)	0.64754 (17)	0.94872 (19)	0.0178 (6)
H27	0.4993	0.6737	1.0008	0.021*
N27	0.6456 (2)	0.56518 (14)	0.94087 (15)	0.0173 (5)
C31	0.3174 (3)	1.00961 (18)	0.92192 (19)	0.0202 (6)
C32	0.4306 (3)	1.02540 (18)	0.8445 (2)	0.0210 (6)
H32	0.5329	0.9781	0.8287	0.025*
C33	0.3873 (3)	1.11389 (19)	0.7910 (2)	0.0230 (6)
N33	0.5045 (3)	1.13006 (17)	0.7079 (2)	0.0342 (6)
O33	0.4431 (3)	1.14733 (18)	0.64263 (17)	0.0503 (7)
O34	0.6588 (2)	1.12465 (17)	0.70740 (18)	0.0486 (7)
C34	0.2382 (3)	1.18656 (19)	0.8158 (2)	0.0246 (7)
Cl34	0.19242 (9)	1.30033 (5)	0.75118 (6)	0.0351 (2)
C35	0.1276 (3)	1.16966 (19)	0.8944 (2)	0.0244 (6)
H35	0.0273	1.2179	0.9111	0.029*
C36	0.1665 (3)	1.08062 (19)	0.9483 (2)	0.0223 (6)
H36	0.0928	1.0682	1.0015	0.027*
C41	0.3533 (3)	0.61046 (19)	0.2126 (2)	0.0254 (7)
O41	0.2137 (2)	0.58404 (16)	0.20296 (15)	0.0329 (5)
H41	0.2225	0.5796	0.1519	0.049*
O42	0.4795 (2)	0.61927 (15)	0.15511 (15)	0.0318 (5)
C42	0.3373 (4)	0.6290 (3)	0.3024 (2)	0.0473 (9)
H42A	0.4483	0.6360	0.3097	0.071*
H42B	0.3020	0.5735	0.3424	0.071*
H42C	0.2512	0.6896	0.3131	0.071*
C51	0.3163 (4)	0.4268 (2)	0.5144 (2)	0.0378 (8)
O51	0.2940 (3)	0.4842 (2)	0.57278 (19)	0.0548 (7)
H51	0.3672	0.5192	0.5583	0.082*
O52	0.4437 (3)	0.42050 (18)	0.45479 (18)	0.0491 (6)
C52	0.1786 (5)	0.3693 (3)	0.5263 (3)	0.0520 (10)
H52A	0.1674	0.3586	0.4709	0.078*
H52B	0.0691	0.4065	0.5549	0.078*
H52C	0.2098	0.3056	0.5608	0.078*
C61	0.8864 (3)	0.1393 (2)	0.4933 (2)	0.0299 (7)
O61	0.9839 (2)	0.10855 (16)	0.55199 (15)	0.0348 (5)
H61	1.0288	0.0486	0.5514	0.052*
O62	0.8689 (3)	0.08503 (15)	0.44639 (16)	0.0371 (6)
C62	0.7966 (4)	0.2472 (2)	0.4893 (2)	0.0400 (8)
H62A	0.6736	0.2527	0.5125	0.060*
H62B	0.8137	0.2787	0.4302	0.060*
H62C	0.8446	0.2799	0.5225	0.060*
C71	0.6959 (3)	0.8590 (2)	0.6418 (2)	0.0239 (7)
O71	0.7975 (2)	0.77024 (14)	0.62854 (14)	0.0272 (5)
H71	0.8338	0.7429	0.6725	0.041*
O72	0.6782 (2)	0.89620 (14)	0.70593 (15)	0.0316 (5)
C72	0.6031 (3)	0.9089 (2)	0.5696 (2)	0.0333 (8)
H72A	0.4879	0.8950	0.5829	0.050*
H72B	0.6679	0.8834	0.5171	0.050*
H72C	0.5940	0.9801	0.5626	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0179 (3)	0.0224 (4)	0.0203 (4)	−0.0036 (2)	−0.0060 (3)	−0.0059 (3)
O1	0.0352 (10)	0.0325 (11)	0.0204 (13)	−0.0055 (8)	−0.0070 (9)	−0.0096 (9)
O2	0.0186 (8)	0.0266 (10)	0.0302 (13)	−0.0039 (7)	−0.0092 (8)	−0.0054 (9)
N11	0.0165 (10)	0.0231 (12)	0.0227 (15)	−0.0043 (8)	−0.0057 (10)	−0.0009 (11)
C12	0.0142 (11)	0.0227 (14)	0.0237 (18)	−0.0045 (9)	−0.0026 (11)	−0.0008 (12)
C13	0.0182 (11)	0.0201 (13)	0.0230 (17)	−0.0059 (9)	−0.0039 (11)	−0.0033 (12)
C14	0.0149 (11)	0.0201 (13)	0.0157 (16)	−0.0073 (9)	−0.0026 (11)	0.0013 (11)
C15	0.0225 (12)	0.0190 (13)	0.0261 (18)	−0.0003 (10)	−0.0083 (12)	−0.0041 (12)
C16	0.0236 (12)	0.0305 (15)	0.0203 (18)	−0.0041 (11)	−0.0049 (12)	−0.0059 (13)
C17	0.0151 (11)	0.0184 (13)	0.0208 (17)	−0.0075 (10)	−0.0030 (11)	−0.0002 (12)
N17	0.0182 (9)	0.0173 (11)	0.0195 (14)	−0.0022 (8)	−0.0068 (10)	−0.0027 (10)
O17	0.0265 (9)	0.0212 (10)	0.0237 (13)	0.0021 (7)	−0.0087 (9)	−0.0081 (9)
C21	0.0148 (10)	0.0163 (13)	0.0191 (16)	−0.0064 (9)	−0.0043 (11)	0.0006 (11)
C22	0.0154 (11)	0.0199 (13)	0.0123 (15)	−0.0068 (9)	−0.0007 (10)	−0.0037 (11)
O22	0.0166 (8)	0.0209 (9)	0.0157 (11)	−0.0048 (6)	−0.0028 (8)	−0.0028 (8)
C23	0.0140 (11)	0.0165 (13)	0.0275 (18)	−0.0048 (9)	−0.0065 (11)	−0.0015 (12)
O23	0.0190 (8)	0.0243 (9)	0.0199 (12)	0.0013 (7)	−0.0076 (8)	−0.0036 (8)
C23A	0.0271 (13)	0.0265 (14)	0.0245 (19)	0.0019 (11)	−0.0139 (13)	0.0029 (13)
C24	0.0189 (11)	0.0238 (14)	0.0166 (16)	−0.0087 (10)	−0.0057 (11)	−0.0011 (12)
C25	0.0217 (12)	0.0239 (14)	0.0167 (16)	−0.0080 (10)	−0.0020 (11)	−0.0064 (12)
C26	0.0182 (11)	0.0181 (13)	0.0266 (18)	−0.0037 (10)	−0.0043 (12)	−0.0063 (12)
C27	0.0175 (11)	0.0206 (13)	0.0164 (16)	−0.0079 (10)	−0.0035 (11)	−0.0002 (11)
N27	0.0161 (9)	0.0174 (11)	0.0194 (14)	−0.0043 (8)	−0.0063 (9)	−0.0008 (9)
C31	0.0165 (11)	0.0208 (13)	0.0270 (18)	−0.0056 (9)	−0.0048 (12)	−0.0099 (12)
C32	0.0156 (11)	0.0191 (13)	0.0281 (18)	0.0008 (9)	−0.0048 (12)	−0.0080 (12)
C33	0.0201 (12)	0.0254 (14)	0.0232 (18)	−0.0062 (10)	0.0001 (12)	−0.0068 (12)
N33	0.0341 (13)	0.0245 (13)	0.0343 (19)	−0.0002 (10)	0.0037 (12)	−0.0027 (12)
O33	0.0529 (13)	0.0589 (15)	0.0228 (15)	0.0053 (11)	0.0007 (12)	−0.0003 (12)
O34	0.0249 (10)	0.0518 (14)	0.0540 (19)	−0.0077 (9)	0.0101 (11)	0.0052 (12)
C34	0.0211 (12)	0.0189 (13)	0.036 (2)	−0.0016 (10)	−0.0101 (13)	−0.0067 (12)
Cl34	0.0359 (4)	0.0236 (4)	0.0399 (5)	0.0018 (3)	−0.0083 (4)	−0.0007 (3)
C35	0.0187 (12)	0.0229 (14)	0.0305 (19)	−0.0001 (10)	−0.0027 (12)	−0.0102 (13)
C36	0.0162 (11)	0.0262 (14)	0.0263 (18)	−0.0056 (10)	−0.0008 (11)	−0.0112 (12)
C41	0.0258 (13)	0.0254 (14)	0.0229 (19)	−0.0002 (11)	−0.0073 (13)	−0.0027 (13)
O41	0.0276 (10)	0.0474 (13)	0.0254 (14)	−0.0059 (8)	−0.0047 (10)	−0.0127 (11)
O42	0.0275 (10)	0.0381 (11)	0.0261 (14)	−0.0023 (8)	−0.0008 (10)	−0.0080 (10)
C42	0.0498 (19)	0.073 (2)	0.027 (2)	−0.0286 (17)	−0.0041 (17)	−0.0110 (19)
C51	0.0457 (18)	0.0357 (18)	0.032 (2)	0.0015 (14)	−0.0159 (17)	−0.0072 (16)
O51	0.0612 (15)	0.0578 (16)	0.050 (2)	−0.0169 (12)	0.0004 (14)	−0.0288 (15)
O52	0.0518 (14)	0.0538 (15)	0.0441 (18)	−0.0069 (11)	−0.0038 (13)	−0.0264 (13)
C52	0.059 (2)	0.061 (2)	0.042 (3)	−0.0182 (17)	−0.0104 (19)	−0.0138 (19)
C61	0.0215 (13)	0.0445 (18)	0.0185 (18)	−0.0082 (12)	0.0015 (12)	0.0021 (15)
O61	0.0312 (10)	0.0453 (12)	0.0282 (14)	−0.0054 (9)	−0.0093 (10)	−0.0054 (10)
O62	0.0427 (12)	0.0388 (12)	0.0330 (15)	−0.0062 (9)	−0.0180 (11)	−0.0033 (11)
C62	0.0346 (15)	0.0464 (19)	0.034 (2)	−0.0027 (13)	−0.0053 (15)	−0.0036 (16)
C71	0.0169 (12)	0.0291 (16)	0.0236 (19)	−0.0072 (11)	−0.0007 (12)	0.0002 (13)
O71	0.0268 (9)	0.0301 (11)	0.0226 (13)	0.0001 (8)	−0.0089 (9)	−0.0017 (9)
O72	0.0359 (10)	0.0298 (11)	0.0283 (14)	0.0003 (8)	−0.0091 (10)	−0.0086 (10)
C72	0.0278 (14)	0.0384 (17)	0.029 (2)	−0.0028 (12)	−0.0090 (14)	0.0035 (14)

Geometric parameters (Å, º) top

S1—O1	1.408 (2)	C32—C33	1.378 (4)
S1—O2	1.4303 (18)	C32—H32	0.9300
S1—O22	1.6107 (17)	C33—C34	1.390 (4)
S1—C31	1.757 (3)	C33—N33	1.453 (4)
N11—C12	1.330 (4)	N33—O33	1.225 (4)
N11—C16	1.334 (3)	N33—O34	1.225 (3)
C12—C13	1.380 (4)	C34—C35	1.377 (4)
C12—H12	0.9300	C34—Cl34	1.726 (3)
C13—C14	1.388 (3)	C35—C36	1.380 (4)
C13—H13	0.9300	C35—H35	0.9300
C14—C15	1.375 (4)	C36—H36	0.9300
C14—C17	1.509 (4)	C41—O42	1.212 (3)
C15—C16	1.393 (4)	C41—O41	1.318 (3)
C15—H15	0.9300	C41—C42	1.486 (5)
C16—H16	0.9300	O41—H41	0.8200
C17—O17	1.223 (3)	C42—H42A	0.9600
C17—N17	1.346 (3)	C42—H42B	0.9600
N17—N27	1.381 (3)	C42—H42C	0.9600
N17—H17	0.8600	C51—O52	1.222 (4)
C21—C26	1.380 (4)	C51—O51	1.297 (4)
C21—C22	1.397 (3)	C51—C52	1.479 (5)
C21—C27	1.475 (3)	O51—H51	0.8200
C22—C23	1.401 (3)	C52—H52A	0.9600
C22—O22	1.404 (3)	C52—H52B	0.9600
C23—O23	1.360 (3)	C52—H52C	0.9600
C23—C24	1.376 (4)	C61—O62	1.216 (4)
O23—C23A	1.450 (3)	C61—O61	1.315 (3)
C23A—H23A	0.9600	C61—C62	1.487 (4)
C23A—H23B	0.9600	O61—H61	0.8200
C23A—H23C	0.9600	C62—H62A	0.9600
C24—C25	1.391 (4)	C62—H62B	0.9600
C24—H24	0.9300	C62—H62C	0.9600
C25—C26	1.383 (4)	C71—O72	1.203 (4)
C25—H25	0.9300	C71—O71	1.320 (3)
C26—H26	0.9300	C71—C72	1.497 (4)
C27—N27	1.279 (3)	O71—H71	0.8200
C27—H27	0.9300	C72—H72A	0.9600
C31—C32	1.371 (4)	C72—H72B	0.9600
C31—C36	1.392 (4)	C72—H72C	0.9600

O1—S1—O2	121.40 (12)	C36—C31—S1	119.3 (2)
O1—S1—O22	103.04 (11)	C31—C32—C33	117.6 (2)
O2—S1—O22	108.77 (10)	C31—C32—H32	121.2
O1—S1—C31	110.02 (13)	C33—C32—H32	121.2
O2—S1—C31	108.32 (12)	C32—C33—C34	121.4 (3)
O22—S1—C31	103.83 (10)	C32—C33—N33	117.9 (2)
C12—N11—C16	118.2 (2)	C34—C33—N33	120.7 (2)
N11—C12—C13	122.7 (2)	O33—N33—O34	124.1 (3)
N11—C12—H12	118.6	O33—N33—C33	118.0 (2)
C13—C12—H12	118.6	O34—N33—C33	117.9 (3)
C12—C13—C14	119.2 (3)	C35—C34—C33	120.0 (2)
C12—C13—H13	120.4	C35—C34—Cl34	119.0 (2)
C14—C13—H13	120.4	C33—C34—Cl34	121.0 (2)
C15—C14—C13	118.3 (2)	C34—C35—C36	119.6 (2)
C15—C14—C17	124.2 (2)	C34—C35—H35	120.2
C13—C14—C17	117.4 (3)	C36—C35—H35	120.2
C14—C15—C16	118.9 (2)	C35—C36—C31	119.1 (3)
C14—C15—H15	120.6	C35—C36—H36	120.4
C16—C15—H15	120.6	C31—C36—H36	120.4
N11—C16—C15	122.6 (3)	O42—C41—O41	124.2 (3)
N11—C16—H16	118.7	O42—C41—C42	123.9 (2)
C15—C16—H16	118.7	O41—C41—C42	111.9 (3)
O17—C17—N17	122.8 (2)	C41—O41—H41	109.5
O17—C17—C14	121.1 (2)	C41—C42—H42A	109.5
N17—C17—C14	116.1 (3)	C41—C42—H42B	109.5
C17—N17—N27	118.7 (2)	H42A—C42—H42B	109.5
C17—N17—H17	120.7	C41—C42—H42C	109.5
N27—N17—H17	120.7	H42A—C42—H42C	109.5
C26—C21—C22	118.6 (2)	H42B—C42—H42C	109.5
C26—C21—C27	121.9 (2)	O52—C51—O51	121.7 (3)
C22—C21—C27	119.5 (3)	O52—C51—C52	123.1 (3)
C21—C22—C23	121.7 (3)	O51—C51—C52	115.2 (3)
C21—C22—O22	120.7 (2)	C51—O51—H51	109.5
C23—C22—O22	117.4 (2)	C51—C52—H52A	109.5
C22—O22—S1	119.17 (15)	C51—C52—H52B	109.5
O23—C23—C24	125.5 (2)	H52A—C52—H52B	109.5
O23—C23—C22	115.7 (3)	C51—C52—H52C	109.5
C24—C23—C22	118.7 (2)	H52A—C52—H52C	109.5
C23—O23—C23A	116.9 (2)	H52B—C52—H52C	109.5
O23—C23A—H23A	109.5	O62—C61—O61	123.7 (3)
O23—C23A—H23B	109.5	O62—C61—C62	122.3 (3)
H23A—C23A—H23B	109.5	O61—C61—C62	114.1 (3)
O23—C23A—H23C	109.5	C61—O61—H61	109.5
H23A—C23A—H23C	109.5	C61—C62—H62A	109.5
H23B—C23A—H23C	109.5	C61—C62—H62B	109.5
C23—C24—C25	119.7 (2)	H62A—C62—H62B	109.5
C23—C24—H24	120.1	C61—C62—H62C	109.5
C25—C24—H24	120.1	H62A—C62—H62C	109.5
C26—C25—C24	121.3 (3)	H62B—C62—H62C	109.5
C26—C25—H25	119.3	O72—C71—O71	123.4 (2)
C24—C25—H25	119.3	O72—C71—C72	123.0 (3)
C21—C26—C25	120.0 (2)	O71—C71—C72	113.5 (3)
C21—C26—H26	120.0	C71—O71—H71	109.5
C25—C26—H26	120.0	C71—C72—H72A	109.5
N27—C27—C21	119.6 (3)	C71—C72—H72B	109.5
N27—C27—H27	120.2	H72A—C72—H72B	109.5
C21—C27—H27	120.2	C71—C72—H72C	109.5
C27—N27—N17	113.8 (2)	H72A—C72—H72C	109.5
C32—C31—C36	122.3 (2)	H72B—C72—H72C	109.5
C32—C31—S1	118.43 (19)

C16—N11—C12—C13	−1.8 (3)	C23—C24—C25—C26	0.8 (3)
N11—C12—C13—C14	0.1 (4)	C22—C21—C26—C25	−1.0 (3)
C12—C13—C14—C15	2.1 (3)	C27—C21—C26—C25	177.3 (2)
C12—C13—C14—C17	−179.6 (2)	C24—C25—C26—C21	−0.3 (3)
C13—C14—C15—C16	−2.5 (3)	C26—C21—C27—N27	−1.0 (3)
C17—C14—C15—C16	179.3 (2)	C22—C21—C27—N27	177.3 (2)
C12—N11—C16—C15	1.4 (4)	C21—C27—N27—N17	178.38 (18)
C14—C15—C16—N11	0.8 (4)	C17—N17—N27—C27	179.00 (19)
C15—C14—C17—O17	175.8 (2)	O1—S1—C31—C32	156.83 (19)
C13—C14—C17—O17	−2.4 (3)	O2—S1—C31—C32	22.0 (2)
C15—C14—C17—N17	−2.9 (3)	O22—S1—C31—C32	−93.5 (2)
C13—C14—C17—N17	178.9 (2)	O1—S1—C31—C36	−22.8 (2)
O17—C17—N17—N27	−3.1 (3)	O2—S1—C31—C36	−157.57 (19)
C14—C17—N17—N27	175.57 (18)	O22—S1—C31—C36	86.9 (2)
C26—C21—C22—C23	1.8 (3)	C36—C31—C32—C33	−2.1 (4)
C27—C21—C22—C23	−176.5 (2)	S1—C31—C32—C33	178.31 (18)
C26—C21—C22—O22	176.0 (2)	C31—C32—C33—C34	2.6 (4)
C27—C21—C22—O22	−2.3 (3)	C31—C32—C33—N33	−178.5 (2)
C21—C22—O22—S1	86.2 (2)	C32—C33—N33—O33	123.9 (3)
C23—C22—O22—S1	−99.4 (2)	C34—C33—N33—O33	−57.3 (4)
O1—S1—O22—C22	−174.26 (16)	C32—C33—N33—O34	−55.5 (3)
O2—S1—O22—C22	−44.21 (18)	C34—C33—N33—O34	123.4 (3)
C31—S1—O22—C22	70.97 (19)	C32—C33—C34—C35	−1.9 (4)
C21—C22—C23—O23	176.15 (19)	N33—C33—C34—C35	179.3 (2)
O22—C22—C23—O23	1.7 (3)	C32—C33—C34—Cl34	175.97 (19)
C21—C22—C23—C24	−1.2 (3)	N33—C33—C34—Cl34	−2.9 (4)
O22—C22—C23—C24	−175.7 (2)	C33—C34—C35—C36	0.5 (4)
C24—C23—O23—C23A	−10.3 (3)	Cl34—C34—C35—C36	−177.41 (19)
C22—C23—O23—C23A	172.6 (2)	C34—C35—C36—C31	0.1 (4)
O23—C23—C24—C25	−177.2 (2)	C32—C31—C36—C35	0.8 (4)
C22—C23—C24—C25	−0.1 (3)	S1—C31—C36—C35	−179.63 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O71—H71···N11ⁱ	0.82	1.84	2.661 (3)	176
C35—H35···O17ⁱⁱ	0.93	2.51	3.360 (3)	152
O41—H41···O17ⁱⁱⁱ	0.82	1.96	2.698 (3)	150
O41—H41···N27ⁱⁱⁱ	0.82	2.59	3.211 (3)	134
N17—H17···O42^iv	0.86	2.10	2.875 (3)	150
C27—H27···O42^iv	0.93	2.43	3.206 (4)	140
O51—H51···O52ⁱⁱⁱ	0.82	1.87	2.672 (3)	167
C24—H24···O62ⁱⁱⁱ	0.93	2.54	3.461 (3)	170
O61—H61···O62^v	0.82	1.83	2.648 (3)	178
C12—H12···O72ⁱ	0.93	2.59	3.255 (3)	129
C32—H32···O72	0.93	2.37	3.122 (4)	137

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₅ClN₄O₇S·4C₂H₄O₂
M_r	731.09
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	8.0565 (16), 13.876 (3), 16.097 (3)
α, β, γ (°)	79.01 (3), 76.01 (3), 75.44 (3)
V (Å³)	1673.8 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.23 × 0.18 × 0.12

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.913, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	9794, 5882, 4448
R_int	0.081
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.146, 1.01
No. of reflections	5882
No. of parameters	451
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.44

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O71—H71···N11ⁱ	0.82	1.84	2.661 (3)	176
C35—H35···O17ⁱⁱ	0.93	2.51	3.360 (3)	152
O41—H41···O17ⁱⁱⁱ	0.82	1.96	2.698 (3)	150
O41—H41···N27ⁱⁱⁱ	0.82	2.59	3.211 (3)	134
N17—H17···O42^iv	0.86	2.10	2.875 (3)	150
C27—H27···O42^iv	0.93	2.43	3.206 (4)	140
O51—H51···O52ⁱⁱⁱ	0.82	1.87	2.672 (3)	167
C24—H24···O62ⁱⁱⁱ	0.93	2.54	3.461 (3)	170
O61—H61···O62^v	0.82	1.83	2.648 (3)	178
C12—H12···O72ⁱ	0.93	2.59	3.255 (3)	129
C32—H32···O72	0.93	2.37	3.122 (4)	137

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

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (1999). SMART and SAINT for Windows NT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Jones, R. D., Summerville, D. A. & Basolo, F. (1979). Chem. Rev. 17, 139–179. CrossRef Web of Science Google Scholar
Larson, E. J. & Pecoraro, V. L. (1991). J. Am. Chem. Soc. 113, 3810–3818. CSD CrossRef CAS Web of Science Google Scholar
Santos, M. L. P., Bagatin, I. A., Pereira, E. M. & Ferreira, A. M. D. C. (2001). J. Chem. Soc. Dalton Trans. pp. 838–844. Web of Science CrossRef Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2170

doi:10.1107/S1600536808034089

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

(E)-N′-[2-(4-Chloro-3-nitro­phenyl­sulfon­yl­oxy)-3-meth­oxy­benzyl­­idene]isonicotinohydrazide acetic acid tetra­solvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

(E)-N′-[2-(4-Chloro-3-nitrophenylsulfonyloxy)-3-methoxybenzylidene]isonicotinohydrazide acetic acid tetrasolvate