






Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015018290/yk2106sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2056989015018290/yk2106Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015018290/yk2106Isup3.cml |
CCDC reference: 1428612
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(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
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 C7═N1 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 C7═N1 and C8═O2 bond distances [1.269 (3) and 1.210 (2) Å, respectively] are very close to the formal C═N and C═O 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.
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.
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.
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 C7═N1 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 C7═N1 and C8═O2 bond distances [1.269 (3) and 1.210 (2) Å, respectively] are very close to the formal C═N and C═O 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).
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.
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.
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).
C14H9Cl2N3O4·C3H7NO | Z = 2 |
Mr = 427.24 | F(000) = 440 |
Triclinic, P1 | Dx = 1.479 Mg m−3 |
a = 7.8853 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.9445 (10) Å | Cell parameters from 2537 reflections |
c = 11.9521 (15) Å | θ = 2.8–28.1° |
α = 114.408 (6)° | µ = 0.38 mm−1 |
β = 102.895 (7)° | T = 296 K |
γ = 98.939 (5)° | Needle, pale yellow |
V = 959.60 (17) Å3 | 0.40 × 0.11 × 0.09 mm |
Bruker Kappa APEXII CCD Diffractometer | 3000 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.019 |
ω and φ scan | θmax = 28.4°, θmin = 2.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −10→9 |
Tmin = 0.834, Tmax = 0.929 | k = −15→15 |
7569 measured reflections | l = −15→15 |
4660 independent reflections |
Refinement on F2 | 2 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.043 | H 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 reflections | Δρmax = 0.23 e Å−3 |
263 parameters | Δρmin = −0.19 e Å−3 |
C14H9Cl2N3O4·C3H7NO | γ = 98.939 (5)° |
Mr = 427.24 | V = 959.60 (17) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.8853 (6) Å | Mo Kα radiation |
b = 11.9445 (10) Å | µ = 0.38 mm−1 |
c = 11.9521 (15) Å | T = 296 K |
α = 114.408 (6)° | 0.40 × 0.11 × 0.09 mm |
β = 102.895 (7)° |
Bruker Kappa APEXII CCD Diffractometer | 4660 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 3000 reflections with I > 2σ(I) |
Tmin = 0.834, Tmax = 0.929 | Rint = 0.019 |
7569 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 2 restraints |
wR(F2) = 0.159 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.95 | Δρmax = 0.23 e Å−3 |
4660 reflections | Δρmin = −0.19 e Å−3 |
263 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 1.35723 (9) | 1.29047 (6) | 1.47197 (6) | 0.0756 (2) | |
Cl2 | 1.23273 (9) | 1.51632 (6) | 1.17091 (7) | 0.0756 (2) | |
O1 | 1.0508 (2) | 1.08266 (15) | 1.27329 (15) | 0.0576 (4) | |
O2 | 0.6756 (2) | 0.77509 (15) | 1.08867 (15) | 0.0652 (4) | |
O3 | −0.0311 (3) | 0.25861 (16) | 0.6472 (2) | 0.0864 (6) | |
O4 | −0.0770 (3) | 0.3439 (2) | 0.5227 (2) | 0.0989 (7) | |
O5 | 0.4796 (2) | 1.06202 (17) | 0.22900 (16) | 0.0668 (4) | |
N1 | 0.78454 (19) | 0.97794 (15) | 1.05922 (16) | 0.0457 (4) | |
N2 | 0.6378 (2) | 0.87905 (15) | 0.96978 (16) | 0.0454 (4) | |
N3 | 0.0045 (2) | 0.34550 (18) | 0.6219 (2) | 0.0619 (5) | |
N4 | 0.5894 (3) | 0.96448 (18) | 0.34168 (18) | 0.0616 (5) | |
C1 | 1.0866 (2) | 1.18037 (18) | 1.24598 (19) | 0.0441 (4) | |
C2 | 1.2306 (3) | 1.2870 (2) | 1.3331 (2) | 0.0512 (5) | |
C3 | 1.2741 (3) | 1.39056 (18) | 1.3111 (2) | 0.0529 (5) | |
H3 | 1.3694 | 1.4622 | 1.3714 | 0.063* | |
C4 | 1.1756 (3) | 1.38669 (19) | 1.1995 (2) | 0.0521 (5) | |
C5 | 1.0326 (2) | 1.28330 (19) | 1.1101 (2) | 0.0489 (5) | |
H5 | 0.9675 | 1.2824 | 1.0344 | 0.059* | |
C6 | 0.9853 (2) | 1.17920 (17) | 1.13350 (19) | 0.0426 (4) | |
C7 | 0.8316 (2) | 1.07285 (19) | 1.03936 (19) | 0.0464 (4) | |
H7 | 0.7673 | 1.0738 | 0.9645 | 0.056* | |
C8 | 0.5925 (2) | 0.77882 (18) | 0.99269 (18) | 0.0428 (4) | |
C9 | 0.4325 (2) | 0.67029 (17) | 0.89195 (18) | 0.0397 (4) | |
C10 | 0.3727 (3) | 0.57541 (19) | 0.9227 (2) | 0.0496 (5) | |
H10 | 0.4276 | 0.5841 | 1.0044 | 0.060* | |
C11 | 0.2333 (3) | 0.4681 (2) | 0.8348 (2) | 0.0548 (5) | |
H11 | 0.1944 | 0.4034 | 0.8551 | 0.066* | |
C12 | 0.1536 (2) | 0.45939 (18) | 0.7164 (2) | 0.0470 (4) | |
C13 | 0.2077 (3) | 0.5529 (2) | 0.6837 (2) | 0.0507 (5) | |
H13 | 0.1497 | 0.5449 | 0.6029 | 0.061* | |
C14 | 0.3485 (2) | 0.65882 (19) | 0.77184 (19) | 0.0456 (4) | |
H14 | 0.3873 | 0.7228 | 0.7506 | 0.055* | |
C15 | 0.4196 (5) | 0.8698 (3) | 0.2961 (4) | 0.1047 (11) | |
H15A | 0.3223 | 0.9022 | 0.2699 | 0.157* | |
H15B | 0.4052 | 0.8506 | 0.3645 | 0.157* | |
H15C | 0.4177 | 0.7934 | 0.2236 | 0.157* | |
C16 | 0.7510 (5) | 0.9501 (3) | 0.4148 (3) | 0.0998 (10) | |
H16A | 0.7692 | 0.8691 | 0.3641 | 0.150* | |
H16B | 0.7365 | 0.9538 | 0.4938 | 0.150* | |
H16C | 0.8541 | 1.0179 | 0.4349 | 0.150* | |
C17 | 0.6030 (3) | 1.0510 (2) | 0.3016 (2) | 0.0531 (5) | |
H17 | 0.7162 | 1.1087 | 0.3310 | 0.064* | |
H2 | 0.589 (3) | 0.888 (2) | 0.9019 (17) | 0.072 (8)* | |
H1 | 0.962 (3) | 1.028 (2) | 1.2106 (19) | 0.090 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0735 (4) | 0.0650 (4) | 0.0560 (3) | −0.0053 (3) | −0.0032 (3) | 0.0191 (3) |
Cl2 | 0.0772 (4) | 0.0489 (3) | 0.1074 (5) | 0.0066 (3) | 0.0394 (4) | 0.0413 (4) |
O1 | 0.0540 (8) | 0.0471 (9) | 0.0590 (9) | −0.0035 (7) | 0.0066 (7) | 0.0249 (8) |
O2 | 0.0644 (9) | 0.0599 (10) | 0.0530 (9) | −0.0038 (7) | −0.0047 (7) | 0.0286 (8) |
O3 | 0.0830 (12) | 0.0449 (10) | 0.1029 (15) | −0.0120 (8) | 0.0080 (11) | 0.0295 (10) |
O4 | 0.0887 (13) | 0.0704 (12) | 0.0839 (13) | −0.0243 (10) | −0.0282 (10) | 0.0310 (11) |
O5 | 0.0629 (9) | 0.0687 (11) | 0.0651 (10) | 0.0103 (8) | 0.0063 (8) | 0.0375 (9) |
N1 | 0.0368 (8) | 0.0370 (8) | 0.0492 (9) | 0.0012 (6) | 0.0089 (7) | 0.0128 (7) |
N2 | 0.0367 (8) | 0.0378 (8) | 0.0467 (9) | −0.0013 (6) | 0.0027 (7) | 0.0152 (8) |
N3 | 0.0514 (10) | 0.0408 (10) | 0.0705 (13) | −0.0025 (8) | 0.0058 (9) | 0.0171 (9) |
N4 | 0.0783 (12) | 0.0453 (10) | 0.0564 (11) | 0.0101 (9) | 0.0138 (9) | 0.0257 (9) |
C1 | 0.0418 (9) | 0.0370 (10) | 0.0489 (11) | 0.0042 (7) | 0.0173 (8) | 0.0169 (9) |
C2 | 0.0449 (10) | 0.0446 (11) | 0.0487 (11) | 0.0018 (8) | 0.0140 (9) | 0.0119 (9) |
C3 | 0.0440 (10) | 0.0368 (11) | 0.0579 (12) | −0.0015 (8) | 0.0172 (9) | 0.0078 (10) |
C4 | 0.0468 (10) | 0.0365 (10) | 0.0702 (14) | 0.0055 (8) | 0.0282 (10) | 0.0197 (10) |
C5 | 0.0441 (10) | 0.0433 (11) | 0.0584 (12) | 0.0096 (8) | 0.0187 (9) | 0.0228 (10) |
C6 | 0.0363 (8) | 0.0342 (9) | 0.0487 (10) | 0.0052 (7) | 0.0155 (8) | 0.0122 (8) |
C7 | 0.0389 (9) | 0.0423 (11) | 0.0495 (11) | 0.0074 (8) | 0.0094 (8) | 0.0174 (9) |
C8 | 0.0372 (9) | 0.0391 (10) | 0.0424 (10) | 0.0035 (7) | 0.0080 (7) | 0.0150 (8) |
C9 | 0.0349 (8) | 0.0351 (9) | 0.0441 (9) | 0.0061 (7) | 0.0098 (7) | 0.0165 (8) |
C10 | 0.0497 (10) | 0.0467 (11) | 0.0499 (11) | 0.0057 (8) | 0.0082 (9) | 0.0267 (10) |
C11 | 0.0526 (11) | 0.0412 (11) | 0.0673 (13) | 0.0016 (8) | 0.0121 (10) | 0.0298 (11) |
C12 | 0.0399 (9) | 0.0345 (10) | 0.0540 (11) | 0.0019 (7) | 0.0092 (8) | 0.0149 (9) |
C13 | 0.0478 (10) | 0.0463 (11) | 0.0484 (11) | 0.0042 (8) | 0.0053 (9) | 0.0214 (9) |
C14 | 0.0424 (9) | 0.0399 (10) | 0.0507 (11) | 0.0031 (8) | 0.0093 (8) | 0.0232 (9) |
C15 | 0.121 (3) | 0.072 (2) | 0.111 (2) | −0.0127 (17) | 0.039 (2) | 0.0468 (19) |
C16 | 0.128 (3) | 0.086 (2) | 0.0810 (19) | 0.041 (2) | 0.0054 (18) | 0.0460 (18) |
C17 | 0.0537 (11) | 0.0449 (11) | 0.0524 (12) | 0.0040 (9) | 0.0108 (9) | 0.0216 (10) |
Cl1—C2 | 1.716 (2) | C5—C6 | 1.397 (3) |
Cl2—C4 | 1.734 (2) | C5—H5 | 0.9300 |
O1—C1 | 1.342 (2) | C6—C7 | 1.442 (3) |
O1—H1 | 0.835 (10) | C7—H7 | 0.9300 |
O2—C8 | 1.210 (2) | C8—C9 | 1.498 (2) |
O3—N3 | 1.206 (2) | C9—C10 | 1.378 (3) |
O4—N3 | 1.207 (3) | C9—C14 | 1.380 (3) |
O5—C17 | 1.214 (2) | C10—C11 | 1.375 (3) |
N1—C7 | 1.269 (2) | C10—H10 | 0.9300 |
N1—N2 | 1.363 (2) | C11—C12 | 1.367 (3) |
N2—C8 | 1.348 (2) | C11—H11 | 0.9300 |
N2—H2 | 0.872 (10) | C12—C13 | 1.367 (3) |
N3—C12 | 1.466 (3) | C13—C14 | 1.372 (3) |
N4—C17 | 1.306 (3) | C13—H13 | 0.9300 |
N4—C15 | 1.437 (3) | C14—H14 | 0.9300 |
N4—C16 | 1.454 (3) | C15—H15A | 0.9600 |
C1—C2 | 1.386 (3) | C15—H15B | 0.9600 |
C1—C6 | 1.396 (3) | C15—H15C | 0.9600 |
C2—C3 | 1.376 (3) | C16—H16A | 0.9600 |
C3—C4 | 1.363 (3) | C16—H16B | 0.9600 |
C3—H3 | 0.9300 | C16—H16C | 0.9600 |
C4—C5 | 1.370 (3) | C17—H17 | 0.9300 |
C1—O1—H1 | 105 (2) | N2—C8—C9 | 116.40 (16) |
C7—N1—N2 | 118.71 (16) | C10—C9—C14 | 119.48 (17) |
C8—N2—N1 | 117.36 (15) | C10—C9—C8 | 116.28 (16) |
C8—N2—H2 | 128.4 (18) | C14—C9—C8 | 124.20 (16) |
N1—N2—H2 | 114.1 (18) | C11—C10—C9 | 121.12 (18) |
O3—N3—O4 | 123.3 (2) | C11—C10—H10 | 119.4 |
O3—N3—C12 | 118.6 (2) | C9—C10—H10 | 119.4 |
O4—N3—C12 | 118.07 (19) | C12—C11—C10 | 117.92 (18) |
C17—N4—C15 | 120.0 (2) | C12—C11—H11 | 121.0 |
C17—N4—C16 | 120.2 (2) | C10—C11—H11 | 121.0 |
C15—N4—C16 | 119.0 (2) | C13—C12—C11 | 122.36 (18) |
O1—C1—C2 | 118.66 (18) | C13—C12—N3 | 119.26 (19) |
O1—C1—C6 | 122.82 (16) | C11—C12—N3 | 118.38 (18) |
C2—C1—C6 | 118.52 (17) | C12—C13—C14 | 119.15 (18) |
C3—C2—C1 | 121.57 (19) | C12—C13—H13 | 120.4 |
C3—C2—Cl1 | 119.12 (16) | C14—C13—H13 | 120.4 |
C1—C2—Cl1 | 119.31 (16) | C13—C14—C9 | 119.95 (17) |
C4—C3—C2 | 119.06 (18) | C13—C14—H14 | 120.0 |
C4—C3—H3 | 120.5 | C9—C14—H14 | 120.0 |
C2—C3—H3 | 120.5 | N4—C15—H15A | 109.5 |
C3—C4—C5 | 121.61 (19) | N4—C15—H15B | 109.5 |
C3—C4—Cl2 | 119.00 (16) | H15A—C15—H15B | 109.5 |
C5—C4—Cl2 | 119.39 (18) | N4—C15—H15C | 109.5 |
C4—C5—C6 | 119.5 (2) | H15A—C15—H15C | 109.5 |
C4—C5—H5 | 120.2 | H15B—C15—H15C | 109.5 |
C6—C5—H5 | 120.2 | N4—C16—H16A | 109.5 |
C1—C6—C5 | 119.70 (17) | N4—C16—H16B | 109.5 |
C1—C6—C7 | 121.85 (16) | H16A—C16—H16B | 109.5 |
C5—C6—C7 | 118.44 (18) | N4—C16—H16C | 109.5 |
N1—C7—C6 | 119.61 (18) | H16A—C16—H16C | 109.5 |
N1—C7—H7 | 120.2 | H16B—C16—H16C | 109.5 |
C6—C7—H7 | 120.2 | O5—C17—N4 | 125.3 (2) |
O2—C8—N2 | 122.52 (17) | O5—C17—H17 | 117.4 |
O2—C8—C9 | 121.07 (17) | N4—C17—H17 | 117.4 |
C7—N1—N2—C8 | 179.15 (17) | N1—N2—C8—C9 | −179.03 (15) |
O1—C1—C2—C3 | −179.80 (17) | O2—C8—C9—C10 | 8.0 (3) |
C6—C1—C2—C3 | 0.3 (3) | N2—C8—C9—C10 | −172.24 (16) |
O1—C1—C2—Cl1 | 0.0 (3) | O2—C8—C9—C14 | −169.75 (19) |
C6—C1—C2—Cl1 | −179.94 (14) | N2—C8—C9—C14 | 10.0 (3) |
C1—C2—C3—C4 | −1.5 (3) | C14—C9—C10—C11 | 1.4 (3) |
Cl1—C2—C3—C4 | 178.75 (15) | C8—C9—C10—C11 | −176.44 (18) |
C2—C3—C4—C5 | 1.2 (3) | C9—C10—C11—C12 | −1.1 (3) |
C2—C3—C4—Cl2 | −179.09 (15) | C10—C11—C12—C13 | −0.1 (3) |
C3—C4—C5—C6 | 0.3 (3) | C10—C11—C12—N3 | −179.89 (18) |
Cl2—C4—C5—C6 | −179.43 (13) | O3—N3—C12—C13 | 173.37 (19) |
O1—C1—C6—C5 | −178.71 (16) | O4—N3—C12—C13 | −7.0 (3) |
C2—C1—C6—C5 | 1.2 (3) | O3—N3—C12—C11 | −6.8 (3) |
O1—C1—C6—C7 | 1.2 (3) | O4—N3—C12—C11 | 172.8 (2) |
C2—C1—C6—C7 | −178.87 (18) | C11—C12—C13—C14 | 0.9 (3) |
C4—C5—C6—C1 | −1.5 (3) | N3—C12—C13—C14 | −179.30 (18) |
C4—C5—C6—C7 | 178.56 (17) | C12—C13—C14—C9 | −0.5 (3) |
N2—N1—C7—C6 | 179.29 (15) | C10—C9—C14—C13 | −0.6 (3) |
C1—C6—C7—N1 | 1.0 (3) | C8—C9—C14—C13 | 177.11 (18) |
C5—C6—C7—N1 | −179.11 (16) | C15—N4—C17—O5 | 2.2 (4) |
N1—N2—C8—O2 | 0.7 (3) | C16—N4—C17—O5 | 172.0 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O5i | 0.87 (1) | 1.90 (1) | 2.757 (2) | 169 (3) |
C3—H3···Cl1ii | 0.93 | 2.92 | 3.836 (2) | 169 |
C7—H7···O5i | 0.93 | 2.38 | 3.145 (3) | 139 |
C13—H13···O4iii | 0.93 | 2.42 | 3.231 (3) | 146 |
O1—H1···N1 | 0.84 (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. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O5i | 0.872 (10) | 1.896 (11) | 2.757 (2) | 169 (3) |
C3—H3···Cl1ii | 0.93 | 2.92 | 3.836 (2) | 168.6 |
C7—H7···O5i | 0.93 | 2.38 | 3.145 (3) | 139.0 |
C13—H13···O4iii | 0.93 | 2.42 | 3.231 (3) | 146.0 |
O1—H1···N1 | 0.835 (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. |