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In the title compound, C14H9Cl2N3O4·C3H7NO, the hydrazone mol­ecule adopts an E conformation with respect to azomethine bond, and the dihedral angle between the two aromatic rings [8.96 (11)°] shows that the rings are almost co-planar. The planar conformation of the mol­ecule is stabilized by the intra­molecular O—H...N hydrogen bond involving the OH group and azomethine N atom. The azomethine and keto bond distances [1.269 (2) and 1.210 (2) Å, respectively] are very close to the formal C=N and C=O bond lengths. The di­methyl­formamide solvent mol­ecule is connected to the hydrazone NH group via an N—H...O hydrogen bond. In the crystal, non-classical C—H...O and C—H...Cl hydrogen bonds link the mol­ecules into chains along [322]. A supra­molecular three-dimensional architecture is created by weak C—Cl...π [4.163 (3) Å, 83.26 (9)°] and π–π [centroid–centroid distance = 4.0395 (14) Å] inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015018290/yk2106sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989015018290/yk2106Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015018290/yk2106Isup3.cml
Supplementary material

CCDC reference: 1428612

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.043
  • wR factor = 0.159
  • Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT242_ALERT_2_C Low Ueq as Compared to Neighbors for ..... N3 Check PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors of N4 Check PLAT334_ALERT_2_C Small Average Benzene C-C Dist. C9 -C14 1.37 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H3 .. CL1 .. 2.92 Ang. PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ... -2.850 Report PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 16 Report
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 4 Note PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 2 Report PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 2 Note PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ... 3 Report PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 117 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 6 ALERT level C = Check. Ensure it is not caused by an omission or oversight 5 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Recent studies of hydrazones emphasis the importance of the hydrazone functional group in various fields ranging from organic synthesis and medicinal chemistry to supra­molecular chemistry (Su & Aprahamian, 2014). They have growing importance because of their biological applications (Nair et al., 2014; Prasanna & Kumar, 2013; Hollo et al., 2014). Here we discuss the synthesis of N'-[(E)-(3,5-di­chloro-2-hy­droxy­phenyl)­methyl­idene]-4-nitro­benzohydrazide di­methyl­formamide monosolvate from 3,5-di­chloro­salicyl­aldehyde and 4-nitro­benzoyl hydrazide. By this reaction, we obtained a novel di­methyl­formamide solvated aroylhydrazone in a simple condensation reaction.

The title compound, C14H9Cl2N3O4·C3H7NO, adopts an E configuration with respect to C7N1 bond (Fig. 1). The two aromatic rings of the molecule are almost in a plane with a slight twist with a dihedral angle of 8.96 (11) °. The C7N1 and C8O2 bond distances [1.269 (3) and 1.210 (2) Å, respectively] are very close to the formal CN and CO bond lengths. An intra­molecular hydrogen bond is found between N1 and the H atom of the phenolic group with a D···A distance of 2.581 (2) Å. Each hydrazone molecule forms one classical inter­molecular N—H···O hydrogen bond (to di­methyl­formamide molecule) and three non-classical C–H···O inter­molecular hydrogen bonds. The pairs of non-classical C13–H···O4 inter­actions with D···A distance of 3.232 (3) Å (Table 1) connect molecules into centrosymmetric dimers, and these dimers are connected by means of C–H···Cl inter­actions into chains along [3 2 2]. The packing diagram showing all hydrogen bonds and C—Cl···π inter­actions viewed along c axis is presented in Fig. 2.

Synthesis and crystallization top

The title compound was prepared by adapting a reported procedure (Bessy et al, 2006) as described below. 3,5-Di­chloro­salicyl­aldehyde (0.191 g, 1 mmol) and 4-nitro­benzoyl hydrazide (0.181 g, 1 mmol) were dissolved in 10 mL of DMF. The solution was heated to boiling for 15 min, cooled to room temperature and then poured to 40 mL of water containing crushed ice and 1 mL of concentrated sulfuric acid. The pale yellow colored solid product was separated, washed with DMF and dried over P4O10 in vacuo. Single crystals of the title compound suitable for X-ray analysis were obtained by recrystallization from di­methyl­formamide.

Refinement top

All H atoms on C were placed in calculated positions, guided by difference map, with C—H bond distances of 0.93-0.96 Å. H atoms were assigned Uiso(H) values of 1.2Ueq(carrier). H atoms attached to N2 and O1 were located from a difference Fourier map and the bond distances are restrained to 0.88±0.01 and 0.84±0.01 Å, respectively. The reflections (0 0 1), (0 -1 1) and (0 1 0) were omitted owing to bad agreement.

Related literature top

For applications of hydrazones in supramolecular chemistry, see: Su & Aprahamian (2014). For biological applications of hydrazones and derivatives, see: Nair et al. (2014); Prasanna & Kumar (2013); Holló et al. (2014); For the synthesis of related compounds, see: Bessy et al. (2006).

Structure description top

Recent studies of hydrazones emphasis the importance of the hydrazone functional group in various fields ranging from organic synthesis and medicinal chemistry to supra­molecular chemistry (Su & Aprahamian, 2014). They have growing importance because of their biological applications (Nair et al., 2014; Prasanna & Kumar, 2013; Hollo et al., 2014). Here we discuss the synthesis of N'-[(E)-(3,5-di­chloro-2-hy­droxy­phenyl)­methyl­idene]-4-nitro­benzohydrazide di­methyl­formamide monosolvate from 3,5-di­chloro­salicyl­aldehyde and 4-nitro­benzoyl hydrazide. By this reaction, we obtained a novel di­methyl­formamide solvated aroylhydrazone in a simple condensation reaction.

The title compound, C14H9Cl2N3O4·C3H7NO, adopts an E configuration with respect to C7N1 bond (Fig. 1). The two aromatic rings of the molecule are almost in a plane with a slight twist with a dihedral angle of 8.96 (11) °. The C7N1 and C8O2 bond distances [1.269 (3) and 1.210 (2) Å, respectively] are very close to the formal CN and CO bond lengths. An intra­molecular hydrogen bond is found between N1 and the H atom of the phenolic group with a D···A distance of 2.581 (2) Å. Each hydrazone molecule forms one classical inter­molecular N—H···O hydrogen bond (to di­methyl­formamide molecule) and three non-classical C–H···O inter­molecular hydrogen bonds. The pairs of non-classical C13–H···O4 inter­actions with D···A distance of 3.232 (3) Å (Table 1) connect molecules into centrosymmetric dimers, and these dimers are connected by means of C–H···Cl inter­actions into chains along [3 2 2]. The packing diagram showing all hydrogen bonds and C—Cl···π inter­actions viewed along c axis is presented in Fig. 2.

For applications of hydrazones in supramolecular chemistry, see: Su & Aprahamian (2014). For biological applications of hydrazones and derivatives, see: Nair et al. (2014); Prasanna & Kumar (2013); Holló et al. (2014); For the synthesis of related compounds, see: Bessy et al. (2006).

Synthesis and crystallization top

The title compound was prepared by adapting a reported procedure (Bessy et al, 2006) as described below. 3,5-Di­chloro­salicyl­aldehyde (0.191 g, 1 mmol) and 4-nitro­benzoyl hydrazide (0.181 g, 1 mmol) were dissolved in 10 mL of DMF. The solution was heated to boiling for 15 min, cooled to room temperature and then poured to 40 mL of water containing crushed ice and 1 mL of concentrated sulfuric acid. The pale yellow colored solid product was separated, washed with DMF and dried over P4O10 in vacuo. Single crystals of the title compound suitable for X-ray analysis were obtained by recrystallization from di­methyl­formamide.

Refinement details top

All H atoms on C were placed in calculated positions, guided by difference map, with C—H bond distances of 0.93-0.96 Å. H atoms were assigned Uiso(H) values of 1.2Ueq(carrier). H atoms attached to N2 and O1 were located from a difference Fourier map and the bond distances are restrained to 0.88±0.01 and 0.84±0.01 Å, respectively. The reflections (0 0 1), (0 -1 1) and (0 1 0) were omitted owing to bad agreement.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. ORTEP view of the title compound, drawn with 50% probability displacement ellipsoids for the non-H atoms.
[Figure 2] Fig. 2. Diagram showing molecular packing viewed along the c axis along with intermolecular interactions.
N'-[(E)-3,5-Dichloro-2-hydroxybenzylidene]-4-nitrobenzohydrazide dimethylformamide monosolvate top
Crystal data top
C14H9Cl2N3O4·C3H7NOZ = 2
Mr = 427.24F(000) = 440
Triclinic, P1Dx = 1.479 Mg m3
a = 7.8853 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.9445 (10) ÅCell parameters from 2537 reflections
c = 11.9521 (15) Åθ = 2.8–28.1°
α = 114.408 (6)°µ = 0.38 mm1
β = 102.895 (7)°T = 296 K
γ = 98.939 (5)°Needle, pale yellow
V = 959.60 (17) Å30.40 × 0.11 × 0.09 mm
Data collection top
Bruker Kappa APEXII CCD Diffractometer3000 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.019
ω and φ scanθmax = 28.4°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
h = 109
Tmin = 0.834, Tmax = 0.929k = 1515
7569 measured reflectionsl = 1515
4660 independent reflections
Refinement top
Refinement on F22 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.043H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.159 w = 1/[σ2(Fo2) + (0.0998P)2 + 0.0446P]
where P = (Fo2 + 2Fc2)/3
S = 0.95(Δ/σ)max = 0.001
4660 reflectionsΔρmax = 0.23 e Å3
263 parametersΔρmin = 0.19 e Å3
Crystal data top
C14H9Cl2N3O4·C3H7NOγ = 98.939 (5)°
Mr = 427.24V = 959.60 (17) Å3
Triclinic, P1Z = 2
a = 7.8853 (6) ÅMo Kα radiation
b = 11.9445 (10) ŵ = 0.38 mm1
c = 11.9521 (15) ÅT = 296 K
α = 114.408 (6)°0.40 × 0.11 × 0.09 mm
β = 102.895 (7)°
Data collection top
Bruker Kappa APEXII CCD Diffractometer4660 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
3000 reflections with I > 2σ(I)
Tmin = 0.834, Tmax = 0.929Rint = 0.019
7569 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0432 restraints
wR(F2) = 0.159H atoms treated by a mixture of independent and constrained refinement
S = 0.95Δρmax = 0.23 e Å3
4660 reflectionsΔρmin = 0.19 e Å3
263 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
xyzUiso*/Ueq
Cl11.35723 (9)1.29047 (6)1.47197 (6)0.0756 (2)
Cl21.23273 (9)1.51632 (6)1.17091 (7)0.0756 (2)
O11.0508 (2)1.08266 (15)1.27329 (15)0.0576 (4)
O20.6756 (2)0.77509 (15)1.08867 (15)0.0652 (4)
O30.0311 (3)0.25861 (16)0.6472 (2)0.0864 (6)
O40.0770 (3)0.3439 (2)0.5227 (2)0.0989 (7)
O50.4796 (2)1.06202 (17)0.22900 (16)0.0668 (4)
N10.78454 (19)0.97794 (15)1.05922 (16)0.0457 (4)
N20.6378 (2)0.87905 (15)0.96978 (16)0.0454 (4)
N30.0045 (2)0.34550 (18)0.6219 (2)0.0619 (5)
N40.5894 (3)0.96448 (18)0.34168 (18)0.0616 (5)
C11.0866 (2)1.18037 (18)1.24598 (19)0.0441 (4)
C21.2306 (3)1.2870 (2)1.3331 (2)0.0512 (5)
C31.2741 (3)1.39056 (18)1.3111 (2)0.0529 (5)
H31.36941.46221.37140.063*
C41.1756 (3)1.38669 (19)1.1995 (2)0.0521 (5)
C51.0326 (2)1.28330 (19)1.1101 (2)0.0489 (5)
H50.96751.28241.03440.059*
C60.9853 (2)1.17920 (17)1.13350 (19)0.0426 (4)
C70.8316 (2)1.07285 (19)1.03936 (19)0.0464 (4)
H70.76731.07380.96450.056*
C80.5925 (2)0.77882 (18)0.99269 (18)0.0428 (4)
C90.4325 (2)0.67029 (17)0.89195 (18)0.0397 (4)
C100.3727 (3)0.57541 (19)0.9227 (2)0.0496 (5)
H100.42760.58411.00440.060*
C110.2333 (3)0.4681 (2)0.8348 (2)0.0548 (5)
H110.19440.40340.85510.066*
C120.1536 (2)0.45939 (18)0.7164 (2)0.0470 (4)
C130.2077 (3)0.5529 (2)0.6837 (2)0.0507 (5)
H130.14970.54490.60290.061*
C140.3485 (2)0.65882 (19)0.77184 (19)0.0456 (4)
H140.38730.72280.75060.055*
C150.4196 (5)0.8698 (3)0.2961 (4)0.1047 (11)
H15A0.32230.90220.26990.157*
H15B0.40520.85060.36450.157*
H15C0.41770.79340.22360.157*
C160.7510 (5)0.9501 (3)0.4148 (3)0.0998 (10)
H16A0.76920.86910.36410.150*
H16B0.73650.95380.49380.150*
H16C0.85411.01790.43490.150*
C170.6030 (3)1.0510 (2)0.3016 (2)0.0531 (5)
H170.71621.10870.33100.064*
H20.589 (3)0.888 (2)0.9019 (17)0.072 (8)*
H10.962 (3)1.028 (2)1.2106 (19)0.090 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0735 (4)0.0650 (4)0.0560 (3)0.0053 (3)0.0032 (3)0.0191 (3)
Cl20.0772 (4)0.0489 (3)0.1074 (5)0.0066 (3)0.0394 (4)0.0413 (4)
O10.0540 (8)0.0471 (9)0.0590 (9)0.0035 (7)0.0066 (7)0.0249 (8)
O20.0644 (9)0.0599 (10)0.0530 (9)0.0038 (7)0.0047 (7)0.0286 (8)
O30.0830 (12)0.0449 (10)0.1029 (15)0.0120 (8)0.0080 (11)0.0295 (10)
O40.0887 (13)0.0704 (12)0.0839 (13)0.0243 (10)0.0282 (10)0.0310 (11)
O50.0629 (9)0.0687 (11)0.0651 (10)0.0103 (8)0.0063 (8)0.0375 (9)
N10.0368 (8)0.0370 (8)0.0492 (9)0.0012 (6)0.0089 (7)0.0128 (7)
N20.0367 (8)0.0378 (8)0.0467 (9)0.0013 (6)0.0027 (7)0.0152 (8)
N30.0514 (10)0.0408 (10)0.0705 (13)0.0025 (8)0.0058 (9)0.0171 (9)
N40.0783 (12)0.0453 (10)0.0564 (11)0.0101 (9)0.0138 (9)0.0257 (9)
C10.0418 (9)0.0370 (10)0.0489 (11)0.0042 (7)0.0173 (8)0.0169 (9)
C20.0449 (10)0.0446 (11)0.0487 (11)0.0018 (8)0.0140 (9)0.0119 (9)
C30.0440 (10)0.0368 (11)0.0579 (12)0.0015 (8)0.0172 (9)0.0078 (10)
C40.0468 (10)0.0365 (10)0.0702 (14)0.0055 (8)0.0282 (10)0.0197 (10)
C50.0441 (10)0.0433 (11)0.0584 (12)0.0096 (8)0.0187 (9)0.0228 (10)
C60.0363 (8)0.0342 (9)0.0487 (10)0.0052 (7)0.0155 (8)0.0122 (8)
C70.0389 (9)0.0423 (11)0.0495 (11)0.0074 (8)0.0094 (8)0.0174 (9)
C80.0372 (9)0.0391 (10)0.0424 (10)0.0035 (7)0.0080 (7)0.0150 (8)
C90.0349 (8)0.0351 (9)0.0441 (9)0.0061 (7)0.0098 (7)0.0165 (8)
C100.0497 (10)0.0467 (11)0.0499 (11)0.0057 (8)0.0082 (9)0.0267 (10)
C110.0526 (11)0.0412 (11)0.0673 (13)0.0016 (8)0.0121 (10)0.0298 (11)
C120.0399 (9)0.0345 (10)0.0540 (11)0.0019 (7)0.0092 (8)0.0149 (9)
C130.0478 (10)0.0463 (11)0.0484 (11)0.0042 (8)0.0053 (9)0.0214 (9)
C140.0424 (9)0.0399 (10)0.0507 (11)0.0031 (8)0.0093 (8)0.0232 (9)
C150.121 (3)0.072 (2)0.111 (2)0.0127 (17)0.039 (2)0.0468 (19)
C160.128 (3)0.086 (2)0.0810 (19)0.041 (2)0.0054 (18)0.0460 (18)
C170.0537 (11)0.0449 (11)0.0524 (12)0.0040 (9)0.0108 (9)0.0216 (10)
Geometric parameters (Å, º) top
Cl1—C21.716 (2)C5—C61.397 (3)
Cl2—C41.734 (2)C5—H50.9300
O1—C11.342 (2)C6—C71.442 (3)
O1—H10.835 (10)C7—H70.9300
O2—C81.210 (2)C8—C91.498 (2)
O3—N31.206 (2)C9—C101.378 (3)
O4—N31.207 (3)C9—C141.380 (3)
O5—C171.214 (2)C10—C111.375 (3)
N1—C71.269 (2)C10—H100.9300
N1—N21.363 (2)C11—C121.367 (3)
N2—C81.348 (2)C11—H110.9300
N2—H20.872 (10)C12—C131.367 (3)
N3—C121.466 (3)C13—C141.372 (3)
N4—C171.306 (3)C13—H130.9300
N4—C151.437 (3)C14—H140.9300
N4—C161.454 (3)C15—H15A0.9600
C1—C21.386 (3)C15—H15B0.9600
C1—C61.396 (3)C15—H15C0.9600
C2—C31.376 (3)C16—H16A0.9600
C3—C41.363 (3)C16—H16B0.9600
C3—H30.9300C16—H16C0.9600
C4—C51.370 (3)C17—H170.9300
C1—O1—H1105 (2)N2—C8—C9116.40 (16)
C7—N1—N2118.71 (16)C10—C9—C14119.48 (17)
C8—N2—N1117.36 (15)C10—C9—C8116.28 (16)
C8—N2—H2128.4 (18)C14—C9—C8124.20 (16)
N1—N2—H2114.1 (18)C11—C10—C9121.12 (18)
O3—N3—O4123.3 (2)C11—C10—H10119.4
O3—N3—C12118.6 (2)C9—C10—H10119.4
O4—N3—C12118.07 (19)C12—C11—C10117.92 (18)
C17—N4—C15120.0 (2)C12—C11—H11121.0
C17—N4—C16120.2 (2)C10—C11—H11121.0
C15—N4—C16119.0 (2)C13—C12—C11122.36 (18)
O1—C1—C2118.66 (18)C13—C12—N3119.26 (19)
O1—C1—C6122.82 (16)C11—C12—N3118.38 (18)
C2—C1—C6118.52 (17)C12—C13—C14119.15 (18)
C3—C2—C1121.57 (19)C12—C13—H13120.4
C3—C2—Cl1119.12 (16)C14—C13—H13120.4
C1—C2—Cl1119.31 (16)C13—C14—C9119.95 (17)
C4—C3—C2119.06 (18)C13—C14—H14120.0
C4—C3—H3120.5C9—C14—H14120.0
C2—C3—H3120.5N4—C15—H15A109.5
C3—C4—C5121.61 (19)N4—C15—H15B109.5
C3—C4—Cl2119.00 (16)H15A—C15—H15B109.5
C5—C4—Cl2119.39 (18)N4—C15—H15C109.5
C4—C5—C6119.5 (2)H15A—C15—H15C109.5
C4—C5—H5120.2H15B—C15—H15C109.5
C6—C5—H5120.2N4—C16—H16A109.5
C1—C6—C5119.70 (17)N4—C16—H16B109.5
C1—C6—C7121.85 (16)H16A—C16—H16B109.5
C5—C6—C7118.44 (18)N4—C16—H16C109.5
N1—C7—C6119.61 (18)H16A—C16—H16C109.5
N1—C7—H7120.2H16B—C16—H16C109.5
C6—C7—H7120.2O5—C17—N4125.3 (2)
O2—C8—N2122.52 (17)O5—C17—H17117.4
O2—C8—C9121.07 (17)N4—C17—H17117.4
C7—N1—N2—C8179.15 (17)N1—N2—C8—C9179.03 (15)
O1—C1—C2—C3179.80 (17)O2—C8—C9—C108.0 (3)
C6—C1—C2—C30.3 (3)N2—C8—C9—C10172.24 (16)
O1—C1—C2—Cl10.0 (3)O2—C8—C9—C14169.75 (19)
C6—C1—C2—Cl1179.94 (14)N2—C8—C9—C1410.0 (3)
C1—C2—C3—C41.5 (3)C14—C9—C10—C111.4 (3)
Cl1—C2—C3—C4178.75 (15)C8—C9—C10—C11176.44 (18)
C2—C3—C4—C51.2 (3)C9—C10—C11—C121.1 (3)
C2—C3—C4—Cl2179.09 (15)C10—C11—C12—C130.1 (3)
C3—C4—C5—C60.3 (3)C10—C11—C12—N3179.89 (18)
Cl2—C4—C5—C6179.43 (13)O3—N3—C12—C13173.37 (19)
O1—C1—C6—C5178.71 (16)O4—N3—C12—C137.0 (3)
C2—C1—C6—C51.2 (3)O3—N3—C12—C116.8 (3)
O1—C1—C6—C71.2 (3)O4—N3—C12—C11172.8 (2)
C2—C1—C6—C7178.87 (18)C11—C12—C13—C140.9 (3)
C4—C5—C6—C11.5 (3)N3—C12—C13—C14179.30 (18)
C4—C5—C6—C7178.56 (17)C12—C13—C14—C90.5 (3)
N2—N1—C7—C6179.29 (15)C10—C9—C14—C130.6 (3)
C1—C6—C7—N11.0 (3)C8—C9—C14—C13177.11 (18)
C5—C6—C7—N1179.11 (16)C15—N4—C17—O52.2 (4)
N1—N2—C8—O20.7 (3)C16—N4—C17—O5172.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O5i0.87 (1)1.90 (1)2.757 (2)169 (3)
C3—H3···Cl1ii0.932.923.836 (2)169
C7—H7···O5i0.932.383.145 (3)139
C13—H13···O4iii0.932.423.231 (3)146
O1—H1···N10.84 (1)1.82 (2)2.581 (2)151 (3)
Symmetry codes: (i) x+1, y+2, z+1; (ii) x+3, y+3, z+3; (iii) x, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O5i0.872 (10)1.896 (11)2.757 (2)169 (3)
C3—H3···Cl1ii0.932.923.836 (2)168.6
C7—H7···O5i0.932.383.145 (3)139.0
C13—H13···O4iii0.932.423.231 (3)146.0
O1—H1···N10.835 (10)1.817 (17)2.581 (2)151 (3)
Symmetry codes: (i) x+1, y+2, z+1; (ii) x+3, y+3, z+3; (iii) x, y+1, z+1.
 

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