organic compounds
2-[(4-Methoxy-2-nitrophenyl)iminomethyl]phenol
aDepartment of Chemistry, Faculty of Science, Golestan University, Gorgan, Iran, and bInstitute of Physics ASCR, v.v.i., Na Slovance 2, 182 21 Prague 8, Czech Republic
*Correspondence e-mail: fejfarov@fzu.cz
The 14H12N2O4, contains four crystallographically independent molecules in the All the molecules have similar conformations; the dihedral angles between the aromatic rings are 33.1 (1), 33.76 (9), 31.41 (9) and 32.56 (10)°. Intramolecular O—H⋯N hydrogen bonds form S(6) ring motifs in each molecule. In the crystal, there are two pairs of pseudo-inversion-related molecules. Along the c axis, molecules are stacked with π–π interactions between the 2-hydroxyphenyl and 4-methoxy-2-nitrophenyl rings [centroid–centroid distances = 3.5441 (12)–3.7698 (12) Å].
of the title compound, CRelated literature
For related structures, see: Akkurt et al. (2008); Fejfarová et al. (2010); Fun et al. (2009); Kargar et al. (2012); Keleşoğlu et al. (2009); Khalaji et al. (2007); Özek et al. (2009); Tanak et al. (2009). For the extinction correction, see: Becker & Coppens (1974).
Experimental
Crystal data
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Data collection: CrysAlis PRO (Agilent, 2012); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: JANA2006 (Petříček et al., 2006); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: JANA2006.
Supporting information
https://doi.org/10.1107/S1600536812031212/fk2064sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812031212/fk2064Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812031212/fk2064Isup3.cml
To a stirred solution of the salicylaldehyde (0.2 mmol, in 5 ml of methanol) was added 4-methoxy-2-nitroaniline (0.2 mmol) in 10 ml of methanol and the mixture was stirred for 1 h in air at 323 K and was then left at room temperature for several days without disturbance yielding suitable crystals of the title compound that subsequently were filtered off and washed with Et2O. Yield: 88%. Yellow crystals. Anal. Calc. for C14H12N2O4: C, 61.76; H, 4.44; N, 10.29%. Found: C, 61.70; H, 4.51; N, 10.38%.
Hydrogen atoms attached to carbons were kept in ideal positions with C–H distance 0.96 Å during the
The methyl H atoms were allowed to rotate freely about the adjacent C—O bonds. The hydroxyl hydrogen atoms were found in difference Fourier maps and their coordinates were refined freely. The isotropic atomic displacement parameters of hydrogen atoms were set to 1.5Ueq (methyl and hydroxyl groups) or 1.2Ueq of the parent atom. Reflections -1 19 - 5 and 1 18 - 5 were omitted in last cycles of as outliers.The present work is part of a structural study of ═N and C—N bond lengths of 1.286 and 1.407 Å agree well with the corresponding distances in other (Akkurt et al., 2008; Fun et al., 2009; Kargar et al., 2012; Keleşoğlu et al., 2009; Özek et al., 2009; Tanak et al., 2009.
(Khalaji et al., 2007; Fejfarová et al., 2010). The contains four crystallographically independent molecules (A–D) in the (Fig. 1 and 2). All the molecules have similar conformations, the dihedral angles between the two aromatic rings are 33.1 (1)°, 33.76 (9)°, 31.41 (9)°, and 32.56 (10)°. The azomethine functional groups are co-planar with the adjacent benzene rings. The dihedral angles between the planes of the benzene ring and the plane defined by C(aromatic)—C=N atoms are 2.8 (2)°, 1.50 (18)°, 3.19 (19)°, and 2.7 (2)°. The methoxy groups are almost coplanar with the adjacent benzene rings as can be seen from the torsion angles Cx03—Cx04—Ox03—Cx07 (x = 1–4 for molecules A–D) of -174.57 (19)°, -176.30 (17)°, 174.10 (17)°, and 176.27 (17)°, respectively. The average of CIn the crystal, there are two pairs (A+C, B+D) of pseudo inversion-related molecules. The phenol H atoms form strong intramolecular Ox04—H···Nx02 hydrogen bonds with the imine N atoms, generating S(6) ring motifs. Along the c axis, the molecules are stacked with π-π interactions between the 2-hydroxyphenyl and 4-methoxy-2-nitrophenyl rings of A+B and C+D pairs [centroid-centroid distances in the range of 3.5441 (12)Å – 3.7698 (12) Å] (Figure 3).
For related structures, see: Akkurt et al. (2008); Fejfarová et al. (2010); Fun et al. (2009); Kargar et al. (2012); Keleşoğlu et al. (2009); Khalaji et al. (2007); Özek et al. (2009); Tanak et al. (2009). For the extinction correction, see: Becker & Coppens (1974).
Data collection: CrysAlis PRO (Agilent, 2012); cell
CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: JANA2006 (Petříček et al., 2006); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: JANA2006 (Petříček et al., 2006).C14H12N2O4 | F(000) = 1136 |
Mr = 272.3 | Dx = 1.438 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.5418 Å |
Hall symbol: P 2yb | Cell parameters from 12919 reflections |
a = 16.8655 (2) Å | θ = 3.4–67.6° |
b = 21.0838 (5) Å | µ = 0.9 mm−1 |
c = 7.0741 (5) Å | T = 120 K |
β = 90.817 (2)° | Prism, yellow |
V = 2515.22 (19) Å3 | 0.25 × 0.20 × 0.16 mm |
Z = 8 |
Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector | 7375 independent reflections |
Radiation source: Enhance Ultra (Cu) X-ray Source | 6684 reflections with I > 3σ(I) |
Mirror monochromator | Rint = 0.024 |
Detector resolution: 10.3784 pixels mm-1 | θmax = 67.1°, θmin = 3.4° |
Rotation method data acquisition using ω scans | h = −20→20 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | k = −25→19 |
Tmin = 0.851, Tmax = 1 | l = −8→8 |
19454 measured reflections |
Refinement on F2 | Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0016I2) |
R[F > 3σ(F)] = 0.033 | (Δ/σ)max = 0.040 |
wR(F) = 0.087 | Δρmax = 0.15 e Å−3 |
S = 1.38 | Δρmin = −0.12 e Å−3 |
7375 reflections | Extinction correction: Becker & Coppens (1974), B-C type 1 Lorentzian isotropic |
735 parameters | Extinction coefficient: 23 (3) |
0 restraints | Absolute structure: Flack (1983), 2778 Friedel pairs |
181 constraints | Absolute structure parameter: −0.06 (15) |
H atoms treated by a mixture of independent and constrained refinement |
C14H12N2O4 | V = 2515.22 (19) Å3 |
Mr = 272.3 | Z = 8 |
Monoclinic, P21 | Cu Kα radiation |
a = 16.8655 (2) Å | µ = 0.9 mm−1 |
b = 21.0838 (5) Å | T = 120 K |
c = 7.0741 (5) Å | 0.25 × 0.20 × 0.16 mm |
β = 90.817 (2)° |
Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector | 7375 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | 6684 reflections with I > 3σ(I) |
Tmin = 0.851, Tmax = 1 | Rint = 0.024 |
19454 measured reflections |
R[F > 3σ(F)] = 0.033 | H atoms treated by a mixture of independent and constrained refinement |
wR(F) = 0.087 | Δρmax = 0.15 e Å−3 |
S = 1.38 | Δρmin = −0.12 e Å−3 |
7375 reflections | Absolute structure: Flack (1983), 2778 Friedel pairs |
735 parameters | Absolute structure parameter: −0.06 (15) |
0 restraints |
Experimental. CrysAlis PRO (Agilent, 2012) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F2 for refinement carried out on F and F2, respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement. The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program. |
x | y | z | Uiso*/Ueq | ||
O101 | 0.75197 (9) | 0.40161 (8) | 0.2684 (2) | 0.0325 (5) | |
O102 | 0.73997 (10) | 0.47881 (8) | 0.0692 (3) | 0.0418 (5) | |
O103 | 0.44321 (9) | 0.47415 (8) | 0.0226 (2) | 0.0353 (5) | |
O104 | 0.84363 (9) | 0.28817 (7) | −0.0391 (2) | 0.0295 (4) | |
O201 | 0.62031 (12) | 0.09153 (10) | 0.5791 (4) | 0.0695 (8) | |
O202 | 0.60210 (9) | 0.17182 (8) | 0.7624 (2) | 0.0325 (5) | |
O203 | 0.91500 (8) | 0.10142 (7) | 0.5481 (2) | 0.0290 (4) | |
O204 | 0.51076 (9) | 0.28366 (7) | 0.4491 (2) | 0.0267 (4) | |
O301 | 0.12187 (11) | 0.09018 (9) | 0.1065 (3) | 0.0560 (7) | |
O302 | 0.09907 (9) | 0.17300 (7) | −0.0624 (2) | 0.0313 (5) | |
O303 | 0.41587 (8) | 0.10577 (7) | 0.1458 (2) | 0.0283 (4) | |
O304 | 0.00811 (9) | 0.28192 (7) | 0.2504 (2) | 0.0286 (4) | |
O401 | 0.23694 (9) | 0.48015 (8) | 0.6054 (3) | 0.0401 (5) | |
O402 | 0.25409 (8) | 0.39560 (7) | 0.4393 (2) | 0.0303 (4) | |
O403 | −0.05477 (8) | 0.46909 (7) | 0.6735 (2) | 0.0283 (4) | |
O404 | 0.34982 (9) | 0.28420 (7) | 0.7316 (2) | 0.0295 (4) | |
N101 | 0.71506 (10) | 0.43047 (8) | 0.1454 (2) | 0.0252 (5) | |
N102 | 0.69505 (10) | 0.30308 (8) | 0.0389 (2) | 0.0231 (5) | |
N201 | 0.64206 (10) | 0.14142 (9) | 0.6521 (2) | 0.0281 (5) | |
N202 | 0.65943 (9) | 0.26907 (8) | 0.5403 (2) | 0.0212 (5) | |
N301 | 0.14073 (10) | 0.14177 (8) | 0.0458 (2) | 0.0263 (5) | |
N302 | 0.15641 (9) | 0.26977 (8) | 0.1656 (2) | 0.0219 (5) | |
N401 | 0.21568 (10) | 0.42781 (8) | 0.5491 (2) | 0.0235 (5) | |
N402 | 0.19913 (10) | 0.29979 (8) | 0.6657 (2) | 0.0219 (5) | |
C101 | 0.62753 (12) | 0.34198 (10) | 0.0459 (2) | 0.0226 (6) | |
C102 | 0.63683 (12) | 0.40674 (10) | 0.0865 (2) | 0.0228 (5) | |
C103 | 0.57583 (12) | 0.45023 (10) | 0.0748 (3) | 0.0250 (6) | |
C104 | 0.50037 (12) | 0.42838 (11) | 0.0271 (3) | 0.0269 (6) | |
C105 | 0.48848 (12) | 0.36469 (11) | −0.0147 (3) | 0.0283 (6) | |
C106 | 0.55178 (12) | 0.32283 (11) | −0.0075 (3) | 0.0256 (6) | |
C107 | 0.36311 (14) | 0.45354 (14) | −0.0091 (4) | 0.0463 (8) | |
C108 | 0.69080 (12) | 0.24352 (10) | 0.0766 (3) | 0.0231 (6) | |
C109 | 0.75967 (12) | 0.20240 (10) | 0.0614 (3) | 0.0233 (6) | |
C110 | 0.83385 (12) | 0.22653 (10) | 0.0064 (3) | 0.0249 (6) | |
C111 | 0.89955 (14) | 0.18668 (11) | 0.0031 (3) | 0.0315 (7) | |
C112 | 0.89183 (15) | 0.12361 (11) | 0.0522 (3) | 0.0349 (7) | |
C113 | 0.81873 (15) | 0.09888 (11) | 0.1029 (3) | 0.0345 (7) | |
C114 | 0.75348 (14) | 0.13811 (10) | 0.1074 (3) | 0.0288 (6) | |
C201 | 0.72755 (11) | 0.23065 (10) | 0.5557 (2) | 0.0211 (5) | |
C202 | 0.71981 (11) | 0.16640 (10) | 0.5997 (2) | 0.0220 (5) | |
C203 | 0.78191 (12) | 0.12391 (10) | 0.5954 (3) | 0.0231 (5) | |
C204 | 0.85700 (12) | 0.14623 (10) | 0.5498 (3) | 0.0235 (5) | |
C205 | 0.86774 (12) | 0.21004 (10) | 0.5059 (3) | 0.0243 (6) | |
C206 | 0.80306 (12) | 0.25102 (10) | 0.5070 (3) | 0.0233 (6) | |
C207 | 0.99420 (13) | 0.12213 (11) | 0.5134 (3) | 0.0344 (7) | |
C208 | 0.66305 (12) | 0.32867 (9) | 0.5764 (2) | 0.0212 (5) | |
C209 | 0.59460 (12) | 0.36982 (9) | 0.5515 (2) | 0.0215 (5) | |
C210 | 0.52078 (12) | 0.34580 (10) | 0.4906 (3) | 0.0225 (5) | |
C211 | 0.45560 (13) | 0.38634 (10) | 0.4734 (3) | 0.0273 (6) | |
C212 | 0.46387 (14) | 0.44984 (11) | 0.5144 (3) | 0.0294 (6) | |
C213 | 0.53661 (13) | 0.47458 (10) | 0.5748 (3) | 0.0292 (6) | |
C214 | 0.60111 (13) | 0.43468 (10) | 0.5936 (3) | 0.0258 (6) | |
C301 | 0.22495 (12) | 0.23216 (10) | 0.1496 (2) | 0.0222 (5) | |
C302 | 0.21824 (11) | 0.16775 (10) | 0.1029 (2) | 0.0219 (5) | |
C303 | 0.28126 (12) | 0.12637 (10) | 0.1048 (3) | 0.0235 (6) | |
C304 | 0.35633 (11) | 0.14957 (10) | 0.1511 (2) | 0.0227 (5) | |
C305 | 0.36609 (12) | 0.21300 (10) | 0.1999 (3) | 0.0248 (6) | |
C306 | 0.30082 (12) | 0.25293 (10) | 0.2010 (3) | 0.0246 (6) | |
C307 | 0.49501 (13) | 0.12832 (11) | 0.1742 (3) | 0.0331 (7) | |
C308 | 0.15887 (12) | 0.32986 (10) | 0.1339 (2) | 0.0225 (6) | |
C309 | 0.09020 (12) | 0.36993 (10) | 0.1613 (3) | 0.0230 (6) | |
C310 | 0.01678 (12) | 0.34448 (10) | 0.2162 (3) | 0.0231 (6) | |
C311 | −0.04890 (13) | 0.38389 (10) | 0.2325 (3) | 0.0275 (6) | |
C312 | −0.04221 (14) | 0.44799 (11) | 0.2012 (3) | 0.0315 (6) | |
C313 | 0.03044 (14) | 0.47442 (11) | 0.1530 (3) | 0.0321 (6) | |
C314 | 0.09536 (14) | 0.43544 (10) | 0.1301 (3) | 0.0285 (6) | |
C401 | 0.13152 (12) | 0.33874 (10) | 0.6584 (2) | 0.0214 (5) | |
C402 | 0.13938 (11) | 0.40338 (10) | 0.6143 (2) | 0.0205 (5) | |
C403 | 0.07786 (11) | 0.44609 (10) | 0.6232 (3) | 0.0221 (5) | |
C404 | 0.00308 (12) | 0.42425 (10) | 0.6733 (3) | 0.0238 (6) | |
C405 | −0.00726 (12) | 0.36086 (10) | 0.7203 (3) | 0.0242 (6) | |
C406 | 0.05651 (12) | 0.31940 (10) | 0.7147 (3) | 0.0236 (6) | |
C407 | −0.13379 (13) | 0.44822 (11) | 0.7128 (3) | 0.0328 (7) | |
C408 | 0.19402 (12) | 0.24032 (10) | 0.6266 (3) | 0.0225 (6) | |
C409 | 0.26229 (12) | 0.19855 (9) | 0.6426 (3) | 0.0227 (6) | |
C410 | 0.33761 (12) | 0.22219 (10) | 0.6938 (3) | 0.0246 (6) | |
C411 | 0.40245 (13) | 0.18123 (11) | 0.7024 (3) | 0.0284 (6) | |
C412 | 0.39276 (14) | 0.11775 (11) | 0.6651 (3) | 0.0319 (6) | |
C413 | 0.31855 (14) | 0.09349 (11) | 0.6156 (3) | 0.0328 (7) | |
C414 | 0.25409 (13) | 0.13381 (10) | 0.6036 (3) | 0.0275 (6) | |
H103 | 0.585237 | 0.494417 | 0.098954 | 0.03* | |
H105 | 0.436446 | 0.349691 | −0.048573 | 0.0339* | |
H106 | 0.542941 | 0.279209 | −0.040526 | 0.0308* | |
H107a | 0.349617 | 0.422274 | 0.083706 | 0.0694* | |
H107b | 0.358146 | 0.435414 | −0.133174 | 0.0694* | |
H107c | 0.32794 | 0.489144 | 0.001004 | 0.0694* | |
H108 | 0.641174 | 0.225844 | 0.115451 | 0.0277* | |
H111 | 0.950222 | 0.203014 | −0.033335 | 0.0378* | |
H112 | 0.93754 | 0.096486 | 0.051263 | 0.0418* | |
H113 | 0.813774 | 0.054795 | 0.134483 | 0.0414* | |
H114 | 0.703024 | 0.121068 | 0.14264 | 0.0346* | |
H203 | 0.773585 | 0.079867 | 0.623359 | 0.0277* | |
H205 | 0.91944 | 0.225647 | 0.475056 | 0.0291* | |
H206 | 0.810756 | 0.294662 | 0.473175 | 0.0279* | |
H207a | 1.028774 | 0.086013 | 0.508641 | 0.0517* | |
H207b | 0.995611 | 0.144328 | 0.395029 | 0.0517* | |
H207c | 1.011379 | 0.149947 | 0.613318 | 0.0517* | |
H208 | 0.712229 | 0.3465 | 0.621055 | 0.0254* | |
H211 | 0.405049 | 0.369938 | 0.432901 | 0.0327* | |
H212 | 0.418902 | 0.477488 | 0.501307 | 0.0353* | |
H213 | 0.541765 | 0.518939 | 0.60294 | 0.0351* | |
H214 | 0.651151 | 0.451524 | 0.63617 | 0.031* | |
H303 | 0.273638 | 0.082359 | 0.074844 | 0.0282* | |
H305 | 0.417752 | 0.229055 | 0.232625 | 0.0298* | |
H306 | 0.308043 | 0.296346 | 0.238293 | 0.0296* | |
H307a | 0.531577 | 0.093827 | 0.159668 | 0.0497* | |
H307b | 0.50616 | 0.160643 | 0.082765 | 0.0497* | |
H307c | 0.500475 | 0.145641 | 0.299198 | 0.0497* | |
H308 | 0.207323 | 0.348547 | 0.091177 | 0.027* | |
H311 | −0.099248 | 0.3662 | 0.265864 | 0.033* | |
H312 | −0.087953 | 0.474743 | 0.212543 | 0.0378* | |
H313 | 0.035335 | 0.519407 | 0.135897 | 0.0386* | |
H314 | 0.144888 | 0.453517 | 0.092136 | 0.0341* | |
H403 | 0.086317 | 0.490123 | 0.595399 | 0.0265* | |
H405 | −0.058516 | 0.345747 | 0.756774 | 0.0291* | |
H406 | 0.048689 | 0.275975 | 0.750693 | 0.0283* | |
H407a | −0.169637 | 0.483457 | 0.702199 | 0.0492* | |
H407b | −0.149166 | 0.415957 | 0.623804 | 0.0492* | |
H407c | −0.13547 | 0.431289 | 0.838642 | 0.0492* | |
H408 | 0.143904 | 0.223143 | 0.585864 | 0.027* | |
H411 | 0.454087 | 0.19746 | 0.73458 | 0.0341* | |
H412 | 0.437627 | 0.089816 | 0.673308 | 0.0382* | |
H413 | 0.312213 | 0.049057 | 0.589897 | 0.0393* | |
H414 | 0.203029 | 0.117191 | 0.567973 | 0.033* | |
H104o | 0.7988 (18) | 0.3068 (15) | −0.021 (4) | 0.0442* | |
H204o | 0.5554 (17) | 0.2640 (14) | 0.477 (4) | 0.04* | |
H304o | 0.0559 (18) | 0.2624 (14) | 0.227 (4) | 0.0429* | |
H404o | 0.3030 (18) | 0.3046 (15) | 0.716 (4) | 0.0442* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O101 | 0.0300 (7) | 0.0356 (9) | 0.0317 (7) | −0.0009 (7) | −0.0051 (6) | 0.0042 (7) |
O102 | 0.0340 (8) | 0.0241 (9) | 0.0675 (11) | −0.0051 (7) | 0.0032 (7) | 0.0137 (8) |
O103 | 0.0268 (7) | 0.0371 (9) | 0.0421 (8) | 0.0079 (7) | 0.0018 (6) | 0.0058 (7) |
O104 | 0.0289 (7) | 0.0236 (8) | 0.0361 (8) | −0.0032 (6) | 0.0050 (6) | −0.0027 (6) |
O201 | 0.0451 (11) | 0.0350 (11) | 0.129 (2) | −0.0194 (9) | 0.0263 (12) | −0.0368 (12) |
O202 | 0.0276 (7) | 0.0353 (9) | 0.0348 (7) | 0.0009 (7) | 0.0082 (6) | −0.0014 (7) |
O203 | 0.0239 (7) | 0.0248 (8) | 0.0383 (8) | 0.0033 (6) | 0.0005 (5) | −0.0023 (6) |
O204 | 0.0271 (7) | 0.0183 (7) | 0.0346 (7) | −0.0015 (6) | −0.0037 (6) | −0.0005 (6) |
O301 | 0.0380 (9) | 0.0309 (10) | 0.0987 (15) | −0.0136 (8) | −0.0127 (9) | 0.0267 (10) |
O302 | 0.0289 (7) | 0.0313 (9) | 0.0336 (7) | −0.0014 (6) | −0.0066 (6) | 0.0010 (6) |
O303 | 0.0243 (7) | 0.0243 (8) | 0.0364 (7) | 0.0028 (6) | 0.0013 (5) | 0.0041 (6) |
O304 | 0.0288 (7) | 0.0189 (8) | 0.0381 (8) | −0.0035 (6) | 0.0052 (6) | −0.0026 (6) |
O401 | 0.0364 (8) | 0.0198 (8) | 0.0643 (10) | −0.0075 (7) | 0.0074 (7) | −0.0083 (8) |
O402 | 0.0279 (7) | 0.0298 (8) | 0.0335 (7) | 0.0019 (6) | 0.0063 (6) | −0.0027 (6) |
O403 | 0.0229 (7) | 0.0236 (8) | 0.0384 (7) | 0.0054 (6) | 0.0025 (5) | −0.0035 (6) |
O404 | 0.0279 (7) | 0.0222 (8) | 0.0383 (8) | −0.0007 (6) | −0.0015 (6) | 0.0021 (6) |
N101 | 0.0276 (8) | 0.0192 (9) | 0.0290 (8) | 0.0009 (7) | 0.0048 (7) | −0.0026 (7) |
N102 | 0.0275 (8) | 0.0215 (9) | 0.0202 (7) | 0.0006 (7) | 0.0015 (6) | −0.0008 (6) |
N201 | 0.0258 (9) | 0.0199 (9) | 0.0388 (9) | −0.0021 (7) | 0.0029 (7) | 0.0007 (7) |
N202 | 0.0244 (8) | 0.0195 (9) | 0.0197 (7) | −0.0003 (7) | 0.0021 (6) | 0.0004 (6) |
N301 | 0.0257 (9) | 0.0201 (9) | 0.0331 (9) | −0.0017 (7) | 0.0006 (7) | 0.0004 (7) |
N302 | 0.0252 (8) | 0.0196 (9) | 0.0210 (7) | 0.0006 (7) | −0.0005 (6) | −0.0014 (6) |
N401 | 0.0243 (8) | 0.0184 (9) | 0.0277 (8) | 0.0004 (7) | −0.0003 (6) | 0.0027 (7) |
N402 | 0.0249 (8) | 0.0189 (9) | 0.0220 (7) | 0.0020 (7) | 0.0015 (6) | 0.0023 (6) |
C101 | 0.0274 (10) | 0.0222 (11) | 0.0181 (8) | −0.0006 (8) | 0.0035 (7) | 0.0019 (7) |
C102 | 0.0267 (9) | 0.0239 (11) | 0.0178 (8) | −0.0007 (8) | 0.0011 (7) | 0.0017 (7) |
C103 | 0.0298 (10) | 0.0218 (11) | 0.0235 (9) | 0.0026 (8) | 0.0041 (7) | 0.0030 (8) |
C104 | 0.0273 (10) | 0.0318 (12) | 0.0218 (9) | 0.0073 (9) | 0.0029 (8) | 0.0052 (8) |
C105 | 0.0256 (10) | 0.0364 (13) | 0.0228 (9) | −0.0030 (9) | −0.0009 (7) | 0.0027 (8) |
C106 | 0.0283 (10) | 0.0274 (11) | 0.0213 (9) | −0.0029 (9) | 0.0009 (7) | −0.0005 (8) |
C107 | 0.0274 (12) | 0.0528 (17) | 0.0588 (15) | 0.0084 (11) | 0.0010 (10) | 0.0112 (13) |
C108 | 0.0266 (10) | 0.0225 (11) | 0.0200 (8) | −0.0032 (8) | −0.0006 (7) | −0.0017 (8) |
C109 | 0.0320 (10) | 0.0212 (11) | 0.0168 (8) | 0.0001 (8) | −0.0009 (7) | −0.0032 (7) |
C110 | 0.0300 (10) | 0.0249 (11) | 0.0197 (8) | −0.0015 (8) | −0.0010 (7) | −0.0062 (7) |
C111 | 0.0319 (11) | 0.0365 (13) | 0.0261 (10) | 0.0031 (9) | −0.0018 (8) | −0.0113 (9) |
C112 | 0.0454 (13) | 0.0328 (13) | 0.0262 (10) | 0.0136 (10) | −0.0056 (9) | −0.0087 (9) |
C113 | 0.0542 (14) | 0.0233 (11) | 0.0258 (10) | 0.0059 (10) | −0.0035 (9) | −0.0026 (8) |
C114 | 0.0420 (12) | 0.0208 (11) | 0.0236 (9) | −0.0014 (9) | −0.0004 (8) | 0.0007 (8) |
C201 | 0.0245 (9) | 0.0214 (10) | 0.0174 (8) | −0.0003 (8) | −0.0002 (7) | −0.0017 (7) |
C202 | 0.0238 (9) | 0.0218 (10) | 0.0206 (8) | −0.0023 (8) | 0.0020 (7) | −0.0034 (7) |
C203 | 0.0288 (10) | 0.0173 (10) | 0.0231 (9) | −0.0010 (8) | 0.0012 (7) | −0.0011 (7) |
C204 | 0.0256 (10) | 0.0245 (11) | 0.0203 (8) | 0.0033 (8) | −0.0017 (7) | −0.0037 (8) |
C205 | 0.0246 (10) | 0.0249 (11) | 0.0234 (9) | −0.0019 (8) | 0.0006 (7) | −0.0009 (8) |
C206 | 0.0264 (10) | 0.0216 (11) | 0.0219 (9) | −0.0021 (8) | 0.0012 (7) | 0.0002 (7) |
C207 | 0.0243 (10) | 0.0339 (13) | 0.0452 (12) | 0.0014 (9) | −0.0002 (9) | −0.0069 (10) |
C208 | 0.0242 (9) | 0.0210 (10) | 0.0185 (8) | −0.0033 (8) | 0.0026 (7) | 0.0010 (7) |
C209 | 0.0282 (10) | 0.0189 (10) | 0.0176 (8) | 0.0002 (8) | 0.0040 (7) | 0.0024 (7) |
C210 | 0.0286 (10) | 0.0201 (10) | 0.0189 (8) | −0.0003 (8) | 0.0016 (7) | 0.0012 (7) |
C211 | 0.0288 (10) | 0.0289 (11) | 0.0242 (9) | 0.0028 (9) | 0.0026 (7) | 0.0055 (8) |
C212 | 0.0378 (12) | 0.0251 (11) | 0.0254 (9) | 0.0082 (9) | 0.0057 (8) | 0.0040 (8) |
C213 | 0.0451 (12) | 0.0172 (10) | 0.0256 (9) | 0.0020 (9) | 0.0094 (8) | 0.0021 (8) |
C214 | 0.0338 (11) | 0.0217 (11) | 0.0221 (9) | −0.0031 (8) | 0.0030 (8) | 0.0002 (8) |
C301 | 0.0274 (10) | 0.0213 (10) | 0.0179 (8) | 0.0007 (8) | 0.0019 (7) | 0.0006 (7) |
C302 | 0.0237 (9) | 0.0218 (10) | 0.0202 (8) | −0.0025 (8) | 0.0022 (7) | 0.0039 (7) |
C303 | 0.0298 (10) | 0.0194 (10) | 0.0213 (8) | −0.0002 (8) | 0.0022 (7) | 0.0025 (8) |
C304 | 0.0244 (9) | 0.0254 (11) | 0.0182 (8) | 0.0014 (8) | 0.0023 (7) | 0.0053 (7) |
C305 | 0.0244 (10) | 0.0278 (11) | 0.0222 (8) | −0.0024 (9) | 0.0001 (7) | 0.0002 (8) |
C306 | 0.0300 (10) | 0.0218 (11) | 0.0221 (9) | −0.0039 (8) | 0.0000 (7) | −0.0019 (7) |
C307 | 0.0240 (10) | 0.0324 (13) | 0.0430 (12) | 0.0006 (9) | 0.0027 (9) | 0.0079 (9) |
C308 | 0.0254 (9) | 0.0240 (11) | 0.0181 (8) | −0.0030 (8) | −0.0002 (7) | −0.0002 (7) |
C309 | 0.0307 (10) | 0.0202 (10) | 0.0180 (8) | 0.0001 (8) | −0.0019 (7) | −0.0003 (7) |
C310 | 0.0302 (10) | 0.0200 (10) | 0.0190 (8) | −0.0009 (8) | −0.0016 (7) | −0.0008 (7) |
C311 | 0.0282 (10) | 0.0302 (12) | 0.0241 (9) | 0.0019 (9) | −0.0009 (8) | −0.0037 (8) |
C312 | 0.0408 (12) | 0.0298 (12) | 0.0238 (9) | 0.0124 (10) | −0.0039 (8) | −0.0015 (8) |
C313 | 0.0499 (13) | 0.0181 (11) | 0.0284 (10) | 0.0052 (10) | −0.0004 (9) | 0.0019 (8) |
C314 | 0.0380 (11) | 0.0229 (11) | 0.0244 (9) | −0.0031 (9) | 0.0004 (8) | 0.0030 (8) |
C401 | 0.0255 (9) | 0.0200 (10) | 0.0185 (8) | 0.0009 (8) | −0.0018 (7) | −0.0011 (7) |
C402 | 0.0249 (9) | 0.0194 (10) | 0.0171 (8) | −0.0019 (8) | −0.0001 (7) | −0.0014 (7) |
C403 | 0.0261 (10) | 0.0178 (10) | 0.0224 (8) | 0.0019 (8) | −0.0006 (7) | −0.0026 (7) |
C404 | 0.0238 (10) | 0.0256 (11) | 0.0220 (9) | 0.0033 (8) | −0.0005 (7) | −0.0044 (8) |
C405 | 0.0244 (10) | 0.0263 (11) | 0.0221 (9) | −0.0018 (8) | 0.0017 (7) | −0.0005 (8) |
C406 | 0.0284 (10) | 0.0212 (10) | 0.0211 (9) | −0.0004 (8) | 0.0021 (7) | 0.0015 (7) |
C407 | 0.0233 (10) | 0.0327 (13) | 0.0426 (12) | 0.0016 (9) | 0.0027 (9) | −0.0070 (10) |
C408 | 0.0270 (10) | 0.0205 (10) | 0.0202 (8) | −0.0013 (8) | 0.0039 (7) | 0.0028 (7) |
C409 | 0.0317 (11) | 0.0188 (10) | 0.0178 (8) | 0.0032 (8) | 0.0032 (7) | 0.0044 (7) |
C410 | 0.0300 (10) | 0.0232 (11) | 0.0207 (8) | 0.0007 (8) | 0.0053 (7) | 0.0052 (7) |
C411 | 0.0298 (11) | 0.0308 (12) | 0.0246 (9) | 0.0065 (9) | 0.0046 (8) | 0.0052 (8) |
C412 | 0.0396 (12) | 0.0303 (12) | 0.0259 (10) | 0.0147 (10) | 0.0088 (8) | 0.0063 (9) |
C413 | 0.0497 (13) | 0.0208 (11) | 0.0280 (10) | 0.0071 (10) | 0.0081 (9) | −0.0013 (8) |
C414 | 0.0358 (11) | 0.0224 (11) | 0.0244 (9) | 0.0017 (9) | 0.0037 (8) | 0.0003 (8) |
O101—N101 | 1.225 (2) | C205—C206 | 1.392 (3) |
O102—N101 | 1.230 (2) | C205—H205 | 0.96 |
O103—C104 | 1.364 (3) | C206—H206 | 0.96 |
O103—C107 | 1.434 (3) | C207—H207a | 0.96 |
O104—C110 | 1.350 (3) | C207—H207b | 0.96 |
O104—H104o | 0.86 (3) | C207—H207c | 0.96 |
O201—N201 | 1.226 (3) | C208—C209 | 1.453 (3) |
O202—N201 | 1.220 (2) | C208—H208 | 0.96 |
O203—C204 | 1.360 (2) | C209—C210 | 1.406 (3) |
O203—C207 | 1.430 (3) | C209—C214 | 1.403 (3) |
O204—C210 | 1.353 (2) | C210—C211 | 1.397 (3) |
O204—H204o | 0.88 (3) | C211—C212 | 1.376 (3) |
O301—N301 | 1.214 (3) | C211—H211 | 0.96 |
O302—N301 | 1.224 (2) | C212—C213 | 1.394 (3) |
O303—C304 | 1.365 (2) | C212—H212 | 0.96 |
O303—C307 | 1.428 (3) | C213—C214 | 1.380 (3) |
O304—C310 | 1.349 (2) | C213—H213 | 0.96 |
O304—H304o | 0.92 (3) | C214—H214 | 0.96 |
O401—N401 | 1.225 (2) | C301—C302 | 1.402 (3) |
O402—N401 | 1.224 (2) | C301—C306 | 1.396 (3) |
O403—C404 | 1.358 (2) | C302—C303 | 1.375 (3) |
O403—C407 | 1.434 (3) | C303—C304 | 1.392 (3) |
O404—C410 | 1.350 (3) | C303—H303 | 0.96 |
O404—H404o | 0.90 (3) | C304—C305 | 1.390 (3) |
N101—C102 | 1.466 (3) | C305—C306 | 1.386 (3) |
N102—C101 | 1.405 (3) | C305—H305 | 0.96 |
N102—C108 | 1.286 (3) | C306—H306 | 0.96 |
N201—C202 | 1.466 (3) | C307—H307a | 0.96 |
N202—C201 | 1.409 (3) | C307—H307b | 0.96 |
N202—C208 | 1.284 (3) | C307—H307c | 0.96 |
N301—C302 | 1.469 (3) | C308—C309 | 1.449 (3) |
N302—C301 | 1.408 (3) | C308—H308 | 0.96 |
N302—C308 | 1.287 (3) | C309—C310 | 1.409 (3) |
N401—C402 | 1.467 (2) | C309—C314 | 1.402 (3) |
N402—C401 | 1.406 (3) | C310—C311 | 1.391 (3) |
N402—C408 | 1.287 (3) | C311—C312 | 1.374 (3) |
C101—C102 | 1.404 (3) | C311—H311 | 0.96 |
C101—C106 | 1.387 (3) | C312—C313 | 1.393 (3) |
C102—C103 | 1.380 (3) | C312—H312 | 0.96 |
C103—C104 | 1.390 (3) | C313—C314 | 1.380 (3) |
C103—H103 | 0.96 | C313—H313 | 0.96 |
C104—C105 | 1.389 (3) | C314—H314 | 0.96 |
C105—C106 | 1.386 (3) | C401—C402 | 1.405 (3) |
C105—H105 | 0.96 | C401—C406 | 1.393 (3) |
C106—H106 | 0.96 | C402—C403 | 1.376 (3) |
C107—H107a | 0.96 | C403—C404 | 1.393 (3) |
C107—H107b | 0.96 | C403—H403 | 0.96 |
C107—H107c | 0.96 | C404—C405 | 1.389 (3) |
C108—C109 | 1.455 (3) | C405—C406 | 1.387 (3) |
C108—H108 | 0.96 | C405—H405 | 0.96 |
C109—C110 | 1.410 (3) | C406—H406 | 0.96 |
C109—C114 | 1.398 (3) | C407—H407a | 0.96 |
C110—C111 | 1.391 (3) | C407—H407b | 0.96 |
C111—C112 | 1.381 (3) | C407—H407c | 0.96 |
C111—H111 | 0.96 | C408—C409 | 1.453 (3) |
C112—C113 | 1.390 (3) | C408—H408 | 0.96 |
C112—H112 | 0.96 | C409—C410 | 1.407 (3) |
C113—C114 | 1.377 (3) | C409—C414 | 1.399 (3) |
C113—H113 | 0.96 | C410—C411 | 1.394 (3) |
C114—H114 | 0.96 | C411—C412 | 1.373 (3) |
C201—C202 | 1.396 (3) | C411—H411 | 0.96 |
C201—C206 | 1.392 (3) | C412—C413 | 1.392 (3) |
C202—C203 | 1.379 (3) | C412—H412 | 0.96 |
C203—C204 | 1.393 (3) | C413—C414 | 1.382 (3) |
C203—H203 | 0.96 | C413—H413 | 0.96 |
C204—C205 | 1.393 (3) | C414—H414 | 0.96 |
C104—O103—C107 | 116.95 (19) | C210—C211—C212 | 120.0 (2) |
C110—O104—H104o | 107 (2) | C210—C211—H211 | 120.01 |
C204—O203—C207 | 117.60 (16) | C212—C211—H211 | 120.01 |
C210—O204—H204o | 107.8 (19) | C211—C212—C213 | 121.0 (2) |
C304—O303—C307 | 117.21 (16) | C211—C212—H212 | 119.52 |
C310—O304—H304o | 107.9 (19) | C213—C212—H212 | 119.52 |
C404—O403—C407 | 117.14 (16) | C212—C213—C214 | 119.4 (2) |
C410—O404—H404o | 107.8 (19) | C212—C213—H213 | 120.32 |
O101—N101—O102 | 123.36 (18) | C214—C213—H213 | 120.32 |
O101—N101—C102 | 118.60 (16) | C209—C214—C213 | 120.94 (19) |
O102—N101—C102 | 118.04 (16) | C209—C214—H214 | 119.53 |
C101—N102—C108 | 121.01 (17) | C213—C214—H214 | 119.53 |
O201—N201—O202 | 123.75 (19) | N302—C301—C302 | 120.06 (17) |
O201—N201—C202 | 117.72 (18) | N302—C301—C306 | 123.60 (18) |
O202—N201—C202 | 118.52 (17) | C302—C301—C306 | 115.84 (18) |
C201—N202—C208 | 120.74 (17) | N301—C302—C301 | 119.65 (17) |
O301—N301—O302 | 123.54 (18) | N301—C302—C303 | 116.81 (18) |
O301—N301—C302 | 118.27 (17) | C301—C302—C303 | 123.54 (18) |
O302—N301—C302 | 118.18 (16) | C302—C303—C304 | 118.67 (19) |
C301—N302—C308 | 120.78 (17) | C302—C303—H303 | 120.67 |
O401—N401—O402 | 123.44 (17) | C304—C303—H303 | 120.67 |
O401—N401—C402 | 117.91 (16) | O303—C304—C303 | 115.01 (18) |
O402—N401—C402 | 118.64 (16) | O303—C304—C305 | 124.95 (17) |
C401—N402—C408 | 120.64 (17) | C303—C304—C305 | 120.03 (19) |
N102—C101—C102 | 119.14 (17) | C304—C305—C306 | 119.63 (19) |
N102—C101—C106 | 124.35 (18) | C304—C305—H305 | 120.19 |
C102—C101—C106 | 116.02 (18) | C306—C305—H305 | 120.19 |
N101—C102—C101 | 119.18 (17) | C301—C306—C305 | 122.24 (19) |
N101—C102—C103 | 117.24 (18) | C301—C306—H306 | 118.88 |
C101—C102—C103 | 123.59 (18) | C305—C306—H306 | 118.88 |
C102—C103—C104 | 118.3 (2) | O303—C307—H307a | 109.47 |
C102—C103—H103 | 120.87 | O303—C307—H307b | 109.47 |
C104—C103—H103 | 120.87 | O303—C307—H307c | 109.47 |
O103—C104—C103 | 114.54 (19) | H307a—C307—H307b | 109.47 |
O103—C104—C105 | 125.39 (19) | H307a—C307—H307c | 109.47 |
C103—C104—C105 | 120.1 (2) | H307b—C307—H307c | 109.47 |
C104—C105—C106 | 119.94 (19) | N302—C308—C309 | 121.52 (18) |
C104—C105—H105 | 120.03 | N302—C308—H308 | 119.24 |
C106—C105—H105 | 120.03 | C309—C308—H308 | 119.24 |
C101—C106—C105 | 122.1 (2) | C308—C309—C310 | 121.47 (18) |
C101—C106—H106 | 118.97 | C308—C309—C314 | 120.14 (19) |
C105—C106—H106 | 118.97 | C310—C309—C314 | 118.38 (19) |
O103—C107—H107a | 109.47 | O304—C310—C309 | 121.30 (18) |
O103—C107—H107b | 109.47 | O304—C310—C311 | 118.73 (18) |
O103—C107—H107c | 109.47 | C309—C310—C311 | 119.96 (19) |
H107a—C107—H107b | 109.47 | C310—C311—C312 | 120.5 (2) |
H107a—C107—H107c | 109.47 | C310—C311—H311 | 119.77 |
H107b—C107—H107c | 109.47 | C312—C311—H311 | 119.77 |
N102—C108—C109 | 121.33 (18) | C311—C312—C313 | 120.5 (2) |
N102—C108—H108 | 119.34 | C311—C312—H312 | 119.76 |
C109—C108—H108 | 119.34 | C313—C312—H312 | 119.76 |
C108—C109—C110 | 121.17 (18) | C312—C313—C314 | 119.5 (2) |
C108—C109—C114 | 119.90 (19) | C312—C313—H313 | 120.24 |
C110—C109—C114 | 118.90 (19) | C314—C313—H313 | 120.24 |
O104—C110—C109 | 121.68 (18) | C309—C314—C313 | 121.1 (2) |
O104—C110—C111 | 118.52 (19) | C309—C314—H314 | 119.43 |
C109—C110—C111 | 119.78 (19) | C313—C314—H314 | 119.43 |
C110—C111—C112 | 120.0 (2) | N402—C401—C402 | 119.72 (17) |
C110—C111—H111 | 120.02 | N402—C401—C406 | 123.94 (18) |
C112—C111—H111 | 120.02 | C402—C401—C406 | 115.88 (18) |
C111—C112—C113 | 120.9 (2) | N401—C402—C401 | 119.78 (17) |
C111—C112—H112 | 119.57 | N401—C402—C403 | 116.75 (17) |
C113—C112—H112 | 119.57 | C401—C402—C403 | 123.44 (18) |
C112—C113—C114 | 119.5 (2) | C402—C403—C404 | 118.77 (19) |
C112—C113—H113 | 120.25 | C402—C403—H403 | 120.61 |
C114—C113—H113 | 120.25 | C404—C403—H403 | 120.61 |
C109—C114—C113 | 121.0 (2) | O403—C404—C403 | 115.03 (18) |
C109—C114—H114 | 119.52 | O403—C404—C405 | 125.22 (18) |
C113—C114—H114 | 119.52 | C403—C404—C405 | 119.74 (19) |
N202—C201—C202 | 119.76 (17) | C404—C405—C406 | 119.97 (19) |
N202—C201—C206 | 123.46 (18) | C404—C405—H405 | 120.02 |
C202—C201—C206 | 116.31 (18) | C406—C405—H405 | 120.02 |
N201—C202—C201 | 119.45 (17) | C401—C406—C405 | 122.12 (19) |
N201—C202—C203 | 117.04 (18) | C401—C406—H406 | 118.94 |
C201—C202—C203 | 123.50 (18) | C405—C406—H406 | 118.94 |
C202—C203—C204 | 118.60 (19) | O403—C407—H407a | 109.47 |
C202—C203—H203 | 120.7 | O403—C407—H407b | 109.47 |
C204—C203—H203 | 120.7 | O403—C407—H407c | 109.47 |
O203—C204—C203 | 115.07 (18) | H407a—C407—H407b | 109.47 |
O203—C204—C205 | 124.95 (18) | H407a—C407—H407c | 109.47 |
C203—C204—C205 | 119.96 (18) | H407b—C407—H407c | 109.47 |
C204—C205—C206 | 119.59 (18) | N402—C408—C409 | 121.56 (18) |
C204—C205—H205 | 120.2 | N402—C408—H408 | 119.22 |
C206—C205—H205 | 120.2 | C409—C408—H408 | 119.22 |
C201—C206—C205 | 121.99 (19) | C408—C409—C410 | 121.12 (18) |
C201—C206—H206 | 119.01 | C408—C409—C414 | 120.01 (18) |
C205—C206—H206 | 119.01 | C410—C409—C414 | 118.86 (19) |
O203—C207—H207a | 109.47 | O404—C410—C409 | 121.93 (18) |
O203—C207—H207b | 109.47 | O404—C410—C411 | 118.29 (18) |
O203—C207—H207c | 109.47 | C409—C410—C411 | 119.77 (19) |
H207a—C207—H207b | 109.47 | C410—C411—C412 | 120.3 (2) |
H207a—C207—H207c | 109.47 | C410—C411—H411 | 119.86 |
H207b—C207—H207c | 109.47 | C412—C411—H411 | 119.86 |
N202—C208—C209 | 121.67 (17) | C411—C412—C413 | 120.7 (2) |
N202—C208—H208 | 119.16 | C411—C412—H412 | 119.65 |
C209—C208—H208 | 119.16 | C413—C412—H412 | 119.65 |
C208—C209—C210 | 121.37 (18) | C412—C413—C414 | 119.5 (2) |
C208—C209—C214 | 119.76 (18) | C412—C413—H413 | 120.22 |
C210—C209—C214 | 118.84 (18) | C414—C413—H413 | 120.23 |
O204—C210—C209 | 121.52 (18) | C409—C414—C413 | 120.8 (2) |
O204—C210—C211 | 118.56 (18) | C409—C414—H414 | 119.58 |
C209—C210—C211 | 119.91 (19) | C413—C414—H414 | 119.58 |
C103—C104—O103—C107 | −174.57 (19) | C303—C304—O303—C307 | 174.10 (17) |
C203—C204—O203—C207 | −176.30 (17) | C403—C404—O403—C407 | 176.27 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
O104—H104o···N102 | 0.86 (3) | 1.81 (3) | 2.593 (2) | 150 (3) |
O204—H204o···N202 | 0.88 (3) | 1.81 (3) | 2.599 (2) | 148 (3) |
O304—H304o···N302 | 0.92 (3) | 1.76 (3) | 2.593 (2) | 148 (3) |
O404—H404o···N402 | 0.90 (3) | 1.79 (3) | 2.598 (2) | 148 (3) |
Experimental details
Crystal data | |
Chemical formula | C14H12N2O4 |
Mr | 272.3 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 120 |
a, b, c (Å) | 16.8655 (2), 21.0838 (5), 7.0741 (5) |
β (°) | 90.817 (2) |
V (Å3) | 2515.22 (19) |
Z | 8 |
Radiation type | Cu Kα |
µ (mm−1) | 0.9 |
Crystal size (mm) | 0.25 × 0.20 × 0.16 |
Data collection | |
Diffractometer | Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2012) |
Tmin, Tmax | 0.851, 1 |
No. of measured, independent and observed [I > 3σ(I)] reflections | 19454, 7375, 6684 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.598 |
Refinement | |
R[F > 3σ(F)], wR(F), S | 0.033, 0.087, 1.38 |
No. of reflections | 7375 |
No. of parameters | 735 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.15, −0.12 |
Absolute structure | Flack (1983), 2778 Friedel pairs |
Absolute structure parameter | −0.06 (15) |
Computer programs: CrysAlis PRO (Agilent, 2012), SIR2002 (Burla et al., 2003), JANA2006 (Petříček et al., 2006), DIAMOND (Brandenburg & Putz, 2005).
D—H···A | D—H | H···A | D···A | D—H···A |
O104—H104o···N102 | 0.86 (3) | 1.81 (3) | 2.593 (2) | 150 (3) |
O204—H204o···N202 | 0.88 (3) | 1.81 (3) | 2.599 (2) | 148 (3) |
O304—H304o···N302 | 0.92 (3) | 1.76 (3) | 2.593 (2) | 148 (3) |
O404—H404o···N402 | 0.90 (3) | 1.79 (3) | 2.598 (2) | 148 (3) |
Acknowledgements
We acknowledge Golestan University for partial support of this work, the Institutional Research Plan No. AVOZ10100521 of the Institute of Physics, Prague, and the Praemium Academiae Project of the Academy of Sciences of the Czech Republic.
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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.
The present work is part of a structural study of Schiff bases (Khalaji et al., 2007; Fejfarová et al., 2010). The crystal structure contains four crystallographically independent molecules (A–D) in the asymmetric unit (Fig. 1 and 2). All the molecules have similar conformations, the dihedral angles between the two aromatic rings are 33.1 (1)°, 33.76 (9)°, 31.41 (9)°, and 32.56 (10)°. The azomethine functional groups are co-planar with the adjacent benzene rings. The dihedral angles between the planes of the benzene ring and the plane defined by C(aromatic)—C=N atoms are 2.8 (2)°, 1.50 (18)°, 3.19 (19)°, and 2.7 (2)°. The methoxy groups are almost coplanar with the adjacent benzene rings as can be seen from the torsion angles Cx03—Cx04—Ox03—Cx07 (x = 1–4 for molecules A–D) of -174.57 (19)°, -176.30 (17)°, 174.10 (17)°, and 176.27 (17)°, respectively. The average of C═N and C—N bond lengths of 1.286 and 1.407 Å agree well with the corresponding distances in other Schiff bases (Akkurt et al., 2008; Fun et al., 2009; Kargar et al., 2012; Keleşoğlu et al., 2009; Özek et al., 2009; Tanak et al., 2009.
In the crystal, there are two pairs (A+C, B+D) of pseudo inversion-related molecules. The phenol H atoms form strong intramolecular Ox04—H···Nx02 hydrogen bonds with the imine N atoms, generating S(6) ring motifs. Along the c axis, the molecules are stacked with π-π interactions between the 2-hydroxyphenyl and 4-methoxy-2-nitrophenyl rings of A+B and C+D pairs [centroid-centroid distances in the range of 3.5441 (12)Å – 3.7698 (12) Å] (Figure 3).